# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20240904_nar6_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2405026'
loop_
_audit_author_name
_audit_author_address
'Bayler Barnes'
;New Mexico State University
United States of America
;
_audit_update_record             
;
2024-11-25 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
bgbarnes@nmsu.edu
rtelloab@nmsu.edu
_chemical_name_common            ?
_chemical_name_systematic        
'(+-)-methyl (3aR,6R,6aS,10aS)-3a-hydroxy-1-oxooctahydro-1H-benzo[d]furo[3,4-c][1,2]dioxine-6-carboxylate'
_chemical_formula_moiety         'C12 H16 O7'
_chemical_formula_sum            'C12 H16 O7'
_chemical_formula_weight         272.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H16 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.8697(2)
_cell_length_b                   8.42300(10)
_cell_length_c                   22.9132(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.9550(10)
_cell_angle_gamma                90
_cell_volume                     2438.56(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0560
_cell_measurement_theta_min      3.9210
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_preparation       
'tetronate was dissolved in chloroform and stirred for six days at room temperature. Product ran through column for purifcation'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.115
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.716
_diffrn_reflns_theta_min         3.930
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -43.00   0.50    0.05    --  -91.75  77.00 150.00   88
  2  ω    -62.00 -21.00   0.50    0.05    --  -91.75  61.00 120.00   82
  3  ω    -46.00 -21.00   0.50    0.05    --  -91.75  45.00 120.00   50
  4  ω    -64.00 -26.00   0.50    0.05    --  -91.75  61.00  90.00   76
  5  ω    -46.00 -21.00   0.50    0.05    --  -91.75  45.00  60.00   50
  6  ω    -46.00 -21.00   0.50    0.05    --  -91.75  45.00  90.00   50
  7  ω    -45.00 -20.00   0.50    0.05    --  -91.75  45.00   0.00   50
  8  ω    -49.00 -19.00   0.50    0.05    --  -91.75  61.00 -30.00   60
  9  ω    -46.00 -21.00   0.50    0.05    --  -91.75  45.00 -30.00   50
 10  ω    -46.00 -20.00   0.50    0.05    --  -91.75  45.00-180.00   52
 11  ω    -71.00 -24.00   0.50    0.05    --  -91.75 125.00-180.00   94
 12  ω    -78.00 -43.00   0.50    0.05    --  -48.13  94.00 148.00   70
 13  ω    -74.00 -48.00   0.50    0.05    --  -91.75  94.00 148.00   52
 14  ω    -17.00   9.00   0.50    0.05    --  -48.13  94.00 148.00   52
 15  ω    -29.00  27.00   0.50    0.05    --  -48.13  19.00 -90.00  112
 16  ω    -40.00  23.00   0.50    0.05    --  -48.13  38.00-150.00  126
 17  ω     12.00  42.00   0.50    0.05    --   48.13 -94.00  37.00   60
 18  ω     57.00 106.00   0.50    0.05    --  106.80 -94.00  37.00   98
 19  ω   -154.00-100.00   0.50    0.05    --  -91.75 -94.00  37.00  108
 20  ω   -118.00 -75.00   0.50    0.05    --  -48.13-125.00-180.00   86
 21  ω     42.00  68.00   0.50    0.05    --  106.80 -61.00-180.00   52
 22  ω     49.00  75.00   0.50    0.05    --  106.80 -61.00-150.00   52
 23  ω     42.00  68.00   0.50    0.05    --  106.80 -61.00-120.00   52
 24  ω     38.00  67.00   0.50    0.05    --  106.80 -61.00 -90.00   58
 25  ω     40.00  65.00   0.50    0.05    --  106.80 -61.00  90.00   50
 26  ω    117.00 168.00   0.50    0.05    --  106.80  94.00 148.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0259032000
_diffrn_orient_matrix_UB_12      -0.0082912000
_diffrn_orient_matrix_UB_13      0.0684058000
_diffrn_orient_matrix_UB_21      -0.0436040000
_diffrn_orient_matrix_UB_22      0.1693627000
_diffrn_orient_matrix_UB_23      0.0034452000
_diffrn_orient_matrix_UB_31      -0.1108566000
_diffrn_orient_matrix_UB_32      -0.0685444000
_diffrn_orient_matrix_UB_33      0.0003232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2168
_reflns_number_total             2364
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00063(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.9727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C5(H5A,H5B), C10(H10A,H10B), C9(H9A,H9B)
1.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
1.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.59814(6) 0.71274(10) 0.71127(4) 0.0183(2) Uani 1 1 d . . . . .
O6 O 0.69223(6) 0.43559(10) 0.76856(4) 0.0186(2) Uani 1 1 d . . . . .
