# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_9490
_database_code_depnum_ccdc_archive 'CCDC 1540237'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N3 S2'
_chemical_formula_weight         303.44

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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'
'-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                   10.5462(6)
_cell_length_b                   11.8138(6)
_cell_length_c                   24.1532(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3009.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5839
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8188
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20165
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0272
_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       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3455
_reflns_number_gt                3130
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0590P)²+2.1451P] 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         3455
_refine_ls_number_parameters     194
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C4A C 0.4329(3) 0.3417(6) 0.5796(4) 0.0267(14) Uani 0.565(19) 1 d PD A 1
H4AA H 0.3758 0.3065 0.6072 0.032 Uiso 0.565(19) 1 calc PR A 1
H4AB H 0.3807 0.3872 0.5538 0.032 Uiso 0.565(19) 1 calc PR A 1
C4B C 0.4522(8) 0.3665(5) 0.5605(4) 0.0235(18) Uani 0.435(19) 1 d PD A 2
H4BA H 0.3629 0.3608 0.5728 0.028 Uiso 0.435(19) 1 calc PR A 2
H4BB H 0.4547 0.4135 0.5266 0.028 Uiso 0.435(19) 1 calc PR A 2
S1 S 0.54726(4) 0.43318(4) 0.61464(2) 0.02048(14) Uani 1 1 d D . .
S2 S 0.32558(5) 0.64905(5) 0.61294(2) 0.02707(15) Uani 1 1 d . . .
N1 N 0.62796(13) 0.24218(12) 0.57351(6) 0.0162(3) Uani 1 1 d . . .
N2 N 0.77862(14) 0.31393(12) 0.62339(6) 0.0149(3) Uani 1 1 d . . .
N3 N 0.26593(17) 0.57066(15) 0.50641(7) 0.0294(4) Uani 1 1 d . . .
C1 C 0.82344(17) 0.21322(14) 0.60023(8) 0.0177(4) Uani 1 1 d . A .
H1 H 0.9054 0.1817 0.6055 0.021 Uiso 1 1 calc R . .
C2 C 0.72971(17) 0.16857(15) 0.56895(7) 0.0188(4) Uani 1 1 d . A .
H2 H 0.7329 0.1005 0.5481 0.023 Uiso 1 1 calc R . .
C3 C 0.50249(17) 0.25096(18) 0.54803(9) 0.0281(4) Uani 1 1 d D A .
H3A H 0.4569 0.1779 0.5507 0.034 Uiso 0.565(19) 1 calc PR A 1
H3B H 0.5101 0.2719 0.5085 0.034 Uiso 0.565(19) 1 calc PR A 1
H3C H 0.4452 0.1926 0.5635 0.034 Uiso 0.435(19) 1 d PR A 2
H3D H 0.5087 0.2394 0.5075 0.034 Uiso 0.435(19) 1 d PR A 2
C5 C 0.65990(16) 0.32861(15) 0.60580(7) 0.0154(3) Uani 1 1 d . A .
C6 C 0.84695(15) 0.39166(14) 0.65889(7) 0.0142(3) Uani 1 1 d . A .
C7 C 0.80564(16) 0.40574(14) 0.71331(7) 0.0155(3) Uani 1 1 d . . .
C8 C 0.86838(16) 0.48648(14) 0.74560(7) 0.0165(3) Uani 1 1 d . A .
H8 H 0.8409 0.4993 0.7825 0.020 Uiso 1 1 calc R . .
C9 C 0.97015(16) 0.54858(14) 0.72493(7) 0.0168(3) Uani 1 1 d . . .
C10 C 1.01035(16) 0.52862(14) 0.67096(7) 0.0175(4) Uani 1 1 d . A .
H10 H 1.0809 0.5697 0.6570 0.021 Uiso 1 1 calc R . .
C11 C 0.95045(16) 0.45031(14) 0.63684(7) 0.0154(3) Uani 1 1 d . . .
C12 C 0.69908(17) 0.33645(15) 0.73760(8) 0.0195(4) Uani 1 1 d . A .
H12A H 0.6176 0.3707 0.7276 0.029 Uiso 1 1 calc R . .
H12B H 0.7074 0.3345 0.7780 0.029 Uiso 1 1 calc R . .
H12C H 0.7030 0.2592 0.7230 0.029 Uiso 1 1 calc R . .
C13 C 1.03941(18) 0.63331(16) 0.76055(8) 0.0217(4) Uani 1 1 d . A .
H13A H 1.1168 0.5987 0.7753 0.032 Uiso 1 1 calc R . .
