# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2279459'
loop_
_audit_author_name
_audit_author_address
'MANNA DEBASIS DAS SRIBASH'
;IITG
India
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H15 F6 N5 S  '
_chemical_formula_sum            'C23 H15 F6 N5 S  '
_chemical_compound_source        SYNTHESIS
_exptl_crystal_recrystallization_method 
'SLOW EVAPORATION OF COMPOUND SOLUTION IN METHANOL- ACETONITRILE SOLVENT MIXTUR'
_chemical_melting_point          ?

_exptl_crystal_description       ROD
_exptl_crystal_colour            YELLOW
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         507.46

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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 2yn'
_chemical_absolute_configuration syn

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'

_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.
;

_cell_length_a                   26.509(6)
_cell_length_b                   8.6693(18)
_cell_length_c                   19.550(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.969(5)
_cell_angle_gamma                90
_cell_volume                     4378.3(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.54
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             2064
_exptl_transmission_factor_min   0.6907
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.176
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49032
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.138
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3865
_reflns_number_gt                2771
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+32.2780P] 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         3865
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.1085
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_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
S1 S 0.53892(6) 0.7155(2) 0.54255(8) 0.060 Uani 1 1 d . . . . .
N5 N 0.55161(17) 0.5487(5) 0.4362(2) 0.049 Uani 1 1 d . . . . .
H5 H 0.534124 0.483444 0.454662 0.059 Uiso 1 1 calc R U . . .
N4 N 0.60426(17) 0.7599(5) 0.4564(2) 0.0530(13) Uani 1 1 d . . . . .
H4 H 0.619578 0.712667 0.428051 0.064 Uiso 1 1 calc R U . . .
F4 F 0.5571(2) 0.0394(4) 0.3179(2) 0.1076(16) Uani 1 1 d . . . . .
F5 F 0.5603(2) 0.0942(5) 0.2135(2) 0.126(2) Uani 1 1 d . . . . .
N1 N 0.68723(18) 0.7045(7) 0.4100(3) 0.0651(15) Uani 1 1 d . . . . .
F6 F 0.6277(2) 0.0934(5) 0.2939(3) 0.1260(19) Uani 1 1 d . . . . .
F2 F 0.61710(19) 0.7747(6) 0.2269(3) 0.1259(19) Uani 1 1 d . . . . .
C16 C 0.56095(19) 0.5051(6) 0.3706(3) 0.0410(12) Uani 1 1 d . . . . .
F1 F 0.5418(2) 0.7636(6) 0.1809(3) 0.132(2) Uani 1 1 d . . . . .
C17 C 0.56577(18) 0.6109(6) 0.3193(3) 0.0420(13) Uani 1 1 d . . . . .
H17 H 0.563402 0.716041 0.327553 0.050 Uiso 1 1 calc R U . . .
C18 C 0.5742(2) 0.5591(6) 0.2557(3) 0.0446(13) Uani 1 1 d . . . . .
C20 C 0.5710(2) 0.3001(6) 0.2927(3) 0.0489(14) Uani 1 1 d . . . . .
C15 C 0.5661(2) 0.6781(6) 0.4745(3) 0.0463(14) Uani 1 1 d . . . . .
C21 C 0.5630(2) 0.3487(6) 0.3567(3) 0.0480(14) Uani 1 1 d . . . . .
