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_7156824
_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         'C24 H23 N O2'
_chemical_formula_sum            'C24 H23 N O2'
_chemical_formula_weight         357.43
_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             2018-12-13
_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                 92.2391(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.18906(5)
_cell_length_b                   17.89980(10)
_cell_length_c                   11.33563(6)
_cell_measurement_reflns_used    31353
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.7980
_cell_measurement_theta_min      3.9140
_cell_volume                     1863.087(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -92.00  -6.00   0.50    0.10    --  -47.20 119.00-154.00  172
  2  \w   -115.00 -27.00   0.50    0.10    --  -47.20 158.00  -0.00  176
  3  \w   -120.00 -48.00   0.50    0.10    --  -47.20-158.00 -34.00  144
  4  \w     33.00 115.00   0.50    0.10    --   47.20-158.00 -34.00  164
  5  \w     12.00  92.00   0.50    0.10    --   47.20-119.00 119.00  160
  6  \w     55.00 120.00   0.50    0.10    --   47.20 158.00  -0.00  130
  7  \w   -165.00 -48.00   0.50    0.40    --  -99.00-158.00 -34.00  234
  8  \w   -112.00 -26.00   0.50    0.40    --  -99.00 119.00-154.00  172
  9  \w   -168.00 -75.00   0.50    0.40    --  -99.00-119.00 119.00  186
 10  \w     33.00 139.00   0.50    0.40    --  103.25-158.00 -34.00  212
 11  \w     31.00 113.00   0.50    0.40    --  103.25-119.00 119.00  164
 12  \w     81.00 169.00   0.50    0.40    --  103.25 119.00-154.00  176
 13  \w   -120.00 -71.00   0.50    0.10    --  -47.20-125.00-180.00   98
 14  \w    -60.00  26.00   0.50    0.10    --  -47.20  38.00  30.00  172
 15  \w   -120.00 -24.00   0.50    0.10    --  -47.20 -77.00  60.00  192
 16  \w     32.00 120.00   0.50    0.10    --   47.20  57.00   0.00  176
 17  \w   -115.00 -26.00   0.50    0.40    --  -99.00  61.00  60.00  178
 18  \w   -112.00 -27.00   0.50    0.40    --  -99.00  45.00  60.00  170
 19  \w   -168.00 -86.00   0.50    0.40    --  -99.00 -45.00-150.00  164
 20  \w   -117.00 -26.00   0.50    0.40    --  -99.00 125.00 -90.00  182
 21  \w   -139.00 -27.00   0.50    0.40    --  -99.00 158.00  -0.00  224
 22  \w   -168.00 -85.00   0.50    0.40    --  -99.00 -15.00-180.00  166
 23  \w   -168.00 -86.00   0.50    0.40    --  -99.00 -45.00  30.00  164
 24  \w     90.00 169.00   0.50    0.40    --  103.25  15.00 -30.00  158
 25  \w     31.00 120.00   0.50    0.40    --  103.25 -61.00  90.00  178
 26  \w     43.00 126.00   0.50    0.40    --  103.25 -77.00 -60.00  166
 27  \w     32.00 109.00   0.50    0.40    --  103.25 -94.00-120.00  154
 28  \w     34.00 117.00   0.50    0.40    --  103.25-125.00-120.00  166
 29  \w     32.00 109.00   0.50    0.40    --  103.25 -45.00  90.00  154
 30  \w     91.00 169.00   0.50    0.40    --  103.25  45.00 -60.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0040684000
_diffrn_orient_matrix_UB_12      -0.0812673000
_diffrn_orient_matrix_UB_13      0.0447814000
_diffrn_orient_matrix_UB_21      -0.0564899000
_diffrn_orient_matrix_UB_22      0.0259591000
_diffrn_orient_matrix_UB_23      0.1194138000
_diffrn_orient_matrix_UB_31      -0.1578660000
_diffrn_orient_matrix_UB_32      -0.0114072000
_diffrn_orient_matrix_UB_33      -0.0473915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35116
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.349
_diffrn_reflns_theta_min         3.903
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.221
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 3356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7394
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0557P)^2^+0.4195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                7274
_reflns_number_total             7394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00770a2.cif
_cod_data_source_block           tx194
_cod_depositor_comments
'Adding full bibliography for 7156822--7156826.cif.'
_cod_original_cell_volume        1863.087(17)
_cod_database_code               7156824
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHON
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C13(H13), C15(H15),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), N1A(H1A), C2A(H2A), C3A(H3A),
  C4A(H4A), C5A(H5A), C7A(H7A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C19A(H19A), C20A(H20A), C22A(H22A), C23A(H23A)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C17A(H17D,H17E,H17F), C24A(H24D,
 H24E,H24F)
;
_shelx_res_checksum              20566
_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 2.032
_oxdiff_exptl_absorpt_empirical_full_min 0.504