##############################################################################
#                                                                            #
# 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_glyg00
_audit_creation_method     CRYSTALS_ver_12.82
_journal_date_recd_electronic     2005-11-14
_journal_date_accepted     2005-12-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     310
_journal_page_last     320
_journal_paper_category     FA
_journal_coeditor_code     GP5004
_publ_contact_author_name     'Stephen A. Moggach'
_chemical_name_systematic     ?
_chemical_formula_moiety     'C4 H8 N2 O3'
_chemical_formula_sum     'C4 H8 N2 O3'
_chemical_formula_weight     132.12
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 1 21/c 1 '
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     8.1233(18)
_cell_length_b     9.554(2)
_cell_length_c     7.8224(17)
_cell_angle_alpha     90
_cell_angle_beta     107.596(4)
_cell_angle_gamma     90
_cell_volume     578.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1501
_cell_measurement_theta_min     5
_cell_measurement_theta_max     56
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.516
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.130
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min     0.86
_exptl_absorpt_correction_T_max     0.98
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEX'
_diffrn_measurement_method     ω
_diffrn_reflns_number     3696
_diffrn_reflns_av_R_equivalents     0.027
_diffrn_reflns_theta_min     2.630
_diffrn_reflns_theta_max     28.669
_diffrn_reflns_theta_full     26.662
_diffrn_measured_fraction_theta_max     0.932
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     1390
_reflns_number_gt     1164
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0570
_refine_ls_R_factor_gt     0.0488
_refine_ls_wR_factor_all     0.1399
_refine_ls_wR_factor_gt     0.1357
_refine_ls_wR_factor_ref     0.1399
_refine_ls_goodness_of_fit_ref     1.0108
_refine_ls_number_reflns     1385
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 w=1/[σ²(F²) + ( 0.08P)² + 0.11P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'Kvick et al., (1979) '
_refine_ls_shift/su_max     0.000206
_refine_diff_density_max     0.28
_refine_diff_density_min     -0.35
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.51455(19) 0.32926(16) 0.2567(2) 0.0224 Uani 1.0000 . .
    N N2 0.38281(17) 0.40729(13) 0.16383(18) 0.0257 Uani 1.0000 . .
    C C3 0.2336(2) 0.34438(17) 0.0343(2) 0.0315 Uani 1.0000 . .
    C C4 0.13810(19) 0.44681(17) -0.11059(19) 0.0226 Uani 1.0000 . .
    O O2 0.17806(16) 0.57319(12) -0.09166(15) 0.0307 Uani 1.0000 . .
    O O3 0.02560(18) 0.39389(16) -0.23924(17) 0.0439 Uani 1.0000 . .
    C C1 0.6569(2) 0.40541(16) 0.3969(2) 0.0244 Uani 1.0000 . .
    N N1 0.82202(16) 0.33096(13) 0.42373(17) 0.0233 Uani 1.0000 . .
    O O1 0.52170(16) 0.20188(12) 0.23929(17) 0.0352 Uani 1.0000 . .
    H H2 0.9065 0.3761 0.5069 0.0259 Uiso 1.0000 . .
    H H1 0.8476 0.3283 0.3196 0.0259 Uiso 1.0000 . .
    H H3 0.8126 0.2431 0.4611 0.0259 Uiso 1.0000 . .
    H H4 0.6673 0.5031 0.3554 0.0274 Uiso 1.0000 . .
    H H5 0.6284 0.4083 0.5126 0.0274 Uiso 1.0000 . .
    H H6 0.3858 0.5005 0.1812 0.0276 Uiso 1.0000 . .
    H H7 0.2735 0.2634 -0.0240 0.0332 Uiso 1.0000 . .
    H H8 0.1524 0.3103 0.0990 0.0332 Uiso 1.0000 . .
