#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017009.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017009
loop_
_publ_author_name
'Koner, Rajesh'
'Goldberg, Israel'
_publ_section_title
;
 Square-grid coordination networks of
 (5,10,15,20-tetra-4-pyridylporphyrinato)zinc(II) in its clathrate with
 two guest molecules of 1,2-dichlorobenzene: supramolecular isomerism
 of the porphyrin self-assembly
;
_journal_coeditor_code           GD3276
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m139
_journal_page_last               m142
_journal_paper_doi               10.1107/S0108270109005691
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (C40 H24 N8)], 2C6 H4 Cl2'
_chemical_formula_moiety         'C40 H24 N8 Zn, 2(C6 H4 Cl2)'
_chemical_formula_sum            'C52 H32 Cl4 N8 Zn'
_chemical_formula_weight         976.03
_chemical_name_systematic
;(5,10,15,20-tetra-4-pyridylporphyrinato)zinc(II) 1,2-dichlorobenzene
 disolvate
;
_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                 90.2383(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0295(2)
_cell_length_b                   13.8207(2)
_cell_length_c                   14.1529(3)
_cell_measurement_reflns_used    4704
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      1.41
_cell_volume                     2157.38(7)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1° φ'
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16059
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.8810
_exptl_absorpt_correction_T_min  0.7811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square block'
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.742
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²+0.9105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3970
_reflns_number_total             5115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3276.cif
_cod_data_source_block           I
_cod_original_cell_volume        2157.39(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017009
_cod_database_fobs_code          2017009
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.0000 0.5000 0.5000 0.01447(11) Uani d S 1 . .
C C1 -0.21505(19) 0.63951(14) 0.47345(14) 0.0168(4) Uani d . 1 . .
C C2 -0.2546(2) 0.72216(15) 0.41873(15) 0.0199(4) Uani d . 1 . .
H H2 -0.3292 0.7558 0.4253 0.024 Uiso calc R 1 . .
C C3 -0.16555(19) 0.74265(15) 0.35657(15) 0.0189(4) Uani d . 1 . .
H H3 -0.1661 0.7930 0.3109 0.023 Uiso calc R 1 . .
C C4 -0.06888(19) 0.67337(14) 0.37269(14) 0.0163(4) Uani d . 1 . .
C C5 0.04325(18) 0.67082(14) 0.32510(14) 0.0156(4) Uani d . 1 . .
C C6 0.13771(19) 0.60363(14) 0.33994(14) 0.0163(4) Uani d . 1 . .
C C7 0.24989(19) 0.60068(15) 0.28690(15) 0.0189(4) Uani d . 1 . .
H H7 0.2738 0.6439 0.2383 0.023 Uiso calc R 1 . .
C C8 0.3139(2) 0.52414(15) 0.32026(15) 0.0195(4) Uani d . 1 . .
H H8 0.3907 0.5026 0.2985 0.023 Uiso calc R 1 . .
C C9 0.24303(18) 0.48127(14) 0.39555(14) 0.0155(4) Uani d . 1 . .
C C10 0.27971(18) 0.40194(14) 0.45126(14) 0.0164(4) Uani d . 1 . .
N N11 -0.10274(15) 0.61094(12) 0.44339(12) 0.0155(3) Uani d . 1 . .
N N12 0.13679(15) 0.53132(12) 0.40536(12) 0.0155(4) Uani d . 1 . .
C C13 0.06132(18) 0.74640(15) 0.25129(14) 0.0164(4) Uani d . 1 . .
C C14 0.07091(19) 0.72181(15) 0.15608(14) 0.0177(4) Uani d . 1 . .
H H14 0.0736 0.6558 0.1376 0.021 Uiso calc R 1 . .
C C15 0.07647(19) 0.79411(15) 0.08886(15) 0.0192(4) Uani d . 1 . .
H H15 0.0824 0.7760 0.0243 0.023 Uiso calc R 1 . .
N N16 0.07393(16) 0.88808(13) 0.11004(12) 0.0190(4) Uani d . 1 . .
C C17 0.07074(19) 0.91193(15) 0.20145(15) 0.0197(4) Uani d . 1 . .
H H17 0.0723 0.9786 0.2177 0.024 Uiso calc R 1 . .
C C18 0.0654(2) 0.84467(15) 0.27368(15) 0.0199(4) Uani d . 1 . .
H H18 0.0644 0.8651 0.3378 0.024 Uiso calc R 1 . .
C C19 0.39785(19) 0.35487(14) 0.42642(15) 0.0180(4) Uani d . 1 . .
C C20 0.5027(2) 0.36887(18) 0.47905(17) 0.0267(5) Uani d . 1 . .
H H20 0.5020 0.4099 0.5329 0.032 Uiso calc R 1 . .
