#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239382.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_2239382
loop_
_publ_author_name
'Gessner, Viktoria H.'
_publ_section_title
;
 Diphenyl[(phenylsulfanyl)methyl]-λ⁵-phosphanethione
;
_journal_coeditor_code           WM5008
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o374
_journal_paper_doi               10.1107/S1600536814004292
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C19 H17 P S2'
_chemical_formula_moiety         'C19 H17 P S2'
_chemical_formula_sum            'C19 H17 P S2'
_chemical_formula_weight         340.42
_chemical_name_systematic
;
Diphenyl[(phenylsulfanyl)methyl]-λ⁵-phosphanethione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.044(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3748(13)
_cell_length_b                   18.598(3)
_cell_length_c                   10.0941(14)
_cell_measurement_reflns_used    4352
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.19
_cell_volume                     1727.3(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10734
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.5374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2663
_reflns_number_total             3033
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wm5008sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239382
_cod_database_fobs_code          2239382
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
C C1 0.52214(19) 0.08028(9) 0.30067(17) 0.0288(4) Uani d . 1
C C2 0.5712(2) 0.02245(10) 0.23596(19) 0.0380(4) Uani d . 1
H H2 0.535 0.0147 0.1425 0.046 Uiso calc R 1
C C3 0.6729(2) -0.02428(11) 0.3069(2) 0.0472(5) Uani d . 1
H H3 0.7053 -0.0643 0.2623 0.057 Uiso calc R 1
C C4 0.7274(2) -0.01291(10) 0.4421(2) 0.0413(5) Uani d . 1
H H4 0.7987 -0.0445 0.49 0.05 Uiso calc R 1
C C5 0.6782(2) 0.04426(10) 0.50795(19) 0.0397(5) Uani d . 1
H H5 0.7153 0.0518 0.6013 0.048 Uiso calc R 1
C C6 0.5750(2) 0.09060(10) 0.43818(18) 0.0356(4) Uani d . 1
H H6 0.5401 0.1295 0.484 0.043 Uiso calc R 1
C C7 0.2351(2) 0.14772(9) 0.28387(18) 0.0311(4) Uani d . 1
C C8 0.1148(2) 0.10634(12) 0.2316(2) 0.0463(5) Uani d . 1
H H8 0.1162 0.0763 0.1558 0.056 Uiso calc R 1
C C9 -0.0079(2) 0.10857(13) 0.2896(2) 0.0551(6) Uani d . 1
H H9 -0.0897 0.0796 0.2539 0.066 Uiso calc R 1
C C10 -0.0118(2) 0.15236(13) 0.3978(2) 0.0510(6) Uani d . 1
H H10 -0.0961 0.1538 0.4372 0.061 Uiso calc R 1
C C11 0.1064(2) 0.19424(11) 0.4494(2) 0.0487(5) Uani d . 1
H H11 0.1031 0.225 0.5239 0.058 Uiso calc R 1
C C12 0.2297(2) 0.19198(10) 0.3942(2) 0.0402(5) Uani d . 1
H H12 0.3114 0.2207 0.4314 0.048 Uiso calc R 1
C C13 0.4787(2) 0.23097(9) 0.24179(18) 0.0322(4) Uani d . 1
H H13A 0.4074 0.2696 0.2109 0.039 Uiso calc R 1
