# 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 2016

####################################################################### 
# 
# 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_fx615
_database_code_depnum_ccdc_archive 'CCDC 1439310'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Wed Dec 22 14:52:38 2010'
;

_chemical_name_systematic        1-(3,5-dinitropyrazol-1-yl)-2-nitrazapropane
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H6 N6 O6'
_chemical_formula_sum            'C5 H6 N6 O6'
_chemical_formula_weight         246.138

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            10170
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996

_reflns_number_total             3961
_reflns_number_gt                2844
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      0.0603064615
_diffrn_orient_matrix_UB_12      0.0303126261
_diffrn_orient_matrix_UB_13      -0.0269010968
_diffrn_orient_matrix_UB_21      -0.0527858501
_diffrn_orient_matrix_UB_22      0.0511336042
_diffrn_orient_matrix_UB_23      -0.0181420282
_diffrn_orient_matrix_UB_31      0.0394304282
_diffrn_orient_matrix_UB_32      0.0454624791
_diffrn_orient_matrix_UB_33      0.0470455634
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    4.00  100.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00  100.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00  100.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000  240.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega  -39.00   56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00   56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega  -39.00   56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000  240.0000 95

;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2316(5)
_cell_length_b                   9.5937(5)
_cell_length_c                   12.7855(7)
_cell_angle_alpha                93.595(4)
_cell_angle_beta                 102.892(5)
_cell_angle_gamma                96.844(4)
_cell_volume                     973.06(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4236
_cell_measurement_theta_min      4.2197
_cell_measurement_theta_max      33.8939
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

_diffrn_special_details          ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0443P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0204(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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
O8 O 0.30712(13) 0.62980(11) 0.40000(9) 0.0389(3) Uani 1 1 d . . .
O9 O 0.44603(15) 0.29433(13) -0.02828(9) 0.0495(3) Uani 1 1 d . . .
N9 N 0.69402(14) 0.40817(12) 0.35955(9) 0.0257(3) Uani 1 1 d . . .
O7 O 0.11437(13) 0.67917(11) 0.26740(9) 0.0406(3) Uani 1 1 d . . .
O6 O 1.22291(14) 0.28964(12) 0.46640(9) 0.0508(3) Uani 1 1 d . . .
O5 O 1.14581(12) 0.28127(10) 0.29170(8) 0.0338(3) Uani 1 1 d . . .
O12 O 0.54434(13) 0.20128(11) 0.36485(8) 0.0394(3) Uani 1 1 d . . .
N2 N 0.83714(15) -0.07353(12) 0.24851(9) 0.0283(3) Uani 1 1 d . . .
N11 N 0.23730(15) 0.62247(12) 0.30444(10) 0.0291(3) Uani 1 1 d . . .
O11 O 0.80825(14) 0.21273(11) 0.36038(9) 0.0404(3) Uani 1 1 d . . .
N8 N 0.46712(14) 0.40307(12) 0.17232(9) 0.0257(3) Uani 1 1 d . . .
N1 N 0.95126(14) 0.00484(11) 0.20887(9) 0.0257(3) Uani 1 1 d . . .
N7 N 0.43853(13) 0.47550(11) 0.25749(8) 0.0222(3) Uani 1 1 d . . .
O4 O 0.40651(14) -0.08411(13) 0.15767(10) 0.0517(3) Uani 1 1 d . . .
N10 N 0.68046(16) 0.26606(12) 0.36105(9) 0.0289(3) Uani 1 1 d . . .
N3 N 1.16294(14) 0.08383(12) 0.37028(10) 0.0304(3) Uani 1 1 d . . .
O3 O 0.54610(15) -0.18884(13) 0.28700(9) 0.0528(3) Uani 1 1 d . . .
N12 N 0.33641(18) 0.36538(14) -0.01580(10) 0.0367(3) Uani 1 1 d . . .
O1 O 1.09825(17) 0.14424(12) 0.05758(9) 0.0504(3) Uani 1 1 d . . .
O2 O 0.89756(17) 0.27438(16) 0.04052(12) 0.0804(5) Uani 1 1 d . . .
O10 O 0.22142(16) 0.38994(13) -0.08765(9) 0.0529(3) Uani 1 1 d . . .
N5 N 0.96406(19) 0.17378(15) 0.07281(10) 0.0431(4) Uani 1 1 d . . .
N6 N 0.53788(17) -0.11075(14) 0.21492(11) 0.0370(3) Uani 1 1 d . . .
C7 C 0.55088(18) 0.47377(16) 0.36583(11) 0.0254(3) Uani 1 1 d . . .
C8 C 0.8431(2) 0.4821(2) 0.33487(16) 0.0360(4) Uani 1 1 d . . .
N4 N 1.17873(14) 0.22556(13) 0.37660(10) 0.0313(3) Uani 1 1 d . . .
C10 C 0.34339(18) 0.42674(14) 0.09164(11) 0.0272(3) Uani 1 1 d . . .
C1 C 0.7056(2) 0.05507(17) 0.12021(12) 0.0349(4) Uani 1 1 d . . .
C9 C 0.30051(16) 0.54097(14) 0.22836(11) 0.0240(3) Uani 1 1 d . . .
C2 C 1.12884(19) 0.01298(16) 0.26417(13) 0.0314(3) Uani 1 1 d . . .
C6 C 0.23449(19) 0.51214(15) 0.12052(12) 0.0287(3) Uani 1 1 d . . .
C4 C 0.69191(18) -0.04338(15) 0.19369(11) 0.0282(3) Uani 1 1 d . . .
C5 C 0.87410(19) 0.08326(15) 0.13293(11) 0.0303(3) Uani 1 1 d . . .
C3 C 1.2161(3) 0.0147(3) 0.46740(18) 0.0597(6) Uani 1 1 d . . .
H7A H 0.5883(17) 0.5710(16) 0.3929(11) 0.027(4) Uiso 1 1 d . . .
H2A H 1.1976(19) 0.0594(16) 0.2182(12) 0.034(4) Uiso 1 1 d . . .
H7B H 0.4857(18) 0.4245(15) 0.4070(12) 0.030(4) Uiso 1 1 d . . .
H2B H 1.1512(18) -0.0859(16) 0.2723(12) 0.033(4) Uiso 1 1 d . . .
H6 H 0.1411(19) 0.5426(15) 0.0795(12) 0.030(4) Uiso 1 1 d . . .
H1 H 0.627(2) 0.0927(16) 0.0769(13) 0.037(5) Uiso 1 1 d . . .
H8C H 0.858(2) 0.4439(18) 0.2672(15) 0.051(5) Uiso 1 1 d . . .
H8B H 0.937(2) 0.4726(17) 0.3862(14) 0.045(5) Uiso 1 1 d . . .
H8A H 0.829(2) 0.5776(19) 0.3296(13) 0.048(5) Uiso 1 1 d . . .
H3C H 1.167(3) -0.080(3) 0.4503(18) 0.084(8) Uiso 1 1 d . . .
H3A H 1.173(3) 0.054(2) 0.5216(18) 0.076(7) Uiso 1 1 d . . .
H3B H 1.342(4) 0.033(2) 0.4940(19) 0.101(8) Uiso 1 1 d . . .


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
O8 N11 1.2224(15) . ?
O9 N12 1.2254(17) . ?
N9 N10 1.3563(16) . ?
N9 C7 1.4154(17) . ?
N9 C8 1.4499(19) . ?
O7 N11 1.2222(14) . ?
O6 N4 1.2249(15) . ?
O5 N4 1.2302(15) . ?
O12 N10 1.2273(15) . ?
N2 C4 1.3183(18) . ?
N2 N1 1.3404(15) . ?
N11 C9 1.4338(18) . ?
O11 N10 1.2248(14) . ?
N8 C10 1.3299(17) . ?
N8 N7 1.3351(15) . ?
N1 C5 1.3574(18) . ?
N1 C2 1.4654(18) . ?
N7 C9 1.3545(16) . ?
N7 C7 1.4863(17) . ?
O4 N6 1.2274(17) . ?
N3 N4 1.3459(16) . ?
N3 C2 1.4319(19) . ?
N3 C3 1.450(2) . ?
O3 N6 1.2190(17) . ?
N12 O10 1.2197(16) . ?
N12 C10 1.4465(18) . ?
O1 N5 1.2256(18) . ?
O2 N5 1.2152(18) . ?
N5 C5 1.4414(19) . ?
N6 C4 1.4419(19) . ?
C7 H7A 0.963(15) . ?
C7 H7B 0.942(15) . ?
C8 H8C 0.958(18) . ?
C8 H8B 0.913(18) . ?
C8 H8A 0.941(17) . ?
C10 C6 1.377(2) . ?
C1 C5 1.352(2) . ?
C1 C4 1.386(2) . ?
C1 H1 0.882(16) . ?
C9 C6 1.362(2) . ?
C2 H2A 0.992(15) . ?
C2 H2B 0.995(15) . ?
C6 H6 0.919(15) . ?
C3 H3C 0.94(2) . ?
C3 H3A 0.93(2) . ?
C3 H3B 1.00(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
N10 N9 C7 117.78(11) . . ?
N10 N9 C8 118.61(12) . . ?
C7 N9 C8 122.88(13) . . ?
C4 N2 N1 103.81(11) . . ?
O7 N11 O8 124.85(13) . . ?
O7 N11 C9 116.21(12) . . ?
O8 N11 C9 118.94(11) . . ?
C10 N8 N7 103.43(11) . . ?
N2 N1 C5 110.43(11) . . ?
N2 N1 C2 117.93(11) . . ?
C5 N1 C2 130.55(12) . . ?
N8 N7 C9 110.72(11) . . ?
N8 N7 C7 119.96(11) . . ?
C9 N7 C7 129.31(11) . . ?
O11 N10 O12 125.08(12) . . ?
O11 N10 N9 116.43(12) . . ?
O12 N10 N9 118.49(11) . . ?
N4 N3 C2 116.19(12) . . ?
N4 N3 C3 119.19(15) . . ?
C2 N3 C3 123.17(15) . . ?
O10 N12 O9 124.94(13) . . ?
O10 N12 C10 116.87(14) . . ?
O9 N12 C10 118.19(13) . . ?
O2 N5 O1 125.31(14) . . ?
O2 N5 C5 115.89(15) . . ?
O1 N5 C5 118.79(14) . . ?
O3 N6 O4 124.78(14) . . ?
O3 N6 C4 118.82(13) . . ?
O4 N6 C4 116.40(13) . . ?
N9 C7 N7 111.40(11) . . ?
N9 C7 H7A 108.2(8) . . ?
N7 C7 H7A 106.2(8) . . ?
N9 C7 H7B 111.1(9) . . ?
N7 C7 H7B 106.2(9) . . ?
H7A C7 H7B 113.6(12) . . ?
N9 C8 H8C 110.5(10) . . ?
N9 C8 H8B 110.7(11) . . ?
H8C C8 H8B 107.6(14) . . ?
N9 C8 H8A 108.8(10) . . ?
H8C C8 H8A 108.2(14) . . ?
H8B C8 H8A 111.2(15) . . ?
O6 N4 O5 124.74(13) . . ?
O6 N4 N3 117.71(12) . . ?
O5 N4 N3 117.55(11) . . ?
N8 C10 C6 114.77(12) . . ?
N8 C10 N12 118.85(13) . . ?
C6 C10 N12 126.37(13) . . ?
C5 C1 C4 102.10(14) . . ?
C5 C1 H1 127.7(10) . . ?
C4 C1 H1 130.2(10) . . ?
N7 C9 C6 109.43(13) . . ?
N7 C9 N11 122.66(12) . . ?
C6 C9 N11 127.87(13) . . ?
N3 C2 N1 111.76(12) . . ?
N3 C2 H2A 112.5(9) . . ?
N1 C2 H2A 108.0(9) . . ?
N3 C2 H2B 107.2(8) . . ?
N1 C2 H2B 106.3(8) . . ?
H2A C2 H2B 110.9(12) . . ?
C9 C6 C10 101.65(13) . . ?
C9 C6 H6 127.9(9) . . ?
C10 C6 H6 130.4(9) . . ?
N2 C4 C1 114.33(13) . . ?
N2 C4 N6 119.32(13) . . ?
C1 C4 N6 126.34(14) . . ?
C1 C5 N1 109.31(13) . . ?
C1 C5 N5 127.44(14) . . ?
N1 C5 N5 123.13(13) . . ?
N3 C3 H3C 105.5(14) . . ?
N3 C3 H3A 109.0(14) . . ?
H3C C3 H3A 109(2) . . ?
N3 C3 H3B 110.7(14) . . ?
H3C C3 H3B 116.7(19) . . ?
H3A C3 H3B 105.9(19) . . ?

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
C4 N2 N1 C5 1.42(14) . . . . ?
C4 N2 N1 C2 170.76(11) . . . . ?
C10 N8 N7 C9 0.07(14) . . . . ?
C10 N8 N7 C7 179.08(12) . . . . ?
C7 N9 N10 O11 -176.84(11) . . . . ?
C8 N9 N10 O11 12.65(18) . . . . ?
C7 N9 N10 O12 1.91(17) . . . . ?
C8 N9 N10 O12 -168.59(13) . . . . ?
N10 N9 C7 N7 -86.63(15) . . . . ?
C8 N9 C7 N7 83.45(16) . . . . ?
N8 N7 C7 N9 9.00(17) . . . . ?
C9 N7 C7 N9 -172.19(12) . . . . ?
C2 N3 N4 O6 -173.52(12) . . . . ?
C3 N3 N4 O6 -6.8(2) . . . . ?
C2 N3 N4 O5 7.31(17) . . . . ?
C3 N3 N4 O5 174.04(16) . . . . ?
N7 N8 C10 C6 0.04(15) . . . . ?
N7 N8 C10 N12 178.80(11) . . . . ?
O10 N12 C10 N8 -179.75(12) . . . . ?
O9 N12 C10 N8 -0.42(19) . . . . ?
O10 N12 C10 C6 -1.2(2) . . . . ?
O9 N12 C10 C6 178.17(13) . . . . ?
N8 N7 C9 C6 -0.16(15) . . . . ?
C7 N7 C9 C6 -179.05(13) . . . . ?
N8 N7 C9 N11 177.87(11) . . . . ?
C7 N7 C9 N11 -1.0(2) . . . . ?
O7 N11 C9 N7 178.16(11) . . . . ?
O8 N11 C9 N7 -2.41(19) . . . . ?
O7 N11 C9 C6 -4.2(2) . . . . ?
O8 N11 C9 C6 175.23(13) . . . . ?
N4 N3 C2 N1 -78.95(15) . . . . ?
C3 N3 C2 N1 114.91(18) . . . . ?
N2 N1 C2 N3 -65.93(15) . . . . ?
C5 N1 C2 N3 100.88(17) . . . . ?
N7 C9 C6 C10 0.17(14) . . . . ?
N11 C9 C6 C10 -177.73(13) . . . . ?
N8 C10 C6 C9 -0.13(16) . . . . ?
N12 C10 C6 C9 -178.78(13) . . . . ?
N1 N2 C4 C1 -1.31(16) . . . . ?
N1 N2 C4 N6 179.56(11) . . . . ?
C5 C1 C4 N2 0.69(17) . . . . ?
C5 C1 C4 N6 179.73(13) . . . . ?
O3 N6 C4 N2 3.61(19) . . . . ?
O4 N6 C4 N2 -176.40(13) . . . . ?
O3 N6 C4 C1 -175.40(14) . . . . ?
O4 N6 C4 C1 4.6(2) . . . . ?
C4 C1 C5 N1 0.25(16) . . . . ?
C4 C1 C5 N5 176.36(14) . . . . ?
N2 N1 C5 C1 -1.08(16) . . . . ?
C2 N1 C5 C1 -168.66(14) . . . . ?
N2 N1 C5 N5 -177.40(12) . . . . ?
C2 N1 C5 N5 15.0(2) . . . . ?
O2 N5 C5 C1 31.7(2) . . . . ?
O1 N5 C5 C1 -147.86(15) . . . . ?
O2 N5 C5 N1 -152.70(15) . . . . ?
O1 N5 C5 N1 27.8(2) . . . . ?

