Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(indolyl)methane and 3,3'-Bisindole Derivatives.
He, Ying-Ying; Sun, Xiao-Xue; Li, Guo-Hao; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 82 (2017) 2462–2471; doi:10.1021/acs.joc.6b02850

data_4032177
_publ_section_title
;
 Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with
 Indoles: Synthesis of Bis(indolyl)methane and 3,3'-Bisindole Derivatives.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2462
_journal_page_last               2471
_journal_paper_doi               10.1021/acs.joc.6b02850
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C29 H21 Br N2'
_chemical_formula_sum            'C29 H21 Br N2'
_chemical_formula_weight         477.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4357(7)
_cell_length_b                   18.8121(14)
_cell_length_c                   12.7774(9)
_cell_measurement_reflns_used    7557
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.177
_cell_measurement_theta_min      2.44
_cell_volume                     2238.3(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.697
_diffrn_reflns_theta_min         1.944
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0360 before and 0.0291 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0396P)^2^+1.0479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5398
_reflns_number_total             6919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02850_si_002.cif
_cod_data_source_block           mo_dm16904_0m
_cod_depositor_comments          'Adding full bibliography for 4032177.cif.'
_cod_database_code               4032177
_shelx_estimated_absorpt_t_max   0.731
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5), C8(H8), C12(H12), C13(H13), C14(H14),
  C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              11030
_shelx_hkl_checksum              87529
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'