# 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_d1
_database_code_depnum_ccdc_archive 'CCDC 1870970'
loop_
_audit_author_name
_audit_author_address
'S. Antony Savarimuthu'
;St.Xavier's college, palayamkottai, Tirunelvelli, Tamil Nadu
India
;
_audit_update_record             
;
2018-10-02 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2017-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O2 S'
_chemical_formula_sum            'C17 H15 N O2 S'
_chemical_formula_weight         297.36
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3519(9)
_cell_length_b                   7.7182(12)
_cell_length_c                   13.473(2)
_cell_angle_alpha                90.118(5)
_cell_angle_beta                 98.358(4)
_cell_angle_gamma                94.483(4)
_cell_volume                     753.98(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.552
_cell_measurement_theta_min      2.647
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0722 before and 0.0379 after correction. The Ratio of minimum to maximum transmission is 0.9473. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10806
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.375
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2154
_reflns_number_total             4010
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C17(H17), C15(H15), C14(H14), C13(H13),
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.17248(7) 0.25574(9) 0.52744(4) 0.0673(2) Uani 1 1 d . . . . .
O1 O 0.83776(17) 0.24535(18) 0.57060(9) 0.0532(4) Uani 1 1 d . . . . .
O2 O 1.14708(16) 0.21825(16) 0.05395(9) 0.0489(3) Uani 1 1 d . . . . .
N1 N 0.84451(18) 0.23453(19) 0.40813(10) 0.0405(4) Uani 1 1 d . . . . .
C6 C 1.0041(2) 0.3841(2) 0.28406(13) 0.0440(4) Uani 1 1 d . . . . .
H6 H 1.009966 0.485988 0.321739 0.053 Uiso 1 1 calc R . . . .
C7 C 1.0806(2) 0.3848(2) 0.19613(13) 0.0436(4) Uani 1 1 d . . . . .
H7 H 1.138422 0.486659 0.174816 0.052 Uiso 1 1 calc R . . . .
C1 C 0.9484(2) 0.2448(2) 0.49971(13) 0.0434(4) Uani 1 1 d . . . . .
C5 C 0.9203(2) 0.2349(2) 0.31581(12) 0.0377(4) Uani 1 1 d . . . . .
C8 C 1.0705(2) 0.2331(2) 0.14011(12) 0.0379(4) Uani 1 1 d . . . . .
C9 C 0.9802(2) 0.0840(2) 0.17067(13) 0.0463(5) Uani 1 1 d . . . . .
H9 H 0.968997 -0.016809 0.131570 0.056 Uiso 1 1 calc R . . . .
C12 C 1.3807(3) 0.3038(2) -0.04517(14) 0.0442(5) Uani 1 1 d . . . . .
C10 C 0.9064(2) 0.0837(2) 0.25913(13) 0.0471(5) Uani 1 1 d . . . . .
H10 H 0.847733 -0.017593 0.280510 0.057 Uiso 1 1 calc R . . . .
C11 C 1.2634(3) 0.3633(2) 0.02764(16) 0.0568(6) Uani 1 1 d . . . . .
H11A H 1.340751 0.411654 0.087272 0.068 Uiso 1 1 calc R . . . .
H11B H 1.188565 0.453058 -0.002207 0.068 Uiso 1 1 calc R . . . .
C2 C 0.6547(2) 0.2298(3) 0.41439(14) 0.0481(5) Uani 1 1 d . . . . .
C3 C 0.6478(3) 0.2408(3) 0.52440(14) 0.0592(6) Uani 1 1 d . . . . .
H3A H 0.592494 0.345196 0.541024 0.071 Uiso 1 1 calc R . . . .
H3B H 0.576930 0.140436 0.546272 0.071 Uiso 1 1 calc R . . . .
C17 C 1.3414(3) 0.3359(3) -0.14591(15) 0.0628(6) Uani 1 1 d . . . . .
H17 H 1.236827 0.392062 -0.170086 0.075 Uiso 1 1 calc R . . . .
C15 C 1.6086(3) 0.2024(3) -0.17772(18) 0.0653(6) Uani 1 1 d . . . . .
H15 H 1.684897 0.167922 -0.222171 0.078 Uiso 1 1 calc R . . . .
C14 C 1.6496(3) 0.1697(3) -0.07774(18) 0.0653(6) Uani 1 1 d . . . . .
H14 H 1.753767 0.112672 -0.053960 0.078 Uiso 1 1 calc R . . . .
C13 C 1.5365(3) 0.2213(3) -0.01227(16) 0.0572(5) Uani 1 1 d . . . . .
