A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines.
Furuyama, Taniyuki; Sato, Takehito; Kobayashi, Nagao; Journal of the American Chemical Society 137 (2015) 13788–13791; doi:10.1021/jacs.5b09853

data_4129719
_publ_section_title
;
 A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines:
 Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13788
_journal_page_last               13791
_journal_paper_doi               10.1021/jacs.5b09853
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C76 H54 F24 N8 O10 3(C5 H5 N)'
_chemical_formula_sum            'C91 H69 F24 N11 O10'
_chemical_formula_weight         1932.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                67.443(2)
_cell_angle_beta                 75.680(2)
_cell_angle_gamma                79.371(3)
_cell_formula_units_Z            2
_cell_length_a                   11.109(2)
_cell_length_b                   19.269(4)
_cell_length_c                   22.218(4)
_cell_measurement_temperature    100(2)
_cell_volume                     4234.3(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.1155
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39197
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.233
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1262
_refine_ls_number_reflns         14794
_refine_ls_number_restraints     399
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0911P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8666
_reflns_number_total             14794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09853_si_003.cif
_cod_data_source_block           test
_cod_original_cell_volume        4234.4(13)
_cod_database_code               4129719
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              29282
_shelx_hkl_checksum              96826