_geom_special_details            ?


####################################################################### 
# 
# 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_gx036
_database_code_depnum_ccdc_archive 'CCDC 1439311'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_vrf_PLAT300_gx036               
;
Problem: Atom site occupancy of hydrogen atoms of C25 is constrained at 0.5
RESPONSE: fixed idealized disordered methyl group
;
_audit_block_code                ?
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        1-(3,4-dinitropyrazol-1-yl)-2-nitrazapropane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N6 O6'
_chemical_formula_sum            'C5 H6 N6 O6'
_chemical_formula_weight         246.16

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1342(16)
_cell_length_b                   9.3680(8)
_cell_length_c                   12.5388(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.400(10)
_cell_angle_gamma                90
_cell_volume                     1920.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1374
_cell_measurement_theta_min      4.1673
_cell_measurement_theta_max      33.7329

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9206
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.180
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3495
_reflns_number_gt                1592
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_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)+(0.0093P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3495
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_restrained_S_all      0.728
_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
O1 O 0.63231(11) 0.6728(2) 0.63078(15) 0.0407(5) Uani 1 1 d . . . . .
O2 O 0.62483(11) 0.5013(2) 0.74384(15) 0.0414(6) Uani 1 1 d . . . . .
O3 O 0.52337(13) 0.2865(2) 0.63182(15) 0.0460(6) Uani 1 1 d . . . . .
O4 O 0.39929(12) 0.2709(2) 0.64254(15) 0.0537(6) Uani 1 1 d . . . . .
O5 O 0.26023(11) 0.6697(2) 0.36036(15) 0.0420(6) Uani 1 1 d . . . . .
O6 O 0.28329(11) 0.8303(2) 0.24674(16) 0.0522(6) Uani 1 1 d . . . . .
N1 N 0.39038(13) 0.6967(2) 0.57664(16) 0.0273(6) Uani 1 1 d . . . . .
N2 N 0.47170(13) 0.7259(2) 0.60823(16) 0.0257(6) Uani 1 1 d . . . . .
N3 N 0.59406(14) 0.5901(3) 0.67196(19) 0.0289(6) Uani 1 1 d . . . . .
N4 N 0.45783(16) 0.3382(3) 0.63243(18) 0.0361(6) Uani 1 1 d . . . . .
N5 N 0.33048(13) 0.8638(2) 0.42900(19) 0.0303(6) Uani 1 1 d . . . . .
N6 N 0.28908(14) 0.7840(3) 0.3407(2) 0.0348(6) Uani 1 1 d . . . . .
C1 C 0.50579(16) 0.6000(3) 0.6329(2) 0.0226(7) Uani 1 1 d . . . . .
C2 C 0.44795(17) 0.4910(3) 0.6195(2) 0.0243(7) Uani 1 1 d . . . . .
C3 C 0.37412(19) 0.5582(3) 0.5820(2) 0.0302(8) Uani 1 1 d . . . . .
C4 C 0.33165(19) 0.8140(4) 0.5371(3) 0.0349(8) Uani 1 1 d . . . . .
C5 C 0.36525(18) 0.9983(3) 0.4096(3) 0.0540(9) Uani 1 1 d . . . . .
H5A H 0.4065 0.9810 0.3713 0.081 Uiso 1 1 calc R U . . .
H5B H 0.3908 1.0455 0.4813 0.081 Uiso 1 1 calc R U . . .
H5C H 0.3220 1.0595 0.3631 0.081 Uiso 1 1 calc R U . . .
O28 O 0.06892(11) 0.75884(19) 0.18928(15) 0.0410(6) Uani 1 1 d . . . . .
O27 O -0.05453(12) 0.6984(2) 0.09158(16) 0.0432(6) Uani 1 1 d . . . . .
O26 O -0.13854(11) 0.45838(19) 0.13895(14) 0.0356(5) Uani 1 1 d . . . . .
O25 O -0.12700(10) 0.3042(2) 0.01569(15) 0.0437(6) Uani 1 1 d . . . . .
O29 O 0.23600(11) 0.3603(2) 0.06787(16) 0.0387(5) Uani 1 1 d . . . . .
O30 O 0.22036(11) 0.1773(2) -0.04544(16) 0.0470(6) Uani 1 1 d . . . . .
N25 N 0.11216(12) 0.3316(2) 0.18514(16) 0.0249(5) Uani 1 1 d . . . . .
C22 C 0.11760(19) 0.4729(3) 0.1938(2) 0.0266(7) Uani 1 1 d . . . . .
N28 N 0.01609(15) 0.6701(3) 0.14610(18) 0.0307(6) Uani 1 1 d . . . . .
N27 N -0.09845(14) 0.3878(2) 0.09249(19) 0.0294(6) Uani 1 1 d . . . . .
N29 N 0.18611(12) 0.1563(2) 0.11049(18) 0.0286(6) Uani 1 1 d . . . . .
N30 N 0.21541(13) 0.2381(3) 0.0397(2) 0.0347(6) Uani 1 1 d . . . . .
C21 C 0.03909(16) 0.5224(3) 0.1591(2) 0.0227(7) Uani 1 1 d . . . . .
C20 C -0.00939(15) 0.4009(3) 0.1313(2) 0.0216(7) Uani 1 1 d . . . . .
N26 N 0.03395(12) 0.2827(2) 0.14689(16) 0.0247(5) Uani 1 1 d . . . . .
C24 C 0.17951(19) 0.2270(4) 0.2083(3) 0.0305(8) Uani 1 1 d . . . . .
C25 C 0.13902(16) 0.0281(3) 0.0662(2) 0.0398(8) Uani 1 1 d . . . . .
H25A H 0.1223 -0.0189 0.1258 0.060 Uiso 0.5 1 calc R U P . .
H25B H 0.0903 0.0545 0.0053 0.060 Uiso 0.5 1 calc R U P . .
H25C H 0.1728 -0.0374 0.0380 0.060 Uiso 0.5 1 calc R U P . .
H25D H 0.1346 0.0177 -0.0131 0.060 Uiso 0.5 1 calc R U P . .
H25E H 0.1667 -0.0557 0.1074 0.060 Uiso 0.5 1 calc R U P . .
H25F H 0.0842 0.0362 0.0747 0.060 Uiso 0.5 1 calc R U P . .
H3A H 0.3225(13) 0.520(2) 0.5575(18) 0.022(7) Uiso 1 1 d . . . . .
H22A H 0.1666(14) 0.520(3) 0.218(2) 0.035(8) Uiso 1 1 d . . . . .
H4B H 0.2742(15) 0.770(3) 0.5383(18) 0.045(8) Uiso 1 1 d . . . . .
H4A H 0.3484(13) 0.892(2) 0.5880(18) 0.024(8) Uiso 1 1 d . . . . .
H24A H 0.2266(14) 0.285(2) 0.2443(17) 0.026(7) Uiso 1 1 d . . . . .
H24B H 0.1664(13) 0.158(2) 0.2526(18) 0.025(8) Uiso 1 1 d . . . . .


_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
O1 N3 1.224(2) . ?
O2 N3 1.224(2) . ?
O3 N4 1.225(2) . ?
O4 N4 1.223(2) . ?
O5 N6 1.234(3) . ?
O6 N6 1.232(2) . ?
N1 C3 1.333(3) . ?
N1 N2 1.358(3) . ?
N1 C4 1.472(3) . ?
N2 C1 1.312(3) . ?
N3 C1 1.447(3) . ?
N4 C2 1.445(3) . ?
N5 N6 1.348(3) . ?
N5 C4 1.427(3) . ?
N5 C5 1.444(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.365(4) . ?
C3 H3A 0.92(2) . ?
C4 H4B 1.07(2) . ?
C4 H4A 0.95(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O28 N28 1.229(3) . ?
O27 N28 1.228(2) . ?
O26 N27 1.220(2) . ?
O25 N27 1.224(2) . ?
O29 N30 1.219(3) . ?
O30 N30 1.235(3) . ?
N25 C22 1.329(3) . ?
N25 N26 1.361(2) . ?
N25 C24 1.476(3) . ?
C22 C21 1.365(3) . ?
C22 H22A 0.91(2) . ?
N28 C21 1.434(3) . ?
N27 C20 1.462(3) . ?
N29 N30 1.376(3) . ?
N29 C24 1.427(3) . ?
N29 C25 1.461(3) . ?
C21 C20 1.391(3) . ?
C20 N26 1.315(3) . ?
C24 H24A 0.96(2) . ?
C24 H24B 0.92(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 H25D 0.9800 . ?
C25 H25E 0.9800 . ?
C25 H25F 0.9800 . ?

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
C3 N1 N2 113.1(2) . . ?
C3 N1 C4 127.7(3) . . ?
N2 N1 C4 119.1(2) . . ?
C1 N2 N1 103.5(2) . . ?
O1 N3 O2 125.0(2) . . ?
O1 N3 C1 117.0(2) . . ?
O2 N3 C1 118.0(2) . . ?
O4 N4 O3 125.4(3) . . ?
O4 N4 C2 116.8(3) . . ?
O3 N4 C2 117.9(2) . . ?
N6 N5 C4 116.9(3) . . ?
N6 N5 C5 119.2(2) . . ?
C4 N5 C5 123.7(3) . . ?
O6 N6 O5 125.0(3) . . ?
O6 N6 N5 117.5(3) . . ?
O5 N6 N5 117.5(2) . . ?
N2 C1 C2 112.3(2) . . ?
N2 C1 N3 118.9(2) . . ?
C2 C1 N3 128.8(3) . . ?
C3 C2 C1 104.8(3) . . ?
C3 C2 N4 124.2(3) . . ?
C1 C2 N4 130.9(3) . . ?
N1 C3 C2 106.3(3) . . ?
N1 C3 H3A 124.1(14) . . ?
C2 C3 H3A 129.3(15) . . ?
N5 C4 N1 112.2(2) . . ?
N5 C4 H4B 112.8(12) . . ?
N1 C4 H4B 104.3(13) . . ?
N5 C4 H4A 107.6(14) . . ?
N1 C4 H4A 107.8(14) . . ?
H4B C4 H4A 112.1(18) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C22 N25 N26 113.7(2) . . ?
C22 N25 C24 127.9(2) . . ?
N26 N25 C24 118.4(2) . . ?
N25 C22 C21 105.9(3) . . ?
N25 C22 H22A 122.6(16) . . ?
C21 C22 H22A 131.5(16) . . ?
O27 N28 O28 124.9(3) . . ?
O27 N28 C21 117.6(2) . . ?
O28 N28 C21 117.5(2) . . ?
O26 N27 O25 125.0(2) . . ?
O26 N27 C20 118.4(2) . . ?
O25 N27 C20 116.6(2) . . ?
N30 N29 C24 115.7(2) . . ?
N30 N29 C25 118.6(2) . . ?
C24 N29 C25 122.1(2) . . ?
O29 N30 O30 126.5(2) . . ?
O29 N30 N29 117.7(2) . . ?
O30 N30 N29 115.7(3) . . ?
C22 C21 C20 105.0(3) . . ?
C22 C21 N28 125.1(3) . . ?
C20 C21 N28 129.6(3) . . ?
N26 C20 C21 112.6(2) . . ?
N26 C20 N27 117.7(2) . . ?
C21 C20 N27 129.6(3) . . ?
C20 N26 N25 102.8(2) . . ?
N29 C24 N25 113.4(2) . . ?
N29 C24 H24A 113.0(13) . . ?
N25 C24 H24A 102.5(14) . . ?
N29 C24 H24B 106.9(14) . . ?
N25 C24 H24B 105.4(14) . . ?
H24A C24 H24B 115.5(19) . . ?
N29 C25 H25A 109.5 . . ?
N29 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N29 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N29 C25 H25D 109.5 . . ?
H25A C25 H25D 141.1 . . ?
H25B C25 H25D 56.3 . . ?
H25C C25 H25D 56.3 . . ?
N29 C25 H25E 109.5 . . ?
H25A C25 H25E 56.3 . . ?
H25B C25 H25E 141.1 . . ?
H25C C25 H25E 56.3 . . ?
H25D C25 H25E 109.5 . . ?
N29 C25 H25F 109.5 . . ?
H25A C25 H25F 56.3 . . ?
H25B C25 H25F 56.3 . . ?
H25C C25 H25F 141.1 . . ?
H25D C25 H25F 109.5 . . ?
H25E C25 H25F 109.5 . . ?