H13B H 0.9846 0.6567 0.7913 0.032 Uiso 1 1 calc R . .
H13C H 1.0618 0.6996 0.7382 0.032 Uiso 1 1 calc R . .
C14 C 0.99772(18) 0.42948(15) 0.57890(7) 0.0200(4) Uani 1 1 d . A .
H14A H 1.0561 0.4902 0.5682 0.030 Uiso 1 1 calc R . .
H14B H 0.9257 0.4280 0.5533 0.030 Uiso 1 1 calc R . .
H14C H 1.0421 0.3567 0.5775 0.030 Uiso 1 1 calc R . .
C15 C 0.29094(16) 0.60431(15) 0.55024(8) 0.0190(4) 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
C4A C3 1.507(4) . ?
C4A S1 1.827(3) . ?
C4B C3 1.495(4) . ?
C4B S1 1.826(4) . ?
S1 C5 1.7271(18) . ?
S2 C15 1.645(2) . ?
N1 C5 1.328(2) . ?
N1 C2 1.386(2) . ?
N1 C3 1.463(2) . ?
N2 C5 1.333(2) . ?
N2 C1 1.397(2) . ?
N2 C6 1.448(2) . ?
N3 C15 1.161(3) . ?
C1 C2 1.351(3) . ?
C6 C7 1.395(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.399(2) . ?
C7 C12 1.509(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.391(3) . ?
C9 C13 1.508(2) . ?
C10 C11 1.391(2) . ?
C11 C14 1.506(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
C3 C4A S1 109.5(2) . . ?
C3 C4B S1 110.1(2) . . ?
C5 S1 C4B 88.88(17) . . ?
C5 S1 C4A 88.50(15) . . ?
C4B S1 C4A 18.38(19) . . ?
C5 N1 C2 109.43(14) . . ?
C5 N1 C3 114.96(15) . . ?
C2 N1 C3 135.35(15) . . ?
C5 N2 C1 107.51(14) . . ?
C5 N2 C6 124.98(14) . . ?
C1 N2 C6 127.49(14) . . ?
C2 C1 N2 107.98(15) . . ?
C1 C2 N1 106.08(15) . . ?
N1 C3 C4B 107.5(2) . . ?
N1 C3 C4A 106.1(2) . . ?
C4B C3 C4A 22.4(2) . . ?
N1 C5 N2 108.98(15) . . ?
N1 C5 S1 116.61(13) . . ?
N2 C5 S1 134.38(14) . . ?
C7 C6 C11 122.94(15) . . ?
C7 C6 N2 118.57(15) . . ?
C11 C6 N2 118.49(15) . . ?
C6 C7 C8 117.33(16) . . ?
C6 C7 C12 122.30(15) . . ?
C8 C7 C12 120.36(16) . . ?
C9 C8 C7 121.59(16) . . ?
C10 C9 C8 118.79(16) . . ?
C10 C9 C13 119.97(16) . . ?
C8 C9 C13 121.21(16) . . ?
C11 C10 C9 121.98(16) . . ?
C10 C11 C6 117.29(16) . . ?
C10 C11 C14 120.60(16) . . ?
C6 C11 C14 122.10(15) . . ?
N3 C15 S2 178.66(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_b296
_database_code_depnum_ccdc_archive 'CCDC 1540240'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.	2020-03-10 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 H14 N4 S2'
_chemical_formula_weight         290.40

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.035(5)
_cell_length_b                   11.727(7)
_cell_length_c                   13.103(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1388.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4103
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.31

_exptl_crystal_description       ROD
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8064
_exptl_absorpt_correction_T_max  0.8959
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9140
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3157
_reflns_number_gt                2985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0504P)²+0.0788P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32281(6) 0.52347(4) 0.49177(3) 0.03415(13) Uani 1 1 d . . .
S2 S 0.84774(7) 0.41664(5) 0.54095(4) 0.04459(16) Uani 1 1 d . . .
N1 N 0.13343(19) 0.54228(13) 0.65732(11) 0.0297(3) Uani 1 1 d . . .
N2 N 0.12823(17) 0.68648(13) 0.55622(12) 0.0281(3) Uani 1 1 d . . .
N3 N 0.02639(19) 0.71069(15) 0.63226(12) 0.0355(4) Uani 1 1 d . . .
N4 N 0.6280(2) 0.45077(19) 0.39356(16) 0.0548(6) Uani 1 1 d . . .
C1 C 0.1922(2) 0.58481(15) 0.57095(13) 0.0254(4) Uani 1 1 d . . .
