#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:48:54 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225190 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156763.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7156763
loop_
_publ_author_name
'Lvov, Andrey G.'
'Kavun, Alexey M.'
'Kachala, Vadim V.'
'Lyssenko, Konstantin A.'
'Shirinian, Valerii Z.'
_publ_section_title
;
 Photorearrangement of dihetarylethenes as a tool for the benzannulation
 of heterocycles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4990
_journal_page_last               5000
_journal_paper_doi               10.1039/c9ob00690g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C12 H10 O2 S2'
_chemical_formula_sum            'C12 H10 O2 S2'
_chemical_formula_weight         250.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-08-01 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4647(5)
_cell_length_b                   10.1476(6)
_cell_length_c                   14.7974(9)
_cell_measurement_reflns_used    259
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1110.83(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.992
_diffrn_reflns_theta_min         2.441
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.294
_exptl_transmission_factor_max   0.857
_exptl_transmission_factor_min   0.809
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.3510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2724
_reflns_number_total             2957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c9ob00690g2.cif
_cod_data_source_block           a_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156762--7156768.cif.'
_cod_database_code               7156763
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.809
_shelx_estimated_absorpt_t_max   0.877
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
