# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1859654'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Cl O2 S2'
_chemical_formula_sum            'C12 H9 Cl O2 S2'
_chemical_formula_weight         284.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2227(9)
_cell_length_b                   8.8688(11)
_cell_length_c                   9.7985(13)
_cell_angle_alpha                72.745(2)
_cell_angle_beta                 86.410(3)
_cell_angle_gamma                77.000(2)
_cell_volume                     584.04(13)
_cell_formula_units_Z            2
_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            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   0.776
_exptl_transmission_factor_max   0.878
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8655
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         33.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4201
_reflns_number_gt                3496
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4201
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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 0.83955(5) 0.42681(5) 0.71292(4) 0.01326(11) Uani 1 1 d . . . . .
S2 S 0.55717(6) 0.72968(5) 0.07320(4) 0.01785(12) Uani 1 1 d . . . . .
Cl1 Cl 0.92952(7) 0.82964(6) -0.02124(5) 0.02602(13) Uani 1 1 d . . . . .
O1 O 0.68054(18) 0.96698(13) 0.40915(13) 0.0178(2) Uani 1 1 d . . . . .
O2 O 0.77715(19) 0.83360(15) 0.63496(13) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.7636(2) 0.52545(18) 0.54023(16) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.7220(2) 0.69167(18) 0.47000(16) 0.0109(3) Uani 1 1 d . . . . .
C3 C 0.7324(2) 0.82974(19) 0.51956(17) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.6294(2) 0.92813(19) 0.28467(17) 0.0160(3) Uani 1 1 d . . . . .
H4A H 0.7107 0.9664 0.2022 0.019 Uiso 1 1 calc R U . . .
H4B H 0.4947 0.9781 0.2579 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6617(2) 0.74740(18) 0.33022(16) 0.0113(3) Uani 1 1 d . . . . .
C6 C 0.6409(2) 0.64329(18) 0.25210(16) 0.0118(3) Uani 1 1 d . . . . .
C7 C 0.6826(2) 0.47534(18) 0.31940(16) 0.0115(3) Uani 1 1 d . . . . .
C8 C 0.7444(2) 0.41767(18) 0.46338(16) 0.0111(3) Uani 1 1 d . . . . .
C9 C 0.7944(2) 0.25275(18) 0.55217(18) 0.0138(3) Uani 1 1 d . . . . .
H9A H 0.7916 0.1620 0.5203 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8460(2) 0.24110(19) 0.68617(18) 0.0161(3) Uani 1 1 d . . . . .
H10A H 0.8821 0.1410 0.7583 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7738(3) 0.6966(2) -0.02328(18) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.7424 0.7105 -0.1238 0.026 Uiso 1 1 calc R U . . .
H11B H 0.8430 0.5834 0.0178 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6661(3) 0.3549(2) 0.24293(18) 0.0175(3) Uani 1 1 d . . . . .
H12A H 0.6061 0.4122 0.1494 0.026 Uiso 1 1 calc R U . . .
H12B H 0.5883 0.2814 0.2996 0.026 Uiso 1 1 calc R U . . .
H12C H 0.7930 0.2927 0.2299 0.026 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 C1 1.7180(15) . ?
S1 C10 1.7332(17) . ?
S2 C6 1.7757(15) . ?
S2 C11 1.7890(18) . ?
Cl1 C11 1.8084(19) . ?
O1 C3 1.363(2) . ?
O1 C4 1.4512(19) . ?
O2 C3 1.2074(19) . ?
C1 C2 1.401(2) . ?
C1 C8 1.414(2) . ?
C2 C5 1.374(2) . ?
C2 C3 1.463(2) . ?
C4 C5 1.498(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.399(2) . ?
C6 C7 1.409(2) . ?
C7 C8 1.414(2) . ?
C7 C12 1.503(2) . ?
C8 C9 1.440(2) . ?
C9 C10 1.355(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
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
C1 S1 C10 90.92(7) . . ?
C6 S2 C11 100.84(8) . . ?
C3 O1 C4 110.44(12) . . ?
C2 C1 C8 118.49(13) . . ?
C2 C1 S1 129.01(11) . . ?
C8 C1 S1 112.50(11) . . ?
C5 C2 C1 120.24(13) . . ?
C5 C2 C3 108.89(13) . . ?
C1 C2 C3 130.87(14) . . ?
O2 C3 O1 121.86(14) . . ?
O2 C3 C2 130.01(15) . . ?
O1 C3 C2 108.13(13) . . ?
O1 C4 C5 104.47(13) . . ?
O1 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
O1 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C2 C5 C6 122.35(14) . . ?
C2 C5 C4 108.05(13) . . ?
C6 C5 C4 129.59(14) . . ?
C5 C6 C7 118.82(14) . . ?
C5 C6 S2 118.27(11) . . ?
C7 C6 S2 122.89(12) . . ?
C6 C7 C8 118.95(13) . . ?
C6 C7 C12 122.29(14) . . ?
C8 C7 C12 118.76(14) . . ?
C1 C8 C7 121.15(14) . . ?
C1 C8 C9 110.59(14) . . ?
C7 C8 C9 128.25(14) . . ?
C10 C9 C8 112.63(14) . . ?
C10 C9 H9A 123.7 . . ?
C8 C9 H9A 123.7 . . ?
C9 C10 S1 113.36(12) . . ?
C9 C10 H10A 123.3 . . ?
S1 C10 H10A 123.3 . . ?
S2 C11 Cl1 114.46(10) . . ?
S2 C11 H11A 108.6 . . ?
Cl1 C11 H11A 108.6 . . ?
S2 C11 H11B 108.6 . . ?
Cl1 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 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
C10 S1 C1 C2 -179.75(15) . . . . ?
C10 S1 C1 C8 -0.25(12) . . . . ?
C8 C1 C2 C5 0.8(2) . . . . ?
S1 C1 C2 C5 -179.69(12) . . . . ?
C8 C1 C2 C3 -178.51(15) . . . . ?
S1 C1 C2 C3 1.0(3) . . . . ?
C4 O1 C3 O2 -178.53(15) . . . . ?
C4 O1 C3 C2 1.48(18) . . . . ?
C5 C2 C3 O2 179.32(17) . . . . ?
C1 C2 C3 O2 -1.3(3) . . . . ?
C5 C2 C3 O1 -0.69(18) . . . . ?
C1 C2 C3 O1 178.72(15) . . . . ?
C3 O1 C4 C5 -1.64(18) . . . . ?
C1 C2 C5 C6 -0.6(2) . . . . ?
C3 C2 C5 C6 178.84(14) . . . . ?
C1 C2 C5 C4 -179.83(14) . . . . ?
C3 C2 C5 C4 -0.35(18) . . . . ?
O1 C4 C5 C2 1.18(17) . . . . ?
O1 C4 C5 C6 -177.93(15) . . . . ?
C2 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C7 179.28(16) . . . . ?
C2 C5 C6 S2 178.75(12) . . . . ?
C4 C5 C6 S2 -2.3(2) . . . . ?
C11 S2 C6 C5 102.83(13) . . . . ?
C11 S2 C6 C7 -78.78(15) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
S2 C6 C7 C8 -178.54(11) . . . . ?
C5 C6 C7 C12 -179.35(14) . . . . ?
S2 C6 C7 C12 2.3(2) . . . . ?
C2 C1 C8 C7 -0.7(2) . . . . ?
S1 C1 C8 C7 179.72(11) . . . . ?
C2 C1 C8 C9 179.55(14) . . . . ?
S1 C1 C8 C9 0.00(16) . . . . ?
C6 C7 C8 C1 0.4(2) . . . . ?
C12 C7 C8 C1 179.61(14) . . . . ?
C6 C7 C8 C9 -179.94(15) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C1 C8 C9 C10 0.36(19) . . . . ?
C7 C8 C9 C10 -179.34(15) . . . . ?
C8 C9 C10 S1 -0.56(19) . . . . ?
C1 S1 C10 C9 0.47(13) . . . . ?
C6 S2 C11 Cl1 -74.62(11) . . . . ?


_refine_diff_density_max         0.688
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.084

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1859655'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 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         'C12 H10 O2 S2'
_chemical_formula_sum            'C12 H10 O2 S2'
_chemical_formula_weight         250.32

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/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                   7.4647(5)
_cell_length_b                   10.1476(6)
_cell_length_c                   14.7974(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.6800(10)
_cell_angle_gamma                90
_cell_volume                     1110.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    259
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.809
_exptl_transmission_factor_max   0.857
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.294
_exptl_absorpt_coefficient_mu    0.458
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13452
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         28.992
_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             2957
_reflns_number_gt                2724
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.3510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2957
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.60689(4) 0.68885(3) 0.42031(2) 0.02182(9) Uani 1 1 d . . . . .
S2 S 0.94883(4) 0.14876(3) 0.56977(2) 0.02184(9) Uani 1 1 d . . . . .
O1 O 0.91389(11) 0.55476(8) 0.70863(5) 0.02047(17) Uani 1 1 d . . . . .
O2 O 0.77902(12) 0.73519(8) 0.64272(6) 0.02597(19) Uani 1 1 d . . . . .
C1 C 0.53927(15) 0.60384(14) 0.31981(8) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.59010(15) 0.47616(13) 0.32280(7) 0.0227(2) Uani 1 1 d . . . . .
C3 C 0.68893(13) 0.43958(11) 0.41009(7) 0.0157(2) Uani 1 1 d . . . . .
C4 C 0.70544(13) 0.54842(10) 0.47008(7) 0.01431(19) Uani 1 1 d . . . . .
C5 C 0.79379(13) 0.53079(10) 0.55862(7) 0.01306(18) Uani 1 1 d . . . . .
C6 C 0.82316(14) 0.62144(11) 0.63648(7) 0.0173(2) Uani 1 1 d . . . . .
C7 C 0.94412(14) 0.41874(11) 0.68355(7) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.86342(13) 0.40929(10) 0.58548(6) 0.01248(18) Uani 1 1 d . . . . .
C9 C 0.85080(13) 0.29968(10) 0.52711(7) 0.01388(19) Uani 1 1 d . . . . .
C10 C 0.76345(14) 0.31498(10) 0.43791(7) 0.0155(2) Uani 1 1 d . . . . .
C11 C 0.74264(19) 0.20230(13) 0.37148(8) 0.0261(3) Uani 1 1 d . . . . .
C12 C 0.75006(19) 0.04827(13) 0.57625(11) 0.0306(3) Uani 1 1 d . . . . .
H7B H 1.0746(19) 0.4031(14) 0.6932(10) 0.018(3) Uiso 1 1 d . . . . .
H7A H 0.882(2) 0.3645(15) 0.7234(10) 0.020(3) Uiso 1 1 d . . . . .
H11C H 0.762(2) 0.2385(17) 0.3127(12) 0.034(4) Uiso 1 1 d . . . . .
H2 H 0.565(2) 0.4184(17) 0.2738(12) 0.034(4) Uiso 1 1 d . . . . .
H12C H 0.683(2) 0.0853(19) 0.6215(13) 0.044(5) Uiso 1 1 d . . . . .
H11B H 0.828(2) 0.1339(18) 0.3901(12) 0.039(5) Uiso 1 1 d . . . . .
H12B H 0.678(3) 0.0432(18) 0.5189(13) 0.040(5) Uiso 1 1 d . . . . .
H1 H 0.467(2) 0.6512(19) 0.2721(13) 0.044(5) Uiso 1 1 d . . . . .
H11A H 0.619(3) 0.165(2) 0.3651(14) 0.052(6) Uiso 1 1 d . . . . .
H12A H 0.792(3) -0.035(2) 0.5931(13) 0.047(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.7232(10) . ?
S1 C1 1.7349(14) . ?
S2 C9 1.7765(10) . ?
S2 C12 1.8134(14) . ?
O1 C6 1.3649(13) . ?
O1 C7 1.4548(13) . ?
O2 C6 1.2072(14) . ?
C1 C2 1.349(2) . ?
C1 H1 0.958(19) . ?
C2 C3 1.4477(14) . ?
C2 H2 0.932(17) . ?
C3 C4 1.4120(15) . ?
C3 C10 1.4199(15) . ?
C4 C5 1.3973(13) . ?
C5 C8 1.3759(14) . ?
C5 C6 1.4677(14) . ?
C7 C8 1.4982(13) . ?
C7 H7B 0.978(14) . ?
C7 H7A 0.968(15) . ?
C8 C9 1.4037(13) . ?
C9 C10 1.4005(14) . ?
C10 C11 1.5024(15) . ?
C11 H11C 0.972(18) . ?
C11 H11B 0.960(19) . ?
C11 H11A 0.99(2) . ?
C12 H12C 0.966(19) . ?
C12 H12B 0.945(19) . ?
C12 H12A 0.93(2) . ?

