A Synthesis of Novel Expanded Porphyrinoids: NiII-Induced Nitrile Cyclization of Dicyanovinylene-Bis(meso-Aryl)Dipyrrin
Faialaga, Nathan Hikaru; Ito, Satoru; Shinokubo, Hiroshi; Kim, Yonghun; Kim, Kimoon; Shin, Ji-Young; Dalton Trans.  (2017) –; doi:10.1039/C7DT01838J

data_7043379
_publ_section_title
;
 A Synthesis of Novel Expanded Porphyrinoids: NiII-Induced Nitrile
 Cyclization of Dicyanovinylene-Bis(meso-Aryl)Dipyrrin
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01838J
_journal_year                    2017
_chemical_formula_moiety         '2(C68 H18 F20 N12 Ni2) 0.5 (C6 H14)'
_chemical_formula_sum            'C69.5 H21.5 F20 N12 Ni2'
_chemical_formula_weight         1521.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                103.63(3)
_cell_angle_beta                 94.83(3)
_cell_angle_gamma                108.69(3)
_cell_formula_units_Z            4
_cell_length_a                   16.065(3)
_cell_length_b                   20.758(4)
_cell_length_c                   21.059(4)
_cell_measurement_reflns_used    69797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.00
_cell_measurement_theta_min      0.63
_cell_volume                     6367(3)
_computing_cell_refinement       HKL3000
_computing_data_collection       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details
'1.00 degrees, 3.0 sec, detector distance 63.00 mm'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.906
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40579
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.523
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  0.6371
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3034
_exptl_crystal_recrystallization_method 'Dichloromethane and Hexane'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.357
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1892
_refine_ls_number_reflns         21255
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0761
_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^)+(0.1697P)^2^+3.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16207
_reflns_number_total             21255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt01838j2.cif
_cod_data_source_block           Ni2MAC-JYS-B
_cod_original_cell_volume        6367(2)
_cod_original_formula_sum        'C69.50 H21.50 F20 N12 Ni2'
_cod_database_code               7043379
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014-3
_shelx_res_checksum              90248