# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1407655'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_chemical_name_systematic        'amino oxadiazolone'
_chemical_name_common            3-amino-1,2,4-oxadiazol-5-one
_chemical_formula_moiety         'C2 H3 N3 O2'
_chemical_formula_sum            'C4 H6 N6 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         202.15
_chemical_absolute_configuration ?

_chemical_melting_point          231

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   9.3860(16)
_cell_length_b                   3.5384(6)
_cell_length_c                   12.154(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.139(6)
_cell_angle_gamma                90
_cell_volume                     381.34(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1099
_cell_measurement_theta_min      3.5487
_cell_measurement_theta_max      31.3745
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208

_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            2638
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         31.43
_diffrn_reflns_theta_full        31.43
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;

Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             1157
_reflns_number_gt                1072
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0875
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.111
_refine_ls_number_reflns         1157
_refine_ls_number_parameters     70
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.262
_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'
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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_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
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) ?

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
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) ?

_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
;

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/Ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hhh12m
_database_code_depnum_ccdc_archive 'CCDC 1561177'
_audit_update_record             
;
2017-12-02 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_chemical_name_systematic        'Dioxime (4c)'
_chemical_name_common            'Dioxime (4c)'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         132.13

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.5972(3)
_cell_length_b                   9.4798(3)
_cell_length_c                   14.2271(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.2613(13)
_cell_angle_gamma                90
_cell_volume                     1152.59(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    99
_cell_measurement_theta_min      3.1991
_cell_measurement_theta_max      27.9048
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.058
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            13893
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         30.98
_diffrn_reflns_theta_full        30.98
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             1830
_reflns_number_gt                1547
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1320
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         1830
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+1.6428P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.652
_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'
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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.63336(15) 0.65963(12) 0.60637(8) 0.0102(2) Uani d . . . 1 . .
C C2 0.79548(15) 0.66388(13) 0.65845(8) 0.0120(3) Uani d . . . 1 . .
H H2C 0.8476 0.7531 0.6438 0.014 Uiso calc U . R 1 . .
H H2D 0.8581 0.5846 0.6374 0.014 Uiso calc U . R 1 . .
C C3 0.78779(14) 0.65349(12) 0.76382(8) 0.0102(2) Uani d . . . 1 . .
N N1 0.58370(13) 0.77208(11) 0.56080(7) 0.0107(2) Uani d . . . 1 . .
N N2 0.54952(14) 0.54094(12) 0.61253(8) 0.0155(3) Uani d . . . 1 . .
H H2A 0.4534 0.5358 0.5843 0.019 Uiso calc U . R 1 . .
H H2B 0.5908 0.4683 0.6448 0.019 Uiso calc U . R 1 . .
N N3 0.73685(14) 0.76885(11) 0.80819(8) 0.0137(2) Uani d . . . 1 . .
H H3A 0.7317 0.7671 0.8696 0.016 Uiso calc U . R 1 . .
H H3B 0.709 0.8453 0.7755 0.016 Uiso calc U . R 1 . .
N N4 0.83214(13) 0.53493(11) 0.80232(7) 0.0109(2) Uani d . . . 1 . .
O O1 0.42667(11) 0.75007(9) 0.51881(7) 0.0135(2) Uani d . . . 1 . .
H H1 0.4003 0.8163 0.4812 0.02 Uiso calc U . R 1 . .
O O2 0.81575(11) 0.53610(9) 0.90197(6) 0.0116(2) Uani d . . . 1 . .
H H2 0.8435 0.4577 0.9256 0.017 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 0.0117(5) 0.0117(5) 0.0067(5) -0.0001(4) -0.0010(4) -0.0010(4)
C2 0.0111(6) 0.0154(6) 0.0091(5) -0.0003(4) -0.0016(4) 0.0018(4)
C3 0.0101(5) 0.0112(5) 0.0085(5) -0.0020(4) -0.0024(4) -0.0001(4)
N1 0.0109(5) 0.0120(5) 0.0082(4) -0.0007(4) -0.0035(4) -0.0004(3)
N2 0.0175(6) 0.0103(5) 0.0167(5) -0.0010(4) -0.0073(4) 0.0029(4)
N3 0.0218(6) 0.0093(5) 0.0092(4) 0.0016(4) -0.0027(4) 0.0008(3)
N4 0.0132(5) 0.0123(5) 0.0066(4) 0.0006(4) -0.0018(4) -0.0007(3)
O1 0.0137(5) 0.0126(4) 0.0126(4) -0.0014(3) -0.0062(3) 0.0040(3)
O2 0.0176(5) 0.0096(4) 0.0068(4) 0.0014(3) -0.0022(3) 0.0006(3)

_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
C1 N1 . 1.2956(15) ?
C1 N2 . 1.3443(16) ?
C1 C2 . 1.5060(17) ?
C2 C3 . 1.5109(17) ?
C3 N4 . 1.2896(16) ?
C3 N3 . 1.3589(16) ?
N1 O1 . 1.4308(14) ?
N4 O2 . 1.4400(13) ?

