# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shrv275
_database_code_depnum_ccdc_archive 'CCDC 1853787'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv275             
;
PROBLEM: Short Inter D...A Contact  O9       ..O13              2.79 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Thursday 05 July 2018 02:10 PM
# end Validation Reply Form


_audit_creation_date             2014-12-09
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 guanidinium dinitro(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methanide hydrate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N5 O5, C H6 N3, H2 O'
_chemical_formula_sum            'C4 H10 N8 O6'
_chemical_formula_weight         266.20

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9400(3)
_cell_length_b                   7.5682(4)
_cell_length_c                   14.0353(7)
_cell_angle_alpha                77.659(2)
_cell_angle_beta                 82.403(2)
_cell_angle_gamma                81.370(2)
_cell_volume                     504.08(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3895
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.35

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9328
_exptl_absorpt_correction_T_max  0.9936

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4870
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2045
_reflns_number_gt                1946
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3782(2) 0.83705(16) 0.38564(8) 0.0181(3) Uani 1 1 d . . .
N2 N 0.4365(2) 0.80046(16) 0.48173(8) 0.0185(3) Uani 1 1 d . . .
H2 H 0.3330 0.8478 0.5283 0.022 Uiso 1 1 calc R . .
C3 C 0.6682(3) 0.68485(17) 0.49673(10) 0.0157(3) Uani 1 1 d . . .
N4 N 0.7628(2) 0.64797(15) 0.40621(8) 0.0155(3) Uani 1 1 d . . .
H4 H 0.9137 0.5764 0.3921 0.019 Uiso 1 1 calc R . .
C5 C 0.5809(3) 0.74231(17) 0.34059(9) 0.0137(3) Uani 1 1 d . . .
C6 C 0.6085(3) 0.73554(17) 0.23637(9) 0.0147(3) Uani 1 1 d . . .
N7 N 0.8347(2) 0.63544(16) 0.19424(8) 0.0157(3) Uani 1 1 d . . .
O8 O 0.8713(2) 0.63150(16) 0.10517(7) 0.0266(3) Uani 1 1 d . . .
O9 O 1.0080(2) 0.54572(14) 0.25000(7) 0.0209(3) Uani 1 1 d . . .
N10 N 0.4034(2) 0.82968(15) 0.17739(8) 0.0159(3) Uani 1 1 d . . .
O11 O 0.2135(2) 0.92758(15) 0.21550(8) 0.0236(3) Uani 1 1 d . . .
O12 O 0.4069(2) 0.81619(18) 0.09099(8) 0.0328(3) Uani 1 1 d . . .
O13 O 0.7723(2) 0.62478(14) 0.57554(7) 0.0207(3) Uani 1 1 d . . .
