# Supplementary Information (SI) for CrystEngComm.
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2450092'
loop_
_audit_author_name
_audit_author_address
'Arshad Khan'
;KAIMRC
Saudi Arabia
;
_audit_update_record             
;
2025-05-11 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H26 F2 N3'
_chemical_formula_weight         586.64

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.7484(6)
_cell_length_b                   13.5215(11)
_cell_length_c                   13.7453(11)
_cell_angle_alpha                73.799(2)
_cell_angle_beta                 75.940(2)
_cell_angle_gamma                81.670(2)
_cell_volume                     1509.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5232
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.95

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30429
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_full        25.067
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5297
_reflns_number_gt                2884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0595P)²+0.6100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5297
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.4538(3) 0.1276(2) 0.1815(2) 0.0469(7) Uani 1 1 d . . . . .
C2 C 0.4550(3) 0.0512(2) 0.1325(2) 0.0546(8) Uani 1 1 d . . . . .
H2 H 0.3621 0.0388 0.1180 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5944(4) -0.0068(3) 0.1048(2) 0.0656(9) Uani 1 1 d . . . . .
H3 H 0.5946 -0.0597 0.0737 0.079 Uiso 1 1 calc R U . . .
C4 C 0.7328(4) 0.0134(3) 0.1234(2) 0.0671(9) Uani 1 1 d . . . . .
H4 H 0.8267 -0.0249 0.1037 0.081 Uiso 1 1 calc R U . . .
C5 C 0.7323(4) 0.0904(3) 0.1711(2) 0.0649(9) Uani 1 1 d . . . . .
H5 H 0.8262 0.1045 0.1828 0.078 Uiso 1 1 calc R U . . .
C6 C 0.5923(3) 0.1468(2) 0.2018(2) 0.0569(8) Uani 1 1 d . . . . .
H6 H 0.5916 0.1974 0.2359 0.068 Uiso 1 1 calc R U . . .
C7 C 0.1685(3) 0.1442(2) 0.2728(2) 0.0467(7) Uani 1 1 d . . . . .
C8 C 0.1328(3) 0.0424(2) 0.3110(2) 0.0574(8) Uani 1 1 d . . . . .
H8 H 0.2058 -0.0112 0.2953 0.069 Uiso 1 1 calc R U . . .
C9 C -0.0153(4) 0.0229(3) 0.3735(2) 0.0669(9) Uani 1 1 d . . . . .
H9 H -0.0418 -0.0450 0.4008 0.080 Uiso 1 1 calc R U . . .
C10 C -0.1250(4) 0.1028(3) 0.3961(3) 0.0694(9) Uani 1 1 d . . . . .
H10 H -0.2242 0.0877 0.4375 0.083 Uiso 1 1 calc R U . . .
C11 C -0.0893(3) 0.2031(3) 0.3586(2) 0.0626(9) Uani 1 1 d . . . . .
H11 H -0.1634 0.2562 0.3742 0.075 Uiso 1 1 calc R U . . .
C12 C 0.0591(3) 0.2253(2) 0.2965(2) 0.0482(7) Uani 1 1 d . . . . .
C13 C 0.1359(3) 0.3193(2) 0.2483(2) 0.0495(7) Uani 1 1 d . . . . .
C14 C 0.2887(3) 0.2925(2) 0.1968(2) 0.0463(7) Uani 1 1 d . . . . .
C15 C 0.3920(3) 0.3676(2) 0.1408(2) 0.0561(8) Uani 1 1 d . . . . .
H15 H 0.4920 0.3499 0.1046 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3416(4) 0.4692(3) 0.1407(3) 0.0650(9) Uani 1 1 d . . . . .
H16 H 0.4092 0.5205 0.1039 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1919(4) 0.4965(3) 0.1943(3) 0.0677(9) Uani 1 1 d . . . . .
H17 H 0.1616 0.5654 0.1941 0.081 Uiso 1 1 calc R U . . .
C18 C 0.0886(4) 0.4225(2) 0.2476(2) 0.0601(8) Uani 1 1 d . . . . .
H18 H -0.0117 0.4409 0.2827 0.072 Uiso 1 1 calc R U . . .
C19 C 0.7333(3) 0.2637(2) 0.6772(2) 0.0496(7) Uani 1 1 d . . . . .
