##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.2
_journal_date_recd_electronic     2003-07-28
_journal_date_accepted     2003-09-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     10
_journal_page_first     o1506
_journal_page_last     o1508
_journal_paper_category     EO
_publ_contact_author_name     'Hamilton B. Napolitano'
_publ_contact_author_address
;
Instituto de Física de São Carlos
Universidade de São Paulo
13560 970 São Carlos, SP
Brazil
;
_publ_contact_author_email     hamilton@if.sc.usp.br
_publ_contact_author_fax     '55(16)2739881'
_publ_contact_author_phone     '55(16)2739868'
_publ_section_title
;
Redetermination and structural comparative study of
isopimpinellin: a new inhibitor against
Leishimania APRT enzyme
;
loop_
    _publ_author_name
    _publ_author_address
    'Napolitano, H. B.'
;    Instituto de Física de São Carlos USP
     Cx Postal 369, 13560-970 São Carlos, SP
     Brazil
;
    'Silva, M.'
;    Instituto de Física de São Carlos USP
     Cx Postal 369, 13560-970 São Carlos, SP
     Brazil
;
    'Ellena, J.'
;    Instituto de Física de São Carlos USP
     Cx Postal 369, 13560-970 São Carlos, SP
     Brazil
;
    'Rocha, W. C.'
;    Depto. Química,  UFSCar
     Cx Postal 676, 13565-905 São Carlos, SP
     Brazil
;
    'Vieira, P. C.'
;    Depto. Química,  UFSCar
     Cx Postal 676, 13565-905 São Carlos, SP
     Brazil
;
    'Thiemann, O. H.'
;    Instituto de Física de São Carlos USP
     Cx Postal 369, 13560-970 São Carlos, SP
     Brazil
;
    'Oliva, G.'
;    Instituto de Física de São Carlos USP
     Cx Postal 369, 13560-970 São Carlos, SP
     Brazil
;
_publ_section_synopsis
;
?
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_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_reflns_used     2772
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     27.485
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.53
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.119
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     KappaCCD
_diffrn_measurement_device     '95mm CCD camera onκ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     4114
_diffrn_reflns_av_R_equivalents     0.0229
_diffrn_reflns_theta_min     2.51
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     none
_reflns_number_total     2450
_reflns_number_gt     1841
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0441
_refine_ls_wR_factor_ref     0.1236
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     2450
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0713P)²+0.1752P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0
_refine_diff_density_max     0.232
_refine_diff_density_min     -0.3
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'HKL Denzo (Otwinowski & Minor, 1997) and Scalepack'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                  'Ortep-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2002)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
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
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances,
angles
 and torsion angles; correlations between esds in cell parameters are
only
 used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s.
planes.
;
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) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9 O1 C1 . . 122.16(11) ?
    C7 O2 C11 . . 105.49(11) ?
    C8 O4 C13 . . 112.89(11) ?
    C5 O5 C12 . . 118.37(11) ?
    O3 C1 O1 . . 116.64(14) ?
    O3 C1 C2 . . 126.23(14) ?
    O1 C1 C2 . . 117.13(12) ?
    C3 C2 C1 . . 121.37(14) ?
    C3 C2 H2 . . 123.4(10) ?
    C1 C2 H2 . . 115.2(10) ?
    C2 C3 C4 . . 121.06(14) ?
    C2 C3 H3 . . 122.2(10) ?
    C4 C3 H3 . . 116.7(10) ?
    C9 C4 C5 . . 120.26(13) ?
    C9 C4 C3 . . 117.27(13) ?
    C5 C4 C3 . . 122.48(13) ?
    O5 C5 C6 . . 127.08(12) ?
    O5 C5 C4 . . 114.05(12) ?
    C6 C5 C4 . . 118.87(12) ?
    C5 C6 C7 . . 117.50(13) ?
    C5 C6 C10 . . 137.99(13) ?
    C7 C6 C10 . . 104.50(12) ?
    O2 C7 C8 . . 123.24(13) ?
    O2 C7 C6 . . 110.85(12) ?
    C8 C7 C6 . . 125.91(13) ?
    O4 C8 C7 . . 122.09(13) ?
    O4 C8 C9 . . 123.19(13) ?
    C7 C8 C9 . . 114.68(13) ?
    O1 C9 C8 . . 116.35(12) ?
    O1 C9 C4 . . 120.91(13) ?
    C8 C9 C4 . . 122.74(13) ?
    C11 C10 C6 . . 106.74(14) ?
    C11 C10 H10 . . 124.6(10) ?
    C6 C10 H10 . . 128.7(10) ?
    C10 C11 O2 . . 112.42(14) ?
    C10 C11 H11 . . 133.3(10) ?
    O2 C11 H11 . . 114.3(10) ?
    O5 C12 H12A . . 109.8(12) ?
    O5 C12 H12B . . 104.3(12) ?
