# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_ic17529
_database_code_depnum_ccdc_archive 'CCDC 1504810'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2017-03-03 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            'C8 H7 N O S'
_chemical_formula_weight         165.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   10.0478(3)
_cell_length_b                   10.3511(3)
_cell_length_c                   14.6556(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1524.27(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9669
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.45

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.357
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9737
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1747
_reflns_number_gt                1553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.5983P] 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         1747
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.19920(4) 0.43315(3) 0.61923(3) 0.03392(13) Uani 1 1 d . . . . .
O1 O 0.28143(10) 0.59566(10) 0.44877(7) 0.0355(2) Uani 1 1 d . . . . .
N1 N 0.46297(11) 0.68420(10) 0.51956(7) 0.0269(2) Uani 1 1 d . . . . .
C1 C 0.24588(17) 0.41154(14) 0.73113(10) 0.0377(3) Uani 1 1 d . . . . .
H1 H 0.2000 0.3563 0.7722 0.045 Uiso 1 1 calc R U . . .
C2 C 0.35446(15) 0.48111(13) 0.75473(9) 0.0341(3) Uani 1 1 d . . . . .
H2 H 0.3929 0.4804 0.8139 0.041 Uiso 1 1 calc R U . . .
C3 C 0.40477(13) 0.55595(12) 0.68027(9) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.51550(14) 0.64085(13) 0.67569(9) 0.0314(3) Uani 1 1 d . . . . .
H4 H 0.5703 0.6550 0.7276 0.038 Uiso 1 1 calc R U . . .
C5 C 0.54113(13) 0.70087(13) 0.59598(10) 0.0309(3) Uani 1 1 d . . . . .
H5 H 0.6159 0.7568 0.5923 0.037 Uiso 1 1 calc R U . . .
C6 C 0.32842(12) 0.53936(12) 0.60239(9) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.35167(12) 0.60507(12) 0.51759(8) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.49064(16) 0.75944(15) 0.43686(10) 0.0400(3) Uani 1 1 d . . . . .
H8A H 0.5699 0.8129 0.4466 0.060 Uiso 1 1 calc R U . . .
H8B H 0.4143 0.8151 0.4231 0.060 Uiso 1 1 calc R U . . .
H8C H 0.5062 0.7006 0.3856 0.060 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 C6 1.7192(13) . ?
S1 C1 1.7202(16) . ?
O1 C7 1.2348(16) . ?
N1 C5 1.3787(17) . ?
N1 C7 1.3865(17) . ?
N1 C8 1.4673(17) . ?
C1 C2 1.352(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.4304(19) . ?
C2 H2 0.9500 . ?
C3 C6 1.3859(18) . ?
C3 C4 1.4194(19) . ?
C4 C5 1.348(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.4359(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C6 S1 C1 90.81(7) . . ?
C5 N1 C7 123.39(11) . . ?
C5 N1 C8 119.77(12) . . ?
C7 N1 C8 116.69(11) . . ?
C2 C1 S1 113.24(11) . . ?
C2 C1 H1 123.4 . . ?
S1 C1 H1 123.4 . . ?
C1 C2 C3 112.23(13) . . ?
C1 C2 H2 123.9 . . ?
C3 C2 H2 123.9 . . ?
C6 C3 C4 118.14(12) . . ?
C6 C3 C2 111.44(12) . . ?
C4 C3 C2 130.42(13) . . ?
C5 C4 C3 118.44(12) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 N1 122.51(12) . . ?
C4 C5 H5 118.7 . . ?
N1 C5 H5 118.7 . . ?
C3 C6 C7 124.34(12) . . ?
C3 C6 S1 112.27(10) . . ?
C7 C6 S1 123.37(10) . . ?
O1 C7 N1 121.64(12) . . ?
O1 C7 C6 125.21(12) . . ?