H13 H 1.566231 0.199745 0.055816 0.069 Uiso 1 1 calc R . . . .
C16 C 1.4564(3) 0.2853(3) -0.21206(16) 0.0728(7) Uani 1 1 d . . . . .
H16 H 1.428815 0.308259 -0.280086 0.087 Uiso 1 1 calc R . . . .
C4 C 0.5193(3) 0.2186(4) 0.33935(19) 0.0760(8) Uani 1 1 d . . . . .
H4A H 0.394(3) 0.221(3) 0.3526(17) 0.092(8) Uiso 1 1 d . . . . .
H4B H 0.540(3) 0.212(3) 0.2730(17) 0.069(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6311(18) . ?
O1 C1 1.342(2) . ?
O1 C3 1.442(2) . ?
O2 C8 1.3700(19) . ?
O2 C11 1.432(2) . ?
N1 C1 1.352(2) . ?
N1 C5 1.435(2) . ?
N1 C2 1.408(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(2) . ?
C6 C5 1.362(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C5 C10 1.382(2) . ?
C8 C9 1.377(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(2) . ?
C12 C11 1.491(2) . ?
C12 C17 1.373(3) . ?
C12 C13 1.371(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 C3 1.493(3) . ?
C2 C4 1.309(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.365(3) . ?
C15 C16 1.356(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.93(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
C1 O1 C3 109.95(13) . . ?
C8 O2 C11 117.27(13) . . ?
C1 N1 C5 123.63(13) . . ?
C1 N1 C2 111.98(14) . . ?
C2 N1 C5 124.36(13) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.38(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.54(16) . . ?
C8 C7 H7 120.2 . . ?
O1 C1 S1 122.10(13) . . ?
O1 C1 N1 109.40(14) . . ?
N1 C1 S1 128.51(13) . . ?
C6 C5 N1 120.00(16) . . ?
C6 C5 C10 120.35(16) . . ?
C10 C5 N1 119.65(15) . . ?
O2 C8 C7 124.23(15) . . ?
O2 C8 C9 115.86(15) . . ?
C9 C8 C7 119.91(15) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.15(16) . . ?
C10 C9 H9 119.9 . . ?
C17 C12 C11 121.5(2) . . ?
C13 C12 C11 120.44(18) . . ?
C13 C12 C17 118.03(18) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.61(17) . . ?
C9 C10 H10 120.2 . . ?
O2 C11 C12 109.00(15) . . ?
O2 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N1 C2 C3 103.87(15) . . ?
C4 C2 N1 126.71(18) . . ?
C4 C2 C3 129.41(19) . . ?
O1 C3 C2 104.76(14) . . ?
O1 C3 H3A 110.8 . . ?
O1 C3 H3B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C12 C17 H17 119.7 . . ?
C12 C17 C16 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C2 C4 H4A 119.5(14) . . ?
C2 C4 H4B 122.0(13) . . ?
H4A C4 H4B 118.5(19) . . ?

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
O2 C8 C9 C10 176.83(16) . . . . ?
N1 C5 C10 C9 -179.65(16) . . . . ?
N1 C2 C3 O1 -1.8(2) . . . . ?
C6 C7 C8 O2 -177.65(16) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C7 C6 C5 N1 178.78(15) . . . . ?
C7 C6 C5 C10 -1.7(3) . . . . ?
C7 C8 C9 C10 -2.7(3) . . . . ?
C1 O1 C3 C2 2.3(2) . . . . ?
C1 N1 C5 C6 -72.2(2) . . . . ?
C1 N1 C5 C10 108.3(2) . . . . ?
C1 N1 C2 C3 0.7(2) . . . . ?
C1 N1 C2 C4 -179.4(2) . . . . ?
C5 N1 C1 S1 -1.2(3) . . . . ?
C5 N1 C1 O1 178.61(15) . . . . ?
C5 N1 C2 C3 -177.14(17) . . . . ?
C5 N1 C2 C4 2.7(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C8 O2 C11 C12 161.14(16) . . . . ?
C8 C9 C10 C5 1.3(3) . . . . ?
C12 C17 C16 C15 0.4(3) . . . . ?
C11 O2 C8 C7 8.0(3) . . . . ?
C11 O2 C8 C9 -171.51(17) . . . . ?
C11 C12 C17 C16 177.52(19) . . . . ?
C11 C12 C13 C14 -178.12(18) . . . . ?
C2 N1 C1 S1 -179.13(15) . . . . ?
C2 N1 C1 O1 0.7(2) . . . . ?
C2 N1 C5 C6 105.4(2) . . . . ?
C2 N1 C5 C10 -74.1(2) . . . . ?
