# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2035445'
loop_
_audit_author_name
_audit_author_address
'Yueting Wei'
;Shihezi University
China
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O2 S2'
_chemical_formula_weight         407.49

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'
O O 0.0106 0.0060 '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 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                   19.019(2)
_cell_length_b                   19.073(2)
_cell_length_c                   10.6129(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.402(6)
_cell_angle_gamma                90
_cell_volume                     3832.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6877
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.78

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4723
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18537
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_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             3577
_reflns_number_gt                2701
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0850P)²+12.4343P] 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_number_reflns         3577
_refine_ls_number_parameters     261
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1997
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_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 0.90207(6) 0.44683(5) 0.28399(9) 0.0431(3) Uani 1 1 d . . . . .
O1 O 0.93130(16) 0.51147(14) 0.3323(3) 0.0486(7) Uani 1 1 d . . . . .
N1 N 0.8001(2) 0.5383(2) 0.4325(4) 0.0513(9) Uani 1 1 d D . . . .
H1B H 0.8456(7) 0.544(3) 0.438(5) 0.059(15) Uiso 1 1 d D . . . .
H1A H 0.772(2) 0.553(3) 0.487(4) 0.061(15) Uiso 1 1 d D . . . .
C1 C 0.9059(2) 0.3848(2) 0.4060(4) 0.0409(9) Uani 1 1 d . . . . .
S2 S 0.63759(6) 0.47869(6) 0.41711(11) 0.0519(3) Uani 1 1 d . . . . .
O2 O 0.92204(16) 0.41759(16) 0.1697(3) 0.0507(8) Uani 1 1 d . . . . .
N2 N 0.81442(19) 0.46096(17) 0.2591(3) 0.0435(8) Uani 1 1 d . . . . .
C2 C 0.8835(2) 0.3167(2) 0.3775(4) 0.0481(10) Uani 1 1 d . . . . .
H2 H 0.871444 0.302615 0.292342 0.058 Uiso 1 1 calc R U . . .
N3 N 0.77621(19) 0.40954(17) 0.1881(3) 0.0444(8) Uani 1 1 d . . . . .
C3 C 0.8792(3) 0.2699(2) 0.4764(4) 0.0521(11) Uani 1 1 d . . . . .
H3A H 0.863928 0.223154 0.459067 0.063 Uiso 1 1 calc R U . . .
C4 C 0.8971(2) 0.2908(2) 0.6005(4) 0.0491(11) Uani 1 1 d . . . . .
H4 H 0.893568 0.258417 0.667628 0.059 Uiso 1 1 calc R U . . .
C5 C 0.9200(2) 0.3582(2) 0.6269(4) 0.0474(10) Uani 1 1 d . . . . .
H5 H 0.932489 0.371943 0.712083 0.057 Uiso 1 1 calc R U . . .
C6 C 0.9248(2) 0.4062(2) 0.5294(4) 0.0469(10) Uani 1 1 d . . . . .
H6 H 0.940723 0.452747 0.546975 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7741(2) 0.4901(2) 0.3482(4) 0.0447(10) Uani 1 1 d . . . . .
C9 C 0.7132(2) 0.4091(2) 0.2295(4) 0.0428(9) Uani 1 1 d . . . . .
C8 C 0.7082(2) 0.4593(2) 0.3301(4) 0.0435(10) Uani 1 1 d . . . . .
C10 C 0.6607(2) 0.3595(2) 0.1703(4) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.6855(3) 0.2959(2) 0.1259(4) 0.0494(11) Uani 1 1 d . . . . .
H11 H 0.734343 0.284945 0.138760 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6389(3) 0.2487(2) 0.0633(4) 0.0565(12) Uani 1 1 d . . . . .
H12 H 0.656257 0.206084 0.031832 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5680(3) 0.2633(3) 0.0465(4) 0.0602(13) Uani 1 1 d . . . . .
H13 H 0.536277 0.230623 0.004232 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5428(3) 0.3261(3) 0.0916(5) 0.0627(13) Uani 1 1 d . . . . .
H14 H 0.493729 0.336481 0.080142 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5895(3) 0.3734(3) 0.1534(4) 0.0549(11) Uani 1 1 d . . . . .
H15 H 0.572045 0.416058 0.184468 0.066 Uiso 1 1 calc R U . . .
C16 C 0.6531(2) 0.4254(2) 0.5547(4) 0.0433(9) Uani 1 1 d . . . . .
C17 C 0.5966(3) 0.4174(2) 0.6275(4) 0.0486(10) Uani 1 1 d . . . . .
H17 H 0.552207 0.438118 0.601182 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6054(3) 0.3792(2) 0.7386(4) 0.0560(12) Uani 1 1 d . . . . .
H18 H 0.566862 0.373162 0.788277 0.067 Uiso 1 1 calc R U . . .
C19 C 0.6697(3) 0.3500(2) 0.7770(4) 0.0547(12) Uani 1 1 d . . . . .
H19 H 0.675630 0.324630 0.854278 0.066 Uiso 1 1 calc R U . . .
C20 C 0.7256(3) 0.3571(2) 0.7050(4) 0.0489(10) Uani 1 1 d . . . . .
H20 H 0.769688 0.335941 0.731932 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7179(2) 0.3954(2) 0.5923(4) 0.0456(10) Uani 1 1 d . . . . .
H21 H 0.756433 0.400789 0.542351 0.055 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 O2 1.419(3) . ?
S1 O1 1.428(3) . ?
S1 N2 1.685(4) . ?
S1 C1 1.751(4) . ?
N1 C7 1.344(6) . ?
N1 H1B 0.869(10) . ?
N1 H1A 0.869(10) . ?
C1 C6 1.387(6) . ?
C1 C2 1.391(6) . ?
S2 C8 1.740(4) . ?
S2 C16 1.781(4) . ?
N2 C7 1.389(5) . ?
N2 N3 1.398(5) . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
N3 C9 1.315(5) . ?
C3 C4 1.387(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.380(6) . ?
C9 C8 1.444(6) . ?
C9 C10 1.471(6) . ?
C10 C15 1.375(6) . ?
C10 C11 1.399(6) . ?
C11 C12 1.387(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.372(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.382(6) . ?
C16 C17 1.389(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
O2 S1 O1 121.33(18) . . ?
O2 S1 N2 105.62(17) . . ?
O1 S1 N2 105.32(18) . . ?
O2 S1 C1 111.75(19) . . ?
O1 S1 C1 109.30(18) . . ?
N2 S1 C1 101.30(18) . . ?
C7 N1 H1B 116(3) . . ?
C7 N1 H1A 116(3) . . ?
H1B N1 H1A 126(5) . . ?
C6 C1 C2 121.9(4) . . ?
C6 C1 S1 119.2(3) . . ?
C2 C1 S1 118.7(3) . . ?
C8 S2 C16 103.7(2) . . ?
