# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2019

####################################################################### 
# 
# 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_n6
_database_code_depnum_ccdc_archive 'CCDC 1903023'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 O S'
_chemical_formula_sum            'C13 H10 O S'
_chemical_formula_weight         214.27

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.0379(3)
_cell_length_b                   10.4847(5)
_cell_length_c                   16.1404(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1021.78(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    373
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17850
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         30.686
_diffrn_reflns_theta_full        25.242
_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             3162
_reflns_number_gt                2964
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     1.000
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0445P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3162
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
S3 S -0.05074(8) 0.36109(4) 0.52644(3) 0.02670(11) Uani 1 1 d . . . . .
O1 O 0.6670(2) 0.37692(13) 0.90659(8) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.3025(3) 0.43578(15) 0.60268(11) 0.0218(3) Uani 1 1 d . . . . .
H1 H 0.438353 0.477530 0.614783 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1898(3) 0.45004(16) 0.53018(11) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.238474 0.503381 0.486218 0.030 Uiso 1 1 calc R U . . .
C3A C -0.0038(3) 0.30169(16) 0.62507(11) 0.0216(3) Uani 1 1 d . . . . .
C4 C -0.1423(3) 0.21597(16) 0.66863(12) 0.0242(3) Uani 1 1 d . . . . .
H4 H -0.275131 0.184853 0.644404 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0803(3) 0.17907(16) 0.74639(11) 0.0241(3) Uani 1 1 d . . . . .
H5 H -0.170374 0.120386 0.775962 0.029 Uiso 1 1 calc R U . . .
C5A C 0.1165(3) 0.22653(15) 0.78424(11) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.1757(3) 0.19181(16) 0.86671(11) 0.0235(3) Uani 1 1 d . . . . .
H6 H 0.087026 0.131851 0.895827 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3569(3) 0.24292(16) 0.90466(12) 0.0247(3) Uani 1 1 d . . . . .
H7 H 0.392706 0.218779 0.959792 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4921(3) 0.33201(15) 0.86205(11) 0.0217(3) Uani 1 1 d . . . . .
C9 C 0.4413(3) 0.36739(15) 0.78176(9) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.532852 0.426911 0.753521 0.023 Uiso 1 1 calc R U . . .
C9A C 0.2539(3) 0.31548(15) 0.74141(10) 0.0182(3) Uani 1 1 d . . . . .
C9B C 0.1925(3) 0.35048(15) 0.65866(9) 0.0192(3) Uani 1 1 d . . . . .
C10 C 0.8022(3) 0.47237(18) 0.86772(13) 0.0272(4) Uani 1 1 d . . . . .
H10A H 0.920165 0.498439 0.905827 0.041 Uiso 1 1 calc R U . . .
H10B H 0.710705 0.546501 0.853707 0.041 Uiso 1 1 calc R U . . .
H10C H 0.867956 0.437320 0.817096 0.041 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
S3 C2 1.727(2) . ?
S3 C3A 1.7327(18) . ?
O1 C8 1.362(2) . ?
O1 C10 1.436(2) . ?
C1 C2 1.362(3) . ?
C1 C9B 1.434(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3A C9B 1.400(2) . ?
C3A C4 1.415(2) . ?
C4 C5 1.366(3) . ?
C4 H4 0.9500 . ?
C5 C5A 1.426(2) . ?
C5 H5 0.9500 . ?
C5A C6 1.425(2) . ?
C5A C9A 1.427(2) . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.418(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C9 C9A 1.415(2) . ?
C9 H9 0.9500 . ?
C9A C9B 1.434(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 S3 C3A 91.40(9) . . ?
C8 O1 C10 116.82(14) . . ?
C2 C1 C9B 112.23(16) . . ?
C2 C1 H1 123.9 . . ?
C9B C1 H1 123.9 . . ?
C1 C2 S3 113.01(13) . . ?
C1 C2 H2 123.5 . . ?
S3 C2 H2 123.5 . . ?
C9B C3A C4 122.68(16) . . ?
C9B C3A S3 111.28(12) . . ?
C4 C3A S3 126.04(14) . . ?
C5 C4 C3A 118.33(16) . . ?
C5 C4 H4 120.8 . . ?
C3A C4 H4 120.8 . . ?
C4 C5 C5A 121.57(16) . . ?
C4 C5 H5 119.2 . . ?
C5A C5 H5 119.2 . . ?
C6 C5A C5 121.33(15) . . ?
C6 C5A C9A 118.27(16) . . ?
C5 C5A C9A 120.34(15) . . ?
C7 C6 C5A 121.35(16) . . ?
C7 C6 H6 119.3 . . ?
C5A C6 H6 119.3 . . ?
C6 C7 C8 120.18(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C8 C9 125.04(15) . . ?
O1 C8 C7 114.72(15) . . ?
C9 C8 C7 120.24(16) . . ?
C8 C9 C9A 120.38(15) . . ?
C8 C9 H9 119.8 . . ?
C9A C9 H9 119.8 . . ?
C9 C9A C5A 119.57(15) . . ?
C9 C9A C9B 122.49(14) . . ?
C5A C9A C9B 117.92(15) . . ?
C3A C9B C9A 119.08(15) . . ?
C3A C9B C1 112.07(15) . . ?
C9A C9B C1 128.81(16) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C9B C1 C2 S3 -0.34(19) . . . . ?
C3A S3 C2 C1 0.17(14) . . . . ?
C2 S3 C3A C9B 0.05(13) . . . . ?
C2 S3 C3A C4 179.46(16) . . . . ?
C9B C3A C4 C5 -0.4(3) . . . . ?
S3 C3A C4 C5 -179.78(13) . . . . ?
C3A C4 C5 C5A 1.1(3) . . . . ?
C4 C5 C5A C6 177.36(16) . . . . ?
C4 C5 C5A C9A 0.5(2) . . . . ?
C5 C5A C6 C7 -176.14(16) . . . . ?
C9A C5A C6 C7 0.8(2) . . . . ?
C5A C6 C7 C8 -0.4(3) . . . . ?
C10 O1 C8 C9 2.8(2) . . . . ?
C10 O1 C8 C7 -176.83(15) . . . . ?
C6 C7 C8 O1 179.54(16) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
O1 C8 C9 C9A -179.44(15) . . . . ?
C7 C8 C9 C9A 0.2(2) . . . . ?
C8 C9 C9A C5A 0.3(2) . . . . ?
C8 C9 C9A C9B 179.09(15) . . . . ?
C6 C5A C9A C9 -0.7(2) . . . . ?
C5 C5A C9A C9 176.24(14) . . . . ?
C6 C5A C9A C9B -179.64(14) . . . . ?
C5 C5A C9A C9B -2.6(2) . . . . ?
C4 C3A C9B C9A -1.8(2) . . . . ?
S3 C3A C9B C9A 177.64(12) . . . . ?
C4 C3A C9B C1 -179.68(15) . . . . ?
S3 C3A C9B C1 -0.25(17) . . . . ?
C9 C9A C9B C3A -175.60(14) . . . . ?
C5A C9A C9B C3A 3.3(2) . . . . ?
C9 C9A C9B C1 1.9(3) . . . . ?
C5A C9A C9B C1 -179.26(15) . . . . ?
C2 C1 C9B C3A 0.4(2) . . . . ?
C2 C1 C9B C9A -177.26(16) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_n7
_database_code_depnum_ccdc_archive 'CCDC 1903026'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N3 S'
_chemical_formula_sum            'C15 H11 N3 S'
_chemical_formula_weight         265.33

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'
N N 0.0061 0.0033 '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                   6.9254(5)
_cell_length_b                   15.9044(11)
_cell_length_c                   23.1610(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.3480(10)
_cell_angle_gamma                90
_cell_volume                     2548.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33697
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.554
_diffrn_reflns_theta_max         30.640
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7848
_reflns_number_gt                6416
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0532P)²+0.9749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         7848
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
S6 S 0.80867(4) 0.52630(2) 0.20909(2) 0.01808(7) Uani 1 1 d . . . . .
N1 N 0.66886(14) 0.21267(6) 0.24000(4) 0.01556(18) Uani 1 1 d . . . . .
N2 N 0.51102(15) 0.17239(6) 0.25991(4) 0.0192(2) Uani 1 1 d . . . . .
N3 N 0.38241(14) 0.22833(6) 0.27371(4) 0.0186(2) Uani 1 1 d . . . . .
C3A C 0.45713(16) 0.30702(7) 0.26303(5) 0.0147(2) Uani 1 1 d . . . . .
C4 C 0.37577(17) 0.38720(7) 0.27220(5) 0.0171(2) Uani 1 1 d . . . . .
H4 H 0.252288 0.393012 0.288159 0.021 Uiso 1 1 calc R U . . .
C5 C 0.48101(17) 0.45622(7) 0.25728(5) 0.0174(2) Uani 1 1 d . . . . .
H5 H 0.431061 0.511070 0.263084 0.021 Uiso 1 1 calc R U . . .
C5A C 0.66467(16) 0.44586(7) 0.23315(5) 0.0148(2) Uani 1 1 d . . . . .
C7 C 0.98119(17) 0.45612(7) 0.18758(5) 0.0193(2) Uani 1 1 d . . . . .
H7 H 1.097112 0.472717 0.170207 0.023 Uiso 1 1 calc R U . . .
C8 C 0.93464(16) 0.37452(7) 0.19799(5) 0.0168(2) Uani 1 1 d . . . . .
H8 H 1.014000 0.327991 0.188983 0.020 Uiso 1 1 calc R U . . .
C8A C 0.75142(16) 0.36727(7) 0.22418(5) 0.0137(2) Uani 1 1 d . . . . .
C8B C 0.64028(16) 0.29741(7) 0.24072(5) 0.01344(19) Uani 1 1 d . . . . .
C9 C 0.83981(17) 0.16534(7) 0.22468(5) 0.0172(2) Uani 1 1 d . . . . .
H9A H 0.829402 0.107391 0.239845 0.021 Uiso 1 1 calc R U . . .
H9B H 0.955276 0.191607 0.243753 0.021 Uiso 1 1 calc R U . . .
C10 C 0.86830(18) 0.16113(7) 0.16038(5) 0.0185(2) Uani 1 1 d . . . . .
C11 C 1.0550(2) 0.15409(10) 0.14086(6) 0.0292(3) Uani 1 1 d . . . . .
H11 H 1.161883 0.152736 0.167904 0.035 Uiso 1 1 calc R U . . .
C12 C 1.0863(2) 0.14902(11) 0.08198(6) 0.0364(3) Uani 1 1 d . . . . .
H12 H 1.214136 0.144537 0.068917 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9303(2) 0.15052(10) 0.04233(6) 0.0348(3) Uani 1 1 d . . . . .
H13 H 0.951042 0.146765 0.002119 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7451(2) 0.15748(11) 0.06155(6) 0.0359(3) Uani 1 1 d . . . . .
H14 H 0.638358 0.158652 0.034450 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7135(2) 0.16282(10) 0.12042(6) 0.0283(3) Uani 1 1 d . . . . .
H15 H 0.585451 0.167625 0.133285 0.034 Uiso 1 1 calc R U . . .
S6' S 0.57769(6) 0.47246(2) 0.41510(2) 0.03017(9) Uani 1 1 d . . . . .
N1' N 0.61104(15) 0.15080(7) 0.39760(4) 0.0203(2) Uani 1 1 d . . . . .
N2' N 0.75148(17) 0.09911(7) 0.37880(5) 0.0263(2) Uani 1 1 d . . . . .
N3' N 0.89842(17) 0.14465(8) 0.36404(5) 0.0269(2) Uani 1 1 d . . . . .
C3A' C 0.85415(18) 0.22798(8) 0.37309(5) 0.0213(2) Uani 1 1 d . . . . .
C4' C 0.96269(19) 0.30060(9) 0.36181(5) 0.0258(3) Uani 1 1 d . . . . .
H4' H 1.087272 0.296510 0.346333 0.031 Uiso 1 1 calc R U . . .
C5' C 0.88376(19) 0.37727(9) 0.37377(5) 0.0257(3) Uani 1 1 d . . . . .
H5' H 0.953180 0.427442 0.366553 0.031 Uiso 1 1 calc R U . . .
C5A' C 0.69708(19) 0.38128(8) 0.39706(5) 0.0222(2) Uani 1 1 d . . . . .
C7' C 0.3809(2) 0.41674(9) 0.43712(6) 0.0285(3) Uani 1 1 d . . . . .
H7' H 0.269031 0.442503 0.451634 0.034 Uiso 1 1 calc R U . . .
C8' C 0.40152(18) 0.33226(8) 0.43167(5) 0.0226(2) Uani 1 1 d . . . . .
H8' H 0.306650 0.292420 0.441947 0.027 Uiso 1 1 calc R U . . .
C8A' C 0.58388(17) 0.31040(8) 0.40853(5) 0.0186(2) Uani 1 1 d . . . . .
C8B' C 0.66883(17) 0.23229(8) 0.39511(5) 0.0181(2) Uani 1 1 d . . . . .
C9' C 0.43105(19) 0.11470(8) 0.41626(5) 0.0228(2) Uani 1 1 d . . . . .
H9'A H 0.425971 0.054563 0.405258 0.027 Uiso 1 1 calc R U . . .
H9'B H 0.321283 0.143502 0.395929 0.027 Uiso 1 1 calc R U . . .
C10' C 0.40912(18) 0.12224(8) 0.48074(5) 0.0202(2) Uani 1 1 d . . . . .
C11' C 0.2265(2) 0.13044(11) 0.50232(6) 0.0354(3) Uani 1 1 d . . . . .
H11' H 0.116470 0.132708 0.476473 0.043 Uiso 1 1 calc R U . . .
C12' C 0.2030(2) 0.13539(13) 0.56173(7) 0.0418(4) Uani 1 1 d . . . . .
H12' H 0.077247 0.140904 0.576212 0.050 Uiso 1 1 calc R U . . .
C13' C 0.3622(2) 0.13230(10) 0.59951(6) 0.0319(3) Uani 1 1 d . . . . .
H13' H 0.346346 0.135773 0.639989 0.038 Uiso 1 1 calc R U . . .
C14' C 0.5439(2) 0.12416(10) 0.57833(6) 0.0316(3) Uani 1 1 d . . . . .
H14' H 0.653553 0.122352 0.604313 0.038 Uiso 1 1 calc R U . . .
C15' C 0.5682(2) 0.11854(9) 0.51898(6) 0.0275(3) Uani 1 1 d . . . . .
H15' H 0.694084 0.112158 0.504731 0.033 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
S6 C7 1.7234(12) . ?
S6 C5A 1.7284(11) . ?
N1 C8B 1.3624(14) . ?
N1 N2 1.3636(13) . ?
N1 C9 1.4589(14) . ?
N2 N3 1.3078(14) . ?
N3 C3A 1.3804(14) . ?
C3A C8B 1.3974(15) . ?
C3A C4 1.4137(15) . ?
C4 C5 1.3698(16) . ?
C4 H4 0.9500 . ?
C5 C5A 1.4197(15) . ?
C5 H5 0.9500 . ?
C5A C8A 1.4060(15) . ?
C7 C8 1.3612(16) . ?
C7 H7 0.9500 . ?
C8 C8A 1.4333(15) . ?
C8 H8 0.9500 . ?
C8A C8B 1.4135(15) . ?
C9 C10 1.5119(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3875(18) . ?
C10 C11 1.3918(18) . ?
C11 C12 1.3918(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3924(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
S6' C7' 1.7204(16) . ?
S6' C5A' 1.7290(13) . ?
N1' C8B' 1.3583(16) . ?
N1' N2' 1.3587(14) . ?
N1' C9' 1.4541(16) . ?
N2' N3' 1.3059(17) . ?
N3' C3A' 1.3782(17) . ?
C3A' C8B' 1.4020(16) . ?
C3A' C4' 1.4084(19) . ?
C4' C5' 1.369(2) . ?
C4' H4' 0.9500 . ?
C5' C5A' 1.4226(18) . ?
C5' H5' 0.9500 . ?
C5A' C8A' 1.4046(18) . ?
C7' C8' 1.3576(19) . ?
C7' H7' 0.9500 . ?
C8' C8A' 1.4348(17) . ?
C8' H8' 0.9500 . ?
C8A' C8B' 1.4146(16) . ?
C9' C10' 1.5121(16) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C10' C11' 1.3852(18) . ?
C10' C15' 1.3864(18) . ?
C11' C12' 1.394(2) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.380(2) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.375(2) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.3947(18) . ?
C14' H14' 0.9500 . ?
C15' H15' 0.9500 . ?

