#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/60/2016068.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_2016068
loop_
_publ_author_name
'Sophia Lipstman'
'Sankar Muniappan'
'Israel Goldberg'
_publ_section_title
;
 The nature of supramolecular interactions in
 tetrakis(4-iodophenyl)porphyrin and its zinc(II) complex
;
_journal_coeditor_code           SK3127
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m300
_journal_page_last               m303
_journal_paper_doi               10.1107/S0108270107023104
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C44 H26 I4 N4 , 0.85C H Cl3'
_chemical_formula_moiety         'C44 H26 I4 N4 , 0.85C H Cl3'
_chemical_formula_sum            'C44.85 H26.85 Cl2.55 I4 N4'
_chemical_formula_weight         1219.99
_chemical_name_systematic
;
tetrakis(4-iodophenyl)porphyrin chloroform 0.85-solvate
;
_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           SHELXL97
_cell_angle_alpha                117.1350(10)
_cell_angle_beta                 100.6121(10)
_cell_angle_gamma                92.7217(19)
_cell_formula_units_Z            1
_cell_length_a                   6.5360(2)
_cell_length_b                   13.4507(3)
_cell_length_c                   13.8558(4)
_cell_measurement_reflns_used    3898
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.93
_cell_volume                     1053.40(5)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1° φ and ω'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11891
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.158
_exptl_absorpt_correction_T_max  0.8582
_exptl_absorpt_correction_T_min  0.4513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             579.4
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.510
_refine_diff_density_min         -1.627
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0471
_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)+(0.0716P)²+2.8926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                3760
_reflns_number_total             5033
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3127.cif
_cod_data_source_block           I
_cod_database_code               2016068
_cod_database_fobs_code          2016068
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1833(8) 0.1556(5) 1.0933(5) 0.0182(11) Uani d . 1
C C2 0.0763(9) 0.2459(5) 1.0855(5) 0.0213(11) Uani d . 1
H H2 -0.0278 0.2811 1.1238 0.026 Uiso calc R 1
C C3 0.1544(9) 0.2692(5) 1.0134(5) 0.0228(12) Uani d . 1
H H3 0.1163 0.3246 0.9917 0.027 Uiso calc R 1