N1 C7 C6 113.14(11) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_ic17694
_database_code_depnum_ccdc_archive 'CCDC 1504811'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2017-03-03 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            'C8 H6 Br N S2'
_chemical_formula_weight         260.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.9208(3)
_cell_length_b                   7.5423(4)
_cell_length_c                   8.8756(5)
_cell_angle_alpha                85.0711(17)
_cell_angle_beta                 82.0272(16)
_cell_angle_gamma                89.0243(17)
_cell_volume                     457.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.51

_exptl_crystal_description       rod
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.891
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5731
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4025
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0090
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.711
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2099
_reflns_number_gt                1988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.9075P] 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         2099
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Br1 Br 0.64947(4) 0.95330(3) 0.18377(3) 0.02607(10) Uani 1 1 d . . . . .
S1 S 0.69699(8) 0.82744(7) 0.51539(6) 0.01256(12) Uani 1 1 d . . . . .
S2 S 0.75203(10) 0.68610(8) 0.86372(7) 0.02084(14) Uani 1 1 d . . . . .
N1 N 0.7898(3) 0.3666(3) 0.7468(2) 0.0130(4) Uani 1 1 d . . . . .
C1 C 0.6942(3) 0.7723(3) 0.3306(3) 0.0132(4) Uani 1 1 d . . . . .
C2 C 0.7219(3) 0.5970(3) 0.3102(2) 0.0131(4) Uani 1 1 d . . . . .
H2 H 0.7233 0.5465 0.2157 0.016 Uiso 1 1 calc R U . . .
C3 C 0.7487(3) 0.4989(3) 0.4512(2) 0.0110(4) Uani 1 1 d . . . . .
C4 C 0.7843(3) 0.3147(3) 0.4841(3) 0.0138(4) Uani 1 1 d . . . . .
H4 H 0.7949 0.2350 0.4061 0.017 Uiso 1 1 calc R U . . .
C5 C 0.8027(3) 0.2558(3) 0.6306(3) 0.0145(4) Uani 1 1 d . . . . .
H5 H 0.8256 0.1325 0.6536 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7388(3) 0.6076(3) 0.5714(2) 0.0105(4) Uani 1 1 d . . . . .
C7 C 0.7608(3) 0.5473(3) 0.7242(3) 0.0123(4) Uani 1 1 d . . . . .
C8 C 0.8094(4) 0.2881(3) 0.9016(3) 0.0208(5) Uani 1 1 d . . . . .
H8A H 0.8305 0.1595 0.8997 0.031 Uiso 1 1 calc R U . . .
H8B H 0.6900 0.3109 0.9707 0.031 Uiso 1 1 calc R U . . .
H8C H 0.9207 0.3418 0.9376 0.031 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
Br1 C1 1.857(2) . ?
S1 C6 1.721(2) . ?
S1 C1 1.729(2) . ?
S2 C7 1.683(2) . ?
N1 C5 1.375(3) . ?
N1 C7 1.376(3) . ?
N1 C8 1.472(3) . ?
C1 C2 1.356(3) . ?
C2 C3 1.432(3) . ?
C2 H2 0.9500 . ?
C3 C6 1.394(3) . ?
C3 C4 1.419(3) . ?
C4 C5 1.360(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.421(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C6 S1 C1 89.71(10) . . ?
C5 N1 C7 122.84(19) . . ?
C5 N1 C8 118.4(2) . . ?
C7 N1 C8 118.76(19) . . ?
C2 C1 S1 114.98(17) . . ?
C2 C1 Br1 127.05(18) . . ?
S1 C1 Br1 117.96(13) . . ?
C1 C2 C3 110.5(2) . . ?
C1 C2 H2 124.7 . . ?
C3 C2 H2 124.7 . . ?
C6 C3 C4 117.5(2) . . ?
C6 C3 C2 112.21(19) . . ?
C4 C3 C2 130.3(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 N1 122.9(2) . . ?
C4 C5 H5 118.5 . . ?
N1 C5 H5 118.5 . . ?
C3 C6 C7 124.7(2) . . ?
C3 C6 S1 112.60(16) . . ?
C7 C6 S1 122.65(17) . . ?
N1 C7 C6 113.93(19) . . ?
