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#$Date: 2021-04-05 18:16:58 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157881.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_7157881
loop_
_publ_author_name
'Welsh, Erin N.'
'Robertson, Katherine N.'
'Speed, Alexander W. H.'
_publ_section_title
;
 Short syntheses of 1-substituted dibenzothiophene derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2000
_journal_page_last               2007
_journal_paper_doi               10.1039/d0ob01839b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H12 O S'
_chemical_formula_sum            'C15 H12 O S'
_chemical_formula_weight         240.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'Intrinsic Phasing'
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-01-31 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.314(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0539(8)
_cell_length_b                   21.767(3)
_cell_length_c                   8.6784(12)
_cell_measurement_reflns_used    9674
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      39.2018
_cell_measurement_theta_min      2.5445
_cell_volume                     1134.3(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14 Patch 4'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            85596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_min         2.544
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       'diamond shaped plate'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         5501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²+0.5905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4412
_reflns_number_total             5501
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01839b2.cif
_cod_data_source_block           compound3k_AS030B
_cod_depositor_comments
'Adding full bibliography for 7157879--7157883.cif.'
_cod_original_cell_volume        1134.3(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157881
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.987
_diffrn_source_source            'microfocus sealed tube'
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'
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 -0.06193(4) 0.28185(2) 0.74189(3) 0.02132(7) Uani 1 1 d . . . . .
O1 O 0.69302(15) 0.39270(4) 0.38965(11) 0.02758(18) Uani 1 1 d . . . . .
C1 C 0.09294(18) 0.34147(5) 0.67652(12) 0.01950(18) Uani 1 1 d . . . . .
C2 C 0.0457(2) 0.40347(6) 0.69540(14) 0.0244(2) Uani 1 1 d . . . . .
H2 H -0.074595 0.415646 0.748965 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1768(2) 0.44685(6) 0.63486(15) 0.0273(2) Uani 1 1 d . . . . .
H3 H 0.149116 0.489375 0.647902 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3496(2) 0.42796(6) 0.55460(14) 0.0263(2) Uani 1 1 d . . . . .
H4 H 0.437953 0.458279 0.512755 0.032 Uiso 1 1 calc R U . . .
C5 C 0.39789(19) 0.36627(5) 0.53341(13) 0.02032(19) Uani 1 1 d . . . . .
C6 C 0.27042(17) 0.32076(5) 0.59782(12) 0.01735(17) Uani 1 1 d . . . . .
C7 C 0.28233(16) 0.25397(5) 0.59718(12) 0.01682(17) Uani 1 1 d . . . . .
C8 C 0.43243(17) 0.21346(5) 0.53850(12) 0.01822(17) Uani 1 1 d . . . . .
H8 H 0.553012 0.229809 0.491406 0.022 Uiso 1 1 calc R U . . .
C9 C 0.40857(17) 0.15029(5) 0.54778(12) 0.01893(18) Uani 1 1 d . . . . .
C10 C 0.23174(18) 0.12543(5) 0.62019(13) 0.01989(18) Uani 1 1 d . . . . .
C11 C 0.08521(18) 0.16434(5) 0.68264(13) 0.02074(19) Uani 1 1 d . . . . .
H11 H -0.031722 0.147945 0.733463 0.025 Uiso 1 1 calc R U . . .
C12 C 0.11068(17) 0.22764(5) 0.67031(12) 0.01819(17) Uani 1 1 d . . . . .
C13 C 0.57098(19) 0.35337(6) 0.43091(13) 0.0226(2) Uani 1 1 d . . . . .
H13 H 0.586970 0.312439 0.395994 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5722(2) 0.10863(6) 0.48311(15) 0.0247(2) Uani 1 1 d . . . . .
H14A H 0.687844 0.133393 0.443457 0.037 Uiso 1 1 calc R U . . .
H14B H 0.494497 0.084027 0.398401 0.037 Uiso 1 1 calc R U . . .
H14C H 0.640967 0.081300 0.565316 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2059(2) 0.05685(6) 0.63282(16) 0.0278(2) Uani 1 1 d . . . . .
H15A H 0.074224 0.047646 0.683742 0.042 Uiso 1 1 calc R U . . .
H15B H 0.338485 0.039619 0.694269 0.042 Uiso 1 1 calc R U . . .
H15C H 0.188135 0.038664 0.528675 0.042 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C12 90.94(5) . . ?
