#------------------------------------------------------------------------------
#$Date: 2022-03-11 12:32:06 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273661 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104750.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_8104750
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of thioxanthen-9-one-10,10-dioxide,
 C13H8O3S -- a second polymorph
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              503
_journal_page_last               505
_journal_paper_doi               10.1515/ncrs-2020-0578
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C13 H8 O3 S'
_chemical_formula_sum            'C13 H8 O3 S'
_chemical_formula_weight         244.25
_chemical_name_common            thioxanthen-9-one-10,10-dioxide
_chemical_name_systematic        thioxanthen-9-one-10,10-dioxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.784(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7499(3)
_cell_length_b                   12.9758(4)
_cell_length_c                   8.2681(3)
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.14
_cell_volume                     1015.90(6)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4481
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         4.305
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8668
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS[6]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.434
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_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)+(0.0452P)²+1.0181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1161
_reflns_number_total             1212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0578_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8104750
_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'
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 0.000000 0.19855(3) 0.750000 0.02738(17) Uani 1 2 d S T P . .
O1 O 0.000000 -0.14230(12) 0.750000 0.0498(5) Uani 1 2 d S T P . .
O2 O -0.06422(12) 0.25645(9) 0.60344(15) 0.0421(3) Uani 1 1 d . . . . .
C1 C 0.000000 -0.04917(15) 0.750000 0.0281(4) Uani 1 2 d S T P . .
C11 C 0.12694(13) 0.11582(10) 0.70096(15) 0.0232(3) Uani 1 1 d . . . . .
C12 C 0.11444(13) 0.00847(10) 0.69697(15) 0.0232(3) Uani 1 1 d . . . . .
C13 C 0.21766(15) -0.04847(11) 0.64499(17) 0.0276(3) Uani 1 1 d . . . . .
H13 H 0.210461 -0.121457 0.639172 0.033 Uiso 1 1 calc R U . . .
C14 C 0.33007(15) -0.00015(12) 0.60193(18) 0.0319(3) Uani 1 1 d . . . . .
H14 H 0.399167 -0.039970 0.566258 0.038 Uiso 1 1 calc R U . . .
C15 C 0.34253(15) 0.10669(12) 0.61059(19) 0.0333(3) Uani 1 1 d . . . . .
H15 H 0.420793 0.139679 0.582694 0.040 Uiso 1 1 calc R U . . .
C16 C 0.24079(14) 0.16460(11) 0.65985(18) 0.0299(3) Uani 1 1 d . . . . .
H16 H 0.248663 0.237548 0.665604 0.036 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
O2 S1 O2 116.93(11) 2_556 .
O2 S1 C11 108.32(6) 2_556 2_556
O2 S1 C11 108.95(6) . 2_556
O2 S1 C11 108.95(6) 2_556 .
O2 S1 C11 108.32(6) . .
C11 S1 C11 104.69(9) 2_556 .
O1 C1 C12 120.05(8) . .
O1 C1 C12 120.05(8) . 2_556
C12 C1 C12 119.89(16) . 2_556
C16 C11 C12 121.24(12) . .
C16 C11 S1 115.22(10) . .
C12 C11 S1 123.50(10) . .
C13 C12 C11 117.99(12) . .
C13 C12 C1 117.98(12) . .
C11 C12 C1 123.99(12) . .
C14 C13 C12 120.90(13) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C13 C14 C15 120.25(13) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 119.80(13) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C15 C16 C11 119.77(13) . .
C15 C16 H16 120.1 . .
C11 C16 H16 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4364(11) 2_556
S1 O2 1.4364(11) .
S1 C11 1.7572(12) 2_556
S1 C11 1.7572(12) .
O1 C1 1.209(2) .
C1 C12 1.4932(15) .
C1 C12 1.4932(15) 2_556
C11 C16 1.3885(18) .
C11 C12 1.3981(18) .
C12 C13 1.3962(18) .
C13 C14 1.381(2) .
C13 H13 0.9500 .
C14 C15 1.392(2) .
C14 H14 0.9500 .
C15 C16 1.3809(19) .
C15 H15 0.9500 .
C16 H16 0.9500 .
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
C14 H14 O2 0.95 2.67 3.3213(18) 125.9 3_545
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
O2 S1 C11 C16 -63.37(12) 2_556 . . .
O2 S1 C11 C16 64.80(12) . . . .
C11 S1 C11 C16 -179.06(12) 2_556 . . .
O2 S1 C11 C12 118.79(11) 2_556 . . .
O2 S1 C11 C12 -113.04(12) . . . .
C11 S1 C11 C12 3.10(8) 2_556 . . .
C16 C11 C12 C13 -2.08(19) . . . .
S1 C11 C12 C13 175.64(9) . . . .
C16 C11 C12 C1 175.91(11) . . . .
S1 C11 C12 C1 -6.38(17) . . . .
O1 C1 C12 C13 1.34(12) . . . .
C12 C1 C12 C13 -178.66(12) 2_556 . . .
O1 C1 C12 C11 -176.65(9) . . . .
C12 C1 C12 C11 3.35(9) 2_556 . . .
C11 C12 C13 C14 1.21(19) . . . .
C1 C12 C13 C14 -176.89(11) . . . .
C12 C13 C14 C15 0.3(2) . . . .
C13 C14 C15 C16 -1.1(2) . . . .
C14 C15 C16 C11 0.2(2) . . . .
C12 C11 C16 C15 1.4(2) . . . .
S1 C11 C16 C15 -176.51(11) . . . .