C20 C 0.6383(4) 0.2484(2) 0.7750(3) 0.0642(9) Uani 1 1 d . . . . .
H20 H 0.5293 0.2621 0.7835 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7067(5) 0.2122(3) 0.8609(3) 0.0783(10) Uani 1 1 d . . . . .
H21 H 0.6432 0.2010 0.9273 0.094 Uiso 1 1 calc R U . . .
C22 C 0.8677(5) 0.1931(3) 0.8480(3) 0.0807(11) Uani 1 1 d . . . . .
H22 H 0.9131 0.1688 0.9058 0.097 Uiso 1 1 calc R U . . .
C23 C 0.9612(4) 0.2094(3) 0.7514(3) 0.0809(11) Uani 1 1 d . . . . .
H23 H 1.0704 0.1970 0.7433 0.097 Uiso 1 1 calc R U . . .
C24 C 0.8949(4) 0.2442(2) 0.6653(3) 0.0624(9) Uani 1 1 d . . . . .
H24 H 0.9593 0.2546 0.5992 0.075 Uiso 1 1 calc R U . . .
C25 C 0.6946(3) 0.3918(2) 0.5119(2) 0.0481(7) Uani 1 1 d . . . . .
C26 C 0.7894(3) 0.4680(2) 0.5063(2) 0.0572(8) Uani 1 1 d . . . . .
H26 H 0.8464 0.4620 0.5570 0.069 Uiso 1 1 calc R U . . .
C27 C 0.7954(4) 0.5529(2) 0.4225(3) 0.0629(9) Uani 1 1 d . . . . .
H27 H 0.8581 0.6052 0.4163 0.075 Uiso 1 1 calc R U . . .
C28 C 0.7102(4) 0.5622(3) 0.3471(3) 0.0672(9) Uani 1 1 d . . . . .
H28 H 0.7179 0.6202 0.2912 0.081 Uiso 1 1 calc R U . . .
C29 C 0.6148(4) 0.4876(3) 0.3534(2) 0.0601(9) Uani 1 1 d . . . . .
H29 H 0.5570 0.4950 0.3029 0.072 Uiso 1 1 calc R U . . .
C30 C 0.6060(3) 0.4002(2) 0.4374(2) 0.0476(7) Uani 1 1 d . . . . .
C31 C 0.5191(3) 0.3105(2) 0.4695(2) 0.0490(7) Uani 1 1 d . . . . .
C32 C 0.4116(4) 0.2758(3) 0.4294(2) 0.0655(9) Uani 1 1 d . . . . .
H32 H 0.3832 0.3148 0.3681 0.079 Uiso 1 1 calc R U . . .
C33 C 0.3477(4) 0.1838(3) 0.4806(3) 0.0777(10) Uani 1 1 d . . . . .
H33 H 0.2758 0.1605 0.4538 0.093 Uiso 1 1 calc R U . . .
C34 C 0.3896(4) 0.1250(3) 0.5721(3) 0.0755(10) Uani 1 1 d . . . . .
H34 H 0.3462 0.0623 0.6051 0.091 Uiso 1 1 calc R U . . .
C35 C 0.4939(3) 0.1574(2) 0.6150(2) 0.0601(8) Uani 1 1 d . . . . .
H35 H 0.5207 0.1182 0.6767 0.072 Uiso 1 1 calc R U . . .
C36 C 0.5571(3) 0.2503(2) 0.5631(2) 0.0471(7) Uani 1 1 d . . . . .
C37 C 0.8504(4) 0.5172(4) 0.0508(3) 0.0700(10) Uani 1 1 d . . . . .
C38 C 0.9103(5) 0.4197(3) 0.0480(3) 0.0741(10) Uani 1 1 d . . . . .
C39 C 1.0607(5) 0.4001(3) -0.0027(3) 0.0694(10) Uani 1 1 d . . . . .
C40 C 1.1185(6) 0.2966(4) -0.0047(4) 0.1229(18) Uani 1 1 d . . . . .
F1 F 0.8167(3) 0.3431(2) 0.0960(2) 0.1433(11) Uani 1 1 d . . . . .
