#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:30:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180265 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/51/7115159.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7115159
loop_
_publ_author_name
'Palacio, Magali'
'Mansuy-Mouries, Virginie'
'Loire, Guillaume'
'Le Barch-Ozette, Karine'
'Leduc, Philippe'
'Battioni, Pierrette'
'Mansuy, Daniel'
'Barkigia, Kathleen M.'
'Fajer, Jack'
_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 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
;
_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       θ/2θ
_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/[σ²(Fo²)+(0.1842P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Zn Zn -1.0000 0.0000 -1.0000 0.0527(8) Uani 1 d S
Cl1 Cl -1.1206(6) -0.4826(4) -1.2340(5) 0.154(2) Uani 1 d .
Cl2 Cl -1.3037(5) -0.2002(4) -1.4031(4) 0.132(2) Uani 1 d .
Cl3 Cl -0.5965(6) -0.0948(6) -1.1695(7) 0.202(4) Uani 1 d .
Cl4 Cl -0.7215(4) 0.2659(5) -1.2606(5) 0.135(2) Uani 1 d .
O1 O -1.5035(12) -0.3677(11) -0.9583(14) 0.167(7) Uani 1 d .
O2 O -1.5408(11) -0.2141(17) -0.9783(11) 0.141(6) Uani 1 d .
O3 O -1.4092(14) -0.4851(13) -1.2057(10) 0.159(7) Uani 1 d .
O4 O -1.4924(12) -0.3692(17) -1.2473(12) 0.168(8) Uani 1 d .
O5 O -1.0019(12) -0.3763(12) -1.4726(11) 0.146(6) Uani 1 d .
O6 O -1.0582(15) -0.2490(14) -1.5274(11) 0.163(7) Uani 1 d .
O7 O -0.7424(15) -0.1651(12) -1.4452(17) 0.226(12) Uani 1 d .
O8 O -0.7922(11) -0.0141(16) -1.4585(9) 0.159(7) Uani 1 d .
O9 O -0.9256(9) -0.1292(8) -0.9389(9) 0.088(3) Uani 1 d .
N1 N -1.1681(7) -0.1282(8) -1.0324(7) 0.052(2) Uani 1 d .
N2 N -0.9628(7) -0.0774(7) -1.1630(7) 0.050(2) Uani 1 d .
N3 N -1.4774(11) -0.2757(13) -0.9782(9) 0.079(4) Uani 1 d .
N4 N -1.4178(12) -0.3849(15) -1.1973(10) 0.092(5) Uani 1 d .
N5 N -1.0168(12) -0.2797(12) -1.4576(10) 0.088(4) Uani 1 d .
N6 N -0.7918(13) -0.0971(14) -1.4152(11) 0.116(6) Uani 1 d .
C1 C -1.2546(9) -0.1330(9) -0.9577(8) 0.054(3) Uani 1 d .
C2 C -1.3592(9) -0.2303(10) -1.0151(9) 0.054(3) Uani 1 d .
C3 C -1.3314(9) -0.2832(9) -1.1193(8) 0.054(3) Uani 1 d .
C4 C -1.2117(9) -0.2181(9) -1.1323(8) 0.048(3) Uani 1 d .
C5 C -1.1519(8) -0.2419(9) -1.2303(8) 0.042(3) Uani 1 d .
C6 C -1.0375(9) -0.1731(9) -1.2415(8) 0.047(3) Uani 1 d .
C7 C -0.9758(10) -0.1921(9) -1.3474(8) 0.053(3) Uani 1 d .
C8 C -0.8697(10) -0.1079(10) -1.3253(8) 0.061(4) Uani 1 d .
C9 C -0.8553(9) -0.0338(9) -1.2095(9) 0.048(3) Uani 1 d .
C10 C -0.7586(9) 0.0612(9) -1.1549(7) 0.048(3) Uani 1 d .
C11 C -1.2160(9) -0.3494(9) -1.3278(9) 0.049(3) Uani 1 d .
C12 C -1.2054(10) -0.4606(11) -1.3371(10) 0.068(4) Uani 1 d .
C13 C -1.2633(14) -0.5618(12) -1.4283(16) 0.095(5) Uani 1 d .
H13 H -1.2543(14) -0.6373(12) -1.4325(16) 0.113 Uiso 1 calc R
C14 C -1.3324(13) -0.5505(15) -1.5106(12) 0.080(4) Uani 1 d .
H14 H -1.3714(13) -0.6176(15) -1.5712(12) 0.096 Uiso 1 calc R
C15 C -1.3434(12) -0.4393(14) -1.5025(10) 0.076(4) Uani 1 d .