C1S C 0.4393(3) 0.73961(18) 0.86250(10) 0.0160(3) Uani 1 1 d . . .
N2S N 0.2302(3) 0.84687(18) 0.89851(9) 0.0210(3) Uani 1 1 d . . .
H2SA H 0.220(4) 0.859(3) 0.9601(16) 0.031 Uiso 1 1 d . . .
H2SB H 0.100(5) 0.904(3) 0.8638(16) 0.031 Uiso 1 1 d . . .
N3S N 0.4473(3) 0.71262(18) 0.77163(9) 0.0210(3) Uani 1 1 d . . .
H3SA H 0.322(5) 0.771(3) 0.7333(16) 0.031 Uiso 1 1 d . . .
H3SB H 0.590(5) 0.650(3) 0.7502(15) 0.031 Uiso 1 1 d . . .
N4S N 0.6405(3) 0.66096(17) 0.91733(9) 0.0201(3) Uani 1 1 d . . .
H4SA H 0.7799 0.5906 0.8935 0.024 Uiso 1 1 calc R . .
H4SB H 0.6344 0.6792 0.9775 0.024 Uiso 1 1 calc R . .
O5S O 0.0493(2) 0.87373(15) 0.63423(7) 0.0207(2) Uani 1 1 d . . .
H5SA H -0.050(4) 0.800(3) 0.6214(15) 0.031 Uiso 1 1 d . . .
H5SB H -0.070(5) 0.966(3) 0.6390(15) 0.031 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0192(6) 0.0216(6) 0.0121(5) -0.0041(4) -0.0045(4) 0.0052(5)
N2 0.0193(6) 0.0234(6) 0.0110(5) -0.0055(4) -0.0037(4) 0.0078(5)
C3 0.0160(6) 0.0163(6) 0.0148(6) -0.0047(5) -0.0033(5) 0.0017(5)
N4 0.0140(5) 0.0188(6) 0.0131(6) -0.0052(4) -0.0042(4) 0.0051(4)
C5 0.0139(6) 0.0140(6) 0.0133(6) -0.0024(5) -0.0038(5) 0.0002(5)
C6 0.0143(6) 0.0159(6) 0.0135(6) -0.0033(5) -0.0039(5) 0.0020(5)
N7 0.0156(6) 0.0183(5) 0.0130(5) -0.0039(4) -0.0030(4) 0.0009(4)
O8 0.0239(6) 0.0408(6) 0.0130(5) -0.0097(4) -0.0029(4) 0.0094(5)
O9 0.0180(5) 0.0257(5) 0.0166(5) -0.0051(4) -0.0060(4) 0.0092(4)
N10 0.0159(6) 0.0180(6) 0.0141(5) -0.0043(4) -0.0046(4) 0.0010(4)
O11 0.0215(5) 0.0284(6) 0.0193(5) -0.0086(4) -0.0070(4) 0.0121(4)
O12 0.0304(6) 0.0517(7) 0.0163(5) -0.0157(5) -0.0121(4) 0.0161(5)
O13 0.0223(5) 0.0252(5) 0.0137(5) -0.0058(4) -0.0075(4) 0.0077(4)
C1S 0.0154(6) 0.0172(6) 0.0155(6) -0.0023(5) -0.0025(5) -0.0029(5)
N2S 0.0183(6) 0.0278(7) 0.0164(6) -0.0070(5) -0.0064(5) 0.0061(5)
N3S 0.0204(6) 0.0265(7) 0.0165(6) -0.0072(5) -0.0035(5) 0.0012(5)
N4S 0.0176(6) 0.0246(6) 0.0178(6) -0.0068(5) -0.0052(4) 0.0055(5)
O5S 0.0186(5) 0.0230(5) 0.0199(5) -0.0080(4) -0.0033(4) 0.0061(4)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3141(18) . ?
N1 N2 1.3776(16) . ?
N2 C3 1.3433(18) . ?
N2 H2 0.8800 . ?
C3 O13 1.2489(16) . ?
C3 N4 1.3660(17) . ?
N4 C5 1.3824(16) . ?
N4 H4 0.8800 . ?
C5 C6 1.4622(18) . ?
C6 N7 1.3909(17) . ?
C6 N10 1.4044(17) . ?
N7 O8 1.2453(15) . ?
N7 O9 1.2578(15) . ?
N10 O12 1.2361(15) . ?
N10 O11 1.2424(15) . ?
C1S N4S 1.3279(18) . ?
C1S N3S 1.3287(18) . ?