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
    C2 0.0237(7) 0.0195(7) 0.0207(7) -0.0007(5) 0.0016(6) 0.0019(5)
    N2 0.0248(7) 0.0171(6) 0.0271(7) 0.0004(5) -0.0044(5) -0.0007(5)
    C3 0.0276(8) 0.0222(8) 0.0333(9) -0.0048(6) -0.0080(6) 0.0035(6)
    C4 0.0230(7) 0.0248(7) 0.0179(7) 0.0009(5) 0.0030(5) -0.0012(5)
    O2 0.0412(7) 0.0229(6) 0.0232(6) 0.0017(5) 0.0028(5) 0.0014(4)
    O3 0.0439(8) 0.0443(8) 0.0284(7) -0.0070(6) -0.0115(6) -0.0041(5)
    C1 0.0254(7) 0.0221(7) 0.0211(7) 0.0025(5) 0.0001(6) -0.0023(5)
    N1 0.0222(6) 0.0214(6) 0.0210(6) -0.0005(5) -0.0015(5) 0.0013(5)
    O1 0.0340(7) 0.0177(6) 0.0418(7) 0.0017(4) -0.0066(5) 0.0006(5)
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
    C2 N2 . . 1.3263(19) yes
    C2 C1 . . 1.517(2) yes
    C2 O1 . . 1.2280(19) yes
    N2 C3 . . 1.4540(19) yes
    N2 H6 . . 0.900 no
    C3 C4 . . 1.521(2) yes
    C3 H7 . . 1.000 no
    C3 H8 . . 1.000 no
    C4 O2 . . 1.2474(19) yes
    C4 O3 . . 1.2440(19) yes
    C1 N1 . . 1.4763(19) yes
    C1 H4 . . 1.000 no
    C1 H5 . . 1.000 no
    N1 H2 . . 0.900 no
    N1 H1 . . 0.900 no
    N1 H3 . . 0.900 no
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 C2 C1 . . . 116.03(13) yes
    N2 C2 O1 . . . 123.62(14) yes
    C1 C2 O1 . . . 120.28(13) yes
    C2 N2 C3 . . . 120.93(13) yes
    C2 N2 H6 . . . 119.5 no
    C3 N2 H6 . . . 119.5 no
    N2 C3 C4 . . . 112.54(13) yes
    N2 C3 H7 . . . 108.7 no
    C4 C3 H7 . . . 108.7 no
    N2 C3 H8 . . . 108.7 no
    C4 C3 H8 . . . 108.7 no
    H7 C3 H8 . . . 109.5 no
    C3 C4 O2 . . . 118.59(13) yes
    C3 C4 O3 . . . 115.21(14) yes
    O2 C4 O3 . . . 126.20(15) yes
    C2 C1 N1 . . . 109.45(12) yes
    C2 C1 H4 . . . 109.5 no
    N1 C1 H4 . . . 109.5 no
    C2 C1 H5 . . . 109.5 no
    N1 C1 H5 . . . 109.5 no
    H4 C1 H5 . . . 109.5 no
    C1 N1 H2 . . . 109.5 no
    C1 N1 H1 . . . 109.5 no
    H2 N1 H1 . . . 109.5 no
    C1 N1 H3 . . . 109.5 no
    H2 N1 H3 . . . 109.5 no
    H1 N1 H3 . . . 109.5 no
data_glyg14
_audit_creation_method     CRYSTALS_ver_12.82
_journal_date_recd_electronic     2005-11-14
_journal_date_accepted     2005-12-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     310
_journal_page_last     320
_journal_paper_category     FA
_journal_coeditor_code     GP5004
_publ_contact_author_name     'Stephen A. Moggach'
_chemical_name_systematic     ?