O19 O 0.83589(6) 0.42720(10) 0.72832(4) 0.0197(2) Uani 1 1 d . . . . .
O2 O 0.61582(6) 0.81087(10) 0.66128(4) 0.0193(2) Uani 1 1 d . . . . .
O18 O 0.47496(6) 0.54640(11) 0.65268(4) 0.0207(2) Uani 1 1 d . . . . .
H18 H 0.426518 0.562064 0.671952 0.031 Uiso 1 1 calc R U . . .
O15 O 0.85326(6) 0.89109(11) 0.61360(4) 0.0213(2) Uani 1 1 d . . . . .
O17 O 0.68701(7) 0.97650(11) 0.57946(4) 0.0256(2) Uani 1 1 d . . . . .
C13 C 0.71019(9) 0.59692(14) 0.62337(5) 0.0159(2) Uani 1 1 d . . . . .
H13 H 0.783560 0.560175 0.621957 0.019 Uiso 1 1 calc R U . . .
C7 C 0.74176(9) 0.44843(14) 0.72198(5) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.71793(9) 0.76334(14) 0.65099(5) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.769918 0.762513 0.689439 0.020 Uiso 1 1 calc R U . . .
C14 C 0.74846(9) 0.89026(15) 0.61039(5) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.64622(9) 0.59720(15) 0.55959(5) 0.0200(3) Uani 1 1 d . . . . .
H12A H 0.576045 0.645697 0.559274 0.024 Uiso 1 1 calc R U . . .
H12B H 0.683387 0.662575 0.534076 0.024 Uiso 1 1 calc R U . . .
C8 C 0.66323(9) 0.48304(14) 0.66450(5) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.63140(10) 0.42990(16) 0.53440(5) 0.0217(3) Uani 1 1 d . . . . .
H11A H 0.590620 0.434353 0.493192 0.026 Uiso 1 1 calc R U . . .
H11B H 0.701450 0.382824 0.533212 0.026 Uiso 1 1 calc R U . . .
C4 C 0.57170(9) 0.55378(14) 0.69061(5) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.57971(9) 0.46518(15) 0.74949(5) 0.0193(3) Uani 1 1 d . . . . .
H5A H 0.552123 0.530869 0.778979 0.023 Uiso 1 1 calc R U . . .
H5B H 0.539645 0.364247 0.743791 0.023 Uiso 1 1 calc R U . . .
C10 C 0.57332(9) 0.32570(15) 0.57190(5) 0.0203(3) Uani 1 1 d . . . . .
H10A H 0.564578 0.217565 0.554729 0.024 Uiso 1 1 calc R U . . .
H10B H 0.502104 0.370056 0.571955 0.024 Uiso 1 1 calc R U . . .
C9 C 0.63607(9) 0.31761(14) 0.63546(5) 0.0188(3) Uani 1 1 d . . . . .
H9A H 0.702768 0.259114 0.635385 0.023 Uiso 1 1 calc R U . . .
H9B H 0.594664 0.256665 0.660077 0.023 Uiso 1 1 calc R U . . .
C16 C 0.89238(11) 1.01272(17) 0.57802(6) 0.0266(3) Uani 1 1 d . . . . .
H16A H 0.867577 0.989937 0.535727 0.040 Uiso 1 1 calc R U . . .
H16B H 0.969929 1.013187 0.586895 0.040 Uiso 1 1 calc R U . . .
H16C H 0.865930 1.116831 0.587526 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 O2 1.4648(11) . ?
O3 C4 1.4393(15) . ?
O6 C7 1.3476(14) . ?
O6 C5 1.4524(14) . ?
O19 C7 1.2057(14) . ?
O2 C1 1.4355(14) . ?
O18 C4 1.3776(14) . ?
O15 C14 1.3367(14) . ?
O15 C16 1.4572(15) . ?
O17 C14 1.2009(15) . ?
C13 C1 1.5335(17) . ?
C13 C12 1.5350(16) . ?
C13 C8 1.5461(16) . ?
C7 C8 1.5281(16) . ?
C1 C14 1.5171(16) . ?
C12 C11 1.5209(18) . ?
C8 C4 1.5389(15) . ?
C8 C9 1.5550(16) . ?
C11 C10 1.5203(17) . ?
C4 C5 1.5280(16) . ?
C10 C9 1.5267(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 O2 109.26(8) . . ?
C7 O6 C5 110.03(9) . . ?
C1 O2 O3 104.73(8) . . ?
C14 O15 C16 115.16(10) . . ?
C1 C13 C12 111.87(10) . . ?
C1 C13 C8 108.53(9) . . ?
C12 C13 C8 112.35(9) . . ?
