The stereoselective conversion of epimerized alkoxyl phosphine–borane to P,C, axial-stereogenic tertiary phosphine via cleavage of P–O bond
Zhai, De-Hua; Yan, Bing-Xia; Li, Zhan-Cai; Lin, Zhu; Li, Qiang; Wang, Yan-Lan; Zheng, Hong-Xing; Zhao, Chang-Qiu; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00351A

data_7158572
_publ_section_title
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 The stereoselective conversion of epimerized alkoxyl phosphine--borane to
 P,C, axial-stereogenic tertiary phosphine via cleavage of P--O bond
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00351A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H35 B O P'
_chemical_formula_sum            'C25 H35 B O P'
_chemical_formula_weight         393.31
_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             2021-09-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-22 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1696(8)
_cell_length_b                   10.0689(9)
_cell_length_c                   25.845(2)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.041
_cell_measurement_theta_min      2.357
_cell_volume                     2386.2(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.987
_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  0.1006
_diffrn_reflns_av_unetI/netI     0.1244
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11197
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.171
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     762
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1715
_refine_ls_R_factor_gt           0.1046
_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^)+(0.1604P)^2^+0.1593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2575
_refine_ls_wR_factor_ref         0.2980
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2139
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00351a2.cif
_cod_data_source_block           210821d
_cod_database_code               7158572
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C12(H12), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C16(H16A,H16B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C15(H15), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              84350
_olex2_submission_special_instructions 'No special instructions were received'