#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:18:08 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179321 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/18/4321837.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_4321837
loop_
_publ_author_name
'Noëlle Ehlinger'
'W. Robert Scheidt'
_publ_section_title
;
 Structure and Apparent Reactivity of the π-Cation Radical Derivatives of
 Zinc and Copper 5,10,15,20-Tetra(2,6-dichlorophenyl)porphyrinate
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1316
_journal_page_last               1321
_journal_paper_doi               10.1021/ic981041n
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C60 H48 Cl8 I4 N4 O4 Zn'
_chemical_formula_weight         1745.59
_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-97
_cell_angle_alpha                99.11(3)
_cell_angle_beta                 103.27(3)
_cell_angle_gamma                106.61(3)
_cell_formula_units_Z            1
_cell_length_a                   9.941(2)
_cell_length_b                   11.615(2)
_cell_length_c                   14.340(3)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      -20.5
_cell_volume                     1499.1(7)
_computing_cell_refinement       MADNES
_computing_data_collection       MADNES
_computing_data_reduction        'MADNES (Messerschmitt & Pflugrath, 1987)'
_computing_molecular_graphics    'ORTEPIII (Burnett, Johnson, 1996)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'Enraf-Nonius FAST area-detector'
_diffrn_measurement_method       'ellipsoid-mask fitting'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1542
_diffrn_reflns_av_sigmaI/netI    0.2007
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13699
_diffrn_reflns_theta_full        29.86
_diffrn_reflns_theta_max         29.86
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_type   refdelf
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'square plate'
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max
;
  1.756 at  1.154 \% from H3B
  1.620 at 1.306 \%A from H1B

;
_refine_diff_density_min
;
-2.138  at 0.1019 \%A from I1
;
_refine_diff_density_rms         0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         7512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2453
_refine_ls_R_factor_gt           0.1178
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1199P)²+29.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2540
_refine_ls_wR_factor_ref         0.3356
_reflns_number_gt                3217
_reflns_number_total             7512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic981041n_3.cif
_cod_data_source_block           sd:ZnTCl2PPI4
_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^)+(0.1199P)^2^+29.1845P] 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^)+(0.1199P)^2^+29.1845P] 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        1499.1(5)
_cod_database_code               4321837
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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.11043(14) 0.35255(14) 0.29426(9) 0.0478(4) Uani 1 d . . .
I2 I 0.26572(15) -0.11354(15) 0.36063(10) 0.0521(5) Uani 1 d . . .
Zn Zn 0.5000 0.0000 0.0000 0.0307(6) Uani 1 d S . .
Cl1 Cl 0.9794(5) 0.0084(4) -0.1316(4) 0.0451(11) Uani 1 d . . .
Cl2 Cl 0.8164(6) 0.4152(4) -0.1026(4) 0.0468(12) Uani 1 d . . .
Cl3 Cl 0.6892(6) 0.3872(5) 0.3165(4) 0.0540(13) Uani 1 d . . .
Cl4 Cl 0.9115(7) 0.0182(6) 0.3571(4) 0.0561(14) Uani 1 d . . .
N1 N 0.7117(15) 0.1242(12) 0.0635(9) 0.028(3) Uani 1 d . . .
N2 N 0.4746(14) -0.0091(11) 0.1382(9) 0.024(3) Uani 1 d . . .
C1A C 0.8036(18) 0.1727(14) 0.0152(11) 0.027(3) Uani 1 d . . .
C2A C 0.7838(16) 0.1689(16) 0.1626(12) 0.031(4) Uani 1 d . . .
C3A C 0.5816(19) 0.0617(18) 0.2262(12) 0.036(4) Uani 1 d . . .
C4A C 0.3507(18) -0.0732(15) 0.1593(12) 0.030(3) Uani 1 d . . .
C1B C 0.9432(18) 0.2476(15) 0.0805(11) 0.029(4) Uani 1 d . . .
H1B H 1.0276 0.2880 0.0625 0.035 Uiso 1 calc R . .