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
C4 S1 C1 90.79(6) . . ?
C9 S2 C12 101.68(6) . . ?
C6 O1 C7 110.40(8) . . ?
C2 C1 S1 113.64(8) . . ?
C2 C1 H1 129.3(11) . . ?
S1 C1 H1 116.9(11) . . ?
C1 C2 C3 112.52(11) . . ?
C1 C2 H2 123.4(11) . . ?
C3 C2 H2 124.0(11) . . ?
C4 C3 C10 121.09(9) . . ?
C4 C3 C2 110.58(10) . . ?
C10 C3 C2 128.33(10) . . ?
C5 C4 C3 118.68(9) . . ?
C5 C4 S1 128.87(8) . . ?
C3 C4 S1 112.44(8) . . ?
C8 C5 C4 119.89(9) . . ?
C8 C5 C6 108.90(9) . . ?
C4 C5 C6 131.15(10) . . ?
O2 C6 O1 121.74(10) . . ?
O2 C6 C5 130.21(10) . . ?
O1 C6 C5 108.05(9) . . ?
O1 C7 C8 104.58(8) . . ?
O1 C7 H7B 107.6(9) . . ?
C8 C7 H7B 113.2(9) . . ?
O1 C7 H7A 106.4(9) . . ?
C8 C7 H7A 113.0(9) . . ?
H7B C7 H7A 111.5(12) . . ?
C5 C8 C9 122.73(9) . . ?
C5 C8 C7 108.06(9) . . ?
C9 C8 C7 129.20(9) . . ?
C10 C9 C8 118.46(9) . . ?
C10 C9 S2 123.25(8) . . ?
C8 C9 S2 118.28(8) . . ?
C9 C10 C3 119.14(9) . . ?
C9 C10 C11 121.78(10) . . ?
C3 C10 C11 119.07(10) . . ?
C10 C11 H11C 106.4(10) . . ?
C10 C11 H11B 110.8(11) . . ?
H11C C11 H11B 111.0(15) . . ?
C10 C11 H11A 111.4(12) . . ?
H11C C11 H11A 107.8(15) . . ?
H11B C11 H11A 109.2(16) . . ?
S2 C12 H12C 108.9(11) . . ?
S2 C12 H12B 110.9(11) . . ?
H12C C12 H12B 110.8(15) . . ?
S2 C12 H12A 106.0(12) . . ?
H12C C12 H12A 111.1(17) . . ?
H12B C12 H12A 108.9(16) . . ?

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
C4 S1 C1 C2 -0.76(9) . . . . ?
S1 C1 C2 C3 0.38(13) . . . . ?
C1 C2 C3 C4 0.33(13) . . . . ?
C1 C2 C3 C10 -179.77(10) . . . . ?
C10 C3 C4 C5 -1.31(14) . . . . ?
C2 C3 C4 C5 178.60(9) . . . . ?
C10 C3 C4 S1 179.20(7) . . . . ?
C2 C3 C4 S1 -0.90(11) . . . . ?
C1 S1 C4 C5 -178.49(10) . . . . ?
C1 S1 C4 C3 0.94(8) . . . . ?
C3 C4 C5 C8 0.38(14) . . . . ?
S1 C4 C5 C8 179.78(8) . . . . ?
C3 C4 C5 C6 -176.36(10) . . . . ?
S1 C4 C5 C6 3.04(17) . . . . ?
C7 O1 C6 O2 177.85(10) . . . . ?
C7 O1 C6 C5 -1.54(11) . . . . ?
C8 C5 C6 O2 -177.84(11) . . . . ?
C4 C5 C6 O2 -0.84(19) . . . . ?
C8 C5 C6 O1 1.47(11) . . . . ?
C4 C5 C6 O1 178.48(10) . . . . ?
C6 O1 C7 C8 1.03(11) . . . . ?
C4 C5 C8 C9 0.31(15) . . . . ?
C6 C5 C8 C9 177.71(9) . . . . ?
C4 C5 C8 C7 -178.21(9) . . . . ?
C6 C5 C8 C7 -0.81(11) . . . . ?
O1 C7 C8 C5 -0.09(11) . . . . ?
O1 C7 C8 C9 -178.48(10) . . . . ?
C5 C8 C9 C10 -0.06(15) . . . . ?
C7 C8 C9 C10 178.12(10) . . . . ?
C5 C8 C9 S2 179.24(8) . . . . ?
C7 C8 C9 S2 -2.58(15) . . . . ?
C12 S2 C9 C10 -70.01(10) . . . . ?
C12 S2 C9 C8 110.73(9) . . . . ?
C8 C9 C10 C3 -0.85(14) . . . . ?
S2 C9 C10 C3 179.89(7) . . . . ?
C8 C9 C10 C11 -179.40(10) . . . . ?
S2 C9 C10 C11 1.34(14) . . . . ?
C4 C3 C10 C9 1.55(15) . . . . ?
C2 C3 C10 C9 -178.34(10) . . . . ?
C4 C3 C10 C11 -179.86(10) . . . . ?
C2 C3 C10 C11 0.25(16) . . . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1859657'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O2 S2'
_chemical_formula_sum            'C15 H14 O2 S2'
_chemical_formula_weight         290.38

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5548(5)
_cell_length_b                   8.9850(6)
_cell_length_c                   11.3559(7)
_cell_angle_alpha                75.4510(10)
_cell_angle_beta                 79.4630(10)
_cell_angle_gamma                65.9620(10)
_cell_volume                     678.58(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5902
_cell_measurement_theta_min      2.532
_cell_measurement_theta_max      36.453

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   0.886
_exptl_transmission_factor_max   0.934
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8441
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3608
_reflns_number_gt                3286
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.4244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     189
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

