# Electronic Supplementary Material (ESI) for ChemComm.
# 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_761
_database_code_depnum_ccdc_archive 'CCDC 1889041'
loop_
_audit_author_name
_audit_author_address
'Sangeetha Subramani'
;IIT Madras, Chennai-600036
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-08-05 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 H14 O S'
_chemical_formula_weight         254.33

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.7107(12)
_cell_length_b                   10.021(2)
_cell_length_c                   27.643(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.105(11)
_cell_angle_gamma                90
_cell_volume                     1301.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      21.46

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.962
_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            7581
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7581
_reflns_number_gt                5000
_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. 
;

_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          
; 
 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)+(0.0687P)²+1.5776P] 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       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7581
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2109
_refine_ls_wR_factor_gt          0.1849
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.5599(17) 0.7957(5) 0.0631(2) 0.062(2) Uani 1 1 d . . . . .
C2 C 0.369(2) 0.8684(6) 0.0344(2) 0.085(3) Uani 1 1 d . . . . .
H2 H 0.2767 0.9413 0.0469 0.102 Uiso 1 1 calc R U . . .
C3 C 0.317(2) 0.8311(7) -0.0137(2) 0.092(3) Uani 1 1 d . . . . .
H3 H 0.1855 0.8785 -0.0338 0.110 Uiso 1 1 calc R U . . .
C4 C 0.457(2) 0.7246(8) -0.0317(2) 0.092(3) Uani 1 1 d . . . . .
H4 H 0.4243 0.7014 -0.0642 0.110 Uiso 1 1 calc R U . . .
C5 C 0.646(2) 0.6523(7) -0.0027(3) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.7369 0.5792 -0.0152 0.097 Uiso 1 1 calc R U . . .
C6 C 0.7013(16) 0.6878(6) 0.0458(2) 0.0613(19) Uani 1 1 d . . . . .
C7 C 0.9018(18) 0.6217(6) 0.0822(2) 0.076(2) Uani 1 1 d . . . . .
H7A H 1.0963 0.6442 0.0761 0.092 Uiso 1 1 calc R U . . .
H7B H 0.8804 0.5256 0.0799 0.092 Uiso 1 1 calc R U . . .
C8 C 0.8364(16) 0.6693(6) 0.1329(2) 0.0636(19) Uani 1 1 d . . . . .
H8 H 1.0135 0.6810 0.1533 0.076 Uiso 1 1 calc R U . . .
C9 C 0.6357(15) 0.5762(5) 0.1576(2) 0.0518(17) Uani 1 1 d . . . . .
C10 C 0.5724(15) 0.6011(5) 0.20916(18) 0.0507(18) Uani 1 1 d . . . . .
C11 C 0.3846(17) 0.5170(5) 0.2304(2) 0.062(2) Uani 1 1 d . . . . .
H11 H 0.3014 0.4471 0.2124 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3183(18) 0.5347(6) 0.2777(2) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.1903 0.4769 0.2909 0.085 Uiso 1 1 calc R U . . .
C13 C 0.4379(18) 0.6365(6) 0.3058(2) 0.065(2) Uani 1 1 d . . . . .
C14 C 0.6290(19) 0.7188(6) 0.2845(2) 0.072(2) Uani 1 1 d . . . . .
H14 H 0.7162 0.7871 0.3029 0.087 Uiso 1 1 calc R U . . .
C15 C 0.6950(17) 0.7031(5) 0.2370(2) 0.066(2) Uani 1 1 d . . . . .
H15 H 0.8222 0.7613 0.2237 0.079 Uiso 1 1 calc R U . . .
C16 C 0.369(2) 0.6579(6) 0.3576(2) 0.104(3) Uani 1 1 d . . . . .
H16A H 0.4831 0.5991 0.3784 0.156 Uiso 1 1 calc R U . . .
H16B H 0.1713 0.6395 0.3607 0.156 Uiso 1 1 calc R U . . .
H16C H 0.4095 0.7488 0.3667 0.156 Uiso 1 1 calc R U . . .
O1 O 0.5253(13) 0.4831(4) 0.13548(14) 0.0841(18) Uani 1 1 d . . . . .
S1 S 0.6512(5) 0.82945(15) 0.12482(6) 0.0792(8) 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 1.365(10) . ?
C1 C6 1.375(8) . ?
C1 S1 1.761(6) . ?
C2 C3 1.387(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(10) . ?
C7 C8 1.534(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.524(9) . ?
C8 S1 1.832(6) . ?
C8 H8 0.9800 . ?
C9 O1 1.213(6) . ?
C9 C10 1.497(7) . ?
C10 C15 1.381(7) . ?
C10 C11 1.382(8) . ?
C11 C12 1.379(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(10) . ?
C13 C16 1.505(8) . ?
C14 C15 1.380(8) . ?
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
C2 C1 C6 122.1(6) . . ?
C2 C1 S1 124.4(5) . . ?
C6 C1 S1 113.5(5) . . ?
C1 C2 C3 118.6(7) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.0(8) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(7) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.3(7) . . ?
C1 C6 C7 114.5(6) . . ?
C5 C6 C7 127.3(6) . . ?
C6 C7 C8 108.8(6) . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 113.0(5) . . ?
C9 C8 S1 106.6(5) . . ?
C7 C8 S1 106.6(4) . . ?
C9 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
S1 C8 H8 110.2 . . ?
O1 C9 C10 120.1(6) . . ?
O1 C9 C8 120.2(5) . . ?
C10 C9 C8 119.8(5) . . ?
C15 C10 C11 118.0(5) . . ?
C15 C10 C9 123.4(6) . . ?
C11 C10 C9 118.7(5) . . ?
C12 C11 C10 121.3(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 121.3(7) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 117.0(6) . . ?
C12 C13 C16 122.3(7) . . ?
C14 C13 C16 120.7(6) . . ?
C15 C14 C13 122.3(6) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C10 120.1(6) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
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 . . ?
C1 S1 C8 91.8(3) . . ?