C7 N2 N3 110.8(3) . . ?
C7 N2 S1 124.0(3) . . ?
N3 N2 S1 115.4(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C9 N3 N2 105.6(3) . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 131.0(4) . . ?
N1 C7 N2 122.3(4) . . ?
C8 C7 N2 106.7(4) . . ?
N3 C9 C8 111.6(4) . . ?
N3 C9 C10 117.7(4) . . ?
C8 C9 C10 130.8(4) . . ?
C7 C8 C9 105.3(4) . . ?
C7 C8 S2 124.8(3) . . ?
C9 C8 S2 129.8(3) . . ?
C15 C10 C11 118.7(4) . . ?
C15 C10 C9 123.5(4) . . ?
C11 C10 C9 117.7(4) . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C10 C15 C14 121.1(5) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C21 C16 C17 120.6(4) . . ?
C21 C16 S2 123.1(3) . . ?
C17 C16 S2 116.2(3) . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 118.8(4) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?

_refine_diff_density_max         0.799
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2035449'
loop_
_audit_author_name
_audit_author_address
'Yueting Wei'
;Shihezi University
China
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N3 S, 2(C4 H5 N O2)'
_chemical_formula_sum            'C23 H23 N5 O4 S'
_chemical_formula_weight         465.52
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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'

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

_cell_length_a                   7.1506(2)
_cell_length_b                   10.5088(3)
_cell_length_c                   15.9913(4)
_cell_angle_alpha                102.8900(10)
_cell_angle_beta                 98.9170(10)
_cell_angle_gamma                106.1600(10)
_cell_volume                     1094.43(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13458
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_min         2.687
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4057
_reflns_number_total             4623
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.5213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 H3A-N3 = N3-H3B = N1-H1
 0.87 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 3.8A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C21(H21A,H21B), C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), N4(H4), N5(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20404(6) 0.80646(4) 0.76108(2) 0.03045(11) Uani 1 1 d . . . . .
N1 N 0.2664(2) 0.55353(12) 0.55978(8) 0.0285(3) Uani 1 1 d D . . . .
H1 H 0.270(3) 0.5267(19) 0.5047(7) 0.042(5) Uiso 1 1 d D . . . .
N2 N 0.2576(2) 0.46703(12) 0.61307(8) 0.0268(3) Uani 1 1 d . . . . .
N3 N 0.2782(3) 0.78209(14) 0.56373(9) 0.0395(4) Uani 1 1 d D . . . .
H3A H 0.253(3) 0.8543(14) 0.5911(11) 0.040(5) Uiso 1 1 d D . . . .
H3B H 0.268(3) 0.7613(19) 0.5068(7) 0.043(5) Uiso 1 1 d D . . . .
C1 C 0.2635(2) 0.67804(14) 0.60223(9) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.2505(2) 0.67536(14) 0.68799(9) 0.0243(3) Uani 1 1 d . . . . .
C3 C 0.2468(2) 0.54014(14) 0.69059(9) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.2342(2) 0.47524(14) 0.76316(9) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.2804(3) 0.55309(16) 0.85099(10) 0.0328(3) Uani 1 1 d . . . . .
H5 H 0.319118 0.650889 0.865125 0.039 Uiso 1 1 calc R . . . .
C6 C 0.2701(3) 0.48882(18) 0.91797(10) 0.0372(4) Uani 1 1 d . . . . .
H6 H 0.302631 0.543436 0.977475 0.045 Uiso 1 1 calc R . . . .
C7 C 0.2136(2) 0.34702(17) 0.89957(11) 0.0349(4) Uani 1 1 d . . . . .
H7 H 0.206117 0.303749 0.945717 0.042 Uiso 1 1 calc R . . . .
C8 C 0.1682(3) 0.26917(17) 0.81276(11) 0.0380(4) Uani 1 1 d . . . . .
H8 H 0.129337 0.171411 0.799130 0.046 Uiso 1 1 calc R . . . .
C9 C 0.1785(2) 0.33200(15) 0.74533(10) 0.0318(3) Uani 1 1 d . . . . .
H9 H 0.147219 0.276681 0.686055 0.038 Uiso 1 1 calc R . . . .
C10 C 0.4398(3) 0.91266(15) 0.83103(9) 0.0324(3) Uani 1 1 d . U . . .
C11 C 0.4410(4) 1.03575(17) 0.88665(11) 0.0522(5) Uani 1 1 d . U . . .
H11 H 0.321839 1.059478 0.884531 0.063 Uiso 1 1 calc R . . . .
C12 C 0.6175(5) 1.1229(2) 0.94493(13) 0.0707(8) Uani 1 1 d . U . . .
H12 H 0.618984 1.206861 0.983042 0.085 Uiso 1 1 calc R . . . .
C13 C 0.7911(4) 1.0896(3) 0.94843(14) 0.0772(9) Uani 1 1 d . U . . .
H13 H 0.912024 1.150923 0.988095 0.093 Uiso 1 1 calc R . . . .
C14 C 0.7889(3) 0.9668(3) 0.89414(14) 0.0652(6) Uani 1 1 d . U . . .
H14 H 0.908093 0.943056 0.896960 0.078 Uiso 1 1 calc R . . . .
C15 C 0.6122(3) 0.87771(19) 0.83519(11) 0.0426(4) Uani 1 1 d . U . . .
H15 H 0.610653 0.793031 0.797961 0.051 Uiso 1 1 calc R . . . .
O1 O 0.76601(19) 0.67710(12) 0.60797(7) 0.0381(3) Uani 1 1 d . . . . .
O2 O 0.75447(19) 0.93813(11) 0.41779(7) 0.0368(3) Uani 1 1 d . . . . .
N4 N 0.75858(19) 0.78505(12) 0.49932(8) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.751987 0.714470 0.455937 0.032 Uiso 1 1 calc R . . . .
C16 C 0.7703(2) 0.78010(15) 0.58478(10) 0.0284(3) Uani 1 1 d . . . . .
C17 C 0.7924(3) 0.92167(17) 0.64109(10) 0.0368(4) Uani 1 1 d . . . . .
H17A H 0.926972 0.964696 0.681307 0.044 Uiso 1 1 calc R . . . .
H17B H 0.690200 0.916574 0.676601 0.044 Uiso 1 1 calc R . . . .
C18 C 0.7624(2) 1.00320(15) 0.57537(10) 0.0312(3) Uani 1 1 d . . . . .
H18A H 0.635005 1.023483 0.574026 0.037 Uiso 1 1 calc R . . . .
H18B H 0.873964 1.091289 0.590811 0.037 Uiso 1 1 calc R . . . .
C19 C 0.7581(2) 0.91061(14) 0.48775(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.8130(2) 0.64254(13) 0.87996(8) 0.0460(3) Uani 1 1 d . . . . .
O4 O 0.6966(2) 0.35252(13) 0.60654(7) 0.0452(3) Uani 1 1 d . . . . .
