##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.0.1.  #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_tzphoh
_audit_creation_method     from_xtal_archive_file_using_CIFIO
_journal_date_recd_electronic     99-02-15
_journal_date_accepted     99-03-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     JUL99
_journal_page_first     1160
_journal_page_last     1163
_journal_paper_category     FO
_publ_contact_author_name
;
Dr. Foces-Foces
;
_publ_contact_author_address
;
     Instituto de Quimica-Fisica Rocasolano CSIC
     Departamento de Cristalografia
     Serrano 119
     E-28006 Madrid
     Spain
;
_publ_contact_author_email     'xconcha@iqfr.csic.es'
_publ_contact_author_fax     34-91-5641431
_publ_contact_author_phone     34-91-5619400
_publ_section_title
;
 4-(1H-1,2,4-Triazol-1-yl)phenol
;
_publ_section_title_footnote
; 1-(4-hydroxyphenyl)-1H-1,2,4-triazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Foces-Foces, C.'
;
     Instituto Rocasolano, CSIC
     Departamento de Cristalografía
     Serrano 119
     E-28006 Madrid
     Spain
;
    'Cabildo, P.'
;
     Facultad de Ciencias, UNED
     Departamento de Química Orgánica y Biología
     Senda del Rey s/n
     E-28040 Madrid
     Spain
;
    'Claramunt, R. M.'
;
     Facultad de Ciencias, UNED
     Departamento de Química Orgánica y Biología
     Senda del Rey s/n
     E-28040 Madrid
     Spain
;
    'Elguero, J.'
;
     Instituto de Química Médica, CSIC
     Juan de la Cierva 3
     E-28006 Madrid
     Spain
;
_chemical_name_systematic     '4-(1H-1,2,4-triazol-1-yl)phenol'
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H7 N3 O'
_chemical_formula_sum     'C8 H7 N3 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     161.163
_chemical_melting_point     528
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     P_1_21/n_1
_symmetry_space_group_name_Hall     -P_2yn
loop_
    _symmetry_equiv_pos_as_xyz
    +x,+y,+z
    1/2-x,1/2+y,1/2-z
    -x,-y,-z
    1/2+x,1/2-y,1/2+z
_cell_length_a     18.409(2)
_cell_length_b     7.2898(6)
_cell_length_c     5.6649(4)
_cell_angle_alpha     90.00000
_cell_angle_beta     94.960(10)
_cell_angle_gamma     90.00000
_cell_volume     757.40(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     44
_cell_measurement_theta_min     2
_cell_measurement_theta_max     45
_cell_measurement_temperature     293
_exptl_crystal_description     'rectangular prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.413
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     336
_exptl_absorpt_coefficient_mu     0.817
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     xray_tube
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Seifert XRD 3000-S'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_reflns_number     1657
_diffrn_reflns_av_R_equivalents     0.01
_diffrn_reflns_av_sigmaI/netI     0.018
_diffrn_reflns_theta_min     4.82
_diffrn_reflns_theta_max     67.47
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -6
_diffrn_reflns_limit_l_max     6
_diffrn_reflns_reduction_process     equatorial_monochr_Lp
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     '100'
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    6 0 0
    -6 0 0
_reflns_number_total     1324
_reflns_number_observed     1104
_reflns_observed_criterion     'I>\s(I)'
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.061
_refine_ls_R_factor_obs     0.051
_refine_ls_wR_factor_all     0.044
_refine_ls_wR_factor_obs     0.039
_refine_ls_goodness_of_fit_all     0.903
_refine_ls_goodness_of_fit_obs     0.895
_refine_ls_number_reflns     1104
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]'
_refine_ls_shift/esd_max     0.006
_refine_ls_shift/esd_mean     0.001
_refine_diff_density_max     0.31
_refine_diff_density_min     -0.29
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_extinction_coef     '5.7(3) \\times 10^2^'
_refine_ls_abs_structure_details     none
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C ? .017 .009 'Int. Tables (1974, Vol IV)'
    H ? 0 0 'Int. Tables (1974, Vol IV)'
    N ? .029 .018 'Int. Tables (1974, Vol IV)'
    O ? .047 .032 'Int. Tables (1974, Vol IV)'
_computing_data_collection     'CRYSOM (Seifert, 1996)'
_computing_cell_refinement     'LSUCRE (Appleman, 1994)'
_computing_data_reduction     'xtal3.2 (Hall et al., 1992)'
_computing_structure_solution     'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement     'xtal3.2'
_computing_molecular_graphics     'xtal3.2'
_computing_publication_material     'xtal3.2'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_calc_attached_atom
    N1 .43675(7) .2069(2) .5584(3) .0393(8) Uani ? ?