H21 H 0.559026 0.276744 0.390314 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6236(2) 0.9088(7) 0.4754(3) 0.0542(15) Uani 1 1 d . . . . .
C19 C 0.5766(2) 0.4040(6) 0.2416(3) 0.0496(14) Uani 1 1 d . . . . .
H19 H 0.581920 0.370178 0.198640 0.059 Uiso 1 1 calc R U . . .
C22 C 0.5818(3) 0.6734(7) 0.2027(3) 0.0621(17) Uani 1 1 d . . . . .
F3 F 0.5917(3) 0.6161(5) 0.1479(3) 0.196(4) Uani 1 1 d . . . . .
C8 C 0.7039(2) 0.8447(10) 0.4281(3) 0.0666(19) Uani 1 1 d . . . . .
N2 N 0.7491(2) 0.9056(9) 0.4200(3) 0.093(2) Uani 1 1 d . . . . .
C9 C 0.6719(2) 0.9489(8) 0.4612(3) 0.0642(18) Uani 1 1 d . . . . .
C13 C 0.5955(3) 1.0177(8) 0.5034(3) 0.0692(19) Uani 1 1 d . . . . .
H13 H 0.563207 0.991722 0.511255 0.083 Uiso 1 1 calc R U . . .
C23 C 0.5774(3) 0.1324(7) 0.2794(4) 0.071(2) Uani 1 1 d . . . . .
C1 C 0.7177(2) 0.6101(11) 0.3794(3) 0.074(2) Uani 1 1 d . . . . .
C12 C 0.6147(4) 1.1628(9) 0.5196(3) 0.086(2) Uani 1 1 d . . . . .
H12 H 0.595825 1.233754 0.539225 0.103 Uiso 1 1 calc R U . . .
C2 C 0.7014(3) 0.4603(11) 0.3601(4) 0.088(2) Uani 1 1 d . . . . .
H2 H 0.670416 0.424127 0.369003 0.106 Uiso 1 1 calc R U . . .
C7 C 0.7792(3) 0.8159(15) 0.3918(4) 0.107(4) Uani 1 1 d . . . . .
C10 C 0.6890(3) 1.0990(10) 0.4782(4) 0.090(3) Uani 1 1 d . . . . .
H10 H 0.720718 1.128784 0.469451 0.108 Uiso 1 1 calc R U . . .
C11 C 0.6617(4) 1.2045(10) 0.5070(4) 0.102(3) Uani 1 1 d . . . . .
H11 H 0.674758 1.303185 0.517951 0.122 Uiso 1 1 calc R U . . .
C6 C 0.7645(3) 0.6634(13) 0.3676(4) 0.093(3) Uani 1 1 d . . . . .
C3 C 0.7306(3) 0.3659(12) 0.3282(4) 0.116(3) Uani 1 1 d . . . . .
H3 H 0.719666 0.265963 0.315234 0.140 Uiso 1 1 calc R U . . .
N3 N 0.8253(3) 0.8754(12) 0.3844(4) 0.155(4) Uani 1 1 d . . . . .
H3A H 0.833759 0.968142 0.397862 0.186 Uiso 1 1 calc R U . . .
H3B H 0.845847 0.820243 0.366202 0.186 Uiso 1 1 calc R U . . .
C5 C 0.7940(4) 0.5639(17) 0.3348(6) 0.131(5) Uani 1 1 d . . . . .
H5A H 0.825501 0.597504 0.326718 0.157 Uiso 1 1 calc R U . . .
C4 C 0.7772(5) 0.4223(18) 0.3153(6) 0.144(5) Uani 1 1 d . . . . .
H4A H 0.796741 0.359443 0.292711 0.173 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
S1 C15 1.681(5) . ?
N5 C15 1.356(7) . ?
N5 C16 1.412(6) . ?
N5 H5 0.8600 . ?
N4 C15 1.346(6) . ?
N4 C14 1.408(7) . ?
N4 H4 0.8600 . ?
F4 C23 1.298(7) . ?
F5 C23 1.308(8) . ?
N1 C8 1.314(8) . ?
N1 C1 1.376(9) . ?
F6 C23 1.343(8) . ?
F2 C22 1.293(7) . ?
C16 C17 1.386(7) . ?
C16 C21 1.386(7) . ?
F1 C22 1.310(8) . ?
C17 C18 1.387(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(7) . ?
C18 C22 1.480(8) . ?
C20 C19 1.377(7) . ?
C20 C21 1.380(7) . ?
C20 C23 1.493(8) . ?
C21 H21 0.9300 . ?
C14 C13 1.389(8) . ?
C14 C9 1.413(8) . ?
C19 H19 0.9300 . ?
C22 F3 1.261(7) . ?
C8 N2 1.352(8) . ?
C8 C9 1.483(9) . ?
N2 C7 1.319(12) . ?
C9 C10 1.394(10) . ?
C13 C12 1.367(9) . ?
C13 H13 0.9300 . ?
C1 C6 1.391(9) . ?
C1 C2 1.394(11) . ?
C12 C11 1.370(10) . ?
C12 H12 0.9300 . ?
C2 C3 1.369(10) . ?
C2 H2 0.9300 . ?
C7 N3 1.363(9) . ?
C7 C6 1.429(13) . ?
C10 C11 1.364(11) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C6 C5 1.413(13) . ?
C3 C4 1.403(14) . ?
C3 H3 0.9300 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C5 C4 1.332(15) . ?
C5 H5A 0.9300 . ?
C4 H4A 0.9300 . ?

