#------------------------------------------------------------------------------
#$Date: 2022-11-16 04:14:40 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/58/7245840.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_7245840
loop_
_publ_author_name
'Li, Haoyuan'
'Yan, Wenjie'
'Ren, Peipei'
'Hu, Huimin'
'Sun, Runbo'
'Liu, Meixia'
'Fu, Zhengjiang'
'Guo, Shengmei'
'Cai, Hu'
_publ_section_title
;
 Bromide ion promoted practical synthesis of phosphinothioates of sulfinic
 acid derivatives and H-phosphine oxides
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              32350
_journal_page_last               32354
_journal_paper_doi               10.1039/D2RA06351D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C18 H15 O P S'
_chemical_formula_sum            'C18 H15 O P S'
_chemical_formula_weight         310.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                100.248(5)
_cell_angle_beta                 96.034(5)
_cell_angle_gamma                108.478(5)
_cell_formula_units_Z            2
_cell_length_a                   6.190(2)
_cell_length_b                   8.426(3)
_cell_length_c                   16.517(5)
_cell_measurement_reflns_used    2073
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      54.426
_cell_measurement_theta_min      5.299
_cell_volume                     791.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.545
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0258 after correction.
The Ratio of minimum to maximum transmission is 0.9231.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0429
_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)+(0.0479P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2711
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra06351d2.cif
_cod_data_source_block           q
_cod_original_cell_volume        791.9(4)
_cod_database_code               7245840
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C14(H14), C10(H10), C11(H11), C9(H9), C1(H1), C16(H16),
 C15(H15), C5(H5), C18(H18), C3(H3), C4(H4), C2(H2), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.58564(9) 0.34270(6) 0.77191(3) 0.03438(15) Uani 1 1 d . . . . .
S1 S 0.66162(11) 0.16398(7) 0.68575(3) 0.04897(18) Uani 1 1 d . . . . .
O1 O 0.3386(2) 0.3269(2) 0.76380(10) 0.0500(4) Uani 1 1 d . . . . .
C7 C 0.7658(3) 0.5555(2) 0.76721(11) 0.0330(4) Uani 1 1 d . . . . .
C13 C 0.6913(4) 0.2980(2) 0.86833(12) 0.0376(4) Uani 1 1 d . . . . .
C6 C 0.5745(4) 0.2159(3) 0.59026(12) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.9807(4) 0.5944(3) 0.74188(13) 0.0438(5) Uani 1 1 d . . . . .
H8 H 1.041556 0.508247 0.725762 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6795(4) 0.6860(3) 0.79253(13) 0.0430(5) Uani 1 1 d . . . . .
H12 H 0.536511 0.660446 0.809743 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9175(4) 0.3127(3) 0.89326(14) 0.0508(6) Uani 1 1 d . . . . .
H14 H 1.026134 0.344464 0.858965 0.061 Uiso 1 1 calc R U . . .
C10 C 1.0141(5) 0.8926(3) 0.76595(16) 0.0596(7) Uani 1 1 d . . . . .
H10 H 1.096232 1.005421 0.764798 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8048(5) 0.8536(3) 0.79229(15) 0.0560(6) Uani 1 1 d . . . . .
H11 H 0.746847 0.940572 0.810137 0.067 Uiso 1 1 calc R U . . .
C9 C 1.1032(4) 0.7642(3) 0.74105(14) 0.0551(6) Uani 1 1 d . . . . .
H9 H 1.245895 0.791279 0.723602 0.066 Uiso 1 1 calc R U . . .
C1 C 0.7403(5) 0.2868(4) 0.54534(16) 0.0647(7) Uani 1 1 d . . . . .
H1 H 0.896012 0.312699 0.566132 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8234(5) 0.2319(4) 1.02051(16) 0.0677(8) Uani 1 1 d . . . . .
H16 H 0.868575 0.211056 1.071935 0.081 Uiso 1 1 calc R U . . .
C15 C 0.9825(5) 0.2798(4) 0.96994(16) 0.0648(7) Uani 1 1 d . . . . .
H15 H 1.135469 0.290393 0.987004 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3449(5) 0.1771(4) 0.55875(16) 0.0649(7) Uani 1 1 d . . . . .
H5 H 0.231535 0.128923 0.588646 0.078 Uiso 1 1 calc R U . . .
