#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:54:13 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302698 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/56/1575630.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_1575630
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         'C15 H21 P S'
_chemical_formula_sum            'C15 H21 P S'
_chemical_formula_weight         264.35
_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
;
2025-07-24 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.283(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.439(14)
_cell_length_b                   8.332(5)
_cell_length_c                   15.055(9)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.479
_cell_measurement_theta_min      2.601
_cell_volume                     2875(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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -29
_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            25186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.516
_diffrn_reflns_theta_min         1.777
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0439 before and 0.0375 after correction.
The Ratio of minimum to maximum transmission is 0.9383.
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    1.221
_exptl_crystal_description       blade
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0326
_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)+(0.0386P)²+3.1621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3811
_reflns_number_total             4393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01781e2.cif
_cod_data_source_block           dg661_a
_cod_depositor_comments
'Adding full bibliography for 1575627--1575631.cif.'
_cod_database_code               1575630
_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   0.971
_shelx_estimated_absorpt_t_min   0.869
_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), C6(H6A,H6B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_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 0.28714(2) 0.45370(4) 0.27602(2) 0.02103(8) Uani 1 1 d . . . . .
P1 P 0.40836(2) 0.56015(4) 0.29694(2) 0.01941(8) Uani 1 1 d . . . . .
C12 C 0.42751(4) 0.46067(13) 0.48455(7) 0.01416(19) Uani 1 1 d . . . . .
C7 C 0.41669(5) 0.41146(14) 0.39068(7) 0.01471(19) Uani 1 1 d . . . . .
C11 C 0.43711(5) 0.34488(14) 0.55520(7) 0.0152(2) Uani 1 1 d . . . . .
H11 H 0.444410 0.378508 0.618569 0.018 Uiso 1 1 calc R U . . .
C10 C 0.43632(5) 0.18182(14) 0.53565(7) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.41694(5) 0.24623(14) 0.37006(7) 0.0162(2) Uani 1 1 d . . . . .
C9 C 0.42647(5) 0.13467(14) 0.44251(8) 0.0168(2) Uani 1 1 d . . . . .
H9 H 0.426262 0.023556 0.428228 0.020 Uiso 1 1 calc R U . . .
C1 C 0.33560(5) 0.56125(13) 0.23769(8) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.31347(5) 0.65581(14) 0.14616(7) 0.0177(2) Uani 1 1 d . . . . .
H2A H 0.344837 0.727984 0.142658 0.021 Uiso 1 1 calc R U . . .
H2B H 0.280283 0.723545 0.146596 0.021 Uiso 1 1 calc R U . . .
C14 C 0.44527(6) 0.05892(15) 0.61253(9) 0.0233(2) Uani 1 1 d . . . . .
H14A H 0.458733 0.112332 0.674359 0.035 Uiso 1 1 calc R U . . .
H14B H 0.474557 -0.019341 0.609718 0.035 Uiso 1 1 calc R U . . .
H14C H 0.408341 0.003669 0.603625 0.035 Uiso 1 1 calc R U . . .
C15 C 0.42850(5) 0.63508(14) 0.51036(9) 0.0206(2) Uani 1 1 d . . . . .
H15A H 0.457837 0.691238 0.491141 0.031 Uiso 1 1 calc R U . . .
H15B H 0.438287 0.645359 0.578975 0.031 Uiso 1 1 calc R U . . .
H15C H 0.390031 0.682438 0.477797 0.031 Uiso 1 1 calc R U . . .
C6 C 0.21628(5) 0.47643(16) 0.18415(10) 0.0246(3) Uani 1 1 d . . . . .
H6A H 0.186504 0.429867 0.207457 0.030 Uiso 1 1 calc R U . . .
H6B H 0.207820 0.592528 0.173874 0.030 Uiso 1 1 calc R U . . .
C3 C 0.29359(6) 0.54779(16) 0.05742(8) 0.0236(2) Uani 1 1 d . . . . .
H3A H 0.302119 0.603589 0.005637 0.028 Uiso 1 1 calc R U . . .
H3B H 0.316936 0.447847 0.071601 0.028 Uiso 1 1 calc R U . . .
C13 C 0.40729(6) 0.18702(17) 0.27116(8) 0.0246(3) Uani 1 1 d . . . . .
H13A H 0.368563 0.220431 0.228913 0.037 Uiso 1 1 calc R U . . .
H13B H 0.409892 0.069631 0.271529 0.037 Uiso 1 1 calc R U . . .