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
C15 N5 C16 129.6(4) . . ?
C15 N5 H5 115.2 . . ?
C16 N5 H5 115.2 . . ?
C15 N4 C14 131.6(5) . . ?
C15 N4 H4 114.2 . . ?
C14 N4 H4 114.2 . . ?
C8 N1 C1 118.2(6) . . ?
C17 C16 C21 119.4(5) . . ?
C17 C16 N5 122.9(5) . . ?
C21 C16 N5 117.6(5) . . ?
C16 C17 C18 119.6(5) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 121.3(5) . . ?
C19 C18 C22 119.6(5) . . ?
C17 C18 C22 119.0(5) . . ?
C19 C20 C21 121.4(5) . . ?
C19 C20 C23 118.4(5) . . ?
C21 C20 C23 120.1(5) . . ?
N4 C15 N5 115.3(4) . . ?
N4 C15 S1 126.0(4) . . ?
N5 C15 S1 118.5(4) . . ?
C20 C21 C16 119.9(5) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C13 C14 N4 122.1(5) . . ?
C13 C14 C9 120.0(6) . . ?
N4 C14 C9 117.7(6) . . ?
C18 C19 C20 118.4(5) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
F3 C22 F2 107.9(6) . . ?
F3 C22 F1 105.4(7) . . ?
F2 C22 F1 100.4(6) . . ?
F3 C22 C18 114.7(5) . . ?
F2 C22 C18 113.6(6) . . ?
F1 C22 C18 113.5(5) . . ?
N1 C8 N2 125.7(7) . . ?
N1 C8 C9 119.3(5) . . ?
N2 C8 C9 115.0(7) . . ?
C7 N2 C8 117.0(8) . . ?
C10 C9 C14 116.4(7) . . ?
C10 C9 C8 119.0(7) . . ?
C14 C9 C8 124.6(6) . . ?
C12 C13 C14 120.7(7) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
F4 C23 F5 108.5(6) . . ?
F4 C23 F6 103.9(6) . . ?
F5 C23 F6 104.7(6) . . ?
F4 C23 C20 115.2(5) . . ?
F5 C23 C20 113.0(6) . . ?
F6 C23 C20 110.7(6) . . ?
N1 C1 C6 120.4(9) . . ?
N1 C1 C2 119.7(6) . . ?
C6 C1 C2 119.9(8) . . ?
C13 C12 C11 120.6(8) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C3 C2 C1 120.5(8) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N2 C7 N3 117.4(11) . . ?
N2 C7 C6 122.5(7) . . ?
N3 C7 C6 120.0(10) . . ?
C11 C10 C9 123.3(7) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C12 119.0(7) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C1 C6 C5 118.6(11) . . ?
C1 C6 C7 116.2(8) . . ?
C5 C6 C7 125.2(9) . . ?
C2 C3 C4 118.9(11) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 C5 C6 120.5(11) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C4 C3 121.5(11) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?