_chemical_formula_moiety     'C4 H8 N2 O3'
_chemical_formula_sum     'C4 H8 N2 O3'
_chemical_formula_weight     132.12
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 1 21/c 1 '
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     7.6428(3)
_cell_length_b     9.3800(4)
_cell_length_c     7.6505(5)
_cell_angle_alpha     90
_cell_angle_beta     103.882(4)
_cell_angle_gamma     90
_cell_volume     532.44(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1234
_cell_measurement_theta_min     5
_cell_measurement_theta_max     52
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.648
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.141
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min     0.85
_exptl_absorpt_correction_T_max     0.99
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEX II'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2911
_diffrn_reflns_av_R_equivalents     0.052
_diffrn_reflns_theta_min     2.745
_diffrn_reflns_theta_max     27.189
_diffrn_reflns_theta_full     25.014
_diffrn_measured_fraction_theta_max     0.400
_diffrn_measured_fraction_theta_full     0.454
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     471
_reflns_number_gt     360
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0932
_refine_ls_R_factor_gt     0.0764
_refine_ls_wR_factor_all     0.1981
_refine_ls_wR_factor_gt     0.1839
_refine_ls_wR_factor_ref     0.1981
_refine_ls_goodness_of_fit_ref     1.0501
_refine_ls_number_reflns     455
_refine_ls_number_parameters     37
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 w=1/[σ²(F²) + ( 0.08P)² + 2.28P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'Kvick et al., (1979) '
_refine_ls_shift/su_max     0.000031
_refine_diff_density_max     0.40
_refine_diff_density_min     -0.38
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.5163(6) 0.3329(5) 0.2639(10) 0.0180(12) Uiso 1.0000 . .
    N N2 0.3837(5) 0.4101(4) 0.1660(9) 0.0206(12) Uiso 1.0000 . .
    C C3 0.2365(7) 0.3412(5) 0.0389(11) 0.0225(13) Uiso 1.0000 . .
    C C4 0.1398(6) 0.4440(5) -0.1066(9) 0.0191(13) Uiso 1.0000 . .
    O O2 0.1754(5) 0.5737(4) -0.0883(8) 0.0278(11) Uiso 1.0000 . .
    O O3 0.0287(5) 0.3884(4) -0.2360(8) 0.0360(13) Uiso 1.0000 . .
    C C1 0.6572(7) 0.4119(5) 0.4032(11) 0.0216(14) Uiso 1.0000 . .
    N N1 0.8326(5) 0.3369(4) 0.4307(9) 0.0217(12) Uiso 1.0000 . .
    O O1 0.5253(5) 0.2024(4) 0.2519(8) 0.0292(12) Uiso 1.0000 . .
    H H2 0.9161 0.3841 0.5133 0.0263 Uiso 1.0000 . .
    H H1 0.8667 0.3330 0.3262 0.0263 Uiso 1.0000 . .
    H H3 0.8210 0.2476 0.4701 0.0263 Uiso 1.0000 . .
    H H4 0.6699 0.5110 0.3587 0.0258 Uiso 1.0000 . .
    H H5 0.6190 0.4161 0.5185 0.0258 Uiso 1.0000 . .
    H H6 0.3849 0.5054 0.1782 0.0245 Uiso 1.0000 . .
    H H7 0.2858 0.2603 -0.0198 0.0267 Uiso 1.0000 . .
    H H8 0.1484 0.3040 0.1052 0.0267 Uiso 1.0000 . .
