Facile Synthesis of Carbazoles via a Tandem Iodocyclization with 1,2-Alkyl Migration and Aromatization.
Wang, Jia; Zhu, Hai-Tao; Qiu, Yi-Feng; Niu, Yuan; Chen, Si; Li, Ying-Xiu; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 17 (2015) 3186–3189; doi:10.1021/acs.orglett.5b01590

data_1520504
_publ_section_title
;
 Facile Synthesis of Carbazoles via a Tandem Iodocyclization with
 1,2-Alkyl Migration and Aromatization.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3186
_journal_page_last               3189
_journal_paper_doi               10.1021/acs.orglett.5b01590
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 I N O'
_chemical_formula_sum            'C20 H16 I N O'
_chemical_formula_weight         413.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-18
_audit_creation_method
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_cell_angle_alpha                94.284(6)
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_cell_formula_units_Z            6
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_cell_length_c                   22.2683(12)
_cell_measurement_reflns_used    3917
_cell_measurement_temperature    291.64(10)
_cell_measurement_theta_max      23.3230
_cell_measurement_theta_min      3.6610
_cell_volume                     2549.0(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      291.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -17.00   26.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000  150.0000 29

  2 omega   28.00   80.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   30.0000 35

  3 omega  -11.00   97.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   38.0000 -120.0000 72

  4 omega    2.00   95.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   38.0000  -30.0000 62

  5 omega   30.00   57.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  -30.0000 18

  6 omega   -1.00   83.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  120.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_22      0.0453124000
_diffrn_orient_matrix_UB_23      0.0210582000
_diffrn_orient_matrix_UB_31      -0.0328248000
_diffrn_orient_matrix_UB_32      -0.0142200000
_diffrn_orient_matrix_UB_33      0.0245441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17352
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.083
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.888
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_exptl_absorpt_correction_T_min  0.79330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.34
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_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.078
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_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0555
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.6800P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
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_reflns_number_gt                5787
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_cod_data_source_file            ol5b01590_si_002.cif
_cod_data_source_block           wangjia0717
_cod_depositor_comments
'Adding full bibliography for 1520504--1520505.cif.'
_cod_database_code               1520504
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_reflns_odcompleteness_completeness 99.83
_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(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31),
  C34(H34), C35(H35), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43),
 C44(H44), C49(H49), C50(H50), C54(H54), C55(H55), C57(H57), C58(H58)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C39(H39A,H39B,H39C), C71(H71A,H71B,
 H71C), C52(H52A,H52B,H52C), C59(H59A,H59B,H59C)
;
_shelx_res_checksum              64981
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_olex2_submission_special_instructions 'No special instructions were received'