# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2ttcv
_audit_block_doi                 10.5517/cc12rqq8
_database_code_depnum_ccdc_archive 'CCDC 1005910'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401513n 2014
_audit_update_record             
;
2014-05-23 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H5 N3 S2'
_chemical_formula_weight         267.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Orthorombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   7.8613(10)
_cell_length_b                   24.495(3)
_cell_length_c                   6.1207(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1178.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_type   multiscan
_exptl_absorpt_correction_T_min  0.8493
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7326
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.99
_reflns_number_total             2372
_reflns_number_gt                2214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0355P)²+0.3066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.59766(6) 0.730917(18) 0.97676(11) 0.02460(12) Uani 1 1 d . . .
S1 S 0.53667(7) 0.85805(2) 0.82591(10) 0.02874(13) Uani 1 1 d . . .
C13 C 0.5107(3) 0.62009(8) 0.7955(4) 0.0249(5) Uani 1 1 d . . .
C12 C 0.6046(3) 0.53655(8) 0.9763(5) 0.0277(4) Uani 1 1 d . . .
N2 N 0.6131(3) 0.49001(7) 0.9707(5) 0.0400(5) Uani 1 1 d . . .
C10 C 0.5939(3) 0.59516(7) 0.9777(5) 0.0246(4) Uani 1 1 d . . .
N3 N 0.4469(3) 0.64021(7) 0.6479(4) 0.0326(4) Uani 1 1 d . . .
N1 N 0.8088(3) 0.57169(7) 1.4570(4) 0.0378(5) Uani 1 1 d . . .
C7 C 0.7325(3) 0.71026(9) 1.3505(4) 0.0275(5) Uani 1 1 d . . .
C6 C 0.7250(3) 0.76692(8) 1.3357(4) 0.0270(4) Uani 1 1 d . . .
C8 C 0.6669(3) 0.68370(8) 1.1691(4) 0.0236(4) Uani 1 1 d . . .
C1 C 0.5739(3) 0.92615(9) 0.8680(5) 0.0306(5) Uani 1 1 d . . .
C5 C 0.6553(3) 0.78514(8) 1.1414(4) 0.0221(4) Uani 1 1 d . . .
C3 C 0.6927(3) 0.88728(8) 1.1785(4) 0.0270(5) Uani 1 1 d . . .
C9 C 0.6626(3) 0.62542(8) 1.1442(4) 0.0239(4) Uani 1 1 d . . .
C11 C 0.7436(3) 0.59457(8) 1.3187(4) 0.0262(4) Uani 1 1 d . . .
C4 C 0.6347(3) 0.84092(8) 1.0699(4) 0.0229(4) Uani 1 1 d . . .
C2 C 0.6563(3) 0.93543(9) 1.0588(4) 0.0292(5) Uani 1 1 d . . .
H3 H 0.741(3) 0.8860(8) 1.293(4) 0.018(6) Uiso 1 1 d . . .
H7 H 0.774(3) 0.6902(10) 1.477(5) 0.034(6) Uiso 1 1 d . . .
H1 H 0.540(3) 0.9518(10) 0.763(5) 0.033(7) Uiso 1 1 d . . .
H2 H 0.689(3) 0.9677(11) 1.105(5) 0.030(7) Uiso 1 1 d . . .
H6 H 0.756(3) 0.7900(10) 1.429(5) 0.034(7) 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
S2 C5 1.728(2) . ?
S2 C8 1.738(2) . ?
S1 C1 1.713(2) . ?
S1 C4 1.732(2) . ?
C13 N3 1.144(3) . ?
C13 C10 1.430(4) . ?
C12 N2 1.142(3) . ?
C12 C10 1.438(3) . ?
C10 C9 1.371(3) . ?
N1 C11 1.137(3) . ?
C7 C8 1.386(3) . ?
C7 C6 1.392(3) . ?
C6 C5 1.383(3) . ?
C8 C9 1.436(3) . ?
C1 C2 1.355(3) . ?
C5 C4 1.444(3) . ?
C3 C4 1.392(3) . ?
C3 C2 1.417(3) . ?
C9 C11 1.455(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
C5 S2 C8 91.97(11) . . ?
C1 S1 C4 91.74(12) . . ?
N3 C13 C10 178.8(3) . . ?
