# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_AB_175
_database_code_depnum_ccdc_archive 'CCDC 2113397'
loop_
_audit_author_name
_audit_author_address
'ARPITA BANERJEE'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2021-10-01 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cl N O2 S'
_chemical_formula_sum            'C15 H14 Cl N O2 S'
_chemical_formula_weight         307.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   9.9201(3)
_cell_length_b                   7.5619(2)
_cell_length_c                   18.7671(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.4780(10)
_cell_angle_gamma                90
_cell_volume                     1388.59(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.39

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.411
_exptl_transmission_factor_max   0.590
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.425
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22751
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3459
_reflns_number_gt                3017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²+0.1551P] 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         3459
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_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 0.15489(3) 0.36814(4) 0.35056(2) 0.01437(12) Uani 1 1 d . . . . .
Cl1 Cl 0.73683(4) 0.25401(5) 0.10196(2) 0.02361(13) Uani 1 1 d . . . . .
O2 O 0.41392(10) 0.58815(12) 0.35037(5) 0.0147(2) Uani 1 1 d . . . . .
O1 O 0.04744(11) 0.28628(14) 0.38320(6) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.27793(12) 0.26130(14) 0.33637(7) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.33276(14) 0.64174(16) 0.39904(7) 0.0139(3) Uani 1 1 d . . . . .
C9 C 0.49303(14) 0.42778(17) 0.36699(7) 0.0146(3) Uani 1 1 d . . . . .
H9 H 0.567456 0.451227 0.407110 0.017 Uiso 1 1 calc R U . . .
C2 C 0.20997(14) 0.55693(17) 0.40459(7) 0.0143(3) Uani 1 1 d . . . . .
C11 C 0.55295(14) 0.38622(17) 0.30024(7) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.54236(14) 0.39306(17) 0.17066(7) 0.0152(3) Uani 1 1 d . . . . .
H12 H 0.498079 0.425814 0.124992 0.018 Uiso 1 1 calc R U . . .
C15 C 0.66660(14) 0.30512(18) 0.17905(7) 0.0164(3) Uani 1 1 d . . . . .
C14 C 0.73599(15) 0.25738(17) 0.24626(8) 0.0170(3) Uani 1 1 d . . . . .
H14 H 0.818969 0.197794 0.250777 0.020 Uiso 1 1 calc R U . . .
C10 C 0.48508(13) 0.43145(17) 0.23172(7) 0.0141(3) Uani 1 1 d . . . . .
H10 H 0.400727 0.487826 0.226734 0.017 Uiso 1 1 calc R U . . .
C8 C 0.40356(14) 0.27711(18) 0.38852(7) 0.0162(3) Uani 1 1 d . . . . .
H8A H 0.453779 0.166645 0.390726 0.019 Uiso 1 1 calc R U . . .
H8B H 0.381381 0.300531 0.436070 0.019 Uiso 1 1 calc R U . . .
C13 C 0.67906(14) 0.30037(18) 0.30713(7) 0.0160(3) Uani 1 1 d . . . . .
H13 H 0.725547 0.271584 0.352814 0.019 Uiso 1 1 calc R U . . .
C6 C 0.37078(15) 0.79149(18) 0.44034(7) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.452314 0.848962 0.436849 0.021 Uiso 1 1 calc R U . . .
C1 C 0.07946(14) 0.45253(18) 0.26586(7) 0.0175(3) Uani 1 1 d . . . . .
H1A H 0.059724 0.356962 0.232080 0.026 Uiso 1 1 calc R U . . .
H1B H 0.141316 0.533781 0.248777 0.026 Uiso 1 1 calc R U . . .
H1C H -0.003781 0.512851 0.270553 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28664(16) 0.85533(19) 0.48696(8) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.311494 0.956929 0.513854 0.025 Uiso 1 1 calc R U . . .
C3 C 0.12751(15) 0.61926(18) 0.45219(7) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.046611 0.560900 0.456262 0.022 Uiso 1 1 calc R U . . .
C4 C 0.16575(16) 0.76871(19) 0.49373(8) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.110940 0.810444 0.525790 0.025 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 O1 1.4524(10) . ?
S1 N1 1.5234(12) . ?
S1 C1 1.7614(13) . ?
S1 C2 1.7839(13) . ?
Cl1 C15 1.7491(13) . ?
O2 C7 1.3742(15) . ?
O2 C9 1.4503(15) . ?
N1 C8 1.4572(18) . ?
C7 C6 1.3889(18) . ?
C7 C2 1.3956(19) . ?
C9 C11 1.5053(18) . ?
C9 C8 1.5386(18) . ?
C2 C3 1.3892(18) . ?
C11 C10 1.3925(18) . ?
C11 C13 1.3964(19) . ?
