#------------------------------------------------------------------------------
#$Date: 2011-09-28 16:24:46 +0200 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100264.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_2100264
_journal_name_full  'Acta Crystallographica, Section B'
_journal_year  2005
_journal_volume  61
_journal_page_first  321
_journal_page_last  328
_publ_section_title
;
Concomitant polymorphism and a temperature-dependent phase change in
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Skakle, Janet M. S.'
  'Low, John N.'
  'Wardell, James L.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C18 H17 N O4'
_chemical_formula_sum  'C18 H17 N O4'
_chemical_formula_weight  311.33
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  12.1552(4)
_cell_length_b  15.8657(4)
_cell_length_c  16.6708(5)
_cell_angle_alpha  90.00
_cell_angle_beta  97.4250(15)
_cell_angle_gamma  90.00
_cell_volume  3188.02(16)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.297
_diffrn_ambient_temperature  120(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
  O11 0.60212(10) 0.56379(9) 0.28717(7) 0.0435(4) Uani d . 1 . . O
  O12 0.42927(11) 0.52190(8) 0.29603(7) 0.0411(3) Uani d . 1 . . O
  O13 0.43379(10) 0.58474(7) 0.44360(7) 0.0323(3) Uani d . 1 . . O
  O124 -0.11867(10) 0.29543(7) 0.59410(7) 0.0331(3) Uani d . 1 . . O
  N14 0.42907(12) 0.64910(9) 0.50237(8) 0.0290(3) Uani d . 1 . . N
  C11 0.51295(14) 0.55789(11) 0.32369(10) 0.0291(4) Uani d . 1 . . C
  C12 0.52739(15) 0.60170(12) 0.40365(11) 0.0352(4) Uani d . 1 . . C
  C15 0.34766(14) 0.63659(10) 0.54340(9) 0.0264(4) Uani d . 1 . . C
  C16 0.26956(14) 0.56694(10) 0.53505(9) 0.0280(4) Uani d . 1 . . C
  C17 0.19449(14) 0.55516(10) 0.58655(10) 0.0281(4) Uani d . 1 . . C
  C111 0.33781(14) 0.70341(10) 0.60582(9) 0.0269(4) Uani d . 1 . . C
  C112 0.25273(17) 0.76212(12) 0.59476(11) 0.0409(5) Uani d . 1 . . C
  C113 0.24311(18) 0.82324(12) 0.65273(11) 0.0444(5) Uani d . 1 . . C
  C114 0.31780(16) 0.82537(11) 0.72226(11) 0.0365(4) Uani d . 1 . . C
  C115 0.40130(15) 0.76687(12) 0.73392(11) 0.0391(5) Uani d . 1 . . C
  C116 0.41229(14) 0.70639(12) 0.67570(10) 0.0348(4) Uani d . 1 . . C
  C121 0.11332(14) 0.48772(10) 0.58652(9) 0.0269(4) Uani d . 1 . . C
  C122 0.11024(14) 0.41659(10) 0.53648(9) 0.0280(4) Uani d . 1 . . C
  C123 0.03236(14) 0.35489(10) 0.54017(10) 0.0290(4) Uani d . 1 . . C
  C124 -0.04624(14) 0.36190(10) 0.59366(9) 0.0268(4) Uani d . 1 . . C
  C127 -0.19932(15) 0.29812(13) 0.64951(11) 0.0388(4) Uani d . 1 . . C
  C125 -0.04615(14) 0.43180(10) 0.64316(10) 0.0290(4) Uani d . 1 . . C
  C126 0.03363(14) 0.49315(10) 0.63944(10) 0.0303(4) Uani d . 1 . . C
  O21 0.40174(10) 0.43730(8) 0.15846(7) 0.0350(3) Uani d . 1 . . O
  O22 0.57373(10) 0.48298(8) 0.14661(7) 0.0344(3) Uani d . 1 . . O
