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#$Date: 2023-06-15 10:18:04 +0300 (Thu, 15 Jun 2023) $
#$Revision: 284464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107359.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_8107359
loop_
_publ_author_name
'Tapala, Kgaugelo C.'
'Clayton, Hadley S.'
_publ_section_title
;
 Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide)
 ethanol solvate, C27H26P2S2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              83
_journal_page_last               85
_journal_paper_doi               10.1515/ncrs-2022-0496
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H26 P2 S2 [+ solvent]'
_chemical_formula_sum            'C27 H26 P2 S2'
_chemical_formula_weight         476.54
_space_group_crystal_system      tetragonal
_space_group_IT_number           79
_space_group_name_Hall           'I 4'
_space_group_name_H-M_alt        'I 4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9196(12)
_cell_length_b                   16.9196(12)
_cell_length_c                   9.4187(8)
_cell_measurement_reflns_used    3452
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      3.41
_cell_measurement_wavelength     0.71073
_cell_volume                     2696.3(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_molecular_graphics
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23943
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.478
_diffrn_reflns_theta_min         3.406
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2150
_reflns_number_total             2519
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0496_suppl.cif
_cod_data_source_block           TKCDPPPS
_cod_database_code               8107359
_shelx_estimated_absorpt_t_min   0.871
_shelx_estimated_absorpt_t_max   0.987
_shelx_shelxl_version_number     2018/3
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+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
C1 C 0.4835(2) 0.0725(2) 0.3939(4) 0.0230(8) Uani 1 1 d . . . . .
H1A H 0.530652 0.082969 0.453356 0.028 Uiso 1 1 calc R U . . .
H1B H 0.438982 0.060132 0.458351 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5 0 0.2994(6) 0.0249(10) Uani 1 2 d S T P . .
H2A H 0.546234 0.010499 0.237823 0.03 Uiso 0.5 1 calc R U P . .
H2B H 0.453767 -0.010499 0.23782 0.03 Uiso 0.5 1 calc R U P . .
C3 C 0.5493(2) 0.1916(2) 0.2026(3) 0.0241(8) Uani 1 1 d . . . . .
C4 C 0.6214(2) 0.1926(2) 0.2714(4) 0.0317(9) Uani 1 1 d . . . . .
H4 H 0.624941 0.174708 0.366807 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6884(3) 0.2196(2) 0.2026(4) 0.0374(10) Uani 1 1 d . . . . .
H5 H 0.737836 0.219749 0.250541 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6837(3) 0.2461(3) 0.0646(4) 0.0424(11) Uani 1 1 d . . . . .
H6 H 0.72944 0.265745 0.018098 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6132(3) 0.2441(3) -0.0050(4) 0.0485(12) Uani 1 1 d . . . . .
H7 H 0.610532 0.260883 -0.101114 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5450(3) 0.2178(2) 0.0628(4) 0.0368(10) Uani 1 1 d . . . . .
H8 H 0.495885 0.217673 0.01396 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4430(2) 0.2384(2) 0.4239(4) 0.0224(8) Uani 1 1 d . . . . .
C10 C 0.4700(2) 0.2333(2) 0.5630(3) 0.0276(8) Uani 1 1 d . . . . .
H10 H 0.497191 0.187345 0.594226 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4570(2) 0.2956(2) 0.6564(4) 0.0328(9) Uani 1 1 d . . . . .
H11 H 0.475015 0.291408 0.751618 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4189(2) 0.3628(2) 0.6136(4) 0.0368(10) Uani 1 1 d . . . . .
H12 H 0.411354 0.405279 0.678015 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3914(3) 0.3683(3) 0.4749(4) 0.0434(11) Uani 1 1 d . . . . .
H13 H 0.364186 0.414413 0.44459 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4035(2) 0.3065(2) 0.3809(4) 0.0334(9) Uani 1 1 d . . . . .
H14 H 0.384675 0.310668 0.286176 0.04 Uiso 1 1 calc R U . . .
P1 P 0.45974(5) 0.16121(5) 0.29354(10) 0.0218(2) Uani 1 1 d . . . . .
S1 S 0.37049(6) 0.14747(5) 0.16383(10) 0.0319(2) Uani 1 1 d . . . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.025
1 -1 0 0.01
0 0 -1 0.217
0 0 1 0.2
-1 0 0 0.019
1 0 0 0.021
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
C2 C1 P1 113.4(2) . .
C2 C1 H1A 108.9 . .
P1 C1 H1A 108.9 . .
