# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_69
_database_code_depnum_ccdc_archive 'CCDC 2031230'
loop_
_audit_author_name
_audit_author_address
'Sundaravelu Nallappan'
;IITM
India
;
_audit_update_record             
;
2020-09-10 deposited with the CCDC.	2021-03-23 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 S2'
_chemical_formula_weight         284.38

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      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                   13.9263(10)
_cell_length_b                   12.3383(9)
_cell_length_c                   7.8707(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.311(3)
_cell_angle_gamma                90
_cell_volume                     1341.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3461
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      26.55

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.384
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.955
_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            8986
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.474
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2350
_reflns_number_gt                1855
_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)+(0.0360P)²+0.6947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2350
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.005
_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 0.52264(14) 0.15514(17) 0.0925(2) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.60316(16) 0.20374(18) 0.0344(3) 0.0435(5) Uani 1 1 d . . . . .
H2 H 0.5961 0.2626 -0.0400 0.052 Uiso 1 1 calc R U . . .
C3 C 0.69303(17) 0.1619(2) 0.0907(3) 0.0520(6) Uani 1 1 d . . . . .
H3 H 0.7475 0.1937 0.0546 0.062 Uiso 1 1 calc R U . . .
C4 C 0.70444(17) 0.0732(2) 0.2003(3) 0.0529(6) Uani 1 1 d . . . . .
H4 H 0.7663 0.0469 0.2362 0.064 Uiso 1 1 calc R U . . .
C5 C 0.62620(16) 0.02400(19) 0.2562(3) 0.0449(5) Uani 1 1 d . . . . .
H5 H 0.6342 -0.0357 0.3288 0.054 Uiso 1 1 calc R U . . .
C6 C 0.53382(15) 0.06548(17) 0.2016(2) 0.0352(5) Uani 1 1 d . . . . .
C7 C 0.44294(15) 0.02772(17) 0.2429(2) 0.0355(5) Uani 1 1 d . . . . .
C8 C 0.36377(15) 0.08901(16) 0.1713(2) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.26516(15) 0.06843(17) 0.1833(2) 0.0386(5) Uani 1 1 d . . . . .
C10 C 0.18912(14) 0.14162(18) 0.0991(3) 0.0397(5) Uani 1 1 d . . . . .
C11 C 0.10704(15) 0.0989(2) 0.0027(3) 0.0477(6) Uani 1 1 d . . . . .
H11 H 0.1012 0.0242 -0.0117 0.057 Uiso 1 1 calc R U . . .
C12 C 0.03431(16) 0.1660(2) -0.0717(3) 0.0546(7) Uani 1 1 d . . . . .
H12 H -0.0194 0.1360 -0.1374 0.066 Uiso 1 1 calc R U . . .
C13 C 0.03987(17) 0.2771(2) -0.0502(3) 0.0539(6) Uani 1 1 d . . . . .
C14 C 0.12149(17) 0.3193(2) 0.0464(3) 0.0527(6) Uani 1 1 d . . . . .
H14 H 0.1265 0.3939 0.0622 0.063 Uiso 1 1 calc R U . . .
C15 C 0.19538(16) 0.25349(19) 0.1194(3) 0.0454(5) Uani 1 1 d . . . . .
H15 H 0.2497 0.2840 0.1826 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0411(2) 0.3503(3) -0.1287(4) 0.0824(10) Uani 1 1 d . . . . .
H16A H -0.0788 0.3735 -0.0414 0.124 Uiso 1 1 calc R U . . .
H16B H -0.0817 0.3113 -0.2157 0.124 Uiso 1 1 calc R U . . .
H16C H -0.0140 0.4124 -0.1786 0.124 Uiso 1 1 calc R U . . .
O1 O 0.43876(12) -0.05977(13) 0.33902(19) 0.0472(4) Uani 1 1 d . . . . .
S1 S 0.40288(4) 0.19498(5) 0.04461(7) 0.04197(18) Uani 1 1 d . . . . .