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
C15 N5 C16 C17 -30.7(9) . . . . ?
C15 N5 C16 C21 152.2(6) . . . . ?
C21 C16 C17 C18 -1.9(8) . . . . ?
N5 C16 C17 C18 -179.0(5) . . . . ?
C16 C17 C18 C19 1.5(8) . . . . ?
C16 C17 C18 C22 -177.0(5) . . . . ?
C14 N4 C15 N5 168.5(5) . . . . ?
C14 N4 C15 S1 -16.2(9) . . . . ?
C16 N5 C15 N4 -17.0(8) . . . . ?
C16 N5 C15 S1 167.3(4) . . . . ?
C19 C20 C21 C16 -0.6(9) . . . . ?
C23 C20 C21 C16 175.3(6) . . . . ?
C17 C16 C21 C20 1.5(8) . . . . ?
N5 C16 C21 C20 178.7(5) . . . . ?
C15 N4 C14 C13 -18.7(9) . . . . ?
C15 N4 C14 C9 165.1(6) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
C22 C18 C19 C20 177.9(6) . . . . ?
C21 C20 C19 C18 0.1(9) . . . . ?
C23 C20 C19 C18 -175.8(6) . . . . ?
C19 C18 C22 F3 -1.9(10) . . . . ?
C17 C18 C22 F3 176.7(7) . . . . ?
C19 C18 C22 F2 -126.7(6) . . . . ?
C17 C18 C22 F2 51.9(8) . . . . ?
C19 C18 C22 F1 119.4(7) . . . . ?
C17 C18 C22 F1 -62.0(8) . . . . ?
C1 N1 C8 N2 -0.7(9) . . . . ?
C1 N1 C8 C9 -180.0(5) . . . . ?
N1 C8 N2 C7 -0.4(10) . . . . ?
C9 C8 N2 C7 178.9(6) . . . . ?
C13 C14 C9 C10 1.4(9) . . . . ?
N4 C14 C9 C10 177.6(5) . . . . ?
C13 C14 C9 C8 -176.8(6) . . . . ?
N4 C14 C9 C8 -0.5(9) . . . . ?
N1 C8 C9 C10 -178.0(6) . . . . ?
N2 C8 C9 C10 2.6(9) . . . . ?
N1 C8 C9 C14 0.2(9) . . . . ?
N2 C8 C9 C14 -179.2(6) . . . . ?
N4 C14 C13 C12 -178.2(6) . . . . ?
C9 C14 C13 C12 -2.1(9) . . . . ?
C19 C20 C23 F4 -160.4(6) . . . . ?
C21 C20 C23 F4 23.6(10) . . . . ?
C19 C20 C23 F5 -34.9(9) . . . . ?
C21 C20 C23 F5 149.1(6) . . . . ?
C19 C20 C23 F6 82.1(8) . . . . ?
C21 C20 C23 F6 -93.9(7) . . . . ?
C8 N1 C1 C6 -0.6(9) . . . . ?
C8 N1 C1 C2 179.4(6) . . . . ?
C14 C13 C12 C11 1.4(11) . . . . ?
N1 C1 C2 C3 178.5(7) . . . . ?
C6 C1 C2 C3 -1.4(12) . . . . ?
C8 N2 C7 N3 -179.0(6) . . . . ?
C8 N2 C7 C6 2.7(11) . . . . ?
C14 C9 C10 C11 -0.1(11) . . . . ?
C8 C9 C10 C11 178.2(7) . . . . ?
C9 C10 C11 C12 -0.6(13) . . . . ?
C13 C12 C11 C10 -0.1(12) . . . . ?
N1 C1 C6 C5 -178.7(7) . . . . ?
C2 C1 C6 C5 1.2(11) . . . . ?
N1 C1 C6 C7 2.7(10) . . . . ?
C2 C1 C6 C7 -177.4(7) . . . . ?
N2 C7 C6 C1 -3.9(12) . . . . ?
N3 C7 C6 C1 177.9(7) . . . . ?
N2 C7 C6 C5 177.6(8) . . . . ?
N3 C7 C6 C5 -0.6(13) . . . . ?
C1 C2 C3 C4 0.1(13) . . . . ?
C1 C6 C5 C4 0.3(16) . . . . ?
C7 C6 C5 C4 178.8(11) . . . . ?
C6 C5 C4 C3 -2(2) . . . . ?
C2 C3 C4 C5 1.4(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 S1 0.93 2.59 3.195(7) 123.4 . yes
N4 H4 N1 0.86 1.91 2.605(6) 137.5 . yes
N5 H5 S1 0.86 2.60 3.410(4) 156.6 5_666 yes

