Tandem addition of nucleophilic and electrophilic reagents to vinyl phosphinates: the stereoselective formation of organophosphorus compounds with congested tertiary carbons
Lin, Zhu; Zhai, De-Hua; Sun, Yong-Ming; Zheng, Hong-Xing; Li, Qiang; Wang, Yan-Lan; Wen, Jing-Hong; Zhao, Chang-Qiu; RSC Advances 13 (2023) 14060–14064; doi:10.1039/D3RA02409A

data_7246765
_publ_section_title
;
 Tandem addition of nucleophilic and electrophilic reagents to vinyl
 phosphinates: the stereoselective formation of organophosphorus compounds
 with congested tertiary carbons
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              14060
_journal_page_last               14064
_journal_paper_doi               10.1039/D3RA02409A
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H27 O P'
_chemical_formula_sum            'C18 H27 O P'
_chemical_formula_weight         290.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-03 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.262(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3136(8)
_cell_length_b                   10.1805(9)
_cell_length_c                   9.9531(8)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.510
_cell_measurement_theta_min      2.346
_cell_volume                     879.49(13)
_computing_cell_refinement       'SAINT V6.36A (?, 2016)'
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.1267
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4105
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.346
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0873
_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/[\s^2^(Fo^2^)+1.1850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.839
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                1773
_reflns_number_total             2842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02409a2.cif
_cod_data_source_block           221102h
_cod_database_code               7246765
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 C25-C24
 1.52 with sigma of 0.02
 C6-C2
 1.37 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C24(H24A,H24B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C21(H21), C22(H22), C23(H23)
3.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              21277
_olex2_submission_special_instructions 'No special instructions were received'