#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200918.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_2200918
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2002
_journal_volume  58
_journal_page_first  o24
_journal_page_last  o26
_publ_section_title
;
4-(Antipyrin-4-yliminomethyl)benzoic acid
;
loop_
_publ_author_name
  'Yu Zhang'
  'Yizhi Li'
  'Hanbin Tao'
  'Longgen Zhu'
_chemical_formula_moiety  'C19 H17 N3 O3'
_chemical_formula_sum  'C19 H17 N3 O3'
_chemical_formula_iupac  'C19 H17 N3 O3'
_chemical_formula_weight  335.36
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x-1/2, y-1/2, z'
_cell_length_a  13.0859(14)
_cell_length_b  11.4837(13)
_cell_length_c  22.422(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3369.5(6)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.322
_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  .33395(16) 1.06156(18)  .23355(9)  .0466(5) Uani d . 1 . . C
  C2  .25674(17)  .99866(19)  .20789(10)  .0634(7) Uani d . 1 . . C
  H2  .2067  .9643  .2315  .076 Uiso calc R 1 . . H
  C3  .2538(2)  .9867(2)  .14697(12)  .0811(8) Uani d . 1 . . C
  H3  .2014  .9444  .1291  .097 Uiso calc R 1 . . H
  C4  .3276(2) 1.0368(2)  .11269(11)  .0802(8) Uani d . 1 . . C
  H4  .3262 1.0273  .0715  .096 Uiso calc R 1 . . H
  C5  .40325(19) 1.1005(2)  .13826(11)  .0786(8) Uani d . 1 . . C
  H5  .4531 1.1349  .1145  .094 Uiso calc R 1 . . H
  C6  .40653(16) 1.1143(2)  .19937(10)  .0633(7) Uani d . 1 . . C
  H6  .4576 1.1590  .2170  .076 Uiso calc R 1 . . H
  C7  .39880(16)  .99487(18)  .33258(9)  .0436(5) Uani d . 1 . . C
  C8  .35261(15) 1.00154(16)  .38990(9)  .0412(5) Uani d . 1 . . C
  C9  .26972(15) 1.07502(18)  .38594(9)  .0456(6) Uani d . 1 . . C
  C10  .45656(16)  .88319(18)  .44854(8)  .0453(5) Uani d . 1 . . C
  H10  .5025  .8769  .4171  .054 Uiso calc R 1 . . H
  C11  .47756(16)  .82356(17)  .50478(8)  .0429(5) Uani d . 1 . . C
  C12  .56452(16)  .75732(18)  .51280(9)  .0506(6) Uani d . 1 . . C
  H12  .6110  .7500  .4817  .061 Uiso calc R 1 . . H
  C13  .58365(15)  .70187(17)  .56612(9)  .0502(6) Uani d . 1 . . C
  H13  .6423  .6569  .5704  .060 Uiso calc R 1 . . H
  C14  .51649(15)  .71240(17)  .61332(9)  .0435(5) Uani d . 1 . . C
  C15  .42974(16)  .77912(18)  .60565(9)  .0586(7) Uani d . 1 . . C
  H15  .3838  .7877  .6370  .070 Uiso calc R 1 . . H
  C16  .41074(15)  .83277(19)  .55226(9)  .0563(6) Uani d . 1 . . C
  H16  .3514  .8765  .5478  .068 Uiso calc R 1 . . H
  C17  .53889(18)  .6524(2)  .67018(9)  .0502(6) Uani d . 1 . . C
  C18  .19721(16) 1.2054(2)  .30667(10)  .0761(8) Uani d . 1 . . C
  H18A  .1499 1.2302  .3368  .114 Uiso calc R 1 . . H
  H18B  .1601 1.1765  .2728  .114 Uiso calc R 1 . . H
  H18C  .2388 1.2702  .2947  .114 Uiso calc R 1 . . H
  C19  .19754(15) 1.1105(2)  .43377(9)  .0672(7) Uani d . 1 . . C
  H19A  .1939 1.1940  .4354  .101 Uiso calc R 1 . . H
  H19B  .2211 1.0811  .4714  .101 Uiso calc R 1 . . H
  H19C  .1310 1.0795  .4254  .101 Uiso calc R 1 . . H
  N1  .34201(13) 1.06922(15)  .29687(7)  .0487(5) Uani d . 1 . . N
  N2  .26160(12) 1.11428(15)  .33023(8)  .0493(5) Uani d . 1 . . N