O6 C7 C8 111.28(9) . . ?
O19 C7 O6 120.55(11) . . ?
O19 C7 C8 128.10(10) . . ?
O2 C1 C13 109.46(9) . . ?
O2 C1 C14 104.84(9) . . ?
C14 C1 C13 113.27(10) . . ?
O15 C14 C1 110.25(10) . . ?
O17 C14 O15 125.01(11) . . ?
O17 C14 C1 124.74(11) . . ?
C11 C12 C13 111.45(10) . . ?
C13 C8 C9 112.15(9) . . ?
C7 C8 C13 111.87(9) . . ?
C7 C8 C4 99.71(9) . . ?
C7 C8 C9 104.83(9) . . ?
C4 C8 C13 114.43(10) . . ?
C4 C8 C9 112.76(9) . . ?
C10 C11 C12 111.11(10) . . ?
O3 C4 C8 109.72(9) . . ?
O3 C4 C5 101.06(9) . . ?
O18 C4 O3 112.23(9) . . ?
O18 C4 C8 113.84(10) . . ?
O18 C4 C5 115.86(10) . . ?
C5 C4 C8 103.05(9) . . ?
O6 C5 C4 104.22(9) . . ?
C11 C10 C9 109.70(10) . . ?
C10 C9 C8 113.79(10) . . ?

_olex2_exptl_crystal_mounting_method 'in NVH oil on 200 micron nylon loop'
_olex2_submission_original_sample_id 20240904_NAR6_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20240926_nar7_5_auto
_database_code_depnum_ccdc_archive 'CCDC 2405027'
loop_
_audit_author_name
_audit_author_address
'Bayler Barnes'
;New Mexico State University
United States of America
;
_audit_update_record             
;
2024-11-25 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
bgbarnes@nmsu.edu
_chemical_name_common            ?
_chemical_name_systematic        
'(+-)-methyl (3aR,5R,5aS,9aS)-3a-hydroxy-1-oxooctahydro-1H-furo[3,4-c]isobenzofuran-5-carboxylate'
_chemical_formula_moiety         'C12 H16 O6'
_chemical_formula_sum            'C12 H16 O6'
_chemical_formula_weight         256.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H16 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4041(2)
_cell_length_b                   8.73516(16)
_cell_length_c                   12.8916(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.9965(18)
_cell_angle_gamma                90
_cell_volume                     1171.43(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4630
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3510
_cell_measurement_theta_min      5.3930
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.103
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8054
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.686
_diffrn_reflns_theta_min         5.418
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  95.00   0.50    0.09    --  106.80 -77.00-150.00  118
  2  ω     35.00  60.00   0.50    0.09    --  106.80 -61.00-180.00   50
  3  ω     41.00  66.00   0.50    0.09    --  106.80 -61.00-150.00   50
  4  ω     34.00  73.00   0.50    0.09    --  106.80 -61.00  30.00   78
  5  ω     38.00  63.00   0.50    0.09    --  106.80 -61.00  60.00   50
  6  ω     36.00  73.00   0.50    0.09    --  106.80 -61.00  90.00   74
  7  ω      8.00  44.00   0.50    0.05    --   47.88 -36.00  27.00   72
  8  ω     54.00  79.00   0.50    0.05    --   47.88  36.00-176.00   50
  9  ω     95.00 178.00   0.50    0.09    --  106.80  36.00-176.00  166
 10  ω    105.00 168.00   0.50    0.09    --  106.80 125.00  60.00  126
 11  ω     74.00 102.00   0.50    0.09    --  106.80 -95.00  60.00   56
 12  ω     34.00  59.00   0.50    0.09    --  106.80 -95.00  60.00   50
 13  ω    -38.00  24.00   0.50    0.05    --  -47.88  36.00-176.00  124
 14  ω    -20.00  18.00   0.50    0.05    --  -47.88  19.00-120.00   76
 15  ω    -24.00  27.00   0.50    0.05    --  -47.88  19.00 -30.00  102
 16  ω    -46.00 -21.00   0.50    0.09    --  -91.75  45.00   0.00   50
 17  ω    -54.00 -28.00   0.50    0.09    --  -91.75  61.00 -30.00   52
 18  ω    -46.00 -21.00   0.50    0.09    --  -91.75  61.00 -90.00   50
 19  ω    -63.00 -23.00   0.50    0.09    --  -91.75  61.00-120.00   80
 20  ω    -64.00 -20.00   0.50    0.09    --  -91.75  61.00-180.00   88
 21  ω    -46.00 -21.00   0.50    0.09    --  -91.75  45.00 -90.00   50
 22  ω    -46.00 -21.00   0.50    0.09    --  -91.75  45.00 120.00   50
 23  ω   -146.00-121.00   0.50    0.09    --  -91.75 -36.00  27.00   50
 24  ω   -124.00 -88.00   0.50    0.09    --  -91.75-125.00-180.00   72
 25  ω   -160.00-134.00   0.50    0.09    --  -91.75-125.00-180.00   52
 26  ω   -120.00 -36.00   0.50    0.05    --  -47.88 -36.00  27.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1133048000
_diffrn_orient_matrix_UB_12      -0.0218034000
_diffrn_orient_matrix_UB_13      0.0771598000
_diffrn_orient_matrix_UB_21      -0.0779910000
_diffrn_orient_matrix_UB_22      0.0786515000
_diffrn_orient_matrix_UB_23      0.0853718000
_diffrn_orient_matrix_UB_31      -0.0549102000
_diffrn_orient_matrix_UB_32      -0.1563249000
_diffrn_orient_matrix_UB_33      0.0322944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2071
_reflns_number_total             2336
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.6965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7), C2(H2A)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C4(H4A,H4B), C6(H6A,H6B)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43631(9) 0.15634(12) 0.54710(8) 0.0209(2) Uani 1 1 d . . . . .