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(12) . . . . ?
S1 C1 C2 C3 180.0(6) . . . . ?
C1 C2 C3 C4 -0.9(12) . . . . ?
C2 C3 C4 C5 1.4(13) . . . . ?
C3 C4 C5 C6 -1.3(13) . . . . ?
C2 C1 C6 C5 -0.2(10) . . . . ?
S1 C1 C6 C5 -179.9(5) . . . . ?
C2 C1 C6 C7 179.6(7) . . . . ?
S1 C1 C6 C7 -0.1(8) . . . . ?
C4 C5 C6 C1 0.7(11) . . . . ?
C4 C5 C6 C7 -179.1(7) . . . . ?
C1 C6 C7 C8 15.2(8) . . . . ?
C5 C6 C7 C8 -165.0(6) . . . . ?
C6 C7 C8 C9 94.4(7) . . . . ?
C6 C7 C8 S1 -22.4(7) . . . . ?
C7 C8 C9 O1 -6.6(9) . . . . ?
S1 C8 C9 O1 110.1(6) . . . . ?
C7 C8 C9 C10 174.1(6) . . . . ?
S1 C8 C9 C10 -69.1(6) . . . . ?
O1 C9 C10 C15 178.4(6) . . . . ?
C8 C9 C10 C15 -2.3(9) . . . . ?
O1 C9 C10 C11 -0.7(9) . . . . ?
C8 C9 C10 C11 178.5(6) . . . . ?
C15 C10 C11 C12 0.7(10) . . . . ?
C9 C10 C11 C12 179.9(6) . . . . ?
C10 C11 C12 C13 -0.4(11) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C11 C12 C13 C16 -180.0(7) . . . . ?
C12 C13 C14 C15 1.4(10) . . . . ?
C16 C13 C14 C15 -179.3(7) . . . . ?
C13 C14 C15 C10 -1.1(10) . . . . ?
C11 C10 C15 C14 0.0(10) . . . . ?
C9 C10 C15 C14 -179.1(6) . . . . ?
C2 C1 S1 C8 168.4(7) . . . . ?
C6 C1 S1 C8 -11.9(5) . . . . ?
C9 C8 S1 C1 -101.5(5) . . . . ?
C7 C8 S1 C1 19.5(5) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.057