H H13B 0.5143 0.2366 0.3401 0.039 Uiso calc R 1
C C14 0.7380(2) 0.30474(9) 0.24404(18) 0.0332(4) Uani d . 1
C C15 0.8792(2) 0.30812(11) 0.2215(2) 0.0467(5) Uani d . 1
H H15 0.9118 0.2738 0.1642 0.056 Uiso calc R 1
C C16 0.9721(2) 0.36083(13) 0.2815(3) 0.0568(6) Uani d . 1
H H16 1.0679 0.3635 0.264 0.068 Uiso calc R 1
C C17 0.9273(3) 0.40970(13) 0.3668(2) 0.0573(6) Uani d . 1
H H17 0.9923 0.4458 0.4087 0.069 Uiso calc R 1
C C18 0.7882(3) 0.40641(12) 0.3914(2) 0.0534(6) Uani d . 1
H H18 0.7574 0.4402 0.4505 0.064 Uiso calc R 1
C C19 0.6925(2) 0.35395(11) 0.3302(2) 0.0432(5) Uani d . 1
H H19 0.5964 0.3518 0.3473 0.052 Uiso calc R 1
P P1 0.39369(5) 0.14308(2) 0.20578(4) 0.02841(14) Uani d . 1
S S1 0.34680(6) 0.12132(3) 0.01308(5) 0.03941(16) Uani d . 1
S S2 0.62814(5) 0.23650(3) 0.15364(5) 0.03730(15) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C2 C1 C6 119.37(17)
C2 C1 P1 119.93(14)
C6 C1 P1 120.68(13)
C1 C2 C3 120.18(17)
C1 C2 H2 119.9
C3 C2 H2 119.9
C4 C3 C2 120.23(19)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 120.05(18)
C5 C4 H4 120
C3 C4 H4 120
C4 C5 C6 120.05(17)
C4 C5 H5 120
C6 C5 H5 120
C5 C6 C1 120.09(17)
C5 C6 H6 120
C1 C6 H6 120
C8 C7 C12 118.81(18)
C8 C7 P1 118.95(15)
C12 C7 P1 122.23(14)
C7 C8 C9 120.2(2)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 120.3(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 119.9(2)
C9 C10 H10 120.1
C11 C10 H10 120.1
C10 C11 C12 120.5(2)
C10 C11 H11 119.7
C12 C11 H11 119.7
C11 C12 C7 120.20(19)
C11 C12 H12 119.9
C7 C12 H12 119.9
S2 C13 P1 107.72(9)
S2 C13 H13A 110.2
P1 C13 H13A 110.2
S2 C13 H13B 110.2
P1 C13 H13B 110.2
H13A C13 H13B 108.5
C19 C14 C15 119.44(18)
C19 C14 S2 125.31(15)
C15 C14 S2 115.23(15)
C16 C15 C14 120.3(2)
C16 C15 H15 119.9
C14 C15 H15 119.9
C17 C16 C15 120.4(2)
C17 C16 H16 119.8
C15 C16 H16 119.8
C16 C17 C18 119.9(2)
C16 C17 H17 120
C18 C17 H17 120
C17 C18 C19 120.4(2)
C17 C18 H18 119.8
C19 C18 H18 119.8
C14 C19 C18 119.6(2)
C14 C19 H19 120.2
C18 C19 H19 120.2
C7 P1 C1 108.53(8)
C7 P1 C13 103.53(8)
C1 P1 C13 104.55(8)
C7 P1 S1 113.32(6)
C1 P1 S1 113.12(6)
C13 P1 S1 112.99(6)
C14 S2 C13 102.51(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(3)
C1 C6 1.395(2)
C1 P1 1.8138(18)
C2 C3 1.384(3)
C2 H2 0.95
C3 C4 1.379(3)
C3 H3 0.95
C4 C5 1.379(3)
C4 H4 0.95
C5 C6 1.384(3)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.384(3)
C7 C12 1.393(3)
C7 P1 1.8137(18)
C8 C9 1.388(3)
C8 H8 0.95
C9 C10 1.369(3)
C9 H9 0.95
C10 C11 1.373(3)
C10 H10 0.95
C11 C12 1.377(3)
C11 H11 0.95
C12 H12 0.95
C13 S2 1.8009(18)
C13 P1 1.8242(18)
C13 H13A 0.99
C13 H13B 0.99
C14 C19 1.385(3)
C14 C15 1.387(3)
C14 S2 1.7729(19)
C15 C16 1.373(3)
C15 H15 0.95
C16 C17 1.371(3)
C16 H16 0.95
C17 C18 1.375(3)
C17 H17 0.95
C18 C19 1.387(3)
C18 H18 0.95
C19 H19 0.95
P1 S1 1.9527(7)