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
N1 C1 N2 . . 124.86(12) ?
N1 C1 C2 . . 117.45(11) ?
N2 C1 C2 . . 117.67(11) ?
C1 C2 C3 . . 110.37(10) ?
N4 C3 N3 . . 126.82(11) ?
N4 C3 C2 . . 115.81(11) ?
N3 C3 C2 . . 117.36(10) ?
C1 N1 O1 . . 109.47(10) ?
C3 N4 O2 . . 110.81(10) ?

_shelx_res_file                  
;


    hhh12m.res created by SHELXL-2014/7


TITL hhh12m in C2/c
CELL 0.71073   8.59720   9.47980  14.22710  90.0000  96.2613  90.0000
ZERR 8.00000 0.00030 0.00030 0.00050 0.0000 0.0013 0.0000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C  H  N  O
UNIT 24  64 32 16
L.S. 4
ACTA
BOND
FMAP 2
PLAN 5
TEMP -173.140
WGHT    0.056400    1.642800
FVAR       0.32819
C1    1    0.633357    0.659630    0.606371    11.00000    0.01168    0.01167 =
         0.00672   -0.00105   -0.00095   -0.00007
C2    1    0.795483    0.663884    0.658451    11.00000    0.01110    0.01540 =
         0.00906    0.00179   -0.00156   -0.00031
AFIX  23
H2C   2    0.847634    0.753075    0.643753    11.00000   -1.20000
H2D   2    0.858079    0.584570    0.637368    11.00000   -1.20000
AFIX   0
C3    1    0.787791    0.653487    0.763815    11.00000    0.01010    0.01119 =
         0.00850   -0.00010   -0.00240   -0.00197
N1    3    0.583700    0.772082    0.560802    11.00000    0.01088    0.01199 =
         0.00818   -0.00039   -0.00348   -0.00073
N2    3    0.549515    0.540936    0.612534    11.00000    0.01747    0.01029 =
         0.01673    0.00290   -0.00732   -0.00101
AFIX  93
H2A   2    0.453366    0.535826    0.584319    11.00000   -1.20000
H2B   2    0.590779    0.468347    0.644784    11.00000   -1.20000
AFIX   0
N3    3    0.736849    0.768849    0.808193    11.00000    0.02180    0.00925 =
         0.00917    0.00077   -0.00266    0.00158
AFIX  93
H3A   2    0.731709    0.767115    0.869620    11.00000   -1.20000
H3B   2    0.709001    0.845287    0.775503    11.00000   -1.20000
AFIX   0
N4    3    0.832144    0.534929    0.802317    11.00000    0.01316    0.01231 =
         0.00656   -0.00066   -0.00175    0.00061
O1    4    0.426667    0.750065    0.518810    11.00000    0.01373    0.01256 =
         0.01262    0.00395   -0.00619   -0.00137
AFIX 147
H1    2    0.400346    0.816312    0.481193    11.00000   -1.50000
AFIX   0
O2    4    0.815748    0.536098    0.901966    11.00000    0.01764    0.00957 =
         0.00683    0.00057   -0.00220    0.00140
AFIX 147
H2    2    0.843547    0.457664    0.925610    11.00000   -1.50000
AFIX   0
HKLF 4

REM  hhh12m in C2/c
REM R1 =  0.0474 for    1547 Fo > 4sig(Fo)  and  0.0589 for all    1830 data
REM     84 parameters refined using      0 restraints

END

WGHT      0.0564      1.6428

REM Highest difference peak  0.578,  deepest hole -0.652,  1-sigma level  0.075
Q1    1   0.7104  0.6663  0.6341  11.00000  0.05    0.58
Q2    1   0.6734  0.7513  0.8604  11.00000  0.05    0.44
Q3    1   0.5974  0.5981  0.6097  11.00000  0.05    0.38
Q4    1   0.6115  0.4772  0.6222  11.00000  0.05    0.34
Q5    1   0.5040  0.7603  0.5419  11.00000  0.05    0.33
;
_shelx_res_checksum              55893

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hot Methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hhh15m
_database_code_depnum_ccdc_archive 'CCDC 1560543'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_chemical_name_systematic        AOD-HyAm
_chemical_name_common            AOD-Hydroxylamine
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H6 N4 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         134.11

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.0644(2)
_cell_length_b                   6.1129(2)
_cell_length_c                   12.3876(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.6560(12)
_cell_angle_gamma                90
_cell_volume                     515.10(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    61
_cell_measurement_theta_min      5.1125
_cell_measurement_theta_max      29.8671
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.068
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280

_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            14096
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         31.03
_diffrn_reflns_theta_full        31.03
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             1625
_reflns_number_gt                1406
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0910
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         1625
_refine_ls_number_parameters     90
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.2769P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.261
_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'
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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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)

_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
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) ?