F2 F 0.7028(2) 0.5364(2) 0.10039(17) 0.1273(10) Uani 1 1 d . . . . .
N1 N 0.3092(3) 0.18573(18) 0.21191(17) 0.0477(6) Uani 1 1 d . . . . .
N2 N 0.6649(3) 0.30020(17) 0.58836(18) 0.0502(6) Uani 1 1 d . . . . .
N3 N 1.1676(7) 0.2155(4) -0.0093(5) 0.196(3) Uani 1 1 d . . . . .


_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 1.380(4) . ?
C1 C6 1.382(4) . ?
C1 N1 1.425(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 C12 1.403(4) . ?
C7 N1 1.403(3) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.437(4) . ?
C13 C18 1.395(4) . ?
C13 C14 1.401(4) . ?
C14 C15 1.390(4) . ?
C14 N1 1.391(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.376(4) . ?
C19 C24 1.378(4) . ?
C19 N2 1.423(3) . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.389(4) . ?
C25 N2 1.393(3) . ?
C25 C30 1.399(4) . ?
C26 C27 1.378(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.399(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.431(4) . ?
C31 C32 1.390(4) . ?
C31 C36 1.405(4) . ?
C32 C33 1.370(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.389(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.379(4) . ?
C35 H35 0.9300 . ?
C36 N2 1.393(3) . ?
C37 F2 1.331(3) . ?
C37 C38 1.354(5) . ?
C37 C39 1.372(5) 2_765 ?
C38 F1 1.334(4) . ?
C38 C39 1.358(5) . ?
C39 C37 1.372(5) 2_765 ?
C39 C40 1.423(6) . ?
C40 N3 1.132(5) . ?

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 C6 119.9(3) . . ?
C2 C1 N1 119.8(3) . . ?
C6 C1 N1 120.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C12 121.4(3) . . ?
C8 C7 N1 129.9(3) . . ?
C12 C7 N1 108.7(2) . . ?
C7 C8 C9 117.7(3) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 C13 133.7(3) . . ?
C7 C12 C13 106.9(2) . . ?
C18 C13 C14 119.6(3) . . ?
C18 C13 C12 132.9(3) . . ?
C14 C13 C12 107.4(2) . . ?
C15 C14 N1 130.1(3) . . ?
C15 C14 C13 121.1(3) . . ?
N1 C14 C13 108.8(2) . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.3(3) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
C20 C19 C24 119.9(3) . . ?
C20 C19 N2 120.1(3) . . ?
C24 C19 N2 120.0(3) . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.0(3) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 N2 128.9(3) . . ?
C26 C25 C30 122.3(3) . . ?
N2 C25 C30 108.7(2) . . ?
C27 C26 C25 117.0(3) . . ?
C27 C26 H26 121.5 . . ?
C25 C26 H26 121.5 . . ?
C26 C27 C28 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 118.7(3) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C25 C30 C29 119.0(3) . . ?
C25 C30 C31 107.2(2) . . ?
C29 C30 C31 133.9(3) . . ?
C32 C31 C36 118.5(3) . . ?
C32 C31 C30 134.2(3) . . ?
C36 C31 C30 107.2(2) . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.5(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 121.6(3) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C36 117.5(3) . . ?
C34 C35 H35 121.3 . . ?
C36 C35 H35 121.3 . . ?
C35 C36 N2 129.3(3) . . ?
C35 C36 C31 122.2(3) . . ?
N2 C36 C31 108.4(2) . . ?
F2 C37 C38 121.2(4) . . ?
F2 C37 C39 117.5(4) . 2_765 ?
C38 C37 C39 121.3(3) . 2_765 ?
F1 C38 C37 118.1(4) . . ?
F1 C38 C39 120.7(4) . . ?
C37 C38 C39 121.2(3) . . ?
C38 C39 C37 117.5(3) . 2_765 ?
C38 C39 C40 119.4(4) . . ?
C37 C39 C40 123.1(4) 2_765 . ?
N3 C40 C39 177.7(7) . . ?
C14 N1 C7 108.3(2) . . ?
C14 N1 C1 125.7(2) . . ?
C7 N1 C1 125.6(2) . . ?
C25 N2 C36 108.4(2) . . ?
C25 N2 C19 125.8(2) . . ?
