Binaphthyl-based chiral ligands: design, synthesis and evaluation of their performance in enantioselective addition of diethylzinc to aromatic aldehydes.
Yao, Chao; Wu, Piao; Huang, Yue; Chen, Yaoqi; Li, Lin; Li, Yue-Ming; Organic & biomolecular chemistry 18 (2020) 9712–9725; doi:10.1039/d0ob02127j

data_7157743
_publ_section_title
;
 Binaphthyl-based chiral ligands: design, synthesis and evaluation of
 their performance in enantioselective addition of diethylzinc to aromatic
 aldehydes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9712
_journal_page_last               9725
_journal_paper_doi               10.1039/d0ob02127j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H29 N O4'
_chemical_formula_sum            'C37 H29 N O4'
_chemical_formula_weight         551.61
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-10-17 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                66.4290(10)
_cell_angle_beta                 80.6470(10)
_cell_angle_gamma                75.0790(10)
_cell_formula_units_Z            2
_cell_length_a                   10.77140(10)
_cell_length_b                   11.31850(10)
_cell_length_c                   13.33430(10)
_cell_measurement_reflns_used    39112
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      73.8640
_cell_measurement_theta_min      3.6000
_cell_volume                     1436.53(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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    -89.00  30.00   0.50    0.50    --    0.00 -57.00   0.00  238
  2  \w    -13.00 113.00   0.50    0.50    --   24.00  81.00 -47.76  252
  3  \w     15.00 141.00   0.50    0.54    --   52.00  82.00   3.65  252
  4  \w     16.00 141.00   0.50    0.54    --   52.00  78.00 130.57  250
  5  \w     27.00 153.00   0.50    0.54    --   64.00  82.00-112.45  252
  6  \w     27.00 153.00   0.50    0.54    --   64.00  82.00-177.79  252
  7  \w     27.00 153.00   0.50    0.54    --   64.00  82.00-112.45  252
  8  \w     31.00 157.00   0.50    0.54    --   68.00  82.00 -70.74  252
  9  \w     31.00 157.00   0.50    0.54    --   68.00  82.00  39.48  252
 10  \w     35.00 161.00   0.50    0.54    --   72.00  82.00 107.48  252
 11  \w     44.00 169.00   0.50    0.54    --   80.00  80.00-143.89  250
 12  \w     43.00 169.00   0.50    0.54    --   80.00  81.00 -33.68  252
 13  \w     43.00 169.00   0.50    0.54    --   80.00  82.00 135.55  252
 14  \w     47.00 173.00   0.50    0.54    --   84.00  82.00  58.47  252
 15  \w     47.00 173.00   0.50    0.54    --   84.00  81.00 -57.75  252
 16  \w     51.00 177.00   0.50    0.54    --   88.00  82.00 161.73  252
 17  \w     52.00 177.00   0.50    0.54    --   88.00  80.00  22.82  250
 18  \w     51.00 177.00   0.50    0.54    --   88.00  81.00   8.51  252
 19  \w      6.00 126.00   0.50    0.54    --   95.80 -61.00 150.00  240
 20  \w     63.00 185.00   0.50    0.54    --   95.80  39.00 113.26  244
 21  \w     65.00 185.00   0.50    0.54    --   95.80  45.00 -90.00  240
 22  \w      6.00 133.00   0.50    0.54    --   95.80 -82.00  60.00  254
 23  \w      6.00 133.00   0.50    0.54    --   95.80 -82.00-120.00  254
 24  \w     58.00 185.00   0.50    0.54    --   95.80  82.00 -30.00  254
 25  \w     65.00 185.00   0.50    0.54    --   95.80  61.00 120.00  240
 26  \w     60.00 185.00   0.50    0.54    --   95.80  77.00-120.00  250
 27  \w     65.00 185.00   0.50    0.54    --   95.80  61.00-150.00  240
 28  \w     60.00 185.00   0.50    0.54    --   95.80  77.00 -90.00  250
 29  \w      6.00 133.00   0.50    0.54    --   95.80 -82.00 150.00  254
 30  \w     65.00 185.00   0.50    0.54    --   95.80  61.00-150.00  240
 31  \w      6.00 133.00   0.50    0.54    --   95.80 -82.00 -30.00  254
 32  \w      6.00 131.00   0.50    0.54    --   95.80 -77.00 -90.00  250
 33  \w     63.00 185.00   0.50    0.54    --   95.80  38.00-149.29  244
 34  \w    -89.00  89.00   0.50    0.50    --    0.00   0.00-150.00  356
 35  \w    -89.00  89.00   0.50    0.50    --    0.00   0.00-180.00  356
 36  \w    -65.00  54.00   0.50    0.50    --   24.00 -47.00 111.51  238
 37  \w      7.00 133.00   0.50    0.50    --   44.00  81.00-113.69  252
 38  \w      6.00  85.00   0.50    0.54    --   95.80 -61.00   0.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0643668000
_diffrn_orient_matrix_UB_12      -0.0533847000
_diffrn_orient_matrix_UB_13      0.1164802000
_diffrn_orient_matrix_UB_21      0.0813729000
_diffrn_orient_matrix_UB_22      -0.1392682000
_diffrn_orient_matrix_UB_23      0.0167635000
_diffrn_orient_matrix_UB_31      0.1060333000
_diffrn_orient_matrix_UB_32      0.0292117000
_diffrn_orient_matrix_UB_33      0.0459582000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54918
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.234
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 5192 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         11105
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0355P)^2^+0.1861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                10914
_reflns_number_total             11105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02127j2.cif
_cod_data_source_block           lym-yc-p9-shang
_cod_depositor_comments
'Adding full bibliography for 7157743--7157745.cif.'
_cod_database_code               7157743
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 99.65
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C54(H54A,H54B), C55(H55A,H55B), C59(H59A,H59B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C8(H8A), C11(H11), C17(H17), C19(H19), C22(H22), C23(H23),
 C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32), C36(H36), C37(H37),
  C39(H39), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47),
 C48(H48), C49(H49), C50(H50), C52(H52), C53(H53), C56(H56), C57(H57), C58(H58),
  C60(H60), C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C66(H66),
 C67(H67), C68(H68), C69(H69), C70(H70), C71(H71), C72(H72), C73(H73), C74(H74)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O8(H8)
;
_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 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.909