H15 H -1.3909(12) -0.4300(14) -1.5580(10) 0.091 Uiso 1 calc R
C16 C -1.2843(11) -0.3384(11) -1.4119(10) 0.064(4) Uani 1 d .
C17 C -0.6517(10) 0.0847(10) -1.2230(9) 0.057(3) Uani 1 d .
C18 C -0.5753(13) 0.0164(13) -1.2317(13) 0.086(4) Uani 1 d .
C19 C -0.4790(15) 0.0396(17) -1.3020(18) 0.132(8) Uani 1 d .
H19 H -0.4296(15) -0.0098(17) -1.3155(18) 0.158 Uiso 1 calc R
C20 C -0.4598(15) 0.1319(18) -1.3484(12) 0.099(6) Uani 1 d .
H20 H -0.3944(15) 0.1480(18) -1.3900(12) 0.119 Uiso 1 calc R
C21 C -0.5318(14) 0.2009(16) -1.3365(12) 0.095(5) Uani 1 d .
H21 H -0.5175(14) 0.2643(16) -1.3693(12) 0.114 Uiso 1 calc R
C22 C -0.6295(10) 0.1759(13) -1.2734(10) 0.074(4) Uani 1 d .
C23 C -0.8480(28) -0.1044(20) -0.8392(17) 0.183(12) Uani 1 d .
H23A H -0.7785(28) -0.1295(20) -0.8625(17) 0.219 Uiso 1 calc R
H23B H -0.8209(28) -0.0171(20) -0.8035(17) 0.219 Uiso 1 calc R
C24 C -0.8980(23) -0.1610(25) -0.7585(19) 0.205(13) Uani 1 d .
H24A H -0.8400(23) -0.1394(25) -0.6951(19) 0.308 Uiso 1 calc R
H24B H -0.9230(23) -0.2477(25) -0.7919(19) 0.308 Uiso 1 calc R
H24C H -0.9655(23) -0.1351(25) -0.7328(19) 0.308 Uiso 1 calc R
O10 O -1.1455(19) 0.2913(20) -0.8990(21) 0.105(8) Uani 0.50 d P
O11 O -1.1989(21) 0.4296(26) -0.7656(23) 0.151(10) Uani 0.50 d P
C25 C -1.1718(17) 0.3914(31) -0.8855(22) 0.174(13) Uani 1 d .
C26 C -1.1747(47) 0.5006(62) -0.9416(49) 0.163(21) Uani 0.50 d P
C27 C -1.1296(52) 0.3838(80) -0.9706(34) 0.256(50) Uani 0.50 d P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Zn N2 180.000(2) 2_353 .
N2 Zn N1 89.4(3) 2_353 2_353
N2 Zn N1 90.6(3) . 2_353
N2 Zn N1 90.6(3) 2_353 .
N2 Zn N1 89.4(3) . .
N1 Zn N1 180.0 2_353 .
N2 Zn O9 88.8(3) 2_353 2_353
N2 Zn O9 91.2(3) . 2_353
N1 Zn O9 90.0(4) 2_353 2_353
N1 Zn O9 90.0(4) . 2_353
N2 Zn O9 91.2(3) 2_353 .
N2 Zn O9 88.8(3) . .
N1 Zn O9 90.0(4) 2_353 .
N1 Zn O9 90.0(4) . .
O9 Zn O9 179.998(3) 2_353 .
C23 O9 Zn 129.0(10) . .
C4 N1 C1 109.1(8) . .
C4 N1 Zn 125.7(6) . .
C1 N1 Zn 125.1(7) . .
C6 N2 C9 110.0(8) . .
C6 N2 Zn 125.7(6) . .
C9 N2 Zn 124.3(6) . .
O1 N3 O2 126.1(14) . .
O1 N3 C2 119.1(15) . .
O2 N3 C2 114.6(13) . .
O4 N4 O3 123.0(17) . .
O4 N4 C3 120.1(19) . .
O3 N4 C3 116.9(17) . .
O6 N5 O5 124.6(14) . .
O6 N5 C7 118.0(16) . .
O5 N5 C7 117.3(16) . .
O7 N6 O8 125.1(15) . .
O7 N6 C8 119.6(19) . .
O8 N6 C8 115.2(17) . .
N1 C1 C10 126.0(9) . 2_353
N1 C1 C2 107.6(8) . .
C10 C1 C2 126.3(9) 2_353 .
C3 C2 C1 107.3(8) . .
