# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_TTF-Qx-Pyrrole
_database_code_depnum_ccdc_archive 'CCDC 1828681'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           'APEX2 v2014.1-1'
_chemical_name_systematic        
;
 2-(5H-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene)-[1,3]dithiolo[4,5-g]quinoxaline
;
_chemical_name_common            Quinoxaline-TTF-pyrrole
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 N3 S4'
_chemical_formula_sum            'C14 H7 N3 S4'
_chemical_formula_weight         345.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2126(3)
_cell_length_b                   17.1917(7)
_cell_length_c                   10.7279(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.846(3)
_cell_angle_gamma                90
_cell_volume                     1325.47(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7996
_cell_measurement_theta_min      2.2435
_cell_measurement_theta_max      26.0731

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44088
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_av_R_equivalents  0.1150
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.244
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3234
_reflns_number_gt                2176
_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 Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1131P)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_number_reflns         3234
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1652(4) 0.04698(18) 0.3811(3) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.1342(4) -0.03091(18) 0.3624(3) 0.0271(7) Uani 1 1 d . . . . .
H2 H 0.2322 -0.0669 0.3822 0.033 Uiso 1 1 calc R U . . .
C3 C -0.0408(4) -0.05802(17) 0.3144(3) 0.0239(7) Uani 1 1 d . . . . .
C4 C -0.2375(5) -0.15675(19) 0.2540(3) 0.0308(8) Uani 1 1 d . . . . .
H4 H -0.2658 -0.2105 0.2453 0.037 Uiso 1 1 calc R U . . .
C5 C -0.3772(4) -0.10312(19) 0.2168(3) 0.0308(8) Uani 1 1 d . . . . .
H5 H -0.4937 -0.1221 0.1816 0.037 Uiso 1 1 calc R U . . .
C6 C -0.1841(4) -0.00316(18) 0.2810(3) 0.0238(7) Uani 1 1 d . . . . .
C7 C -0.1534(5) 0.07707(18) 0.3018(3) 0.0249(7) Uani 1 1 d . . . . .
H7 H -0.2506 0.1135 0.2821 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0203(4) 0.10211(18) 0.3513(3) 0.0231(7) Uani 1 1 d . . . . .
C9 C 0.3074(4) 0.18347(18) 0.4358(3) 0.0267(7) Uani 1 1 d . . . . .
C10 C 0.4267(4) 0.23924(18) 0.4768(3) 0.0256(7) Uani 1 1 d . . . . .
C11 C 0.5971(4) 0.36749(18) 0.5399(3) 0.0269(7) Uani 1 1 d . . . . .
C12 C 0.6831(4) 0.43801(18) 0.5696(3) 0.0289(8) Uani 1 1 d . . . . .
H12 H 0.6271 0.4881 0.5647 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8959(4) 0.34248(18) 0.6052(3) 0.0267(7) Uani 1 1 d . . . . .
H13 H 1.0094 0.3164 0.6293 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7302(4) 0.30869(17) 0.5613(3) 0.0264(7) Uani 1 1 d . . . . .
N1 N -0.0676(4) -0.13699(15) 0.3008(2) 0.0307(7) Uani 1 1 d . . . . .
N2 N -0.3543(4) -0.02775(16) 0.2285(2) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.8653(4) 0.42115(16) 0.6075(2) 0.0345(7) Uani 1 1 d . . . . .
H3 H 0.9508 0.4561 0.6302 0.041 Uiso 1 1 calc R U . . .
S1 S 0.37821(10) 0.08559(5) 0.44002(8) 0.0295(3) Uani 1 1 d . . . . .
S2 S 0.07494(11) 0.19959(5) 0.38220(8) 0.0301(3) Uani 1 1 d . . . . .
S3 S 0.36891(10) 0.33869(5) 0.48822(9) 0.0329(3) Uani 1 1 d . . . . .
S4 S 0.65788(12) 0.21360(5) 0.53075(9) 0.0365(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(4) . ?
C1 C8 1.427(4) . ?
C1 S1 1.742(3) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9500 . ?
C3 N1 1.377(4) . ?
C3 C6 1.422(4) . ?
C4 N1 1.329(4) . ?
C4 C5 1.399(5) . ?
C4 H4 0.9500 . ?
C5 N2 1.311(4) . ?
C5 H5 0.9500 . ?
C6 N2 1.374(4) . ?
C6 C7 1.412(4) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 S2 1.747(3) . ?
C9 C10 1.338(5) . ?
C9 S2 1.748(3) . ?
C9 S1 1.758(3) . ?
C10 S3 1.767(3) . ?
C10 S4 1.774(3) . ?
C11 C12 1.387(4) . ?
C11 C14 1.400(4) . ?
C11 S3 1.763(3) . ?
C12 N3 1.373(4) . ?
C12 H12 0.9500 . ?
C13 N3 1.371(4) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9500 . ?
C14 S4 1.739(3) . ?
