Synthesis of P-chiral phosphine compounds by palladium-catalyzed C-P coupling reactions.
Wang, Cuiying; Yue, Chang-Duo; Yuan, Jia; Zheng, Jia-Lian; Zhang, Ying; Yu, Hong; Chen, Jian; Meng, Sixuan; Yu, Yang; Yu, Guang-Ao; Che, Chi-Ming; Chemical communications (Cambridge, England) 56 (2020) 11775–11778; doi:10.1039/d0cc05340f

data_7127181
_publ_section_title
;
 Synthesis of P-chiral phosphine compounds by palladium-catalyzed C-P
 coupling reactions.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11775
_journal_page_last               11778
_journal_paper_doi               10.1039/d0cc05340f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H28 B P'
_chemical_formula_sum            'C20 H28 B P'
_chemical_formula_weight         310.20
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-12
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-07-21 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2902(16)
_cell_length_b                   12.3392(18)
_cell_length_c                   13.6341(19)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.81
_cell_measurement_theta_min      2.34
_cell_volume                     1899.4(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.866
_diffrn_reflns_theta_min         2.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 2397 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.007(14)
_refine_ls_extinction_coef       0.049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         6144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.2237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                5696
_reflns_number_total             6144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05340f2.cif
_cod_data_source_block           mo_191104b_0m
_cod_depositor_comments
'Adding full bibliography for 7127180--7127181.cif.'
_cod_database_code               7127181
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All B(H,H,H) groups, All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13) 
2.b Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B, 
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C) 
;
_shelx_res_checksum              8149
_olex2_submission_special_instructions 'No special instructions were received'