N5 N 0.7549(2) 0.52004(14) 0.73510(8) 0.0315(3) Uani 1 1 d . . . . .
H5A H 0.776879 0.590570 0.712651 0.038 Uiso 1 1 calc R . . . .
C20 C 0.7668(2) 0.53424(17) 0.82418(10) 0.0312(3) Uani 1 1 d . . . . .
C21 C 0.7104(2) 0.39111(17) 0.83614(10) 0.0338(3) Uani 1 1 d . . . . .
H21A H 0.590711 0.372659 0.861278 0.041 Uiso 1 1 calc R . . . .
H21B H 0.821867 0.380254 0.875972 0.041 Uiso 1 1 calc R . . . .
C22 C 0.6664(3) 0.29354(17) 0.74409(10) 0.0348(4) Uani 1 1 d . . . . .
H22A H 0.755301 0.236145 0.741941 0.042 Uiso 1 1 calc R . . . .
H22B H 0.525484 0.232107 0.726155 0.042 Uiso 1 1 calc R . . . .
C23 C 0.7059(2) 0.38653(17) 0.68528(10) 0.0314(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
S1 C2 1.7410(14) . ?
S1 C10 1.7750(17) . ?
N1 H1 0.870(9) . ?
N1 N2 1.3736(16) . ?
N1 C1 1.3403(18) . ?
N2 C3 1.3305(18) . ?
N3 H3A 0.866(9) . ?
N3 H3B 0.873(9) . ?
N3 C1 1.3573(19) . ?
C1 C2 1.3949(19) . ?
C2 C3 1.4239(19) . ?
C3 C4 1.4736(19) . ?
C4 C5 1.394(2) . ?
C4 C9 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 C15 1.377(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9500 . ?
O1 C16 1.2142(18) . ?
O2 C19 1.2148(18) . ?
N4 H4 0.8800 . ?
N4 C16 1.3698(18) . ?
N4 C19 1.3735(18) . ?
C16 C17 1.509(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.523(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.507(2) . ?
O3 C20 1.203(2) . ?
O4 C23 1.2156(19) . ?
N5 H5A 0.8800 . ?
N5 C20 1.3853(19) . ?
N5 C23 1.366(2) . ?
C20 C21 1.509(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.523(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.503(2) . ?

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 S1 C10 106.14(8) . . ?
N2 N1 H1 121.9(13) . . ?
C1 N1 H1 126.0(13) . . ?
C1 N1 N2 112.13(12) . . ?
C3 N2 N1 105.37(11) . . ?
H3A N3 H3B 121.2(18) . . ?
C1 N3 H3A 117.7(13) . . ?
C1 N3 H3B 117.2(13) . . ?
N1 C1 N3 122.58(13) . . ?
N1 C1 C2 107.05(12) . . ?
N3 C1 C2 130.34(13) . . ?
C1 C2 S1 122.41(11) . . ?
C1 C2 C3 104.68(12) . . ?
C3 C2 S1 131.95(11) . . ?
N2 C3 C2 110.77(12) . . ?
N2 C3 C4 118.88(12) . . ?
C2 C3 C4 130.35(13) . . ?
C5 C4 C3 121.96(13) . . ?
C5 C4 C9 117.88(13) . . ?
C9 C4 C3 120.15(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.53(14) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.13(15) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.71(14) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.76(15) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.00(14) . . ?
C8 C9 H9 119.5 . . ?
C11 C10 S1 115.49(15) . . ?
C15 C10 S1 124.27(12) . . ?
C15 C10 C11 120.18(17) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 N4 H4 123.2 . . ?
C16 N4 C19 113.62(12) . . ?
C19 N4 H4 123.2 . . ?
O1 C16 N4 123.63(14) . . ?
O1 C16 C17 128.15(14) . . ?
N4 C16 C17 108.21(12) . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C16 C17 C18 104.57(12) . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 C17 104.71(12) . . ?
C19 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
O2 C19 N4 124.23(13) . . ?
O2 C19 C18 127.66(13) . . ?
N4 C19 C18 108.11(12) . . ?
C20 N5 H5A 123.1 . . ?
C23 N5 H5A 123.1 . . ?
C23 N5 C20 113.87(13) . . ?
O3 C20 N5 124.83(16) . . ?
O3 C20 C21 127.79(15) . . ?
N5 C20 C21 107.37(13) . . ?
C20 C21 H21A 110.7 . . ?
C20 C21 H21B 110.7 . . ?
C20 C21 C22 105.33(12) . . ?
H21A C21 H21B 108.8 . . ?
C22 C21 H21A 110.7 . . ?
C22 C21 H21B 110.7 . . ?
C21 C22 H22A 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 C21 104.79(13) . . ?
C23 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
O4 C23 N5 124.17(15) . . ?
O4 C23 C22 127.32(15) . . ?
N5 C23 C22 108.51(13) . . ?

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
N1 H1 O1 0.870(9) 2.393(14) 3.1173(17) 141.0(16) 2_666 yes
N1 H1 O4 0.870(9) 2.409(15) 3.0599(17) 132.0(15) 2_666 yes
N3 H3A O2 0.866(9) 2.233(14) 2.9669(17) 142.5(16) 2_676 yes
N3 H3B O4 0.873(9) 2.031(12) 2.8325(18) 152.1(18) 2_666 yes
N4 H4 N2 0.88 1.96 2.8110(17) 163.6 2_666 yes
N5 H5A O1 0.88 2.08 2.8876(17) 152.8 . yes

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
S1 C2 C3 N2 168.91(12) . . . . ?
S1 C2 C3 C4 -11.3(2) . . . . ?
S1 C10 C11 C12 178.34(14) . . . . ?
S1 C10 C15 C14 -178.26(14) . . . . ?
N1 N2 C3 C2 -0.53(16) . . . . ?
N1 N2 C3 C4 179.66(12) . . . . ?
N1 C1 C2 S1 -169.87(11) . . . . ?
N1 C1 C2 C3 0.16(17) . . . . ?
N2 N1 C1 N3 177.52(15) . . . . ?
N2 N1 C1 C2 -0.51(18) . . . . ?
N2 C3 C4 C5 161.01(15) . . . . ?
N2 C3 C4 C9 -17.7(2) . . . . ?
N3 C1 C2 S1 12.3(2) . . . . ?
N3 C1 C2 C3 -177.66(17) . . . . ?
C1 N1 N2 C3 0.65(17) . . . . ?
C1 C2 C3 N2 0.24(17) . . . . ?
C1 C2 C3 C4 -179.97(15) . . . . ?
C2 S1 C10 C11 171.08(12) . . . . ?
C2 S1 C10 C15 -11.64(15) . . . . ?
C2 C3 C4 C5 -18.8(2) . . . . ?
C2 C3 C4 C9 162.49(16) . . . . ?
