3-Pyrrolyl-oxindoles as efficient nucleophiles for organocatalytic asymmetric synthesis of structurally diverse 3,3'-disubstituted oxindole derivatives
Bao-Dong Cui; Yong You; Jian-Qiang Zhao; Jian Zuo; Zhi-Jun Wu; Xiao-Ying Xu; Xiao-Mei Zhang; Wei-Cheng Yuan; Chem.Commun. 51 (2015) 757–; doi:10.1039/C4cc08364D

data_7116405
_publ_section_title
;
 3-Pyrrolyl-oxindoles as efficient nucleophiles for organocatalytic
 asymmetric synthesis of structurally diverse 3,3'-disubstituted oxindole
 derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              757
_journal_paper_doi               10.1039/C4cc08364D
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 Br N3 O3'
_chemical_formula_weight         441.30
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.736(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7543(7)
_cell_length_b                   6.8067(3)
_cell_length_c                   15.8605(4)
_cell_measurement_reflns_used    1630
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.5071
_cell_measurement_theta_min      4.5254
_cell_volume                     2107.89(13)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4694
_diffrn_reflns_point_group_measured_fraction_full 0.653
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.635
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0839
_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^)+(0.0780P)^2^+6.3900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2290
_reflns_Friedel_coverage         0.214
_reflns_Friedel_fraction_full    0.256
_reflns_Friedel_fraction_max     0.247
_reflns_number_gt                1722
_reflns_number_total             2537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08364d2.cif
_cod_data_source_block           shelxl
_cod_database_code               7116405
_shelx_estimated_absorpt_t_min   0.425
_shelx_estimated_absorpt_t_max   0.534
_shelxl_version_number           2013-4
_shelx_res_checksum              15049