# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_cl-dtphz
_database_code_depnum_ccdc_archive 'CCDC 1576235'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-05-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H6 Cl2 N2 S2'
_chemical_formula_sum            'C16 H6 Cl2 N2 S2'
_chemical_formula_weight         361.25
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9687(7)
_cell_length_b                   18.077(3)
_cell_length_c                   15.442(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.142(2)
_cell_angle_gamma                90
_cell_volume                     1386.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7278
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0772 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Slow evaporation of solvent chloroform'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.670
_diffrn_reflns_theta_min         1.735
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3615
_reflns_number_total             4257
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.052
_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)+(0.0410P)²+0.5810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C7(H7), C2(H2), C1(H1), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2 Cl -0.22206(7) 0.98830(2) 0.20166(2) 0.01456(9) Uani 1 1 d . . . . .
S2 S 1.24175(7) 0.60806(2) 0.18755(2) 0.01237(9) Uani 1 1 d . . . . .
S1 S 1.21999(7) 0.59291(2) 0.41511(2) 0.01383(9) Uani 1 1 d . . . . .
Cl1 Cl -0.22719(7) 0.98022(2) 0.40518(2) 0.01616(9) Uani 1 1 d . . . . .
N1 N 0.5048(2) 0.78479(7) 0.39444(8) 0.0113(2) Uani 1 1 d . . . . .
N2 N 0.5189(2) 0.79615(7) 0.21089(8) 0.0110(2) Uani 1 1 d . . . . .
C16 C 0.1571(3) 0.87642(8) 0.39416(10) 0.0126(3) Uani 1 1 d . . . . .
H16 H 0.1516 0.8733 0.4555 0.015 Uiso 1 1 calc R . . . .
C12 C 0.3464(3) 0.83675(8) 0.25691(9) 0.0101(3) Uani 1 1 d . . . . .
C3 C 0.8539(3) 0.69336(8) 0.39387(9) 0.0110(3) Uani 1 1 d . . . . .
C13 C 0.1680(3) 0.88637(8) 0.21244(9) 0.0118(3) Uani 1 1 d . . . . .
H13 H 0.1698 0.8900 0.1511 0.014 Uiso 1 1 calc R . . . .
C4 C 1.0285(3) 0.64973(8) 0.34760(9) 0.0106(3) Uani 1 1 d . . . . .
C10 C 0.6805(3) 0.74993(8) 0.25561(9) 0.0098(3) Uani 1 1 d . . . . .
C9 C 0.6735(3) 0.74422(8) 0.34904(9) 0.0098(3) Uani 1 1 d . . . . .
C11 C 0.3392(3) 0.83123(8) 0.34899(9) 0.0105(3) Uani 1 1 d . . . . .
C6 C 0.8685(3) 0.70483(8) 0.21009(9) 0.0100(3) Uani 1 1 d . . . . .
C5 C 1.0374(3) 0.65587(8) 0.25566(9) 0.0101(3) Uani 1 1 d . . . . .
C15 C -0.0096(3) 0.92417(8) 0.34981(10) 0.0117(3) Uani 1 1 d . . . . .
C14 C -0.0055(3) 0.92883(8) 0.25712(9) 0.0111(3) Uani 1 1 d . . . . .
C7 C 0.9079(3) 0.70241(8) 0.11897(9) 0.0124(3) Uani 1 1 d . . . . .
H7 H 0.8098 0.7317 0.0777 0.015 Uiso 1 1 calc R . . . .
C2 C 0.8811(3) 0.68048(8) 0.48510(9) 0.0137(3) Uani 1 1 d . . . . .
H2 H 0.7792 0.7056 0.5268 0.016 Uiso 1 1 calc R . . . .
C1 C 1.0693(3) 0.62817(9) 0.50528(10) 0.0158(3) Uani 1 1 d . . . . .
H1 H 1.1135 0.6126 0.5628 0.019 Uiso 1 1 calc R . . . .
C8 C 1.1023(3) 0.65320(8) 0.09825(9) 0.0138(3) Uani 1 1 d . . . . .
H8 H 1.1557 0.6446 0.0407 0.017 Uiso 1 1 calc R . . . .


_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
Cl2 C14 1.7257(15) . ?
S2 C5 1.7215(14) . ?
S2 C8 1.7252(15) . ?
S1 C4 1.7240(15) . ?
S1 C1 1.7271(16) . ?
Cl1 C15 1.7308(15) . ?
N1 C9 1.3327(18) . ?
N1 C11 1.3528(18) . ?
N2 C12 1.3506(18) . ?
N2 C10 1.3335(18) . ?
C16 C11 1.421(2) . ?
C16 C15 1.363(2) . ?
C12 C13 1.420(2) . ?
C12 C11 1.427(2) . ?
C3 C4 1.390(2) . ?
C3 C9 1.443(2) . ?
C3 C2 1.429(2) . ?
C13 C14 1.361(2) . ?
C4 C5 1.426(2) . ?
C10 C9 1.4482(19) . ?
C10 C6 1.4421(19) . ?
C6 C5 1.392(2) . ?
C6 C7 1.4286(19) . ?
C15 C14 1.435(2) . ?
C7 C8 1.360(2) . ?
C2 C1 1.358(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
C5 S2 C8 91.29(7) . . ?
C4 S1 C1 91.24(7) . . ?
C9 N1 C11 116.79(12) . . ?
C10 N2 C12 116.74(12) . . ?
C15 C16 C11 120.24(13) . . ?
N2 C12 C13 119.07(13) . . ?
N2 C12 C11 121.73(13) . . ?
C13 C12 C11 119.19(13) . . ?
C4 C3 C9 120.25(13) . . ?
C4 C3 C2 112.12(13) . . ?
C2 C3 C9 127.64(13) . . ?
C14 C13 C12 120.45(13) . . ?
C3 C4 S1 111.60(11) . . ?
C3 C4 C5 120.70(13) . . ?
C5 C4 S1 127.68(11) . . ?
N2 C10 C9 121.59(13) . . ?
N2 C10 C6 119.36(12) . . ?
C6 C10 C9 119.04(12) . . ?
N1 C9 C3 119.35(12) . . ?
N1 C9 C10 121.60(13) . . ?
C3 C9 C10 119.05(12) . . ?
N1 C11 C16 119.21(13) . . ?
N1 C11 C12 121.54(13) . . ?
C16 C11 C12 119.25(13) . . ?
C5 C6 C10 120.14(13) . . ?
C5 C6 C7 112.08(13) . . ?
C7 C6 C10 127.77(13) . . ?
C4 C5 S2 127.58(11) . . ?
C6 C5 S2 111.62(10) . . ?
C6 C5 C4 120.79(13) . . ?
C16 C15 Cl1 120.11(11) . . ?
C16 C15 C14 120.50(13) . . ?
C14 C15 Cl1 119.39(11) . . ?
C13 C14 Cl2 119.65(11) . . ?
C13 C14 C15 120.36(13) . . ?
C15 C14 Cl2 120.00(11) . . ?
C8 C7 C6 112.12(13) . . ?
C1 C2 C3 112.23(13) . . ?
C2 C1 S1 112.80(11) . . ?
C7 C8 S2 112.88(11) . . ?

_shelx_SHELXL_version_number     2015/1
_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_all
_database_code_depnum_ccdc_archive 'CCDC 1576244'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 F2 N2 S2'
_chemical_formula_weight         328.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   26.697(18)
_cell_length_b                   4.815(3)
_cell_length_c                   20.821(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.905(14)
_cell_angle_gamma                90
_cell_volume                     2586(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    4926
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.39

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.431
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'twinabs 2008/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            3758
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3758
_reflns_number_gt                2488
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+4.7654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3758
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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 0.25153(3) 0.57783(15) 0.42684(3) 0.03207(18) Uani 1 1 d . . . . .
S2 S 0.35583(3) 0.48423(15) 0.56915(3) 0.03449(19) Uani 1 1 d . . . . .
F1 F 0.48664(7) -0.9068(4) 0.31986(8) 0.0458(5) Uani 1 1 d . . . . .
F2 F 0.41083(7) -0.8161(4) 0.21196(8) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.33967(8) -0.1193(4) 0.32036(10) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.42100(8) -0.2132(4) 0.43634(10) 0.0264(5) Uani 1 1 d . . . . .
C5 C 0.37720(9) -0.3097(5) 0.32178(12) 0.0239(5) Uani 1 1 d . . . . .
C6 C 0.41768(9) -0.3569(5) 0.38032(12) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.45553(10) -0.5621(6) 0.37938(13) 0.0304(6) Uani 1 1 d . . . . .
C8 C 0.30248(9) 0.2178(5) 0.37831(11) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.45221(10) -0.7068(6) 0.32310(14) 0.0311(6) Uani 1 1 d . . . . .
C10 C 0.41188(10) -0.6596(6) 0.26540(12) 0.0302(6) Uani 1 1 d . . . . .
C11 C 0.34226(9) 0.0185(5) 0.37629(11) 0.0228(5) Uani 1 1 d . . . . .
C12 C 0.38385(9) -0.0274(5) 0.43502(11) 0.0231(5) Uani 1 1 d . . . . .
C13 C 0.34564(10) 0.3180(5) 0.49392(11) 0.0254(5) Uani 1 1 d . . . . .
C14 C 0.37514(10) -0.4634(6) 0.26359(13) 0.0286(6) Uani 1 1 d . . . . .
C15 C 0.30400(9) 0.3598(5) 0.43619(12) 0.0239(5) Uani 1 1 d . . . . .
C16 C 0.38504(10) 0.1328(5) 0.49364(12) 0.0265(5) Uani 1 1 d . . . . .
C17 C 0.25835(9) 0.2904(6) 0.32572(13) 0.0263(5) Uani 1 1 d . . . . .
C18 C 0.42358(12) 0.1290(6) 0.55532(13) 0.0354(7) Uani 1 1 d . . . . .
C19 C 0.22847(10) 0.4806(6) 0.34546(13) 0.0320(6) Uani 1 1 d . . . . .
C20 C 0.41289(11) 0.3046(7) 0.59937(14) 0.0387(7) Uani 1 1 d . . . . .
H1 H 0.3470(11) -0.440(6) 0.2229(15) 0.036(8) Uiso 1 1 d . . . . .
H2 H 0.4816(13) -0.606(7) 0.4191(16) 0.048(9) Uiso 1 1 d . . . . .
H3 H 0.4521(14) 0.025(7) 0.5625(17) 0.052(10) Uiso 1 1 d . . . . .
H4 H 0.4320(13) 0.339(7) 0.6465(17) 0.051(9) Uiso 1 1 d . . . . .
H5 H 0.2517(10) 0.218(6) 0.2823(13) 0.025(7) Uiso 1 1 d . . . . .
H6 H 0.1963(12) 0.560(6) 0.3215(15) 0.037(8) 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
S1 C19 1.713(3) . ?
S1 C15 1.721(3) . ?
S2 C13 1.717(3) . ?
S2 C20 1.724(3) . ?
F1 C9 1.345(3) . ?
F2 C10 1.338(3) . ?
N1 C11 1.327(3) . ?
N1 C5 1.353(3) . ?
N2 C12 1.331(3) . ?
N2 C6 1.339(3) . ?
C5 C14 1.409(4) . ?
C5 C6 1.424(3) . ?
C6 C7 1.417(4) . ?
C7 C9 1.346(4) . ?
C8 C15 1.377(3) . ?
C8 C17 1.430(3) . ?
C8 C11 1.440(3) . ?
C9 C10 1.410(4) . ?
C10 C14 1.355(4) . ?
C11 C12 1.442(3) . ?
C12 C16 1.437(4) . ?
C13 C16 1.380(4) . ?
C13 C15 1.426(3) . ?
C16 C18 1.424(3) . ?
C17 C19 1.346(4) . ?
C18 C20 1.331(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 S1 C15 91.16(13) . . ?
C13 S2 C20 90.97(14) . . ?
C11 N1 C5 116.7(2) . . ?
C12 N2 C6 116.6(2) . . ?
N1 C5 C14 118.2(2) . . ?
N1 C5 C6 121.4(2) . . ?
C14 C5 C6 120.4(2) . . ?
N2 C6 C7 119.0(2) . . ?
N2 C6 C5 121.9(2) . . ?
C7 C6 C5 119.1(2) . . ?
C9 C7 C6 119.0(2) . . ?
C15 C8 C17 112.4(2) . . ?
C15 C8 C11 120.0(2) . . ?
C17 C8 C11 127.5(2) . . ?
F1 C9 C7 121.4(2) . . ?
F1 C9 C10 117.0(2) . . ?
C7 C9 C10 121.5(2) . . ?
F2 C10 C14 120.6(2) . . ?
F2 C10 C9 117.7(2) . . ?
C14 C10 C9 121.7(2) . . ?
N1 C11 C8 119.1(2) . . ?
N1 C11 C12 121.5(2) . . ?
C8 C11 C12 119.4(2) . . ?
N2 C12 C16 119.3(2) . . ?
N2 C12 C11 121.9(2) . . ?
C16 C12 C11 118.8(2) . . ?
C16 C13 C15 121.1(2) . . ?
C16 C13 S2 111.27(18) . . ?
C15 C13 S2 127.5(2) . . ?
C10 C14 C5 118.3(2) . . ?
C8 C15 C13 120.6(2) . . ?
C8 C15 S1 111.34(18) . . ?
C13 C15 S1 128.1(2) . . ?
C13 C16 C18 112.3(2) . . ?
C13 C16 C12 120.0(2) . . ?
C18 C16 C12 127.7(2) . . ?
C19 C17 C8 111.6(2) . . ?
C20 C18 C16 112.3(3) . . ?
C17 C19 S1 113.4(2) . . ?
C18 C20 S2 113.1(2) . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'obtained during attempt to cocrystallize with TCNQ from dichloromethane solution'
####################################################################### 
# 
# 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_006a
_database_code_depnum_ccdc_archive 'CCDC 1576241'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        "Dithieno[3,2-a:2',3'-c]phenazine "
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 N2 S2'
_chemical_formula_weight         292.36

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3173(12)
_cell_length_b                   10.8742(16)
_cell_length_c                   14.978(2)
_cell_angle_alpha                99.580(2)
_cell_angle_beta                 102.642(2)
_cell_angle_gamma                101.257(2)
_cell_volume                     1265.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    6754
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      32.15

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.409
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            15435
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.957
_diffrn_reflns_theta_max         32.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             8105
_reflns_number_gt                6740
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0582P)²+0.1855P] 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         8105
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
S1A S 0.43281(5) 0.19344(3) -0.08213(2) 0.03103(9) Uani 1 1 d . . . . .
S2A S 0.56980(4) 0.26461(3) 0.16246(2) 0.03026(8) Uani 1 1 d . . . . .
N1A N 0.03379(14) -0.19042(10) -0.05195(7) 0.0245(2) Uani 1 1 d . . . . .
N2A N 0.14445(13) -0.13416(10) 0.14733(7) 0.0240(2) Uani 1 1 d . . . . .
C1A C 0.29384(19) 0.08547(14) -0.17816(10) 0.0324(3) Uani 1 1 d . . . . .
H1A H 0.2877 0.0930 -0.2404 0.039 Uiso 1 1 calc R U . . .
C2A C 0.19384(17) -0.01190(13) -0.15445(9) 0.0279(3) Uani 1 1 d . . . . .
H2A H 0.1108 -0.0790 -0.1981 0.034 Uiso 1 1 calc R U . . .
C3A C 0.23003(16) -0.00009(11) -0.05527(8) 0.0231(2) Uani 1 1 d . . . . .
C4A C 0.35753(16) 0.10775(11) -0.00720(9) 0.0237(2) Uani 1 1 d . . . . .
C5A C 0.41361(15) 0.13641(11) 0.09251(9) 0.0239(2) Uani 1 1 d . . . . .
C6A C 0.34234(15) 0.05698(11) 0.14435(9) 0.0233(2) Uani 1 1 d . . . . .
C7A C 0.41990(17) 0.10230(13) 0.24261(9) 0.0290(3) Uani 1 1 d . . . . .
H7A H 0.3890 0.0605 0.2886 0.035 Uiso 1 1 calc R U . . .
C8A C 0.54317(18) 0.21245(13) 0.26202(10) 0.0317(3) Uani 1 1 d . . . . .
H8A H 0.6069 0.2555 0.3230 0.038 Uiso 1 1 calc R U . . .
C9A C 0.15275(15) -0.08607(11) -0.00437(8) 0.0216(2) Uani 1 1 d . . . . .
C10A C 0.20955(15) -0.05713(11) 0.09710(8) 0.0214(2) Uani 1 1 d . . . . .
C11A C -0.03279(16) -0.26927(12) -0.00115(9) 0.0243(2) Uani 1 1 d . . . . .
C12A C 0.02275(15) -0.24074(11) 0.09869(9) 0.0230(2) Uani 1 1 d . . . . .
C13A C -0.05019(17) -0.32777(13) 0.14812(10) 0.0289(3) Uani 1 1 d . . . . .
H13A H -0.0155 -0.3101 0.2140 0.035 Uiso 1 1 calc R U . . .
C14A C -0.17040(19) -0.43699(14) 0.10038(11) 0.0335(3) Uani 1 1 d . . . . .
H14A H -0.2164 -0.4949 0.1336 0.040 Uiso 1 1 calc R U . . .
C15A C -0.2265(2) -0.46386(14) 0.00137(11) 0.0369(3) Uani 1 1 d . . . . .
H15A H -0.3110 -0.5386 -0.0305 0.044 Uiso 1 1 calc R U . . .
C16A C -0.15939(19) -0.38253(13) -0.04835(10) 0.0326(3) Uani 1 1 d . . . . .
H16A H -0.1973 -0.4017 -0.1141 0.039 Uiso 1 1 calc R U . . .
S1B S 0.42263(4) 0.79102(3) 0.33170(2) 0.03155(9) Uani 1 1 d . . . . .
S2B S 0.71654(5) 0.97133(4) 0.54095(3) 0.03796(10) Uani 1 1 d . . . . .
N1B N 0.83160(13) 0.51745(10) 0.31369(7) 0.0249(2) Uani 1 1 d . . . . .
N2B N 1.07734(15) 0.67124(12) 0.47687(8) 0.0319(2) Uani 1 1 d . . . . .
C1B C 0.38564(18) 0.66033(14) 0.24111(10) 0.0326(3) Uani 1 1 d . . . . .
H1B H 0.2879 0.6348 0.1906 0.039 Uiso 1 1 calc R U . . .
C2B C 0.51284(17) 0.59804(13) 0.25044(9) 0.0285(3) Uani 1 1 d . . . . .
H2B H 0.5130 0.5247 0.2072 0.034 Uiso 1 1 calc R U . . .
C3B C 0.64580(15) 0.65645(12) 0.33311(8) 0.0232(2) Uani 1 1 d . . . . .
C4B C 0.61381(16) 0.76331(12) 0.38487(9) 0.0252(2) Uani 1 1 d . . . . .
C5B C 0.73418(18) 0.83675(12) 0.46873(9) 0.0272(2) Uani 1 1 d . . . . .
C6B C 0.88725(18) 0.80601(13) 0.50061(9) 0.0285(3) Uani 1 1 d . . . . .
C7B C 0.9898(2) 0.89266(15) 0.58561(10) 0.0367(3) Uani 1 1 d . . . . .
H7B H 1.0975 0.8862 0.6174 0.044 Uiso 1 1 calc R U . . .
C8B C 0.9130(2) 0.98504(15) 0.61481(10) 0.0415(4) Uani 1 1 d . . . . .
H8B H 0.9616 1.0498 0.6696 0.050 Uiso 1 1 calc R U . . .
C9B C 0.80361(15) 0.61982(11) 0.36428(8) 0.0227(2) Uani 1 1 d . . . . .
C10B C 0.92759(16) 0.69705(12) 0.44784(9) 0.0259(2) Uani 1 1 d . . . . .
C11B C 0.98475(16) 0.49146(12) 0.34226(9) 0.0261(2) Uani 1 1 d . . . . .
C12B C 1.10807(17) 0.56929(14) 0.42361(9) 0.0301(3) Uani 1 1 d . . . . .
C13B C 1.2679(2) 0.53989(18) 0.44861(12) 0.0465(4) Uani 1 1 d . . . . .
H13B H 1.3512 0.5905 0.5019 0.056 Uiso 1 1 calc R U . . .
C14B C 1.3015(2) 0.4385(2) 0.39568(13) 0.0501(4) Uani 1 1 d . . . . .
H14B H 1.4079 0.4195 0.4133 0.060 Uiso 1 1 calc R U . . .
C15B C 1.1794(2) 0.36112(16) 0.31468(12) 0.0399(3) Uani 1 1 d . . . . .
H15B H 1.2055 0.2917 0.2789 0.048 Uiso 1 1 calc R U . . .
C16B C 1.02493(18) 0.38660(13) 0.28840(11) 0.0320(3) Uani 1 1 d . . . . .
H16B H 0.9442 0.3349 0.2345 0.038 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
S1A C4A 1.7168(13) . ?
S1A C1A 1.7216(15) . ?
S2A C5A 1.7145(12) . ?
S2A C8A 1.7237(15) . ?
N1A C9A 1.3260(15) . ?
N1A C11A 1.3553(16) . ?
N2A C10A 1.3311(16) . ?
N2A C12A 1.3553(15) . ?
C1A C2A 1.3600(19) . ?
C1A H1A 0.9400 . ?
C2A C3A 1.4281(17) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.3847(16) . ?
C3A C9A 1.4442(17) . ?
C4A C5A 1.4243(17) . ?
C5A C6A 1.3874(17) . ?
C6A C7A 1.4296(18) . ?
C6A C10A 1.4459(16) . ?
C7A C8A 1.3582(19) . ?
C7A H7A 0.9400 . ?
C8A H8A 0.9400 . ?
C9A C10A 1.4494(17) . ?
C11A C16A 1.4154(17) . ?
C11A C12A 1.4258(17) . ?
C12A C13A 1.4203(17) . ?
C13A C14A 1.3646(19) . ?
C13A H13A 0.9400 . ?
C14A C15A 1.415(2) . ?
C14A H14A 0.9400 . ?
C15A C16A 1.363(2) . ?
C15A H15A 0.9400 . ?
C16A H16A 0.9400 . ?
S1B C1B 1.7205(14) . ?
S1B C4B 1.7222(13) . ?
S2B C5B 1.7203(13) . ?
S2B C8B 1.7245(17) . ?
N1B C9B 1.3286(16) . ?
N1B C11B 1.3520(16) . ?
N2B C10B 1.3264(18) . ?
N2B C12B 1.3550(19) . ?
C1B C2B 1.3581(19) . ?
C1B H1B 0.9400 . ?
C2B C3B 1.4227(17) . ?
C2B H2B 0.9400 . ?
C3B C4B 1.3904(17) . ?
C3B C9B 1.4481(17) . ?
C4B C5B 1.4217(18) . ?
C5B C6B 1.383(2) . ?
C6B C7B 1.4309(18) . ?
C6B C10B 1.4494(19) . ?
C7B C8B 1.355(2) . ?
C7B H7B 0.9400 . ?
C8B H8B 0.9400 . ?
C9B C10B 1.4430(17) . ?
C11B C16B 1.4224(19) . ?
C11B C12B 1.4226(18) . ?
C12B C13B 1.414(2) . ?
C13B C14B 1.359(3) . ?
C13B H13B 0.9400 . ?
C14B C15B 1.414(3) . ?
C14B H14B 0.9400 . ?
C15B C16B 1.355(2) . ?
C15B H15B 0.9400 . ?
C16B H16B 0.9400 . ?

