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_7158573
_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         'C24 H33 B O P'
_chemical_formula_sum            'C24 H33 B O P'
_chemical_formula_weight         379.28
_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             2021-09-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-23 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.398(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6028(9)
_cell_length_b                   14.6741(13)
_cell_length_c                   16.2270(15)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.955
_cell_measurement_theta_min      2.521
_cell_volume                     2276.4(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11606
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.522
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         6809
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0858P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.628
_reflns_Friedel_fraction_full    0.666
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                4270
_reflns_number_total             6809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00351a2.cif
_cod_data_source_block           210821c
_cod_database_code               7158573
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C19(H19), C20(H20), C27(H27), C33(H33), C38(H38), C43(H43)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C18(H18A,H18B), C22(H22A,H22B), C31(H31A,H31B),
 C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B)
1.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C21(H21),
 C32(H32), C34(H34), C35(H35), C37(H37), C39(H39), C41(H41), C45(H45), C47(H47)
1.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,
 H52B,H52C)
1.e Idealised tetrahedral OH refined as rotating group:
 O9(H9), O36(H36)
;
_shelx_res_checksum              27012
_olex2_submission_special_instructions 'No special instructions were received'