N2 C12 C10 178.6(3) . . ?
C9 C10 C13 121.95(17) . . ?
C9 C10 C12 121.4(2) . . ?
C13 C10 C12 116.6(2) . . ?
C8 C7 C6 113.6(2) . . ?
C5 C6 C7 113.2(2) . . ?
C7 C8 C9 124.1(2) . . ?
C7 C8 S2 110.28(15) . . ?
C9 C8 S2 125.63(18) . . ?
C2 C1 S1 112.00(19) . . ?
C6 C5 C4 127.60(19) . . ?
C6 C5 S2 110.94(15) . . ?
C4 C5 S2 121.43(17) . . ?
C4 C3 C2 111.5(2) . . ?
C10 C9 C8 128.7(2) . . ?
C10 C9 C11 115.92(19) . . ?
C8 C9 C11 115.4(2) . . ?
N1 C11 C9 178.2(2) . . ?
C3 C4 C5 126.2(2) . . ?
C3 C4 S1 111.07(17) . . ?
C5 C4 S1 122.70(16) . . ?
C1 C2 C3 113.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_03168z
_database_code_depnum_ccdc_archive 'CCDC 1502184'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;
(E)-2-(5-(2-(thiophen-2-yl)vinyl)-thiophen-2-yl)-ethene-1,1,2-tricarbonitrile
;
_chemical_name_common            2
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 N3 S2'
_chemical_formula_sum            'C15 H7 N3 S2'
_chemical_formula_weight         293.36

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

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

_cell_length_a                   5.560(5)
_cell_length_b                   14.516(13)
_cell_length_c                   16.611(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.872(16)
_cell_angle_gamma                90
_cell_volume                     1338(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      2.458
_cell_measurement_theta_max      24.908

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.6605
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.389
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Siemnes SMART-1K CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9168
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2372
_reflns_number_gt                1774
_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 SMART'
_computing_cell_refinement       'Bruker SAINT V6.26A'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXL'
_computing_publication_material  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0369P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.54675(11) 0.71181(4) 0.11203(3) 0.02689(18) Uani 1 1 d . . . . .
C1 C 0.3110(4) 0.75553(16) 0.16306(13) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.1833(4) 0.68399(16) 0.19629(13) 0.0280(5) Uani 1 1 d . . . . .
H2 H 0.0481 0.6937 0.2273 0.028(6) Uiso 1 1 calc R . . . .
C3 C 0.2715(4) 0.59811(16) 0.18001(13) 0.0282(6) Uani 1 1 d . . . . .
H3 H 0.2021 0.5426 0.1980 0.038(7) Uiso 1 1 calc R . . . .
C4 C 0.4718(4) 0.60051(16) 0.13463(13) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.6098(4) 0.52462(16) 0.10577(13) 0.0265(5) Uani 1 1 d . . . . .
H5 H 0.7473 0.5377 0.0767 0.029(6) Uiso 1 1 calc R . . . .
C6 C 0.5517(4) 0.43646(16) 0.11834(13) 0.0252(5) Uani 1 1 d . . . . .
H6 H 0.4127 0.4263 0.1474 0.026(6) Uiso 1 1 calc R . . . .
S2 S 0.93208(11) 0.35811(5) 0.04114(4) 0.03246(19) Uani 1 1 d . . . . .
C7 C 0.6741(4) 0.35556(16) 0.09320(13) 0.0242(5) Uani 1 1 d . . . . .
C8 C 0.6092(4) 0.26579(16) 0.10851(13) 0.0276(6) Uani 1 1 d . . . . .
H8 H 0.4722 0.2496 0.1367 0.035(7) Uiso 1 1 calc R . . . .
C9 C 0.7665(5) 0.20117(18) 0.07822(15) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.7472 0.1365 0.0835 0.042(7) Uiso 1 1 calc R . . . .
C10 C 0.9496(5) 0.24051(18) 0.04045(15) 0.0370(6) Uani 1 1 d . . . . .
H10 H 1.0726 0.2068 0.0165 0.064(9) Uiso 1 1 calc R . . . .
C11 C 0.2530(4) 0.85056(16) 0.17094(13) 0.0267(5) Uani 1 1 d . . . . .
