# 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_113
_audit_block_doi                 10.5517/ccdc.csd.cc29xgl9
_database_code_depnum_ccdc_archive 'CCDC 2142521'
loop_
_audit_author_name
_audit_author_address
'V. Ramkumar'
;Department of chemistry, IIT Madras
India
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2022-09-06 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            'C15 H9 Cl O S'
_chemical_formula_weight         272.73

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   21.345(3)
_cell_length_b                   3.9444(5)
_cell_length_c                   14.7541(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.455(5)
_cell_angle_gamma                90
_cell_volume                     1221.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1970
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.73

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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            3475
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        24.989
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.808
_reflns_number_total             1747
_reflns_number_gt                1614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.646
_reflns_Friedel_fraction_full    0.646

_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    '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)+(0.0198P)²+0.6737P] 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_abs_structure_details 
; 
 Flack x determined using 612 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.92(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1747
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.29225(19) 0.5688(10) 1.1448(3) 0.0426(10) Uani 1 1 d . . . . .
C2 C 0.3529(2) 0.4452(11) 1.1482(3) 0.0526(11) Uani 1 1 d . . . . .
H2 H 0.3751 0.3532 1.2027 0.063 Uiso 1 1 calc R U . . .
C3 C 0.38034(18) 0.4572(11) 1.0717(3) 0.0541(12) Uani 1 1 d . . . . .
H3 H 0.4215 0.3757 1.0739 0.065 Uiso 1 1 calc R U . . .
C4 C 0.34642(19) 0.5923(12) 0.9906(3) 0.0540(13) Uani 1 1 d . . . . .
H4 H 0.3646 0.5993 0.9379 0.065 Uiso 1 1 calc R U . . .
C5 C 0.28576(16) 0.7160(11) 0.9882(3) 0.0446(10) Uani 1 1 d . . . . .
H5 H 0.2636 0.8048 0.9333 0.054 Uiso 1 1 calc R U . . .
C6 C 0.25648(15) 0.7128(10) 1.0650(2) 0.0354(9) Uani 1 1 d . . . . .
C7 C 0.19308(15) 0.8466(9) 1.0646(2) 0.0374(9) Uani 1 1 d . . . . .
H7 H 0.1787 0.8205 1.1200 0.045 Uiso 1 1 calc R U . . .
C8 C 0.15143(16) 1.0024(9) 0.9978(3) 0.0340(8) Uani 1 1 d . . . . .
C9 C 0.08440(14) 1.2819(9) 0.8591(2) 0.0356(9) Uani 1 1 d . . . . .
C10 C 0.05651(18) 1.4186(11) 0.7744(3) 0.0456(10) Uani 1 1 d . . . . .
H10 H 0.0776 1.4155 0.7246 0.055 Uiso 1 1 calc R U . . .
C11 C -0.0033(2) 1.5589(11) 0.7668(3) 0.0545(12) Uani 1 1 d . . . . .
H11 H -0.0224 1.6544 0.7110 0.065 Uiso 1 1 calc R U . . .
C12 C -0.03542(19) 1.5614(12) 0.8394(3) 0.0536(13) Uani 1 1 d . . . . .
H12 H -0.0759 1.6567 0.8319 0.064 Uiso 1 1 calc R U . . .
C13 C -0.00861(16) 1.4254(10) 0.9229(3) 0.0457(10) Uani 1 1 d . . . . .
H13 H -0.0305 1.4274 0.9719 0.055 Uiso 1 1 calc R U . . .
C14 C 0.05232(15) 1.2835(10) 0.9330(2) 0.0353(9) Uani 1 1 d . . . . .
C15 C 0.08818(16) 1.1214(10) 1.0155(3) 0.0390(9) Uani 1 1 d . . . . .
Cl1 Cl 0.26074(6) 0.5437(4) 1.24524(7) 0.0820(5) Uani 1 1 d . . . . .
O1 O 0.06965(13) 1.0848(8) 1.0889(2) 0.0622(9) Uani 1 1 d . . . . .
S1 S 0.16010(4) 1.0958(3) 0.88433(5) 0.0400(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(5) . ?
C1 C6 1.403(5) . ?
C1 Cl1 1.737(4) . ?
C2 C3 1.364(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(5) . ?
C7 C8 1.349(5) . ?
C7 H7 0.9300 . ?
C8 C15 1.496(5) . ?
C8 S1 1.757(4) . ?
C9 C14 1.388(4) . ?
C9 C10 1.391(5) . ?
C9 S1 1.752(3) . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.463(5) . ?
C15 O1 1.227(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.6(4) . . ?
C2 C1 Cl1 117.1(3) . . ?
C6 C1 Cl1 120.2(3) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.4(4) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 115.6(3) . . ?
C5 C6 C7 123.4(3) . . ?
C1 C6 C7 121.0(3) . . ?
C8 C7 C6 131.2(3) . . ?
C8 C7 H7 114.4 . . ?
C6 C7 H7 114.4 . . ?
C7 C8 C15 120.7(4) . . ?
C7 C8 S1 128.5(3) . . ?
C15 C8 S1 110.8(3) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 S1 113.7(3) . . ?
C10 C9 S1 125.5(3) . . ?
C11 C10 C9 117.9(4) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 118.8(4) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 C15 113.2(3) . . ?
C13 C14 C15 126.8(3) . . ?
O1 C15 C14 125.6(3) . . ?
O1 C15 C8 124.2(4) . . ?
C14 C15 C8 110.1(3) . . ?
C8 S1 C9 92.16(17) . . ?