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_178
_database_code_depnum_ccdc_archive 'CCDC 1998140'
loop_
_audit_author_name
_audit_author_address
'Subramani Sangeetha'
;IIT Madras 
India
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-05 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            'C14 H10 O2 S2'
_chemical_formula_weight         274.34

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.9604(9)
_cell_length_b                   5.9708(3)
_cell_length_c                   16.2069(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.6217(18)
_cell_angle_gamma                90
_cell_volume                     1237.73(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7010
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.72

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.419
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.951
_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            15195
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2167
_reflns_number_gt                1798
_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)+(0.0495P)²+1.0945P] 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         2167
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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 0.9919(3) 0.4328(6) 0.1147(2) 0.0482(8) Uani 1 1 d . . . . .
H1 H 1.0567 0.4198 0.1114 0.058 Uiso 1 1 calc R U . . .
C2 C 0.9533(3) 0.2792(6) 0.1553(2) 0.0477(8) Uani 1 1 d . . . . .
H2 H 0.9890 0.1497 0.1826 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8531(2) 0.3361(5) 0.1521(2) 0.0435(7) Uani 1 1 d . . . . .
H3 H 0.8158 0.2505 0.1770 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8181(2) 0.5401(5) 0.10602(17) 0.0359(6) Uani 1 1 d . . . . .
C5 C 0.7223(2) 0.6731(5) 0.08348(19) 0.0392(7) Uani 1 1 d . . . . .
C6 C 0.6351(2) 0.6010(5) 0.10720(17) 0.0346(6) Uani 1 1 d . . . . .
C7 C 0.5054(2) 0.4218(5) 0.15622(18) 0.0355(6) Uani 1 1 d . . . . .
C8 C 0.4436(3) 0.2983(5) 0.18995(19) 0.0433(7) Uani 1 1 d . . . . .
H8 H 0.4652 0.1589 0.2165 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3513(2) 0.3881(5) 0.18273(19) 0.0434(8) Uani 1 1 d . . . . .
H9 H 0.3103 0.3100 0.2063 0.052 Uiso 1 1 calc R U . . .
C10 C 0.3157(2) 0.5961(5) 0.14059(18) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.3742(2) 0.7173(5) 0.10527(18) 0.0376(7) Uani 1 1 d . . . . .
H11 H 0.3500 0.8530 0.0761 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4718(2) 0.6299(4) 0.11453(17) 0.0331(6) Uani 1 1 d . . . . .
C13 C 0.5479(2) 0.7270(5) 0.08716(18) 0.0362(7) Uani 1 1 d . . . . .
H13 H 0.5384 0.8647 0.0581 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1798(3) 0.8697(6) 0.0952(3) 0.0576(9) Uani 1 1 d . . . . .
H14A H 0.2265 0.9898 0.1252 0.086 Uiso 1 1 calc R U . . .
H14B H 0.1128 0.8964 0.0970 0.086 Uiso 1 1 calc R U . . .
H14C H 0.1720 0.8618 0.0337 0.086 Uiso 1 1 calc R U . . .
O1 O 0.71406(19) 0.8514(4) 0.04381(17) 0.0583(7) Uani 1 1 d . . . . .
O2 O 0.22128(17) 0.6640(4) 0.13934(15) 0.0520(6) Uani 1 1 d . . . . .
S1 S 0.90942(7) 0.64973(14) 0.07072(6) 0.0517(3) Uani 1 1 d . . . . .
S2 S 0.62830(6) 0.35159(12) 0.16059(5) 0.0428(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 1.361(5) . ?
C1 S1 1.689(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.419(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.470(4) . ?
C4 S1 1.722(3) . ?
C5 O1 1.225(3) . ?
C5 C6 1.480(4) . ?
C6 C13 1.355(4) . ?
C6 S2 1.744(3) . ?
C7 C8 1.402(4) . ?
C7 C12 1.402(4) . ?
C7 S2 1.739(3) . ?
C8 C9 1.356(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(4) . ?
C9 H9 0.9300 . ?
C10 O2 1.372(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.410(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.428(4) . ?
C13 H13 0.9300 . ?
C14 O2 1.423(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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 S1 112.6(3) . . ?
C2 C1 H1 123.7 . . ?
S1 C1 H1 123.7 . . ?
C1 C2 C3 113.4(3) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
C4 C3 C2 110.8(3) . . ?
C4 C3 H3 124.6 . . ?
C2 C3 H3 124.6 . . ?
C3 C4 C5 133.4(3) . . ?
C3 C4 S1 111.0(2) . . ?
C5 C4 S1 115.7(2) . . ?
O1 C5 C4 119.0(3) . . ?
O1 C5 C6 118.4(3) . . ?
C4 C5 C6 122.7(2) . . ?
C13 C6 C5 122.0(2) . . ?
C13 C6 S2 111.8(2) . . ?
C5 C6 S2 126.2(2) . . ?
C8 C7 C12 120.9(3) . . ?
C8 C7 S2 127.5(2) . . ?
C12 C7 S2 111.6(2) . . ?
C9 C8 C7 118.1(3) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
O2 C10 C11 124.4(3) . . ?
O2 C10 C9 114.7(3) . . ?
C11 C10 C9 120.9(3) . . ?
C10 C11 C12 118.0(3) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 C13 111.2(3) . . ?
C11 C12 C13 128.6(2) . . ?
C6 C13 C12 114.1(2) . . ?
C6 C13 H13 122.9 . . ?
C12 C13 H13 122.9 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 O2 C14 117.3(2) . . ?
C1 S1 C4 92.27(15) . . ?
C7 S2 C6 91.30(13) . . ?