C2 C 0.3650(3) 0.39635(17) 0.56781(18) 0.0424(5) Uani 1 1 d . . .
H2A H 0.4050 0.3372 0.5227 0.051 Uiso 1 1 calc R . .
H2B H 0.4417 0.4155 0.6179 0.051 Uiso 1 1 calc R . .
C3 C 0.2310(3) 0.34910(18) 0.62351(19) 0.0462(6) Uani 1 1 d . . .
H3A H 0.1529 0.3327 0.5737 0.055 Uiso 1 1 calc R . .
H3B H 0.2583 0.2771 0.6564 0.055 Uiso 1 1 calc R . .
C4 C 0.1709(3) 0.43025(18) 0.70367(15) 0.0427(5) Uani 1 1 d . . .
H4A H 0.0822 0.3972 0.7349 0.051 Uiso 1 1 calc R . .
H4B H 0.2450 0.4411 0.7574 0.051 Uiso 1 1 calc R . .
C5 C 0.0333(2) 0.62163(19) 0.69113(15) 0.0373(5) Uani 1 1 d . . .
H5 H -0.0241 0.6126 0.7504 0.045 Uiso 1 1 calc R . .
C6 C 0.1634(2) 0.77057(16) 0.47749(13) 0.0321(4) Uani 1 1 d . . .
H6A H 0.2655 0.7583 0.4549 0.039 Uiso 1 1 calc R . .
H6B H 0.1581 0.8468 0.5078 0.039 Uiso 1 1 calc R . .
C7 C 0.0628(2) 0.76734(16) 0.38485(13) 0.0262(4) Uani 1 1 d . . .
C8 C 0.0760(2) 0.85736(17) 0.31475(15) 0.0333(4) Uani 1 1 d . . .
H8 H 0.1454 0.9157 0.3259 0.040 Uiso 1 1 calc R . .
C9 C -0.0138(3) 0.85975(18) 0.22899(15) 0.0396(5) Uani 1 1 d . . .
H9 H -0.0048 0.9198 0.1819 0.048 Uiso 1 1 calc R . .
C10 C -0.1170(3) 0.77396(19) 0.21207(15) 0.0395(5) Uani 1 1 d . . .
H10 H -0.1777 0.7765 0.1539 0.047 Uiso 1 1 calc R . .
C11 C -0.1308(2) 0.68453(19) 0.28075(15) 0.0362(5) Uani 1 1 d . . .
H11 H -0.2008 0.6267 0.2692 0.043 Uiso 1 1 calc R . .
C12 C -0.0400(2) 0.68078(16) 0.36718(14) 0.0297(4) Uani 1 1 d . . .
H12 H -0.0483 0.6198 0.4134 0.036 Uiso 1 1 calc R . .
C13 C 0.7183(2) 0.43536(17) 0.45446(16) 0.0342(4) 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 C1 1.728(2) . ?
S1 C2 1.833(2) . ?
S2 C13 1.643(2) . ?
N1 C1 1.346(2) . ?
N1 C5 1.371(3) . ?
N1 C4 1.486(3) . ?
N2 C1 1.339(2) . ?
N2 N3 1.386(2) . ?
N2 C6 1.462(2) . ?
N3 C5 1.300(3) . ?
N4 C13 1.156(3) . ?
C2 C3 1.518(3) . ?
C3 C4 1.518(3) . ?
C6 C7 1.517(3) . ?
C7 C12 1.395(3) . ?
C7 C8 1.404(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.389(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.399(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
C1 S1 C2 98.87(10) . . ?
C1 N1 C5 106.28(16) . . ?
C1 N1 C4 125.55(17) . . ?
C5 N1 C4 128.16(17) . . ?
C1 N2 N3 111.43(15) . . ?
C1 N2 C6 127.50(16) . . ?
N3 N2 C6 120.89(15) . . ?
C5 N3 N2 103.31(16) . . ?
N2 C1 N1 106.32(15) . . ?
N2 C1 S1 125.37(14) . . ?
N1 C1 S1 128.31(14) . . ?
C3 C2 S1 113.09(16) . . ?
C4 C3 C2 112.91(19) . . ?
N1 C4 C3 110.66(16) . . ?
N3 C5 N1 112.65(18) . . ?
N2 C6 C7 114.70(15) . . ?
C12 C7 C8 119.67(17) . . ?
C12 C7 C6 123.35(16) . . ?
C8 C7 C6 116.98(17) . . ?
C9 C8 C7 119.71(19) . . ?
C8 C9 C10 120.49(19) . . ?
C11 C10 C9 120.26(19) . . ?