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
C4A S1A C1A 91.30(6) . . ?
C5A S2A C8A 91.31(6) . . ?
C9A N1A C11A 116.82(11) . . ?
C10A N2A C12A 116.56(11) . . ?
C2A C1A S1A 112.82(10) . . ?
C2A C1A H1A 123.6 . . ?
S1A C1A H1A 123.6 . . ?
C1A C2A C3A 111.93(12) . . ?
C1A C2A H2A 124.0 . . ?
C3A C2A H2A 124.0 . . ?
C4A C3A C2A 112.17(11) . . ?
C4A C3A C9A 120.04(11) . . ?
C2A C3A C9A 127.78(11) . . ?
C3A C4A C5A 120.97(11) . . ?
C3A C4A S1A 111.77(9) . . ?
C5A C4A S1A 127.25(10) . . ?
C6A C5A C4A 120.99(11) . . ?
C6A C5A S2A 112.10(9) . . ?
C4A C5A S2A 126.91(10) . . ?
C5A C6A C7A 111.58(11) . . ?
C5A C6A C10A 119.95(11) . . ?
C7A C6A C10A 128.45(12) . . ?
C8A C7A C6A 112.45(12) . . ?
C8A C7A H7A 123.8 . . ?
C6A C7A H7A 123.8 . . ?
C7A C8A S2A 112.55(10) . . ?
C7A C8A H8A 123.7 . . ?
S2A C8A H8A 123.7 . . ?
N1A C9A C3A 119.01(11) . . ?
N1A C9A C10A 121.88(11) . . ?
C3A C9A C10A 119.10(10) . . ?
N2A C10A C6A 119.51(11) . . ?
N2A C10A C9A 121.54(11) . . ?
C6A C10A C9A 118.94(11) . . ?
N1A C11A C16A 119.22(12) . . ?
N1A C11A C12A 121.34(11) . . ?
C16A C11A C12A 119.43(12) . . ?
N2A C12A C13A 119.32(11) . . ?
N2A C12A C11A 121.85(11) . . ?
C13A C12A C11A 118.82(11) . . ?
C14A C13A C12A 120.26(13) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C13A C14A C15A 120.61(13) . . ?
C13A C14A H14A 119.7 . . ?
C15A C14A H14A 119.7 . . ?
C16A C15A C14A 120.72(13) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A H15A 119.6 . . ?
C15A C16A C11A 120.14(13) . . ?
C15A C16A H16A 119.9 . . ?
C11A C16A H16A 119.9 . . ?
C1B S1B C4B 91.40(6) . . ?
C5B S2B C8B 91.26(7) . . ?
C9B N1B C11B 116.80(11) . . ?
C10B N2B C12B 116.52(11) . . ?
C2B C1B S1B 112.76(10) . . ?
C2B C1B H1B 123.6 . . ?
S1B C1B H1B 123.6 . . ?
C1B C2B C3B 112.27(12) . . ?
C1B C2B H2B 123.9 . . ?
C3B C2B H2B 123.9 . . ?
C4B C3B C2B 112.25(11) . . ?
C4B C3B C9B 119.87(11) . . ?
C2B C3B C9B 127.84(11) . . ?
C3B C4B C5B 120.63(12) . . ?
C3B C4B S1B 111.33(9) . . ?
C5B C4B S1B 128.02(10) . . ?
C6B C5B C4B 121.44(12) . . ?
C6B C5B S2B 111.57(10) . . ?
C4B C5B S2B 126.97(11) . . ?
C5B C6B C7B 112.33(13) . . ?
C5B C6B C10B 119.83(11) . . ?
C7B C6B C10B 127.84(13) . . ?
C8B C7B C6B 111.93(14) . . ?
C8B C7B H7B 124.0 . . ?
C6B C7B H7B 124.0 . . ?
C7B C8B S2B 112.91(11) . . ?
C7B C8B H8B 123.5 . . ?
S2B C8B H8B 123.5 . . ?
N1B C9B C10B 121.87(11) . . ?
N1B C9B C3B 118.86(11) . . ?
C10B C9B C3B 119.25(11) . . ?
N2B C10B C9B 121.62(12) . . ?
N2B C10B C6B 119.47(12) . . ?
C9B C10B C6B 118.91(12) . . ?
N1B C11B C16B 119.32(12) . . ?
N1B C11B C12B 121.19(12) . . ?
C16B C11B C12B 119.46(12) . . ?
N2B C12B C13B 119.29(13) . . ?
N2B C12B C11B 121.95(12) . . ?
C13B C12B C11B 118.75(13) . . ?
C14B C13B C12B 120.12(15) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 121.32(15) . . ?
C13B C14B H14B 119.3 . . ?
C15B C14B H14B 119.3 . . ?
C16B C15B C14B 120.22(15) . . ?
C16B C15B H15B 119.9 . . ?
C14B C15B H15B 119.9 . . ?
C15B C16B C11B 120.12(14) . . ?
C15B C16B H16B 119.9 . . ?
C11B C16B H16B 119.9 . . ?

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
C4A S1A C1A C2A 0.07(12) . . . . ?
S1A C1A C2A C3A -0.18(16) . . . . ?
C1A C2A C3A C4A 0.24(17) . . . . ?
C1A C2A C3A C9A -178.62(13) . . . . ?
C2A C3A C4A C5A -179.46(12) . . . . ?
C9A C3A C4A C5A -0.51(18) . . . . ?
C2A C3A C4A S1A -0.18(14) . . . . ?
C9A C3A C4A S1A 178.77(9) . . . . ?
C1A S1A C4A C3A 0.07(10) . . . . ?
C1A S1A C4A C5A 179.29(12) . . . . ?
C3A C4A C5A C6A 0.12(19) . . . . ?
S1A C4A C5A C6A -179.04(10) . . . . ?
C3A C4A C5A S2A 179.61(10) . . . . ?
S1A C4A C5A S2A 0.45(18) . . . . ?
C8A S2A C5A C6A 0.61(11) . . . . ?
C8A S2A C5A C4A -178.92(12) . . . . ?
C4A C5A C6A C7A 178.76(11) . . . . ?
S2A C5A C6A C7A -0.80(14) . . . . ?
C4A C5A C6A C10A 0.26(19) . . . . ?
S2A C5A C6A C10A -179.30(9) . . . . ?
C5A C6A C7A C8A 0.61(17) . . . . ?
C10A C6A C7A C8A 178.95(13) . . . . ?
C6A C7A C8A S2A -0.15(16) . . . . ?
C5A S2A C8A C7A -0.26(12) . . . . ?
C11A N1A C9A C3A 178.88(11) . . . . ?
C11A N1A C9A C10A 0.03(18) . . . . ?
C4A C3A C9A N1A -178.36(11) . . . . ?
C2A C3A C9A N1A 0.4(2) . . . . ?
C4A C3A C9A C10A 0.51(18) . . . . ?
C2A C3A C9A C10A 179.29(12) . . . . ?
C12A N2A C10A C6A -178.77(11) . . . . ?
C12A N2A C10A C9A 0.04(17) . . . . ?
C5A C6A C10A N2A 178.59(11) . . . . ?
C7A C6A C10A N2A 0.4(2) . . . . ?
C5A C6A C10A C9A -0.24(18) . . . . ?
C7A C6A C10A C9A -178.46(12) . . . . ?
N1A C9A C10A N2A -0.11(19) . . . . ?
C3A C9A C10A N2A -178.95(11) . . . . ?
N1A C9A C10A C6A 178.71(11) . . . . ?
C3A C9A C10A C6A -0.14(17) . . . . ?
C9A N1A C11A C16A -179.56(12) . . . . ?
C9A N1A C11A C12A 0.10(18) . . . . ?
C10A N2A C12A C13A 179.16(11) . . . . ?
C10A N2A C12A C11A 0.10(18) . . . . ?
N1A C11A C12A N2A -0.17(19) . . . . ?
C16A C11A C12A N2A 179.49(12) . . . . ?
N1A C11A C12A C13A -179.24(12) . . . . ?
C16A C11A C12A C13A 0.42(19) . . . . ?
N2A C12A C13A C14A -178.65(13) . . . . ?
C11A C12A C13A C14A 0.4(2) . . . . ?
C12A C13A C14A C15A -1.3(2) . . . . ?
C13A C14A C15A C16A 1.2(2) . . . . ?
C14A C15A C16A C11A -0.4(2) . . . . ?
N1A C11A C16A C15A 179.21(14) . . . . ?
C12A C11A C16A C15A -0.5(2) . . . . ?
C4B S1B C1B C2B -0.08(12) . . . . ?
S1B C1B C2B C3B -0.02(17) . . . . ?
C1B C2B C3B C4B 0.14(18) . . . . ?
C1B C2B C3B C9B -177.55(13) . . . . ?
C2B C3B C4B C5B -178.36(12) . . . . ?
C9B C3B C4B C5B -0.46(19) . . . . ?
C2B C3B C4B S1B -0.19(14) . . . . ?
C9B C3B C4B S1B 177.70(9) . . . . ?
C1B S1B C4B C3B 0.15(11) . . . . ?
C1B S1B C4B C5B 178.15(13) . . . . ?
C3B C4B C5B C6B 1.1(2) . . . . ?
S1B C4B C5B C6B -176.71(10) . . . . ?
C3B C4B C5B S2B 179.69(10) . . . . ?
S1B C4B C5B S2B 1.86(19) . . . . ?
C8B S2B C5B C6B -0.82(11) . . . . ?
C8B S2B C5B C4B -179.52(13) . . . . ?
C4B C5B C6B C7B 179.54(13) . . . . ?
S2B C5B C6B C7B 0.76(15) . . . . ?
C4B C5B C6B C10B 0.2(2) . . . . ?
S2B C5B C6B C10B -178.56(10) . . . . ?
C5B C6B C7B C8B -0.25(19) . . . . ?
C10B C6B C7B C8B 179.01(14) . . . . ?
C6B C7B C8B S2B -0.38(18) . . . . ?
C5B S2B C8B C7B 0.69(13) . . . . ?
C11B N1B C9B C10B -2.34(18) . . . . ?
C11B N1B C9B C3B 176.07(11) . . . . ?
C4B C3B C9B N1B -179.93(11) . . . . ?
C2B C3B C9B N1B -2.4(2) . . . . ?
C4B C3B C9B C10B -1.48(18) . . . . ?
C2B C3B C9B C10B 176.06(13) . . . . ?
C12B N2B C10B C9B 0.47(19) . . . . ?
C12B N2B C10B C6B -179.02(12) . . . . ?
N1B C9B C10B N2B 1.7(2) . . . . ?
C3B C9B C10B N2B -176.74(12) . . . . ?
N1B C9B C10B C6B -178.84(11) . . . . ?
C3B C9B C10B C6B 2.75(18) . . . . ?
C5B C6B C10B N2B 177.36(12) . . . . ?
C7B C6B C10B N2B -1.8(2) . . . . ?
C5B C6B C10B C9B -2.15(19) . . . . ?
C7B C6B C10B C9B 178.65(13) . . . . ?
C9B N1B C11B C16B -177.11(12) . . . . ?
C9B N1B C11B C12B 1.04(18) . . . . ?
C10B N2B C12B C13B 177.42(14) . . . . ?
C10B N2B C12B C11B -1.8(2) . . . . ?
N1B C11B C12B N2B 1.1(2) . . . . ?
C16B C11B C12B N2B 179.22(13) . . . . ?
N1B C11B C12B C13B -178.12(14) . . . . ?
C16B C11B C12B C13B 0.0(2) . . . . ?
N2B C12B C13B C14B -179.55(17) . . . . ?
C11B C12B C13B C14B -0.3(3) . . . . ?
C12B C13B C14B C15B 0.5(3) . . . . ?
C13B C14B C15B C16B -0.3(3) . . . . ?
C14B C15B C16B C11B 0.0(2) . . . . ?
N1B C11B C16B C15B 178.33(14) . . . . ?
C12B C11B C16B C15B 0.1(2) . . . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'physical vapor transport  during attempts to cocrystallize with TCNQ'
####################################################################### 
# 
# 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_TMS-Cl-DTPhz
_database_code_depnum_ccdc_archive 'CCDC 1576240'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H22 Cl2 N2 S2 Si2'
_chemical_formula_sum            'C22 H22 Cl2 N2 S2 Si2'
_chemical_formula_weight         505.61
_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'
Si Si 0.0817 0.0704 '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'
Cl Cl 0.1484 0.1585 '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                   7.3053(19)
_cell_length_b                   10.911(3)
_cell_length_c                   15.153(4)
_cell_angle_alpha                88.935(4)
_cell_angle_beta                 85.183(4)
_cell_angle_gamma                82.192(4)
_cell_volume                     1192.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5685
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      29.07
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.8736.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method 'Slow evaporation of chloroform'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16833
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.884
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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                4419
_reflns_number_total             5707
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.035
_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)+(0.0471P)²+0.9679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C2(H2), C7(H7), C13(H13)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C17(H17A,H17B,H17C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2 Cl 0.33234(9) -0.03779(6) 1.32271(4) 0.02032(15) Uani 1 1 d . . . . .
Cl1 Cl 0.49117(8) -0.30142(6) 1.24494(4) 0.01931(15) Uani 1 1 d . . . . .
S1 S 0.18673(8) -0.01741(5) 0.63439(4) 0.01423(14) Uani 1 1 d . . . . .
S2 S 0.02085(8) 0.28153(5) 0.72253(4) 0.01303(14) Uani 1 1 d . . . . .
Si2 Si -0.09478(9) 0.54021(6) 0.82277(4) 0.01464(16) Uani 1 1 d . . . . .
Si1 Si 0.37295(9) -0.28015(6) 0.56888(4) 0.01452(16) Uani 1 1 d . . . . .
N2 N 0.1840(3) 0.10027(18) 1.01280(13) 0.0127(4) Uani 1 1 d . . . . .
C15 C 0.4021(3) -0.1846(2) 1.17541(16) 0.0144(5) Uani 1 1 d . . . . .
N1 N 0.3312(3) -0.13634(18) 0.94132(13) 0.0134(4) Uani 1 1 d . . . . .
C16 C 0.4019(3) -0.2067(2) 1.08688(16) 0.0148(5) Uani 1 1 d . . . . .
H16 H 0.4509 -0.2859 1.0639 0.018 Uiso 1 1 calc R . . . .
C10 C 0.1863(3) 0.0762(2) 0.92678(15) 0.0116(5) Uani 1 1 d . . . . .
C5 C 0.1100(3) 0.1506(2) 0.77770(15) 0.0117(5) Uani 1 1 d . . . . .
C9 C 0.2599(3) -0.0440(2) 0.89063(15) 0.0118(5) Uani 1 1 d . . . . .
C3 C 0.2562(3) -0.0640(2) 0.79661(15) 0.0116(5) Uani 1 1 d . . . . .
C6 C 0.1135(3) 0.1734(2) 0.86759(15) 0.0111(5) Uani 1 1 d . . . . .
C11 C 0.3291(3) -0.1120(2) 1.02916(15) 0.0128(5) Uani 1 1 d . . . . .
C14 C 0.3294(3) -0.0655(2) 1.21085(15) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.3239(3) -0.1735(2) 0.74739(15) 0.0132(5) Uani 1 1 d . . . . .
H2 H 0.3827 -0.2465 0.7738 0.016 Uiso 1 1 calc R . . . .
C12 C 0.2555(3) 0.0065(2) 1.06488(15) 0.0119(5) Uani 1 1 d . . . . .
C22 C 0.0909(4) 0.6089(2) 0.87385(18) 0.0229(6) Uani 1 1 d . . . . .
H22A H 0.1140 0.5679 0.9307 0.034 Uiso 1 1 calc GR . . . .
H22B H 0.0515 0.6974 0.8835 0.034 Uiso 1 1 calc GR . . . .
H22C H 0.2049 0.5975 0.8342 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.4149(4) -0.4362(2) 0.62251(18) 0.0227(6) Uani 1 1 d . . . . .
H19A H 0.4803 -0.4301 0.6758 0.034 Uiso 1 1 calc GR . . . .
H19B H 0.4905 -0.4941 0.5810 0.034 Uiso 1 1 calc GR . . . .
H19C H 0.2960 -0.4661 0.6388 0.034 Uiso 1 1 calc GR . . . .
C7 C 0.0457(3) 0.2986(2) 0.88939(15) 0.0129(5) Uani 1 1 d . . . . .
H7 H 0.0398 0.3300 0.9478 0.015 Uiso 1 1 calc R . . . .
C13 C 0.2577(3) 0.0273(2) 1.15672(16) 0.0144(5) Uani 1 1 d . . . . .
H13 H 0.2092 0.1060 1.1808 0.017 Uiso 1 1 calc R . . . .
C8 C -0.0105(3) 0.3697(2) 0.81862(16) 0.0132(5) Uani 1 1 d . . . . .
C4 C 0.1790(3) 0.0304(2) 0.74244(15) 0.0121(5) Uani 1 1 d . . . . .
C1 C 0.2974(3) -0.1649(2) 0.65927(16) 0.0139(5) Uani 1 1 d . . . . .
C18 C 0.1854(4) -0.2747(3) 0.49206(17) 0.0235(6) Uani 1 1 d . . . . .
H18A H 0.2291 -0.3278 0.4410 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.1523 -0.1895 0.4717 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.0764 -0.3042 0.5231 0.035 Uiso 1 1 calc GR . . . .
C20 C -0.1228(4) 0.6028(3) 0.70860(18) 0.0271(6) Uani 1 1 d . . . . .
H20A H -0.1914 0.6865 0.7120 0.041 Uiso 1 1 calc GR . . . .
H20B H -0.1913 0.5492 0.6765 0.041 Uiso 1 1 calc GR . . . .
H20C H -0.0003 0.6056 0.6774 0.041 Uiso 1 1 calc GR . . . .
C17 C 0.5890(4) -0.2374(3) 0.50890(18) 0.0243(6) Uani 1 1 d . . . . .
H17A H 0.6863 -0.2408 0.5500 0.037 Uiso 1 1 calc GR . . . .
H17B H 0.5645 -0.1534 0.4848 0.037 Uiso 1 1 calc GR . . . .
H17C H 0.6298 -0.2956 0.4604 0.037 Uiso 1 1 calc GR . . . .
C21 C -0.3195(4) 0.5681(3) 0.89279(19) 0.0257(6) Uani 1 1 d . . . . .
H21A H -0.3042 0.5297 0.9512 0.038 Uiso 1 1 calc GR . . . .
H21B H -0.4148 0.5319 0.8642 0.038 Uiso 1 1 calc GR . . . .
H21C H -0.3571 0.6573 0.8997 0.038 Uiso 1 1 calc GR . . . .


_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
Cl2 C14 1.730(2) . ?
Cl1 C15 1.732(2) . ?
S1 C4 1.722(2) . ?
S1 C1 1.750(2) . ?
S2 C5 1.720(2) . ?
S2 C8 1.742(2) . ?
Si2 C22 1.864(3) . ?
Si2 C8 1.879(2) . ?
Si2 C20 1.865(3) . ?
Si2 C21 1.870(3) . ?
Si1 C19 1.871(3) . ?
Si1 C1 1.873(3) . ?
Si1 C18 1.865(3) . ?
Si1 C17 1.865(3) . ?
N2 C10 1.333(3) . ?
N2 C12 1.355(3) . ?
C15 C16 1.368(3) . ?
C15 C14 1.432(4) . ?
N1 C9 1.331(3) . ?
N1 C11 1.361(3) . ?
C16 C11 1.418(3) . ?
C10 C9 1.448(3) . ?
C10 C6 1.450(3) . ?
C5 C6 1.392(3) . ?
C5 C4 1.435(3) . ?
C9 C3 1.448(3) . ?
C3 C2 1.428(3) . ?
C3 C4 1.394(3) . ?
C6 C7 1.424(3) . ?
C11 C12 1.428(3) . ?
C14 C13 1.367(3) . ?
C2 C1 1.365(3) . ?
C12 C13 1.416(3) . ?
C7 C8 1.370(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
C4 S1 C1 92.57(11) . . ?
C5 S2 C8 92.62(11) . . ?
C22 Si2 C8 104.59(11) . . ?
C22 Si2 C20 110.62(13) . . ?
C22 Si2 C21 111.10(13) . . ?
C20 Si2 C8 110.16(12) . . ?
C20 Si2 C21 110.64(13) . . ?
C21 Si2 C8 109.57(12) . . ?
C19 Si1 C1 107.31(11) . . ?
C18 Si1 C19 110.68(13) . . ?
C18 Si1 C1 108.90(12) . . ?
C18 Si1 C17 110.39(13) . . ?
C17 Si1 C19 111.41(13) . . ?
C17 Si1 C1 108.03(12) . . ?
C10 N2 C12 116.6(2) . . ?
C16 C15 Cl1 119.73(19) . . ?
C16 C15 C14 120.4(2) . . ?
C14 C15 Cl1 119.86(18) . . ?
C9 N1 C11 116.3(2) . . ?
C15 C16 C11 120.4(2) . . ?
N2 C10 C9 121.9(2) . . ?
N2 C10 C6 119.1(2) . . ?
C9 C10 C6 119.0(2) . . ?
C6 C5 S2 111.09(17) . . ?
C6 C5 C4 120.3(2) . . ?
C4 C5 S2 128.62(18) . . ?
N1 C9 C10 121.8(2) . . ?
N1 C9 C3 119.2(2) . . ?
C10 C9 C3 118.9(2) . . ?
C2 C3 C9 128.1(2) . . ?
C4 C3 C9 120.3(2) . . ?
C4 C3 C2 111.6(2) . . ?
C5 C6 C10 120.6(2) . . ?
C5 C6 C7 112.1(2) . . ?
C7 C6 C10 127.3(2) . . ?
N1 C11 C16 119.1(2) . . ?
N1 C11 C12 121.8(2) . . ?
C16 C11 C12 119.1(2) . . ?
C15 C14 Cl2 120.12(18) . . ?
C13 C14 Cl2 119.46(19) . . ?
C13 C14 C15 120.4(2) . . ?
C1 C2 C3 114.6(2) . . ?
N2 C12 C11 121.5(2) . . ?
N2 C12 C13 118.9(2) . . ?
C13 C12 C11 119.6(2) . . ?
C8 C7 C6 113.9(2) . . ?
C14 C13 C12 120.2(2) . . ?
S2 C8 Si2 124.61(14) . . ?
C7 C8 S2 110.27(18) . . ?
C7 C8 Si2 125.01(18) . . ?
C5 C4 S1 127.83(18) . . ?
C3 C4 S1 111.31(17) . . ?
C3 C4 C5 120.8(2) . . ?
S1 C1 Si1 120.25(13) . . ?
C2 C1 S1 109.94(18) . . ?
C2 C1 Si1 129.70(19) . . ?