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
C3 N1 N2 C1 0.4(3) . . . . ?
C4 N1 N2 C1 -177.1(2) . . . . ?
C4 N5 N6 O6 175.6(2) . . . . ?
C5 N5 N6 O6 0.3(3) . . . . ?
C4 N5 N6 O5 -4.8(3) . . . . ?
C5 N5 N6 O5 179.9(2) . . . . ?
N1 N2 C1 C2 -1.0(3) . . . . ?
N1 N2 C1 N3 -179.3(2) . . . . ?
O1 N3 C1 N2 -35.9(3) . . . . ?
O2 N3 C1 N2 143.5(2) . . . . ?
O1 N3 C1 C2 146.2(3) . . . . ?
O2 N3 C1 C2 -34.5(4) . . . . ?
N2 C1 C2 C3 1.2(3) . . . . ?
N3 C1 C2 C3 179.3(2) . . . . ?
N2 C1 C2 N4 177.1(2) . . . . ?
N3 C1 C2 N4 -4.9(4) . . . . ?
O4 N4 C2 C3 -22.3(4) . . . . ?
O3 N4 C2 C3 157.3(3) . . . . ?
O4 N4 C2 C1 162.5(3) . . . . ?
O3 N4 C2 C1 -17.9(4) . . . . ?
N2 N1 C3 C2 0.3(3) . . . . ?
C4 N1 C3 C2 177.5(2) . . . . ?
C1 C2 C3 N1 -0.8(3) . . . . ?
N4 C2 C3 N1 -177.1(2) . . . . ?
N6 N5 C4 N1 78.1(3) . . . . ?
C5 N5 C4 N1 -106.8(3) . . . . ?
C3 N1 C4 N5 -105.1(3) . . . . ?
N2 N1 C4 N5 71.9(3) . . . . ?
N26 N25 C22 C21 -0.3(3) . . . . ?
C24 N25 C22 C21 177.6(2) . . . . ?
C24 N29 N30 O29 2.8(3) . . . . ?
C25 N29 N30 O29 161.9(2) . . . . ?
C24 N29 N30 O30 -179.3(2) . . . . ?
C25 N29 N30 O30 -20.2(3) . . . . ?
N25 C22 C21 C20 0.1(3) . . . . ?
N25 C22 C21 N28 -174.7(2) . . . . ?
O27 N28 C21 C22 164.2(2) . . . . ?
O28 N28 C21 C22 -15.0(4) . . . . ?
O27 N28 C21 C20 -9.3(4) . . . . ?
O28 N28 C21 C20 171.5(2) . . . . ?
C22 C21 C20 N26 0.1(3) . . . . ?
N28 C21 C20 N26 174.6(2) . . . . ?
C22 C21 C20 N27 177.8(2) . . . . ?
N28 C21 C20 N27 -7.7(4) . . . . ?
O26 N27 C20 N26 133.7(2) . . . . ?
O25 N27 C20 N26 -45.4(3) . . . . ?
O26 N27 C20 C21 -43.9(4) . . . . ?
O25 N27 C20 C21 137.0(3) . . . . ?
C21 C20 N26 N25 -0.3(3) . . . . ?
N27 C20 N26 N25 -178.3(2) . . . . ?
C22 N25 N26 C20 0.4(3) . . . . ?
C24 N25 N26 C20 -177.7(2) . . . . ?
N30 N29 C24 N25 72.1(3) . . . . ?
C25 N29 C24 N25 -86.3(3) . . . . ?
C22 N25 C24 N29 -111.6(3) . . . . ?
N26 N25 C24 N29 66.2(3) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_gx141
_database_code_depnum_ccdc_archive 'CCDC 1439312'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Fri Mar 04 13:38:26 2011'
;

_chemical_name_systematic        
1-(3,4,4'-Trinitro-1,3'-bipyrazol-2'-yl)-2-nitrazapropane
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H7 N9 O8'
_chemical_formula_sum            'C8 H7 N9 O8'
_chemical_formula_weight         357.197

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            3705
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.989

_reflns_number_total             2777
_reflns_number_gt                1700
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0508783649
_diffrn_orient_matrix_UB_12      -0.0271516868
_diffrn_orient_matrix_UB_13      0.0339257805
_diffrn_orient_matrix_UB_21      0.0031421413
_diffrn_orient_matrix_UB_22      -0.0787714722
_diffrn_orient_matrix_UB_23      -0.0479093015
_diffrn_orient_matrix_UB_31      0.0711745840
_diffrn_orient_matrix_UB_32      0.0012848803
_diffrn_orient_matrix_UB_33      0.0590658296
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00  103.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00  103.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   39.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.0000   80.0000  250.0000 104

;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5617(9)
_cell_length_b                   9.3986(9)
_cell_length_c                   9.7876(10)
_cell_angle_alpha                113.277(9)
_cell_angle_beta                 106.073(9)
_cell_angle_gamma                92.266(8)
_cell_volume                     685.23(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1305
_cell_measurement_theta_min      4.3459
_cell_measurement_theta_max      33.6791
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?


_diffrn_special_details          ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.042

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0272P)²+0.0000P] 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_extinction_expression ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2777
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_restrained_S_all      0.822
_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
O4 O -0.00196(16) 0.13947(16) 0.63844(16) 0.0366(4) Uani 1 1 d . . .
O6 O 0.13891(16) 0.62468(16) 0.57076(17) 0.0367(4) Uani 1 1 d . . .
O3 O 0.00720(16) -0.02072(18) 0.75004(17) 0.0425(4) Uani 1 1 d . . .
O2 O 0.58443(18) 0.47192(16) 0.85380(17) 0.0400(4) Uani 1 1 d . . .
O7 O 0.24118(17) 0.21227(17) 0.14074(15) 0.0412(4) Uani 1 1 d . . .
O1 O 0.7958(2) 0.55922(17) 1.06774(17) 0.0483(4) Uani 1 1 d . . .
O8 O 0.50067(17) 0.30104(16) 0.27368(16) 0.0375(4) Uani 1 1 d . . .
O5 O 0.20693(18) 0.54742(16) 0.35762(17) 0.0428(4) Uani 1 1 d . . .
N7 N 0.19215(19) 0.53288(18) 0.4718(2) 0.0284(4) Uani 1 1 d . . .
N5 N 0.0724(2) 0.06486(19) 0.70697(19) 0.0292(4) Uani 1 1 d . . .
N1 N 0.50034(18) 0.13280(17) 0.75074(17) 0.0228(4) Uani 1 1 d . . .
N6 N 0.31074(18) 0.22996(17) 0.59108(17) 0.0228(4) Uani 1 1 d . . .
N2 N 0.50711(19) 0.05158(18) 0.84069(18) 0.0277(4) Uani 1 1 d . . .
N8 N 0.3569(2) 0.26528(18) 0.26177(19) 0.0271(4) Uani 1 1 d . . .
N4 N 0.7085(2) 0.4561(2) 0.9411(2) 0.0326(4) Uani 1 1 d . . .
N9 N 0.36595(18) 0.18261(17) 0.46280(17) 0.0237(4) Uani 1 1 d . . .
N3 N 0.75608(19) 0.31294(18) 0.89497(18) 0.0288(4) Uani 1 1 d . . .
C6 C 0.2439(2) 0.3967(2) 0.4923(2) 0.0220(4) Uani 1 1 d . . .
C8 C 0.3457(2) 0.1504(2) 0.6887(2) 0.0209(4) Uani 1 1 d . . .
C7 C 0.2473(2) 0.0784(2) 0.7399(2) 0.0229(4) Uani 1 1 d . . .
C2 C 0.6581(2) 0.1944(2) 0.7454(2) 0.0250(4) Uani 1 1 d . . .
C4 C 0.2385(2) 0.3587(2) 0.6119(2) 0.0253(4) Uani 1 1 d . . .
C5 C 0.3233(2) 0.2854(2) 0.4050(2) 0.0218(4) Uani 1 1 d . . .
C3 C 0.3522(2) 0.0194(2) 0.8336(2) 0.0276(5) Uani 1 1 d . . .
C1 C 0.8812(3) 0.2815(4) 1.0105(3) 0.0433(6) Uani 1 1 d . . .
H2A H 0.715(2) 0.104(2) 0.718(2) 0.035(6) Uiso 1 1 d . . .
H3A H 0.325(2) -0.037(2) 0.889(2) 0.032(5) Uiso 1 1 d . . .
H2B H 0.635(2) 0.236(2) 0.666(2) 0.033(5) Uiso 1 1 d . . .
H4A H 0.199(2) 0.405(2) 0.699(2) 0.038(6) Uiso 1 1 d . . .
H1A H 0.885(3) 0.167(3) 0.960(3) 0.065(8) Uiso 1 1 d . . .
H1C H 0.844(3) 0.294(2) 1.091(3) 0.044(7) Uiso 1 1 d . . .
H1B H 0.980(4) 0.349(3) 1.041(3) 0.093(10) Uiso 1 1 d . . .


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
O4 N5 1.2317(19) . ?
O6 N7 1.2270(19) . ?
O3 N5 1.2241(19) . ?
O2 N4 1.221(2) . ?
O7 N8 1.2158(18) . ?
O1 N4 1.230(2) . ?
O8 N8 1.2239(19) . ?
O5 N7 1.2170(19) . ?
N7 C6 1.440(2) . ?
N5 C7 1.431(2) . ?
N1 C8 1.342(2) . ?
N1 N2 1.367(2) . ?
N1 C2 1.471(2) . ?
N6 C4 1.350(2) . ?
N6 N9 1.3789(19) . ?
N6 C8 1.409(2) . ?
N2 C3 1.325(2) . ?
N8 C5 1.451(2) . ?
N4 N3 1.359(2) . ?
N9 C5 1.316(2) . ?
N3 C2 1.430(2) . ?
N3 C1 1.460(3) . ?
C6 C4 1.364(3) . ?
C6 C5 1.399(2) . ?
C8 C7 1.370(2) . ?
C7 C3 1.393(3) . ?
C2 H2A 0.975(19) . ?
C2 H2B 0.978(19) . ?
C4 H4A 0.957(19) . ?
C3 H3A 0.958(18) . ?
C1 H1A 1.00(3) . ?
C1 H1C 0.90(2) . ?
C1 H1B 0.93(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
O5 N7 O6 125.65(16) . . ?
O5 N7 C6 116.62(16) . . ?
O6 N7 C6 117.73(16) . . ?
O3 N5 O4 124.59(16) . . ?
O3 N5 C7 116.97(16) . . ?
O4 N5 C7 118.43(16) . . ?
C8 N1 N2 111.98(14) . . ?
C8 N1 C2 130.79(16) . . ?
N2 N1 C2 117.09(15) . . ?
C4 N6 N9 112.95(15) . . ?
C4 N6 C8 128.24(15) . . ?
N9 N6 C8 118.61(14) . . ?
C3 N2 N1 104.82(15) . . ?
O7 N8 O8 125.87(16) . . ?
O7 N8 C5 117.46(15) . . ?
O8 N8 C5 116.66(16) . . ?
O2 N4 O1 125.72(18) . . ?
O2 N4 N3 117.65(17) . . ?
O1 N4 N3 116.63(17) . . ?
C5 N9 N6 103.05(15) . . ?
N4 N3 C2 116.77(16) . . ?
N4 N3 C1 118.29(18) . . ?
C2 N3 C1 123.86(19) . . ?
C4 C6 C5 105.73(15) . . ?
C4 C6 N7 126.03(17) . . ?
C5 C6 N7 127.99(16) . . ?
N1 C8 C7 106.30(15) . . ?
N1 C8 N6 121.31(15) . . ?
C7 C8 N6 132.39(16) . . ?
C8 C7 C3 106.07(17) . . ?
C8 C7 N5 128.23(17) . . ?
C3 C7 N5 125.70(17) . . ?
N3 C2 N1 111.65(15) . . ?
N3 C2 H2A 108.6(11) . . ?
N1 C2 H2A 104.7(10) . . ?
N3 C2 H2B 110.9(11) . . ?
N1 C2 H2B 108.4(11) . . ?
H2A C2 H2B 112.5(15) . . ?
N6 C4 C6 105.73(17) . . ?
N6 C4 H4A 120.8(11) . . ?
C6 C4 H4A 133.4(11) . . ?
N9 C5 C6 112.53(16) . . ?
N9 C5 N8 117.72(16) . . ?
C6 C5 N8 129.69(16) . . ?
N2 C3 C7 110.83(17) . . ?
N2 C3 H3A 120.8(11) . . ?
C7 C3 H3A 128.4(11) . . ?
N3 C1 H1A 105.9(14) . . ?
N3 C1 H1C 108.1(14) . . ?
H1A C1 H1C 105.5(19) . . ?
N3 C1 H1B 108.8(17) . . ?
H1A C1 H1B 116(2) . . ?
H1C C1 H1B 113(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
C8 N1 N2 C3 -0.2(2) . . . . ?
C2 N1 N2 C3 175.90(16) . . . . ?
C4 N6 N9 C5 -0.74(19) . . . . ?
C8 N6 N9 C5 -175.97(15) . . . . ?
O2 N4 N3 C2 1.6(2) . . . . ?
O1 N4 N3 C2 -177.93(15) . . . . ?
O2 N4 N3 C1 -167.02(19) . . . . ?
O1 N4 N3 C1 13.5(3) . . . . ?
O5 N7 C6 C4 179.73(17) . . . . ?
O6 N7 C6 C4 0.5(3) . . . . ?
O5 N7 C6 C5 6.3(3) . . . . ?
O6 N7 C6 C5 -172.94(17) . . . . ?
N2 N1 C8 C7 0.1(2) . . . . ?
C2 N1 C8 C7 -175.35(17) . . . . ?
N2 N1 C8 N6 -179.59(15) . . . . ?
C2 N1 C8 N6 5.0(3) . . . . ?
C4 N6 C8 N1 -121.1(2) . . . . ?
N9 N6 C8 N1 53.3(2) . . . . ?
C4 N6 C8 C7 59.3(3) . . . . ?
N9 N6 C8 C7 -126.3(2) . . . . ?
N1 C8 C7 C3 0.1(2) . . . . ?
N6 C8 C7 C3 179.71(19) . . . . ?
N1 C8 C7 N5 179.80(17) . . . . ?
N6 C8 C7 N5 -0.6(3) . . . . ?
O3 N5 C7 C8 171.59(17) . . . . ?
O4 N5 C7 C8 -8.6(3) . . . . ?
O3 N5 C7 C3 -8.8(3) . . . . ?
O4 N5 C7 C3 171.04(18) . . . . ?
N4 N3 C2 N1 -74.6(2) . . . . ?
C1 N3 C2 N1 93.3(2) . . . . ?
C8 N1 C2 N3 109.5(2) . . . . ?
N2 N1 C2 N3 -65.8(2) . . . . ?
N9 N6 C4 C6 0.8(2) . . . . ?
C8 N6 C4 C6 175.51(16) . . . . ?
C5 C6 C4 N6 -0.6(2) . . . . ?
N7 C6 C4 N6 -175.17(16) . . . . ?
N6 N9 C5 C6 0.34(19) . . . . ?
N6 N9 C5 N8 -177.21(15) . . . . ?
C4 C6 C5 N9 0.1(2) . . . . ?
N7 C6 C5 N9 174.59(16) . . . . ?
C4 C6 C5 N8 177.32(18) . . . . ?
N7 C6 C5 N8 -8.2(3) . . . . ?
O7 N8 C5 N9 104.0(2) . . . . ?
O8 N8 C5 N9 -74.8(2) . . . . ?
O7 N8 C5 C6 -73.0(3) . . . . ?
O8 N8 C5 C6 108.2(2) . . . . ?
N1 N2 C3 C7 0.3(2) . . . . ?
C8 C7 C3 N2 -0.2(2) . . . . ?
N5 C7 C3 N2 -179.95(17) . . . . ?

_geom_special_details            ?



####################################################################### 
# 
# 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_gx173
_database_code_depnum_ccdc_archive 'CCDC 1439313'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Fri Mar 18 10:41:27 2011'
;

_chemical_name_systematic        
1-(5-chloro-3,4-dinitropyrazol-1-yl)-2-nitrazapropane
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H5 Cl N6 O6'
_chemical_formula_sum            'C5 H5 Cl N6 O6'
_chemical_formula_weight         280.583

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            10410
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996

_reflns_number_total             2100
_reflns_number_gt                1327
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0353685606
_diffrn_orient_matrix_UB_12      -0.0288603173
_diffrn_orient_matrix_UB_13      -0.0399000525
_diffrn_orient_matrix_UB_21      -0.0061275399
_diffrn_orient_matrix_UB_22      0.0507133014
_diffrn_orient_matrix_UB_23      -0.0233792830
_diffrn_orient_matrix_UB_31      0.1215116488
_diffrn_orient_matrix_UB_32      -0.0058057655
_diffrn_orient_matrix_UB_33      -0.0060881310
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   70.0000  240.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega  -41.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega  -41.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -70.0000  240.0000 101

;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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                   5.6441(6)
_cell_length_b                   12.0820(12)
_cell_length_c                   15.3446(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.068(10)
_cell_angle_gamma                90.00
_cell_volume                     1036.02(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2325
_cell_measurement_theta_min      4.1972
_cell_measurement_theta_max      32.4066
_cell_special_details            ?