C12 C 0.0454(4) 0.86750(16) 0.21767(13) 0.0273(5) Uani 1 1 d . . . . .
N1 N -0.1219(4) 0.87887(15) 0.25246(12) 0.0376(5) Uani 1 1 d . . . . .
C13 C 0.3597(4) 0.92690(17) 0.14078(13) 0.0277(5) Uani 1 1 d . . . . .
C14 C 0.2790(4) 1.01736(17) 0.16144(14) 0.0303(6) Uani 1 1 d . . . . .
N2 N 0.2231(4) 1.08943(15) 0.17990(13) 0.0407(6) Uani 1 1 d . . . . .
C15 C 0.5573(4) 0.92283(16) 0.09014(14) 0.0303(6) Uani 1 1 d . . . . .
N3 N 0.7145(4) 0.92330(15) 0.04972(13) 0.0403(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
S1 C4 1.716(3) . ?
S1 C1 1.729(2) . ?
C1 C2 1.393(3) . ?
C1 C11 1.425(4) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.443(3) . ?
C5 C6 1.340(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.433(3) . ?
C6 H6 0.9500 . ?
S2 C10 1.710(3) . ?
S2 C7 1.725(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.399(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.357(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C13 1.368(3) . ?
C11 C12 1.455(3) . ?
C12 N1 1.140(3) . ?
C13 C15 1.430(3) . ?
C13 C14 1.437(4) . ?
C14 N2 1.139(3) . ?
C15 N3 1.138(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 92.00(12) . . ?
C2 C1 C11 124.1(2) . . ?
C2 C1 S1 110.13(18) . . ?
C11 C1 S1 125.75(18) . . ?
C3 C2 C1 113.6(2) . . ?
C3 C2 H2 123.2 . . ?
C1 C2 H2 123.2 . . ?
C2 C3 C4 113.2(2) . . ?
C2 C3 H3 123.4 . . ?
C4 C3 H3 123.4 . . ?
C3 C4 C5 128.8(2) . . ?
C3 C4 S1 110.99(18) . . ?
C5 C4 S1 120.24(17) . . ?
C6 C5 C4 122.6(2) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 127.8(2) . . ?
C5 C6 H6 116.1 . . ?
C7 C6 H6 116.1 . . ?
C10 S2 C7 91.81(12) . . ?
C8 C7 C6 125.8(2) . . ?
C8 C7 S2 110.44(17) . . ?
C6 C7 S2 123.77(18) . . ?
C7 C8 C9 112.9(2) . . ?
C7 C8 H8 123.5 . . ?
C9 C8 H8 123.5 . . ?
C10 C9 C8 113.0(2) . . ?
C10 C9 H9 123.5 . . ?
C8 C9 H9 123.5 . . ?
C9 C10 S2 111.85(19) . . ?
C9 C10 H10 124.1 . . ?
S2 C10 H10 124.1 . . ?
C13 C11 C1 130.1(2) . . ?
C13 C11 C12 116.0(2) . . ?
C1 C11 C12 113.9(2) . . ?
N1 C12 C11 177.6(3) . . ?
C11 C13 C15 123.5(2) . . ?
C11 C13 C14 120.2(2) . . ?
C15 C13 C14 116.3(2) . . ?
N2 C14 C13 177.2(3) . . ?
N3 C15 C13 177.3(3) . . ?

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
C4 S1 C1 C2 0.44(18) . . . . ?
C4 S1 C1 C11 -179.8(2) . . . . ?
C11 C1 C2 C3 179.4(2) . . . . ?
S1 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 S1 -0.5(3) . . . . ?
C1 S1 C4 C3 0.00(18) . . . . ?
C1 S1 C4 C5 179.06(19) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
S1 C4 C5 C6 -176.63(18) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C5 C6 C7 C8 179.1(2) . . . . ?
C5 C6 C7 S2 1.0(4) . . . . ?
C10 S2 C7 C8 0.05(19) . . . . ?
C10 S2 C7 C6 178.4(2) . . . . ?
C6 C7 C8 C9 -178.4(2) . . . . ?
S2 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 S2 -0.1(3) . . . . ?
C7 S2 C10 C9 0.0(2) . . . . ?
C2 C1 C11 C13 -178.9(2) . . . . ?
S1 C1 C11 C13 1.3(4) . . . . ?
