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_7157177
_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 H56 N6 O8 P2'
_chemical_formula_sum            'C68 H56 N6 O8 P2'
_chemical_formula_weight         1147.12
_chemical_properties_physical    Oxygen-sensitive
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-10
_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                104.059(13)
_cell_angle_beta                 92.816(11)
_cell_angle_gamma                92.523(13)
_cell_formula_units_Z            2
_cell_length_a                   13.6368(19)
_cell_length_b                   14.139(2)
_cell_length_c                   15.614(2)
_cell_measurement_reflns_used    2026
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.7050
_cell_measurement_theta_min      4.1050
_cell_volume                     2912.0(7)
_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)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_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    -72.00  28.00   1.00    5.00    --  -39.74  77.00-150.00  100
  2  \w    -61.00  29.00   1.00    5.00    --  -39.74  37.00 120.00   90
  3  \w   -114.00 -15.00   1.00    5.00    --  -39.74 -37.00 -60.00   99
  4  \w     89.00 128.00   1.00    5.00    --   39.74 178.00-180.00   39
  5  \w     65.00 120.00   1.00    5.00    --   39.74 178.00   0.00   55
  6  \w     81.00 131.00   1.00   22.50    --  107.19  45.00-180.00   50
  7  \w     82.00 178.00   1.00   22.50    --  107.19  61.00 120.00   96
  8  \w     33.00 137.00   1.00   22.50    --  107.19 -77.00  30.00  104
  9  \w    108.00 138.00   1.00   22.50    --  107.19 125.00  60.00   30
 10  \w     43.00 136.00   1.00   22.50    --  107.19 -61.00 150.00   93
 11  \w     81.00 120.00   1.00   22.50    --  107.19-125.00-150.00   39
 12  \w     62.00 121.00   1.00   22.50    --  107.19-125.00  30.00   59
 13  \w     79.00 128.00   1.00   22.50    --  107.19 -45.00 -30.00   49
 14  \w    134.00 161.00   1.00   22.50    --  107.19  45.00-180.00   27
 15  \w     85.00 149.00   1.00   22.50    --  107.19  45.00 -90.00   64
 16  \w     34.00  73.00   1.00   22.50    --  107.19 -45.00 -30.00   39
 17  \w     47.00  90.00   1.00   22.50    --  107.19-125.00   0.00   43
 18  \w     70.00  97.00   1.00   22.50    --  107.19 -95.00-104.00   27
 19  \w     86.00 174.00   1.00   22.50    --  107.19  15.00-120.00   88
;
_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      0.0796014000
_diffrn_orient_matrix_UB_12      -0.0438658000
_diffrn_orient_matrix_UB_13      -0.0620875000
_diffrn_orient_matrix_UB_21      0.0805252000
_diffrn_orient_matrix_UB_22      0.0480384000
_diffrn_orient_matrix_UB_23      0.0720113000
_diffrn_orient_matrix_UB_31      -0.0039183000
_diffrn_orient_matrix_UB_32      -0.0917995000
_diffrn_orient_matrix_UB_33      0.0366737000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1968
_diffrn_reflns_av_unetI/netI     0.2452
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19760
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.614
_diffrn_reflns_theta_min         3.786
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35674
_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 light yellow'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.421
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         11269
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.3369
_refine_ls_R_factor_gt           0.2094
_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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4609
_refine_ls_wR_factor_ref         0.5529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2792
_reflns_number_total             11269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01649j2.cif
_cod_data_source_block           20180510b
_cod_original_cell_volume        2911.9(8)
_cod_database_code               7157177
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         C1H1N1O1P1
_reflns_odcompleteness_completeness 99.75
_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(C61) \\sim Ueq: with sigma of 0.007 and sigma for terminal atoms of 0.013
3.a Riding coordinates:
 N3(H3)
3.b Ternary CH refined with riding coordinates:
 C33(H33), C47(H47)
3.c Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C46(H46A,H46B)
3.d Aromatic/amide H refined with riding coordinates:
 C16(H16), N5(H5), C11(H11), C4(H4), C00L(H00L), C21(H21), C55(H55), C24(H24),
 C18(H18), C3(H3A), C44(H44), C12(H12), C30(H30), C8(H8), C60(H60), C15(H15),
 C39(H39), C67(H67), C56(H56), C14(H14), C2(H2), C19(H19), C40(H40), C13(H13),
 C68(H68), C26(H26), C64(H64), C66(H66), C41(H41), C65(H65), C25(H25), C62(H62),
  C59(H59), C54(H54), C61(H61), C52(H52)
3.e Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C49(H49A,H49B,H49C), C48(H48A,H48B,
 H48C)
;
_shelx_res_checksum              50690
_shelx_hkl_checksum              42197
_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 5.779
_oxdiff_exptl_absorpt_empirical_full_min 0.274