C3 O1 C1 S1 177.92(15) . . . . ?
C3 O1 C1 N1 -1.9(2) . . . . ?
C17 C12 C11 O2 102.5(2) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C15 C14 C13 C12 0.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C13 C12 C11 O2 -80.3(2) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
C16 C15 C14 C13 -0.1(3) . . . . ?
C4 C2 C3 O1 178.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_I1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1879214'
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2020-04-06 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            'C22 H16 Cl N O S'
_chemical_formula_weight         377.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.729(5)
_cell_length_b                   9.766(5)
_cell_length_c                   10.945(6)
_cell_angle_alpha                67.938(14)
_cell_angle_beta                 81.050(14)
_cell_angle_gamma                73.602(14)
_cell_volume                     923.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      2.185
_cell_measurement_theta_max      26.447

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.330
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25680
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.1480
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3797
_reflns_number_gt                3310
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.4154P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3797
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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 0.13599(5) 0.55510(5) 0.71361(4) 0.03894(17) Uani 1 1 d . . . . .
Cl1 Cl 0.49331(7) 0.23343(7) 1.07930(7) 0.0695(2) Uani 1 1 d . . . . .
O1 O 0.24075(13) 0.71217(13) 0.80134(12) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.24912(17) 0.47777(16) 0.95242(15) 0.0371(3) Uani 1 1 d . . . . .
C17 C 0.20391(19) 0.70255(19) 0.38913(17) 0.0344(4) Uani 1 1 d . . . . .
C8 C 0.21094(18) 0.80059(18) 0.66999(17) 0.0326(4) Uani 1 1 d . . . . .
C7 C 0.21377(18) 0.57214(18) 0.84034(17) 0.0313(4) Uani 1 1 d . . . . .
C9 C 0.24550(18) 0.94869(19) 0.62689(18) 0.0350(4) Uani 1 1 d . . . . .
C6 C 0.2237(2) 0.3319(2) 0.99534(17) 0.0374(4) Uani 1 1 d . . . . .
C15 C 0.15455(18) 0.73612(19) 0.60850(17) 0.0338(4) Uani 1 1 d . . . . .
C16 C 0.1065(2) 0.7903(2) 0.47134(18) 0.0394(4) Uani 1 1 d . . . . .
H16A H 0.1046 0.8976 0.4288 0.047 Uiso 1 1 calc R U . . .
H16B H 0.0097 0.7793 0.4754 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2365(2) 1.0199(2) 0.7179(2) 0.0413(4) Uani 1 1 d . . . . .
H10 H 0.2104 0.9720 0.8059 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3503(2) 0.6769(2) 0.3858(2) 0.0468(5) Uani 1 1 d . . . . .
H18 H 0.3908 0.7111 0.4371 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1466(2) 0.6480(2) 0.3136(2) 0.0466(5) Uani 1 1 d . . . . .
H22 H 0.0478 0.6625 0.3154 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2877(2) 1.0219(2) 0.4964(2) 0.0497(5) Uani 1 1 d . . . . .
H14 H 0.2971 0.9751 0.4346 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3324(3) 0.2064(2) 1.0574(2) 0.0484(5) Uani 1 1 d . . . . .
C5 C 0.0939(2) 0.3063(2) 0.9848(2) 0.0482(5) Uani 1 1 d . . . . .
H5 H 0.0191 0.3886 0.9461 0.058 Uiso 1 1 calc R U . . .
C20 C 0.3803(3) 0.5492(3) 0.2314(2) 0.0579(6) Uani 1 1 d . . . . .
H20 H 0.4393 0.4992 0.1778 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2660(2) 1.1609(2) 0.6784(2) 0.0510(5) Uani 1 1 d . . . . .
H11 H 0.2596 1.2072 0.7401 0.061 Uiso 1 1 calc R U . . .
C19 C 0.4387(2) 0.6008(3) 0.3071(3) 0.0582(6) Uani 1 1 d . . . . .
H19 H 0.5378 0.5846 0.3056 0.070 Uiso 1 1 calc R U . . .
C13 C 0.3159(3) 1.1639(3) 0.4581(3) 0.0606(6) Uani 1 1 d . . . . .
H13 H 0.3425 1.2125 0.3703 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3049(3) 1.2337(2) 0.5487(3) 0.0563(6) Uani 1 1 d . . . . .
H12 H 0.3236 1.3293 0.5224 0.068 Uiso 1 1 calc R U . . .
C21 C 0.2356(3) 0.5721(3) 0.2357(2) 0.0591(6) Uani 1 1 d . . . . .