C3 C4 C5 C6 -178.93(15) . . . . ?
C3 C4 C9 C8 179.21(15) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C4 C9 C8 0.4(2) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
C10 S1 C2 C1 -99.81(13) . . . . ?
C10 S1 C2 C3 93.20(15) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
O1 C16 C17 C18 -173.37(16) . . . . ?
N4 C16 C17 C18 7.73(18) . . . . ?
C16 N4 C19 O2 177.78(15) . . . . ?
C16 N4 C19 C18 -2.32(18) . . . . ?
C16 C17 C18 C19 -8.71(17) . . . . ?
C17 C18 C19 O2 -173.07(16) . . . . ?
C17 C18 C19 N4 7.03(17) . . . . ?
C19 N4 C16 O1 177.48(15) . . . . ?
C19 N4 C16 C17 -3.56(18) . . . . ?
O3 C20 C21 C22 -179.99(17) . . . . ?
N5 C20 C21 C22 0.42(17) . . . . ?
C20 N5 C23 O4 -176.58(16) . . . . ?
C20 N5 C23 C22 3.64(18) . . . . ?
C20 C21 C22 C23 1.57(17) . . . . ?
C21 C22 C23 O4 177.14(17) . . . . ?
C21 C22 C23 N5 -3.09(17) . . . . ?
C23 N5 C20 O3 177.83(16) . . . . ?
C23 N5 C20 C21 -2.56(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2035452'
loop_
_audit_author_name
_audit_author_address
'Yueting Wei'
;Shihezi University
China
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, 3(C16 H12 F3 N3 S)'
_chemical_formula_sum            'C49 H37 Cl3 F9 N9 S3'
_chemical_formula_weight         1125.40
_chemical_melting_point          ?
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'

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

_cell_length_a                   13.8799(8)
_cell_length_b                   14.9130(8)
_cell_length_c                   14.9991(7)
_cell_angle_alpha                106.397(2)
_cell_angle_beta                 108.593(2)
_cell_angle_gamma                108.531(2)
_cell_volume                     2523.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         2.294
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8785
_reflns_number_total             10688
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         10688
_refine_ls_number_restraints     219
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+6.9390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C49A-Cl3A \\sim C49-Cl3
 with sigma of 0.02
 Cl1A-C49A \\sim Cl1-C49
 with sigma of 0.02
 Cl1A-Cl3A \\sim Cl1-Cl3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl1A \\sim Cl2 \\sim Cl2A \\sim Cl3 \\sim Cl3A \\sim C49 \\sim C49A:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A, Cl2A, Cl3A, C49A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C49A)=Sof(H49A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C49)=Sof(H49)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C49(H49), C49A(H49A)
6.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
 C30(H30), C31(H31), N8(H8), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C43(H43), C44(H44), C46(H46), C47(H47), N2(H2), C5(H5A), C6(H6), C7(H7),
 C8(H8A), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25809(16) 0.38373(14) 0.35658(15) 0.0641(6) Uani 0.836(4) 1 d D U P A
1
Cl1A Cl 0.3673(12) 0.4535(8) 0.4383(9) 0.092(3) Uani 0.164(4) 1 d D U P A 2
Cl2 Cl 0.4005(3) 0.3645(2) 0.25662(18) 0.0535(6) Uani 0.836(4) 1 d . U P A 1
Cl2A Cl 0.4249(13) 0.3924(13) 0.2881(13) 0.061(3) Uani 0.164(4) 1 d . U P A 2
Cl3 Cl 0.3757(2) 0.25861(18) 0.3890(2) 0.0530(6) Uani 0.836(4) 1 d D U P A 1
Cl3A Cl 0.4135(13) 0.2851(12) 0.4113(15) 0.071(3) Uani 0.164(4) 1 d D U P A 2
C49 C 0.3167(6) 0.3076(6) 0.3058(6) 0.0505(14) Uani 0.836(4) 1 d D U P A 1
H49 H 0.250361 0.244742 0.244127 0.061 Uiso 0.836(4) 1 calc R . P A 1
C49A C 0.330(3) 0.333(2) 0.348(2) 0.061(5) Uani 0.164(4) 1 d D U P A 2
H49A H 0.247809 0.284894 0.300695 0.074 Uiso 0.164(4) 1 calc R . P A 2
S2 S 0.88040(8) 0.54748(6) 0.99853(7) 0.0275(2) Uani 1 1 d . . . . .
F4 F 0.4159(3) 0.1713(3) 0.5758(3) 0.0884(12) Uani 1 1 d . . . . .
F5 F 0.5347(4) 0.1603(3) 0.5229(3) 0.0963(13) Uani 1 1 d . . . . .
F6 F 0.4975(3) 0.0792(2) 0.6120(3) 0.0908(12) Uani 1 1 d . U . . .
N4 N 0.7378(3) 0.6831(3) 1.0146(3) 0.0365(8) Uani 1 1 d . . . . .
N5 N 0.8647(2) 0.7952(2) 0.9742(2) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.837998 0.841663 0.980257 0.031 Uiso 1 1 calc R . . . .
N6 N 0.9530(2) 0.8021(2) 0.9496(2) 0.0258(6) Uani 1 1 d . . . . .
C17 C 0.8243(3) 0.7084(3) 0.9879(3) 0.0250(7) Uani 1 1 d . . . . .
C18 C 0.8883(3) 0.6551(3) 0.9722(3) 0.0244(7) Uani 1 1 d . . . . .
C19 C 0.9673(3) 0.7169(3) 0.9475(2) 0.0228(7) Uani 1 1 d . . . . .
C20 C 1.0547(3) 0.7007(3) 0.9194(2) 0.0240(7) Uani 1 1 d . . . . .
C21 C 1.0369(3) 0.6016(3) 0.8596(3) 0.0282(7) Uani 1 1 d . . . . .
H21 H 0.968752 0.542251 0.839307 0.034 Uiso 1 1 calc R . . . .
C22 C 1.1181(3) 0.5886(3) 0.8291(3) 0.0355(9) Uani 1 1 d . . . . .
H22 H 1.105468 0.520402 0.788932 0.043 Uiso 1 1 calc R . . . .
C23 C 1.2167(3) 0.6741(3) 0.8568(3) 0.0377(9) Uani 1 1 d . . . . .
H23 H 1.271023 0.665023 0.834357 0.045 Uiso 1 1 calc R . . . .
C24 C 1.2360(3) 0.7729(3) 0.9175(3) 0.0369(9) Uani 1 1 d . . . . .
H24 H 1.304666 0.831754 0.937940 0.044 Uiso 1 1 calc R . . . .
C25 C 1.1565(3) 0.7868(3) 0.9485(3) 0.0300(8) Uani 1 1 d . . . . .
H25 H 1.170677 0.855227 0.990003 0.036 Uiso 1 1 calc R . . . .
C26 C 0.7728(3) 0.4387(3) 0.8808(3) 0.0256(7) Uani 1 1 d . . . . .