O2 O 0.59187(10) 0.01228(12) 0.63411(8) 0.0224(3) Uani 1 1 d . . . . .
H2 H 0.594169 -0.051537 0.585429 0.034 Uiso 1 1 calc R U . . .
O6 O 0.13941(10) 0.29211(12) 0.64464(9) 0.0258(3) Uani 1 1 d . . . . .
O4 O 0.58467(11) 0.55468(12) 0.62998(9) 0.0275(3) Uani 1 1 d . . . . .
O3 O 0.65682(10) 0.37678(12) 0.52196(8) 0.0256(3) Uani 1 1 d . . . . .
O5 O 0.19317(11) 0.05900(13) 0.58653(10) 0.0342(3) Uani 1 1 d . . . . .
C7 C 0.35224(13) 0.26058(16) 0.59918(11) 0.0188(3) Uani 1 1 d . . . . .
H7 H 0.344958 0.357611 0.558327 0.023 Uiso 1 1 calc R U . . .
C1 C 0.55921(13) 0.28379(16) 0.67529(11) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.41692(14) 0.29434(16) 0.70491(11) 0.0194(3) Uani 1 1 d . . . . .
H2A H 0.395859 0.400607 0.727924 0.023 Uiso 1 1 calc R U . . .
C11 C 0.22088(14) 0.18829(16) 0.60772(11) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.59828(14) 0.42157(17) 0.61011(12) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.38249(14) 0.17869(18) 0.78932(11) 0.0231(3) Uani 1 1 d . . . . .
H3A H 0.292946 0.196415 0.811149 0.028 Uiso 1 1 calc R U . . .
H3B H 0.387744 0.073707 0.760773 0.028 Uiso 1 1 calc R U . . .
C8 C 0.56339(13) 0.15597(17) 0.59434(11) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.61104(15) 0.16164(19) 0.85220(12) 0.0256(3) Uani 1 1 d . . . . .
H5A H 0.618095 0.055233 0.826477 0.031 Uiso 1 1 calc R U . . .
H5B H 0.668428 0.172098 0.913850 0.031 Uiso 1 1 calc R U . . .
C9 C 0.65897(14) 0.21163(17) 0.51413(12) 0.0233(3) Uani 1 1 d . . . . .
H9A H 0.746153 0.171508 0.529820 0.028 Uiso 1 1 calc R U . . .
H9B H 0.632479 0.178184 0.443566 0.028 Uiso 1 1 calc R U . . .
C4 C 0.47286(15) 0.19255(19) 0.88337(12) 0.0264(3) Uani 1 1 d . . . . .
H4A H 0.466437 0.296743 0.913053 0.032 Uiso 1 1 calc R U . . .
H4B H 0.447261 0.118246 0.937193 0.032 Uiso 1 1 calc R U . . .
C6 C 0.65446(14) 0.27200(18) 0.76806(12) 0.0240(3) Uani 1 1 d . . . . .
H6A H 0.738944 0.238002 0.742441 0.029 Uiso 1 1 calc R U . . .
H6B H 0.666035 0.374937 0.798970 0.029 Uiso 1 1 calc R U . . .
C12 C 0.01137(15) 0.2379(2) 0.66628(14) 0.0324(4) Uani 1 1 d . . . . .
H12A H -0.027691 0.195334 0.602841 0.049 Uiso 1 1 calc R U . . .
H12B H -0.041090 0.323218 0.690883 0.049 Uiso 1 1 calc R U . . .
