N-Heterocyclic carbene catalyzed chemo- and enantioselective cross-benzoin reaction of aldehydes with isatins
Xu, Jianfeng; Peng, Jingyi; He, Chonglong; Ren, Hongjun; Organic Chemistry Frontiers 6 (2019) 172–; doi:10.1039/C8QO01085D

data_1554496
_publ_section_title
;
 N-Heterocyclic carbene catalyzed chemo- and enantioselective
 cross-benzoin reaction of aldehydes with isatins
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              172
_journal_paper_doi               10.1039/C8QO01085D
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C30 H25 N O3'
_chemical_formula_weight         447.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-09-01 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.310(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5256(3)
_cell_length_b                   16.9053(5)
_cell_length_c                   8.9274(3)
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1340
_cell_measurement_theta_min      5.6330
_cell_volume                     1190.37(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4216
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        67.249
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_min         5.233
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_coef       0.0103(11)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0601P)^2^+0.1634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.430
_reflns_Friedel_fraction_full    0.463
_reflns_Friedel_fraction_max     0.463
_reflns_number_gt                3081
_reflns_number_total             3161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01085d2.cif
_cod_data_source_block           exp_9466
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554496
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              50213
_shelx_hkl_checksum              75235