S2 S 0.22932(4) -0.03966(5) 0.28982(8) 0.0541(2) Uani 1 1 d . . . . .
H1O H 0.375(2) -0.072(3) 0.348(4) 0.095(11) 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
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C1 S1 1.734(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.424(3) . ?
C7 O1 1.324(2) . ?
C7 C8 1.395(3) . ?
C8 C9 1.411(3) . ?
C8 S1 1.772(2) . ?
C9 C10 1.482(3) . ?
C9 S2 1.684(2) . ?
C10 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C16 1.513(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 H1O 0.91(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.6(2) . . ?
C6 C1 S1 112.76(15) . . ?
C2 C1 S1 126.63(17) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 C7 111.50(18) . . ?
C5 C6 C7 128.2(2) . . ?
O1 C7 C8 125.65(19) . . ?
O1 C7 C6 120.13(19) . . ?
C8 C7 C6 114.21(18) . . ?
C7 C8 C9 126.95(19) . . ?
C7 C8 S1 110.09(15) . . ?
C9 C8 S1 122.80(16) . . ?
C8 C9 C10 120.42(19) . . ?
C8 C9 S2 121.88(16) . . ?
C10 C9 S2 117.69(15) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 121.49(19) . . ?
C11 C10 C9 120.2(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 118.0(2) . . ?
C12 C13 C16 121.0(3) . . ?
C14 C13 C16 121.0(3) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 O1 H1O 107(2) . . ?
C1 S1 C8 91.41(10) . . ?

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 -1.2(3) . . . . ?
S1 C1 C2 C3 178.20(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
S1 C1 C6 C5 -178.67(15) . . . . ?
C2 C1 C6 C7 -179.07(18) . . . . ?
S1 C1 C6 C7 1.4(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C1 C6 C7 O1 177.00(17) . . . . ?
C5 C6 C7 O1 -2.9(3) . . . . ?
C1 C6 C7 C8 -1.8(2) . . . . ?
C5 C6 C7 C8 178.25(19) . . . . ?
O1 C7 C8 C9 -1.8(3) . . . . ?
C6 C7 C8 C9 176.95(19) . . . . ?
O1 C7 C8 S1 -177.35(16) . . . . ?
C6 C7 C8 S1 1.4(2) . . . . ?
C7 C8 C9 C10 -179.86(19) . . . . ?
S1 C8 C9 C10 -4.9(3) . . . . ?
C7 C8 C9 S2 -0.7(3) . . . . ?
S1 C8 C9 S2 174.25(11) . . . . ?
C8 C9 C10 C15 -49.0(3) . . . . ?
S2 C9 C10 C15 131.87(19) . . . . ?
C8 C9 C10 C11 133.7(2) . . . . ?
S2 C9 C10 C11 -45.4(2) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C11 C12 C13 C16 -178.6(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C16 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
C9 C10 C15 C14 -176.93(19) . . . . ?
C6 C1 S1 C8 -0.53(15) . . . . ?
C2 C1 S1 C8 179.99(18) . . . . ?
C7 C8 S1 C1 -0.50(15) . . . . ?
C9 C8 S1 C1 -176.25(18) . . . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2043956'
loop_
_audit_author_name
_audit_author_address
'Rintu robert'
;IIT
India
;
_audit_update_record             
;
2020-11-12 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 O2 S2'
_chemical_formula_weight         298.36

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                   6.9373(3)
_cell_length_b                   9.0024(4)
_cell_length_c                   11.0434(5)
_cell_angle_alpha                88.3339(18)
_cell_angle_beta                 86.4577(18)
_cell_angle_gamma                76.6509(16)
_cell_volume                     669.69(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6286
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.12

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.394
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.954
_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            8889
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.848
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8889
_reflns_number_gt                7875
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1010P)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         8889
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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 0.2368(3) 0.6021(2) -0.1812(2) 0.0328(5) Uani 1 1 d . . . . .
C2 C 0.2644(3) 0.5391(3) -0.2971(2) 0.0426(6) Uani 1 1 d . . . . .
