#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150016.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_7150016
loop_
_publ_author_name
'Uno, Hidemitsu'
'Watanabe, Hikaru'
'Yamashita, Yuko'
'Ono, Noboru'
_publ_section_title
;
 Extremely large cavity assembled by self-interlocking of distorted
 biconcave porphyrins.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              448
_journal_page_last               453
_journal_paper_doi               10.1039/b413082k
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C108 H62 N4, 12(C6 H6)'
_chemical_formula_sum            'C180 H134 N4'
_chemical_formula_weight         2352.91
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3904(10)
_cell_length_b                   19.3904(10)
_cell_length_c                   36.077(2)
_cell_measurement_reflns_used    12512
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     13564.5(12)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure Ver. 3.5.1'
_computing_structure_refinement  'SHELXH-97 and PLATON SQUEEZE'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo Ka'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            55378
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   Coppens_numerical
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             4968
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         7742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0658
_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/[s²(Fo²)+(0.1210P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                4993
_reflns_number_total             7742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b413082k.txt
_cod_data_source_block           12-12PhHsqueezed(12)
_cod_original_cell_volume        13564.4(12)
_cod_original_sg_symbol_Hall     '-I 4ad '
_cod_original_sg_symbol_H-M      'I 41/a '
_cod_original_formula_sum        'C180 H134 N4 '
_cod_database_code               7150016
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.52912(6) 0.64759(6) 0.12386(3) 0.0247(3) Uani 1 1 d . . .
C1 C 0.48448(7) 0.59215(7) 0.12274(3) 0.0247(3) Uani 1 1 d . . .
C2 C 0.52563(7) 0.53007(7) 0.12191(3) 0.0252(3) Uani 1 1 d . . .
C3 C 0.59314(7) 0.54889(7) 0.12292(3) 0.0256(3) Uani 1 1 d . . .
C4 C 0.59552(7) 0.62289(7) 0.12452(3) 0.0251(3) Uani 1 1 d . . .
C5 C 0.65460(7) 0.66323(7) 0.12638(3) 0.0264(3) Uani 1 1 d . . .
C6 C 0.51223(7) 0.45358(7) 0.12272(4) 0.0269(3) Uani 1 1 d . . .
C7 C 0.54971(7) 0.42889(7) 0.15770(4) 0.0284(3) Uani 1 1 d . . .
C8 C 0.52146(8) 0.39315(8) 0.18635(4) 0.0321(3) Uani 1 1 d . . .
C9 C 0.56266(9) 0.37408(8) 0.21731(4) 0.0370(4) Uani 1 1 d . . .
C10 C 0.53571(10) 0.33662(9) 0.24781(5) 0.0470(4) Uani 1 1 d . . .
C11 C 0.57709(12) 0.31803(11) 0.27661(5) 0.0572(5) Uani 1 1 d . . .
C12 C 0.64683(11) 0.33580(11) 0.27705(5) 0.0564(5) Uani 1 1 d . . .
C13 C 0.67478(10) 0.37149(9) 0.24840(4) 0.0443(4) Uani 1 1 d . . .
C14 C 0.63364(9) 0.39169(8) 0.21768(4) 0.0368(4) Uani 1 1 d . . .
C15 C 0.66181(8) 0.42942(8) 0.18738(4) 0.0327(3) Uani 1 1 d . . .
C16 C 0.62088(7) 0.44813(7) 0.15870(4) 0.0281(3) Uani 1 1 d . . .
C17 C 0.64328(7) 0.48956(7) 0.12436(4) 0.0287(3) Uani 1 1 d . . .
C18 C 0.62553(7) 0.44289(7) 0.09162(4) 0.0283(3) Uani 1 1 d . . .
C19 C 0.66999(8) 0.41953(8) 0.06573(4) 0.0363(4) Uani 1 1 d . . .
C20 C 0.64548(9) 0.37758(8) 0.03573(4) 0.0413(4) Uani 1 1 d . . .
C21 C 0.69027(11) 0.35369(10) 0.00775(5) 0.0567(5) Uani 1 1 d . . .
C22 C 0.66402(14) 0.31733(12) -0.02203(6) 0.0721(7) Uani 1 1 d . . .
C23 C 0.59439(14) 0.30384(12) -0.02475(5) 0.0698(7) Uani 1 1 d . . .
C24 C 0.55029(12) 0.32564(10) 0.00228(5) 0.0568(5) Uani 1 1 d . . .