C10 C11 C12 119.8(2) . . ?
C7 C12 C11 120.10(17) . . ?
N4 C13 S2 178.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_9309
_database_code_depnum_ccdc_archive 'CCDC 1540239'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 S2'
_chemical_formula_weight         325.44

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   5.3591(3)
_cell_length_b                   19.3576(11)
_cell_length_c                   15.0546(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0410(10)
_cell_angle_gamma                90.00
_cell_volume                     1553.08(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5027
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8586
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10876
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3537
_reflns_number_gt                3142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0616P)²+0.4063P] 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         3537
_refine_ls_number_parameters     227
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2A S 0.8215(3) 0.56628(10) 0.67931(11) 0.0293(4) Uani 0.553(4) 1 d PD A 1
N3A N 1.0558(12) 0.6381(3) 0.5496(4) 0.0476(14) Uani 0.553(4) 1 d PD A 1
C17A C 0.9638(6) 0.60896(18) 0.6045(2) 0.0262(7) Uani 0.553(4) 1 d PD A 1
S2B S 1.0717(4) 0.63817(11) 0.58282(13) 0.0361(5) Uani 0.447(4) 1 d PD A 2
N3B N 0.7886(17) 0.5475(4) 0.6764(6) 0.059(3) Uani 0.447(4) 1 d PD A 2
C17B C 0.9063(8) 0.5847(2) 0.6380(3) 0.0255(8) Uani 0.447(4) 1 d PD A 2
S1 S -0.06826(7) 0.822075(18) 0.93929(2) 0.02699(12) Uani 1 1 d . . .
N1 N 0.2275(2) 0.75836(6) 0.82134(7) 0.0214(2) Uani 1 1 d . . .
N2 N 0.2527(2) 0.87071(6) 0.83668(7) 0.0214(2) Uani 1 1 d . . .
C1 C 0.1438(2) 0.81333(7) 0.86246(9) 0.0216(3) Uani 1 1 d . . .
C2 C 0.4063(2) 0.78153(7) 0.76678(8) 0.0218(3) Uani 1 1 d . . .
C3 C 0.5584(3) 0.74514(7) 0.71357(9) 0.0255(3) Uani 1 1 d . . .
H3 H 0.5474 0.6964 0.7070 0.031 Uiso 1 1 calc R . .
C4 C 0.7266(3) 0.78412(8) 0.67072(9) 0.0288(3) Uani 1 1 d . . .
H4 H 0.8354 0.7614 0.6343 0.035 Uiso 1 1 calc R . .
C5 C 0.7410(3) 0.85604(8) 0.67962(9) 0.0284(3) Uani 1 1 d . . .
H5 H 0.8589 0.8807 0.6489 0.034 Uiso 1 1 calc R . .
C6 C 0.5876(3) 0.89247(7) 0.73213(9) 0.0253(3) Uani 1 1 d . . .
H6 H 0.5958 0.9413 0.7376 0.030 Uiso 1 1 calc R . .
C7 C 0.4219(2) 0.85335(7) 0.77614(8) 0.0219(3) Uani 1 1 d . . .
C8 C 0.1627(3) 0.68611(7) 0.83674(10) 0.0251(3) Uani 1 1 d . . .
H8A H 0.1233 0.6625 0.7786 0.030 Uiso 1 1 calc R . .
H8B H 0.0115 0.6842 0.8692 0.030 Uiso 1 1 calc R . .
C9 C 0.3773(3) 0.64923(7) 0.89049(9) 0.0240(3) Uani 1 1 d . . .
C10 C 0.4465(4) 0.58398(9) 0.86615(13) 0.0528(5) Uani 1 1 d . . .
H10 H 0.3597 0.5620 0.8156 0.063 Uiso 1 1 calc R . .
C11 C 0.6429(5) 0.55037(11) 0.91552(16) 0.0733(8) Uani 1 1 d . . .
H11 H 0.6896 0.5053 0.8986 0.088 Uiso 1 1 calc R . .
C12 C 0.7717(4) 0.58166(10) 0.98901(12) 0.0479(5) Uani 1 1 d . . .
H12 H 0.9067 0.5583 1.0224 0.057 Uiso 1 1 calc R . .
C13 C 0.7033(3) 0.64672(8) 1.01349(10) 0.0302(3) Uani 1 1 d . . .
H13 H 0.7905 0.6685 1.0641 0.036 Uiso 1 1 calc R . .
C14 C 0.5071(3) 0.68053(7) 0.96435(9) 0.0248(3) Uani 1 1 d . . .
