#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202273.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_2202273
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1503
_journal_page_last  o1505
_publ_section_title
;
Redetermination of skimmianine: a new inhibitor against Leishimania APRT
enzyme
;
loop_
_publ_author_name
  'Napolitano, H. B.'
  'Silva, M.'
  'Ellena, J.'
  'Rocha, W. C.'
  'Vieira, P. C.'
  'Thiemann, O. H.'
  'Oliva, G.'
_chemical_formula_moiety  'C14 H13 N O4'
_chemical_formula_sum  'C14 H13 N O4'
_chemical_formula_weight  259.25
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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  7.24290(10)
_cell_length_b  10.4418(2)
_cell_length_c  15.4618(3)
_cell_angle_alpha  90
_cell_angle_beta  94.3530(10)
_cell_angle_gamma  90
_cell_volume  1165.99(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.477
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
  N 0.33424(12) 0.57374(9) 0.13399(5) 0.0194(2) Uani d . 1 . . N
  O1 0.42550(11) 0.43483(8) 0.24532(5) 0.0243(2) Uani d . 1 . . O
  O2 0.28060(11) 0.25320(7) -0.03212(5) 0.0233(2) Uani d . 1 . . O
  O3 0.27979(10) 0.81129(7) 0.06424(5) 0.02058(19) Uani d . 1 . . O
  O4 0.13823(11) 0.84432(7) -0.09956(5) 0.0245(2) Uani d . 1 . . O
  C1 0.36749(14) 0.45696(11) 0.15976(6) 0.0194(2) Uani d . 1 . . C
  C2 0.35529(13) 0.33930(10) 0.11348(7) 0.0192(2) Uani d . 1 . . C
  C3 0.29818(13) 0.34916(10) 0.02597(7) 0.0186(2) Uani d . 1 . . C
  C4 0.25319(13) 0.47355(10) -0.00799(6) 0.0177(2) Uani d . 1 . . C
  C5 0.27531(13) 0.58198(10) 0.04770(6) 0.0175(2) Uani d . 1 . . C
  C6 0.18805(14) 0.49268(11) -0.09582(7) 0.0200(2) Uani d . 1 . . C
  C7 0.14623(14) 0.61268(11) -0.12728(7) 0.0208(2) Uani d . 1 . . C
  C8 0.17206(14) 0.72110(10) -0.07294(6) 0.0186(2) Uani d . 1 . . C
  C9 0.23761(13) 0.70556(10) 0.01291(7) 0.0178(2) Uani d . 1 . . C
  C10 0.45022(15) 0.30320(11) 0.25283(8) 0.0253(3) Uani d . 1 . . C
  C11 0.41129(14) 0.24193(11) 0.17749(7) 0.0234(2) Uani d . 1 . . C
  C12 0.32400(16) 0.12536(11) -0.00303(8) 0.0261(3) Uani d . 1 . . C
  C13 0.13052(15) 0.85758(11) 0.11072(7) 0.0249(2) Uani d . 1 . . C
  H13A 0.0434 0.9021 0.0716 0.037 Uiso calc R 1 . . H
  H13B 0.1777 0.9151 0.1555 0.037 Uiso calc R 1 . . H
  H13C 0.07 0.7867 0.1363 0.037 Uiso calc R 1 . . H
  C14 0.09275(16) 0.86442(11) -0.19021(7) 0.0244(2) Uani d . 1 . . C
  H6 0.1727(18) 0.4202(15) -0.1341(8) 0.027(3) Uiso d . 1 . . H
  H7 0.0956(19) 0.6262(15) -0.1894(10) 0.035(4) Uiso d . 1 . . H
  H11 0.4213(18) 0.1499(14) 0.1694(9) 0.027(3) Uiso d . 1 . . H