H2 H 0.295897 0.433851 -0.306781 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2440(3) 0.6354(3) -0.3959(2) 0.0513(6) Uani 1 1 d . . . . .
H3 H 0.263083 0.594736 -0.473349 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1953(3) 0.7932(3) -0.3825(2) 0.0527(7) Uani 1 1 d . . . . .
H4 H 0.180876 0.855928 -0.451344 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1680(3) 0.8587(3) -0.2694(2) 0.0453(6) Uani 1 1 d . . . . .
H5 H 0.136000 0.964217 -0.261106 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1900(3) 0.7614(2) -0.1676(2) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.2144(3) 0.6263(2) 0.0313(2) 0.0293(5) Uani 1 1 d . . . . .
C8 C 0.2189(3) 0.5777(2) 0.1545(2) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.2623(3) 0.4110(2) 0.16875(19) 0.0287(5) Uani 1 1 d . . . . .
C10 C 0.2724(3) 0.3403(2) 0.28365(19) 0.0331(5) Uani 1 1 d . . . . .
H10 H 0.252935 0.399605 0.352817 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3108(3) 0.1839(2) 0.2950(2) 0.0359(5) Uani 1 1 d . . . . .
C12 C 0.3381(3) 0.0939(2) 0.1913(2) 0.0404(6) Uani 1 1 d . . . . .
H12 H 0.362087 -0.011808 0.199308 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3298(3) 0.1605(2) 0.0781(2) 0.0364(5) Uani 1 1 d . . . . .
H13 H 0.348526 0.100241 0.009500 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2933(3) 0.3185(2) 0.06603(19) 0.0299(5) Uani 1 1 d . . . . .
C15 C 0.2482(3) 0.5293(2) -0.06533(19) 0.0299(5) Uani 1 1 d . . . . .
C16 C 0.3017(4) 0.1914(3) 0.5106(2) 0.0543(7) Uani 1 1 d . . . . .
H16A H 0.400623 0.250513 0.509021 0.081 Uiso 1 1 calc R U . . .
H16B H 0.317040 0.123125 0.579569 0.081 Uiso 1 1 calc R U . . .
H16C H 0.172076 0.258465 0.516171 0.081 Uiso 1 1 calc R U . . .
O1 O 0.28796(19) 0.37471(14) -0.05162(13) 0.0328(4) Uani 1 1 d . . . . .
O2 O 0.3244(2) 0.10526(16) 0.40223(15) 0.0500(5) Uani 1 1 d . . . . .
S1 S 0.16463(7) 0.81637(5) -0.01665(5) 0.0367(2) Uani 1 1 d . . . . .
S2 S 0.17859(10) 0.69999(6) 0.26752(5) 0.0539(3) 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 1.400(3) . ?
C1 C6 1.406(3) . ?
C1 C15 1.419(3) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.739(2) . ?
C7 C15 1.373(3) . ?
C7 C8 1.417(3) . ?
C7 S1 1.7393(18) . ?
C8 C9 1.466(3) . ?
C8 S2 1.656(2) . ?
C9 C10 1.402(3) . ?
C9 C14 1.403(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 O2 1.359(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 O1 1.380(2) . ?
C15 O1 1.361(2) . ?
C16 O2 1.426(3) . ?
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
C2 C1 C6 120.2(2) . . ?
C2 C1 C15 130.10(19) . . ?
C6 C1 C15 109.67(19) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 S1 126.39(18) . . ?
C1 C6 S1 113.11(16) . . ?
C15 C7 C8 124.30(17) . . ?
C15 C7 S1 111.42(16) . . ?
C8 C7 S1 124.28(16) . . ?
C7 C8 C9 112.74(18) . . ?
C7 C8 S2 122.22(15) . . ?
C9 C8 S2 125.04(16) . . ?
C10 C9 C14 118.43(17) . . ?
C10 C9 C8 121.52(18) . . ?
C14 C9 C8 120.04(18) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O2 C11 C10 124.7(2) . . ?
