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_7157744
_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         'C36 H26 N2 O2'
_chemical_formula_sum            'C36 H26 N2 O2'
_chemical_formula_weight         518.59
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-17 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   12.96320(10)
_cell_length_b                   12.96320(10)
_cell_length_c                   16.2424(2)
_cell_measurement_reflns_used    12431
_cell_measurement_temperature    294
_cell_measurement_theta_max      79.1950
_cell_measurement_theta_min      2.7300
_cell_volume                     2363.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_temperature      294
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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      8.00  36.00   0.50    0.50    --    5.00  29.00 -11.00   56
  2  \w    -66.00 -21.00   0.50    0.50    --  -50.90  29.00 -11.00   90
  3  \w   -163.00-138.00   0.50    1.00    -- -110.00 -29.00-172.00   50
  4  \w    -85.00 -59.00   0.50    1.00    -- -110.00  29.00 -11.00   52
  5  \w    -49.00 -24.00   0.50    0.50    --  -50.90 -42.00  60.05   50
  6  \w   -139.00 -24.00   0.50    0.50    --  -50.90 -44.00 100.54  230
  7  \w   -186.00-149.00   0.50    1.00    -- -110.00 -42.00   1.12   74
  8  \w   -130.00 -97.00   0.50    1.00    -- -110.00  72.00-180.00   66
  9  \w   -190.00-113.00   0.50    1.00    -- -110.00 -49.00  75.21  154
 10  \w   -133.00 -83.00   0.50    1.00    -- -110.00 -60.00 110.15  100
 11  \w   -103.00 -49.00   0.50    1.00    -- -110.00  72.00  90.00  108
 12  \w   -122.00 -96.00   0.50    1.00    -- -110.00 -64.00   3.21   52
 13  \w   -166.00 -84.00   0.50    1.00    -- -110.00 -50.00  35.14  164
 14  \w   -168.00-142.00   0.50    1.00    -- -110.00 -42.00 122.79   52
 15  \w   -198.00-168.00   0.50    1.00    -- -110.00 -69.00  23.16   60
 16  \w   -134.00 -83.00   0.50    1.00    -- -110.00 -69.00  23.16  102
 17  \w   -195.00-103.00   0.50    1.00    -- -110.00 -41.00 -70.08  184
 18  \w   -105.00 -33.00   0.50    1.00    -- -110.00  48.00 143.24  144
 19  \w   -180.00-154.00   0.50    1.00    -- -110.00 -64.00   3.21   52
 20  \w   -130.00 -88.00   0.50    1.00    -- -110.00 -43.00 -11.79   84
 21  \w    -95.00 -70.00   0.50    1.00    -- -110.00  72.00 120.00   50
 22  \w   -123.00 -97.00   0.50    1.00    -- -110.00 -42.00   1.12   52
 23  \w   -199.00 -90.00   0.50    1.00    -- -110.00 -51.00 -54.56  218
 24  \w    -97.00 -71.00   0.50    1.00    -- -110.00  57.00 150.00   52
 25  \w   -127.00-101.00   0.50    1.00    -- -110.00  72.00 150.00   52
 26  \w   -137.00 -74.00   0.50    1.00    -- -110.00  57.00  60.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0978241000
_diffrn_orient_matrix_UB_12      0.0344163000
_diffrn_orient_matrix_UB_13      -0.0011927000
_diffrn_orient_matrix_UB_21      0.0894600000
_diffrn_orient_matrix_UB_22      0.1227089000
_diffrn_orient_matrix_UB_23      -0.0361474000
_diffrn_orient_matrix_UB_31      -0.0355350000
_diffrn_orient_matrix_UB_32      -0.0509810000
_diffrn_orient_matrix_UB_33      -0.0876543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21690
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         79.925
_diffrn_reflns_theta_min         3.938
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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    1.093
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_coef       0.0095(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6231
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.0188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.806
_reflns_number_gt                5726
_reflns_number_total             6231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02127j2.cif
_cod_data_source_block           p20190115a_sq
_cod_depositor_comments
'Adding full bibliography for 7157743--7157745.cif.'
_cod_original_cell_volume        2363.77(5)
_cod_database_code               7157744
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C37H27NO3
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C23-C24 = C23-C24A
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C24A) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C26A) \\sim Ueq,
Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C29A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H23A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=
 Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=1-FVAR(1)
 Sof(H23)=Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C23(H23), C23(H23A)
5.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C25A(H25A),
 C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A)
5.d Fitted hexagon refined as free rotating group:
 C24(C25,C26,C27,C28,C29), C24A(C25A,C26A,C27A,C28A,C29A)
;
_shelx_res_checksum              13080
_shelx_hkl_checksum              92005
_shelx_fab_checksum              56412
_platon_squeeze_void_probe_radius 1.20
_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 1.434
_oxdiff_exptl_absorpt_empirical_full_min 0.778