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 0.86888(5) 0.33610(5) 0.25914(3) 0.02237(11) Uani 1 1 d . . . . .
S2 S 0.51640(7) 0.24738(6) 1.03912(4) 0.03163(13) Uani 0.9607(12) 1 d D . P A 1
S2' S 0.8046(14) 0.3313(14) 0.9352(10) 0.03163(13) Uani 0.0393(12) 1 d D . P A
2
O1 O 0.73577(15) 0.68438(12) 0.54300(10) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.83165(15) 0.68049(13) 0.34357(10) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.79624(18) 0.33170(16) 0.41326(12) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.76154(19) 0.18707(16) 0.47172(13) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.8022(2) 0.07793(18) 0.38752(14) 0.0224(3) Uani 1 1 d . . . . .
H3A H 0.7897 -0.0268 0.4100 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8600(2) 0.1419(2) 0.27292(15) 0.0256(3) Uani 1 1 d . . . . .
H4A H 0.8926 0.0861 0.2065 0.031 Uiso 1 1 calc R U . . .
C5 C 0.76664(18) 0.45074(16) 0.48152(12) 0.0149(2) Uani 1 1 d . . . . .
C6 C 0.78433(19) 0.61244(17) 0.44323(13) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.6849(2) 0.57622(17) 0.65060(13) 0.0184(3) Uani 1 1 d . . . . .
H7A H 0.5502 0.6320 0.6854 0.022 Uiso 1 1 calc R U . . .
H7B H 0.7750 0.5438 0.7140 0.022 Uiso 1 1 calc R U . . .
C8 C 0.70382(18) 0.42672(16) 0.60427(12) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.66077(19) 0.28617(16) 0.66466(12) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.68940(19) 0.16616(16) 0.59665(13) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.5679(2) 0.27109(18) 0.79165(13) 0.0192(3) Uani 1 1 d . . . . .
H11A H 0.4428 0.2655 0.8026 0.023 Uiso 1 1 d R U . . .
C12 C 0.6410(2) 0.2644(2) 0.89233(13) 0.0231(3) Uani 1 1 d D . . . .
C13 C 0.8392(3) 0.2647(3) 0.89695(16) 0.0323(4) Uani 0.9607(12) 1 d D . P A 1
H13A H 0.9106 0.2612 0.8158 0.048 Uiso 0.9607(12) 1 calc R U P A 1
H13B H 0.9114 0.1671 0.9556 0.048 Uiso 0.9607(12) 1 calc R U P A 1
H13C H 0.8241 0.3659 0.9224 0.048 Uiso 0.9607(12) 1 calc R U P A 1
C14 C 0.2938(3) 0.2383(3) 1.01226(17) 0.0374(4) Uani 0.9607(12) 1 d D . P A 1
H14A H 0.2123 0.2312 1.0896 0.056 Uiso 0.9607(12) 1 calc R U P A 1
H14B H 0.3240 0.1401 0.9778 0.056 Uiso 0.9607(12) 1 calc R U P A 1
H14C H 0.2239 0.3386 0.9548 0.056 Uiso 0.9607(12) 1 calc R U P A 1
C15 C 0.6420(2) 0.01460(18) 0.65321(15) 0.0245(3) Uani 1 1 d . . . . .
H15A H 0.6063 0.0110 0.7410 0.037 Uiso 1 1 calc R U . . .
H15B H 0.7560 -0.0855 0.6404 0.037 Uiso 1 1 calc R U . . .
H15D H 0.5329 0.0197 0.6150 0.037 Uiso 1 1 calc R U . . .
C13' C 0.450(2) 0.311(5) 0.971(3) 0.0323(4) Uani 0.0393(12) 1 d D . P A 2
H13D H 0.4735 0.3134 1.0528 0.048 Uiso 0.0393(12) 1 calc R U P A 2
H13G H 0.3613 0.4213 0.9343 0.048 Uiso 0.0393(12) 1 calc R U P A 2
H13E H 0.3927 0.2292 0.9777 0.048 Uiso 0.0393(12) 1 calc R U P A 2
C14' C 1.0374(10) 0.166(3) 0.916(4) 0.0374(4) Uani 0.0393(12) 1 d D . P A 2
H14D H 1.1389 0.1926 0.9384 0.056 Uiso 0.0393(12) 1 calc R U P A 2
H14E H 1.0349 0.0620 0.9693 0.056 Uiso 0.0393(12) 1 calc R U P A 2
H14F H 1.0650 0.1527 0.8309 0.056 Uiso 0.0393(12) 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 C1 1.7313(14) . ?
S1 C4 1.7398(17) . ?
S2 C12 1.7618(15) . ?
S2 C14 1.800(2) . ?
S2' C12 1.760(3) . ?
S2' C14' 1.800(4) . ?
O1 C6 1.3634(17) . ?
O1 C7 1.4564(17) . ?
O2 C6 1.2103(18) . ?
C1 C5 1.3975(18) . ?
C1 C2 1.4067(18) . ?
C2 C10 1.4184(19) . ?
C2 C3 1.4452(19) . ?
C3 C4 1.355(2) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C5 C8 1.3803(18) . ?
C5 C6 1.4620(18) . ?
C7 C8 1.5076(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4102(18) . ?
C9 C10 1.4047(19) . ?
C9 C11 1.4832(18) . ?
C10 C15 1.5063(19) . ?
C11 C12 1.336(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.508(2) . ?
C12 C13' 1.509(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15D 0.9800 . ?
C13' H13D 0.9800 . ?
C13' H13G 0.9800 . ?
C13' H13E 0.9800 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 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
C1 S1 C4 90.67(7) . . ?
C12 S2 C14 103.51(8) . . ?
C12 S2' C14' 103.7(2) . . ?
C6 O1 C7 110.69(10) . . ?
C5 C1 C2 118.95(12) . . ?
C5 C1 S1 128.76(11) . . ?
C2 C1 S1 112.28(10) . . ?
C1 C2 C10 120.37(12) . . ?
C1 C2 C3 111.14(12) . . ?
C10 C2 C3 128.46(13) . . ?
C4 C3 C2 112.36(13) . . ?
C4 C3 H3A 123.8 . . ?
C2 C3 H3A 123.8 . . ?
C3 C4 S1 113.52(11) . . ?
C3 C4 H4A 123.2 . . ?
S1 C4 H4A 123.2 . . ?
C8 C5 C1 120.43(12) . . ?
C8 C5 C6 109.44(12) . . ?
C1 C5 C6 130.09(13) . . ?
O2 C6 O1 122.03(13) . . ?
O2 C6 C5 129.99(14) . . ?
O1 C6 C5 107.98(12) . . ?
O1 C7 C8 104.41(11) . . ?
O1 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
O1 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C5 C8 C9 122.08(12) . . ?
C5 C8 C7 107.45(11) . . ?
C9 C8 C7 130.41(12) . . ?
C10 C9 C8 117.86(12) . . ?
C10 C9 C11 119.66(12) . . ?
C8 C9 C11 122.14(12) . . ?
C9 C10 C2 120.22(12) . . ?
C9 C10 C15 121.28(13) . . ?
C2 C10 C15 118.50(12) . . ?
C12 C11 C9 127.03(13) . . ?
C12 C11 H11A 116.5 . . ?
C9 C11 H11A 116.5 . . ?
C11 C12 C13 125.47(14) . . ?
C11 C12 C13' 96.5(9) . . ?
C11 C12 S2' 139.2(4) . . ?
C13' C12 S2' 111.4(3) . . ?
C11 C12 S2 123.10(12) . . ?
C13 C12 S2 111.41(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15D 109.5 . . ?
H15A C15 H15D 109.5 . . ?
H15B C15 H15D 109.5 . . ?
C12 C13' H13D 109.5 . . ?
C12 C13' H13G 109.5 . . ?
H13D C13' H13G 109.5 . . ?
C12 C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
H13G C13' H13E 109.5 . . ?
S2' C14' H14D 109.5 . . ?
S2' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
S2' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 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
C4 S1 C1 C5 179.61(13) . . . . ?
C4 S1 C1 C2 -1.60(10) . . . . ?
C5 C1 C2 C10 2.77(19) . . . . ?
S1 C1 C2 C10 -176.15(10) . . . . ?
C5 C1 C2 C3 -179.24(12) . . . . ?
S1 C1 C2 C3 1.84(14) . . . . ?
C1 C2 C3 C4 -1.12(17) . . . . ?
C10 C2 C3 C4 176.66(13) . . . . ?
C2 C3 C4 S1 -0.09(17) . . . . ?
C1 S1 C4 C3 0.97(12) . . . . ?
C2 C1 C5 C8 -0.18(19) . . . . ?
S1 C1 C5 C8 178.54(10) . . . . ?
C2 C1 C5 C6 -177.42(13) . . . . ?
S1 C1 C5 C6 1.3(2) . . . . ?
C7 O1 C6 O2 179.98(12) . . . . ?
C7 O1 C6 C5 0.16(14) . . . . ?
C8 C5 C6 O2 -178.72(14) . . . . ?
C1 C5 C6 O2 -1.2(2) . . . . ?
C8 C5 C6 O1 1.08(15) . . . . ?
C1 C5 C6 O1 178.56(13) . . . . ?
C6 O1 C7 C8 -1.21(14) . . . . ?
C1 C5 C8 C9 -2.21(19) . . . . ?
C6 C5 C8 C9 175.55(11) . . . . ?
C1 C5 C8 C7 -179.58(11) . . . . ?
C6 C5 C8 C7 -1.82(14) . . . . ?
O1 C7 C8 C5 1.85(14) . . . . ?
O1 C7 C8 C9 -175.22(12) . . . . ?
C5 C8 C9 C10 1.92(19) . . . . ?
C7 C8 C9 C10 178.62(13) . . . . ?
C5 C8 C9 C11 -171.41(12) . . . . ?
C7 C8 C9 C11 5.3(2) . . . . ?
C8 C9 C10 C2 0.71(19) . . . . ?
C11 C9 C10 C2 174.21(12) . . . . ?
C8 C9 C10 C15 -178.35(12) . . . . ?
C11 C9 C10 C15 -4.85(19) . . . . ?
C1 C2 C10 C9 -3.05(19) . . . . ?
C3 C2 C10 C9 179.35(13) . . . . ?
C1 C2 C10 C15 176.04(12) . . . . ?
C3 C2 C10 C15 -1.6(2) . . . . ?
C10 C9 C11 C12 123.46(17) . . . . ?
C8 C9 C11 C12 -63.3(2) . . . . ?
C9 C11 C12 C13 -2.4(3) . . . . ?
C9 C11 C12 C13' 161.0(14) . . . . ?
C9 C11 C12 S2' 26.9(7) . . . . ?
C9 C11 C12 S2 179.68(11) . . . . ?
C14' S2' C12 C11 -87.3(15) . . . . ?
C14' S2' C12 C13' 143(2) . . . . ?
C14 S2 C12 C11 1.18(17) . . . . ?
C14 S2 C12 C13 -177.02(14) . . . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.060



_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_R598
_database_code_depnum_ccdc_archive 'CCDC 1859658'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_weight         318.32

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   16.7044(15)
_cell_length_b                   4.7039(4)
_cell_length_c                   18.5969(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1461.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2602
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16893
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         28.995
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3901
_reflns_number_gt                3549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.999
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0619P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         3901
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
N1 N 0.29172(12) -0.1478(4) 0.31630(10) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.39329(11) 0.4285(4) 0.51094(10) 0.0174(4) Uani 1 1 d . . . . .
H2N H 0.4449 0.4365 0.4925 0.021 Uiso 1 1 d R U . . .
O1 O 0.13784(9) 0.6932(3) 0.51188(10) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.04909(9) 0.4948(4) 0.43705(10) 0.0228(4) Uani 1 1 d . . . . .
O3 O 0.33408(10) 0.3096(4) 0.61686(10) 0.0282(4) Uani 1 1 d . . . . .
C1 C 0.32920(13) 0.3315(5) 0.46753(12) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.25111(14) 0.4402(5) 0.47853(12) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.22157(13) 0.6553(5) 0.53090(13) 0.0202(5) Uani 1 1 d . . . . .
H3A H 0.2270 0.5853 0.5809 0.024 Uiso 1 1 calc R U . . .
H3B H 0.2514 0.8361 0.5261 0.024 Uiso 1 1 calc R U . . .
C4 C 0.11733(14) 0.5108(5) 0.45870(13) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.18863(13) 0.3543(5) 0.43654(12) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.19757(13) 0.1534(5) 0.38056(12) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.13537(13) 0.0562(5) 0.33626(13) 0.0206(5) Uani 1 1 d . . . . .
H7A H 0.0824 0.1252 0.3424 0.025 Uiso 1 1 calc R U . . .
C8 C 0.15228(15) -0.1397(5) 0.28410(13) 0.0234(5) Uani 1 1 d . . . . .
H8A H 0.1112 -0.2101 0.2536 0.028 Uiso 1 1 calc R U . . .
C9 C 0.23120(15) -0.2345(5) 0.27655(13) 0.0226(5) Uani 1 1 d . . . . .
H9A H 0.2419 -0.3710 0.2402 0.027 Uiso 1 1 calc R U . . .
C10 C 0.27589(13) 0.0473(5) 0.36897(12) 0.0160(4) Uani 1 1 d . . . . .
C11 C 0.34187(13) 0.1384(5) 0.41256(11) 0.0156(4) Uani 1 1 d . . . . .
C12 C 0.42301(13) 0.0188(5) 0.39656(13) 0.0197(5) Uani 1 1 d . . . . .
H12A H 0.4577 0.0426 0.4387 0.029 Uiso 1 1 calc R U . . .
H12B H 0.4463 0.1195 0.3555 0.029 Uiso 1 1 calc R U . . .
H12C H 0.4182 -0.1838 0.3851 0.029 Uiso 1 1 calc R U . . .
C13 C 0.39089(13) 0.4097(5) 0.58449(13) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.46373(13) 0.5177(5) 0.62225(12) 0.0179(4) Uani 1 1 d . . . . .
C15 C 0.48433(15) 0.3902(5) 0.68702(13) 0.0237(5) Uani 1 1 d . . . . .
H15A H 0.4516 0.2439 0.7064 0.028 Uiso 1 1 calc R U . . .
C16 C 0.55245(16) 0.4759(6) 0.72347(15) 0.0276(5) Uani 1 1 d . . . . .
H16A H 0.5668 0.3865 0.7674 0.033 Uiso 1 1 calc R U . . .
C17 C 0.59950(16) 0.6907(6) 0.69601(15) 0.0272(5) Uani 1 1 d . . . . .
H17A H 0.6464 0.7481 0.7209 0.033 Uiso 1 1 calc R U . . .
C18 C 0.57870(16) 0.8224(5) 0.63251(14) 0.0260(5) Uani 1 1 d . . . . .
H18A H 0.6107 0.9728 0.6142 0.031 Uiso 1 1 calc R U . . .
C19 C 0.51081(15) 0.7355(5) 0.59516(13) 0.0217(5) Uani 1 1 d . . . . .
H19A H 0.4967 0.8252 0.5512 0.026 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
N1 C9 1.317(3) . ?
N1 C10 1.368(3) . ?
N2 C13 1.371(3) . ?
N2 C1 1.416(3) . ?
N2 H2N 0.9281 . ?
O1 C4 1.353(3) . ?
O1 C3 1.454(3) . ?
O2 C4 1.211(3) . ?
O3 C13 1.218(3) . ?
C1 C11 1.384(3) . ?
C1 C2 1.416(3) . ?
C2 C5 1.365(3) . ?
C2 C3 1.489(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.460(3) . ?
C5 C6 1.414(3) . ?
C6 C7 1.403(3) . ?
C6 C10 1.417(3) . ?
C7 C8 1.367(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.399(4) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.433(3) . ?
C11 C12 1.497(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.494(3) . ?
C14 C19 1.386(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.378(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.391(3) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
C9 N1 C10 117.5(2) . . ?
C13 N2 C1 121.71(19) . . ?
C13 N2 H2N 113.5 . . ?
C1 N2 H2N 120.3 . . ?
C4 O1 C3 110.11(17) . . ?
C11 C1 C2 119.0(2) . . ?
C11 C1 N2 121.12(19) . . ?
C2 C1 N2 119.9(2) . . ?
C5 C2 C1 121.0(2) . . ?
C5 C2 C3 108.79(19) . . ?
C1 C2 C3 130.2(2) . . ?
O1 C3 C2 104.07(18) . . ?
O1 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
O2 C4 O1 121.4(2) . . ?
O2 C4 C5 130.0(2) . . ?
O1 C4 C5 108.62(19) . . ?
C2 C5 C6 122.6(2) . . ?
C2 C5 C4 108.3(2) . . ?
C6 C5 C4 129.1(2) . . ?
C7 C6 C5 124.9(2) . . ?
C7 C6 C10 118.7(2) . . ?
C5 C6 C10 116.4(2) . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 H8A 120.6 . . ?
C9 C8 H8A 120.6 . . ?
N1 C9 C8 124.6(2) . . ?
N1 C9 H9A 117.7 . . ?
C8 C9 H9A 117.7 . . ?
N1 C10 C6 121.6(2) . . ?
N1 C10 C11 117.17(19) . . ?
C6 C10 C11 121.3(2) . . ?
C1 C11 C10 119.75(19) . . ?
C1 C11 C12 122.12(19) . . ?
C10 C11 C12 118.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 N2 122.7(2) . . ?
O3 C13 C14 122.2(2) . . ?
N2 C13 C14 115.0(2) . . ?
C19 C14 C15 119.6(2) . . ?
C19 C14 C13 122.9(2) . . ?
C15 C14 C13 117.6(2) . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C14 C19 C18 119.9(2) . . ?
C14 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?