C2 C1 C11 C12 0.1(3) . . . . ?
S1 C1 C11 C12 -179.66(17) . . . . ?
C1 C11 C13 C15 2.4(4) . . . . ?
C12 C11 C13 C15 -176.6(2) . . . . ?
C1 C11 C13 C14 -175.7(2) . . . . ?
C12 C11 C13 C14 5.2(3) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_01385z
_database_code_depnum_ccdc_archive 'CCDC 1502185'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
;         
(E)-2-(3,4-dibu-tyl-5-(2-(3,4-dibutylthiophen-2-yl)vinyl)thiophen-2-yl)
ethene-1,1,2-tricarbo-nitrile
;
_chemical_name_common            3
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H39 N3 S2'
_chemical_formula_sum            'C31 H39 N3 S2'
_chemical_formula_weight         517.77

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                   9.1187(16)
_cell_length_b                   10.6243(18)
_cell_length_c                   16.361(3)
_cell_angle_alpha                73.912(3)
_cell_angle_beta                 82.666(3)
_cell_angle_gamma                70.835(3)
_cell_volume                     1437.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    946
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.82

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   0.6228
_exptl_transmission_factor_max   0.8620
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Siemnes SMART-1K CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9453
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.296
_diffrn_reflns_theta_max         25.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5413
_reflns_number_gt                3751
_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 SMART'
_computing_cell_refinement       'Bruker SAINT V6.26A'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXL'
_computing_publication_material  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0785P)²+0.2168P] 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         5413
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.010
_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 1.02108(9) 0.22631(8) 0.01089(5) 0.0281(2) Uani 1 1 d . . . . .
C1 C 1.0456(3) 0.1779(3) -0.08446(19) 0.0258(7) Uani 1 1 d . . . . .
C2 C 0.9374(3) 0.2723(3) -0.14352(19) 0.0251(7) Uani 1 1 d . . . . .
C3 C 0.8314(3) 0.3778(3) -0.10817(19) 0.0250(7) Uani 1 1 d . . . . .
C4 C 0.8638(3) 0.3676(3) -0.02590(19) 0.0255(7) Uani 1 1 d . . . . .
C5 C 0.9288(4) 0.2707(3) -0.23479(19) 0.0280(7) Uani 1 1 d . . . . .
H5A H 1.0342 0.2264 -0.2565 0.034 Uiso 1 1 calc R U . . .
H5B H 0.8930 0.3667 -0.2698 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8200(4) 0.1946(3) -0.2451(2) 0.0322(8) Uani 1 1 d . . . . .
H6A H 0.7154 0.2370 -0.2216 0.039 Uiso 1 1 calc R U . . .
H6B H 0.8578 0.0978 -0.2115 0.039 Uiso 1 1 calc R U . . .
C7 C 0.8071(4) 0.1967(3) -0.3382(2) 0.0410(9) Uani 1 1 d . . . . .
H7A H 0.9128 0.1608 -0.3627 0.049 Uiso 1 1 calc R U . . .
H7B H 0.7481 0.1339 -0.3395 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7284(5) 0.3380(4) -0.3933(2) 0.0541(11) Uani 1 1 d . . . . .
H8A H 0.7243 0.3315 -0.4515 0.081 Uiso 1 1 calc R U . . .
H8B H 0.6226 0.3735 -0.3704 0.081 Uiso 1 1 calc R U . . .
H8C H 0.7875 0.4004 -0.3937 0.081 Uiso 1 1 calc R U . . .
C9 C 0.6984(4) 0.4899(3) -0.1559(2) 0.0281(7) Uani 1 1 d . . . . .
H9A H 0.6083 0.5102 -0.1156 0.034 Uiso 1 1 calc R U . . .
H9B H 0.6676 0.4559 -0.1996 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7368(4) 0.6232(3) -0.1994(2) 0.0314(8) Uani 1 1 d . . . . .
H10A H 0.7516 0.6653 -0.1554 0.038 Uiso 1 1 calc R U . . .
H10B H 0.8358 0.6013 -0.2332 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6098(4) 0.7267(3) -0.2578(2) 0.0378(8) Uani 1 1 d . . . . .
H11A H 0.6033 0.6886 -0.3055 0.045 Uiso 1 1 calc R U . . .