_refine_diff_density_max         0.737
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2279460'
loop_
_audit_author_name
_audit_author_address
'MANNA DEBASIS DAS SRIBASH'
;IITG
India
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H15 F6 N5 S, C16 H30 N, Cl '
_chemical_formula_sum            'C39 H45 Cl F6 N6 S'
_chemical_compound_source        SYNTHESIS
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION OF DMSO SOLUTION'
_chemical_melting_point          ?

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            WHITE
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         779.32

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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration syn

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

_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.
;

_cell_length_a                   9.2259(11)
_cell_length_b                   17.758(2)
_cell_length_c                   25.991(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.635(4)
_cell_angle_gamma                90
_cell_volume                     4237.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.54
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   0.7083
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            95469
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.575
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7444
_reflns_number_gt                4450
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0941P)²+5.8609P] 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         7444
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2645
_refine_ls_wR_factor_gt          0.2113
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
Cl1 Cl 0.05558(12) 0.37966(7) 0.44572(4) 0.0745(4) Uani 1 1 d . . . . .
S1 S 0.64378(18) 0.23981(9) 0.30294(6) 0.0990(5) Uani 1 1 d . . . . .
N2 N 0.8134(4) 0.5108(2) 0.35635(13) 0.0620(9) Uani 1 1 d . . . . .
N5 N 0.7983(4) 0.3667(2) 0.32335(13) 0.0670(10) Uani 1 1 d . . . . .
H5 H 0.845007 0.393865 0.346873 0.080 Uiso 1 1 calc R U . . .
N1 N 0.6623(4) 0.5910(2) 0.30011(14) 0.0685(10) Uani 1 1 d . . . . .
N4 N 0.8034(4) 0.2843(2) 0.38867(14) 0.0716(10) Uani 1 1 d . . . . .
H4 H 0.867870 0.315457 0.402076 0.086 Uiso 1 1 calc R U . . .
N3 N 0.8831(4) 0.5399(2) 0.44039(14) 0.0811(12) Uani 1 1 d . . . . .
H3A H 0.928513 0.497551 0.443064 0.097 Uiso 1 1 calc R U . . .
H3B H 0.884425 0.569416 0.466647 0.097 Uiso 1 1 calc R U . . .
C7 C 0.8102(5) 0.5598(3) 0.39528(16) 0.0633(11) Uani 1 1 d . . . . .
C8 C 0.7395(5) 0.5298(3) 0.31042(16) 0.0614(11) Uani 1 1 d . . . . .
C6 C 0.7347(5) 0.6299(3) 0.38868(17) 0.0630(11) Uani 1 1 d . . . . .
C14 C 0.7793(5) 0.3987(3) 0.27336(17) 0.0700(12) Uani 1 1 d . . . . .
C1 C 0.6611(5) 0.6419(3) 0.33963(18) 0.0677(12) Uani 1 1 d . . . . .
C21 C 0.8731(6) 0.1999(3) 0.45778(18) 0.0762(13) Uani 1 1 d . . . . .
H21 H 0.966756 0.219598 0.458604 0.091 Uiso 1 1 calc R U . . .
C15 C 0.7522(5) 0.2984(3) 0.33900(17) 0.0671(12) Uani 1 1 d . . . . .
N6 N 0.2817(5) 0.4529(3) 0.31458(19) 0.0958(14) Uani 1 1 d . . . . .
C9 C 0.7505(5) 0.4759(3) 0.26728(16) 0.0669(12) Uani 1 1 d . . . . .
C16 C 0.7657(5) 0.2258(3) 0.42142(18) 0.0687(12) Uani 1 1 d . . . . .
F6 F 0.3455(5) 0.1671(4) 0.4518(2) 0.178(2) Uani 1 1 d . . . . .
F1 F 1.0801(6) 0.1084(4) 0.5154(2) 0.220(3) Uani 1 1 d . . . . .
C20 C 0.8435(6) 0.1452(3) 0.4929(2) 0.0849(15) Uani 1 1 d . . . . .
F5 F 0.4162(5) 0.0839(3) 0.5013(3) 0.181(2) Uani 1 1 d . . . . .
C5 C 0.7305(6) 0.6849(3) 0.4267(2) 0.0873(15) Uani 1 1 d . . . . .
H5A H 0.779502 0.677080 0.459247 0.105 Uiso 1 1 calc R U . . .
C13 C 0.7931(6) 0.3536(3) 0.22982(19) 0.0883(16) Uani 1 1 d . . . . .
H13 H 0.812553 0.302397 0.233868 0.106 Uiso 1 1 calc R U . . .
F3 F 0.9248(6) 0.0592(4) 0.5568(2) 0.208(3) Uani 1 1 d . . . . .
C2 C 0.5836(6) 0.7095(3) 0.3306(2) 0.0836(15) Uani 1 1 d . . . . .
H2 H 0.533543 0.718192 0.298354 0.100 Uiso 1 1 calc R U . . .
C3 C 0.5805(7) 0.7618(3) 0.3679(2) 0.0982(17) Uani 1 1 d . . . . .
H3 H 0.528437 0.806175 0.361125 0.118 Uiso 1 1 calc R U . . .
C19 C 0.7038(7) 0.1162(3) 0.4927(2) 0.0958(17) Uani 1 1 d . . . . .