O2 C11 C12 115.21(18) . . ?
C10 C11 C12 120.0(2) . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O1 C14 C13 115.51(18) . . ?
O1 C14 C9 123.77(17) . . ?
C13 C14 C9 120.72(19) . . ?
O1 C15 C7 122.74(18) . . ?
O1 C15 C1 122.18(18) . . ?
C7 C15 C1 115.07(17) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 O1 C14 116.40(15) . . ?
C11 O2 C16 117.48(16) . . ?
C7 S1 C6 90.72(10) . . ?

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 -0.3(3) . . . . ?
C15 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 S1 179.58(15) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C15 C1 C6 C5 -179.22(17) . . . . ?
C2 C1 C6 S1 -179.29(15) . . . . ?
C15 C1 C6 S1 0.7(2) . . . . ?
C15 C7 C8 C9 -0.4(3) . . . . ?
S1 C7 C8 C9 179.35(13) . . . . ?
C15 C7 C8 S2 179.52(14) . . . . ?
S1 C7 C8 S2 -0.7(3) . . . . ?
C7 C8 C9 C10 -179.70(16) . . . . ?
S2 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C14 -0.3(3) . . . . ?
S2 C8 C9 C14 179.79(13) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 179.14(16) . . . . ?
C9 C10 C11 O2 179.61(18) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
O2 C11 C12 C13 -179.30(17) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O1 179.94(16) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C10 C9 C14 O1 -179.74(16) . . . . ?
C8 C9 C14 O1 0.8(3) . . . . ?
C10 C9 C14 C13 1.1(3) . . . . ?
C8 C9 C14 C13 -178.40(17) . . . . ?
C8 C7 C15 O1 0.7(3) . . . . ?
S1 C7 C15 O1 -179.16(13) . . . . ?
C8 C7 C15 C1 -179.91(17) . . . . ?
S1 C7 C15 C1 0.3(2) . . . . ?
C2 C1 C15 O1 -1.2(3) . . . . ?
C6 C1 C15 O1 178.81(15) . . . . ?
C2 C1 C15 C7 179.37(19) . . . . ?
C6 C1 C15 C7 -0.6(2) . . . . ?
C7 C15 O1 C14 -0.1(3) . . . . ?
C1 C15 O1 C14 -179.50(16) . . . . ?
C13 C14 O1 C15 178.63(15) . . . . ?
C9 C14 O1 C15 -0.6(3) . . . . ?
C10 C11 O2 C16 -1.5(3) . . . . ?
C12 C11 O2 C16 178.78(17) . . . . ?
C15 C7 S1 C6 0.11(14) . . . . ?
C8 C7 S1 C6 -179.70(17) . . . . ?
C5 C6 S1 C7 179.43(19) . . . . ?
C1 C6 S1 C7 -0.48(15) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_925
_database_code_depnum_ccdc_archive 'CCDC 2031231'
loop_
_audit_author_name
_audit_author_address
'Sundaravelu Nallappan'
;IITM
India
;
_audit_update_record             
;
2020-09-10 deposited with the CCDC.	2021-03-23 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 H15 N O S2'
_chemical_formula_weight         313.42

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'
N N 0.0061 0.0033 '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                   9.1370(3)
_cell_length_b                   9.3396(4)
_cell_length_c                   9.3410(3)
_cell_angle_alpha                105.2378(17)
_cell_angle_beta                 102.3386(17)
_cell_angle_gamma                91.2454(18)
_cell_volume                     748.76(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6231
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.03

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.353
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.949
_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            11007
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_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             2625
_reflns_number_gt                2248
_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)+(0.0449P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.2236(2) 0.4528(2) 0.4782(2) 0.0550(5) Uani 1 1 d . . . . .
H1 H 0.1829 0.5228 0.4297 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1767(2) 0.4339(2) 0.6014(3) 0.0615(5) Uani 1 1 d . . . . .
H2 H 0.1044 0.4924 0.6379 0.074 Uiso 1 1 calc R U . . .
