Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton shift and [3+2] cycloaddition: an efficient strategy for the synthesis of oxindole derivatives
Li Tian; Xiu-Qin Hu; Yun-Han Li; Peng-Fei Xu; Chem.Commun. 49 (2013) 7213–; doi:10.1039/c3cc43755h

data_7109606
_publ_section_title
;
 Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton
 shift and [3+2] cycloaddition: an efficient strategy for the synthesis of
 oxindole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              7213
_journal_paper_doi               10.1039/c3cc43755h
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H24 Br N3 O3'
_chemical_formula_sum            'C30 H24 Br N3 O3'
_chemical_formula_weight         554.43
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-29
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4213(5)
_cell_length_b                   13.1929(4)
_cell_length_c                   17.2730(5)
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3190
_cell_measurement_theta_min      3.7340
_cell_volume                     2602.70(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8791
_diffrn_measurement_details
;
  1 omega   -4.00   22.40   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000 -120.0000 22

  2 omega   24.00   84.00   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  -90.0000 50

  3 omega   24.00   48.00   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  -30.0000 20

  4 omega   -2.00   89.20   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000   30.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0102751000
_diffrn_orient_matrix_UB_12      -0.0023609000
_diffrn_orient_matrix_UB_13      -0.0404571000
_diffrn_orient_matrix_UB_21      0.0604670000
_diffrn_orient_matrix_UB_22      -0.0086097000
_diffrn_orient_matrix_UB_23      -0.0065707000
_diffrn_orient_matrix_UB_31      -0.0093614000
_diffrn_orient_matrix_UB_32      -0.0530335000
_diffrn_orient_matrix_UB_33      0.0029279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9098
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0177P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                3382
_reflns_number_total             5296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43755h.txt
_cod_data_source_block           tianli0327
_cod_original_cell_volume        2602.68(16)
_cod_database_code               7109606
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H29 of C29, H14 of C14, H21 of C21, H12 of C12, H15 of C15, H13 of C13, H20
  of C20, H30 of C30, H16 of C16, H17 of C17, H24 of C24, H23 of C23, H26 of
  C26, H22 of C22, H18 of C18, H27 of C27, H11 of C11, {H9A,H9B} of C9, H5 of
  C5, H4 of C4, H3 of C3, H2A of C2
2.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C29(H29), C30(H30)
;