#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202553.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_2202553
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1000
_journal_page_last  o1001
_publ_section_title
;
4,4'-(N-Phenyl-2,2'-iminodiethanoxy)diphthalonitrile
;
loop_
_publ_author_name
  'Ocak, Nazan '
  'A\<gar, Ay\,sen'
  'Akdemir, Nesuhi'
  'A\<gar, Erbil'
  'Garc\'ia-Granda, S.'
  'Erd\"onmez, Ahmet'
_chemical_formula_moiety  'C26 H19 N5 O2'
_chemical_formula_sum  'C26 H19 N5 O2'
_chemical_formula_iupac  'C26 H19 N5 O2'
_chemical_formula_weight  433.46
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  '-x-1/2, y-1/2, z'
  'x, -y-1/2, z-1/2'
_cell_length_a  16.621(5)
_cell_length_b  9.004(5)
_cell_length_c  31.494(5)
_cell_angle_alpha  90.000(5)
_cell_angle_beta  90.000(5)
_cell_angle_gamma  90.000(5)
_cell_volume  4713(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.222
_diffrn_ambient_temperature  293(2)
loop_
_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
_atom_site_type_symbol
  O1 1.11340(10) 0.54371(19) 0.59502(6) 0.0864(6) Uani d . 1 . . O
  N2 0.99288(12) 0.3341(2) 0.62351(7) 0.0787(6) Uani d . 1 . . N
  C3 1.00467(14) 0.1828(3) 0.62566(8) 0.0690(7) Uani d . 1 . . C
  C4 1.18079(16) 0.5885(3) 0.57522(9) 0.0763(7) Uani d . 1 . . C
  C5 1.05667(15) 0.1218(3) 0.65566(9) 0.0852(8) Uani d . 1 . . C
  H5 1.0828 0.1838 0.6748 0.102 Uiso calc R 1 . . H
  O6 0.85398(11) 0.4874(2) 0.65186(7) 0.1084(7) Uani d . 1 . . O
  C7 0.79704(17) 0.6020(3) 0.71028(10) 0.0908(9) Uani d . 1 . . C
  H7 0.8484 0.6318 0.7184 0.109 Uiso calc R 1 . . H
  C8 1.31338(18) 0.6958(3) 0.53085(10) 0.0880(9) Uani d . 1 . . C
  C9 1.03740(17) 0.4346(3) 0.65037(9) 0.0907(9) Uani d . 1 . . C
  H9A 1.0406 0.3929 0.6787 0.109 Uiso calc R 1 . . H
  H9B 1.0085 0.5279 0.6523 0.109 Uiso calc R 1 . . H
  C10 1.12138(16) 0.4644(3) 0.63439(9) 0.0875(8) Uani d . 1 . . C
  H10A 1.1511 0.5234 0.6548 0.105 Uiso calc R 1 . . H
  H10B 1.1499 0.3718 0.6299 0.105 Uiso calc R 1 . . H
  C11 1.16970(17) 0.6789(3) 0.53976(9) 0.0842(8) Uani d . 1 . . C
  H11 1.1180 0.7031 0.5309 0.101 Uiso calc R 1 . . H
  C12 0.78608(18) 0.5158(3) 0.67405(10) 0.0881(8) Uani d . 1 . . C
  C13 1.23535(18) 0.7325(3) 0.51787(9) 0.0843(8) Uani d . 1 . . C
  C14 0.65391(17) 0.5975(3) 0.72282(10) 0.0875(8) Uani d . 1 . . C
  C15 1.32313(17) 0.6049(4) 0.56557(10) 0.0958(9) Uani d . 1 . . C
  H15 1.3748 0.5785 0.5740 0.115 Uiso calc R 1 . . H
  C16 1.25782(17) 0.5516(3) 0.58828(9) 0.0891(8) Uani d . 1 . . C
  H16 1.2656 0.4918 0.6120 0.107 Uiso calc R 1 . . H