_exptl_crystal_description       bar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

_diffrn_special_details          ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.050

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0340P)²+0.0000P] 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_extinction_expression ?
_refine_ls_number_reflns         2100
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_restrained_S_all      0.849
_refine_ls_shift/su_max          0.001
_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
Cl Cl 0.82704(10) 0.27152(5) 0.71540(3) 0.03401(17) Uani 1 1 d . . .
O6 O 0.9464(3) 0.02841(13) 0.75193(10) 0.0417(4) Uani 1 1 d . . .
O1 O 0.6111(3) 0.39713(13) 0.38951(10) 0.0432(4) Uani 1 1 d . . .
N4 N 0.2651(3) 0.14042(14) 0.58241(10) 0.0249(4) Uani 1 1 d . . .
O5 O 0.6692(3) -0.09775(13) 0.72899(10) 0.0405(4) Uani 1 1 d . . .
O2 O 0.7598(3) 0.39746(14) 0.52929(11) 0.0426(4) Uani 1 1 d . . .
O3 O 0.0503(3) -0.06660(14) 0.59148(11) 0.0442(4) Uani 1 1 d . . .
O4 O 0.3904(3) -0.12361(14) 0.55922(11) 0.0475(5) Uani 1 1 d . . .
N5 N 0.2620(3) -0.05696(15) 0.58702(10) 0.0257(4) Uani 1 1 d . . .
N2 N 0.5960(3) 0.38186(14) 0.46803(12) 0.0302(4) Uani 1 1 d . . .
N3 N 0.4164(3) 0.22334(14) 0.61338(10) 0.0225(4) Uani 1 1 d . . .
C3 C 0.6139(3) 0.18595(17) 0.66523(12) 0.0228(5) Uani 1 1 d . . .
N1 N 0.3844(3) 0.34624(14) 0.48836(11) 0.0256(4) Uani 1 1 d . . .
N6 N 0.7471(3) -0.00373(17) 0.71983(10) 0.0305(5) Uani 1 1 d . . .
C2 C 0.3563(4) 0.33560(18) 0.58002(14) 0.0249(5) Uani 1 1 d . . .
C4 C 0.5908(4) 0.07209(17) 0.66764(12) 0.0225(5) Uani 1 1 d . . .
C5 C 0.3726(4) 0.05056(17) 0.61522(13) 0.0228(5) Uani 1 1 d . . .
C1 C 0.1947(5) 0.3211(3) 0.41663(17) 0.0355(6) Uani 1 1 d . . .
H2B H 0.192(4) 0.3487(16) 0.5871(12) 0.022(5) Uiso 1 1 d . . .
H2A H 0.452(4) 0.3864(17) 0.6136(14) 0.028(6) Uiso 1 1 d . . .
H1A H 0.061(4) 0.287(2) 0.4386(15) 0.049(8) Uiso 1 1 d . . .
H1C H 0.135(5) 0.385(2) 0.3888(18) 0.068(9) Uiso 1 1 d . . .
H1B H 0.255(5) 0.273(2) 0.3788(18) 0.061(9) Uiso 1 1 d . . .


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
Cl C3 1.688(2) . ?
O6 N6 1.226(2) . ?
O1 N2 1.234(2) . ?
N4 C5 1.309(2) . ?
N4 N3 1.358(2) . ?
O5 N6 1.233(2) . ?
O2 N2 1.237(2) . ?
O3 N5 1.212(2) . ?
O4 N5 1.201(2) . ?
N5 C5 1.480(3) . ?
N2 N1 1.347(2) . ?
N3 C3 1.353(2) . ?
N3 C2 1.472(3) . ?
C3 C4 1.383(3) . ?
N1 C2 1.443(3) . ?
N1 C1 1.456(3) . ?
N6 C4 1.436(3) . ?
C2 H2B 0.96(2) . ?
C2 H2A 0.92(2) . ?
C4 C5 1.398(3) . ?
C1 H1A 0.96(3) . ?
C1 H1C 0.92(3) . ?
C1 H1B 0.92(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
C5 N4 N3 104.03(15) . . ?
O4 N5 O3 127.2(2) . . ?
O4 N5 C5 116.19(18) . . ?
O3 N5 C5 116.54(18) . . ?
O1 N2 O2 124.93(19) . . ?
O1 N2 N1 117.34(18) . . ?
O2 N2 N1 117.73(18) . . ?
C3 N3 N4 112.65(16) . . ?
C3 N3 C2 129.99(18) . . ?
N4 N3 C2 117.06(16) . . ?
N3 C3 C4 105.95(17) . . ?
N3 C3 Cl 122.64(16) . . ?
C4 C3 Cl 131.39(16) . . ?
N2 N1 C2 118.46(18) . . ?
N2 N1 C1 118.27(18) . . ?
C2 N1 C1 123.3(2) . . ?
O6 N6 O5 124.60(18) . . ?
O6 N6 C4 118.65(19) . . ?
O5 N6 C4 116.75(19) . . ?
N1 C2 N3 111.68(17) . . ?
N1 C2 H2B 109.6(11) . . ?
N3 C2 H2B 106.9(12) . . ?
N1 C2 H2A 110.3(13) . . ?
N3 C2 H2A 109.3(13) . . ?
H2B C2 H2A 108.9(17) . . ?
C3 C4 C5 104.40(17) . . ?
C3 C4 N6 126.64(19) . . ?
C5 C4 N6 128.7(2) . . ?
N4 C5 C4 112.97(18) . . ?
N4 C5 N5 117.50(17) . . ?
C4 C5 N5 129.30(18) . . ?
N1 C1 H1A 110.7(14) . . ?
N1 C1 H1C 111.0(17) . . ?
H1A C1 H1C 105(2) . . ?
N1 C1 H1B 108.0(17) . . ?
H1A C1 H1B 109(2) . . ?
H1C C1 H1B 112(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 N4 N3 C3 -0.5(2) . . . . ?
C5 N4 N3 C2 173.79(16) . . . . ?
N4 N3 C3 C4 0.5(2) . . . . ?
C2 N3 C3 C4 -172.92(18) . . . . ?
N4 N3 C3 Cl -177.78(13) . . . . ?
C2 N3 C3 Cl 8.9(3) . . . . ?
O1 N2 N1 C2 -175.46(17) . . . . ?
O2 N2 N1 C2 4.1(3) . . . . ?
O1 N2 N1 C1 4.1(3) . . . . ?
O2 N2 N1 C1 -176.3(2) . . . . ?
N2 N1 C2 N3 -92.1(2) . . . . ?
C1 N1 C2 N3 88.3(3) . . . . ?
C3 N3 C2 N1 103.9(2) . . . . ?
N4 N3 C2 N1 -69.2(2) . . . . ?
N3 C3 C4 C5 -0.2(2) . . . . ?
Cl C3 C4 C5 177.82(16) . . . . ?
N3 C3 C4 N6 -174.76(18) . . . . ?
Cl C3 C4 N6 3.3(3) . . . . ?
O6 N6 C4 C3 -16.5(3) . . . . ?
O5 N6 C4 C3 163.57(19) . . . . ?
O6 N6 C4 C5 170.29(19) . . . . ?
O5 N6 C4 C5 -9.7(3) . . . . ?
N3 N4 C5 C4 0.4(2) . . . . ?
N3 N4 C5 N5 -174.71(15) . . . . ?
C3 C4 C5 N4 -0.1(2) . . . . ?
N6 C4 C5 N4 174.29(19) . . . . ?
C3 C4 C5 N5 174.24(19) . . . . ?
N6 C4 C5 N5 -11.3(3) . . . . ?
O4 N5 C5 N4 127.6(2) . . . . ?
O3 N5 C5 N4 -49.8(2) . . . . ?
O4 N5 C5 C4 -46.6(3) . . . . ?
O3 N5 C5 C4 136.1(2) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

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
? ? ? ? ? ? ? ?

_geom_special_details            ?



####################################################################### 
# 
# 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_gx534
_database_code_depnum_ccdc_archive 'CCDC 1439314'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 1-(5-amino-3-nitro-1,2,4-triazol-1-yl)-2-nitrazapropane
;
_chemical_name_common            ANTAnap
_chemical_melting_point          202
_chemical_formula_moiety         'C4 H7 N7 O4'
_chemical_formula_sum            'C4 H7 N7 O4'
_chemical_formula_weight         217.14

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.3027(8)
_cell_length_b                   6.8628(8)
_cell_length_c                   10.6253(14)
_cell_angle_alpha                72.876(11)
_cell_angle_beta                 87.968(11)
_cell_angle_gamma                77.540(11)
_cell_volume                     428.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1302
_cell_measurement_theta_min      4.3204
_cell_measurement_theta_max      29.9990

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4326
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1671
_reflns_number_gt                1330
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;

_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 > 2σ(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)+(0.0347P)²+0.0735P] 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         1671
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
O4 O -0.06852(18) 0.74997(17) 0.10436(11) 0.0285(3) Uani 1 1 d . . .
O2 O 0.71294(19) -0.1361(2) 0.34351(12) 0.0349(3) Uani 1 1 d . . .
O3 O -0.26376(18) 0.52881(18) 0.20720(11) 0.0296(3) Uani 1 1 d . . .
O1 O 0.6253(2) -0.2516(2) 0.54840(11) 0.0417(4) Uani 1 1 d . . .
N1 N 0.2721(2) 0.43425(19) 0.09879(12) 0.0210(3) Uani 1 1 d . . .
N2 N 0.0762(2) 0.2085(2) 0.22544(12) 0.0216(3) Uani 1 1 d . . .
N5 N 0.5864(2) 0.1830(3) 0.07544(15) 0.0275(3) Uani 1 1 d . . .
N6 N -0.0947(2) 0.5714(2) 0.15873(12) 0.0223(3) Uani 1 1 d . . .
N4 N 0.3858(2) -0.2014(2) 0.38933(12) 0.0243(3) Uani 1 1 d . . .
N3 N 0.2769(2) 0.10298(19) 0.20077(12) 0.0206(3) Uani 1 1 d . . .
N7 N 0.5843(2) -0.1951(2) 0.42909(13) 0.0272(3) Uani 1 1 d . . .
C3 C 0.3924(2) 0.2390(2) 0.12448(14) 0.0208(3) Uani 1 1 d . . .
C2 C 0.3326(3) -0.1238(2) 0.24951(15) 0.0228(4) Uani 1 1 d . . .
C4 C 0.0893(2) 0.3998(2) 0.16264(14) 0.0197(3) Uani 1 1 d . . .
C1 C 0.2222(3) -0.2390(4) 0.4892(2) 0.0359(5) Uani 1 1 d . . .
H2A H 0.203(3) -0.177(2) 0.2369(15) 0.021(4) Uiso 1 1 d . . .
H2B H 0.454(3) -0.172(2) 0.2005(16) 0.023(4) Uiso 1 1 d . . .
H5A H 0.671(3) 0.072(3) 0.1181(19) 0.035(5) Uiso 1 1 d . . .
H5B H 0.647(3) 0.282(3) 0.0316(19) 0.040(6) Uiso 1 1 d . . .
H1A H 0.093(4) -0.223(4) 0.445(2) 0.067(7) Uiso 1 1 d . . .
H1B H 0.266(4) -0.368(5) 0.552(3) 0.079(8) Uiso 1 1 d . . .
H1C H 0.197(4) -0.134(4) 0.535(2) 0.073(8) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O4 N6 1.2354(16) . ?
O2 N7 1.2332(17) . ?
O3 N6 1.2220(16) . ?
O1 N7 1.2308(17) . ?
N1 C3 1.344(2) . ?
N1 C4 1.3458(19) . ?
N2 C4 1.3049(19) . ?
N2 N3 1.3732(17) . ?
N5 C3 1.336(2) . ?
N5 H5A 0.84(2) . ?
N5 H5B 0.86(2) . ?
N6 C4 1.455(2) . ?
N4 N7 1.3482(19) . ?
N4 C2 1.448(2) . ?
N4 C1 1.460(2) . ?
N3 C3 1.3651(19) . ?
N3 C2 1.4550(19) . ?
C2 H2A 0.995(16) . ?
C2 H2B 0.964(17) . ?
C1 H1A 0.93(3) . ?
C1 H1B 0.93(3) . ?
C1 H1C 0.97(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
C3 N1 C4 101.37(12) . . ?
C4 N2 N3 100.17(11) . . ?
C3 N5 H5A 118.7(13) . . ?
C3 N5 H5B 116.9(13) . . ?
H5A N5 H5B 115.8(19) . . ?
O3 N6 O4 124.87(13) . . ?
O3 N6 C4 118.01(13) . . ?
O4 N6 C4 117.11(12) . . ?
N7 N4 C2 117.68(13) . . ?
N7 N4 C1 117.82(14) . . ?
C2 N4 C1 122.90(14) . . ?
C3 N3 N2 110.47(12) . . ?
C3 N3 C2 129.88(13) . . ?
N2 N3 C2 119.58(12) . . ?
O1 N7 O2 124.61(14) . . ?
O1 N7 N4 117.58(14) . . ?
O2 N7 N4 117.80(13) . . ?
N5 C3 N1 126.02(14) . . ?
N5 C3 N3 124.75(15) . . ?
N1 C3 N3 109.03(13) . . ?
N4 C2 N3 113.08(13) . . ?
N4 C2 H2A 105.9(9) . . ?
N3 C2 H2A 108.0(9) . . ?
N4 C2 H2B 110.2(10) . . ?
N3 C2 H2B 107.7(9) . . ?
H2A C2 H2B 112.0(13) . . ?
N2 C4 N1 118.96(13) . . ?
N2 C4 N6 120.03(13) . . ?
N1 C4 N6 120.98(13) . . ?
N4 C1 H1A 107.0(14) . . ?
N4 C1 H1B 111.3(16) . . ?
H1A C1 H1B 114(2) . . ?
N4 C1 H1C 111.1(14) . . ?
H1A C1 H1C 106(2) . . ?
H1B C1 H1C 107(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
C4 N2 N3 C3 -0.58(15) . . . . ?
C4 N2 N3 C2 -177.64(13) . . . . ?
C2 N4 N7 O1 176.52(14) . . . . ?
C1 N4 N7 O1 10.5(2) . . . . ?
C2 N4 N7 O2 -4.5(2) . . . . ?
C1 N4 N7 O2 -170.52(15) . . . . ?
C4 N1 C3 N5 174.88(16) . . . . ?
C4 N1 C3 N3 -0.20(15) . . . . ?
N2 N3 C3 N5 -174.63(14) . . . . ?
C2 N3 C3 N5 2.0(2) . . . . ?
N2 N3 C3 N1 0.52(16) . . . . ?
C2 N3 C3 N1 177.19(14) . . . . ?
N7 N4 C2 N3 -77.63(17) . . . . ?
C1 N4 C2 N3 87.62(19) . . . . ?
C3 N3 C2 N4 107.22(18) . . . . ?
N2 N3 C2 N4 -76.38(17) . . . . ?
N3 N2 C4 N1 0.50(17) . . . . ?
N3 N2 C4 N6 178.49(12) . . . . ?
C3 N1 C4 N2 -0.21(17) . . . . ?
C3 N1 C4 N6 -178.18(13) . . . . ?
O3 N6 C4 N2 -5.2(2) . . . . ?
O4 N6 C4 N2 175.94(13) . . . . ?
O3 N6 C4 N1 172.75(13) . . . . ?
O4 N6 C4 N1 -6.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_gx685
_database_code_depnum_ccdc_archive 'CCDC 1439315'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 5,5-bis(1-(2-aza-2-nitropropanyl)-3-nitro-1,2,4-triazole
;
_chemical_name_common            DNBTdinap
_chemical_melting_point          225
_chemical_formula_moiety         'C8 H10 N12 O8'
_chemical_formula_sum            'C8 H10 N12 O8'
_chemical_formula_weight         402.28