C27 C 0.7209(3) 0.4475(3) 0.7905(3) 0.0356(9) Uani 1 1 d . . . . .
H27 H 0.742475 0.514386 0.789751 0.043 Uiso 1 1 calc R . . . .
C28 C 0.6376(4) 0.3593(3) 0.7011(3) 0.0427(10) Uani 1 1 d . . . . .
H28 H 0.602286 0.365465 0.639035 0.051 Uiso 1 1 calc R . . . .
C29 C 0.6058(3) 0.2616(3) 0.7023(3) 0.0343(8) Uani 1 1 d . . . . .
C30 C 0.6572(3) 0.2526(3) 0.7914(3) 0.0356(9) Uani 1 1 d . . . . .
H30 H 0.635439 0.185794 0.792284 0.043 Uiso 1 1 calc R . . . .
C31 C 0.7415(3) 0.3414(3) 0.8808(3) 0.0311(8) Uani 1 1 d . . . . .
H31 H 0.777712 0.334934 0.942398 0.037 Uiso 1 1 calc R . . . .
C32 C 0.5149(4) 0.1682(3) 0.6052(4) 0.0493(12) Uani 1 1 d . . . . .
S3 S 0.47871(8) 0.95146(7) 0.85066(7) 0.0328(2) Uani 1 1 d . . . . .
F7 F 0.1575(3) 0.5671(3) 0.3766(2) 0.1007(15) Uani 1 1 d . . . . .
F8 F 0.0258(3) 0.5657(3) 0.4215(3) 0.0911(12) Uani 1 1 d . U . . .
F9 F 0.1137(4) 0.4796(3) 0.4582(3) 0.0998(14) Uani 1 1 d . . . . .
N7 N 0.6475(4) 0.9968(3) 0.7428(3) 0.0388(8) Uani 1 1 d . . . . .
N8 N 0.7676(3) 0.9614(2) 0.8670(2) 0.0275(6) Uani 1 1 d . . . . .
H8 H 0.822268 0.973661 0.847643 0.033 Uiso 1 1 calc R . . . .
N9 N 0.7699(3) 0.9331(2) 0.9468(2) 0.0276(6) Uani 1 1 d . . . . .
C33 C 0.6711(3) 0.9678(3) 0.8223(3) 0.0280(7) Uani 1 1 d . . . . .
C34 C 0.6059(3) 0.9425(3) 0.8738(3) 0.0276(7) Uani 1 1 d . . . . .
C35 C 0.6718(3) 0.9211(3) 0.9507(3) 0.0262(7) Uani 1 1 d . . . . .
C36 C 0.6484(3) 0.8859(3) 1.0277(3) 0.0263(7) Uani 1 1 d . . . . .
C37 C 0.5400(3) 0.8120(3) 1.0015(3) 0.0346(8) Uani 1 1 d . . . . .
H37 H 0.478666 0.787984 0.935394 0.042 Uiso 1 1 calc R . . . .
C38 C 0.5224(4) 0.7743(3) 1.0716(3) 0.0421(10) Uani 1 1 d . . . . .
H38 H 0.448937 0.723010 1.052866 0.050 Uiso 1 1 calc R . . . .
C39 C 0.6097(4) 0.8097(3) 1.1688(3) 0.0433(10) Uani 1 1 d . . . . .
H39 H 0.596306 0.783346 1.216599 0.052 Uiso 1 1 calc R . . . .
C40 C 0.7164(4) 0.8836(3) 1.1960(3) 0.0420(10) Uani 1 1 d . . . . .
H40 H 0.776486 0.908605 1.263071 0.050 Uiso 1 1 calc R . . . .
C41 C 0.7366(3) 0.9218(3) 1.1261(3) 0.0338(8) Uani 1 1 d . . . . .
H41 H 0.810498 0.972342 1.145209 0.041 Uiso 1 1 calc R . . . .
C42 C 0.3784(3) 0.8367(3) 0.7344(3) 0.0287(7) Uani 1 1 d . . . . .
C43 C 0.3945(3) 0.7484(3) 0.7029(3) 0.0383(9) Uani 1 1 d . . . . .
H43 H 0.462379 0.747833 0.743644 0.046 Uiso 1 1 calc R . . . .
C44 C 0.3124(4) 0.6609(3) 0.6126(3) 0.0460(11) Uani 1 1 d . . . . .
H44 H 0.323200 0.599920 0.591809 0.055 Uiso 1 1 calc R . . . .
C45 C 0.2145(4) 0.6624(3) 0.5527(3) 0.0420(10) Uani 1 1 d . . . . .
C46 C 0.1982(3) 0.7501(4) 0.5831(3) 0.0410(10) Uani 1 1 d . . . . .
H46 H 0.130670 0.750638 0.541488 0.049 Uiso 1 1 calc R . . . .
C47 C 0.2793(3) 0.8376(3) 0.6741(3) 0.0356(9) Uani 1 1 d . . . . .
H47 H 0.267434 0.897871 0.695184 0.043 Uiso 1 1 calc R . . . .
C48 C 0.1289(4) 0.5699(4) 0.4525(4) 0.0589(14) Uani 1 1 d . . . . .
S1 S 1.00526(8) 0.89811(7) 0.56008(7) 0.0296(2) Uani 1 1 d . . . . .
F1 F 0.5173(3) 0.5353(3) 0.1474(3) 0.1016(14) Uani 1 1 d . . . . .
F2 F 0.6347(3) 0.5082(3) 0.0913(2) 0.0863(11) Uani 1 1 d . U . . .
F3 F 0.5889(3) 0.4387(2) 0.1848(2) 0.0712(9) Uani 1 1 d . . . . .
N1 N 1.0279(4) 0.7712(3) 0.7061(3) 0.0422(9) Uani 1 1 d . . . . .
N2 N 0.9706(3) 0.8807(2) 0.8025(2) 0.0284(6) Uani 1 1 d . . . . .
H2 H 0.978594 0.858083 0.851408 0.034 Uiso 1 1 calc R . . . .
N3 N 0.9349(2) 0.9560(2) 0.7992(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.9915(3) 0.8460(3) 0.7218(3) 0.0290(7) Uani 1 1 d . . . . .
C2 C 0.9698(3) 0.9009(3) 0.6622(3) 0.0264(7) Uani 1 1 d . . . . .
C3 C 0.9337(3) 0.9681(3) 0.7137(3) 0.0256(7) Uani 1 1 d . . . . .
C4 C 0.8955(3) 1.0423(3) 0.6876(3) 0.0263(7) Uani 1 1 d . . . . .
C5 C 0.8288(3) 1.0194(3) 0.5847(3) 0.0322(8) Uani 1 1 d . . . . .
H5A H 0.810959 0.956719 0.529753 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7883(3) 1.0891(3) 0.5629(3) 0.0385(9) Uani 1 1 d . . . . .