C C4 0.3076(8) 0.1939(5) 0.9750(5) 0.0187(11) Uani d . 1
C C5 0.4319(8) 0.1964(5) 0.9036(5) 0.0202(11) Uani d . 1
C C6 0.5798(8) 0.1245(5) 0.8664(5) 0.0172(11) Uani d . 1
C C7 0.6835(9) 0.1118(5) 0.7788(5) 0.0217(12) Uani d . 1
H H7 0.6740 0.1562 0.7415 0.026 Uiso calc R 1
C C8 0.7969(9) 0.0254(5) 0.7590(5) 0.0236(12) Uani d . 1
H H8 0.8793 -0.0022 0.7049 0.028 Uiso calc R 1
C C9 0.7694(8) -0.0167(5) 0.8347(5) 0.0171(11) Uani d . 1
C C10 0.8512(8) -0.1105(5) 0.8376(5) 0.0197(11) Uani d . 1
N N11 0.3196(7) 0.1257(4) 1.0243(4) 0.0186(9) Uani d . 1
H H11 0.3999 0.0727 1.0136 0.022 Uiso calc PR 0.50
N N12 0.6385(7) 0.0454(4) 0.8988(4) 0.0162(9) Uani d . 1
H H12 0.5988 0.0361 0.9518 0.019 Uiso calc PR 0.50
C C13 0.4083(8) 0.2831(5) 0.8647(5) 0.0197(11) Uani d . 1
C C14 0.2174(9) 0.2884(6) 0.8046(6) 0.0289(13) Uani d . 1
H H14 0.0981 0.2346 0.7861 0.035 Uiso calc R 1
C C15 0.1978(10) 0.3719(6) 0.7708(6) 0.0303(14) Uani d . 1
H H15 0.0656 0.3761 0.7318 0.036 Uiso calc R 1
C C16 0.3727(9) 0.4477(5) 0.7950(5) 0.0216(11) Uani d . 1
C C17 0.5656(9) 0.4438(5) 0.8528(5) 0.0247(12) Uani d . 1
H H17 0.6855 0.4961 0.8682 0.030 Uiso calc R 1
C C18 0.5819(9) 0.3625(5) 0.8882(5) 0.0221(12) Uani d . 1
H H18 0.7138 0.3606 0.9293 0.026 Uiso calc R 1
I I19 0.34452(6) 0.57354(3) 0.74490(3) 0.02362(13) Uani d . 1
C C20 0.9730(8) -0.1723(5) 0.7503(5) 0.0195(11) Uani d . 1
C C21 0.8798(8) -0.2768(5) 0.6623(5) 0.0208(11) Uani d . 1
H H21 0.7459 -0.3091 0.6607 0.025 Uiso calc R 1
C C22 0.9786(8) -0.3355(5) 0.5761(5) 0.0214(12) Uani d . 1
H H22 0.9120 -0.4063 0.5151 0.026 Uiso calc R 1
C C23 1.1765(8) -0.2883(5) 0.5813(5) 0.0188(11) Uani d . 1
C C24 1.2754(9) -0.1843(5) 0.6703(5) 0.0245(12) Uani d . 1
H H24 1.4113 -0.1530 0.6733 0.029 Uiso calc R 1
C C25 1.1726(9) -0.1271(5) 0.7544(5) 0.0248(13) Uani d . 1
H H25 1.2390 -0.0563 0.8155 0.030 Uiso calc R 1
I I26 1.32858(6) -0.37844(3) 0.45233(3) 0.02612(13) Uani d . 1
C C27 0.831(3) -0.049(2) 0.449(2) 0.062(6) Uiso d P 0.426(5)
H H27 0.7957 -0.0677 0.3691 0.075 Uiso d PR 0.426(5)
Cl Cl28 0.6598(8) -0.1488(4) 0.4580(4) 0.0537(14) Uiso d P 0.426(5)
Cl Cl29 0.7716(11) 0.0848(6) 0.5204(6) 0.077(2) Uiso d P 0.426(5)
Cl Cl30 1.0911(11) -0.0657(6) 0.4783(6) 0.0719(18) Uiso d P 0.426(5)
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'
I I -0.4742 1.8119 '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'
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
N11 C1 C10 . 2_657 126.8(5)
N11 C1 C2 . . 109.5(5)
C10 C1 C2 2_657 . 123.7(5)
C3 C2 C1 . . 106.6(5)
C3 C2 H2 . . 126.7
C1 C2 H2 . . 126.7
C2 C3 C4 . . 107.3(5)
