#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012024.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_2012024
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  737
_journal_page_last  739
_publ_section_title
;
4-(4-Methoxyphenylamino)-3-phenylazo-3-penten-2-one
;
loop_
_publ_author_name
  'Kettmann, Viktor'
  'Lokaj, Jan'
  "Petr \<Simunek"
  "Vladim\'ir Mach\'a\<cek"
_chemical_formula_moiety  'C18 H19 N3 O2 '
_chemical_formula_sum  'C18 H19 N3 O2 '
_chemical_formula_weight  309.36
_chemical_melting_point  412
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P2~1~/c'
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'
_cell_length_a  11.525(5)
_cell_length_b  14.465(6)
_cell_length_c  9.761(3)
_cell_angle_alpha  90.00
_cell_angle_beta  92.82(4)
_cell_angle_gamma  90.00
_cell_volume  1625.3(11)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.264
_exptl_crystal_density_meas  1.270(10)
_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
  C1  .6983(3)  .97733(19)  .1612(3)  .0525(9) Uani d . 1 . . C
  C2  .7262(3) 1.0639(2)  .2188(3)  .0625(10) Uani d . 1 . . C
  H2  .6680 1.1019  .2500  .075 Uiso calc R 1 . . H
  C3  .8417(3) 1.0922(2)  .2287(3)  .0607(9) Uani d . 1 . . C
  H3  .8611 1.1488  .2688  .073 Uiso calc R 1 . . H
  C4  .9270(3) 1.0369(2)  .1796(3)  .0624(9) Uani d . 1 . . C
  H4 1.0035 1.0576  .1831  .075 Uiso calc R 1 . . H
  C5  .9009(3)  .9522(2)  .1258(3)  .0603(10) Uani d . 1 . . C
  H5  .9597  .9140  .0966  .072 Uiso calc R 1 . . H
  C6  .7841(3)  .9225(2)  .1145(3)  .0541(9) Uani d . 1 . . C
  H6  .7656  .8655  .0752  .065 Uiso calc R 1 . . H
  N7  .58126(19)  .95294(17)  .1578(2)  .0454(7) Uani d . 1 . . N
  N8  .55000(19)  .87400(16)  .1000(2)  .0457(7) Uani d . 1 . . N
  C9  .4402(2)  .8507(2)  .1000(3)  .0481(8) Uani d . 1 . . C
  C10  .4202(3)  .7588(2)  .0333(3)  .0523(9) Uani d . 1 . . C
  O11  .3278(2)  .71984(16)  .0303(3)  .1059(10) Uani d . 1 . . O
  C12  .5196(3)  .7141(2)  -.0345(4)  .0879(12) Uani d . 1 . . C
  H12A  .5805  .7005  .0331  .132 Uiso calc R 1 . . H
  H12B  .5484  .7553  -.1020  .132 Uiso calc R 1 . . H
  H12C  .4935  .6578  -.0782  .132 Uiso calc R 1 . . H
  C13  .3489(2)  .9028(2)  .1669(3)  .0461(8) Uani d . 1 . . C
  C14  .2265(2)  .8675(2)  .1566(3)  .0638(10) Uani d . 1 . . C
  H14A  .2219  .8107  .2072  .096 Uiso calc R 1 . . H
  H14B  .2036  .8565  .0621  .096 Uiso calc R 1 . . H
  H14C  .1757  .9125  .1941  .096 Uiso calc R 1 . . H
  N15  .37957(19)  .97722(16)  .2277(2)  .0456(7) Uani d . 1 . . N
  H15  .503(3)  .995(2)  .235(3)  .120(12) Uiso d . 1 . . H
  C16  .2957(2) 1.0332(2)  .2927(3)  .0454(8) Uani d . 1 . . C
  C17  .2460(3) 1.0090(2)  .4108(3)  .0636(10) Uani d . 1 . . C
  H17  .2631  .9518  .4506  .076 Uiso calc R 1 . . H
  C18  .1697(2) 1.0687(2)  .4731(3)  .0569(9) Uani d . 1 . . C
  H18  .1360 1.0521  .5542  .068 Uiso calc R 1 . . H
  C19  .1452(3) 1.1529(2)  .4119(4)  .0590(10) Uani d . 1 . . C
  C20  .1978(3) 1.1773(2)  .2932(3)  .0644(10) Uani d . 1 . . C
  H20  .1807 1.2338  .2515  .077 Uiso calc R 1 . . H