N1 C7 S2 123.58(17) . . ?
C6 C7 S2 122.49(17) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 S1 0.95 2.91 3.588(2) 129.6 1_545
C8 H8A Br1 0.98 2.98 3.481(2) 113.1 1_546

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_ic17528
_database_code_depnum_ccdc_archive 'CCDC 1504809'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2017-03-03 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            'C8 H7 N S2'
_chemical_formula_weight         181.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   7.0250(3)
_cell_length_b                   8.6002(4)
_cell_length_c                   13.5237(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.7881(17)
_cell_angle_gamma                90
_cell_volume                     802.61(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7635
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.66

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.588
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7044
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6215
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1841
_reflns_number_gt                1636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.7275P] 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         1841
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.34953(7) 0.44543(6) 0.68415(3) 0.02786(14) Uani 1 1 d . . . . .
S2 S 0.29516(9) 0.81084(6) 0.61158(4) 0.03496(15) Uani 1 1 d . . . . .
N1 N 0.2039(2) 0.68113(18) 0.42769(11) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.3381(3) 0.2530(2) 0.64764(16) 0.0307(4) Uani 1 1 d . . . . .
H1 H 0.3685 0.1692 0.6937 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2819(3) 0.2326(2) 0.54757(16) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.2679 0.1338 0.5156 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2458(3) 0.3775(2) 0.49531(14) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.1890(3) 0.4086(2) 0.39135(14) 0.0305(4) Uani 1 1 d . . . . .
H4 H 0.1642 0.3262 0.3439 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1709(3) 0.5585(3) 0.36108(14) 0.0298(4) Uani 1 1 d . . . . .
H5 H 0.1341 0.5801 0.2912 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2768(2) 0.5034(2) 0.56083(13) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.2559(3) 0.6611(2) 0.53004(13) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.1841(3) 0.8396(2) 0.38667(15) 0.0335(5) Uani 1 1 d . . . . .
H8A H 0.0796 0.8935 0.4117 0.050 Uiso 1 1 calc R U . . .
H8B H 0.1533 0.8349 0.3130 0.050 Uiso 1 1 calc R U . . .
H8C H 0.3060 0.8961 0.4080 0.050 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 C6 1.7239(18) . ?
S1 C1 1.725(2) . ?
S2 C7 1.6839(18) . ?
N1 C7 1.375(2) . ?
N1 C5 1.378(3) . ?
N1 C8 1.468(2) . ?
C1 C2 1.348(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.431(3) . ?
C2 H2 0.9500 . ?
C3 C6 1.391(2) . ?
C3 C4 1.413(3) . ?
C4 C5 1.351(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.418(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C6 S1 C1 90.64(9) . . ?
C7 N1 C5 122.88(16) . . ?
C7 N1 C8 119.02(16) . . ?
C5 N1 C8 118.10(16) . . ?
C2 C1 S1 113.66(15) . . ?
C2 C1 H1 123.2 . . ?
S1 C1 H1 123.2 . . ?
C1 C2 C3 111.96(18) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 H2 124.0 . . ?
C6 C3 C4 117.87(17) . . ?
C6 C3 C2 111.79(16) . . ?
C4 C3 C2 130.33(18) . . ?
C5 C4 C3 118.38(18) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 N1 122.50(18) . . ?
C4 C5 H5 118.8 . . ?
N1 C5 H5 118.8 . . ?
C3 C6 C7 124.23(16) . . ?
C3 C6 S1 111.95(14) . . ?
C7 C6 S1 123.80(14) . . ?
N1 C7 C6 114.12(16) . . ?
N1 C7 S2 122.95(14) . . ?
C6 C7 S2 122.93(13) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.234
_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_ic17611
_database_code_depnum_ccdc_archive 'CCDC 1504812'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2017-03-03 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            'C8 H6 I N S2'
_chemical_formula_weight         307.16

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.3765(2)
_cell_length_b                   18.9914(7)
_cell_length_c                   7.7127(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.0593(13)
_cell_angle_gamma                90
_cell_volume                     953.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5962
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.738
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6979
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2186
_reflns_number_gt                1940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0212P)²+0.4237P] 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         2186
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0468
_refine_ls_wR_factor_gt          0.0452
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.61021(2) 0.31421(2) 0.18640(2) 0.02326(6) Uani 1 1 d . . . . .
