Rational Synthesis of 5,10-Diazaporphyrins via Nucleophilic Substitution Reactions of α,α'-Dibromotripyrrin and Dihydrogenation to Give 5,10-Diazachlorins.
Umetani, Masataka; Kim, Gakhyun; Tanaka, Takayuki; Kim, Dongho; Osuka, Atsuhiro; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03467

data_4037934
_publ_section_title
;
 Rational Synthesis of 5,10-Diazaporphyrins via Nucleophilic Substitution
 Reactions of \a,\a'-Dibromotripyrrin and Dihydrogenation to Give
 5,10-Diazachlorins.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03467
_journal_year                    2020
_chemical_formula_moiety         '2(C30 H20 N6 O Zn), 0.5(C4 H8 O)'
_chemical_formula_sum            'C62 H44 N12 O2.5 Zn2'
_chemical_formula_weight         1127.83
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
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_cell_length_a                   6.9194(2)
_cell_length_b                   20.1673(5)
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_cell_measurement_temperature    93(2)
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.978
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
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_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34621
_diffrn_reflns_point_group_measured_fraction_full 0.978
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_diffrn_reflns_theta_max         74.510
_diffrn_reflns_theta_min         2.465
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.14
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_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.623
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_refine_ls_extinction_method     none
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+1.9479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8009
_reflns_number_total             9814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03467_si_002.cif
_cod_data_source_block           190622umetani
_cod_original_cell_volume        2519.28(14)
_cod_original_formula_sum        'C62 H44 N12 O2.50 Zn2'
_cod_database_code               4037934
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              85319
_shelx_hkl_checksum              84800