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
C7 S6 C5A 91.71(6) . . ?
C8B N1 N2 109.98(9) . . ?
C8B N1 C9 129.29(10) . . ?
N2 N1 C9 120.64(9) . . ?
N3 N2 N1 109.05(9) . . ?
N2 N3 C3A 107.99(9) . . ?
N3 C3A C8B 108.65(10) . . ?
N3 C3A C4 129.51(10) . . ?
C8B C3A C4 121.84(10) . . ?
C5 C4 C3A 117.75(10) . . ?
C5 C4 H4 121.1 . . ?
C3A C4 H4 121.1 . . ?
C4 C5 C5A 120.05(10) . . ?
C4 C5 H5 120.0 . . ?
C5A C5 H5 120.0 . . ?
C8A C5A C5 123.82(10) . . ?
C8A C5A S6 110.78(8) . . ?
C5 C5A S6 125.39(9) . . ?
C8 C7 S6 113.22(9) . . ?
C8 C7 H7 123.4 . . ?
S6 C7 H7 123.4 . . ?
C7 C8 C8A 111.83(10) . . ?
C7 C8 H8 124.1 . . ?
C8A C8 H8 124.1 . . ?
C5A C8A C8B 114.71(10) . . ?
C5A C8A C8 112.46(10) . . ?
C8B C8A C8 132.79(10) . . ?
N1 C8B C3A 104.32(9) . . ?
N1 C8B C8A 133.88(10) . . ?
C3A C8B C8A 121.80(10) . . ?
N1 C9 C10 113.72(9) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 119.19(12) . . ?
C15 C10 C9 121.85(11) . . ?
C11 C10 C9 118.95(11) . . ?
C10 C11 C12 120.45(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.91(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.76(13) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.43(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.26(13) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C7' S6' C5A' 91.83(6) . . ?
C8B' N1' N2' 110.35(10) . . ?
C8B' N1' C9' 130.32(10) . . ?
N2' N1' C9' 119.34(11) . . ?
N3' N2' N1' 108.90(11) . . ?
N2' N3' C3A' 108.24(10) . . ?
N3' C3A' C8B' 108.36(11) . . ?
N3' C3A' C4' 129.55(12) . . ?
C8B' C3A' C4' 122.06(12) . . ?
C5' C4' C3A' 118.19(12) . . ?
C5' C4' H4' 120.9 . . ?
C3A' C4' H4' 120.9 . . ?
C4' C5' C5A' 119.55(12) . . ?
C4' C5' H5' 120.2 . . ?
C5A' C5' H5' 120.2 . . ?
C8A' C5A' C5' 123.96(12) . . ?
C8A' C5A' S6' 110.57(10) . . ?
C5' C5A' S6' 125.47(10) . . ?
C8' C7' S6' 113.24(10) . . ?
C8' C7' H7' 123.4 . . ?
S6' C7' H7' 123.4 . . ?
C7' C8' C8A' 111.84(12) . . ?
C7' C8' H8' 124.1 . . ?
C8A' C8' H8' 124.1 . . ?
C5A' C8A' C8B' 115.02(11) . . ?
C5A' C8A' C8' 112.51(11) . . ?
C8B' C8A' C8' 132.47(12) . . ?
N1' C8B' C3A' 104.15(10) . . ?
N1' C8B' C8A' 134.64(11) . . ?
C3A' C8B' C8A' 121.20(12) . . ?
N1' C9' C10' 112.60(10) . . ?
N1' C9' H9'A 109.1 . . ?
C10' C9' H9'A 109.1 . . ?
N1' C9' H9'B 109.1 . . ?
C10' C9' H9'B 109.1 . . ?
H9'A C9' H9'B 107.8 . . ?
C11' C10' C15' 119.15(12) . . ?
C11' C10' C9' 119.60(12) . . ?
C15' C10' C9' 121.22(11) . . ?
C10' C11' C12' 120.43(13) . . ?
C10' C11' H11' 119.8 . . ?
C12' C11' H11' 119.8 . . ?
C13' C12' C11' 120.08(14) . . ?
C13' C12' H12' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C14' C13' C12' 119.74(13) . . ?
C14' C13' H13' 120.1 . . ?
C12' C13' H13' 120.1 . . ?
C13' C14' C15' 120.47(13) . . ?
C13' C14' H14' 119.8 . . ?
C15' C14' H14' 119.8 . . ?
C10' C15' C14' 120.13(13) . . ?
C10' C15' H15' 119.9 . . ?
C14' C15' H15' 119.9 . . ?

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
C8B N1 N2 N3 -0.35(13) . . . . ?
C9 N1 N2 N3 176.35(10) . . . . ?
N1 N2 N3 C3A -0.35(12) . . . . ?
N2 N3 C3A C8B 0.90(13) . . . . ?
N2 N3 C3A C4 -178.33(11) . . . . ?
N3 C3A C4 C5 -179.50(11) . . . . ?
C8B C3A C4 C5 1.36(17) . . . . ?
C3A C4 C5 C5A 0.41(17) . . . . ?
C4 C5 C5A C8A -1.39(17) . . . . ?
C4 C5 C5A S6 176.73(9) . . . . ?
C7 S6 C5A C8A -0.05(9) . . . . ?
C7 S6 C5A C5 -178.38(11) . . . . ?
C5A S6 C7 C8 -0.18(10) . . . . ?
S6 C7 C8 C8A 0.35(13) . . . . ?
C5 C5A C8A C8B 0.53(16) . . . . ?
S6 C5A C8A C8B -177.83(8) . . . . ?
C5 C5A C8A C8 178.62(10) . . . . ?
S6 C5A C8A C8 0.26(12) . . . . ?
C7 C8 C8A C5A -0.39(14) . . . . ?
C7 C8 C8A C8B 177.24(12) . . . . ?
N2 N1 C8B C3A 0.87(12) . . . . ?
C9 N1 C8B C3A -175.46(10) . . . . ?
N2 N1 C8B C8A -178.54(11) . . . . ?
C9 N1 C8B C8A 5.1(2) . . . . ?
N3 C3A C8B N1 -1.07(12) . . . . ?
C4 C3A C8B N1 178.23(10) . . . . ?
N3 C3A C8B C8A 178.43(10) . . . . ?
C4 C3A C8B C8A -2.27(17) . . . . ?
C5A C8A C8B N1 -179.41(11) . . . . ?
C8 C8A C8B N1 3.0(2) . . . . ?
C5A C8A C8B C3A 1.26(15) . . . . ?
C8 C8A C8B C3A -176.33(11) . . . . ?
C8B N1 C9 C10 -75.80(15) . . . . ?
N2 N1 C9 C10 108.21(12) . . . . ?
N1 C9 C10 C15 -30.12(16) . . . . ?
N1 C9 C10 C11 150.87(12) . . . . ?
C15 C10 C11 C12 0.2(2) . . . . ?
C9 C10 C11 C12 179.21(13) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C9 C10 C15 C14 -178.99(13) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C8B' N1' N2' N3' -0.17(13) . . . . ?
C9' N1' N2' N3' 179.63(10) . . . . ?
N1' N2' N3' C3A' -0.17(14) . . . . ?
N2' N3' C3A' C8B' 0.44(14) . . . . ?
N2' N3' C3A' C4' -177.51(12) . . . . ?
N3' C3A' C4' C5' 178.67(12) . . . . ?
C8B' C3A' C4' C5' 0.97(18) . . . . ?
C3A' C4' C5' C5A' 0.16(18) . . . . ?
C4' C5' C5A' C8A' -0.63(19) . . . . ?
C4' C5' C5A' S6' 179.45(10) . . . . ?
C7' S6' C5A' C8A' -0.23(10) . . . . ?
C7' S6' C5A' C5' 179.71(12) . . . . ?
C5A' S6' C7' C8' 0.23(11) . . . . ?
S6' C7' C8' C8A' -0.17(15) . . . . ?
C5' C5A' C8A' C8B' -0.05(17) . . . . ?
S6' C5A' C8A' C8B' 179.89(8) . . . . ?
C5' C5A' C8A' C8' -179.76(11) . . . . ?
S6' C5A' C8A' C8' 0.18(13) . . . . ?
C7' C8' C8A' C5A' -0.01(15) . . . . ?
C7' C8' C8A' C8B' -179.65(12) . . . . ?
N2' N1' C8B' C3A' 0.43(13) . . . . ?
C9' N1' C8B' C3A' -179.34(11) . . . . ?
N2' N1' C8B' C8A' 179.59(12) . . . . ?
C9' N1' C8B' C8A' -0.2(2) . . . . ?
N3' C3A' C8B' N1' -0.52(13) . . . . ?
C4' C3A' C8B' N1' 177.61(11) . . . . ?
N3' C3A' C8B' C8A' -179.83(10) . . . . ?
C4' C3A' C8B' C8A' -1.69(18) . . . . ?
C5A' C8A' C8B' N1' -177.88(12) . . . . ?
C8' C8A' C8B' N1' 1.8(2) . . . . ?
C5A' C8A' C8B' C3A' 1.17(16) . . . . ?
C8' C8A' C8B' C3A' -179.19(12) . . . . ?
C8B' N1' C9' C10' -70.01(16) . . . . ?
N2' N1' C9' C10' 110.23(12) . . . . ?
N1' C9' C10' C11' 148.83(13) . . . . ?
N1' C9' C10' C15' -33.15(17) . . . . ?
C15' C10' C11' C12' 0.4(2) . . . . ?
C9' C10' C11' C12' 178.42(15) . . . . ?
C10' C11' C12' C13' 0.1(3) . . . . ?
C11' C12' C13' C14' -0.1(3) . . . . ?
C12' C13' C14' C15' -0.4(3) . . . . ?
C11' C10' C15' C14' -0.8(2) . . . . ?
C9' C10' C15' C14' -178.86(13) . . . . ?
C13' C14' C15' C10' 0.9(2) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_nd674
_database_code_depnum_ccdc_archive 'CCDC 1903027'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 O S'
_chemical_formula_sum            'C13 H10 O S'
_chemical_formula_weight         214.27

