(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_1502080
_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         'C32 H29 N O Si'
_chemical_formula_sum            'C32 H29 N O Si'
_chemical_formula_weight         471.65
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.96(2)
_cell_angle_beta                 96.20(2)
_cell_angle_gamma                100.08(2)
_cell_formula_units_Z            4
_cell_length_a                   8.497(2)
_cell_length_b                   17.410(3)
_cell_length_c                   17.576(3)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.4885
_cell_measurement_theta_min      2.8390
_cell_volume                     2543.3(9)
_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      100(2)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_av_sigmaI/netI    0.2146
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22783
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         8452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1960
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.2314
_reflns_number_gt                3433
_reflns_number_total             8452
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol200350a_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502080