Rhodium-Catalyzed NH-Indole-Directed C-H Carbonylation with Carbon Monoxide: Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones.
Huang, Qiufeng; Han, Qingshuai; Fu, Shurong; Yao, Zizhu; Su, Lv; Zhang, Xiaofeng; Lin, Shen; Xiang, Shengchang; The Journal of organic chemistry 81 (2016) 12135–12142; doi:10.1021/acs.joc.6b01200

data_4036997
_publ_section_title
;
 Rhodium-Catalyzed NH-Indole-Directed C-H Carbonylation with Carbon
 Monoxide: Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12135
_journal_page_last               12142
_journal_paper_doi               10.1021/acs.joc.6b01200
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C10 H15 Cl2 Rh, C14 H11 N'
_chemical_formula_sum            'C24 H26 Cl2 N Rh'
_chemical_formula_weight         502.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-25
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Olex2 1.2
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_cell_length_c                   26.3974(15)
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    291.98(10)
_cell_measurement_theta_max      25.4500
_cell_measurement_theta_min      3.7490
_cell_volume                     4381.5(4)
_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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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)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
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  1 omega   22.00   72.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       10.9934   38.0000  -60.0000 50

  2 omega  -83.00    5.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1497  -57.0000 -180.0000 88
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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      0.0199766000
_diffrn_orient_matrix_UB_12      0.0125420000
_diffrn_orient_matrix_UB_13      -0.0244137000
_diffrn_orient_matrix_UB_21      -0.0262557000
_diffrn_orient_matrix_UB_22      0.0342845000
_diffrn_orient_matrix_UB_23      0.0066109000
_diffrn_orient_matrix_UB_31      0.0736909000
_diffrn_orient_matrix_UB_32      0.0088489000
_diffrn_orient_matrix_UB_33      0.0090234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.1440
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14849
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         89.149
_diffrn_reflns_theta_min         7.500
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68092
_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)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       bulk
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_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.609
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_restraints     0
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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^)+(0.0040P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2445
_reflns_number_total             4887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01200_si_002.cif
_cod_data_source_block           hqf-crf-61
_cod_database_code               4036997
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.48
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C12(H12), C17(H17), C22(H22), C21(H21), N1(H1), C16(H16),
 C11(H11), C24(H24), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c),
 C6(H6a,H6b,H6c)
;
_shelx_res_checksum              21495
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_olex2_submission_special_instructions 'No special instructions were received'