  O23 0.56570(9) 0.41308(7) -0.00042(7) 0.0292(3) Uani d . 1 . . O
  O224 1.13190(9) 0.69604(7) -0.09055(7) 0.0304(3) Uani d . 1 . . O
  N24 0.58213(11) 0.33839(8) -0.04476(8) 0.0258(3) Uani d . 1 . . N
  C21 0.48979(14) 0.44498(10) 0.12040(10) 0.0276(4) Uani d . 1 . . C
  C22 0.47239(14) 0.39976(10) 0.04122(10) 0.0285(4) Uani d . 1 . . C
  C25 0.67422(13) 0.34212(10) -0.07630(9) 0.0232(3) Uani d . 1 . . C
  C26 0.75050(13) 0.41265(10) -0.06827(9) 0.0247(4) Uani d . 1 . . C
  C27 0.83773(13) 0.42128(10) -0.10911(9) 0.0244(4) Uani d . 1 . . C
  C211 0.69586(13) 0.26371(10) -0.12096(9) 0.0234(4) Uani d . 1 . . C
  C212 0.78964(14) 0.21562(10) -0.09741(10) 0.0272(4) Uani d . 1 . . C
  C213 0.80524(14) 0.13922(10) -0.13449(10) 0.0305(4) Uani d . 1 . . C
  C214 0.72783(15) 0.11144(11) -0.19686(10) 0.0330(4) Uani d . 1 . . C
  C215 0.63508(15) 0.15915(11) -0.22151(10) 0.0342(4) Uani d . 1 . . C
  C216 0.61770(14) 0.23510(11) -0.18340(10) 0.0296(4) Uani d . 1 . . C
  C221 0.91380(13) 0.49278(10) -0.10393(9) 0.0234(4) Uani d . 1 . . C
  C222 0.89385(13) 0.56883(10) -0.06499(9) 0.0254(4) Uani d . 1 . . C
  C223 0.96769(14) 0.63421(10) -0.06110(9) 0.0263(4) Uani d . 1 . . C
  C224 1.06506(13) 0.62654(10) -0.09646(9) 0.0246(4) Uani d . 1 . . C
  C227 1.22717(15) 0.69469(12) -0.13253(11) 0.0374(4) Uani d . 1 . . C
  C225 1.08826(13) 0.55199(10) -0.13456(9) 0.0261(4) Uani d . 1 . . C
  C226 1.01226(13) 0.48678(10) -0.13817(9) 0.0255(4) Uani d . 1 . . C
  H11 0.5911 0.5390 0.2423 0.065 Uiso calc R 1 . . H
  H12A 0.5956 0.5814 0.4369 0.042 Uiso calc R 1 . . H
  H12B 0.5346 0.6632 0.3957 0.042 Uiso calc R 1 . . H
  H112 0.2007 0.7604 0.5471 0.049 Uiso calc R 1 . . H
  H113 0.1851 0.8636 0.6446 0.053 Uiso calc R 1 . . H
  H114 0.3115 0.8673 0.7621 0.044 Uiso calc R 1 . . H
  H115 0.4520 0.7679 0.7823 0.047 Uiso calc R 1 . . H
  H116 0.4713 0.6668 0.6838 0.042 Uiso calc R 1 . . H
  H16 0.2716 0.5283 0.4917 0.034 Uiso calc R 1 . . H
  H17 0.1944 0.5960 0.6282 0.034 Uiso calc R 1 . . H
  H122 0.1630 0.4111 0.4994 0.034 Uiso calc R 1 . . H
  H123 0.0319 0.3069 0.5060 0.035 Uiso calc R 1 . . H
  H12C -0.2455 0.3485 0.6390 0.058 Uiso calc R 1 . . H
  H12D -0.1614 0.2999 0.7051 0.058 Uiso calc R 1 . . H
  H12E -0.2462 0.2477 0.6424 0.058 Uiso calc R 1 . . H
  H125 -0.1002 0.4376 0.6792 0.035 Uiso calc R 1 . . H
  H126 0.0342 0.5407 0.6741 0.036 Uiso calc R 1 . . H
  H21 0.4122 0.4637 0.2024 0.053 Uiso calc R 1 . . H
  H22A 0.4628 0.3387 0.0504 0.034 Uiso calc R 1 . . H
  H22B 0.4045 0.4211 0.0083 0.034 Uiso calc R 1 . . H
  H212 0.8438 0.2353 -0.0554 0.033 Uiso calc R 1 . . H
  H213 0.8689 0.1060 -0.1171 0.037 Uiso calc R 1 . . H
  H214 0.7386 0.0593 -0.2228 0.040 Uiso calc R 1 . . H
  H215 0.5825 0.1401 -0.2649 0.041 Uiso calc R 1 . . H
  H216 0.5528 0.2673 -0.1999 0.035 Uiso calc R 1 . . H
  H26 0.7377 0.4560 -0.0313 0.030 Uiso calc R 1 . . H