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
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) ?

_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

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_properties_physical    ', Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hhh18m
_database_code_depnum_ccdc_archive 'CCDC 1561922'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2017-12-27 downloaded from the CCDC.
;
_chemical_name_systematic        AOD-Hydrazinium
_chemical_name_common            AOD-HY
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H7 N5 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         133.13
_chemical_absolute_configuration unk

_chemical_melting_point          324

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   13.3609(4)
_cell_length_b                   10.8742(4)
_cell_length_c                   3.70460(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     538.24(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5095
_cell_measurement_theta_min      2.4149
_cell_measurement_theta_max      27.0649
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280

_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            11594
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4

_refine_special_details          Twin

_reflns_number_total             1180
_reflns_number_gt                1121
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0730
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         1180
_refine_ls_number_parameters     95
_refine_ls_number_restraints     5
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.1002P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.22679(14) -0.06059(17) 0.0350(5) 0.0115(4) Uani d . . . 1 . .
C C2 0.35079(14) 0.03785(17) 0.2523(6) 0.0103(4) Uani d . . . 1 . .
N N1 0.25605(12) 0.05307(14) 0.1257(5) 0.0117(4) Uani d . . . 1 . .
N N2 0.38562(13) -0.07616(15) 0.2439(5) 0.0126(4) Uani d . . . 1 . .
N N3 0.40764(12) 0.13302(15) 0.3684(6) 0.0139(4) Uani d . . D 1 . .
H H3N 0.3742(18) 0.202(2) 0.410(9) 0.021 Uiso d U . D 1 . .
H H4N 0.4596(17) 0.116(2) 0.515(7) 0.021 Uiso d U . D 1 . .
N N4 0.08925(12) 0.20312(14) 0.1513(5) 0.0106(3) Uani d . . . 1 . .
H H4A 0.089234 0.284962 0.100052 0.016 Uiso calc U . R 1 . .
H H4B 0.153262 0.174546 0.150403 0.016 Uiso calc U . R 1 . .
H H4C 0.06165 0.190687 0.372871 0.016 Uiso calc U . R 1 . .
N N5 0.03124(12) 0.13804(15) -0.1188(5) 0.0123(4) Uani d . . D 1 . .
H H1N -0.0329(15) 0.145(2) -0.059(8) 0.018 Uiso d U . D 1 . .
H H2N 0.0539(18) 0.0597(19) -0.103(8) 0.018 Uiso d U . D 1 . .
O O1 0.30137(10) -0.14395(12) 0.0962(4) 0.0128(3) Uani d . . . 1 . .
O O2 0.14548(10) -0.09692(13) -0.0874(5) 0.0150(3) 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 0.0126(9) 0.0107(8) 0.0113(9) 0.0012(7) 0.0015(8) 0.0000(7)
C2 0.0102(8) 0.0106(9) 0.0101(8) 0.0001(7) 0.0023(7) 0.0012(8)
N1 0.0107(8) 0.0099(7) 0.0145(7) 0.0006(6) 0.0004(7) -0.0009(7)
N2 0.0109(7) 0.0104(7) 0.0166(8) -0.0004(6) -0.0018(7) -0.0014(7)
N3 0.0123(8) 0.0098(8) 0.0195(9) -0.0001(6) -0.0025(8) -0.0011(7)
N4 0.0115(7) 0.0105(7) 0.0099(8) -0.0001(6) -0.0013(6) -0.0008(7)
N5 0.0126(7) 0.0120(8) 0.0122(8) -0.0025(6) -0.0025(7) -0.0014(7)
O1 0.0120(6) 0.0099(6) 0.0166(8) -0.0001(5) -0.0013(6) -0.0010(6)
O2 0.0126(6) 0.0129(7) 0.0195(7) -0.0025(5) -0.0016(6) -0.0018(6)

