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_7156823
_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_formula_moiety         'C36 H39 Ir N2 P, C32 H12 B F24'
_chemical_formula_sum            'C68 H51 B F24 Ir N2 P'
_chemical_formula_weight         1586.08
_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             2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-22 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.88950(10)
_cell_length_b                   18.6285(2)
_cell_length_c                   13.36600(10)
_cell_measurement_reflns_used    58401
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.6920
_cell_measurement_theta_min      3.5620
_cell_volume                     3204.74(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -104.00  74.00   0.50    7.00    --  -15.00  45.00 160.58  356
  2  \w   -104.00  74.00   0.50    7.00    --  -15.00  45.00  30.00  356
  3  \w   -104.00  74.00   0.50    7.00    --  -15.00  45.00  60.00  356
  4  \w   -104.00 -57.00   0.50    7.00    --  -15.00  45.00  -1.68   94
  5  \w    -18.00  53.00   0.50    7.00    --  -15.00  45.00  -1.68  142
  6  \w   -104.00 -70.00   0.50    7.00    --  -15.00  45.00  83.06   68
  7  \w     17.00  74.00   0.50    7.00    --  -15.00  45.00  83.06  114
  8  \w     23.00  49.00   0.50    7.00    --  -15.00  45.00 173.59   52
  9  \w   -104.00 -58.00   0.50    7.00    --  -15.00  45.00  10.93   92
 10  \w   -104.00  74.00   0.50    7.00    --  -15.00  45.00 102.36  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547268000
_diffrn_orient_matrix_UB_12      0.0045038000
_diffrn_orient_matrix_UB_13      -0.0010815000
_diffrn_orient_matrix_UB_21      0.0022631000
_diffrn_orient_matrix_UB_22      0.0030639000
_diffrn_orient_matrix_UB_23      0.0529787000
_diffrn_orient_matrix_UB_31      0.0061999000
_diffrn_orient_matrix_UB_32      0.0376656000
_diffrn_orient_matrix_UB_33      -0.0041476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            82317
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.813
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'intense orange'
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       block
_exptl_crystal_F_000             1572
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.356
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 7673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0143(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     876
_refine_ls_number_reflns         18000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                17226
_reflns_number_total             18000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00770a2.cif
_cod_data_source_block           mx7689b
_cod_depositor_comments
'Adding full bibliography for 7156822--7156826.cif.'
_cod_database_code               7156823
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNBPFIr
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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:
 C1(H1), C29(H29), C30(H30), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C31(H31A,H31B), C32(H32A,H32B), C35(H35A,H35B),
 C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C38(H38), C40(H40), C42(H42), C46(H46), C48(H48), C50(H50), C54(H54),
 C56(H56), C58(H58), C62(H62), C64(H64), C66(H66)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              80282
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.877