# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_SMRN233
_database_code_depnum_ccdc_archive 'CCDC 2332011'
loop_
_audit_author_name
_audit_author_address
'Sengodagounder Muthusamy'
;Bharathidasan University
India
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         234.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.8862(3)
_cell_length_b                   10.3502(4)
_cell_length_c                   14.3311(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.6680(10)
_cell_angle_gamma                90
_cell_volume                     1136.63(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8338
_cell_measurement_theta_min      2.4518
_cell_measurement_theta_max      37.1655
_cell_measurement_temperature    159.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.156
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496

_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.8650
_exptl_absorpt_correction_T_max  0.9600

_exptl_special_details           
;
;

_diffrn_ambient_temperature      159.(2)

_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_source_type              ?

_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            39684
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         39.44
_diffrn_reflns_theta_full        39.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             6788
_reflns_number_gt                4696
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1278
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         6788
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.2698P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.99211(3) 0.72849(3) 0.61740(2) 0.02194(6) Uani d . . . 1 . .
O O1 0.64990(12) 0.86700(8) 0.59284(6) 0.03025(18) Uani d . . . 1 . .
O O2 0.49251(9) 0.73631(8) 0.48104(6) 0.02436(15) Uani d . . . 1 . .
C C1 0.86710(13) 0.86232(9) 0.41580(7) 0.02109(17) Uani d . . . 1 . .
C C2 0.90770(14) 0.90233(11) 0.33116(8) 0.02580(19) Uani d . . . 1 . .
C C3 0.91552(14) 0.81250(12) 0.26020(8) 0.0263(2) Uani d . . . 1 . .
C C4 0.88323(14) 0.68325(11) 0.27454(7) 0.02466(19) Uani d . . . 1 . .
C C5 0.84248(13) 0.64270(10) 0.35925(7) 0.02054(16) Uani d . . . 1 . .
C C6 0.83450(11) 0.73179(9) 0.43094(6) 0.01624(14) Uani d . . . 1 . .
C C7 0.79431(11) 0.69241(8) 0.52603(6) 0.01610(14) Uani d . . . 1 . .
C C8 0.75089(12) 0.54813(9) 0.53294(7) 0.01754(15) Uani d . . . 1 . .
C C9 0.73054(14) 0.51172(10) 0.63135(7) 0.02220(17) Uani d . . . 1 . .
C C10 0.80421(14) 0.57137(11) 0.71326(8) 0.02451(19) Uani d . . . 1 . .
C C11 0.92022(16) 0.68689(12) 0.72419(8) 0.0269(2) Uani d . . . 1 . .
C C12 0.64094(12) 0.77608(9) 0.53975(7) 0.01802(15) Uani d . . . 1 . .
C C13 0.33815(15) 0.81133(13) 0.48187(10) 0.0288(2) Uani d . . . 1 . .
H H1 0.863(2) 0.9215(16) 0.4656(11) 0.028(4) Uiso d . . . 1 . .
H H2 0.932(2) 0.9899(18) 0.3229(12) 0.039(5) Uiso d . . . 1 . .