_shelx_SHELXL_version_number     2014/7
_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_diphenyldiamine
_database_code_depnum_ccdc_archive 'CCDC 1576236'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        "Dithieno[3,2-a:2',3'-c]phenazine "
_chemical_formula_moiety         'C16 H8 N2 S2'
_chemical_formula_sum            'C16 H8 N2 S2'
_chemical_formula_weight         292.36
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'-x+, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+'

_cell_length_a                   4.8175(7)
_cell_length_b                   15.993(2)
_cell_length_c                   16.143(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1243.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6950
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'Slow evaporation in dichloromethane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19365
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3354
_reflns_number_total             3622
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.042
_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)+(0.0333P)²+0.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C2(H2), C15(H15), C14(H14), C7(H7), C13(H13), C1(H1), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S2 S 0.14707(12) 0.15387(3) 0.17276(3) 0.01561(13) Uani 1 1 d . . . . .
S1 S 0.27926(12) 0.32666(4) 0.04280(3) 0.01621(13) Uani 1 1 d . . . . .
N2 N 0.8532(4) 0.27694(11) 0.36112(11) 0.0122(4) Uani 1 1 d . . . . .
C3 C 0.6355(5) 0.36175(13) 0.15691(13) 0.0125(4) Uani 1 1 d . . . . .
C12 C 1.0472(5) 0.33521(13) 0.38025(13) 0.0118(4) Uani 1 1 d . . . . .
C4 C 0.4368(5) 0.30281(14) 0.13562(13) 0.0130(4) Uani 1 1 d . . . . .
C11 C 1.1136(4) 0.40176(13) 0.32484(13) 0.0112(4) Uani 1 1 d . . . . .
C9 C 0.7878(5) 0.35416(13) 0.23337(13) 0.0113(4) Uani 1 1 d . . . . .
C16 C 1.3246(5) 0.45977(13) 0.34681(14) 0.0148(4) Uani 1 1 d . . . . .
H16 H 1.3722 0.5037 0.3099 0.018 Uiso 1 1 calc R . . . .
N1 N 0.9813(4) 0.41099(12) 0.25129(12) 0.0120(4) Uani 1 1 d . . . . .
C2 C 0.6568(5) 0.42701(14) 0.09624(13) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.7817 0.4728 0.1003 0.018 Uiso 1 1 calc R . . . .
C6 C 0.5168(5) 0.22523(14) 0.26425(13) 0.0122(4) Uani 1 1 d . . . . .
C15 C 1.4587(5) 0.45248(15) 0.42072(14) 0.0162(5) Uani 1 1 d . . . . .
H15 H 1.5992 0.4915 0.4351 0.019 Uiso 1 1 calc R . . . .
C10 C 0.7246(5) 0.28553(13) 0.28880(12) 0.0112(4) Uani 1 1 d . . . . .
C5 C 0.3796(5) 0.23376(13) 0.18890(13) 0.0128(4) Uani 1 1 d . . . . .
C14 C 1.3898(5) 0.38667(15) 0.47658(14) 0.0164(5) Uani 1 1 d . . . . .
H14 H 1.4841 0.3825 0.5281 0.020 Uiso 1 1 calc R . . . .
C7 C 0.4287(5) 0.15246(14) 0.30835(14) 0.0149(4) Uani 1 1 d . . . . .
H7 H 0.5004 0.1364 0.3608 0.018 Uiso 1 1 calc R . . . .
C13 C 1.1902(5) 0.32958(13) 0.45686(14) 0.0147(4) Uani 1 1 d . . . . .
H13 H 1.1467 0.2859 0.4946 0.018 Uiso 1 1 calc R . . . .
C1 C 0.4782(5) 0.41564(15) 0.03260(14) 0.0171(5) Uani 1 1 d . . . . .
H1 H 0.4639 0.4529 -0.0131 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2309(5) 0.10894(14) 0.26685(14) 0.0164(5) Uani 1 1 d . . . . .
H8 H 0.1476 0.0592 0.2873 0.020 Uiso 1 1 calc R . . . .


_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
S2 C5 1.719(2) . ?
S2 C8 1.728(2) . ?
S1 C4 1.722(2) . ?
S1 C1 1.724(3) . ?
N2 C12 1.355(3) . ?
N2 C10 1.329(3) . ?
C3 C4 1.387(3) . ?
C3 C9 1.441(3) . ?
C3 C2 1.435(3) . ?
C12 C11 1.427(3) . ?
C12 C13 1.419(3) . ?
C4 C5 1.426(3) . ?
C11 C16 1.421(3) . ?
C11 N1 1.356(3) . ?
C9 N1 1.334(3) . ?
C9 C10 1.448(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.362(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.352(3) . ?
C6 C10 1.446(3) . ?
C6 C5 1.391(3) . ?
C6 C7 1.429(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.425(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.364(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.357(3) . ?
C13 H13 0.9500 . ?
C1 H1 0.9500 . ?
C8 H8 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
C5 S2 C8 91.35(11) . . ?
C4 S1 C1 91.20(11) . . ?
C10 N2 C12 116.77(18) . . ?
C4 C3 C9 120.42(19) . . ?
C4 C3 C2 112.0(2) . . ?
C2 C3 C9 127.6(2) . . ?
N2 C12 C11 121.65(19) . . ?
N2 C12 C13 119.3(2) . . ?
C13 C12 C11 119.0(2) . . ?
C3 C4 S1 111.66(17) . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 S1 127.65(18) . . ?
C16 C11 C12 119.4(2) . . ?
N1 C11 C12 121.67(19) . . ?
N1 C11 C16 118.93(19) . . ?
C3 C9 C10 119.09(19) . . ?
N1 C9 C3 118.96(19) . . ?
N1 C9 C10 122.0(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C9 N1 C11 116.38(19) . . ?
C3 C2 H2 124.0 . . ?
C1 C2 C3 112.0(2) . . ?
C1 C2 H2 124.0 . . ?
C5 C6 C10 120.23(19) . . ?
C5 C6 C7 112.0(2) . . ?
C7 C6 C10 127.8(2) . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
N2 C10 C9 121.6(2) . . ?
N2 C10 C6 119.65(19) . . ?
C6 C10 C9 118.79(19) . . ?
C4 C5 S2 127.58(17) . . ?
C6 C5 S2 111.67(16) . . ?
C6 C5 C4 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C6 C7 H7 123.8 . . ?
C8 C7 C6 112.4(2) . . ?
C8 C7 H7 123.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
S1 C1 H1 123.5 . . ?
C2 C1 S1 113.09(18) . . ?
C2 C1 H1 123.5 . . ?
S2 C8 H8 123.7 . . ?
C7 C8 S2 112.62(17) . . ?
C7 C8 H8 123.7 . . ?

_shelx_SHELXL_version_number     2015/1
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1576239'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 F2 N2 S2 Si2'
_chemical_formula_weight         472.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   26.626(4)
_cell_length_b                   6.9557(11)
_cell_length_c                   12.568(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2327.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    8022
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      29.90

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.360
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            25793
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.530
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3666
_reflns_number_gt                2853
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0593P)²+0.4444P] 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         3666
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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 0.18209(2) 0.2500 0.08341(4) 0.03073(14) Uani 1 2 d S T P B .
S2 S 0.12688(2) 0.2500 0.33610(4) 0.04284(18) Uani 1 2 d S T P A .
Si1 Si 0.22770(2) 0.2500 -0.14286(5) 0.03078(16) Uani 1 2 d S T P . .
Si2 Si 0.07124(3) 0.2863(2) 0.55441(6) 0.0353(5) Uani 0.5 1 d . . P A -1
F1 F -0.15488(5) 0.2500 -0.20651(12) 0.0568(5) Uani 1 2 d S T P B .
F2 F -0.19618(5) 0.2500 -0.01516(13) 0.0477(4) Uani 1 2 d S T P . .
N1 N 0.00830(6) 0.2500 -0.05811(13) 0.0255(4) Uani 1 2 d S T P B .
N2 N -0.03599(6) 0.2500 0.14739(13) 0.0272(4) Uani 1 2 d S T P . .
C1 C 0.17142(8) 0.2500 -0.05277(15) 0.0265(4) Uani 1 2 d S T P B .
C2 C 0.12078(7) 0.2500 -0.07247(16) 0.0261(4) Uani 1 2 d S T P . .
H2A H 0.1073 0.2500 -0.1416 0.031 Uiso 1 2 calc R U P B .
C3 C 0.09026(7) 0.2500 0.02089(15) 0.0240(4) Uani 1 2 d S T P B .
C4 C 0.11938(8) 0.2500 0.11233(16) 0.0267(4) Uani 1 2 d S T P . .
C5 C 0.09685(8) 0.2500 0.21538(15) 0.0293(4) Uani 1 2 d S T P A .
C6 C 0.04540(8) 0.2500 0.22690(15) 0.0274(4) Uani 1 2 d S T P . .
C7 C 0.03127(9) 0.2500 0.33649(16) 0.0354(5) Uani 1 2 d S T P A .
H7A H -0.0024 0.2500 0.3591 0.042 Uiso 1 2 calc R U P . .
C8 C 0.07062(9) 0.2500 0.40519(18) 0.0423(6) Uani 1 2 d S T P . .
C9 C 0.03601(7) 0.2500 0.02964(15) 0.0228(4) Uani 1 2 d S T P . .
C10 C 0.01341(7) 0.2500 0.13425(15) 0.0238(4) Uani 1 2 d S T P B .
C11 C -0.04199(8) 0.2500 -0.04473(16) 0.0252(4) Uani 1 2 d S T P . .
C12 C -0.06431(8) 0.2500 0.05834(17) 0.0261(4) Uani 1 2 d S T P B .
C13 C -0.11734(8) 0.2500 0.06819(18) 0.0309(5) Uani 1 2 d S T P . .
H13A H -0.1325 0.2500 0.1357 0.037 Uiso 1 2 calc R U P B .
C14 C -0.14566(8) 0.2500 -0.0206(2) 0.0336(5) Uani 1 2 d S T P B .
C15 C -0.12354(8) 0.2500 -0.12216(19) 0.0359(5) Uani 1 2 d S T P . .
C16 C -0.07358(8) 0.2500 -0.13600(18) 0.0331(5) Uani 1 2 d S T P B .
H16A H -0.0597 0.2500 -0.2048 0.040 Uiso 1 2 calc R U P . .
C17 C 0.28273(13) 0.3113(8) -0.0578(3) 0.067(2) Uani 0.5 1 d . . P B -1
H17A H 0.2777 0.4369 -0.0259 0.101 Uiso 0.5 1 calc R U P B -1
H17B H 0.2863 0.2157 -0.0021 0.101 Uiso 0.5 1 calc R U P B -1
H17C H 0.3129 0.3133 -0.1010 0.101 Uiso 0.5 1 calc R U P B -1
C18 C 0.2346(2) 0.0144(9) -0.2057(5) 0.0563(15) Uani 0.5 1 d . . P B -1
H18A H 0.2388 -0.0831 -0.1512 0.084 Uiso 0.5 1 calc R U P B -1
H18B H 0.2049 -0.0138 -0.2475 0.084 Uiso 0.5 1 calc R U P B -1
H18C H 0.2639 0.0152 -0.2516 0.084 Uiso 0.5 1 calc R U P B -1
C19 C 0.2197(2) 0.4393(9) -0.2451(5) 0.0571(14) Uani 0.5 1 d . . P B -1
H19A H 0.2161 0.5633 -0.2106 0.086 Uiso 0.5 1 calc R U P B -1
H19B H 0.2490 0.4414 -0.2912 0.086 Uiso 0.5 1 calc R U P B -1
H19C H 0.1900 0.4124 -0.2871 0.086 Uiso 0.5 1 calc R U P B -1
C20 C 0.00626(13) 0.275(3) 0.6051(3) 0.051(4) Uani 0.5 1 d . . P A -1
H20A H -0.0086 0.1528 0.5860 0.077 Uiso 0.5 1 calc R U P A -1
H20B H 0.0065 0.2886 0.6820 0.077 Uiso 0.5 1 calc R U P A -1
H20C H -0.0133 0.3788 0.5741 0.077 Uiso 0.5 1 calc R U P A -1
C21 C 0.1095(2) 0.0836(8) 0.6059(4) 0.0654(15) Uani 0.5 1 d . . P A -1
H21A H 0.1434 0.0930 0.5780 0.098 Uiso 0.5 1 calc R U P A -1
H21B H 0.1105 0.0889 0.6830 0.098 Uiso 0.5 1 calc R U P A -1
H21C H 0.0946 -0.0372 0.5836 0.098 Uiso 0.5 1 calc R U P A -1
C22 C 0.0991(2) 0.5202(8) 0.5913(4) 0.0525(11) Uani 0.5 1 d . . P A -1
H22A H 0.1333 0.5269 0.5648 0.079 Uiso 0.5 1 calc R U P A -1
H22B H 0.0795 0.6234 0.5603 0.079 Uiso 0.5 1 calc R U P A -1
H22C H 0.0993 0.5332 0.6681 0.079 Uiso 0.5 1 calc R U P A -1


_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 C4 1.709(2) . ?
S1 C1 1.735(2) . ?
S2 C5 1.715(2) . ?
S2 C8 1.731(2) . ?
Si1 C18 1.828(6) . ?
Si1 C19 1.852(6) . ?
Si1 C17 1.863(4) . ?
Si1 C1 1.878(2) . ?
Si2 C20 1.846(3) . ?
Si2 C22 1.847(5) . ?
Si2 C21 1.856(6) . ?
Si2 C8 1.892(2) . ?
F1 C15 1.349(3) . ?
F2 C14 1.347(2) . ?
N1 C9 1.327(2) . ?
N1 C11 1.350(3) . ?
N2 C10 1.325(2) . ?
N2 C12 1.349(3) . ?
C1 C2 1.371(3) . ?
C2 C3 1.427(3) . ?
C3 C4 1.386(3) . ?
C3 C9 1.449(3) . ?
C4 C5 1.427(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.428(3) . ?
C6 C10 1.443(3) . ?
C7 C8 1.358(3) . ?
C9 C10 1.446(3) . ?
C11 C16 1.422(3) . ?
C11 C12 1.425(3) . ?
C12 C13 1.417(3) . ?
C13 C14 1.347(3) . ?
C14 C15 1.406(3) . ?
C15 C16 1.342(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
C4 S1 C1 92.85(10) . . ?
C5 S2 C8 92.31(11) . . ?
C18 Si1 C19 110.4(3) . . ?
C18 Si1 C17 111.9(2) . . ?
C19 Si1 C17 109.0(2) . . ?
C18 Si1 C1 109.94(19) . . ?
C19 Si1 C1 109.1(2) . . ?
C17 Si1 C1 106.34(13) . . ?
C20 Si2 C22 109.1(7) . . ?
C20 Si2 C21 111.3(7) . . ?
C22 Si2 C21 111.2(3) . . ?
C20 Si2 C8 109.19(18) . . ?
C22 Si2 C8 111.71(18) . . ?
C21 Si2 C8 104.40(18) . . ?
C9 N1 C11 116.62(17) . . ?
C10 N2 C12 116.82(17) . . ?
C2 C1 S1 109.83(14) . . ?
C2 C1 Si1 132.52(15) . . ?
S1 C1 Si1 117.65(12) . . ?
C1 C2 C3 114.30(18) . . ?
C4 C3 C2 111.30(18) . . ?
C4 C3 C9 119.65(17) . . ?
C2 C3 C9 129.06(18) . . ?
C3 C4 C5 121.15(19) . . ?
C3 C4 S1 111.72(15) . . ?
C5 C4 S1 127.13(16) . . ?
C6 C5 C4 120.88(18) . . ?
C6 C5 S2 111.76(14) . . ?
C4 C5 S2 127.36(16) . . ?
C5 C6 C7 111.31(18) . . ?
C5 C6 C10 120.15(17) . . ?
C7 C6 C10 128.54(19) . . ?
C8 C7 C6 114.2(2) . . ?
C7 C8 S2 110.41(17) . . ?
C7 C8 Si2 129.56(17) . . ?
S2 C8 Si2 119.31(14) . . ?
N1 C9 C10 121.62(18) . . ?
N1 C9 C3 119.43(17) . . ?
C10 C9 C3 118.95(17) . . ?
N2 C10 C6 119.03(17) . . ?
N2 C10 C9 121.75(18) . . ?
C6 C10 C9 119.22(17) . . ?
N1 C11 C16 119.09(18) . . ?
N1 C11 C12 121.81(18) . . ?
C16 C11 C12 119.10(19) . . ?
N2 C12 C13 118.97(19) . . ?
N2 C12 C11 121.38(18) . . ?
C13 C12 C11 119.66(19) . . ?
C14 C13 C12 119.1(2) . . ?
C13 C14 F2 121.2(2) . . ?
C13 C14 C15 121.2(2) . . ?
F2 C14 C15 117.7(2) . . ?
C16 C15 F1 120.8(2) . . ?
C16 C15 C14 122.2(2) . . ?
F1 C15 C14 117.0(2) . . ?
C15 C16 C11 118.8(2) . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform '
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1576237'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-05-09
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) 
;
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C16 H6 Cl2 N2 S2'
_chemical_formula_sum            'C16 H6 Cl2 N2 S2'
_chemical_formula_weight         361.25
_chemical_absolute_configuration ?
_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'
S S 0.1246 0.1234 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, -y+, z+1/2'
'-x+, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+'

