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_7246766
_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 multi-scan
_chemical_formula_moiety         'C27 H38 Cl O2 P'
_chemical_formula_sum            'C27 H38 Cl O2 P'
_chemical_formula_weight         460.99
_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             2022-06-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-31 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.214(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7102(11)
_cell_length_b                   5.9519(5)
_cell_length_c                   18.9788(18)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      23.552
_cell_measurement_theta_min      2.094
_cell_volume                     1417.2(2)
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_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 0.975
_diffrn_measured_fraction_theta_max 0.995
_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  0.1000
_diffrn_reflns_av_unetI/netI     0.1211
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.093
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.1149
_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^)+(0.1807P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2925
_refine_ls_wR_factor_ref         0.3311
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                2203
_reflns_number_total             4720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02409a2.cif
_cod_data_source_block           220605d
_cod_database_code               7246766
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.980
_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:
 C3(H3), C6(H6), C7(H7), C10(H10), C14(H14), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C19(H19A,H19B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              95202
_olex2_submission_special_instructions 'No special instructions were received'