C36 N2 C19 125.8(2) . . ?

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
C6 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
N1 C1 C6 C5 -179.5(3) . . . . ?
C4 C5 C6 C1 -1.9(5) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
N1 C7 C8 C9 177.3(3) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C7 0.7(4) . . . . ?
C10 C11 C12 C13 -177.4(3) . . . . ?
C8 C7 C12 C11 -0.9(4) . . . . ?
N1 C7 C12 C11 -178.6(2) . . . . ?
C8 C7 C12 C13 177.7(3) . . . . ?
N1 C7 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C18 0.7(5) . . . . ?
C7 C12 C13 C18 -177.6(3) . . . . ?
C11 C12 C13 C14 178.5(3) . . . . ?
C7 C12 C13 C14 0.2(3) . . . . ?
C18 C13 C14 C15 -3.0(4) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C18 C13 C14 N1 177.8(2) . . . . ?
C12 C13 C14 N1 -0.4(3) . . . . ?
N1 C14 C15 C16 -178.6(3) . . . . ?
C13 C14 C15 C16 2.4(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -1.3(5) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
C14 C13 C18 C17 1.4(4) . . . . ?
C12 C13 C18 C17 179.0(3) . . . . ?
C24 C19 C20 C21 -0.7(5) . . . . ?
N2 C19 C20 C21 179.7(3) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C21 C22 C23 C24 -0.8(6) . . . . ?
C20 C19 C24 C23 0.1(4) . . . . ?
N2 C19 C24 C23 179.6(3) . . . . ?
C22 C23 C24 C19 0.7(5) . . . . ?
N2 C25 C26 C27 -178.6(3) . . . . ?
C30 C25 C26 C27 -1.1(4) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C29 0.7(5) . . . . ?
C27 C28 C29 C30 -0.8(4) . . . . ?
C26 C25 C30 C29 1.0(4) . . . . ?
N2 C25 C30 C29 178.9(2) . . . . ?
C26 C25 C30 C31 -177.9(2) . . . . ?
N2 C25 C30 C31 0.0(3) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C28 C29 C30 C31 178.5(3) . . . . ?
C25 C30 C31 C32 179.2(3) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C25 C30 C31 C36 0.3(3) . . . . ?
C29 C30 C31 C36 -178.4(3) . . . . ?
C36 C31 C32 C33 -1.1(4) . . . . ?
C30 C31 C32 C33 -179.9(3) . . . . ?
C31 C32 C33 C34 0.0(5) . . . . ?
C32 C33 C34 C35 1.0(5) . . . . ?
C33 C34 C35 C36 -0.7(5) . . . . ?
C34 C35 C36 N2 -179.4(3) . . . . ?
C34 C35 C36 C31 -0.4(4) . . . . ?
C32 C31 C36 C35 1.3(4) . . . . ?
C30 C31 C36 C35 -179.5(3) . . . . ?
C32 C31 C36 N2 -179.6(2) . . . . ?
C30 C31 C36 N2 -0.4(3) . . . . ?
F2 C37 C38 F1 0.4(5) . . . . ?
C39 C37 C38 F1 -179.6(3) 2_765 . . . ?
F2 C37 C38 C39 179.9(3) . . . . ?
C39 C37 C38 C39 -0.2(6) 2_765 . . . ?
F1 C38 C39 C37 179.6(3) . . . 2_765 ?
C37 C38 C39 C37 0.1(6) . . . 2_765 ?
F1 C38 C39 C40 0.1(5) . . . . ?
C37 C38 C39 C40 -179.4(3) . . . . ?
C15 C14 N1 C7 -178.8(3) . . . . ?
C13 C14 N1 C7 0.4(3) . . . . ?
C15 C14 N1 C1 8.1(4) . . . . ?
C13 C14 N1 C1 -172.7(2) . . . . ?
C8 C7 N1 C14 -177.7(3) . . . . ?
C12 C7 N1 C14 -0.2(3) . . . . ?
C8 C7 N1 C1 -4.6(4) . . . . ?
C12 C7 N1 C1 172.9(2) . . . . ?
C2 C1 N1 C14 -134.6(3) . . . . ?
C6 C1 N1 C14 46.0(4) . . . . ?
C2 C1 N1 C7 53.4(4) . . . . ?