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
    C2 N2 . . 1.322(7) yes
    C2 C1 . . 1.515(8) yes
    C2 O1 . . 1.231(6) yes
    N2 C3 . . 1.450(8) yes
    N2 H6 . . 0.898 no
    C3 C4 . . 1.524(9) yes
    C3 H7 . . 1.000 no
    C3 H8 . . 0.998 no
    C4 O2 . . 1.247(6) yes
    C4 O3 . . 1.253(8) yes
    C1 N1 . . 1.483(6) yes
    C1 H4 . . 1.003 no
    C1 H5 . . 0.994 no
    N1 H2 . . 0.899 no
    N1 H1 . . 0.899 no
    N1 H3 . . 0.902 no
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 C2 C1 . . . 116.7(4) yes
    N2 C2 O1 . . . 123.5(5) yes
    C1 C2 O1 . . . 119.8(4) yes
    C2 N2 C3 . . . 120.1(4) yes
    C2 N2 H6 . . . 119.9 no
    C3 N2 H6 . . . 120.0 no
    N2 C3 C4 . . . 111.7(4) yes
    N2 C3 H7 . . . 108.9 no
    C4 C3 H7 . . . 108.7 no
    N2 C3 H8 . . . 109.0 no
    C4 C3 H8 . . . 108.9 no
    H7 C3 H8 . . . 109.6 no
    C3 C4 O2 . . . 118.7(5) yes
    C3 C4 O3 . . . 115.6(4) yes
    O2 C4 O3 . . . 125.7(5) yes
    C2 C1 N1 . . . 109.5(4) yes
    C2 C1 H4 . . . 109.0 no
    N1 C1 H4 . . . 109.3 no
    C2 C1 H5 . . . 109.5 no
    N1 C1 H5 . . . 109.9 no
    H4 C1 H5 . . . 109.7 no
    C1 N1 H2 . . . 109.4 no
    C1 N1 H1 . . . 109.8 no
    H2 N1 H1 . . . 109.6 no
    C1 N1 H3 . . . 109.3 no
    H2 N1 H3 . . . 109.4 no
    H1 N1 H3 . . . 109.4 no
data_glyg30
_audit_creation_method     CRYSTALS_ver_12.82
_journal_date_recd_electronic     2005-11-14
_journal_date_accepted     2005-12-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     310
_journal_page_last     320
_journal_paper_category     FA
_journal_coeditor_code     GP5004
_publ_contact_author_name     'Stephen A. Moggach'
_chemical_name_systematic     ?
_chemical_formula_moiety     'C4 H8 N2 O3'
_chemical_formula_sum     'C4 H8 N2 O3'
_chemical_formula_weight     132.12
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 1 21/c 1 '
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     7.4304(4)
_cell_length_b     9.2896(7)
_cell_length_c     7.5943(9)
_cell_angle_alpha     90
_cell_angle_beta     102.465(7)
_cell_angle_gamma     90
_cell_volume     511.84(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1235
_cell_measurement_theta_min     6
_cell_measurement_theta_max     53
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.714
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.147
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min     0.86
_exptl_absorpt_correction_T_max     0.99
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEX II'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2733
_diffrn_reflns_av_R_equivalents     0.048
_diffrn_reflns_theta_min     2.807
_diffrn_reflns_theta_max     26.833
_diffrn_reflns_theta_full     25.223
_diffrn_measured_fraction_theta_max     0.410
_diffrn_measured_fraction_theta_full     0.452
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     451
_reflns_number_gt     348
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0907
_refine_ls_R_factor_gt     0.0745
_refine_ls_wR_factor_all     0.1891
_refine_ls_wR_factor_gt     0.1748
_refine_ls_wR_factor_ref     0.1891
_refine_ls_goodness_of_fit_ref     1.0349
_refine_ls_number_reflns     434
_refine_ls_number_parameters     37
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 w=1/[σ²(F²) + ( 0.08P)² + 1.99P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'Kvick et al., (1979) '
_refine_ls_shift/su_max     0.000042
_refine_diff_density_max     0.38
_refine_diff_density_min     -0.35
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.5186(6) 0.3349(5) 0.2671(9) 0.0183(12) Uiso 1.0000 . .
    N N2 0.3838(5) 0.4116(4) 0.1676(8) 0.0193(11) Uiso 1.0000 . .
    C C3 0.2380(6) 0.3406(5) 0.0406(10) 0.0216(13) Uiso 1.0000 . .
    C C4 0.1405(6) 0.4433(5) -0.1046(9) 0.0172(12) Uiso 1.0000 . .
    O O2 0.1757(5) 0.5747(4) -0.0868(7) 0.0266(11) Uiso 1.0000 . .