H19 H 0.683352 0.079011 0.516077 0.115 Uiso 1 1 calc R U . . .
C17 C 0.6253(6) 0.1979(3) 0.4213(2) 0.0847(15) Uani 1 1 d . . . . .
H17 H 0.551393 0.215550 0.397387 0.102 Uiso 1 1 calc R U . . .
C18 C 0.5962(6) 0.1435(3) 0.4572(3) 0.0913(17) Uani 1 1 d . . . . .
C4 C 0.6548(7) 0.7502(3) 0.4165(3) 0.1046(19) Uani 1 1 d . . . . .
H4A H 0.652877 0.786789 0.441989 0.126 Uiso 1 1 calc R U . . .
C33 C 0.1864(6) 0.3830(4) 0.3113(3) 0.0992(18) Uani 1 1 d . . . . .
H33A H 0.167608 0.368834 0.346120 0.119 Uiso 1 1 calc R U . . .
H33B H 0.093542 0.395689 0.292552 0.119 Uiso 1 1 calc R U . . .
C10 C 0.7345(6) 0.5048(4) 0.21714(18) 0.0916(16) Uani 1 1 d . . . . .
H10 H 0.713682 0.555667 0.212219 0.110 Uiso 1 1 calc R U . . .
C12 C 0.7780(7) 0.3848(4) 0.1812(2) 0.107(2) Uani 1 1 d . . . . .
H12 H 0.787745 0.354619 0.152515 0.129 Uiso 1 1 calc R U . . .
F4 F 0.4138(7) 0.0649(5) 0.4230(3) 0.297(6) Uani 1 1 d . . . . .
C37 C 0.4258(6) 0.4383(4) 0.3481(3) 0.107(2) Uani 1 1 d . . . . .
H37A H 0.479849 0.400404 0.331073 0.128 Uiso 1 1 calc R U . . .
H37B H 0.482767 0.484304 0.349388 0.128 Uiso 1 1 calc R U . . .
C29 C 0.1944(6) 0.5136(4) 0.3379(3) 0.1029(18) Uani 1 1 d . . . . .
H29A H 0.163612 0.495040 0.370228 0.123 Uiso 1 1 calc R U . . .
H29B H 0.107422 0.523266 0.314787 0.123 Uiso 1 1 calc R U . . .
C11 C 0.7487(8) 0.4599(4) 0.1747(2) 0.112(2) Uani 1 1 d . . . . .
H11 H 0.738484 0.480591 0.141724 0.134 Uiso 1 1 calc R U . . .
F2 F 0.9847(8) 0.1668(4) 0.5697(2) 0.223(3) Uani 1 1 d . . . . .
C38 C 0.4123(7) 0.4128(5) 0.4028(3) 0.119(2) Uani 1 1 d . . . . .
H38A H 0.341484 0.444061 0.417908 0.143 Uiso 1 1 calc R U . . .
H38B H 0.377447 0.361247 0.402362 0.143 Uiso 1 1 calc R U . . .
C23 C 0.9590(10) 0.1173(5) 0.5311(3) 0.123(2) Uani 1 1 d . . . . .
C24 C 0.3244(7) 0.4756(4) 0.2622(3) 0.117(2) Uani 1 1 d . . . . .
H24A H 0.389679 0.518496 0.266566 0.140 Uiso 1 1 calc R U . . .
H24B H 0.377946 0.434478 0.248437 0.140 Uiso 1 1 calc R U . . .
C22 C 0.4454(9) 0.1129(6) 0.4554(4) 0.137(3) Uani 1 1 d . . . . .
C39 C 0.5519(7) 0.4173(5) 0.4345(3) 0.122(2) Uani 1 1 d . . . . .
H39A H 0.583341 0.469434 0.436035 0.146 Uiso 1 1 calc R U . . .
H39B H 0.623521 0.388783 0.417739 0.146 Uiso 1 1 calc R U . . .
C34 C 0.2484(9) 0.3153(4) 0.2856(3) 0.139(3) Uani 1 1 d . . . . .
H34A H 0.343885 0.303970 0.302904 0.166 Uiso 1 1 calc R U . . .
H34B H 0.260476 0.327708 0.249953 0.166 Uiso 1 1 calc R U . . .
C25 C 0.1993(9) 0.4958(5) 0.2235(3) 0.146(3) Uani 1 1 d . . . . .
H25A H 0.147851 0.538969 0.235645 0.175 Uiso 1 1 calc R U . . .
H25B H 0.131650 0.453966 0.219122 0.175 Uiso 1 1 calc R U . . .
C30 C 0.2753(9) 0.5875(5) 0.3484(4) 0.151(3) Uani 1 1 d . . . . .
H30A H 0.299551 0.608584 0.315858 0.181 Uiso 1 1 calc R U . . .
H30B H 0.365632 0.577894 0.369705 0.181 Uiso 1 1 calc R U . . .
C26 C 0.2597(12) 0.5150(7) 0.1702(4) 0.179(4) Uiso 1 1 d . . . . .
C40 C 0.5494(10) 0.3884(5) 0.4890(3) 0.157(3) Uani 1 1 d . . . . .
H40A H 0.486323 0.419472 0.507265 0.235 Uiso 1 1 calc R U . . .
H40B H 0.646162 0.389885 0.506411 0.235 Uiso 1 1 calc R U . . .
H40C H 0.514285 0.337499 0.488149 0.235 Uiso 1 1 calc R U . . .
C31 C 0.1814(11) 0.6471(7) 0.3767(5) 0.188(5) Uani 1 1 d . . . . .
H31A H 0.130810 0.623624 0.403466 0.225 Uiso 1 1 calc R U . . .
H31B H 0.241198 0.688091 0.391485 0.225 Uiso 1 1 calc R U . . .
C35 C 0.1514(12) 0.2447(6) 0.2868(5) 0.172(4) Uani 1 1 d . . . . .
H35 H 0.097699 0.225818 0.257444 0.207 Uiso 1 1 calc R U . . .
C32 C 0.0865(15) 0.6710(7) 0.3362(5) 0.221(6) Uani 1 1 d . . . . .
H32A H 0.139165 0.681464 0.306935 0.331 Uiso 1 1 calc R U . . .
H32B H 0.038128 0.715900 0.345963 0.331 Uiso 1 1 calc R U . . .
H32C H 0.015575 0.632402 0.327291 0.331 Uiso 1 1 calc R U . . .
C36 C 0.1509(17) 0.2136(8) 0.3323(6) 0.243(6) Uani 1 1 d . . . . .
H36A H 0.249283 0.206595 0.347229 0.365 Uiso 1 1 calc R U . . .
H36B H 0.102839 0.165600 0.328807 0.365 Uiso 1 1 calc R U . . .
H36C H 0.100029 0.245567 0.354240 0.365 Uiso 1 1 calc R U . . .
C27A C 0.296(2) 0.4625(12) 0.1385(8) 0.169(7) Uiso 0.5 1 d . . P . .
C27B C 0.158(2) 0.5328(11) 0.1365(7) 0.154(6) Uiso 0.5 1 d . . P . .


