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_7043378
_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
'C41 H16 F10 N6 Ni O,1.428(C H2 Cl2), 0.572(C H? O), 1.717(H)'
_chemical_formula_sum            'C43 H21.14 Cl2.86 F10 N6 Ni O1.57'
_chemical_formula_weight         996.94
_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
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.469(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4324(4)
_cell_length_b                   29.5119(5)
_cell_length_c                   10.4236(2)
_cell_measurement_reflns_used    15539
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      30.8430
_cell_measurement_theta_min      2.0670
_cell_volume                     3962.55(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32914
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.725
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            'pale red'
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2001
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         9032
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0637
_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^)+(0.1148P)^2^+4.4566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7182
_reflns_number_total             9032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt01838j2.cif
_cod_data_source_block           v160528jys_a
_cod_database_code               7043378
_shelx_estimated_absorpt_t_min   0.860
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-3
_shelx_res_checksum              6985