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                   14.7585(13)
_cell_length_b                   5.6771(5)
_cell_length_c                   12.3197(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.4501(18)
_cell_angle_gamma                90
_cell_volume                     1023.50(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    310
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.281
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13447
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.784
_diffrn_reflns_theta_max         30.644
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3146
_reflns_number_gt                2685
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0496P)²+0.3960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3146
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.37882(2) 0.59161(5) 0.75495(2) 0.01888(9) Uani 1 1 d . . . . .
O1 O 0.07378(6) 0.94236(16) 0.91442(7) 0.01914(18) Uani 1 1 d . . . . .
C2 C 0.45637(9) 0.5840(2) 0.66181(11) 0.0230(2) Uani 1 1 d . . . . .
H2 H 0.505075 0.473806 0.665108 0.028 Uiso 1 1 calc R U . . .
C3 C 0.44067(8) 0.7512(2) 0.58362(10) 0.0223(2) Uani 1 1 d . . . . .
H3 H 0.476723 0.770153 0.525684 0.027 Uiso 1 1 calc R U . . .
C3A C 0.36363(8) 0.8970(2) 0.59757(10) 0.0186(2) Uani 1 1 d . . . . .
C4 C 0.32753(8) 1.0915(2) 0.53338(10) 0.0207(2) Uani 1 1 d . . . . .
H4 H 0.354791 1.139339 0.471194 0.025 Uiso 1 1 calc R U . . .
C5 C 0.25365(9) 1.2087(2) 0.56163(10) 0.0202(2) Uani 1 1 d . . . . .
H5 H 0.230282 1.339922 0.519050 0.024 Uiso 1 1 calc R U . . .
C5A C 0.21047(8) 1.1393(2) 0.65350(9) 0.0172(2) Uani 1 1 d . . . . .
C6 C 0.13163(8) 1.2576(2) 0.67988(10) 0.0197(2) Uani 1 1 d . . . . .
H6 H 0.108170 1.388123 0.636826 0.024 Uiso 1 1 calc R U . . .
C7 C 0.08892(8) 1.1870(2) 0.76613(10) 0.0194(2) Uani 1 1 d . . . . .
H7 H 0.036060 1.268087 0.782558 0.023 Uiso 1 1 calc R U . . .
C8 C 0.12300(8) 0.9940(2) 0.83096(9) 0.0163(2) Uani 1 1 d . . . . .
C9 C 0.19947(8) 0.8735(2) 0.80851(9) 0.0160(2) Uani 1 1 d . . . . .
H9 H 0.221948 0.743555 0.852565 0.019 Uiso 1 1 calc R U . . .
C9A C 0.24417(7) 0.9455(2) 0.71912(9) 0.0155(2) Uani 1 1 d . . . . .
C9B C 0.32254(8) 0.8288(2) 0.68864(9) 0.0160(2) Uani 1 1 d . . . . .
C10 C 0.09899(9) 0.7353(2) 0.97677(10) 0.0213(2) Uani 1 1 d . . . . .
H10A H 0.057169 0.713044 1.031552 0.032 Uiso 1 1 calc R U . . .
H10B H 0.161589 0.752166 1.013649 0.032 Uiso 1 1 calc R U . . .
H10C H 0.095515 0.598432 0.927918 0.032 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 C2 1.7231(13) . ?
S1 C9B 1.7307(12) . ?
O1 C8 1.3654(14) . ?
O1 C10 1.4270(15) . ?
C2 C3 1.3506(18) . ?
C2 H2 0.9500 . ?
C3 C3A 1.4347(17) . ?
C3 H3 0.9500 . ?
C3A C9B 1.3973(16) . ?
C3A C4 1.4209(17) . ?
C4 C5 1.3606(17) . ?
C4 H4 0.9500 . ?
C5 C5A 1.4245(16) . ?
C5 H5 0.9500 . ?
C5A C9A 1.4166(16) . ?
C5A C6 1.4172(17) . ?
C6 C7 1.3643(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4098(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3778(16) . ?
C9 C9A 1.4155(15) . ?
C9 H9 0.9500 . ?
C9A C9B 1.4248(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 S1 C9B 91.41(6) . . ?
C8 O1 C10 117.07(9) . . ?
C3 C2 S1 112.96(10) . . ?
C3 C2 H2 123.5 . . ?
S1 C2 H2 123.5 . . ?
C2 C3 C3A 112.65(11) . . ?
C2 C3 H3 123.7 . . ?
C3A C3 H3 123.7 . . ?
C9B C3A C4 119.45(11) . . ?
C9B C3A C3 111.70(11) . . ?
C4 C3A C3 128.85(11) . . ?
C5 C4 C3A 119.51(11) . . ?
C5 C4 H4 120.2 . . ?
C3A C4 H4 120.2 . . ?
C4 C5 C5A 121.60(11) . . ?
C4 C5 H5 119.2 . . ?
C5A C5 H5 119.2 . . ?
C9A C5A C6 118.37(11) . . ?
C9A C5A C5 120.52(11) . . ?
C6 C5A C5 121.08(11) . . ?
C7 C6 C5A 121.02(11) . . ?
C7 C6 H6 119.5 . . ?
C5A C6 H6 119.5 . . ?
C6 C7 C8 120.19(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C8 C9 125.05(11) . . ?
O1 C8 C7 114.06(10) . . ?
C9 C8 C7 120.88(11) . . ?
C8 C9 C9A 119.31(11) . . ?
C8 C9 H9 120.3 . . ?
C9A C9 H9 120.3 . . ?
C9 C9A C5A 120.24(10) . . ?
C9 C9A C9B 123.16(10) . . ?
C5A C9A C9B 116.59(10) . . ?
C3A C9B C9A 122.31(11) . . ?
C3A C9B S1 111.27(9) . . ?
C9A C9B S1 126.42(9) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C9B S1 C2 C3 -0.38(11) . . . . ?
S1 C2 C3 C3A 0.65(15) . . . . ?
C2 C3 C3A C9B -0.64(16) . . . . ?
C2 C3 C3A C4 178.85(12) . . . . ?
C9B C3A C4 C5 0.12(18) . . . . ?
C3 C3A C4 C5 -179.34(12) . . . . ?
C3A C4 C5 C5A -0.86(19) . . . . ?
C4 C5 C5A C9A 0.52(18) . . . . ?
C4 C5 C5A C6 -177.78(12) . . . . ?
C9A C5A C6 C7 -0.12(18) . . . . ?
C5 C5A C6 C7 178.22(11) . . . . ?
C5A C6 C7 C8 0.14(18) . . . . ?
C10 O1 C8 C9 -5.84(16) . . . . ?
C10 O1 C8 C7 174.06(10) . . . . ?
C6 C7 C8 O1 179.99(11) . . . . ?
C6 C7 C8 C9 -0.11(18) . . . . ?
O1 C8 C9 C9A 179.95(10) . . . . ?
C7 C8 C9 C9A 0.06(17) . . . . ?
C8 C9 C9A C5A -0.05(17) . . . . ?
C8 C9 C9A C9B -178.78(11) . . . . ?
C6 C5A C9A C9 0.07(17) . . . . ?
C5 C5A C9A C9 -178.27(11) . . . . ?
C6 C5A C9A C9B 178.89(10) . . . . ?
C5 C5A C9A C9B 0.54(16) . . . . ?
C4 C3A C9B C9A 0.99(18) . . . . ?
C3 C3A C9B C9A -179.46(11) . . . . ?
C4 C3A C9B S1 -179.20(9) . . . . ?
C3 C3A C9B S1 0.35(13) . . . . ?
C9 C9A C9B C3A 177.48(11) . . . . ?
C5A C9A C9B C3A -1.29(17) . . . . ?
C9 C9A C9B S1 -2.29(17) . . . . ?
C5A C9A C9B S1 178.93(9) . . . . ?
C2 S1 C9B C3A 0.00(9) . . . . ?
C2 S1 C9B C9A 179.80(11) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_n13
_database_code_depnum_ccdc_archive 'CCDC 1903030'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 O2 S'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.30

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      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                   5.1488(12)
_cell_length_b                   10.707(2)
_cell_length_c                   20.672(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.856(4)
_cell_angle_gamma                90
_cell_volume                     1139.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    224
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3794
_exptl_absorpt_correction_T_max  0.4935
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14960
_diffrn_reflns_av_unetI/netI     0.1381
_diffrn_reflns_av_R_equivalents  0.1554
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         30.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3476
_reflns_number_gt                1799
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0778P)²+0.2113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3476
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.1882
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S3 S 0.38805(18) 0.56687(8) 0.08169(4) 0.0246(2) Uani 1 1 d . . . . .
O1 O 0.5610(5) 0.6890(2) 0.46584(11) 0.0240(5) Uani 1 1 d . . . . .
O2 O 0.8950(4) 0.5317(2) 0.42639(11) 0.0239(6) Uani 1 1 d . . . . .
C1 C 0.7092(7) 0.4802(3) 0.16846(16) 0.0221(7) Uani 1 1 d . . . . .
H1 H 0.847097 0.434467 0.188883 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6466(7) 0.4719(3) 0.10484(16) 0.0248(8) Uani 1 1 d . . . . .
H2 H 0.735076 0.419424 0.075749 0.030 Uiso 1 1 calc R U . . .
C3A C 0.3584(7) 0.6202(3) 0.16050(15) 0.0200(7) Uani 1 1 d . . . . .
C4 C 0.1752(7) 0.7073(3) 0.18222(16) 0.0227(7) Uani 1 1 d . . . . .
H4 H 0.049804 0.743104 0.153037 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1827(7) 0.7390(3) 0.24649(16) 0.0223(7) Uani 1 1 d . . . . .
H5 H 0.061158 0.797968 0.261733 0.027 Uiso 1 1 calc R U . . .
C5A C 0.3686(6) 0.6854(3) 0.29109(15) 0.0189(7) Uani 1 1 d . . . . .
C6 C 0.3705(7) 0.7180(3) 0.35774(15) 0.0211(7) Uani 1 1 d . . . . .
H6 H 0.248366 0.777163 0.372487 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5444(6) 0.6657(3) 0.40089(15) 0.0199(7) Uani 1 1 d . . . . .
C8 C 0.7310(6) 0.5774(3) 0.37898(15) 0.0200(7) Uani 1 1 d . . . . .
C9 C 0.7314(6) 0.5439(3) 0.31494(15) 0.0215(7) Uani 1 1 d . . . . .
H9 H 0.854140 0.484431 0.300799 0.026 Uiso 1 1 calc R U . . .
C9A C 0.5502(7) 0.5973(3) 0.26948(15) 0.0190(7) Uani 1 1 d . . . . .
C9B C 0.5458(6) 0.5653(3) 0.20225(15) 0.0198(7) Uani 1 1 d . . . . .
C10 C 0.3491(7) 0.7551(3) 0.49263(16) 0.0247(8) Uani 1 1 d . . . . .
H10A H 0.368929 0.755510 0.539939 0.037 Uiso 1 1 calc R U . . .
H10B H 0.185444 0.713901 0.479788 0.037 Uiso 1 1 calc R U . . .
H10C H 0.347432 0.841193 0.476559 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0723(7) 0.4357(3) 0.40816(16) 0.0256(7) Uani 1 1 d . . . . .
H11A H 1.182917 0.412402 0.445693 0.038 Uiso 1 1 calc R U . . .
H11B H 1.180946 0.466659 0.373545 0.038 Uiso 1 1 calc R U . . .
H11C H 0.974235 0.362519 0.392757 0.038 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
S3 C2 1.730(4) . ?
S3 C3A 1.738(3) . ?
O1 C7 1.365(4) . ?
O1 C10 1.427(4) . ?
O2 C8 1.364(4) . ?
O2 C11 1.433(4) . ?
C1 C2 1.347(5) . ?
C1 C9B 1.436(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3A C9B 1.403(4) . ?
C3A C4 1.410(5) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9500 . ?
C5 C5A 1.427(4) . ?
C5 H5 0.9500 . ?
C5A C9A 1.412(4) . ?
C5A C6 1.421(4) . ?
C6 C7 1.363(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.432(5) . ?
C8 C9 1.372(4) . ?
C9 C9A 1.422(4) . ?
C9 H9 0.9500 . ?
C9A C9B 1.431(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 S3 C3A 91.36(17) . . ?
C7 O1 C10 116.6(3) . . ?
C8 O2 C11 116.9(2) . . ?
C2 C1 C9B 113.0(3) . . ?
C2 C1 H1 123.5 . . ?
C9B C1 H1 123.5 . . ?
C1 C2 S3 112.9(3) . . ?
C1 C2 H2 123.6 . . ?
S3 C2 H2 123.6 . . ?
C9B C3A C4 122.4(3) . . ?
C9B C3A S3 111.1(3) . . ?
C4 C3A S3 126.6(3) . . ?
C5 C4 C3A 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C3A C4 H4 120.8 . . ?
C4 C5 C5A 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C5A C5 H5 119.2 . . ?
C9A C5A C6 119.1(3) . . ?
C9A C5A C5 120.1(3) . . ?
C6 C5A C5 120.7(3) . . ?
C7 C6 C5A 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5A C6 H6 119.4 . . ?
C6 C7 O1 126.0(3) . . ?
C6 C7 C8 119.8(3) . . ?
O1 C7 C8 114.2(3) . . ?
O2 C8 C9 125.4(3) . . ?
O2 C8 C7 114.6(3) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C9A 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C9A C9 H9 119.6 . . ?
C5A C9A C9 119.1(3) . . ?
C5A C9A C9B 118.5(3) . . ?
C9 C9A C9B 122.4(3) . . ?
C3A C9B C9A 119.1(3) . . ?
C3A C9B C1 111.6(3) . . ?
C9A C9B C1 129.3(3) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C9B C1 C2 S3 0.4(4) . . . . ?
C3A S3 C2 C1 -0.4(3) . . . . ?
C2 S3 C3A C9B 0.3(3) . . . . ?
C2 S3 C3A C4 -180.0(3) . . . . ?
C9B C3A C4 C5 0.1(5) . . . . ?
S3 C3A C4 C5 -179.5(3) . . . . ?
C3A C4 C5 C5A -0.4(5) . . . . ?
C4 C5 C5A C9A -0.2(5) . . . . ?
C4 C5 C5A C6 -179.0(3) . . . . ?
C9A C5A C6 C7 0.1(5) . . . . ?
C5 C5A C6 C7 178.9(3) . . . . ?
C5A C6 C7 O1 -179.1(3) . . . . ?
C5A C6 C7 C8 0.7(5) . . . . ?
C10 O1 C7 C6 12.5(5) . . . . ?
C10 O1 C7 C8 -167.4(3) . . . . ?
C11 O2 C8 C9 -3.7(5) . . . . ?
C11 O2 C8 C7 175.2(3) . . . . ?
C6 C7 C8 O2 179.9(3) . . . . ?
O1 C7 C8 O2 -0.3(4) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
O1 C7 C8 C9 178.6(3) . . . . ?
O2 C8 C9 C9A 179.7(3) . . . . ?
C7 C8 C9 C9A 0.9(5) . . . . ?
C6 C5A C9A C9 -0.4(5) . . . . ?
C5 C5A C9A C9 -179.2(3) . . . . ?
C6 C5A C9A C9B 179.9(3) . . . . ?
C5 C5A C9A C9B 1.1(5) . . . . ?
C8 C9 C9A C5A -0.1(5) . . . . ?
C8 C9 C9A C9B 179.6(3) . . . . ?
C4 C3A C9B C9A 0.8(5) . . . . ?
S3 C3A C9B C9A -179.5(2) . . . . ?
C4 C3A C9B C1 -179.9(3) . . . . ?
S3 C3A C9B C1 -0.2(4) . . . . ?
C5A C9A C9B C3A -1.4(5) . . . . ?
C9 C9A C9B C3A 178.9(3) . . . . ?
C5A C9A C9B C1 179.4(3) . . . . ?
C9 C9A C9B C1 -0.2(5) . . . . ?
C2 C1 C9B C3A -0.1(4) . . . . ?
C2 C1 C9B C9A 179.1(3) . . . . ?

