Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation.
Liu, Youran; Chen, Fei; He, Yan-Mei; Li, Chenghao; Fan, Qing-Hua; Organic & biomolecular chemistry 17 (2019) 5099–5105; doi:10.1039/c9ob00770a

data_7156822
_publ_section_title
;
 Enantioselective synthesis of tunable chiral pyridine-aminophosphine
 ligands and their applications in asymmetric hydrogenation.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5099
_journal_page_last               5105
_journal_paper_doi               10.1039/c9ob00770a
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H12 B F24, C40 H39 Ir N2 P'
_chemical_formula_sum            'C72 H51 B F24 Ir N2 P'
_chemical_formula_weight         1634.12
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-03-22 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4591(5)
_cell_length_b                   18.4591(5)
_cell_length_c                   40.8718(14)
_cell_measurement_reflns_used    35145
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4036
_cell_measurement_theta_min      1.1031
_cell_volume                     13926.6(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            121575
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.377
_diffrn_reflns_theta_min         1.210
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.048
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             6480
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.043
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 5077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1021
_refine_ls_number_reflns         15775
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0679
_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^)+40.8591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                15024
_reflns_number_total             15775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00770a2.cif
_cod_data_source_block           mx6494
_cod_depositor_comments
'Adding full bibliography for 7156822--7156826.cif.'
_cod_original_cell_volume        13926.6(9)
_cod_database_code               7156822
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.572
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F19A-C71 = F21A-C71 = F21-C71 = F20-C71 = F20A-C71 = F19-C71
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C71 \\sim F19 \\sim F20 \\sim F21 \\sim F20A \\sim F19A \\sim F21A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C71) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F21)
\\sim Ueq, Uanis(F20A) \\sim Ueq, Uanis(F19A) \\sim Ueq, Uanis(F21A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F11A)
\\sim Ueq, Uanis(F12A) \\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F4) \\sim Ueq,
Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F5A)
\\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq,
Uanis(F13A) \\sim Ueq, Uanis(F15A) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F14A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F6A)=Sof(F5A)=Sof(F4A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(F11A)=Sof(F12A)=Sof(F10A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
 Sof(F14A)=Sof(F13A)=Sof(F15A)=1-FVAR(3)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(3)
 Sof(F20A)=Sof(F19A)=Sof(F21A)=1-FVAR(4)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(4)
 Fixed X: F11A(0.44118)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C33(H33), C34(H34), C37(H37), C38(H38)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C35(H35A,H35B), C36(H36A,H36B), C39(H39A,H39B),
 C40(H40A,H40B)
5.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C44(H44), C46(H46), C50(H50), C52(H52), C54(H54), C58(H58),
 C60(H60), C62(H62), C66(H66), C68(H68), C70(H70), C2(H2), C3(H3), C4(H4),
 C5(H5), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              49352
_olex2_submission_special_instructions 'No special instructions were received'