    N2 .47453(8) .2201(3) .3621(3) .0500(10)
                                           Uani ? ?
    C3 .53950(10)
                .2711(3) .4528(4) .0530(10)
                                          Uani ? ?
    N4 .54636(8) .2907(3) .6906(3) .0530(10)
                                           Uani ? ?
    C5 .48070(10)
                .2496(3) .7494(4) .0500(10)
                                          Uani ? ?
    C6 .36086(9) .1616(2) .5425(3) .0365(9) Uani ? ?
    C7 .31620(9) .2142(3) .3463(3) .0390(10)
                                           Uani ? ?
    C8 .24220(10)
                .1807(3) .3377(3) .0390(10)
                                          Uani ? ?
    C9 .21293(9) .0951(2) .5266(3) .0372(9) Uani ? ?
    C10 .25840(10)
                 .0399(3) .7206(3) .0410(10)
                                           Uani ? ?
    C11 .33250(10)
                 .0719(3) .7296(3) .0420(10)
                                           Uani ? ?
    O12 .14021(7) .0613(2) .5320(3) .0483(8) Uani ? ?
    H3 .5770(10)
               .301(3) .351(4) .031(6) Uiso ? ?
    H5 .4640(10)
               .253(3) .907(4) .028(6) Uiso ? ?
    H7 .3380(10)
               .273(3) .216(4) .025(6) Uiso ? ?
    H8 .2100(10)
               .217(3) .201(4) .018(5) Uiso ? ?
    H10 .2380(10)
                -.019(3) .852(4) .023(5) Uiso ? ?
    H11 .3650(10)
                .031(3) .867(4) .016(5) Uiso ? ?
    H12 .112(2) .119(4) .391(5) .057(8) Uiso ? ?
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
    N1 .0313(7) .0475(9) .0395(9) -.0002(7) .0061(7) -.0011(7)
    N2 .0402(9) .0640(10)
                        .0460(10)
                                -.0019(8) .0123(7) .0020(8)
    C3 .0380(10)
               .0620(10)
                       .0620(10)
                               -.0008(9) .0130(10)
                                                 .0020(10)
    N4 .0335(8) .0660(10)
                        .0610(10)
                                -.0041(8) .0041(8) -.0073(9)
    C5 .0350(10)
               .0660(10)
                       .0470(10)
                               -.0035(9) .0036(9) -.0080(10)
    C6 .0327(9) .0380(10)
                        .0390(10)
                                .0020(7) .0051(7) -.0022(8)
    C7 .0380(10)
               .0430(10)
                       .0370(10)
                               .0008(8) .0059(8) .0009(8)
    C8 .0374(9) .0450(10)
                        .0350(10)
                                .0021(8) .0015(8) -.0021(8)
    C9 .0327(9) .0360(10)
                        .0430(10)
                                .0003(7) .0056(8) -.0062(8)
    C10 .0390(10)
                .0440(10)
                        .0400(10)
                                -.0003(8) .0089(8) .0057(9)
    C11 .0400(10)
                .0470(10)
                        .0400(10)
                                .0036(9) .0021(8) .0068(9)
    O12 .0303(7) .0616(9) .0536(9) -.0017(6) .0066(6) .0027(7)
_geom_special_details     ?
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 N2 . . 1.365(2) yes
    N1 C5 . . 1.331(2) yes
    N1 C6 . . 1.431(2) yes
    N2 C3 . . 1.314(2) yes
    C3 N4 . . 1.350(3) yes
    C3 H3 . . 0.97(2) ?
    N4 C5 . . 1.316(3) yes
    C5 H5 . . 0.96(2) ?