H H3 0.942(2) 0.8370(18) 0.2031(14) 0.043(5) Uiso d . . . 1 . .
H H4 0.888(2) 0.6212(16) 0.2260(12) 0.033(4) Uiso d . . . 1 . .
H H5 0.8261(19) 0.5527(16) 0.3674(11) 0.028(4) Uiso d . . . 1 . .
H H9 0.663(2) 0.4346(16) 0.6341(12) 0.032(4) Uiso d . . . 1 . .
H H8A 0.6489(19) 0.5294(15) 0.4856(11) 0.024(4) Uiso d . . . 1 . .
H H8B 0.8383(19) 0.4969(15) 0.5188(11) 0.024(4) Uiso d . . . 1 . .
H H10 0.780(2) 0.5374(17) 0.7718(11) 0.032(4) Uiso d . . . 1 . .
H H11A 0.869(2) 0.7627(16) 0.7450(13) 0.032(4) Uiso d . . . 1 . .
H H11B 1.028(2) 0.6734(18) 0.7741(13) 0.039(4) Uiso d . . . 1 . .
H H13A 0.245(2) 0.7751(17) 0.4365(13) 0.038(5) Uiso d . . . 1 . .
H H13B 0.316(2) 0.8081(19) 0.5439(14) 0.042(5) Uiso d . . . 1 . .
H H13C 0.354(2) 0.8999(18) 0.4631(12) 0.038(4) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.8053(12) ?
S1 C7 . 1.8226(9) ?
O1 C12 . 1.2016(12) ?
O2 C12 . 1.3350(12) ?
O2 C13 . 1.4463(13) ?
C1 C2 . 1.3889(15) ?
C1 C6 . 1.4017(13) ?
C1 H1 . 0.947(16) ?
C2 C3 . 1.3900(17) ?
C2 H2 . 0.938(18) ?
C3 C4 . 1.3862(17) ?
C3 H3 . 0.926(19) ?
C4 C5 . 1.3920(15) ?
C4 H4 . 0.955(17) ?
C5 C6 . 1.3929(13) ?
C5 H5 . 0.951(16) ?
C6 C7 . 1.5258(13) ?
C7 C12 . 1.5375(13) ?
C7 C8 . 1.5405(13) ?
C8 C9 . 1.5047(14) ?
C8 H8A . 0.942(15) ?
C8 H8B . 0.929(15) ?
C9 C10 . 1.3320(15) ?
C9 H9 . 0.966(17) ?
C10 C11 . 1.4911(17) ?
C10 H10 . 0.969(16) ?
C11 H11A . 0.960(17) ?
C11 H11B . 0.982(18) ?
C13 H13A . 0.936(19) ?
C13 H13B . 0.94(2) ?
C13 H13C . 0.972(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C7 . . 99.98(5) ?
C12 O2 C13 . . 116.33(9) ?
C2 C1 C6 . . 120.73(10) ?
C2 C1 H1 . . 121.5(10) ?
C6 C1 H1 . . 117.8(10) ?
C1 C2 C3 . . 119.92(10) ?
C1 C2 H2 . . 119.5(11) ?
C3 C2 H2 . . 120.6(11) ?
C4 C3 C2 . . 119.71(10) ?
C4 C3 H3 . . 118.8(12) ?
C2 C3 H3 . . 121.5(12) ?
C3 C4 C5 . . 120.57(10) ?
C3 C4 H4 . . 120.0(10) ?
C5 C4 H4 . . 119.4(10) ?
C4 C5 C6 . . 120.24(9) ?
C4 C5 H5 . . 117.9(10) ?
C6 C5 H5 . . 121.8(10) ?
C5 C6 C1 . . 118.82(9) ?
C5 C6 C7 . . 122.49(8) ?
C1 C6 C7 . . 118.69(8) ?
C6 C7 C12 . . 107.43(7) ?
C6 C7 C8 . . 114.37(7) ?
C12 C7 C8 . . 110.14(7) ?
C6 C7 S1 . . 105.30(6) ?
C12 C7 S1 . . 111.00(6) ?
C8 C7 S1 . . 108.54(6) ?
C9 C8 C7 . . 112.18(8) ?
C9 C8 H8A . . 111.2(9) ?
C7 C8 H8A . . 108.5(9) ?
C9 C8 H8B . . 108.1(9) ?
C7 C8 H8B . . 110.6(9) ?
H8A C8 H8B . . 106.1(13) ?
C10 C9 C8 . . 126.09(10) ?
C10 C9 H9 . . 118.5(10) ?
C8 C9 H9 . . 115.3(10) ?
C9 C10 C11 . . 126.39(10) ?
C9 C10 H10 . . 117.4(10) ?
C11 C10 H10 . . 116.2(10) ?
C10 C11 S1 . . 114.20(8) ?
C10 C11 H11A . . 113.4(10) ?
S1 C11 H11A . . 107.8(10) ?
C10 C11 H11B . . 111.5(11) ?
S1 C11 H11B . . 105.1(11) ?
H11A C11 H11B . . 104.0(15) ?
O1 C12 O2 . . 123.51(9) ?
O1 C12 C7 . . 126.28(9) ?
O2 C12 C7 . . 110.17(8) ?
O2 C13 H13A . . 107.5(11) ?
O2 C13 H13B . . 109.2(12) ?
H13A C13 H13B . . 110.7(16) ?
O2 C13 H13C . . 109.9(10) ?
H13A C13 H13C . . 108.5(15) ?
H13B C13 H13C . . 110.9(16) ?

