Highly Efficient Synthesis of Mixed 3,3′-Bisindoles via Rh(II)-Catalyzed Three-Component Reaction of 3-Diazooxindoles with Indoles and Ethyl Glyoxylate
Xing, Dong; Jing, Changcheng; Li, Xinfeng; Qiu, Huang; Hu, Wenhao; Organic Letters 15 (2013) 3578–; doi:10.1021/ol401414w

data_1512173
_publ_section_title
;
 Highly Efficient Synthesis of Mixed 3,3&#x2032;-Bisindoles via
 Rh(II)-Catalyzed Three-Component Reaction of 3-Diazooxindoles with
 Indoles and Ethyl Glyoxylate
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3578
_journal_paper_doi               10.1021/ol401414w
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C34 H29 Br N2 O4'
_chemical_formula_weight         609.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.703(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0261(3)
_cell_length_b                   12.2758(4)
_cell_length_c                   20.3157(6)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.33
_cell_volume                     2887.27(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
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_diffrn_reflns_limit_h_max       14
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_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35443
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    1.466
_exptl_absorpt_correction_T_max  0.8211
_exptl_absorpt_correction_T_min  0.5162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.419
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5674
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_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0520P)^2^+1.6463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                4871
_reflns_number_total             5674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401414w_si_002.cif
_cod_data_source_block           z
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1512173