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
C6 C1 C2 C3 -0.5(6) . . . . ?
Cl1 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C2 C1 C6 C5 1.4(6) . . . . ?
Cl1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C7 -178.8(4) . . . . ?
Cl1 C1 C6 C7 0.7(5) . . . . ?
C5 C6 C7 C8 -2.3(6) . . . . ?
C1 C6 C7 C8 177.9(4) . . . . ?
C6 C7 C8 C15 -179.4(4) . . . . ?
C6 C7 C8 S1 0.6(6) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
S1 C9 C10 C11 -179.3(3) . . . . ?
C9 C10 C11 C12 -0.9(6) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C10 C9 C14 C13 -0.3(5) . . . . ?
S1 C9 C14 C13 179.8(3) . . . . ?
C10 C9 C14 C15 178.5(3) . . . . ?
S1 C9 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C12 C13 C14 C15 -178.8(4) . . . . ?
C9 C14 C15 O1 -178.5(4) . . . . ?
C13 C14 C15 O1 0.3(6) . . . . ?
C9 C14 C15 C8 1.2(4) . . . . ?
C13 C14 C15 C8 179.9(4) . . . . ?
C7 C8 C15 O1 -0.8(6) . . . . ?
S1 C8 C15 O1 179.2(3) . . . . ?
C7 C8 C15 C14 179.5(3) . . . . ?
S1 C8 C15 C14 -0.5(4) . . . . ?
C7 C8 S1 C9 179.7(3) . . . . ?
C15 C8 S1 C9 -0.2(3) . . . . ?
C14 C9 S1 C8 1.0(3) . . . . ?
C10 C9 S1 C8 -178.9(3) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033



####################################################################### 
# 
# 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_120
_database_code_depnum_ccdc_archive 'CCDC 2142524'
loop_
_audit_author_name
_audit_author_address
'Ramkumar V'
;Department of chemistry, IIT Madras
India
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2022-09-06 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            'C16 H12 O S'
_chemical_formula_weight         252.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.0327(12)
_cell_length_b                   7.7486(14)
_cell_length_c                   11.892(2)
_cell_angle_alpha                84.539(9)
_cell_angle_beta                 79.040(9)
_cell_angle_gamma                76.596(9)
_cell_volume                     617.99(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1386
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      21.60

