Synthesis of 1-(2-Aminovinyl)indoles and 1,3'-Biindoles by Reaction of 2,2-Diaryl-Substituted 2 H-Azirines with α-Imino Rh(II) Carbenoids.
Khaidarov, Adel R.; Rostovskii, Nikolai V.; Zolotarev, Andrey A.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; The Journal of organic chemistry 84 (2019) 3743–3753; doi:10.1021/acs.joc.8b03205

data_4034245
_publ_section_title
;
 Synthesis of 1-(2-Aminovinyl)indoles and 1,3'-Biindoles by Reaction of
 2,2-Diaryl-Substituted 2 H-Azirines with \a-Imino Rh(II) Carbenoids.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3743
_journal_page_last               3753
_journal_paper_doi               10.1021/acs.joc.8b03205
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C35 H27 F N2 O2 S'
_chemical_formula_sum            'C35 H27 F N2 O2 S'
_chemical_formula_weight         558.64
_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
_audit_creation_date             2017-02-08
_audit_creation_method
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Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
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_cell_angle_alpha                71.982(9)
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_cell_formula_units_Z            2
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_cell_length_b                   12.1732(12)
_cell_length_c                   15.8235(17)
_cell_measurement_reflns_used    3785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5200
_cell_measurement_theta_min      3.2450
_cell_volume                     1766.3(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
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  1 omega  -34.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000  -90.0000 80

  2 omega  -93.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000  150.0000 100

  3 omega  -93.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000  -90.0000 100

  4 omega  -80.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000   30.0000 87

  5 omega   44.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -178.0000 -150.0000 55
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_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      0.0663852000
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_diffrn_orient_matrix_UB_13      0.0196314000
_diffrn_orient_matrix_UB_21      -0.0293328000
_diffrn_orient_matrix_UB_22      0.0559292000
_diffrn_orient_matrix_UB_23      0.0127669000
_diffrn_orient_matrix_UB_31      -0.0119670000
_diffrn_orient_matrix_UB_32      -0.0360491000
_diffrn_orient_matrix_UB_33      0.0413327000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14905
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.728
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_description       tables
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         7884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0828
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+2.0316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                5788
_reflns_number_total             7884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03205_si_004.cif
_cod_data_source_block           rnv30
_cod_database_code               4034245
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c35 h27 n2 F1 S1 O2 o6 br'
_reflns_odcompleteness_completeness 96.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C29(H29), C25(H25), C35(H35), C10(H10), C31(H31), C28(H28), C34(H34),
 C26(H26), C7(H7), C27(H27), C32(H32), C33(H33), C18(H18), C22(H22), C4(H4),
 C5(H5), C19(H19), C14(H14), C21(H21), C12(H12), C6(H6), C15(H15), C13(H13)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
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_olex2_submission_special_instructions 'No special instructions were received'