C3 C 0.2358(2) 0.3279(3) 0.6734(3) 0.0625(6) Uani 1 1 d . . . . .
H3 H 0.2019 0.3168 0.7572 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3427(2) 0.2398(2) 0.6235(2) 0.0572(5) Uani 1 1 d . . . . .
H4 H 0.3811 0.1688 0.6717 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3923(2) 0.2595(2) 0.4982(2) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.50929(19) 0.26798(19) 0.28023(18) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.40014(19) 0.36811(19) 0.3007(2) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.33391(19) 0.36557(19) 0.4254(2) 0.0429(4) Uani 1 1 d . . . . .
C9 C 0.58888(19) 0.23765(19) 0.16134(19) 0.0409(4) Uani 1 1 d . . . . .
C10 C 0.70410(19) 0.13004(19) 0.15928(18) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.8165(2) 0.1322(2) 0.2878(2) 0.0471(4) Uani 1 1 d . . . . .
H11 H 0.8164 0.2012 0.3800 0.056 Uiso 1 1 calc R U . . .
C12 C 0.9271(2) 0.0349(2) 0.2816(2) 0.0490(5) Uani 1 1 d . . . . .
H12 H 1.0025 0.0421 0.3682 0.059 Uiso 1 1 calc R U . . .
C13 C 0.92848(19) -0.0753(2) 0.1464(2) 0.0433(4) Uani 1 1 d . . . . .
C14 C 0.81635(19) -0.0757(2) 0.0169(2) 0.0446(4) Uani 1 1 d . . . . .
H14 H 0.8141 -0.1463 -0.0749 0.053 Uiso 1 1 calc R U . . .
C15 C 0.71047(19) 0.02574(19) 0.02365(19) 0.0426(4) Uani 1 1 d . . . . .
H15 H 0.6406 0.0251 -0.0650 0.051 Uiso 1 1 calc R U . . .
C16 C 1.1543(3) -0.1712(3) 0.2697(3) 0.0746(7) Uani 1 1 d . . . . .
H16A H 1.2109 -0.0760 0.2998 0.112 Uiso 1 1 calc R U . . .
H16B H 1.2189 -0.2486 0.2427 0.112 Uiso 1 1 calc R U . . .
H16C H 1.1140 -0.1842 0.3527 0.112 Uiso 1 1 calc R U . . .
C17 C 1.0278(2) -0.2932(2) 0.0005(3) 0.0655(6) Uani 1 1 d . . . . .
H17A H 0.9357 -0.3556 -0.0262 0.098 Uiso 1 1 calc R U . . .
H17B H 1.1116 -0.3523 0.0151 0.098 Uiso 1 1 calc R U . . .
H17C H 1.0328 -0.2483 -0.0799 0.098 Uiso 1 1 calc R U . . .
N1 N 1.03270(18) -0.17807(19) 0.13996(19) 0.0539(4) Uani 1 1 d . . . . .
O1 O 0.35421(16) 0.45963(15) 0.21515(17) 0.0570(4) Uani 1 1 d . . . . .
S1 S 0.52871(6) 0.16584(6) 0.41672(5) 0.05044(16) Uani 1 1 d . . . . .
S2 S 0.54830(6) 0.31811(6) 0.01866(6) 0.05773(18) Uani 1 1 d . . . . .
H1O H 0.406(3) 0.432(3) 0.131(4) 0.114(11) 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
C1 C2 1.362(3) . ?
C1 C8 1.400(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.396(3) . ?
C5 S1 1.7328(18) . ?
C6 C7 1.391(2) . ?
C6 C9 1.425(3) . ?
C6 S1 1.7654(17) . ?
C7 O1 1.333(2) . ?
C7 C8 1.428(3) . ?
C9 C10 1.471(2) . ?
C9 S2 1.6750(17) . ?
C10 C15 1.394(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.366(2) . ?
C13 C14 1.407(2) . ?
C14 C15 1.368(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.445(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.446(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1 H1O 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 119.15(19) . . ?