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
S1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 179.8(3) . . . . ?
C2 C3 C4 S1 -0.5(3) . . . . ?
C3 C4 C5 O1 178.1(3) . . . . ?
S1 C4 C5 O1 -1.6(4) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
S1 C4 C5 C6 178.8(2) . . . . ?
O1 C5 C6 C13 -0.7(4) . . . . ?
C4 C5 C6 C13 179.0(3) . . . . ?
O1 C5 C6 S2 178.1(2) . . . . ?
C4 C5 C6 S2 -2.2(4) . . . . ?
C12 C7 C8 C9 -1.3(4) . . . . ?
S2 C7 C8 C9 177.3(2) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 C9 C10 O2 -179.6(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
O2 C10 C11 C12 177.7(2) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
S2 C7 C12 C11 -179.4(2) . . . . ?
C8 C7 C12 C13 178.8(3) . . . . ?
S2 C7 C12 C13 0.0(3) . . . . ?
C10 C11 C12 C7 2.0(4) . . . . ?
C10 C11 C12 C13 -177.3(3) . . . . ?
C5 C6 C13 C12 179.5(2) . . . . ?
S2 C6 C13 C12 0.5(3) . . . . ?
C7 C12 C13 C6 -0.3(3) . . . . ?
C11 C12 C13 C6 179.0(3) . . . . ?
C11 C10 O2 C14 2.6(4) . . . . ?
C9 C10 O2 C14 -178.1(3) . . . . ?
C2 C1 S1 C4 0.0(3) . . . . ?
C3 C4 S1 C1 0.3(2) . . . . ?
C5 C4 S1 C1 -180.0(2) . . . . ?
C8 C7 S2 C6 -178.5(3) . . . . ?
C12 C7 S2 C6 0.3(2) . . . . ?
C13 C6 S2 C7 -0.5(2) . . . . ?
C5 C6 S2 C7 -179.4(3) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059



