Nucleophilic Ring Opening of meso-Substituted 5-Oxaporphyrin by Oxygen, Nitrogen, Sulfur, and Carbon Nucleophiles.
Kakeya, Kazuhisa; Aozasa, Masakatsu; Mizutani, Tadashi; Hitomi, Yutaka; Kodera, Masahito; The Journal of organic chemistry 79 (2014) 2591–2600; doi:10.1021/jo5000412

data_4029202
_publ_section_title
;
 Nucleophilic Ring Opening of meso-Substituted 5-Oxaporphyrin by Oxygen,
 Nitrogen, Sulfur, and Carbon Nucleophiles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2591
_journal_page_last               2600
_journal_paper_doi               10.1021/jo5000412
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C47 H40 N4 O8'
_chemical_formula_weight         788.83
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                83.4051(13)
_cell_angle_beta                 83.9689(12)
_cell_angle_gamma                76.2855(12)
_cell_formula_units_Z            2
_cell_length_a                   7.6123(2)
_cell_length_b                   12.0814(3)
_cell_length_c                   22.5696(5)
_cell_measurement_reflns_used    14625
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.785
_cell_volume                     1996.62(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXISIP'
_diffrn_measurement_method       \w
_diffrn_radiation_detector       IP
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31941
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0899P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1753
_reflns_number_gt                4739
_reflns_number_total             7143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5000412_si_002.cif
_cod_data_source_block           ydkr
_cod_original_cell_volume        1996.62(8)
_cod_database_code               4029202