_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
S1 C15 1.666(5) . ?
N2 C7 1.337(5) . ?
N2 C8 1.358(5) . ?
N5 C15 1.362(6) . ?
N5 C14 1.413(6) . ?
N5 H5 0.8600 . ?
N1 C8 1.311(5) . ?
N1 C1 1.370(6) . ?
N4 C15 1.354(5) . ?
N4 C16 1.409(6) . ?
N4 H4 0.8600 . ?
N3 C7 1.341(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C7 C6 1.428(6) . ?
C8 C9 1.486(6) . ?
C6 C5 1.392(7) . ?
C6 C1 1.401(6) . ?
C14 C9 1.402(7) . ?
C14 C13 1.403(7) . ?
C1 C2 1.405(7) . ?
C21 C20 1.378(7) . ?
C21 C16 1.379(6) . ?
C21 H21 0.9300 . ?
N6 C29 1.508(7) . ?
N6 C24 1.509(7) . ?
N6 C33 1.519(7) . ?
N6 C37 1.538(7) . ?
C9 C10 1.395(6) . ?
C16 C17 1.386(7) . ?
F6 C22 1.329(9) . ?
F1 C23 1.236(9) . ?
C20 C19 1.387(8) . ?
C20 C23 1.469(9) . ?
F5 C22 1.352(10) . ?
C5 C4 1.366(8) . ?
C5 H5A 0.9300 . ?
C13 C12 1.374(8) . ?
C13 H13 0.9300 . ?
F3 C23 1.284(8) . ?
C2 C3 1.344(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(8) . ?
C3 H3 0.9300 . ?
C19 C18 1.375(8) . ?
C19 H19 0.9300 . ?
C17 C18 1.388(8) . ?
C17 H17 0.9300 . ?
C18 C22 1.490(9) . ?
C4 H4A 0.9300 . ?
C33 C34 1.515(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C10 C11 1.377(8) . ?
C10 H10 0.9300 . ?
C12 C11 1.368(9) . ?
C12 H12 0.9300 . ?
F4 C22 1.214(10) . ?
C37 C38 1.509(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C29 C30 1.521(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C11 H11 0.9300 . ?
F2 C23 1.338(10) . ?
C38 C39 1.461(8) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C24 C25 1.498(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C39 C40 1.509(10) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C34 C35 1.542(12) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C25 C26 1.580(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C30 C31 1.592(13) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C26 C27B 1.257(19) . ?
C26 C27A 1.31(2) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C31 C32 1.369(15) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C35 C36 1.306(14) . ?
C35 H35 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C27A C27B 1.78(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
C7 N2 C8 117.2(4) . . ?
C15 N5 C14 128.2(4) . . ?
C15 N5 H5 115.9 . . ?
C14 N5 H5 115.9 . . ?
C8 N1 C1 116.0(4) . . ?
C15 N4 C16 128.9(4) . . ?
C15 N4 H4 115.5 . . ?
C16 N4 H4 115.5 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N2 C7 N3 116.4(4) . . ?
N2 C7 C6 121.5(4) . . ?
N3 C7 C6 122.1(4) . . ?
N1 C8 N2 127.0(4) . . ?
N1 C8 C9 117.1(4) . . ?
N2 C8 C9 116.0(4) . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 125.0(4) . . ?
C1 C6 C7 115.4(4) . . ?
C9 C14 C13 120.0(4) . . ?
C9 C14 N5 120.1(4) . . ?
C13 C14 N5 119.9(5) . . ?
N1 C1 C6 122.9(4) . . ?
N1 C1 C2 118.8(4) . . ?
C6 C1 C2 118.4(5) . . ?
C20 C21 C16 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N4 C15 N5 111.0(4) . . ?
N4 C15 S1 123.8(4) . . ?
N5 C15 S1 125.2(3) . . ?
C29 N6 C24 111.7(5) . . ?
C29 N6 C33 106.1(4) . . ?
C24 N6 C33 111.7(5) . . ?
C29 N6 C37 111.0(5) . . ?
C24 N6 C37 105.5(4) . . ?
C33 N6 C37 110.9(5) . . ?
C10 C9 C14 117.8(4) . . ?
C10 C9 C8 117.3(5) . . ?
C14 C9 C8 124.8(4) . . ?
C21 C16 C17 119.4(5) . . ?
C21 C16 N4 117.2(4) . . ?
C17 C16 N4 123.2(5) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 C23 120.5(6) . . ?
C19 C20 C23 119.3(6) . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.5(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C18 C19 C20 118.8(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C16 C17 C18 119.3(5) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 121.5(5) . . ?
C19 C18 C22 120.2(7) . . ?
C17 C18 C22 118.3(7) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C34 C33 N6 115.6(5) . . ?
C34 C33 H33A 108.4 . . ?
N6 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
N6 C33 H33B 108.4 . . ?
H33A C33 H33B 107.4 . . ?
C11 C10 C9 121.7(6) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C38 C37 N6 115.9(5) . . ?
C38 C37 H37A 108.3 . . ?
N6 C37 H37A 108.3 . . ?
C38 C37 H37B 108.3 . . ?
N6 C37 H37B 108.3 . . ?
H37A C37 H37B 107.4 . . ?
N6 C29 C30 114.6(5) . . ?
N6 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
N6 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C39 C38 C37 111.5(5) . . ?
C39 C38 H38A 109.3 . . ?
C37 C38 H38A 109.3 . . ?
C39 C38 H38B 109.3 . . ?
C37 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
F1 C23 F3 110.1(8) . . ?
F1 C23 F2 103.4(8) . . ?
F3 C23 F2 99.9(7) . . ?
F1 C23 C20 116.1(7) . . ?
F3 C23 C20 115.1(7) . . ?
F2 C23 C20 110.4(7) . . ?
C25 C24 N6 114.6(5) . . ?
C25 C24 H24A 108.6 . . ?
N6 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
N6 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
F4 C22 F6 110.0(10) . . ?
F4 C22 F5 106.9(8) . . ?
F6 C22 F5 98.2(7) . . ?
F4 C22 C18 115.9(8) . . ?
F6 C22 C18 112.2(7) . . ?
F5 C22 C18 112.2(8) . . ?
C38 C39 C40 114.7(6) . . ?
C38 C39 H39A 108.6 . . ?
C40 C39 H39A 108.6 . . ?
C38 C39 H39B 108.6 . . ?
C40 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
C33 C34 C35 113.1(7) . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C24 C25 C26 109.0(7) . . ?
C24 C25 H25A 109.9 . . ?
C26 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
C26 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C29 C30 C31 112.1(7) . . ?
C29 C30 H30A 109.2 . . ?
C31 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C31 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C27B C26 C27A 87.6(14) . . ?
C27B C26 C25 111.3(13) . . ?
C27A C26 C25 122.2(13) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C32 C31 C30 100.8(12) . . ?
C32 C31 H31A 111.6 . . ?
C30 C31 H31A 111.6 . . ?
C32 C31 H31B 111.6 . . ?
C30 C31 H31B 111.6 . . ?
H31A C31 H31B 109.4 . . ?
C36 C35 C34 114.6(11) . . ?
C36 C35 H35 122.7 . . ?
C34 C35 H35 122.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C26 C27A C27B 45.0(10) . . ?
C26 C27B C27A 47.5(10) . . ?