C6 C1 N1 C7 -126.0(3) . . . . ?
C26 C25 N2 C36 177.5(3) . . . . ?
C30 C25 N2 C36 -0.3(3) . . . . ?
C26 C25 N2 C19 -2.6(5) . . . . ?
C30 C25 N2 C19 179.7(2) . . . . ?
C35 C36 N2 C25 179.5(3) . . . . ?
C31 C36 N2 C25 0.4(3) . . . . ?
C35 C36 N2 C19 -0.5(5) . . . . ?
C31 C36 N2 C19 -179.5(2) . . . . ?
C20 C19 N2 C25 119.3(3) . . . . ?
C24 C19 N2 C25 -60.3(4) . . . . ?
C20 C19 N2 C36 -60.8(4) . . . . ?
C24 C19 N2 C36 119.6(3) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2450093'
loop_
_audit_author_name
_audit_author_address
'Arshad Khan'
;KAIMRC
Saudi Arabia
;
_audit_update_record             
;
2025-05-11 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H15 F4 N3'
_chemical_formula_weight         457.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.571(12)
_cell_length_b                   12.724(10)
_cell_length_c                   13.505(11)
_cell_angle_alpha                90
_cell_angle_beta                 125.20
_cell_angle_gamma                90
_cell_volume                     2186(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1263
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      19.15

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8034
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_full        25.067
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1918
_reflns_number_gt                997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0679P)²+0.0741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1918
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.078
_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_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 0.9113(2) 0.14005(19) 0.6958(2) 0.0590(7) Uani 1 1 d . . . . .
C2 C 0.8063(2) 0.1678(2) 0.6305(2) 0.0704(8) Uani 1 1 d . . . . .
H2 H 0.7858 0.2379 0.6182 0.084 Uiso 1 1 calc R U . . .
C3 C 0.7330(3) 0.0880(2) 0.5841(3) 0.0834(9) Uani 1 1 d . . . . .
H3 H 0.6619 0.1047 0.5392 0.100 Uiso 1 1 calc R U . . .
C4 C 0.7635(3) -0.0172(2) 0.6035(3) 0.0850(9) Uani 1 1 d . . . . .
H4 H 0.7126 -0.0696 0.5716 0.102 Uiso 1 1 calc R U . . .
C5 C 0.8671(3) -0.0444(2) 0.6684(3) 0.0727(9) Uani 1 1 d . . . . .
H5 H 0.8867 -0.1148 0.6812 0.087 Uiso 1 1 calc R U . . .
C6 C 0.9436(2) 0.03463(18) 0.7155(2) 0.0592(7) Uani 1 1 d . . . . .
C7 C 1.0000 0.3170(2) 0.7500 0.0574(10) Uani 1 2 d S T P . .
C8 C 0.9495(2) 0.3717(2) 0.7904(2) 0.0669(8) Uani 1 1 d . . . . .
H8 H 0.9155 0.3355 0.8184 0.080 Uiso 1 1 calc R U . . .
C9 C 0.9493(2) 0.4802(2) 0.7892(3) 0.0749(8) Uani 1 1 d . . . . .
H9 H 0.9140 0.5163 0.8155 0.090 Uiso 1 1 calc R U . . .
C10 C 1.0000 0.5361(3) 0.7500 0.0740(12) Uani 1 2 d S T P . .
C11 C 1.0000 0.6562(3) 0.7500 0.1155(18) Uani 1 2 d S T P . .
H11A H 1.0342 0.6814 0.8315 0.173 Uiso 0.5 1 calc R U P . .
H11B H 0.9289 0.6814 0.7013 0.173 Uiso 0.5 1 calc R U P . .
H11C H 1.0369 0.6814 0.7172 0.173 Uiso 0.5 1 calc R U P . .
C12 C 0.3383(3) 0.3499(3) 0.4120(3) 0.0843(10) Uani 1 1 d . . . . .
C13 C 0.4205(3) 0.4255(2) 0.4565(3) 0.0670(8) Uani 1 1 d . . . . .
C14 C 0.5242(3) 0.3963(2) 0.5196(3) 0.0669(8) Uani 1 1 d . . . . .
C15 C 0.6022(2) 0.4682(2) 0.5624(2) 0.0684(8) Uani 1 1 d . . . . .