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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            9200
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             2173
_reflns_number_gt                1503
_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    '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)+(0.1670P)²] 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         2173
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.2128
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.2417(5) 0.2922(5) 0.2913(3) 0.0424(9) Uani 1 1 d . . . . .
C2 C 0.2277(6) 0.4584(5) 0.2340(4) 0.0585(12) Uani 1 1 d . . . . .
H2 H 0.1965 0.5615 0.2741 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2615(7) 0.4653(6) 0.1163(4) 0.0675(13) Uani 1 1 d . . . . .
H3 H 0.2540 0.5755 0.0768 0.081 Uiso 1 1 calc R U . . .
C4 C 0.3061(7) 0.3149(7) 0.0545(4) 0.0648(12) Uani 1 1 d . . . . .
H4 H 0.3267 0.3242 -0.0252 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3200(6) 0.1507(6) 0.1120(4) 0.0524(11) Uani 1 1 d . . . . .
H5 H 0.3508 0.0480 0.0716 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2878(5) 0.1405(5) 0.2298(3) 0.0403(9) Uani 1 1 d . . . . .
C7 C 0.3023(5) -0.0230(5) 0.3044(3) 0.0397(9) Uani 1 1 d . . . . .
C8 C 0.2613(5) 0.0208(5) 0.4274(3) 0.0381(9) Uani 1 1 d . . . . .
C9 C 0.2695(5) -0.1095(5) 0.5114(3) 0.0411(9) Uani 1 1 d . . . . .
H9 H 0.3026 -0.2234 0.4845 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2368(5) -0.1063(5) 0.6351(3) 0.0392(9) Uani 1 1 d . . . . .
C11 C 0.2549(5) -0.2683(5) 0.7028(3) 0.0417(9) Uani 1 1 d . . . . .
C12 C 0.2231(6) -0.2614(6) 0.8200(4) 0.0535(11) Uani 1 1 d . . . . .
H12 H 0.2336 -0.3672 0.8648 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1764(6) -0.1040(6) 0.8733(4) 0.0569(12) Uani 1 1 d . . . . .
H13 H 0.1560 -0.1040 0.9529 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1596(6) 0.0550(6) 0.8081(4) 0.0575(12) Uani 1 1 d . . . . .
H14 H 0.1286 0.1624 0.8435 0.069 Uiso 1 1 calc R U . . .
C15 C 0.1889(6) 0.0525(5) 0.6921(4) 0.0514(10) Uani 1 1 d . . . . .
H15 H 0.1767 0.1598 0.6489 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3073(7) -0.4457(5) 0.6497(4) 0.0575(11) Uani 1 1 d . . . . .
H16A H 0.3184 -0.5389 0.7090 0.086 Uiso 1 1 calc R U . . .
H16B H 0.4315 -0.4568 0.5979 0.086 Uiso 1 1 calc R U . . .
H16C H 0.2053 -0.4545 0.6085 0.086 Uiso 1 1 calc R U . . .
O1 O 0.3449(4) -0.1738(4) 0.2715(2) 0.0586(8) Uani 1 1 d . . . . .
S1 S 0.20859(15) 0.25154(12) 0.44025(9) 0.0471(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(5) . ?
C1 C2 1.390(5) . ?
C1 S1 1.750(4) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.471(5) . ?
C7 O1 1.220(4) . ?
C7 C8 1.492(5) . ?
C8 C9 1.350(5) . ?
C8 S1 1.755(4) . ?
C9 C10 1.447(5) . ?
C9 H9 0.9300 . ?
C10 C15 1.402(5) . ?
C10 C11 1.419(5) . ?
C11 C12 1.373(6) . ?
C11 C16 1.505(5) . ?
C12 C13 1.371(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C6 C1 C2 120.1(4) . . ?
C6 C1 S1 114.3(3) . . ?
C2 C1 S1 125.6(3) . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.1(4) . . ?
C5 C6 C7 126.4(3) . . ?
C1 C6 C7 112.5(3) . . ?
O1 C7 C6 125.4(3) . . ?
O1 C7 C8 124.3(4) . . ?
C6 C7 C8 110.3(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 S1 128.6(3) . . ?
C7 C8 S1 110.8(3) . . ?
C8 C9 C10 132.4(4) . . ?
C8 C9 H9 113.8 . . ?
C10 C9 H9 113.8 . . ?
C15 C10 C11 117.8(3) . . ?
C15 C10 C9 122.4(3) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 118.6(4) . . ?
C12 C11 C16 119.6(4) . . ?
C10 C11 C16 121.9(3) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 122.3(4) . . ?
C14 C15 H15 118.9 . . ?
C10 C15 H15 118.9 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 S1 C8 92.07(17) . . ?

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
C6 C1 C2 C3 -0.2(6) . . . . ?
S1 C1 C2 C3 179.0(3) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
S1 C1 C6 C5 -179.4(3) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
S1 C1 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 O1 -0.2(6) . . . . ?
C1 C6 C7 O1 -178.4(3) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C1 C6 C7 C8 0.4(4) . . . . ?
O1 C7 C8 C9 -0.1(6) . . . . ?
C6 C7 C8 C9 -179.0(3) . . . . ?
O1 C7 C8 S1 179.3(3) . . . . ?
C6 C7 C8 S1 0.4(4) . . . . ?
C7 C8 C9 C10 -179.7(3) . . . . ?
S1 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C15 -1.1(6) . . . . ?
C8 C9 C10 C11 179.5(3) . . . . ?
C15 C10 C11 C12 0.5(5) . . . . ?
C9 C10 C11 C12 180.0(3) . . . . ?
C15 C10 C11 C16 -179.5(3) . . . . ?
C9 C10 C11 C16 -0.1(5) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C16 C11 C12 C13 179.5(4) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C13 C14 C15 C10 -0.3(6) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C9 C10 C15 C14 -179.5(3) . . . . ?
C6 C1 S1 C8 1.1(3) . . . . ?
C2 C1 S1 C8 -178.1(3) . . . . ?
C9 C8 S1 C1 178.5(3) . . . . ?
C7 C8 S1 C1 -0.8(3) . . . . ?

_refine_diff_density_max         0.909
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.111



