#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:22:48 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179575 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504095.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_4504095
loop_
_publ_author_name
'Adilov, Salimgerey'
'Thalladi, Venkat R.'
_publ_section_title
;
 Layered Porphyrin Coordination Polymers Based on
 Zinc···Nitro Recognition:  Reversible
 Intercalation of Nitrobenzene
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              481
_journal_paper_doi               10.1021/cg0607957
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C58 H40 N8 O8 Zn'
_chemical_formula_sum            'C58 H40 N8 O8 Zn'
_chemical_formula_weight         1042.35
_chemical_melting_point_gt       673.15
_chemical_name_systematic
; 
Zn-5,15-di(4-methylphenyl)-10,20-di(4-nitrophenyl)
porphyrin-Nitrobenzene Solvate  
;
_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                 94.312(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.321(2)
_cell_length_b                   11.925(2)
_cell_length_c                   18.146(3)
_cell_measurement_reflns_used    17312
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      1.80
_cell_volume                     2442.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17312
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0864P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1661
_reflns_number_gt                4175
_reflns_number_total             6051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0607957si20061109_112701.cif
_cod_data_source_block           1-Zn-PhNO2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '> 400 C' was changed to
'673.15' - it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 
;
_cod_original_cell_volume        2443.0(8)
_cod_database_code               4504095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.0000 0.0000 0.0000 0.03362(16) Uani 1 2 d S
N1 N 0.1017(2) 0.0515(2) 0.09071(12) 0.0336(5) Uani 1 1 d .
N2 N -0.0846(2) -0.1093(2) 0.06397(12) 0.0355(6) Uani 1 1 d .
N3 N 0.1063(3) -0.2196(3) 0.48363(16) 0.0575(8) Uani 1 1 d .
O1 O 0.0898(3) -0.1540(3) 0.53310(15) 0.0904(10) Uani 1 1 d .
O2 O 0.1417(2) -0.3163(3) 0.49419(14) 0.0682(8) Uani 1 1 d .
C1 C 0.2229(3) 0.1922(3) 0.03183(16) 0.0381(7) Uani 1 1 d .
C2 C 0.1902(3) 0.1306(3) 0.09245(15) 0.0364(6) Uani 1 1 d .
C3 C 0.2467(3) 0.1383(3) 0.16610(16) 0.0402(7) Uani 1 1 d .
H3 H 0.3100 0.1869 0.1820 0.048 Uiso 1 1 calc R
C4 C 0.1930(3) 0.0639(3) 0.20809(15) 0.0378(7) Uani 1 1 d .
H4 H 0.2117 0.0498 0.2592 0.045 Uiso 1 1 calc R
C5 C 0.1025(3) 0.0100(2) 0.16145(15) 0.0336(6) Uani 1 1 d .
C6 C 0.0257(2) -0.0737(2) 0.18434(14) 0.0337(6) Uani 1 1 d .
C7 C -0.0618(3) -0.1279(3) 0.13791(15) 0.0367(7) Uani 1 1 d .
C8 C -0.1414(3) -0.2115(3) 0.16248(17) 0.0468(8) Uani 1 1 d .
H8 H -0.1449 -0.2383 0.2116 0.056 Uiso 1 1 calc R
C9 C -0.2102(3) -0.2444(3) 0.10258(17) 0.0493(9) Uani 1 1 d .
H9 H -0.2713 -0.2991 0.1015 0.059 Uiso 1 1 calc R
C10 C -0.1740(3) -0.1813(3) 0.04068(16) 0.0390(7) Uani 1 1 d .
C11 C 0.3189(3) 0.2778(3) 0.04755(16) 0.0424(7) Uani 1 1 d .
C12 C 0.4350(3) 0.2508(4) 0.0434(2) 0.0705(12) Uani 1 1 d .
H12 H 0.4561 0.1785 0.0267 0.085 Uiso 1 1 calc R
C13 C 0.5238(4) 0.3298(5) 0.0637(3) 0.0861(15) Uani 1 1 d .
H13 H 0.6046 0.3093 0.0617 0.103 Uiso 1 1 calc R
C14 C 0.4969(4) 0.4336(4) 0.0861(2) 0.0740(14) Uani 1 1 d .