  C17 0.64556(17) 0.5084(3) 0.68754(10) 0.0959(9) Uani d . 1 . . C
  H17 0.5945 0.4749 0.6801 0.115 Uiso calc R 1 . . H
  C18 0.96601(16) 0.0857(4) 0.59793(9) 0.0909(9) Uani d . 1 . . C
  H18 0.9301 0.1223 0.5779 0.109 Uiso calc R 1 . . H
  C19 0.84996(17) 0.3978(4) 0.61419(10) 0.0999(10) Uani d . 1 . . C
  H19A 0.8116 0.4392 0.5942 0.120 Uiso calc R 1 . . H
  H19B 0.8336 0.2973 0.6211 0.120 Uiso calc R 1 . . H
  C20 0.71044(18) 0.4672(3) 0.66285(10) 0.0939(9) Uani d . 1 . . C
  H20 0.7032 0.4077 0.6390 0.113 Uiso calc R 1 . . H
  C21 0.73120(18) 0.6426(3) 0.73402(10) 0.0866(8) Uani d . 1 . . C
  C22 0.93342(17) 0.3988(3) 0.59559(9) 0.0980(9) Uani d . 1 . . C
  H22A 0.9330 0.3441 0.5690 0.118 Uiso calc R 1 . . H
  H22B 0.9487 0.5004 0.5893 0.118 Uiso calc R 1 . . H
  C23 1.22418(19) 0.8288(4) 0.48186(13) 0.1080(11) Uani d . 1 . . C
  C24 1.3821(2) 0.7532(4) 0.50859(11) 0.1144(11) Uani d . 1 . . C
  C25 0.74284(19) 0.7335(4) 0.77131(13) 0.1090(11) Uani d . 1 . . C
  C26 0.5848(2) 0.6437(4) 0.74660(10) 0.1051(10) Uani d . 1 . . C
  C27 1.0698(2) -0.0271(5) 0.65729(14) 0.1229(13) Uani d . 1 . . C
  H27 1.1044 -0.0653 0.6778 0.148 Uiso calc R 1 . . H
  C28 0.9811(2) -0.0658(5) 0.60024(14) 0.1262(13) Uani d . 1 . . C
  H28 0.9554 -0.1303 0.5816 0.151 Uiso calc R 1 . . H
  C29 1.0335(3) -0.1208(5) 0.62975(19) 0.1436(18) Uani d . 1 . . C
  H29 1.0441 -0.2221 0.6309 0.172 Uiso calc R 1 . . H
  N30 1.43768(19) 0.7975(4) 0.49135(10) 0.1578(13) Uani d . 1 . . N
  N31 1.21692(18) 0.9059(4) 0.45360(11) 0.1447(13) Uani d . 1 . . N
  N32 0.75208(19) 0.8047(4) 0.80074(11) 0.1499(13) Uani d . 1 . . N
  N33 0.52887(18) 0.6815(4) 0.76449(10) 0.1413(12) Uani d . 1 . . N
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.0728(12) 0.0835(13) 0.1028(15) -0.0038(9) 0.0040(10) 0.0121(11)
  N2 0.0726(14) 0.0626(15) 0.1008(18) 0.0058(11) -0.0062(12) 0.0022(13)
  C3 0.0611(15) 0.0595(17) 0.087(2) 0.0032(13) 0.0066(14) 0.0035(15)
  C4 0.0698(19) 0.0695(18) 0.090(2) -0.0049(14) -0.0016(16) -0.0078(16)
  C5 0.0727(18) 0.078(2) 0.105(2) 0.0000(14) 0.0021(16) 0.0188(17)
  O6 0.0786(13) 0.1229(17) 0.1237(18) 0.0178(11) 0.0018(12) -0.0206(15)
  C7 0.081(2) 0.088(2) 0.104(2) 0.0054(16) -0.0099(18) 0.0013(19)
  C8 0.080(2) 0.102(2) 0.083(2) -0.0168(17) 0.0021(17) -0.0142(19)
  C9 0.101(2) 0.0676(18) 0.104(2) -0.0067(16) 0.0154(18) -0.0056(16)
  C10 0.088(2) 0.0780(19) 0.096(2) -0.0096(15) -0.0038(17) 0.0045(17)
  C11 0.080(2) 0.082(2) 0.091(2) -0.0069(15) -0.0068(16) 0.0012(17)
  C12 0.074(2) 0.090(2) 0.100(2) 0.0199(16) -0.0018(18) 0.0029(19)