C2B C 0.9328(17) 0.2506(18) 0.1749(12) 0.038(5) Uani 1 d . . .
C3B C 0.520(2) 0.0338(17) 0.3044(13) 0.038(4) Uani 1 d . . .
H3B H 0.5694 0.0681 0.3727 0.046 Uiso 1 calc R . .
C4B C 0.386(2) -0.0459(18) 0.2684(13) 0.038(4) Uani 1 d . . .
C1M C 0.7784(16) 0.1490(14) -0.0895(12) 0.025(3) Uani 1 d . . .
C2M C 0.7237(19) 0.1427(17) 0.2387(14) 0.037(4) Uani 1 d . . .
C1 C 0.9069(19) 0.2171(16) -0.1203(13) 0.032(4) Uani 1 d . . .
C2 C 1.006(2) 0.1590(16) -0.1441(14) 0.036(4) Uani 1 d . . .
C3 C 1.1240(19) 0.2159(19) -0.1728(14) 0.042(5) Uani 1 d . . .
H3 H 1.1904 0.1748 -0.1854 0.051 Uiso 1 calc R . .
C4 C 1.1451(18) 0.3392(16) -0.1833(13) 0.033(4) Uani 1 d . . .
H4 H 1.2245 0.3802 -0.2057 0.040 Uiso 1 calc R . .
C5 C 1.050(2) 0.4006(18) -0.1610(12) 0.040(4) Uani 1 d . . .
H5 H 1.0652 0.4832 -0.1674 0.048 Uiso 1 calc R . .
C6 C 0.930(2) 0.3390(19) -0.1289(14) 0.043(5) Uani 1 d . . .
C7 C 0.8024(17) 0.2053(17) 0.3416(11) 0.032(4) Uani 1 d . . .
C8 C 0.7938(19) 0.3208(17) 0.3901(14) 0.038(4) Uani 1 d . . .
C9 C 0.863(2) 0.3736(19) 0.4841(14) 0.045(5) Uani 1 d . . .
H9 H 0.8488 0.4475 0.5123 0.055 Uiso 1 calc R . .
C10 C 0.952(2) 0.329(2) 0.5429(14) 0.044(5) Uani 1 d . . .
H10 H 1.0042 0.3723 0.6092 0.053 Uiso 1 calc R . .
C11 C 0.9642(19) 0.2117(18) 0.5013(13) 0.039(4) Uani 1 d . . .
H11 H 1.0239 0.1757 0.5402 0.046 Uiso 1 calc R . .
C12 C 0.8915(19) 0.1567(17) 0.4091(15) 0.040(4) Uani 1 d . . .
O1 O 0.5917(14) -0.1671(12) 0.0034(10) 0.042(3) Uani 1 d . . .
C91 C 0.5054(19) -0.278(2) 0.0241(15) 0.044(5) Uani 1 d . . .
H91A H 0.5629 -0.2979 0.0818 0.052 Uiso 1 calc . . .
H91B H 0.4155 -0.2686 0.0376 0.052 Uiso 1 calc . . .
C92 C 0.469(2) -0.374(2) -0.0637(15) 0.050(5) Uani 1 d . . .
H92A H 0.3889 -0.3691 -0.1169 0.060 Uiso 1 calc . . .
H92B H 0.4402 -0.4574 -0.0504 0.060 Uiso 1 calc . . .
C93 C 0.607(3) -0.345(2) -0.0883(16) 0.060(6) Uani 1 d . . .
H93A H 0.5922 -0.3846 -0.1580 0.072 Uiso 1 calc . . .
H93B H 0.6788 -0.3721 -0.0450 0.072 Uiso 1 calc . . .
C94 C 0.658(2) -0.207(2) -0.0709(16) 0.046(5) Uani 1 d . . .
H94A H 0.7660 -0.1710 -0.0465 0.056 Uiso 1 calc . . .
H94B H 0.6233 -0.1812 -0.1323 0.056 Uiso 1 calc . . .
