##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It 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 may be obtained 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                 #
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data_alpha-NTO
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-05-02
_journal_date_accepted     2005-07-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2005
_journal_volume     61
_journal_issue      5
_journal_page_first     577
_journal_page_last     584
_journal_paper_category     FA
_journal_coeditor_code     SN5022
_chemical_name_systematic     '5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one'
_chemical_name_common     'alpha-NTO'
_chemical_formula_moiety     'C2 H2 N4 O3'
_chemical_formula_sum     'C2 H2 N4 O3'
_chemical_formula_weight     130.08
_chemical_melting_point     ?
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.1233(8)
_cell_length_b     10.3140(16)
_cell_length_c     17.998(3)
_cell_angle_alpha     106.610(2)
_cell_angle_beta     97.810(2)
_cell_angle_gamma     90.130(2)
_cell_volume     902.1(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3399
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'parallelpiped'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.916
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.178
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
;
_exptl_absorpt_correction_T_min     0.851
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
 identical or equivalent reflections were not merged
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker platform with 1K CCD'
_diffrn_measurement_method     ω-scans
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8966
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0423
_diffrn_reflns_theta_min     2.06
_diffrn_reflns_theta_max     28.70
_diffrn_reflns_theta_full     28.70
_diffrn_measured_fraction_theta_max     0.877
_diffrn_measured_fraction_theta_full     0.877
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.
Using the twin laws above, the structural model was refined as a
four-component twin using the procedure associated with the HKLF 5 format for
merohedral twins. Fractional contributions k1, k2, k3, k4 of the twin
components were refined constraining k1 = 1 - k2 - k3 - k4.
An HKLF 5 format data file was created where each line contained
h,k,l, Fo^2, σ(Fo^2), m where m is the twin component number. Thus, four lines
of the data
file correspond to each measured reflection:
h,   k,   l,           Fo^2, σ(Fo^2),  -1
h,   -k, -h-l,       Fo^2, σ(Fo^2),  -2
-h,   k, -k-l,       Fo^2, σ(Fo^2),  -3
-h, -k,  h+k+l,  Fo^2, σ(Fo^2),   4
The volumes of the fourling domains refine to 55 : 9 : 20 : 16.
;
_reflns_number_total     8966
_reflns_number_gt     8202
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0478
_refine_ls_R_factor_gt     0.0432
_refine_ls_wR_factor_gt     0.1123
_refine_ls_wR_factor_ref     0.1150
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     8966
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0554P)²+0.2255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.341
_refine_diff_density_min     -0.358
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         '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'
    'O' 'O' 0.0106 0.0060
                         '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     ?
_computing_cell_refinement     ?
_computing_data_reduction     ?
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material     ?
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
    N11 0.3084(4) -0.06728(18) 0.89274(10) 0.0254(4) Uani d . 1 . . N
    N21 0.4387(4) -0.1449(2) 0.93397(11) 0.0264(4) Uani d . 1 . . N
    H21 0.3621 -0.1907 0.9586 0.037 Uiso calc R 1 . . H
    C31 0.7044(5) -0.1426(3) 0.93212(13) 0.0264(5) Uani d . 1 . . C
    O31 0.8741(3) -0.20130(18) 0.96269(9) 0.0356(4) Uani d . 1 . . O