H12C H 0.016081 0.158265 0.719781 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.4372(17) . ?
O1 C8 1.4460(16) . ?
O2 H2 0.8400 . ?
O2 C8 1.3859(17) . ?
O6 C11 1.3347(18) . ?
O6 C12 1.4457(18) . ?
O4 C10 1.1995(19) . ?
O3 C10 1.3563(18) . ?
O3 C9 1.4463(19) . ?
O5 C11 1.1960(18) . ?
C7 H7 1.0000 . ?
C7 C2 1.5381(19) . ?
C7 C11 1.511(2) . ?
C1 C2 1.5380(19) . ?
C1 C10 1.527(2) . ?
C1 C8 1.5294(19) . ?
C1 C6 1.543(2) . ?
C2 H2A 1.0000 . ?
C2 C3 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(2) . ?
C8 C9 1.527(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.524(2) . ?
C5 C6 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 111.35(10) . . ?
C8 O2 H2 109.5 . . ?
C11 O6 C12 116.05(12) . . ?
C10 O3 C9 110.73(11) . . ?
O1 C7 H7 109.4 . . ?
O1 C7 C2 105.96(11) . . ?
O1 C7 C11 109.13(11) . . ?
C2 C7 H7 109.4 . . ?
C11 C7 H7 109.4 . . ?
C11 C7 C2 113.44(12) . . ?
C2 C1 C6 114.80(12) . . ?
C10 C1 C2 110.85(12) . . ?
C10 C1 C8 100.89(11) . . ?
C10 C1 C6 107.79(11) . . ?
C8 C1 C2 104.60(11) . . ?
C8 C1 C6 117.04(12) . . ?
C7 C2 H2A 110.3 . . ?
C1 C2 C7 100.18(11) . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 C7 113.51(12) . . ?
C3 C2 C1 112.01(12) . . ?
C3 C2 H2A 110.3 . . ?
O6 C11 C7 108.83(12) . . ?
O5 C11 O6 124.82(14) . . ?
O5 C11 C7 126.34(13) . . ?
O4 C10 O3 120.99(14) . . ?
O4 C10 C1 127.81(14) . . ?
O3 C10 C1 111.19(12) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.32(12) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
O1 C8 C1 104.43(11) . . ?
O1 C8 C9 108.40(11) . . ?
O2 C8 O1 110.23(11) . . ?
O2 C8 C1 114.66(11) . . ?
O2 C8 C9 113.67(12) . . ?
C9 C8 C1 104.85(11) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.59(13) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
O3 C9 C8 105.03(11) . . ?
O3 C9 H9A 110.7 . . ?
O3 C9 H9B 110.7 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 C3 110.34(12) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C1 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
C5 C6 C1 113.52(12) . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C2 C1 32.42(13) . . . . ?
O1 C7 C2 C3 -87.14(14) . . . . ?
O1 C7 C11 O6 -172.60(11) . . . . ?
O1 C7 C11 O5 8.3(2) . . . . ?
O1 C8 C9 O3 85.63(13) . . . . ?
O2 C8 C9 O3 -151.43(11) . . . . ?
C7 O1 C8 O2 117.46(12) . . . . ?
C7 O1 C8 C1 -6.17(14) . . . . ?
C7 O1 C8 C9 -117.54(12) . . . . ?
C7 C2 C3 C4 165.82(12) . . . . ?
C1 C2 C3 C4 53.25(16) . . . . ?
C1 C8 C9 O3 -25.46(14) . . . . ?
C2 C7 C11 O6 69.51(15) . . . . ?
C2 C7 C11 O5 -109.58(17) . . . . ?
C2 C1 C10 O4 52.7(2) . . . . ?
C2 C1 C10 O3 -128.70(12) . . . . ?
C2 C1 C8 O1 26.96(14) . . . . ?
C2 C1 C8 O2 -93.77(13) . . . . ?
C2 C1 C8 C9 140.87(12) . . . . ?
C2 C1 C6 C5 43.45(17) . . . . ?
C2 C3 C4 C5 -60.49(17) . . . . ?
C11 C7 C2 C1 152.13(12) . . . . ?
C11 C7 C2 C3 32.57(17) . . . . ?
C10 O3 C9 C8 14.43(15) . . . . ?
C10 C1 C2 C7 72.09(13) . . . . ?
C10 C1 C2 C3 -167.26(12) . . . . ?
C10 C1 C8 O1 -88.17(12) . . . . ?
C10 C1 C8 O2 151.10(11) . . . . ?
C10 C1 C8 C9 25.75(14) . . . . ?
C10 C1 C6 C5 167.51(12) . . . . ?
C8 O1 C7 C2 -17.14(14) . . . . ?
