N-heterocyclic carbene-catalyzed synthesis of spirocyclopentene-oxindoles from bromoenals.
Zhang, Zhao-Fei; Chen, Kun-Quan; Zhang, Chun-Lin; Ye, Song; Chemical communications (Cambridge, England) 53 (2017) 4327–4330; doi:10.1039/c6cc10304a

data_7120086
_publ_section_title
;
 N-heterocyclic carbene-catalyzed synthesis of spirocyclopentene-oxindoles
 from bromoenals.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4327
_journal_page_last               4330
_journal_paper_doi               10.1039/c6cc10304a
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H24 Br N O'
_chemical_formula_sum            'C31 H24 Br N O'
_chemical_formula_weight         506.42
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-12-29 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.263(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.615(5)
_cell_length_b                   9.870(4)
_cell_length_c                   19.820(9)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      1.6519
_cell_volume                     2411.5(18)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.1745
              2theta: -19.9484
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.1745
              2theta: -19.9484
scan:
    Number of images: 300
               Slice: -110.0000 - 40.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.1745
              2theta: -19.9484
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0148
_diffrn_orient_matrix_UB_12      -0.0734
_diffrn_orient_matrix_UB_13      -0.0312
_diffrn_orient_matrix_UB_21      0.0996
_diffrn_orient_matrix_UB_22      -0.0180
_diffrn_orient_matrix_UB_23      -0.0052
_diffrn_orient_matrix_UB_31      -0.0031
_diffrn_orient_matrix_UB_32      -0.0295
_diffrn_orient_matrix_UB_33      0.0423
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22968
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.198
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.760
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         8634
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.1015
_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^)+4.9160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6805
_reflns_number_total             8634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc10304a2.cif
_cod_data_source_block           sa5000c
_cod_original_cell_volume        2411.7(18)
_cod_database_code               7120086
_diffrn_number_total             10795
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C13(H13C,H13D), C5A(H5AA,H5AB), C13A(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C29(H29), C30(H30), C31A(H31A), C8A(H8A), C3A(H3A), C30A(H30A),
 C31(H31), C18(H18), C16(H16), C28(H28), C27(H27), C9(H9), C9A(H9A), C19(H19),
 C29A(H29A), C21A(H21A), C3(H3), C22A(H22A), C21(H21), C24(H24), C19A(H19A),
 C11(H11), C27A(H27A), C17(H17), C8(H8), C24A(H24A), C28A(H28A), C15(H15),
 C11A(H11A), C17A(H17A), C16A(H16A), C18A(H18A), C15A(H15A), C23A(H23A),
 C10(H10), C23(H23), C22(H22)
;
_shelx_res_checksum              9248
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'