H14 H 0.4609 0.7256 0.9814 0.030 Uiso 1 1 calc R . .
C15 C 0.1831(3) 0.93502(7) 0.87868(11) 0.0323(3) Uani 1 1 d . . .
H15A H 0.1139 0.9685 0.8328 0.039 Uiso 1 1 calc R . .
H15B H 0.3315 0.9560 0.9132 0.039 Uiso 1 1 calc R . .
C16 C -0.0153(3) 0.91608(7) 0.94078(9) 0.0263(3) Uani 1 1 d . . .
H16A H -0.1745 0.9402 0.9211 0.032 Uiso 1 1 calc R . .
H16B H 0.0415 0.9312 1.0024 0.032 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
S2A C17A 1.648(5) . ?
N3A C17A 1.153(6) . ?
S2B C17B 1.644(6) . ?
N3B C17B 1.151(7) . ?
S1 C1 1.7131(14) . ?
S1 C16 1.8414(15) . ?
N1 C1 1.3322(17) . ?
N1 C2 1.4000(17) . ?
N1 C8 1.4654(17) . ?
N2 C1 1.3313(17) . ?
N2 C7 1.3926(17) . ?
N2 C15 1.4623(18) . ?
C2 C3 1.3927(19) . ?
C2 C7 1.3990(19) . ?
C3 C4 1.386(2) . ?
C4 C5 1.400(2) . ?
C5 C6 1.391(2) . ?
C6 C7 1.387(2) . ?
C8 C9 1.5139(19) . ?
C9 C10 1.377(2) . ?
C9 C14 1.387(2) . ?
C10 C11 1.385(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.373(2) . ?
C13 C14 1.385(2) . ?
C15 C16 1.533(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
N3A C17A S2A 177.2(4) . . ?
N3B C17B S2B 179.4(6) . . ?
C1 S1 C16 89.63(7) . . ?
C1 N1 C2 107.54(11) . . ?
C1 N1 C8 126.29(12) . . ?
C2 N1 C8 125.93(11) . . ?
C1 N2 C7 108.97(11) . . ?
C1 N2 C15 116.41(12) . . ?
C7 N2 C15 134.54(12) . . ?
N2 C1 N1 110.58(12) . . ?
N2 C1 S1 117.17(10) . . ?
N1 C1 S1 132.24(11) . . ?
C3 C2 C7 121.89(13) . . ?
C3 C2 N1 130.82(13) . . ?
C7 C2 N1 107.25(11) . . ?
C4 C3 C2 116.18(13) . . ?
C3 C4 C5 121.92(13) . . ?
C6 C5 C4 121.91(13) . . ?
C7 C6 C5 116.18(13) . . ?
C6 C7 N2 132.41(13) . . ?
C6 C7 C2 121.91(12) . . ?
N2 C7 C2 105.64(11) . . ?
N1 C8 C9 110.81(11) . . ?
C10 C9 C14 119.19(14) . . ?
C10 C9 C8 120.07(13) . . ?
C14 C9 C8 120.75(12) . . ?
C9 C10 C11 119.92(16) . . ?
C12 C11 C10 120.76(17) . . ?
C13 C12 C11 119.50(15) . . ?
C12 C13 C14 119.96(14) . . ?
C13 C14 C9 120.69(13) . . ?
N2 C15 C16 106.55(12) . . ?
C15 C16 S1 110.18(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_9558
_database_code_depnum_ccdc_archive 'CCDC 1540238'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N3 S2'
_chemical_formula_weight         379.53

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.1553(5)
_cell_length_b                   16.6915(10)
_cell_length_c                   14.5815(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2050(10)
_cell_angle_gamma                90.00
_cell_volume                     1940.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1863
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      22.05

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13597
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4462
_reflns_number_gt                3004
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0695P)²+0.0766P] 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         4462
_refine_ls_number_parameters     266
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.063
_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
S1 S 1.05589(8) 0.66300(3) 0.84113(4) 0.03672(19) Uani 1 1 d . . .
N1 N 0.9844(3) 0.52678(11) 0.74449(13) 0.0356(5) Uani 1 1 d . . .
N2 N 0.8161(3) 0.62095(11) 0.67936(13) 0.0349(5) Uani 1 1 d . . .
C1 C 0.9458(3) 0.60497(13) 0.74974(16) 0.0320(5) Uani 1 1 d . . .
C2 C 0.8763(3) 0.49330(15) 0.66789(17) 0.0449(7) Uani 1 1 d . . .
H2 H 0.8754 0.4396 0.6482 0.054 Uiso 1 1 calc R . .
