Enantioselective construction of a 2,2'-bisindolylmethane scaffold via catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles.
Gong, Yu-Xin; Wu, Qiong; Zhang, Hong-Hao; Zhu, Qiu-Ning; Shi, Feng; Organic & biomolecular chemistry 13 (2015) 7993–8000; doi:10.1039/c5ob00815h

data_7154534
_publ_section_title
;
 Enantioselective construction of a 2,2'-bisindolylmethane scaffold via
 catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7993
_journal_page_last               8000
_journal_paper_doi               10.1039/c5ob00815h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H28 N2'
_chemical_formula_sum            'C28 H28 N2'
_chemical_formula_weight         392.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-04-21 deposited with the CCDC.
2015-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.20980(10)
_cell_length_b                   8.35700(10)
_cell_length_c                   14.8849(2)
_cell_measurement_reflns_used    5514
_cell_measurement_temperature    130
_cell_measurement_theta_max      69.206
_cell_measurement_theta_min      3.079
_cell_volume                     1104.62(2)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8154
_diffrn_reflns_point_group_measured_fraction_full 0.834
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.612
_diffrn_reflns_theta_min         3.079
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.6881.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0781P)^2^+0.1966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.551
_reflns_Friedel_fraction_full    0.647
_reflns_Friedel_fraction_max     0.627
_reflns_number_gt                3327
_reflns_number_total             3399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00815h2.cif
_cod_data_source_block           cu_sf150318_0m
_cod_depositor_comments          'Adding full bibliography for 7154534.cif.'
_cod_database_code               7154534
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C22(H22), C24(H24), C26(H26)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              59550
_olex2_submission_special_instructions 'No special instructions were received'