#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200013.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_2200013
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2005
_journal_volume  61
_journal_page_first  o3825
_journal_page_last  o3827
_publ_section_title
;
Intramolecular hydrogen transfer in
(<i>S</i>)-2-[(1-benzyl-2-hydroxyethylimino)methyl]-4-nitrophenol, a new
chiral Schiff base
;
loop_
_publ_author_name
  "Pradeep, Chullikkattil P."
_chemical_formula_moiety  'C16 H16 N2 O4'
_chemical_formula_sum  'C16 H16 N2 O4'
_chemical_formula_iupac  'C16 H16 N2 O4'
_chemical_formula_weight  300.31
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  5.8623(8)
_cell_length_b  8.1322(10)
_cell_length_c  30.674(4)
_cell_angle_alpha  90.00
_cell_angle_beta  91.450(2)
_cell_angle_gamma  90.00
_cell_volume  1461.9(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  295(2)
_exptl_crystal_density_diffrn  1.364
_diffrn_ambient_temperature  295(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
  O5 0.0514(3) 0.9170(3) 0.68955(7) 0.0682(6) Uani d . 1 . . O
  C21 0.4332(5) 0.6879(3) 0.76162(9) 0.0476(6) Uani d . 1 . . C
  H21 0.5757 0.6378 0.7615 0.057 Uiso calc R 1 . . H
  C20 0.3046(5) 0.6789(3) 0.79777(9) 0.0495(6) Uani d . 1 . . C
  N4 0.4450(4) 0.8581(3) 0.65274(7) 0.0529(6) Uani d . 1 . . N
  C22 0.3522(4) 0.7722(3) 0.72463(8) 0.0455(6) Uani d . 1 . . C
  C17 0.1305(4) 0.8474(4) 0.72367(9) 0.0507(7) Uani d . 1 . . C
  C18 0.0071(5) 0.8357(4) 0.76324(10) 0.0588(7) Uani d . 1 . . C
  H18 -0.1358 0.8849 0.7646 0.071 Uiso calc R 1 . . H
  N3 0.3936(5) 0.5900(4) 0.83504(7) 0.0641(7) Uani d . 1 . . N
  C31 0.5463(5) 0.8528(4) 0.49793(10) 0.0603(8) Uani d . 1 . . C
  H31 0.4093 0.9105 0.4971 0.072 Uiso calc R 1 . . H
  C19 0.0918(5) 0.7550(4) 0.79890(9) 0.0575(8) Uani d . 1 . . C
  H19 0.0075 0.7505 0.8241 0.069 Uiso calc R 1 . . H
  C26 0.6196(5) 0.7796(4) 0.53630(9) 0.0548(7) Uani d . 1 . . C
  C23 0.4985(5) 0.7837(3) 0.68855(8) 0.0488(6) Uani d . 1 . . C
  H23 0.6414 0.7344 0.6910 0.059 Uiso calc R 1 . . H
  O8 0.7657(4) 1.1251(3) 0.64267(8) 0.0757(6) Uani d . 1 . . O
  H8 0.8688 1.0665 0.6524 0.114 Uiso calc R 1 . . H
  O7 0.2810(5) 0.5851(5) 0.86777(7) 0.1011(10) Uani d . 1 . . O
  O6 0.5793(5) 0.5209(4) 0.83292(7) 0.0889(8) Uani d . 1 . . O
  C24 0.5963(5) 0.8688(4) 0.61579(8) 0.0532(7) Uani d . 1 . . C
  H24 0.7364 0.8072 0.6226 0.064 Uiso calc R 1 . . H
  C30 0.6732(6) 0.8418(4) 0.46088(9) 0.0664(8) Uani d . 1 . . C
  H30 0.6202 0.8909 0.4352 0.080 Uiso calc R 1 . . H
  C27 0.8242(5) 0.6938(4) 0.53647(10) 0.0627(8) Uani d . 1 . . C
  H27 0.8758 0.6420 0.5619 0.075 Uiso calc R 1 . . H
