Preparation of 3-Aryl-2-aminoindoles via Rhodium-Catalyzed Coupling Reaction between 2-Arylpyridines and 3-Diazoindolin-2-imines.
Li, Zhenmin; Zhou, Xiaorong; Lu, Ping; Wang, Yanguang; The Journal of organic chemistry 81 (2016) 9433–9437; doi:10.1021/acs.joc.6b01678

data_4037187
_publ_section_title
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 Preparation of 3-Aryl-2-aminoindoles via Rhodium-Catalyzed Coupling
 Reaction between 2-Arylpyridines and 3-Diazoindolin-2-imines.
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_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9433
_journal_page_last               9437
_journal_paper_doi               10.1021/acs.joc.6b01678
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C28 H22 F3 N3 O2 S'
_chemical_formula_sum            'C28 H22 F3 N3 O2 S'
_chemical_formula_weight         521.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-22
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90.495(6)
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_cell_angle_gamma                99.530(5)
_cell_formula_units_Z            2
_cell_length_a                   8.6878(5)
_cell_length_b                   11.5528(7)
_cell_length_c                   13.1521(10)
_cell_measurement_reflns_used    2860
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5418
_cell_measurement_theta_min      3.2688
_cell_volume                     1228.05(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0089885000
_diffrn_orient_matrix_UB_12      -0.0052301000
_diffrn_orient_matrix_UB_13      -0.0514601000
_diffrn_orient_matrix_UB_21      -0.0831113000
_diffrn_orient_matrix_UB_22      -0.0298266000
_diffrn_orient_matrix_UB_23      -0.0216218000
_diffrn_orient_matrix_UB_31      -0.0267019000
_diffrn_orient_matrix_UB_32      0.0545554000
_diffrn_orient_matrix_UB_33      -0.0123661000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7861
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+1.0084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                3594
_reflns_number_total             4481
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01678_si_002.cif
_cod_data_source_block           160421_lzm9366_1
_cod_original_cell_volume        1228.04(14)
_cod_database_code               4037187
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1 f6'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C28(H28A,H28B,H28C)
;