Synthesis of a Series of Aromatic Benziporphyrins and Heteroanalogues via Tripyrrane-Like Intermediates Derived from Resorcinol and 2-Methylresorcinol
Timothy D. Lash; Kae Miyake; Linlin Xu; Gregory M. Ferrence; Journal of Organic Chemistry 76 (2011) 6295–6308; doi:10.1021/jo201098c

data_4026499
_publ_contact_author_address
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790
;
_publ_contact_author_email       Ferrence@IllinoisState.edu
_publ_contact_author_fax         (309)4385538
_publ_contact_author_name        'Ferrence, Gregory M.'
_publ_contact_author_phone       (309)4387971
_publ_section_title
;
 Synthesis of a Series of Aromatic Benziporphyrins and Heteroanalogues via
 Tripyrrane-Like Intermediates Derived from Resorcinol and
 2-Methylresorcinol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6295
_journal_page_last               6308
_journal_paper_doi               10.1021/jo201098c
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C29 H28 N2 O3 Se, C H4 O'
_chemical_formula_sum            'C30 H32 N2 O4 Se'
_chemical_formula_weight         563.54
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-05-22T06:00:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.857(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3698(9)
_cell_length_b                   12.8502(12)
_cell_length_c                   21.309(2)
_cell_measurement_reflns_used    6734
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.493
_cell_measurement_theta_min      2.307
_cell_measurement_wavelength     0.71073
_cell_volume                     2556.5(4)
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25832
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2008.2-4 (Bruker, 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+1.3175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                5751
_reflns_number_total             6349
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo201098c_si_001.cif
_cod_data_source_block           06mz203m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026499