Organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 3-alkenyl-5-arylfuran-2(3H)-ones.
Wang, Zhen-Hua; Wu, Zhi-Jun; Yue, Deng-Feng; Hu, Wen-Fei; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 52 (2016) 11708–11711; doi:10.1039/c6cc06367e

data_7125043
_publ_section_title
;
 Organocatalytic asymmetric [3+2] cycloaddition of
 N-2,2,2-trifluoroethylisatin ketimines with
 3-alkenyl-5-arylfuran-2(3H)-ones.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11708
_journal_page_last               11711
_journal_paper_doi               10.1039/c6cc06367e
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H20 Br F3 N2 O3, C H Cl3'
_chemical_formula_sum            'C29 H21 Br Cl3 F3 N2 O3'
_chemical_formula_weight         688.74
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-17 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0262(12)
_cell_length_b                   13.8263(14)
_cell_length_c                   17.0090(17)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      2.24
_cell_volume                     2828.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31413
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.013
_diffrn_reflns_theta_min         1.898
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.290
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.5384
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         8298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0423P)^2^+0.0585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                6990
_reflns_number_total             8298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06367e2.cif
_cod_data_source_block           mo_wlx_wzh1_0m
_cod_database_code               7125043
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.403
_shelx_estimated_absorpt_t_max   0.625
_shelx_res_checksum              6659