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
C13 N2 C1 C11 -125.9(2) . . . . ?
C13 N2 C1 C2 56.3(3) . . . . ?
C11 C1 C2 C5 0.9(3) . . . . ?
N2 C1 C2 C5 178.7(2) . . . . ?
C11 C1 C2 C3 -177.3(2) . . . . ?
N2 C1 C2 C3 0.5(3) . . . . ?
C4 O1 C3 C2 4.0(2) . . . . ?
C5 C2 C3 O1 -2.9(2) . . . . ?
C1 C2 C3 O1 175.5(2) . . . . ?
C3 O1 C4 O2 176.0(2) . . . . ?
C3 O1 C4 C5 -3.7(2) . . . . ?
C1 C2 C5 C6 0.4(3) . . . . ?
C3 C2 C5 C6 179.0(2) . . . . ?
C1 C2 C5 C4 -177.69(19) . . . . ?
C3 C2 C5 C4 0.9(3) . . . . ?
O2 C4 C5 C2 -177.9(2) . . . . ?
O1 C4 C5 C2 1.7(3) . . . . ?
O2 C4 C5 C6 4.2(4) . . . . ?
O1 C4 C5 C6 -176.2(2) . . . . ?
C2 C5 C6 C7 179.4(2) . . . . ?
C4 C5 C6 C7 -2.9(4) . . . . ?
C2 C5 C6 C10 -1.1(3) . . . . ?
C4 C5 C6 C10 176.5(2) . . . . ?
C5 C6 C7 C8 -179.8(2) . . . . ?
C10 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C10 N1 C9 C8 0.5(4) . . . . ?
C7 C8 C9 N1 -0.2(4) . . . . ?
C9 N1 C10 C6 -0.1(3) . . . . ?
C9 N1 C10 C11 179.3(2) . . . . ?
C7 C6 C10 N1 -0.5(3) . . . . ?
C5 C6 C10 N1 -180.0(2) . . . . ?
C7 C6 C10 C11 -179.9(2) . . . . ?
C5 C6 C10 C11 0.6(3) . . . . ?
C2 C1 C11 C10 -1.4(3) . . . . ?
N2 C1 C11 C10 -179.16(19) . . . . ?
C2 C1 C11 C12 178.6(2) . . . . ?
N2 C1 C11 C12 0.9(3) . . . . ?
N1 C10 C11 C1 -178.8(2) . . . . ?
C6 C10 C11 C1 0.6(3) . . . . ?
N1 C10 C11 C12 1.2(3) . . . . ?
C6 C10 C11 C12 -179.4(2) . . . . ?
C1 N2 C13 O3 0.0(4) . . . . ?
C1 N2 C13 C14 179.19(19) . . . . ?
O3 C13 C14 C19 -150.3(2) . . . . ?
N2 C13 C14 C19 30.4(3) . . . . ?
O3 C13 C14 C15 30.0(3) . . . . ?
N2 C13 C14 C15 -149.2(2) . . . . ?
C19 C14 C15 C16 -1.4(4) . . . . ?
C13 C14 C15 C16 178.2(2) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C13 C14 C19 C18 -178.9(2) . . . . ?
C17 C18 C19 C14 0.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O2 0.93 2.05 2.965(2) 168.8 3_565

