The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: asymmetric synthesis of 3,3-disubstituted oxindoles.
Lachia, Mathilde; Poriel, Cyril; Slawin, Alexandra M Z; Moody, Christopher J; Chemical communications (Cambridge, England)  (2007) 286–288; doi:10.1039/b613716d

data_7101649
_publ_section_title
;
 The remarkable effect of the 7-substituent in the diastereoselective
 oxidative rearrangement of indoles: asymmetric synthesis of
 3,3-disubstituted oxindoles.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              286
_journal_page_last               288
_journal_paper_doi               10.1039/b613716d
_journal_year                    2007
_chemical_formula_moiety         'C21 H21 Br N2 O3.(C H Cl3)0.5'
_chemical_formula_sum            'C21.5 H21.5 Br Cl1.5 N2 O3'
_chemical_formula_weight         488.99
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.099(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.64370(19)
_cell_length_b                   12.4445(12)
_cell_length_c                   18.3737(17)
_cell_measurement_reflns_used    7230
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.35
_cell_measurement_theta_min      2.46
_cell_volume                     2156.1(3)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1652
_diffrn_reflns_av_sigmaI/netI    0.1397
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28203
_diffrn_reflns_theta_full        67.98
_diffrn_reflns_theta_max         67.98
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    4.520
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3940
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         7217
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0858
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0122P)^2^+14.1128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                4900
_reflns_number_total             7217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b613716d.txt
_cod_data_source_block           8b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C21.50 H21.50 Br Cl1.50 N2 O3'
_cod_database_code               7101649