(E)-9-(2-iodovinyl)-9H-carbazole: a new coupling reagent for the synthesis of π-conjugated carbazoles.
Pawluć, Piotr; Franczyk, Adrian; Walkowiak, Jędrzej; Hreczycho, Grzegorz; Kubicki, Maciej; Marciniec, Bogdan; Organic letters 13 (2011) 1976–1979; doi:10.1021/ol200350a

data_1502079
_publ_contact_author
;  
Kubicki, Maciej
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Pozna\'n
Poland
;
_publ_section_title
;
 (E)-9-(2-iodovinyl)-9H-carbazole: a new coupling reagent for the
 synthesis of \p-conjugated carbazoles.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1976
_journal_page_last               1979
_journal_paper_doi               10.1021/ol200350a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H10 I N'
_chemical_formula_sum            'C14 H10 I N'
_chemical_formula_weight         319.13
_chemical_name_systematic
;
9-[(E)-2-iodoethenyl]-9H-carbazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.514(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.8893(10)
_cell_length_b                   5.4460(2)
_cell_length_c                   19.6525(7)
_cell_measurement_reflns_used    5367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8781
_cell_measurement_theta_min      3.1534
_cell_volume                     2361.95(18)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction (2009))'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction (2009))'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction (2009))'
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989), Mercury (Macrae et al, 2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7762
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.666
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+3.7278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                2239
_reflns_number_total             2706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200350a_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502079