N3 H3 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 120.6(3) . . ?
C2 C1 S1 123.6(2) . . ?
C8 C1 S1 115.8(2) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
N1 C3 C2 118.7(3) . . ?
N1 C3 C6 122.3(3) . . ?
C2 C3 C6 119.0(3) . . ?
N1 C4 C5 123.9(3) . . ?
N1 C4 H4 118.0 . . ?
C5 C4 H4 118.0 . . ?
N2 C5 C4 122.8(3) . . ?
N2 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 C7 119.2(3) . . ?
N2 C6 C3 120.3(3) . . ?
C7 C6 C3 120.5(3) . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C1 120.0(3) . . ?
C7 C8 S2 123.5(2) . . ?
C1 C8 S2 116.5(2) . . ?
C10 C9 S2 124.6(3) . . ?
C10 C9 S1 120.0(3) . . ?
S2 C9 S1 115.38(17) . . ?
C9 C10 S3 124.6(3) . . ?
C9 C10 S4 119.4(3) . . ?
S3 C10 S4 116.02(17) . . ?
C12 C11 C14 107.8(3) . . ?
C12 C11 S3 134.9(2) . . ?
C14 C11 S3 117.3(2) . . ?
N3 C12 C11 106.4(3) . . ?
N3 C12 H12 126.8 . . ?
C11 C12 H12 126.8 . . ?
N3 C13 C14 106.6(3) . . ?
N3 C13 H13 126.7 . . ?
C14 C13 H13 126.7 . . ?
C13 C14 C11 108.4(3) . . ?
C13 C14 S4 134.4(3) . . ?
C11 C14 S4 117.2(2) . . ?
C4 N1 C3 114.1(3) . . ?
C5 N2 C6 116.4(3) . . ?
C13 N3 C12 110.8(3) . . ?
C13 N3 H3 124.6 . . ?
C12 N3 H3 124.6 . . ?
C1 S1 C9 96.31(14) . . ?
C8 S2 C9 96.02(14) . . ?
C11 S3 C10 94.25(14) . . ?
C14 S4 C10 94.98(14) . . ?

_refine_diff_density_max         1.270
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.125

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ye445C2c
_database_code_depnum_ccdc_archive 'CCDC 1828682'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_ye445C2c            
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        439 Ang**3
RESPONSE: Data were not of the highest quality, and highly disordered solvent molecules could not be refined.
;
# Added during the CSD deposition process: Friday 09 March 2018 03:02 PM
# end Validation Reply Form


_audit_creation_method           'APEX2 v2014.1-1'
_chemical_name_systematic        
;
 2-(5H-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene)-6,7-bis(2,5-dimethylthiophen-3-yl)-[1,3]dithiolo[4,5-g]quinoxaline
;
_chemical_name_common            Ts-pyrrole-TTF-quinoxaline
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 N3 S6'
_chemical_formula_sum            'C26 H19 N3 S6'
_chemical_formula_weight         565.80

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      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                   29.9118(11)
_cell_length_b                   20.1932(11)
_cell_length_c                   9.8958(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.473(4)
_cell_angle_gamma                90
_cell_volume                     5836.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    192(2)
_cell_measurement_reflns_used    9499
_cell_measurement_theta_min      2.3047
_cell_measurement_theta_max      26.0544

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.488
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      192(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            47517
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_av_R_equivalents  0.1451
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             5542
_reflns_number_gt                3132
_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 Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1344P)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_number_reflns         5542
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1556
_refine_ls_R_factor_gt           0.0949
_refine_ls_wR_factor_ref         0.2445
_refine_ls_wR_factor_gt          0.2104
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20185(19) -0.2690(3) 0.8613(5) 0.0590(14) Uani 1 1 d . . . . .
H1 H 0.2145 -0.3121 0.8584 0.071 Uiso 1 1 calc R U . . .
C2 C 0.20096(17) -0.2200(2) 0.7673(5) 0.0513(13) Uani 1 1 d . . . . .
C3 C 0.17831(17) -0.1644(2) 0.8103(5) 0.0505(13) Uani 1 1 d . . . . .
C4 C 0.16694(18) -0.1818(3) 0.9329(5) 0.0567(13) Uani 1 1 d . . . . .
H4 H 0.1519 -0.1546 0.9877 0.068 Uiso 1 1 calc R U . . .
C5 C 0.21013(16) -0.1264(2) 0.6039(4) 0.0463(12) Uani 1 1 d . . . . .
C6 C 0.23007(17) -0.0854(2) 0.5283(4) 0.0482(12) Uani 1 1 d . . . . .
C7 C 0.26619(16) 0.0173(2) 0.4375(4) 0.0435(11) Uani 1 1 d . . . . .
C8 C 0.27997(15) 0.0814(2) 0.4150(5) 0.0445(12) Uani 1 1 d . . . . .
H8 H 0.2662 0.1183 0.4495 0.053 Uiso 1 1 calc R U . . .
