Direct synthesis of aryl-annulated [<i>c</i>]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes.
Kawada, Yuiki; Ohmura, Shunsuke; Kobayashi, Misaki; Nojo, Wataru; Kondo, Masaki; Matsuda, Yuka; Matsuoka, Junpei; Inuki, Shinsuke; Oishi, Shinya; Wang, Chao; Saito, Tatsuo; Uchiyama, Masanobu; Suzuki, Takanori; Ohno, Hiroaki; Chemical science 9 (2018) 8416–8425; doi:10.1039/c8sc03525c

data_1549908
_publ_section_title
;
 Direct synthesis of aryl-annulated [<i>c</i>]carbazoles by
 gold(i)-catalysed cascade reaction of azide-diynes and arenes.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              8416
_journal_page_last               8425
_journal_paper_doi               10.1039/c8sc03525c
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.40
_chemical_name_systematic        7aF-Me2
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   13.252(6)
_cell_length_b                   5.704(2)
_cell_length_c                   42.601(19)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      3.10
_cell_volume                     3220(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            15881
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1312.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     425
_refine_ls_number_reflns         4996
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1196P)^2^+0.9057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2052
_reflns_number_gt                3665
_reflns_number_total             4996
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8sc03525c2.cif
_cod_data_source_block           160520r
_cod_depositor_comments
'Adding full bibliography for 1549906--1549908.cif.'
_cod_original_cell_volume        3220(3)
_cod_database_code               1549908