_cell_length_a                   9.0758(11)
_cell_length_b                   10.1834(13)
_cell_length_c                   29.957(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2768.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100.1
_cell_measurement_theta_max      32.62
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0506 before and 0.0326 after correction. 
The Ratio of minimum to maximum transmission is 0.9018. 
The λ/2 correction factor is 0.0015. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method 
'Slow evaporation in a mixture 1:1 of toluene and dichloromethane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            36797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         2.112
_diffrn_ambient_temperature      100.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                7941
_reflns_number_total             8042
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3388 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.518(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         8042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.113
_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)+(0.0358P)²+1.5064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C16B(H16B), C16A(H16A), C13B(H13B), C13A(H13A), C8A(H8A), C7B(H7B), C7A(H7A), 
 C2A(H2A), C8B(H8B), C2B(H2B), C1A(H1A), C1B(H1B) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2B Cl 0.97492(6) 1.11581(5) 0.55669(2) 0.01527(10) Uani 1 1 d . . . . .
S2B S 0.25947(6) 0.37329(5) 0.60055(2) 0.01349(10) Uani 1 1 d . . . . .
Cl1B Cl 1.04878(6) 1.11702(6) 0.65921(2) 0.01832(11) Uani 1 1 d . . . . .
Cl2A Cl 0.48565(6) 0.13151(5) 0.53062(2) 0.01630(10) Uani 1 1 d . . . . .
Cl1A Cl 0.47118(6) 0.07725(5) 0.63445(2) 0.01784(11) Uani 1 1 d . . . . .
S2A S 1.23167(6) 0.84522(6) 0.57687(2) 0.01574(11) Uani 1 1 d . . . . .
S1B S 0.35033(6) 0.37337(6) 0.71476(2) 0.01583(11) Uani 1 1 d . . . . .
S1A S 1.21058(7) 0.78963(6) 0.69247(2) 0.01883(12) Uani 1 1 d . . . . .
C11A C 0.7673(2) 0.3677(2) 0.62674(7) 0.0118(4) Uani 1 1 d . . . . .
N2B N 0.6207(2) 0.73910(18) 0.58569(6) 0.0111(3) Uani 1 1 d . . . . .
C6A C 1.0368(2) 0.6603(2) 0.57434(7) 0.0124(4) Uani 1 1 d . . . . .
C5B C 0.3822(2) 0.4753(2) 0.62753(7) 0.0117(4) Uani 1 1 d . . . . .
C16B C 0.8547(2) 0.9205(2) 0.66681(7) 0.0125(4) Uani 1 1 d . . . . .
H16B H 0.8762 0.9231 0.6978 0.015 Uiso 1 1 calc R . . . .
N1B N 0.6880(2) 0.74176(18) 0.67856(6) 0.0112(3) Uani 1 1 d . . . . .
C12B C 0.7190(2) 0.8252(2) 0.60307(7) 0.0104(4) Uani 1 1 d . . . . .
C10B C 0.5575(2) 0.6555(2) 0.61414(7) 0.0105(4) Uani 1 1 d . . . . .
C16A C 0.6740(2) 0.2670(2) 0.64282(7) 0.0139(4) Uani 1 1 d . . . . .
H16A H 0.6712 0.2479 0.6739 0.017 Uiso 1 1 calc R . . . .
C15A C 0.5881(2) 0.1972(2) 0.61402(8) 0.0129(4) Uani 1 1 d . . . . .
C5A C 1.1250(2) 0.7302(2) 0.60399(8) 0.0137(4) Uani 1 1 d . . . . .
C12A C 0.7700(2) 0.3961(2) 0.57964(7) 0.0113(4) Uani 1 1 d . . . . .
N1A N 0.8510(2) 0.43749(19) 0.65568(6) 0.0131(3) Uani 1 1 d . . . . .
C15B C 0.9217(2) 1.0060(2) 0.63852(7) 0.0126(4) Uani 1 1 d . . . . .
C10 C 0.9400(2) 0.5586(2) 0.59093(7) 0.0120(4) Uani 1 1 d . . . . .
C3B C 0.5226(2) 0.5626(2) 0.69065(7) 0.0125(4) Uani 1 1 d . . . . .
C4B C 0.4180(2) 0.4758(2) 0.67382(7) 0.0126(4) Uani 1 1 d . . . . .
C11B C 0.7522(2) 0.8270(2) 0.64986(7) 0.0103(4) Uani 1 1 d . . . . .
C13B C 0.7904(2) 0.9165(2) 0.57457(7) 0.0118(4) Uani 1 1 d . . . . .
H13B H 0.7693 0.9167 0.5435 0.014 Uiso 1 1 calc R . . . .
CC9B C 0.5919(2) 0.6565(2) 0.66130(7) 0.0105(4) Uani 1 1 d . . . . .
N2A N 0.8564(2) 0.49159(18) 0.56233(6) 0.0120(3) Uani 1 1 d . . . . .
C6B C 0.4510(2) 0.5612(2) 0.59784(7) 0.0108(4) Uani 1 1 d . . . . .
C4A C 1.1183(2) 0.7062(2) 0.65083(8) 0.0137(4) Uani 1 1 d . . . . .
C13A C 0.6792(2) 0.3217(2) 0.55017(8) 0.0129(4) Uani 1 1 d . . . . .
H13A H 0.6795 0.3395 0.5190 0.016 Uiso 1 1 calc R . . . .
C9 C 0.9364(2) 0.5317(2) 0.63867(7) 0.0128(4) Uani 1 1 d . . . . .
C14B C 0.8899(2) 1.0047(2) 0.59176(7) 0.0113(4) Uani 1 1 d . . . . .
C8A C 1.1594(3) 0.7992(2) 0.52579(8) 0.0158(4) Uani 1 1 d . . . . .
H8A H 1.1875 0.8383 0.4983 0.019 Uiso 1 1 calc R . . . .
C7B C 0.4024(2) 0.5418(2) 0.55279(8) 0.0132(4) Uani 1 1 d . . . . .
H7B H 0.4374 0.5911 0.5281 0.016 Uiso 1 1 calc R . . . .
C3A C 1.0255(2) 0.6104(2) 0.66881(8) 0.0136(4) Uani 1 1 d . . . . .
C7A C 1.0580(2) 0.7013(2) 0.52913(8) 0.0140(4) Uani 1 1 d . . . . .
H7A H 1.0073 0.6645 0.5044 0.017 Uiso 1 1 calc R . . . .
C14A C 0.5915(2) 0.2241(2) 0.56714(7) 0.0124(4) Uani 1 1 d . . . . .
C2A C 1.0283(3) 0.6074(2) 0.71628(8) 0.0190(4) Uani 1 1 d . . . . .
H2A H 0.9713 0.5489 0.7339 0.023 Uiso 1 1 calc R . . . .
C8B C 0.3001(2) 0.4445(2) 0.54959(8) 0.0141(4) Uani 1 1 d . . . . .
H8B H 0.2558 0.4184 0.5223 0.017 Uiso 1 1 calc R . . . .
C2B C 0.5476(3) 0.5440(2) 0.73723(8) 0.0156(4) Uani 1 1 d . . . . .
H2B H 0.6153 0.5942 0.7544 0.019 Uiso 1 1 calc R . . . .
C1A C 1.1225(3) 0.6982(3) 0.73329(8) 0.0208(5) Uani 1 1 d . . . . .
H1A H 1.1384 0.7103 0.7644 0.025 Uiso 1 1 calc R . . . .
C1B C 0.4628(3) 0.4458(2) 0.75416(8) 0.0186(5) Uani 1 1 d . . . . .
H1B H 0.4653 0.4198 0.7846 0.022 Uiso 1 1 calc R . . . .


_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
Cl2B C14B 1.726(2) . ?
S2B C5B 1.724(2) . ?
S2B C8B 1.730(2) . ?
Cl1B C15B 1.730(2) . ?
Cl2A C14A 1.735(2) . ?
Cl1A C15A 1.730(2) . ?
S2A C5A 1.723(2) . ?
S2A C8A 1.729(2) . ?
S1B C4B 1.723(2) . ?
S1B C1B 1.727(3) . ?
S1A C4A 1.726(2) . ?
S1A C1A 1.733(3) . ?
C11A C16A 1.415(3) . ?
C11A C12A 1.440(3) . ?
C11A N1A 1.354(3) . ?
N2B C12B 1.355(3) . ?
N2B C10B 1.334(3) . ?
C6A C5A 1.392(3) . ?
C6A C10 1.446(3) . ?
C6A C7A 1.431(3) . ?
C5B C4B 1.424(3) . ?
C5B C6B 1.395(3) . ?
C16B C15B 1.359(3) . ?
C16B C11B 1.425(3) . ?
N1B C11B 1.354(3) . ?
N1B CC9B 1.335(3) . ?
C12B C11B 1.434(3) . ?
C12B C13B 1.419(3) . ?
C10B CC9B 1.447(3) . ?
C10B C6B 1.448(3) . ?
C16A C15A 1.363(3) . ?
C15A C14A 1.431(3) . ?
C5A C4A 1.426(3) . ?
C12A N2A 1.353(3) . ?
C12A C13A 1.426(3) . ?
N1A C9 1.335(3) . ?
C15B C14B 1.430(3) . ?
C10 N2A 1.332(3) . ?
C10 C9 1.456(3) . ?
C3B C4B 1.392(3) . ?
C3B CC9B 1.444(3) . ?
C3B C2B 1.426(3) . ?
C13B C14B 1.374(3) . ?
C6B C7B 1.434(3) . ?
C4A C3A 1.397(3) . ?
C13A C14A 1.371(3) . ?
C9 C3A 1.453(3) . ?
C8A C7A 1.360(3) . ?
C7B C8B 1.361(3) . ?
C3A C2A 1.423(3) . ?
C2A C1A 1.358(4) . ?
C2B C1B 1.359(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
C5B S2B C8B 91.35(11) . . ?
C5A S2A C8A 91.15(12) . . ?
C4B S1B C1B 90.98(11) . . ?
C4A S1A C1A 91.24(12) . . ?
C16A C11A C12A 119.30(19) . . ?
N1A C11A C16A 119.9(2) . . ?
N1A C11A C12A 120.8(2) . . ?
C10B N2B C12B 116.77(18) . . ?
C5A C6A C10 119.8(2) . . ?
C5A C6A C7A 112.2(2) . . ?
C7A C6A C10 128.1(2) . . ?
C4B C5B S2B 127.31(17) . . ?
C6B C5B S2B 111.60(16) . . ?
C6B C5B C4B 121.1(2) . . ?
C15B C16B C11B 119.9(2) . . ?
CC9B N1B C11B 116.87(18) . . ?
N2B C12B C11B 121.48(19) . . ?
N2B C12B C13B 119.57(19) . . ?
C13B C12B C11B 118.95(19) . . ?
N2B C10B CC9B 121.76(19) . . ?
N2B C10B C6B 119.67(19) . . ?
CC9B C10B C6B 118.57(19) . . ?
C15A C16A C11A 120.3(2) . . ?
C16A C15A Cl1A 119.67(18) . . ?
C16A C15A C14A 120.6(2) . . ?
C14A C15A Cl1A 119.74(17) . . ?
C6A C5A S2A 111.71(17) . . ?
C6A C5A C4A 121.0(2) . . ?
C4A C5A S2A 127.23(18) . . ?
N2A C12A C11A 121.98(19) . . ?
N2A C12A C13A 118.67(19) . . ?
C13A C12A C11A 119.3(2) . . ?
C9 N1A C11A 117.28(19) . . ?
C16B C15B Cl1B 119.59(17) . . ?
C16B C15B C14B 121.0(2) . . ?
C14B C15B Cl1B 119.46(17) . . ?
C6A C10 C9 119.1(2) . . ?
N2A C10 C6A 119.4(2) . . ?
N2A C10 C9 121.5(2) . . ?
C4B C3B CC9B 119.8(2) . . ?
C4B C3B C2B 112.2(2) . . ?
C2B C3B CC9B 127.9(2) . . ?
C5B C4B S1B 127.55(17) . . ?
C3B C4B S1B 111.70(17) . . ?
C3B C4B C5B 120.7(2) . . ?
C16B C11B C12B 119.61(19) . . ?
N1B C11B C16B 118.89(19) . . ?
N1B C11B C12B 121.50(19) . . ?
C14B C13B C12B 120.2(2) . . ?
N1B CC9B C10B 121.61(19) . . ?
N1B CC9B C3B 118.67(19) . . ?
C3B CC9B C10B 119.72(19) . . ?
C10 N2A C12A 116.85(19) . . ?
C5B C6B C10B 120.0(2) . . ?
C5B C6B C7B 112.09(19) . . ?
C7B C6B C10B 127.91(19) . . ?
C5A C4A S1A 127.30(18) . . ?
C3A C4A S1A 110.96(17) . . ?
C3A C4A C5A 121.7(2) . . ?
C14A C13A C12A 119.4(2) . . ?
N1A C9 C10 121.5(2) . . ?
N1A C9 C3A 118.8(2) . . ?
C3A C9 C10 119.6(2) . . ?
C15B C14B Cl2B 119.97(17) . . ?
C13B C14B Cl2B 119.62(17) . . ?
C13B C14B C15B 120.4(2) . . ?
C7A C8A S2A 112.96(18) . . ?
C8B C7B C6B 112.1(2) . . ?
C4A C3A C9 118.8(2) . . ?
C4A C3A C2A 112.9(2) . . ?
C2A C3A C9 128.3(2) . . ?
C8A C7A C6A 112.0(2) . . ?
C15A C14A Cl2A 120.15(17) . . ?
C13A C14A Cl2A 118.80(17) . . ?
C13A C14A C15A 121.0(2) . . ?
C1A C2A C3A 111.8(2) . . ?
C7B C8B S2B 112.85(18) . . ?
C1B C2B C3B 111.9(2) . . ?
C2A C1A S1A 113.04(19) . . ?
C2B C1B S1B 113.20(18) . . ?

_shelx_SHELXL_version_number     2015/1
_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_010c
_database_code_depnum_ccdc_archive 'CCDC 1576242'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 F2 N2 S2'
_chemical_formula_sum            'C16 H6 F2 N2 S2'
_chemical_formula_weight         328.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.175(4)
_cell_length_b                   14.277(4)
_cell_length_c                   16.501(4)
_cell_angle_alpha                112.680(3)
_cell_angle_beta                 95.238(3)
_cell_angle_gamma                115.518(3)
_cell_volume                     2644.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.59

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.422
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            43579
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.674
_diffrn_reflns_theta_max         32.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             17407
_reflns_number_gt                12125
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.054P)²+0.0494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17407
_refine_ls_number_parameters     793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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 0.68402(3) 0.17842(3) 0.35057(3) 0.03313(9) Uani 1 1 d . . . . .
S2 S 0.77305(3) 0.29936(3) 0.59249(3) 0.03253(9) Uani 1 1 d . . . . .
F1 F 1.45097(9) 0.54092(11) 0.38261(8) 0.0588(3) Uani 1 1 d . . . . .
F2 F 1.51759(8) 0.63945(11) 0.56505(9) 0.0654(3) Uani 1 1 d . . . . .
N1 N 1.07903(10) 0.36890(11) 0.37513(9) 0.0300(3) Uani 1 1 d . . . . .
N2 N 1.15134(10) 0.47046(11) 0.57097(9) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.72937(13) 0.16980(14) 0.25595(11) 0.0365(4) Uani 1 1 d . . . . .
H1 H 0.6820 0.1279 0.1951 0.044 Uiso 1 1 calc R U . . .
C2 C 0.83984(13) 0.22947(14) 0.27822(10) 0.0326(3) Uani 1 1 d . . . . .
H2 H 0.8779 0.2336 0.2348 0.039 Uiso 1 1 calc R U . . .
C3 C 0.89242(12) 0.28566(12) 0.37515(10) 0.0271(3) Uani 1 1 d . . . . .
C4 C 1.00850(12) 0.35483(12) 0.42383(10) 0.0264(3) Uani 1 1 d . . . . .
C5 C 1.04501(11) 0.40484(12) 0.52239(10) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.96415(11) 0.38299(12) 0.57037(10) 0.0267(3) Uani 1 1 d . . . . .
C7 C 0.98294(13) 0.42425(13) 0.66733(10) 0.0319(3) Uani 1 1 d . . . . .
H7 H 1.0531 0.4726 0.7114 0.038 Uiso 1 1 calc R U . . .
C8 C 0.88804(13) 0.38560(14) 0.68827(11) 0.0351(3) Uani 1 1 d . . . . .
H8 H 0.8851 0.4038 0.7488 0.042 Uiso 1 1 calc R U . . .
C9 C 0.85314(12) 0.31405(12) 0.52106(10) 0.0266(3) Uani 1 1 d . . . . .
C10 C 0.81714(11) 0.26558(12) 0.42342(10) 0.0262(3) Uani 1 1 d . . . . .
C11 C 1.18640(12) 0.43409(13) 0.42414(11) 0.0299(3) Uani 1 1 d . . . . .
C12 C 1.26524(14) 0.45091(16) 0.37554(12) 0.0380(4) Uani 1 1 d . . . . .
H12 H 1.2427 0.4152 0.3107 0.046 Uiso 1 1 calc R U . . .
C13 C 1.37277(14) 0.51919(16) 0.42462(13) 0.0411(4) Uani 1 1 d . . . . .
C14 C 1.40851(13) 0.57241(16) 0.52209(13) 0.0422(4) Uani 1 1 d . . . . .
C15 C 1.33695(13) 0.55694(15) 0.57045(12) 0.0380(4) Uani 1 1 d . . . . .
H15 H 1.3621 0.5926 0.6352 0.046 Uiso 1 1 calc R U . . .
C16 C 1.22282(12) 0.48596(13) 0.52207(11) 0.0295(3) Uani 1 1 d . . . . .
S3 S 0.71856(3) 0.74801(4) 0.50225(3) 0.04176(11) Uani 1 1 d . . . . .
S4 S 0.89570(4) 0.89051(4) 0.72768(3) 0.04270(11) Uani 1 1 d . . . . .
F3 F 1.37041(10) 0.99474(12) 0.30961(9) 0.0687(4) Uani 1 1 d . . . . .
F4 F 1.50219(9) 1.10089(12) 0.47998(9) 0.0709(4) Uani 1 1 d . . . . .
N3 N 1.05675(10) 0.87789(11) 0.40956(9) 0.0307(3) Uani 1 1 d . . . . .
N4 N 1.19913(11) 0.99033(11) 0.59205(9) 0.0317(3) Uani 1 1 d . . . . .
C17 C 0.71416(14) 0.71517(15) 0.38998(13) 0.0433(4) Uani 1 1 d . . . . .
H17 H 0.6483 0.6710 0.3410 0.052 Uiso 1 1 calc R U . . .
C18 C 0.81503(13) 0.75917(14) 0.37894(12) 0.0367(4) Uani 1 1 d . . . . .
H18 H 0.8272 0.7491 0.3219 0.044 Uiso 1 1 calc R U . . .
C19 C 0.90057(12) 0.82251(12) 0.46424(11) 0.0302(3) Uani 1 1 d . . . . .
C20 C 1.01791(12) 0.87931(12) 0.48040(10) 0.0276(3) Uani 1 1 d . . . . .
C21 C 1.09009(12) 0.93608(12) 0.57265(10) 0.0282(3) Uani 1 1 d . . . . .
C22 C 1.04404(13) 0.93526(13) 0.64692(10) 0.0308(3) Uani 1 1 d . . . . .
C23 C 1.10118(15) 0.98294(14) 0.74149(11) 0.0366(3) Uani 1 1 d . . . . .
H23 H 1.1781 1.0221 0.7659 0.044 Uiso 1 1 calc R U . . .
C24 C 1.03185(16) 0.96518(16) 0.79195(12) 0.0426(4) Uani 1 1 d . . . . .
H24 H 1.0554 0.9909 0.8556 0.051 Uiso 1 1 calc R U . . .
C25 C 0.93120(13) 0.88113(13) 0.62904(11) 0.0324(3) Uani 1 1 d . . . . .
C26 C 0.85957(12) 0.82405(13) 0.53810(12) 0.0319(3) Uani 1 1 d . . . . .
C27 C 1.16683(13) 0.93255(13) 0.42910(11) 0.0309(3) Uani 1 1 d . . . . .
C28 C 1.21282(14) 0.93391(15) 0.35626(12) 0.0386(4) Uani 1 1 d . . . . .
H28 H 1.1672 0.8963 0.2953 0.046 Uiso 1 1 calc R U . . .
C29 C 1.32294(15) 0.99009(17) 0.37624(13) 0.0445(4) Uani 1 1 d . . . . .
C30 C 1.39322(14) 1.04644(17) 0.46657(14) 0.0463(4) Uani 1 1 d . . . . .
C31 C 1.35365(14) 1.04641(16) 0.53791(13) 0.0414(4) Uani 1 1 d . . . . .
H31 H 1.4016 1.0835 0.5979 0.050 Uiso 1 1 calc R U . . .
C32 C 1.23810(12) 0.98903(13) 0.52032(11) 0.0309(3) Uani 1 1 d . . . . .
S5 S 0.45073(4) 0.34407(4) -0.08009(3) 0.04088(11) Uani 1 1 d . . . . .
S6 S 0.62949(4) 0.47874(4) 0.14424(3) 0.04056(10) Uani 1 1 d . . . . .
F5 F 0.59028(13) -0.30088(11) -0.22530(9) 0.0739(4) Uani 1 1 d . . . . .
F6 F 0.70303(12) -0.21183(11) -0.05147(9) 0.0684(4) Uani 1 1 d . . . . .
N5 N 0.52852(10) 0.01888(11) -0.14823(9) 0.0310(3) Uani 1 1 d . . . . .
N6 N 0.65794(10) 0.11917(12) 0.03635(9) 0.0314(3) Uani 1 1 d . . . . .
C33 C 0.39190(14) 0.22141(15) -0.18653(12) 0.0418(4) Uani 1 1 d . . . . .
H33 H 0.3428 0.2098 -0.2365 0.050 Uiso 1 1 calc R U . . .
C34 C 0.42379(13) 0.14297(14) -0.19092(11) 0.0352(3) Uani 1 1 d . . . . .
H34 H 0.3995 0.0713 -0.2440 0.042 Uiso 1 1 calc R U . . .
C35 C 0.49851(12) 0.18230(13) -0.10535(10) 0.0297(3) Uani 1 1 d . . . . .
C36 C 0.54818(11) 0.12180(13) -0.08292(10) 0.0272(3) Uani 1 1 d . . . . .
C37 C 0.61593(12) 0.17429(13) 0.01026(10) 0.0288(3) Uani 1 1 d . . . . .
C38 C 0.63802(12) 0.28794(13) 0.07713(10) 0.0295(3) Uani 1 1 d . . . . .
C39 C 0.70626(13) 0.35633(14) 0.17121(10) 0.0345(3) Uani 1 1 d . . . . .
H39 H 0.7451 0.3321 0.1996 0.041 Uiso 1 1 calc R U . . .
C40 C 0.70889(14) 0.45932(15) 0.21479(11) 0.0405(4) Uani 1 1 d . . . . .
H40 H 0.7496 0.5147 0.2770 0.049 Uiso 1 1 calc R U . . .
C41 C 0.59137(12) 0.34486(13) 0.05277(10) 0.0313(3) Uani 1 1 d . . . . .
C42 C 0.52014(12) 0.29076(14) -0.03869(11) 0.0312(3) Uani 1 1 d . . . . .
C43 C 0.57471(12) -0.03496(14) -0.12245(10) 0.0310(3) Uani 1 1 d . . . . .
C44 C 0.55902(15) -0.14338(15) -0.19029(12) 0.0420(4) Uani 1 1 d . . . . .
H44 H 0.5188 -0.1762 -0.2522 0.050 Uiso 1 1 calc R U . . .
C45 C 0.60293(17) -0.19828(16) -0.16411(14) 0.0479(4) Uani 1 1 d . . . . .
C46 C 0.66278(16) -0.15078(17) -0.07134(14) 0.0460(4) Uani 1 1 d . . . . .
C47 C 0.68003(14) -0.04808(16) -0.00487(12) 0.0395(4) Uani 1 1 d . . . . .
H47 H 0.7199 -0.0181 0.0566 0.047 Uiso 1 1 calc R U . . .
C48 C 0.63703(12) 0.01413(14) -0.02923(11) 0.0320(3) Uani 1 1 d . . . . .
S7 S 0.68202(4) 0.52206(5) -0.15251(3) 0.04636(12) Uani 1 1 d . . . . .
S8 S 0.83652(4) 0.73409(4) 0.08047(3) 0.03928(10) Uani 1 1 d . . . . .
F7 F 0.92329(11) 0.02471(10) -0.05156(9) 0.0601(3) Uani 1 1 d . . . . .
F8 F 1.05463(11) 0.19248(11) 0.11717(9) 0.0626(3) Uani 1 1 d . . . . .
N7 N 0.80941(11) 0.27357(12) -0.09332(9) 0.0370(3) Uani 1 1 d . . . . .
N8 N 0.93942(11) 0.44791(12) 0.09162(9) 0.0339(3) Uani 1 1 d . . . . .
C49 C 0.64056(15) 0.38071(18) -0.23464(13) 0.0494(5) Uani 1 1 d . . . . .
H49 H 0.5929 0.3441 -0.2946 0.059 Uiso 1 1 calc R U . . .
C50 C 0.68359(14) 0.32801(17) -0.20386(12) 0.0414(4) Uani 1 1 d . . . . .
H50 H 0.6690 0.2509 -0.2397 0.050 Uiso 1 1 calc R U . . .
C51 C 0.75379(13) 0.40313(15) -0.11052(11) 0.0351(3) Uani 1 1 d . . . . .
C52 C 0.81453(12) 0.37768(14) -0.05583(11) 0.0324(3) Uani 1 1 d . . . . .
C53 C 0.88028(12) 0.46574(14) 0.03828(11) 0.0310(3) Uani 1 1 d . . . . .
C54 C 0.88201(13) 0.57605(14) 0.07532(11) 0.0318(3) Uani 1 1 d . . . . .
C55 C 0.93853(13) 0.67193(14) 0.16674(11) 0.0346(3) Uani 1 1 d . . . . .
H55 H 0.9825 0.6726 0.2134 0.042 Uiso 1 1 calc R U . . .
C56 C 0.92132(14) 0.76207(15) 0.17845(12) 0.0386(4) Uani 1 1 d . . . . .
H56 H 0.9525 0.8325 0.2343 0.046 Uiso 1 1 calc R U . . .
C57 C 0.82286(13) 0.59773(15) 0.02019(11) 0.0339(3) Uani 1 1 d . . . . .
C58 C 0.75930(13) 0.51147(15) -0.07311(11) 0.0351(3) Uani 1 1 d . . . . .
C59 C 0.86833(13) 0.25524(14) -0.03901(11) 0.0345(3) Uani 1 1 d . . . . .
C60 C 0.86511(15) 0.14534(16) -0.07528(13) 0.0425(4) Uani 1 1 d . . . . .
H60 H 0.8216 0.0860 -0.1360 0.051 Uiso 1 1 calc R U . . .
C61 C 0.92555(16) 0.12818(16) -0.02093(14) 0.0446(4) Uani 1 1 d . . . . .
C62 C 0.99312(16) 0.21590(17) 0.06966(13) 0.0437(4) Uani 1 1 d . . . . .
C63 C 0.99735(15) 0.32061(16) 0.10822(12) 0.0407(4) Uani 1 1 d . . . . .
H63 H 1.0410 0.3774 0.1695 0.049 Uiso 1 1 calc R U . . .
C64 C 0.93435(13) 0.34304(14) 0.05409(11) 0.0347(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 C10 1.7214(15) . ?
S1 C1 1.7232(17) . ?
S2 C9 1.7182(15) . ?
S2 C8 1.7236(17) . ?
F1 C13 1.3474(18) . ?
F2 C14 1.346(2) . ?
N1 C4 1.3356(19) . ?
N1 C11 1.3459(19) . ?
N2 C5 1.3326(18) . ?
N2 C16 1.3492(19) . ?
C1 C2 1.348(2) . ?
C1 H1 0.9400 . ?
C2 C3 1.427(2) . ?
C2 H2 0.9400 . ?
C3 C10 1.387(2) . ?
C3 C4 1.441(2) . ?
C4 C5 1.433(2) . ?
C5 C6 1.444(2) . ?
C6 C9 1.386(2) . ?
C6 C7 1.428(2) . ?
C7 C8 1.351(2) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C10 1.422(2) . ?
C11 C16 1.422(2) . ?
C11 C12 1.425(2) . ?
C12 C13 1.347(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.414(3) . ?
C14 C15 1.343(2) . ?
C15 C16 1.417(2) . ?
C15 H15 0.9400 . ?
S3 C17 1.714(2) . ?
S3 C26 1.7156(16) . ?
S4 C25 1.7204(16) . ?
S4 C24 1.723(2) . ?
F3 C29 1.3486(19) . ?
F4 C30 1.345(2) . ?
N3 C20 1.3337(19) . ?
N3 C27 1.346(2) . ?
N4 C21 1.334(2) . ?
N4 C32 1.348(2) . ?
C17 C18 1.354(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.425(2) . ?
C18 H18 0.9400 . ?
C19 C26 1.394(2) . ?
C19 C20 1.444(2) . ?
C20 C21 1.439(2) . ?
C21 C22 1.442(2) . ?
C22 C25 1.384(2) . ?
C22 C23 1.425(2) . ?
C23 C24 1.349(2) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.419(2) . ?
C27 C28 1.421(2) . ?
C27 C32 1.422(2) . ?
C28 C29 1.346(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.405(3) . ?
C30 C31 1.350(2) . ?
C31 C32 1.418(2) . ?
C31 H31 0.9400 . ?
S5 C42 1.7139(15) . ?
S5 C33 1.7174(18) . ?
S6 C41 1.7205(16) . ?
S6 C40 1.7255(17) . ?
F5 C45 1.341(2) . ?
F6 C46 1.345(2) . ?
N5 C36 1.3302(19) . ?
N5 C43 1.3547(19) . ?
N6 C37 1.3333(19) . ?
N6 C48 1.347(2) . ?
C33 C34 1.358(2) . ?
C33 H33 0.9400 . ?
C34 C35 1.426(2) . ?
C34 H34 0.9400 . ?
C35 C42 1.385(2) . ?
C35 C36 1.450(2) . ?
C36 C37 1.439(2) . ?
C37 C38 1.438(2) . ?
C38 C41 1.388(2) . ?
C38 C39 1.429(2) . ?
C39 C40 1.346(2) . ?
C39 H39 0.9400 . ?
C40 H40 0.9400 . ?
C41 C42 1.430(2) . ?
C43 C44 1.421(2) . ?
C43 C48 1.423(2) . ?
C44 C45 1.349(2) . ?
C44 H44 0.9400 . ?
C45 C46 1.410(3) . ?
C46 C47 1.347(2) . ?
C47 C48 1.421(2) . ?
C47 H47 0.9400 . ?
S7 C58 1.7242(16) . ?
S7 C49 1.726(2) . ?
S8 C56 1.7180(18) . ?
S8 C57 1.7216(18) . ?
F7 C61 1.349(2) . ?
F8 C62 1.347(2) . ?
N7 C52 1.337(2) . ?
N7 C59 1.342(2) . ?
N8 C53 1.328(2) . ?
N8 C64 1.347(2) . ?
C49 C50 1.353(3) . ?
C49 H49 0.9400 . ?
C50 C51 1.428(2) . ?
C50 H50 0.9400 . ?
C51 C58 1.389(2) . ?
C51 C52 1.438(2) . ?
C52 C53 1.443(2) . ?
C53 C54 1.441(2) . ?
C54 C57 1.388(2) . ?
C54 C55 1.426(2) . ?
C55 C56 1.357(2) . ?
C55 H55 0.9400 . ?
C56 H56 0.9400 . ?
C57 C58 1.424(2) . ?
C59 C60 1.425(2) . ?
C59 C64 1.431(2) . ?
C60 C61 1.345(3) . ?
C60 H60 0.9400 . ?
C61 C62 1.408(3) . ?
C62 C63 1.351(2) . ?
C63 C64 1.421(2) . ?
C63 H63 0.9400 . ?