F1 F 0.54789(14) 0.29323(11) 0.53934(16) 0.0959(6) Uani 1 1 d . . . . .
F2 F 0.70150(15) 0.43583(13) 0.62307(17) 0.0963(6) Uani 1 1 d . . . . .
N1 N 1.0000 0.2045(2) 0.7500 0.0611(8) Uani 1 2 d S T P . .
N2 N 0.2746(3) 0.2877(2) 0.3778(3) 0.1165(11) Uani 1 1 d . . . . .


_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 1.383(4) . ?
C1 N1 1.397(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C6 1.437(5) 2_756 ?
C7 C8 1.376(3) . ?
C7 C8 1.376(3) 2_756 ?
C7 N1 1.432(4) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C9 1.375(3) 2_756 ?
C10 C11 1.529(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.138(4) . ?
C12 C13 1.428(4) . ?
C13 C14 1.373(4) . ?
C13 C15 1.384(4) 5_666 ?
C14 F1 1.347(3) . ?
C14 C15 1.354(4) . ?
C15 F2 1.331(3) . ?
C15 C13 1.384(4) 5_666 ?
N1 C1 1.397(3) 2_756 ?

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 N1 129.3(2) . . ?
C2 C1 C6 121.9(2) . . ?
N1 C1 C6 108.9(2) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C6 134.10(18) . 2_756 ?
C1 C6 C6 107.08(15) . 2_756 ?
C8 C7 C8 119.3(3) . 2_756 ?
C8 C7 N1 120.34(17) . . ?
C8 C7 N1 120.34(17) 2_756 . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C9 117.7(3) 2_756 . ?
C9 C10 C11 121.13(17) 2_756 . ?
C9 C10 C11 121.13(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 178.3(4) . . ?
C14 C13 C15 117.5(3) . 5_666 ?
C14 C13 C12 121.8(3) . . ?
C15 C13 C12 120.7(3) 5_666 . ?
F1 C14 C15 119.8(3) . . ?
F1 C14 C13 118.4(3) . . ?
C15 C14 C13 121.8(3) . . ?
F2 C15 C14 119.5(3) . . ?
F2 C15 C13 119.8(3) . 5_666 ?
C14 C15 C13 120.7(3) . 5_666 ?
C1 N1 C1 108.1(3) 2_756 . ?
C1 N1 C7 125.94(14) 2_756 . ?
C1 N1 C7 125.94(14) . . ?

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
N1 C1 C2 C3 178.8(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C6 -179.0(3) . . . 2_756 ?
C2 C1 C6 C5 -0.6(4) . . . . ?
N1 C1 C6 C5 -179.77(19) . . . . ?
C2 C1 C6 C6 179.3(3) . . . 2_756 ?
N1 C1 C6 C6 0.1(3) . . . 2_756 ?
C8 C7 C8 C9 0.47(17) 2_756 . . . ?
N1 C7 C8 C9 -179.53(17) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C9 0.48(18) . . . 2_756 ?
C8 C9 C10 C11 -179.52(18) . . . . ?
C15 C13 C14 F1 179.8(2) 5_666 . . . ?
C12 C13 C14 F1 -0.1(4) . . . . ?
C15 C13 C14 C15 0.2(4) 5_666 . . . ?
C12 C13 C14 C15 -179.6(2) . . . . ?
F1 C14 C15 F2 0.4(4) . . . . ?
C13 C14 C15 F2 180.0(2) . . . . ?
F1 C14 C15 C13 -179.8(2) . . . 5_666 ?
C13 C14 C15 C13 -0.2(4) . . . 5_666 ?
C2 C1 N1 C1 -179.1(3) . . . 2_756 ?
C6 C1 N1 C1 -0.05(11) . . . 2_756 ?
C2 C1 N1 C7 0.9(3) . . . . ?
C6 C1 N1 C7 179.95(11) . . . . ?
C8 C7 N1 C1 -126.03(18) . . . 2_756 ?
C8 C7 N1 C1 53.97(18) 2_756 . . 2_756 ?
C8 C7 N1 C1 53.97(18) . . . . ?
C8 C7 N1 C1 -126.03(18) 2_756 . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.047