C25 C 0.57449(10) 0.36212(8) 0.03347(4) 0.0407(4) Uani 1 1 d . . .
C26 C 0.52909(8) 0.38542(8) 0.06202(4) 0.0338(3) Uani 1 1 d . . .
C27 C 0.55411(8) 0.42438(7) 0.09037(4) 0.0288(3) Uani 1 1 d . . .
H1 H 0.5174 0.6903 0.1241 0.030 Uiso 0.50 1 c P . .
H2 H 0.6965 0.6398 0.1271 0.032 Uiso 1 1 c . . .
H3 H 0.4632 0.4413 0.1220 0.032 Uiso 1 1 c . . .
H4 H 0.4750 0.3811 0.1857 0.039 Uiso 1 1 c . . .
H5 H 0.4893 0.3246 0.2481 0.056 Uiso 1 1 c . . .
H6 H 0.5586 0.2931 0.2963 0.069 Uiso 1 1 c . . .
H7 H 0.6743 0.3231 0.2971 0.068 Uiso 1 1 c . . .
H8 H 0.7214 0.3828 0.2489 0.053 Uiso 1 1 c . . .
H9 H 0.7083 0.4412 0.1873 0.039 Uiso 1 1 c . . .
H10 H 0.6917 0.5040 0.1250 0.034 Uiso 1 1 c . . .
H11 H 0.7166 0.4306 0.0673 0.044 Uiso 1 1 c . . .
H12 H 0.7374 0.3624 0.0093 0.068 Uiso 1 1 c . . .
H13 H 0.6937 0.3018 -0.0405 0.086 Uiso 1 1 c . . .
H14 H 0.5774 0.2798 -0.0451 0.084 Uiso 1 1 c . . .
H15 H 0.5034 0.3162 0.0001 0.068 Uiso 1 1 c . . .
H16 H 0.4825 0.3740 0.0612 0.041 Uiso 1 1 c . . .
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'
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
C4 N1 C1 108.45(11) . . ?
C4 N1 H1 125.78 . . ?
C1 N1 H1 125.77 . . ?
N1 C1 C5 126.14(13) . 14_565 ?
N1 C1 C2 107.65(11) . . ?
C5 C1 C2 126.17(13) 14_565 . ?
C3 C2 C1 107.91(12) . . ?
C3 C2 C6 115.47(12) . . ?
C1 C2 C6 136.47(13) . . ?
C2 C3 C4 107.46(12) . . ?
C2 C3 C17 114.66(12) . . ?
C4 C3 C17 137.76(13) . . ?
N1 C4 C5 125.27(13) . . ?
N1 C4 C3 108.51(12) . . ?
C5 C4 C3 126.22(13) . . ?
C1 C5 C4 126.96(13) 12_766 . ?
C1 C5 H2 116.51 12_766 . ?
C4 C5 H2 116.53 . . ?
C2 C6 C27 104.96(11) . . ?
C2 C6 C7 103.99(11) . . ?
C27 C6 C7 105.10(11) . . ?
C2 C6 H3 113.92 . . ?
C27 C6 H3 113.91 . . ?
C7 C6 H3 113.92 . . ?
C8 C7 C16 120.17(13) . . ?
C8 C7 C6 126.44(13) . . ?
C16 C7 C6 113.39(12) . . ?
C7 C8 C9 120.21(14) . . ?
C7 C8 H4 119.90 . . ?
C9 C8 H4 119.89 . . ?
C14 C9 C10 118.26(15) . . ?
C14 C9 C8 119.35(13) . . ?
C10 C9 C8 122.38(15) . . ?
C11 C10 C9 120.70(17) . . ?
C11 C10 H5 119.65 . . ?
C9 C10 H5 119.64 . . ?
C10 C11 C12 120.97(16) . . ?
C10 C11 H6 119.5 . . ?
C12 C11 H6 119.5 . . ?
C13 C12 C11 120.28(17) . . ?
C13 C12 H7 119.9 . . ?
C11 C12 H7 119.86 . . ?
C12 C13 C14 120.71(17) . . ?
C12 C13 H8 119.64 . . ?
C14 C13 H8 119.65 . . ?
C9 C14 C13 119.08(14) . . ?
C9 C14 C15 119.25(14) . . ?
C13 C14 C15 121.67(15) . . ?
C16 C15 C14 119.97(14) . . ?
C16 C15 H9 120.01 . . ?
C14 C15 H9 120.03 . . ?