H21 H 0.1958 0.5362 0.1853 0.071 Uiso 1 1 calc R U . . .
C4 C 0.0737(3) 0.1597(3) 1.0311(3) 0.0685(7) Uani 1 1 d . . . . .
H4 H -0.0140 0.1439 1.0236 0.082 Uiso 1 1 calc R U . . .
C2 C 0.3126(4) 0.0603(3) 1.1022(3) 0.0708(7) Uani 1 1 d . . . . .
H2 H 0.3866 -0.0224 1.1419 0.085 Uiso 1 1 calc R U . . .
C3 C 0.1849(4) 0.0376(3) 1.0883(3) 0.0814(9) Uani 1 1 d . . . . .
H3 H 0.1726 -0.0610 1.1177 0.098 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 C15 1.7518(19) . ?
S1 C7 1.7593(19) . ?
Cl1 C1 1.725(3) . ?
O1 C7 1.360(2) . ?
O1 C8 1.397(2) . ?
N1 C7 1.255(2) . ?
N1 C6 1.404(2) . ?
C17 C18 1.372(3) . ?
C17 C22 1.385(3) . ?
C17 C16 1.515(3) . ?
C8 C15 1.334(2) . ?
C8 C9 1.463(2) . ?
C9 C14 1.391(3) . ?
C9 C10 1.394(3) . ?
C6 C1 1.395(3) . ?
C6 C5 1.384(3) . ?
C15 C16 1.495(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9300 . ?
C22 C21 1.382(3) . ?
C22 H22 0.9300 . ?
C14 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C1 C2 1.383(3) . ?
C5 C4 1.389(3) . ?
C5 H5 0.9300 . ?
C20 C21 1.359(4) . ?
C20 C19 1.372(3) . ?
C20 H20 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C13 C12 1.376(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C4 C3 1.381(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.362(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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
C15 S1 C7 90.49(9) . . ?
C7 O1 C8 113.38(13) . . ?
C7 N1 C6 120.29(15) . . ?
C18 C17 C22 118.28(17) . . ?
C18 C17 C16 121.19(16) . . ?
C22 C17 C16 120.53(17) . . ?
C15 C8 O1 114.59(15) . . ?
C15 C8 C9 132.20(17) . . ?
O1 C8 C9 113.20(14) . . ?
N1 C7 O1 118.85(15) . . ?
N1 C7 S1 130.80(14) . . ?
O1 C7 S1 110.31(12) . . ?
C14 C9 C10 118.31(17) . . ?
C14 C9 C8 121.86(16) . . ?
C10 C9 C8 119.82(17) . . ?
C1 C6 C5 118.07(19) . . ?
C1 C6 N1 118.50(18) . . ?
C5 C6 N1 123.37(18) . . ?
C8 C15 C16 131.98(17) . . ?
C8 C15 S1 111.05(14) . . ?
C16 C15 S1 116.97(13) . . ?
C15 C16 C17 112.25(15) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C11 C10 C9 120.57(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C17 C18 C19 120.93(19) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C21 C22 C17 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C13 C14 C9 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 Cl1 119.4(2) . . ?
C6 C1 Cl1 119.73(16) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_MKB_F_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1879222'
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2020-04-06 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            'C17 H13 Cl2 N O S'
_chemical_formula_weight         350.24

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'
Cl Cl 0.1484 0.1585 '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                   7.656(4)
_cell_length_b                   21.804(10)
_cell_length_c                   10.011(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.066(18)
_cell_angle_gamma                90
_cell_volume                     1605.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      2.314
_cell_measurement_theta_max      26.461

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.534
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44307
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3312
_reflns_number_gt                2960
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1715P)²+2.5619P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   0.657
_refine_ls_restrained_S_all      0.657
_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 0.39386(8) 0.33043(3) 0.37400(7) 0.0429(2) Uani 1 1 d . . . . .
Cl02 Cl 0.45974(10) 0.49907(4) 0.73788(10) 0.0713(3) Uani 1 1 d . . . . .
Cl03 Cl 0.21867(17) 0.36331(7) -0.06197(13) 0.1136(6) Uani 1 1 d . . . . .
O1 O 0.4505(3) 0.22682(8) 0.2644(2) 0.0532(5) Uani 1 1 d . . . . .
N1 N 0.1876(3) 0.27081(10) 0.1483(2) 0.0528(6) Uani 1 1 d . . . . .
C11 C 0.7625(3) 0.38230(10) 0.5899(2) 0.0326(5) Uani 1 1 d . . . . .
