N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.
Chen, Xiang-Yu; Chen, Kun-Quan; Sun, De-Qun; Ye, Song; Chemical science 8 (2017) 1936–1941; doi:10.1039/c6sc04135c

data_1544536
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of
 dioxindoles and enals: cross coupling of homoenolate and enolate.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1936
_journal_page_last               1941
_journal_paper_doi               10.1039/c6sc04135c
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Br N O3'
_chemical_formula_sum            'C24 H18 Br N O3'
_chemical_formula_weight         448.30
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8078(18)
_cell_length_b                   9.5713(19)
_cell_length_c                   23.675(5)
_cell_measurement_reflns_used    6395
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      2.2952
_cell_volume                     1995.9(7)
_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., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0021
_diffrn_orient_matrix_UB_12      0.0936
_diffrn_orient_matrix_UB_13      -0.0642
_diffrn_orient_matrix_UB_21      0.0039
_diffrn_orient_matrix_UB_22      0.0591
_diffrn_orient_matrix_UB_23      0.0860
_diffrn_orient_matrix_UB_31      0.0422
_diffrn_orient_matrix_UB_32      -0.0003
_diffrn_orient_matrix_UB_33      -0.0017
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21667
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0275P)^2^+0.6964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0671
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4407
_reflns_number_total             4513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc04135c2.cif
_cod_data_source_block           sa3789
_cod_depositor_comments
;Adding full bibliography for 1544536.cif.

 Adding full bibliography for 1544536.cif.
;
_cod_original_cell_volume        1995.8(7)
_cod_database_code               1544536
_shelxl_version_number           2013-4
_diffrn_number_total             2619
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              41738