####################################################################### 
# 
# 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 2332012'
loop_
_audit_author_name
_audit_author_address
'Sengodagounder Muthusamy'
;Bharathidasan University
India
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-07-15 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            'C14 H16 O2 S'
_chemical_formula_weight         248.33

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      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                   7.7176(9)
_cell_length_b                   8.7676(11)
_cell_length_c                   10.6594(13)
_cell_angle_alpha                84.913(5)
_cell_angle_beta                 82.334(4)
_cell_angle_gamma                65.082(4)
_cell_volume                     647.86(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6904
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27420
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.329
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2847
_reflns_number_gt                2222
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/2 (Sheldrick, 2018)'

_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)+(0.0950P)²+0.2006P] 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         2847
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1614
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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 0.5716(3) 0.6939(3) 0.2779(2) 0.0320(5) Uani 1 1 d . . . . .
C2 C 0.3733(3) 0.7039(3) 0.3392(2) 0.0362(5) Uani 1 1 d . . . . .
H2 H 0.397519 0.609261 0.400837 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2571(4) 0.6853(3) 0.2440(3) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.155795 0.657315 0.276414 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2823(4) 0.7042(4) 0.1196(3) 0.0496(7) Uani 1 1 d . . . . .
H4 H 0.196847 0.689779 0.073150 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4363(4) 0.7467(4) 0.0472(3) 0.0507(7) Uani 1 1 d . . . . .
H5A H 0.383927 0.822269 -0.023740 0.061 Uiso 1 1 calc R U . . .
H5B H 0.538550 0.644651 0.013278 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6629(4) 0.7532(3) 0.3709(2) 0.0415(6) Uani 1 1 d . . . . .
C7 C 0.7779(6) 0.6997(5) 0.5712(3) 0.0700(10) Uani 1 1 d . . . . .
H7A H 0.895189 0.707364 0.535748 0.105 Uiso 1 1 calc R U . . .
H7B H 0.804033 0.616422 0.639257 0.105 Uiso 1 1 calc R U . . .
H7C H 0.688118 0.806855 0.602864 0.105 Uiso 1 1 calc R U . . .
C8 C 0.7143(3) 0.5166(3) 0.2382(2) 0.0328(5) Uani 1 1 d . . . . .
C9 C 0.8928(4) 0.4955(4) 0.1747(2) 0.0461(6) Uani 1 1 d . . . . .
H9 H 0.920536 0.588838 0.155186 0.055 Uiso 1 1 calc R U . . .
C10 C 1.0284(4) 0.3386(5) 0.1406(3) 0.0606(9) Uani 1 1 d . . . . .
H10 H 1.147241 0.326871 0.099538 0.073 Uiso 1 1 calc R U . . .
C11 C 0.9891(5) 0.1983(4) 0.1670(3) 0.0634(9) Uani 1 1 d . . . . .
H11 H 1.080124 0.092559 0.142635 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8149(5) 0.2169(4) 0.2292(3) 0.0590(8) Uani 1 1 d . . . . .
H12 H 0.788000 0.122984 0.248076 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6780(4) 0.3745(3) 0.2644(3) 0.0463(6) Uani 1 1 d . . . . .
H13 H 0.559960 0.385009 0.306270 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2530(4) 0.8657(4) 0.4113(3) 0.0543(7) Uani 1 1 d . . . . .
H14A H 0.237211 0.961687 0.355514 0.081 Uiso 1 1 calc R U . . .
H14B H 0.317405 0.868551 0.481599 0.081 Uiso 1 1 calc R U . . .
H14C H 0.129246 0.867930 0.441993 0.081 Uiso 1 1 calc R U . . .
O1 O 0.6983(4) 0.8738(3) 0.3544(2) 0.0739(7) Uani 1 1 d . . . . .
O2 O 0.6971(3) 0.6524(2) 0.47422(18) 0.0519(5) Uani 1 1 d . . . . .
S1 S 0.53576(10) 0.84425(8) 0.14171(6) 0.0445(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 C6 1.529(3) . ?
C1 C8 1.535(3) . ?
C1 C2 1.552(3) . ?
C1 S1 1.839(2) . ?
C2 C3 1.502(3) . ?
C2 C14 1.535(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.321(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.491(4) . ?
C4 H4 0.9300 . ?
C5 S1 1.802(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.192(3) . ?
C6 O2 1.331(3) . ?
C7 O2 1.448(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.386(3) . ?
C8 C9 1.396(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
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
C6 C1 C8 107.93(18) . . ?
C6 C1 C2 109.62(18) . . ?
C8 C1 C2 113.95(18) . . ?
C6 C1 S1 105.31(15) . . ?
C8 C1 S1 110.61(15) . . ?
C2 C1 S1 109.05(15) . . ?
C3 C2 C14 109.1(2) . . ?
C3 C2 C1 112.15(19) . . ?
C14 C2 C1 113.5(2) . . ?
C3 C2 H2 107.2 . . ?
C14 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C4 C3 C2 127.4(2) . . ?
C4 C3 H3 116.3 . . ?
C2 C3 H3 116.3 . . ?
C3 C4 C5 125.5(2) . . ?
C3 C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
C4 C5 S1 113.18(19) . . ?
C4 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
O1 C6 O2 124.1(2) . . ?
O1 C6 C1 125.0(2) . . ?
O2 C6 C1 110.86(19) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.7(2) . . ?
C13 C8 C1 123.7(2) . . ?
C9 C8 C1 118.6(2) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 121.0(3) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 O2 C7 115.7(2) . . ?
C5 S1 C1 96.92(12) . . ?