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_R466a
_database_code_depnum_ccdc_archive 'CCDC 1859659'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C23 H18 N2 O3), H2 O'
_chemical_formula_sum            'C23 H19 N2 O3.50'
_chemical_formula_weight         379.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.522(2)
_cell_length_b                   9.502(3)
_cell_length_c                   26.913(8)
_cell_angle_alpha                86.186(5)
_cell_angle_beta                 89.331(5)
_cell_angle_gamma                69.408(5)
_cell_volume                     1796.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_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 APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27572
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         0.758
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7754
_reflns_number_gt                7068
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7754
_refine_ls_number_parameters     520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.1027
_refine_ls_wR_factor_ref         0.2668
_refine_ls_wR_factor_gt          0.2634
_refine_ls_goodness_of_fit_ref   1.615
_refine_ls_restrained_S_all      1.615
_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
N1 N 0.1474(5) 0.6075(4) 0.45117(15) 0.0196(8) Uani 1 1 d . . . . .
N2 N 0.3629(6) 0.4019(4) 0.62326(15) 0.0205(8) Uani 1 1 d . . . . .
H2N H 0.3777 0.4829 0.6338 0.025 Uiso 1 1 d R U . . .
O1 O 0.7045(5) 0.0326(4) 0.53085(14) 0.0254(8) Uani 1 1 d . . . . .
O2 O 0.6850(5) 0.0576(4) 0.44764(14) 0.0279(8) Uani 1 1 d . . . . .
O3 O 0.3176(5) 0.1828(4) 0.64715(14) 0.0278(8) Uani 1 1 d . . . . .
C1 C 0.6285(6) 0.1097(5) 0.48704(19) 0.0218(9) Uani 1 1 d . . . . .
C2 C 0.6115(7) 0.1180(6) 0.5728(2) 0.0256(10) Uani 1 1 d . . . . .
H2A H 0.7052 0.1378 0.5942 0.031 Uiso 1 1 calc R U . . .
H2B H 0.5437 0.0628 0.5932 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4753(6) 0.2616(5) 0.54935(17) 0.0188(9) Uani 1 1 d . . . . .
C4 C 0.3556(6) 0.3907(5) 0.57098(17) 0.0185(9) Uani 1 1 d . . . . .
C5 C 0.2365(6) 0.5135(5) 0.54147(17) 0.0178(9) Uani 1 1 d . . . . .
C6 C 0.2445(6) 0.5026(5) 0.48924(18) 0.0184(9) Uani 1 1 d . . . . .
C7 C 0.2082(6) 0.5494(5) 0.40595(17) 0.0196(9) Uani 1 1 d . . . . .
C8 C 0.1524(7) 0.6164(6) 0.35796(18) 0.0247(10) Uani 1 1 d . . . . .
H8A H 0.0593 0.7143 0.3528 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2403(8) 0.5325(6) 0.3181(2) 0.0283(11) Uani 1 1 d . . . . .
H9A H 0.2062 0.5744 0.2851 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3775(8) 0.3878(6) 0.3256(2) 0.0285(11) Uani 1 1 d . . . . .
H10A H 0.4339 0.3340 0.2976 0.034 Uiso 1 1 calc R U . . .
C11 C 0.4320(7) 0.3224(6) 0.37274(18) 0.0241(10) Uani 1 1 d . . . . .
H11A H 0.5251 0.2243 0.3774 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3475(6) 0.4030(5) 0.41400(18) 0.0191(9) Uani 1 1 d . . . . .
C13 C 0.3707(6) 0.3732(5) 0.46705(17) 0.0176(9) Uani 1 1 d . . . . .
C14 C 0.4826(6) 0.2545(5) 0.49857(18) 0.0190(9) Uani 1 1 d . . . . .
C15 C -0.0002(7) 0.7554(5) 0.45573(18) 0.0220(9) Uani 1 1 d . . . . .
H15A H -0.0487 0.8002 0.4225 0.033 Uiso 1 1 calc R U . . .
H15B H 0.0536 0.8211 0.4719 0.033 Uiso 1 1 calc R U . . .
H15C H -0.1043 0.7438 0.4758 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1094(7) 0.6501(5) 0.56700(18) 0.0227(9) Uani 1 1 d . . . . .
H16A H 0.0938 0.6209 0.6019 0.034 Uiso 1 1 calc R U . . .
H16B H -0.0151 0.6897 0.5503 0.034 Uiso 1 1 calc R U . . .
H16C H 0.1673 0.7279 0.5653 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3512(7) 0.2936(6) 0.65837(17) 0.0221(9) Uani 1 1 d . . . . .
C18 C 0.3897(7) 0.3203(6) 0.71007(18) 0.0227(9) Uani 1 1 d . . . . .
C19 C 0.3192(8) 0.4608(6) 0.72985(19) 0.0287(11) Uani 1 1 d . . . . .
H19A H 0.2357 0.5447 0.7105 0.034 Uiso 1 1 calc R U . . .
C20 C 0.3698(8) 0.4787(7) 0.7774(2) 0.0340(12) Uani 1 1 d . . . . .
H20A H 0.3191 0.5746 0.7908 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4934(8) 0.3587(7) 0.8057(2) 0.0361(13) Uani 1 1 d . . . . .
H21A H 0.5290 0.3718 0.8383 0.043 Uiso 1 1 calc R U . . .
C22 C 0.5651(10) 0.2190(7) 0.7861(2) 0.0442(16) Uani 1 1 d . . . . .
H22A H 0.6527 0.1367 0.8052 0.053 Uiso 1 1 calc R U . . .
C23 C 0.5112(9) 0.1972(7) 0.73911(19) 0.0341(12) Uani 1 1 d . . . . .
H23A H 0.5561 0.0997 0.7267 0.041 Uiso 1 1 calc R U . . .
N1A N -0.1911(6) 0.4478(5) -0.02587(16) 0.0227(8) Uani 1 1 d . . . . .
N2A N -0.0419(6) 0.1787(5) 0.14133(15) 0.0223(8) Uani 1 1 d . . . . .
H2NA H -0.1542 0.1777 0.1505 0.027 Uiso 1 1 d R U . . .
O1A O 0.3710(5) -0.1367(4) 0.04418(13) 0.0252(7) Uani 1 1 d . . . . .
O2A O 0.3747(5) -0.0859(4) -0.03784(14) 0.0277(8) Uani 1 1 d . . . . .
O3A O 0.2447(5) 0.1694(4) 0.16888(14) 0.0288(8) Uani 1 1 d . . . . .
C1A C 0.3078(7) -0.0470(5) 0.00161(18) 0.0216(9) Uani 1 1 d . . . . .
C2A C 0.2738(7) -0.0625(5) 0.08744(18) 0.0239(10) Uani 1 1 d . . . . .
H2AA H 0.3639 -0.0433 0.1102 0.029 Uiso 1 1 calc R U . . .
H2AB H 0.2096 -0.1243 0.1059 0.029 Uiso 1 1 calc R U . . .
C3A C 0.1319(7) 0.0826(6) 0.06578(19) 0.0229(10) Uani 1 1 d . . . . .
C4A C -0.0073(6) 0.1969(5) 0.08955(18) 0.0201(9) Uani 1 1 d . . . . .
C5A C -0.1248(6) 0.3264(6) 0.06206(19) 0.0229(10) Uani 1 1 d . . . . .
C6A C -0.0973(7) 0.3345(6) 0.00980(18) 0.0223(9) Uani 1 1 d . . . . .
C7A C -0.1173(7) 0.4040(6) -0.07188(19) 0.0230(9) Uani 1 1 d . . . . .
C8A C -0.1667(7) 0.4819(6) -0.1181(2) 0.0273(10) Uani 1 1 d . . . . .
H8AA H -0.2644 0.5782 -0.1212 0.033 Uiso 1 1 calc R U . . .
C9A C -0.0701(9) 0.4160(7) -0.1599(2) 0.0342(12) Uani 1 1 d . . . . .
H9AA H -0.1031 0.4675 -0.1918 0.041 Uiso 1 1 calc R U . . .
C10A C 0.0755(8) 0.2742(6) -0.1554(2) 0.0300(11) Uani 1 1 d . . . . .
H10B H 0.1411 0.2316 -0.1843 0.036 Uiso 1 1 calc R U . . .
C11A C 0.1243(7) 0.1966(6) -0.10976(19) 0.0263(10) Uani 1 1 d . . . . .
H11B H 0.2224 0.1005 -0.1070 0.032 Uiso 1 1 calc R U . . .
C12A C 0.0272(7) 0.2611(5) -0.06721(18) 0.0228(10) Uani 1 1 d . . . . .
C13A C 0.0394(7) 0.2162(5) -0.01484(19) 0.0215(9) Uani 1 1 d . . . . .
C14A C 0.1540(6) 0.0916(5) 0.01492(18) 0.0199(9) Uani 1 1 d . . . . .
C15A C -0.3272(7) 0.5986(6) -0.0189(2) 0.0303(11) Uani 1 1 d . . . . .
H15D H -0.3442 0.6607 -0.0502 0.046 Uiso 1 1 calc R U . . .
H15E H -0.2794 0.6446 0.0069 0.046 Uiso 1 1 calc R U . . .
H15F H -0.4494 0.5915 -0.0086 0.046 Uiso 1 1 calc R U . . .
C16A C -0.2689(7) 0.4505(6) 0.08911(19) 0.0274(11) Uani 1 1 d . . . . .
H16D H -0.3069 0.4072 0.1197 0.041 Uiso 1 1 calc R U . . .
H16E H -0.3806 0.5001 0.0676 0.041 Uiso 1 1 calc R U . . .
H16F H -0.2124 0.5244 0.0976 0.041 Uiso 1 1 calc R U . . .
C17A C 0.0876(7) 0.1629(5) 0.17748(17) 0.0199(9) Uani 1 1 d . . . . .
C18A C 0.0281(7) 0.1370(5) 0.22969(17) 0.0212(9) Uani 1 1 d . . . . .
C19A C -0.1085(8) 0.0726(6) 0.2408(2) 0.0291(11) Uani 1 1 d . . . . .
H19B H -0.1724 0.0463 0.2147 0.035 Uiso 1 1 calc R U . . .
C20A C -0.1518(9) 0.0466(7) 0.2902(2) 0.0335(12) Uani 1 1 d . . . . .
H20B H -0.2451 0.0024 0.2977 0.040 Uiso 1 1 calc R U . . .
C21A C -0.0602(8) 0.0846(6) 0.3284(2) 0.0319(11) Uani 1 1 d . . . . .
H21B H -0.0900 0.0659 0.3620 0.038 Uiso 1 1 calc R U . . .
C22A C 0.0763(8) 0.1505(6) 0.3178(2) 0.0309(11) Uani 1 1 d . . . . .
H22B H 0.1382 0.1784 0.3439 0.037 Uiso 1 1 calc R U . . .
C23A C 0.1206(7) 0.1750(6) 0.26820(18) 0.0238(9) Uani 1 1 d . . . . .
H23B H 0.2150 0.2181 0.2607 0.029 Uiso 1 1 calc R U . . .
O1W O -0.4128(5) 0.1757(5) 0.13719(14) 0.0334(9) Uani 1 1 d . . . . .
H1WA H -0.4991 0.1580 0.1614 0.040 Uiso 1 1 d R U . . .
H1WB H -0.4571 0.1468 0.1087 0.040 Uiso 1 1 d 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
N1 C7 1.376(6) . ?
N1 C6 1.395(6) . ?
N1 C15 1.465(6) . ?
N2 C17 1.375(6) . ?
N2 C4 1.421(6) . ?
N2 H2N 0.8800 . ?
O1 C1 1.364(6) . ?
O1 C2 1.459(6) . ?
O2 C1 1.209(6) . ?
O3 C17 1.222(6) . ?
C1 C14 1.477(6) . ?
C2 C3 1.493(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C14 1.372(7) . ?
C3 C4 1.400(6) . ?
C4 C5 1.397(6) . ?
C5 C6 1.415(7) . ?
C5 C16 1.517(6) . ?
C6 C13 1.426(6) . ?
C7 C8 1.402(7) . ?
C7 C12 1.421(6) . ?
C8 C9 1.396(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.402(8) . ?
C9 H9A 0.9500 . ?
C10 C11 1.375(7) . ?
C10 H10A 0.9500 . ?
C11 C12 1.407(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.437(7) . ?
C13 C14 1.386(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.481(7) . ?
C18 C19 1.392(7) . ?
C18 C23 1.399(7) . ?
C19 C20 1.377(8) . ?
C19 H19A 0.9500 . ?
C20 C21 1.378(8) . ?
C20 H20A 0.9500 . ?
C21 C22 1.384(8) . ?
C21 H21A 0.9500 . ?
C22 C23 1.382(8) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
N1A C7A 1.380(6) . ?
N1A C6A 1.386(6) . ?
N1A C15A 1.462(6) . ?
N2A C17A 1.348(6) . ?
N2A C4A 1.425(6) . ?
N2A H2NA 0.8800 . ?
O1A C1A 1.365(6) . ?
O1A C2A 1.454(6) . ?
O2A C1A 1.194(6) . ?
O3A C17A 1.224(6) . ?
C1A C14A 1.477(6) . ?
C2A C3A 1.501(7) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C14A 1.378(7) . ?
C3A C4A 1.401(6) . ?
C4A C5A 1.405(7) . ?
C5A C6A 1.420(7) . ?
C5A C16A 1.513(6) . ?
C6A C13A 1.425(7) . ?
C7A C8A 1.390(7) . ?
C7A C12A 1.408(7) . ?
C8A C9A 1.393(8) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.404(8) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.374(8) . ?
C10A H10B 0.9500 . ?
C11A C12A 1.407(7) . ?
C11A H11B 0.9500 . ?
C12A C13A 1.440(7) . ?
C13A C14A 1.400(7) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C17A C18A 1.500(6) . ?
C18A C23A 1.390(7) . ?
C18A C19A 1.390(7) . ?
C19A C20A 1.392(7) . ?
C19A H19B 0.9500 . ?
C20A C21A 1.378(8) . ?
C20A H20B 0.9500 . ?
C21A C22A 1.397(8) . ?
C21A H21B 0.9500 . ?
C22A C23A 1.395(7) . ?
C22A H22B 0.9500 . ?
C23A H23B 0.9500 . ?
O1W H1WA 0.9618 . ?
O1W H1WB 0.9352 . ?

