#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:23:14 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/14/2311433.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311433
loop_
_publ_author_name
'Hübscher, Jörg'
'Augustin, André U'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Crystal structure of a new polymorph of di(thio-phen-3-yl) ketone.
;
_journal_coeditor_code           QM2119
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1560
_journal_page_last               1562
_journal_paper_doi               10.1107/S2056989017013342
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C9 H6 O S2'
_chemical_formula_moiety         'C9 H6 O S2'
_chemical_formula_sum            'C9 H6 O S2'
_chemical_formula_weight         194.26
_chemical_name_common
;
Di(thiophen-3-yl) ketone
;
_chemical_name_systematic
;
Bis(thiophen-3-yl)methanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9464(2)
_cell_length_b                   11.5015(5)
_cell_length_c                   19.2970(9)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      3.17
_cell_volume                     875.88(7)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6469
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.191
_diffrn_reflns_theta_min         3.543
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_correction_T_min  0.7593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0472
_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)+(0.0648P)²+0.6490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1608
_reflns_number_gt                667
_reflns_number_total             972
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qm2119sup1.cif
_cod_data_source_block           I
_cod_database_code               2311433
_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   0.759
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.1430(3) 0.46670(8) 0.08955(5) 0.0781(4) Uani d 1
O O1 0.0000 0.1486(3) 0.2500 0.1066(15) Uani d 1
C C1 -0.0185(11) 0.3364(3) 0.0641(2) 0.0791(11) Uani d 1
H H1 -0.0650 0.3163 0.0184 0.095 Uiso calc 1
C C2 -0.0701(9) 0.2660(3) 0.1189(2) 0.0755(10) Uani d 1
H H2 -0.1562 0.1910 0.1148 0.091 Uiso calc 1
C C3 0.0202(8) 0.3174(2) 0.18397(18) 0.0608(8) Uani d 1
C C4 0.1397(8) 0.4274(2) 0.17415(17) 0.0604(8) Uani d 1
H H4 0.2116 0.4755 0.2100 0.073 Uiso calc 1
C C5 0.0000 0.2550(3) 0.2500 0.0672(13) Uani d 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C4 S1 C1 . . 92.30(18)
C2 C1 S1 . . 111.1(3)
C2 C1 H1 . . 124.5
S1 C1 H1 . . 124.5
C1 C2 C3 . . 113.7(3)
C1 C2 H2 . . 123.2
C3 C2 H2 . . 123.2
C4 C3 C2 . . 110.3(3)
C4 C3 C5 . . 126.5(3)
C2 C3 C5 . . 123.1(3)
C3 C4 S1 . . 112.6(2)
C3 C4 H4 . . 123.7
S1 C4 H4 . . 123.7
O1 C5 C3 . 3 119.34(17)
O1 C5 C3 . . 119.34(17)
C3 C5 C3 3 . 121.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C4 . 1.694(3)
S1 C1 . 1.701(4)
O1 C5 . 1.225(5)
C1 C2 . 1.347(6)
C1 H1 . 0.9300
C2 C3 . 1.434(5)
C2 H2 . 0.9300
C3 C4 . 1.363(4)
C3 C5 . 1.464(4)
C4 H4 . 0.9300
C5 C3 3 1.464(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 O1 6_666 0.93 2.42 3.261(4) 150.5
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_site_symmetry_4
_geom_torsion
C4 S1 C1 C2 . -0.3(3)
S1 C1 C2 C3 . 0.3(4)
C1 C2 C3 C4 . -0.2(4)
C1 C2 C3 C5 . -177.1(3)
C2 C3 C4 S1 . -0.1(4)
C5 C3 C4 S1 . 176.8(2)
C1 S1 C4 C3 . 0.2(3)
C4 C3 C5 O1 . -155.2(3)
C2 C3 C5 O1 . 21.2(3)
C4 C3 C5 C3 3 24.8(3)
C2 C3 C5 C3 3 -158.8(3)