C15 C 0.3808(5) 0.4621(4) 0.0884(2) 0.0802(14) Uani 1 1 d .
H15 H 0.3600 0.5356 0.1030 0.096 Uiso 1 1 calc R
C16 C 0.2920(4) 0.3837(3) 0.0694(2) 0.0636(11) Uani 1 1 d .
H16 H 0.2113 0.4044 0.0718 0.076 Uiso 1 1 calc R
C17 C 0.5938(5) 0.5164(5) 0.1121(3) 0.123(3) Uani 1 1 d .
H17C H 0.5868 0.5841 0.0815 0.185 Uiso 1 1 calc R
H17A H 0.6715 0.4820 0.1076 0.185 Uiso 1 1 calc R
H17B H 0.5853 0.5363 0.1638 0.185 Uiso 1 1 calc R
C18 C 0.0425(2) -0.1118(3) 0.26289(15) 0.0351(6) Uani 1 1 d .
C19 C 0.0217(3) -0.0390(3) 0.32077(16) 0.0427(7) Uani 1 1 d .
H19 H -0.0069 0.0346 0.3104 0.051 Uiso 1 1 calc R
C20 C 0.0426(3) -0.0741(3) 0.39341(17) 0.0479(8) Uani 1 1 d .
H20 H 0.0297 -0.0246 0.4330 0.057 Uiso 1 1 calc R
C21 C 0.0819(3) -0.1811(3) 0.40721(17) 0.0436(8) Uani 1 1 d .
C22 C 0.1025(3) -0.2562(3) 0.35152(18) 0.0466(8) Uani 1 1 d .
H22 H 0.1294 -0.3302 0.3624 0.056 Uiso 1 1 calc R
C23 C 0.0822(3) -0.2194(3) 0.27911(17) 0.0439(7) Uani 1 1 d .
H23 H 0.0959 -0.2692 0.2398 0.053 Uiso 1 1 calc R
N101 N 0.6469(6) 1.0125(5) 0.1659(5) 0.116(2) Uani 1 1 d .
O101 O 0.7094(6) 1.0170(6) 0.2223(5) 0.179(3) Uani 1 1 d .
O102 O 0.6551(6) 1.0564(6) 0.1066(5) 0.236(4) Uani 1 1 d .
C101 C 0.5432(4) 0.9306(4) 0.1655(2) 0.0646(10) Uani 1 1 d .
C102 C 0.4622(7) 0.9295(6) 0.1092(3) 0.115(2) Uani 1 1 d .
H102 H 0.4685 0.9772 0.0678 0.139 Uiso 1 1 calc R
C103 C 0.3722(7) 0.8597(9) 0.1125(5) 0.148(4) Uani 1 1 d .
H103 H 0.3136 0.8601 0.0722 0.178 Uiso 1 1 calc R
C104 C 0.3573(7) 0.7896(8) 0.1671(7) 0.153(5) Uani 1 1 d .
H104 H 0.2922 0.7393 0.1659 0.183 Uiso 1 1 calc R
C105 C 0.4427(8) 0.7934(6) 0.2269(5) 0.137(3) Uani 1 1 d .
H105 H 0.4350 0.7466 0.2686 0.164 Uiso 1 1 calc R
C106 C 0.5365(5) 0.8639(4) 0.2254(2) 0.0811(13) Uani 1 1 d .
H106 H 0.5959 0.8663 0.2652 0.097 Uiso 1 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'
Zn Zn 0.2839 1.4301 '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
N1 Zn1 N1 180.00(15) . 3
N1 Zn1 N2 89.64(9) . .
N1 Zn1 N2 90.36(9) 3 .
N1 Zn1 N2 90.36(9) . 3
N1 Zn1 N2 89.64(9) 3 3
N2 Zn1 N2 180.00(17) . 3
C5 N1 C2 105.8(2) . .
C5 N1 Zn1 127.68(19) . .
C2 N1 Zn1 126.41(18) . .
C7 N2 C10 106.4(2) . .
C7 N2 Zn1 127.11(18) . .
C10 N2 Zn1 126.49(19) . .
O1 N3 O2 123.7(3) . .
