#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:42:22 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/68/7056847.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_7056847
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_sum            'C2 H6 N4 O3'
_chemical_formula_weight         134.11
_chemical_name_common            AOD-Hydroxylamine
_chemical_name_systematic        AOD-HyAm
_chemical_properties_physical    ', Heat-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.6560(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0644(2)
_cell_length_b                   6.1129(2)
_cell_length_c                   12.3876(5)
_cell_measurement_reflns_used    61
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      29.8671
_cell_measurement_theta_min      5.1125
_cell_volume                     515.10(3)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14096
_diffrn_reflns_theta_full        31.03
_diffrn_reflns_theta_max         31.03
_diffrn_reflns_theta_min         3.75
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1625
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0384
_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)+(0.0370P)²+0.2769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                1406
_reflns_number_total             1625
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj03950f2.cif
_cod_data_source_block           hhh15m
_cod_depositor_comments
'Adding full bibliography for 7056845--7056848.cif.'
_cod_database_code               7056847
_shelx_res_file
;


    hhh15m.res created by SHELXL-2014/7


TITL hhh15m in P2(1)/c
CELL 0.71073   7.06440   6.11290  12.38760  90.0000 105.6560  90.0000
ZERR 4.00000 0.00020 0.00020 0.00050 0.0000 0.0012 0.0000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 8 24 16 12
L.S. 4
ACTA
BOND
FMAP 2
PLAN 5
SIZE 0.068 0.157 0.208
DFIX 0.88 0.02 N3 H1N  N3 H2N
TEMP -173
WGHT    0.037000    0.276900
FVAR       0.62737
C1    1    0.679574    0.235219    0.554956    11.00000    0.01056    0.00787 =
         0.00903    0.00003    0.00072   -0.00023
C2    1    0.415778    0.284133    0.602911    11.00000    0.00899    0.00972 =
         0.01273    0.00036    0.00230   -0.00032
N1    3    0.351503    0.268583    0.493183    11.00000    0.00843    0.01288 =
         0.01256    0.00017    0.00210    0.00118
N2    3    0.613885    0.263974    0.645583    11.00000    0.00825    0.01405 =
         0.00978   -0.00044    0.00168    0.00050
N3    3    0.293867    0.307778    0.670218    11.00000    0.01013    0.02398 =
         0.01443   -0.00109    0.00443    0.00052
H1N   2    0.177592    0.356740    0.639114    11.00000   -1.50000
H2N   2    0.351661    0.362762    0.736060    11.00000   -1.50000
N4    3    0.906039    0.353961    0.839307    11.00000    0.00982    0.01172 =
         0.00968   -0.00032    0.00279    0.00068
AFIX 137
H4A   2    0.873991    0.345002    0.905560    11.00000   -1.50000
H4B   2    0.794414    0.352180    0.781651    11.00000   -1.50000
H4C   2    0.972692    0.480588    0.837224    11.00000   -1.50000
AFIX   0
O1    4    0.527717    0.233113    0.459061    11.00000    0.00903    0.01366 =
         0.00933   -0.00040    0.00067    0.00075
O2    4    0.850798    0.211855    0.548210    11.00000    0.00994    0.01506 =
         0.01148   -0.00060    0.00324    0.00093
O3    4    1.026121    0.173282    0.829155    11.00000    0.01035    0.01679 =
         0.01343   -0.00405   -0.00060    0.00453
AFIX 147
H3    2    1.131300    0.177928    0.880798    11.00000   -1.50000
AFIX   0
HKLF 4

REM  hhh15m in P2(1)/c
REM R1 =  0.0384 for    1406 Fo > 4sig(Fo)  and  0.0466 for all    1625 data
REM     90 parameters refined using      2 restraints

END

WGHT      0.0370      0.2774

REM Highest difference peak  0.363,  deepest hole -0.261,  1-sigma level  0.058
Q1    1   0.5143  0.2714  0.6284  11.00000  0.05    0.36
Q2    1   0.6491  0.2162  0.6016  11.00000  0.05    0.34
Q3    1   0.6093  0.2452  0.5041  11.00000  0.05    0.33
Q4    1   0.3626  0.3126  0.6395  11.00000  0.05    0.29
Q5    1   0.3719  0.2627  0.5495  11.00000  0.05    0.27
;
_shelx_res_checksum              15994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.67957(15) 0.23522(16) 0.55496(9) 0.0095(2) Uani d . . 1
C C2 0.41578(15) 0.28413(17) 0.60291(9) 0.0106(2) Uani d . . 1
N N1 0.35150(13) 0.26858(15) 0.49318(8) 0.01143(19) Uani d . . 1
N N2 0.61388(13) 0.26397(15) 0.64558(8) 0.01084(19) Uani d . . 1
N N3 0.29387(15) 0.30778(18) 0.67022(9) 0.0160(2) Uani d . D 1
H H1N 0.178(2) 0.357(3) 0.6391(14) 0.024 Uiso d U D 1
H H2N 0.352(2) 0.363(3) 0.7361(12) 0.024 Uiso d U D 1
N N4 0.90604(13) 0.35396(15) 0.83931(8) 0.01038(19) Uani d . . 1
H H4A 0.874 0.345 0.9056 0.016 Uiso calc U R 1
H H4B 0.7944 0.3522 0.7817 0.016 Uiso calc U R 1
H H4C 0.9727 0.4806 0.8372 0.016 Uiso calc U R 1
O O1 0.52772(11) 0.23311(13) 0.45906(6) 0.01102(17) Uani d . . 1
O O2 0.85080(11) 0.21185(13) 0.54821(7) 0.01210(18) Uani d . . 1
O O3 1.02612(11) 0.17328(14) 0.82915(7) 0.01426(18) Uani d . . 1
H H3 1.1313 0.1779 0.8808 0.021 Uiso calc U R 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 0.0106(4) 0.0079(4) 0.0090(4) -0.0002(3) 0.0007(4) 0.0000(3)
C2 0.0090(4) 0.0097(5) 0.0127(5) -0.0003(3) 0.0023(4) 0.0004(4)
N1 0.0084(4) 0.0129(4) 0.0126(4) 0.0012(3) 0.0021(3) 0.0002(3)
N2 0.0083(4) 0.0141(4) 0.0098(4) 0.0005(3) 0.0017(3) -0.0004(3)
N3 0.0101(4) 0.0240(5) 0.0144(5) 0.0005(4) 0.0044(3) -0.0011(4)
N4 0.0098(4) 0.0117(4) 0.0097(4) 0.0007(3) 0.0028(3) -0.0003(3)
O1 0.0090(3) 0.0137(4) 0.0093(3) 0.0008(3) 0.0007(3) -0.0004(3)
O2 0.0099(3) 0.0151(4) 0.0115(4) 0.0009(3) 0.0032(3) -0.0006(3)
O3 0.0103(3) 0.0168(4) 0.0134(4) 0.0045(3) -0.0006(3) -0.0041(3)
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
O2 C1 N2 129.50(10)
O2 C1 O1 119.31(9)
N2 C1 O1 111.19(9)
N1 C2 N3 122.87(10)
N1 C2 N2 115.26(10)
N3 C2 N2 121.79(10)
C2 N1 O1 103.32(8)
C1 N2 C2 103.84(9)
C1 O1 N1 106.37(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2430(13)
C1 N2 1.3371(14)
C1 O1 1.3691(13)
C2 N1 1.3152(14)
C2 N3 1.3584(14)
C2 N2 1.3616(13)
N1 O1 1.4350(12)
N4 O3 1.4188(12)
