# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2088155'
loop_
_audit_author_name
_audit_author_address
'Yi An'
;SHIHEZI University
China
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-11-01 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            'C20 H16 O S'
_chemical_formula_weight         304.39

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                   14.5191(13)
_cell_length_b                   7.2625(5)
_cell_length_c                   15.2169(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.832(3)
_cell_angle_gamma                90
_cell_volume                     1551.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    305(2)
_cell_measurement_reflns_used    4434
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.56

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      305(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15306
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         26.966
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3349
_reflns_number_gt                2617
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.4419P] 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         3349
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.40617(4) 0.85916(7) 0.54133(3) 0.05147(16) Uani 1 1 d . . . . .
O1 O 0.35441(9) 0.61528(16) 0.65451(8) 0.0465(3) Uani 1 1 d . . . . .
C1 C 0.43138(12) 0.7320(2) 0.64971(11) 0.0422(4) Uani 1 1 d . . . . .
C2 C 0.52329(13) 0.6259(3) 0.65867(12) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.53335(16) 0.4527(3) 0.69808(15) 0.0621(5) Uani 1 1 d . . . . .
H3 H 0.482912 0.400755 0.716689 0.075 Uiso 1 1 calc R U . . .
C4 C 0.61780(18) 0.3564(3) 0.70994(17) 0.0754(7) Uani 1 1 d . . . . .
H4 H 0.623615 0.239814 0.736026 0.090 Uiso 1 1 calc R U . . .
C5 C 0.69309(17) 0.4319(4) 0.68348(16) 0.0737(7) Uani 1 1 d . . . . .
H5 H 0.749944 0.367098 0.691978 0.088 Uiso 1 1 calc R U . . .
C7 C 0.59980(14) 0.6997(3) 0.63188(13) 0.0547(5) Uani 1 1 d . . . . .
H7 H 0.594253 0.815692 0.605096 0.066 Uiso 1 1 calc R U . . .
C6 C 0.68403(15) 0.6036(3) 0.64438(15) 0.0646(6) Uani 1 1 d . . . . .
H6 H 0.734873 0.655165 0.626297 0.077 Uiso 1 1 calc R U . . .
C9 C 0.50971(14) 0.8745(3) 0.80320(13) 0.0531(5) Uani 1 1 d . . . . .
H9 H 0.560124 0.792539 0.808993 0.064 Uiso 1 1 calc R U . . .
C8 C 0.43503(13) 0.8724(2) 0.72492(11) 0.0424(4) Uani 1 1 d . . . . .
C10 C 0.50952(16) 0.9980(3) 0.87276(14) 0.0632(6) Uani 1 1 d . . . . .
H10 H 0.559986 0.999464 0.924685 0.076 Uiso 1 1 calc R U . . .
C11 C 0.43474(17) 1.1180(3) 0.86482(14) 0.0634(6) Uani 1 1 d . . . . .
H11 H 0.434055 1.199404 0.911837 0.076 Uiso 1 1 calc R U . . .
C12 C 0.36085(15) 1.1180(3) 0.78740(13) 0.0548(5) Uani 1 1 d . . . . .
H12 H 0.310888 1.200688 0.782521 0.066 Uiso 1 1 calc R U . . .
C13 C 0.35929(13) 0.9966(2) 0.71612(12) 0.0435(4) Uani 1 1 d . . . . .
C14 C 0.28109(13) 1.0072(2) 0.63164(12) 0.0424(4) Uani 1 1 d . . . . .
C15 C 0.29740(13) 0.9563(2) 0.54781(12) 0.0449(4) Uani 1 1 d . . . . .
C16 C 0.22708(15) 0.9827(3) 0.46749(13) 0.0565(5) Uani 1 1 d . . . . .
H16 H 0.238785 0.950442 0.412196 0.068 Uiso 1 1 calc R U . . .
C17 C 0.14018(16) 1.0563(3) 0.46939(15) 0.0631(6) Uani 1 1 d . . . . .
H17 H 0.093838 1.075822 0.415390 0.076 Uiso 1 1 calc R U . . .
C18 C 0.12186(15) 1.1012(3) 0.55145(15) 0.0589(5) Uani 1 1 d . . . . .
H18 H 0.062682 1.148219 0.552880 0.071 Uiso 1 1 calc R U . . .
C19 C 0.19149(14) 1.0761(3) 0.63134(14) 0.0512(5) Uani 1 1 d . . . . .
H19 H 0.178283 1.105900 0.686293 0.061 Uiso 1 1 calc R U . . .
C20 C 0.31926(17) 0.4925(3) 0.57980(15) 0.0655(6) Uani 1 1 d . . . . .
H20A H 0.285521 0.561560 0.527680 0.098 Uiso 1 1 calc R U . . .
H20B H 0.276953 0.404572 0.595853 0.098 Uiso 1 1 calc R U . . .
H20C H 0.371743 0.429067 0.565780 0.098 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.7553(19) . ?
S1 C1 1.8435(17) . ?
O1 C1 1.419(2) . ?
O1 C20 1.432(2) . ?
C1 C2 1.516(3) . ?
C1 C8 1.524(2) . ?
C2 C3 1.385(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C7 C6 1.378(3) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.388(3) . ?
C9 C8 1.391(2) . ?
C9 H9 0.9300 . ?
C8 C13 1.402(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.483(2) . ?
C14 C19 1.393(3) . ?
C14 C15 1.405(2) . ?
C15 C16 1.391(3) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C15 S1 C1 97.27(8) . . ?
C1 O1 C20 117.14(14) . . ?
O1 C1 C2 112.25(14) . . ?
O1 C1 C8 103.74(13) . . ?
C2 C1 C8 114.32(14) . . ?
O1 C1 S1 111.51(11) . . ?
C2 C1 S1 107.67(12) . . ?
C8 C1 S1 107.29(12) . . ?
C3 C2 C7 118.37(19) . . ?
C3 C2 C1 119.53(17) . . ?
C7 C2 C1 122.04(17) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C10 C9 C8 120.46(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C8 C13 119.71(17) . . ?
C9 C8 C1 121.34(17) . . ?
C13 C8 C1 118.90(15) . . ?
C11 C10 C9 119.93(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.06(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.46(17) . . ?
C12 C13 C14 119.88(17) . . ?
C8 C13 C14 121.59(16) . . ?
C19 C14 C15 117.77(17) . . ?
C19 C14 C13 121.90(17) . . ?
C15 C14 C13 120.25(16) . . ?
C16 C15 C14 120.35(18) . . ?
C16 C15 S1 118.33(15) . . ?
C14 C15 S1 121.32(14) . . ?
C17 C16 C15 120.36(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.56(19) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_11_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2088156'
loop_
_audit_author_name
_audit_author_address
'Yi An '
;SHIHEZI University
China
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-11-01 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 H12 O S'
_chemical_formula_weight         228.30

