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_7246764
_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         'C31 H38 Cl O3 P'
_chemical_formula_sum            'C31 H38 Cl O3 P'
_chemical_formula_weight         525.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-30
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5468(7)
_cell_length_b                   16.2047(16)
_cell_length_c                   27.749(3)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.471
_cell_measurement_theta_min      2.514
_cell_volume                     2943.9(5)
_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 0.978
_diffrn_measured_fraction_theta_max 0.999
_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  0.0963
_diffrn_reflns_av_unetI/netI     0.1371
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11499
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         1.932
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_coef       0.0034(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     918
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0740
_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^)+(0.0944P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.2052
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2227
_reflns_number_total             5177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02409a2.cif
_cod_data_source_block           220530d
_cod_original_cell_volume        2943.8(5)
_cod_database_code               7246764
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.939
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Ternary CH refined with riding coordinates:
 C16(H16), C20(H20), C24(H24), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C23(H23A,H23B), C29(H29A,H29B), C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C32(H32)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C33(H33A,H33B,H33C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              31057
_olex2_submission_special_instructions 'No special instructions were received'