  C25 0.4749(5) 0.7899(5) 0.57625(9) 0.0676(9) Uani d . 1 . . C
  H25A 0.4271 0.6798 0.5841 0.081 Uiso calc R 1 . . H
  H25B 0.3387 0.8530 0.5691 0.081 Uiso calc R 1 . . H
  C28 0.9520(6) 0.6845(5) 0.49946(12) 0.0694(9) Uani d . 1 . . C
  H28 1.0896 0.6276 0.5002 0.083 Uiso calc R 1 . . H
  C29 0.8771(6) 0.7589(4) 0.46151(10) 0.0687(9) Uani d . 1 . . C
  H29 0.9636 0.7531 0.4366 0.082 Uiso calc R 1 . . H
  C32 0.6568(6) 1.0463(4) 0.60716(9) 0.0643(8) Uani d . 1 . . C
  H32A 0.7559 1.0508 0.5823 0.077 Uiso calc R 1 . . H
  H32B 0.5183 1.1060 0.5994 0.077 Uiso calc R 1 . . H
  N2 1.0757(4) 0.1642(4) 0.85038(7) 0.0570(6) Uani d . 1 . . N
  C5 1.0232(5) 0.3484(4) 0.74284(8) 0.0486(6) Uani d . 1 . . C
  H5 0.8812 0.3976 0.7458 0.058 Uiso calc R 1 . . H
  C6 1.1195(5) 0.2585(3) 0.77740(8) 0.0472(6) Uani d . 1 . . C
  O1 1.4308(3) 0.0996(3) 0.80363(7) 0.0704(6) Uani d . 1 . . O
  N1 1.0349(5) 0.4586(3) 0.66934(8) 0.0620(6) Uani d . 1 . . N
  C4 1.1367(5) 0.3646(3) 0.70460(8) 0.0502(6) Uani d . 1 . . C
  C1 1.3402(5) 0.1826(4) 0.77287(9) 0.0534(7) Uani d . 1 . . C
  C7 1.0002(5) 0.2455(4) 0.81706(9) 0.0528(7) Uani d . 1 . . C
  H7 0.8603 0.2986 0.8190 0.063 Uiso calc R 1 . . H
  C2 1.4483(5) 0.2052(4) 0.73233(10) 0.0592(8) Uani d . 1 . . C
  H2 1.5906 0.1578 0.7284 0.071 Uiso calc R 1 . . H
  C8 0.9640(5) 0.1523(4) 0.89292(8) 0.0560(7) Uani d . 1 . . C
  H8A 1.0469 0.0708 0.9107 0.067 Uiso calc R 1 . . H
  O2 0.8404(4) 0.5107(3) 0.67306(7) 0.0787(7) Uani d . 1 . . O
  C10 0.8667(5) 0.3199(4) 0.96000(8) 0.0549(7) Uani d . 1 . . C
  C14 0.8619(6) 0.2458(5) 1.03549(10) 0.0706(9) Uani d . 1 . . C
  H14 0.9306 0.1934 1.0594 0.085 Uiso calc R 1 . . H
  O3 1.1463(5) 0.4825(4) 0.63664(7) 0.0946(8) Uani d . 1 . . O
  C11 0.6609(5) 0.4003(4) 0.96533(10) 0.0627(8) Uani d . 1 . . C
  H11 0.5917 0.4536 0.9416 0.075 Uiso calc R 1 . . H
  C12 0.5578(5) 0.4028(5) 1.00491(11) 0.0700(9) Uani d . 1 . . C
  H12 0.4195 0.4572 1.0078 0.084 Uiso calc R 1 . . H
  C3 1.3520(5) 0.2931(4) 0.69932(9) 0.0576(7) Uani d . 1 . . C
  H3 1.4280 0.3061 0.6733 0.069 Uiso calc R 1 . . H
  C13 0.6570(6) 0.3257(5) 1.04009(10) 0.0704(9) Uani d . 1 . . C
  H13 0.5867 0.3271 1.0669 0.084 Uiso calc R 1 . . H
  O4 0.6985(5) -0.0523(3) 0.86423(7) 0.0824(7) Uani d . 1 . . O
  H4 0.6410 -0.0339 0.8401 0.124 Uiso calc R 1 . . H
  C15 0.9656(6) 0.2431(4) 0.99587(11) 0.0631(8) Uani d . 1 . . C
  H15 1.1042 0.1888 0.9932 0.076 Uiso calc R 1 . . H
  C16 0.7187(5) 0.0961(4) 0.88770(9) 0.0657(8) Uani d . 1 . . C
  H16A 0.6551 0.0814 0.9163 0.079 Uiso calc R 1 . . H
  H16B 0.6308 0.1807 0.8726 0.079 Uiso calc R 1 . . H