    N41 0.7383(4) -0.0578(2) 0.88705(10) 0.0260(4) Uani d . 1 . . N
    H41 0.8842 -0.0346 0.8747 0.037 Uiso calc R 1 . . H
    C51 0.4949(5) -0.0188(2) 0.86632(11) 0.0236(5) Uani d . 1 . . C
    N51 0.4449(4) 0.0715(2) 0.81750(10) 0.0272(5) Uani d . 1 . . N
    O51 0.6354(4) 0.1093(2) 0.79429(11) 0.0372(5) Uani d . 1 . . O
    O61 0.2172(4) 0.1003(2) 0.80308(11) 0.0409(5) Uani d . 1 . . O
    N12 1.0939(4) 0.43300(19) 0.89177(10) 0.0272(4) Uani d . 1 . . N
    N22 1.0000(4) 0.3554(2) 0.93374(10) 0.0285(5) Uani d . 1 . . N
    H22 1.1004 0.3106 0.9588 0.037 Uiso calc R 1 . . H
    C32 0.7344(5) 0.3559(2) 0.93208(13) 0.0247(5) Uani d . 1 . . C
    O32 0.5925(4) 0.29716(17) 0.96306(9) 0.0349(4) Uani d . 1 . . O
    N42 0.6593(4) 0.4398(2) 0.88654(10) 0.0256(4) Uani d . 1 . . N
    H42 0.5014 0.4622 0.8741 0.037 Uiso calc R 1 . . H
    C52 0.8799(5) 0.4801(2) 0.86520(11) 0.0228(5) Uani d . 1 . . C
    N52 0.8821(4) 0.5705(2) 0.81713(11) 0.0266(4) Uani d . 1 . . N
    O52 0.6643(4) 0.6049(2) 0.79464(11) 0.0383(5) Uani d . 1 . . O
    O62 1.0904(4) 0.6061(2) 0.80328(12) 0.0443(5) Uani d . 1 . . O
    N13 -0.0965(4) 0.04197(19) 0.60938(10) 0.0262(4) Uani d . 1 . . N
    N23 -0.0007(4) -0.07541(19) 0.56712(11) 0.0263(4) Uani d . 1 . . N
    H23 -0.0993 -0.1459 0.5415 0.037 Uiso calc R 1 . . H
    C33 0.2647(5) -0.0701(2) 0.56948(13) 0.0251(5) Uani d . 1 . . C
    O33 0.4089(4) -0.15743(16) 0.53844(9) 0.0365(4) Uani d . 1 . . O
    N43 0.3376(4) 0.0603(2) 0.61626(11) 0.0258(4) Uani d . 1 . . N
    H43 0.4944 0.0968 0.6293 0.037 Uiso calc R 1 . . H
    C53 0.1129(4) 0.1182(2) 0.63718(12) 0.0211(4) Uani d . 1 . . C
    N53 0.1048(4) 0.2559(2) 0.68601(11) 0.0266(4) Uani d . 1 . . N
    O53 0.3155(4) 0.31856(19) 0.70961(11) 0.0388(5) Uani d . 1 . . O
    O63 -0.1129(4) 0.2971(2) 0.69924(11) 0.0422(5) Uani d . 1 . . O
    N14 0.7013(4) 0.53429(19) 0.60426(10) 0.0274(4) Uani d . 1 . . N
    N24 0.5640(4) 0.41422(19) 0.56377(11) 0.0259(4) Uani d . 1 . . N
    H24 0.6379 0.3433 0.5389 0.037 Uiso calc R 1 . . H
    C34 0.3013(5) 0.4189(2) 0.56700(13) 0.0269(5) Uani d . 1 . . C
    O34 0.1287(4) 0.33027(16) 0.53764(9) 0.0374(4) Uani d . 1 . . O
    N44 0.2754(4) 0.5511(2) 0.61176(11) 0.0262(4) Uani d . 1 . . N
    H44 0.1314 0.5879 0.6246 0.037 Uiso calc R 1 . . H
    C54 0.5181(5) 0.6103(2) 0.63109(12) 0.0248(5) Uani d . 1 . . C
    N54 0.5689(4) 0.7486(2) 0.67853(11) 0.0271(4) Uani d . 1 . . N
    O54 0.3796(4) 0.80735(19) 0.70440(11) 0.0392(5) Uani d . 1 . . O
    O64 0.7956(4) 0.7932(2) 0.68975(11) 0.0423(5) Uani d . 1 . . O
_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
    N11 C51 . 1.283(3) ?
    N11 N21 . 1.358(3) ?
    N21 C31 . 1.367(3) ?
    N21 H21 . 0.8600 ?
    C31 O31 . 1.220(3) ?
    C31 N41 . 1.377(3) ?
    N41 H41 . 0.8600 ?
    N41 C51 . 1.348(3) ?
    C51 N51 . 1.454(3) ?
    N51 O51 . 1.217(3) ?
    N51 O61 . 1.217(3) ?
    N12 C52 . 1.288(3) ?
    N12 N22 . 1.373(3) ?
    N22 C32 . 1.357(3) ?
    N22 H22 . 0.8600 ?
    C32 O32 . 1.228(3) ?
    C32 N42 . 1.374(3) ?
    N42 C52 . 1.343(3) ?
    N42 H42 . 0.8600 ?
    C52 N52 . 1.443(3) ?
    N52 O62 . 1.208(3) ?
    N52 O52 . 1.223(3) ?
    N13 C53 . 1.283(3) ?
    N13 N23 . 1.365(3) ?
    N23 C33 . 1.355(3) ?
    N23 H23 . 0.8600 ?
    C33 O33 . 1.223(3) ?
    C33 N43 . 1.386(3) ?
    N43 C53 . 1.348(3) ?
    N43 H43 . 0.8600 ?
    C53 N53 . 1.444(3) ?
    N53 O53 . 1.216(3) ?
    N53 O63 . 1.224(3) ?
    N14 C54 . 1.280(3) ?
    N14 N24 . 1.378(3) ?
    N24 C34 . 1.356(3) ?
    N24 H24 . 0.8600 ?
    C34 O34 . 1.220(3) ?
    C34 N44 . 1.389(3) ?
    N44 C54 . 1.341(3) ?
    N44 H44 . 0.8600 ?
    C54 N54 . 1.440(3) ?
    N54 O64 . 1.217(3) ?
    N54 O54 . 1.220(3) ?
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
    C51 N11 N21 . . 102.69(18) ?
    N11 N21 C31 . . 112.8(2) ?
    N11 N21 H21 . . 123.6 ?
    C31 N21 H21 . . 123.6 ?
    O31 C31 N21 . . 128.8(2) ?
    O31 C31 N41 . . 127.4(2) ?
    N21 C31 N41 . . 103.7(2) ?
    C51 N41 C31 . . 105.5(2) ?