C15 C16 C7 121.01(13) . . ?
C15 C16 C17 126.14(13) . . ?
C7 C16 C17 112.84(12) . . ?
C3 C17 C18 106.27(11) . . ?
C3 C17 C16 104.13(11) . . ?
C18 C17 C16 104.46(11) . . ?
C3 C17 H10 113.66 . . ?
C18 C17 H10 113.68 . . ?
C16 C17 H10 113.69 . . ?
C19 C18 C27 120.82(13) . . ?
C19 C18 C17 126.17(13) . . ?
C27 C18 C17 113.01(12) . . ?
C18 C19 C20 120.05(14) . . ?
C18 C19 H11 119.99 . . ?
C20 C19 H11 119.95 . . ?
C21 C20 C25 119.32(16) . . ?
C21 C20 C19 121.48(16) . . ?
C25 C20 C19 119.15(14) . . ?
C22 C21 C20 119.81(19) . . ?
C22 C21 H12 120.10 . . ?
C20 C21 H12 120.09 . . ?
C23 C22 C21 120.86(18) . . ?
C23 C22 H13 119.6 . . ?
C21 C22 H13 119.6 . . ?
C24 C23 C22 120.27(19) . . ?
C24 C23 H14 119.9 . . ?
C22 C23 H14 119.9 . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H15 119.42 . . ?
C25 C24 H15 119.41 . . ?
C24 C25 C20 118.52(16) . . ?
C24 C25 C26 121.96(17) . . ?
C20 C25 C26 119.49(14) . . ?
C27 C26 C25 119.87(14) . . ?
C27 C26 H16 120.08 . . ?
C25 C26 H16 120.06 . . ?
C26 C27 C18 120.52(14) . . ?
C26 C27 C6 126.11(13) . . ?
C18 C27 C6 113.38(12) . . ?
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
N1 C4 1.3739(18) . ?
N1 C1 1.3808(18) . ?
N1 H1 0.8600 . ?
C1 C5 1.383(2) 14_565 ?
C1 C2 1.4444(19) . ?
C2 C3 1.360(2) . ?
C2 C6 1.506(2) . ?
C3 C4 1.4367(19) . ?
C3 C17 1.507(2) . ?
C4 C5 1.389(2) . ?
C5 C1 1.383(2) 12_766 ?
C5 H2 0.9300 . ?
C6 C27 1.5303(19) . ?
C6 C7 1.5329(19) . ?
C6 H3 0.9802 . ?
C7 C8 1.3598(19) . ?
C7 C16 1.430(2) . ?
C8 C9 1.422(2) . ?
C8 H4 0.9300 . ?
C9 C14 1.418(2) . ?
C9 C10 1.418(2) . ?
C10 C11 1.362(3) . ?
C10 H5 0.9300 . ?
C11 C12 1.396(3) . ?
C11 H6 0.9299 . ?
C12 C13 1.357(2) . ?
C12 H7 0.9299 . ?
C13 C14 1.421(2) . ?
C13 H8 0.9300 . ?
C14 C15 1.424(2) . ?
C15 C16 1.354(2) . ?
C15 H9 0.9299 . ?
C16 C17 1.5391(18) . ?
C17 C18 1.5274(19) . ?
C17 H10 0.9799 . ?
C18 C19 1.349(2) . ?
C18 C27 1.431(2) . ?
C19 C20 1.435(2) . ?
C19 H11 0.9300 . ?
C20 C21 1.410(2) . ?
C20 C25 1.411(3) . ?
C21 C22 1.382(3) . ?
C21 H12 0.930 . ?
C22 C23 1.379(4) . ?
C22 H13 0.9301 . ?
C23 C24 1.364(3) . ?
C23 H14 0.930 . ?
C24 C25 1.410(2) . ?
C24 H15 0.930 . ?
C25 C26 1.428(2) . ?
C26 C27 1.361(2) . ?
C26 H16 0.9301 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C5 176.66(12) . . . 14_565 ?
C4 N1 C1 C2 -1.20(13) . . . . ?
N1 C1 C2 C3 0.62(14) . . . . ?
C5 C1 C2 C3 -177.24(12) 14_565 . . . ?
N1 C1 C2 C6 175.77(13) . . . . ?
C5 C1 C2 C6 -2.1(2) 14_565 . . . ?
C1 C2 C3 C4 0.18(14) . . . . ?
C6 C2 C3 C4 -176.12(10) . . . . ?