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   17.5192(17)
_cell_length_b                   6.4082(6)
_cell_length_c                   14.2000(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.184(9)
_cell_angle_gamma                90.00
_cell_volume                     1573.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    956
_cell_measurement_theta_min      4.3346
_cell_measurement_theta_max      33.5324

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3779
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         25.57
_reflns_number_total             1472
_reflns_number_gt                1102
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;

_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 > 2σ(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)+(0.0442P)²+0.0000P] 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         1472
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O1 O 0.21270(9) 0.0337(3) 0.10273(11) 0.0427(4) Uani 1 1 d . . .
O2 O 0.28739(9) 0.0903(3) 0.23718(12) 0.0506(5) Uani 1 1 d . . .
O3 O -0.00748(9) 0.4972(2) 0.35222(11) 0.0403(4) Uani 1 1 d . . .
O4 O 0.06314(10) 0.7311(2) 0.43782(11) 0.0508(5) Uani 1 1 d . . .
N1 N 0.08435(9) 0.0486(3) 0.18786(11) 0.0271(4) Uani 1 1 d . . .
N2 N 0.16353(9) 0.1203(3) 0.32751(12) 0.0286(4) Uani 1 1 d . . .
N3 N 0.08866(9) 0.1261(3) 0.34005(11) 0.0253(4) Uani 1 1 d . . .
N4 N 0.22385(10) 0.0645(3) 0.18851(13) 0.0336(5) Uani 1 1 d . . .
N5 N 0.09279(10) 0.3976(3) 0.45741(12) 0.0317(5) Uani 1 1 d . . .
N6 N 0.04699(11) 0.5494(3) 0.41310(13) 0.0339(5) Uani 1 1 d . . .
C1 C 0.04223(11) 0.0830(3) 0.25654(14) 0.0260(5) Uani 1 1 d . . .
C2 C 0.15617(11) 0.0753(3) 0.23608(14) 0.0269(5) Uani 1 1 d . . .
C3 C 0.07005(13) 0.1862(3) 0.43398(14) 0.0264(5) Uani 1 1 d . . .
C4 C 0.15644(16) 0.4545(5) 0.53177(19) 0.0405(6) Uani 1 1 d . . .
H3A H 0.0161(12) 0.167(3) 0.4315(13) 0.022(5) Uiso 1 1 d . . .
H3B H 0.1005(11) 0.096(3) 0.4818(14) 0.026(5) Uiso 1 1 d . . .
H4A H 0.1374(16) 0.497(4) 0.583(2) 0.064(9) Uiso 1 1 d . . .
H4B H 0.1839(15) 0.568(4) 0.5104(18) 0.059(8) Uiso 1 1 d . . .
H4C H 0.1931(18) 0.338(5) 0.547(2) 0.090(11) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 N4 1.218(2) . ?
O2 N4 1.224(2) . ?
O3 N6 1.227(2) . ?
O4 N6 1.236(2) . ?
N1 C1 1.332(3) . ?
N1 C2 1.344(2) . ?
N2 C2 1.316(2) . ?
N2 N3 1.352(2) . ?
N3 C1 1.355(2) . ?
N3 C3 1.474(2) . ?
N4 C2 1.457(3) . ?
N5 N6 1.351(2) . ?
N5 C3 1.436(3) . ?
N5 C4 1.454(3) . ?
C1 C1 1.462(4) 2 ?
C3 H3A 0.949(19) . ?
C3 H3B 0.98(2) . ?
C4 H4A 0.89(3) . ?
C4 H4B 0.95(3) . ?
C4 H4C 0.98(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
C1 N1 C2 100.89(16) . . ?
C2 N2 N3 101.05(15) . . ?
N2 N3 C1 109.78(16) . . ?
N2 N3 C3 119.06(16) . . ?
C1 N3 C3 131.05(17) . . ?
O1 N4 O2 124.92(18) . . ?
O1 N4 C2 117.30(17) . . ?
O2 N4 C2 117.76(18) . . ?
N6 N5 C3 116.69(17) . . ?
N6 N5 C4 119.15(19) . . ?
C3 N5 C4 123.84(19) . . ?
O3 N6 O4 125.01(19) . . ?
O3 N6 N5 117.98(18) . . ?
O4 N6 N5 117.01(19) . . ?
N1 C1 N3 110.44(17) . . ?
N1 C1 C1 125.1(2) . 2 ?
N3 C1 C1 124.4(2) . 2 ?
N2 C2 N1 117.83(18) . . ?
N2 C2 N4 120.59(17) . . ?
N1 C2 N4 121.51(18) . . ?
N5 C3 N3 111.27(16) . . ?
N5 C3 H3A 111.8(11) . . ?
N3 C3 H3A 107.2(11) . . ?
N5 C3 H3B 107.1(12) . . ?
N3 C3 H3B 107.3(11) . . ?
H3A C3 H3B 112.1(16) . . ?
N5 C4 H4A 108.9(18) . . ?
N5 C4 H4B 109.2(15) . . ?
H4A C4 H4B 107(2) . . ?
N5 C4 H4C 111.7(18) . . ?
H4A C4 H4C 112(2) . . ?
H4B C4 H4C 108(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
C2 N2 N3 C1 0.51(19) . . . . ?
C2 N2 N3 C3 -176.12(16) . . . . ?
C3 N5 N6 O3 -4.4(3) . . . . ?
C4 N5 N6 O3 -178.26(19) . . . . ?
C3 N5 N6 O4 175.08(17) . . . . ?
C4 N5 N6 O4 1.2(3) . . . . ?
C2 N1 C1 N3 -0.3(2) . . . . ?
C2 N1 C1 C1 177.35(11) . . . 2 ?
N2 N3 C1 N1 -0.1(2) . . . . ?
C3 N3 C1 N1 175.97(18) . . . . ?
N2 N3 C1 C1 -177.81(11) . . . 2 ?
C3 N3 C1 C1 -1.7(3) . . . 2 ?
N3 N2 C2 N1 -0.8(2) . . . . ?
N3 N2 C2 N4 176.50(17) . . . . ?
C1 N1 C2 N2 0.7(2) . . . . ?
C1 N1 C2 N4 -176.55(17) . . . . ?
O1 N4 C2 N2 -175.96(18) . . . . ?
O2 N4 C2 N2 2.8(3) . . . . ?
O1 N4 C2 N1 1.2(3) . . . . ?
O2 N4 C2 N1 -179.97(18) . . . . ?
N6 N5 C3 N3 76.4(2) . . . . ?
C4 N5 C3 N3 -110.1(2) . . . . ?
N2 N3 C3 N5 63.9(2) . . . . ?
C1 N3 C3 N5 -111.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.57
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_hx326
_database_code_depnum_ccdc_archive 'CCDC 1439316'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
1-(4-amino-3,5-dinitropyrazol-1-yl)-2-nitrazapropane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N7 O6'
_chemical_formula_sum            'C5 H7 N7 O6'
_chemical_formula_weight         261.18

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9508(16)
_cell_length_b                   5.6426(7)
_cell_length_c                   10.6832(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.579(9)
_cell_angle_gamma                90
_cell_volume                     953.13(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      4.2051
_cell_measurement_theta_max      28.7128

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            3684
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.214
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1929
_reflns_number_gt                1528
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_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)+(0.0387P)²+0.1854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
O1 O 0.18117(10) -0.4836(3) 0.51139(14) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.06221(9) -0.2906(3) 0.47551(15) 0.0359(4) Uani 1 1 d . . . . .
O3 O 0.12755(9) 0.4677(3) 0.19142(15) 0.0359(4) Uani 1 1 d . . . . .
O4 O 0.26000(9) 0.4419(3) 0.16522(14) 0.0297(4) Uani 1 1 d . . . . .
O5 O 0.44726(9) -0.3399(3) 0.08670(13) 0.0276(4) Uani 1 1 d . . . . .
O6 O 0.42632(9) -0.3692(3) 0.28361(13) 0.0265(4) Uani 1 1 d . . . . .
N1 N 0.27396(9) 0.0255(3) 0.31238(14) 0.0175(4) Uani 1 1 d . . . . .
N2 N 0.25804(10) -0.1587(3) 0.38257(14) 0.0202(4) Uani 1 1 d . . . . .
N3 N 0.13813(11) -0.3170(3) 0.46617(16) 0.0257(4) Uani 1 1 d . . . . .
N4 N 0.05401(11) 0.1226(4) 0.32555(19) 0.0319(5) Uani 1 1 d . . . . .
N5 N 0.19746(10) 0.3669(3) 0.20818(15) 0.0232(4) Uani 1 1 d . . . . .
N6 N 0.37990(10) -0.0513(3) 0.17161(14) 0.0186(4) Uani 1 1 d . . . . .
N7 N 0.42015(10) -0.2640(3) 0.18169(15) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.17622(12) -0.1416(4) 0.39526(18) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.13558(12) 0.0555(4) 0.33355(17) 0.0203(4) Uani 1 1 d . . . . .
C3 C 0.20205(12) 0.1589(4) 0.28063(18) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.36232(11) 0.0596(4) 0.28689(17) 0.0185(4) Uani 1 1 d . . . . .
H4A H 0.3738 0.2316 0.2822 0.022 Uiso 1 1 calc R U . . .
H4B H 0.4012 -0.0060 0.3584 0.022 Uiso 1 1 calc R U . . .
C5 C 0.38392(13) 0.0805(4) 0.05476(18) 0.0235(5) Uani 1 1 d . . . . .
H5A H 0.3508 0.2267 0.0559 0.035 Uiso 1 1 calc R U . . .
H5B H 0.3607 -0.0168 -0.0176 0.035 Uiso 1 1 calc R U . . .
H5C H 0.4429 0.1202 0.0476 0.035 Uiso 1 1 calc R U . . .
H1 H 0.0243(14) 0.053(4) 0.379(2) 0.028 Uiso 1 1 d . U . . .
H2 H 0.0412(15) 0.261(5) 0.294(2) 0.028 Uiso 1 1 d . U . . .


_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
O1 N3 1.225(2) . ?
O2 N3 1.237(2) . ?
O3 N5 1.243(2) . ?
O4 N5 1.227(2) . ?
O5 N7 1.231(2) . ?
O6 N7 1.233(2) . ?
N1 N2 1.325(2) . ?
N1 C3 1.377(2) . ?
N1 C4 1.483(2) . ?
N2 C1 1.333(2) . ?
N3 C1 1.430(3) . ?
N4 C2 1.347(3) . ?
N4 H1 0.88(2) . ?
N4 H2 0.86(3) . ?
N5 C3 1.403(3) . ?
N6 N7 1.359(2) . ?
N6 C4 1.442(2) . ?
N6 C5 1.462(2) . ?
C1 C2 1.407(3) . ?
C2 C3 1.394(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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 C3 110.64(14) . . ?
N2 N1 C4 117.62(15) . . ?
C3 N1 C4 131.67(16) . . ?
N1 N2 C1 105.32(16) . . ?
O1 N3 O2 124.35(19) . . ?
O1 N3 C1 119.01(17) . . ?
O2 N3 C1 116.63(18) . . ?
C2 N4 H1 115.6(15) . . ?
C2 N4 H2 117.2(16) . . ?
H1 N4 H2 122(2) . . ?
O4 N5 O3 123.12(17) . . ?
O4 N5 C3 120.60(16) . . ?
O3 N5 C3 116.27(16) . . ?
N7 N6 C4 117.32(15) . . ?
N7 N6 C5 116.34(15) . . ?
C4 N6 C5 122.95(16) . . ?
O5 N7 O6 124.39(17) . . ?
O5 N7 N6 117.11(16) . . ?
O6 N7 N6 118.50(15) . . ?
N2 C1 C2 113.96(18) . . ?
N2 C1 N3 119.60(19) . . ?
C2 C1 N3 126.43(18) . . ?
N4 C2 C3 129.6(2) . . ?
N4 C2 C1 129.3(2) . . ?
C3 C2 C1 101.12(16) . . ?
N1 C3 C2 108.95(17) . . ?
N1 C3 N5 125.09(16) . . ?
C2 C3 N5 125.95(17) . . ?
N6 C4 N1 113.39(15) . . ?
N6 C4 H4A 108.9 . . ?
N1 C4 H4A 108.9 . . ?
N6 C4 H4B 108.9 . . ?
N1 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N6 C5 H5A 109.5 . . ?
N6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
C3 N1 N2 C1 0.0(2) . . . . ?
C4 N1 N2 C1 177.30(16) . . . . ?
C4 N6 N7 O5 -168.52(15) . . . . ?
C5 N6 N7 O5 -8.6(2) . . . . ?
C4 N6 N7 O6 12.3(2) . . . . ?
C5 N6 N7 O6 172.21(16) . . . . ?
N1 N2 C1 C2 -0.1(2) . . . . ?
N1 N2 C1 N3 179.52(16) . . . . ?
O1 N3 C1 N2 -1.9(3) . . . . ?
O2 N3 C1 N2 179.41(17) . . . . ?
O1 N3 C1 C2 177.67(18) . . . . ?
O2 N3 C1 C2 -1.1(3) . . . . ?
N2 C1 C2 N4 178.8(2) . . . . ?
N3 C1 C2 N4 -0.8(3) . . . . ?
N2 C1 C2 C3 0.1(2) . . . . ?
N3 C1 C2 C3 -179.42(18) . . . . ?
N2 N1 C3 C2 0.1(2) . . . . ?
C4 N1 C3 C2 -176.72(18) . . . . ?
N2 N1 C3 N5 179.27(17) . . . . ?
C4 N1 C3 N5 2.4(3) . . . . ?
N4 C2 C3 N1 -178.8(2) . . . . ?
C1 C2 C3 N1 -0.1(2) . . . . ?
N4 C2 C3 N5 2.1(4) . . . . ?
C1 C2 C3 N5 -179.29(18) . . . . ?
O4 N5 C3 N1 1.5(3) . . . . ?
O3 N5 C3 N1 -178.27(17) . . . . ?
O4 N5 C3 C2 -179.50(18) . . . . ?
O3 N5 C3 C2 0.7(3) . . . . ?
N7 N6 C4 N1 -99.81(19) . . . . ?
C5 N6 C4 N1 101.7(2) . . . . ?
N2 N1 C4 N6 92.28(19) . . . . ?
C3 N1 C4 N6 -91.1(2) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_fx408
_database_code_depnum_ccdc_archive 'CCDC 1439317'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_vrf_PLAT915_fx408               
;
Problem: Low Friedel Pair Coverage 18%
RESPONSE: absolute structure was not determined
;
_audit_block_code                ?
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
1-(3,5-Dinitro-1,2,4-triazol-1-yl)-2-nitrazapropane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 N7 O6'
_chemical_formula_sum            'C4 H5 N7 O6'
_chemical_formula_weight         247.15

