Novel Route to Functionalized Tetraaryltetra[2,3]naphthaloporphyrins via Oxidative Aromatization
Olga S. Finikova; Andrei V. Cheprakov; Patrick J. Carroll; Sergei A. Vinogradov; Journal of Organic Chemistry 68 (2003) 7517–7520; doi:10.1021/jo0347819

data_4022515
_publ_contact_author             'Sergei Vinogradov'
_publ_contact_author_email       vinograd@mail.med.upenn.edu
_publ_section_title
;
 Novel Route to Functionalized Tetraaryltetra[2,3]naphthaloporphyrins
 via Oxidative Aromatization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7517
_journal_page_last               7520
_journal_paper_doi               10.1021/jo0347819
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C86 H56 Cl4 N4 O8 Pd'
_chemical_formula_weight         1521.55
_chemical_name_common
;
 meso-tetra-(4-methoxycarbonyl-phenyl)tetranaphthaloporphyrin
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.628(3)
_cell_length_b                   17.628(3)
_cell_length_c                   23.372(5)
_cell_measurement_temperature    143(1)
_cell_volume                     7262.5(24)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24216
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prism
_exptl_crystal_F_000             3112
_exptl_crystal_preparation       C6H5CN/C5H5N
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.884
_refine_ls_goodness_of_fit_obs   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      0.945
_refine_ls_restrained_S_obs      0.984
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_obs          0.0817
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1741P)^2^+108.0003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2624
_refine_ls_wR_factor_obs         0.2561
_reflns_number_observed          3574
_reflns_number_total             4046
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo0347819si20030610_115748.cif
_cod_data_source_block           Compound_Pd-7a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1741P)^2^+108.0003P] where P=(Fo^2^+2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1741P)^2^+108.0003P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'I 41/a     '
_cod_database_code               4022515