  C9 0.9802(5) 0.3182(4) 0.91641(9) 0.0630(8) Uani d . 1 . . C
  H9A 1.1399 0.3467 0.9207 0.076 Uiso calc R 1 . . H
  H9B 0.9103 0.4019 0.8979 0.076 Uiso calc R 1 . . H
  H1A 1.224(6) 0.118(5) 0.8444(10) 0.077(10) Uiso d . 1 . . H
  H1B 0.308(5) 0.910(4) 0.6516(9) 0.067(10) Uiso d . 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
  O5 0.0569(12) 0.0763(16) 0.0709(13) 0.0051(11) -0.0091(10) 0.0083(12)
  C21 0.0527(15) 0.0406(15) 0.0498(15) -0.0013(13) 0.0061(12) 0.0005(12)
  C20 0.0571(16) 0.0433(15) 0.0484(15) -0.0089(13) 0.0060(12) 0.0014(12)
  N4 0.0569(14) 0.0561(15) 0.0458(13) -0.0015(12) 0.0063(10) 0.0049(11)
  C22 0.0502(15) 0.0402(15) 0.0462(14) -0.0053(12) 0.0049(11) -0.0026(11)
  C17 0.0480(15) 0.0469(16) 0.0571(16) -0.0075(13) -0.0028(12) -0.0016(14)
  C18 0.0407(14) 0.0569(18) 0.079(2) -0.0027(14) 0.0077(13) -0.0092(17)
  N3 0.0830(19) 0.0623(17) 0.0473(13) -0.0117(15) 0.0085(13) 0.0072(13)
  C31 0.0635(18) 0.0593(19) 0.0579(16) 0.0037(16) -0.0021(14) -0.0051(15)
  C19 0.0603(17) 0.0585(18) 0.0545(17) -0.0139(15) 0.0187(14) -0.0066(14)
  C26 0.0563(16) 0.0568(19) 0.0515(15) -0.0117(14) 0.0024(12) -0.0071(13)
  C23 0.0558(15) 0.0457(16) 0.0449(15) -0.0010(13) 0.0014(12) 0.0007(12)
  O8 0.0808(16) 0.0607(14) 0.0848(15) 0.0020(12) -0.0122(12) -0.0153(13)
  O7 0.114(2) 0.134(3) 0.0567(13) -0.010(2) 0.0251(13) 0.0240(16)
  O6 0.1046(19) 0.0932(19) 0.0691(14) 0.0266(17) 0.0054(13) 0.0257(14)
  C24 0.0592(16) 0.0589(18) 0.0417(13) -0.0059(14) 0.0074(12) 0.0050(13)
  C30 0.093(2) 0.059(2) 0.0467(15) -0.0004(19) 0.0002(15) -0.0009(15)
  C27 0.0692(19) 0.064(2) 0.0548(16) -0.0044(17) -0.0055(14) 0.0027(15)
  C25 0.0664(18) 0.080(2) 0.0570(17) -0.0210(18) 0.0079(14) -0.0104(16)
  C28 0.063(2) 0.067(2) 0.0774(19) 0.0078(17) 0.0067(16) -0.0069(18)
  C29 0.082(2) 0.062(2) 0.0628(19) 0.0013(18) 0.0174(16) -0.0097(16)
  C32 0.076(2) 0.063(2) 0.0541(16) -0.0113(16) -0.0007(14) 0.0074(15)
  N2 0.0610(15) 0.0632(16) 0.0468(13) 0.0008(13) 0.0031(11) 0.0007(12)
  C5 0.0501(15) 0.0430(15) 0.0532(15) -0.0038(13) 0.0098(12) -0.0055(13)
  C6 0.0531(15) 0.0447(15) 0.0441(14) -0.0067(13) 0.0070(12) -0.0032(12)
  O1 0.0622(12) 0.0818(16) 0.0668(12) 0.0090(12) -0.0079(10) -0.0036(13)
  N1 0.0816(18) 0.0511(15) 0.0538(14) -0.0023(15) 0.0122(13) 0.0019(12)
  C4 0.0596(16) 0.0428(15) 0.0486(15) -0.0079(13) 0.0102(12) -0.0055(12)
  C1 0.0534(16) 0.0479(16) 0.0586(17) -0.0063(14) -0.0047(13) -0.0118(14)
  C7 0.0558(16) 0.0498(16) 0.0530(16) -0.0002(13) 0.0059(12) -0.0032(13)
  C2 0.0459(15) 0.062(2) 0.070(2) -0.0061(14) 0.0130(14) -0.0172(16)
  C8 0.0681(18) 0.0597(18) 0.0402(14) 0.0001(15) 0.0011(12) 0.0065(13)