C16 C 0.9214(3) 0.41624(10) 0.6022(2) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.6028(3) 0.29467(9) 0.4470(2) 0.0367(5) Uani 1 1 d . . . . .
C10 C 0.7475(3) 0.31983(10) 0.5323(3) 0.0378(5) Uani 1 1 d . . . . .
H10 H 0.8512 0.2955 0.5589 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6201(3) 0.40815(11) 0.6321(2) 0.0382(5) Uani 1 1 d . . . . .
H12 H 0.5157 0.3855 0.6273 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0646(3) 0.32017(11) 0.1301(2) 0.0426(6) Uani 1 1 d . . . . .
C14 C 0.7871(3) 0.50223(11) 0.6897(3) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.7943 0.5425 0.7211 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3285(3) 0.27241(10) 0.2474(2) 0.0398(5) Uani 1 1 d . . . . .
C15 C 0.9288(3) 0.47583(11) 0.6506(3) 0.0404(5) Uani 1 1 d . . . . .
H15 H 1.0330 0.4989 0.6571 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6352(3) 0.46754(11) 0.6809(2) 0.0408(5) Uani 1 1 d . . . . .
C17 C 1.0802(3) 0.38984(12) 0.5609(3) 0.0442(6) Uani 1 1 d . . . . .
H17A H 1.1754 0.4199 0.5758 0.066 Uiso 1 1 calc R U . . .
H17B H 1.0425 0.3786 0.4644 0.066 Uiso 1 1 calc R U . . .
H17C H 1.1241 0.3542 0.6162 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0639(4) 0.32362(14) 0.2028(3) 0.0553(7) Uani 1 1 d . . . . .
H5 H -0.0633 0.2944 0.2706 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5913(4) 0.23018(11) 0.3926(3) 0.0510(6) Uani 1 1 d . . . . .
H8A H 0.7066 0.2184 0.3776 0.061 Uiso 1 1 calc R U . . .
H8B H 0.5649 0.2022 0.4597 0.061 Uiso 1 1 calc R U . . .
C1 C 0.0591(4) 0.36438(14) 0.0307(3) 0.0509(6) Uani 1 1 d . . . . .
C2 C -0.0708(4) 0.40959(15) 0.0038(3) 0.0588(7) Uani 1 1 d . . . . .
H2 H -0.0726 0.4388 -0.0642 0.071 Uiso 1 1 calc R U . . .
C3 C -0.1979(4) 0.41174(15) 0.0768(3) 0.0582(7) Uani 1 1 d . . . . .
H3 H -0.2869 0.4420 0.0580 0.070 Uiso 1 1 calc R U . . .
C4 C -0.1924(4) 0.36900(16) 0.1777(3) 0.0602(7) Uani 1 1 d . . . . .
H4 H -0.2762 0.3707 0.2294 0.072 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 C9 1.747(2) . ?
S1 C7 1.762(2) . ?
Cl02 C13 1.740(2) . ?
Cl03 C1 1.726(3) . ?
O1 C7 1.342(3) . ?
O1 C8 1.431(3) . ?
N1 C7 1.248(3) . ?
N1 C6 1.408(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.400(3) . ?
C11 C10 1.471(3) . ?
C16 C15 1.383(3) . ?
C16 C17 1.502(3) . ?
C9 C10 1.317(3) . ?
C9 C8 1.502(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C6 C1 1.378(4) . ?
C6 C5 1.379(4) . ?
C14 C15 1.377(4) . ?
C14 C13 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.369(4) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.373(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
C9 S1 C7 91.46(11) . . ?
C7 O1 C8 113.63(19) . . ?
C7 N1 C6 118.8(2) . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 C10 120.7(2) . . ?
C16 C11 C10 119.7(2) . . ?
C15 C16 C11 118.5(2) . . ?
C15 C16 C17 119.9(2) . . ?
C11 C16 C17 121.5(2) . . ?
C10 C9 C8 125.4(2) . . ?
C10 C9 S1 126.43(18) . . ?
C8 C9 S1 108.12(17) . . ?
C9 C10 C11 126.9(2) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 H10 116.5 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C1 C6 N1 120.9(3) . . ?
C1 C6 C5 117.4(2) . . ?
N1 C6 C5 121.5(3) . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
N1 C7 O1 119.9(2) . . ?
N1 C7 S1 127.09(19) . . ?
O1 C7 S1 113.03(17) . . ?
C16 C15 C14 122.3(2) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 Cl02 119.43(19) . . ?
C14 C13 Cl02 118.67(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
O1 C8 C9 109.1(2) . . ?
O1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 Cl03 119.6(2) . . ?
C2 C1 Cl03 119.1(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.073