C9 C 0.31426(15) 0.0909(2) 0.3411(4) 0.0373(10) Uani 1 1 d . . . . .
C10 C 0.33256(16) 0.0370(2) 0.2831(4) 0.0432(11) Uani 1 1 d . . . . .
C11 C 0.32002(16) -0.0285(2) 0.3099(4) 0.0440(11) Uani 1 1 d . . . . .
H11 H 0.3335 -0.0654 0.2745 0.053 Uiso 1 1 calc R U . . .
C12 C 0.28771(16) -0.0372(2) 0.3886(4) 0.0414(11) Uani 1 1 d . . . . .
C13 C 0.37442(16) 0.1078(2) 0.1759(4) 0.0401(11) Uani 1 1 d . . . . .
C14 C 0.39990(16) 0.1190(2) 0.0643(4) 0.0417(11) Uani 1 1 d . . . . .
C15 C 0.39635(17) 0.1787(3) -0.0160(5) 0.0488(12) Uani 1 1 d . . . . .
H15 H 0.3795 0.2164 0.0021 0.059 Uiso 1 1 calc R U . . .
C16 C 0.41907(17) 0.1764(3) -0.1191(5) 0.0539(13) Uani 1 1 d . . . . .
C17 C 0.42624(16) 0.0719(2) 0.0199(5) 0.0473(12) Uani 1 1 d . . . . .
C18 C 0.4243(2) 0.2291(3) -0.2216(6) 0.0827(19) Uani 1 1 d . . . . .
H18A H 0.4068 0.2684 -0.2066 0.124 Uiso 1 1 calc R U . . .
H18B H 0.4129 0.2124 -0.3158 0.124 Uiso 1 1 calc R U . . .
H18C H 0.4568 0.2408 -0.2094 0.124 Uiso 1 1 calc R U . . .
C19 C 0.4381(2) 0.0031(3) 0.0679(7) 0.0813(19) Uani 1 1 d . . . . .
H19A H 0.4487 0.0028 0.1688 0.122 Uiso 1 1 calc R U . . .
H19B H 0.4624 -0.0138 0.0249 0.122 Uiso 1 1 calc R U . . .
H19C H 0.4109 -0.0252 0.0418 0.122 Uiso 1 1 calc R U . . .
C20 C 0.36184(16) 0.1616(2) 0.2569(4) 0.0441(12) Uani 1 1 d . . . . .
C21 C 0.38392(17) 0.2272(2) 0.2673(4) 0.0404(11) Uani 1 1 d . . . . .
C22 C 0.35863(18) 0.2881(2) 0.2358(5) 0.0477(12) Uani 1 1 d . . . . .
H22 H 0.3265 0.2896 0.2006 0.057 Uiso 1 1 calc R U . . .
C23 C 0.3851(2) 0.3426(3) 0.2612(5) 0.0603(14) Uani 1 1 d . . . . .
C24 C 0.42955(18) 0.2376(3) 0.3201(5) 0.0559(13) Uani 1 1 d . . . . .
C25 C 0.3726(3) 0.4143(3) 0.2447(7) 0.089(2) Uani 1 1 d . . . . .
H25A H 0.3877 0.4344 0.1761 0.134 Uiso 1 1 calc R U . . .
H25B H 0.3826 0.4370 0.3337 0.134 Uiso 1 1 calc R U . . .
H25C H 0.3393 0.4186 0.2135 0.134 Uiso 1 1 calc R U . . .
C26 C 0.4658(2) 0.1866(4) 0.3784(7) 0.087(2) Uani 1 1 d . . . . .
H26A H 0.4598 0.1686 0.4647 0.130 Uiso 1 1 calc R U . . .
H26B H 0.4960 0.2076 0.3968 0.130 Uiso 1 1 calc R U . . .
H26C H 0.4649 0.1507 0.3113 0.130 Uiso 1 1 calc R U . . .
N1 N 0.18109(15) -0.2446(2) 0.9608(4) 0.0627(12) Uani 1 1 d . . . . .
H1A H 0.1774 -0.2670 1.0339 0.075 Uiso 1 1 calc R U . . .
N2 N 0.36129(13) 0.04669(18) 0.1957(3) 0.0427(9) Uani 1 1 d . . . . .
N3 N 0.33061(13) 0.15330(19) 0.3308(4) 0.0435(9) Uani 1 1 d . . . . .
S1 S 0.21909(5) -0.21207(6) 0.61163(12) 0.0540(4) Uani 1 1 d . . . . .
S2 S 0.17081(5) -0.09560(7) 0.70011(12) 0.0544(4) Uani 1 1 d . . . . .
S3 S 0.22158(4) 0.00012(6) 0.52110(13) 0.0500(4) Uani 1 1 d . . . . .
S4 S 0.26730(5) -0.11532(6) 0.42529(13) 0.0518(4) Uani 1 1 d . . . . .