C3 C 0.7735(4) 0.55161(14) 0.62715(18) 0.0458(7) Uani 1 1 d . . .
H3 H 0.6880 0.5465 0.5730 0.055 Uiso 1 1 calc R . .
C4 C 1.1072(3) 0.48378(12) 0.81348(16) 0.0311(5) Uani 1 1 d . . .
C5 C 1.0498(3) 0.43929(13) 0.88059(16) 0.0325(5) Uani 1 1 d . . .
C6 C 1.1688(3) 0.39713(13) 0.94527(16) 0.0357(6) Uani 1 1 d . . .
H6 H 1.1331 0.3657 0.9909 0.043 Uiso 1 1 calc R . .
C7 C 1.3385(3) 0.40006(13) 0.94445(17) 0.0370(6) Uani 1 1 d . . .
C8 C 1.3882(3) 0.44548(13) 0.87594(18) 0.0392(6) Uani 1 1 d . . .
H8 H 1.5030 0.4478 0.8749 0.047 Uiso 1 1 calc R . .
C9 C 1.2758(3) 0.48795(13) 0.80849(17) 0.0354(5) Uani 1 1 d . . .
C10 C 0.8671(3) 0.43714(16) 0.8859(2) 0.0489(7) Uani 1 1 d . . .
H10A H 0.8259 0.4914 0.8885 0.073 Uiso 1 1 calc R . .
H10B H 0.8548 0.4083 0.9418 0.073 Uiso 1 1 calc R . .
H10C H 0.8030 0.4103 0.8308 0.073 Uiso 1 1 calc R . .
C11 C 1.4660(4) 0.35496(16) 1.0160(2) 0.0565(8) Uani 1 1 d . . .
H11A H 1.5126 0.3116 0.9854 0.085 Uiso 1 1 calc R . .
H11B H 1.4121 0.3332 1.0639 0.085 Uiso 1 1 calc R . .
H11C H 1.5552 0.3911 1.0449 0.085 Uiso 1 1 calc R . .
C12 C 1.3347(4) 0.53579(16) 0.7346(2) 0.0551(8) Uani 1 1 d . . .
H12A H 1.3291 0.5924 0.7484 0.083 Uiso 1 1 calc R . .
H12B H 1.2636 0.5245 0.6737 0.083 Uiso 1 1 calc R . .
H12C H 1.4496 0.5213 0.7338 0.083 Uiso 1 1 calc R . .
C13 C 0.7336(3) 0.69896(14) 0.65040(17) 0.0386(6) Uani 1 1 d . . .
H13A H 0.6313 0.6890 0.6028 0.046 Uiso 1 1 calc R . .
H13B H 0.8087 0.7313 0.6211 0.046 Uiso 1 1 calc R . .
C14 C 0.6883(3) 0.74620(13) 0.72837(16) 0.0340(5) Uani 1 1 d . . .
C15 C 0.5207(3) 0.76038(15) 0.72994(18) 0.0429(6) Uani 1 1 d . . .
H15 H 0.4359 0.7369 0.6840 0.051 Uiso 1 1 calc R . .
C16 C 0.4776(4) 0.80834(17) 0.7979(2) 0.0531(7) Uani 1 1 d . . .
H16 H 0.3639 0.8172 0.7983 0.064 Uiso 1 1 calc R . .
C17 C 0.6001(4) 0.84335(17) 0.8652(2) 0.0512(7) Uani 1 1 d . . .
H17 H 0.5699 0.8768 0.9107 0.061 Uiso 1 1 calc R . .
C18 C 0.7679(3) 0.82952(14) 0.86618(18) 0.0419(6) Uani 1 1 d . . .
H18 H 0.8513 0.8529 0.9129 0.050 Uiso 1 1 calc R . .
C19 C 0.8132(3) 0.78091(12) 0.79790(16) 0.0321(5) Uani 1 1 d . . .
C20 C 0.9938(3) 0.76416(12) 0.79946(16) 0.0329(5) Uani 1 1 d . . .
H20A H 1.0635 0.8032 0.8404 0.040 Uiso 1 1 calc R . .
H20B H 1.0142 0.7708 0.7360 0.040 Uiso 1 1 calc R . .