S1 S 0.70848(9) 0.48320(3) 0.28199(10) 0.02104(14) Uani 1 1 d . . . . .
S2 S 0.81493(9) 0.64835(3) 0.39611(11) 0.02661(15) Uani 1 1 d . . . . .
N1 N 0.4165(3) 0.65485(11) 0.3145(3) 0.0206(4) Uani 1 1 d . . . . .
C1 C 0.5294(4) 0.41650(13) 0.2217(4) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.3455(4) 0.43827(13) 0.2030(4) 0.0238(5) Uani 1 1 d . . . . .
H2 H 0.2319 0.4080 0.1724 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3446(4) 0.51209(13) 0.2350(4) 0.0202(5) Uani 1 1 d . . . . .
C4 C 0.5322(3) 0.54342(13) 0.2800(3) 0.0181(5) Uani 1 1 d . . . . .
C5 C 0.5779(3) 0.61531(13) 0.3263(4) 0.0184(5) Uani 1 1 d . . . . .
C6 C 0.1867(4) 0.55652(14) 0.2285(4) 0.0248(5) Uani 1 1 d . . . . .
H6 H 0.0554 0.5380 0.1981 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2279(4) 0.62574(14) 0.2666(4) 0.0249(6) Uani 1 1 d . . . . .
H7 H 0.1219 0.6557 0.2602 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4460(4) 0.73078(14) 0.3555(4) 0.0274(6) Uani 1 1 d . . . . .
H8A H 0.5746 0.7386 0.4766 0.041 Uiso 1 1 calc R U . . .
H8B H 0.3308 0.7495 0.3713 0.041 Uiso 1 1 calc R U . . .
H8C H 0.4523 0.7548 0.2460 0.041 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
I1 C1 2.087(2) . ?
S1 C4 1.726(2) . ?
S1 C1 1.728(2) . ?
S2 C5 1.690(2) . ?
N1 C5 1.374(3) . ?
N1 C7 1.376(3) . ?
N1 C8 1.470(3) . ?
C1 C2 1.360(3) . ?
C2 C3 1.424(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C6 1.419(3) . ?
C4 C5 1.411(3) . ?
C6 C7 1.350(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 90.35(12) . . ?
C5 N1 C7 122.2(2) . . ?
C5 N1 C8 119.09(19) . . ?
C7 N1 C8 118.7(2) . . ?
C2 C1 S1 113.81(19) . . ?
C2 C1 I1 126.95(18) . . ?
S1 C1 I1 119.24(13) . . ?
C1 C2 C3 111.5(2) . . ?
C1 C2 H2 124.2 . . ?
C3 C2 H2 124.2 . . ?
C4 C3 C6 117.2(2) . . ?
C4 C3 C2 112.2(2) . . ?
C6 C3 C2 130.5(2) . . ?
C3 C4 C5 124.6(2) . . ?
C3 C4 S1 112.06(18) . . ?
C5 C4 S1 123.31(17) . . ?
N1 C5 C4 114.6(2) . . ?
N1 C5 S2 123.54(19) . . ?
C4 C5 S2 121.88(18) . . ?
C7 C6 C3 118.3(2) . . ?
C7 C6 H6 120.9 . . ?
C3 C6 H6 120.9 . . ?
C6 C7 N1 123.0(2) . . ?
C6 C7 H7 118.5 . . ?
N1 C7 H7 118.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 S2 0.95 2.91 3.650(2) 135.5 1_455
C8 H8B I1 0.98 3.31 4.266(2) 166.9 2
C8 H8C I1 0.98 3.22 3.785(3) 118.3 2_655
C8 H8C S2 0.98 3.02 3.941(3) 157.2 4_575

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.105