S5 S 0.44653(4) 0.10132(7) -0.11865(12) 0.0537(4) Uani 1 1 d . . . . .
S6 S 0.44186(5) 0.32036(8) 0.32798(17) 0.0726(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.355(7) . ?
C1 N1 1.365(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.423(7) . ?
C2 S1 1.747(5) . ?
C3 C4 1.375(6) . ?
C3 S2 1.750(5) . ?
C4 N1 1.347(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.339(6) . ?
C5 S1 1.750(5) . ?
C5 S2 1.778(5) . ?
C6 S3 1.746(5) . ?
C6 S4 1.770(5) . ?
C7 C8 1.390(6) . ?
C7 C12 1.411(6) . ?
C7 S3 1.750(5) . ?
C8 C9 1.395(6) . ?
C8 H8 0.9500 . ?
C9 N3 1.364(5) . ?
C9 C10 1.396(6) . ?
C10 N2 1.358(5) . ?
C10 C11 1.414(6) . ?
C11 C12 1.378(6) . ?
C11 H11 0.9500 . ?
C12 S4 1.758(5) . ?
C13 N2 1.323(5) . ?
C13 C20 1.447(6) . ?
C13 C14 1.489(6) . ?
C14 C17 1.368(6) . ?
C14 C15 1.435(6) . ?
C15 C16 1.343(7) . ?
C15 H15 0.9500 . ?
C16 C18 1.502(8) . ?
C16 S5 1.724(6) . ?
C17 C19 1.486(7) . ?
C17 S5 1.721(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.315(5) . ?
C20 C21 1.474(6) . ?
C21 C24 1.368(7) . ?
C21 C22 1.442(6) . ?
C22 C23 1.349(7) . ?
C22 H22 0.9500 . ?
C23 C25 1.495(8) . ?
C23 S6 1.742(6) . ?
C24 C26 1.516(8) . ?
C24 S6 1.709(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H1A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 106.6(5) . . ?
C2 C1 H1 126.7 . . ?
N1 C1 H1 126.7 . . ?
C1 C2 C3 108.2(4) . . ?
C1 C2 S1 135.1(4) . . ?
C3 C2 S1 116.7(4) . . ?
C4 C3 C2 106.7(4) . . ?
C4 C3 S2 136.9(4) . . ?
C2 C3 S2 116.4(3) . . ?
N1 C4 C3 107.1(5) . . ?
N1 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C6 C5 S1 123.5(4) . . ?
C6 C5 S2 120.6(4) . . ?
S1 C5 S2 115.8(3) . . ?
C5 C6 S3 123.7(4) . . ?
C5 C6 S4 121.5(4) . . ?
S3 C6 S4 114.7(3) . . ?
C8 C7 C12 119.8(4) . . ?
C8 C7 S3 122.9(4) . . ?
C12 C7 S3 117.3(4) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N3 C9 C8 118.9(4) . . ?
N3 C9 C10 120.7(4) . . ?
C8 C9 C10 120.4(4) . . ?
N2 C10 C9 120.5(4) . . ?
N2 C10 C11 119.0(4) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C11 C10 118.2(4) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C7 121.5(4) . . ?
C11 C12 S4 123.3(4) . . ?
C7 C12 S4 115.1(4) . . ?
N2 C13 C20 119.8(4) . . ?
N2 C13 C14 117.9(4) . . ?
C20 C13 C14 122.2(4) . . ?
C17 C14 C15 112.7(4) . . ?
C17 C14 C13 123.7(4) . . ?
C15 C14 C13 123.4(4) . . ?
C16 C15 C14 113.7(4) . . ?
C16 C15 H15 123.2 . . ?
C14 C15 H15 123.2 . . ?
C15 C16 C18 129.2(5) . . ?
C15 C16 S5 110.4(4) . . ?
C18 C16 S5 120.3(4) . . ?
C14 C17 C19 131.5(4) . . ?
C14 C17 S5 110.0(3) . . ?
C19 C17 S5 118.5(4) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C13 120.9(4) . . ?
N3 C20 C21 115.9(4) . . ?
C13 C20 C21 123.2(4) . . ?
C24 C21 C22 112.7(4) . . ?
C24 C21 C20 124.0(4) . . ?
C22 C21 C20 123.0(4) . . ?
C23 C22 C21 113.3(5) . . ?
C23 C22 H22 123.3 . . ?
C21 C22 H22 123.3 . . ?
C22 C23 C25 130.3(5) . . ?
C22 C23 S6 110.2(4) . . ?
C25 C23 S6 119.5(4) . . ?
C21 C24 C26 127.8(5) . . ?
C21 C24 S6 110.8(4) . . ?
C26 C24 S6 121.2(4) . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C4 N1 C1 111.4(4) . . ?
C4 N1 H1A 124.3 . . ?
C1 N1 H1A 124.3 . . ?
C13 N2 C10 118.6(4) . . ?
C20 N3 C9 118.0(4) . . ?