H11B H 0.5087 0.7405 -0.2255 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6388(5) 0.8644(3) -0.2934(2) 0.0559(12) Uani 1 1 d . . . . .
H12A H 0.5544 0.9270 -0.3303 0.084 Uiso 1 1 calc R U . . .
H12B H 0.6431 0.9036 -0.2464 0.084 Uiso 1 1 calc R U . . .
H12C H 0.7377 0.8516 -0.3264 0.084 Uiso 1 1 calc R U . . .
C13 C 0.7849(4) 0.4606(3) 0.0270(2) 0.0282(7) Uani 1 1 d . . . . .
H13A H 0.7054 0.5418 0.0024 0.034 Uiso 1 1 calc R U . . .
C14 C 0.8162(3) 0.4399(3) 0.1081(2) 0.0274(7) Uani 1 1 d . . . . .
H14A H 0.8904 0.3546 0.1323 0.033 Uiso 1 1 calc R U . . .
S2 S 0.62963(9) 0.69773(7) 0.12641(5) 0.0273(2) Uani 1 1 d . . . . .
C15 C 0.7509(3) 0.5316(3) 0.16354(19) 0.0242(7) Uani 1 1 d . . . . .
C16 C 0.7793(3) 0.5040(3) 0.24825(19) 0.0249(7) Uani 1 1 d . . . . .
C17 C 0.7038(4) 0.6209(3) 0.28320(19) 0.0269(7) Uani 1 1 d . . . . .
C18 C 0.6203(4) 0.7302(3) 0.22422(19) 0.0287(7) Uani 1 1 d . . . . .
H18A H 0.5625 0.8161 0.2360 0.034 Uiso 1 1 calc R U . . .
C19 C 0.8686(4) 0.3669(3) 0.3022(2) 0.0302(7) Uani 1 1 d . . . . .
H19A H 0.9292 0.3820 0.3427 0.036 Uiso 1 1 calc R U . . .
H19B H 0.9431 0.3139 0.2651 0.036 Uiso 1 1 calc R U . . .
C20 C 0.7651(4) 0.2819(3) 0.3522(2) 0.0295(7) Uani 1 1 d . . . . .
H20A H 0.6837 0.3381 0.3850 0.035 Uiso 1 1 calc R U . . .
H20B H 0.7128 0.2581 0.3119 0.035 Uiso 1 1 calc R U . . .
C21 C 0.8561(4) 0.1502(3) 0.4131(2) 0.0378(8) Uani 1 1 d . . . . .
H21A H 0.9381 0.0946 0.3803 0.045 Uiso 1 1 calc R U . . .
H21B H 0.9078 0.1742 0.4537 0.045 Uiso 1 1 calc R U . . .
C22 C 0.7553(5) 0.0649(4) 0.4623(3) 0.0508(10) Uani 1 1 d . . . . .
H22A H 0.8194 -0.0184 0.5004 0.076 Uiso 1 1 calc R U . . .
H22B H 0.6753 0.1186 0.4960 0.076 Uiso 1 1 calc R U . . .
H22C H 0.7056 0.0390 0.4226 0.076 Uiso 1 1 calc R U . . .
C23 C 0.7203(4) 0.6165(3) 0.3743(2) 0.0346(8) Uani 1 1 d . . . . .
H23A H 0.8322 0.5797 0.3864 0.041 Uiso 1 1 calc R U . . .
H23B H 0.6692 0.5507 0.4114 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6534(4) 0.7530(3) 0.3989(2) 0.0328(8) Uani 1 1 d . . . . .
H24A H 0.5425 0.7930 0.3846 0.039 Uiso 1 1 calc R U . . .
H24B H 0.7088 0.8177 0.3651 0.039 Uiso 1 1 calc R U . . .
C25 C 0.6670(4) 0.7376(3) 0.4934(2) 0.0339(8) Uani 1 1 d . . . . .
H25A H 0.6096 0.6743 0.5269 0.041 Uiso 1 1 calc R U . . .
H25B H 0.6168 0.8284 0.5061 0.041 Uiso 1 1 calc R U . . .
C26 C 0.8338(4) 0.6829(4) 0.5218(2) 0.0438(9) Uani 1 1 d . . . . .
H26A H 0.8341 0.6755 0.5828 0.066 Uiso 1 1 calc R U . . .