_refine_diff_density_max         0.811
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_n8
_database_code_depnum_ccdc_archive 'CCDC 1903029'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 O2 S'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.30

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.3332(6)
_cell_length_b                   14.5631(9)
_cell_length_c                   15.1782(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2284.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    247
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7116
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29007
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.684
_diffrn_reflns_theta_max         30.563
_diffrn_reflns_theta_full        25.242
_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             3510
_reflns_number_gt                3018
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0527P)²+0.9920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3510
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.73651(3) 0.95617(2) 0.41531(2) 0.01682(8) Uani 1 1 d . . . . .
O1 O 0.53621(8) 0.53261(5) 0.27876(5) 0.01966(17) Uani 1 1 d . . . . .
O2 O 0.76017(8) 0.81707(6) 0.29193(5) 0.01781(17) Uani 1 1 d . . . . .
C2 C 0.70236(11) 1.01829(8) 0.50948(8) 0.0194(2) Uani 1 1 d . . . . .
H2 H 0.734218 1.078485 0.520011 0.023 Uiso 1 1 calc R U . . .
C3 C 0.62543(11) 0.97228(8) 0.56679(7) 0.0184(2) Uani 1 1 d . . . . .
H3 H 0.597506 0.996547 0.621687 0.022 Uiso 1 1 calc R U . . .
C3A C 0.59103(10) 0.88279(7) 0.53509(7) 0.01536(19) Uani 1 1 d . . . . .
C4 C 0.50672(11) 0.81779(8) 0.57497(7) 0.0174(2) Uani 1 1 d . . . . .
H4 H 0.468657 0.830742 0.630574 0.021 Uiso 1 1 calc R U . . .
C5 C 0.48044(10) 0.73679(8) 0.53340(7) 0.0171(2) Uani 1 1 d . . . . .
H5 H 0.423202 0.694239 0.560457 0.020 Uiso 1 1 calc R U . . .
C5A C 0.53703(10) 0.71439(7) 0.45004(7) 0.01424(19) Uani 1 1 d . . . . .
C6 C 0.50631(10) 0.62992(7) 0.40780(7) 0.0158(2) Uani 1 1 d . . . . .
H6 H 0.448434 0.587802 0.434862 0.019 Uiso 1 1 calc R U . . .
C7 C 0.56107(10) 0.60969(7) 0.32749(7) 0.0158(2) Uani 1 1 d . . . . .
C8 C 0.65009(10) 0.67053(7) 0.28696(7) 0.0159(2) Uani 1 1 d . . . . .
H8 H 0.689792 0.654412 0.232673 0.019 Uiso 1 1 calc R U . . .
C9 C 0.67868(10) 0.75285(7) 0.32652(7) 0.01420(19) Uani 1 1 d . . . . .
C9A C 0.62265(10) 0.77796(7) 0.40910(7) 0.01365(19) Uani 1 1 d . . . . .
C9B C 0.64601(10) 0.86336(7) 0.45267(7) 0.01414(19) Uani 1 1 d . . . . .
C10 C 0.43987(12) 0.47133(8) 0.31175(8) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.429850 0.419577 0.271047 0.036 Uiso 1 1 calc R U . . .
H10B H 0.357290 0.503951 0.317123 0.036 Uiso 1 1 calc R U . . .
H10C H 0.466320 0.448398 0.369717 0.036 Uiso 1 1 calc R U . . .
C11 C 0.81321(12) 0.79959(8) 0.20635(8) 0.0223(2) Uani 1 1 d . . . . .
H11A H 0.864841 0.852508 0.187494 0.033 Uiso 1 1 calc R U . . .
H11B H 0.742716 0.789410 0.164278 0.033 Uiso 1 1 calc R U . . .
H11C H 0.868359 0.744900 0.208734 0.033 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 C2 1.7280(12) . ?
S1 C9B 1.7386(11) . ?
O1 C7 1.3686(13) . ?
O1 C10 1.4277(14) . ?
O2 C9 1.3636(12) . ?
O2 C11 1.4327(13) . ?
C2 C3 1.3555(16) . ?
C2 H2 0.9500 . ?
C3 C3A 1.4339(15) . ?
C3 H3 0.9500 . ?
C3A C9B 1.4028(14) . ?
C3A C4 1.4217(15) . ?
C4 C5 1.3651(15) . ?
C4 H4 0.9500 . ?
C5 C5A 1.4315(14) . ?
C5 H5 0.9500 . ?
C5A C6 1.4231(14) . ?
C5A C9A 1.4233(14) . ?
C6 C7 1.3759(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4175(15) . ?
C8 C9 1.3729(14) . ?
C8 H8 0.9500 . ?
C9 C9A 1.4283(14) . ?
C9A C9B 1.4291(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 S1 C9B 91.57(5) . . ?
C7 O1 C10 117.01(9) . . ?
C9 O2 C11 117.61(9) . . ?
C3 C2 S1 113.07(9) . . ?
C3 C2 H2 123.5 . . ?
S1 C2 H2 123.5 . . ?
C2 C3 C3A 112.29(10) . . ?
C2 C3 H3 123.9 . . ?
C3A C3 H3 123.9 . . ?
C9B C3A C4 119.57(10) . . ?
C9B C3A C3 112.47(10) . . ?
C4 C3A C3 127.89(10) . . ?
C5 C4 C3A 120.03(10) . . ?
C5 C4 H4 120.0 . . ?
C3A C4 H4 120.0 . . ?
C4 C5 C5A 121.62(10) . . ?
C4 C5 H5 119.2 . . ?
C5A C5 H5 119.2 . . ?
C6 C5A C9A 120.28(9) . . ?
C6 C5A C5 120.27(9) . . ?
C9A C5A C5 119.44(9) . . ?
C7 C6 C5A 119.50(10) . . ?
C7 C6 H6 120.2 . . ?
C5A C6 H6 120.2 . . ?
O1 C7 C6 125.25(10) . . ?
O1 C7 C8 113.58(9) . . ?
C6 C7 C8 121.16(10) . . ?
C9 C8 C7 119.72(10) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O2 C9 C8 124.29(9) . . ?
O2 C9 C9A 114.37(9) . . ?
C8 C9 C9A 121.34(9) . . ?
C5A C9A C9 117.94(9) . . ?
C5A C9A C9B 117.97(9) . . ?
C9 C9A C9B 124.08(9) . . ?
C3A C9B C9A 121.32(9) . . ?
C3A C9B S1 110.60(8) . . ?
C9A C9B S1 128.06(8) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C9B S1 C2 C3 -0.48(9) . . . . ?
S1 C2 C3 C3A 0.01(13) . . . . ?
C2 C3 C3A C9B 0.62(14) . . . . ?
C2 C3 C3A C4 -176.29(11) . . . . ?
C9B C3A C4 C5 0.47(16) . . . . ?
C3 C3A C4 C5 177.18(11) . . . . ?
C3A C4 C5 C5A 0.69(17) . . . . ?
C4 C5 C5A C6 -179.13(11) . . . . ?
C4 C5 C5A C9A -0.13(16) . . . . ?
C9A C5A C6 C7 0.68(15) . . . . ?
C5 C5A C6 C7 179.67(10) . . . . ?
C10 O1 C7 C6 4.02(16) . . . . ?
C10 O1 C7 C8 -175.22(9) . . . . ?
C5A C6 C7 O1 -177.62(10) . . . . ?
C5A C6 C7 C8 1.55(16) . . . . ?
O1 C7 C8 C9 176.65(9) . . . . ?
C6 C7 C8 C9 -2.62(16) . . . . ?
C11 O2 C9 C8 3.85(15) . . . . ?
C11 O2 C9 C9A -175.82(9) . . . . ?
C7 C8 C9 O2 -178.23(9) . . . . ?
C7 C8 C9 C9A 1.42(16) . . . . ?
C6 C5A C9A C9 -1.81(15) . . . . ?
C5 C5A C9A C9 179.19(9) . . . . ?
C6 C5A C9A C9B 177.47(9) . . . . ?
C5 C5A C9A C9B -1.53(14) . . . . ?
O2 C9 C9A C5A -179.57(9) . . . . ?
C8 C9 C9A C5A 0.75(15) . . . . ?
O2 C9 C9A C9B 1.20(14) . . . . ?
C8 C9 C9A C9B -178.48(10) . . . . ?
C4 C3A C9B C9A -2.21(15) . . . . ?
C3 C3A C9B C9A -179.40(9) . . . . ?
C4 C3A C9B S1 176.24(8) . . . . ?
C3 C3A C9B S1 -0.96(11) . . . . ?
C5A C9A C9B C3A 2.71(15) . . . . ?
C9 C9A C9B C3A -178.06(10) . . . . ?
C5A C9A C9B S1 -175.44(8) . . . . ?
C9 C9A C9B S1 3.79(15) . . . . ?
C2 S1 C9B C3A 0.81(8) . . . . ?
C2 S1 C9B C9A 179.13(10) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_nat24-26
_database_code_depnum_ccdc_archive 'CCDC 1903031'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O2 S'
_chemical_formula_sum            'C14 H14 O2 S'
_chemical_formula_weight         246.31

