Copper-Catalyzed Indole-Selective C-N Coupling Reaction of Indolyl(2-alkoxy-phenyl)iodonium Imides: Effect of Substituent on Iodoarene as Dummy Ligand.
Watanabe, Kazuhiro; Moriyama, Katsuhiko; The Journal of organic chemistry 83 (2018) 14827–14833; doi:10.1021/acs.joc.8b02676

data_4035678
_publ_section_title
;
 Copper-Catalyzed Indole-Selective C-N Coupling Reaction of
 Indolyl(2-alkoxy-phenyl)iodonium Imides: Effect of Substituent on
 Iodoarene as Dummy Ligand.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14827
_journal_page_last               14833
_journal_paper_doi               10.1021/acs.joc.8b02676
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C27 H28 N2 O5 S2'
_chemical_formula_weight         524.63
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                98.118(3)
_cell_angle_beta                 91.348(3)
_cell_angle_gamma                100.871(3)
_cell_formula_units_Z            2
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_cell_length_b                   10.144(2)
_cell_length_c                   13.660(3)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.1036
_cell_measurement_theta_min      2.7372
_cell_volume                     1274.7(5)
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_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
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_computing_publication_material  'XCIF (Bruker AXS, 2001)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.948
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_min         1.51
_diffrn_source                   'fine-focus sealed tube'
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_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
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_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0892
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_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^)+(0.0446P)^2^+0.1253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3559
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_reflns_threshold_expression     'I > 2\s(I)'
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