C1S N2S 1.3294(18) . ?
N2S H2SA 0.88(2) . ?
N2S H2SB 0.86(2) . ?
N3S H3SA 0.88(2) . ?
N3S H3SB 0.85(2) . ?
N4S H4SA 0.8800 . ?
N4S H4SB 0.8800 . ?
O5S H5SA 0.85(2) . ?
O5S H5SB 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 104.50(11) . . ?
C3 N2 N1 112.83(11) . . ?
C3 N2 H2 123.6 . . ?
N1 N2 H2 123.6 . . ?
O13 C3 N2 127.78(12) . . ?
O13 C3 N4 128.09(12) . . ?
N2 C3 N4 104.13(11) . . ?
C3 N4 C5 108.33(11) . . ?
C3 N4 H4 125.8 . . ?
C5 N4 H4 125.8 . . ?
N1 C5 N4 110.21(11) . . ?
N1 C5 C6 125.00(12) . . ?
N4 C5 C6 124.80(12) . . ?
N7 C6 N10 118.99(11) . . ?
N7 C6 C5 121.04(11) . . ?
N10 C6 C5 119.97(12) . . ?
O8 N7 O9 119.51(11) . . ?
O8 N7 C6 123.10(11) . . ?
O9 N7 C6 117.39(11) . . ?
O12 N10 O11 120.36(11) . . ?
O12 N10 C6 122.19(12) . . ?
O11 N10 C6 117.45(11) . . ?
N4S C1S N3S 120.27(13) . . ?
N4S C1S N2S 119.80(13) . . ?
N3S C1S N2S 119.93(13) . . ?
C1S N2S H2SA 119.7(14) . . ?
C1S N2S H2SB 122.0(14) . . ?
H2SA N2S H2SB 118(2) . . ?
C1S N3S H3SA 120.7(14) . . ?
C1S N3S H3SB 116.6(14) . . ?
H3SA N3S H3SB 122(2) . . ?
C1S N4S H4SA 120.0 . . ?
C1S N4S H4SB 120.0 . . ?
H4SA N4S H4SB 120.0 . . ?
H5SA O5S H5SB 101(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.47(16) . . . . ?
N1 N2 C3 O13 -179.16(13) . . . . ?
N1 N2 C3 N4 0.67(16) . . . . ?
O13 C3 N4 C5 179.22(13) . . . . ?
N2 C3 N4 C5 -0.60(14) . . . . ?
N2 N1 C5 N4 0.06(15) . . . . ?
N2 N1 C5 C6 179.32(12) . . . . ?
C3 N4 C5 N1 0.35(15) . . . . ?
C3 N4 C5 C6 -178.91(12) . . . . ?
N1 C5 C6 N7 178.12(12) . . . . ?
N4 C5 C6 N7 -2.7(2) . . . . ?
N1 C5 C6 N10 -2.5(2) . . . . ?
N4 C5 C6 N10 176.67(11) . . . . ?
N10 C6 N7 O8 3.4(2) . . . . ?
C5 C6 N7 O8 -177.24(12) . . . . ?
N10 C6 N7 O9 -176.69(11) . . . . ?
C5 C6 N7 O9 2.71(19) . . . . ?
N7 C6 N10 O12 5.3(2) . . . . ?
C5 C6 N10 O12 -174.11(13) . . . . ?
N7 C6 N10 O11 -175.31(11) . . . . ?
C5 C6 N10 O11 5.29(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O5S 0.88 1.92 2.7667(16) 159.7 .
N4 H4 O13 0.88 2.03 2.8475(15) 154.5 2_766
N2S H2SA O12 0.88(2) 2.11(2) 2.8999(17) 149.2(19) 1_556
N2S H2SB O11 0.86(2) 2.13(2) 2.9857(17) 172.9(19) 2_576
N3S H3SA O5S 0.88(2) 2.02(2) 2.8894(17) 171.2(19) .
N3S H3SB O9 0.85(2) 2.29(2) 3.1008(17) 159.8(19) 2_766
N4S H4SA O8 0.88 2.22 3.0513(16) 157.8 2_766
N4S H4SB O12 0.88 2.18 2.9540(17) 146.2 1_556
O5S H5SA O13 0.85(2) 1.95(2) 2.7994(16) 171(2) 1_455
O5S H5SB N1 0.85(2) 1.97(2) 2.7995(16) 163(2) 2_576