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
C10 S1 C1 91.10(8) . . ?
C9 S2 C8 91.16(8) . . ?
C4 N1 C11 116.06(13) . . ?
C5 N2 C16 116.25(13) . . ?
C2 C1 S1 112.99(12) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 C3 112.33(14) . . ?
C1 C2 H2 123.8 . . ?
C3 C2 H2 123.8 . . ?
C10 C3 C2 112.02(13) . . ?
C10 C3 C4 119.97(13) . . ?
C2 C3 C4 128.00(14) . . ?
N1 C4 C5 121.97(13) . . ?
N1 C4 C3 118.61(13) . . ?
C5 C4 C3 119.41(13) . . ?
N2 C5 C4 121.93(13) . . ?
N2 C5 C6 119.06(13) . . ?
C4 C5 C6 119.01(13) . . ?
C9 C6 C7 112.17(13) . . ?
C9 C6 C5 119.98(13) . . ?
C7 C6 C5 127.85(13) . . ?
C8 C7 C6 112.06(14) . . ?
C8 C7 H7 124.0 . . ?
C6 C7 H7 124.0 . . ?
C7 C8 S2 113.00(12) . . ?
C7 C8 H8 123.5 . . ?
S2 C8 H8 123.5 . . ?
C6 C9 C10 120.90(13) . . ?
C6 C9 S2 111.60(11) . . ?
C10 C9 S2 127.50(11) . . ?
C3 C10 C9 120.71(13) . . ?
C3 C10 S1 111.56(11) . . ?
C9 C10 S1 127.73(12) . . ?
N1 C11 C16 122.07(14) . . ?
N1 C11 C12 118.40(14) . . ?
C16 C11 C12 119.54(14) . . ?
C13 C12 C11 118.51(16) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 F1 121.17(17) . . ?
C12 C13 C14 121.70(15) . . ?
F1 C13 C14 117.12(16) . . ?
C15 C14 F2 120.96(17) . . ?
C15 C14 C13 121.67(16) . . ?
F2 C14 C13 117.37(15) . . ?
C14 C15 C16 118.85(16) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N2 C16 C15 118.60(14) . . ?
N2 C16 C11 121.70(13) . . ?
C15 C16 C11 119.69(14) . . ?
C17 S3 C26 91.42(8) . . ?
C25 S4 C24 91.08(8) . . ?
C20 N3 C27 116.44(13) . . ?
C21 N4 C32 116.25(13) . . ?
C18 C17 S3 113.23(14) . . ?
C18 C17 H17 123.4 . . ?
S3 C17 H17 123.4 . . ?
C17 C18 C19 111.88(16) . . ?
C17 C18 H18 124.1 . . ?
C19 C18 H18 124.1 . . ?
C26 C19 C18 112.12(14) . . ?
C26 C19 C20 119.49(14) . . ?
C18 C19 C20 128.37(14) . . ?
N3 C20 C21 121.61(13) . . ?
N3 C20 C19 119.27(14) . . ?
C21 C20 C19 119.12(13) . . ?
N4 C21 C20 121.97(14) . . ?
N4 C21 C22 118.54(14) . . ?
C20 C21 C22 119.49(14) . . ?
C25 C22 C23 112.39(14) . . ?
C25 C22 C21 119.79(14) . . ?
C23 C22 C21 127.81(15) . . ?
C24 C23 C22 111.99(16) . . ?
C24 C23 H23 124.0 . . ?
C22 C23 H23 124.0 . . ?
C23 C24 S4 113.10(14) . . ?
C23 C24 H24 123.5 . . ?
S4 C24 H24 123.5 . . ?
C22 C25 C26 120.97(14) . . ?
C22 C25 S4 111.44(12) . . ?
C26 C25 S4 127.56(12) . . ?
C19 C26 C25 121.12(14) . . ?
C19 C26 S3 111.34(12) . . ?
C25 C26 S3 127.53(12) . . ?
N3 C27 C28 118.87(15) . . ?
N3 C27 C32 121.92(14) . . ?
C28 C27 C32 119.21(14) . . ?
C29 C28 C27 118.73(17) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 F3 120.89(18) . . ?
C28 C29 C30 121.94(16) . . ?
F3 C29 C30 117.17(16) . . ?
F4 C30 C31 120.66(18) . . ?
F4 C30 C29 117.72(16) . . ?
C31 C30 C29 121.63(16) . . ?
C30 C31 C32 118.46(17) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
N4 C32 C31 118.16(15) . . ?
N4 C32 C27 121.81(14) . . ?
C31 C32 C27 120.03(15) . . ?
C42 S5 C33 91.23(8) . . ?
C41 S6 C40 91.23(8) . . ?
C36 N5 C43 116.62(13) . . ?
C37 N6 C48 116.92(13) . . ?
C34 C33 S5 112.96(12) . . ?
C34 C33 H33 123.5 . . ?
S5 C33 H33 123.5 . . ?
C33 C34 C35 111.94(15) . . ?
C33 C34 H34 124.0 . . ?
C35 C34 H34 124.0 . . ?
C42 C35 C34 111.99(13) . . ?
C42 C35 C36 120.07(13) . . ?
C34 C35 C36 127.92(14) . . ?
N5 C36 C37 121.92(13) . . ?
N5 C36 C35 119.36(13) . . ?
C37 C36 C35 118.71(13) . . ?
N6 C37 C38 119.10(13) . . ?
N6 C37 C36 121.36(14) . . ?
C38 C37 C36 119.54(13) . . ?
C41 C38 C39 111.80(14) . . ?
C41 C38 C37 120.22(13) . . ?
C39 C38 C37 127.97(14) . . ?
C40 C39 C38 112.62(14) . . ?
C40 C39 H39 123.7 . . ?
C38 C39 H39 123.7 . . ?
C39 C40 S6 112.74(12) . . ?
C39 C40 H40 123.6 . . ?
S6 C40 H40 123.6 . . ?
C38 C41 C42 120.44(14) . . ?
C38 C41 S6 111.60(11) . . ?
C42 C41 S6 127.96(12) . . ?
C35 C42 C41 120.93(14) . . ?
C35 C42 S5 111.88(11) . . ?
C41 C42 S5 127.18(12) . . ?
N5 C43 C44 118.84(14) . . ?
N5 C43 C48 121.37(14) . . ?
C44 C43 C48 119.79(14) . . ?
C45 C44 C43 118.77(17) . . ?
C45 C44 H44 120.6 . . ?
C43 C44 H44 120.6 . . ?
F5 C45 C44 121.15(18) . . ?
F5 C45 C46 117.44(16) . . ?
C44 C45 C46 121.41(17) . . ?
F6 C46 C47 120.85(17) . . ?
F6 C46 C45 117.32(16) . . ?
C47 C46 C45 121.83(16) . . ?
C46 C47 C48 118.92(16) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 H47 120.5 . . ?
N6 C48 C47 119.06(15) . . ?
N6 C48 C43 121.66(14) . . ?
C47 C48 C43 119.27(15) . . ?
C58 S7 C49 91.04(9) . . ?
C56 S8 C57 91.40(8) . . ?
C52 N7 C59 116.66(14) . . ?
C53 N8 C64 116.88(14) . . ?
C50 C49 S7 113.11(14) . . ?
C50 C49 H49 123.4 . . ?
S7 C49 H49 123.4 . . ?
C49 C50 C51 112.13(17) . . ?
C49 C50 H50 123.9 . . ?
C51 C50 H50 123.9 . . ?
C58 C51 C50 112.14(15) . . ?
C58 C51 C52 120.22(15) . . ?
C50 C51 C52 127.64(16) . . ?
N7 C52 C51 119.43(15) . . ?
N7 C52 C53 121.51(15) . . ?
C51 C52 C53 119.06(15) . . ?
N8 C53 C54 119.13(14) . . ?
N8 C53 C52 121.75(15) . . ?
C54 C53 C52 119.12(14) . . ?
C57 C54 C55 112.28(15) . . ?
C57 C54 C53 120.15(15) . . ?
C55 C54 C53 127.57(14) . . ?
C56 C55 C54 112.05(15) . . ?
C56 C55 H55 124.0 . . ?
C54 C55 H55 124.0 . . ?
C55 C56 S8 112.94(13) . . ?
C55 C56 H56 123.5 . . ?
S8 C56 H56 123.5 . . ?
C54 C57 C58 120.70(15) . . ?
C54 C57 S8 111.32(12) . . ?
C58 C57 S8 127.96(13) . . ?
C51 C58 C57 120.73(15) . . ?
C51 C58 S7 111.57(12) . . ?
C57 C58 S7 127.71(13) . . ?
N7 C59 C60 118.97(16) . . ?
N7 C59 C64 121.81(15) . . ?
C60 C59 C64 119.21(16) . . ?
C61 C60 C59 118.67(18) . . ?
C61 C60 H60 120.7 . . ?
C59 C60 H60 120.7 . . ?
C60 C61 F7 120.78(18) . . ?
C60 C61 C62 122.10(16) . . ?
F7 C61 C62 117.11(17) . . ?
F8 C62 C63 120.59(18) . . ?
F8 C62 C61 117.72(16) . . ?
C63 C62 C61 121.68(16) . . ?
C62 C63 C64 118.52(17) . . ?
C62 C63 H63 120.7 . . ?
C64 C63 H63 120.7 . . ?
N8 C64 C63 118.85(15) . . ?
N8 C64 C59 121.38(15) . . ?
C63 C64 C59 119.76(15) . . ?