C2 S1 C5 93.2(2) . . ?
C3 S2 C5 92.6(2) . . ?
C6 S3 C7 95.5(2) . . ?
C12 S4 C6 95.9(2) . . ?
C17 S5 C16 93.2(2) . . ?
C24 S6 C23 93.0(3) . . ?

_refine_diff_density_max         1.159
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.115

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_No2
_database_code_depnum_ccdc_archive 'CCDC 1828683'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
2-(5H-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene)-6,7-bis(2,5-dimethylthiophen-3-yl)-[1,3]dithiolo[4,5-g]quinoxaline
;
_chemical_name_common            Ts-Qx-TTF-pyrrole,2MSA
_chemical_melting_point          ?
_chemical_formula_moiety         'C33H26N3O2S7, CH4O3S,CH3O3S,CHCl3'
_chemical_formula_sum            'C36 H34 Cl3 N3 O8 S9'
_chemical_formula_weight         1031.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.8535(3)
_cell_length_b                   12.4996(4)
_cell_length_c                   18.2429(5)
_cell_angle_alpha                109.3710(12)
_cell_angle_beta                 93.9288(12)
_cell_angle_gamma                103.0890(13)
_cell_volume                     2246.19(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9520
_cell_measurement_theta_min      2.599
_cell_measurement_theta_max      77.667

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   0.57
_exptl_transmission_factor_max   1.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    6.202
_shelx_estimated_absorpt_T_min   0.318
_shelx_estimated_absorpt_T_max   0.637
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4311
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63643
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.599
_diffrn_reflns_theta_max         77.667
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             9367
_reflns_number_gt                8054
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1557P)²+2.8076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         9367
_refine_ls_number_parameters     539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2310
_refine_ls_wR_factor_gt          0.1990
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1328(3) -0.1187(3) 1.17967(19) 0.0287(7) Uani 1 1 d . . . . .
H1 H -0.220913 -0.152886 1.174922 0.034 Uiso 1 1 calc R U . . .
C2 C -0.0776(3) -0.0382(3) 1.14860(18) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.0584(3) -0.0086(3) 1.17109(18) 0.0271(6) Uani 1 1 d . . . . .
C4 C 0.0846(3) -0.0702(3) 1.2161(2) 0.0312(7) Uani 1 1 d . . . . .
H4 H 0.165786 -0.066373 1.240043 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0189(3) 0.1148(3) 1.08865(18) 0.0277(6) Uani 1 1 d . . . . .
C6 C 0.0359(3) 0.1981(3) 1.05613(19) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.1408(3) 0.3444(3) 0.99117(18) 0.0246(6) Uani 1 1 d . . . . .
C8 C 0.0052(3) 0.3194(3) 0.96863(18) 0.0239(6) Uani 1 1 d . . . . .
C9 C -0.0427(3) 0.3629(3) 0.91631(19) 0.0268(6) Uani 1 1 d . . . . .
H9 H -0.131569 0.347164 0.901980 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0430(3) 0.4317(3) 0.88424(18) 0.0237(6) Uani 1 1 d . . . . .
C11 C 0.1762(3) 0.4572(3) 0.90924(18) 0.0237(6) Uani 1 1 d . . . . .
C12 C 0.2264(3) 0.4144(3) 0.96338(18) 0.0263(6) Uani 1 1 d . . . . .
H12 H 0.315053 0.432922 0.979894 0.032 Uiso 1 1 calc R U . . .
C13 C 0.0776(3) 0.5271(3) 0.79561(18) 0.0247(6) Uani 1 1 d . . . . .
C14 C 0.2126(3) 0.5660(3) 0.82423(18) 0.0237(6) Uani 1 1 d . . . . .
C15 C 0.3045(3) 0.6492(3) 0.80110(18) 0.0266(6) Uani 1 1 d . . . . .
C16 C 0.4246(3) 0.6400(3) 0.7867(2) 0.0328(7) Uani 1 1 d . . . . .
C17 C 0.4872(4) 0.5440(4) 0.7840(3) 0.0460(10) Uani 1 1 d . . . . .
H17A H 0.542132 0.565476 0.833717 0.069 Uiso 1 1 calc R U . . .
H17B H 0.538177 0.532731 0.741782 0.069 Uiso 1 1 calc R U . . .
H17C H 0.422037 0.471620 0.774820 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3708(4) 0.8161(4) 0.7693(2) 0.0396(8) Uani 1 1 d . . . . .
C19 C 0.3725(6) 0.9260(5) 0.7516(4) 0.0643(14) Uani 1 1 d . . . . .
H19A H 0.371256 0.909039 0.695582 0.096 Uiso 1 1 calc R U . . .
H19B H 0.449507 0.986902 0.780395 0.096 Uiso 1 1 calc R U . . .
H19C H 0.297842 0.952691 0.767265 0.096 Uiso 1 1 calc R U . . .
C20 C 0.2749(4) 0.7499(3) 0.7901(2) 0.0311(7) Uani 1 1 d . . . . .