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                   15.2689(10)
_cell_length_b                   5.1860(3)
_cell_length_c                   15.3921(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.0580(10)
_cell_angle_gamma                90
_cell_volume                     1212.01(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    197
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15504
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         30.655
_diffrn_reflns_theta_full        25.242
_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             3756
_reflns_number_gt                2998
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0553P)²+0.5210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3756
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.72815(2) 0.63873(7) 0.37055(2) 0.01822(10) Uani 1 1 d . . . . .
O22 O 0.53777(6) 0.78400(19) 0.59827(6) 0.0197(2) Uani 1 1 d . . . . .
O42 O 0.54421(6) 0.43664(19) 0.88526(6) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.76709(8) 0.3877(2) 0.43859(8) 0.0144(2) Uani 1 1 d . . . . .
C3 C 0.83890(9) 0.2719(3) 0.40764(8) 0.0163(2) Uani 1 1 d . . . . .
H3 H 0.869447 0.129341 0.435209 0.020 Uiso 1 1 calc R U . . .
C4 C 0.86234(9) 0.3905(3) 0.32926(8) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.910292 0.335197 0.299278 0.021 Uiso 1 1 calc R U . . .
C5 C 0.80860(9) 0.5905(3) 0.30237(9) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.814855 0.691505 0.251897 0.023 Uiso 1 1 calc R U . . .
C1' C 0.73105(9) 0.3327(3) 0.52026(8) 0.0166(2) Uani 1 1 d . . . . .
H1' H 0.751947 0.183793 0.551896 0.020 Uiso 1 1 calc R U . . .
C2' C 0.67036(9) 0.4776(3) 0.55401(8) 0.0167(2) Uani 1 1 d . . . . .
H2' H 0.645633 0.614093 0.518258 0.020 Uiso 1 1 calc R U . . .
C1" C 0.63779(8) 0.4501(3) 0.63950(8) 0.0146(2) Uani 1 1 d . . . . .
C2" C 0.57042(8) 0.6172(2) 0.66226(8) 0.0143(2) Uani 1 1 d . . . . .
C3" C 0.54069(8) 0.6072(2) 0.74449(8) 0.0144(2) Uani 1 1 d . . . . .
H3" H 0.495717 0.721176 0.758946 0.017 Uiso 1 1 calc R U . . .
C4" C 0.57747(8) 0.4282(2) 0.80577(8) 0.0139(2) Uani 1 1 d . . . . .
C5" C 0.64284(8) 0.2586(3) 0.78517(8) 0.0162(2) Uani 1 1 d . . . . .
H5" H 0.667129 0.135360 0.826576 0.019 Uiso 1 1 calc R U . . .
C6" C 0.67188(8) 0.2736(3) 0.70246(9) 0.0169(2) Uani 1 1 d . . . . .
H6" H 0.716773 0.158690 0.688436 0.020 Uiso 1 1 calc R U . . .
C21 C 0.46890(9) 0.9554(3) 0.61681(9) 0.0198(3) Uani 1 1 d . . . . .
H21A H 0.452051 1.063942 0.565654 0.030 Uiso 1 1 calc R U . . .
H21B H 0.489591 1.064655 0.666737 0.030 Uiso 1 1 calc R U . . .
H21C H 0.417812 0.855082 0.630752 0.030 Uiso 1 1 calc R U . . .
C41 C 0.57262(9) 0.2374(3) 0.94610(8) 0.0191(3) Uani 1 1 d . . . . .
H41A H 0.542518 0.256595 0.998902 0.029 Uiso 1 1 calc R U . . .
H41B H 0.636395 0.250508 0.961506 0.029 Uiso 1 1 calc R U . . .
H41C H 0.558397 0.068758 0.919574 0.029 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 C5 1.7161(13) . ?
S1 C2 1.7359(13) . ?
O22 C2" 1.3652(15) . ?
O22 C21 1.4284(16) . ?
O42 C4" 1.3740(14) . ?
O42 C41 1.4306(16) . ?
C2 C3 1.3785(18) . ?
C2 C1' 1.4527(17) . ?
C3 C4 1.4326(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3600(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C1' C2' 1.3398(18) . ?
C1' H1' 0.9500 . ?
C2' C1" 1.4619(17) . ?
C2' H2' 0.9500 . ?
C1" C6" 1.3933(18) . ?
C1" C2" 1.4170(17) . ?
C2" C3" 1.3900(17) . ?
C3" C4" 1.3982(17) . ?
C3" H3" 0.9500 . ?
C4" C5" 1.3918(18) . ?
C5" C6" 1.3937(17) . ?
C5" H5" 0.9500 . ?
C6" H6" 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?

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
C5 S1 C2 92.18(6) . . ?
C2" O22 C21 118.08(10) . . ?
C4" O42 C41 116.42(10) . . ?
C3 C2 C1' 126.95(12) . . ?
C3 C2 S1 110.64(10) . . ?
C1' C2 S1 122.17(10) . . ?
C2 C3 C4 112.49(12) . . ?
C2 C3 H3 123.8 . . ?
C4 C3 H3 123.8 . . ?
C5 C4 C3 112.79(12) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
C4 C5 S1 111.89(10) . . ?
C4 C5 H5 124.1 . . ?
S1 C5 H5 124.1 . . ?
C2' C1' C2 124.47(12) . . ?
C2' C1' H1' 117.8 . . ?
C2 C1' H1' 117.8 . . ?
C1' C2' C1" 127.52(12) . . ?
C1' C2' H2' 116.2 . . ?
C1" C2' H2' 116.2 . . ?
C6" C1" C2" 117.22(11) . . ?
C6" C1" C2' 123.55(12) . . ?
C2" C1" C2' 119.18(11) . . ?
O22 C2" C3" 123.43(11) . . ?
O22 C2" C1" 115.38(11) . . ?
C3" C2" C1" 121.19(11) . . ?
C2" C3" C4" 119.49(12) . . ?
C2" C3" H3" 120.3 . . ?
C4" C3" H3" 120.3 . . ?
O42 C4" C5" 124.35(11) . . ?
O42 C4" C3" 114.82(11) . . ?
C5" C4" C3" 120.83(11) . . ?
C4" C5" C6" 118.55(12) . . ?
C4" C5" H5" 120.7 . . ?
C6" C5" H5" 120.7 . . ?
C1" C6" C5" 122.70(12) . . ?
C1" C6" H6" 118.6 . . ?
C5" C6" H6" 118.6 . . ?
O22 C21 H21A 109.5 . . ?
O22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O42 C41 H41A 109.5 . . ?
O42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

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
C5 S1 C2 C3 -0.80(10) . . . . ?
C5 S1 C2 C1' 174.04(11) . . . . ?
C1' C2 C3 C4 -173.83(12) . . . . ?
S1 C2 C3 C4 0.70(14) . . . . ?
C2 C3 C4 C5 -0.18(17) . . . . ?
C3 C4 C5 S1 -0.43(15) . . . . ?
C2 S1 C5 C4 0.71(11) . . . . ?
C3 C2 C1' C2' 168.73(14) . . . . ?
S1 C2 C1' C2' -5.22(19) . . . . ?
C2 C1' C2' C1" -173.16(12) . . . . ?
C1' C2' C1" C6" 5.2(2) . . . . ?
C1' C2' C1" C2" -177.52(13) . . . . ?
C21 O22 C2" C3" -0.58(19) . . . . ?
C21 O22 C2" C1" 179.23(12) . . . . ?
C6" C1" C2" O22 -178.91(11) . . . . ?
C2' C1" C2" O22 3.64(18) . . . . ?
C6" C1" C2" C3" 0.90(19) . . . . ?
C2' C1" C2" C3" -176.54(12) . . . . ?
O22 C2" C3" C4" 179.42(12) . . . . ?
C1" C2" C3" C4" -0.38(19) . . . . ?
C41 O42 C4" C5" -7.26(18) . . . . ?
C41 O42 C4" C3" 172.95(11) . . . . ?
C2" C3" C4" O42 179.22(11) . . . . ?
C2" C3" C4" C5" -0.57(19) . . . . ?
O42 C4" C5" C6" -178.81(12) . . . . ?
C3" C4" C5" C6" 0.96(19) . . . . ?
C2" C1" C6" C5" -0.51(19) . . . . ?
C2' C1" C6" C5" 176.82(13) . . . . ?
C4" C5" C6" C1" -0.4(2) . . . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_n4
_database_code_depnum_ccdc_archive 'CCDC 1903024'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 O S'
_chemical_formula_sum            'C13 H12 O S'
_chemical_formula_weight         216.29

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                   5.9726(3)
_cell_length_b                   7.5101(4)
_cell_length_c                   24.2373(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.8230(10)
_cell_angle_gamma                90
_cell_volume                     1085.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    257
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18771
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.682
_diffrn_reflns_theta_max         30.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3364
_reflns_number_gt                2917
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0473P)²+0.3091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3364
_refine_ls_number_parameters     274
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.030
_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 0.64380(7) 0.25975(7) 0.90327(2) 0.02066(10) Uani 0.8898(15) 1 d D . P A 1
O1 O 0.0980(4) 0.3783(5) 0.56000(8) 0.0203(4) Uani 0.8898(15) 1 d D . P A 1
C2 C 0.77954(18) 0.36719(14) 0.85120(4) 0.0159(2) Uani 0.8898(15) 1 d D . P A 1
C3 C 0.9834(6) 0.4381(6) 0.87165(16) 0.0219(5) Uani 0.8898(15) 1 d D . P A 1
H3 H 1.083773 0.502094 0.849788 0.026 Uiso 0.8898(15) 1 calc R U P A 1
C4 C 1.0229(5) 0.4037(5) 0.92873(9) 0.0233(3) Uani 0.8898(15) 1 d D . P A 1
H4 H 1.153002 0.443274 0.949298 0.028 Uiso 0.8898(15) 1 calc R U P A 1
C5 C 0.8565(5) 0.3084(7) 0.95127(10) 0.0239(4) Uani 0.8898(15) 1 d D . P A 1
H5 H 0.857668 0.273059 0.988919 0.029 Uiso 0.8898(15) 1 calc R U P A 1
C1' C 0.68529(17) 0.38040(13) 0.79515(4) 0.0168(2) Uani 0.8898(15) 1 d D . P A
1
H1' H 0.770782 0.442474 0.769287 0.020 Uiso 0.8898(15) 1 calc R U P A 1
C2' C 0.48676(19) 0.31232(14) 0.77642(4) 0.0163(2) Uani 0.8898(15) 1 d D . P A
1
H2' H 0.405730 0.244533 0.801843 0.020 Uiso 0.8898(15) 1 calc R U P A 1
C1" C 0.3842(2) 0.33290(19) 0.72064(5) 0.0151(2) Uani 0.8898(15) 1 d D . P A 1
C2" C 0.1733(2) 0.2584(2) 0.70785(7) 0.0173(3) Uani 0.8898(15) 1 d D . P A 1
H2" H 0.098580 0.197166 0.735876 0.021 Uiso 0.8898(15) 1 calc R U P A 1
C3" C 0.0691(4) 0.2715(4) 0.65496(9) 0.0183(4) Uani 0.8898(15) 1 d D . P A 1
H3" H -0.074689 0.220517 0.647314 0.022 Uiso 0.8898(15) 1 calc R U P A 1
C4" C 0.1792(6) 0.3604(7) 0.61371(8) 0.0166(3) Uani 0.8898(15) 1 d D . P A 1
C5" C 0.3863(5) 0.4413(6) 0.62605(11) 0.0195(4) Uani 0.8898(15) 1 d D . P A 1
H5" H 0.458443 0.505713 0.598240 0.023 Uiso 0.8898(15) 1 calc R U P A 1
C6" C 0.4870(3) 0.4281(3) 0.67863(6) 0.0186(3) Uani 0.8898(15) 1 d D . P A 1
H6" H 0.627549 0.484141 0.686491 0.022 Uiso 0.8898(15) 1 calc R U P A 1
C7 C -0.1100(5) 0.2922(3) 0.54537(12) 0.0245(4) Uani 0.8898(15) 1 d D . P A 1
H7A H -0.154746 0.319759 0.506870 0.037 Uiso 0.8898(15) 1 calc R U P A 1
H7B H -0.225520 0.334601 0.569533 0.037 Uiso 0.8898(15) 1 calc R U P A 1
H7C H -0.092361 0.163095 0.549668 0.037 Uiso 0.8898(15) 1 calc R U P A 1
S1A S 0.9570(17) 0.4329(16) 0.8627(4) 0.0382(17) Uani 0.1102(15) 1 d D U P A 2
O1A O 0.071(4) 0.358(4) 0.5625(7) 0.022(2) Uani 0.1102(15) 1 d D U P A 2
C2A C 0.706(2) 0.3195(17) 0.8627(5) 0.0367(16) Uani 0.1102(15) 1 d D U P A 2
C3A C 0.664(4) 0.255(3) 0.9151(7) 0.037(2) Uani 0.1102(15) 1 d D U P A 2
H3A H 0.537379 0.186353 0.923895 0.045 Uiso 0.1102(15) 1 calc R U P A 2
C4A C 0.834(6) 0.304(7) 0.9520(10) 0.036(2) Uani 0.1102(15) 1 d D U P A 2
H4A H 0.828387 0.278418 0.990286 0.044 Uiso 0.1102(15) 1 calc R U P A 2
C5A C 1.006(5) 0.391(6) 0.9319(9) 0.038(2) Uani 0.1102(15) 1 d D U P A 2
H5A H 1.138084 0.424597 0.952790 0.045 Uiso 0.1102(15) 1 calc R U P A 2
C1'A C 0.550(2) 0.2919(16) 0.8141(4) 0.0390(17) Uani 0.1102(15) 1 d D U P A 2
H1'A H 0.420258 0.222250 0.819388 0.047 Uiso 0.1102(15) 1 calc R U P A 2
C2'A C 0.574(2) 0.3514(16) 0.7671(4) 0.0347(17) Uani 0.1102(15) 1 d D U P A 2
H2'A H 0.715297 0.407232 0.764112 0.042 Uiso 0.1102(15) 1 calc R U P A 2
C1"A C 0.435(2) 0.358(2) 0.7133(5) 0.0289(18) Uani 0.1102(15) 1 d D U P A 2
C2"A C 0.232(2) 0.278(2) 0.7091(7) 0.026(2) Uani 0.1102(15) 1 d D U P A 2
H2"A H 0.175630 0.229261 0.741787 0.032 Uiso 0.1102(15) 1 calc R U P A 2
C3"A C 0.097(4) 0.261(4) 0.6595(8) 0.026(2) Uani 0.1102(15) 1 d D U P A 2
H3"A H -0.032326 0.187828 0.656958 0.031 Uiso 0.1102(15) 1 calc R U P A 2
C4"A C 0.166(6) 0.359(7) 0.6153(8) 0.025(2) Uani 0.1102(15) 1 d D U P A 2
C5"A C 0.369(5) 0.452(6) 0.6214(11) 0.027(2) Uani 0.1102(15) 1 d D U P A 2
H5"A H 0.412829 0.529189 0.592732 0.032 Uiso 0.1102(15) 1 calc R U P A 2
C6"A C 0.503(3) 0.435(3) 0.6666(6) 0.028(2) Uani 0.1102(15) 1 d D U P A 2
H6"A H 0.651992 0.477674 0.666022 0.034 Uiso 0.1102(15) 1 calc R U P A 2
C7A C -0.126(4) 0.254(3) 0.5505(11) 0.025(3) Uani 0.1102(15) 1 d D U P A 2
H7D H -0.147386 0.238733 0.510411 0.038 Uiso 0.1102(15) 1 calc R U P A 2
H7E H -0.255868 0.315062 0.564658 0.038 Uiso 0.1102(15) 1 calc R U P A 2
H7F H -0.108769 0.136942 0.568103 0.038 Uiso 0.1102(15) 1 calc R U P A 2