    O O3 0.0294(5) 0.3870(4) -0.2341(8) 0.0331(12) Uiso 1.0000 . .
    C C1 0.6579(6) 0.4149(5) 0.4052(10) 0.0206(13) Uiso 1.0000 . .
    N N1 0.8378(5) 0.3392(4) 0.4331(8) 0.0225(12) Uiso 1.0000 . .
    O O1 0.5283(5) 0.2027(4) 0.2550(7) 0.0279(11) Uiso 1.0000 . .
    H H2 0.9216 0.3867 0.5157 0.0273 Uiso 1.0000 . .
    H H1 0.8757 0.3347 0.3286 0.0273 Uiso 1.0000 . .
    H H3 0.8248 0.2489 0.4730 0.0273 Uiso 1.0000 . .
    H H4 0.6720 0.5148 0.3601 0.0250 Uiso 1.0000 . .
    H H5 0.6154 0.4195 0.5205 0.0250 Uiso 1.0000 . .
    H H6 0.3830 0.5076 0.1801 0.0227 Uiso 1.0000 . .
    H H7 0.2921 0.2603 -0.0189 0.0255 Uiso 1.0000 . .
    H H8 0.1461 0.3014 0.1060 0.0255 Uiso 1.0000 . .
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
    C2 N2 . . 1.325(7) yes
    C2 C1 . . 1.501(7) yes
    C2 O1 . . 1.235(5) yes
    N2 C3 . . 1.445(7) yes
    N2 H6 . . 0.898 no
    C3 C4 . . 1.518(8) yes
    C3 H7 . . 1.001 no
    C3 H8 . . 0.996 no
    C4 O2 . . 1.250(5) yes
    C4 O3 . . 1.254(7) yes
    C1 N1 . . 1.484(6) yes
    C1 H4 . . 1.003 no
    C1 H5 . . 0.994 no
    N1 H2 . . 0.898 no
    N1 H1 . . 0.899 no
    N1 H3 . . 0.903 no
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 C2 C1 . . . 117.1(4) yes
    N2 C2 O1 . . . 122.7(4) yes
    C1 C2 O1 . . . 120.1(4) yes
    C2 N2 C3 . . . 120.1(4) yes
    C2 N2 H6 . . . 119.7 no
    C3 N2 H6 . . . 120.2 no
    N2 C3 C4 . . . 111.7(4) yes
    N2 C3 H7 . . . 108.9 no
    C4 C3 H7 . . . 108.4 no
    N2 C3 H8 . . . 109.3 no
    C4 C3 H8 . . . 108.7 no
    H7 C3 H8 . . . 109.7 no
    C3 C4 O2 . . . 118.6(5) yes
    C3 C4 O3 . . . 115.9(4) yes
    O2 C4 O3 . . . 125.4(5) yes
    C2 C1 N1 . . . 109.2(4) yes
    C2 C1 H4 . . . 109.0 no
    N1 C1 H4 . . . 109.3 no
    C2 C1 H5 . . . 109.6 no
    N1 C1 H5 . . . 110.0 no
    H4 C1 H5 . . . 109.7 no
    C1 N1 H2 . . . 109.5 no
    C1 N1 H1 . . . 109.9 no
    H2 N1 H1 . . . 109.7 no
    C1 N1 H3 . . . 109.2 no
    H2 N1 H3 . . . 109.3 no
    H1 N1 H3 . . . 109.3 no
data_glyg37
_audit_creation_method     CRYSTALS_ver_12.82
_journal_date_recd_electronic     2005-11-14
_journal_date_accepted     2005-12-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     310
_journal_page_last     320
_journal_paper_category     FA
_journal_coeditor_code     GP5004
_publ_contact_author_name     'Stephen A. Moggach'
_chemical_name_systematic     ?