C C21 0.6086(2) 0.32235(19) 0.45236(18) 0.0312(5) Uani d . 1 . .
H H21 0.6795 0.3337 0.4890 0.037 Uiso calc R 1 . .
N N22 0.61716(18) 0.26284(15) 0.37886(14) 0.0289(5) Uani d . 1 . .
C C23 0.5162(2) 0.24968(19) 0.32870(18) 0.0339(6) Uani d . 1 . .
H H23 0.5196 0.2076 0.2757 0.041 Uiso calc R 1 . .
C C24 0.4062(2) 0.29363(18) 0.34906(18) 0.0297(5) Uani d . 1 . .
H H24 0.3372 0.2819 0.3103 0.036 Uiso calc R 1 . .
Cl Cl25 0.65049(6) 0.52317(5) 0.26423(5) 0.03981(18) Uani d . 1 . .
Cl Cl26 0.53532(13) 0.38155(10) 0.11492(8) 0.1045(5) Uani d . 1 . .
C C27 0.7049(2) 0.51767(18) 0.14968(19) 0.0307(5) Uani d . 1 . .
C C28 0.6557(3) 0.4547(2) 0.0851(2) 0.0479(8) Uani d . 1 . .
C C29 0.7026(4) 0.4503(3) -0.0060(2) 0.0615(10) Uani d . 1 . .
H H29 0.6690 0.4063 -0.0506 0.074 Uiso calc R 1 . .
C C30 0.7973(3) 0.5093(2) -0.0316(2) 0.0436(7) Uani d . 1 . .
H H30 0.8291 0.5064 -0.0938 0.052 Uiso calc R 1 . .
C C31 0.8460(3) 0.5727(2) 0.0336(2) 0.0373(6) Uani d . 1 . .
H H31 0.9114 0.6135 0.0159 0.045 Uiso calc R 1 . .
C C32 0.8011(2) 0.57769(19) 0.12369(18) 0.0323(6) Uani d . 1 . .
H H32 0.8352 0.6216 0.1681 0.039 Uiso calc R 1 . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N11 Zn1 N11 3_566 . 180.00(8) yes
N11 Zn1 N12 3_566 . 90.35(7) yes
N11 Zn1 N12 . . 89.65(7) yes
N11 Zn1 N12 3_566 3_566 89.65(7) yes
N11 Zn1 N12 . 3_566 90.35(7) yes
N12 Zn1 N12 . 3_566 180.00(6) yes
N11 Zn1 N16 3_566 4_576 92.49(6) yes
N11 Zn1 N16 . 4_576 87.51(6) yes
N12 Zn1 N16 . 4_576 92.27(6) yes
N12 Zn1 N16 3_566 4_576 87.73(6) yes
N11 Zn1 N16 3_566 2_545 87.51(6) yes
N11 Zn1 N16 . 2_545 92.49(6) yes
N12 Zn1 N16 . 2_545 87.73(6) yes
N12 Zn1 N16 3_566 2_545 92.27(7) yes
N16 Zn1 N16 4_576 2_545 180.0 yes
N11 C1 C10 . 3_566 125.45(18) ?
N11 C1 C2 . . 109.41(18) ?
C10 C1 C2 3_566 . 125.07(19) ?
C3 C2 C1 . . 107.20(18) ?
C3 C2 H2 . . 126.4 ?
C1 C2 H2 . . 126.4 ?
C2 C3 C4 . . 107.16(18) ?
C2 C3 H3 . . 126.4 ?
C4 C3 H3 . . 126.4 ?
N11 C4 C5 . . 124.98(18) ?
N11 C4 C3 . . 109.10(17) ?
C5 C4 C3 . . 125.91(19) ?
C6 C5 C4 . . 126.40(18) ?
C6 C5 C13 . . 117.69(18) ?
C4 C5 C13 . . 115.91(18) ?
N12 C6 C5 . . 125.20(18) ?
N12 C6 C7 . . 109.87(18) ?
C5 C6 C7 . . 124.92(18) ?
C8 C7 C6 . . 106.60(18) ?
C8 C7 H7 . . 126.7 ?
C6 C7 H7 . . 126.7 ?
C7 C8 C9 . . 107.05(18) ?
C7 C8 H8 . . 126.5 ?
C9 C8 H8 . . 126.5 ?
N12 C9 C10 . . 125.50(18) ?
N12 C9 C8 . . 109.41(18) ?
C10 C9 C8 . . 125.08(19) ?
C1 C10 C9 3_566 . 126.56(19) ?
C1 C10 C19 3_566 . 116.41(18) ?
C9 C10 C19 . . 117.01(18) ?
C1 N11 C4 . . 107.11(16) ?
C1 N11 Zn1 . . 126.06(13) ?
C4 N11 Zn1 . . 126.73(13) ?