_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 C5 1.719(2) . ?
S1 C2 1.7325(12) . ?
O1 C4" 1.3731(14) . ?
O1 C7 1.4299(18) . ?
C2 C3 1.397(3) . ?
C2 C1' 1.4481(14) . ?
C3 C4 1.416(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C1' C2' 1.3493(15) . ?
C1' H1' 0.9500 . ?
C2' C1" 1.4647(16) . ?
C2' H2' 0.9500 . ?
C1" C2" 1.3987(16) . ?
C1" C6" 1.4093(17) . ?
C2" C3" 1.4007(19) . ?
C2" H2" 0.9500 . ?
C3" C4" 1.394(2) . ?
C3" H3" 0.9500 . ?
C4" C5" 1.3973(19) . ?
C5" C6" 1.386(2) . ?
C5" H5" 0.9500 . ?
C6" H6" 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
S1A C5A 1.717(18) . ?
S1A C2A 1.725(13) . ?
O1A C4"A 1.372(5) . ?
O1A C7A 1.429(5) . ?
C2A C3A 1.393(15) . ?
C2A C1'A 1.479(13) . ?
C3A C4A 1.369(19) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.331(17) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C1'A C2'A 1.237(13) . ?
C1'A H1'A 0.9500 . ?
C2'A C1"A 1.510(13) . ?
C2'A H2'A 0.9500 . ?
C1"A C6"A 1.347(14) . ?
C1"A C2"A 1.354(14) . ?
C2"A C3"A 1.419(15) . ?
C2"A H2"A 0.9500 . ?
C3"A C4"A 1.379(15) . ?
C3"A H3"A 0.9500 . ?
C4"A C5"A 1.403(16) . ?
C5"A C6"A 1.328(16) . ?
C5"A H5"A 0.9500 . ?
C6"A H6"A 0.9500 . ?
C7A H7D 0.9800 . ?
C7A H7E 0.9800 . ?
C7A H7F 0.9800 . ?

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
C5 S1 C2 92.14(10) . . ?
C4" O1 C7 116.92(16) . . ?
C3 C2 C1' 126.7(2) . . ?
C3 C2 S1 110.49(19) . . ?
C1' C2 S1 122.75(8) . . ?
C2 C3 C4 112.2(3) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
C5 C4 C3 113.5(2) . . ?
C5 C4 H4 123.3 . . ?
C3 C4 H4 123.3 . . ?
C4 C5 S1 111.72(18) . . ?
C4 C5 H5 124.1 . . ?
S1 C5 H5 124.1 . . ?
C2' C1' C2 125.75(10) . . ?
C2' C1' H1' 117.1 . . ?
C2 C1' H1' 117.1 . . ?
C1' C2' C1" 126.25(11) . . ?
C1' C2' H2' 116.9 . . ?
C1" C2' H2' 116.9 . . ?
C2" C1" C6" 117.53(12) . . ?
C2" C1" C2' 119.57(11) . . ?
C6" C1" C2' 122.90(12) . . ?
C1" C2" C3" 121.98(14) . . ?
C1" C2" H2" 119.0 . . ?
C3" C2" H2" 119.0 . . ?
C4" C3" C2" 119.07(17) . . ?
C4" C3" H3" 120.5 . . ?
C2" C3" H3" 120.5 . . ?
O1 C4" C3" 124.75(15) . . ?
O1 C4" C5" 115.32(14) . . ?
C3" C4" C5" 119.92(15) . . ?
C6" C5" C4" 120.34(19) . . ?
C6" C5" H5" 119.8 . . ?
C4" C5" H5" 119.8 . . ?
C5" C6" C1" 121.06(17) . . ?
C5" C6" H6" 119.5 . . ?
C1" C6" H6" 119.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5A S1A C2A 90.9(10) . . ?
C4"A O1A C7A 119.5(14) . . ?
C3A C2A C1'A 123.0(13) . . ?
C3A C2A S1A 111.4(10) . . ?
C1'A C2A S1A 125.5(9) . . ?
C4A C3A C2A 110.1(16) . . ?
C4A C3A H3A 125.0 . . ?
C2A C3A H3A 125.0 . . ?
C5A C4A C3A 117(2) . . ?
C5A C4A H4A 121.5 . . ?
C3A C4A H4A 121.5 . . ?
C4A C5A S1A 110.5(17) . . ?
C4A C5A H5A 124.8 . . ?
S1A C5A H5A 124.8 . . ?
C2'A C1'A C2A 126.0(12) . . ?
C2'A C1'A H1'A 117.0 . . ?
C2A C1'A H1'A 117.0 . . ?
C1'A C2'A C1"A 136.4(14) . . ?
C1'A C2'A H2'A 111.8 . . ?
C1"A C2'A H2'A 111.8 . . ?
C6"A C1"A C2"A 115.5(13) . . ?
C6"A C1"A C2'A 124.5(13) . . ?
C2"A C1"A C2'A 120.0(12) . . ?
C1"A C2"A C3"A 124.9(15) . . ?
C1"A C2"A H2"A 117.5 . . ?
C3"A C2"A H2"A 117.5 . . ?
C4"A C3"A C2"A 115.6(16) . . ?
C4"A C3"A H3"A 122.2 . . ?
C2"A C3"A H3"A 122.2 . . ?
O1A C4"A C3"A 126.5(13) . . ?
O1A C4"A C5"A 114.7(11) . . ?
C3"A C4"A C5"A 118.2(13) . . ?
C6"A C5"A C4"A 121.2(19) . . ?
C6"A C5"A H5"A 119.4 . . ?
C4"A C5"A H5"A 119.4 . . ?
C5"A C6"A C1"A 122.9(19) . . ?
C5"A C6"A H6"A 118.5 . . ?
C1"A C6"A H6"A 118.5 . . ?
O1A C7A H7D 109.5 . . ?
O1A C7A H7E 109.5 . . ?
H7D C7A H7E 109.5 . . ?
O1A C7A H7F 109.5 . . ?
H7D C7A H7F 109.5 . . ?
H7E C7A H7F 109.5 . . ?