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
C8 N2 C7 N3 179.6(4) . . . . ?
C8 N2 C7 C6 -1.2(6) . . . . ?
C1 N1 C8 N2 2.5(7) . . . . ?
C1 N1 C8 C9 -176.2(4) . . . . ?
C7 N2 C8 N1 -1.3(6) . . . . ?
C7 N2 C8 C9 177.4(4) . . . . ?
N2 C7 C6 C5 -177.7(5) . . . . ?
N3 C7 C6 C5 1.5(7) . . . . ?
N2 C7 C6 C1 2.2(6) . . . . ?
N3 C7 C6 C1 -178.7(4) . . . . ?
C15 N5 C14 C9 141.7(5) . . . . ?
C15 N5 C14 C13 -40.0(7) . . . . ?
C8 N1 C1 C6 -1.2(6) . . . . ?
C8 N1 C1 C2 178.3(4) . . . . ?
C5 C6 C1 N1 178.9(5) . . . . ?
C7 C6 C1 N1 -1.0(6) . . . . ?
C5 C6 C1 C2 -0.6(7) . . . . ?
C7 C6 C1 C2 179.5(4) . . . . ?
C16 N4 C15 N5 170.4(4) . . . . ?
C16 N4 C15 S1 -8.3(7) . . . . ?
C14 N5 C15 N4 173.9(4) . . . . ?
C14 N5 C15 S1 -7.5(7) . . . . ?
C13 C14 C9 C10 0.9(7) . . . . ?
N5 C14 C9 C10 179.2(4) . . . . ?
C13 C14 C9 C8 -177.4(4) . . . . ?
N5 C14 C9 C8 0.9(7) . . . . ?
N1 C8 C9 C10 26.2(6) . . . . ?
N2 C8 C9 C10 -152.7(4) . . . . ?
N1 C8 C9 C14 -155.6(4) . . . . ?
N2 C8 C9 C14 25.6(6) . . . . ?
C20 C21 C16 C17 1.9(8) . . . . ?
C20 C21 C16 N4 177.0(5) . . . . ?
C15 N4 C16 C21 148.2(5) . . . . ?
C15 N4 C16 C17 -37.0(7) . . . . ?
C16 C21 C20 C19 -1.0(8) . . . . ?
C16 C21 C20 C23 179.2(6) . . . . ?
C1 C6 C5 C4 0.2(8) . . . . ?
C7 C6 C5 C4 -180.0(5) . . . . ?
C9 C14 C13 C12 -0.2(8) . . . . ?
N5 C14 C13 C12 -178.5(5) . . . . ?
N1 C1 C2 C3 -179.1(5) . . . . ?
C6 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C21 C20 C19 C18 -0.5(9) . . . . ?
C23 C20 C19 C18 179.2(7) . . . . ?
C21 C16 C17 C18 -1.2(8) . . . . ?
N4 C16 C17 C18 -175.9(5) . . . . ?
C20 C19 C18 C17 1.3(9) . . . . ?
C20 C19 C18 C22 179.2(7) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C16 C17 C18 C22 -178.4(6) . . . . ?
C6 C5 C4 C3 0.4(10) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C29 N6 C33 C34 176.2(6) . . . . ?
C24 N6 C33 C34 54.3(8) . . . . ?
C37 N6 C33 C34 -63.1(7) . . . . ?
C14 C9 C10 C11 -1.1(8) . . . . ?
C8 C9 C10 C11 177.3(5) . . . . ?
C14 C13 C12 C11 -0.3(10) . . . . ?
C29 N6 C37 C38 60.2(7) . . . . ?
C24 N6 C37 C38 -178.7(6) . . . . ?
C33 N6 C37 C38 -57.6(7) . . . . ?
C24 N6 C29 C30 -62.4(8) . . . . ?
C33 N6 C29 C30 175.6(6) . . . . ?
C37 N6 C29 C30 55.0(8) . . . . ?
C13 C12 C11 C10 0.1(11) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
N6 C37 C38 C39 -166.8(6) . . . . ?
C21 C20 C23 F1 -39.7(12) . . . . ?
C19 C20 C23 F1 140.6(8) . . . . ?
C21 C20 C23 F3 -170.4(7) . . . . ?
C19 C20 C23 F3 9.9(12) . . . . ?
C21 C20 C23 F2 77.5(9) . . . . ?
C19 C20 C23 F2 -102.2(8) . . . . ?
C29 N6 C24 C25 -56.9(8) . . . . ?
C33 N6 C24 C25 61.8(8) . . . . ?
C37 N6 C24 C25 -177.6(7) . . . . ?
C19 C18 C22 F4 -97.9(11) . . . . ?
C17 C18 C22 F4 80.1(12) . . . . ?
C19 C18 C22 F6 134.7(8) . . . . ?
C17 C18 C22 F6 -47.3(11) . . . . ?
C19 C18 C22 F5 25.3(11) . . . . ?
C17 C18 C22 F5 -156.7(7) . . . . ?
C37 C38 C39 C40 -176.6(7) . . . . ?
N6 C33 C34 C35 176.2(7) . . . . ?
N6 C24 C25 C26 -177.7(7) . . . . ?
N6 C29 C30 C31 -175.9(7) . . . . ?
C24 C25 C26 C27B -179.6(12) . . . . ?
C24 C25 C26 C27A 79.3(16) . . . . ?
C29 C30 C31 C32 -77.0(11) . . . . ?
C33 C34 C35 C36 -71.8(14) . . . . ?
C25 C26 C27A C27B 113.8(17) . . . . ?
C25 C26 C27B C27A -123.8(15) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.050