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
C10 S1 C1 C2 0.27(13) . . . . ?
S1 C1 C2 C3 -0.15(18) . . . . ?
C1 C2 C3 C10 -0.09(19) . . . . ?
C1 C2 C3 C4 178.80(14) . . . . ?
C11 N1 C4 C5 -0.8(2) . . . . ?
C11 N1 C4 C3 -179.85(13) . . . . ?
C10 C3 C4 N1 177.47(13) . . . . ?
C2 C3 C4 N1 -1.4(2) . . . . ?
C10 C3 C4 C5 -1.6(2) . . . . ?
C2 C3 C4 C5 179.60(14) . . . . ?
C16 N2 C5 C4 -0.8(2) . . . . ?
C16 N2 C5 C6 178.87(12) . . . . ?
N1 C4 C5 N2 1.6(2) . . . . ?
C3 C4 C5 N2 -179.35(13) . . . . ?
N1 C4 C5 C6 -178.06(13) . . . . ?
C3 C4 C5 C6 0.95(19) . . . . ?
N2 C5 C6 C9 -179.39(13) . . . . ?
C4 C5 C6 C9 0.3(2) . . . . ?
N2 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C7 -179.94(14) . . . . ?
C9 C6 C7 C8 0.51(19) . . . . ?
C5 C6 C7 C8 -179.24(14) . . . . ?
C6 C7 C8 S2 -0.45(18) . . . . ?
C9 S2 C8 C7 0.22(13) . . . . ?
C7 C6 C9 C10 179.23(13) . . . . ?
C5 C6 C9 C10 -1.0(2) . . . . ?
C7 C6 C9 S2 -0.34(16) . . . . ?
C5 C6 C9 S2 179.43(10) . . . . ?
C8 S2 C9 C6 0.08(12) . . . . ?
C8 S2 C9 C10 -179.45(14) . . . . ?
C2 C3 C10 C9 179.93(13) . . . . ?
C4 C3 C10 C9 0.9(2) . . . . ?
C2 C3 C10 S1 0.30(16) . . . . ?
C4 C3 C10 S1 -178.70(10) . . . . ?
C6 C9 C10 C3 0.4(2) . . . . ?
S2 C9 C10 C3 179.87(11) . . . . ?
C6 C9 C10 S1 179.94(11) . . . . ?
S2 C9 C10 S1 -0.6(2) . . . . ?
C1 S1 C10 C3 -0.32(11) . . . . ?
C1 S1 C10 C9 -179.92(14) . . . . ?
C4 N1 C11 C16 -0.6(2) . . . . ?
C4 N1 C11 C12 179.36(13) . . . . ?
N1 C11 C12 C13 177.93(15) . . . . ?
C16 C11 C12 C13 -2.1(2) . . . . ?
C11 C12 C13 F1 -178.15(14) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
F1 C13 C14 C15 179.47(16) . . . . ?
C12 C13 C14 F2 -179.76(16) . . . . ?
F1 C13 C14 F2 -0.7(2) . . . . ?
F2 C14 C15 C16 179.71(15) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C5 N2 C16 C15 178.77(14) . . . . ?
C5 N2 C16 C11 -0.6(2) . . . . ?
C14 C15 C16 N2 179.81(15) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
N1 C11 C16 N2 1.4(2) . . . . ?
C12 C11 C16 N2 -178.57(14) . . . . ?
N1 C11 C16 C15 -177.97(14) . . . . ?
C12 C11 C16 C15 2.1(2) . . . . ?
C26 S3 C17 C18 0.22(14) . . . . ?
S3 C17 C18 C19 -0.03(19) . . . . ?
C17 C18 C19 C26 -0.23(19) . . . . ?
C17 C18 C19 C20 178.32(15) . . . . ?
C27 N3 C20 C21 -0.2(2) . . . . ?
C27 N3 C20 C19 179.86(13) . . . . ?
C26 C19 C20 N3 -179.81(13) . . . . ?
C18 C19 C20 N3 1.7(2) . . . . ?
C26 C19 C20 C21 0.2(2) . . . . ?
C18 C19 C20 C21 -178.25(14) . . . . ?
C32 N4 C21 C20 0.0(2) . . . . ?
C32 N4 C21 C22 -179.74(13) . . . . ?
N3 C20 C21 N4 0.2(2) . . . . ?
C19 C20 C21 N4 -179.79(13) . . . . ?
N3 C20 C21 C22 179.96(13) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
N4 C21 C22 C25 179.05(13) . . . . ?
C20 C21 C22 C25 -0.7(2) . . . . ?
N4 C21 C22 C23 -2.4(2) . . . . ?
C20 C21 C22 C23 177.86(14) . . . . ?
C25 C22 C23 C24 -0.6(2) . . . . ?
C21 C22 C23 C24 -179.24(15) . . . . ?
C22 C23 C24 S4 0.06(18) . . . . ?
C25 S4 C24 C23 0.36(14) . . . . ?
C23 C22 C25 C26 -177.47(13) . . . . ?
C21 C22 C25 C26 1.3(2) . . . . ?
C23 C22 C25 S4 0.85(17) . . . . ?
C21 C22 C25 S4 179.62(11) . . . . ?
C24 S4 C25 C22 -0.69(12) . . . . ?
C24 S4 C25 C26 177.49(14) . . . . ?
C18 C19 C26 C25 179.08(14) . . . . ?
C20 C19 C26 C25 0.4(2) . . . . ?
C18 C19 C26 S3 0.39(16) . . . . ?
C20 C19 C26 S3 -178.30(11) . . . . ?
C22 C25 C26 C19 -1.2(2) . . . . ?
S4 C25 C26 C19 -179.18(11) . . . . ?
C22 C25 C26 S3 177.30(12) . . . . ?
S4 C25 C26 S3 -0.7(2) . . . . ?
C17 S3 C26 C19 -0.35(12) . . . . ?
C17 S3 C26 C25 -178.93(14) . . . . ?
C20 N3 C27 C28 -179.94(13) . . . . ?
C20 N3 C27 C32 -0.1(2) . . . . ?
N3 C27 C28 C29 179.06(16) . . . . ?
C32 C27 C28 C29 -0.8(2) . . . . ?
C27 C28 C29 F3 -179.36(15) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C28 C29 C30 F4 -179.63(17) . . . . ?
F3 C29 C30 F4 0.2(3) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
F3 C29 C30 C31 -179.80(17) . . . . ?
F4 C30 C31 C32 179.20(16) . . . . ?
C29 C30 C31 C32 -0.8(3) . . . . ?
C21 N4 C32 C31 179.57(14) . . . . ?
C21 N4 C32 C27 -0.3(2) . . . . ?
C30 C31 C32 N4 -179.36(15) . . . . ?
C30 C31 C32 C27 0.5(2) . . . . ?
N3 C27 C32 N4 0.3(2) . . . . ?
C28 C27 C32 N4 -179.84(14) . . . . ?
N3 C27 C32 C31 -179.49(15) . . . . ?
C28 C27 C32 C31 0.3(2) . . . . ?
C42 S5 C33 C34 -0.22(14) . . . . ?
S5 C33 C34 C35 0.12(19) . . . . ?
C33 C34 C35 C42 0.1(2) . . . . ?
C33 C34 C35 C36 178.54(15) . . . . ?
C43 N5 C36 C37 0.6(2) . . . . ?
C43 N5 C36 C35 -178.20(13) . . . . ?
C42 C35 C36 N5 -178.54(13) . . . . ?
C34 C35 C36 N5 3.1(2) . . . . ?
C42 C35 C36 C37 2.6(2) . . . . ?
C34 C35 C36 C37 -175.75(14) . . . . ?
C48 N6 C37 C38 -178.55(13) . . . . ?
C48 N6 C37 C36 2.2(2) . . . . ?
N5 C36 C37 N6 -3.2(2) . . . . ?
C35 C36 C37 N6 175.63(13) . . . . ?
N5 C36 C37 C38 177.50(13) . . . . ?
C35 C36 C37 C38 -3.7(2) . . . . ?
N6 C37 C38 C41 -177.19(14) . . . . ?
C36 C37 C38 C41 2.1(2) . . . . ?
N6 C37 C38 C39 3.5(2) . . . . ?
C36 C37 C38 C39 -177.25(15) . . . . ?
C41 C38 C39 C40 0.6(2) . . . . ?
C37 C38 C39 C40 180.00(15) . . . . ?
C38 C39 C40 S6 -0.2(2) . . . . ?
C41 S6 C40 C39 -0.21(14) . . . . ?
C39 C38 C41 C42 -179.96(14) . . . . ?
C37 C38 C41 C42 0.6(2) . . . . ?
C39 C38 C41 S6 -0.75(17) . . . . ?
C37 C38 C41 S6 179.80(11) . . . . ?
C40 S6 C41 C38 0.55(12) . . . . ?
C40 S6 C41 C42 179.69(15) . . . . ?
C34 C35 C42 C41 178.67(14) . . . . ?
C36 C35 C42 C41 0.1(2) . . . . ?
C34 C35 C42 S5 -0.26(17) . . . . ?
C36 C35 C42 S5 -178.85(11) . . . . ?
C38 C41 C42 C35 -1.7(2) . . . . ?
S6 C41 C42 C35 179.22(12) . . . . ?
C38 C41 C42 S5 177.04(12) . . . . ?
S6 C41 C42 S5 -2.0(2) . . . . ?
C33 S5 C42 C35 0.28(13) . . . . ?
C33 S5 C42 C41 -178.57(15) . . . . ?
C36 N5 C43 C44 -178.08(14) . . . . ?
C36 N5 C43 C48 2.6(2) . . . . ?
N5 C43 C44 C45 -178.48(16) . . . . ?
C48 C43 C44 C45 0.8(3) . . . . ?
C43 C44 C45 F5 179.81(17) . . . . ?
C43 C44 C45 C46 0.5(3) . . . . ?
F5 C45 C46 F6 0.3(3) . . . . ?
C44 C45 C46 F6 179.63(18) . . . . ?
F5 C45 C46 C47 179.88(18) . . . . ?
C44 C45 C46 C47 -0.8(3) . . . . ?
F6 C46 C47 C48 179.28(16) . . . . ?
C45 C46 C47 C48 -0.3(3) . . . . ?
C37 N6 C48 C47 179.97(14) . . . . ?
C37 N6 C48 C43 1.1(2) . . . . ?
C46 C47 C48 N6 -177.32(16) . . . . ?
C46 C47 C48 C43 1.6(2) . . . . ?
N5 C43 C48 N6 -3.7(2) . . . . ?
C44 C43 C48 N6 177.02(14) . . . . ?
N5 C43 C48 C47 177.43(14) . . . . ?
C44 C43 C48 C47 -1.8(2) . . . . ?
C58 S7 C49 C50 -0.40(14) . . . . ?
S7 C49 C50 C51 -0.4(2) . . . . ?
C49 C50 C51 C58 1.2(2) . . . . ?
C49 C50 C51 C52 -179.04(15) . . . . ?
C59 N7 C52 C51 179.65(13) . . . . ?
C59 N7 C52 C53 0.1(2) . . . . ?
C58 C51 C52 N7 -179.13(14) . . . . ?
C50 C51 C52 N7 1.1(2) . . . . ?
C58 C51 C52 C53 0.5(2) . . . . ?
C50 C51 C52 C53 -179.25(15) . . . . ?
C64 N8 C53 C54 179.46(13) . . . . ?
C64 N8 C53 C52 -0.7(2) . . . . ?
N7 C52 C53 N8 0.6(2) . . . . ?
C51 C52 C53 N8 -178.96(13) . . . . ?
N7 C52 C53 C54 -179.49(14) . . . . ?
C51 C52 C53 C54 0.9(2) . . . . ?
N8 C53 C54 C57 178.51(14) . . . . ?
C52 C53 C54 C57 -1.4(2) . . . . ?
N8 C53 C54 C55 -2.3(2) . . . . ?
C52 C53 C54 C55 177.87(15) . . . . ?
C57 C54 C55 C56 0.0(2) . . . . ?
C53 C54 C55 C56 -179.33(15) . . . . ?
C54 C55 C56 S8 0.28(18) . . . . ?
C57 S8 C56 C55 -0.34(13) . . . . ?
C55 C54 C57 C58 -178.91(14) . . . . ?
C53 C54 C57 C58 0.4(2) . . . . ?
C55 C54 C57 S8 -0.20(17) . . . . ?
C53 C54 C57 S8 179.14(11) . . . . ?
C56 S8 C57 C54 0.30(12) . . . . ?
C56 S8 C57 C58 178.89(15) . . . . ?
C50 C51 C58 C57 178.33(14) . . . . ?
C52 C51 C58 C57 -1.4(2) . . . . ?
C50 C51 C58 S7 -1.50(17) . . . . ?
C52 C51 C58 S7 178.74(11) . . . . ?
C54 C57 C58 C51 1.0(2) . . . . ?
S8 C57 C58 C51 -177.49(12) . . . . ?
C54 C57 C58 S7 -179.21(12) . . . . ?
S8 C57 C58 S7 2.3(2) . . . . ?
C49 S7 C58 C51 1.09(13) . . . . ?
C49 S7 C58 C57 -178.73(15) . . . . ?
C52 N7 C59 C60 179.49(14) . . . . ?
C52 N7 C59 C64 -0.6(2) . . . . ?
N7 C59 C60 C61 179.08(15) . . . . ?
C64 C59 C60 C61 -0.8(2) . . . . ?
C59 C60 C61 F7 178.57(14) . . . . ?
C59 C60 C61 C62 -1.2(3) . . . . ?
C60 C61 C62 F8 -176.85(15) . . . . ?
F7 C61 C62 F8 3.4(2) . . . . ?
C60 C61 C62 C63 2.8(3) . . . . ?
F7 C61 C62 C63 -177.01(15) . . . . ?
F8 C62 C63 C64 177.49(15) . . . . ?
C61 C62 C63 C64 -2.1(3) . . . . ?
C53 N8 C64 C63 179.22(14) . . . . ?
C53 N8 C64 C59 0.1(2) . . . . ?
C62 C63 C64 N8 -179.04(15) . . . . ?
C62 C63 C64 C59 0.1(2) . . . . ?
N7 C59 C64 N8 0.6(2) . . . . ?
C60 C59 C64 N8 -179.53(14) . . . . ?
N7 C59 C64 C63 -178.52(14) . . . . ?
C60 C59 C64 C63 1.3(2) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'physical vapor transport  during attempts to cocrystallize with TCNQ'
####################################################################### 
# 
# 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_Br_DTPhz
_database_code_depnum_ccdc_archive 'CCDC 1576243'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 Br2 N2 S2'
_chemical_formula_weight         450.17

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.0340(18)
_cell_length_b                   10.366(2)
_cell_length_c                   30.468(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2853.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    215(2)
_cell_measurement_reflns_used    9484
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.11

_exptl_crystal_description       cube
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    5.970
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3451
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      215(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            40804
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8357
_reflns_number_gt                7595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0448P)²] 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_abs_structure_details 
; 
 Flack x determined using 3036 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.064(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8357
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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
S1A S 0.73512(15) 0.79257(13) 0.31526(5) 0.0216(3) Uani 1 1 d . . . . .
S2A S 0.75179(14) 0.84230(12) 0.42868(5) 0.0186(3) Uani 1 1 d . . . . .
Br1A Br -0.01571(5) 0.08023(4) 0.36322(2) 0.01738(11) Uani 1 1 d . . . . .
Br2A Br -0.00189(5) 0.13061(4) 0.47220(2) 0.01518(10) Uani 1 1 d . . . . .
N1A N 0.3690(5) 0.4491(4) 0.34816(13) 0.0142(8) Uani 1 1 d . . . . .
N2A N 0.3720(4) 0.4976(4) 0.44017(13) 0.0123(8) Uani 1 1 d . . . . .
C1A C 0.6496(6) 0.7044(6) 0.27501(19) 0.0262(12) Uani 1 1 d . . . . .
H1A H 0.6688 0.7165 0.2450 0.031 Uiso 1 1 calc R U . . .
C2A C 0.5521(6) 0.6160(5) 0.29011(16) 0.0218(10) Uani 1 1 d . . . . .
H2A H 0.4961 0.5606 0.2722 0.026 Uiso 1 1 calc R U . . .
C3A C 0.5454(5) 0.6178(4) 0.33740(16) 0.0146(9) Uani 1 1 d . . . . .
C4A C 0.6380(5) 0.7108(5) 0.35499(17) 0.0155(10) Uani 1 1 d . . . . .
C5A C 0.6431(5) 0.7329(4) 0.40137(17) 0.0149(9) Uani 1 1 d . . . . .
C6A C 0.5541(5) 0.6631(4) 0.42987(15) 0.0124(9) Uani 1 1 d . . . . .
C7A C 0.5748(5) 0.7014(4) 0.47500(16) 0.0135(9) Uani 1 1 d . . . . .
H7A H 0.5236 0.6655 0.4989 0.016 Uiso 1 1 calc R U . . .
C8A C 0.6785(5) 0.7964(5) 0.47834(18) 0.0184(10) Uani 1 1 d . . . . .
H8A H 0.7072 0.8333 0.5052 0.022 Uiso 1 1 calc R U . . .
C9A C 0.4535(5) 0.5410(4) 0.36566(16) 0.0137(9) Uani 1 1 d . . . . .
C10A C 0.4570(5) 0.5638(4) 0.41257(16) 0.0132(9) Uani 1 1 d . . . . .
C11A C 0.2858(5) 0.3794(5) 0.37622(15) 0.0121(8) Uani 1 1 d . . . . .
C12A C 0.2867(5) 0.4049(4) 0.42231(16) 0.0115(9) Uani 1 1 d . . . . .
C13A C 0.1953(5) 0.3296(4) 0.45036(16) 0.0130(9) Uani 1 1 d . . . . .
H13A H 0.1935 0.3458 0.4807 0.016 Uiso 1 1 calc R U . . .
C14A C 0.1095(5) 0.2330(4) 0.43281(15) 0.0114(9) Uani 1 1 d . . . . .
C15A C 0.1096(5) 0.2084(4) 0.38705(16) 0.0140(9) Uani 1 1 d . . . . .
C16A C 0.1948(5) 0.2801(4) 0.35928(16) 0.0146(9) Uani 1 1 d . . . . .
H16A H 0.1931 0.2636 0.3289 0.018 Uiso 1 1 calc R U . . .
S1B S -0.14220(14) 0.37176(12) 0.28818(4) 0.0173(2) Uani 1 1 d . . . . .
S2B S -0.22483(12) 0.37781(12) 0.40076(4) 0.0154(2) Uani 1 1 d . . . . .
Br1B Br 0.55811(6) 1.12470(5) 0.33127(2) 0.02012(12) Uani 1 1 d . . . . .
Br2B Br 0.49452(5) 1.11964(4) 0.43945(2) 0.01670(10) Uani 1 1 d . . . . .
N1B N 0.1954(4) 0.7383(4) 0.31882(13) 0.0124(8) Uani 1 1 d . . . . .
N2B N 0.1388(5) 0.7359(4) 0.41093(13) 0.0127(8) Uani 1 1 d . . . . .
C1B C -0.0345(6) 0.4429(5) 0.24830(18) 0.0216(11) Uani 1 1 d . . . . .
H1B H -0.0346 0.4161 0.2188 0.026 Uiso 1 1 calc R U . . .
C2B C 0.0495(6) 0.5401(5) 0.26316(16) 0.0164(9) Uani 1 1 d . . . . .
H2B H 0.1133 0.5893 0.2454 0.020 Uiso 1 1 calc R U . . .
C3B C 0.0301(5) 0.5598(4) 0.30924(15) 0.0124(9) Uani 1 1 d . . . . .
C4B C -0.0710(5) 0.4748(4) 0.32688(16) 0.0134(9) Uani 1 1 d . . . . .
C5B C -0.1035(5) 0.4764(4) 0.37293(16) 0.0120(9) Uani 1 1 d . . . . .
C6B C -0.0331(5) 0.5615(4) 0.40098(15) 0.0114(9) Uani 1 1 d . . . . .
C7B C -0.0786(5) 0.5447(4) 0.44590(16) 0.0133(9) Uani 1 1 d . . . . .
H7B H -0.0420 0.5930 0.4696 0.016 Uiso 1 1 calc R U . . .
C8B C -0.1805(6) 0.4504(5) 0.44942(17) 0.0172(10) Uani 1 1 d . . . . .
H8B H -0.2235 0.4266 0.4763 0.021 Uiso 1 1 calc R U . . .
C9B C 0.1022(5) 0.6536(4) 0.33721(16) 0.0122(9) Uani 1 1 d . . . . .
C10B C 0.0721(5) 0.6532(4) 0.38370(15) 0.0113(9) Uani 1 1 d . . . . .
C11B C 0.2611(5) 0.8226(4) 0.34680(15) 0.0105(8) Uani 1 1 d . . . . .
C12B C 0.2340(5) 0.8210(4) 0.39255(16) 0.0132(9) Uani 1 1 d . . . . .
C13B C 0.3076(5) 0.9116(4) 0.42005(16) 0.0118(8) Uani 1 1 d . . . . .
H13B H 0.2914 0.9104 0.4505 0.014 Uiso 1 1 calc R U . . .
C14B C 0.4013(5) 0.9998(4) 0.40225(16) 0.0130(9) Uani 1 1 d . . . . .
C15B C 0.4275(5) 1.0018(4) 0.35572(17) 0.0144(9) Uani 1 1 d . . . . .
C16B C 0.3587(5) 0.9157(4) 0.32877(15) 0.0128(8) Uani 1 1 d . . . . .
H16B H 0.3758 0.9180 0.2984 0.015 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
S1A C1A 1.714(6) . ?
S1A C4A 1.718(5) . ?
S2A C5A 1.715(5) . ?
S2A C8A 1.719(5) . ?
Br1A C15A 1.890(5) . ?
Br2A C14A 1.892(5) . ?
N1A C9A 1.332(6) . ?
N1A C11A 1.349(6) . ?
N2A C10A 1.329(6) . ?
N2A C12A 1.347(6) . ?
C1A C2A 1.352(7) . ?
C2A C3A 1.442(7) . ?
C3A C4A 1.385(7) . ?
C3A C9A 1.437(6) . ?
C4A C5A 1.432(7) . ?
C5A C6A 1.387(6) . ?
C6A C7A 1.443(7) . ?
C6A C10A 1.452(7) . ?
C7A C8A 1.363(7) . ?
C9A C10A 1.449(7) . ?
C11A C16A 1.415(7) . ?
C11A C12A 1.429(7) . ?
C12A C13A 1.422(6) . ?
C13A C14A 1.374(6) . ?
C14A C15A 1.417(7) . ?
C15A C16A 1.364(7) . ?
S1B C4B 1.716(5) . ?
S1B C1B 1.723(5) . ?
S2B C8B 1.710(5) . ?
S2B C5B 1.721(5) . ?
Br1B C15B 1.889(5) . ?
Br2B C14B 1.881(5) . ?
N1B C9B 1.340(6) . ?
N1B C11B 1.357(6) . ?
N2B C10B 1.336(6) . ?
N2B C12B 1.354(6) . ?
C1B C2B 1.340(7) . ?
C2B C3B 1.430(7) . ?
C3B C4B 1.378(6) . ?
C3B C9B 1.447(6) . ?
C4B C5B 1.434(7) . ?
C5B C6B 1.383(6) . ?
C6B C7B 1.440(6) . ?
C6B C10B 1.444(6) . ?
C7B C8B 1.346(7) . ?
C9B C10B 1.442(6) . ?
C11B C12B 1.415(7) . ?
C11B C16B 1.418(6) . ?
C12B C13B 1.423(7) . ?
C13B C14B 1.359(6) . ?
C14B C15B 1.438(7) . ?
C15B C16B 1.363(6) . ?

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
C1A S1A C4A 90.6(3) . . ?
C5A S2A C8A 91.3(2) . . ?
C9A N1A C11A 116.7(4) . . ?
C10A N2A C12A 116.3(4) . . ?
C2A C1A S1A 114.3(4) . . ?
C1A C2A C3A 111.0(5) . . ?
C4A C3A C9A 120.2(4) . . ?
C4A C3A C2A 111.7(4) . . ?
C9A C3A C2A 128.0(5) . . ?
C3A C4A C5A 120.8(4) . . ?
C3A C4A S1A 112.3(4) . . ?
C5A C4A S1A 126.9(4) . . ?
C6A C5A C4A 121.0(4) . . ?
C6A C5A S2A 111.9(4) . . ?
C4A C5A S2A 127.1(4) . . ?
C5A C6A C7A 112.2(4) . . ?
C5A C6A C10A 119.5(4) . . ?
C7A C6A C10A 128.2(4) . . ?
C8A C7A C6A 111.0(5) . . ?
C7A C8A S2A 113.5(4) . . ?
N1A C9A C3A 119.2(4) . . ?
N1A C9A C10A 121.6(4) . . ?
C3A C9A C10A 119.2(4) . . ?
N2A C10A C9A 121.8(4) . . ?
N2A C10A C6A 119.0(4) . . ?
C9A C10A C6A 119.1(4) . . ?
N1A C11A C16A 118.9(4) . . ?
N1A C11A C12A 121.4(4) . . ?
C16A C11A C12A 119.8(4) . . ?
N2A C12A C13A 118.8(4) . . ?
N2A C12A C11A 122.2(4) . . ?
C13A C12A C11A 119.1(4) . . ?
C14A C13A C12A 119.6(4) . . ?
C13A C14A C15A 120.9(4) . . ?
C13A C14A Br2A 117.5(4) . . ?
C15A C14A Br2A 121.5(3) . . ?
C16A C15A C14A 120.8(4) . . ?
C16A C15A Br1A 118.9(4) . . ?
C14A C15A Br1A 120.3(4) . . ?
C15A C16A C11A 119.9(4) . . ?
C4B S1B C1B 90.3(2) . . ?
C8B S2B C5B 90.9(2) . . ?
C9B N1B C11B 115.7(4) . . ?
C10B N2B C12B 116.6(4) . . ?
C2B C1B S1B 113.8(4) . . ?
C1B C2B C3B 111.7(4) . . ?
C4B C3B C2B 111.9(4) . . ?
C4B C3B C9B 119.9(4) . . ?
C2B C3B C9B 128.3(4) . . ?
C3B C4B C5B 120.7(4) . . ?
C3B C4B S1B 112.3(4) . . ?
C5B C4B S1B 127.0(4) . . ?
C6B C5B C4B 121.1(4) . . ?
C6B C5B S2B 111.5(4) . . ?
C4B C5B S2B 127.3(4) . . ?
C5B C6B C7B 112.2(4) . . ?
C5B C6B C10B 119.8(4) . . ?
C7B C6B C10B 127.9(4) . . ?
C8B C7B C6B 111.0(4) . . ?
C7B C8B S2B 114.2(4) . . ?
N1B C9B C10B 122.1(4) . . ?
N1B C9B C3B 118.5(4) . . ?
C10B C9B C3B 119.4(4) . . ?
N2B C10B C9B 121.5(4) . . ?
N2B C10B C6B 119.5(4) . . ?
C9B C10B C6B 119.0(4) . . ?
N1B C11B C12B 122.4(4) . . ?
N1B C11B C16B 117.8(4) . . ?
C12B C11B C16B 119.8(4) . . ?
N2B C12B C11B 121.6(4) . . ?
N2B C12B C13B 118.9(4) . . ?
C11B C12B C13B 119.5(4) . . ?
C14B C13B C12B 120.0(4) . . ?
C13B C14B C15B 120.4(4) . . ?
C13B C14B Br2B 118.9(4) . . ?
C15B C14B Br2B 120.7(3) . . ?
C16B C15B C14B 120.6(4) . . ?
C16B C15B Br1B 119.3(4) . . ?
C14B C15B Br1B 120.1(3) . . ?
C15B C16B C11B 119.8(4) . . ?