    C6 C7 . . 1.379(2) ?
    C6 C11 . . 1.385(3) ?
    C7 C8 . . 1.382(3) ?
    C7 H7 . . 0.97(2) ?
    C8 C9 . . 1.387(3) ?
    C8 H8 . . 0.97(2) ?
    C9 C10 . . 1.382(2) ?
    C9 O12 . . 1.364(2) yes
    C10 C11 . . 1.381(3) ?
    C10 H10 . . 0.96(2) ?
    C11 H11 . . 0.98(2) ?
    O12 H12 . . 1.00(3) ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    N4 H12 1.72(3) . 4 ?
    C9 H12 1.95(3) . . ?
    N2 H3 1.99(2) . . ?
    N1 H5 2.02(2) . . ?
    C6 H7 2.03(2) . . ?
    C9 H10 2.04(2) . . ?
    C11 H10 2.04(2) . . ?
    N4 H5 2.04(2) . . ?
    C9 H8 2.05(2) . . ?
    C7 H8 2.05(2) . . ?
    N4 H3 2.06(2) . . ?
    C10 H11 2.06(2) . . ?
    C8 H7 2.06(2) . . ?
    C6 H11 2.06(2) . . ?
    C3 C5 2.082(3) . . ?
    N1 C3 2.085(3) . . ?
    N1 N4 2.178(2) . . ?
    N2 C5 2.197(3) . . ?
    N2 N4 2.247(2) . . ?
    H8 H12 2.29(4) . . ?
    C10 O12 2.344(2) . . ?
    H10 H11 2.36(3) . . ?
    H7 H8 2.38(3) . . ?
    C6 C10 2.386(3) . . ?
    C6 C8 2.388(2) . . ?
    C8 C10 2.395(3) . . ?
    C7 C9 2.397(3) . . ?
    C9 C11 2.400(2) . . ?
    C7 C11 2.402(3) . . ?
    C8 O12 2.418(2) . . ?
    N1 C7 2.431(2) . . ?
    N1 C11 2.432(2) . . ?
    H5 H11 2.44(3) . . ?
    O12 H3 2.44(2) . 4_455 ?
    N2 C6 2.444(2) . . ?
    C8 H12 2.48(3) . . ?
    C5 C6 2.491(3) . . ?
    O12 H10 2.51(2) . . ?
    O12 H7 2.58(2) . 2_545 ?
    N2 H5 2.58(2) . 1_554 ?
    N1 H7 2.59(2) . . ?
    N2 H7 2.61(2) . . ?
    N1 H11 2.62(2) . . ?
    O12 H8 2.62(2) . . ?
    C5 H12 2.66(3) . 4 ?
    H8 H10 2.70(3) . 1_554 ?
    N4 O12 2.704(2) . 4 ?
    H7 H11 2.73(3) . 1_554 ?
    C6 C9 2.760(2) . . ?
    C7 C10 2.763(3) . . ?
    C6 H5 2.76(2) . . ?
    H7 H12 2.77(4) . 2 ?
    C8 C11 2.772(3) . . ?
    C5 H11 2.79(2) . . ?
    H3 H12 2.79(4) . 4_554 ?
    C8 H10 2.81(2) . 2_556 ?
    C7 H10 2.83(2) . 2_556 ?
    C3 H12 2.83(3) . 4 ?
    C9 H7 2.84(2) . 2_545 ?
    C11 H5 2.87(2) . . ?
    H5 H12 2.89(4) . 4 ?
    N2 C7 2.909(2) . . ?
    H3 H11 2.96(3) . 3_656 ?
    O12 H5 3.00(2) . 2_546 ?
    N4 H8 3.01(2) . 4 ?
    C5 C11 3.013(3) . . ?
    H3 H8 3.01(3) . 4 ?
    N1 H3 3.02(2) . . ?
    C9 H10 3.02(2) . 2_556 ?
    C5 H3 3.02(2) . . ?
    C3 H5 3.03(2) . . ?
    H5 H7 3.04(3) . 1_556 ?
    C6 H10 3.04(2) . 2_556 ?
    C8 H10 3.11(2) . 1_554 ?
