##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2009-02-03
_journal_date_accepted     2009-02-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o552
_journal_page_last     o552
_journal_paper_category     QO
_journal_coeditor_code     HG2475
_publ_contact_author_name     'Dr P. A. Crooks'
_publ_contact_author_address
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
_publ_contact_author_email     pcrooks@email.uky.edu
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;\
3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1<i>H</i>-imidazol-5-yl)-3-\
hydroxyindolin-2-one monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Narsimha Reddy Penthala'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Thirupathi Reddy Yerram Reddy'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1<i>H</i>-imidazol-5-yl)-3-
hydroxyindolin-2-one monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 N4 O3 , H2 O'
_chemical_formula_sum     'C12 H14 N4 O4'
_chemical_formula_iupac     'C12 H12 N4 O3 , H2 O'
_chemical_formula_weight     278.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.35140(10)
_cell_length_b     10.7166(2)
_cell_length_c     13.9679(2)
_cell_angle_alpha     90.00
_cell_angle_beta     104.7550(10)
_cell_angle_gamma     90.00
_cell_volume     1208.88(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9952
_cell_measurement_theta_min     5.27
_cell_measurement_theta_max     67.95
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.529
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu     0.991
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in APEX2; Bruker, 2006)'
_exptl_absorpt_correction_T_min     0.780
_exptl_absorpt_correction_T_max     0.943
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus rotating anode'
_diffrn_radiation_monochromator     'graded multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     17255
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     5.27
_diffrn_reflns_theta_max     67.95
_diffrn_reflns_theta_full     67.95
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
2\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2181
_reflns_number_gt     2121
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0350
_refine_ls_R_factor_gt     0.0344
_refine_ls_wR_factor_gt     0.0878
_refine_ls_wR_factor_ref     0.0884
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2181
_refine_ls_number_parameters     191
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.777P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.258
_refine_diff_density_min     -0.267
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0029(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
loop_
    _atom_site_type_symbol
    _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
    O O1 -0.09392(12) 0.10429(9) 0.10391(7) 0.0184(2) Uani d . 1 . .
    N N1 -0.15262(14) 0.29911(10) 0.15528(8) 0.0158(3) Uani d . 1 . .
    H H1 -0.2381 0.3179 0.1060 0.019 Uiso calc R 1 . .
    C C1 -0.06677(16) 0.19095(12) 0.16253(9) 0.0146(3) Uani d . 1 . .
    C C2 -0.08770(16) 0.37782(12) 0.23678(9) 0.0150(3) Uani d . 1 . .
    C C3 -0.14037(16) 0.49625(13) 0.25289(10) 0.0183(3) Uani d . 1 . .
    H H3 -0.2307 0.5349 0.2072 0.022 Uiso calc R 1 . .
    C C4 -0.05487(17) 0.55663(13) 0.33926(10) 0.0192(3) Uani d . 1 . .
    H H4 -0.0875 0.6383 0.3527 0.023 Uiso calc R 1 . .
    C C5 0.07679(16) 0.49981(13) 0.40589(10) 0.0179(3) Uani d . 1 . .
    H H5 0.1332 0.5433 0.4640 0.021 Uiso calc R 1 . .
    C C6 0.12728(16) 0.37988(12) 0.38869(9) 0.0161(3) Uani d . 1 . .
    H H6 0.2163 0.3405 0.4348 0.019 Uiso calc R 1 . .
    C C7 0.04456(16) 0.31943(12) 0.30268(9) 0.0143(3) Uani d . 1 . .
    O O8 0.03982(11) 0.09668(8) 0.32447(6) 0.0154(2) Uani d . 1 . .
    H H8 0.0481 0.0270 0.2986 0.023 Uiso calc R 1 . .
    C C8 0.07032(16) 0.19298(12) 0.26163(9) 0.0142(3) Uani d . 1 . .
    C C9 0.24325(16) 0.17641(12) 0.24175(9) 0.0134(3) Uani d . 1 . .
    H H9 0.2513 0.0945 0.2090 0.016 Uiso calc R 1 . .
