A chemo- and regioselective C6-functionalization of 2,3-disubstituted indoles: highly efficient synthesis of diarylindol-6-ylmethanes.
Wu, Qiong; Li, Gui-Lin; Yang, Shuang; Shi, Xiao-Qin; Huang, Tian-Zi; Du, Xi-Hua; Chen, Yan; Organic & biomolecular chemistry 17 (2019) 3462–3470; doi:10.1039/c9ob00283a

data_7156729
_publ_section_title
;
 A chemo- and regioselective C6-functionalization of 2,3-disubstituted
 indoles: highly efficient synthesis of diarylindol-6-ylmethanes.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3462
_journal_page_last               3470
_journal_paper_doi               10.1039/c9ob00283a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 Cl N O'
_chemical_formula_sum            'C24 H22 Cl N O'
_chemical_formula_weight         375.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-01-26 deposited with the CCDC.    2019-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.189(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.424(3)
_cell_length_b                   12.100(2)
_cell_length_c                   19.028(3)
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.66
_cell_measurement_theta_min      2.182
_cell_volume                     3935.4(11)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19722
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.714
_diffrn_reflns_theta_min         2.062
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0462 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.9264.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         6111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.5889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2999
_reflns_number_total             6111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00283a2.cif
_cod_data_source_block           mo_dm16164_0m
_cod_depositor_comments          'Adding full bibliography for 7156729.cif.'
_cod_original_cell_volume        3935.4(12)
_cod_database_code               7156729
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H18)=Sof(O1')=Sof(H1')=1-FVAR(1)
 Sof(H24)=Sof(O1)=Sof(H1A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.d Tetrahedral OH refined with riding coordinates:
 O1'(H1')
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              93944
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'