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_4129718
_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         'C24 H16 F12 N4 O4, 2(C H4 O)'
_chemical_formula_sum            'C26 H24 F12 N4 O6'
_chemical_formula_weight         716.49
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.9330(10)
_cell_angle_beta                 102.8530(10)
_cell_angle_gamma                91.4830(10)
_cell_formula_units_Z            1
_cell_length_a                   7.2292(6)
_cell_length_b                   8.3533(7)
_cell_length_c                   11.9019(10)
_cell_measurement_temperature    100(2)
_cell_volume                     699.91(10)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0146
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6694
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.441
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.3143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2296
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09853_si_002.cif
_cod_data_source_block           test
_cod_database_code               4129718
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.983
_exptl_absorpt_special_details
; 
 SADABS (Sheldrick, 1997) 
;
_shelx_res_checksum              97475
_shelx_hkl_checksum              1367