H13C H 0.437137 0.232515 0.248741 0.037 Uiso 1 1 calc R U . . .
C4 C 0.22928(6) 0.50330(18) 0.02275(9) 0.0283(3) Uani 1 1 d . . . . .
H4A H 0.220012 0.445842 -0.038272 0.034 Uiso 1 1 calc R U . . .
H4B H 0.206159 0.603659 0.010142 0.034 Uiso 1 1 calc R U . . .
C5 C 0.20940(6) 0.39986(17) 0.08914(10) 0.0309(3) Uani 1 1 d . . . . .
H5A H 0.167788 0.372343 0.056948 0.037 Uiso 1 1 calc R U . . .
H5B H 0.231841 0.298348 0.100829 0.037 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 105.89(7) . . ?
C1 P1 C7 103.02(5) . . ?
C7 C12 C15 121.52(10) . . ?
C11 C12 C7 119.23(11) . . ?
C11 C12 C15 119.25(10) . . ?
C12 C7 P1 120.54(9) . . ?
C12 C7 C8 119.46(10) . . ?
C8 C7 P1 119.80(9) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 121.93(10) . . ?
C10 C11 H11 119.0 . . ?
C11 C10 C9 118.27(10) . . ?
C11 C10 C14 121.02(10) . . ?
C9 C10 C14 120.70(11) . . ?
C7 C8 C13 121.68(10) . . ?
C9 C8 C7 119.47(10) . . ?
C9 C8 C13 118.85(11) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.62(11) . . ?
C8 C9 H9 119.2 . . ?
P1 C1 S1 122.40(7) . . ?
C2 C1 S1 120.09(9) . . ?
C2 C1 P1 117.47(8) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.97(11) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C6 H6A 108.3 . . ?
S1 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C5 C6 S1 116.00(10) . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.67(10) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
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 . . ?
C3 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C3 C4 C5 116.11(11) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C6 C5 C4 115.08(12) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
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 1.7357(13) . ?
S1 C6 1.8132(15) . ?
P1 C7 1.8354(13) . ?
P1 C1 1.6906(15) . ?
C12 C7 1.4057(16) . ?
C12 C11 1.3943(16) . ?
C12 C15 1.5022(18) . ?
C7 C8 1.4117(18) . ?
C11 H11 0.9500 . ?
C11 C10 1.3887(18) . ?
C10 C9 1.3943(17) . ?
C10 C14 1.5035(17) . ?
C8 C9 1.3899(16) . ?
C8 C13 1.5075(17) . ?
C9 H9 0.9500 . ?
C1 C2 1.5150(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5429(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.521(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.520(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(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 -71.32(12) . . . . ?
S1 C6 C5 C4 -85.52(14) . . . . ?
P1 C7 C8 C9 176.48(8) . . . . ?
P1 C7 C8 C13 -3.33(15) . . . . ?
P1 C1 C2 C3 106.47(10) . . . . ?
C12 C7 C8 C9 1.57(16) . . . . ?
C12 C7 C8 C13 -178.25(10) . . . . ?
C12 C11 C10 C9 1.01(16) . . . . ?
C12 C11 C10 C14 -178.42(10) . . . . ?
C7 P1 C1 S1 5.80(9) . . . . ?
C7 P1 C1 C2 -171.93(8) . . . . ?
C7 C12 C11 C10 0.00(16) . . . . ?
C7 C8 C9 C10 -0.55(17) . . . . ?
C11 C12 C7 P1 -176.18(8) . . . . ?
C11 C12 C7 C8 -1.30(15) . . . . ?
C11 C10 C9 C8 -0.73(16) . . . . ?
C1 S1 C6 C5 66.08(11) . . . . ?
C1 P1 C7 C12 -104.58(9) . . . . ?
C1 P1 C7 C8 80.56(10) . . . . ?
C1 C2 C3 C4 91.60(13) . . . . ?
C2 C3 C4 C5 -64.93(16) . . . . ?
C14 C10 C9 C8 178.70(11) . . . . ?
C15 C12 C7 P1 4.30(14) . . . . ?
C15 C12 C7 C8 179.18(10) . . . . ?
C15 C12 C11 C10 179.54(10) . . . . ?
C6 S1 C1 P1 -174.40(8) . . . . ?
C6 S1 C1 C2 3.27(11) . . . . ?
C3 C4 C5 C6 62.49(16) . . . . ?
C13 C8 C9 C10 179.27(10) . . . . ?
