Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy.
Wan, Ying; Wang, Hai-Qing; Xu, Meng-Meng; Mei, Guang-Jian; Shi, Feng; Organic & biomolecular chemistry 16 (2018) 1536–1542; doi:10.1039/c7ob03182c

data_7156088
_publ_section_title
;
 Direct C3-arylations of 2-indolylmethanols with tryptamines and
 tryptophols via an umpolung strategy.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1536
_journal_page_last               1542
_journal_paper_doi               10.1039/c7ob03182c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C32 H28 N2 O2'
_chemical_formula_sum            'C32 H28 N2 O2'
_chemical_formula_weight         472.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-12-13 deposited with the CCDC.
2018-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.451(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.672(3)
_cell_length_b                   17.459(4)
_cell_length_c                   23.660(5)
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.52
_cell_volume                     5642(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27698
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.487
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0597 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.8887. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     672
_refine_ls_number_reflns         9858
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1349P)^2^+1.7626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5870
_reflns_number_total             9858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03182c2.cif
_cod_data_source_block           sf20170406_xmm_0m
_cod_depositor_comments
'Adding full bibliography for 7156088--7156089.cif.'
_cod_database_code               7156088
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4-C65 = O5-C64
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C63 \\sim O5 \\sim O4 \\sim C64 \\sim C65: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O4(0.5) H4(0.5) O5(0.5) H5(0.5) H63A(0.5) H63B(0.5) H63C(0.5)
 H63D(0.5) C64(0.5) H64A(0.5) H64B(0.5) C65(0.5) H65A(0.5) H65B(0.5)
5.a Ternary CH refined with riding coordinates:
 C50(H50), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C63(H63A,H63B), C63(H63C,H63D), C64(H64A,H64B), C65(H65A,H65B), C31(H31A,
 H31B), C32(H32A,H32B)
5.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4A), C34(H34), C35(H35), C36(H36), C37(H37), C44(H44), C45(H45),
 C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C58(H58), C59(H59),
  C60(H60), C61(H61), C62(H62), N1(H1), N2(H2A), C2(H2B), C3(H3A), C4(H4B),
 C5(H5A), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
5.d Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C17(H17A,H17B,H17C)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O2(H2)
;
_shelx_res_checksum              49432
_shelx_fab_checksum              73335
_olex2_submission_special_instructions 'No special instructions were received'