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 N1 C6 109.1(4) . . ?
C7 N1 C15 122.8(4) . . ?
C6 N1 C15 128.1(4) . . ?
C17 N2 C4 124.3(4) . . ?
C17 N2 H2N 118.0 . . ?
C4 N2 H2N 117.6 . . ?
C1 O1 C2 110.2(4) . . ?
O2 C1 O1 120.7(4) . . ?
O2 C1 C14 131.0(5) . . ?
O1 C1 C14 108.3(4) . . ?
O1 C2 C3 104.4(4) . . ?
O1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C14 C3 C4 120.7(4) . . ?
C14 C3 C2 108.8(4) . . ?
C4 C3 C2 130.4(4) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 N2 119.1(4) . . ?
C3 C4 N2 120.0(4) . . ?
C4 C5 C6 117.4(4) . . ?
C4 C5 C16 118.5(4) . . ?
C6 C5 C16 124.2(4) . . ?
N1 C6 C5 129.9(4) . . ?
N1 C6 C13 108.2(4) . . ?
C5 C6 C13 121.9(4) . . ?
N1 C7 C8 128.7(4) . . ?
N1 C7 C12 109.3(4) . . ?
C8 C7 C12 121.9(4) . . ?
C9 C8 C7 116.8(5) . . ?
C9 C8 H8A 121.6 . . ?
C7 C8 H8A 121.6 . . ?
C8 C9 C10 121.8(5) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
C11 C12 C7 119.3(4) . . ?
C11 C12 C13 134.3(4) . . ?
C7 C12 C13 106.5(4) . . ?
C14 C13 C6 117.7(4) . . ?
C14 C13 C12 135.4(4) . . ?
C6 C13 C12 107.0(4) . . ?
C3 C14 C13 121.5(4) . . ?
C3 C14 C1 108.2(4) . . ?
C13 C14 C1 130.3(4) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N2 122.2(4) . . ?
O3 C17 C18 123.5(4) . . ?
N2 C17 C18 114.3(4) . . ?
C19 C18 C23 119.3(5) . . ?
C19 C18 C17 123.6(4) . . ?
C23 C18 C17 117.0(5) . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 120.6(5) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C22 119.4(5) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C23 C22 C21 121.0(6) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C18 119.3(5) . . ?
C22 C23 H23A 120.4 . . ?
C18 C23 H23A 120.4 . . ?
C7A N1A C6A 108.4(4) . . ?
C7A N1A C15A 122.2(4) . . ?
C6A N1A C15A 128.9(4) . . ?
C17A N2A C4A 123.8(4) . . ?
C17A N2A H2NA 117.6 . . ?
C4A N2A H2NA 118.5 . . ?
C1A O1A C2A 110.8(4) . . ?
O2A C1A O1A 121.1(4) . . ?
O2A C1A C14A 130.8(5) . . ?
O1A C1A C14A 108.2(4) . . ?
O1A C2A C3A 103.9(4) . . ?
O1A C2A H2AA 111.0 . . ?
C3A C2A H2AA 111.0 . . ?
O1A C2A H2AB 111.0 . . ?
C3A C2A H2AB 111.0 . . ?
H2AA C2A H2AB 109.0 . . ?
C14A C3A C4A 121.3(5) . . ?
C14A C3A C2A 109.0(4) . . ?
C4A C3A C2A 129.7(5) . . ?
C3A C4A C5A 120.5(4) . . ?
C3A C4A N2A 120.6(4) . . ?
C5A C4A N2A 118.7(4) . . ?
C4A C5A C6A 117.2(4) . . ?
C4A C5A C16A 119.2(4) . . ?
C6A C5A C16A 123.6(5) . . ?
N1A C6A C5A 129.4(4) . . ?
N1A C6A C13A 108.1(4) . . ?
C5A C6A C13A 122.5(5) . . ?
N1A C7A C8A 128.6(5) . . ?
N1A C7A C12A 110.5(4) . . ?
C8A C7A C12A 120.9(5) . . ?
C7A C8A C9A 118.6(5) . . ?
C7A C8A H8AA 120.7 . . ?
C9A C8A H8AA 120.7 . . ?
C8A C9A C10A 120.8(5) . . ?
C8A C9A H9AA 119.6 . . ?
C10A C9A H9AA 119.6 . . ?
C11A C10A C9A 120.7(5) . . ?
C11A C10A H10B 119.6 . . ?
C9A C10A H10B 119.6 . . ?
C10A C11A C12A 119.2(5) . . ?
C10A C11A H11B 120.4 . . ?
C12A C11A H11B 120.4 . . ?
C11A C12A C7A 119.8(5) . . ?
C11A C12A C13A 134.9(5) . . ?
C7A C12A C13A 105.3(4) . . ?
C14A C13A C6A 117.2(4) . . ?
C14A C13A C12A 135.1(4) . . ?
C6A C13A C12A 107.6(4) . . ?
C3A C14A C13A 121.1(4) . . ?
C3A C14A C1A 107.9(4) . . ?
C13A C14A C1A 130.9(4) . . ?
N1A C15A H15D 109.5 . . ?
N1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
N1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C5A C16A H16D 109.5 . . ?
C5A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C5A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
O3A C17A N2A 122.7(4) . . ?
O3A C17A C18A 121.2(4) . . ?
N2A C17A C18A 116.1(4) . . ?
C23A C18A C19A 119.5(5) . . ?
C23A C18A C17A 117.5(4) . . ?
C19A C18A C17A 123.0(4) . . ?
C18A C19A C20A 120.0(5) . . ?
C18A C19A H19B 120.0 . . ?
C20A C19A H19B 120.0 . . ?
C21A C20A C19A 120.4(5) . . ?
C21A C20A H20B 119.8 . . ?
C19A C20A H20B 119.8 . . ?
C20A C21A C22A 120.2(5) . . ?
C20A C21A H21B 119.9 . . ?
C22A C21A H21B 119.9 . . ?
C23A C22A C21A 119.1(5) . . ?
C23A C22A H22B 120.4 . . ?
C21A C22A H22B 120.4 . . ?
C18A C23A C22A 120.7(5) . . ?
C18A C23A H23B 119.6 . . ?
C22A C23A H23B 119.6 . . ?
H1WA O1W H1WB 99.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 O2 -179.4(4) . . . . ?
C2 O1 C1 C14 1.6(5) . . . . ?
C1 O1 C2 C3 -2.9(5) . . . . ?
O1 C2 C3 C14 3.2(5) . . . . ?
O1 C2 C3 C4 -175.6(4) . . . . ?
C14 C3 C4 C5 2.0(6) . . . . ?
C2 C3 C4 C5 -179.3(4) . . . . ?
C14 C3 C4 N2 -174.1(4) . . . . ?
C2 C3 C4 N2 4.6(7) . . . . ?
C17 N2 C4 C5 132.6(5) . . . . ?
C17 N2 C4 C3 -51.3(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
N2 C4 C5 C6 175.1(4) . . . . ?
C3 C4 C5 C16 179.8(4) . . . . ?
N2 C4 C5 C16 -4.1(6) . . . . ?
C7 N1 C6 C5 177.1(4) . . . . ?
C15 N1 C6 C5 -4.4(7) . . . . ?
C7 N1 C6 C13 -0.3(5) . . . . ?
C15 N1 C6 C13 178.2(4) . . . . ?
C4 C5 C6 N1 -178.1(4) . . . . ?
C16 C5 C6 N1 1.1(7) . . . . ?
C4 C5 C6 C13 -1.0(6) . . . . ?
C16 C5 C6 C13 178.2(4) . . . . ?
C6 N1 C7 C8 -178.6(4) . . . . ?
C15 N1 C7 C8 2.8(7) . . . . ?
C6 N1 C7 C12 0.3(5) . . . . ?
C15 N1 C7 C12 -178.3(4) . . . . ?
N1 C7 C8 C9 178.9(5) . . . . ?
C12 C7 C8 C9 0.0(7) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C10 C11 C12 C13 -178.5(5) . . . . ?
N1 C7 C12 C11 -179.2(4) . . . . ?
C8 C7 C12 C11 -0.2(6) . . . . ?
N1 C7 C12 C13 -0.2(5) . . . . ?
C8 C7 C12 C13 178.8(4) . . . . ?
N1 C6 C13 C14 179.7(4) . . . . ?
C5 C6 C13 C14 2.1(6) . . . . ?
N1 C6 C13 C12 0.2(5) . . . . ?
C5 C6 C13 C12 -177.5(4) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C7 C12 C13 C14 -179.4(5) . . . . ?
C11 C12 C13 C6 178.8(5) . . . . ?
C7 C12 C13 C6 0.0(5) . . . . ?
C4 C3 C14 C13 -0.9(7) . . . . ?
C2 C3 C14 C13 -179.8(4) . . . . ?
C4 C3 C14 C1 176.6(4) . . . . ?
C2 C3 C14 C1 -2.3(5) . . . . ?
C6 C13 C14 C3 -1.1(6) . . . . ?
C12 C13 C14 C3 178.3(5) . . . . ?
C6 C13 C14 C1 -178.0(4) . . . . ?
C12 C13 C14 C1 1.4(8) . . . . ?
O2 C1 C14 C3 -178.3(5) . . . . ?
O1 C1 C14 C3 0.5(5) . . . . ?
O2 C1 C14 C13 -1.2(8) . . . . ?
O1 C1 C14 C13 177.7(4) . . . . ?
C4 N2 C17 O3 -6.2(7) . . . . ?
C4 N2 C17 C18 171.6(4) . . . . ?
O3 C17 C18 C19 -139.5(5) . . . . ?
N2 C17 C18 C19 42.7(7) . . . . ?
O3 C17 C18 C23 43.5(7) . . . . ?
N2 C17 C18 C23 -134.2(5) . . . . ?
C23 C18 C19 C20 0.6(8) . . . . ?
C17 C18 C19 C20 -176.3(5) . . . . ?
C18 C19 C20 C21 1.1(9) . . . . ?
C19 C20 C21 C22 -0.7(9) . . . . ?
C20 C21 C22 C23 -1.5(10) . . . . ?
C21 C22 C23 C18 3.3(10) . . . . ?
C19 C18 C23 C22 -2.8(8) . . . . ?
C17 C18 C23 C22 174.4(6) . . . . ?
C2A O1A C1A O2A 177.6(4) . . . . ?
C2A O1A C1A C14A -3.1(5) . . . . ?
C1A O1A C2A C3A 3.4(5) . . . . ?
O1A C2A C3A C14A -2.5(5) . . . . ?
O1A C2A C3A C4A 176.8(4) . . . . ?
C14A C3A C4A C5A -1.8(7) . . . . ?
C2A C3A C4A C5A 178.9(4) . . . . ?
C14A C3A C4A N2A 173.2(4) . . . . ?
C2A C3A C4A N2A -6.1(7) . . . . ?
C17A N2A C4A C3A 63.2(6) . . . . ?
C17A N2A C4A C5A -121.6(5) . . . . ?
C3A C4A C5A C6A 0.7(7) . . . . ?
N2A C4A C5A C6A -174.5(4) . . . . ?
C3A C4A C5A C16A -177.8(4) . . . . ?
N2A C4A C5A C16A 7.1(7) . . . . ?
C7A N1A C6A C5A -178.9(5) . . . . ?
C15A N1A C6A C5A 8.9(8) . . . . ?
C7A N1A C6A C13A 0.0(5) . . . . ?
C15A N1A C6A C13A -172.3(4) . . . . ?
C4A C5A C6A N1A -179.7(4) . . . . ?
C16A C5A C6A N1A -1.3(8) . . . . ?
C4A C5A C6A C13A 1.6(7) . . . . ?
C16A C5A C6A C13A 180.0(4) . . . . ?
C6A N1A C7A C8A -179.4(5) . . . . ?
C15A N1A C7A C8A -6.6(8) . . . . ?
C6A N1A C7A C12A -0.3(5) . . . . ?
C15A N1A C7A C12A 172.6(4) . . . . ?
N1A C7A C8A C9A 179.0(5) . . . . ?
C12A C7A C8A C9A -0.1(7) . . . . ?
C7A C8A C9A C10A -0.6(8) . . . . ?
C8A C9A C10A C11A 0.8(8) . . . . ?
C9A C10A C11A C12A -0.4(8) . . . . ?
C10A C11A C12A C7A -0.3(7) . . . . ?
C10A C11A C12A C13A -179.2(5) . . . . ?
N1A C7A C12A C11A -178.7(4) . . . . ?
C8A C7A C12A C11A 0.5(7) . . . . ?
N1A C7A C12A C13A 0.4(5) . . . . ?
C8A C7A C12A C13A 179.7(4) . . . . ?
N1A C6A C13A C14A 178.3(4) . . . . ?
C5A C6A C13A C14A -2.7(7) . . . . ?
N1A C6A C13A C12A 0.3(5) . . . . ?
C5A C6A C13A C12A 179.3(4) . . . . ?
C11A C12A C13A C14A 1.1(9) . . . . ?
C7A C12A C13A C14A -177.9(5) . . . . ?
C11A C12A C13A C6A 178.5(5) . . . . ?
C7A C12A C13A C6A -0.5(5) . . . . ?
C4A C3A C14A C13A 0.7(7) . . . . ?
C2A C3A C14A C13A -179.9(4) . . . . ?
C4A C3A C14A C1A -178.6(4) . . . . ?
C2A C3A C14A C1A 0.8(5) . . . . ?
C6A C13A C14A C3A 1.6(7) . . . . ?
C12A C13A C14A C3A 178.8(5) . . . . ?
C6A C13A C14A C1A -179.4(4) . . . . ?
C12A C13A C14A C1A -2.1(9) . . . . ?
O2A C1A C14A C3A -179.4(5) . . . . ?
O1A C1A C14A C3A 1.4(5) . . . . ?
O2A C1A C14A C13A 1.5(9) . . . . ?
O1A C1A C14A C13A -177.8(4) . . . . ?
C4A N2A C17A O3A 3.3(7) . . . . ?
C4A N2A C17A C18A -177.0(4) . . . . ?
O3A C17A C18A C23A 23.1(7) . . . . ?
N2A C17A C18A C23A -156.7(4) . . . . ?
O3A C17A C18A C19A -154.5(5) . . . . ?
N2A C17A C18A C19A 25.7(7) . . . . ?
C23A C18A C19A C20A 0.0(8) . . . . ?
C17A C18A C19A C20A 177.6(5) . . . . ?
C18A C19A C20A C21A 0.1(9) . . . . ?
C19A C20A C21A C22A 0.4(9) . . . . ?
C20A C21A C22A C23A -1.0(8) . . . . ?
C19A C18A C23A C22A -0.7(8) . . . . ?
C17A C18A C23A C22A -178.4(4) . . . . ?
C21A C22A C23A C18A 1.2(8) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.144