C1 C2 C3 C17 176.79(10) . . . . ?
C6 C2 C3 C17 0.49(16) . . . . ?
C1 N1 C4 C5 -178.73(12) . . . . ?
C1 N1 C4 C3 1.32(13) . . . . ?
C2 C3 C4 N1 -0.92(14) . . . . ?
C17 C3 C4 N1 -176.35(14) . . . . ?
C2 C3 C4 C5 179.13(12) . . . . ?
C17 C3 C4 C5 3.7(2) . . . . ?
N1 C4 C5 C1 -1.2(2) . . . 12_766 ?
C3 C4 C5 C1 178.75(12) . . . 12_766 ?
C3 C2 C6 C27 -54.85(14) . . . . ?
C1 C2 C6 C27 130.27(15) . . . . ?
C3 C2 C6 C7 55.30(14) . . . . ?
C1 C2 C6 C7 -119.58(16) . . . . ?
C2 C6 C7 C8 124.53(15) . . . . ?
C27 C6 C7 C8 -125.43(15) . . . . ?
C2 C6 C7 C16 -54.37(15) . . . . ?
C27 C6 C7 C16 55.67(15) . . . . ?
C16 C7 C8 C9 -0.6(2) . . . . ?
C6 C7 C8 C9 -179.47(13) . . . . ?
C7 C8 C9 C14 -1.1(2) . . . . ?
C7 C8 C9 C10 -179.79(15) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 178.62(17) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C8 C9 C14 C13 -178.97(14) . . . . ?
C10 C9 C14 C15 -179.87(14) . . . . ?
C8 C9 C14 C15 1.4(2) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C12 C13 C14 C15 179.73(17) . . . . ?
C9 C14 C15 C16 0.1(2) . . . . ?
C13 C14 C15 C16 -179.58(15) . . . . ?
C14 C15 C16 C7 -1.8(2) . . . . ?
C14 C15 C16 C17 179.18(13) . . . . ?
C8 C7 C16 C15 2.1(2) . . . . ?
C6 C7 C16 C15 -178.89(13) . . . . ?
C8 C7 C16 C17 -178.75(12) . . . . ?
C6 C7 C16 C17 0.23(16) . . . . ?
C2 C3 C17 C18 53.93(14) . . . . ?
C4 C3 C17 C18 -130.88(16) . . . . ?
C2 C3 C17 C16 -56.06(15) . . . . ?
C4 C3 C17 C16 119.14(16) . . . . ?
C15 C16 C17 C3 -126.44(15) . . . . ?
C7 C16 C17 C3 54.50(15) . . . . ?
C15 C16 C17 C18 122.26(15) . . . . ?
C7 C16 C17 C18 -56.81(15) . . . . ?
C3 C17 C18 C19 128.21(15) . . . . ?
C16 C17 C18 C19 -122.04(15) . . . . ?
C3 C17 C18 C27 -52.06(15) . . . . ?
C16 C17 C18 C27 57.69(15) . . . . ?
C27 C18 C19 C20 2.2(2) . . . . ?
C17 C18 C19 C20 -178.04(13) . . . . ?
C18 C19 C20 C21 178.48(16) . . . . ?
C18 C19 C20 C25 0.9(2) . . . . ?
C25 C20 C21 C22 1.9(3) . . . . ?
C19 C20 C21 C22 -175.65(19) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C20 1.8(3) . . . . ?
C23 C24 C25 C26 179.9(2) . . . . ?
C21 C20 C25 C24 -2.7(2) . . . . ?
C19 C20 C25 C24 174.92(16) . . . . ?
C21 C20 C25 C26 179.14(16) . . . . ?
C19 C20 C25 C26 -3.2(2) . . . . ?
C24 C25 C26 C27 -175.66(16) . . . . ?
C20 C25 C26 C27 2.4(2) . . . . ?
C25 C26 C27 C18 0.7(2) . . . . ?
C25 C26 C27 C6 179.51(14) . . . . ?
C19 C18 C27 C26 -3.1(2) . . . . ?
C17 C18 C27 C26 177.15(13) . . . . ?
C19 C18 C27 C6 177.95(13) . . . . ?
C17 C18 C27 C6 -1.81(16) . . . . ?
C2 C6 C27 C26 -124.45(15) . . . . ?
C7 C6 C27 C26 126.21(15) . . . . ?
C2 C6 C27 C18 54.44(15) . . . . ?
C7 C6 C27 C18 -54.90(15) . . . . ?