    C51 N41 H41 . . 127.2 ?
    C31 N41 H41 . . 127.2 ?
    N11 C51 N41 . . 115.2(2) ?
    N11 C51 N51 . . 121.9(2) ?
    N41 C51 N51 . . 122.8(2) ?
    O51 N51 O61 . . 126.5(2) ?
    O51 N51 C51 . . 116.5(2) ?
    O61 N51 C51 . . 117.0(2) ?
    C52 N12 N22 . . 101.7(2) ?
    C32 N22 N12 . . 113.9(2) ?
    C32 N22 H22 . . 123.0 ?
    N12 N22 H22 . . 123.0 ?
    O32 C32 N22 . . 129.6(2) ?
    O32 C32 N42 . . 127.7(2) ?
    N22 C32 N42 . . 102.7(2) ?
    C52 N42 C32 . . 106.9(2) ?
    C52 N42 H42 . . 126.6 ?
    C32 N42 H42 . . 126.6 ?
    N12 C52 N42 . . 114.8(2) ?
    N12 C52 N52 . . 121.7(2) ?
    N42 C52 N52 . . 123.5(2) ?
    O62 N52 O52 . . 126.1(2) ?
    O62 N52 C52 . . 119.2(2) ?
    O52 N52 C52 . . 114.6(2) ?
    C53 N13 N23 . . 102.64(19) ?
    C33 N23 N13 . . 113.47(19) ?
    C33 N23 H23 . . 123.3 ?
    N13 N23 H23 . . 123.3 ?
    O33 C33 N23 . . 129.4(2) ?
    O33 C33 N43 . . 127.5(2) ?
    N23 C33 N43 . . 103.10(19) ?
    C53 N43 C33 . . 106.10(19) ?
    C53 N43 H43 . . 127.0 ?
    C33 N43 H43 . . 127.0 ?
    N13 C53 N43 . . 114.70(19) ?
    N13 C53 N53 . . 122.04(19) ?
    N43 C53 N53 . . 123.3(2) ?
    O53 N53 O63 . . 126.9(2) ?
    O53 N53 C53 . . 116.43(19) ?
    O63 N53 C53 . . 116.7(2) ?
    C54 N14 N24 . . 102.31(19) ?
    C34 N24 N14 . . 113.47(19) ?
    C34 N24 H24 . . 123.3 ?
    N14 N24 H24 . . 123.3 ?
    O34 C34 N24 . . 129.2(2) ?
    O34 C34 N44 . . 128.2(2) ?
    N24 C34 N44 . . 102.6(2) ?
    C54 N44 C34 . . 106.8(2) ?
    C54 N44 H44 . . 126.6 ?
    C34 N44 H44 . . 126.6 ?
    N14 C54 N44 . . 114.8(2) ?
    N14 C54 N54 . . 122.6(2) ?
    N44 C54 N54 . . 122.6(2) ?
    O64 N54 O54 . . 127.2(2) ?
    O64 N54 C54 . . 116.8(2) ?
    O54 N54 C54 . . 116.0(2) ?
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
    N21 H21 O32 2_657 0.86 2.01 2.769(2) 146.5
    N21 H21 O31 1_455 0.86 2.51 3.089(3) 125.0
    N41 H41 N11 1_655 0.86 2.20 2.912(3) 140.6
    N22 H22 O31 2_757 0.86 2.04 2.791(3) 146.1
    N22 H22 O32 1_655 0.86 2.52 3.100(3) 125.8
    N42 H42 N12 1_455 0.86 2.19 2.913(3) 141.9
    N23 H23 O34 2_556 0.86 2.01 2.778(2) 147.4
    N23 H23 O33 1_455 0.86 2.51 3.073(3) 123.4
    N43 H43 N13 1_655 0.86 2.22 2.923(3) 138.7
    N24 H24 O33 2_656 0.86 2.01 2.776(2) 147.4
    N24 H24 O34 1_655 0.86 2.52 3.081(3) 123.5
    N44 H44 N14 1_455 0.86 2.23 2.928(3) 138.8
data_global
_journal_date_recd_electronic     2005-05-02
_journal_date_accepted     2005-07-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2005
_journal_volume     61
_journal_issue      5
_journal_page_first     577
_journal_page_last     584
_journal_paper_category     FA
_journal_coeditor_code     SN5022
_publ_contact_author
;
        A. Alan Pinkerton
;
_publ_contact_author_email     apinker@uoft02.utoledo.edu
_publ_contact_author_fax     '419-5301533'
_publ_contact_author_phone     '419-5304580'
_publ_section_title
;
;
loop_
    _publ_author_name
    _publ_author_address
    'Bolotina, Nadezhda B.'
;  Department of Chemistry
 University of Toledo
      Toledo, Ohio 43606-3390 USA
;
    'Kirschbaum, Kristin'
;       Department of Chemistry
        University of Toledo
        Toledo, Ohio 43606-3390 USA
;
    'Pinkerton, A.Alan'
;       Department of Chemistry
        University of Toledo
        Toledo, Ohio 43606-3390 USA
;
