Vanadium-catalyzed regioselective oxidative coupling of 2-hydroxycarbazoles.
Liu, Lei; Carroll, Patrick J.; Kozlowski, Marisa C.; Organic letters 17 (2015) 508–511; doi:10.1021/ol503521b

data_1518586
_publ_section_title
;
 Vanadium-catalyzed regioselective oxidative coupling of
 2-hydroxycarbazoles.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              508
_journal_page_last               511
_journal_paper_doi               10.1021/ol503521b
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C60.5 H56 N4 O6'
_chemical_formula_weight         935.09
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.474(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.1723(13)
_cell_length_b                   24.7158(17)
_cell_length_c                   24.1251(18)
_cell_measurement_temperature    100(1)
_cell_volume                     9642.7(12)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            78535
_diffrn_reflns_theta_full        25.55
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1287
_refine_ls_number_reflns         17225
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0735
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+54.4232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                15120
_reflns_number_total             17225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503521b_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1518586.cif.'
_cod_original_sg_symbol_H-M      'C c      '
_cod_database_code               1518586