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_7157745
_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 syn
_chemical_formula_moiety         'C36 H32 N2 O2'
_chemical_formula_sum            'C36 H32 N2 O2'
_chemical_formula_weight         524.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_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                90
_cell_formula_units_Z            4
_cell_length_a                   9.3208(3)
_cell_length_b                   15.9714(5)
_cell_length_c                   19.0521(6)
_cell_measurement_reflns_used    20002
_cell_measurement_temperature    133.15
_cell_measurement_theta_max      32.6990
_cell_measurement_theta_min      2.4180
_cell_volume                     2836.21(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear(Rigaku, 2008)'
_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      133.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0108446000
_diffrn_orient_matrix_UB_12      -0.0239886000
_diffrn_orient_matrix_UB_13      0.0308794000
_diffrn_orient_matrix_UB_21      -0.0727992000
_diffrn_orient_matrix_UB_22      0.0062017000
_diffrn_orient_matrix_UB_23      0.0095124000
_diffrn_orient_matrix_UB_31      -0.0192958000
_diffrn_orient_matrix_UB_32      -0.0368552000
_diffrn_orient_matrix_UB_33      -0.0185083000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38259
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78355
_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    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         7943
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0446P)^2^+0.2840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6741
_reflns_number_total             7943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02127j2.cif
_cod_data_source_block           r20200109b
_cod_depositor_comments
'Adding full bibliography for 7157743--7157745.cif.'
_cod_database_code               7157745
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C36H32N2O2
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-C31 = N2-C31A
 1.48 with sigma of 0.01
 C31-C32 = C32-C33 = C33-C34 = C34-C35 = C35-C36 = C36-C31
 1.54 with sigma of 0.01
 C31A-C32A = C32A-C33A = C33A-C34A = C34A-C35A = C35A-C36A = C36A-C31A
 1.54 with sigma of 0.01
 C31-C33 = C33-C35 = C35-C31 = C32-C34 = C34-C36 = C36-C32
 2.52 with sigma of 0.01
 C31A-C33A = C33A-C35A = C35A-C31A = C32A-C34A = C34A-C36A = C36A-C32A
 2.52 with sigma of 0.01
3. Others
 Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=
 Sof(H33D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)=Sof(H35D)=
 Sof(C36A)=Sof(H36C)=Sof(H36D)=1-FVAR(1)
 Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C22(H22), C31(H31), C31A(H31A)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C32A(H32C,H32D), C33A(H33C,H33D), C34A(H34C,H34D),
 C35A(H35C,H35D), C36A(H36C,H36D)
4.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)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.441
_oxdiff_exptl_absorpt_empirical_full_min 0.620