H6 H 0.741487 1.072749 0.492995 0.046 Uiso 1 1 calc R . . . .
C7 C 0.8156(4) 1.1812(3) 0.6417(4) 0.0422(10) Uani 1 1 d . . . . .
H7 H 0.788802 1.228723 0.625847 0.051 Uiso 1 1 calc R . . . .
C8 C 0.8817(4) 1.2046(3) 0.7436(3) 0.0392(9) Uani 1 1 d . . . . .
H8A H 0.899392 1.267660 0.797920 0.047 Uiso 1 1 calc R . . . .
C9 C 0.9225(3) 1.1363(3) 0.7671(3) 0.0310(8) Uani 1 1 d . . . . .
H9 H 0.968915 1.153311 0.837338 0.037 Uiso 1 1 calc R . . . .
C10 C 0.8867(3) 0.7884(3) 0.4487(3) 0.0278(7) Uani 1 1 d . . . . .
C11 C 0.8972(3) 0.7608(3) 0.3576(3) 0.0404(10) Uani 1 1 d . . . . .
H11 H 0.965489 0.800268 0.356790 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8095(4) 0.6764(3) 0.2678(3) 0.0436(10) Uani 1 1 d . . . . .
H12 H 0.817306 0.658067 0.205400 0.052 Uiso 1 1 calc R . . . .
C13 C 0.7109(3) 0.6189(3) 0.2690(3) 0.0364(9) Uani 1 1 d . . . . .
C14 C 0.6995(4) 0.6462(4) 0.3593(3) 0.0507(12) Uani 1 1 d . . . . .
H14 H 0.630914 0.606515 0.359678 0.061 Uiso 1 1 calc R . . . .
C15 C 0.7872(4) 0.7313(3) 0.4500(3) 0.0437(10) Uani 1 1 d . . . . .
H15 H 0.779018 0.749932 0.512234 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6141(4) 0.5269(4) 0.1733(3) 0.0503(12) Uani 1 1 d . . . . .
H4A H 0.709(4) 0.619(4) 1.005(3) 0.035(11) Uiso 1 1 d . . . . .
H1A H 1.045(4) 0.752(4) 0.756(4) 0.043(13) Uiso 1 1 d . . . . .
H7A H 0.577(4) 0.980(4) 0.707(4) 0.044(13) Uiso 1 1 d . . . . .
H1B H 1.035(4) 0.751(4) 0.659(4) 0.040(14) Uiso 1 1 d . . . . .
H7B H 0.694(5) 1.004(4) 0.717(4) 0.055(16) Uiso 1 1 d . . . . .
H4B H 0.701(5) 0.720(5) 1.025(5) 0.073(18) Uiso 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
Cl1 C49 1.740(6) . ?
Cl1A C49A 1.71(2) . ?
Cl2 C49 1.700(7) . ?
Cl2A C49A 1.94(4) . ?
Cl3 C49 1.733(6) . ?
Cl3A C49A 1.720(19) . ?
C49 H49 1.0000 . ?
C49A H49A 1.0000 . ?
S2 C18 1.737(3) . ?
S2 C26 1.773(4) . ?
F4 C32 1.323(6) . ?
F5 C32 1.330(6) . ?
F6 C32 1.311(5) . ?
N4 C17 1.360(5) . ?
N4 H4A 0.86(5) . ?
N4 H4B 0.88(6) . ?
N5 H5 0.8800 . ?
N5 N6 1.372(4) . ?
N5 C17 1.339(4) . ?
N6 C19 1.339(4) . ?
C17 C18 1.397(5) . ?
C18 C19 1.413(5) . ?
C19 C20 1.471(5) . ?
C20 C21 1.389(5) . ?
C20 C25 1.405(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.376(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(5) . ?
C26 C31 1.375(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(6) . ?
C29 C30 1.367(6) . ?
C29 C32 1.490(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.390(5) . ?
C31 H31 0.9500 . ?
S3 C34 1.743(4) . ?
S3 C42 1.778(4) . ?
F7 C48 1.313(6) . ?
F8 C48 1.331(6) . ?
F9 C48 1.328(7) . ?
N7 C33 1.360(5) . ?
N7 H7A 0.86(5) . ?
N7 H7B 0.85(6) . ?
N8 H8 0.8800 . ?
N8 N9 1.372(4) . ?
N8 C33 1.342(5) . ?
N9 C35 1.338(5) . ?
C33 C34 1.396(5) . ?
C34 C35 1.410(5) . ?
C35 C36 1.480(5) . ?
C36 C37 1.399(5) . ?
C36 C41 1.396(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(6) . ?
C38 H38 0.9500 . ?
C38 C39 1.379(6) . ?
C39 H39 0.9500 . ?
C39 C40 1.377(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.387(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.382(5) . ?
C42 C47 1.391(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.382(6) . ?
C44 H44 0.9500 . ?
C44 C45 1.381(6) . ?
C45 C46 1.374(6) . ?
C45 C48 1.491(6) . ?
C46 H46 0.9500 . ?
C46 C47 1.383(6) . ?
C47 H47 0.9500 . ?
S1 C2 1.745(3) . ?
S1 C10 1.780(4) . ?
F1 C16 1.331(6) . ?
F2 C16 1.323(5) . ?
F3 C16 1.325(6) . ?
N1 C1 1.357(5) . ?
N1 H1A 0.87(5) . ?
N1 H1B 0.73(5) . ?
N2 H2 0.8800 . ?
N2 N3 1.372(4) . ?
N2 C1 1.336(5) . ?
N3 C3 1.341(4) . ?
C1 C2 1.399(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.463(5) . ?
C4 C5 1.396(5) . ?
C4 C9 1.401(5) . ?
C5 H5A 0.9500 . ?
C5 C6 1.395(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(6) . ?
C8 H8A 0.9500 . ?
C8 C9 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 C15 1.382(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(6) . ?
C13 C14 1.375(6) . ?
C13 C16 1.495(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(6) . ?
C15 H15 0.9500 . ?

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
Cl1 C49 H49 104.9 . . ?
Cl2 C49 Cl1 113.2(4) . . ?
Cl2 C49 Cl3 115.3(4) . . ?
Cl2 C49 H49 104.9 . . ?
Cl3 C49 Cl1 112.4(4) . . ?
Cl3 C49 H49 104.9 . . ?
Cl1A C49A Cl2A 92.6(18) . . ?
Cl1A C49A Cl3A 105.8(14) . . ?
Cl1A C49A H49A 118.5 . . ?
Cl2A C49A H49A 118.5 . . ?
Cl3A C49A Cl2A 98(2) . . ?
Cl3A C49A H49A 118.5 . . ?
C18 S2 C26 104.27(16) . . ?
C17 N4 H4A 113(3) . . ?
C17 N4 H4B 126(4) . . ?
H4A N4 H4B 119(5) . . ?