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_shrv273
_database_code_depnum_ccdc_archive 'CCDC 1853948'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_shrv273             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.815 Why?
RESPONSE: Low data completeness is often encountered in triclinic unit cells when utilizing Cu radiation.
;
_vrf_PLAT430_shrv273             
;
PROBLEM: Short Inter D...A Contact  O9       ..O9               2.81 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Thursday 05 July 2018 02:20 PM
# end Validation Reply Form


_audit_creation_date             2014-11-04
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
'amino(hydrazinyl)methaniminium dinitro(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl) methanide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N5 O5, C H7 N4'
_chemical_formula_sum            'C4 H9 N9 O5'
_chemical_formula_weight         263.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.64810(10)
_cell_length_b                   10.9836(4)
_cell_length_c                   13.2014(4)
_cell_angle_alpha                107.196(2)
_cell_angle_beta                 95.394(2)
_cell_angle_gamma                99.113(2)
_cell_volume                     493.35(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1777
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      67.82

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.8730
_exptl_absorpt_correction_T_max  0.9726

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2603
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         68.05
_reflns_number_total             1476
_reflns_number_gt                1359
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker PROTEUM v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker PROTEUM v2009.7-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.66A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0797P)²+0.1701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5905(4) 0.86528(14) 0.47019(11) 0.0195(4) Uani 1 1 d . . .
N2 N 0.7142(4) 0.92710(14) 0.57725(11) 0.0204(4) Uani 1 1 d . . .
H2 H 0.7097 1.0092 0.6095 0.024 Uiso 1 1 calc R . .
C3 C 0.8449(5) 0.84825(17) 0.62848(14) 0.0177(4) Uani 1 1 d . . .
N4 N 0.7999(4) 0.73222(14) 0.54799(11) 0.0177(4) Uani 1 1 d . . .
H4 H 0.8588 0.6601 0.5549 0.021 Uiso 1 1 calc R . .
C5 C 0.6462(5) 0.74823(17) 0.45444(13) 0.0163(4) Uani 1 1 d . . .
O6 O 0.9728(4) 0.87446(12) 0.72388(10) 0.0231(3) Uani 1 1 d . . .
C7 C 0.5725(5) 0.64733(17) 0.35011(13) 0.0175(4) Uani 1 1 d . . .
N8 N 0.3675(4) 0.52487(15) 0.34071(11) 0.0188(4) Uani 1 1 d . . .
O9 O 0.2121(4) 0.51800(12) 0.42019(10) 0.0216(3) Uani 1 1 d . . .
O10 O 0.3472(4) 0.42825(13) 0.26188(10) 0.0295(4) Uani 1 1 d . . .
N11 N 0.7027(5) 0.67332(15) 0.26242(12) 0.0199(4) Uani 1 1 d . . .
O12 O 0.6167(5) 0.59384(14) 0.17058(10) 0.0343(4) Uani 1 1 d . . .
O13 O 0.9063(4) 0.78240(13) 0.27710(10) 0.0275(4) Uani 1 1 d . . .
N14 N 1.4188(5) 0.95131(16) 0.12152(13) 0.0224(4) Uani 1 1 d . . .
H14A H 1.293(7) 1.007(2) 0.1632(19) 0.027 Uiso 1 1 d . . .
H14B H 1.616(7) 0.952(2) 0.163(2) 0.027 Uiso 1 1 d . . .
N15 N 1.2021(5) 0.82430(15) 0.09417(12) 0.0226(4) Uani 1 1 d . . .
H15 H 1.1510 0.7901 0.1449 0.027 Uiso 1 1 calc R . .
C16 C 1.0759(5) 0.75674(18) -0.00757(14) 0.0196(4) Uani 1 1 d . . .
N17 N 1.1650(5) 0.80474(16) -0.08456(12) 0.0248(4) Uani 1 1 d . . .
H17 H 1.3091 0.8821 -0.0684 0.030 Uiso 1 1 calc R . .
H17B H 1.0802 0.7594 -0.1520 0.030 Uiso 1 1 calc R . .
N18 N 0.8673(5) 0.63900(16) -0.02895(12) 0.0252(4) Uani 1 1 d . . .
H18A H 0.7848 0.5908 -0.0959 0.030 Uiso 1 1 calc R . .
H18B H 0.8117 0.6091 0.0238 0.030 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0290(9) 0.0137(8) 0.0137(8) 0.0031(6) -0.0007(6) 0.0029(6)
