A new general method for selective β-polynitration of porphyrins; preparation and redox properties of Zn-porphyrins bearing one through to eight β-nitro substituents and X-ray structure of the first Zn β-pernitro porphyrin
Palacio, Magali; Mansuy-Mouries, Virginie; Loire, Guillaume; Le Barch-Ozette, Karine; Leduc, Philippe; Battioni, Pierrette; Mansuy, Daniel; Barkigia, Kathleen M.; Fajer, Jack; Chemical Communications  (2000) 1907–; doi:10.1039/b004160m

data_7115159
_publ_contact_author
;
 K.M. Barkigia (regarding crystallographic details and this CIF)
 Energy Sciences and Technology Department
 Bldg. 555
 Brookhaven National Laboratory
 Upton, NY 11973 USA
;
_publ_section_title
;
 A new general method for selective \b-polynitration of porphyrins;
 preparation and redox properties of Zn-porphyrins bearing one through to
 eight \b-nitro substituents and X-ray structure of the first Zn
 \b-pernitro porphyrin
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              1907
_journal_paper_doi               10.1039/b004160m
_journal_year                    2000
_chemical_compound_source        'methylene chloride'
_chemical_formula_structural
'C44 H12 Cl8 N12 O16 Zn, 2(C2 H5 OH), 2(C2 H5 OH)'
_chemical_formula_sum            'C52 H36 Cl8 N12 O20 Zn'
_chemical_formula_weight         1497.90
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                106.04(2)
_cell_angle_beta                 90.24(3)
_cell_angle_gamma                106.87(3)
_cell_formula_units_Z            1
_cell_length_a                   11.792(3)
_cell_length_b                   11.993(2)
_cell_length_c                   12.279(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     1590.4(8)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1977)
_computing_data_collection       CAD4_(Enraf-Nonius,_1977)
_computing_data_reduction        'XCAD4VAX provided with SHELXL-93'
_computing_molecular_graphics    'SHELXTL and other in  house programs'
_computing_publication_material  'CIFTAB provided with SHELXS-86'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Burla et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_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  0.0911
_diffrn_reflns_av_sigmaI/netI    0.1332
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4210
_diffrn_reflns_theta_max         55.06
_diffrn_reflns_theta_min         3.76
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.343
_exptl_absorpt_correction_T_max  0.5966
_exptl_absorpt_correction_T_min  0.2851
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
 The faces of the crystal were indexed, and the face-indexed absorption
 correction program in the SHELXTL package was used.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             758.
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.993
_refine_diff_density_min         -1.051
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.031
_refine_ls_goodness_of_fit_obs   1.180
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.180
_refine_ls_R_factor_all          0.2087
_refine_ls_R_factor_obs          0.0936
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3169
_refine_ls_wR_factor_obs         0.2343
_reflns_number_gt                1938
_reflns_number_total             3973
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b004160m.txt
_cod_data_source_block           zn8nofinabs1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1842P)^2^+0.0000P] 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^)+(0.1842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1590.4(7)
_cod_database_code               7115159