N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines.
Wang, Ming; Huang, Zhijian; Xu, Jianfeng; Chi, Yonggui Robin; Journal of the American Chemical Society 136 (2014) 1214–1217; doi:10.1021/ja411110f

data_4120466
_publ_section_title
;
 N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic
 resolution of azomethine imines.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1214
_journal_page_last               1217
_journal_paper_doi               10.1021/ja411110f
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27.5 H25 Cl N2 O2.5'
_chemical_formula_weight         458.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 110.476(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2680(14)
_cell_length_b                   9.7295(6)
_cell_length_c                   13.1749(10)
_cell_measurement_reflns_used    7365
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      29.2595
_cell_measurement_theta_min      2.2828
_cell_volume                     2313.8(3)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8704
_diffrn_reflns_theta_full        30.65
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.582
_refine_ls_abs_structure_details
;
Flack x determined using 1949 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6194
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0566P)^2^+1.5312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                5258
_reflns_number_total             6194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja411110f_si_002.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C27.50 H25 Cl N2 O2.50'
_cod_database_code               4120466
_shelx_res_checksum              61724
_shelx_hkl_checksum              13014