_chemical_formula_moiety     'C4 H8 N2 O3'
_chemical_formula_sum     'C4 H8 N2 O3'
_chemical_formula_weight     132.12
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 1 21/c 1 '
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     7.3100(15)
_cell_length_b     9.232(2)
_cell_length_c     7.550(3)
_cell_angle_alpha     90
_cell_angle_beta     101.51(3)
_cell_angle_gamma     90
_cell_volume     499.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1211
_cell_measurement_theta_min     6
_cell_measurement_theta_max     53
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.758
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.150
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min     0.84
_exptl_absorpt_correction_T_max     0.99
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEX II'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2678
_diffrn_reflns_av_R_equivalents     0.048
_diffrn_reflns_theta_min     2.844
_diffrn_reflns_theta_max     26.908
_diffrn_reflns_theta_full     25.024
_diffrn_measured_fraction_theta_max     0.403
_diffrn_measured_fraction_theta_full     0.458
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     435
_reflns_number_gt     332
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0837
_refine_ls_R_factor_gt     0.0677
_refine_ls_wR_factor_all     0.1628
_refine_ls_wR_factor_gt     0.1503
_refine_ls_wR_factor_ref     0.1628
_refine_ls_goodness_of_fit_ref     1.0429
_refine_ls_number_reflns     419
_refine_ls_number_parameters     37
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 w=1/[σ²(F²) + ( 0.05P)² + 2.18P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'Kvick et al., (1979) '
_refine_ls_shift/su_max     0.000042
_refine_diff_density_max     0.31
_refine_diff_density_min     -0.30
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.5201(6) 0.3365(5) 0.2673(9) 0.0185(12) Uiso 1.0000 . .
    N N2 0.3840(5) 0.4127(4) 0.1685(8) 0.0180(11) Uiso 1.0000 . .
    C C3 0.2390(6) 0.3411(5) 0.0401(10) 0.0197(12) Uiso 1.0000 . .
    C C4 0.1420(6) 0.4432(5) -0.1037(9) 0.0163(12) Uiso 1.0000 . .
    O O2 0.1770(5) 0.5760(4) -0.0861(7) 0.0259(10) Uiso 1.0000 . .
    O O3 0.0294(5) 0.3866(4) -0.2322(8) 0.0300(11) Uiso 1.0000 . .
    C C1 0.6588(6) 0.4168(5) 0.4061(10) 0.0198(13) Uiso 1.0000 . .
    N N1 0.8408(5) 0.3403(4) 0.4349(8) 0.0202(11) Uiso 1.0000 . .
    O O1 0.5306(5) 0.2029(4) 0.2570(7) 0.0266(11) Uiso 1.0000 . .
    H H2 0.9246 0.3881 0.5179 0.0249 Uiso 1.0000 . .
    H H1 0.8820 0.3357 0.3303 0.0249 Uiso 1.0000 . .
    H H3 0.8266 0.2496 0.4748 0.0249 Uiso 1.0000 . .
    H H4 0.6746 0.5174 0.3609 0.0242 Uiso 1.0000 . .
    H H5 0.6131 0.4217 0.5213 0.0242 Uiso 1.0000 . .
    H H6 0.3812 0.5091 0.1821 0.0210 Uiso 1.0000 . .
    H H7 0.2966 0.2614 -0.0201 0.0228 Uiso 1.0000 . .
    H H8 0.1450 0.3003 0.1049 0.0228 Uiso 1.0000 . .