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_1_q
_database_code_depnum_ccdc_archive 'CCDC 1859656'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O S, C2 H6 O S'
_chemical_formula_sum            'C21 H22 N2 O2 S2'
_chemical_formula_weight         398.52

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'
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                   8.7979(18)
_cell_length_b                   24.844(5)
_cell_length_c                   9.4540(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.09(3)
_cell_angle_gamma                90
_cell_volume                     1927.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    554
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   0.891
_exptl_transmission_factor_max   0.949
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.295
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19659
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         28.999
_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             5117
_reflns_number_gt                4332
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.9837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5117
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1S S -0.10236(5) 0.69450(2) -0.05497(5) 0.03301(11) Uani 1 1 d . . . . .
O1S O -0.05938(17) 0.68092(8) 0.10738(18) 0.0585(5) Uani 1 1 d . . . . .
C1S C -0.0614(3) 0.76334(8) -0.0616(3) 0.0519(6) Uani 1 1 d . . . . .
H1SA H -0.0885 0.7744 -0.1673 0.078 Uiso 1 1 calc R U . . .
H1SB H 0.0544 0.7701 -0.0049 0.078 Uiso 1 1 calc R U . . .
H1SC H -0.1272 0.7840 -0.0163 0.078 Uiso 1 1 calc R U . . .
C2S C 0.0616(3) 0.67003(12) -0.1055(3) 0.0628(7) Uani 1 1 d . . . . .
H2SA H 0.0383 0.6768 -0.2133 0.094 Uiso 1 1 calc R U . . .
H2SB H 0.0744 0.6312 -0.0859 0.094 Uiso 1 1 calc R U . . .
H2SC H 0.1624 0.6885 -0.0449 0.094 Uiso 1 1 calc R U . . .
S1 S 0.30438(5) 0.53430(2) 0.98114(4) 0.02727(10) Uani 1 1 d . . . . .
O1 O 0.05475(13) 0.39840(4) 0.48166(12) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.43251(14) 0.59825(5) 0.50943(13) 0.0208(2) Uani 1 1 d . . . . .
N2 N 0.18136(15) 0.64048(5) 0.38371(15) 0.0259(3) Uani 1 1 d . . . . .
H1N H 0.1244 0.6536 0.3010 0.031 Uiso 1 1 d R U . . .
H2N H 0.1253 0.6198 0.4270 0.031 Uiso 1 1 d R U . . .
C1 C 0.1976(2) 0.47468(6) 0.95531(17) 0.0286(3) Uani 1 1 d . . . . .
H1A H 0.1683 0.4581 1.0324 0.034 Uiso 1 1 calc R U . . .
C2 C 0.15969(19) 0.45371(6) 0.81474(16) 0.0232(3) Uani 1 1 d . . . . .
H2A H 0.1020 0.4209 0.7825 0.028 Uiso 1 1 calc R U . . .
C3 C 0.21677(17) 0.48673(5) 0.72074(15) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.29980(18) 0.53229(6) 0.79686(15) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.37165(17) 0.57068(6) 0.73139(15) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.35662(16) 0.56327(6) 0.58116(15) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.27492(16) 0.51743(6) 0.50297(15) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.25437(17) 0.50202(6) 0.34374(15) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.3614 0.4981 0.3325 0.024 Uiso 1 1 calc R U . . .
H8B H 0.1894 0.5293 0.2706 0.024 Uiso 1 1 calc R U . . .
C9 C 0.16439(18) 0.44803(6) 0.31925(15) 0.0207(3) Uani 1 1 d . . . . .
H9A H 0.0612 0.4501 0.2308 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2326 0.4191 0.3011 0.025 Uiso 1 1 calc R U . . .
C10 C 0.13048(17) 0.43687(6) 0.46233(15) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.20603(16) 0.48016(5) 0.56991(15) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.4623(2) 0.61744(6) 0.82306(17) 0.0286(3) Uani 1 1 d . . . . .
H12A H 0.5378 0.6046 0.9212 0.043 Uiso 1 1 calc R U . . .
H12B H 0.3848 0.6427 0.8394 0.043 Uiso 1 1 calc R U . . .
H12C H 0.5236 0.6356 0.7686 0.043 Uiso 1 1 calc R U . . .
C13 C 0.34048(17) 0.63136(5) 0.41103(15) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.41296(16) 0.66390(5) 0.31940(15) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.53804(17) 0.64212(6) 0.28079(16) 0.0214(3) Uani 1 1 d . . . . .
H15A H 0.5780 0.6071 0.3151 0.026 Uiso 1 1 calc R U . . .
C16 C 0.60458(18) 0.67111(6) 0.19272(17) 0.0262(3) Uani 1 1 d . . . . .
H16A H 0.6904 0.6561 0.1668 0.031 Uiso 1 1 calc R U . . .
C17 C 0.54668(19) 0.72198(6) 0.14214(17) 0.0271(3) Uani 1 1 d . . . . .
H17A H 0.5925 0.7418 0.0813 0.032 Uiso 1 1 calc R U . . .
C18 C 0.42274(19) 0.74400(6) 0.17979(17) 0.0261(3) Uani 1 1 d . . . . .
H18A H 0.3830 0.7790 0.1448 0.031 Uiso 1 1 calc R U . . .
C19 C 0.35588(18) 0.71524(6) 0.26866(16) 0.0225(3) Uani 1 1 d . . . . .
H19A H 0.2708 0.7306 0.2950 0.027 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
S1S O1S 1.4815(15) . ?
S1S C1S 1.754(2) . ?
S1S C2S 1.782(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
S1 C1 1.7235(18) . ?
S1 C4 1.7288(14) . ?
O1 C10 1.2158(17) . ?
N1 C13 1.2867(18) . ?
N1 C6 1.4095(18) . ?
N2 C13 1.3482(18) . ?
N2 H1N 0.8291 . ?
N2 H2N 0.9053 . ?
C1 C2 1.353(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4269(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(2) . ?
C3 C11 1.4042(18) . ?
C4 C5 1.405(2) . ?
C5 C6 1.3904(19) . ?
C5 C12 1.496(2) . ?
C6 C7 1.406(2) . ?
C7 C11 1.3789(19) . ?
C7 C8 1.4998(18) . ?
C8 C9 1.532(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5121(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.465(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.4860(19) . ?
C14 C15 1.3879(19) . ?
C14 C19 1.3912(19) . ?
C15 C16 1.380(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.376(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
O1S S1S C1S 106.27(11) . . ?
O1S S1S C2S 105.69(12) . . ?
C1S S1S C2S 97.27(13) . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
S1S C2S H2SA 109.5 . . ?
S1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
S1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1 S1 C4 91.06(7) . . ?
C13 N1 C6 117.28(12) . . ?
C13 N2 H1N 118.7 . . ?
C13 N2 H2N 121.0 . . ?
H1N N2 H2N 114.0 . . ?
C2 C1 S1 113.54(12) . . ?
C2 C1 H1A 123.2 . . ?
S1 C1 H1A 123.2 . . ?
C1 C2 C3 111.88(14) . . ?
C1 C2 H2A 124.1 . . ?
C3 C2 H2A 124.1 . . ?
C4 C3 C11 116.65(13) . . ?
C4 C3 C2 112.38(12) . . ?
C11 C3 C2 130.95(14) . . ?
C3 C4 C5 123.88(12) . . ?
C3 C4 S1 111.13(10) . . ?
C5 C4 S1 124.99(11) . . ?
C6 C5 C4 117.88(13) . . ?
C6 C5 C12 121.96(13) . . ?
C4 C5 C12 120.16(13) . . ?
C5 C6 C7 119.13(13) . . ?
C5 C6 N1 121.49(13) . . ?
C7 C6 N1 119.17(12) . . ?
C11 C7 C6 121.90(12) . . ?
C11 C7 C8 112.04(12) . . ?
C6 C7 C8 126.05(12) . . ?
C7 C8 C9 104.14(11) . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C8 106.44(11) . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O1 C10 C11 127.52(12) . . ?
O1 C10 C9 125.02(13) . . ?
C11 C10 C9 107.46(12) . . ?
C7 C11 C3 120.53(13) . . ?
C7 C11 C10 109.80(12) . . ?
C3 C11 C10 129.66(13) . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 N2 125.86(13) . . ?
N1 C13 C14 118.62(12) . . ?
N2 C13 C14 115.51(12) . . ?
C15 C14 C19 119.26(13) . . ?
C15 C14 C13 119.23(12) . . ?
C19 C14 C13 121.50(12) . . ?
C16 C15 C14 120.25(14) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.15(14) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 120.10(14) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 120.06(14) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C18 C19 C14 120.18(14) . . ?
C18 C19 H19A 119.9 . . ?
C14 C19 H19A 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
C4 S1 C1 C2 0.10(13) . . . . ?
S1 C1 C2 C3 -0.52(18) . . . . ?
C1 C2 C3 C4 0.80(18) . . . . ?
C1 C2 C3 C11 179.21(15) . . . . ?
C11 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 178.40(13) . . . . ?
C11 C3 C4 S1 -179.37(10) . . . . ?
C2 C3 C4 S1 -0.71(15) . . . . ?
C1 S1 C4 C3 0.36(11) . . . . ?
C1 S1 C4 C5 -178.75(13) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
S1 C4 C5 C6 -179.85(11) . . . . ?
C3 C4 C5 C12 -178.26(14) . . . . ?
S1 C4 C5 C12 0.7(2) . . . . ?
C4 C5 C6 C7 -1.70(19) . . . . ?
C12 C5 C6 C7 177.70(13) . . . . ?
C4 C5 C6 N1 -176.50(12) . . . . ?
C12 C5 C6 N1 2.9(2) . . . . ?
C13 N1 C6 C5 -106.74(16) . . . . ?
C13 N1 C6 C7 78.47(17) . . . . ?
C5 C6 C7 C11 1.5(2) . . . . ?
N1 C6 C7 C11 176.39(12) . . . . ?
C5 C6 C7 C8 -177.08(13) . . . . ?
N1 C6 C7 C8 -2.2(2) . . . . ?
C11 C7 C8 C9 -1.25(15) . . . . ?
C6 C7 C8 C9 177.41(13) . . . . ?
C7 C8 C9 C10 2.89(14) . . . . ?
C8 C9 C10 O1 176.88(13) . . . . ?
C8 C9 C10 C11 -3.55(15) . . . . ?
C6 C7 C11 C3 -0.6(2) . . . . ?
C8 C7 C11 C3 178.17(12) . . . . ?
C6 C7 C11 C10 -179.72(12) . . . . ?
C8 C7 C11 C10 -0.99(16) . . . . ?
C4 C3 C11 C7 -0.06(19) . . . . ?
C2 C3 C11 C7 -178.42(14) . . . . ?
C4 C3 C11 C10 178.92(13) . . . . ?
C2 C3 C11 C10 0.6(3) . . . . ?
O1 C10 C11 C7 -177.58(14) . . . . ?
C9 C10 C11 C7 2.87(15) . . . . ?
O1 C10 C11 C3 3.4(2) . . . . ?
C9 C10 C11 C3 -176.20(13) . . . . ?
C6 N1 C13 N2 8.9(2) . . . . ?
C6 N1 C13 C14 -172.38(12) . . . . ?
N1 C13 C14 C15 32.62(19) . . . . ?
N2 C13 C14 C15 -148.54(13) . . . . ?
N1 C13 C14 C19 -148.81(14) . . . . ?
N2 C13 C14 C19 30.03(19) . . . . ?
C19 C14 C15 C16 -0.1(2) . . . . ?
C13 C14 C15 C16 178.45(13) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 -0.4(2) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C13 C14 C19 C18 -178.15(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1S 0.83 2.07 2.887(2) 167.6 .
N2 H2N O1 0.91 2.11 2.9617(17) 156.8 3_566