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.831(4)
_cell_length_b                   7.0572(7)
_cell_length_c                   11.133(3)
_cell_angle_alpha                90.000
_cell_angle_beta                 132.07(4)
_cell_angle_gamma                90.000
_cell_volume                     923.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    788
_cell_measurement_theta_min      4.8067
_cell_measurement_theta_max      28.8240

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            1859
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.813
_diffrn_reflns_theta_max         28.954
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.995
_reflns_number_total             1260
_reflns_number_gt                957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.213
_reflns_Friedel_fraction_max     0.181
_reflns_Friedel_fraction_full    0.244

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_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)+(0.0212P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1260
_refine_ls_number_parameters     174
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0515
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.894
_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
N2 N 0.4912(2) 0.0474(4) 0.1281(3) 0.0265(6) Uani 1 1 d . . . . .
N6 N 0.3214(2) -0.1725(4) 0.0599(3) 0.0294(6) Uani 1 1 d . . . . .
O1 O 0.6352(2) 0.0430(4) 0.0762(3) 0.0493(7) Uani 1 1 d . . . . .
O2 O 0.7376(2) 0.2626(4) 0.2548(3) 0.0490(7) Uani 1 1 d . . . . .
O5 O 0.46430(19) -0.3086(4) 0.2906(3) 0.0530(8) Uani 1 1 d . . . . .
N3 N 0.6059(2) 0.2654(4) 0.3278(3) 0.0279(6) Uani 1 1 d . . . . .
O4 O 0.4075(2) 0.2850(4) 0.3687(3) 0.0470(7) Uani 1 1 d . . . . .
N1 N 0.45007(19) 0.0925(3) 0.1983(3) 0.0238(6) Uani 1 1 d . . . . .
N4 N 0.6576(2) 0.1540(4) 0.1778(3) 0.0322(7) Uani 1 1 d . . . . .
N5 N 0.5012(3) 0.3064(4) 0.4146(3) 0.0331(7) Uani 1 1 d . . . . .
O6 O 0.3477(2) -0.4819(4) 0.0730(3) 0.0489(7) Uani 1 1 d . . . . .
N7 N 0.3807(2) -0.3300(5) 0.1462(4) 0.0391(8) Uani 1 1 d . . . . .
O3 O 0.5812(2) 0.3911(4) 0.5346(3) 0.0472(7) Uani 1 1 d . . . . .
C1 C 0.5824(2) 0.1567(5) 0.2105(3) 0.0242(7) Uani 1 1 d . . . . .
C3 C 0.3465(3) -0.0027(5) 0.1489(4) 0.0312(8) Uani 1 1 d . . . . .
C2 C 0.5195(2) 0.2222(5) 0.3148(3) 0.0251(7) Uani 1 1 d . . . . .
C4 C 0.2205(3) -0.1948(6) -0.1095(4) 0.0359(9) Uani 1 1 d . . . . .
H3A H 0.283(3) 0.075(5) 0.072(4) 0.044(10) Uiso 1 1 d . . . . .
H4A H 0.238(3) -0.268(6) -0.159(5) 0.046(10) Uiso 1 1 d . . . . .
H3B H 0.371(3) -0.023(5) 0.257(4) 0.034(9) Uiso 1 1 d . . . . .
H4C H 0.204(3) -0.069(7) -0.150(4) 0.065(13) Uiso 1 1 d . . . . .
H4B H 0.159(4) -0.259(6) -0.121(5) 0.076(14) Uiso 1 1 d . . . . .


_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
N2 C1 1.322(4) . ?
N2 N1 1.349(3) . ?
N6 N7 1.353(4) . ?
N6 C3 1.431(4) . ?
N6 C4 1.447(4) . ?
O1 N4 1.217(3) . ?
O2 N4 1.213(4) . ?
O5 N7 1.228(4) . ?
N3 C2 1.312(3) . ?
N3 C1 1.334(4) . ?
O4 N5 1.211(3) . ?
N1 C2 1.348(4) . ?
N1 C3 1.495(4) . ?
N4 C1 1.460(4) . ?
N5 O3 1.216(3) . ?
N5 C2 1.451(4) . ?
O6 N7 1.232(4) . ?
C3 H3A 0.94(4) . ?
C3 H3B 1.00(3) . ?
C4 H4A 0.93(4) . ?
C4 H4C 0.95(5) . ?
C4 H4B 1.00(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
C1 N2 N1 100.8(2) . . ?
N7 N6 C3 117.2(3) . . ?
N7 N6 C4 118.1(3) . . ?
C3 N6 C4 123.0(3) . . ?
C2 N3 C1 99.9(3) . . ?
C2 N1 N2 108.6(2) . . ?
C2 N1 C3 130.2(3) . . ?
N2 N1 C3 121.1(2) . . ?
O2 N4 O1 125.5(3) . . ?
O2 N4 C1 117.0(3) . . ?
O1 N4 C1 117.5(3) . . ?
O4 N5 O3 127.2(3) . . ?
O4 N5 C2 116.2(3) . . ?
O3 N5 C2 116.6(3) . . ?
O5 N7 O6 125.5(3) . . ?
O5 N7 N6 117.1(3) . . ?
O6 N7 N6 117.4(3) . . ?
N2 C1 N3 118.3(2) . . ?
N2 C1 N4 120.8(3) . . ?
N3 C1 N4 120.8(3) . . ?
N6 C3 N1 111.0(3) . . ?
N6 C3 H3A 103(2) . . ?
N1 C3 H3A 108(2) . . ?
N6 C3 H3B 114.6(19) . . ?
N1 C3 H3B 100.2(18) . . ?
H3A C3 H3B 120(2) . . ?
N3 C2 N1 112.4(3) . . ?
N3 C2 N5 123.4(3) . . ?
N1 C2 N5 124.2(2) . . ?
N6 C4 H4A 109(2) . . ?
N6 C4 H4C 103(2) . . ?
H4A C4 H4C 110(3) . . ?
N6 C4 H4B 110(2) . . ?
H4A C4 H4B 109(4) . . ?
H4C C4 H4B 116(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
C1 N2 N1 C2 -0.2(3) . . . . ?
C1 N2 N1 C3 -177.7(3) . . . . ?
C3 N6 N7 O5 -12.5(4) . . . . ?
C4 N6 N7 O5 -178.2(3) . . . . ?
C3 N6 N7 O6 169.0(3) . . . . ?
C4 N6 N7 O6 3.3(4) . . . . ?
N1 N2 C1 N3 1.0(3) . . . . ?
N1 N2 C1 N4 179.0(2) . . . . ?
N1 N2 C1 C2 0.10(19) . . . . ?
C2 N3 C1 N2 -1.3(4) . . . . ?
C2 N3 C1 N4 -179.4(3) . . . . ?
O2 N4 C1 N2 177.7(3) . . . . ?
O1 N4 C1 N2 -2.5(4) . . . . ?
O2 N4 C1 N3 -4.3(4) . . . . ?
O1 N4 C1 N3 175.5(3) . . . . ?
N7 N6 C3 N1 81.4(3) . . . . ?
C4 N6 C3 N1 -113.6(3) . . . . ?
C2 N1 C3 N6 -160.6(3) . . . . ?
N2 N1 C3 N6 16.4(4) . . . . ?
C1 N3 C2 N1 1.1(3) . . . . ?
C1 N3 C2 N5 -178.5(3) . . . . ?
N2 N1 C2 N3 -0.7(3) . . . . ?
C3 N1 C2 N3 176.6(3) . . . . ?
N2 N1 C2 N5 179.0(3) . . . . ?
C3 N1 C2 N5 -3.8(5) . . . . ?
O4 N5 C2 N3 165.1(3) . . . . ?
O3 N5 C2 N3 -14.7(4) . . . . ?
O4 N5 C2 N1 -14.6(4) . . . . ?
O3 N5 C2 N1 165.7(3) . . . . ?


_refine_diff_density_max         0.142
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_fx488
_database_code_depnum_ccdc_archive 'CCDC 1439318'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        1-(4,5-dinitroimidazol-1-yl)-2-nitrazapropane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N6 O6'
_chemical_formula_sum            'C5 H6 N6 O6'
_chemical_formula_weight         246.16
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.7787(8)
_cell_length_b                   20.764(3)
_cell_length_c                   7.7190(11)
_cell_angle_alpha                90.000
_cell_angle_beta                 92.393(12)
_cell_angle_gamma                90.000
_cell_volume                     925.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    966
_cell_measurement_theta_min      4.4058
_cell_measurement_theta_max      33.5513

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            2573
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.430
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_reflns_number_total             1820
_reflns_number_gt                1216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.721
_reflns_Friedel_fraction_full    0.770

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_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)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1820
_refine_ls_number_parameters     167
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_restrained_S_all      0.861
_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
O1 O 0.3969(5) -0.04349(15) 0.4988(4) 0.0367(8) Uani 1 1 d . . . . .
O3 O 0.2272(5) 0.15831(16) 0.5974(4) 0.0411(9) Uani 1 1 d . . . . .
O2 O 0.2789(6) 0.04837(17) 0.3987(4) 0.0446(9) Uani 1 1 d . . . . .
N3 N 0.4024(6) 0.01491(19) 0.4945(5) 0.0273(8) Uani 1 1 d . . . . .
O4 O 0.5413(6) 0.21491(14) 0.5810(4) 0.0373(7) Uani 1 1 d . . . . .
O5 O 0.4197(5) 0.19301(15) 0.9504(4) 0.0340(7) Uani 1 1 d . . . . .
N6 N 0.5392(6) 0.17916(15) 1.0794(5) 0.0276(8) Uani 1 1 d . . . . .
N5 N 0.7634(5) 0.16298(17) 1.0545(5) 0.0279(8) Uani 1 1 d . . . . .
O6 O 0.4769(5) 0.17852(16) 1.2288(4) 0.0423(9) Uani 1 1 d . . . . .
N1 N 0.7687(5) 0.11628(16) 0.7696(4) 0.0238(8) Uani 1 1 d . . . . .
N2 N 0.7477(6) 0.01371(17) 0.6846(5) 0.0305(8) Uani 1 1 d . . . . .
C4 C 0.8412(8) 0.1702(2) 0.8822(6) 0.0260(9) Uani 1 1 d . . . . .
C3 C 0.5754(6) 0.11033(19) 0.6574(5) 0.0226(9) Uani 1 1 d . . . . .
N4 N 0.4382(6) 0.16538(17) 0.6086(4) 0.0278(8) Uani 1 1 d . . . . .
C2 C 0.5689(7) 0.04730(19) 0.6096(6) 0.0240(9) Uani 1 1 d . . . . .
C5 C 0.9083(7) 0.1463(2) 1.2066(6) 0.0344(11) Uani 1 1 d . . . . .
H5A H 0.9123 0.1824 1.2883 0.052 Uiso 1 1 calc R U . . .
H5C H 1.0658 0.1369 1.1714 0.052 Uiso 1 1 calc R U . . .
H5B H 0.8444 0.1082 1.2626 0.052 Uiso 1 1 calc R U . . .
C1 C 0.8604(7) 0.0566(2) 0.7792(6) 0.0298(10) Uani 1 1 d . . . . .
H4A H 0.792(6) 0.2090(18) 0.827(5) 0.006(9) Uiso 1 1 d . . . . .
H4B H 1.009(7) 0.1688(17) 0.896(5) 0.016(10) Uiso 1 1 d . . . . .
H1A H 0.981(9) 0.049(2) 0.856(7) 0.045(13) Uiso 1 1 d . . . . .


_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
O1 N3 1.214(4) . ?
O3 N4 1.228(4) . ?
O2 N3 1.223(5) . ?
N3 C2 1.448(5) . ?
O4 N4 1.212(4) . ?
O5 N6 1.222(5) . ?
N6 O6 1.222(5) . ?
N6 N5 1.360(4) . ?
N5 C4 1.430(6) . ?
N5 C5 1.456(5) . ?
N1 C1 1.349(5) . ?
N1 C3 1.390(5) . ?
N1 C4 1.468(5) . ?
N2 C1 1.307(6) . ?
N2 C2 1.356(5) . ?
C4 H4A 0.95(4) . ?
C4 H4B 0.97(4) . ?
C3 C2 1.360(6) . ?
C3 N4 1.432(5) . ?
C5 H5A 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5B 0.9800 . ?
C1 H1A 0.91(5) . ?

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
O1 N3 O2 124.7(4) . . ?
O1 N3 C2 117.7(4) . . ?
O2 N3 C2 117.6(3) . . ?
O6 N6 O5 126.3(4) . . ?
O6 N6 N5 116.8(3) . . ?
O5 N6 N5 116.9(3) . . ?
N6 N5 C4 116.4(3) . . ?
N6 N5 C5 117.6(3) . . ?
C4 N5 C5 125.6(4) . . ?
C1 N1 C3 104.8(3) . . ?
C1 N1 C4 124.5(3) . . ?
C3 N1 C4 129.7(3) . . ?
C1 N2 C2 103.9(4) . . ?
N5 C4 N1 112.1(4) . . ?
N5 C4 H4A 114(2) . . ?
N1 C4 H4A 108(2) . . ?
N5 C4 H4B 104(2) . . ?
N1 C4 H4B 107(2) . . ?
H4A C4 H4B 111(3) . . ?
C2 C3 N1 105.5(3) . . ?
C2 C3 N4 133.5(4) . . ?
N1 C3 N4 120.9(3) . . ?
O4 N4 O3 125.7(4) . . ?
O4 N4 C3 116.9(3) . . ?
O3 N4 C3 117.4(4) . . ?
N2 C2 C3 111.6(4) . . ?
N2 C2 N3 119.9(3) . . ?
C3 C2 N3 128.6(4) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
N2 C1 N1 114.2(4) . . ?
N2 C1 H1A 126(3) . . ?
N1 C1 H1A 119(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
O6 N6 N5 C4 -173.8(4) . . . . ?
O5 N6 N5 C4 6.1(5) . . . . ?
O6 N6 N5 C5 0.2(5) . . . . ?
O5 N6 N5 C5 -179.9(4) . . . . ?
N6 N5 C4 N1 -79.9(4) . . . . ?
C5 N5 C4 N1 106.7(5) . . . . ?
C1 N1 C4 N5 -73.0(5) . . . . ?
C3 N1 C4 N5 94.3(5) . . . . ?
C1 N1 C3 C2 0.0(4) . . . . ?
C4 N1 C3 C2 -169.2(4) . . . . ?
C1 N1 C3 N4 -177.0(3) . . . . ?
C4 N1 C3 N4 13.8(6) . . . . ?
C2 C3 N4 O4 -136.0(5) . . . . ?
N1 C3 N4 O4 39.9(5) . . . . ?
C2 C3 N4 O3 43.6(6) . . . . ?
N1 C3 N4 O3 -140.5(4) . . . . ?
C1 N2 C2 C3 0.6(5) . . . . ?
C1 N2 C2 N3 -179.5(4) . . . . ?
N1 C3 C2 N2 -0.4(5) . . . . ?
N4 C3 C2 N2 176.0(4) . . . . ?
N1 C3 C2 N3 179.8(4) . . . . ?
N4 C3 C2 N3 -3.8(8) . . . . ?
O1 N3 C2 N2 16.3(6) . . . . ?
O2 N3 C2 N2 -163.0(4) . . . . ?
O1 N3 C2 C3 -163.8(4) . . . . ?
O2 N3 C2 C3 16.8(6) . . . . ?
C2 N2 C1 N1 -0.7(5) . . . . ?
C3 N1 C1 N2 0.5(5) . . . . ?
C4 N1 C1 N2 170.4(4) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_fx520
_database_code_depnum_ccdc_archive 'CCDC 1439319'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_vrf_PLAT242_fx520               
;
Problem: Low 'MainMol' Ueq of N3 compared to neighbors
RESPONSE: Atoms are correctly assigned
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Thu Nov 04 17:39:29 2010'
;

