Phospha-Peterson reactions with esters and thioesters: isolation of phosphaalkenes bearing C-heteroatom substituents.
Mitchell, Aaron A.; Heine, Paul A.; Chang, Joseph; De Paolis, Adam; Patrick, Brian O.; Gates, Derek P.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 14277–14285; doi:10.1039/d5dt01781e

data_1575631
_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         'C21 H33 P S'
_chemical_formula_sum            'C21 H33 P S'
_chemical_formula_weight         348.50
_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'
_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                 113.080(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6018(4)
_cell_length_b                   29.0289(11)
_cell_length_c                   12.3545(4)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.46
_cell_measurement_theta_min      3.04
_cell_volume                     4157.7(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 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            69739
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.749
_diffrn_reflns_theta_min         3.045
_exptl_absorpt_coefficient_mu    2.070
_exptl_absorpt_correction_T_max  0.8300
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8367.
The \l/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    1.113
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0432
_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/[\s^2^(Fo^2^)+(0.0591P)^2^+3.2677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6551
_reflns_number_total             7503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01781e2.cif
_cod_data_source_block           dg691_a
_cod_depositor_comments
'Adding full bibliography for 1575627--1575631.cif.'
_cod_database_code               1575631
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.647
_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 Ternary CH refined with riding coordinates:
 C16(H16), C37(H37), C40(H40), C34(H34), C19(H19), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C23(H23A,H23B), C27(H27A,H27B), C24(H24A,H24B),
 C3(H3A,H3B), C5(H5A,H5B), C26(H26A,H26B), C25(H25A,H25B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C32(H32), C9(H9), C30(H30)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C41(H41A,H41B,H41C), C20(H20A,H20B,H20C), C42(H42A,H42B,
 H42C), C17(H17A,H17B,H17C), C39(H39A,H39B,H39C), C18(H18A,H18B,H18C), C36(H36A,
 H36B,H36C), C38(H38A,H38B,H38C), C35(H35A,H35B,H35C), C15(H15A,H15B,H15C),
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              61048
_shelx_hkl_checksum              80851
_olex2_submission_special_instructions 'No special instructions were received'