N6 N5 H5 124.5 . . ?
C17 N5 H5 124.5 . . ?
C17 N5 N6 111.0(3) . . ?
C19 N6 N5 106.3(3) . . ?
N4 C17 C18 129.0(3) . . ?
N5 C17 N4 123.3(3) . . ?
N5 C17 C18 107.6(3) . . ?
C17 C18 S2 124.4(3) . . ?
C17 C18 C19 105.0(3) . . ?
C19 C18 S2 129.9(3) . . ?
N6 C19 C18 110.0(3) . . ?
N6 C19 C20 118.9(3) . . ?
C18 C19 C20 131.1(3) . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 C25 118.4(3) . . ?
C25 C20 C19 120.1(3) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C27 C26 S2 123.2(3) . . ?
C31 C26 S2 117.4(3) . . ?
C31 C26 C27 119.4(3) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C32 118.6(4) . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 C32 121.3(4) . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.6(3) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
F4 C32 F5 103.0(4) . . ?
F4 C32 C29 112.4(4) . . ?
F5 C32 C29 113.4(4) . . ?
F6 C32 F4 107.0(4) . . ?
F6 C32 F5 106.4(4) . . ?
F6 C32 C29 113.8(4) . . ?
C34 S3 C42 102.98(17) . . ?
C33 N7 H7A 116(3) . . ?
C33 N7 H7B 116(4) . . ?
H7A N7 H7B 122(5) . . ?
N9 N8 H8 124.5 . . ?
C33 N8 H8 124.5 . . ?
C33 N8 N9 110.9(3) . . ?
C35 N9 N8 106.1(3) . . ?
N7 C33 C34 128.7(4) . . ?
N8 C33 N7 123.5(4) . . ?
N8 C33 C34 107.7(3) . . ?
C33 C34 S3 124.4(3) . . ?
C33 C34 C35 104.7(3) . . ?
C35 C34 S3 130.6(3) . . ?
N9 C35 C34 110.5(3) . . ?
N9 C35 C36 118.1(3) . . ?
C34 C35 C36 131.4(3) . . ?
C37 C36 C35 120.9(3) . . ?
C41 C36 C35 120.0(3) . . ?
C41 C36 C37 119.0(4) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.8(4) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 H38 119.5 . . ?
C37 C38 C39 121.0(4) . . ?
C39 C38 H38 119.5 . . ?
C38 C39 H39 120.2 . . ?
C40 C39 C38 119.7(4) . . ?
C40 C39 H39 120.2 . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.4(4) . . ?
C41 C40 H40 119.8 . . ?
C36 C41 H41 120.0 . . ?
C40 C41 C36 120.1(4) . . ?
C40 C41 H41 120.0 . . ?
C43 C42 S3 123.2(3) . . ?
C43 C42 C47 119.6(3) . . ?
C47 C42 S3 117.2(3) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.4(4) . . ?
C44 C43 H43 119.8 . . ?
C43 C44 H44 120.2 . . ?
C45 C44 C43 119.7(4) . . ?
C45 C44 H44 120.2 . . ?
C44 C45 C48 119.5(4) . . ?
C46 C45 C44 120.2(4) . . ?
C46 C45 C48 120.2(4) . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.4(4) . . ?
C47 C46 H46 119.8 . . ?
C42 C47 H47 120.2 . . ?
C46 C47 C42 119.6(4) . . ?
C46 C47 H47 120.2 . . ?
F7 C48 F8 107.8(5) . . ?
F7 C48 F9 105.8(5) . . ?
F7 C48 C45 112.6(4) . . ?
F8 C48 C45 112.7(4) . . ?
F9 C48 F8 104.3(5) . . ?
F9 C48 C45 113.0(5) . . ?
C2 S1 C10 104.58(17) . . ?
C1 N1 H1A 116(3) . . ?
C1 N1 H1B 120(4) . . ?
H1A N1 H1B 124(5) . . ?
N3 N2 H2 124.5 . . ?
C1 N2 H2 124.5 . . ?
C1 N2 N3 111.0(3) . . ?
C3 N3 N2 106.3(3) . . ?
N1 C1 C2 129.2(3) . . ?
N2 C1 N1 123.3(4) . . ?
N2 C1 C2 107.6(3) . . ?
C1 C2 S1 124.7(3) . . ?
C1 C2 C3 105.1(3) . . ?
C3 C2 S1 129.3(3) . . ?
N3 C3 C2 110.0(3) . . ?
N3 C3 C4 118.8(3) . . ?
C2 C3 C4 131.2(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 C9 119.1(3) . . ?
C9 C4 C3 119.9(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8A 119.9 . . ?
C7 C8 C9 120.3(4) . . ?
C9 C8 H8A 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 S1 116.9(3) . . ?
C11 C10 C15 119.8(3) . . ?
C15 C10 S1 123.3(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 C16 121.3(4) . . ?
C14 C13 C16 118.8(4) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 119.2(4) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
F1 C16 C13 113.0(4) . . ?
F2 C16 F1 108.2(4) . . ?
F2 C16 F3 104.9(4) . . ?
F2 C16 C13 113.4(4) . . ?
F3 C16 F1 104.1(4) . . ?
F3 C16 C13 112.5(4) . . ?

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
N5 H5 N9 0.88 1.98 2.826(4) 161.5 . yes
N8 H8 N3 0.88 1.98 2.829(4) 162.0 . yes
C43 H43 Cl2 0.95 2.91 3.717(5) 143.9 2_666 yes
N2 H2 N6 0.88 1.96 2.814(4) 164.1 . yes
C15 H15 Cl3 0.95 2.96 3.803(5) 148.0 2_666 yes

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
S2 C18 C19 N6 -170.0(3) . . . . ?
S2 C18 C19 C20 11.6(6) . . . . ?
S2 C26 C27 C28 179.8(3) . . . . ?
S2 C26 C31 C30 179.6(3) . . . . ?
N4 C17 C18 S2 -7.7(6) . . . . ?
N4 C17 C18 C19 -179.2(4) . . . . ?
N5 N6 C19 C18 -0.7(4) . . . . ?
N5 N6 C19 C20 177.9(3) . . . . ?
N5 C17 C18 S2 170.9(2) . . . . ?
N5 C17 C18 C19 -0.6(4) . . . . ?
N6 N5 C17 N4 178.9(3) . . . . ?
N6 N5 C17 C18 0.2(4) . . . . ?
N6 C19 C20 C21 -142.3(3) . . . . ?
N6 C19 C20 C25 34.3(5) . . . . ?
C17 N5 N6 C19 0.3(4) . . . . ?
C17 C18 C19 N6 0.8(4) . . . . ?
C17 C18 C19 C20 -177.6(3) . . . . ?
C18 S2 C26 C27 5.4(4) . . . . ?
C18 S2 C26 C31 -175.2(3) . . . . ?
C18 C19 C20 C21 36.0(5) . . . . ?