_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
C1 O2 . 1.242(2) ?
C1 N1 . 1.339(2) ?
C1 O1 . 1.366(2) ?
C2 N2 . 1.325(2) ?
C2 N3 . 1.354(3) ?
C2 N1 . 1.360(3) ?
N2 O1 . 1.452(2) ?
N4 N5 . 1.450(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_3
_geom_angle
_geom_angle_publ_flag
O2 C1 N1 . . 129.84(18) ?
O2 C1 O1 . . 119.19(17) ?
N1 C1 O1 . . 110.97(16) ?
N2 C2 N3 . . 121.73(17) ?
N2 C2 N1 . . 115.64(17) ?
N3 C2 N1 . . 122.60(17) ?
C1 N1 C2 . . 104.24(15) ?
C2 N2 O1 . . 102.22(15) ?
C1 O1 N2 . . 106.92(13) ?

_shelx_res_file                  
;

TITL hhh18m in Pna2(1)
    hhh18m.res
    created by SHELXL-2016/6 at 16:12:13 on 12-Jul-2017
CELL 0.71073  13.36090  10.87420   3.70460  90.0000  90.0000  90.0000
ZERR 4.00000 0.00040 0.00040 0.00010 0.0000 0.0000 0.0000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5+X, 0.5-Y, Z
SYMM 0.5-X, 0.5+Y, 0.5+Z
SFAC C  H  N  O
UNIT 8  28  20  8
L.S. 4
ACTA
BOND
FMAP 2
PLAN 5
SIZE 0.04 0.08 0.10
DFIX 0.90 0.02 N5 H1N  N5 H2N
DFIX 0.90 0.02 N3 H3N  N3 H4N
TEMP -173
WGHT    0.041500    0.100200
FVAR       0.65777
MOLE 1
C1    1    0.226788   -0.060593    0.035005    11.00000    0.01263    0.01066 =
         0.01130   -0.00002    0.00154    0.00118
C2    1    0.350793    0.037852    0.252326    11.00000    0.01016    0.01058 =
         0.01007    0.00118    0.00230    0.00006
N1    3    0.256046    0.053068    0.125670    11.00000    0.01073    0.00987 =
         0.01455   -0.00094    0.00045    0.00063
N2    3    0.385622   -0.076158    0.243894    11.00000    0.01093    0.01036 =
         0.01655   -0.00141   -0.00185   -0.00044
N3    3    0.407643    0.133019    0.368350    11.00000    0.01228    0.00975 =
         0.01954   -0.00114   -0.00253   -0.00007
H3N   2    0.374243    0.201794    0.410118    11.00000   -1.50000
H4N   2    0.459596    0.115652    0.514505    11.00000   -1.50000
N4    3    0.089246    0.203118    0.151280    11.00000    0.01152    0.01051 =
         0.00987   -0.00082   -0.00133   -0.00011
AFIX 137
H4A   2    0.089234    0.284962    0.100052    11.00000   -1.50000
H4B   2    0.153262    0.174546    0.150403    11.00000   -1.50000
H4C   2    0.061650    0.190687    0.372871    11.00000   -1.50000
AFIX   0
N5    3    0.031236    0.138042   -0.118762    11.00000    0.01258    0.01199 =
         0.01219   -0.00136   -0.00246   -0.00250
H1N   2   -0.032852    0.144920   -0.059447    11.00000   -1.50000
H2N   2    0.053860    0.059738   -0.103468    11.00000   -1.50000
O1    4    0.301374   -0.143951    0.096246    11.00000    0.01195    0.00985 =
         0.01662   -0.00097   -0.00130   -0.00006
O2    4    0.145481   -0.096922   -0.087389    11.00000    0.01260    0.01291 =
         0.01950   -0.00176   -0.00156   -0.00245
HKLF 4




REM  hhh18m in Pna2(1)
REM R1 =  0.0296 for    1121 Fo > 4sig(Fo)  and  0.0320 for all    1180 data
REM     95 parameters refined using      5 restraints

END

WGHT      0.0441      0.0765

REM Highest difference peak  0.154,  deepest hole -0.220,  1-sigma level  0.044
Q1    1   0.5383  0.1787  0.6111  11.00000  0.05    0.15
Q2    1   0.2324  0.0043  0.1426  11.00000  0.05    0.15
Q3    1   0.1585 -0.0896  0.1345  11.00000  0.05    0.15
Q4    1   0.4081 -0.0863  0.4376  11.00000  0.05    0.14
Q5    1   0.3127  0.0561  0.1136  11.00000  0.05    0.14
;
_shelx_res_checksum              72193

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hot Methanol'
_exptl_crystal_preparation       'Energetic Properties'