_refine_diff_density_max         0.902
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.141


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene '
####################################################################### 
# 
# 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_yag-xii-007-6
_database_code_depnum_ccdc_archive 'CCDC 1576238'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H6 F2 N2 S2'
_chemical_formula_sum            'C16 H6 F2 N2 S2'
_chemical_formula_weight         328.35
_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'
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                   13.5360(16)
_cell_length_b                   15.4460(18)
_cell_length_c                   19.582(2)
_cell_angle_alpha                80.141(2)
_cell_angle_beta                 84.184(2)
_cell_angle_gamma                78.220(2)
_cell_volume                     3939.3(8)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9043
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      32.66
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.8678.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1992
_exptl_crystal_preparation       'Slow evaporation in dichloromethane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            55540
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         1.363
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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                17353
_reflns_number_total             20489
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.260
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1189
_refine_ls_number_reflns         20489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.073
_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)+(0.0437P)²+15.3373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1542
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16E(H16E), C7F(H7F), C7A(H7A), C13E(H13E), C13B(H13B), C13F(H13F),
 C16B(H16B), C8A(H8A), C2A(H2A), C16F(H16F), C2F(H2F), C16A(H16A), C7B(H7B),
 C8F(H8F), C1A(H1A), C2B(H2B), C1B(H1B), C1F(H1F), C8B(H8B), C13A(H13A),
 C2E(H2E), C1E(H1E), C7E(H7E), C8E(H8E), C2D(H2D), C16D(H16D), C13D(H13D),
 C8D(H8D), C1D(H1D), C7D(H7D), C2C(H2C), C16C(H16C), C1C(H1C), C13C(H13C),
 C7C(H7C), C8C(H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1A S 0.04391(6) 0.28803(5) 0.45888(4) 0.01582(15) Uani 1 1 d . . . . .
S2A S 0.08357(6) 0.06061(5) 0.44732(4) 0.01597(15) Uani 1 1 d . . . . .
S1F S 0.62154(6) 1.04177(5) 0.54927(4) 0.01890(16) Uani 1 1 d . . . . .
S2F S 0.66564(6) 0.81552(5) 0.52737(4) 0.01829(15) Uani 1 1 d . . . . .
S2B S 0.56766(7) 0.05728(6) 0.02942(4) 0.02190(17) Uani 1 1 d . . . . .
S1B S 0.50876(6) 0.28043(6) -0.04523(4) 0.02042(16) Uani 1 1 d . . . . .
S1E S 0.17397(7) 0.88819(7) 0.97784(4) 0.02691(19) Uani 1 1 d . . . . .
S2E S 0.23218(7) 0.65461(7) 1.01776(4) 0.02689(19) Uani 1 1 d . . . . .
F1B F 0.53527(15) 0.42881(14) 0.41449(10) 0.0238(4) Uani 1 1 d . . . . .
F2E F 0.22336(16) 0.63704(13) 0.52577(10) 0.0221(4) Uani 1 1 d . . . . .
F2F F 0.75256(16) 0.66327(14) 1.02135(10) 0.0262(4) Uani 1 1 d . . . . .
F1E F 0.18200(16) 0.81336(13) 0.49556(9) 0.0229(4) Uani 1 1 d . . . . .
N1B N 0.52079(19) 0.35068(17) 0.19201(14) 0.0148(5) Uani 1 1 d . . . . .
F2B F 0.56993(15) 0.25956(14) 0.47081(10) 0.0239(4) Uani 1 1 d . . . . .
F1F F 0.72259(18) 0.83308(16) 1.03752(10) 0.0315(5) Uani 1 1 d . . . . .
N2A N 0.06223(19) 0.15517(18) 0.19315(13) 0.0153(5) Uani 1 1 d . . . . .
C4A C 0.0563(2) 0.24088(19) 0.38448(14) 0.0116(5) Uani 1 1 d . . . . .
N1E N 0.17848(19) 0.84253(17) 0.73287(13) 0.0137(5) Uani 1 1 d . . . . .
N2E N 0.22309(19) 0.65283(17) 0.76514(13) 0.0139(5) Uani 1 1 d . . . . .
N2F N 0.70552(18) 0.74509(17) 0.78079(13) 0.0138(5) Uani 1 1 d . . . . .
N2B N 0.56338(19) 0.16787(17) 0.25327(13) 0.0155(5) Uani 1 1 d . . . . .
C16E C 0.1779(2) 0.8309(2) 0.61264(15) 0.0145(5) Uani 1 1 d . . . . .
H16E H 0.1625 0.8942 0.6010 0.017 Uiso 1 1 calc R . . . .
C5A C 0.0726(2) 0.14843(19) 0.37967(15) 0.0122(5) Uani 1 1 d . . . . .
C7F C 0.7017(2) 0.7028(2) 0.63914(16) 0.0154(6) Uani 1 1 d . . . . .
H7F H 0.7169 0.6486 0.6706 0.018 Uiso 1 1 calc R . . . .
C6A C 0.0731(2) 0.11964(19) 0.31634(15) 0.0118(5) Uani 1 1 d . . . . .
C5F C 0.6645(2) 0.8578(2) 0.60321(15) 0.0143(5) Uani 1 1 d . . . . .
N1F N 0.67306(19) 0.92792(17) 0.79849(14) 0.0151(5) Uani 1 1 d . . . . .
C3A C 0.0421(2) 0.30542(19) 0.32596(15) 0.0128(5) Uani 1 1 d . . . . .
C6F C 0.6850(2) 0.78953(19) 0.65904(15) 0.0126(5) Uani 1 1 d . . . . .
C3F C 0.6496(2) 0.9729(2) 0.67710(16) 0.0143(5) Uani 1 1 d . . . . .
C12F C 0.7073(2) 0.7692(2) 0.84368(15) 0.0142(5) Uani 1 1 d . . . . .
C10B C 0.5531(2) 0.1920(2) 0.18514(16) 0.0144(5) Uani 1 1 d . . . . .
N1A N 0.03128(19) 0.34063(18) 0.20241(13) 0.0164(5) Uani 1 1 d . . . . .
C5B C 0.5566(2) 0.1485(2) 0.07065(16) 0.0152(6) Uani 1 1 d . . . . .
C9A C 0.0451(2) 0.27823(19) 0.25862(15) 0.0122(5) Uani 1 1 d . . . . .
C12B C 0.5533(2) 0.2340(2) 0.29143(16) 0.0145(5) Uani 1 1 d . . . . .
C4F C 0.6464(2) 0.9491(2) 0.61231(15) 0.0147(6) Uani 1 1 d . . . . .
C11E C 0.1888(2) 0.78976(19) 0.68286(15) 0.0110(5) Uani 1 1 d . . . . .
F1A F 0.00667(19) 0.40361(19) -0.04147(11) 0.0427(6) Uani 1 1 d . . . . .
C9E C 0.1919(2) 0.8012(2) 0.79746(15) 0.0132(5) Uani 1 1 d . . . . .
C7A C 0.0817(2) 0.02453(19) 0.32384(16) 0.0158(6) Uani 1 1 d . . . . .
H7A H 0.0833 -0.0072 0.2861 0.019 Uiso 1 1 calc R . . . .
C10E C 0.2146(2) 0.7051(2) 0.81384(15) 0.0134(5) Uani 1 1 d . . . . .
C5E C 0.2172(2) 0.7175(2) 0.93679(16) 0.0184(6) Uani 1 1 d . . . . .
C9F C 0.6704(2) 0.90427(19) 0.73644(16) 0.0140(5) Uani 1 1 d . . . . .
C11A C 0.0318(2) 0.3113(2) 0.14140(16) 0.0183(6) Uani 1 1 d . . . . .
C11B C 0.5329(2) 0.3262(2) 0.26083(16) 0.0148(6) Uani 1 1 d . . . . .
C10A C 0.0605(2) 0.18425(19) 0.25346(15) 0.0122(5) Uani 1 1 d . . . . .
C3B C 0.5172(2) 0.3070(2) 0.08075(16) 0.0145(5) Uani 1 1 d . . . . .
C13E C 0.2214(2) 0.6419(2) 0.64541(15) 0.0142(5) Uani 1 1 d . . . . .
H13E H 0.2349 0.5784 0.6557 0.017 Uiso 1 1 calc R . . . .
C13B C 0.5649(2) 0.2110(2) 0.36396(16) 0.0169(6) Uani 1 1 d . . . . .
H13B H 0.5774 0.1501 0.3853 0.020 Uiso 1 1 calc R . . . .
C13F C 0.7275(2) 0.7012(2) 0.90167(16) 0.0179(6) Uani 1 1 d . . . . .
H13F H 0.7383 0.6399 0.8965 0.022 Uiso 1 1 calc R . . . .
C3E C 0.1815(2) 0.8544(2) 0.85266(16) 0.0161(6) Uani 1 1 d . . . . .
C9B C 0.5306(2) 0.2851(2) 0.15418(16) 0.0136(5) Uani 1 1 d . . . . .
C12A C 0.0466(2) 0.2187(2) 0.13654(16) 0.0172(6) Uani 1 1 d . . . . .
C16B C 0.5261(2) 0.3939(2) 0.30305(16) 0.0164(6) Uani 1 1 d . . . . .
H16B H 0.5132 0.4554 0.2835 0.020 Uiso 1 1 calc R . . . .
C10F C 0.6874(2) 0.81122(19) 0.72744(15) 0.0117(5) Uani 1 1 d . . . . .
C12E C 0.2110(2) 0.69472(19) 0.69921(14) 0.0116(5) Uani 1 1 d . . . . .
C8A C 0.0872(2) -0.0149(2) 0.39113(17) 0.0181(6) Uani 1 1 d . . . . .
H8A H 0.0925 -0.0775 0.4058 0.022 Uiso 1 1 calc R . . . .
C2A C 0.0219(2) 0.3942(2) 0.34254(17) 0.0172(6) Uani 1 1 d . . . . .
H2A H 0.0106 0.4469 0.3090 0.021 Uiso 1 1 calc R . . . .
C16F C 0.6957(2) 0.8827(2) 0.91949(17) 0.0194(6) Uani 1 1 d . . . . .
H16F H 0.6849 0.9434 0.9264 0.023 Uiso 1 1 calc R . . . .
C11F C 0.6912(2) 0.8612(2) 0.85221(16) 0.0151(6) Uani 1 1 d . . . . .
C4B C 0.5328(2) 0.2395(2) 0.04025(16) 0.0160(6) Uani 1 1 d . . . . .
C14E C 0.2117(2) 0.6840(2) 0.57886(15) 0.0145(5) Uani 1 1 d . . . . .
C15B C 0.5384(2) 0.3684(2) 0.37174(17) 0.0183(6) Uani 1 1 d . . . . .
C2F C 0.6311(2) 1.0679(2) 0.67466(17) 0.0173(6) Uani 1 1 d . . . . .
H2F H 0.6297 1.0965 0.7141 0.021 Uiso 1 1 calc R . . . .
C16A C 0.0175(3) 0.3760(3) 0.08010(18) 0.0254(7) Uani 1 1 d . . . . .
H16A H 0.0077 0.4382 0.0823 0.030 Uiso 1 1 calc R . . . .
F2 F 0.03094(19) 0.2312(2) -0.04852(11) 0.0408(6) Uani 1 1 d . . . . .
C6B C 0.5628(2) 0.1237(2) 0.14228(16) 0.0155(6) Uani 1 1 d . . . . .
C7B C 0.5751(3) 0.0294(2) 0.16215(18) 0.0210(6) Uani 1 1 d . . . . .
H7B H 0.5809 0.0002 0.2088 0.025 Uiso 1 1 calc R . . . .
C8F C 0.6934(2) 0.7065(2) 0.57014(17) 0.0185(6) Uani 1 1 d . . . . .
H8F H 0.7018 0.6552 0.5479 0.022 Uiso 1 1 calc R . . . .
C1A C 0.0208(2) 0.3941(2) 0.41190(17) 0.0174(6) Uani 1 1 d . . . . .
H1A H 0.0085 0.4471 0.4324 0.021 Uiso 1 1 calc R . . . .
C15F C 0.7154(2) 0.8158(2) 0.97334(16) 0.0207(6) Uani 1 1 d . . . . .
C4E C 0.1938(2) 0.8124(2) 0.92060(16) 0.0190(6) Uani 1 1 d . . . . .
C2B C 0.4836(3) 0.3929(2) 0.04102(17) 0.0199(6) Uani 1 1 d . . . . .
H2B H 0.4691 0.4472 0.0598 0.024 Uiso 1 1 calc R . . . .
C14B C 0.5578(2) 0.2775(2) 0.40208(16) 0.0186(6) Uani 1 1 d . . . . .
C1B C 0.4748(3) 0.3880(2) -0.02677(18) 0.0231(7) Uani 1 1 d . . . . .
H1B H 0.4523 0.4386 -0.0603 0.028 Uiso 1 1 calc R . . . .
C15E C 0.1899(2) 0.7782(2) 0.56265(15) 0.0143(5) Uani 1 1 d . . . . .
C6E C 0.2269(2) 0.6641(2) 0.88548(16) 0.0165(6) Uani 1 1 d . . . . .
C1F C 0.6157(2) 1.1124(2) 0.60973(18) 0.0200(6) Uani 1 1 d . . . . .
H1F H 0.6030 1.1758 0.5985 0.024 Uiso 1 1 calc R . . . .
C8B C 0.5776(3) -0.0142(2) 0.10797(19) 0.0246(7) Uani 1 1 d . . . . .
H8B H 0.5842 -0.0772 0.1123 0.030 Uiso 1 1 calc R . . . .
C13A C 0.0462(2) 0.1908(3) 0.07128(17) 0.0229(7) Uani 1 1 d . . . . .
H13A H 0.0559 0.1291 0.0675 0.027 Uiso 1 1 calc R . . . .
C2E C 0.1563(3) 0.9495(2) 0.84764(18) 0.0221(7) Uani 1 1 d . . . . .
H2E H 0.1452 0.9893 0.8052 0.027 Uiso 1 1 calc R . . . .
C14F C 0.7313(2) 0.7253(2) 0.96478(16) 0.0193(6) Uani 1 1 d . . . . .
C15A C 0.0182(3) 0.3465(3) 0.01865(18) 0.0295(8) Uani 1 1 d . . . . .
C1E C 0.1502(3) 0.9765(3) 0.9108(2) 0.0289(8) Uani 1 1 d . . . . .
H1E H 0.1344 1.0375 0.9173 0.035 Uiso 1 1 calc R . . . .
C7E C 0.2475(3) 0.5711(2) 0.91282(17) 0.0230(7) Uani 1 1 d . . . . .
H7E H 0.2570 0.5246 0.8853 0.028 Uiso 1 1 calc R . . . .
C14A C 0.0318(3) 0.2547(3) 0.01440(17) 0.0284(8) Uani 1 1 d . . . . .
C8E C 0.2518(3) 0.5567(3) 0.98325(19) 0.0292(8) Uani 1 1 d . . . . .
H8E H 0.2643 0.4989 1.0104 0.035 Uiso 1 1 calc R . . . .
S1D S 0.64565(6) 0.91177(5) 0.34449(4) 0.01614(15) Uani 1 1 d . . . . .
S2D S 0.61608(6) 0.68838(5) 0.39436(4) 0.01884(16) Uani 1 1 d . . . . .
N1D N 1.01473(19) 0.79368(16) 0.35401(12) 0.0132(5) Uani 1 1 d . . . . .
F1D F 1.36994(14) 0.69302(14) 0.34801(12) 0.0268(4) Uani 1 1 d . . . . .
C11D C 1.0956(2) 0.72597(19) 0.36195(14) 0.0126(5) Uani 1 1 d . . . . .
F2D F 1.34726(15) 0.52462(14) 0.38230(12) 0.0284(5) Uani 1 1 d . . . . .
N2D N 0.99079(19) 0.61291(16) 0.39143(13) 0.0143(5) Uani 1 1 d . . . . .
C5D C 0.7277(2) 0.7280(2) 0.38045(15) 0.0140(5) Uani 1 1 d . . . . .
C4D C 0.7393(2) 0.81858(19) 0.36054(15) 0.0127(5) Uani 1 1 d . . . . .
C3D C 0.8346(2) 0.84070(19) 0.35307(14) 0.0126(5) Uani 1 1 d . . . . .
C6D C 0.8110(2) 0.65978(19) 0.39209(15) 0.0136(5) Uani 1 1 d . . . . .
C2D C 0.8302(2) 0.9348(2) 0.33388(16) 0.0166(6) Uani 1 1 d . . . . .
H2D H 0.8879 0.9623 0.3267 0.020 Uiso 1 1 calc R . . . .
C12D C 1.0835(2) 0.63462(19) 0.38065(15) 0.0134(5) Uani 1 1 d . . . . .
C10D C 0.9115(2) 0.67972(19) 0.38236(14) 0.0119(5) Uani 1 1 d . . . . .
C16D C 1.1943(2) 0.7463(2) 0.35105(15) 0.0157(6) Uani 1 1 d . . . . .
H16D H 1.2036 0.8065 0.3390 0.019 Uiso 1 1 calc R . . . .
C9D C 0.9238(2) 0.77130(18) 0.36292(14) 0.0115(5) Uani 1 1 d . . . . .
C15D C 1.2748(2) 0.6778(2) 0.35830(17) 0.0180(6) Uani 1 1 d . . . . .
C13D C 1.1704(2) 0.5653(2) 0.38748(16) 0.0169(6) Uani 1 1 d . . . . .
H13D H 1.1638 0.5044 0.3997 0.020 Uiso 1 1 calc R . . . .
C14D C 1.2629(2) 0.5878(2) 0.37624(17) 0.0190(6) Uani 1 1 d . . . . .
C8D C 0.6808(3) 0.5802(2) 0.41726(19) 0.0211(7) Uani 1 1 d . . . . .
H8D H 0.6487 0.5300 0.4309 0.025 Uiso 1 1 calc R . . . .
C1D C 0.7339(2) 0.9804(2) 0.32714(17) 0.0180(6) Uani 1 1 d . . . . .
H1D H 0.7168 1.0435 0.3142 0.022 Uiso 1 1 calc R . . . .
C7D C 0.7824(3) 0.5748(2) 0.41358(17) 0.0185(6) Uani 1 1 d . . . . .
H7D H 0.8294 0.5204 0.4241 0.022 Uiso 1 1 calc R . . . .
S2C S 0.34418(6) 0.58340(6) 0.19023(4) 0.02051(16) Uani 1 1 d . . . . .
S1C S 0.28736(7) 0.82007(6) 0.17254(4) 0.02199(17) Uani 1 1 d . . . . .
N1C N -0.0731(2) 0.78953(17) 0.19224(13) 0.0150(5) Uani 1 1 d . . . . .
F1C F -0.42070(16) 0.77592(16) 0.20312(13) 0.0348(5) Uani 1 1 d . . . . .
C11C C -0.1460(2) 0.7401(2) 0.19916(15) 0.0169(6) Uani 1 1 d . . . . .
N2C N -0.0268(2) 0.59958(17) 0.20825(13) 0.0153(5) Uani 1 1 d . . . . .
C9C C 0.0220(2) 0.74457(19) 0.19188(14) 0.0139(5) Uani 1 1 d . . . . .
C3C C 0.1039(2) 0.7933(2) 0.18270(15) 0.0156(6) Uani 1 1 d . . . . .
F2C F -0.37794(17) 0.59903(17) 0.21693(14) 0.0389(6) Uani 1 1 d . . . . .
C10C C 0.0453(2) 0.64847(19) 0.19965(15) 0.0137(5) Uani 1 1 d . . . . .
C4C C 0.2034(2) 0.7476(2) 0.18223(15) 0.0163(6) Uani 1 1 d . . . . .
C5C C 0.2264(2) 0.6523(2) 0.19029(15) 0.0150(6) Uani 1 1 d . . . . .
C6C C 0.1498(2) 0.6031(2) 0.19836(15) 0.0155(6) Uani 1 1 d . . . . .
C12C C -0.1231(2) 0.6448(2) 0.20725(15) 0.0164(6) Uani 1 1 d . . . . .
C2C C 0.0968(3) 0.8877(2) 0.17645(17) 0.0207(6) Uani 1 1 d . . . . .
H2C H 0.0347 0.9295 0.1763 0.025 Uiso 1 1 calc R . . . .
C16C C -0.2489(3) 0.7852(2) 0.19793(16) 0.0202(6) Uani 1 1 d . . . . .
H16C H -0.2658 0.8486 0.1931 0.024 Uiso 1 1 calc R . . . .
C1C C 0.1895(3) 0.9113(2) 0.17077(18) 0.0248(7) Uani 1 1 d . . . . .
H1C H 0.1990 0.9713 0.1663 0.030 Uiso 1 1 calc R . . . .
C13C C -0.2026(3) 0.5957(2) 0.21426(18) 0.0216(6) Uani 1 1 d . . . . .
H13C H -0.1884 0.5321 0.2202 0.026 Uiso 1 1 calc R . . . .
