N-Heterocyclic Carbene-Catalyzed Diastereoselective and Enantioselective Reaction of 2-Aroylvinylcinnamaldehydes with α,β-Unsaturated Imines: Complete Control and Switch of Diastereoselectivity by N-Substituents of Catalysts.
Wang, Zi-Tian; Zhao, Yuan; Wang, Zhan-Yong; Cheng, Ying; The Journal of organic chemistry 80 (2015) 1727–1734; doi:10.1021/jo502668c

data_4030589
_publ_section_title
;
 N-Heterocyclic Carbene-Catalyzed Diastereoselective and Enantioselective
 Reaction of 2-Aroylvinylcinnamaldehydes with \a,\b-Unsaturated Imines:
 Complete Control and Switch of Diastereoselectivity by N-Substituents of
 Catalysts.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1727
_journal_page_last               1734
_journal_paper_doi               10.1021/jo502668c
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C44 H40 Br N O6 S'
_chemical_formula_sum            'C44 H40 Br N O6 S'
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_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                95.904(9)
_cell_angle_beta                 103.415(6)
_cell_angle_gamma                92.267(4)
_cell_formula_units_Z            4
_cell_length_a                   13.0210(13)
_cell_length_b                   13.5047(14)
_cell_length_c                   22.336(2)
_cell_measurement_reflns_used    11810
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      1.66
_cell_volume                     3792.1(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
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_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51194
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_min         1.519
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.149
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.0115(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     968
_refine_ls_number_reflns         21845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.7179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17128
_reflns_number_total             21845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502668c_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4030588--4030589.cif.'
_cod_original_cell_volume        3792.0(7)
_cod_database_code               4030589
_shelx_estimated_absorpt_t_min   0.763
_shelx_estimated_absorpt_t_max   0.832
_shelxl_version_number           2014-1
_shelx_res_checksum              15186
_shelx_hkl_checksum              30763