    N2 H5 3.12(2) . . ?
    C11 H7 3.12(2) . 1_556 ?
    H3 H12 3.13(4) . 4 ?
    H3 H5 3.14(3) . 1_554 ?
    C10 H12 3.19(3) . . ?
    C10 H8 3.21(2) . 1_556 ?
    C7 H11 3.22(2) . 1_554 ?
    C11 H3 3.24(2) . 3_656 ?
    C10 H10 3.24(2) . 2_556 ?
    H8 H10 3.26(3) . 2_556 ?
    C6 H10 3.26(2) . . ?
    C8 H10 3.26(2) . . ?
    C11 H7 3.27(2) . . ?
    C10 H8 3.27(2) . . ?
    C6 H8 3.27(2) . . ?
    C11 H10 3.27(2) . 2_556 ?
    H5 H12 3.27(4) . 2_556 ?
    C3 H5 3.28(2) . 1_554 ?
    C9 H7 3.28(2) . . ?
    C9 H11 3.29(2) . . ?
    H7 H10 3.29(3) . 2_556 ?
    C7 H11 3.29(2) . . ?
    C9 H3 3.31(2) . 4_455 ?
    H11 H12 3.31(4) . 2_546 ?
    C8 H7 3.32(2) . 2_545 ?
    C3 H8 3.33(2) . 4 ?
    H3 H10 3.35(3) . 4_554 ?
    C3 O12 3.373(3) . 4_554 ?
    H7 H10 3.40(3) . 1_554 ?
    H7 H8 3.40(3) . 2 ?
    C9 H8 3.40(2) . 2_545 ?
    C3 H11 3.44(2) . 3_656 ?
    C10 H8 3.44(2) . 2_545 ?
    C7 O12 3.455(2) . 2 ?
    C3 C6 3.464(3) . . ?
    C5 H3 3.47(2) . 3_666 ?
    O12 H11 3.48(2) . 2_556 ?
    C7 H10 3.48(2) . 1_554 ?
    H10 H12 3.48(3) . . ?
    C5 O12 3.483(3) . 2_556 ?
    N2 C5 3.489(3) . 1_554 ?
    C10 H7 3.49(2) . 1_556 ?
    C7 C9 3.503(3) . 2 ?
    C8 H8 3.50(2) . 2_545 ?
    C5 O12 3.503(2) . 4 ?
    C10 H7 3.51(2) . 2_545 ?
    N1 C3 3.513(3) . 3_656 ?
    O12 H5 3.53(2) . 4_454 ?
    N1 N2 3.526(2) . 3_656 ?
    C7 H12 3.54(3) . 2 ?
    C9 H11 3.56(2) . 2_556 ?
    N2 H12 3.56(3) . 2 ?
    N4 C9 3.565(2) . 4 ?
    C9 C10 3.565(3) . 2_556 ?
    N4 C6 3.572(2) . . ?
    N2 H11 3.59(2) . 1_554 ?
    N2 C5 3.590(3) . 3_656 ?
    C11 H8 3.59(2) . 2_545 ?
    C6 H3 3.60(2) . 3_656 ?
    N2 N4 3.596(3) . 3_666 ?
    H3 H5 3.62(3) . 3_666 ?
    C11 O12 3.620(2) . . ?
    C8 C10 3.622(3) . 2_556 ?
    C3 N4 3.625(3) . 3_666 ?
    N1 H3 3.63(2) . 3_666 ?
    N4 C8 3.635(2) . 4 ?
    C5 C7 3.640(3) . . ?
    N2 C11 3.644(3) . . ?
    C3 H12 3.65(3) . 4_554 ?
    C3 C11 3.646(3) . 3_656 ?
    C3 C6 3.648(3) . 3_656 ?
    N2 N2 3.655(3) . 3_656 ?
    C10 H3 3.66(2) . 4_455 ?
    C7 H8 3.66(2) . 2_545 ?
    C7 O12 3.665(2) . . ?
    C10 C10 3.675(3) . 2_556 ?
    C10 C10 3.675(3) . 2_546 ?
    C8 C10 3.680(3) . 1_554 ?
    C7 C11 3.681(3) . 1_554 ?