N2 0.0325(9) 0.0107(8) 0.0153(8) 0.0018(6) -0.0010(7) 0.0039(6)
C3 0.0200(9) 0.0157(9) 0.0154(9) 0.0046(7) 0.0005(7) -0.0004(7)
N4 0.0248(8) 0.0133(8) 0.0149(7) 0.0059(6) -0.0012(6) 0.0033(6)
C5 0.0196(9) 0.0139(9) 0.0150(9) 0.0059(7) -0.0001(7) 0.0006(7)
O6 0.0322(8) 0.0187(7) 0.0146(7) 0.0040(5) -0.0041(6) 0.0015(5)
C7 0.0228(10) 0.0133(9) 0.0147(9) 0.0041(7) -0.0007(7) 0.0013(7)
N8 0.0245(9) 0.0157(8) 0.0148(8) 0.0051(6) -0.0023(6) 0.0022(6)
O9 0.0291(8) 0.0174(7) 0.0204(7) 0.0092(5) 0.0053(5) 0.0033(5)
O10 0.0503(10) 0.0141(7) 0.0172(7) -0.0005(5) 0.0029(6) -0.0022(6)
N11 0.0251(9) 0.0168(8) 0.0161(8) 0.0049(6) 0.0003(6) 0.0012(6)
O12 0.0575(10) 0.0218(7) 0.0138(7) -0.0002(6) 0.0047(7) -0.0095(7)
O13 0.0380(8) 0.0194(7) 0.0189(7) 0.0049(5) 0.0024(6) -0.0090(6)
N14 0.0253(9) 0.0171(9) 0.0197(8) 0.0024(7) 0.0002(7) -0.0023(7)
N15 0.0313(9) 0.0176(8) 0.0156(8) 0.0055(6) 0.0009(7) -0.0035(7)
C16 0.0210(10) 0.0179(9) 0.0189(9) 0.0055(7) 0.0004(7) 0.0030(7)
N17 0.0327(9) 0.0215(9) 0.0161(8) 0.0061(7) -0.0010(7) -0.0046(7)
N18 0.0351(10) 0.0192(9) 0.0158(8) 0.0040(6) -0.0009(7) -0.0049(7)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.292(2) . ?
N1 N2 1.370(2) . ?
N2 C3 1.361(2) . ?
N2 H2 0.8800 . ?
C3 O6 1.233(2) . ?
C3 N4 1.371(2) . ?
N4 C5 1.378(2) . ?
N4 H4 0.8800 . ?
C5 C7 1.460(2) . ?
C7 N11 1.379(2) . ?
C7 N8 1.396(2) . ?
N8 O10 1.234(2) . ?
N8 O9 1.254(2) . ?
N11 O12 1.244(2) . ?
N11 O13 1.256(2) . ?
N14 N15 1.414(2) . ?
N14 H14A 0.91(3) . ?
N14 H14B 0.86(3) . ?
N15 C16 1.324(2) . ?
N15 H15 0.8800 . ?
C16 N17 1.320(2) . ?
C16 N18 1.328(2) . ?
N17 H17 0.8800 . ?
N17 H17B 0.8800 . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 104.53(14) . . ?
C3 N2 N1 112.97(14) . . ?
C3 N2 H2 123.5 . . ?
N1 N2 H2 123.5 . . ?
O6 C3 N2 128.59(17) . . ?
O6 C3 N4 128.36(17) . . ?
N2 C3 N4 103.05(14) . . ?
C3 N4 C5 108.08(14) . . ?
C3 N4 H4 126.0 . . ?
C5 N4 H4 126.0 . . ?
N1 C5 N4 111.37(15) . . ?
N1 C5 C7 124.44(15) . . ?
N4 C5 C7 124.14(15) . . ?
N11 C7 N8 120.80(16) . . ?
N11 C7 C5 120.27(15) . . ?
N8 C7 C5 118.93(15) . . ?
O10 N8 O9 121.48(15) . . ?
O10 N8 C7 123.22(15) . . ?
O9 N8 C7 115.26(15) . . ?
O12 N11 O13 120.03(14) . . ?
O12 N11 C7 121.99(15) . . ?
O13 N11 C7 117.96(15) . . ?
N15 N14 H14A 107.8(15) . . ?
N15 N14 H14B 105.4(16) . . ?
H14A N14 H14B 105(2) . . ?
C16 N15 N14 120.17(15) . . ?
C16 N15 H15 119.9 . . ?
N14 N15 H15 119.9 . . ?
N17 C16 N15 120.41(17) . . ?
N17 C16 N18 121.70(17) . . ?
N15 C16 N18 117.86(16) . . ?
C16 N17 H17 120.0 . . ?
C16 N17 H17B 120.0 . . ?
H17 N17 H17B 120.0 . . ?
C16 N18 H18A 120.0 . . ?
C16 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.4(2) . . . . ?
N1 N2 C3 O6 -179.72(17) . . . . ?
N1 N2 C3 N4 0.32(19) . . . . ?
O6 C3 N4 C5 179.96(18) . . . . ?
N2 C3 N4 C5 -0.09(18) . . . . ?
N2 N1 C5 N4 0.4(2) . . . . ?
N2 N1 C5 C7 -176.98(16) . . . . ?
C3 N4 C5 N1 -0.2(2) . . . . ?
C3 N4 C5 C7 177.17(16) . . . . ?
N1 C5 C7 N11 48.5(3) . . . . ?
N4 C5 C7 N11 -128.51(19) . . . . ?
N1 C5 C7 N8 -131.24(19) . . . . ?
N4 C5 C7 N8 51.7(2) . . . . ?
N11 C7 N8 O10 13.3(3) . . . . ?
C5 C7 N8 O10 -166.99(17) . . . . ?
N11 C7 N8 O9 -168.92(16) . . . . ?
C5 C7 N8 O9 10.8(2) . . . . ?
N8 C7 N11 O12 6.4(3) . . . . ?
C5 C7 N11 O12 -173.34(17) . . . . ?
N8 C7 N11 O13 -175.41(16) . . . . ?
C5 C7 N11 O13 4.9(3) . . . . ?
N14 N15 C16 N17 3.1(3) . . . . ?
N14 N15 C16 N18 -178.66(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.88 2.31 2.889(2) 123.6 2_676
N4 H4 O9 0.88 2.06 2.8949(19) 158.2 2_666
N14 H14A O6 0.91(3) 2.09(3) 2.995(2) 172(2) 2_776
N14 H14B O6 0.86(3) 2.26(3) 2.872(2) 128(2) 2_876
N15 H15 O13 0.88 2.05 2.8632(19) 153.0 .
N17 H17 N14 0.88 2.27 3.057(2) 149.4 2_875
N17 H17B O6 0.88 2.39 2.9077(19) 118.2 1_554
N18 H18A O10 0.88 2.14 2.939(2) 150.7 2_665
N18 H18B O12 0.88 2.17 3.017(2) 161.8 .