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
C5 S1 C2 C3 -0.2(3) . . . . ?
C5 S1 C2 C1' -179.2(2) . . . . ?
C1' C2 C3 C4 178.8(3) . . . . ?
S1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 S1 -0.7(6) . . . . ?
C2 S1 C5 C4 0.5(4) . . . . ?
C3 C2 C1' C2' -179.3(3) . . . . ?
S1 C2 C1' C2' -0.44(16) . . . . ?
C2 C1' C2' C1" 176.50(11) . . . . ?
C1' C2' C1" C2" -178.10(12) . . . . ?
C1' C2' C1" C6" 0.8(2) . . . . ?
C6" C1" C2" C3" 2.1(3) . . . . ?
C2' C1" C2" C3" -178.93(19) . . . . ?
C1" C2" C3" C4" 0.4(4) . . . . ?
C7 O1 C4" C3" -2.9(7) . . . . ?
C7 O1 C4" C5" 178.0(4) . . . . ?
C2" C3" C4" O1 178.2(4) . . . . ?
C2" C3" C4" C5" -2.7(7) . . . . ?
O1 C4" C5" C6" -178.4(4) . . . . ?
C3" C4" C5" C6" 2.4(7) . . . . ?
C4" C5" C6" C1" 0.2(6) . . . . ?
C2" C1" C6" C5" -2.4(3) . . . . ?
C2' C1" C6" C5" 178.7(3) . . . . ?
C5A S1A C2A C3A 1(2) . . . . ?
C5A S1A C2A C1'A -179(2) . . . . ?
C1'A C2A C3A C4A -178(3) . . . . ?
S1A C2A C3A C4A 2(3) . . . . ?
C2A C3A C4A C5A -4(6) . . . . ?
C3A C4A C5A S1A 5(6) . . . . ?
C2A S1A C5A C4A -3(4) . . . . ?
C3A C2A C1'A C2'A 177.2(17) . . . . ?
S1A C2A C1'A C2'A -3(2) . . . . ?
C2A C1'A C2'A C1"A -173.0(14) . . . . ?
C1'A C2'A C1"A C6"A 179.7(18) . . . . ?
C1'A C2'A C1"A C2"A -3(3) . . . . ?
C6"A C1"A C2"A C3"A 4(3) . . . . ?
C2'A C1"A C2"A C3"A -174(2) . . . . ?
C1"A C2"A C3"A C4"A -11(5) . . . . ?
C7A O1A C4"A C3"A 4(7) . . . . ?
C7A O1A C4"A C5"A 175(4) . . . . ?
C2"A C3"A C4"A O1A 176(4) . . . . ?
C2"A C3"A C4"A C5"A 5(6) . . . . ?
O1A C4"A C5"A C6"A -166(4) . . . . ?
C3"A C4"A C5"A C6"A 6(7) . . . . ?
C4"A C5"A C6"A C1"A -14(6) . . . . ?
C2"A C1"A C6"A C5"A 9(4) . . . . ?
C2'A C1"A C6"A C5"A -174(3) . . . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.253
_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_a
_database_code_depnum_ccdc_archive 'CCDC 1903025'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.7010(6)
_cell_length_b                   7.6258(5)
_cell_length_c                   20.3847(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.9390(10)
_cell_angle_gamma                90
_cell_volume                     1339.60(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    338
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17797
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         30.494
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4069
_reflns_number_gt                3191
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0580P)²+0.2989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4069
_refine_ls_number_parameters     203
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.019
_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 0.6571(4) 0.1985(5) 0.37112(15) 0.0260(5) Uani 0.4189(19) 1 d . U P A 1
C2 C 0.7215(10) 0.2707(11) 0.4510(3) 0.0348(13) Uani 0.4189(19) 1 d . U P A 1
H2 H 0.696048 0.215918 0.489940 0.042 Uiso 0.4189(19) 1 calc R U P A 1
C3 C 0.8094(13) 0.4097(14) 0.4510(3) 0.0420(16) Uani 0.4189(19) 1 d . U P A 1
H3 H 0.853706 0.466407 0.490607 0.050 Uiso 0.4189(19) 1 calc R U P A 1
S3' S 0.8070(2) 0.4043(2) 0.46934(5) 0.0262(2) Uani 0.5811(19) 1 d . U P A 2
C2' C 0.6837(7) 0.2369(8) 0.4399(2) 0.0284(9) Uani 0.5811(19) 1 d . U P A 2
H2' H 0.635390 0.160727 0.467773 0.034 Uiso 0.5811(19) 1 calc R U P A 2
C1' C 0.6628(13) 0.2252(15) 0.3740(5) 0.0338(19) Uani 0.5811(19) 1 d . U P A 2
H1' H 0.598036 0.139289 0.350414 0.041 Uiso 0.5811(19) 1 calc R U P A 2
O1 O 0.78120(10) 0.50708(12) 0.07164(4) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.63202(10) 0.22436(11) 0.10253(4) 0.02491(19) Uani 1 1 d . . . . .
O3 O 0.59804(9) 0.14723(11) 0.23308(4) 0.02245(18) Uani 1 1 d . . . . .
C3A C 0.83296(13) 0.46808(16) 0.38895(6) 0.0228(2) Uani 1 1 d . U . . .
C4 C 0.92152(14) 0.61290(16) 0.37186(6) 0.0250(2) Uani 1 1 d . . . . .
H4 H 0.976964 0.683909 0.405409 0.030 Uiso 1 1 calc R U . . .
C5 C 0.92612(13) 0.64900(15) 0.30665(6) 0.0222(2) Uani 1 1 d . . . . .
H5 H 0.984377 0.746975 0.295192 0.027 Uiso 1 1 calc R U . . .
C5A C 0.84541(12) 0.54304(14) 0.25499(5) 0.0186(2) Uani 1 1 d . . . . .
C6 C 0.85540(13) 0.58396(14) 0.18783(6) 0.0200(2) Uani 1 1 d . . . . .
H6 H 0.913958 0.682651 0.177279 0.024 Uiso 1 1 calc R U . . .
C7 C 0.78050(13) 0.48106(15) 0.13796(5) 0.0198(2) Uani 1 1 d . . . . .
C8 C 0.69478(12) 0.33179(14) 0.15351(5) 0.0192(2) Uani 1 1 d . . . . .
C9 C 0.68365(12) 0.29074(14) 0.21862(5) 0.0183(2) Uani 1 1 d . . . . .
C9A C 0.75767(12) 0.39600(14) 0.27140(5) 0.0184(2) Uani 1 1 d . . . . .
C9B C 0.75131(13) 0.36053(15) 0.34011(6) 0.0214(2) Uani 1 1 d . U . . .
C10 C 0.87394(18) 0.6482(2) 0.05341(7) 0.0369(3) Uani 1 1 d . . . . .
H10A H 0.870463 0.650202 0.005158 0.055 Uiso 1 1 calc R U . . .
H10B H 0.981398 0.632203 0.074296 0.055 Uiso 1 1 calc R U . . .
H10C H 0.833749 0.759288 0.068239 0.055 Uiso 1 1 calc R U . . .
C11 C 0.47062(16) 0.2485(3) 0.08260(9) 0.0500(5) Uani 1 1 d . . . . .
H11A H 0.433172 0.161545 0.048742 0.075 Uiso 1 1 calc R U . . .
H11B H 0.452005 0.366704 0.064327 0.075 Uiso 1 1 calc R U . . .
H11C H 0.415213 0.234038 0.120965 0.075 Uiso 1 1 calc R U . . .
C12 C 0.67300(16) -0.01788(16) 0.22537(8) 0.0320(3) Uani 1 1 d . . . . .
H12A H 0.609024 -0.113104 0.239225 0.048 Uiso 1 1 calc R U . . .
H12B H 0.774768 -0.019008 0.252823 0.048 Uiso 1 1 calc R U . . .
H12C H 0.686353 -0.034146 0.178806 0.048 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 C9B 1.656(3) . ?
S1 C2 1.737(8) . ?
C2 C3 1.307(11) . ?
C2 H2 0.9500 . ?
C3 C3A 1.382(7) . ?
C3 H3 0.9500 . ?
S3' C2' 1.722(4) . ?
S3' C3A 1.7536(15) . ?
C2' C1' 1.334(12) . ?
C2' H2' 0.9500 . ?
C1' C9B 1.511(9) . ?
C1' H1' 0.9500 . ?
O1 C7 1.3673(13) . ?
O1 C10 1.4249(15) . ?
O2 C8 1.3757(13) . ?
O2 C11 1.4191(17) . ?
O3 C9 1.3785(13) . ?
O3 C12 1.4365(15) . ?
C3A C9B 1.4046(16) . ?
C3A C4 1.4174(18) . ?
C4 C5 1.3634(17) . ?
C4 H4 0.9500 . ?
C5 C5A 1.4321(15) . ?
C5 H5 0.9500 . ?
C5A C6 1.4185(15) . ?
C5A C9A 1.4222(15) . ?
C6 C7 1.3751(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4205(15) . ?
C8 C9 1.3800(15) . ?
C9 C9A 1.4231(15) . ?
C9A C9B 1.4352(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C9B S1 C2 90.5(3) . . ?
C3 C2 S1 111.7(6) . . ?
C3 C2 H2 124.1 . . ?
S1 C2 H2 124.1 . . ?
C2 C3 C3A 115.0(7) . . ?
C2 C3 H3 122.5 . . ?
C3A C3 H3 122.5 . . ?
C2' S3' C3A 91.97(19) . . ?
C1' C2' S3' 113.1(5) . . ?
C1' C2' H2' 123.4 . . ?
S3' C2' H2' 123.4 . . ?
C2' C1' C9B 114.0(8) . . ?
C2' C1' H1' 123.0 . . ?
C9B C1' H1' 123.0 . . ?
C7 O1 C10 116.58(9) . . ?
C8 O2 C11 114.38(10) . . ?
C9 O3 C12 113.92(9) . . ?
C3 C3A C9B 109.6(4) . . ?
C3 C3A C4 129.1(4) . . ?
C9B C3A C4 121.31(11) . . ?
C9B C3A S3' 112.51(10) . . ?
C4 C3A S3' 126.17(10) . . ?
C5 C4 C3A 119.15(11) . . ?
C5 C4 H4 120.4 . . ?
C3A C4 H4 120.4 . . ?
C4 C5 C5A 121.71(11) . . ?
C4 C5 H5 119.1 . . ?
C5A C5 H5 119.1 . . ?
C6 C5A C9A 120.46(10) . . ?
C6 C5A C5 119.77(10) . . ?
C9A C5A C5 119.77(10) . . ?
C7 C6 C5A 120.13(10) . . ?
C7 C6 H6 119.9 . . ?
C5A C6 H6 119.9 . . ?
O1 C7 C6 125.58(10) . . ?
O1 C7 C8 114.28(9) . . ?
C6 C7 C8 120.14(10) . . ?
O2 C8 C9 121.21(10) . . ?
O2 C8 C7 118.32(10) . . ?
C9 C8 C7 120.34(10) . . ?
O3 C9 C8 119.84(10) . . ?
O3 C9 C9A 119.19(10) . . ?
C8 C9 C9A 120.97(10) . . ?
C5A C9A C9 117.94(10) . . ?
C5A C9A C9B 118.19(10) . . ?
C9 C9A C9B 123.86(10) . . ?
C3A C9B C9A 119.85(11) . . ?
C3A C9B C1' 108.4(4) . . ?
C9A C9B C1' 131.7(4) . . ?
C3A C9B S1 113.20(15) . . ?
C9A C9B S1 126.94(15) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C9B S1 C2 C3 -0.2(8) . . . . ?
S1 C2 C3 C3A -0.4(12) . . . . ?
C3A S3' C2' C1' 0.8(7) . . . . ?
S3' C2' C1' C9B -0.1(11) . . . . ?
C2 C3 C3A C9B 1.0(10) . . . . ?
C2 C3 C3A C4 -179.7(6) . . . . ?
C2' S3' C3A C9B -1.3(3) . . . . ?
C2' S3' C3A C4 177.1(3) . . . . ?
C3 C3A C4 C5 -178.6(6) . . . . ?
C9B C3A C4 C5 0.58(17) . . . . ?
S3' C3A C4 C5 -177.78(12) . . . . ?
C3A C4 C5 C5A -0.81(17) . . . . ?
C4 C5 C5A C6 -179.04(10) . . . . ?
C4 C5 C5A C9A 0.03(17) . . . . ?
C9A C5A C6 C7 -0.22(16) . . . . ?
C5 C5A C6 C7 178.85(10) . . . . ?
C10 O1 C7 C6 3.21(17) . . . . ?
C10 O1 C7 C8 -175.96(11) . . . . ?
C5A C6 C7 O1 179.89(10) . . . . ?
C5A C6 C7 C8 -0.97(16) . . . . ?
C11 O2 C8 C9 82.09(15) . . . . ?
C11 O2 C8 C7 -101.92(14) . . . . ?
O1 C7 C8 O2 4.38(15) . . . . ?
C6 C7 C8 O2 -174.85(10) . . . . ?
O1 C7 C8 C9 -179.59(10) . . . . ?
C6 C7 C8 C9 1.18(16) . . . . ?
C12 O3 C9 C8 75.28(13) . . . . ?
C12 O3 C9 C9A -105.59(12) . . . . ?
O2 C8 C9 O3 -5.15(16) . . . . ?
C7 C8 C9 O3 178.94(10) . . . . ?
O2 C8 C9 C9A 175.73(10) . . . . ?
C7 C8 C9 C9A -0.18(16) . . . . ?
C6 C5A C9A C9 1.18(15) . . . . ?
C5 C5A C9A C9 -177.88(10) . . . . ?
C6 C5A C9A C9B -179.96(10) . . . . ?
C5 C5A C9A C9B 0.97(15) . . . . ?
O3 C9 C9A C5A 179.90(9) . . . . ?
C8 C9 C9A C5A -0.98(16) . . . . ?
O3 C9 C9A C9B 1.12(16) . . . . ?
C8 C9 C9A C9B -179.76(10) . . . . ?
C3 C3A C9B C9A 179.8(5) . . . . ?
C4 C3A C9B C9A 0.43(17) . . . . ?
S3' C3A C9B C9A 179.00(10) . . . . ?
C4 C3A C9B C1' -177.1(5) . . . . ?
S3' C3A C9B C1' 1.5(5) . . . . ?
C3 C3A C9B S1 -1.1(5) . . . . ?
C4 C3A C9B S1 179.53(17) . . . . ?
C5A C9A C9B C3A -1.19(15) . . . . ?
C9 C9A C9B C3A 177.59(10) . . . . ?
C5A C9A C9B C1' 175.7(6) . . . . ?
C9 C9A C9B C1' -5.6(6) . . . . ?
C5A C9A C9B S1 179.84(19) . . . . ?
C9 C9A C9B S1 -1.4(2) . . . . ?
C2' C1' C9B C3A -0.9(10) . . . . ?
C2' C1' C9B C9A -178.0(5) . . . . ?
C2 S1 C9B C3A 0.8(4) . . . . ?
C2 S1 C9B C9A 179.8(3) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.225
_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_nd620
_database_code_depnum_ccdc_archive 'CCDC 1903028'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 O2 S'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.30

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      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                   11.3769(10)
_cell_length_b                   10.1584(9)
_cell_length_c                   20.2218(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.6730(19)
_cell_angle_gamma                90
_cell_volume                     2336.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    756
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31554
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.015
_diffrn_reflns_theta_max         30.624
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7191
_reflns_number_gt                5544
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0588P)²+0.6873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         7191
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.98207(3) 0.66590(4) 0.06319(2) 0.02749(10) Uani 1 1 d . . . . .
O1 O 0.80674(9) 1.24632(11) 0.14352(5) 0.0247(2) Uani 1 1 d . . . . .
O2 O 1.02968(9) 1.32151(11) 0.12629(6) 0.0284(2) Uani 1 1 d . . . . .
C2 C 0.86744(15) 0.55794(16) 0.07431(8) 0.0311(3) Uani 1 1 d . . . . .
H2 H 0.872541 0.465880 0.066638 0.037 Uiso 1 1 calc R U . . .
C3 C 0.76992(14) 0.61837(17) 0.09505(8) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.698497 0.573626 0.103280 0.035 Uiso 1 1 calc R U . . .
C3A C 0.78534(13) 0.75737(15) 0.10339(7) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.70474(13) 0.85238(16) 0.12671(7) 0.0245(3) Uani 1 1 d . . . . .
H4 H 0.627355 0.826357 0.137373 0.029 Uiso 1 1 calc R U . . .
C5 C 0.73779(12) 0.98015(16) 0.13383(7) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.682689 1.042766 0.148964 0.027 Uiso 1 1 calc R U . . .
C5A C 0.85416(12) 1.02223(15) 0.11894(7) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.88941(12) 1.15403(14) 0.12727(7) 0.0207(3) Uani 1 1 d . . . . .
C7 C 1.00388(13) 1.19223(15) 0.11599(7) 0.0231(3) Uani 1 1 d . . . . .
C8 C 1.08528(13) 1.09866(16) 0.09479(8) 0.0275(3) Uani 1 1 d . . . . .
H8 H 1.164145 1.124352 0.087505 0.033 Uiso 1 1 calc R U . . .
C9 C 1.05206(13) 0.97107(16) 0.08455(8) 0.0262(3) Uani 1 1 d . . . . .
H9 H 1.107981 0.909418 0.069383 0.031 Uiso 1 1 calc R U . . .
C9A C 0.93669(12) 0.92901(14) 0.09601(7) 0.0206(3) Uani 1 1 d . . . . .
C9B C 0.89783(12) 0.79716(15) 0.08791(7) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.81170(15) 1.28468(18) 0.21187(8) 0.0320(4) Uani 1 1 d . . . . .
H10A H 0.755894 1.356482 0.218856 0.048 Uiso 1 1 calc R U . . .
H10B H 0.891419 1.314433 0.223929 0.048 Uiso 1 1 calc R U . . .
H10C H 0.791185 1.209296 0.239491 0.048 Uiso 1 1 calc R U . . .
C11 C 1.14615(14) 1.36370(17) 0.11306(8) 0.0294(3) Uani 1 1 d . . . . .
H11A H 1.154501 1.457236 0.124091 0.044 Uiso 1 1 calc R U . . .
H11B H 1.161422 1.350627 0.066070 0.044 Uiso 1 1 calc R U . . .
H11C H 1.202598 1.312245 0.139924 0.044 Uiso 1 1 calc R U . . .
S1' S 0.44005(4) 0.43153(4) 0.08984(2) 0.02675(10) Uani 1 1 d . . . . .
O1' O 0.41046(9) -0.16959(10) 0.19066(5) 0.0227(2) Uani 1 1 d . . . . .
O2' O 0.35123(10) -0.23033(10) 0.06511(5) 0.0264(2) Uani 1 1 d . . . . .
C2' C 0.47602(14) 0.52748(16) 0.15781(9) 0.0311(4) Uani 1 1 d . . . . .
H2' H 0.481990 0.620699 0.156165 0.037 Uiso 1 1 calc R U . . .
C3' C 0.49474(14) 0.45691(15) 0.21334(9) 0.0290(3) Uani 1 1 d . . . . .
H3' H 0.515824 0.494475 0.255038 0.035 Uiso 1 1 calc R U . . .
C3A' C 0.47925(13) 0.31843(14) 0.20244(8) 0.0227(3) Uani 1 1 d . . . . .
C4' C 0.48802(14) 0.21426(15) 0.24906(7) 0.0255(3) Uani 1 1 d . . . . .
H4' H 0.511465 0.232371 0.293609 0.031 Uiso 1 1 calc R U . . .
C5' C 0.46300(13) 0.08869(14) 0.23024(7) 0.0213(3) Uani 1 1 d . . . . .
H5' H 0.468136 0.019975 0.262060 0.026 Uiso 1 1 calc R U . . .
C5A' C 0.42914(11) 0.05836(13) 0.16345(7) 0.0173(3) Uani 1 1 d . . . . .
C6' C 0.40159(12) -0.07131(13) 0.14387(7) 0.0179(3) Uani 1 1 d . . . . .
C7' C 0.37155(12) -0.10081(14) 0.07890(7) 0.0193(3) Uani 1 1 d . . . . .
C8' C 0.36489(12) -0.00005(14) 0.03164(7) 0.0211(3) Uani 1 1 d . . . . .
H8' H 0.342663 -0.019985 -0.012891 0.025 Uiso 1 1 calc R U . . .
C9' C 0.39036(12) 0.12727(14) 0.04946(7) 0.0206(3) Uani 1 1 d . . . . .
H9' H 0.385798 0.194701 0.016936 0.025 Uiso 1 1 calc R U . . .
C9A' C 0.42306(11) 0.15972(13) 0.11494(7) 0.0179(3) Uani 1 1 d . . . . .
C9B' C 0.44864(12) 0.29000(14) 0.13703(7) 0.0197(3) Uani 1 1 d . . . . .
C10' C 0.29843(15) -0.21611(18) 0.21132(8) 0.0329(4) Uani 1 1 d . . . . .
H10D H 0.310055 -0.282335 0.246137 0.049 Uiso 1 1 calc R U . . .
H10E H 0.255636 -0.255568 0.173510 0.049 Uiso 1 1 calc R U . . .
H10F H 0.252988 -0.142256 0.228427 0.049 Uiso 1 1 calc R U . . .
C11' C 0.30783(14) -0.26283(16) -0.00004(8) 0.0274(3) Uani 1 1 d . . . . .
H11D H 0.292601 -0.357660 -0.002727 0.041 Uiso 1 1 calc R U . . .
H11E H 0.366478 -0.238520 -0.032415 0.041 Uiso 1 1 calc R U . . .
H11F H 0.234699 -0.214553 -0.009560 0.041 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 C2 1.7237(17) . ?
S1 C9B 1.7246(15) . ?
O1 C6 1.3746(17) . ?
O1 C10 1.4356(18) . ?
O2 C7 1.3604(18) . ?
O2 C11 1.4253(18) . ?
C2 C3 1.346(2) . ?
C2 H2 0.9500 . ?
C3 C3A 1.432(2) . ?
C3 H3 0.9500 . ?
C3A C9B 1.387(2) . ?
C3A C4 1.421(2) . ?
C4 C5 1.358(2) . ?
C4 H4 0.9500 . ?
C5 C5A 1.432(2) . ?
C5 H5 0.9500 . ?
C5A C6 1.406(2) . ?
C5A C9A 1.4209(19) . ?
C6 C7 1.384(2) . ?
C7 C8 1.403(2) . ?
C8 C9 1.364(2) . ?
C8 H8 0.9500 . ?
C9 C9A 1.406(2) . ?
C9 H9 0.9500 . ?
C9A C9B 1.418(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
S1' C2' 1.7245(18) . ?
S1' C9B' 1.7267(14) . ?
O1' C6' 1.3771(16) . ?
O1' C10' 1.4329(19) . ?
O2' C7' 1.3633(17) . ?
O2' C11' 1.4319(18) . ?
C2' C3' 1.344(2) . ?
C2' H2' 0.9500 . ?
C3' C3A' 1.434(2) . ?
C3' H3' 0.9500 . ?
C3A' C9B' 1.388(2) . ?
C3A' C4' 1.419(2) . ?
C4' C5' 1.359(2) . ?
C4' H4' 0.9500 . ?
C5' C5A' 1.4273(19) . ?
C5' H5' 0.9500 . ?
C5A' C6' 1.4081(19) . ?
C5A' C9A' 1.4224(19) . ?
C6' C7' 1.3808(19) . ?
C7' C8' 1.401(2) . ?
C8' C9' 1.371(2) . ?
C8' H8' 0.9500 . ?
C9' C9A' 1.4042(19) . ?
C9' H9' 0.9500 . ?
C9A' C9B' 1.4241(19) . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?