_refine_diff_density_max         0.423
_refine_diff_density_min         -0.369

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_b_a
_database_code_depnum_ccdc_archive 'CCDC 1859660'
loop_
_audit_author_name
_audit_author_address
'Konstantin A. Lyssenko'
;A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 O3 S'
_chemical_formula_sum            'C11 H8 O3 S'
_chemical_formula_weight         220.23

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   16.1338(3)
_cell_length_b                   8.52590(10)
_cell_length_c                   14.3640(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.5437(8)
_cell_angle_gamma                90
_cell_volume                     1797.31(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8653
_cell_measurement_theta_min      2.322
_cell_measurement_theta_max      36.354

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.882
_exptl_transmission_factor_max   0.932
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.339
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81008
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.763
_diffrn_reflns_theta_max         39.997
_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             5578
_reflns_number_gt                4975
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.8582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5578
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.003
_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 0.62138(2) 0.70864(2) 0.38812(2) 0.01368(4) Uani 1 1 d . . . . .
O1 O 0.31515(3) 0.65382(6) 0.35093(4) 0.01559(9) Uani 1 1 d . . . . .
O2 O 0.41622(4) 0.84486(6) 0.36748(5) 0.01941(10) Uani 1 1 d . . . . .
O3 O 0.38735(4) 0.16408(6) 0.36150(5) 0.01656(9) Uani 1 1 d . . . . .
H3O H 0.4124 0.0753 0.3649 0.045(5) Uiso 1 1 d R . . . .
C1 C 0.70447(4) 0.57346(8) 0.39754(5) 0.01522(10) Uani 1 1 d . . . . .
H1A H 0.7633 0.6021 0.4034 0.018 Uiso 1 1 calc R U . . .
C2 C 0.67718(4) 0.42188(8) 0.39576(5) 0.01340(9) Uani 1 1 d . . . . .
H2A H 0.7148 0.3338 0.4004 0.016 Uiso 1 1 calc R U . . .
C3 C 0.58477(4) 0.41019(7) 0.38602(5) 0.01061(8) Uani 1 1 d . . . . .
C4 C 0.54634(4) 0.56015(7) 0.38099(5) 0.01077(8) Uani 1 1 d . . . . .
C5 C 0.45625(4) 0.57061(6) 0.36989(5) 0.01069(8) Uani 1 1 d . . . . .
C6 C 0.39858(4) 0.70596(7) 0.36325(5) 0.01310(9) Uani 1 1 d . . . . .
C7 C 0.31280(4) 0.48326(7) 0.34998(5) 0.01337(9) Uani 1 1 d . . . . .
H7A H 0.2662 0.4436 0.2843 0.016 Uiso 1 1 calc R U . . .
H7B H 0.2993 0.4425 0.4067 0.016 Uiso 1 1 calc R U . . .
C8 C 0.40645(4) 0.43638(7) 0.36326(5) 0.01072(8) Uani 1 1 d . . . . .
C9 C 0.44388(4) 0.28647(7) 0.36878(5) 0.01106(9) Uani 1 1 d . . . . .
C10 C 0.53392(4) 0.27166(7) 0.38058(5) 0.01107(9) Uani 1 1 d . . . . .
C11 C 0.57718(5) 0.11355(8) 0.38781(6) 0.01658(11) Uani 1 1 d . . . . .
H11C H 0.5298 0.0354 0.3532 0.025 Uiso 1 1 calc R U . . .
H11B H 0.6104 0.0846 0.4599 0.025 Uiso 1 1 calc R U . . .
H11A H 0.6196 0.1175 0.3550 0.025 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 C4 1.7251(6) . ?
S1 C1 1.7301(7) . ?
O1 C6 1.3575(9) . ?
O1 C7 1.4546(8) . ?
O2 C6 1.2136(8) . ?
O3 C9 1.3610(8) . ?
O3 H3O 0.8499 . ?
C1 C2 1.3620(10) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4419(8) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4096(8) . ?
C3 C10 1.4215(8) . ?
C4 C5 1.3977(8) . ?
C5 C8 1.3786(8) . ?
C5 C6 1.4603(8) . ?
C7 C8 1.4965(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4017(8) . ?
C9 C10 1.3965(8) . ?
C10 C11 1.5016(8) . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11A 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
C4 S1 C1 91.01(3) . . ?
C6 O1 C7 110.44(5) . . ?
C9 O3 H3O 113.0 . . ?
C2 C1 S1 113.37(5) . . ?
C2 C1 H1A 123.3 . . ?
S1 C1 H1A 123.3 . . ?
C1 C2 C3 112.37(6) . . ?
C1 C2 H2A 123.8 . . ?
C3 C2 H2A 123.8 . . ?
C4 C3 C10 121.28(5) . . ?
C4 C3 C2 110.93(5) . . ?
C10 C3 C2 127.78(5) . . ?
C5 C4 C3 118.56(5) . . ?
C5 C4 S1 129.11(4) . . ?
C3 C4 S1 112.32(4) . . ?
C8 C5 C4 120.23(5) . . ?
C8 C5 C6 108.32(5) . . ?
C4 C5 C6 131.45(5) . . ?
O2 C6 O1 121.69(6) . . ?
O2 C6 C5 129.65(6) . . ?
O1 C6 C5 108.66(5) . . ?
O1 C7 C8 104.17(5) . . ?
O1 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
O1 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C5 C8 C9 121.87(5) . . ?
C5 C8 C7 108.40(5) . . ?
C9 C8 C7 129.73(5) . . ?
O3 C9 C10 124.76(5) . . ?
O3 C9 C8 115.82(5) . . ?
C10 C9 C8 119.42(5) . . ?
C9 C10 C3 118.62(5) . . ?
C9 C10 C11 121.31(5) . . ?
C3 C10 C11 120.07(5) . . ?
C10 C11 H11C 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 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
C4 S1 C1 C2 -0.19(6) . . . . ?
S1 C1 C2 C3 0.20(8) . . . . ?
C1 C2 C3 C4 -0.10(8) . . . . ?
C1 C2 C3 C10 179.27(6) . . . . ?
C10 C3 C4 C5 -0.34(9) . . . . ?
C2 C3 C4 C5 179.08(6) . . . . ?
C10 C3 C4 S1 -179.46(5) . . . . ?
C2 C3 C4 S1 -0.04(7) . . . . ?
C1 S1 C4 C5 -178.87(6) . . . . ?
C1 S1 C4 C3 0.13(5) . . . . ?
C3 C4 C5 C8 -0.51(9) . . . . ?
S1 C4 C5 C8 178.44(5) . . . . ?
C3 C4 C5 C6 179.49(6) . . . . ?
S1 C4 C5 C6 -1.56(11) . . . . ?
C7 O1 C6 O2 -179.11(6) . . . . ?
C7 O1 C6 C5 0.71(7) . . . . ?
C8 C5 C6 O2 178.70(7) . . . . ?
C4 C5 C6 O2 -1.30(12) . . . . ?
C8 C5 C6 O1 -1.10(7) . . . . ?
C4 C5 C6 O1 178.89(6) . . . . ?
C6 O1 C7 C8 -0.09(7) . . . . ?
C4 C5 C8 C9 0.94(9) . . . . ?
C6 C5 C8 C9 -179.06(6) . . . . ?
C4 C5 C8 C7 -178.97(6) . . . . ?
C6 C5 C8 C7 1.03(7) . . . . ?
O1 C7 C8 C5 -0.60(7) . . . . ?
O1 C7 C8 C9 179.50(6) . . . . ?
C5 C8 C9 O3 179.79(6) . . . . ?
C7 C8 C9 O3 -0.31(10) . . . . ?
C5 C8 C9 C10 -0.49(9) . . . . ?
C7 C8 C9 C10 179.40(6) . . . . ?
O3 C9 C10 C3 179.32(6) . . . . ?
C8 C9 C10 C3 -0.36(9) . . . . ?
O3 C9 C10 C11 -0.87(10) . . . . ?
C8 C9 C10 C11 179.44(6) . . . . ?
C4 C3 C10 C9 0.78(9) . . . . ?
C2 C3 C10 C9 -178.53(6) . . . . ?
C4 C3 C10 C11 -179.03(6) . . . . ?
C2 C3 C10 C11 1.66(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.85 1.97 2.7565(7) 154.3 1_545
C1 H1A O3 0.95 2.38 3.2925(8) 162.0 3
C2 H2A O1 0.95 2.54 3.4328(8) 157.1 3_545

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.078

_shelxl_version_number           2014/6