C8 O1 C7 C11 -139.63(12) . . . . ?
C8 C1 C2 C7 -35.86(13) . . . . ?
C8 C1 C2 C3 84.80(14) . . . . ?
C8 C1 C10 O4 163.11(15) . . . . ?
C8 C1 C10 O3 -18.35(15) . . . . ?
C8 C1 C6 C5 -79.75(16) . . . . ?
C9 O3 C10 O4 -178.62(13) . . . . ?
C9 O3 C10 C1 2.72(16) . . . . ?
C4 C5 C6 C1 -49.79(17) . . . . ?
C6 C1 C2 C7 -165.49(12) . . . . ?
C6 C1 C2 C3 -44.83(16) . . . . ?
C6 C1 C10 O4 -73.67(19) . . . . ?
C6 C1 C10 O3 104.88(13) . . . . ?
C6 C1 C8 O1 155.24(12) . . . . ?
C6 C1 C8 O2 34.51(17) . . . . ?
C6 C1 C8 C9 -90.84(15) . . . . ?
C6 C5 C4 C3 58.42(17) . . . . ?
C12 O6 C11 O5 4.3(2) . . . . ?
C12 O6 C11 C7 -174.78(12) . . . . ?

_olex2_exptl_crystal_mounting_method 
'on 200 micron loop in NVH oil under a cold stream of nitrogen (100 K)'
_olex2_submission_original_sample_id 20240926_NAR7_5
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.618
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20250701_nar9_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2476611'
loop_
_audit_author_name
_audit_author_address
'Bayler Barnes'
;New Mexico State University
United States of America
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2025-07-28
_audit_creation_method           
;
Olex2 1.5-ac6-015
(compiled 2023.12.04 svn.r209d9fb2 for Rigaku Oxford Diffraction, GUI svn.r6873)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
rtelloab@nmsu.edu
bgbarnes@nmsu.edu
_chemical_name_common            ?
_chemical_name_systematic        
(3aR,6aS,10aS)-3a-hydroxyoctahydro-1H-benzo[d]furo[3,4-c][1,2]dioxin-1-one
_chemical_formula_moiety         'C10 H14 O5'
_chemical_formula_sum            'C10 H14 O5'
_chemical_formula_weight         214.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9717(4)
_cell_length_b                   8.9531(3)
_cell_length_c                   11.4158(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.398(4)
_cell_angle_gamma                90
_cell_volume                     972.55(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4695
_cell_measurement_temperature    120.3(4)
_cell_measurement_theta_max      80.0400
_cell_measurement_theta_min      5.1550
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Clear - Colorless'
_exptl_crystal_colour_lustre     Clear
_exptl_crystal_colour_modifier   -
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_preparation       
'Stirring 3-(hex-5-en-1-yl)-4-hydroxyfuran-2(5H)-one in dichloromethane at room temperature for 6 days'
_exptl_crystal_recrystallization_method 
'Vapour diffusion of hexane into a DCM solution'
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.946
_diffrn_reflns_theta_min         5.177
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.3(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -22.00   0.50    0.18    --  -38.28 142.00 160.00  154
  2  ω   -123.00 -63.00   0.50    0.18    --  -38.28-142.00 103.00  120
  3  ω   -122.00 -72.00   0.50    0.18    --  -38.28-129.00 -84.00  100
  4  ω     44.00 120.00   0.50    0.18    --   38.28-142.00 103.00  152
  5  ω   -165.00 -71.00   0.50    0.70    --  -84.64-129.00 -84.00  188
  6  ω    -98.00 -22.00   0.50    0.70    --  -84.64 142.00 160.00  152
  7  ω   -155.00 -62.00   0.50    0.70    --  -84.64-142.00 103.00  186
  8  ω     44.00 124.00   0.50    0.70    --   84.64-142.00 103.00  160
  9  ω     37.00 114.00   0.50    0.70    --   84.64-129.00 -84.00  154
 10  ω    -98.00 -23.00   0.50    0.70    -- -106.00 142.00 160.00  150
 11  ω     46.00 115.00   0.50    0.70    --  131.00-129.00 -84.00  138
 12  ω     45.00 125.00   0.50    0.70    --  131.00-142.00 103.00  160
 13  ω     84.00 172.00   0.50    0.70    --  131.00 142.00 160.00  176
 14  ω    -31.00  44.00   0.50    0.18    --  -38.28  19.00-180.00  150
 15  ω    -31.00  44.00   0.50    0.18    --  -38.28  19.00 -60.00  150