H20 H 0.195815 0.767529 0.797003 0.037 Uiso 1 1 calc R U . . .
C21 C 0.0230(3) 0.5564(3) 0.73049(18) 0.0249(6) Uani 1 1 d . . . . .
C22 C -0.0840(3) 0.6066(3) 0.7367(2) 0.0317(7) Uani 1 1 d . . . . .
H22 H -0.125492 0.621907 0.781210 0.038 Uiso 1 1 calc R U . . .
C23 C -0.1195(4) 0.6297(4) 0.6720(2) 0.0395(8) Uani 1 1 d . . . . .
C24 C -0.2236(6) 0.6837(6) 0.6567(3) 0.0651(15) Uani 1 1 d . . . . .
H24A H -0.264733 0.705605 0.703043 0.098 Uiso 1 1 calc R U . . .
H24B H -0.286418 0.627434 0.612528 0.098 Uiso 1 1 calc R U . . .
H24C H -0.187283 0.753212 0.644714 0.098 Uiso 1 1 calc R U . . .
C25 C 0.0656(3) 0.5398(3) 0.65954(19) 0.0295(7) Uani 1 1 d . . . . .
C26 C 0.1708(4) 0.4872(4) 0.6284(2) 0.0421(9) Uani 1 1 d . . . . .
H26A H 0.247020 0.549565 0.634767 0.063 Uiso 1 1 calc R U . . .
H26B H 0.144281 0.439452 0.573106 0.063 Uiso 1 1 calc R U . . .
H26C H 0.189194 0.438516 0.657305 0.063 Uiso 1 1 calc R U . . .
C27 C -0.0860(3) -0.0666(3) 1.3679(2) 0.0317(7) Uani 1 1 d . . . . .
C28 C -0.2109(4) -0.0669(4) 1.3799(2) 0.0385(8) Uani 1 1 d . . . . .
H28 H -0.278675 -0.133595 1.352271 0.046 Uiso 1 1 calc R U . . .
C29 C -0.2346(4) 0.0312(4) 1.4327(2) 0.0428(9) Uani 1 1 d . . . . .
H29 H -0.318935 0.029837 1.442018 0.051 Uiso 1 1 calc R U . . .
C30 C -0.1367(4) 0.1325(4) 1.4725(2) 0.0381(8) Uani 1 1 d . . . . .
C31 C -0.0127(4) 0.1304(4) 1.4604(2) 0.0455(9) Uani 1 1 d . . . . .
H31 H 0.054685 0.197472 1.488082 0.055 Uiso 1 1 calc R U . . .
C32 C 0.0155(4) 0.0324(4) 1.4088(2) 0.0406(8) Uani 1 1 d . . . . .
H32 H 0.100380 0.032448 1.401577 0.049 Uiso 1 1 calc R U . . .
C33 C -0.1656(5) 0.2419(5) 1.5255(3) 0.0547(12) Uani 1 1 d . . . . .
H33A H -0.092215 0.287630 1.566112 0.082 Uiso 1 1 calc R U . . .
H33B H -0.239394 0.220215 1.549766 0.082 Uiso 1 1 calc R U . . .
H33C H -0.183678 0.288380 1.494894 0.082 Uiso 1 1 calc R U . . .
N1 N -0.0330(3) -0.1407(3) 1.22007(17) 0.0308(6) Uani 1 1 d . . . . .
N2 N 0.2547(3) 0.5284(2) 0.87947(16) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.336386 0.550623 0.897225 0.031 Uiso 1 1 calc R U . . .
N3 N -0.0036(3) 0.4677(2) 0.82828(16) 0.0260(5) Uani 1 1 d . . . . .
S1 S 0.15143(8) 0.08658(8) 1.13306(5) 0.0338(2) Uani 1 1 d . . . . .
S2 S -0.13402(8) 0.02749(8) 1.08787(5) 0.0289(2) Uani 1 1 d . . . . .
S3 S -0.09110(8) 0.23193(8) 1.01118(5) 0.0295(2) Uani 1 1 d . . . . .
S4 S 0.19001(8) 0.28054(8) 1.05559(5) 0.0322(2) Uani 1 1 d . . . . .
S5 S -0.02338(10) 0.58861(9) 0.60220(5) 0.0409(3) Uani 1 1 d . . . . .
S6 S 0.50012(10) 0.75618(10) 0.76097(7) 0.0457(3) Uani 1 1 d . . . . .
S7 S -0.05558(9) -0.18629(8) 1.29635(5) 0.0341(2) Uani 1 1 d . . . . .
O1 O 0.0640(3) -0.2034(3) 1.31984(18) 0.0473(7) Uani 1 1 d . . . . .
O2 O -0.1693(3) -0.2824(2) 1.27026(17) 0.0452(7) Uani 1 1 d . . . . .
S8 S 0.40859(9) 0.79840(9) 0.28395(5) 0.0373(2) Uani 1 1 d . . . . .
