An organocatalytic enantioselective vinylogous Mannich reaction of α,α-dicyanoolefins with isatin N-Boc ketimines
Zhu, Yi; Li, Yao; Meng, Qingbin; Li, Xin; Organic Chemistry Frontiers 3 (2016) 709–; doi:10.1039/C6QO00038J

data_1553431
_publ_section_title
;
 An organocatalytic enantioselective vinylogous Mannich reaction of
 \a,\a-dicyanoolefins with isatin N-Boc ketimines
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              709
_journal_paper_doi               10.1039/C6QO00038J
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H28 N4 O3'
_chemical_formula_sum            'C31 H28 N4 O3'
_chemical_formula_weight         504.57
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.063(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.837(2)
_cell_length_b                   10.113(2)
_cell_length_c                   14.456(3)
_cell_measurement_reflns_used    934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      77.70
_cell_measurement_theta_min      30.30
_cell_volume                     1382.0(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23289
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         77.819
_diffrn_reflns_theta_min         6.351
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 2210 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5369
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0422P)^2^+0.1432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                5303
_reflns_number_total             5369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00038j2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1553431
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.812
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              62922
_shelx_hkl_checksum              61579