 16  ω   -132.00 -86.00   0.50    0.18    --  -38.28 -99.00 120.00   92
 17  ω    -31.00  44.00   0.50    0.18    --  -38.28  19.00-180.00  150
 18  ω   -177.00-145.00   0.50    0.70    --  -84.64  15.00-180.00   64
 19  ω   -177.00-145.00   0.50    0.70    --  -84.64  15.00-150.00   64
 20  ω    -46.00  -2.00   0.50    0.70    --  -84.64  45.00   0.00   88
 21  ω   -177.00-145.00   0.50    0.70    --  -84.64  15.00 -30.00   64
 22  ω     -8.00  47.00   0.50    0.70    --   84.64 -30.00  60.00  110
 23  ω     -8.00  47.00   0.50    0.70    --   84.64 -30.00 150.00  110
 24  ω    103.00 163.00   0.50    0.70    --   84.64 111.00 -90.00  120
 25  ω    -81.00 -25.00   0.50    0.70    -- -106.00 104.00 -30.00  112
 26  ω    -51.00 -23.00   0.50    0.70    -- -106.00  50.00 -60.00   56
 27  ω    -51.00 -23.00   0.50    0.70    -- -106.00  50.00 -30.00   56
 28  ω    -51.00 -23.00   0.50    0.70    -- -106.00  50.00  30.00   56
 29  ω    106.00 178.00   0.50    0.70    --  131.00 104.00 -30.00  144
 30  ω     43.00  80.00   0.50    0.70    --  131.00 -64.00 -30.00   74
 31  ω     38.00 107.00   0.50    0.70    --  131.00-104.00  90.00  138
 32  ω     43.00  80.00   0.50    0.70    --  131.00 -64.00  30.00   74
 33  ω     89.00 178.00   0.50    0.70    --  131.00  64.00-180.00  178
 34  ω     38.00 107.00   0.50    0.70    --  131.00-104.00  90.00  138
 35  ω     38.00 107.00   0.50    0.70    --  131.00-104.00 120.00  138
 36  ω    151.00 178.00   0.50    0.70    --  131.00 -12.00  90.00   54
 37  ω    151.00 178.00   0.50    0.70    --  131.00 -12.00-180.00   54
 38  ω     34.00 106.00   0.50    0.70    --  131.00 -92.00 150.00  144
 39  ω     89.00 178.00   0.50    0.70    --  131.00  64.00  90.00  178
 40  ω     38.00 107.00   0.50    0.70    --  131.00-104.00 150.00  138
 41  ω     35.00 101.00   0.50    0.70    --  131.00 -77.00 -30.00  132
 42  ω    151.00 178.00   0.50    0.70    --  131.00 -12.00 120.00   54
 43  ω     38.00 107.00   0.50    0.70    --  131.00-104.00 -90.00  138
 44  ω     89.00 178.00   0.50    0.70    --  131.00  64.00  90.00  178
 45  ω     83.00 178.00   0.50    0.70    --  131.00  50.00-150.00  190
 46  ω     34.00 106.00   0.50    0.70    --  131.00 -92.00 120.00  144
 47  ω     35.00 101.00   0.50    0.70    --  131.00 -77.00 120.00  132
 48  ω     35.00 101.00   0.50    0.70    --  131.00 -77.00 150.00  132
 49  ω     38.00 107.00   0.50    0.70    --  131.00-104.00-120.00  138
 50  ω    106.00 178.00   0.50    0.70    --  131.00 104.00  60.00  144
 51  ω     89.00 178.00   0.50    0.70    --  131.00  64.00 120.00  178
 52  ω     43.00  80.00   0.50    0.70    --  131.00 -64.00 150.00   74
 53  ω   -128.00  33.00   0.50    0.18    --  -38.28 -38.00 150.00  322
 54  ω    -21.00  18.00   0.50    0.18    --   38.28 101.00  67.87   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0766415000
_diffrn_orient_matrix_UB_12      0.1149459000
_diffrn_orient_matrix_UB_13      -0.0574167000
_diffrn_orient_matrix_UB_21      0.0757671000
_diffrn_orient_matrix_UB_22      -0.1279507000
_diffrn_orient_matrix_UB_23      -0.0448878000
_diffrn_orient_matrix_UB_31      -0.1206691000
_diffrn_orient_matrix_UB_32      -0.0071094000
_diffrn_orient_matrix_UB_33      -0.1211896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1795
_reflns_number_total             2102
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-015 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-015 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²+0.6295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C7(H7A,H7B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.11525(15) 0.36623(17) 0.31476(12) 0.0315(4) Uani 1 1 d . . . . .
H3 H 0.081920 0.368223 0.237940 0.047 Uiso 1 1 calc R U . . .
O2 O 0.17329(15) 0.11318(16) 0.31462(12) 0.0304(3) Uani 1 1 d . . . . .