    C C10 0.41472(17) 0.10072(12) 0.41347(9) 0.0171(3) Uani d . 1 . .
    H H10A 0.5352 0.0920 0.4366 0.026 Uiso calc R 1 . .
    H H10B 0.3655 0.0195 0.3909 0.026 Uiso calc R 1 . .
    H H10C 0.3705 0.1309 0.4678 0.026 Uiso calc R 1 . .
    N N10 0.37459(13) 0.18921(10) 0.33208(8) 0.0138(3) Uani d . 1 . .
    C C11 0.45660(16) 0.29528(12) 0.32705(9) 0.0148(3) Uani d . 1 . .
    N N11 0.57702(14) 0.33716(11) 0.40073(8) 0.0195(3) Uani d . 1 . .
    H H11A 0.6067 0.2948 0.4564 0.023 Uiso calc R 1 . .
    H H11B 0.6276 0.4075 0.3942 0.023 Uiso calc R 1 . .
    N N12 0.40787(14) 0.35577(10) 0.23870(8) 0.0156(3) Uani d . 1 . .
    O O13 0.21974(12) 0.30271(8) 0.09262(7) 0.0174(2) Uani d . 1 . .
    C C13 0.28724(16) 0.28445(12) 0.18112(9) 0.0140(3) Uani d . 1 . .
    O O1W 0.03730(13) 0.14500(11) 0.52700(8) 0.0256(3) Uani d D 1 . .
    H H1W 0.023(2) 0.1260(19) 0.4666(13) 0.038 Uiso d D 1 . .
    H H2W -0.058(2) 0.1453(19) 0.5402(14) 0.038 Uiso d D 1 . .
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 0.0209(5) 0.0161(5) 0.0156(5) -0.0002(4) -0.0002(4) -0.0028(4)
    N1 0.0151(5) 0.0148(6) 0.0149(5) 0.0014(4) -0.0010(4) 0.0007(4)
    C1 0.0150(6) 0.0141(6) 0.0140(6) -0.0015(5) 0.0025(5) 0.0010(5)
    C2 0.0149(6) 0.0147(6) 0.0155(6) -0.0017(5) 0.0043(5) 0.0001(5)
    C3 0.0161(6) 0.0153(7) 0.0238(7) 0.0021(5) 0.0058(5) 0.0026(5)
    C4 0.0205(7) 0.0123(6) 0.0278(7) -0.0005(5) 0.0117(6) -0.0025(5)
    C5 0.0201(7) 0.0169(7) 0.0182(7) -0.0046(5) 0.0079(5) -0.0044(5)
    C6 0.0170(6) 0.0160(7) 0.0153(6) -0.0013(5) 0.0040(5) -0.0002(5)
    C7 0.0157(6) 0.0120(6) 0.0151(6) -0.0003(5) 0.0038(5) 0.0003(5)
    O8 0.0198(5) 0.0106(5) 0.0151(5) -0.0008(4) 0.0032(4) 0.0000(3)
    C8 0.0164(7) 0.0116(6) 0.0128(6) 0.0004(5) 0.0007(5) 0.0007(5)
    C9 0.0155(6) 0.0111(6) 0.0115(6) 0.0006(5) -0.0004(5) -0.0004(5)
    C10 0.0201(7) 0.0139(6) 0.0146(6) 0.0003(5) -0.0006(5) 0.0034(5)
    N10 0.0153(5) 0.0113(5) 0.0124(5) -0.0002(4) -0.0009(4) 0.0013(4)
    C11 0.0156(6) 0.0132(6) 0.0147(6) 0.0008(5) 0.0026(5) -0.0001(5)
    N11 0.0228(6) 0.0159(6) 0.0156(6) -0.0059(5) -0.0029(5) 0.0029(4)
    N12 0.0186(6) 0.0129(5) 0.0134(5) -0.0008(4) 0.0006(4) 0.0011(4)
    O13 0.0215(5) 0.0154(5) 0.0128(5) 0.0004(4) -0.0003(4) 0.0010(3)
    C13 0.0157(6) 0.0116(6) 0.0140(6) 0.0030(5) 0.0024(5) 0.0000(5)
    O1W 0.0214(5) 0.0353(6) 0.0184(5) -0.0051(4) 0.0019(4) -0.0057(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C1 . 1.2206(16) ?