  H27 0.8513 0.3768 -0.1447 0.029 Uiso calc R 1 . . H
  H222 0.8276 0.5749 -0.0409 0.030 Uiso calc R 1 . . H
  H223 0.9526 0.6849 -0.0343 0.032 Uiso calc R 1 . . H
  H22C 1.2756 0.6479 -0.1124 0.056 Uiso calc R 1 . . H
  H22D 1.2676 0.7480 -0.1234 0.056 Uiso calc R 1 . . H
  H22E 1.2036 0.6873 -0.1906 0.056 Uiso calc R 1 . . H
  H225 1.1552 0.5459 -0.1577 0.031 Uiso calc R 1 . . H
  H226 1.0277 0.4361 -0.1649 0.031 Uiso calc R 1 . . H
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
  C11 0.0307(10) 0.0267(9) 0.0316(9) -0.0005(8) 0.0104(8) 0.0013(7)
  O11 0.0345(7) 0.0610(9) 0.0377(8) -0.0131(7) 0.0156(6) -0.0155(6)
  O12 0.0376(7) 0.0514(8) 0.0376(7) -0.0158(7) 0.0177(6) -0.0152(6)
  C12 0.0310(10) 0.0381(10) 0.0385(10) -0.0020(8) 0.0118(8) -0.0098(8)
  O13 0.0366(7) 0.0296(6) 0.0330(7) -0.0050(6) 0.0132(5) -0.0097(5)
  N14 0.0338(8) 0.0269(8) 0.0262(7) 0.0003(6) 0.0040(6) -0.0066(6)
  C15 0.0296(9) 0.0268(9) 0.0220(8) 0.0020(8) 0.0008(7) 0.0032(7)
  C111 0.0330(9) 0.0244(8) 0.0249(9) -0.0028(8) 0.0093(7) 0.0000(7)
  C112 0.0525(12) 0.0370(11) 0.0310(10) 0.0113(10) -0.0030(9) -0.0033(8)
  C113 0.0592(13) 0.0330(10) 0.0417(11) 0.0104(10) 0.0094(10) -0.0056(8)
  C114 0.0461(11) 0.0322(10) 0.0349(10) -0.0142(9) 0.0192(9) -0.0102(8)
  C115 0.0332(10) 0.0507(12) 0.0339(10) -0.0095(10) 0.0061(8) -0.0147(9)
  C116 0.0260(9) 0.0434(11) 0.0354(10) 0.0001(8) 0.0054(8) -0.0058(8)
  C16 0.0349(10) 0.0248(9) 0.0245(9) 0.0025(8) 0.0048(7) -0.0023(7)
  C17 0.0344(10) 0.0253(9) 0.0246(9) 0.0030(8) 0.0036(7) -0.0014(7)
  C121 0.0313(9) 0.0253(9) 0.0242(8) 0.0052(8) 0.0041(7) 0.0049(7)
  C122 0.0339(10) 0.0267(9) 0.0243(9) 0.0054(8) 0.0076(7) 0.0024(7)
  C123 0.0371(10) 0.0233(9) 0.0275(9) 0.0029(8) 0.0076(7) -0.0017(7)
  C124 0.0304(9) 0.0249(8) 0.0247(8) 0.0017(8) 0.0022(7) 0.0053(7)
  O124 0.0367(7) 0.0309(7) 0.0329(7) -0.0058(6) 0.0094(5) 0.0008(5)
  C127 0.0342(10) 0.0457(11) 0.0385(10) -0.0068(9) 0.0123(8) 0.0033(9)
  C125 0.0319(9) 0.0313(9) 0.0253(9) 0.0035(8) 0.0102(7) 0.0008(7)
  C126 0.0403(11) 0.0247(9) 0.0268(9) 0.0032(8) 0.0079(7) -0.0012(7)
  C21 0.0281(9) 0.0235(9) 0.0329(9) 0.0026(8) 0.0113(7) 0.0040(7)
  O21 0.0304(7) 0.0436(8) 0.0336(7) -0.0068(6) 0.0142(5) -0.0096(6)
  O22 0.0309(7) 0.0415(7) 0.0326(7) -0.0067(6) 0.0109(5) -0.0060(5)
  C22 0.0281(9) 0.0236(8) 0.0363(9) -0.0022(8) 0.0143(7) -0.0029(7)
  O23 0.0318(7) 0.0220(6) 0.0372(7) -0.0035(5) 0.0169(5) -0.0064(5)
  N24 0.0321(8) 0.0185(7) 0.0279(7) -0.0002(6) 0.0076(6) -0.0051(5)
  C25 0.0240(9) 0.0250(8) 0.0205(8) 0.0000(7) 0.0028(6) 0.0011(6)
  C211 0.0236(8) 0.0251(8) 0.0228(8) -0.0051(7) 0.0080(7) -0.0003(6)
  C212 0.0264(9) 0.0273(9) 0.0282(9) -0.0044(7) 0.0055(7) -0.0020(7)
  C213 0.0282(9) 0.0264(9) 0.0390(10) -0.0012(8) 0.0121(8) -0.0025(7)
  C214 0.0351(10) 0.0286(9) 0.0384(10) -0.0067(8) 0.0166(8) -0.0106(8)
