Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives.
Li, Can; Zhang, Hong-Hao; Fan, Tao; Shen, Yang; Wu, Qiong; Shi, Feng; Organic & biomolecular chemistry 14 (2016) 6932–6936; doi:10.1039/c6ob01282e

data_7155167
_publ_section_title
;
 Br\/onsted acid-catalyzed regioselective reactions of 2-indolylmethanols
 with cyclic enaminone and anhydride leading to C3-functionalized indole
 derivatives.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6932
_journal_page_last               6936
_journal_paper_doi               10.1039/c6ob01282e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C36 H34 N2 O2'
_chemical_formula_sum            'C36 H34 N2 O2'
_chemical_formula_weight         526.65
_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             2015-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.456(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.463(5)
_cell_length_b                   12.095(2)
_cell_length_c                   20.499(5)
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.328
_cell_measurement_theta_min      2.503
_cell_volume                     5780(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      296.15
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 1.000
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19894
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.747
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0540 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.8399. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1492P)^2^+3.8797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             5384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01282e2.cif
_cod_data_source_block           dm15813
_cod_depositor_comments
'Adding full bibliography for 7155167--7155168.cif.'
_cod_original_cell_volume        5781(2)
_cod_database_code               7155167
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.977
_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. Restrained distances
 O2-C36
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C33 \\sim O2 \\sim C36: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(O2) \\sim Ueq, Uanis(C36) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C31(H31), C32(H32), C34(H34), C35(H35)
4.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              56751
_olex2_submission_special_instructions 'No special instructions were received'