    N1 C1 . 1.3531(17) ?
    N1 C2 . 1.4096(17) ?
    N1 H1 . 0.8800 ?
    C1 C8 . 1.5557(17) ?
    C2 C3 . 1.3803(19) ?
    C2 C7 . 1.3932(18) ?
    C3 C4 . 1.395(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.387(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3925(19) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.3847(18) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.5080(17) ?
    O8 C8 . 1.4192(15) ?
    O8 H8 . 0.8400 ?
    C8 C9 . 1.5488(18) ?
    C9 N10 . 1.4522(16) ?
    C9 C13 . 1.5334(17) ?
    C9 H9 . 1.0000 ?
    C10 N10 . 1.4525(16) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    N10 C11 . 1.3382(17) ?
    C11 N11 . 1.3209(17) ?
    C11 N12 . 1.3612(17) ?
    N11 H11A . 0.8800 ?
    N11 H11B . 0.8800 ?
    N12 C13 . 1.3540(17) ?
    O13 C13 . 1.2366(16) ?
    O1W H1W . 0.847(18) ?
    O1W H2W . 0.861(18) ?
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
    C1 N1 C2 . . 111.39(11) ?
    C1 N1 H1 . . 124.3 ?
    C2 N1 H1 . . 124.3 ?
    O1 C1 N1 . . 126.67(12) ?
    O1 C1 C8 . . 125.20(11) ?
    N1 C1 C8 . . 108.08(10) ?
    C3 C2 C7 . . 122.50(12) ?
    C3 C2 N1 . . 127.51(12) ?
    C7 C2 N1 . . 109.99(11) ?
    C2 C3 C4 . . 116.96(12) ?
    C2 C3 H3 . . 121.5 ?
    C4 C3 H3 . . 121.5 ?
    C5 C4 C3 . . 121.36(12) ?
    C5 C4 H4 . . 119.3 ?
    C3 C4 H4 . . 119.3 ?
    C4 C5 C6 . . 120.82(12) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C7 C6 C5 . . 118.39(12) ?
    C7 C6 H6 . . 120.8 ?
    C5 C6 H6 . . 120.8 ?
    C6 C7 C2 . . 119.96(12) ?
    C6 C7 C8 . . 131.47(12) ?
    C2 C7 C8 . . 108.56(11) ?
    C8 O8 H8 . . 109.5 ?
    O8 C8 C7 . . 110.67(10) ?
    O8 C8 C9 . . 110.48(10) ?
    C7 C8 C9 . . 113.64(10) ?
    O8 C8 C1 . . 109.44(10) ?
    C7 C8 C1 . . 101.94(10) ?
    C9 C8 C1 . . 110.33(10) ?
    N10 C9 C13 . . 100.04(10) ?
    N10 C9 C8 . . 111.46(10) ?
    C13 C9 C8 . . 112.21(10) ?
    N10 C9 H9 . . 110.9 ?
    C13 C9 H9 . . 110.9 ?
    C8 C9 H9 . . 110.9 ?
    N10 C10 H10A . . 109.5 ?
    N10 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N10 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C11 N10 C9 . . 108.54(10) ?
    C11 N10 C10 . . 125.20(11) ?
    C9 N10 C10 . . 126.23(10) ?
    N11 C11 N10 . . 123.09(12) ?
    N11 C11 N12 . . 122.48(12) ?
    N10 C11 N12 . . 114.41(11) ?
    C11 N11 H11A . . 120.0 ?
    C11 N11 H11B . . 120.0 ?
    H11A N11 H11B . . 120.0 ?
    C13 N12 C11 . . 105.97(11) ?
    O13 C13 N12 . . 125.82(12) ?
    O13 C13 C9 . . 124.01(11) ?