  O2 0.0958(17) 0.0692(15) 0.0716(14) 0.0243(14) 0.0126(12) 0.0130(12)
  C10 0.0614(17) 0.0555(17) 0.0479(15) -0.0097(15) 0.0013(12) -0.0013(13)
  C14 0.098(3) 0.067(2) 0.0461(16) 0.004(2) 0.0018(16) 0.0040(15)
  O3 0.1143(19) 0.115(2) 0.0562(12) -0.0013(19) 0.0304(12) 0.0214(15)
  C11 0.0688(19) 0.0627(19) 0.0562(16) 0.0023(16) -0.0087(14) 0.0008(14)
  C12 0.065(2) 0.071(2) 0.074(2) 0.0040(17) 0.0083(16) -0.0076(18)
  C3 0.0620(17) 0.0557(18) 0.0560(17) -0.0094(15) 0.0180(14) -0.0096(15)
  C13 0.087(2) 0.065(2) 0.0597(18) -0.0014(19) 0.0214(16) -0.0076(17)
  O4 0.1115(19) 0.0591(14) 0.0757(14) -0.0156(14) -0.0140(13) -0.0012(12)
  C15 0.0661(19) 0.066(2) 0.0575(17) 0.0033(16) 0.0026(14) 0.0009(16)
  C16 0.082(2) 0.066(2) 0.0487(15) -0.0183(17) 0.0084(14) -0.0004(15)
  C9 0.0745(19) 0.067(2) 0.0480(15) -0.0151(17) 0.0062(13) 0.0003(15)
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
  O5 C17 . 1.267(3) yes
  C21 C20 . 1.358(4) yes
  C21 C22 . 1.398(4) yes
  C21 H21 . 0.9300 ?
  C20 C19 . 1.394(4) yes
  C20 N3 . 1.439(4) ?
  N4 C23 . 1.286(3) yes
  N4 C24 . 1.460(3) yes
  N4 H1B . 0.91(3) ?
  C22 C23 . 1.420(3) yes
  C22 C17 . 1.436(4) yes
  C17 C18 . 1.432(4) yes
  C18 C19 . 1.359(4) yes
  C18 H18 . 0.9300 ?
  N3 O7 . 1.216(3) ?
  N3 O6 . 1.228(4) ?
  C31 C30 . 1.377(4) ?
  C31 C26 . 1.378(4) ?
  C31 H31 . 0.9300 ?
  C19 H19 . 0.9300 ?
  C26 C27 . 1.387(4) ?
  C26 C25 . 1.510(4) ?
  C23 H23 . 0.9300 ?
  O8 C32 . 1.404(3) ?
  O8 H8 . 0.8200 ?
  C24 C32 . 1.511(5) ?
  C24 C25 . 1.531(4) ?
  C24 H24 . 0.9800 ?
  C30 C29 . 1.372(5) ?
  C30 H30 . 0.9300 ?
  C27 C28 . 1.378(5) ?
  C27 H27 . 0.9300 ?
  C25 H25A . 0.9700 ?
  C25 H25B . 0.9700 ?
  C28 C29 . 1.374(5) ?
  C28 H28 . 0.9300 ?
  C29 H29 . 0.9300 ?
  C32 H32A . 0.9700 ?
  C32 H32B . 0.9700 ?
  N2 C7 . 1.287(4) yes
  N2 C8 . 1.478(3) yes
  N2 H1A . 0.97(3) ?
  C5 C4 . 1.370(3) yes
  C5 C6 . 1.395(4) yes
  C5 H5 . 0.9300 ?
  C6 C7 . 1.422(4) yes
  C6 C1 . 1.444(4) yes
  O1 C1 . 1.266(3) yes
  N1 O2 . 1.224(3) ?
  N1 O3 . 1.226(3) ?
  N1 C4 . 1.442(4) ?
  C4 C3 . 1.403(4) yes
  C1 C2 . 1.422(4) yes
  C7 H7 . 0.9300 ?
  C2 C3 . 1.351(4) yes
  C2 H2 . 0.9300 ?
  C8 C16 . 1.514(4) ?
  C8 C9 . 1.531(4) ?
  C8 H8A . 0.9800 ?
  C10 C15 . 1.380(4) ?
  C10 C11 . 1.386(4) ?
  C10 C9 . 1.509(4) ?
  C14 C15 . 1.373(5) ?
  C14 C13 . 1.376(5) ?
  C14 H14 . 0.9300 ?
  C11 C12 . 1.370(4) ?
  C11 H11 . 0.9300 ?
  C12 C13 . 1.366(5) ?
  C12 H12 . 0.9300 ?
  C3 H3 . 0.9300 ?
  C13 H13 . 0.9300 ?
  O4 C16 . 1.408(4) ?
  O4 H4 . 0.8200 ?
  C15 H15 . 0.9300 ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?