5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1): A Stable Hückel Antiaromatic Hexaphyrin Stabilized by Intramolecular Hydrogen Bonding and Protonation-Induced Conformational Twist To Gain Möbius Aromaticity.
Naoda, Koji; Mori, Hirotaka; Oh, Juwon; Park, Kyu Hyung; Kim, Dongho; Osuka, Atsuhiro; The Journal of organic chemistry 80 (2015) 11726–11733; doi:10.1021/acs.joc.5b01348

data_4036268
_publ_section_title
;
 5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1): A Stable H\"uckel
 Antiaromatic Hexaphyrin Stabilized by Intramolecular Hydrogen Bonding and
 Protonation-Induced Conformational Twist To Gain M\"obius Aromaticity.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11726
_journal_page_last               11733
_journal_paper_doi               10.1021/acs.joc.5b01348
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C64 H24 F20 N8, 4(C H2 Cl2)'
_chemical_formula_sum            'C68 H32 Cl8 F20 N8'
_chemical_formula_weight         1624.62
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.46(2)
_cell_angle_beta                 86.21(3)
_cell_angle_gamma                80.53(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5903(18)
_cell_length_b                   14.3500(16)
_cell_length_c                   16.671(5)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.4
_cell_volume                     1642.0(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19438
_diffrn_reflns_theta_full        63.99
_diffrn_reflns_theta_max         63.99
_diffrn_reflns_theta_min         6.58
_exptl_absorpt_coefficient_mu    4.105
_exptl_absorpt_correction_T_max  0.8211
_exptl_absorpt_correction_T_min  0.3928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1481P)^2^+0.9318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2122
_reflns_number_gt                4771
_reflns_number_total             5292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01348_si_002.cif
_cod_data_source_block           40901n
_cod_original_formula_sum        'C68 H32 Cl8 F20 N8 '
_cod_database_code               4036268