C2 C3 H3 . . 126.3
C4 C3 H3 . . 126.3
N11 C4 C5 . . 125.8(5)
N11 C4 C3 . . 109.6(5)
C5 C4 C3 . . 124.6(5)
C4 C5 C6 . . 125.0(5)
C4 C5 C13 . . 118.2(5)
C6 C5 C13 . . 116.8(5)
N12 C6 C5 . . 126.4(5)
N12 C6 C7 . . 107.2(5)
C5 C6 C7 . . 126.1(5)
C8 C7 C6 . . 108.2(5)
C8 C7 H7 . . 125.9
C6 C7 H7 . . 125.9
C7 C8 C9 . . 107.3(5)
C7 C8 H8 . . 126.3
C9 C8 H8 . . 126.3
N12 C9 C10 . . 125.9(5)
N12 C9 C8 . . 108.3(5)
C10 C9 C8 . . 125.6(5)
C1 C10 C9 2_657 . 126.1(5)
C1 C10 C20 2_657 . 117.8(5)
C9 C10 C20 . . 115.8(5)
C1 N11 C4 . . 107.0(4)
C1 N11 H11 . . 126.5
C4 N11 H11 . . 126.5
C6 N12 C9 . . 108.9(4)
C6 N12 H12 . . 125.6
C9 N12 H12 . . 125.6
C14 C13 C18 . . 117.7(5)
C14 C13 C5 . . 122.2(5)
C18 C13 C5 . . 120.1(5)
C13 C14 C15 . . 121.2(6)
C13 C14 H14 . . 119.4
C15 C14 H14 . . 119.4
C16 C15 C14 . . 119.1(5)
C16 C15 H15 . . 120.5
C14 C15 H15 . . 120.5
C15 C16 C17 . . 121.3(5)
C15 C16 I19 . . 119.3(4)
C17 C16 I19 . . 119.3(4)
C16 C17 C18 . . 119.1(5)
C16 C17 H17 . . 120.5
C18 C17 H17 . . 120.5
C17 C18 C13 . . 121.5(5)
C17 C18 H18 . . 119.2
C13 C18 H18 . . 119.2
C21 C20 C25 . . 119.2(5)
C21 C20 C10 . . 118.3(5)
C25 C20 C10 . . 122.5(5)
C20 C21 C22 . . 121.2(5)
C20 C21 H21 . . 119.4
C22 C21 H21 . . 119.4
C23 C22 C21 . . 118.6(5)
C23 C22 H22 . . 120.7
C21 C22 H22 . . 120.7
C22 C23 C24 . . 121.2(5)
C22 C23 I26 . . 118.6(4)
C24 C23 I26 . . 120.2(4)
C25 C24 C23 . . 119.0(5)
C25 C24 H24 . . 120.5
C23 C24 H24 . . 120.5
C24 C25 C20 . . 120.8(5)
C24 C25 H25 . . 119.6
C20 C25 H25 . . 119.6
Cl29 C27 Cl30 . . 116.5(14)
Cl29 C27 Cl28 . . 110.8(13)
Cl30 C27 Cl28 . . 112.3(13)
Cl29 C27 H27 . . 105.3
Cl30 C27 H27 . . 105.6
Cl28 C27 H27 . . 105.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N11 . 1.366(7)
C1 C10 2_657 1.391(8)
C1 C2 . 1.465(8)
C2 C3 . 1.348(8)
C2 H2 . 0.9500
C3 C4 . 1.454(7)
C3 H3 . 0.9500
C4 N11 . 1.368(7)
C4 C5 . 1.402(8)
C5 C6 . 1.397(7)
C5 C13 . 1.495(8)
C6 N12 . 1.374(7)
C6 C7 . 1.445(8)
C7 C8 . 1.357(8)
C7 H7 . 0.9500
C8 C9 . 1.433(8)
C8 H8 . 0.9500
C9 N12 . 1.374(7)
C9 C10 . 1.408(8)
C10 C1 2_657 1.390(8)
C10 C20 . 1.512(8)
N11 H11 . 0.8800
N12 H12 . 0.8800
C13 C14 . 1.391(8)
C13 C18 . 1.402(8)
C14 C15 . 1.402(9)
C14 H14 . 0.9500
C15 C16 . 1.376(8)
C15 H15 . 0.9500
C16 C17 . 1.381(8)
C16 I19 . 2.106(6)
C17 C18 . 1.389(8)
C17 H17 . 0.9500
C18 H18 . 0.9500
C20 C21 . 1.383(8)
C20 C25 . 1.393(8)
C21 C22 . 1.393(8)
C21 H21 . 0.9500
C22 C23 . 1.388(8)
C22 H22 . 0.9500
C23 C24 . 1.394(8)
C23 I26 . 2.108(5)
C24 C25 . 1.386(8)
C24 H24 . 0.9500
C25 H25 . 0.9500
C27 Cl29 . 1.72(2)
C27 Cl30 . 1.72(2)
C27 Cl28 . 1.76(2)
C27 H27 . 1.0000