O1 N3 C21 117.9(3) . .
O2 N3 C21 118.5(3) . .
C10 C1 C2 125.8(3) 3 .
C10 C1 C11 118.2(3) 3 .
C2 C1 C11 116.0(3) . .
N1 C2 C1 125.4(3) . .
N1 C2 C3 109.7(2) . .
C1 C2 C3 124.9(3) . .
C4 C3 C2 107.2(3) . .
C3 C4 C5 107.2(3) . .
N1 C5 C6 124.7(2) . .
N1 C5 C4 110.1(2) . .
C6 C5 C4 125.1(3) . .
C5 C6 C7 124.9(3) . .
C5 C6 C18 117.4(2) . .
C7 C6 C18 117.7(2) . .
N2 C7 C6 125.8(2) . .
N2 C7 C8 110.0(3) . .
C6 C7 C8 124.2(3) . .
C9 C8 C7 106.8(3) . .
C8 C9 C10 107.2(3) . .
N2 C10 C1 125.6(3) . 3
N2 C10 C9 109.6(3) . .
C1 C10 C9 124.9(3) 3 .
C12 C11 C16 118.3(3) . .
C12 C11 C1 121.1(3) . .
C16 C11 C1 120.6(3) . .
C11 C12 C13 120.0(4) . .
C14 C13 C12 121.5(4) . .
C13 C14 C15 118.7(4) . .
C13 C14 C17 121.0(5) . .
C15 C14 C17 120.2(5) . .
C14 C15 C16 120.3(5) . .
C11 C16 C15 121.2(4) . .
C23 C18 C19 119.1(3) . .
C23 C18 C6 120.0(3) . .
C19 C18 C6 120.8(3) . .
C20 C19 C18 120.1(3) . .
C21 C20 C19 119.1(3) . .
C20 C21 C22 122.7(3) . .
C20 C21 N3 120.1(3) . .
C22 C21 N3 117.2(3) . .
C21 C22 C23 117.5(3) . .
C18 C23 C22 121.5(3) . .
O101 N101 O102 131.3(9) . .
O101 N101 C101 115.8(7) . .
O102 N101 C101 112.7(8) . .
C102 C101 C106 122.5(6) . .
C102 C101 N101 119.9(6) . .
C106 C101 N101 117.5(5) . .
C103 C102 C101 117.7(7) . .
C104 C103 C102 125.3(8) . .
C103 C104 C105 116.3(7) . .
C106 C105 C104 120.1(7) . .
C101 C106 C105 118.1(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.031(2) .
Zn1 N1 2.031(2) 3
Zn1 N2 2.033(2) .
Zn1 N2 2.033(2) 3
N1 C5 1.375(3) .
N1 C2 1.375(4) .
N2 C7 1.365(3) .
N2 C10 1.369(4) .
N3 O1 1.216(4) .
N3 O2 1.231(4) .
N3 C21 1.467(4) .
C1 C10 1.395(4) 3
C1 C2 1.395(4) .
C1 C11 1.504(4) .
C2 C3 1.440(4) .
C3 C4 1.344(4) .
C4 C5 1.432(4) .
C5 C6 1.406(4) .
C6 C7 1.409(4) .
C6 C18 1.495(4) .
C7 C8 1.437(4) .
C8 C9 1.347(4) .
C9 C10 1.437(4) .
C10 C1 1.395(4) 3
C11 C12 1.361(5) .
C11 C16 1.365(5) .
C12 C13 1.407(6) .
C13 C14 1.345(7) .
C14 C15 1.362(7) .
C14 C17 1.524(5) .
C15 C16 1.397(5) .
C18 C23 1.385(4) .
C18 C19 1.396(4) .
C19 C20 1.386(4) .
C20 C21 1.367(5) .
C21 C22 1.383(5) .
C22 C23 1.388(4) .
N101 O101 1.201(9) .
N101 O102 1.206(8) .
N101 C101 1.527(8) .
C101 C102 1.321(7) .
C101 C106 1.352(6) .
C102 C103 1.320(11) .
C103 C104 1.316(12) .
C104 C105 1.398(12) .
C105 C106 1.356(8) .