    C3 C5 3.686(3) . 3_666 ?
    C7 C8 3.690(3) . 2 ?
    N1 C10 3.692(2) . . ?
    N1 C8 3.696(2) . . ?
    C3 C3 3.697(3) . 3_666 ?
    C7 H8 3.70(2) . 2 ?
    C8 H11 3.71(2) . 2_556 ?
    N4 H11 3.71(2) . 3_657 ?
    C6 H8 3.71(2) . 2_545 ?
    C5 H3 3.72(2) . 1_556 ?
    C7 H10 3.73(2) . . ?
    C10 H7 3.73(2) . . ?
    N4 H3 3.73(2) . 1_556 ?
    N4 H3 3.74(2) . 3_666 ?
    C11 H8 3.74(2) . . ?
    N2 C3 3.746(3) . 3_656 ?
    N2 N4 3.753(3) . 3_656 ?
    N1 H3 3.75(2) . 3_656 ?
    C8 H11 3.75(2) . . ?
    C7 C10 3.758(3) . 2_556 ?
    C6 O12 3.783(2) . 2_556 ?
    N1 H5 3.79(2) . 1_554 ?
    C11 H8 3.79(2) . 1_556 ?
    C8 C9 3.790(3) . 2 ?
    C8 C8 3.796(3) . 2_545 ?
    C8 C8 3.796(3) . 2 ?
    C8 H11 3.80(2) . 1_554 ?
    N2 H11 3.80(2) . 3_656 ?
    N1 H12 3.82(3) . 4 ?
    O12 H10 3.82(2) . 2_556 ?
    C10 C11 3.821(3) . 2_546 ?
    N1 O12 3.826(2) . 2_556 ?
    C3 O12 3.827(3) . 4 ?
    C7 C10 3.829(3) . 1_554 ?
    N1 C3 3.832(3) . 3_666 ?
    C5 H7 3.83(2) . . ?
    C11 O12 3.833(2) . 2_556 ?
    C3 H7 3.83(2) . . ?
    N4 H7 3.84(2) . 3_666 ?
    C6 C10 3.838(3) . 2_556 ?
    C7 H12 3.85(3) . . ?
    N2 O12 3.849(2) . 2 ?
    N1 H10 3.86(2) . 2_556 ?
    C9 C11 3.858(3) . 2_556 ?
    C7 H5 3.86(2) . 1_554 ?
    C5 H12 3.86(3) . 2_556 ?
    N2 C3 3.869(3) . 3_666 ?
    C5 H7 3.89(2) . 1_556 ?
    N2 H11 3.89(2) . . ?
    N1 N1 3.902(2) . 3_656 ?
    O12 H11 3.91(2) . 2_546 ?
    N1 N4 3.914(2) . 3_656 ?
    C8 H3 3.92(2) . 4_454 ?
    C9 H8 3.93(2) . 1_556 ?
    N2 H12 3.93(3) . 4 ?
    N1 N4 3.946(2) . 3_666 ?
    C6 H11 3.95(2) . 1_554 ?
    C6 H7 3.96(2) . 1_556 ?
    C10 H3 3.96(2) . 3_656 ?
    N2 H5 3.97(2) . 3_656 ?
    C3 C5 3.972(3) . 3_656 ?
    C9 H10 3.98(2) . 1_554 ?
    C11 O12 3.976(2) . 2_546 ?
    N4 C6 3.990(3) . 3_656 ?
    N1 H12 3.99(3) . 2 ?
    C5 H11 3.99(2) . 3_657 ?
    C3 H3 4.00(2) . 3_666 ?
    N2 H3 4.00(2) . 3_666 ?
    C7 H5 4.01(2) . . ?
    N2 C5 4.015(3) . 3_666 ?
    C8 H8 4.02(2) . 2 ?
    C11 H12 4.02(3) . 2_546 ?
    C3 H5 4.02(2) . 3_666 ?
    N4 N4 4.031(3) . 3_666 ?
    C8 C11 4.031(3) . 1_554 ?
    C10 H8 4.04(2) . 2_546 ?
    N2 O12 4.041(2) . 4_554 ?
    C3 C5 4.041(3) . 1_554 ?