  H10 0.4961(18) 0.2723(14) 0.3098(9) 0.027(3) Uiso d . 1 . . H
  H12A 0.454(2) 0.1187(15) 0.0224(10) 0.041 Uiso d . 1 . . H
  H12B 0.307(2) 0.0721(16) -0.0552(10) 0.041 Uiso d . 1 . . H
  H12C 0.241(2) 0.0970(16) 0.0400(10) 0.041 Uiso d . 1 . . H
  H14A 0.189(2) 0.8265(15) -0.2252(10) 0.041 Uiso d . 1 . . H
  H14B 0.089(2) 0.9608(17) -0.1963(9) 0.041 Uiso d . 1 . . H
  H14C -0.032(2) 0.8273(15) -0.2072(10) 0.041 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
  N 0.0198(4) 0.0202(4) 0.0179(4) 0.0013(3) -0.0001(3) -0.0006(3)
  O1 0.0288(4) 0.0239(4) 0.0194(4) 0.0034(3) -0.0040(3) 0.0025(3)
  O2 0.0292(4) 0.0149(4) 0.0253(4) 0.0008(3) -0.0002(3) -0.0024(3)
  O3 0.0217(4) 0.0172(4) 0.0228(4) -0.0003(3) 0.0019(3) -0.0052(3)
  O4 0.0351(4) 0.0183(4) 0.0198(4) 0.0040(3) -0.0003(3) 0.0022(3)
  C1 0.0175(5) 0.0227(5) 0.0178(5) 0.0017(4) -0.0002(4) 0.0017(4)
  C2 0.0155(5) 0.0196(5) 0.0225(5) 0.0002(4) 0.0017(4) 0.0013(4)
  C3 0.0161(4) 0.0180(5) 0.0219(5) -0.0007(4) 0.0024(4) -0.0026(4)
  C4 0.0157(5) 0.0182(5) 0.0195(5) -0.0007(4) 0.0026(4) -0.0012(4)
  C5 0.0150(4) 0.0187(5) 0.0188(5) -0.0002(4) 0.0015(4) -0.0005(4)
  C6 0.0207(5) 0.0205(5) 0.0188(5) -0.0009(4) 0.0012(4) -0.0031(4)
  C7 0.0220(5) 0.0230(5) 0.0172(5) 0.0001(4) 0.0006(4) -0.0010(4)
  C8 0.0191(5) 0.0174(5) 0.0193(5) 0.0012(4) 0.0024(4) 0.0017(4)
  C9 0.0174(5) 0.0171(5) 0.0191(5) -0.0004(4) 0.0016(4) -0.0022(4)
  C10 0.0248(5) 0.0241(6) 0.0265(6) 0.0028(4) -0.0013(4) 0.0063(4)
  C11 0.0214(5) 0.0220(5) 0.0267(5) 0.0018(4) 0.0002(4) 0.0051(4)
  C12 0.0283(6) 0.0155(5) 0.0340(6) 0.0004(4) 0.0002(5) -0.0015(4)
  C13 0.0270(5) 0.0240(6) 0.0240(5) 0.0017(4) 0.0043(4) -0.0052(4)
  C14 0.0280(6) 0.0250(6) 0.0202(5) 0.0045(4) 0.0013(4) 0.0050(4)
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
  N C1 . 1.2996(14) ?
  N C5 . 1.3723(13) ?
  O1 C1 . 1.3769(12) ?
  O1 C10 . 1.3898(14) ?
  O2 C3 . 1.3452(12) ?
  O2 C12 . 1.4358(13) ?
  O3 C9 . 1.3804(12) ?
  O3 C13 . 1.4272(12) ?
  O4 C8 . 1.3674(13) ?
  O4 C14 . 1.4306(13) ?
  C1 C2 . 1.4211(15) ?
  C2 C3 . 1.3883(15) ?
  C2 C11 . 1.4549(14) ?
  C3 C4 . 1.4293(14) ?
  C4 C6 . 1.4176(14) ?
  C4 C5 . 1.4240(14) ?
  C5 C9 . 1.4166(14) ?
  C6 C7 . 1.3697(15) ?
  C6 H6 . 0.962(15) ?
  C7 C8 . 1.4137(15) ?
  C7 H7 . 1.012(15) ?
  C8 C9 . 1.3848(14) ?
  C10 C11 . 1.3401(16) ?
  C10 H10 . 0.973(14) ?
  C11 H11 . 0.973(15) ?
  C12 H12A . 0.992(16) ?
  C12 H12B . 0.980(16) ?
  C12 H12C . 0.976(15) ?
  C13 H13A . 0.96 ?
  C13 H13B . 0.96 ?
  C13 H13C . 0.96 ?
  C14 H14A . 0.999(16) ?
  C14 H14B . 1.011(17) ?
  C14 H14C . 0.998(16) ?