# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_(3R,6S,7S)-3

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 Br2 O4'
_chemical_formula_sum            'C10 H20 Br2 O4'
_chemical_formula_weight         364.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2172(3)
_cell_length_b                   12.8186(6)
_cell_length_c                   21.7125(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.07(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    1036
_cell_measurement_theta_min      3.6800
_cell_measurement_theta_max      23.3810

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    5.580
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.252
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            4605
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         28.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2874
_reflns_number_gt                2040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    0.983

_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.
;

_computing_data_collection       CrysAlisPro,
_computing_cell_refinement       CrysAlisPro,
_computing_data_reduction        CrysAlisPro,
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+1.4062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.014(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     163
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.9755(13) 0.6635(5) 0.4571(3) 0.0325(18) Uani 1 1 d . . . . .
H1A H 1.0213 0.7119 0.4239 0.049 Uiso 1 1 calc R U . . .
H1B H 1.1319 0.6346 0.4753 0.049 Uiso 1 1 calc R U . . .
H1C H 0.8780 0.7008 0.4888 0.049 Uiso 1 1 calc R U . . .
C2 C 0.8131(12) 0.5755(5) 0.4311(3) 0.0242(17) Uani 1 1 d . . . . .
C3 C 0.9731(13) 0.5061(5) 0.3879(3) 0.0251(17) Uani 1 1 d . . . . .
H3A H 1.0985 0.4663 0.4136 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8130(12) 0.4278(5) 0.3518(4) 0.0292(19) Uani 1 1 d . . . . .
H4A H 0.7005 0.4661 0.3229 0.035 Uiso 1 1 calc R U . . .
H4B H 0.7018 0.3890 0.3808 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9756(13) 0.3499(5) 0.3154(4) 0.0335(19) Uani 1 1 d . . . . .
H5A H 1.0602 0.3873 0.2811 0.040 Uiso 1 1 calc R U . . .
H5B H 1.1120 0.3226 0.3428 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8268(13) 0.2578(5) 0.2890(4) 0.034(2) Uani 1 1 d . . . . .
C7 C 0.6141(14) 0.2940(5) 0.2443(3) 0.0292(18) Uani 1 1 d . . . . .
H7A H 0.4855 0.3361 0.2677 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7195(15) 0.3592(6) 0.1922(4) 0.045(2) Uani 1 1 d . . . . .
H8A H 0.8415 0.3171 0.1676 0.054 Uiso 1 1 calc R U . . .
H8B H 0.8130 0.4200 0.2091 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6994(14) 0.5115(6) 0.4834(4) 0.039(2) Uani 1 1 d . . . . .
H9A H 0.6116 0.5581 0.5124 0.058 Uiso 1 1 calc R U . . .
H9B H 0.8368 0.4743 0.5049 0.058 Uiso 1 1 calc R U . . .
H9C H 0.5766 0.4611 0.4667 0.058 Uiso 1 1 calc R U . . .
C10 C 0.6946(15) 0.1910(6) 0.3379(4) 0.044(2) Uani 1 1 d . . . . .
H10A H 0.6171 0.1293 0.3179 0.053 Uiso 1 1 calc R U . . .
H10B H 0.5545 0.2320 0.3569 0.053 Uiso 1 1 calc R U . . .
Br1 Br 0.9284(3) 0.14444(8) 0.40231(6) 0.0987(5) Uani 1 1 d . . . . .
Br2 Br 0.43956(19) 0.40739(6) 0.13935(4) 0.0529(3) Uani 1 1 d . . . . .
O1 O 0.5954(9) 0.6174(3) 0.3984(2) 0.0266(11) Uani 1 1 d D . . . .
H1 H 0.639(11) 0.672(3) 0.375(2) 0.04(2) Uiso 1 1 d D . . . .
O2 O 1.1142(9) 0.5656(3) 0.3438(2) 0.0285(12) Uani 1 1 d D . . . .
H2 H 1.272(5) 0.580(5) 0.358(3) 0.04(2) Uiso 1 1 d D . . . .
O3 O 1.0061(10) 0.1949(4) 0.2563(3) 0.0553(17) Uani 1 1 d D . . . .
H3 H 0.921(10) 0.155(4) 0.229(2) 0.06(3) Uiso 1 1 d D . . . .
O4 O 0.4912(9) 0.2044(4) 0.2196(2) 0.0331(13) Uani 1 1 d D . . . .
H4 H 0.330(5) 0.199(6) 0.234(3) 0.06(3) Uiso 1 1 d D . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.023(4) 0.039(4) 0.036(4) -0.009(4) -0.001(4) 0.000(4)
C2 0.018(4) 0.029(4) 0.026(4) 0.003(4) -0.007(3) -0.002(3)
C3 0.017(4) 0.024(3) 0.035(4) 0.005(3) -0.001(4) -0.005(3)
C4 0.017(4) 0.024(4) 0.047(5) -0.004(4) 0.004(4) -0.004(3)
C5 0.016(4) 0.025(3) 0.059(5) -0.010(4) 0.002(4) 0.001(3)
C6 0.019(4) 0.018(3) 0.064(6) -0.014(4) -0.002(4) 0.002(3)
C7 0.024(4) 0.023(3) 0.041(5) -0.005(4) 0.010(4) -0.004(3)
C8 0.044(5) 0.040(4) 0.051(6) -0.005(5) 0.014(4) -0.005(5)
C9 0.041(5) 0.047(5) 0.028(5) 0.005(4) 0.002(4) -0.003(4)
C10 0.042(5) 0.030(4) 0.061(6) 0.011(4) -0.022(4) -0.003(4)
Br1 0.1016(9) 0.0668(6) 0.1275(11) 0.0384(7) -0.0779(9) -0.0226(7)
Br2 0.0775(6) 0.0401(4) 0.0412(5) 0.0025(4) -0.0022(5) -0.0052(5)
O1 0.021(3) 0.026(3) 0.034(3) 0.005(2) -0.003(2) -0.001(2)
O2 0.023(3) 0.030(3) 0.033(3) 0.003(2) 0.004(2) -0.007(2)
O3 0.026(3) 0.035(3) 0.105(5) -0.040(3) -0.008(3) 0.008(3)
O4 0.029(4) 0.027(2) 0.044(3) -0.014(2) 0.005(3) -0.009(2)