_diffrn_measured_fraction_theta_max 0.815
_diffrn_reflns_theta_full        68.05
_diffrn_measured_fraction_theta_full 0.815
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_shrv294
_database_code_depnum_ccdc_archive 'CCDC 1853790'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N6 O5'
_chemical_formula_weight         206.14

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.785(2)
_cell_length_b                   7.137(2)
_cell_length_c                   7.965(2)
_cell_angle_alpha                85.052(5)
_cell_angle_beta                 74.005(5)
_cell_angle_gamma                84.941(5)
_cell_volume                     368.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    676
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      23.84

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_T_max  0.7454
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3362
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.666
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1494
_reflns_number_gt                1018
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1494
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6437(4) 0.2529(3) 0.4763(3) 0.0168(6) Uani 1 1 d . . . . .
H1 H 0.617(5) 0.329(5) 0.394(4) 0.020 Uiso 1 1 d . U . . .
C2 C 0.7301(4) 0.0702(4) 0.4634(3) 0.0160(6) Uani 1 1 d . . . . .
N3 N 0.7541(4) 0.0002(3) 0.6154(3) 0.0184(6) Uani 1 1 d . . . . .
N4 N 0.6813(4) 0.1443(3) 0.7259(3) 0.0181(6) Uani 1 1 d . . . . .
H4 H 0.683(4) 0.124(4) 0.848(4) 0.022 Uiso 1 1 d . U . . .
C5 C 0.6098(4) 0.2996(4) 0.6460(4) 0.0171(6) Uani 1 1 d . . . . .
O6 O 0.5297(3) 0.4487(3) 0.7127(3) 0.0229(5) Uani 1 1 d . . . . .
C7 C 0.7802(4) -0.0310(4) 0.3039(3) 0.0169(6) Uani 1 1 d . . . . .
N8 N 0.7412(4) 0.0546(3) 0.1524(3) 0.0200(6) Uani 1 1 d . . . . .
O9 O 0.7515(4) -0.0379(3) 0.0230(3) 0.0283(6) Uani 1 1 d . . . . .
O10 O 0.6874(4) 0.2255(3) 0.1476(3) 0.0328(6) Uani 1 1 d . . . . .
N11 N 0.8638(4) -0.2190(3) 0.3029(3) 0.0183(6) Uani 1 1 d . . . . .
O12 O 0.9267(3) -0.3021(3) 0.1647(3) 0.0281(6) Uani 1 1 d . . . . .
O13 O 0.8788(4) -0.2992(3) 0.4439(3) 0.0271(5) Uani 1 1 d . . . . .
N1S N 0.1937(5) 1.3582(4) 0.1748(4) 0.0249(6) Uani 1 1 d . . . . .
H1S H 0.212(5) 1.314(5) 0.061(5) 0.030 Uiso 1 1 d . U . . .
H2S H 0.184(5) 1.258(6) 0.249(5) 0.030 Uiso 1 1 d . U . . .
H3S H 0.099(6) 1.442(5) 0.187(4) 0.030 Uiso 1 1 d . U . . .
H4S H 0.320(5) 1.419(5) 0.171(4) 0.030 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0246(13) 0.0111(12) 0.0154(13) 0.0009(10) -0.0094(10) 0.0061(10)
C2 0.0161(15) 0.0158(15) 0.0167(15) -0.0010(12) -0.0063(11) 0.0014(12)
N3 0.0223(13) 0.0179(13) 0.0153(12) -0.0057(10) -0.0065(9) 0.0057(10)
N4 0.0240(14) 0.0166(13) 0.0144(13) -0.0031(10) -0.0076(10) 0.0045(10)
C5 0.0201(15) 0.0166(15) 0.0160(15) -0.0013(12) -0.0080(11) 0.0019(12)
O6 0.0330(12) 0.0154(11) 0.0221(11) -0.0061(8) -0.0124(9) 0.0095(9)