_chemical_name_systematic        1-(2,4-dinitroimidazol-1-yl)-2-nitrazapropane
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H6 N6 O6'
_chemical_formula_sum            'C5 H6 N6 O6'
_chemical_formula_weight         246.138

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            4194
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.995

_reflns_number_total             1920
_reflns_number_gt                1157
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0414650703
_diffrn_orient_matrix_UB_12      0.0307273437
_diffrn_orient_matrix_UB_13      0.0251900383
_diffrn_orient_matrix_UB_21      0.0488524345
_diffrn_orient_matrix_UB_22      -0.0140755652
_diffrn_orient_matrix_UB_23      0.0543940639
_diffrn_orient_matrix_UB_31      0.0204423921
_diffrn_orient_matrix_UB_32      0.0962225820
_diffrn_orient_matrix_UB_33      -0.0000293357
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00    1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -38.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932    0.0000 -120.0000 129

#__ type_ start__ end____ width___ exp.time_
  3 omega   58.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000   90.0000 47

;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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                   11.4913(12)
_cell_length_b                   6.9525(5)
_cell_length_c                   12.8652(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.537(10)
_cell_angle_gamma                90.00
_cell_volume                     942.33(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1471
_cell_measurement_theta_min      4.2287
_cell_measurement_theta_max      32.1662
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

_diffrn_special_details          ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0325P)²+0.0000P] 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_extinction_expression ?
_refine_ls_number_reflns         1920
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   0.835
_refine_ls_restrained_S_all      0.835
_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
O3 O 0.10811(12) 0.14298(19) 0.01676(10) 0.0443(4) Uani 1 1 d . . .
O4 O 0.06034(12) 0.33699(19) 0.12669(11) 0.0474(4) Uani 1 1 d . . .
O6 O 0.53182(12) 0.03494(19) 0.63688(11) 0.0474(4) Uani 1 1 d . . .
O5 O 0.35342(13) 0.17828(17) 0.53482(10) 0.0445(4) Uani 1 1 d . . .
N1 N 0.19610(12) -0.10195(19) 0.35724(10) 0.0249(3) Uani 1 1 d . . .
N5 N 0.36102(13) -0.1403(2) 0.54436(11) 0.0291(3) Uani 1 1 d . . .
N2 N 0.18472(12) -0.1315(2) 0.18005(10) 0.0273(3) Uani 1 1 d . . .
N6 N 0.41819(15) 0.0340(2) 0.57408(12) 0.0348(4) Uani 1 1 d . . .
O1 O 0.24831(17) -0.49427(18) 0.37508(12) 0.0658(5) Uani 1 1 d . . .
N4 N 0.10131(14) 0.1842(2) 0.10664(12) 0.0346(4) Uani 1 1 d . . .
O2 O 0.30586(14) -0.47707(18) 0.23626(11) 0.0491(4) Uani 1 1 d . . .
N3 N 0.26198(14) -0.4117(2) 0.30012(12) 0.0309(4) Uani 1 1 d . . .
C4 C 0.22703(17) -0.1397(3) 0.47905(13) 0.0279(4) Uani 1 1 d . . .
C2 C 0.14465(16) 0.0444(2) 0.19710(13) 0.0255(4) Uani 1 1 d . . .
C3 C 0.15137(16) 0.0684(3) 0.30447(15) 0.0281(4) Uani 1 1 d . . .
C5 C 0.4351(2) -0.3092(3) 0.60021(19) 0.0420(5) Uani 1 1 d . . .
C1 C 0.21474(15) -0.2136(2) 0.27802(13) 0.0256(4) Uani 1 1 d . . .
H5A H 0.3781(18) -0.425(3) 0.5726(15) 0.042(5) Uiso 1 1 d . . .
H4A H 0.1837(15) -0.038(2) 0.5006(12) 0.022(4) Uiso 1 1 d . . .
H4B H 0.1945(14) -0.269(2) 0.4864(12) 0.026(4) Uiso 1 1 d . . .
H3A H 0.1355(16) 0.177(2) 0.3442(14) 0.040(5) Uiso 1 1 d . . .
H5C H 0.4666(19) -0.293(3) 0.6807(19) 0.060(6) Uiso 1 1 d . . .
H5B H 0.507(2) -0.329(3) 0.5740(17) 0.062(6) Uiso 1 1 d . . .


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
O3 N4 1.2237(18) . ?
O4 N4 1.2304(18) . ?
O6 N6 1.2310(18) . ?
O5 N6 1.2308(17) . ?
N1 C3 1.360(2) . ?
N1 C1 1.3642(19) . ?
N1 C4 1.4853(19) . ?
N5 N6 1.3586(19) . ?
N5 C4 1.430(2) . ?
N5 C5 1.460(2) . ?
N2 C1 1.2983(19) . ?
N2 C2 1.356(2) . ?
O1 N3 1.1856(17) . ?
N4 C2 1.443(2) . ?
O2 N3 1.2112(18) . ?
N3 C1 1.466(2) . ?
C4 H4A 0.965(15) . ?
C4 H4B 0.991(16) . ?
C2 C3 1.363(2) . ?
C3 H3A 0.967(17) . ?
C5 H5A 1.008(19) . ?
C5 H5C 0.96(2) . ?
C5 H5B 1.01(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
C3 N1 C1 105.27(13) . . ?
C3 N1 C4 124.33(14) . . ?
C1 N1 C4 130.17(14) . . ?
N6 N5 C4 116.68(14) . . ?
N6 N5 C5 117.21(15) . . ?
C4 N5 C5 124.85(17) . . ?
C1 N2 C2 102.42(13) . . ?
O5 N6 O6 125.05(16) . . ?
O5 N6 N5 117.79(15) . . ?
O6 N6 N5 117.15(15) . . ?
O3 N4 O4 125.06(15) . . ?
O3 N4 C2 118.20(15) . . ?
O4 N4 C2 116.73(15) . . ?
O1 N3 O2 126.59(16) . . ?
O1 N3 C1 116.99(15) . . ?
O2 N3 C1 116.32(14) . . ?
N5 C4 N1 111.62(14) . . ?
N5 C4 H4A 113.0(9) . . ?
N1 C4 H4A 103.9(9) . . ?
N5 C4 H4B 107.5(9) . . ?
N1 C4 H4B 108.7(9) . . ?
H4A C4 H4B 112.1(13) . . ?
N2 C2 C3 112.89(14) . . ?
N2 C2 N4 120.48(14) . . ?
C3 C2 N4 126.63(15) . . ?
N1 C3 C2 104.87(15) . . ?
N1 C3 H3A 121.8(10) . . ?
C2 C3 H3A 133.2(10) . . ?
N5 C5 H5A 107.3(10) . . ?
N5 C5 H5C 109.2(12) . . ?
H5A C5 H5C 112.8(16) . . ?
N5 C5 H5B 109.8(11) . . ?
H5A C5 H5B 105.8(15) . . ?
H5C C5 H5B 111.7(17) . . ?
N2 C1 N1 114.54(15) . . ?
N2 C1 N3 122.36(15) . . ?
N1 C1 N3 123.09(14) . . ?

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
C4 N5 N6 O5 -6.2(2) . . . . ?
C5 N5 N6 O5 -174.03(15) . . . . ?
C4 N5 N6 O6 175.08(14) . . . . ?
C5 N5 N6 O6 7.2(2) . . . . ?
N6 N5 C4 N1 80.24(18) . . . . ?
C5 N5 C4 N1 -112.95(18) . . . . ?
C3 N1 C4 N5 -104.48(18) . . . . ?
C1 N1 C4 N5 69.1(2) . . . . ?
C1 N2 C2 C3 0.43(19) . . . . ?
C1 N2 C2 N4 -179.81(15) . . . . ?
O3 N4 C2 N2 -3.8(2) . . . . ?
O4 N4 C2 N2 176.39(15) . . . . ?
O3 N4 C2 C3 175.95(16) . . . . ?
O4 N4 C2 C3 -3.9(2) . . . . ?
C1 N1 C3 C2 0.99(17) . . . . ?
C4 N1 C3 C2 175.89(15) . . . . ?
N2 C2 C3 N1 -0.93(19) . . . . ?
N4 C2 C3 N1 179.34(16) . . . . ?
C2 N2 C1 N1 0.25(18) . . . . ?
C2 N2 C1 N3 178.92(15) . . . . ?
C3 N1 C1 N2 -0.82(19) . . . . ?
C4 N1 C1 N2 -175.31(15) . . . . ?
C3 N1 C1 N3 -179.48(14) . . . . ?
C4 N1 C1 N3 6.0(2) . . . . ?
O1 N3 C1 N2 -156.35(17) . . . . ?
O2 N3 C1 N2 20.4(2) . . . . ?
O1 N3 C1 N1 22.2(2) . . . . ?
O2 N3 C1 N1 -161.07(15) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

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
? ? ? ? ? ? ? ?

_geom_special_details            ?

####################################################################### 
# 
# 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_fx528
_database_code_depnum_ccdc_archive 'CCDC 1439320'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Wed Nov 10 18:06:48 2010'
;

_chemical_name_systematic        
2,4-bis(methyl(nitro)amino)methyl)-3-nitro-1,2,4-triazol-5-one
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H10 N8 O7, H1 N1 O3'
_chemical_formula_sum            'C6 H11 N9 O10'
_chemical_formula_weight         369.24

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            3846
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             2832
_reflns_number_gt                2094
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0314423482
_diffrn_orient_matrix_UB_12      0.0345095443
_diffrn_orient_matrix_UB_13      0.0403639312
_diffrn_orient_matrix_UB_21      0.0526765936
_diffrn_orient_matrix_UB_22      -0.0463645965
_diffrn_orient_matrix_UB_23      0.0442984449
_diffrn_orient_matrix_UB_31      0.0313257711
_diffrn_orient_matrix_UB_32      0.1131786532
_diffrn_orient_matrix_UB_33      0.0059638396
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.0000   80.0000  250.0000 104

;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.828(2)
_cell_length_b                   5.5849(11)
_cell_length_c                   12.363(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.59(3)
_cell_angle_gamma                90.00
_cell_volume                     712.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      4.1482
_cell_measurement_theta_max      33.5594
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?


_diffrn_special_details          ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0210P)²+0.0000P] 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_extinction_expression ?
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_restrained_S_all      0.864
_refine_ls_shift/su_max          0.001
_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
O1 O 0.69166(14) 0.2549(3) 0.67492(12) 0.0310(4) Uani 1 1 d . . .
O4 O 1.12545(15) 0.2787(3) 0.62105(14) 0.0397(5) Uani 1 1 d . . .
O10 O 0.36759(14) 0.7429(4) 0.54639(14) 0.0322(4) Uani 1 1 d . . .
O6 O 0.59716(15) 0.7063(3) 0.95862(12) 0.0314(4) Uani 1 1 d . . .
O5 O 0.91635(15) 0.2192(4) 0.57283(13) 0.0376(4) Uani 1 1 d . . .
N1 N 0.87468(16) 0.7286(4) 0.82378(14) 0.0254(4) Uani 1 1 d . . .
N3 N 0.75462(16) 0.4270(4) 0.85478(14) 0.0231(4) Uani 1 1 d . . .
O3 O 0.89778(18) 0.9144(4) 1.03057(15) 0.0470(5) Uani 1 1 d . . .
O8 O 0.56040(13) 0.7411(4) 0.51998(12) 0.0341(4) Uani 1 1 d . . .
O2 O 0.86468(16) 0.5555(4) 1.08425(14) 0.0453(5) Uani 1 1 d . . .
N7 N 0.53277(17) 0.3776(4) 0.85725(15) 0.0244(5) Uani 1 1 d . . .
O7 O 0.39141(15) 0.6519(3) 0.87020(13) 0.0352(5) Uani 1 1 d . . .
O9 O 0.54152(15) 0.7464(4) 0.69017(13) 0.0366(4) Uani 1 1 d . . .
N5 N 0.99696(17) 0.5747(4) 0.63652(16) 0.0280(5) Uani 1 1 d . . .
N2 N 0.82866(16) 0.5908(4) 0.72768(14) 0.0234(4) Uani 1 1 d . . .
N8 N 0.50504(19) 0.5878(4) 0.89747(16) 0.0264(5) Uani 1 1 d . . .
N6 N 1.01364(19) 0.3459(4) 0.60955(16) 0.0295(5) Uani 1 1 d . . .
N9 N 0.49880(17) 0.7429(4) 0.58762(16) 0.0293(5) Uani 1 1 d . . .
C3 C 0.8671(2) 0.6511(5) 0.6272(2) 0.0257(6) Uani 1 1 d . . .
N4 N 0.86541(17) 0.7046(5) 1.01306(17) 0.0323(5) Uani 1 1 d . . .
C5 C 0.6644(2) 0.2916(5) 0.9000(2) 0.0263(6) Uani 1 1 d . . .
C1 C 0.7527(2) 0.4064(4) 0.74218(18) 0.0234(5) Uani 1 1 d . . .
C2 C 0.8272(2) 0.6260(4) 0.89507(18) 0.0241(5) Uani 1 1 d . . .
C4 C 1.1118(3) 0.7079(6) 0.7000(2) 0.0344(6) Uani 1 1 d . . .
C6 C 0.4266(3) 0.2436(7) 0.7803(2) 0.0346(6) Uani 1 1 d . . .
H3A H 0.862(2) 0.830(5) 0.6191(19) 0.028(7) Uiso 1 1 d . . .
H5A H 0.667(2) 0.124(4) 0.8733(18) 0.023(6) Uiso 1 1 d . . .
H3B H 0.804(2) 0.574(4) 0.5631(18) 0.023(6) Uiso 1 1 d . . .
H10 H 0.351(2) 0.745(6) 0.472(2) 0.047(8) Uiso 1 1 d . . .
H5B H 0.6975(19) 0.295(4) 0.9821(18) 0.029(6) Uiso 1 1 d . . .
H4A H 1.150(2) 0.632(5) 0.770(2) 0.049(8) Uiso 1 1 d . . .
H6C H 0.359(2) 0.206(5) 0.812(2) 0.051(8) Uiso 1 1 d . . .
H6A H 0.385(3) 0.337(6) 0.719(2) 0.063(10) Uiso 1 1 d . . .
H4B H 1.178(2) 0.699(5) 0.6596(19) 0.051(8) Uiso 1 1 d . . .
H6B H 0.458(3) 0.118(6) 0.755(3) 0.077(12) Uiso 1 1 d . . .
H4C H 1.084(2) 0.861(5) 0.703(2) 0.048(9) Uiso 1 1 d . . .


