data_2202274
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1506
_journal_page_last  o1508
_publ_section_title
;
Redetermination and structural comparative study of
isopimpinellin: 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  'C13 H10 O5'
_chemical_formula_sum  'C13 H10 O5'
_chemical_formula_weight  246.21
_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  16.9357(5)
_cell_length_b  4.36690(10)
_cell_length_c  16.2558(4)
_cell_angle_alpha  90
_cell_angle_beta  117.2180(10)
_cell_angle_gamma  90
_cell_volume  1069.10(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.53
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
  O1 0.25821(7) -0.3321(2) 0.15311(7) 0.0290(3) Uani d . 1 . . O
  O2 0.08783(6) -1.0025(3) 0.24125(7) 0.0324(3) Uani d . 1 . . O
  O3 0.33339(8) 0.0004(2) 0.11387(8) 0.0366(3) Uani d . 1 . . O
  O4 0.09680(7) -0.6081(3) 0.10486(7) 0.0350(3) Uani d . 1 . . O
  O5 0.39331(6) -0.8340(2) 0.44430(7) 0.0268(3) Uani d . 1 . . O
  C1 0.33592(11) -0.1792(3) 0.17207(10) 0.0288(3) Uani d . 1 . . C
  C2 0.41263(10) -0.2493(3) 0.25869(11) 0.0283(3) Uani d . 1 . . C
  C3 0.40727(9) -0.4432(3) 0.31994(10) 0.0249(3) Uani d . 1 . . C
  C4 0.32509(9) -0.5916(3) 0.30127(9) 0.0231(3) Uani d . 1 . . C
  C5 0.31677(9) -0.7921(3) 0.36502(9) 0.0231(3) Uani d . 1 . . C
  C6 0.23412(9) -0.9258(3) 0.34167(9) 0.0239(3) Uani d . 1 . . C
  C7 0.16400(9) -0.8570(3) 0.25405(10) 0.0268(3) Uani d . 1 . . C
  C8 0.16904(9) -0.6663(3) 0.18827(10) 0.0271(3) Uani d . 1 . . C
  C9 0.25149(9) -0.5312(3) 0.21538(10) 0.0248(3) Uani d . 1 . . C
  C10 0.19474(10) -1.1281(4) 0.38392(11) 0.0289(3) Uani d . 1 . . C
  C11 0.10984(10) -1.1639(4) 0.32247(11) 0.0336(4) Uani d . 1 . . C
  C12 0.39212(10) -1.0369(4) 0.51305(10) 0.0271(3) Uani d . 1 . . C
  C13 0.09892(11) -0.7760(4) 0.02912(11) 0.0371(4) Uani d . 1 . . C
  H12A 0.3524(14) -0.951(5) 0.5385(13) 0.056 Uiso d . 1 . . H
  H12B 0.4561(14) -1.050(5) 0.5612(13) 0.056 Uiso d . 1 . . H
  H12C 0.3734(13) -1.249(5) 0.4877(13) 0.056 Uiso d . 1 . . H
  H13A 0.1549(14) -0.721(5) 0.0262(13) 0.056 Uiso d . 1 . . H
  H13B 0.0463(14) -0.713(5) -0.0271(14) 0.056 Uiso d . 1 . . H
  H13C 0.0966(13) -1.003(6) 0.0418(13) 0.056 Uiso d . 1 . . H
  H3 0.4575(11) -0.486(4) 0.3790(11) 0.028(4) Uiso d . 1 . . H
  H2 0.4666(12) -0.144(4) 0.2690(11) 0.034(4) Uiso d . 1 . . H
  H11 0.0613(11) -1.279(4) 0.3229(11) 0.032(4) Uiso d . 1 . . H
  H10 0.2229(11) -1.225(4) 0.4447(12) 0.035(4) 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
  O1 0.0350(6) 0.0248(5) 0.0288(5) 0.0057(4) 0.0159(5) 0.0061(4)
  O2 0.0219(5) 0.0350(6) 0.0388(6) -0.0003(4) 0.0127(4) 0.0017(5)
  O3 0.0556(7) 0.0274(6) 0.0362(6) 0.0048(5) 0.0292(5) 0.0063(5)
  O4 0.0284(5) 0.0386(6) 0.0300(6) 0.0096(5) 0.0065(4) 0.0029(5)
  O5 0.0241(5) 0.0284(6) 0.0247(5) -0.0007(4) 0.0084(4) 0.0040(4)
  C1 0.0405(8) 0.0210(7) 0.0331(8) 0.0032(6) 0.0239(7) -0.0006(6)
  C2 0.0334(8) 0.0228(7) 0.0352(8) -0.0001(6) 0.0213(7) -0.0009(6)
  C3 0.0266(7) 0.0213(7) 0.0290(7) 0.0032(6) 0.0146(6) -0.0012(6)
  C4 0.0250(7) 0.0204(7) 0.0255(7) 0.0041(5) 0.0129(6) 0.0005(6)
  C5 0.0224(6) 0.0206(7) 0.0256(7) 0.0036(5) 0.0105(6) -0.0010(6)
  C6 0.0241(7) 0.0208(7) 0.0278(7) 0.0036(6) 0.0126(6) 0.0004(6)
  C7 0.0222(7) 0.0250(7) 0.0338(8) 0.0025(6) 0.0134(6) -0.0018(6)
  C8 0.0241(7) 0.0278(8) 0.0256(7) 0.0081(6) 0.0082(6) 0.0023(6)
  C9 0.0304(7) 0.0209(7) 0.0260(7) 0.0059(6) 0.0155(6) 0.0026(6)
  C10 0.0292(7) 0.0272(8) 0.0337(8) -0.0004(6) 0.0173(6) 0.0013(6)
  C11 0.0289(7) 0.0354(9) 0.0398(8) -0.0015(7) 0.0186(7) 0.0019(7)
  C12 0.0314(8) 0.0244(7) 0.0248(7) 0.0012(6) 0.0122(6) 0.0029(6)
  C13 0.0330(9) 0.0427(10) 0.0291(8) 0.0024(8) 0.0085(7) 0.0015(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
  O1 C9 . 1.3781(17) ?
  O1 C1 . 1.3789(19) ?
  O2 C7 . 1.3658(17) ?
  O2 C11 . 1.3888(19) ?
  O3 C1 . 1.2145(18) ?
  O4 C8 . 1.3721(17) ?
  O4 C13 . 1.447(2) ?
  O5 C5 . 1.3590(16) ?
  O5 C12 . 1.4336(17) ?
  C1 C2 . 1.446(2) ?
  C2 C3 . 1.341(2) ?
  C2 H2 . 0.966(18) ?
  C3 C4 . 1.436(2) ?
  C3 H3 . 0.967(16) ?
  C4 C9 . 1.4072(19) ?
  C4 C5 . 1.412(2) ?
  C5 C6 . 1.3993(19) ?
  C6 C7 . 1.4078(19) ?
  C6 C10 . 1.455(2) ?
  C7 C8 . 1.388(2) ?
  C8 C9 . 1.389(2) ?
  C10 C11 . 1.333(2) ?
  C10 H10 . 0.976(18) ?
  C11 H11 . 0.966(18) ?
  C12 H12A . 1.01(2) ?
  C12 H12B . 1.01(2) ?
  C12 H12C . 1.00(2) ?
  C13 H13A . 1.00(2) ?
  C13 H13B . 0.98(2) ?
  C13 H13C . 1.02(2) ?