C82 C 0.381(4) 0.280(4) 0.631(3) 0.109(12) Uiso 1 d G . .
H82A H 0.3166 0.3123 0.6631 0.131 Uiso 1 calc R . .
H82B H 0.3793 0.1997 0.6457 0.131 Uiso 1 calc R . .
C83 C 0.335(3) 0.268(5) 0.527(2) 0.18(2) Uiso 1 d G . .
H83A H 0.2708 0.3175 0.5098 0.214 Uiso 1 calc R . .
H83B H 0.2822 0.1805 0.4911 0.214 Uiso 1 calc R . .
C84 C 0.475(5) 0.317(4) 0.502(3) 0.138(16) Uiso 1 d G . .
H84A H 0.5166 0.2503 0.4869 0.166 Uiso 1 calc R . .
H84B H 0.4603 0.3540 0.4444 0.166 Uiso 1 calc R . .
O2 O 0.571(3) 0.410(3) 0.590(2) 0.143(10) Uiso 1 d . . .
C81 C 0.525(5) 0.365(4) 0.663(3) 0.133(15) Uiso 1 d . . .
H81A H 0.5305 0.4353 0.7142 0.160 Uiso 1 calc R . .
H81B H 0.5923 0.3241 0.6929 0.160 Uiso 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_publ_flag
N2 Zn N2 180.0 2_655 . ?
N2 Zn N1 90.7(5) 2_655 2_655 ?
N2 Zn N1 89.3(5) . 2_655 ?
N2 Zn N1 89.3(5) 2_655 . ?
N2 Zn N1 90.7(5) . . ?
N1 Zn N1 180.0 2_655 . ?
N2 Zn O1 88.2(5) 2_655 2_655 ?
N2 Zn O1 91.8(5) . 2_655 ?
N1 Zn O1 89.9(5) 2_655 2_655 ?
N1 Zn O1 90.1(5) . 2_655 ?
N2 Zn O1 91.8(5) 2_655 . ?
N2 Zn O1 88.2(5) . . ?
N1 Zn O1 90.1(5) 2_655 . ?
N1 Zn O1 89.9(5) . . ?
O1 Zn O1 180.0 2_655 . ?
C1A N1 C2A 107.3(12) . . ?
C1A N1 Zn 125.9(10) . . ?
C2A N1 Zn 126.7(10) . . ?
C4A N2 C3A 109.2(12) . . ?
C4A N2 Zn 127.2(11) . . ?
C3A N2 Zn 123.3(10) . . ?
N1 C1A C1B 111.8(13) . . ?
N1 C1A C1M 127.2(13) . . ?
C1B C1A C1M 120.8(14) . . ?
N1 C2A C2M 125.4(14) . . ?
N1 C2A C2B 108.8(13) . . ?
C2M C2A C2B 125.7(14) . . ?
N2 C3A C2M 128.3(15) . . ?
N2 C3A C3B 106.3(14) . . ?
C2M C3A C3B 125.4(16) . . ?
N2 C4A C1M 124.7(15) . 2_655 ?
N2 C4A C4B 106.7(14) . . ?
C1M C4A C4B 128.6(15) 2_655 . ?
C2B C1B C1A 106.8(14) . . ?
C1B C2B C2A 105.2(13) . . ?
C1B C2B I1 120.2(11) . . ?
C2A C2B I1 134.6(12) . . ?
C4B C3B C3A 110.5(16) . . ?
C3B C4B C4A 107.2(15) . . ?
C3B C4B I2 121.2(14) . . ?
C4A C4B I2 131.6(13) . . ?
C4A C1M C1A 125.6(14) 2_655 . ?
C4A C1M C1 120.6(15) 2_655 . ?
C1A C1M C1 113.8(13) . . ?
C2A C2M C3A 125.3(16) . . ?
C2A C2M C7 121.6(15) . . ?
C3A C2M C7 112.9(16) . . ?
C6 C1 C2 118.1(16) . . ?