C14C C -0.2992(3) 0.6417(3) 0.21224(19) 0.0255(7) Uani 1 1 d . . . . .
C7C C 0.1877(2) 0.5093(2) 0.20350(16) 0.0175(6) Uani 1 1 d . . . . .
H7C H 0.1459 0.4657 0.2089 0.021 Uiso 1 1 calc R . . . .
C8C C 0.2898(3) 0.4893(2) 0.19976(17) 0.0223(7) Uani 1 1 d . . . . .
H8C H 0.3278 0.4300 0.2021 0.027 Uiso 1 1 calc R . . . .
C15C C -0.3224(3) 0.7357(2) 0.20376(18) 0.0247(7) 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
S1A C4A 1.716(3) . ?
S1A C1A 1.721(3) . ?
S2A C5A 1.720(3) . ?
S2A C8A 1.726(3) . ?
S1F C4F 1.723(3) . ?
S1F C1F 1.728(3) . ?
S2F C5F 1.719(3) . ?
S2F C8F 1.732(3) . ?
S2B C5B 1.715(3) . ?
S2B C8B 1.733(4) . ?
S1B C4B 1.724(3) . ?
S1B C1B 1.722(4) . ?
S1E C4E 1.720(3) . ?
S1E C1E 1.727(4) . ?
S2E C5E 1.719(3) . ?
S2E C8E 1.721(4) . ?
F1B C15B 1.348(3) . ?
F2E C14E 1.345(3) . ?
F2F C14F 1.348(4) . ?
F1E C15E 1.339(3) . ?
N1B C11B 1.353(4) . ?
N1B C9B 1.332(4) . ?
F2B C14B 1.347(4) . ?
F1F C15F 1.345(4) . ?
N2A C10A 1.330(4) . ?
N2A C12A 1.351(4) . ?
C4A C5A 1.418(4) . ?
C4A C3A 1.385(4) . ?
N1E C11E 1.357(4) . ?
N1E C9E 1.328(4) . ?
N2E C10E 1.333(4) . ?
N2E C12E 1.351(4) . ?
N2F C12F 1.350(4) . ?
N2F C10F 1.334(4) . ?
N2B C10B 1.336(4) . ?
N2B C12B 1.343(4) . ?
C16E H16E 0.9500 . ?
C16E C11E 1.421(4) . ?
C16E C15E 1.354(4) . ?
C5A C6A 1.386(4) . ?
C7F H7F 0.9500 . ?
C7F C6F 1.427(4) . ?
C7F C8F 1.358(4) . ?
C6A C7A 1.433(4) . ?
C6A C10A 1.447(4) . ?
C5F C6F 1.390(4) . ?
C5F C4F 1.420(4) . ?
N1F C9F 1.333(4) . ?
N1F C11F 1.344(4) . ?
C3A C9A 1.445(4) . ?
C3A C2A 1.430(4) . ?
C6F C10F 1.440(4) . ?
C3F C4F 1.387(4) . ?
C3F C9F 1.440(4) . ?
C3F C2F 1.431(4) . ?
C12F C13F 1.416(4) . ?
C12F C11F 1.429(4) . ?
C10B C9B 1.446(4) . ?
C10B C6B 1.434(4) . ?
N1A C9A 1.334(4) . ?
N1A C11A 1.347(4) . ?
C5B C4B 1.414(4) . ?
C5B C6B 1.396(4) . ?
C9A C10A 1.443(4) . ?
C12B C11B 1.430(4) . ?
C12B C13B 1.420(4) . ?
C11E C12E 1.423(4) . ?
F1A C15A 1.346(4) . ?
C9E C10E 1.439(4) . ?
C9E C3E 1.446(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.356(4) . ?
C10E C6E 1.448(4) . ?
C5E C4E 1.422(5) . ?
C5E C6E 1.385(4) . ?
C9F C10F 1.447(4) . ?
C11A C12A 1.422(5) . ?
C11A C16A 1.426(4) . ?
C11B C16B 1.423(4) . ?
C3B C9B 1.441(4) . ?
C3B C4B 1.386(4) . ?
C3B C2B 1.429(4) . ?
C13E H13E 0.9500 . ?
C13E C12E 1.419(4) . ?
C13E C14E 1.360(4) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.353(4) . ?
C13F H13F 0.9500 . ?
C13F C14F 1.359(5) . ?
C3E C4E 1.387(4) . ?
C3E C2E 1.427(5) . ?
C12A C13A 1.417(4) . ?
C16B H16B 0.9500 . ?
C16B C15B 1.353(5) . ?
C8A H8A 0.9500 . ?
C2A H2A 0.9500 . ?
C2A C1A 1.357(5) . ?
C16F H16F 0.9500 . ?
C16F C11F 1.423(4) . ?
C16F C15F 1.350(5) . ?
C14E C15E 1.411(4) . ?
C15B C14B 1.410(5) . ?
C2F H2F 0.9500 . ?
C2F C1F 1.352(5) . ?
C16A H16A 0.9500 . ?
C16A C15A 1.356(5) . ?
F2 C14A 1.344(4) . ?
C6B C7B 1.422(4) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.344(5) . ?
C8F H8F 0.9500 . ?
C1A H1A 0.9500 . ?
C15F C14F 1.407(5) . ?
C2B H2B 0.9500 . ?
C2B C1B 1.361(5) . ?
C1B H1B 0.9500 . ?
C6E C7E 1.425(5) . ?
C1F H1F 0.9500 . ?
C8B H8B 0.9500 . ?
C13A H13A 0.9500 . ?
C13A C14A 1.357(5) . ?
C2E H2E 0.9500 . ?
C2E C1E 1.360(5) . ?
C15A C14A 1.409(6) . ?
C1E H1E 0.9500 . ?
C7E H7E 0.9500 . ?
C7E C8E 1.364(5) . ?
C8E H8E 0.9500 . ?
S1D C4D 1.720(3) . ?
S1D C1D 1.726(3) . ?
S2D C5D 1.723(3) . ?
S2D C8D 1.728(3) . ?
N1D C11D 1.351(4) . ?
N1D C9D 1.332(4) . ?
F1D C15D 1.345(4) . ?
C11D C12D 1.434(4) . ?
C11D C16D 1.422(4) . ?
F2D C14D 1.343(4) . ?
N2D C12D 1.352(4) . ?
N2D C10D 1.331(4) . ?
C5D C4D 1.423(4) . ?
C5D C6D 1.385(4) . ?
C4D C3D 1.389(4) . ?
C3D C2D 1.429(4) . ?
C3D C9D 1.447(4) . ?
C6D C10D 1.442(4) . ?
C6D C7D 1.427(4) . ?
C2D H2D 0.9500 . ?
C2D C1D 1.357(4) . ?
C12D C13D 1.420(4) . ?
C10D C9D 1.440(4) . ?
C16D H16D 0.9500 . ?
C16D C15D 1.356(4) . ?
C15D C14D 1.411(5) . ?
C13D H13D 0.9500 . ?
C13D C14D 1.354(5) . ?
C8D H8D 0.9500 . ?
C8D C7D 1.357(5) . ?
C1D H1D 0.9500 . ?
C7D H7D 0.9500 . ?
S2C C5C 1.727(3) . ?
S2C C8C 1.734(4) . ?
S1C C4C 1.727(3) . ?
S1C C1C 1.724(4) . ?
N1C C11C 1.348(4) . ?
N1C C9C 1.332(4) . ?
F1C C15C 1.349(4) . ?
C11C C12C 1.426(4) . ?
C11C C16C 1.426(5) . ?
N2C C10C 1.332(4) . ?
N2C C12C 1.348(4) . ?
C9C C3C 1.442(4) . ?
C9C C10C 1.438(4) . ?
C3C C4C 1.387(4) . ?
C3C C2C 1.427(4) . ?
F2C C14C 1.352(4) . ?
C10C C6C 1.444(4) . ?
C4C C5C 1.426(4) . ?
C5C C6C 1.387(4) . ?
C6C C7C 1.426(4) . ?
C12C C13C 1.422(4) . ?
C2C H2C 0.9500 . ?
C2C C1C 1.364(5) . ?
C16C H16C 0.9500 . ?
C16C C15C 1.357(5) . ?
C1C H1C 0.9500 . ?
C13C H13C 0.9500 . ?
C13C C14C 1.355(5) . ?
C14C C15C 1.406(5) . ?
C7C H7C 0.9500 . ?
C7C C8C 1.351(5) . ?
C8C H8C 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
C4A S1A C1A 91.30(15) . . ?
C5A S2A C8A 91.24(15) . . ?
C4F S1F C1F 91.11(15) . . ?
C5F S2F C8F 91.64(15) . . ?
C5B S2B C8B 91.06(16) . . ?
C1B S1B C4B 91.06(16) . . ?
C4E S1E C1E 91.11(17) . . ?
C5E S2E C8E 91.27(17) . . ?
C9B N1B C11B 117.0(3) . . ?
C10A N2A C12A 116.3(3) . . ?
C5A C4A S1A 127.1(2) . . ?
C3A C4A S1A 111.7(2) . . ?
C3A C4A C5A 121.2(3) . . ?
C9E N1E C11E 116.7(3) . . ?
C10E N2E C12E 116.6(3) . . ?
C10F N2F C12F 116.7(3) . . ?
C10B N2B C12B 117.0(3) . . ?
C11E C16E H16E 120.6 . . ?
C15E C16E H16E 120.6 . . ?
C15E C16E C11E 118.8(3) . . ?
C4A C5A S2A 127.0(2) . . ?
C6A C5A S2A 111.8(2) . . ?
C6A C5A C4A 121.1(3) . . ?
C6F C7F H7F 123.8 . . ?
C8F C7F H7F 123.8 . . ?
C8F C7F C6F 112.4(3) . . ?
C5A C6A C7A 112.0(3) . . ?
C5A C6A C10A 120.0(3) . . ?
C7A C6A C10A 127.9(3) . . ?
C6F C5F S2F 111.2(2) . . ?
C6F C5F C4F 121.0(3) . . ?
C4F C5F S2F 127.7(2) . . ?
C9F N1F C11F 116.7(3) . . ?
C4A C3A C9A 119.6(3) . . ?
C4A C3A C2A 112.3(3) . . ?
C2A C3A C9A 128.1(3) . . ?
C7F C6F C10F 127.7(3) . . ?
C5F C6F C7F 112.5(3) . . ?
C5F C6F C10F 119.8(3) . . ?
C4F C3F C9F 119.8(3) . . ?
C4F C3F C2F 112.1(3) . . ?
C2F C3F C9F 128.1(3) . . ?
N2F C12F C13F 118.7(3) . . ?
N2F C12F C11F 121.3(3) . . ?
C13F C12F C11F 119.9(3) . . ?
N2B C10B C9B 121.4(3) . . ?
N2B C10B C6B 119.1(3) . . ?
C6B C10B C9B 119.6(3) . . ?
C9A N1A C11A 116.6(3) . . ?
C4B C5B S2B 126.6(2) . . ?
C6B C5B S2B 111.7(2) . . ?
C6B C5B C4B 121.3(3) . . ?
N1A C9A C3A 119.3(3) . . ?
N1A C9A C10A 121.1(3) . . ?
C10A C9A C3A 119.5(3) . . ?
N2B C12B C11B 121.8(3) . . ?
N2B C12B C13B 118.7(3) . . ?
C13B C12B C11B 119.5(3) . . ?
C5F C4F S1F 127.3(2) . . ?
C3F C4F S1F 111.7(2) . . ?
C3F C4F C5F 121.0(3) . . ?
N1E C11E C16E 118.9(3) . . ?
N1E C11E C12E 121.5(3) . . ?
C16E C11E C12E 119.6(3) . . ?
N1E C9E C10E 121.7(3) . . ?
N1E C9E C3E 118.9(3) . . ?
C10E C9E C3E 119.5(3) . . ?
C6A C7A H7A 124.0 . . ?
C8A C7A C6A 112.1(3) . . ?
C8A C7A H7A 124.0 . . ?
N2E C10E C9E 121.9(3) . . ?
N2E C10E C6E 119.1(3) . . ?
C9E C10E C6E 119.0(3) . . ?
C4E C5E S2E 127.1(2) . . ?
C6E C5E S2E 111.7(3) . . ?
C6E C5E C4E 121.2(3) . . ?
N1F C9F C3F 119.3(3) . . ?
N1F C9F C10F 121.5(3) . . ?
C3F C9F C10F 119.3(3) . . ?
N1A C11A C12A 122.1(3) . . ?
N1A C11A C16A 118.3(3) . . ?
C12A C11A C16A 119.6(3) . . ?
N1B C11B C12B 121.2(3) . . ?
N1B C11B C16B 119.0(3) . . ?
C16B C11B C12B 119.8(3) . . ?
N2A C10A C6A 119.0(3) . . ?
N2A C10A C9A 122.3(3) . . ?
C9A C10A C6A 118.7(3) . . ?
C4B C3B C9B 119.9(3) . . ?
C4B C3B C2B 111.6(3) . . ?
C2B C3B C9B 128.4(3) . . ?
C12E C13E H13E 120.7 . . ?
C14E C13E H13E 120.7 . . ?
C14E C13E C12E 118.6(3) . . ?
C12B C13B H13B 120.6 . . ?
C14B C13B C12B 118.7(3) . . ?
C14B C13B H13B 120.6 . . ?
C12F C13F H13F 120.6 . . ?
C14F C13F C12F 118.8(3) . . ?
C14F C13F H13F 120.6 . . ?
C4E C3E C9E 119.7(3) . . ?
C4E C3E C2E 112.2(3) . . ?
C2E C3E C9E 128.1(3) . . ?
N1B C9B C10B 121.6(3) . . ?
N1B C9B C3B 119.5(3) . . ?
C3B C9B C10B 118.9(3) . . ?
N2A C12A C11A 121.5(3) . . ?
N2A C12A C13A 118.3(3) . . ?
C13A C12A C11A 120.2(3) . . ?
C11B C16B H16B 120.8 . . ?
C15B C16B C11B 118.4(3) . . ?
C15B C16B H16B 120.8 . . ?
N2F C10F C6F 119.2(3) . . ?
N2F C10F C9F 121.7(3) . . ?
C6F C10F C9F 119.1(3) . . ?
N2E C12E C11E 121.6(3) . . ?
N2E C12E C13E 118.6(3) . . ?
C13E C12E C11E 119.8(3) . . ?
S2A C8A H8A 123.6 . . ?
C7A C8A S2A 112.9(2) . . ?
C7A C8A H8A 123.6 . . ?
C3A C2A H2A 124.1 . . ?
C1A C2A C3A 111.8(3) . . ?
C1A C2A H2A 124.1 . . ?
C11F C16F H16F 120.4 . . ?
C15F C16F H16F 120.4 . . ?
C15F C16F C11F 119.2(3) . . ?
N1F C11F C12F 122.0(3) . . ?
N1F C11F C16F 119.1(3) . . ?
C16F C11F C12F 118.9(3) . . ?
C5B C4B S1B 126.9(2) . . ?
C3B C4B S1B 112.1(2) . . ?
C3B C4B C5B 120.8(3) . . ?
F2E C14E C13E 121.0(3) . . ?
F2E C14E C15E 117.5(3) . . ?
C13E C14E C15E 121.6(3) . . ?
F1B C15B C16B 121.6(3) . . ?
F1B C15B C14B 116.5(3) . . ?
C16B C15B C14B 121.9(3) . . ?
C3F C2F H2F 123.9 . . ?
C1F C2F C3F 112.2(3) . . ?
C1F C2F H2F 123.9 . . ?
C11A C16A H16A 120.8 . . ?
C15A C16A C11A 118.3(4) . . ?
C15A C16A H16A 120.8 . . ?
C5B C6B C10B 119.2(3) . . ?
C5B C6B C7B 111.6(3) . . ?
C7B C6B C10B 129.1(3) . . ?
C6B C7B H7B 123.6 . . ?
C8B C7B C6B 112.9(3) . . ?
C8B C7B H7B 123.6 . . ?
S2F C8F H8F 123.9 . . ?
C7F C8F S2F 112.2(2) . . ?
C7F C8F H8F 123.9 . . ?
S1A C1A H1A 123.5 . . ?
C2A C1A S1A 113.0(2) . . ?
C2A C1A H1A 123.5 . . ?
F1F C15F C16F 121.1(3) . . ?
F1F C15F C14F 117.1(3) . . ?
C16F C15F C14F 121.8(3) . . ?
C5E C4E S1E 127.3(2) . . ?
C3E C4E S1E 111.8(3) . . ?
C3E C4E C5E 120.9(3) . . ?
C3B C2B H2B 123.8 . . ?
C1B C2B C3B 112.4(3) . . ?
C1B C2B H2B 123.8 . . ?
F2B C14B C13B 121.2(3) . . ?
F2B C14B C15B 117.0(3) . . ?
C13B C14B C15B 121.7(3) . . ?
S1B C1B H1B 123.6 . . ?
C2B C1B S1B 112.8(3) . . ?
C2B C1B H1B 123.6 . . ?
F1E C15E C16E 121.4(3) . . ?
F1E C15E C14E 117.1(3) . . ?
C16E C15E C14E 121.6(3) . . ?
C5E C6E C10E 119.8(3) . . ?
C5E C6E C7E 112.3(3) . . ?
C7E C6E C10E 127.9(3) . . ?
S1F C1F H1F 123.5 . . ?
C2F C1F S1F 112.9(2) . . ?
C2F C1F H1F 123.5 . . ?
S2B C8B H8B 123.7 . . ?
C7B C8B S2B 112.7(3) . . ?
C7B C8B H8B 123.7 . . ?
C12A C13A H13A 120.9 . . ?
C14A C13A C12A 118.2(3) . . ?
C14A C13A H13A 120.9 . . ?
C3E C2E H2E 124.0 . . ?
C1E C2E C3E 112.0(3) . . ?
C1E C2E H2E 124.0 . . ?
F2F C14F C13F 121.2(3) . . ?
F2F C14F C15F 117.4(3) . . ?
C13F C14F C15F 121.4(3) . . ?
F1A C15A C16A 121.7(4) . . ?
F1A C15A C14A 116.6(3) . . ?
C16A C15A C14A 121.7(3) . . ?
S1E C1E H1E 123.6 . . ?
C2E C1E S1E 112.8(3) . . ?
C2E C1E H1E 123.6 . . ?
C6E C7E H7E 124.1 . . ?
C8E C7E C6E 111.9(3) . . ?
C8E C7E H7E 124.1 . . ?
F2 C14A C13A 120.2(4) . . ?
F2 C14A C15A 117.9(3) . . ?
C13A C14A C15A 122.0(3) . . ?
S2E C8E H8E 123.6 . . ?
C7E C8E S2E 112.8(3) . . ?
C7E C8E H8E 123.6 . . ?
C4D S1D C1D 91.19(15) . . ?
C5D S2D C8D 91.14(15) . . ?
C9D N1D C11D 116.8(2) . . ?
N1D C11D C12D 121.4(3) . . ?
N1D C11D C16D 118.9(3) . . ?
C16D C11D C12D 119.7(3) . . ?
C10D N2D C12D 117.1(3) . . ?
C4D C5D S2D 127.2(2) . . ?
C6D C5D S2D 111.9(2) . . ?
C6D C5D C4D 121.0(3) . . ?
C5D C4D S1D 127.7(2) . . ?
C3D C4D S1D 111.7(2) . . ?
C3D C4D C5D 120.6(3) . . ?
C4D C3D C2D 112.1(3) . . ?
C4D C3D C9D 120.2(3) . . ?
C2D C3D C9D 127.6(3) . . ?
C5D C6D C10D 120.1(3) . . ?
C5D C6D C7D 111.9(3) . . ?
C7D C6D C10D 128.1(3) . . ?
C3D C2D H2D 124.0 . . ?
C1D C2D C3D 112.0(3) . . ?
C1D C2D H2D 124.0 . . ?
N2D C12D C11D 121.2(3) . . ?
N2D C12D C13D 119.1(3) . . ?
C13D C12D C11D 119.6(3) . . ?
N2D C10D C6D 119.2(3) . . ?
N2D C10D C9D 121.5(3) . . ?
C9D C10D C6D 119.3(3) . . ?
C11D C16D H16D 120.8 . . ?
C15D C16D C11D 118.4(3) . . ?
C15D C16D H16D 120.8 . . ?
N1D C9D C3D 119.3(3) . . ?
N1D C9D C10D 121.9(3) . . ?
C10D C9D C3D 118.8(3) . . ?
F1D C15D C16D 121.0(3) . . ?
F1D C15D C14D 117.2(3) . . ?
C16D C15D C14D 121.8(3) . . ?
C12D C13D H13D 120.7 . . ?
C14D C13D C12D 118.6(3) . . ?
C14D C13D H13D 120.7 . . ?
F2D C14D C15D 117.5(3) . . ?
F2D C14D C13D 120.7(3) . . ?
C13D C14D C15D 121.8(3) . . ?
S2D C8D H8D 123.7 . . ?
C7D C8D S2D 112.5(2) . . ?
C7D C8D H8D 123.7 . . ?
S1D C1D H1D 123.5 . . ?
C2D C1D S1D 112.9(2) . . ?
C2D C1D H1D 123.5 . . ?
C6D C7D H7D 123.7 . . ?
C8D C7D C6D 112.6(3) . . ?
C8D C7D H7D 123.7 . . ?
C5C S2C C8C 91.08(16) . . ?
C1C S1C C4C 91.35(16) . . ?
C9C N1C C11C 116.4(3) . . ?
N1C C11C C12C 122.1(3) . . ?
N1C C11C C16C 118.6(3) . . ?
C16C C11C C12C 119.3(3) . . ?
C10C N2C C12C 116.6(3) . . ?
N1C C9C C3C 119.4(3) . . ?
N1C C9C C10C 121.6(3) . . ?
C10C C9C C3C 119.0(3) . . ?
C4C C3C C9C 120.2(3) . . ?
C4C C3C C2C 112.1(3) . . ?
C2C C3C C9C 127.6(3) . . ?
N2C C10C C9C 122.0(3) . . ?
N2C C10C C6C 118.7(3) . . ?
C9C C10C C6C 119.3(3) . . ?
C3C C4C S1C 111.6(2) . . ?
C3C C4C C5C 120.7(3) . . ?
C5C C4C S1C 127.7(2) . . ?
C4C C5C S2C 127.9(2) . . ?
C6C C5C S2C 111.3(2) . . ?
C6C C5C C4C 120.8(3) . . ?
C5C C6C C10C 120.0(3) . . ?
C5C C6C C7C 112.5(3) . . ?
C7C C6C C10C 127.5(3) . . ?
N2C C12C C11C 121.3(3) . . ?
N2C C12C C13C 118.8(3) . . ?
C13C C12C C11C 120.0(3) . . ?
C3C C2C H2C 123.8 . . ?
C1C C2C C3C 112.4(3) . . ?
C1C C2C H2C 123.8 . . ?
C11C C16C H16C 120.6 . . ?
C15C C16C C11C 118.8(3) . . ?
C15C C16C H16C 120.6 . . ?
S1C C1C H1C 123.7 . . ?
C2C C1C S1C 112.6(3) . . ?
C2C C1C H1C 123.7 . . ?
C12C C13C H13C 120.8 . . ?
C14C C13C C12C 118.4(3) . . ?
C14C C13C H13C 120.8 . . ?
F2C C14C C13C 121.2(3) . . ?
F2C C14C C15C 116.7(3) . . ?
C13C C14C C15C 122.0(3) . . ?
C6C C7C H7C 123.8 . . ?
C8C C7C C6C 112.4(3) . . ?
C8C C7C H7C 123.8 . . ?
S2C C8C H8C 123.6 . . ?
C7C C8C S2C 112.7(2) . . ?
C7C C8C H8C 123.6 . . ?
F1C C15C C16C 120.5(3) . . ?
F1C C15C C14C 118.0(3) . . ?
C16C C15C C14C 121.5(3) . . ?

_shelx_SHELXL_version_number     2015/1
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Slow evaporation in dichloromethane'