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
    C2 N2 . . 1.321(7) yes
    C2 C1 . . 1.501(8) yes
    C2 O1 . . 1.239(5) yes
    N2 C3 . . 1.446(7) yes
    N2 H6 . . 0.897 no
    C3 C4 . . 1.504(8) yes
    C3 H7 . . 1.001 no
    C3 H8 . . 0.994 no
    C4 O2 . . 1.253(5) yes
    C4 O3 . . 1.255(7) yes
    C1 N1 . . 1.484(6) yes
    C1 H4 . . 1.004 no
    C1 H5 . . 0.993 no
    N1 H2 . . 0.899 no
    N1 H1 . . 0.900 no
    N1 H3 . . 0.903 no
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 C2 C1 . . . 117.3(4) yes
    N2 C2 O1 . . . 122.9(4) yes
    C1 C2 O1 . . . 119.6(4) yes
    C2 N2 C3 . . . 120.3(4) yes
    C2 N2 H6 . . . 119.7 no
    C3 N2 H6 . . . 120.0 no
    N2 C3 C4 . . . 112.0(4) yes
    N2 C3 H7 . . . 108.8 no
    C4 C3 H7 . . . 108.3 no
    N2 C3 H8 . . . 109.2 no
    C4 C3 H8 . . . 108.7 no
    H7 C3 H8 . . . 109.9 no
    C3 C4 O2 . . . 118.7(5) yes
    C3 C4 O3 . . . 116.0(4) yes
    O2 C4 O3 . . . 125.3(5) yes
    C2 C1 N1 . . . 109.2(4) yes
    C2 C1 H4 . . . 109.1 no
    N1 C1 H4 . . . 109.2 no
    C2 C1 H5 . . . 109.6 no
    N1 C1 H5 . . . 110.0 no
    H4 C1 H5 . . . 109.7 no
    C1 N1 H2 . . . 109.6 no
    C1 N1 H1 . . . 109.9 no
    H2 N1 H1 . . . 109.5 no
    C1 N1 H3 . . . 109.3 no
    H2 N1 H3 . . . 109.3 no
    H1 N1 H3 . . . 109.2 no
data_glyg47
_audit_creation_method     CRYSTALS_ver_12.82
_journal_date_recd_electronic     2005-11-14
_journal_date_accepted     2005-12-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     310
_journal_page_last     320
_journal_paper_category     FA
_journal_coeditor_code     GP5004
_publ_contact_author_name     'Stephen A. Moggach'
_chemical_name_systematic     ?
_chemical_formula_moiety     'C4 H8 N2 O3'
_chemical_formula_sum     'C4 H8 N2 O3'
_chemical_formula_weight     132.12
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 1 21/c 1 '
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x,y+1/2,-z+1/2'
    'x,-y+1/2,z+1/2'
_cell_length_a     7.2437(8)
_cell_length_b     9.2083(13)
_cell_length_c     7.5328(17)
_cell_angle_alpha     90
_cell_angle_beta     101.214(14)
_cell_angle_gamma     90
_cell_volume     492.86(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1070
_cell_measurement_theta_min     6
_cell_measurement_theta_max     52
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.780
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.152
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min     0.75
_exptl_absorpt_correction_T_max     0.98
_diffrn_ambient_temperature     293
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEX II'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2669
_diffrn_reflns_av_R_equivalents     0.052
_diffrn_reflns_theta_min     2.867
_diffrn_reflns_theta_max     27.164
_diffrn_reflns_theta_full     25.262
_diffrn_measured_fraction_theta_max     0.401
_diffrn_measured_fraction_theta_full     0.458
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     437
_reflns_number_gt     318
_reflns_threshold_expression     I>2.00u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0919
_refine_ls_R_factor_gt     0.0719
_refine_ls_wR_factor_all     0.1874
_refine_ls_wR_factor_gt     0.1692
_refine_ls_wR_factor_ref     0.1874
_refine_ls_goodness_of_fit_ref     1.0294
_refine_ls_number_reflns     422
_refine_ls_number_parameters     37
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 w=1/[σ²(F²) + ( 0.08P)² + 2.23P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'Kvick et al., (1979)'
_refine_ls_shift/su_max     0.000038
_refine_diff_density_max     0.35
_refine_diff_density_min     -0.33
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1993)'
_computing_cell_refinement     'SAINT (Siemens ,1995)'
_computing_data_reduction     'SAINT (Siemens ,1995)'
_computing_structure_solution     'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.5214(6) 0.3376(5) 0.2692(10) 0.0177(13) Uiso 1.0000 . .