C36 C 0.2982(5) 0.6638(5) 0.2557(4) 0.0604(13) Uani 1 1 d . . . . .
H36A H 0.215092 0.675042 0.267061 0.091 Uiso 1 1 calc R U . . .
H36B H 0.324547 0.617785 0.284501 0.091 Uiso 1 1 calc R U . . .
H36C H 0.292891 0.622571 0.199766 0.091 Uiso 1 1 calc R U . . .
O6A O 0.5271(3) 0.7701(3) 0.24861(19) 0.0537(8) Uani 1 1 d . . . . .
H6A H 0.507297 0.735564 0.200302 0.081 Uiso 1 1 calc R U . . .
O7A O 0.3603(3) 0.8710(3) 0.2511(2) 0.0581(9) Uani 1 1 d . . . . .
O8A O 0.4458(4) 0.8412(3) 0.36693(18) 0.0612(9) Uani 1 1 d . . . . .
S9 S 0.46386(8) 0.72903(9) 0.04132(5) 0.0386(2) Uani 1 1 d . . . . .
C35 C 0.4841(7) 0.8566(5) 0.0164(4) 0.0802(19) Uani 1 1 d . . . . .
H35A H 0.422627 0.840601 -0.029561 0.120 Uiso 1 1 calc R U . . .
H35B H 0.570241 0.878702 0.005085 0.120 Uiso 1 1 calc R U . . .
H35C H 0.470521 0.920371 0.060152 0.120 Uiso 1 1 calc R U . . .
O3A O 0.4880(3) 0.6388(3) -0.02711(16) 0.0414(6) Uani 1 1 d . . . . .
O4A O 0.5612(3) 0.7591(3) 0.10982(18) 0.0536(8) Uani 1 1 d . . . . .
O5A O 0.3349(3) 0.6983(3) 0.0564(2) 0.0557(8) Uani 1 1 d . . . . .
C34 C 0.5222(6) 0.7423(5) 0.4958(3) 0.0628(14) Uani 1 1 d . . . . .
H34 H 0.465236 0.758596 0.458440 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6441(2) 0.6914(2) 0.44883(11) 0.0949(6) Uani 1 1 d . . . . .
Cl2 Cl 0.4326(2) 0.6369(2) 0.52869(14) 0.0977(6) Uani 1 1 d . . . . .
Cl3 Cl 0.5889(2) 0.87149(18) 0.57679(12) 0.1009(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.358(5) . ?
C1 N1 1.397(4) . ?
C2 C3 1.433(4) . ?
C2 S2 1.736(3) . ?
C3 C4 1.355(5) . ?
C3 S1 1.737(3) . ?
C4 N1 1.398(5) . ?
C5 C6 1.344(5) . ?
C5 S2 1.764(4) . ?
C5 S1 1.764(3) . ?
C6 S4 1.757(4) . ?
C6 S3 1.759(3) . ?
C7 C12 1.369(5) . ?
C7 C8 1.434(4) . ?
C7 S4 1.742(3) . ?
C8 C9 1.372(4) . ?
C8 S3 1.745(3) . ?
C9 C10 1.411(5) . ?
C10 N3 1.356(4) . ?
C10 C11 1.416(4) . ?
C11 N2 1.361(4) . ?
C11 C12 1.403(4) . ?
C13 N3 1.324(4) . ?
C13 C14 1.435(4) . ?
C13 C21 1.479(4) . ?
C14 N2 1.339(4) . ?
C14 C15 1.460(5) . ?
C15 C16 1.370(5) . ?
C15 C20 1.439(5) . ?
C16 C17 1.496(5) . ?
C16 S6 1.723(4) . ?
C18 C20 1.335(5) . ?
C18 C19 1.509(6) . ?
C18 S6 1.728(4) . ?
C21 C25 1.371(5) . ?
C21 C22 1.434(5) . ?
C22 C23 1.355(5) . ?
C23 C24 1.497(5) . ?
C23 S5 1.722(4) . ?
C25 C26 1.496(5) . ?
C25 S5 1.718(3) . ?
C27 C28 1.387(5) . ?
C27 C32 1.400(6) . ?
C27 S7 1.743(4) . ?
C28 C29 1.375(6) . ?
C29 C30 1.391(6) . ?
C30 C31 1.383(6) . ?
C30 C33 1.504(6) . ?
C31 C32 1.387(6) . ?
N1 S7 1.682(3) . ?
S7 O1 1.423(3) . ?
S7 O2 1.436(3) . ?
S8 O7A 1.411(3) . ?
S8 O8A 1.422(3) . ?
S8 O6A 1.537(3) . ?
S8 C36 1.720(5) . ?
S9 O5A 1.436(3) . ?
S9 O3A 1.464(3) . ?
S9 O4A 1.465(3) . ?
S9 C35 1.770(6) . ?
C34 Cl3 1.748(7) . ?