    H12A C12 H12B . . 112.6(16) ?
    O5 C12 H12C . . 111.4(11) ?
    H12A C12 H12C . . 111.6(17) ?
    H12B C12 H12C . . 106.9(17) ?
    O4 C13 H13A . . 108.2(12) ?
    O4 C13 H13B . . 106.6(12) ?
    H13A C13 H13B . . 111.5(16) ?
    O4 C13 H13C . . 107.7(11) ?
    H13A C13 H13C . . 111.6(17) ?
    H13B C13 H13C . . 111.1(17) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9 O1 C1 O3 . . . . -177.04(12) ?
    C9 O1 C1 C2 . . . . 3.43(19) ?
    O3 C1 C2 C3 . . . . 177.32(14) ?
    O1 C1 C2 C3 . . . . -3.2(2) ?
    C1 C2 C3 C4 . . . . 0.7(2) ?
    C2 C3 C4 C9 . . . . 1.7(2) ?
    C2 C3 C4 C5 . . . . -178.70(13) ?
    C12 O5 C5 C6 . . . . 0.3(2) ?
    C12 O5 C5 C4 . . . . -179.20(11) ?
    C9 C4 C5 O5 . . . . 178.82(12) ?
    C3 C4 C5 O5 . . . . -0.82(19) ?
    C9 C4 C5 C6 . . . . -0.8(2) ?
    C3 C4 C5 C6 . . . . 179.60(12) ?
    O5 C5 C6 C7 . . . . -178.03(13) ?
    C4 C5 C6 C7 . . . . 1.49(19) ?
    O5 C5 C6 C10 . . . . 3.0(3) ?
    C4 C5 C6 C10 . . . . -177.52(16) ?
    C11 O2 C7 C8 . . . . -178.94(14) ?
    C11 O2 C7 C6 . . . . 0.55(15) ?
    C5 C6 C7 O2 . . . . -179.81(12) ?
    C10 C6 C7 O2 . . . . -0.50(15) ?
    C5 C6 C7 C8 . . . . -0.3(2) ?
    C10 C6 C7 C8 . . . . 178.98(14) ?
    C13 O4 C8 C7 . . . . -103.24(16) ?
    C13 O4 C8 C9 . . . . 79.52(18) ?
    O2 C7 C8 O4 . . . . 0.4(2) ?
    C6 C7 C8 O4 . . . . -179.00(13) ?
    O2 C7 C8 C9 . . . . 177.88(12) ?
    C6 C7 C8 C9 . . . . -1.5(2) ?
    C1 O1 C9 C8 . . . . 178.98(12) ?
    C1 O1 C9 C4 . . . . -1.16(19) ?
    O4 C8 C9 O1 . . . . -0.4(2) ?
    C7 C8 C9 O1 . . . . -177.84(12) ?
    O4 C8 C9 C4 . . . . 179.73(12) ?
    C7 C8 C9 C4 . . . . 2.3(2) ?
    C5 C4 C9 O1 . . . . 178.89(12) ?
    C3 C4 C9 O1 . . . . -1.45(19) ?
    C5 C4 C9 C8 . . . . -1.3(2) ?
    C3 C4 C9 C8 . . . . 178.39(13) ?
    C5 C6 C10 C11 . . . . 179.33(17) ?
    C7 C6 C10 C11 . . . . 0.24(16) ?
    C6 C10 C11 O2 . . . . 0.09(18) ?
    C7 O2 C11 C10 . . . . -0.40(17) ?
    O1 O2 O4 O5 . . . . 2.02(5) ?
    O2 O4 O5 C1 . . . . -177.46(5) ?
    O4 O5 C1 C2 . . . . -177.19(11) ?
    O5 C1 C2 C3 . . . . 0.57(9) ?
    C1 C2 C3 C4 . . . . 0.7(2) ?
    C2 C3 C4 C5 . . . . -178.70(13) ?
    C3 C4 C5 C6 . . . . 179.60(12) ?
    C4 C5 C6 C7 . . . . 1.49(19) ?
    C5 C6 C7 C8 . . . . -0.3(2) ?
    C6 C7 C8 C9 . . . . -1.5(2) ?
    C7 C8 C9 C10 . . . . -0.14(9) ?
    C8 C9 C10 C11 . . . . -1.91(12) ?
    C9 C10 C11 C12 . . . . 27.4(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C12 H12B O5 3_636 1.01(2) 2.64(2) 3.4200(10)
                                               134.2(14)
    C13 H13B O4 3_545 0.98(2) 2.58(2) 3.455(2) 149.4(16)
    C12 H12A O3 4_556 1.01(2) 2.41(2) 3.2640(10)
                                               141.3(16)
    C12 H12C O3 4_546 1.00(2) 2.67(2) 3.0430(10)
                                               102.0(13)
    C11 H11 O2 2_545 0.960(10)
                             2.450(10)
                                     3.3600(10)
                                              156.7(13)
