#------------------------------------------------------------------------------
#$Date: 2025-08-21 16:09:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301850 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/29/7042991.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_7042991
loop_
_publ_author_name
'Kosnik, Stephanie C.'
'Nascimento, Maxemilian C.'
'Rawson, Jeremy Michael'
'Macdonald, Charles L. B.'
_publ_section_title
;
 Synthesis of Bis(trithio)phosphines by Oxidative Transfer of
 Phosphorus(I)
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01345K
_journal_year                    2017
_chemical_formula_moiety         'C16 H16 O4 P2 S4'
_chemical_formula_sum            'C16 H16 O4 P2 S4'
_chemical_formula_weight         462.47
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-12 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.786(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6592(5)
_cell_length_b                   8.9815(4)
_cell_length_c                   10.3322(5)
_cell_measurement_reflns_used    3124
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.16
_cell_volume                     974.22(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11795
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.985
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2015'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       Block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0434
_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)+(0.0335P)²+1.4163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1641
_reflns_number_total             2233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01345k2.cif
_cod_data_source_block           shelx
_cod_database_code               7042991
_shelx_shelxl_version_number     2014/7
_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   0.909
_shelx_estimated_absorpt_t_max   0.967
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_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
P P 0.54336(7) 0.11173(9) 0.00325(8) 0.0250(2) Uani 1 1 d . .
S1 S 0.54751(7) 0.17995(9) 0.19983(8) 0.02441(19) Uani 1 1 d . .
S2 S 0.73554(7) 0.04320(10) 0.08955(8) 0.0305(2) Uani 1 1 d . .
C1 C 0.6679(2) 0.0543(3) 0.3112(3) 0.0200(6) Uani 1 1 d . .
C2 C 0.6823(2) 0.0216(3) 0.4499(3) 0.0196(6) Uani 1 1 d . .
H2 H 0.6238 0.0607 0.4825 0.023 Uiso 1 1 calc R U
C3 C 0.7815(3) -0.0674(3) 0.5391(3) 0.0203(6) Uani 1 1 d . .
C4 C 0.8671(3) -0.1281(3) 0.4900(3) 0.0206(6) Uani 1 1 d . .
C5 C 0.8517(3) -0.0967(3) 0.3525(3) 0.0222(6) Uani 1 1 d . .
H5 H 0.9089 -0.1375 0.3187 0.027 Uiso 1 1 calc R U
C6 C 0.7524(3) -0.0053(3) 0.2635(3) 0.0209(6) Uani 1 1 d . .
C11 C 0.7078(3) -0.0708(4) 0.7200(3) 0.0288(7) Uani 1 1 d . .
H11A H 0.6959 0.0372 0.7194 0.043 Uiso 1 1 calc R U
H11B H 0.7325 -0.1093 0.8172 0.043 Uiso 1 1 calc R U
H11C H 0.6279 -0.1178 0.6535 0.043 Uiso 1 1 calc R U
C21 C 1.0443(3) -0.2871(4) 0.5374(4) 0.0346(8) Uani 1 1 d . .
H21A H 0.9956 -0.3445 0.4497 0.052 Uiso 1 1 calc R U
H21B H 1.1021 -0.3537 0.6125 0.052 Uiso 1 1 calc R U
H21C H 1.0939 -0.2101 0.5172 0.052 Uiso 1 1 calc R U
O1 O 0.80502(19) -0.1036(2) 0.6762(2) 0.0271(5) Uani 1 1 d . .
O2 O 0.95861(18) -0.2183(2) 0.5849(2) 0.0295(5) 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 0.0000 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'
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
_geom_angle_site_symmetry_3
S1 P S2 95.90(4) .
S1 P P 96.36(5) 3_655
S2 P P 97.70(6) 3_655
C1 S1 P 96.90(10) .
C6 S2 P 97.41(10) .
C6 C1 C2 119.7(3) .
C6 C1 S1 119.9(2) .
C2 C1 S1 120.3(2) .
C3 C2 C1 119.9(3) .
C3 C2 H2 120.0 .
C1 C2 H2 120.0 .
O1 C3 C2 124.5(2) .
O1 C3 C4 115.3(2) .
C2 C3 C4 120.2(2) .
O2 C4 C5 125.0(3) .
O2 C4 C3 115.3(2) .
C5 C4 C3 119.7(3) .
C4 C5 C6 119.9(3) .
C4 C5 H5 120.1 .
C6 C5 H5 120.1 .
C1 C6 C5 120.6(3) .
C1 C6 S2 118.8(2) .
C5 C6 S2 120.5(2) .
O1 C11 H11A 109.5 .
O1 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
O1 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
O2 C21 H21A 109.5 .
O2 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
O2 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C3 O1 C11 117.0(2) .
C4 O2 C21 117.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P S1 2.1017(11) .
P S2 2.1110(11) .
P P 2.2350(16) 3_655
S1 C1 1.778(3) .
S2 C6 1.775(3) .
C1 C6 1.387(4) .
C1 C2 1.399(4) .
C2 C3 1.378(4) .
C2 H2 0.9500 .
C3 O1 1.361(3) .
C3 C4 1.411(4) .
C4 O2 1.358(3) .
C4 C5 1.382(4) .
C5 C6 1.391(4) .
C5 H5 0.9500 .
C11 O1 1.422(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C21 O2 1.431(4) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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
P S1 C1 C6 22.7(2)
P S1 C1 C2 -160.9(2)
C6 C1 C2 C3 1.1(4)
S1 C1 C2 C3 -175.3(2)
C1 C2 C3 O1 178.9(3)
C1 C2 C3 C4 -1.3(4)
O1 C3 C4 O2 2.1(4)
C2 C3 C4 O2 -177.8(2)
O1 C3 C4 C5 -179.5(2)
C2 C3 C4 C5 0.7(4)
O2 C4 C5 C6 178.5(3)
C3 C4 C5 C6 0.2(4)
C2 C1 C6 C5 -0.3(4)
S1 C1 C6 C5 176.2(2)
C2 C1 C6 S2 -177.8(2)
S1 C1 C6 S2 -1.3(3)
C4 C5 C6 C1 -0.4(4)
C4 C5 C6 S2 177.1(2)
P S2 C6 C1 -20.7(2)
P S2 C6 C5 161.8(2)
C2 C3 O1 C11 12.3(4)
C4 C3 O1 C11 -167.6(3)
C5 C4 O2 C21 -0.8(4)
C3 C4 O2 C21 177.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139170767