C7 0.0218(16) 0.0148(15) 0.0145(14) -0.0022(11) -0.0071(11) 0.0045(12)
N8 0.0260(14) 0.0172(14) 0.0167(13) -0.0026(10) -0.0073(10) 0.0060(11)
O9 0.0506(15) 0.0206(12) 0.0175(11) -0.0059(8) -0.0170(9) 0.0073(10)
O10 0.0580(16) 0.0182(12) 0.0184(11) -0.0033(9) -0.0095(10) 0.0170(11)
N11 0.0221(14) 0.0161(13) 0.0176(13) -0.0024(10) -0.0080(10) 0.0029(10)
O12 0.0409(14) 0.0237(13) 0.0201(12) -0.0109(9) -0.0115(10) 0.0156(10)
O13 0.0440(14) 0.0191(12) 0.0184(11) 0.0006(9) -0.0123(9) 0.0082(10)
N1S 0.0377(18) 0.0153(15) 0.0254(15) -0.0057(12) -0.0169(13) 0.0089(13)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.372(3) . ?
N1 C2 1.382(4) . ?
N1 H1 0.86(3) . ?
C2 N3 1.316(3) . ?
C2 C7 1.459(4) . ?
N3 N4 1.380(3) . ?
N4 C5 1.350(4) . ?
N4 H4 0.98(3) . ?
C5 O6 1.244(3) . ?
C7 N8 1.386(4) . ?
C7 N11 1.410(4) . ?
N8 O10 1.243(3) . ?
N8 O9 1.254(3) . ?
N11 O13 1.242(3) . ?
N11 O12 1.247(3) . ?
N1S H1S 0.96(4) . ?
N1S H2S 0.89(4) . ?
N1S H3S 0.83(4) . ?
N1S H4S 0.99(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 108.3(2) . . ?
C5 N1 H1 124(2) . . ?
C2 N1 H1 128(2) . . ?
N3 C2 N1 110.5(2) . . ?
N3 C2 C7 125.4(3) . . ?
N1 C2 C7 124.1(2) . . ?
C2 N3 N4 104.4(2) . . ?
C5 N4 N3 112.9(2) . . ?
C5 N4 H4 128.1(18) . . ?
N3 N4 H4 119.0(18) . . ?
O6 C5 N4 127.5(3) . . ?
O6 C5 N1 128.5(3) . . ?
N4 C5 N1 103.9(2) . . ?
N8 C7 N11 119.0(2) . . ?
N8 C7 C2 120.5(3) . . ?
N11 C7 C2 120.5(2) . . ?
O10 N8 O9 119.5(2) . . ?
O10 N8 C7 119.0(2) . . ?
O9 N8 C7 121.5(2) . . ?
O13 N11 O12 120.4(2) . . ?
O13 N11 C7 118.0(2) . . ?
O12 N11 C7 121.6(2) . . ?
H1S N1S H2S 107(3) . . ?
H1S N1S H3S 106(3) . . ?
H2S N1S H3S 120(3) . . ?
H1S N1S H4S 107(3) . . ?
H2S N1S H4S 109(3) . . ?
H3S N1S H4S 108(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.5(3) . . . . ?
C5 N1 C2 C7 177.5(2) . . . . ?
N1 C2 N3 N4 -0.4(3) . . . . ?
C7 C2 N3 N4 -178.3(3) . . . . ?
C2 N3 N4 C5 1.2(3) . . . . ?
N3 N4 C5 O6 177.7(3) . . . . ?
N3 N4 C5 N1 -1.5(3) . . . . ?
C2 N1 C5 O6 -178.0(3) . . . . ?
C2 N1 C5 N4 1.2(3) . . . . ?
N3 C2 C7 N8 177.5(3) . . . . ?
N1 C2 C7 N8 -0.2(4) . . . . ?
N3 C2 C7 N11 -0.8(4) . . . . ?
N1 C2 C7 N11 -178.5(3) . . . . ?
N11 C7 N8 O10 -172.8(3) . . . . ?
C2 C7 N8 O10 8.9(4) . . . . ?
N11 C7 N8 O9 10.0(4) . . . . ?
C2 C7 N8 O9 -168.3(3) . . . . ?
N8 C7 N11 O13 -173.1(2) . . . . ?
C2 C7 N11 O13 5.2(4) . . . . ?
N8 C7 N11 O12 9.0(4) . . . . ?
C2 C7 N11 O12 -172.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.86(3) 2.05(3) 2.858(3) 157(3) 2_666
N1 H1 O10 0.86(3) 2.08(3) 2.575(3) 116(3) .
N4 H4 N8 0.98(3) 2.56(3) 3.529(3) 172(2) 1_556
N4 H4 O9 0.98(3) 1.86(3) 2.739(3) 148(3) 1_556
N4 H4 O10 0.98(3) 2.56(3) 3.470(3) 155(2) 1_556
N1S H1S O9 0.96(4) 2.11(4) 2.827(3) 131(3) 2_665
N1S H1S O12 0.96(4) 2.26(4) 3.098(3) 146(3) 2_665
N1S H2S N3 0.89(4) 2.12(4) 2.982(4) 164(3) 2_666
N1S H2S O13 0.89(4) 2.40(3) 2.939(4) 119(3) 2_666
N1S H3S O12 0.83(4) 2.10(4) 2.905(4) 163(3) 1_475
N1S H4S O6 0.99(4) 1.91(4) 2.797(4) 149(3) 2_676