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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                   8.8355(6)
_cell_length_b                   15.5836(11)
_cell_length_c                   8.5018(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1170.60(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    305(2)
_cell_measurement_reflns_used    7505
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.76

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      305(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13698
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         26.867
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2518
_reflns_number_gt                2373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.0818P] 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 1039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2518
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68201(6) 0.58133(4) 0.30619(7) 0.04923(17) Uani 1 1 d . . . . .
O1 O 0.47798(17) 0.52756(11) 0.5200(2) 0.0521(4) Uani 1 1 d . . . . .
C1 C 0.3405(3) 0.5606(2) 0.4586(4) 0.0710(8) Uani 1 1 d . . . . .
H1A H 0.362325 0.604304 0.382395 0.107 Uiso 1 1 calc R U . . .
H1B H 0.281429 0.584614 0.542489 0.107 Uiso 1 1 calc R U . . .
H1C H 0.284601 0.515071 0.409293 0.107 Uiso 1 1 calc R U . . .
C2 C 0.5761(2) 0.49651(14) 0.4033(3) 0.0430(4) Uani 1 1 d . . . . .
H2 H 0.515221 0.466844 0.323676 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6809(2) 0.43208(15) 0.4774(3) 0.0431(5) Uani 1 1 d . . . . .
C5 C 0.7301(3) 0.28368(17) 0.5390(4) 0.0626(7) Uani 1 1 d . . . . .
H5 H 0.702774 0.226165 0.532324 0.075 Uiso 1 1 calc R U . . .
C4 C 0.6424(3) 0.34593(16) 0.4678(3) 0.0559(6) Uani 1 1 d . . . . .
H4 H 0.556083 0.329830 0.412570 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8589(3) 0.30764(17) 0.6204(3) 0.0601(7) Uani 1 1 d . . . . .
H6 H 0.918169 0.266200 0.669401 0.072 Uiso 1 1 calc R U . . .
C7 C 0.8993(3) 0.39287(17) 0.6290(3) 0.0538(6) Uani 1 1 d . . . . .
H7 H 0.987239 0.408123 0.682147 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8561(2) 0.54813(15) 0.5707(2) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.8106(2) 0.45732(15) 0.5590(2) 0.0418(5) Uani 1 1 d . . . . .
C10 C 0.8049(2) 0.60928(16) 0.4607(3) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.8561(3) 0.69329(17) 0.4669(3) 0.0573(6) Uani 1 1 d . . . . .
H11 H 0.822019 0.732927 0.393174 0.069 Uiso 1 1 calc R U . . .
C12 C 0.9577(3) 0.71861(19) 0.5820(4) 0.0662(7) Uani 1 1 d . . . . .
H12 H 0.993614 0.774688 0.584232 0.079 Uiso 1 1 calc R U . . .
C13 C 1.0051(3) 0.66000(19) 0.6932(4) 0.0658(7) Uani 1 1 d . . . . .
H13 H 1.071748 0.677011 0.771938 0.079 Uiso 1 1 calc R U . . .
C14 C 0.9546(3) 0.57692(17) 0.6885(3) 0.0557(6) Uani 1 1 d . . . . .
H14 H 0.986462 0.538635 0.765620 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.760(2) . ?
S1 C2 1.818(2) . ?
O1 C2 1.404(3) . ?
O1 C1 1.419(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.504(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.387(3) . ?
C3 C8 1.396(3) . ?
C5 C4 1.381(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9300 . ?
C9 C14 1.401(3) . ?
C9 C10 1.409(3) . ?
C9 C8 1.475(3) . ?
C10 C11 1.386(4) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C2 99.14(11) . . ?
C2 O1 C1 113.2(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 108.30(17) . . ?
O1 C2 S1 112.85(15) . . ?
C3 C2 S1 111.00(14) . . ?
O1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
S1 C2 H2 108.2 . . ?
C4 C3 C8 120.2(2) . . ?
C4 C3 C2 118.1(2) . . ?
C8 C3 C2 121.7(2) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C14 C9 C10 117.2(2) . . ?
C14 C9 C8 121.7(2) . . ?
C10 C9 C8 121.12(19) . . ?
C3 C8 C7 117.8(2) . . ?
C3 C8 C9 121.85(19) . . ?
C7 C8 C9 120.3(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 S1 117.60(19) . . ?
C9 C10 S1 121.74(18) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 121.7(2) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.027