H26B H 0.8837 0.5919 0.5109 0.066 Uiso 1 1 calc R U . . .
H26C H 0.8910 0.7461 0.4900 0.066 Uiso 1 1 calc R U . . .
C27 C 1.1635(3) 0.0539(3) -0.09390(19) 0.0260(7) Uani 1 1 d . . . . .
C28 C 1.1645(4) 0.0026(3) -0.1667(2) 0.0344(8) Uani 1 1 d . . . . .
N1 N 1.1734(4) -0.0446(3) -0.2229(2) 0.0522(9) Uani 1 1 d . . . . .
C29 C 1.2782(3) -0.0308(3) -0.03699(19) 0.0254(7) Uani 1 1 d . . . . .
C30 C 1.3770(3) -0.1612(3) -0.0509(2) 0.0280(7) Uani 1 1 d . . . . .
N2 N 1.4551(3) -0.2658(3) -0.05828(18) 0.0398(7) Uani 1 1 d . . . . .
C31 C 1.3147(4) -0.0005(3) 0.0357(2) 0.0267(7) Uani 1 1 d . . . . .
N3 N 1.3546(3) 0.0150(3) 0.09480(18) 0.0356(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
S1 C4 1.726(3) . ?
S1 C1 1.740(3) . ?
C1 C2 1.404(4) . ?
C1 C27 1.434(4) . ?
C2 C3 1.424(4) . ?
C2 C5 1.511(4) . ?
C3 C4 1.382(4) . ?
C3 C9 1.509(4) . ?
C4 C13 1.445(4) . ?
C5 C6 1.520(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.536(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.513(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.336(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.449(4) . ?
C14 H14A 0.9500 . ?
S2 C18 1.714(3) . ?
S2 C15 1.733(3) . ?
C15 C16 1.375(4) . ?
C16 C17 1.441(4) . ?
C16 C19 1.502(4) . ?
C17 C18 1.358(4) . ?
C17 C23 1.503(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.525(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.506(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.522(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.526(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.523(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C29 1.392(4) . ?
C27 C28 1.439(4) . ?
C28 N1 1.146(4) . ?
C29 C31 1.418(4) . ?
C29 C30 1.444(4) . ?
C30 N2 1.135(4) . ?
C31 N3 1.146(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
C4 S1 C1 91.84(14) . . ?
C2 C1 C27 128.6(3) . . ?
C2 C1 S1 111.2(2) . . ?
C27 C1 S1 120.2(2) . . ?
C1 C2 C3 111.9(3) . . ?
C1 C2 C5 126.8(3) . . ?
C3 C2 C5 121.3(3) . . ?
C4 C3 C2 113.1(3) . . ?
C4 C3 C9 123.4(3) . . ?
C2 C3 C9 123.5(3) . . ?
C3 C4 C13 127.6(3) . . ?
C3 C4 S1 111.9(2) . . ?
C13 C4 S1 120.5(2) . . ?
C2 C5 C6 113.0(3) . . ?
C2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 113.1(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 113.9(3) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C10 113.6(3) . . ?
C3 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C3 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 112.4(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 112.6(3) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 124.3(3) . . ?
C14 C13 H13A 117.8 . . ?
C4 C13 H13A 117.8 . . ?
C13 C14 C15 127.9(3) . . ?
C13 C14 H14A 116.0 . . ?
C15 C14 H14A 116.0 . . ?
C18 S2 C15 91.18(15) . . ?
C16 C15 C14 126.4(3) . . ?
C16 C15 S2 111.6(2) . . ?
C14 C15 S2 121.9(2) . . ?
C15 C16 C17 112.2(3) . . ?
C15 C16 C19 125.6(3) . . ?
C17 C16 C19 122.1(3) . . ?
C18 C17 C16 111.7(3) . . ?
C18 C17 C23 126.3(3) . . ?
C16 C17 C23 122.0(3) . . ?
C17 C18 S2 113.3(2) . . ?
C17 C18 H18A 123.4 . . ?
S2 C18 H18A 123.4 . . ?
C16 C19 C20 113.3(2) . . ?
C16 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C16 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 112.4(3) . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 112.8(3) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 C24 116.1(3) . . ?
C17 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
C17 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C23 C24 C25 112.5(3) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 113.7(3) . . ?
