Organocatalytic Arylation of 3-Indolylmethanols via Chemo- and Regiospecific C6-Functionalization of Indoles.
Zhou, Lu-Jia; Zhang, Yu-Chen; Zhao, Jia-Jia; Shi, Feng; Tu, Shu-Jiang; The Journal of organic chemistry 79 (2014) 10390–; doi:10.1021/jo501989x

data_4030091
_publ_section_title
;
 Organocatalytic Arylation of 3-Indolylmethanols via Chemo- and
 Regiospecific C6-Functionalization of Indoles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10390
_journal_paper_doi               10.1021/jo501989x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C33 H27 N3 O, C3 H6 O'
_chemical_formula_sum            'C36 H33 N3 O2'
_chemical_formula_weight         539.68
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                94.978(10)
_cell_angle_beta                 104.479(9)
_cell_angle_gamma                90.047(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0471(13)
_cell_length_b                   11.2646(16)
_cell_length_c                   14.820(2)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      2.31
_cell_volume                     1456.5(4)
_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  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24084
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8491.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2305
_exptl_crystal_description       block
_exptl_crystal_F_000             572.2396
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.4228
_refine_diff_density_min         -0.4479
_refine_diff_density_rms         0.1231
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             14.2918
_refine_ls_goodness_of_fit_ref   1.0897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    57
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0897
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0826
_refine_ls_shift/su_max          0.0637
_refine_ls_shift/su_mean         0.0013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1418P)^2^+0.5263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2873
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3055
_reflns_number_total             5699
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo501989x_si_002.cif
_cod_data_source_block           SF140710_ZYC_0m
_cod_depositor_comments          'Adding full bibliography for 4030091.cif.'
_cod_database_code               4030091
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25),
  C26(H26), C29(H29)
2.c Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C33(H33a,H33b,H33c), C34(H34a,H34b,H34c), C36(H36a,H36b,
 H36c)
;
_olex2_submission_special_instructions 'No special instructions were received'