#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:18:48 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245868 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/14/2311416.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_2311416
loop_
_publ_author_name
'Tanaka, Syuto'
'Masu, Hyuma'
'Sasanuma, Yuji'
_publ_section_title
;
 Crystal structures of 2-(benzene-carbo-thio-yloxy)ethyl
 benzene-carbo-thio-ate and 2-(benzene-carbo-thio-yloxy)ethyl benzoate.
;
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1430
_journal_page_last               1433
_journal_paper_doi               10.1107/S2056989017012701
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C16 H14 O2 S2'
_chemical_formula_moiety         'C16 H14 O2 S2'
_chemical_formula_sum            'C16 H14 O2 S2'
_chemical_formula_weight         302.39
_chemical_name_common            EBTB
_chemical_name_systematic
;
2-(Benzenecarbothioyloxy)ethyl benzenecarbothioate
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 113.475(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.829(5)
_cell_length_b                   11.680(7)
_cell_length_c                   7.727(5)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5942
_cell_measurement_theta_min      2.5309
_cell_volume                     730.9(8)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
XSHEL (Bruker, 2012)
;
_computing_publication_material
;
XCIF (Bruker, 2012)
;
_computing_structure_refinement
;
SHELXL-2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_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  0.0136
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4017
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.401
_diffrn_reflns_theta_min         2.515
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0291
_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)+(0.0425P)²+0.2706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                1487
_reflns_number_total             1617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5479sup1.cif
_cod_data_source_block           model_D
_cod_database_code               2311416
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_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
C C1 0.70662(15) 0.86862(11) 0.98706(17) 0.0209(3) Uani d 1
C C2 0.52641(15) 0.87852(10) 0.86705(17) 0.0205(3) Uani d 1
C C3 0.41444(16) 0.80285(12) 0.89460(19) 0.0271(3) Uani d 1
H H3 0.4532 0.7468 0.9916 0.033 Uiso calc 1
C C4 0.24591(17) 0.80973(13) 0.7796(2) 0.0312(3) Uani d 1
H H4 0.1705 0.7586 0.7991 0.037 Uiso calc 1
C C5 0.18837(16) 0.89124(13) 0.6367(2) 0.0309(3) Uani d 1
H H5 0.0741 0.8947 0.5572 0.037 Uiso calc 1
C C6 0.29824(17) 0.96779(13) 0.6101(2) 0.0316(3) Uani d 1
H H6 0.2585 1.024 0.5136 0.038 Uiso calc 1
C C7 0.46690(16) 0.96209(11) 0.72503(19) 0.0259(3) Uani d 1
H H7 0.5413 1.0148 0.707 0.031 Uiso calc 1
C C8 0.97120(15) 0.94978(12) 1.04144(19) 0.0267(3) Uani d 1
H H8A 1.0184 0.8771 1.0194 0.032 Uiso calc 1
H H8B 1.0041 0.9599 1.1788 0.032 Uiso calc 1
O O1 0.79324(11) 0.95006(8) 0.94319(13) 0.0252(2) Uani d 1
S S1 0.79118(4) 0.77062(3) 1.15081(5) 0.02945(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
O1 C1 C2 . . 111.15(11)
O1 C1 S1 . . 123.72(10)
C2 C1 S1 . . 125.13(9)
C3 C2 C7 . . 119.27(12)
C3 C2 C1 . . 119.84(12)
C7 C2 C1 . . 120.89(11)
C4 C3 C2 . . 120.17(13)
C4 C3 H3 . . 119.9
C2 C3 H3 . . 119.9
C5 C4 C3 . . 120.21(13)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C6 . . 120.02(13)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C5 C6 C7 . . 120.22(13)
C5 C6 H6 . . 119.9
C7 C6 H6 . . 119.9
C6 C7 C2 . . 120.09(12)
C6 C7 H7 . . 120.0
C2 C7 H7 . . 120.0
O1 C8 C8 . 3_777 104.66(13)
O1 C8 H8A . . 110.8
C8 C8 H8A 3_777 . 110.8
O1 C8 H8B . . 110.8
C8 C8 H8B 3_777 . 110.8
H8A C8 H8B . . 108.9
C1 O1 C8 . . 118.26(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.3458(16)
C1 C2 . 1.4931(18)
C1 S1 . 1.6481(14)
C2 C3 . 1.4042(19)
C2 C7 . 1.4049(19)
C3 C4 . 1.399(2)
C3 H3 . 0.95
C4 C5 . 1.392(2)
C4 H4 . 0.95
C5 C6 . 1.393(2)
C5 H5 . 0.95
C6 C7 . 1.399(2)
C6 H6 . 0.95
C7 H7 . 0.95
C8 O1 . 1.4474(17)
C8 C8 3_777 1.518(3)
C8 H8A . 0.99
C8 H8B . 0.99