C2 C1 H1B 108.9 . .
P1 C1 H1B 108.9 . .
H1A C1 H1B 107.7 . .
C1 C2 C1 109.4(4) . 2_655
C1 C2 H2A 109.8 . .
C1 C2 H2A 109.8 2_655 .
C1 C2 H2B 109.8 . .
C1 C2 H2B 109.8 2_655 .
H2A C2 H2B 108.2 . .
C4 C3 C8 119.1(4) . .
C4 C3 P1 121.3(3) . .
C8 C3 P1 119.5(3) . .
C3 C4 C5 120.5(3) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 120.1(4) . .
C6 C5 H5 120 . .
C4 C5 H5 120 . .
C7 C6 C5 119.9(4) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C8 120.9(4) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C3 C8 C7 119.5(4) . .
C3 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C10 C9 C14 118.9(3) . .
C10 C9 P1 122.8(3) . .
C14 C9 P1 118.3(3) . .
C11 C10 C9 119.8(3) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C12 C11 C10 121.2(4) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C11 C12 C13 119.4(4) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C14 C13 C12 120.0(4) . .
C14 C13 H13 120 . .
C12 C13 H13 120 . .
C13 C14 C9 120.7(3) . .
C13 C14 H14 119.7 . .
C9 C14 H14 119.7 . .
C9 P1 C3 104.25(16) . .
C9 P1 C1 106.05(16) . .
C3 P1 C1 107.09(17) . .
C9 P1 S1 112.80(12) . .
C3 P1 S1 112.56(12) . .
C1 P1 S1 113.41(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.541(4) .
C1 P1 1.820(3) .
C1 H1A 0.99 .
C1 H1B 0.99 .
C2 H2A 0.99 .
C2 H2B 0.99 .
C3 C4 1.381(5) .
C3 C8 1.391(5) .
C3 P1 1.815(4) .
C4 C5 1.384(5) .
C4 H4 0.95 .
C5 C6 1.377(6) .
C5 H5 0.95 .
C6 C7 1.361(6) .
C6 H6 0.95 .
C7 C8 1.392(6) .
C7 H7 0.95 .
C8 H8 0.95 .
C9 C10 1.390(5) .
C9 C14 1.393(5) .
C9 P1 1.815(3) .
C10 C11 1.390(5) .
C10 H10 0.95 .
C11 C12 1.368(5) .
C11 H11 0.95 .
C12 C13 1.390(5) .
C12 H12 0.95 .
C13 C14 1.385(5) .
C13 H13 0.95 .
C14 H14 0.95 .
P1 S1 1.9563(13) .
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
P1 C1 C2 C1 -177.9(3) . . . 2_655
C8 C3 C4 C5 0.2(6) . . . .
P1 C3 C4 C5 -176.9(3) . . . .
C3 C4 C5 C6 0.4(6) . . . .
C4 C5 C6 C7 -1.5(6) . . . .
C5 C6 C7 C8 2.0(7) . . . .
C4 C3 C8 C7 0.3(6) . . . .
P1 C3 C8 C7 177.4(3) . . . .
C6 C7 C8 C3 -1.4(7) . . . .
C14 C9 C10 C11 0.2(5) . . . .
P1 C9 C10 C11 178.1(3) . . . .
C9 C10 C11 C12 -0.9(6) . . . .
C10 C11 C12 C13 1.2(6) . . . .
C11 C12 C13 C14 -0.8(7) . . . .
C12 C13 C14 C9 0.2(7) . . . .
C10 C9 C14 C13 0.1(6) . . . .
P1 C9 C14 C13 -177.9(3) . . . .
C10 C9 P1 C3 -93.8(3) . . . .
C14 C9 P1 C3 84.1(3) . . . .
C10 C9 P1 C1 19.0(4) . . . .
C14 C9 P1 C1 -163.0(3) . . . .
C10 C9 P1 S1 143.7(3) . . . .
C14 C9 P1 S1 -38.3(3) . . . .
C4 C3 P1 C9 67.5(3) . . . .
C8 C3 P1 C9 -109.5(3) . . . .
C4 C3 P1 C1 -44.6(3) . . . .
C8 C3 P1 C1 138.4(3) . . . .
C4 C3 P1 S1 -169.9(3) . . . .
C8 C3 P1 S1 13.1(3) . . . .
C2 C1 P1 C9 -179.9(2) . . . .
C2 C1 P1 C3 -69.0(2) . . . .
C2 C1 P1 S1 55.8(2) . . . .
