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_7156089
_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_absolute_configuration unk
_chemical_formula_sum            'C36 H35 N3 O2'
_chemical_formula_weight         541.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-12-13 deposited with the CCDC.
2018-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.500(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9636(17)
_cell_length_b                   12.2439(14)
_cell_length_c                   33.362(4)
_cell_measurement_reflns_used    2601
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      41.166
_cell_measurement_theta_min      4.396
_cell_volume                     6073.1(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
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_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            20737
_diffrn_reflns_point_group_measured_fraction_full 0.768
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_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.229
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1142 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   4.5(10)
_refine_ls_extinction_coef       0.00051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         8659
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_full    0.536
_reflns_Friedel_fraction_max     0.533
_reflns_number_gt                4647
_reflns_number_total             8659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03182c2.cif
_cod_data_source_block           mo_dm16248_0m
_cod_depositor_comments
'Adding full bibliography for 7156088--7156089.cif.'
_cod_database_code               7156089
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
_shelx_res_checksum              3910