C24 C25 H25A 108.8 . . ?
C26 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
C26 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C29 C27 C1 127.0(3) . . ?
C29 C27 C28 113.6(3) . . ?
C1 C27 C28 119.3(3) . . ?
N1 C28 C27 175.8(3) . . ?
C27 C29 C31 126.1(3) . . ?
C27 C29 C30 120.2(3) . . ?
C31 C29 C30 113.7(3) . . ?
N2 C30 C29 177.2(3) . . ?
N3 C31 C29 174.5(3) . . ?

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
C4 S1 C1 C2 2.0(2) . . . . ?
C4 S1 C1 C27 -177.0(3) . . . . ?
C27 C1 C2 C3 175.7(3) . . . . ?
S1 C1 C2 C3 -3.3(3) . . . . ?
C27 C1 C2 C5 -5.4(5) . . . . ?
S1 C1 C2 C5 175.6(2) . . . . ?
C1 C2 C3 C4 3.2(4) . . . . ?
C5 C2 C3 C4 -175.8(3) . . . . ?
C1 C2 C3 C9 -177.4(3) . . . . ?
C5 C2 C3 C9 3.6(5) . . . . ?
C2 C3 C4 C13 176.8(3) . . . . ?
C9 C3 C4 C13 -2.6(5) . . . . ?
C2 C3 C4 S1 -1.7(3) . . . . ?
C9 C3 C4 S1 178.9(2) . . . . ?
C1 S1 C4 C3 -0.2(2) . . . . ?
C1 S1 C4 C13 -178.8(3) . . . . ?
C1 C2 C5 C6 92.9(4) . . . . ?
C3 C2 C5 C6 -88.2(3) . . . . ?
C2 C5 C6 C7 178.2(2) . . . . ?
C5 C6 C7 C8 -67.1(4) . . . . ?
C4 C3 C9 C10 84.1(4) . . . . ?
C2 C3 C9 C10 -95.3(4) . . . . ?
C3 C9 C10 C11 171.4(3) . . . . ?
C9 C10 C11 C12 173.7(3) . . . . ?
C3 C4 C13 C14 175.6(3) . . . . ?
S1 C4 C13 C14 -6.0(5) . . . . ?
C4 C13 C14 C15 175.3(3) . . . . ?
C13 C14 C15 C16 176.1(3) . . . . ?
C13 C14 C15 S2 -6.8(5) . . . . ?
C18 S2 C15 C16 1.0(2) . . . . ?
C18 S2 C15 C14 -176.6(3) . . . . ?
C14 C15 C16 C17 176.1(3) . . . . ?
S2 C15 C16 C17 -1.3(3) . . . . ?
C14 C15 C16 C19 -7.8(5) . . . . ?
S2 C15 C16 C19 174.7(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C19 C16 C17 C18 -175.2(3) . . . . ?
C15 C16 C17 C23 -178.8(3) . . . . ?
C19 C16 C17 C23 5.0(5) . . . . ?
C16 C17 C18 S2 -0.3(4) . . . . ?
C23 C17 C18 S2 179.5(3) . . . . ?
C15 S2 C18 C17 -0.4(3) . . . . ?
C15 C16 C19 C20 -94.9(4) . . . . ?
C17 C16 C19 C20 80.8(4) . . . . ?
C16 C19 C20 C21 -174.2(3) . . . . ?
C19 C20 C21 C22 -179.5(3) . . . . ?
C18 C17 C23 C24 -8.2(5) . . . . ?
C16 C17 C23 C24 171.6(3) . . . . ?
C17 C23 C24 C25 176.7(3) . . . . ?
C23 C24 C25 C26 61.5(4) . . . . ?
C2 C1 C27 C29 173.6(3) . . . . ?
S1 C1 C27 C29 -7.6(5) . . . . ?
C2 C1 C27 C28 -9.9(5) . . . . ?
S1 C1 C27 C28 169.0(2) . . . . ?
C1 C27 C29 C31 -9.8(5) . . . . ?
C28 C27 C29 C31 173.5(3) . . . . ?
C1 C27 C29 C30 172.5(3) . . . . ?
C28 C27 C29 C30 -4.3(4) . . . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.070

_shelxl_version_number           2014/6