S2A S 0.8744(3) 0.28502(16) 0.4448(2) 0.0617(8) Uani 0.656(7) 1 d PD A 1
N3A N 0.6420(10) 0.3980(4) 0.4831(5) 0.0680(17) Uani 0.656(7) 1 d PD A 1
C1A C 0.7414(9) 0.3530(4) 0.4680(5) 0.0470(18) Uani 0.656(7) 1 d PD A 1
C1B C 0.8288(17) 0.3171(8) 0.4423(9) 0.040(3) Uani 0.344(7) 1 d PD A 2
N3B N 0.9100(14) 0.2878(7) 0.3989(10) 0.081(4) Uani 0.344(7) 1 d PD A 2
S2B S 0.6964(6) 0.3613(3) 0.5008(3) 0.0581(14) Uani 0.344(7) 1 d PD A 2


_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 C1 1.736(2) . ?
S1 C20 1.829(2) . ?
N1 C1 1.349(3) . ?
N1 C2 1.386(3) . ?
N1 C4 1.450(3) . ?
N2 C1 1.336(3) . ?
N2 C3 1.388(3) . ?
N2 C13 1.485(3) . ?
C2 C3 1.339(3) . ?
C4 C5 1.386(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.508(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.382(3) . ?
C7 C11 1.509(3) . ?
C8 C9 1.389(3) . ?
C9 C12 1.500(3) . ?
C13 C14 1.493(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.401(3) . ?
C15 C16 1.376(4) . ?
C16 C17 1.374(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.393(3) . ?
C19 C20 1.495(3) . ?
S2A C1A 1.653(8) . ?
N3A C1A 1.161(12) . ?
C1B N3B 1.121(16) . ?
C1B S2B 1.680(11) . ?

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
C1 S1 C20 101.43(11) . . ?
C1 N1 C2 108.65(19) . . ?
C1 N1 C4 125.08(19) . . ?
C2 N1 C4 125.98(18) . . ?
C1 N2 C3 108.69(19) . . ?
C1 N2 C13 129.13(19) . . ?
C3 N2 C13 121.94(19) . . ?
N2 C1 N1 107.82(19) . . ?
N2 C1 S1 132.48(17) . . ?
N1 C1 S1 119.64(17) . . ?
C3 C2 N1 107.2(2) . . ?
C2 C3 N2 107.6(2) . . ?
C5 C4 C9 123.2(2) . . ?
C5 C4 N1 117.9(2) . . ?
C9 C4 N1 118.9(2) . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 C10 122.2(2) . . ?
C6 C5 C10 120.5(2) . . ?
C7 C6 C5 122.0(2) . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 C11 120.6(2) . . ?
C6 C7 C11 121.3(2) . . ?
C7 C8 C9 122.8(2) . . ?
C8 C9 C4 116.7(2) . . ?
C8 C9 C12 121.1(2) . . ?
C4 C9 C12 122.3(2) . . ?
N2 C13 C14 114.63(19) . . ?
C15 C14 C19 118.9(2) . . ?
C15 C14 C13 120.3(2) . . ?
C19 C14 C13 120.7(2) . . ?
C16 C15 C14 120.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 120.3(3) . . ?
C17 C18 C19 120.0(3) . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 C20 120.5(2) . . ?
C14 C19 C20 119.8(2) . . ?
C19 C20 S1 112.36(15) . . ?
N3A C1A S2A 176.8(6) . . ?
N3B C1B S2B 176.1(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_G262
_database_code_depnum_ccdc_archive 'CCDC 1540241'
_audit_update_record             
;
2017-03-26 deposited with the CCDC.	2020-03-10 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            'C11 H10 N2 S'
_chemical_formula_weight         202.27

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'
S S 0.3331 0.5567 '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                   11.0937(7)
_cell_length_b                   6.0127(4)
_cell_length_c                   13.9608(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.459(5)
_cell_angle_gamma                90
_cell_volume                     929.53(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3464
_cell_measurement_theta_min      4.95
_cell_measurement_theta_max      69.81

_exptl_crystal_description       Thin_Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    2.716
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5482
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7913
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.949
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1764
_reflns_number_gt                1331
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0625P)²+1.5032P] 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         1764
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56537(8) 0.20177(13) 0.57557(6) 0.0234(3) Uani 1 1 d . . . . .
N1 N 0.7738(3) 0.4163(5) 0.5902(2) 0.0245(7) Uani 1 1 d . . . . .
N2 N 0.6327(3) 0.6150(4) 0.6593(2) 0.0210(6) Uani 1 1 d . . . . .
C1 C 0.6599(3) 0.4248(5) 0.6110(2) 0.0215(7) Uani 1 1 d . . . . .
C2 C 0.8233(3) 0.6128(6) 0.6266(3) 0.0262(8) Uani 1 1 d . . . . .
H2 H 0.9054 0.6551 0.6228 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7391(3) 0.7360(5) 0.6682(2) 0.0237(7) Uani 1 1 d . . . . .