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
O1 C1 1.230(3) . ?
O4 N6 1.234(2) . ?
O10 N9 1.357(2) . ?
O10 H10 0.88(2) . ?
O6 N8 1.245(2) . ?
O5 N6 1.236(3) . ?
N1 C2 1.282(3) . ?
N1 N2 1.376(2) . ?
N3 C2 1.365(3) . ?
N3 C1 1.391(3) . ?
N3 C5 1.473(3) . ?
O3 N4 1.224(3) . ?
O8 N9 1.217(2) . ?
O2 N4 1.213(3) . ?
N7 N8 1.344(3) . ?
N7 C5 1.444(3) . ?
N7 C6 1.458(3) . ?
O7 N8 1.227(2) . ?
O9 N9 1.211(2) . ?
N5 N6 1.346(3) . ?
N5 C3 1.440(3) . ?
N5 C4 1.458(3) . ?
N2 C1 1.363(3) . ?
N2 C3 1.464(3) . ?
C3 H3A 1.00(3) . ?
C3 H3B 0.98(2) . ?
N4 C2 1.458(3) . ?
C5 H5A 0.99(2) . ?
C5 H5B 0.97(2) . ?
C4 H4A 0.94(3) . ?
C4 H4B 0.99(2) . ?
C4 H4C 0.91(3) . ?
C6 H6C 0.96(3) . ?
C6 H6A 0.92(3) . ?
C6 H6B 0.88(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
N9 O10 H10 104.7(14) . . ?
C2 N1 N2 103.16(19) . . ?
C2 N3 C1 105.40(18) . . ?
C2 N3 C5 130.85(19) . . ?
C1 N3 C5 121.8(2) . . ?
N8 N7 C5 117.5(2) . . ?
N8 N7 C6 118.0(2) . . ?
C5 N7 C6 124.3(2) . . ?
N6 N5 C3 117.5(2) . . ?
N6 N5 C4 117.5(2) . . ?
C3 N5 C4 123.0(2) . . ?
C1 N2 N1 112.61(16) . . ?
C1 N2 C3 128.5(2) . . ?
N1 N2 C3 118.83(19) . . ?
O7 N8 O6 124.4(2) . . ?
O7 N8 N7 118.1(2) . . ?
O6 N8 N7 117.49(19) . . ?
O4 N6 O5 124.5(2) . . ?
O4 N6 N5 117.4(2) . . ?
O5 N6 N5 118.10(19) . . ?
O9 N9 O8 127.16(18) . . ?
O9 N9 O10 114.74(16) . . ?
O8 N9 O10 118.09(17) . . ?
N5 C3 N2 112.6(2) . . ?
N5 C3 H3A 108.7(13) . . ?
N2 C3 H3A 107.1(13) . . ?
N5 C3 H3B 111.4(13) . . ?
N2 C3 H3B 106.1(12) . . ?
H3A C3 H3B 110.8(19) . . ?
O2 N4 O3 126.4(2) . . ?
O2 N4 C2 117.2(2) . . ?
O3 N4 C2 116.4(2) . . ?
N7 C5 N3 112.63(19) . . ?
N7 C5 H5A 108.3(13) . . ?
N3 C5 H5A 105.7(13) . . ?
N7 C5 H5B 112.9(12) . . ?
N3 C5 H5B 108.0(13) . . ?
H5A C5 H5B 109.1(19) . . ?
O1 C1 N2 130.8(2) . . ?
O1 C1 N3 125.2(2) . . ?
N2 C1 N3 104.00(19) . . ?
N1 C2 N3 114.8(2) . . ?
N1 C2 N4 120.1(2) . . ?
N3 C2 N4 124.6(2) . . ?
N5 C4 H4A 109.6(17) . . ?
N5 C4 H4B 109.2(15) . . ?
H4A C4 H4B 105(2) . . ?
N5 C4 H4C 105.5(17) . . ?
H4A C4 H4C 116(2) . . ?
H4B C4 H4C 112(2) . . ?
N7 C6 H6C 113.6(15) . . ?
N7 C6 H6A 109.7(19) . . ?
H6C C6 H6A 103(2) . . ?
N7 C6 H6B 109(2) . . ?
H6C C6 H6B 113(3) . . ?
H6A C6 H6B 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
C2 N1 N2 C1 0.4(2) . . . . ?
C2 N1 N2 C3 -178.2(2) . . . . ?
C5 N7 N8 O7 -173.21(18) . . . . ?
C6 N7 N8 O7 2.3(3) . . . . ?
C5 N7 N8 O6 7.9(3) . . . . ?
C6 N7 N8 O6 -176.6(2) . . . . ?
C3 N5 N6 O4 -177.75(19) . . . . ?
C4 N5 N6 O4 -13.3(3) . . . . ?
C3 N5 N6 O5 3.8(3) . . . . ?
C4 N5 N6 O5 168.2(2) . . . . ?
N6 N5 C3 N2 83.5(3) . . . . ?
C4 N5 C3 N2 -80.0(3) . . . . ?
C1 N2 C3 N5 -101.1(3) . . . . ?
N1 N2 C3 N5 77.2(3) . . . . ?
N8 N7 C5 N3 -73.1(2) . . . . ?
C6 N7 C5 N3 111.7(3) . . . . ?
C2 N3 C5 N7 90.5(3) . . . . ?
C1 N3 C5 N7 -71.0(3) . . . . ?
N1 N2 C1 O1 176.7(2) . . . . ?
C3 N2 C1 O1 -4.9(4) . . . . ?
N1 N2 C1 N3 -1.7(2) . . . . ?
C3 N2 C1 N3 176.7(2) . . . . ?
C2 N3 C1 O1 -176.3(2) . . . . ?
C5 N3 C1 O1 -10.7(3) . . . . ?
C2 N3 C1 N2 2.2(2) . . . . ?
C5 N3 C1 N2 167.79(19) . . . . ?
N2 N1 C2 N3 1.1(2) . . . . ?
N2 N1 C2 N4 173.35(19) . . . . ?
C1 N3 C2 N1 -2.2(2) . . . . ?
C5 N3 C2 N1 -166.0(2) . . . . ?
C1 N3 C2 N4 -174.0(2) . . . . ?
C5 N3 C2 N4 22.2(3) . . . . ?
O2 N4 C2 N1 -150.2(2) . . . . ?
O3 N4 C2 N1 28.3(3) . . . . ?
O2 N4 C2 N3 21.1(3) . . . . ?
O3 N4 C2 N3 -160.3(2) . . . . ?

_geom_special_details            ?

####################################################################### 
# 
# 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_fx530
_database_code_depnum_ccdc_archive 'CCDC 1439321'

_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           SHELXL-97
_audit_creation_date             
;
'Thu Nov 11 13:20:25 2010'
;

_chemical_name_systematic        
1-(3-nitro-1H-1,2,4-triazol-5-on-4-yl)-2-nitrazapropane
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C4 H6 N6 O5'
_chemical_formula_sum            'C4 H6 N6 O5'
_chemical_formula_weight         218.128

_diffrn_ambient_temperature      173(2)
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ?
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            2241
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         26.30
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             1644
_reflns_number_gt                1177
_reflns_threshold_expression     >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0667444186
_diffrn_orient_matrix_UB_12      -0.0052167196
_diffrn_orient_matrix_UB_13      -0.0532399537
_diffrn_orient_matrix_UB_21      -0.0780492918
_diffrn_orient_matrix_UB_22      -0.0356645486
_diffrn_orient_matrix_UB_23      0.0327960243
_diffrn_orient_matrix_UB_31      -0.0254716760
_diffrn_orient_matrix_UB_32      0.1237040477
_diffrn_orient_matrix_UB_33      0.0071823693
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00  103.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00  103.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000   79.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   39.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.0000   80.0000  250.0000 104

;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7610(6)
_cell_length_b                   5.5064(6)
_cell_length_c                   11.3925(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.072(9)
_cell_angle_gamma                90.00
_cell_volume                     420.90(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    849
_cell_measurement_theta_min      4.4103
_cell_measurement_theta_max      33.8119
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

_diffrn_special_details          ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.036

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_computing_publication_material  
;
Diamond Version 3.2k (K. Brandenburg, Crystal Impact GbR, Berlin, 2014).
;
_refine_special_details          ?

_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)+(0.0133P)²+0.0000P] 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_extinction_expression ?
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.839
_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
O5 O 0.6050(2) 0.7904(3) 0.59511(13) 0.0366(5) Uani 1 1 d . . .
O4 O 1.2640(3) 0.1642(3) 0.69802(15) 0.0412(5) Uani 1 1 d . . .
O1 O 0.7402(3) 0.5158(4) 1.00738(15) 0.0416(5) Uani 1 1 d . . .
N5 N 0.8030(3) 0.7509(4) 0.85949(15) 0.0274(5) Uani 1 1 d . . .
N4 N 1.2138(3) 0.3758(4) 0.70273(16) 0.0311(5) Uani 1 1 d . . .
O2 O 0.9759(2) 0.4162(3) 0.90062(13) 0.0336(4) Uani 1 1 d . . .
N3 N 0.9154(3) 0.6431(3) 0.67397(15) 0.0229(5) Uani 1 1 d . . .
N2 N 0.9161(3) 0.2955(4) 0.57346(16) 0.0297(5) Uani 1 1 d . . .
N1 N 0.7422(3) 0.4206(4) 0.54299(17) 0.0298(5) Uani 1 1 d . . .
N6 N 0.8408(3) 0.5524(4) 0.92669(17) 0.0288(5) Uani 1 1 d . . .
O3 O 1.3170(2) 0.5423(4) 0.74473(16) 0.0486(5) Uani 1 1 d . . .
C4 C 0.6476(4) 0.9163(6) 0.8880(3) 0.0384(7) Uani 1 1 d . . .
C3 C 0.9415(4) 0.8065(5) 0.7758(2) 0.0263(6) Uani 1 1 d . . .
C2 C 1.0111(3) 0.4354(5) 0.65236(18) 0.0241(5) Uani 1 1 d . . .
C1 C 0.7342(4) 0.6364(5) 0.59986(19) 0.0282(6) Uani 1 1 d . . .
H3B H 1.083(3) 0.799(4) 0.8122(16) 0.017(5) Uiso 1 1 d . . .
H1 H 0.636(3) 0.357(4) 0.4929(18) 0.039(7) Uiso 1 1 d . . .
H3A H 0.911(3) 0.972(4) 0.7421(16) 0.014(6) Uiso 1 1 d . . .
H4A H 0.689(4) 0.991(5) 0.966(2) 0.058(9) Uiso 1 1 d . . .
H4C H 0.632(4) 1.052(7) 0.827(2) 0.080(11) Uiso 1 1 d . . .
H4B H 0.528(4) 0.820(6) 0.886(2) 0.069(10) Uiso 1 1 d . . .


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
O5 C1 1.214(3) . ?
O4 N4 1.216(2) . ?
O1 N6 1.226(2) . ?
N5 N6 1.341(2) . ?
N5 C3 1.449(3) . ?
N5 C4 1.458(3) . ?
N4 O3 1.214(3) . ?
N4 C2 1.457(3) . ?
O2 N6 1.246(2) . ?
N3 C2 1.351(3) . ?
N3 C1 1.400(3) . ?
N3 C3 1.462(3) . ?
N2 C2 1.293(3) . ?
N2 N1 1.370(2) . ?
N1 C1 1.358(3) . ?
N1 H1 0.93(2) . ?
C4 H4A 0.98(3) . ?
C4 H4C 1.01(3) . ?
C4 H4B 0.97(3) . ?
C3 H3B 0.992(18) . ?
C3 H3A 1.00(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
N6 N5 C3 117.05(19) . . ?
N6 N5 C4 118.3(2) . . ?
C3 N5 C4 123.8(2) . . ?
O3 N4 O4 126.2(2) . . ?
O3 N4 C2 116.9(2) . . ?
O4 N4 C2 116.9(2) . . ?
C2 N3 C1 105.71(19) . . ?
C2 N3 C3 130.66(19) . . ?
C1 N3 C3 120.4(2) . . ?
C2 N2 N1 102.37(19) . . ?
C1 N1 N2 113.7(2) . . ?
C1 N1 H1 123.4(14) . . ?
N2 N1 H1 122.7(14) . . ?
O1 N6 O2 124.8(2) . . ?
O1 N6 N5 118.6(2) . . ?
O2 N6 N5 116.6(2) . . ?
N5 C4 H4A 109.2(15) . . ?
N5 C4 H4C 108.9(17) . . ?
H4A C4 H4C 107(2) . . ?
N5 C4 H4B 106.1(18) . . ?
H4A C4 H4B 114(2) . . ?
H4C C4 H4B 112(2) . . ?
N5 C3 N3 111.5(2) . . ?
N5 C3 H3B 112.4(11) . . ?
N3 C3 H3B 108.7(12) . . ?
N5 C3 H3A 108.9(11) . . ?
N3 C3 H3A 104.9(11) . . ?
H3B C3 H3A 110.1(17) . . ?
N2 C2 N3 115.00(19) . . ?
N2 C2 N4 120.2(2) . . ?
N3 C2 N4 124.6(2) . . ?
O5 C1 N1 131.3(2) . . ?
O5 C1 N3 125.4(2) . . ?
N1 C1 N3 103.2(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
C2 N2 N1 C1 1.9(3) . . . . ?
C3 N5 N6 O1 171.7(2) . . . . ?
C4 N5 N6 O1 1.6(3) . . . . ?
C3 N5 N6 O2 -9.2(3) . . . . ?
C4 N5 N6 O2 -179.3(2) . . . . ?
N6 N5 C3 N3 74.6(2) . . . . ?
C4 N5 C3 N3 -115.9(3) . . . . ?
C2 N3 C3 N5 -95.2(3) . . . . ?
C1 N3 C3 N5 61.5(3) . . . . ?
N1 N2 C2 N3 -1.3(2) . . . . ?
N1 N2 C2 N4 -175.61(18) . . . . ?
C1 N3 C2 N2 0.4(2) . . . . ?
C3 N3 C2 N2 159.6(2) . . . . ?
C1 N3 C2 N4 174.4(2) . . . . ?
C3 N3 C2 N4 -26.4(4) . . . . ?
O3 N4 C2 N2 156.8(2) . . . . ?
O4 N4 C2 N2 -22.7(3) . . . . ?
O3 N4 C2 N3 -16.9(3) . . . . ?
O4 N4 C2 N3 163.5(2) . . . . ?
N2 N1 C1 O5 -179.4(2) . . . . ?
N2 N1 C1 N3 -1.7(2) . . . . ?
C2 N3 C1 O5 178.7(2) . . . . ?
C3 N3 C1 O5 16.9(4) . . . . ?
C2 N3 C1 N1 0.8(2) . . . . ?
C3 N3 C1 N1 -161.1(2) . . . . ?


_geom_special_details            ?

