#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:54:13 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302698 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/56/1575628.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_1575628
loop_
_publ_author_name
'Mitchell, Aaron A.'
'Heine, Paul A.'
'Chang, Joseph'
'De Paolis, Adam'
'Patrick, Brian O.'
'Gates, Derek P.'
_publ_section_title
;
 Phospha-Peterson reactions with esters and thioesters: isolation of
 phosphaalkenes bearing C-heteroatom substituents.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14277
_journal_page_last               14285
_journal_paper_doi               10.1039/d5dt01781e
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C14 H19 P S'
_chemical_formula_sum            'C14 H19 P S'
_chemical_formula_weight         250.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-08-18 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.280(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.5639(14)
_cell_length_b                   7.9075(5)
_cell_length_c                   14.7859(9)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.545
_cell_measurement_theta_min      2.730
_cell_volume                     2630.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0426
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            61754
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.577
_diffrn_reflns_theta_min         1.810
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.9166.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.295
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0385
_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)+(0.0487P)²+3.6693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3493
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01781e2.cif
_cod_data_source_block           dg689_a
_cod_depositor_comments
'Adding full bibliography for 1575627--1575631.cif.'
_cod_database_code               1575628
_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.
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29132(2) 0.41402(5) 0.75380(2) 0.01967(10) Uani 1 1 d . . . . .
P1 P 0.41543(2) 0.50231(5) 0.70882(2) 0.01676(10) Uani 1 1 d . . . . .
C1 C 0.34077(6) 0.52265(17) 0.69008(8) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.43150(6) 0.36870(19) 0.88685(9) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.31719(6) 0.63553(18) 0.61266(9) 0.0161(2) Uani 1 1 d . . . . .
H2A H 0.349629 0.709820 0.594722 0.019 Uiso 1 1 calc R U . . .
H2B H 0.285386 0.708585 0.633807 0.019 Uiso 1 1 calc R U . . .
C7 C 0.42278(6) 0.33153(18) 0.79362(9) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.42278(6) 0.16198(19) 0.76375(9) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.29221(7) 0.5338(2) 0.52895(9) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.299223 0.599057 0.473626 0.024 Uiso 1 1 calc R U . . .
H3B H 0.314682 0.426540 0.526424 0.024 Uiso 1 1 calc R U . . .
C6 C 0.21770(6) 0.44559(19) 0.69790(10) 0.0193(3) Uani 1 1 d . . . . .
H6A H 0.188236 0.393716 0.735807 0.023 Uiso 1 1 calc R U . . .
H6B H 0.209523 0.568549 0.695065 0.023 Uiso 1 1 calc R U . . .
C11 C 0.43905(6) 0.2354(2) 0.94891(9) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.444390 0.259369 1.011949 0.024 Uiso 1 1 calc R U . . .
C9 C 0.43117(6) 0.0322(2) 0.82740(11) 0.0205(3) Uani 1 1 d . . . . .
H9 H 0.431667 -0.082096 0.807663 0.025 Uiso 1 1 calc R U . . .
C10 C 0.43883(6) 0.0691(2) 0.91967(10) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.443920 -0.020094 0.962605 0.026 Uiso 1 1 calc R U . . .
C13 C 0.41269(7) 0.1178(2) 0.66445(10) 0.0230(3) Uani 1 1 d . . . . .
H13A H 0.372485 0.151900 0.642060 0.034 Uiso 1 1 calc R U . . .
H13B H 0.417186 -0.004506 0.656654 0.034 Uiso 1 1 calc R U . . .
H13C H 0.441840 0.177262 0.630182 0.034 Uiso 1 1 calc R U . . .
C14 C 0.43210(7) 0.5486(2) 0.91984(10) 0.0221(3) Uani 1 1 d . . . . .
H14A H 0.464683 0.610065 0.894352 0.033 Uiso 1 1 calc R U . . .
H14B H 0.437775 0.550052 0.986196 0.033 Uiso 1 1 calc R U . . .
H14C H 0.394216 0.602898 0.900478 0.033 Uiso 1 1 calc R U . . .
C4 C 0.22600(7) 0.4923(2) 0.52775(10) 0.0230(3) Uani 1 1 d . . . . .
H4A H 0.203787 0.599504 0.532460 0.028 Uiso 1 1 calc R U . . .
H4B H 0.213356 0.440970 0.468345 0.028 Uiso 1 1 calc R U . . .
C5 C 0.20818(7) 0.3734(2) 0.60233(11) 0.0232(3) Uani 1 1 d . . . . .
H5A H 0.165655 0.344109 0.590435 0.028 Uiso 1 1 calc R U . . .
H5B H 0.231359 0.267519 0.599314 0.028 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'
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
C1 S1 C6 106.70(7) . . ?
C1 P1 C7 102.64(6) . . ?
P1 C1 S1 122.31(8) . . ?
C2 C1 S1 119.76(10) . . ?
C2 C1 P1 117.90(10) . . ?
C7 C12 C14 120.80(13) . . ?
C11 C12 C7 119.06(14) . . ?
C11 C12 C14 120.14(13) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.59(12) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C12 C7 P1 120.80(11) . . ?
C12 C7 C8 120.07(13) . . ?
C8 C7 P1 119.05(10) . . ?
C7 C8 C13 121.37(13) . . ?
C9 C8 C7 119.38(13) . . ?
C9 C8 C13 119.24(14) . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.73(12) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
S1 C6 H6A 108.4 . . ?
S1 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C5 C6 S1 115.54(10) . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.89(13) . . ?
C10 C11 H11 119.6 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.47(14) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.13(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 115.72(12) . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C6 C5 C4 114.39(12) . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
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
S1 C1 1.7399(14) . ?
S1 C6 1.8165(15) . ?
P1 C1 1.6944(14) . ?
P1 C7 1.8418(14) . ?
C1 C2 1.5163(18) . ?
C12 C7 1.4088(18) . ?
C12 C11 1.400(2) . ?
C12 C14 1.504(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5469(19) . ?
C7 C8 1.412(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.510(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.524(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C10 H10 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
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
S1 C1 C2 C3 -73.75(14) . . . . ?
S1 C6 C5 C4 -86.80(14) . . . . ?
P1 C1 C2 C3 104.20(12) . . . . ?
P1 C7 C8 C9 176.96(10) . . . . ?
P1 C7 C8 C13 -4.24(18) . . . . ?
C1 S1 C6 C5 63.22(12) . . . . ?
C1 P1 C7 C12 -96.35(11) . . . . ?
C1 P1 C7 C8 87.03(11) . . . . ?
C1 C2 C3 C4 90.63(15) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
C12 C7 C8 C13 179.12(12) . . . . ?
C12 C11 C10 C9 0.1(2) . . . . ?
C2 C3 C4 C5 -65.49(17) . . . . ?
C7 P1 C1 S1 6.86(10) . . . . ?
C7 P1 C1 C2 -171.04(10) . . . . ?
C7 C12 C11 C10 0.9(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C3 C4 C5 C6 65.50(17) . . . . ?
C6 S1 C1 P1 -170.37(8) . . . . ?
C6 S1 C1 C2 7.48(12) . . . . ?
C11 C12 C7 P1 -177.69(10) . . . . ?
C11 C12 C7 C8 -1.11(19) . . . . ?
C13 C8 C9 C10 -178.11(13) . . . . ?
C14 C12 C7 P1 2.96(18) . . . . ?
C14 C12 C7 C8 179.54(13) . . . . ?
C14 C12 C11 C10 -179.76(13) . . . . ?