C34 Cl1 1.751(5) . ?
C34 Cl2 1.751(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
C2 C1 N1 106.6(3) . . ?
C1 C2 C3 108.3(3) . . ?
C1 C2 S2 134.8(3) . . ?
C3 C2 S2 116.9(2) . . ?
C4 C3 C2 108.6(3) . . ?
C4 C3 S1 134.4(3) . . ?
C2 C3 S1 117.0(2) . . ?
C3 C4 N1 106.5(3) . . ?
C6 C5 S2 122.5(3) . . ?
C6 C5 S1 120.6(3) . . ?
S2 C5 S1 116.85(19) . . ?
C5 C6 S4 121.3(3) . . ?
C5 C6 S3 123.4(3) . . ?
S4 C6 S3 115.39(18) . . ?
C12 C7 C8 121.8(3) . . ?
C12 C7 S4 122.1(2) . . ?
C8 C7 S4 116.1(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 S3 123.4(3) . . ?
C7 C8 S3 116.2(2) . . ?
C8 C9 C10 119.3(3) . . ?
N3 C10 C9 119.4(3) . . ?
N3 C10 C11 121.6(3) . . ?
C9 C10 C11 118.9(3) . . ?
N2 C11 C12 120.9(3) . . ?
N2 C11 C10 116.7(3) . . ?
C12 C11 C10 122.4(3) . . ?
C7 C12 C11 117.2(3) . . ?
N3 C13 C14 121.5(3) . . ?
N3 C13 C21 117.3(3) . . ?
C14 C13 C21 121.1(3) . . ?
N2 C14 C13 117.0(3) . . ?
N2 C14 C15 118.3(3) . . ?
C13 C14 C15 124.5(3) . . ?
C16 C15 C20 113.2(3) . . ?
C16 C15 C14 124.8(3) . . ?
C20 C15 C14 122.1(3) . . ?
C15 C16 C17 130.1(3) . . ?
C15 C16 S6 109.4(3) . . ?
C17 C16 S6 120.3(3) . . ?
C20 C18 C19 127.9(4) . . ?
C20 C18 S6 110.5(3) . . ?
C19 C18 S6 121.6(3) . . ?
C18 C20 C15 113.5(3) . . ?
C25 C21 C22 112.9(3) . . ?
C25 C21 C13 125.7(3) . . ?
C22 C21 C13 121.4(3) . . ?
C23 C22 C21 113.3(3) . . ?
C22 C23 C24 129.3(4) . . ?
C22 C23 S5 110.4(3) . . ?
C24 C23 S5 120.3(3) . . ?
C21 C25 C26 130.0(3) . . ?
C21 C25 S5 110.1(2) . . ?
C26 C25 S5 119.9(3) . . ?
C28 C27 C32 120.6(4) . . ?
C28 C27 S7 119.9(3) . . ?
C32 C27 S7 119.3(3) . . ?
C29 C28 C27 119.4(4) . . ?
C28 C29 C30 121.5(4) . . ?
C31 C30 C29 118.0(4) . . ?
C31 C30 C33 121.1(4) . . ?
C29 C30 C33 120.8(4) . . ?
C30 C31 C32 122.1(4) . . ?
C31 C32 C27 118.2(4) . . ?
C1 N1 C4 110.0(3) . . ?
C1 N1 S7 121.2(2) . . ?
C4 N1 S7 121.9(2) . . ?
C14 N2 C11 123.3(3) . . ?
C13 N3 C10 119.1(3) . . ?
C3 S1 C5 94.21(16) . . ?
C2 S2 C5 94.33(16) . . ?
C8 S3 C6 95.42(16) . . ?
C7 S4 C6 95.69(15) . . ?
C25 S5 C23 93.36(17) . . ?
C16 S6 C18 93.41(18) . . ?
O1 S7 O2 120.60(19) . . ?
O1 S7 N1 104.99(16) . . ?
O2 S7 N1 106.18(17) . . ?
O1 S7 C27 110.58(19) . . ?
O2 S7 C27 109.29(18) . . ?
N1 S7 C27 103.69(16) . . ?
O7A S8 O8A 117.6(2) . . ?
O7A S8 O6A 110.5(2) . . ?
O8A S8 O6A 105.8(2) . . ?
O7A S8 C36 109.1(2) . . ?
O8A S8 C36 108.8(3) . . ?
O6A S8 C36 104.2(2) . . ?
O5A S9 O3A 112.14(18) . . ?
O5A S9 O4A 113.6(2) . . ?
O3A S9 O4A 110.99(18) . . ?
O5A S9 C35 107.7(3) . . ?
O3A S9 C35 105.6(3) . . ?
O4A S9 C35 106.2(3) . . ?
Cl3 C34 Cl1 109.8(3) . . ?
Cl3 C34 Cl2 108.7(3) . . ?
Cl1 C34 Cl2 110.4(3) . . ?

_refine_diff_density_max         0.817
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.144