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.098

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL shrv294 in P-1
CELL  0.71073   6.7853   7.1372   7.9650   85.052   74.005   84.941
ZERR     2.00   0.0021   0.0022   0.0024   0.0051    0.0048  0.0054
LATT   1
SFAC  C    H    N    O
UNIT  6 12 12 10
MERG   2
EQIV $1 -x+1, -y+1, -z+1
EQIV $2 x, y, z+1
EQIV $3 -x+1, -y+1, -z
EQIV $4 x-1, y+2, z
EQIV $5 -x+1, -y+2, -z+1
HTAB N1 O6_$1
HTAB N1 O10
HTAB N4 N8_$2
HTAB N4 O9_$2
HTAB N4 O10_$2
HTAB N1S O9_$3
HTAB N1S O12_$3
HTAB N1S N3_$1
HTAB N1S O13_$1
HTAB N1S O12_$4
HTAB N1S O6_$5
FMAP   2
PLAN   20
SIZE     0.028   0.063   0.095
ACTA
HTAB    2.00000
BOND   $H
CONF
LIST   4
WPDB  -2
L.S.  10
TEMP  -123.00
WGHT    0.078100
FVAR       0.24527
N1    3    0.643683    0.252886    0.476277    11.00000    0.02464    0.01110 =
         0.01541    0.00090   -0.00945    0.00610
H1    2    0.616554    0.329159    0.394397    11.00000   -1.20000
C2    1    0.730149    0.070199    0.463371    11.00000    0.01614    0.01583 =
         0.01674   -0.00099   -0.00631    0.00136
N3    3    0.754052    0.000153    0.615369    11.00000    0.02233    0.01786 =
         0.01529   -0.00566   -0.00648    0.00569
N4    3    0.681280    0.144275    0.725874    11.00000    0.02398    0.01657 =
         0.01438   -0.00311   -0.00757    0.00450
H4    2    0.683136    0.123533    0.848146    11.00000   -1.20000
C5    1    0.609823    0.299567    0.645971    11.00000    0.02006    0.01658 =
         0.01598   -0.00130   -0.00800    0.00192
O6    4    0.529696    0.448657    0.712684    11.00000    0.03303    0.01544 =
         0.02206   -0.00608   -0.01236    0.00951
C7    1    0.780202   -0.030969    0.303892    11.00000    0.02182    0.01477 =
         0.01447   -0.00220   -0.00712    0.00448
N8    3    0.741236    0.054582    0.152357    11.00000    0.02604    0.01718 =
         0.01672   -0.00265   -0.00732    0.00604
O9    4    0.751492   -0.037934    0.023015    11.00000    0.05062    0.02061 =
         0.01746   -0.00588   -0.01703    0.00726
O10   4    0.687376    0.225535    0.147601    11.00000    0.05799    0.01820 =
         0.01836   -0.00327   -0.00947    0.01704
N11   3    0.863804   -0.219015    0.302878    11.00000    0.02213    0.01612 =
         0.01759   -0.00240   -0.00799    0.00295
O12   4    0.926731   -0.302073    0.164704    11.00000    0.04095    0.02370 =
         0.02014   -0.01089   -0.01149    0.01558
O13   4    0.878787   -0.299169    0.443921    11.00000    0.04397    0.01906 =
         0.01841    0.00063   -0.01229    0.00817
N1S   3    0.193685    1.358173    0.174752    11.00000    0.03774    0.01528 =
         0.02541   -0.00567   -0.01689    0.00888
H1S   2    0.211588    1.314338    0.061128    11.00000   -1.20000
H2S   2    0.183557    1.257500    0.249028    11.00000   -1.20000
H3S   2    0.099092    1.441527    0.186877    11.00000   -1.20000
H4S   2    0.320015    1.418590    0.171295    11.00000   -1.20000
HKLF    4

REM  shrv294 in P-1
REM R1 =  0.0451 for    1018 Fo > 4sig(Fo)  and  0.0828 for all    1494 data
REM    145 parameters refined using      0 restraints

END

WGHT      0.0768      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 O6_$1
HTAB N1 O10
HTAB N4 N8_$2
HTAB N4 O9_$2
HTAB N4 O10_$2
HTAB N1S O9_$3
HTAB N1S O12_$3
HTAB N1S N3_$1
HTAB N1S O13_$1
HTAB N1S O12_$4
HTAB N1S O6_$5

REM Highest difference peak  0.366,  deepest hole -0.337,  1-sigma level  0.098
Q1    1   0.6053  0.2558  0.0232  11.00000  0.05    0.37
Q2    1   0.7062  0.0878 -0.0177  11.00000  0.05    0.30
Q3    1   0.9109  0.1558  0.0618  11.00000  0.05    0.29
Q4    1   0.7622  0.1805  0.0053  11.00000  0.05    0.27
Q5    1   0.8021 -0.1489 -0.0543  11.00000  0.05    0.26
Q6    1   0.3395  1.3389  0.0143  11.00000  0.05    0.26
Q7    1   0.4991  0.5094  0.8370  11.00000  0.05    0.26
Q8    1   0.0758  1.5250 -0.0284  11.00000  0.05    0.25
Q9    1   0.6387  0.2504  0.1604  11.00000  0.05    0.25
Q10   1   0.0647  1.3722  0.0060  11.00000  0.05    0.25
Q11   1   0.1335  1.2741  0.1118  11.00000  0.05    0.25
Q12   1   0.5406  0.0191  0.9366  11.00000  0.05    0.25
Q13   1   0.8044 -0.0423  0.0041  11.00000  0.05    0.25
Q14   1   1.0000  0.0000  0.0000  10.50000  0.05    0.24
Q15   1   0.8301 -0.0176 -0.0393  11.00000  0.05    0.24
Q16   1   0.8902  0.0823 -0.0401  11.00000  0.05    0.24
Q17   1   0.8267 -0.2903  0.1999  11.00000  0.05    0.24
Q18   1   0.7993  0.2982  0.1256  11.00000  0.05    0.24
Q19   1   0.9663 -0.3634  0.1191  11.00000  0.05    0.24
Q20   1   0.2631  1.1976  0.0067  11.00000  0.05    0.23
;
_shelx_res_checksum              39862

# start Validation Reply Form
_vrf_PLAT430_shrv294             
;
PROBLEM: Short Inter D...A Contact  O6     ..  O10     ..       2.79 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
# end Validation Reply Form
