Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds.
Guo, Xin; Han, Jianwei; Liu, Yafeng; Qin, Mingda; Zhang, Xueguo; Chen, Baohua; The Journal of organic chemistry 82 (2017) 11505–11511; doi:10.1021/acs.joc.7b02105

data_4032934
_publ_section_title
;
 Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H
 Activation of Arylnitrones and Coupling with Diazo Compounds.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11505
_journal_page_last               11511
_journal_paper_doi               10.1021/acs.joc.7b02105
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-20
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
;
2017-04-25 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90.53(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.865(4)
_cell_length_b                   10.825(2)
_cell_length_c                   9.0227(14)
_cell_measurement_reflns_used    1063
_cell_measurement_temperature    287.51(10)
_cell_measurement_theta_max      28.2120
_cell_measurement_theta_min      4.1370
_cell_volume                     1354.1(5)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      287.51(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.858
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details
;
  1 omega   -5.00   21.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -19.6617  -99.0000  120.0000 26

  2 omega   -1.00   82.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       23.0992   57.0000    0.0000 83

  3 omega   13.00   58.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       23.0992   19.0000  150.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0512387000
_diffrn_orient_matrix_UB_12      -0.0036684000
_diffrn_orient_matrix_UB_13      0.0001276000
_diffrn_orient_matrix_UB_21      -0.0027463000
_diffrn_orient_matrix_UB_22      -0.0641263000
_diffrn_orient_matrix_UB_23      -0.0146568000
_diffrn_orient_matrix_UB_31      0.0001862000
_diffrn_orient_matrix_UB_32      0.0119793000
_diffrn_orient_matrix_UB_33      -0.0772240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.858
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3054
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0518P)^2^+0.2180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1717
_reflns_number_total             2056
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {ad16ff72-db00-4935-805f-f0876624e419}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            jo7b02105_si_001.cif
_cod_data_source_block           syt-1
_cod_depositor_comments          'Adding full bibliography for 4032934.cif.'
_cod_original_cell_volume        1354.2(5)
_cod_database_code               4032934
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 H15 N1 O2'
_reflns_odcompleteness_completeness 84.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C4(H4), C10(H10), C7(H7), C6(H6), C14(H14), C13(H13),
 C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'