  N3  .37562(12)  .94371(14)  .44242(7)  .0461(5) Uani d . 1 . . N
  O1  .47157(11)  .93502(12)  .31377(5)  .0534(4) Uani d . 1 . . O
  O2  .61096(12)  .58904(15)  .67767(6)  .0788(6) Uani d . 1 . . O
  O3  .47082(10)  .67435(12)  .71210(6)  .0590(4) Uani d . 1 . . O
  H33  .4770  .6319  .7413  .071 Uiso d 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  .0481(15)  .0546(14)  .0372(13)  -.0006(12)  -.0047(12)  .0114(12)
  C2  .0618(17)  .0786(19)  .0497(16)  -.0124(14)  -.0068(13)  .0135(14)
  C3  .081(2)  .100(2)  .0624(19)  -.0123(17)  -.0240(16)  -.0001(17)
  C4  .080(2)  .120(3)  .0411(16)  .0199(19)  -.0082(16)  .0042(17)
  C5  .0651(19)  .119(3)  .0516(18)  .0014(16)  .0061(14)  .0278(17)
  C6  .0582(17)  .0842(19)  .0474(16)  -.0071(14)  -.0036(12)  .0137(14)
  C7  .0489(15)  .0460(14)  .0360(13)  -.0004(11)  -.0050(11)  -.0001(12)
  C8  .0498(15)  .0417(13)  .0322(12)  .0035(11)  -.0029(10)  .0029(11)
  C9  .0475(15)  .0498(14)  .0395(14)  .0002(11)  .0017(11)  .0026(12)
  C10  .0574(15)  .0479(14)  .0305(12)  -.0029(12)  .0000(11)  -.0006(11)
  C11  .0532(15)  .0423(14)  .0331(13)  .0015(11)  -.0043(11)  -.0036(11)
  C12  .0588(16)  .0564(15)  .0367(13)  .0088(12)  .0070(11)  .0017(12)
  C13  .0500(15)  .0577(16)  .0428(14)  .0093(11)  .0009(11)  .0022(12)
  C14  .0500(14)  .0439(13)  .0375(13)  .0033(11)  .0048(11)  .0026(11)
  C15  .0500(17)  .0536(17)  .0360(14)  .0148(14)  .0099(11)  .0116(13)
  C16  .0559(15)  .0704(17)  .0428(14)  .0201(12)  .0041(12)  .0101(13)
  C17  .0557(16)  .0558(16)  .0392(14)  -.0002(13)  .0001(13)  .0018(12)
  C18  .0666(17)  .0797(19)  .0818(18)  .0251(14)  .0012(14)  .0262(15)
  C19  .0668(16)  .0752(18)  .0598(16)  .0135(13)  .0117(13)  .0018(14)
  N1  .0492(12)  .0650(13)  .0319(11)  .0075(10)  -.0007(9)  .0062(10)
  N2  .0483(12)  .0535(12)  .0461(12)  .0097(9)  -.0007(9)  .0071(10)
  N3  .0569(12)  .0446(12)  .0368(11)  .0031(10)  -.0028(9)  .0007(9)
  O1  .0550(10)  .0682(10)  .0369(8)  .0156(8)  -.0019(7)  -.0071(8)
  O2  .0723(12)  .1058(14)  .0583(11)  .0342(11)  .0032(9)  .0273(10)
  O3  .0729(11)  .0659(11)  .0382(9)  .0089(8)  .0039(8)  .0123(8)
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(3) y
  C1 C2 . 1.369(3) ?
  C1 N1 . 1.426(2) y
  C2 C3 . 1.373(3) ?
  C2 H2 .  .9300 ?
  C3 C4 . 1.362(3) ?
  C3 H3 .  .9300 ?
  C4 C5 . 1.358(3) ?
  C4 H4 .  .9300 ?
  C5 C6 . 1.380(3) ?
  C5 H5 .  .9300 ?
  C6 H6 .  .9300 ?
  C7 O1 . 1.248(2) y
  C7 N1 . 1.387(2) y
  C7 C8 . 1.422(2) ?
  C8 C9 . 1.377(2) ?
  C8 N3 . 1.385(2) y
  C9 N2 . 1.332(2) y
  C9 C19 . 1.486(2) ?
  C10 N3 . 1.274(2) y
  C10 C11 . 1.461(2) y
  C10 H10 .  .9300 ?
  C11 C12 . 1.381(2) y
  C11 C16 . 1.382(2) ?
  C12 C13 . 1.377(2) ?
  C12 H12 .  .9300 ?
  C13 C14 . 1.381(2) ?
  C13 H13 .  .9300 ?
  C14 C15 . 1.380(2) ?
  C14 C17 . 1.479(3) y
  C15 C16 . 1.369(2) ?
  C15 H15 .  .9300 ?
  C16 H16 .  .9300 ?
  C17 O2 . 1.203(2) y
  C17 O3 . 1.319(2) y
  C18 N2 . 1.444(2) y
  C18 H18A .  .9600 ?
  C18 H18B .  .9600 ?
  C18 H18C .  .9600 ?
  C19 H19A .  .9600 ?
  C19 H19B .  .9600 ?
  C19 H19C .  .9600 ?
  N1 N2 . 1.391(2) y
  O3 H33 .  .8202 ?