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_1520505
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2355(5)
_cell_length_b                   20.9295(19)
_cell_length_c                   23.0167(15)
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    293.10(12)
_cell_measurement_theta_max      23.1770
_cell_measurement_theta_min      3.8480
_cell_volume                     3485.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.10(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -26.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 119

  2 omega   72.00   97.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000  150.0000 25
;
_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      -0.0114876000
_diffrn_orient_matrix_UB_12      -0.0336596000
_diffrn_orient_matrix_UB_13      -0.0002537000
_diffrn_orient_matrix_UB_21      0.0559822000
_diffrn_orient_matrix_UB_22      -0.0019405000
_diffrn_orient_matrix_UB_23      -0.0252237000
_diffrn_orient_matrix_UB_31      0.0796653000
_diffrn_orient_matrix_UB_32      -0.0034128000
_diffrn_orient_matrix_UB_33      0.0176990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8621
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.680
_refine_diff_density_min         -1.606
_refine_diff_density_rms         0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1839
_reflns_number_gt                1933
_reflns_number_total             3426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01590_si_003.cif
_cod_data_source_block           wangjia0512
_cod_depositor_comments
'Adding full bibliography for 1520504--1520505.cif.'
_cod_database_code               1520505
_reflns_odcompleteness_completeness 99.58
_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), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC), C19(H19A,H19B,H19C)
;
_olex2_date_sample_data_collection 2015-05-13
_olex2_submission_special_instructions 'No special instructions were received'