C18 C19 C20 C25 -147.4(4) . . . . ?
C19 C20 C21 C22 176.5(3) . . . . ?
C19 C20 C25 C24 -176.2(3) . . . . ?
C20 C21 C22 C23 -0.8(6) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
C22 C23 C24 C25 -1.4(6) . . . . ?
C23 C24 C25 C20 0.3(6) . . . . ?
C25 C20 C21 C22 -0.3(5) . . . . ?
C26 S2 C18 C17 90.0(3) . . . . ?
C26 S2 C18 C19 -100.8(3) . . . . ?
C26 C27 C28 C29 0.3(7) . . . . ?
C27 C26 C31 C30 -0.9(6) . . . . ?
C27 C28 C29 C30 -0.4(7) . . . . ?
C27 C28 C29 C32 179.2(4) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C28 C29 C32 F4 -63.3(6) . . . . ?
C28 C29 C32 F5 53.1(6) . . . . ?
C28 C29 C32 F6 174.8(5) . . . . ?
C29 C30 C31 C26 0.7(6) . . . . ?
C30 C29 C32 F4 116.4(5) . . . . ?
C30 C29 C32 F5 -127.2(5) . . . . ?
C30 C29 C32 F6 -5.5(7) . . . . ?
C31 C26 C27 C28 0.4(6) . . . . ?
C32 C29 C30 C31 -179.7(4) . . . . ?
S3 C34 C35 N9 -173.2(3) . . . . ?
S3 C34 C35 C36 9.2(6) . . . . ?
S3 C42 C43 C44 178.9(4) . . . . ?
S3 C42 C47 C46 -179.7(3) . . . . ?
N7 C33 C34 S3 -4.4(6) . . . . ?
N7 C33 C34 C35 -178.5(4) . . . . ?
N8 N9 C35 C34 -0.5(4) . . . . ?
N8 N9 C35 C36 177.4(3) . . . . ?
N8 C33 C34 S3 174.0(3) . . . . ?
N8 C33 C34 C35 -0.1(4) . . . . ?
N9 N8 C33 N7 178.3(3) . . . . ?
N9 N8 C33 C34 -0.3(4) . . . . ?
N9 C35 C36 C37 -138.6(4) . . . . ?
N9 C35 C36 C41 37.6(5) . . . . ?
C33 N8 N9 C35 0.5(4) . . . . ?
C33 C34 C35 N9 0.4(4) . . . . ?
C33 C34 C35 C36 -177.2(3) . . . . ?
C34 S3 C42 C43 23.5(4) . . . . ?
C34 S3 C42 C47 -156.9(3) . . . . ?
C34 C35 C36 C37 38.8(6) . . . . ?
C34 C35 C36 C41 -145.0(4) . . . . ?
C35 C36 C37 C38 174.9(4) . . . . ?
C35 C36 C41 C40 -175.8(4) . . . . ?
C36 C37 C38 C39 1.3(6) . . . . ?
C37 C36 C41 C40 0.5(6) . . . . ?
C37 C38 C39 C40 -0.4(7) . . . . ?
C38 C39 C40 C41 -0.5(7) . . . . ?
C39 C40 C41 C36 0.5(6) . . . . ?
C41 C36 C37 C38 -1.4(6) . . . . ?
C42 S3 C34 C33 78.8(3) . . . . ?
C42 S3 C34 C35 -108.7(4) . . . . ?
C42 C43 C44 C45 1.0(7) . . . . ?
C43 C42 C47 C46 -0.1(6) . . . . ?
C43 C44 C45 C46 -0.7(7) . . . . ?
C43 C44 C45 C48 176.8(5) . . . . ?
C44 C45 C46 C47 -0.1(7) . . . . ?
C44 C45 C48 F7 -79.6(7) . . . . ?
C44 C45 C48 F8 158.2(5) . . . . ?
C44 C45 C48 F9 40.3(7) . . . . ?
C45 C46 C47 C42 0.5(6) . . . . ?
C46 C45 C48 F7 98.0(6) . . . . ?
C46 C45 C48 F8 -24.3(7) . . . . ?
C46 C45 C48 F9 -142.1(5) . . . . ?
C47 C42 C43 C44 -0.6(6) . . . . ?
C48 C45 C46 C47 -177.6(4) . . . . ?
S1 C2 C3 N3 -169.1(3) . . . . ?
S1 C2 C3 C4 12.4(6) . . . . ?
S1 C10 C11 C12 179.6(4) . . . . ?
S1 C10 C15 C14 -179.5(4) . . . . ?
N1 C1 C2 S1 -9.8(6) . . . . ?
N1 C1 C2 C3 179.7(4) . . . . ?
N2 N3 C3 C2 -0.5(4) . . . . ?
N2 N3 C3 C4 178.3(3) . . . . ?
N2 C1 C2 S1 169.7(3) . . . . ?
N2 C1 C2 C3 -0.7(4) . . . . ?
N3 N2 C1 N1 -180.0(4) . . . . ?
N3 N2 C1 C2 0.4(4) . . . . ?
N3 C3 C4 C5 -140.8(3) . . . . ?
N3 C3 C4 C9 36.9(5) . . . . ?
C1 N2 N3 C3 0.1(4) . . . . ?
C1 C2 C3 N3 0.8(4) . . . . ?
C1 C2 C3 C4 -177.8(3) . . . . ?
C2 S1 C10 C11 -173.2(3) . . . . ?
C2 S1 C10 C15 6.7(4) . . . . ?
C2 C3 C4 C5 37.7(6) . . . . ?
C2 C3 C4 C9 -144.6(4) . . . . ?
C3 C4 C5 C6 176.4(3) . . . . ?
C3 C4 C9 C8 -176.6(3) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
C5 C4 C9 C8 1.1(5) . . . . ?
C5 C6 C7 C8 -1.2(6) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C7 C8 C9 C4 -0.9(6) . . . . ?
C9 C4 C5 C6 -1.3(5) . . . . ?
C10 S1 C2 C1 87.3(3) . . . . ?
C10 S1 C2 C3 -104.6(3) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C10 C15 C14 0.4(7) . . . . ?
C11 C12 C13 C14 0.6(7) . . . . ?
C11 C12 C13 C16 -180.0(5) . . . . ?
C12 C13 C14 C15 -0.4(8) . . . . ?
C12 C13 C16 F1 -123.1(5) . . . . ?
C12 C13 C16 F2 0.4(7) . . . . ?
C12 C13 C16 F3 119.3(5) . . . . ?
C13 C14 C15 C10 -0.1(8) . . . . ?
C14 C13 C16 F1 56.3(6) . . . . ?
C14 C13 C16 F2 179.9(5) . . . . ?
C14 C13 C16 F3 -61.2(6) . . . . ?
C15 C10 C11 C12 -0.2(7) . . . . ?
C16 C13 C14 C15 -179.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