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 S1 C9B 91.44(8) . . ?
C6 O1 C10 114.03(11) . . ?
C7 O2 C11 117.33(12) . . ?
C3 C2 S1 112.59(13) . . ?
C3 C2 H2 123.7 . . ?
S1 C2 H2 123.7 . . ?
C2 C3 C3A 112.78(15) . . ?
C2 C3 H3 123.6 . . ?
C3A C3 H3 123.6 . . ?
C9B C3A C4 119.06(14) . . ?
C9B C3A C3 111.81(14) . . ?
C4 C3A C3 129.09(14) . . ?
C5 C4 C3A 120.32(14) . . ?
C5 C4 H4 119.8 . . ?
C3A C4 H4 119.8 . . ?
C4 C5 C5A 121.21(14) . . ?
C4 C5 H5 119.4 . . ?
C5A C5 H5 119.4 . . ?
C6 C5A C9A 119.00(13) . . ?
C6 C5A C5 121.42(13) . . ?
C9A C5A C5 119.58(13) . . ?
O1 C6 C7 120.12(13) . . ?
O1 C6 C5A 118.90(13) . . ?
C7 C6 C5A 120.90(13) . . ?
O2 C7 C6 116.44(13) . . ?
O2 C7 C8 124.02(14) . . ?
C6 C7 C8 119.54(14) . . ?
C9 C8 C7 120.51(14) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C9A 121.30(14) . . ?
C8 C9 H9 119.3 . . ?
C9A C9 H9 119.3 . . ?
C9 C9A C9B 123.87(13) . . ?
C9 C9A C5A 118.70(14) . . ?
C9B C9A C5A 117.41(13) . . ?
C3A C9B C9A 122.40(13) . . ?
C3A C9B S1 111.37(11) . . ?
C9A C9B S1 126.13(11) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2' S1' C9B' 91.25(8) . . ?
C6' O1' C10' 113.04(12) . . ?
C7' O2' C11' 117.55(12) . . ?
C3' C2' S1' 113.11(12) . . ?
C3' C2' H2' 123.4 . . ?
S1' C2' H2' 123.4 . . ?
C2' C3' C3A' 112.28(15) . . ?
C2' C3' H3' 123.9 . . ?
C3A' C3' H3' 123.9 . . ?
C9B' C3A' C4' 119.26(13) . . ?
C9B' C3A' C3' 112.13(14) . . ?
C4' C3A' C3' 128.58(14) . . ?
C5' C4' C3A' 120.26(14) . . ?
C5' C4' H4' 119.9 . . ?
C3A' C4' H4' 119.9 . . ?
C4' C5' C5A' 121.08(13) . . ?
C4' C5' H5' 119.5 . . ?
C5A' C5' H5' 119.5 . . ?
C6' C5A' C9A' 118.51(12) . . ?
C6' C5A' C5' 121.31(13) . . ?
C9A' C5A' C5' 120.18(12) . . ?
O1' C6' C7' 120.50(12) . . ?
O1' C6' C5A' 118.28(12) . . ?
C7' C6' C5A' 121.16(13) . . ?
O2' C7' C6' 116.10(12) . . ?
O2' C7' C8' 124.06(12) . . ?
C6' C7' C8' 119.84(13) . . ?
C9' C8' C7' 120.20(13) . . ?
C9' C8' H8' 119.9 . . ?
C7' C8' H8' 119.9 . . ?
C8' C9' C9A' 121.16(13) . . ?
C8' C9' H9' 119.4 . . ?
C9A' C9' H9' 119.4 . . ?
C9' C9A' C5A' 119.12(12) . . ?
C9' C9A' C9B' 124.05(13) . . ?
C5A' C9A' C9B' 116.82(12) . . ?
C3A' C9B' C9A' 122.36(13) . . ?
C3A' C9B' S1' 111.22(11) . . ?
C9A' C9B' S1' 126.35(11) . . ?
O1' C10' H10D 109.5 . . ?
O1' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
O1' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
O2' C11' H11D 109.5 . . ?
O2' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
O2' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?

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
C9B S1 C2 C3 0.60(13) . . . . ?
S1 C2 C3 C3A -0.50(18) . . . . ?
C2 C3 C3A C9B 0.10(19) . . . . ?
C2 C3 C3A C4 -177.37(15) . . . . ?
C9B C3A C4 C5 -0.2(2) . . . . ?
C3 C3A C4 C5 177.16(15) . . . . ?
C3A C4 C5 C5A -0.8(2) . . . . ?
C4 C5 C5A C6 -178.94(13) . . . . ?
C4 C5 C5A C9A 0.3(2) . . . . ?
C10 O1 C6 C7 -80.34(17) . . . . ?
C10 O1 C6 C5A 103.00(15) . . . . ?
C9A C5A C6 O1 174.03(12) . . . . ?
C5 C5A C6 O1 -6.7(2) . . . . ?
C9A C5A C6 C7 -2.6(2) . . . . ?
C5 C5A C6 C7 176.63(13) . . . . ?
C11 O2 C7 C6 -178.17(13) . . . . ?
C11 O2 C7 C8 1.5(2) . . . . ?
O1 C6 C7 O2 4.3(2) . . . . ?
C5A C6 C7 O2 -179.12(13) . . . . ?
O1 C6 C7 C8 -175.40(13) . . . . ?
C5A C6 C7 C8 1.2(2) . . . . ?
O2 C7 C8 C9 -178.94(15) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C9A -1.2(2) . . . . ?
C8 C9 C9A C9B -178.30(15) . . . . ?
C8 C9 C9A C5A -0.2(2) . . . . ?
C6 C5A C9A C9 2.1(2) . . . . ?
C5 C5A C9A C9 -177.13(13) . . . . ?
C6 C5A C9A C9B -179.71(12) . . . . ?
C5 C5A C9A C9B 1.05(19) . . . . ?
C4 C3A C9B C9A 1.6(2) . . . . ?
C3 C3A C9B C9A -176.18(13) . . . . ?
C4 C3A C9B S1 178.10(11) . . . . ?
C3 C3A C9B S1 0.35(16) . . . . ?
C9 C9A C9B C3A 176.08(14) . . . . ?
C5A C9A C9B C3A -2.0(2) . . . . ?
C9 C9A C9B S1 0.1(2) . . . . ?
C5A C9A C9B S1 -178.00(10) . . . . ?
C2 S1 C9B C3A -0.53(11) . . . . ?
C2 S1 C9B C9A 175.84(13) . . . . ?
C9B' S1' C2' C3' 0.55(13) . . . . ?
S1' C2' C3' C3A' -0.44(18) . . . . ?
C2' C3' C3A' C9B' 0.0(2) . . . . ?
C2' C3' C3A' C4' -178.02(15) . . . . ?
C9B' C3A' C4' C5' -2.1(2) . . . . ?
C3' C3A' C4' C5' 175.84(15) . . . . ?
C3A' C4' C5' C5A' 0.9(2) . . . . ?
C4' C5' C5A' C6' -179.14(14) . . . . ?
C4' C5' C5A' C9A' 1.1(2) . . . . ?
C10' O1' C6' C7' -76.10(17) . . . . ?
C10' O1' C6' C5A' 106.76(15) . . . . ?
C9A' C5A' C6' O1' 178.40(12) . . . . ?
C5' C5A' C6' O1' -1.3(2) . . . . ?
C9A' C5A' C6' C7' 1.3(2) . . . . ?
C5' C5A' C6' C7' -178.46(13) . . . . ?
C11' O2' C7' C6' 173.52(12) . . . . ?
C11' O2' C7' C8' -7.2(2) . . . . ?
O1' C6' C7' O2' 0.40(19) . . . . ?
C5A' C6' C7' O2' 177.46(12) . . . . ?
O1' C6' C7' C8' -178.88(12) . . . . ?
C5A' C6' C7' C8' -1.8(2) . . . . ?
O2' C7' C8' C9' -177.94(13) . . . . ?
C6' C7' C8' C9' 1.3(2) . . . . ?
C7' C8' C9' C9A' -0.2(2) . . . . ?
C8' C9' C9A' C5A' -0.3(2) . . . . ?
C8' C9' C9A' C9B' -178.86(13) . . . . ?
C6' C5A' C9A' C9' -0.21(19) . . . . ?
C5' C5A' C9A' C9' 179.54(12) . . . . ?
C6' C5A' C9A' C9B' 178.44(12) . . . . ?
C5' C5A' C9A' C9B' -1.81(19) . . . . ?
C4' C3A' C9B' C9A' 1.4(2) . . . . ?
C3' C3A' C9B' C9A' -176.90(13) . . . . ?
C4' C3A' C9B' S1' 178.62(11) . . . . ?
C3' C3A' C9B' S1' 0.36(16) . . . . ?
C9' C9A' C9B' C3A' 179.15(13) . . . . ?
C5A' C9A' C9B' C3A' 0.57(19) . . . . ?
C9' C9A' C9B' S1' 2.3(2) . . . . ?
C5A' C9A' C9B' S1' -176.25(10) . . . . ?
C2' S1' C9B' C3A' -0.50(11) . . . . ?
C2' S1' C9B' C9A' 176.62(13) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058

