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_7156825
_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         'C27 H24 N2 O2 S'
_chemical_formula_sum            'C27 H24 N2 O2 S'
_chemical_formula_weight         440.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-23
_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                86.3960(10)
_cell_angle_beta                 79.0400(10)
_cell_angle_gamma                84.8070(10)
_cell_formula_units_Z            2
_cell_length_a                   7.62910(10)
_cell_length_b                   10.7430(2)
_cell_length_c                   13.7168(2)
_cell_measurement_reflns_used    34190
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.6830
_cell_measurement_theta_min      3.6570
_cell_volume                     1097.99(3)
_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 2018/2 (Sheldrick, 2018)'
_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 0.903
_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    -84.00  94.00   0.50    3.00    --    5.00  45.00  60.00  356
  2  \w    -84.00  94.00   0.50    3.00    --    5.00  45.00 120.00  356
  3  \w    -84.00  94.00   0.50    3.00    --    5.00  45.00  60.00  356
  4  \w    -84.00  94.00   0.50    3.00    --    5.00  45.00  90.00  356
  5  \w    -84.00  94.00   0.50    3.00    --    5.00  45.00 120.00  356
  6  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00 -18.93  356
  7  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00  90.00  356
  8  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00  30.00  356
  9  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00 150.00  356
 10  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00  90.00  356
 11  \w   -104.00  74.00   0.50    3.00    --  -15.00  45.00 179.61  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      0.0246648000
_diffrn_orient_matrix_UB_12      -0.0002504000
_diffrn_orient_matrix_UB_13      -0.0525253000
_diffrn_orient_matrix_UB_21      -0.0861594000
_diffrn_orient_matrix_UB_22      -0.0176231000
_diffrn_orient_matrix_UB_23      -0.0029408000
_diffrn_orient_matrix_UB_31      -0.0315352000
_diffrn_orient_matrix_UB_32      0.0639858000
_diffrn_orient_matrix_UB_33      -0.0035687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54082
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.629
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80645
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0564P)^2^+0.2842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5442
_reflns_number_total             6122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00770a2.cif
_cod_data_source_block           mx7654
_cod_depositor_comments
'Adding full bibliography for 7156822--7156826.cif.'
_cod_database_code               7156825
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHONS
_reflns_odcompleteness_completeness 99.73
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              57718
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.770