Chiral Bisphosphine Ligands based on Quinoline Oligoamide Foldamer: Application in Asymmetric Hydrogenation
Zheng, Lu; Zheng, Dan; Wang, Yanru; Yu, Chengyuan; Zhang, Kun; Jiang, Hua; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB01649J

data_7157178
_publ_section_title
;
 Chiral Bisphosphine Ligands based on Quinoline Oligoamide Foldamer:
 Application in Asymmetric Hydrogenation
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB01649J
_journal_year                    2019
_chemical_formula_moiety         'C68 H57 N7 O7 P2, 3(C H Cl3)'
_chemical_formula_sum            'C71 H60 Cl9 N7 O7 P2'
_chemical_formula_weight         1504.25
_chemical_properties_physical    Oxygen-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-10 deposited with the CCDC.    2019-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.948(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2392(7)
_cell_length_b                   11.0026(5)
_cell_length_c                   33.5952(16)
_cell_measurement_reflns_used    7460
_cell_measurement_temperature    101
_cell_measurement_theta_max      72.8780
_cell_measurement_theta_min      3.9140
_cell_volume                     6957.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.958
_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    -46.00 -13.00   1.00    6.00    --  -41.62 -57.00 -90.00   33
  2  \w   -122.00 -43.00   1.00    6.00    --  -41.62 -19.00 150.00   79
  3  \w    -72.00  37.00   1.00    6.00    --  -41.62  19.00 -30.00  109
  4  \w     83.00 176.00   1.00   35.00    --  107.19  45.00 150.00   93
  5  \w     96.00 178.00   1.00   35.00    --  107.19 125.00  30.00   82
  6  \w     39.00 135.00   1.00   35.00    --  107.19 -30.00 -30.00   96
  7  \w    104.00 171.00   1.00   35.00    --  107.19 125.00  90.00   67
  8  \w     65.00 107.00   1.00   35.00    --  107.19 -61.00 -60.00   42
  9  \w     52.00 105.00   1.00   35.00    --  107.19 -94.00 120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0687953000
_diffrn_orient_matrix_UB_12      0.0103057000
_diffrn_orient_matrix_UB_13      0.0327622000
_diffrn_orient_matrix_UB_21      0.0427751000
_diffrn_orient_matrix_UB_22      -0.0509746000
_diffrn_orient_matrix_UB_23      -0.0301883000
_diffrn_orient_matrix_UB_31      0.0113444000
_diffrn_orient_matrix_UB_32      0.1301426000
_diffrn_orient_matrix_UB_33      -0.0145509000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.1093
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            25470
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.555
_diffrn_reflns_theta_min         3.920
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     888
_refine_ls_number_reflns         13445
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.1092
_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^)+(0.1027P)^2^+63.1562P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2783
_refine_ls_wR_factor_ref         0.2979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9796
_reflns_number_total             13445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01649j2.cif
_cod_data_source_block           20180712b
_cod_database_code               7157178
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c1h1n1o1p1
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.485
_reflns_odcompleteness_completeness 99.70
_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. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O2A)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C42) \\sim Ueq,
Uanis(C37) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C30)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C47(H47), C33(H33), C88(H88), C92(H92), C96(H96)
4.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C32(H32A,H32B)
4.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N5(H5), N3(H3), C44(H44), C40(H40), C39(H39), C38(H38), C24(H24),
 C25(H25), C26(H26), C30(H30), C8(H8), C4(H4), C3(H3A), C2(H2), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C11(H11), C12(H12), C13(H13), C14(H14),
  C15(H15), C54(H54), C55(H55), C56(H56), C52(H52), C58(H58), C59(H59),
 C60(H60), C61(H61), C62(H62), C68(H68), C67(H67), C66(H66), C65(H65), C64(H64)
4.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C)
;
_shelx_res_checksum              14711
_shelx_hkl_checksum              20544
_shelx_fab_checksum              738
_olex2_date_sample_data_collection 2018-07-12
_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 3.960
_oxdiff_exptl_absorpt_empirical_full_min 0.405