C12 C15 1.3864(19) . ?
C12 C10 1.3909(18) . ?
C15 C14 1.382(2) . ?
C14 C13 1.394(2) . ?
C6 C5 1.391(2) . ?
C5 C4 1.391(2) . ?
C3 C4 1.390(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
O1 S1 N1 120.83(7) . . ?
O1 S1 C1 107.63(7) . . ?
N1 S1 C1 105.54(7) . . ?
O1 S1 C2 106.18(6) . . ?
N1 S1 C2 110.16(6) . . ?
C1 S1 C2 105.54(6) . . ?
C7 O2 C9 117.34(10) . . ?
C8 N1 S1 117.40(10) . . ?
O2 C7 C6 118.45(12) . . ?
O2 C7 C2 121.88(11) . . ?
C6 C7 C2 119.54(13) . . ?
O2 C9 C11 105.64(10) . . ?
O2 C9 C8 111.13(11) . . ?
C11 C9 C8 112.82(11) . . ?
C3 C2 C7 120.38(12) . . ?
C3 C2 S1 118.64(10) . . ?
C7 C2 S1 120.98(10) . . ?
C10 C11 C13 119.29(12) . . ?
C10 C11 C9 121.34(12) . . ?
C13 C11 C9 119.37(12) . . ?
C15 C12 C10 118.86(12) . . ?
C14 C15 C12 121.93(13) . . ?
C14 C15 Cl1 119.40(11) . . ?
C12 C15 Cl1 118.67(11) . . ?
C15 C14 C13 118.63(13) . . ?
C12 C10 C11 120.57(12) . . ?
N1 C8 C9 110.55(11) . . ?
C14 C13 C11 120.69(13) . . ?
C7 C6 C5 119.87(13) . . ?
C4 C5 C6 120.65(13) . . ?
C2 C3 C4 120.09(13) . . ?
C3 C4 C5 119.44(14) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_AB_176A
_database_code_depnum_ccdc_archive 'CCDC 2113503'
loop_
_audit_author_name
_audit_author_address
'ARPITA BANERJEE'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2021-10-02 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 Cl N O2 S'
_chemical_formula_sum            'C17 H18 Cl N O2 S'
_chemical_formula_weight         335.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4820(5)
_cell_length_b                   9.2719(6)
_cell_length_c                   20.5792(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.217(2)
_cell_angle_gamma                90
_cell_volume                     1611.73(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9776
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.36

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   0.914
_exptl_transmission_factor_max   0.949
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25439
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4027
_reflns_number_gt                3461
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²+0.8103P] 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         4027
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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 0.23911(4) 0.18884(4) 0.57160(2) 0.01576(12) Uani 1 1 d . . . . .
Cl1 Cl 0.81035(5) 0.87522(5) 0.70570(2) 0.03239(15) Uani 1 1 d . . . . .
O2 O 0.16784(13) 0.48092(12) 0.63688(5) 0.0174(2) Uani 1 1 d . . . . .
O1 O 0.20257(15) 0.08431(14) 0.51949(6) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.35413(15) 0.31213(14) 0.56324(6) 0.0160(3) Uani 1 1 d . . . . .
C12 C 0.38738(17) 0.62691(15) 0.61661(7) 0.0147(3) Uani 1 1 d . . . . .
C5 C 0.03891(18) 0.39524(17) 0.61889(7) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.43552(18) 0.61330(17) 0.68278(7) 0.0171(3) Uani 1 1 d . . . . .
H17 H 0.380404 0.552456 0.708627 0.021 Uiso 1 1 calc R U . . .
C11 C 0.24272(17) 0.55047(17) 0.58484(7) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.169823 0.622906 0.564580 0.019 Uiso 1 1 calc R U . . .
C13 C 0.47338(18) 0.71598(17) 0.57811(8) 0.0178(3) Uani 1 1 d . . . . .
H13 H 0.442155 0.724830 0.533783 0.021 Uiso 1 1 calc R U . . .
C14 C 0.60469(19) 0.79152(17) 0.60490(8) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.662669 0.849475 0.578893 0.023 Uiso 1 1 calc R U . . .
C16 C 0.56570(19) 0.69018(17) 0.71058(8) 0.0192(3) Uani 1 1 d . . . . .
H16 H 0.597080 0.682082 0.754916 0.023 Uiso 1 1 calc R U . . .
C4 C 0.05255(17) 0.25801(17) 0.59104(7) 0.0162(3) Uani 1 1 d . . . . .
C6 C -0.10927(19) 0.44513(19) 0.63226(8) 0.0208(3) Uani 1 1 d . . . . .
H6 H -0.119177 0.535690 0.650891 0.025 Uiso 1 1 calc R U . . .
C2 C -0.22922(18) 0.2251(2) 0.58930(8) 0.0236(4) Uani 1 1 d . . . . .
