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_7156826
_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 H45 Ir N2 P'
_chemical_formula_sum            'C72 H57 B F24 Ir N2 P'
_chemical_formula_weight         1640.17
_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                   18.457(3)
_cell_length_b                   18.457(3)
_cell_length_c                   41.453(8)
_cell_measurement_reflns_used    29773
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4828
_cell_measurement_theta_min      1.1033
_cell_volume                     14121(4)
_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 1.000
_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  0.1635
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            111062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.199
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.208
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       plate
_exptl_crystal_F_000             6528
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.029
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details
;
 Flack x determined using 3892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     994
_refine_ls_number_reflns         12715
_refine_ls_number_restraints     342
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0900
_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^)+(0.0002P)^2^+118.0183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                12207
_reflns_number_total             12715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00770a2.cif
_cod_data_source_block           mx6497b
_cod_depositor_comments
'Adding full bibliography for 7156822--7156826.cif.'
_cod_original_cell_volume        14121(5)
_cod_database_code               7156826
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.741
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C56 \\sim F10 \\sim F11 \\sim F12 \\sim F10A \\sim F11A \\sim F12A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
C63 \\sim F13 \\sim F14 \\sim F15 \\sim F15A \\sim F13A \\sim F14A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
C72 \\sim F19 \\sim F20 \\sim F21 \\sim F21A \\sim F20A \\sim F19A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C63) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15)
\\sim Ueq, Uanis(F15A) \\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F14A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C72) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F21)
\\sim Ueq, Uanis(F21A) \\sim Ueq, Uanis(F20A) \\sim Ueq, Uanis(F19A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C56) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12)
\\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F12A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(F15A)=Sof(F13A)=Sof(F14A)=1-FVAR(1)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(1)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
 Sof(F21A)=Sof(F20A)=Sof(F19A)=1-FVAR(3)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C15(H15), C35(H35), C36(H36), C39(H39), C40(H40)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B), C20(H20A,H20B), C33(H33A,H33B), C34(H34A,H34B), C37(H37A,H37B),
  C38(H38A,H38B)
4.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), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              91923
_olex2_submission_special_instructions 'No special instructions were received'