#------------------------------------------------------------------------------
#$Date: 2024-08-07 01:06:27 +0300 (Wed, 07 Aug 2024) $
#$Revision: 294000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023172.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_2023172
loop_
_publ_author_name
'Risken, Robin'
'Kuzu, Yasin Mehmet'
'Schmidt, Annika'
'Strohmann, Carsten'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 dimeth-yl(phen-yl)phosphine sulfide.
;
_journal_coeditor_code           HB8100
_journal_issue                   'Pt 7'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              755
_journal_page_last               758
_journal_paper_doi               10.1107/S2056989024005668
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C8 H11 P S'
_chemical_formula_moiety         'C8 H11 P S'
_chemical_formula_sum            'C8 H11 P S'
_chemical_formula_weight         170.20
_chemical_name_common
;
Dimethyl(phenyl)phosphine sulfide
;
_chemical_name_systematic
;
Dimethyl(phenyl)phosphanethione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.372(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2805(2)
_cell_length_b                   7.6549(2)
_cell_length_c                   19.3578(8)
_cell_measurement_reflns_used    3458
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.23
_cell_measurement_theta_min      4.63
_cell_volume                     918.23(5)
_computing_cell_refinement
;
SAINT V8.38A (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT V8.38A (Bruker, 2018)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12606
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.716
_diffrn_reflns_theta_min         4.630
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.172
_exptl_absorpt_correction_T_max  0.5871
_exptl_absorpt_correction_T_min  0.4645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0243
_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)+(0.0310P)²+0.3420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                1745
_reflns_number_total             1886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8100.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023172.cif.'
_cod_database_code               2023172
_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   0.593
_shelx_estimated_absorpt_t_max   0.693
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.42807(5) 0.75930(4) 0.57224(2) 0.02071(10) Uani d 1 . .
S S1 0.73232(5) 0.79603(5) 0.56424(2) 0.02966(11) Uani d 1 . .
C C3 0.3919(2) 0.57849(16) 0.62992(6) 0.0225(3) Uani d 1 . .
C C8 0.1928(2) 0.49493(18) 0.62617(7) 0.0280(3) Uani d 1 . .
H H8 0.0754 0.5285 0.5913 0.034 Uiso calc 1 . .
C C2 0.2586(2) 0.71634(18) 0.48984(7) 0.0267(3) Uani d 1 . .
H H2A 0.3014 0.6055 0.4708 0.040 Uiso calc 1 . .
H H2B 0.2743 0.8110 0.4570 0.040 Uiso calc 1 . .
H H2C 0.1078 0.7091 0.4968 0.040 Uiso calc 1 . .
C C1 0.3115(2) 0.94645(17) 0.60830(7) 0.0268(3) Uani d 1 . .
H H1A 0.1620 0.9205 0.6133 0.040 Uiso calc 1 . .
H H1B 0.3142 1.0466 0.5769 0.040 Uiso calc 1 . .
H H1C 0.3950 0.9741 0.6543 0.040 Uiso calc 1 . .
C C4 0.5618(2) 0.52745(19) 0.68113(7) 0.0320(3) Uani d 1 . .
H H4 0.6990 0.5816 0.6836 0.038 Uiso calc 1 . .
C C7 0.1657(2) 0.36298(19) 0.67315(8) 0.0331(3) Uani d 1 . .
H H7 0.0303 0.3056 0.6700 0.040 Uiso calc 1 . .
C C6 0.3345(3) 0.31482(19) 0.72440(8) 0.0357(3) Uani d 1 . .
H H6 0.3152 0.2250 0.7567 0.043 Uiso calc 1 . .
C C5 0.5320(3) 0.3975(2) 0.72876(8) 0.0398(4) Uani d 1 . .
H H5 0.6477 0.3654 0.7645 0.048 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C3 P1 S1 . . 112.26(4) ?
C2 P1 S1 . . 113.55(5) ?
C2 P1 C3 . . 106.91(6) ?
C2 P1 C1 . . 105.68(6) ?
C1 P1 S1 . . 112.28(5) ?
C1 P1 C3 . . 105.58(6) ?
C8 C3 P1 . . 121.21(10) ?
C4 C3 P1 . . 119.64(10) ?
C4 C3 C8 . . 119.08(12) ?
C3 C8 H8 . . 119.9 ?
C7 C8 C3 . . 120.25(13) ?
C7 C8 H8 . . 119.9 ?
P1 C2 H2A . . 109.5 ?
P1 C2 H2B . . 109.5 ?
P1 C2 H2C . . 109.5 ?
H2A C2 H2B . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
P1 C1 H1A . . 109.5 ?
P1 C1 H1B . . 109.5 ?
P1 C1 H1C . . 109.5 ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C4 H4 . . 119.9 ?
C3 C4 C5 . . 120.24(14) ?
C5 C4 H4 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C6 C7 C8 . . 120.26(14) ?
C6 C7 H7 . . 119.9 ?
C7 C6 H6 . . 120.1 ?
C7 C6 C5 . . 119.89(13) ?
C5 C6 H6 . . 120.1 ?
C4 C5 H5 . . 119.9 ?
C6 C5 C4 . . 120.26(14) ?
C6 C5 H5 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 S1 . 1.9623(5) ?
P1 C3 . 1.8158(13) ?
P1 C2 . 1.7977(13) ?
P1 C1 . 1.8004(13) ?
C3 C8 . 1.3957(19) ?
C3 C4 . 1.3893(18) ?
C8 H8 . 0.9500 ?
C8 C7 . 1.388(2) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C4 H4 . 0.9500 ?
C4 C5 . 1.390(2) ?
C7 H7 . 0.9500 ?
C7 C6 . 1.379(2) ?
C6 H6 . 0.9500 ?
C6 C5 . 1.383(2) ?
C5 H5 . 0.9500 ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
P1 C3 C8 C7 . . . . -176.66(10) ?
P1 C3 C4 C5 . . . . 175.48(12) ?
S1 P1 C3 C8 . . . . -159.38(10) ?
S1 P1 C3 C4 . . . . 23.85(12) ?
C3 C8 C7 C6 . . . . 0.8(2) ?
C3 C4 C5 C6 . . . . 1.7(2) ?
C8 C3 C4 C5 . . . . -1.4(2) ?
C8 C7 C6 C5 . . . . -0.4(2) ?
C2 P1 C3 C8 . . . . -34.24(12) ?
C2 P1 C3 C4 . . . . 148.99(11) ?
C1 P1 C3 C8 . . . . 77.98(12) ?
C1 P1 C3 C4 . . . . -98.79(12) ?
C4 C3 C8 C7 . . . . 0.1(2) ?
C7 C6 C5 C4 . . . . -0.8(2) ?