    C8 C11 4.075(3) . 2_556 ?
    C8 C10 4.106(3) . 2 ?
    N1 C5 4.108(3) . 3_656 ?
    N2 C6 4.115(2) . 3_656 ?
    C6 O12 4.123(2) . . ?
    C3 C7 4.123(3) . . ?
    C7 C10 4.132(3) . 2 ?
    C10 O12 4.144(2) . 2_546 ?
    C7 C8 4.144(3) . 2_545 ?
    C9 C11 4.166(3) . 2_546 ?
    N2 N4 4.166(2) . 1_554 ?
    C3 C8 4.171(3) . 4 ?
    N4 C5 4.180(3) . 3_666 ?
    N1 C9 4.189(2) . . ?
    C8 O12 4.190(2) . 2 ?
    N2 C11 4.212(3) . 3_656 ?
    C10 C11 4.242(3) . 2_556 ?
    C3 C3 4.261(3) . 3_656 ?
    N4 C11 4.271(3) . . ?
    N2 C8 4.278(2) . . ?
    C3 C9 4.279(3) . 4_554 ?
    C6 C9 4.285(3) . 2_556 ?
    N4 C11 4.306(3) . 3_656 ?
    C9 C10 4.311(3) . 2_546 ?
    C3 N4 4.333(3) . 1_554 ?
    C7 O12 4.355(2) . 2_556 ?
    C5 C10 4.359(3) . . ?
    N1 O12 4.364(2) . 2 ?
    C6 O12 4.367(2) . 2 ?
    N4 O12 4.369(2) . 2_556 ?
    N4 O12 4.380(2) . 4_554 ?
    N2 C11 4.384(2) . 1_554 ?
    C10 O12 4.410(2) . 2_556 ?
    C8 C11 4.426(3) . 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 N1 C5 . . . 109.20(10)
                            yes
    N2 N1 C6 . . . 121.90(10)
                            yes
    C5 N1 C6 . . . 128.8(2) yes
    N1 N2 C3 . . . 102.3(2) yes
    N2 C3 N4 . . . 115.1(2) yes
    N2 C3 H3 . . . 121.0(10)
                          ?
    N4 C3 H3 . . . 124.0(10)
                          ?
    C3 N4 C5 . . . 102.7(2) yes
    N1 C5 N4 . . . 110.8(2) yes
    N1 C5 H5 . . . 123.0(10)
                          ?
    N4 C5 H5 . . . 127.0(10)
                          ?
    N1 C6 C7 . . . 119.8(2) ?
    N1 C6 C11 . . . 119.4(2) ?
    C7 C6 C11 . . . 120.7(2) yes
    C6 C7 C8 . . . 119.8(2) ?
    C6 C7 H7 . . . 119.0(10)
                          ?
    C8 C7 H7 . . . 121.0(10)
                          ?
    C7 C8 C9 . . . 120.0(2) ?
    C7 C8 H8 . . . 121.0(10)
                          ?
    C9 C8 H8 . . . 119.0(10)
                          ?
    C8 C9 C10 . . . 119.7(2) yes
    C8 C9 O12 . . . 123.0(2) ?
    C10 C9 O12 . . . 117.2(2) ?
    C9 C10 C11 . . . 120.6(2) ?
    C9 C10 H10 . . . 120.0(10)
                            ?
    C11 C10 H10 . . . 120.0(10)
                             ?
    C6 C11 C10 . . . 119.2(2) ?
    C6 C11 H11 . . . 120.0(10)
                            ?
    C10 C11 H11 . . . 120.0(10)
                             ?
    C9 O12 H12 . . . 110(2) ?
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
    N2 N1 C6 C7 . . . . -31.3(2) yes
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
    _geom_hbond_publ_flag
    O12 H12 N4 4_454 1.00(3) 1.72(3) 2.704(2) 166(3) yes
    C5 H5 N2 1_556 0.97(2) 2.58(2) 3.489(3) 157(2) yes
    C3 H3 O12 4_554 0.97(2) 2.44(2) 3.373(3) 161(2) yes
    C7 H7 O12 2_555 0.97(2) 2.58(2) 3.455(2) 151(2) yes