H2 H -0.319117 0.169103 0.579345 0.028 Uiso 1 1 calc R U . . .
C10 C 0.28152(18) 0.44204(17) 0.53250(7) 0.0169(3) Uani 1 1 d . . . . .
H10A H 0.185353 0.415972 0.505966 0.020 Uiso 1 1 calc R U . . .
H10B H 0.353790 0.485587 0.504269 0.020 Uiso 1 1 calc R U . . .
C3 C -0.08181(19) 0.17393(19) 0.57560(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H -0.072916 0.084029 0.556225 0.025 Uiso 1 1 calc R U . . .
C15 C 0.64771(18) 0.77880(17) 0.67129(8) 0.0186(3) Uani 1 1 d . . . . .
C1 C -0.24252(19) 0.3599(2) 0.61784(9) 0.0236(4) Uani 1 1 d . . . . .
H1 H -0.341249 0.393288 0.627343 0.028 Uiso 1 1 calc R U . . .
C7 C 0.32227(19) 0.08916(18) 0.64115(8) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.422426 0.047967 0.629627 0.026 Uiso 1 1 calc R U . . .
C8 C 0.3610(2) 0.1861(2) 0.70010(9) 0.0287(4) Uani 1 1 d . . . . .
H8A H 0.265870 0.231814 0.711681 0.043 Uiso 1 1 calc R U . . .
H8B H 0.435602 0.258489 0.689669 0.043 Uiso 1 1 calc R U . . .
H8C H 0.405828 0.129304 0.736155 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2147(2) -0.03642(19) 0.65490(9) 0.0278(4) Uani 1 1 d . . . . .
H9A H 0.266672 -0.096539 0.688274 0.042 Uiso 1 1 calc R U . . .
H9B H 0.191786 -0.091901 0.615797 0.042 Uiso 1 1 calc R U . . .
H9C H 0.117803 -0.000044 0.669311 0.042 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 O1 1.4577(12) . ?
S1 N1 1.5227(13) . ?
S1 C4 1.7862(15) . ?
S1 C7 1.7935(17) . ?
Cl1 C15 1.7396(16) . ?
O2 C5 1.3749(18) . ?
O2 C11 1.4455(18) . ?
N1 C10 1.470(2) . ?
C12 C17 1.392(2) . ?
C12 C13 1.395(2) . ?
C12 C11 1.513(2) . ?
C5 C6 1.390(2) . ?
C5 C4 1.404(2) . ?
C17 C16 1.393(2) . ?
C17 H17 0.9300 . ?
C11 C10 1.531(2) . ?
C11 H11 0.9800 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9300 . ?
C16 C15 1.384(2) . ?
C16 H16 0.9300 . ?
C4 C3 1.394(2) . ?
C6 C1 1.389(2) . ?
C6 H6 0.9300 . ?
C2 C1 1.390(3) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C7 C9 1.522(2) . ?
C7 C8 1.522(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
O1 S1 N1 120.77(7) . . ?
O1 S1 C4 105.67(7) . . ?
N1 S1 C4 110.21(7) . . ?
O1 S1 C7 106.64(8) . . ?
N1 S1 C7 105.51(8) . . ?
C4 S1 C7 107.36(7) . . ?
C5 O2 C11 116.78(12) . . ?
C10 N1 S1 114.60(10) . . ?
C17 C12 C13 119.17(14) . . ?
C17 C12 C11 122.32(13) . . ?
C13 C12 C11 118.51(14) . . ?
O2 C5 C6 117.76(14) . . ?
O2 C5 C4 122.70(13) . . ?
C6 C5 C4 119.46(14) . . ?
C12 C17 C16 120.44(14) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O2 C11 C12 106.42(12) . . ?
O2 C11 C10 111.43(12) . . ?
C12 C11 C10 113.19(12) . . ?
O2 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C14 C13 C12 121.03(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.60(14) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C15 C16 C17 119.07(15) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C3 C4 C5 120.26(14) . . ?
C3 C4 S1 118.09(12) . . ?
C5 C4 S1 121.62(11) . . ?
C1 C6 C5 120.09(16) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C2 C3 120.13(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N1 C10 C11 110.11(12) . . ?
N1 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C2 C3 C4 119.65(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C16 C15 C14 121.66(15) . . ?
C16 C15 Cl1 119.30(13) . . ?
C14 C15 Cl1 119.04(12) . . ?
C6 C1 C2 120.40(15) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C9 C7 C8 113.17(14) . . ?
C9 C7 S1 110.11(12) . . ?
C8 C7 S1 111.86(12) . . ?
C9 C7 H7 107.1 . . ?
C8 C7 H7 107.1 . . ?
S1 C7 H7 107.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.073