C6 C1 C1M 120.8(17) . . ?
C2 C1 C1M 121.1(15) . . ?
C3 C2 C1 123.7(17) . . ?
C3 C2 Cl1 118.0(15) . . ?
C1 C2 Cl1 118.2(12) . . ?
C2 C3 C4 117.8(18) . . ?
C5 C4 C3 120.6(16) . . ?
C4 C5 C6 119.8(18) . . ?
C1 C6 C5 120.0(19) . . ?
C1 C6 Cl2 121.2(15) . . ?
C5 C6 Cl2 118.8(16) . . ?
C8 C7 C12 111.8(14) . . ?
C8 C7 C2M 123.5(16) . . ?
C12 C7 C2M 124.6(18) . . ?
C9 C8 C7 122.3(18) . . ?
C9 C8 Cl3 121.8(17) . . ?
C7 C8 Cl3 115.9(13) . . ?
C8 C9 C10 124(2) . . ?
C9 C10 C11 117.7(19) . . ?
C12 C11 C10 118.5(19) . . ?
C11 C12 C7 125.6(19) . . ?
C11 C12 Cl4 118.7(17) . . ?
C7 C12 Cl4 115.5(14) . . ?
C91 O1 C94 106.8(15) . . ?
C91 O1 Zn 118.7(11) . . ?
C94 O1 Zn 121.7(11) . . ?
C92 C91 O1 105.0(16) . . ?
C91 C92 C93 101.4(17) . . ?
C92 C93 C94 103(2) . . ?
O1 C94 C93 104.2(16) . . ?
C81 C82 C83 105(3) . . ?
C82 C83 C84 104.0 . . ?
O2 C84 C83 104(3) . . ?
C81 O2 C84 103(3) . . ?
O2 C81 C82 114(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2B 2.055(15) . ?
I2 C4B 2.075(17) . ?
Zn N2 2.069(12) 2_655 ?
Zn N2 2.069(12) . ?
Zn N1 2.075(12) 2_655 ?
Zn N1 2.075(12) . ?
Zn O1 2.370(14) 2_655 ?
Zn O1 2.371(14) . ?
Cl1 C2 1.738(17) . ?
Cl2 C6 1.69(2) . ?
Cl3 C8 1.732(18) . ?
Cl4 C12 1.75(2) . ?
N1 C1A 1.323(19) . ?
N1 C2A 1.375(19) . ?
N2 C4A 1.372(19) . ?
N2 C3A 1.40(2) . ?
C1A C1B 1.42(2) . ?
C1A C1M 1.43(2) . ?
C2A C2M 1.39(2) . ?
C2A C2B 1.47(2) . ?
C3A C2M 1.41(2) . ?
C3A C3B 1.43(2) . ?
C4A C1M 1.38(2) 2_655 ?
C4A C4B 1.48(2) . ?
C1B C2B 1.38(2) . ?
C3B C4B 1.32(2) . ?
C1M C4A 1.38(2) 2_655 ?
C1M C1 1.50(2) . ?
C2M C7 1.46(2) . ?
C1 C6 1.40(3) . ?
C1 C2 1.42(3) . ?
C2 C3 1.36(2) . ?
C3 C4 1.42(3) . ?
C4 C5 1.40(3) . ?
C5 C6 1.42(3) . ?
C7 C8 1.44(3) . ?
C7 C12 1.45(3) . ?
C8 C9 1.32(3) . ?
C9 C10 1.35(3) . ?
C10 C11 1.44(3) . ?
C11 C12 1.31(3) . ?
O1 C91 1.45(2) . ?
O1 C94 1.45(2) . ?
C91 C92 1.44(3) . ?
C92 C93 1.46(3) . ?
C93 C94 1.50(3) . ?
C82 C81 1.41(5) . ?
C82 C83 1.43(3) . ?
C83 C84 1.49(3) . ?
C84 O2 1.45(4) . ?
O2 C81 1.35(4) . ?