C6 N12 C9 . . 107.04(17) ?
C6 N12 Zn1 . . 126.97(14) ?
C9 N12 Zn1 . . 125.98(14) ?
C14 C13 C18 . . 117.03(19) ?
C14 C13 C5 . . 121.15(18) ?
C18 C13 C5 . . 121.79(18) ?
C15 C14 C13 . . 119.54(19) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
N16 C15 C14 . . 123.3(2) ?
N16 C15 H15 . . 118.4 ?
C14 C15 H15 . . 118.4 ?
C15 N16 C17 . . 117.32(18) ?
C15 N16 Zn1 . 2 120.13(14) ?
C17 N16 Zn1 . 2 118.11(14) ?
N16 C17 C18 . . 123.46(19) ?
N16 C17 H17 . . 118.3 ?
C18 C17 H17 . . 118.3 ?
C17 C18 C13 . . 119.2(2) ?
C17 C18 H18 . . 120.4 ?
C13 C18 H18 . . 120.4 ?
C20 C19 C24 . . 116.8(2) ?
C20 C19 C10 . . 122.50(19) ?
C24 C19 C10 . . 120.7(2) ?
C19 C20 C21 . . 119.4(2) ?
C19 C20 H20 . . 120.3 ?
C21 C20 H20 . . 120.3 ?
N22 C21 C20 . . 124.2(2) ?
N22 C21 H21 . . 117.9 ?
C20 C21 H21 . . 117.9 ?
C21 N22 C23 . . 116.1(2) ?
N22 C23 C24 . . 124.0(2) ?
N22 C23 H23 . . 118.0 ?
C24 C23 H23 . . 118.0 ?
C19 C24 C23 . . 119.4(2) ?
C19 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C28 C27 C32 . . 120.0(3) ?
C28 C27 Cl25 . . 120.9(2) ?
C32 C27 Cl25 . . 119.1(2) ?
C27 C28 C29 . . 119.8(3) ?
C27 C28 Cl26 . . 120.8(2) ?
C29 C28 Cl26 . . 119.4(2) ?
C30 C29 C28 . . 120.2(3) ?
C30 C29 H29 . . 119.9 ?
C28 C29 H29 . . 119.9 ?
C29 C30 C31 . . 119.6(3) ?
C29 C30 H30 . . 120.2 ?
C31 C30 H30 . . 120.2 ?
C32 C31 C30 . . 120.8(3) ?
C32 C31 H31 . . 119.6 ?
C30 C31 H31 . . 119.6 ?
C31 C32 C27 . . 119.5(2) ?
C31 C32 H32 . . 120.3 ?
C27 C32 H32 . . 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 N11 3_566 2.0662(16) yes
Zn1 N11 . 2.0663(16) yes
Zn1 N12 . 2.0675(17) yes
Zn1 N12 3_566 2.0675(17) yes
Zn1 N16 4_576 2.3393(17) yes
Zn1 N16 2_545 2.3393(17) yes
C1 N11 . 1.370(3) ?
C1 C10 3_566 1.407(3) ?
C1 C2 . 1.446(3) ?
C2 C3 . 1.351(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.450(3) ?
C3 H3 . 0.9500 ?
C4 N11 . 1.374(3) ?
C4 C5 . 1.411(3) ?
C5 C6 . 1.411(3) ?
C5 C13 . 1.491(3) ?
C6 N12 . 1.362(3) ?
C6 C7 . 1.450(3) ?
C7 C8 . 1.356(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.451(3) ?
C8 H8 . 0.9500 ?
C9 N12 . 1.368(3) ?
C9 C10 . 1.409(3) ?
C10 C1 3_566 1.407(3) ?
C10 C19 . 1.499(3) ?
C13 C14 . 1.394(3) ?
C13 C18 . 1.395(3) ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9500 ?
C15 N16 . 1.333(3) ?
C15 H15 . 0.9500 ?
N16 C17 . 1.336(3) ?
N16 Zn1 2 2.3393(17) yes
C17 C18 . 1.383(3) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.386(3) ?
C19 C24 . 1.387(3) ?
C20 C21 . 1.387(3) ?
C20 H20 . 0.9500 ?
C21 N22 . 1.330(3) ?
C21 H21 . 0.9500 ?
N22 C23 . 1.331(3) ?
C23 C24 . 1.388(3) ?
C23 H23 . 0.9500 ?
C24 H24 . 0.9500 ?
Cl25 C27 . 1.733(3) ?
Cl26 C28 . 1.723(3) ?
C27 C28 . 1.372(4) ?
C27 C32 . 1.398(4) ?
C28 C29 . 1.392(4) ?
C29 C30 . 1.375(4) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.380(4) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.371(4) ?
C31 H31 . 0.9500 ?
C32 H32 . 0.9500 ?