  C21  .2751(2) 1.1184(2)  .2368(3)  .0586(9) Uani d . 1 . . C
  H21  .3139 1.1366  .1599  .070 Uiso calc R 1 . . H
  O22  .06806(18) 1.21518(14)  .4597(2)  .0770(7) Uani d . 1 . . O
  C23  -.0094(2) 1.18568(19)  .5605(4)  .0714(11) Uani d . 1 . . C
  H23A  -.0645 1.2339  .5762  .107 Uiso calc R 1 . . H
  H23B  .0339 1.1721  .6446  .107 Uiso calc R 1 . . H
  H23C  -.0500 1.1312  .5287  .107 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
  C1  .056(2)  .0324(19)  .069(2)  -.0064(16)  .0055(18)  -.0121(17)
  C2  .039(2)  .070(2)  .079(3)  .0056(16)  .0113(18)  .002(2)
  C3  .064(2)  .049(2)  .070(3)  .0104(18)  .015(2)  -.0175(19)
  C4  .063(2)  .062(2)  .062(2)  -.0142(19)  -.0026(19)  -.006(2)
  C5  .066(2)  .066(2)  .049(2)  .0209(18)  .0157(19)  .0100(19)
  C6  .052(2)  .058(2)  .052(2)  .0055(17)  -.0027(18)  -.0086(17)
  N7  .0356(14)  .0576(16)  .0439(17)  -.0232(12)  .0120(12)  -.0028(13)
  N8  .0427(15)  .0389(14)  .0545(18)  -.0025(12)  -.0063(13)  -.0051(13)
  C9  .0416(19)  .053(2)  .049(2)  -.0174(16)  .0004(16)  -.0040(16)
  C10  .0539(19)  .0397(19)  .063(2)  .0066(16)  -.0007(19)  -.0003(17)
  O11  .0709(16)  .0846(18)  .164(3)  -.0283(14)  .0229(18)  -.0453(19)
  C12  .065(2)  .091(3)  .109(3)  -.012(2)  .007(2)  -.041(3)
  C13  .0350(17)  .0443(19)  .059(2)  -.0272(15)  .0005(16)  .0094(17)
  C14  .0419(18)  .067(2)  .082(3)  .0021(16)  -.0025(18)  -.005(2)
  N15  .0320(14)  .0431(16)  .0604(19)  -.0080(12)  -.0094(13)  .0027(14)
  C16  .056(2)  .0377(18)  .042(2)  -.0041(15)  -.0098(17)  .0109(16)
  C17  .067(2)  .071(2)  .053(2)  .0060(18)  .0068(19)  .023(2)
  C18  .059(2)  .058(2)  .056(2)  -.0032(17)  .0255(18)  .0011(19)
  C19  .058(2)  .0317(18)  .089(3)  .0066(15)  .019(2)  -.021(2)
  C20  .060(2)  .071(2)  .064(3)  .0157(18)  .016(2)  .009(2)
  C21  .059(2)  .055(2)  .064(2)  -.0007(17)  .0183(18)  .002(2)
  O22  .0817(16)  .0501(14)  .1017(19)  -.0072(13)  .0286(15)  .0179(14)
  C23  .053(2)  .055(2)  .107(3)  .0091(16)  .009(2)  .001(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
  C1 C6 . 1.362(4) yes
  C1 N7 . 1.394(3) yes
  C1 C2 . 1.403(4) yes
  C2 C3 . 1.392(4) yes
  C2 H2 .  .9300 ?
  C3 C4 . 1.372(4) yes
  C3 H3 .  .9300 ?
  C4 C5 . 1.362(4) yes
  C4 H4 .  .9300 ?
  C5 C6 . 1.412(4) yes
  C5 H5 .  .9300 ?
  C6 H6 .  .9300 ?
  N7 N8 . 1.316(3) yes
  N7 H15 . 1.35(3) ?
  N8 C9 . 1.309(3) yes
  C9 C13 . 1.473(4) yes
  C9 C10 . 1.493(4) yes
  C10 O11 . 1.204(3) yes
  C10 C12 . 1.498(4) ?
  C12 H12A .  .9600 ?
  C12 H12B .  .9600 ?
  C12 H12C .  .9600 ?
  C13 N15 . 1.271(3) yes
  C13 C14 . 1.499(3) ?
  C14 H14A .  .9600 ?
  C14 H14B .  .9600 ?
  C14 H14C .  .9600 ?
  N15 C16 . 1.433(3) yes
  N15 H15 . 1.45(3) ?
  C16 C17 . 1.359(4) ?
  C16 C21 . 1.364(3) ?
  C17 C18 . 1.393(4) ?
  C17 H17 .  .9300 ?
  C18 C19 . 1.381(4) ?
  C18 H18 .  .9300 ?
  C19 O22 . 1.364(3) ?
  C19 C20 . 1.379(4) ?
  C20 C21 . 1.367(4) ?
  C20 H20 .  .9300 ?
  C21 H21 .  .9300 ?
  O22 C23 . 1.426(3) ?
  C23 H23A .  .9600 ?
  C23 H23B .  .9600 ?
  C23 H23C .  .9600 ?