  C215 0.0342(10) 0.0393(10) 0.0298(9) -0.0118(9) 0.0068(8) -0.0119(8)
  C216 0.0267(9) 0.0344(10) 0.0275(9) -0.0027(8) 0.0032(7) -0.0025(7)
  C26 0.0268(9) 0.0232(8) 0.0239(8) 0.0009(7) 0.0029(7) -0.0020(6)
  C27 0.0277(9) 0.0220(8) 0.0237(8) 0.0010(7) 0.0040(7) -0.0027(6)
  C221 0.0238(9) 0.0240(8) 0.0222(8) -0.0004(7) 0.0025(6) 0.0006(6)
  C222 0.0231(9) 0.0275(9) 0.0264(9) 0.0015(7) 0.0066(7) 0.0002(7)
  C223 0.0293(9) 0.0239(8) 0.0260(9) 0.0005(7) 0.0044(7) -0.0017(7)
  C224 0.0245(9) 0.0270(9) 0.0213(8) -0.0038(7) -0.0012(6) 0.0028(6)
  O224 0.0290(6) 0.0282(6) 0.0348(7) -0.0081(5) 0.0073(5) -0.0010(5)
  C227 0.0321(10) 0.0422(11) 0.0393(10) -0.0120(9) 0.0095(8) 0.0003(8)
  C225 0.0235(9) 0.0296(9) 0.0262(9) 0.0023(7) 0.0066(7) 0.0014(7)
  C226 0.0265(9) 0.0248(8) 0.0259(9) 0.0033(7) 0.0066(7) -0.0020(7)
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
  C11 O12 . 1.205(2) no
  C11 O11 . 1.3133(19) no
  C11 C12 . 1.493(2) no
  O11 H11 . 0.84 no
  C12 O13 . 1.416(2) no
  C12 H12A . 0.99 no
  C12 H12B . 0.99 no
  O13 N14 . 1.4214(16) no
  N14 C15 . 1.289(2) no
  C15 C16 . 1.452(2) no
  C15 C111 . 1.501(2) no
  C111 C116 . 1.381(2) no
  C111 C112 . 1.386(2) no
  C112 C113 . 1.385(2) no
  C112 H112 . 0.95 no
  C113 C114 . 1.377(3) no
  C113 H113 . 0.95 no
  C114 C115 . 1.370(3) no
  C114 H114 . 0.95 no
  C115 C116 . 1.383(2) no
  C115 H115 . 0.95 no
  C116 H116 . 0.95 no
  C16 C17 . 1.344(2) no
  C16 H16 . 0.95 no
  C17 C121 . 1.455(2) no
  C17 H17 . 0.95 no
  C121 C126 . 1.395(2) no
  C121 C122 . 1.401(2) no
  C122 C123 . 1.369(2) no
  C122 H122 . 0.95 no
  C123 C124 . 1.393(2) no
  C123 H123 . 0.95 no
  C124 O124 . 1.374(2) no
  C124 C125 . 1.382(2) no
  O124 C127 . 1.432(2) no
  C127 H12C . 0.98 no
  C127 H12D . 0.98 no
  C127 H12E . 0.98 no
  C125 C126 . 1.381(2) no
  C125 H125 . 0.95 no
  C126 H126 . 0.95 no
  C21 O22 . 1.217(2) no
  C21 O21 . 1.3184(19) no
  C21 C22 . 1.493(2) no
  O21 H21 . 0.84 no
  C22 O23 . 1.4200(18) no
  C22 H22A . 0.99 no
  C22 H22B . 0.99 no
  O23 N24 . 1.4243(16) no
  N24 C25 . 1.298(2) no
  C25 C26 . 1.448(2) no
  C25 C211 . 1.491(2) no
  C211 C212 . 1.386(2) no
  C211 C216 . 1.392(2) no
  C212 C213 . 1.385(2) no
  C212 H212 . 0.95 no
  C213 C214 . 1.381(2) no
  C213 H213 . 0.95 no
  C214 C215 . 1.376(3) no
  C214 H214 . 0.95 no
  C215 C216 . 1.391(2) no
  C215 H215 . 0.95 no
  C216 H216 . 0.95 no
  C26 C27 . 1.339(2) no
  C26 H26 . 0.95 no
  C27 C221 . 1.459(2) no
  C27 H27 . 0.95 no
  C221 C226 . 1.394(2) no
  C221 C222 . 1.406(2) no
  C222 C223 . 1.368(2) no
  C222 H222 . 0.95 no
  C223 C224 . 1.394(2) no
  C223 H223 . 0.95 no
  C224 O224 . 1.3655(19) no
  C224 C225 . 1.389(2) no
  O224 C227 . 1.428(2) no
  C227 H22C . 0.98 no
  C227 H22D . 0.98 no
  C227 H22E . 0.98 no
  C225 C226 . 1.383(2) no
  C225 H225 . 0.95 no
  C226 H226 . 0.95 no
_cod_database_code 2100264