Regioselective Internal Carbonylation of the 2-Aza-21-carbaporphyrin: Access to Configurationally Stable Chiral Porphyrinoids.
Liu, Bin; Li, Xiaofang; Maciołek, Justyna; Stępień, Marcin; Chmielewski, Piotr J; The Journal of organic chemistry 79 (2014) 3129–3139; doi:10.1021/jo500272t

data_4029242
_publ_section_title
;
 Regioselective Internal Carbonylation of the 2-Aza-21-carbaporphyrin:
 Access to Configurationally Stable Chiral Porphyrinoids.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3129
_journal_page_last               3139
_journal_paper_doi               10.1021/jo500272t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C49 H34 N4 O'
_chemical_formula_sum            'C49 H34 N4 O'
_chemical_formula_weight         694.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.824(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.5162(12)
_cell_length_b                   8.5913(10)
_cell_length_c                   15.4670(14)
_cell_measurement_reflns_used    1298
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.7248
_cell_measurement_theta_min      2.8648
_cell_volume                     1922.1(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9229
_diffrn_reflns_theta_full        72.42
_diffrn_reflns_theta_max         72.42
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.445
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.469
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0987
_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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2186
_refine_ls_wR_factor_ref         0.2296
_reflns_number_gt                1652
_reflns_number_total             3735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500272t_si_003.cif
_cod_data_source_block           oncp
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029242.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4029242