NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3'-spirocyclic oxindoles via a C-F bond cleavage protocol.
Yan, Jun; Shi, Kuangxi; Zhao, Chengtao; Ding, Liyuan; Jiang, Shengsheng; Yang, Limin; Zhong, Guofu; Chemical communications (Cambridge, England) 54 (2018) 1567–1570; doi:10.1039/c7cc08048d

data_7120960
_publ_section_title
;
 NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of
 3'-spirocyclic oxindoles via a C-F bond cleavage protocol.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1567
_journal_page_last               1570
_journal_paper_doi               10.1039/c7cc08048d
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H26 Br N O3'
_chemical_formula_sum            'C37 H26 Br N O3'
_chemical_formula_weight         612.50
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-02 deposited with the CCDC.
2017-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0961(5)
_cell_length_b                   18.4979(11)
_cell_length_c                   9.1885(11)
_cell_measurement_reflns_used    14356
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3075.8(4)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1688
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7016
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.7153
_exptl_absorpt_correction_T_min  0.6400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T.(1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.039(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2007
_refine_ls_R_factor_gt           0.0917
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0807P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                3202
_reflns_number_total             7016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc08048d2.cif
_cod_data_source_block           yj-br-sq
_cod_depositor_comments          'Adding full bibliography for 7120960.cif.'
_cod_database_code               7120960