O4 O 0.46086(14) 0.21348(17) 0.36766(12) 0.0303(3) Uani 1 1 d . . . . .
O5 O 0.54120(14) 0.15996(17) 0.56456(13) 0.0319(4) Uani 1 1 d . . . . .
O1 O 0.08974(15) 0.05969(18) 0.39079(13) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.44685(19) 0.2068(2) 0.48056(17) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.30638(19) 0.2708(2) 0.48495(16) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.2223(2) 0.2618(2) 0.34811(17) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.2444(2) 0.1789(2) 0.57030(17) 0.0282(4) Uani 1 1 d . . . . .
H1 H 0.321703 0.156934 0.647258 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3348(2) 0.2746(2) 0.28220(18) 0.0306(4) Uani 1 1 d . . . . .
H9A H 0.307562 0.216714 0.204758 0.037 Uiso 1 1 calc R U . . .
H9B H 0.349144 0.380177 0.263203 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3393(2) 0.4340(2) 0.53102(19) 0.0326(5) Uani 1 1 d . . . . .
H3A H 0.425656 0.433888 0.601963 0.039 Uiso 1 1 calc R U . . .
H3B H 0.358811 0.493761 0.464997 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1889(2) 0.0307(2) 0.50873(18) 0.0333(5) Uani 1 1 d . . . . .
H7A H 0.267778 -0.029980 0.498769 0.040 Uiso 1 1 calc R U . . .
H7B H 0.142837 -0.025905 0.560489 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1281(2) 0.2618(3) 0.60542(19) 0.0357(5) Uani 1 1 d . . . . .
H6A H 0.046073 0.274098 0.531508 0.043 Uiso 1 1 calc R U . . .
H6B H 0.097880 0.201284 0.665611 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2218(2) 0.5097(3) 0.5693(2) 0.0403(5) Uani 1 1 d . . . . .
H4A H 0.255073 0.607751 0.606979 0.048 Uiso 1 1 calc R U . . .
H4B H 0.140530 0.527390 0.495791 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1759(2) 0.4144(3) 0.6603(2) 0.0423(6) Uani 1 1 d . . . . .
H5A H 0.097820 0.464364 0.681760 0.051 Uiso 1 1 calc R U . . .
H5B H 0.255118 0.402568 0.736430 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C8 1.384(2) . ?
O2 O1 1.4535(19) . ?
O2 C8 1.430(2) . ?
O4 C10 1.339(2) . ?
O4 C9 1.449(2) . ?
O5 C10 1.200(2) . ?
O1 C7 1.436(2) . ?
C10 C2 1.528(3) . ?
C2 C8 1.538(2) . ?
C2 C1 1.539(3) . ?
C2 C3 1.554(3) . ?
C8 C9 1.530(3) . ?
C1 C7 1.526(3) . ?
C1 C6 1.528(3) . ?
C3 C4 1.526(3) . ?
C6 C5 1.519(3) . ?
C4 C5 1.517(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 O1 110.97(13) . . ?
C10 O4 C9 110.23(14) . . ?
C7 O1 O2 105.25(13) . . ?
O4 C10 C2 112.05(15) . . ?
O5 C10 O4 120.15(17) . . ?
O5 C10 C2 127.73(17) . . ?
C10 C2 C8 99.99(14) . . ?
C10 C2 C1 111.45(16) . . ?
C10 C2 C3 105.12(15) . . ?
C8 C2 C1 114.49(15) . . ?
C8 C2 C3 112.90(16) . . ?
C1 C2 C3 111.87(16) . . ?
O3 C8 O2 112.42(15) . . ?
O3 C8 C2 112.65(15) . . ?
O3 C8 C9 115.63(16) . . ?
O2 C8 C2 111.07(15) . . ?
O2 C8 C9 100.39(15) . . ?
C9 C8 C2 103.79(15) . . ?
C7 C1 C2 109.40(15) . . ?
C7 C1 C6 110.13(17) . . ?
C6 C1 C2 112.75(17) . . ?
O4 C9 C8 104.88(14) . . ?
C4 C3 C2 114.32(17) . . ?
O1 C7 C1 109.16(16) . . ?
C5 C6 C1 112.07(18) . . ?
C5 C4 C3 111.17(19) . . ?
C4 C5 C6 110.20(17) . . ?


_olex2_date_sample_data_collection 2025-07-01
_olex2_exptl_crystal_mounting_method 
'in NVH oil on a nylon loop under a nitrogen cold stream'
_olex2_submission_original_sample_id 20250701_NAR9_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.072
_oxdiff_exptl_absorpt_empirical_full_min 0.657