    N12 C13 C9 . . 110.17(10) ?
    H1W O1W H2W . . 108.3(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
    C2 N1 C1 O1 . . . . 179.49(12) ?
    C2 N1 C1 C8 . . . . 1.73(14) ?
    C1 N1 C2 C3 . . . . 177.98(13) ?
    C1 N1 C2 C7 . . . . -1.42(15) ?
    C7 C2 C3 C4 . . . . -0.05(19) ?
    N1 C2 C3 C4 . . . . -179.38(12) ?
    C2 C3 C4 C5 . . . . -0.16(19) ?
    C3 C4 C5 C6 . . . . -0.3(2) ?
    C4 C5 C6 C7 . . . . 1.00(19) ?
    C5 C6 C7 C2 . . . . -1.19(19) ?
    C5 C6 C7 C8 . . . . 178.47(13) ?
    C3 C2 C7 C6 . . . . 0.7(2) ?
    N1 C2 C7 C6 . . . . -179.82(11) ?
    C3 C2 C7 C8 . . . . -179.00(12) ?
    N1 C2 C7 C8 . . . . 0.44(14) ?
    C6 C7 C8 O8 . . . . 64.51(18) ?
    C2 C7 C8 O8 . . . . -115.79(12) ?
    C6 C7 C8 C9 . . . . -60.47(18) ?
    C2 C7 C8 C9 . . . . 119.23(12) ?
    C6 C7 C8 C1 . . . . -179.17(13) ?
    C2 C7 C8 C1 . . . . 0.53(13) ?
    O1 C1 C8 O8 . . . . -61.96(16) ?
    N1 C1 C8 O8 . . . . 115.85(11) ?
    O1 C1 C8 C7 . . . . -179.17(12) ?
    N1 C1 C8 C7 . . . . -1.36(13) ?
    O1 C1 C8 C9 . . . . 59.80(16) ?
    N1 C1 C8 C9 . . . . -122.39(11) ?
    O8 C8 C9 N10 . . . . -64.03(13) ?
    C7 C8 C9 N10 . . . . 61.06(14) ?
    C1 C8 C9 N10 . . . . 174.83(10) ?
    O8 C8 C9 C13 . . . . -175.30(10) ?
    C7 C8 C9 C13 . . . . -50.22(14) ?
    C1 C8 C9 C13 . . . . 63.55(13) ?
    C13 C9 N10 C11 . . . . 8.33(13) ?
    C8 C9 N10 C11 . . . . -110.49(12) ?
    C13 C9 N10 C10 . . . . -169.97(11) ?
    C8 C9 N10 C10 . . . . 71.21(15) ?
    C9 N10 C11 N11 . . . . 175.73(12) ?
    C10 N10 C11 N11 . . . . -5.9(2) ?
    C9 N10 C11 N12 . . . . -5.46(15) ?
    C10 N10 C11 N12 . . . . 172.86(11) ?
    N11 C11 N12 C13 . . . . 178.05(12) ?
    N10 C11 N12 C13 . . . . -0.77(15) ?
    C11 N12 C13 O13 . . . . -174.16(12) ?
    C11 N12 C13 C9 . . . . 6.41(14) ?
    N10 C9 C13 O13 . . . . 171.44(12) ?
    C8 C9 C13 O13 . . . . -70.29(16) ?
    N10 C9 C13 N12 . . . . -9.12(13) ?
    C8 C9 C13 N12 . . . . 109.15(12) ?
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
    N1 H1 O1W 4_565 0.88 1.96 2.8128(15) 163.1
    O8 H8 N12 2_545 0.84 1.97 2.7984(14) 169.8
    N11 H11A O13 4_666 0.88 2.17 3.0371(15) 170.8
    N11 H11B O1 2 0.88 2.13 2.8678(15) 141.1
    O1W H1W O8 . 0.847(18) 2.049(18) 2.8812(14) 167.4(19)
    O1W H2W O13 4_566 0.861(18) 2.233(18) 3.0702(14) 164.1(19)