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_4034247
_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         'C36 H27 F3 N2 O2 S'
_chemical_formula_sum            'C36 H27 F3 N2 O2 S'
_chemical_formula_weight         608.65
_space_group_crystal_system      hexagonal
_space_group_IT_number           179
_space_group_name_Hall           'P 65 2 (0 0 1)'
_space_group_name_H-M_alt        'P 65 2 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-02-15
_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                90
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_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   17.6547(3)
_cell_length_b                   17.6547(3)
_cell_length_c                   42.2964(7)
_cell_measurement_reflns_used    22341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.7370
_cell_measurement_theta_min      3.5430
_cell_volume                     11417.1(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    6.00   80.10   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.7157   38.0000   90.0000 247

  2 omega   39.00   86.10   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.7157  178.0000  -60.0000 157

  3 omega  -39.00   31.20   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -77.0000   60.0000 234

  4 omega   -9.00   70.20   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.7157   19.0000  -90.0000 264
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_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0434757000
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_diffrn_orient_matrix_UB_13      -0.0004900000
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_diffrn_orient_matrix_UB_31      0.0134399000
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            83686
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_description
;
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_exptl_crystal_F_000             3792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         8740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.9196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0866
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_reflns_Friedel_fraction_max     1.000
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03205_si_002.cif
_cod_data_source_block           rnv_31_sq
_cod_original_cell_volume        11417.1(4)
_cod_database_code               4034247
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C36 H27 F3 N2 O2 S'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
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_olex2_submission_special_instructions 'No special instructions were received'