C2 C1 H1 120.4 . . ?
C8 C1 H1 120.4 . . ?
C1 C2 C3 120.73(19) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C8 120.90(17) . . ?
C4 C5 S1 126.90(15) . . ?
C8 C5 S1 112.19(14) . . ?
C7 C6 C9 127.36(16) . . ?
C7 C6 S1 110.27(13) . . ?
C9 C6 S1 122.18(13) . . ?
O1 C7 C6 126.11(17) . . ?
O1 C7 C8 120.00(16) . . ?
C6 C7 C8 113.88(16) . . ?
C5 C8 C1 119.66(18) . . ?
C5 C8 C7 111.89(16) . . ?
C1 C8 C7 128.46(18) . . ?
C6 C9 C10 120.12(15) . . ?
C6 C9 S2 120.81(14) . . ?
C10 C9 S2 119.02(13) . . ?
C15 C10 C11 116.89(16) . . ?
C15 C10 C9 120.29(15) . . ?
C11 C10 C9 122.71(16) . . ?
C12 C11 C10 121.71(17) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.17(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N1 C13 C12 122.06(16) . . ?
N1 C13 C14 121.09(17) . . ?
C12 C13 C14 116.85(16) . . ?
C15 C14 C13 121.20(17) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 122.04(16) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C16 121.11(17) . . ?
C13 N1 C17 120.69(16) . . ?
C16 N1 C17 118.15(17) . . ?
C7 O1 H1O 104.5(18) . . ?
C5 S1 C6 91.77(8) . . ?

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
C8 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C8 -0.4(3) . . . . ?
C3 C4 C5 S1 178.34(16) . . . . ?
C9 C6 C7 O1 -3.1(3) . . . . ?
S1 C6 C7 O1 -178.07(14) . . . . ?
C9 C6 C7 C8 175.92(16) . . . . ?
S1 C6 C7 C8 0.93(19) . . . . ?
C4 C5 C8 C1 -0.3(3) . . . . ?
S1 C5 C8 C1 -179.19(14) . . . . ?
C4 C5 C8 C7 179.75(17) . . . . ?
S1 C5 C8 C7 0.88(19) . . . . ?
C2 C1 C8 C5 0.9(3) . . . . ?
C2 C1 C8 C7 -179.18(18) . . . . ?
O1 C7 C8 C5 177.88(15) . . . . ?
C6 C7 C8 C5 -1.2(2) . . . . ?
O1 C7 C8 C1 -2.0(3) . . . . ?
C6 C7 C8 C1 178.90(17) . . . . ?
C7 C6 C9 C10 178.51(16) . . . . ?
S1 C6 C9 C10 -7.0(2) . . . . ?
C7 C6 C9 S2 -4.0(3) . . . . ?
S1 C6 C9 S2 170.48(9) . . . . ?
C6 C9 C10 C15 136.16(17) . . . . ?
S2 C9 C10 C15 -41.4(2) . . . . ?
C6 C9 C10 C11 -47.8(2) . . . . ?
S2 C9 C10 C11 134.63(16) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 C12 -176.94(17) . . . . ?
C10 C11 C12 C13 -2.6(3) . . . . ?
C11 C12 C13 N1 -176.39(18) . . . . ?
C11 C12 C13 C14 3.3(3) . . . . ?
N1 C13 C14 C15 179.01(16) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C10 -2.8(3) . . . . ?
C11 C10 C15 C14 3.4(3) . . . . ?
C9 C10 C15 C14 179.70(16) . . . . ?
C12 C13 N1 C16 -4.9(3) . . . . ?
C14 C13 N1 C16 175.46(19) . . . . ?
C12 C13 N1 C17 177.79(18) . . . . ?
C14 C13 N1 C17 -1.9(3) . . . . ?
C4 C5 S1 C6 -179.10(18) . . . . ?
C8 C5 S1 C6 -0.31(14) . . . . ?
C7 C6 S1 C5 -0.35(13) . . . . ?
C9 C6 S1 C5 -175.65(15) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056