C3 C2 N3 121.0(9) . .
C1 C2 N3 131.7(9) . .
C2 C3 C4 108.4(8) . .
C2 C3 N4 120.7(9) . .
C4 C3 N4 130.9(9) . .
N1 C4 C5 126.7(8) . .
N1 C4 C3 107.5(8) . .
C5 C4 C3 125.8(9) . .
C6 C5 C4 124.2(8) . .
C6 C5 C11 118.8(8) . .
C4 C5 C11 117.1(8) . .
N2 C6 C5 128.3(8) . .
N2 C6 C7 106.9(8) . .
C5 C6 C7 124.8(8) . .
C8 C7 N5 123.0(9) . .
C8 C7 C6 107.1(8) . .
N5 C7 C6 129.9(9) . .
C7 C8 C9 110.0(8) . .
C7 C8 N6 120.2(9) . .
C9 C8 N6 129.7(9) . .
C10 C9 N2 126.6(9) . .
C10 C9 C8 127.4(8) . .
N2 C9 C8 106.0(8) . .
C9 C10 C1 127.1(8) . 2_353
C9 C10 C17 115.8(8) . .
C1 C10 C17 117.0(8) 2_353 .
C12 C11 C16 117.5(10) . .
C12 C11 C5 120.8(12) . .
C16 C11 C5 121.6(11) . .
C11 C12 C13 121.6(14) . .
C11 C12 Cl1 120.5(9) . .
C13 C12 Cl1 117.8(13) . .
C14 C13 C12 120.5(15) . .
C15 C14 C13 118.5(13) . .
C14 C15 C16 120.7(14) . .
C11 C16 C15 121.1(13) . .
C11 C16 Cl2 119.6(9) . .
C15 C16 Cl2 119.2(12) . .
C22 C17 C18 119.7(11) . .
C22 C17 C10 120.2(12) . .
C18 C17 C10 120.1(11) . .
C17 C18 C19 117.2(14) . .
C17 C18 Cl3 121.8(10) . .
C19 C18 Cl3 120.9(13) . .
C20 C19 C18 120.7(16) . .
C21 C20 C19 121.8(14) . .
C20 C21 C22 118.4(15) . .
C17 C22 C21 122.0(15) . .
C17 C22 Cl4 120.7(9) . .
C21 C22 Cl4 117.3(13) . .
C24 C23 O9 115.2(25) . .
C27 C25 O11 165.1(34) . .
O10 C25 C26 146.0(31) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn N2 2.068(8) 2_353
Zn N2 2.068(8) .
Zn N1 2.083(8) 2_353
Zn N1 2.083(8) .
Zn O9 2.272(10) 2_353
Zn O9 2.272(10) .
Cl1 C12 1.732(14) .
Cl2 C16 1.713(14) .
Cl3 C18 1.67(2) .
Cl4 C22 1.720(15) .
O1 N3 1.15(2) .
O2 N3 1.19(2) .
O3 N4 1.21(2) .
O4 N4 1.16(2) .
O5 N5 1.19(2) .
O6 N5 1.18(2) .
O7 N6 1.12(2) .
O8 N6 1.25(2) .
O9 C23 1.43(2) .
N1 C4 1.369(12) .
N1 C1 1.374(12) .
N2 C6 1.348(11) .
N2 C9 1.411(12) .
N3 C2 1.465(14) .
N4 C3 1.44(2) .
N5 C7 1.443(14) .
N6 C8 1.448(14) .
C1 C10 1.393(13) 2_353
C1 C2 1.443(14) .
C2 C3 1.350(13) .
C3 C4 1.435(13) .
C4 C5 1.400(12) .
C5 C6 1.392(12) .
C5 C11 1.497(13) .
C6 C7 1.489(12) .
C7 C8 1.331(14) .
C8 C9 1.434(14) .
C9 C10 1.365(13) .
C10 C1 1.393(13) 2_353
C10 C17 1.517(13) .
C11 C12 1.35(2) .
C11 C16 1.37(2) .
C12 C13 1.40(2) .
C13 C14 1.35(2) .
C14 C15 1.35(2) .
C15 C16 1.40(2) .
C17 C22 1.36(2) .
C17 C18 1.37(2) .
C18 C19 1.44(2) .
C19 C20 1.34(2) .
C20 C21 1.33(2) .
C21 C22 1.40(2) .
C23 C24 1.39(3) .
O10 C25 1.29(4) .
O11 C25 1.48(3) .
C25 C27 1.15(4) .
C25 C26 1.65(6) .
