# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
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data_shrv208
_database_code_depnum_ccdc_archive 'CCDC 897415'
#TrackingRef 'shrv208-final.cif'


_audit_creation_date             2012-08-21
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
;
N-(5-nitro-2H-1,2,3-triazol-4-yl)nitramide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H2 N6 O4'
_chemical_formula_sum            'C2 H2 N6 O4'
_chemical_formula_weight         174.10

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.430(7)
_cell_length_b                   5.989(4)
_cell_length_c                   8.915(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.043(8)
_cell_angle_gamma                90.00
_cell_volume                     602.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9893

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5068
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.47
_reflns_number_total             1242
_reflns_number_gt                836
_reflns_threshold_expression     I>2\s(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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1242
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.19527(19) 0.1071(4) 0.2507(3) 0.0410(6) Uani 1 1 d . . .
N2 N 0.0969(2) 0.2161(4) 0.2501(3) 0.0438(7) Uani 1 1 d . . .
H2 H 0.0305 0.1649 0.2044 0.053 Uiso 1 1 calc R . .
N3 N 0.10352(19) 0.4104(4) 0.3234(3) 0.0392(6) Uani 1 1 d . . .
C4 C 0.2182(2) 0.4263(4) 0.3777(3) 0.0310(6) Uani 1 1 d . . .
C5 C 0.2743(2) 0.2393(5) 0.3306(3) 0.0329(6) Uani 1 1 d . . .
N6 N 0.27330(19) 0.6039(4) 0.4584(3) 0.0387(6) Uani 1 1 d . . .
H6 H 0.3494 0.6086 0.4715 0.046 Uiso 1 1 calc R . .
N7 N 0.2162(2) 0.7704(4) 0.5183(2) 0.0380(6) Uani 1 1 d . . .
O8 O 0.10930(18) 0.7754(4) 0.4934(2) 0.0538(6) Uani 1 1 d . . .
O9 O 0.28032(19) 0.9072(4) 0.5921(2) 0.0514(6) Uani 1 1 d . . .
N10 N 0.39641(19) 0.1817(4) 0.3587(2) 0.0391(6) Uani 1 1 d . . .
O11 O 0.42967(19) 0.0183(4) 0.2981(3) 0.0641(7) Uani 1 1 d . . .
O12 O 0.45947(17) 0.3050(4) 0.4461(2) 0.0523(7) Uani 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 0.0341(12) 0.0363(15) 0.0497(13) -0.0043(10) -0.0026(10) -0.0009(10)
N2 0.0304(11) 0.0372(16) 0.0593(15) -0.0045(11) -0.0075(10) -0.0037(10)
N3 0.0321(12) 0.0313(14) 0.0517(13) -0.0020(10) -0.0014(10) 0.0004(9)
C4 0.0297(12) 0.0266(15) 0.0351(13) 0.0028(10) 0.0005(10) -0.0018(10)
C5 0.0295(13) 0.0304(16) 0.0366(13) 0.0028(11) -0.0017(10) -0.0021(11)
N6 0.0284(11) 0.0328(14) 0.0545(14) -0.0110(11) 0.0054(10) -0.0010(9)
N7 0.0397(13) 0.0325(14) 0.0413(12) 0.0001(10) 0.0047(10) 0.0029(10)
O8 0.0392(12) 0.0467(14) 0.0739(15) -0.0116(11) 0.0037(10) 0.0117(10)
O9 0.0561(13) 0.0413(14) 0.0547(12) -0.0156(10) 0.0018(10) -0.0019(10)
N10 0.0336(12) 0.0325(14) 0.0496(13) -0.0031(11) 0.0022(10) 0.0017(10)
O11 0.0496(13) 0.0510(16) 0.0883(16) -0.0255(13) 0.0005(11) 0.0144(11)
O12 0.0327(10) 0.0475(15) 0.0726(14) -0.0139(11) -0.0042(10) -0.0015(9)

_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 N2 1.299(3) . ?
N1 C5 1.322(3) . ?
N2 N3 1.331(3) . ?
N2 H2 0.8600 . ?
N3 C4 1.328(3) . ?
C4 N6 1.379(3) . ?
C4 C5 1.388(4) . ?
C5 N10 1.421(3) . ?
N6 N7 1.347(3) . ?
N6 H6 0.8600 . ?
N7 O8 1.208(3) . ?
N7 O9 1.220(3) . ?
N10 O11 1.208(3) . ?
N10 O12 1.223(3) . ?

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
N2 N1 C5 102.6(2) . . ?
N1 N2 N3 117.1(2) . . ?
N1 N2 H2 121.5 . . ?
N3 N2 H2 121.5 . . ?
C4 N3 N2 102.6(2) . . ?
N3 C4 N6 126.1(2) . . ?
N3 C4 C5 107.9(2) . . ?
N6 C4 C5 125.9(2) . . ?
N1 C5 C4 109.7(2) . . ?
N1 C5 N10 121.2(3) . . ?
C4 C5 N10 129.0(2) . . ?
N7 N6 C4 124.6(2) . . ?
N7 N6 H6 117.7 . . ?
C4 N6 H6 117.7 . . ?
O8 N7 O9 125.9(2) . . ?
O8 N7 N6 119.0(2) . . ?
O9 N7 N6 115.1(2) . . ?
O11 N10 O12 125.4(2) . . ?
O11 N10 C5 119.2(2) . . ?
O12 N10 C5 115.4(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 N3 -0.1(3) . . . . ?
N1 N2 N3 C4 -0.6(3) . . . . ?
N2 N3 C4 N6 177.2(2) . . . . ?
N2 N3 C4 C5 1.0(3) . . . . ?
N2 N1 C5 C4 0.7(3) . . . . ?
N2 N1 C5 N10 -179.7(2) . . . . ?
N3 C4 C5 N1 -1.1(3) . . . . ?
N6 C4 C5 N1 -177.4(2) . . . . ?
N3 C4 C5 N10 179.4(2) . . . . ?
N6 C4 C5 N10 3.1(4) . . . . ?
N3 C4 N6 N7 12.7(4) . . . . ?
C5 C4 N6 N7 -171.7(2) . . . . ?
C4 N6 N7 O8 -4.7(4) . . . . ?
C4 N6 N7 O9 176.7(2) . . . . ?
N1 C5 N10 O11 6.1(4) . . . . ?
C4 C5 N10 O11 -174.5(3) . . . . ?
N1 C5 N10 O12 -173.1(2) . . . . ?
C4 C5 N10 O12 6.3(4) . . . . ?

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 N3 0.86 2.15 2.925(3) 150.3 2_545
N6 H6 O12 0.86 2.25 3.088(3) 163.8 3_666

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.079