Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis
Lu, Zhiwu; Zhang, Haoyang; Yang, Zhiping; Ding, Ning; Meng, Ling; Wang, Jun; ACS Catalysis 9 (2019) 1457–; doi:10.1021/acscatal.8b04787

data_4514764
_publ_section_title
;
 Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to
 Phosphine Ligands for Asymmetric Catalysis
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1457
_journal_paper_doi               10.1021/acscatal.8b04787
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H26 F2 N O2 P'
_chemical_formula_sum            'C27 H26 F2 N O2 P'
_chemical_formula_weight         465.46
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.744(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6041(14)
_cell_length_b                   11.5598(16)
_cell_length_c                   19.577(3)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.611
_cell_volume                     2391.6(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            42394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1173 before and 0.0751 after correction. The Ratio of minimum to maximum transmission is 0.9127. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(4)
_refine_ls_extinction_coef       0.0062(12)
_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   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         10947
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0567P)^2^+0.5140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                9085
_reflns_number_total             10947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04787_si_002.cif
_cod_data_source_block           mo_cxy0268_0m
_cod_database_code               4514764
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.941
_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:
 C13(H13), C15(H15), C22(H22), C40(H40), C41(H41), C48(H48)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C49(H49A,H49B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35),
  C36(H36), C38(H38), C39(H39), C43(H43), C44(H44), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C52(H52B,H52C,
 H52A), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              58264
_shelx_hkl_checksum              66068
_olex2_submission_special_instructions 'No special instructions were received'