Regioselective synthesis of 2,3′-biindoles mediated by an NBS-induced homo-coupling of indoles
Liu, Liangxian; Huang, Panpan; Peng, Xiangjun; Hu, Dan; Liao, Huiwu; Tang, Shaobin; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02312J

data_7155956
_publ_section_title
;
 Regioselective synthesis of 2,3&#x2032;-biindoles mediated by an
 NBS-induced homo-coupling of indoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02312J
_journal_year                    2017
_chemical_formula_moiety         'C24 H14 Cl3 N3'
_chemical_formula_sum            'C24 H14 Cl3 N3'
_chemical_formula_weight         450.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                108.992(5)
_cell_angle_beta                 90.760(5)
_cell_angle_gamma                104.392(5)
_cell_formula_units_Z            2
_cell_length_a                   8.9064(8)
_cell_length_b                   11.4166(9)
_cell_length_c                   12.9485(12)
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.37
_cell_volume                     1199.49(19)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_number            4695
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0515 before and 0.0376 after correction. The Ratio of minimum to maximum transmission is 0.8785. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
;
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1851P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2677
_refine_ls_wR_factor_ref         0.2951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             4695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02312j2.cif
_cod_data_source_block           p-1-sr
_cod_original_cell_volume        1199.48(19)
_cod_database_code               7155956
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C10(H10), C16(H16), C18(H18), C2(H2A), C17(H17), C3(H3),
 C4(H4), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'