  C13 0.088(2) 0.088(2) 0.077(2) -0.0142(17) -0.0054(17) -0.0044(17)
  C14 0.076(2) 0.100(2) 0.087(2) 0.0087(16) -0.0084(17) 0.0042(19)
  C15 0.0679(19) 0.112(2) 0.107(3) -0.0072(17) -0.0114(17) -0.011(2)
  C16 0.0724(19) 0.096(2) 0.099(2) -0.0059(16) -0.0106(17) 0.0026(17)
  C17 0.074(2) 0.111(2) 0.103(3) 0.0093(17) -0.0156(18) -0.001(2)
  C18 0.0749(18) 0.093(2) 0.105(2) -0.0066(16) 0.0077(16) -0.0163(19)
  C19 0.087(2) 0.115(2) 0.098(2) 0.0336(17) -0.0096(17) 0.000(2)
  C20 0.074(2) 0.105(2) 0.103(2) 0.0201(17) -0.0148(18) -0.0103(18)
  C21 0.087(2) 0.083(2) 0.090(2) 0.0065(16) -0.0061(18) 0.0002(17)
  C22 0.101(2) 0.091(2) 0.102(2) 0.0266(17) 0.0050(18) 0.0197(17)
  C23 0.103(2) 0.124(3) 0.097(3) -0.030(2) -0.004(2) 0.007(2)
  C24 0.092(2) 0.149(3) 0.102(3) -0.028(2) 0.011(2) -0.025(2)
  C25 0.094(2) 0.119(3) 0.115(3) 0.009(2) -0.007(2) -0.008(2)
  C26 0.093(2) 0.135(3) 0.088(3) 0.008(2) -0.0004(19) 0.000(2)
  C27 0.090(2) 0.094(3) 0.185(4) 0.015(2) 0.019(2) 0.050(3)
  C28 0.114(3) 0.096(3) 0.168(4) -0.025(2) 0.035(3) -0.045(3)
  C29 0.124(4) 0.068(3) 0.238(6) 0.010(2) 0.057(4) 0.006(3)
  N30 0.121(3) 0.208(3) 0.144(3) -0.054(2) 0.036(2) -0.023(2)
  N31 0.130(3) 0.182(3) 0.122(3) -0.042(2) -0.013(2) 0.045(2)
  N32 0.127(2) 0.181(3) 0.141(3) 0.008(2) -0.020(2) -0.056(3)
  N33 0.111(2) 0.191(3) 0.123(3) 0.007(2) 0.0179(19) -0.017(2)
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
  O1 C4 . 1.344(3) yes
  O1 C10 . 1.437(3) yes
  N2 C3 . 1.378(3) yes
  N2 C9 . 1.443(3) yes
  N2 C22 . 1.445(3) yes
  C3 C18 . 1.393(3) ?
  C3 C5 . 1.393(3) ?
  C4 C16 . 1.385(3) ?
  C4 C11 . 1.394(3) ?
  C5 C27 . 1.359(4) ?
  C5 H5 . 0.9300 ?
  O6 C12 . 1.352(3) yes
  O6 C19 . 1.436(3) yes
  C7 C21 . 1.375(3) ?
  C7 C12 . 1.392(4) ?
  C7 H7 . 0.9300 ?
  C8 C15 . 1.376(4) ?
  C8 C13 . 1.399(4) ?
  C8 C24 . 1.436(4) ?
  C9 C10 . 1.508(3) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C11 C13 . 1.378(3) ?
  C11 H11 . 0.9300 ?
  C12 C20 . 1.377(4) ?
  C13 C23 . 1.440(5) ?
  C14 C17 . 1.377(4) ?
  C14 C21 . 1.393(4) ?
  C14 C26 . 1.433(4) ?
  C15 C16 . 1.386(4) ?
  C15 H15 . 0.9300 ?
  C16 H16 . 0.9300 ?
  C17 C20 . 1.380(4) ?
  C17 H17 . 0.9300 ?
  C18 C28 . 1.389(4) ?
  C18 H18 . 0.9300 ?
  C19 C22 . 1.506(4) ?
  C19 H19A . 0.9700 ?
  C19 H19B . 0.9700 ?
  C20 H20 . 0.9300 ?
  C21 C25 . 1.445(5) ?
  C22 H22A . 0.9700 ?
  C22 H22B . 0.9700 ?
  C23 N31 . 1.135(4) yes
  C24 N30 . 1.144(4) yes
  C25 N32 . 1.137(4) yes
  C26 N33 . 1.139(4) yes
  C27 C29 . 1.352(5) ?
  C27 H27 . 0.9300 ?
  C28 C29 . 1.367(5) ?
  C28 H28 . 0.9300 ?
  C29 H29 . 0.9300 ?