    N N2 0.3849(6) 0.4133(4) 0.1709(9) 0.0181(12) Uiso 1.0000 . .
    C C3 0.2395(7) 0.3405(5) 0.0407(11) 0.0195(13) Uiso 1.0000 . .
    C C4 0.1426(6) 0.4434(5) -0.1027(10) 0.0183(13) Uiso 1.0000 . .
    O O2 0.1782(5) 0.5760(4) -0.0852(8) 0.0252(11) Uiso 1.0000 . .
    O O3 0.0300(5) 0.3862(4) -0.2332(8) 0.0301(12) Uiso 1.0000 . .
    C C1 0.6607(7) 0.4177(5) 0.4085(11) 0.0198(14) Uiso 1.0000 . .
    N N1 0.8432(6) 0.3422(5) 0.4362(9) 0.0203(12) Uiso 1.0000 . .
    O O1 0.5317(5) 0.2038(4) 0.2573(8) 0.0262(12) Uiso 1.0000 . .
    H H2 0.9270 0.3901 0.5197 0.0244 Uiso 1.0000 . .
    H H1 0.8846 0.3395 0.3310 0.0244 Uiso 1.0000 . .
    H H3 0.8294 0.2510 0.4746 0.0244 Uiso 1.0000 . .
    H H4 0.6758 0.5190 0.3657 0.0237 Uiso 1.0000 . .
    H H5 0.6145 0.4207 0.5252 0.0237 Uiso 1.0000 . .
    H H6 0.3814 0.5103 0.1842 0.0217 Uiso 1.0000 . .
    H H7 0.2985 0.2604 -0.0187 0.0235 Uiso 1.0000 . .
    H H8 0.1440 0.2988 0.1059 0.0235 Uiso 1.0000 . .
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
    C2 N2 . . 1.314(7) yes
    C2 C1 . . 1.501(8) yes
    C2 O1 . . 1.239(6) yes
    N2 C3 . . 1.456(8) yes
    N2 H6 . . 0.900 no
    C3 C4 . . 1.504(9) yes
    C3 H7 . . 1.000 no
    C3 H8 . . 1.000 no
    C4 O2 . . 1.250(6) yes
    C4 O3 . . 1.264(8) yes
    C1 N1 . . 1.472(6) yes
    C1 H4 . . 1.000 no
    C1 H5 . . 1.000 no
    N1 H2 . . 0.900 no
    N1 H1 . . 0.900 no
    N1 H3 . . 0.900 no
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 C2 C1 . . . 117.6(4) yes
    N2 C2 O1 . . . 122.4(5) yes
    C1 C2 O1 . . . 119.8(4) yes
    C2 N2 C3 . . . 120.1(4) yes
    C2 N2 H6 . . . 119.9 no
    C3 N2 H6 . . . 120.0 no
    N2 C3 C4 . . . 111.7(4) yes
    N2 C3 H7 . . . 108.9 no
    C4 C3 H7 . . . 108.9 no
    N2 C3 H8 . . . 108.9 no
    C4 C3 H8 . . . 108.9 no
    H7 C3 H8 . . . 109.5 no
    C3 C4 O2 . . . 118.8(5) yes
    C3 C4 O3 . . . 115.9(4) yes
    O2 C4 O3 . . . 125.3(5) yes
    C2 C1 N1 . . . 109.3(4) yes
    C2 C1 H4 . . . 109.5 no
    N1 C1 H4 . . . 109.5 no
    C2 C1 H5 . . . 109.5 no
    N1 C1 H5 . . . 109.5 no
    H4 C1 H5 . . . 109.5 no
    C1 N1 H2 . . . 109.5 no
    C1 N1 H1 . . . 109.5 no
    H2 N1 H1 . . . 109.5 no
    C1 N1 H3 . . . 109.5 no
    H2 N1 H3 . . . 109.5 no
    H1 N1 H3 . . . 109.5 no