_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
C1 C2 1.520(9) . ?
C2 O1 1.442(8) . ?
C2 C9 1.522(9) . ?
C2 C3 1.539(9) . ?
C3 O2 1.429(7) . ?
C3 C4 1.523(8) . ?
C4 C5 1.531(8) . ?
C5 C6 1.525(9) . ?
C6 O3 1.425(8) . ?
C6 C10 1.529(11) . ?
C6 C7 1.545(10) . ?
C7 O4 1.421(8) . ?
C7 C8 1.511(10) . ?
C8 Br2 1.957(8) . ?
C10 Br1 1.949(7) . ?

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
O1 C2 C1 110.2(5) . . ?
O1 C2 C9 105.1(5) . . ?
C1 C2 C9 109.9(6) . . ?
O1 C2 C3 110.1(5) . . ?
C1 C2 C3 110.7(5) . . ?
C9 C2 C3 110.8(6) . . ?
O2 C3 C4 106.8(6) . . ?
O2 C3 C2 112.3(5) . . ?
C4 C3 C2 113.4(5) . . ?
C3 C4 C5 113.1(5) . . ?
C6 C5 C4 114.7(5) . . ?
O3 C6 C5 107.0(5) . . ?
O3 C6 C10 109.0(6) . . ?
C5 C6 C10 113.6(7) . . ?
O3 C6 C7 109.2(7) . . ?
C5 C6 C7 111.7(6) . . ?
C10 C6 C7 106.3(6) . . ?
O4 C7 C8 109.1(6) . . ?
O4 C7 C6 108.6(5) . . ?
C8 C7 C6 112.0(6) . . ?
C7 C8 Br2 110.0(5) . . ?
C6 C10 Br1 112.8(5) . . ?

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4
_database_code_depnum_ccdc_archive 'CCDC 1017806'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 Br2 O2'
_chemical_formula_sum            'C5 H10 Br2 O2'
_chemical_formula_weight         261.95

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   5.56972(10)
_cell_length_b                   9.61673(17)
_cell_length_c                   15.4286(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5499(16)
_cell_angle_gamma                90.00
_cell_volume                     819.23(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    3944
_cell_measurement_theta_min      2.8868
_cell_measurement_theta_max      71.7933

