5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity switching
Umetani, Masataka; Kim, Jinseok; Tanaka, Takayuki; Kim, Dongho; Osuka, Atsuhiro; Chemical Communications  (2019) –; doi:10.1039/C9CC05580K

data_7123964
_publ_section_title
;
 5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity
 switching
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05580K
_journal_year                    2019
_chemical_formula_moiety
'C52 H36 N8, 0.696(C H Cl3), 0.304(C2 H4 Cl2)'
_chemical_formula_sum            'C53.3 H37.91 Cl2.7 N8'
_chemical_formula_weight         886.03
_chemical_name_systematic        5,20-diaza[28]hexaphyrin
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-15 deposited with the CCDC.    2019-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.757(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.818(2)
_cell_length_b                   8.0037(16)
_cell_length_c                   28.018(6)
_cell_measurement_reflns_used    1311
_cell_measurement_temperature    90
_cell_measurement_theta_max      21.54
_cell_measurement_theta_min      2.48
_cell_volume                     2199.1(8)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11394
_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         2.077
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prism
_exptl_crystal_F_000             919
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1107P)^2^+2.8847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2643
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05580k2.cif
_cod_data_source_block           71106MU_0m
_cod_original_cell_volume        2199.2(8)
_cod_original_formula_sum        'C53.30 H37.91 Cl2.70 N8'
_cod_database_code               7123964
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              27222