#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:42:22 +0100 (dom 17 de nov de 2019) $
#$Revision: 230573 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/68/7056845.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7056845
loop_
_publ_author_name
'Kumar, A. Sudheer'
'Sasidharan, Nimesh'
'Ganguly, Rakesh'
'Leow, Dasheng'
'Hng, Huey Hoon'
_publ_section_title
;
 3-Amino-1,2,4(4H)-oxadiazol-5-one (AOD) and its nitrogen-rich salts: a
 class of insensitive energetic materials
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1840
_journal_paper_doi               10.1039/C7NJ03950F
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C2 H3 N3 O2'
_chemical_formula_sum            'C2 H3 N3 O2'
_chemical_formula_weight         101.07
_chemical_melting_point          231
_chemical_name_common            3-amino-1,2,4-oxadiazol-5-one
_chemical_name_systematic        'amino oxadiazolone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2017-11-29 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.139(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3860(16)
_cell_length_b                   3.5384(6)
_cell_length_c                   12.154(2)
_cell_measurement_reflns_used    1099
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      31.3745
_cell_measurement_theta_min      3.5487
_cell_volume                     381.34(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2638
_diffrn_reflns_theta_full        31.43
_diffrn_reflns_theta_max         31.43
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             208
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/Ethanol'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         1157
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                1072
_reflns_number_total             1157
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj03950f2.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2018-03-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 7056845--7056848.cif.
;
_cod_original_cell_volume        381.34(12)
_cod_original_formula_sum        'C4 H6 N6 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     202.15
_cod_database_code               7056845
_shelx_res_file
;
TITL ahg6s in Cc
CELL 0.71073   9.38600   3.53840  12.15410  90.0000 109.1391  90.0000
ZERR    2.00   0.00160   0.00060   0.00220   0.0000   0.0057   0.0000
LATT -7
SYMM X, -Y, 0.5+Z
SFAC C  H  N  O
UNIT 8  12  12  8
MERG 2
L.S. 4
ACTA
BOND
FMAP 2
PLAN 5
sadi n2 h1n n2 h2n
SIZE 0.10 0.12 0.40
TEMP -170
WGHT    0.033000
FVAR       0.40783
MOLE 1
C1    1    0.113321    0.961073   -0.013045    11.00000    0.00794    0.01180 =
         0.01219   -0.00202    0.00322   -0.00189
C2    1    0.213133    0.706999    0.160922    11.00000    0.00964    0.01137 =
         0.01076   -0.00052    0.00215    0.00124
N1    3    0.086488    0.878215    0.087291    11.00000    0.00714    0.01474 =
         0.01048    0.00088    0.00283    0.00206
AFIX  43
H1    2    0.002809    0.925732    0.102490    11.00000   -1.50000
AFIX   0
N2    3    0.221511    0.578291    0.266713    11.00000    0.01210    0.01895 =
         0.01181    0.00075    0.00444    0.00369
H1N   2    0.305888    0.493968    0.314213    11.00000   -1.50000
H2N   2    0.163066    0.677266    0.299829    11.00000   -1.50000
N3    3    0.318238    0.666055    0.112560    11.00000    0.01051    0.02037 =
         0.01012    0.00224    0.00220    0.00424
O1    4    0.033655    1.125080   -0.099939    11.00000    0.00964    0.01896 =
         0.01346    0.00333    0.00182    0.00066
O2    4    0.252527    0.831113   -0.002259    11.00000    0.00979    0.01876 =
         0.01103    0.00240    0.00425    0.00238
HKLF 4

REM  ahg6s in Cc
REM R1 =  0.0388 for    1072 Fo > 4sig(Fo)  and  0.0417 for all    1157 data
REM     70 parameters refined using      3 restraints

END

WGHT      0.0330      0.0000

REM Highest difference peak  0.270,  deepest hole -0.262,  1-sigma level  0.059
Q1    1  -0.0522  1.2027 -0.1035  11.00000  0.05    0.27
Q2    1   0.2038  0.9809 -0.0029  11.00000  0.05    0.26
Q3    1   0.1828  0.8691 -0.0067  11.00000  0.05    0.25
Q4    1   0.1395  0.5526  0.2617  11.00000  0.05    0.23
Q5    1   0.3693  0.4902  0.1199  11.00000  0.05    0.23
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.1133(2) 0.9611(6) -0.01304(19) 0.0107(4) Uani d . . 1
C C2 0.2131(2) 0.7070(6) 0.16092(19) 0.0109(4) Uani d . . 1
N N1 0.0865(2) 0.8782(5) 0.08729(17) 0.0108(4) Uani d . . 1
H H1 0.0028 0.9257 0.1025 0.016 Uiso calc U R 1
N N2 0.2215(2) 0.5783(6) 0.26671(17) 0.0142(4) Uani d . D 1
H H1N 0.306(3) 0.494(8) 0.314(2) 0.021 Uiso d U D 1
H H2N 0.163(4) 0.677(9) 0.300(2) 0.021 Uiso d U D 1
N N3 0.3182(2) 0.6661(5) 0.11256(16) 0.0140(4) Uani d . . 1
O O1 0.03366(17) 1.1251(4) -0.09994(14) 0.0145(4) Uani d . . 1
O O2 0.25253(15) 0.8311(4) -0.00226(12) 0.0130(4) Uani 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
C1 0.0079(8) 0.0118(9) 0.0122(9) -0.0019(7) 0.0032(7) -0.0020(8)
C2 0.0096(8) 0.0114(9) 0.0108(9) 0.0012(7) 0.0021(7) -0.0005(8)
N1 0.0071(8) 0.0147(8) 0.0105(8) 0.0021(6) 0.0028(7) 0.0009(7)
N2 0.0121(9) 0.0189(9) 0.0118(9) 0.0037(7) 0.0044(7) 0.0007(7)
N3 0.0105(8) 0.0204(10) 0.0101(9) 0.0042(7) 0.0022(7) 0.0022(7)
O1 0.0096(8) 0.0190(8) 0.0135(8) 0.0007(6) 0.0018(6) 0.0033(6)
O2 0.0098(8) 0.0188(8) 0.0110(7) 0.0024(6) 0.0042(6) 0.0024(6)
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'
H H 0.0000 0.0000 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 123.0(2)
O1 C1 N1 129.7(2)
O2 C1 N1 107.35(19)
N3 C2 N2 125.1(2)
N3 C2 N1 111.99(19)
N2 C2 N1 122.7(2)
C1 N1 C2 107.8(2)
C2 N3 O2 103.98(15)
C1 O2 N3 108.85(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.222(3)
C1 O2 1.350(3)
C1 N1 1.356(3)
C2 N3 1.311(3)
C2 N2 1.342(3)
C2 N1 1.372(3)
N3 O2 1.451(2)