H3 H 0.7505 0.8775 0.6976 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5179(3) 0.6934(5) 0.6945(2) 0.0228(7) Uani 1 1 d . . . . .
H4A H 0.4626 0.7328 0.6388 0.027 Uiso 1 1 calc R U . . .
H4B H 0.5332 0.8301 0.7328 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4565(3) 0.5246(5) 0.7553(2) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.4447(3) 0.5639(5) 0.8521(3) 0.0247(8) Uani 1 1 d . . . . .
H6 H 0.4780 0.6953 0.8808 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3845(3) 0.4128(6) 0.9077(3) 0.0253(8) Uani 1 1 d . . . . .
H7 H 0.3751 0.4423 0.9737 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3381(3) 0.2185(6) 0.8662(3) 0.0254(8) Uani 1 1 d . . . . .
H8 H 0.2984 0.1134 0.9042 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3496(3) 0.1776(5) 0.7693(2) 0.0232(7) Uani 1 1 d . . . . .
H9 H 0.3178 0.0441 0.7415 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4071(3) 0.3296(5) 0.7126(2) 0.0212(7) Uani 1 1 d . . . . .
C11 C 0.4159(3) 0.2909(6) 0.6070(2) 0.0237(7) Uani 1 1 d . . . . .
H11A H 0.3946 0.4302 0.5721 0.028 Uiso 1 1 calc R U . . .
H11B H 0.3562 0.1762 0.5854 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.755(3) . ?
S1 C11 1.821(4) . ?
N1 C1 1.314(4) . ?
N1 C2 1.387(4) . ?
N2 C1 1.371(4) . ?
N2 C3 1.386(4) . ?
N2 C4 1.470(4) . ?
C2 C3 1.351(5) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.511(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.387(5) . ?
C5 C10 1.411(5) . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.502(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C1 S1 C11 104.17(16) . . ?
C1 N1 C2 104.5(3) . . ?
C1 N2 C3 105.7(3) . . ?
C1 N2 C4 130.8(3) . . ?
C3 N2 C4 123.5(3) . . ?
N1 C1 N2 112.6(3) . . ?
N1 C1 S1 118.3(2) . . ?
N2 C1 S1 129.1(3) . . ?
C3 C2 N1 110.9(3) . . ?
C3 C2 H2 124.6 . . ?
N1 C2 H2 124.6 . . ?
C2 C3 N2 106.3(3) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
N2 C4 C5 113.6(3) . . ?
N2 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N2 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C10 119.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
C10 C5 C4 119.9(3) . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 119.1(3) . . ?
C9 C10 C11 121.1(3) . . ?
C5 C10 C11 119.8(3) . . ?
C10 C11 S1 113.3(2) . . ?
C10 C11 H11A 108.9 . . ?
S1 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
S1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?

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
C2 N1 C1 N2 -0.4(4) . . . . ?
C2 N1 C1 S1 179.8(2) . . . . ?
C3 N2 C1 N1 0.8(4) . . . . ?
C4 N2 C1 N1 178.8(3) . . . . ?
C3 N2 C1 S1 -179.5(3) . . . . ?
C4 N2 C1 S1 -1.4(5) . . . . ?
C11 S1 C1 N1 -174.6(3) . . . . ?
C11 S1 C1 N2 5.6(3) . . . . ?
C1 N1 C2 C3 -0.2(4) . . . . ?
N1 C2 C3 N2 0.6(4) . . . . ?
C1 N2 C3 C2 -0.8(4) . . . . ?
C4 N2 C3 C2 -179.1(3) . . . . ?
C1 N2 C4 C5 52.2(5) . . . . ?
C3 N2 C4 C5 -130.0(3) . . . . ?
N2 C4 C5 C6 113.3(3) . . . . ?
N2 C4 C5 C10 -69.0(4) . . . . ?
C10 C5 C6 C7 0.0(5) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C6 C7 C8 C9 -1.3(5) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C5 1.5(5) . . . . ?
C8 C9 C10 C11 -177.7(3) . . . . ?
C6 C5 C10 C9 -1.4(5) . . . . ?
C4 C5 C10 C9 -179.2(3) . . . . ?
C6 C5 C10 C11 177.8(3) . . . . ?
C4 C5 C10 C11 0.1(5) . . . . ?
C9 C10 C11 S1 -104.4(3) . . . . ?
C5 C10 C11 S1 76.4(3) . . . . ?
C1 S1 C11 C10 -62.0(3) . . . . ?

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.081

