Synthesis and Isolation of Antiaromatic Expanded Azacoronene via Intramolecular Vilsmeier-Type Reaction.
Oki, Kosuke; Takase, Masayoshi; Mori, Shigeki; Uno, Hidemitsu; Journal of the American Chemical Society 141 (2019) 16255–16259; doi:10.1021/jacs.9b09260

data_4127662
_publ_section_title
;
 Synthesis and Isolation of Antiaromatic Expanded Azacoronene via
 Intramolecular Vilsmeier-Type Reaction.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16255
_journal_page_last               16259
_journal_paper_doi               10.1021/jacs.9b09260
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C61 H65 N6, C7 H8 O, 3(F6 Sb), C H Cl3 '
_chemical_formula_sum            'C69 H74 Cl3 F18 N6 O Sb3'
_chemical_formula_weight         1816.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.041(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   31.6033(8)
_cell_length_b                   15.2402(2)
_cell_length_c                   32.1689(7)
_cell_measurement_reflns_used    57593
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      1.51
_cell_volume                     14037.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.2 (Rigaku, 2019)'
_computing_publication_material  'CrystalStructure 4.3.2 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            193052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.508
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.355
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             7232.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         2.32
_refine_diff_density_min         -1.87
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     2075
_refine_ls_number_reflns         32256
_refine_ls_number_restraints     1123
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0526P)^2^+64.0611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21938
_reflns_number_total             32256
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja9b09260_si_003.cif
_cod_data_source_block           xcalibur
_cod_database_code               4127662
_shelx_res_checksum              67911
_shelx_hkl_checksum              12026