C18 C 0.5324(5) 0.2468(4) 0.91945(16) 0.0701(8) Uani 1 1 d . . . . .
H18 H 0.378301 0.233457 0.902552 0.084 Uiso 1 1 calc R U . . .
C3 C 0.4476(7) 0.2803(4) 0.43794(17) 0.0797(9) Uani 1 1 d . . . . .
H3 H 0.404790 0.301591 0.386367 0.096 Uiso 1 1 calc R U . . .
C4 C 0.2836(6) 0.2104(5) 0.48201(18) 0.0824(9) Uani 1 1 d . . . . .
H4 H 0.128365 0.184559 0.460557 0.099 Uiso 1 1 calc R U . . .
C2 C 0.6748(7) 0.3193(4) 0.46929(18) 0.0846(10) Uani 1 1 d . . . . .
H2 H 0.787121 0.368385 0.439202 0.101 Uiso 1 1 calc R U . . .
C17 C 0.6004(6) 0.2150(5) 0.99570(18) 0.0867(10) Uani 1 1 d . . . . .
H17 H 0.492364 0.181934 1.030041 0.104 Uiso 1 1 calc R U . . .
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 S1 115.52(7) . . ?
O1 P1 C7 111.30(9) . . ?
O1 P1 C13 112.54(9) . . ?
C7 P1 S1 108.52(7) . . ?
C13 P1 S1 100.32(7) . . ?
C13 P1 C7 107.90(9) . . ?
C6 S1 P1 100.78(7) . . ?
C8 C7 P1 124.58(15) . . ?
C12 C7 P1 115.70(15) . . ?
C12 C7 C8 119.71(19) . . ?
C14 C13 P1 124.20(16) . . ?
C14 C13 C18 119.0(2) . . ?
C18 C13 P1 116.77(18) . . ?
C1 C6 S1 119.04(19) . . ?
C5 C6 S1 121.18(18) . . ?
C5 C6 C1 119.7(2) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.7(3) . . ?
C2 C1 H1 120.1 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C13 C18 H18 119.8 . . ?
C13 C18 C17 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.0836(9) . ?
P1 O1 1.4817(16) . ?
P1 C7 1.807(2) . ?
P1 C13 1.804(2) . ?
S1 C6 1.785(2) . ?
C7 C8 1.393(3) . ?
C7 C12 1.387(3) . ?
C13 C14 1.377(3) . ?
C13 C18 1.380(3) . ?
C6 C1 1.375(3) . ?
C6 C5 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C10 C9 1.383(4) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(4) . ?
C16 C17 1.352(4) . ?
C15 H15 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(4) . ?
C3 C2 1.359(5) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
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
_geom_torsion_publ_flag
P1 S1 C6 C1 112.02(19) . . . . ?
P1 S1 C6 C5 -71.8(2) . . . . ?
P1 C7 C8 C9 -179.96(16) . . . . ?
P1 C7 C12 C11 179.22(16) . . . . ?
P1 C13 C14 C15 178.21(19) . . . . ?
P1 C13 C18 C17 -178.0(3) . . . . ?
S1 P1 C7 C8 -26.50(19) . . . . ?
S1 P1 C7 C12 154.69(14) . . . . ?
S1 P1 C13 C14 60.33(19) . . . . ?
S1 P1 C13 C18 -119.9(2) . . . . ?
S1 C6 C1 C2 176.6(2) . . . . ?
S1 C6 C5 C4 -176.3(2) . . . . ?
O1 P1 C7 C8 -154.69(17) . . . . ?
O1 P1 C7 C12 26.50(18) . . . . ?
O1 P1 C13 C14 -176.33(18) . . . . ?
O1 P1 C13 C18 3.4(2) . . . . ?
C7 P1 C13 C14 -53.1(2) . . . . ?
C7 P1 C13 C18 126.6(2) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C7 C12 C11 C10 0.9(3) . . . . ?
C13 P1 C7 C8 81.37(19) . . . . ?
C13 P1 C7 C12 -97.45(17) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C13 C18 C17 C16 -0.8(5) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C5 C4 C3 0.1(5) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C14 C13 C18 C17 1.7(4) . . . . ?
C11 C10 C9 C8 0.5(4) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
C4 C3 C2 C1 0.7(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C17 C16 C15 C14 0.5(5) . . . . ?