C2 C1 C6 122.96(10) . . ?
C2 C1 S1 123.87(8) . . ?
C6 C1 S1 113.15(8) . . ?
C3 C2 C1 118.76(11) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.63(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 122.36(11) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 119.32(10) . . ?
C4 C5 C13 115.95(10) . . ?
C6 C5 C13 124.51(10) . . ?
C5 C6 C1 116.92(10) . . ?
C5 C6 C7 131.95(9) . . ?
C1 C6 C7 111.12(9) . . ?
C12 C7 C8 117.14(9) . . ?
C12 C7 C6 111.43(9) . . ?
C8 C7 C6 131.43(9) . . ?
C9 C8 C7 121.58(9) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.68(10) . . ?
C8 C9 C14 119.88(9) . . ?
C10 C9 C14 120.43(10) . . ?
C11 C10 C9 119.85(10) . . ?
C11 C10 C15 119.97(10) . . ?
C9 C10 C15 120.16(10) . . ?
C10 C11 C12 119.49(9) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 122.23(10) . . ?
C11 C12 S1 124.45(8) . . ?
C7 C12 S1 113.33(8) . . ?
O1 C13 C5 123.07(11) . . ?
O1 C13 H13 118.5 . . ?
C5 C13 H13 118.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 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 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 1.7379(11) . ?
S1 C12 1.7423(11) . ?
O1 C13 1.2141(13) . ?
C1 C2 1.3936(16) . ?
C1 C6 1.4181(14) . ?
C2 C3 1.3797(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3911(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3915(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4139(14) . ?
C5 C13 1.4851(15) . ?
C6 C7 1.4556(15) . ?
C7 C12 1.4067(14) . ?
C7 C8 1.4072(14) . ?
C8 C9 1.3861(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4160(14) . ?
C9 C14 1.5035(16) . ?
C10 C11 1.3858(16) . ?
C10 C15 1.5064(16) . ?
C11 C12 1.3921(15) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
C12 S1 C1 C2 179.92(11) . . . . ?
C12 S1 C1 C6 1.45(9) . . . . ?
C6 C1 C2 C3 0.08(18) . . . . ?
S1 C1 C2 C3 -178.24(10) . . . . ?
C1 C2 C3 C4 1.07(19) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -1.25(19) . . . . ?
C3 C4 C5 C13 173.59(12) . . . . ?
C4 C5 C6 C1 2.29(16) . . . . ?
C13 C5 C6 C1 -172.08(10) . . . . ?
C4 C5 C6 C7 -179.12(11) . . . . ?
C13 C5 C6 C7 6.52(19) . . . . ?
C2 C1 C6 C5 -1.77(16) . . . . ?
S1 C1 C6 C5 176.72(8) . . . . ?
C2 C1 C6 C7 179.35(11) . . . . ?
S1 C1 C6 C7 -2.16(12) . . . . ?
C5 C6 C7 C12 -176.78(11) . . . . ?
C1 C6 C7 C12 1.88(13) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C1 C6 C7 C8 -177.68(11) . . . . ?
C12 C7 C8 C9 1.99(16) . . . . ?
C6 C7 C8 C9 -178.48(11) . . . . ?
C7 C8 C9 C10 -1.11(16) . . . . ?
C7 C8 C9 C14 179.78(10) . . . . ?
C8 C9 C10 C11 -0.65(16) . . . . ?
C14 C9 C10 C11 178.45(11) . . . . ?
C8 C9 C10 C15 -179.20(11) . . . . ?
C14 C9 C10 C15 -0.10(17) . . . . ?
C9 C10 C11 C12 1.44(17) . . . . ?
C15 C10 C11 C12 179.99(11) . . . . ?
C10 C11 C12 C7 -0.51(17) . . . . ?
C10 C11 C12 S1 179.50(9) . . . . ?
C8 C7 C12 C11 -1.18(16) . . . . ?
C6 C7 C12 C11 179.20(10) . . . . ?
C8 C7 C12 S1 178.81(8) . . . . ?
C6 C7 C12 S1 -0.82(12) . . . . ?
C1 S1 C12 C11 179.65(10) . . . . ?
C1 S1 C12 C7 -0.34(9) . . . . ?
C4 C5 C13 O1 12.95(18) . . . . ?
C6 C5 C13 O1 -172.51(12) . . . . ?