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    12.043
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_T_max  0.514
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) 
(compiled Aug  3 2011,13:03:54) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.2556
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5638
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.43
_diffrn_reflns_theta_max         71.94
_reflns_number_total             1597
_reflns_number_gt                1440
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0215P)²+0.7173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00224(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1597
_refine_ls_number_parameters     91
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4891(5) 0.0295(3) 0.21227(18) 0.0277(6) Uani 1 1 d . . .
H1A H 0.5391 -0.0544 0.1820 0.033 Uiso 1 1 calc R . .
H1B H 0.3492 0.0035 0.2423 0.033 Uiso 1 1 calc R . .
C2 C 0.4076(4) 0.1410(3) 0.14373(16) 0.0219(5) Uani 1 1 d . . .
C3 C 0.6160(4) 0.1859(3) 0.09335(16) 0.0212(5) Uani 1 1 d . . .
H3A H 0.7387 0.2391 0.1334 0.025 Uiso 1 1 calc R . .
C4 C 0.5218(5) 0.2767(3) 0.01560(18) 0.0300(6) Uani 1 1 d . . .
H4A H 0.4388 0.3591 0.0361 0.036 Uiso 1 1 calc R . .
H4B H 0.4029 0.2238 -0.0249 0.036 Uiso 1 1 calc R . .
C5 C 0.2952(5) 0.2646(3) 0.18503(18) 0.0268(6) Uani 1 1 d . . .
H5A H 0.2462 0.3347 0.1401 0.040 Uiso 1 1 calc R . .
H5B H 0.4141 0.3050 0.2305 0.040 Uiso 1 1 calc R . .
H5C H 0.1530 0.2337 0.2110 0.040 Uiso 1 1 calc R . .
Br1 Br 0.75590(5) 0.08648(3) 0.299959(18) 0.03480(12) Uani 1 1 d . . .
Br2 Br 0.78942(6) 0.33696(4) -0.04585(2) 0.03796(12) Uani 1 1 d . . .
O1 O 0.2177(3) 0.0758(2) 0.08632(12) 0.0271(4) Uani 1 1 d D . .
H1 H 0.272(6) 0.019(3) 0.0469(18) 0.051(10) Uiso 1 1 d D . .
O2 O 0.7262(3) 0.06386(19) 0.06409(12) 0.0238(4) Uani 1 1 d D . .
H2 H 0.8883(8) 0.067(4) 0.077(2) 0.053(11) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0241(14) 0.0263(13) 0.0327(14) 0.0016(11) 0.0035(11) -0.0043(10)
C2 0.0151(11) 0.0271(12) 0.0233(12) -0.0043(10) 0.0020(9) -0.0011(10)
C3 0.0156(12) 0.0246(12) 0.0235(12) -0.0025(10) 0.0026(9) -0.0004(10)
C4 0.0222(13) 0.0394(15) 0.0294(14) 0.0098(12) 0.0068(11) 0.0035(12)
C5 0.0227(13) 0.0280(13) 0.0307(14) -0.0075(11) 0.0078(11) -0.0014(11)
Br1 0.03132(18) 0.0457(2) 0.02635(16) 0.00359(12) -0.00011(11) 0.00192(13)
Br2 0.03069(18) 0.0490(2) 0.03543(18) 0.01434(14) 0.00899(12) -0.00192(13)
O1 0.0156(9) 0.0338(10) 0.0318(10) -0.0107(8) 0.0029(7) -0.0030(7)
O2 0.0150(9) 0.0270(9) 0.0296(9) -0.0056(7) 0.0040(7) 0.0015(7)

_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
C1 C2 1.532(4) . ?
C1 Br1 1.952(3) . ?
C2 O1 1.432(3) . ?
C2 C5 1.522(3) . ?
C2 C3 1.541(3) . ?
C3 O2 1.425(3) . ?
C3 C4 1.520(4) . ?
C4 Br2 1.956(3) . ?

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
C2 C1 Br1 114.30(18) . . ?
O1 C2 C5 106.9(2) . . ?
O1 C2 C1 104.4(2) . . ?
C5 C2 C1 111.0(2) . . ?
O1 C2 C3 110.8(2) . . ?
C5 C2 C3 111.8(2) . . ?
C1 C2 C3 111.7(2) . . ?
O2 C3 C4 110.0(2) . . ?
O2 C3 C2 108.26(19) . . ?
C4 C3 C2 110.7(2) . . ?
C3 C4 Br2 110.28(18) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        71.94
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.074

#===END


_database_code_depnum_ccdc_archive 'CCDC 1017807'