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 167.1(2) . . . . ?
C8 C1 C2 C3 -71.9(2) . . . . ?
S1 C1 C2 C3 52.2(2) . . . . ?
C6 C1 C2 C14 42.8(3) . . . . ?
C8 C1 C2 C14 163.9(2) . . . . ?
S1 C1 C2 C14 -72.0(2) . . . . ?
C14 C2 C3 C4 108.4(3) . . . . ?
C1 C2 C3 C4 -18.2(4) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 S1 -21.1(4) . . . . ?
C8 C1 C6 O1 118.9(3) . . . . ?
C2 C1 C6 O1 -116.4(3) . . . . ?
S1 C1 C6 O1 0.7(3) . . . . ?
C8 C1 C6 O2 -61.5(3) . . . . ?
C2 C1 C6 O2 63.2(3) . . . . ?
S1 C1 C6 O2 -179.63(17) . . . . ?
C6 C1 C8 C13 116.4(2) . . . . ?
C2 C1 C8 C13 -5.6(3) . . . . ?
S1 C1 C8 C13 -128.9(2) . . . . ?
C6 C1 C8 C9 -62.1(3) . . . . ?
C2 C1 C8 C9 175.9(2) . . . . ?
S1 C1 C8 C9 52.7(2) . . . . ?
C13 C8 C9 C10 -0.6(4) . . . . ?
C1 C8 C9 C10 177.9(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C1 C8 C13 C12 -178.1(2) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
O1 C6 O2 C7 1.6(4) . . . . ?
C1 C6 O2 C7 -178.0(2) . . . . ?
C4 C5 S1 C1 47.5(2) . . . . ?
C6 C1 S1 C5 178.55(17) . . . . ?
C8 C1 S1 C5 62.19(17) . . . . ?
C2 C1 S1 C5 -63.87(18) . . . . ?

_refine_diff_density_max         0.668
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.091

