# 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 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gx503
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Tue Aug 30 01:49:49 2011'
;
_audit_update_record             30.08.2011

_chemical_name_systematic        3,4-Dicarboxamidoximyl-furoxane
_chemical_compound_source        ?
_chemical_name_common            3,4-Dicarboxamidoximyl-furoxane
_chemical_formula_moiety         'C4 H6 N6 O4'
_chemical_formula_sum            'C4 H6 N6 O4'
_chemical_formula_weight         202.15


_cell_length_a                   6.9708(14)
_cell_length_b                   14.408(2)
_cell_length_c                   7.8104(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.99(2)
_cell_angle_gamma                90.00
_cell_volume                     754.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1346
_cell_measurement_theta_min      4.2348
_cell_measurement_theta_max      33.5682
_cell_special_details            ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9783
_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 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            3900
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.48
_diffrn_reflns_theta_max         26.49
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.990

_reflns_number_total             1547
_reflns_number_gt                1301
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0320607000
_diffrn_orient_matrix_UB_12      -0.0126115000
_diffrn_orient_matrix_UB_13      0.0912031000
_diffrn_orient_matrix_UB_21      0.1006255000
_diffrn_orient_matrix_UB_22      0.0003901000
_diffrn_orient_matrix_UB_23      -0.0035637000
_diffrn_orient_matrix_UB_31      0.0080078000
_diffrn_orient_matrix_UB_32      0.0475486000
_diffrn_orient_matrix_UB_33      0.0244626000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2yn

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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.060

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1547
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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 -0.2454(2) 0.15860(11) 0.0266(2) 0.0269(4) Uani 1 1 d . . .
O2 O -0.1086(3) 0.20202(13) 0.3137(2) 0.0323(4) Uani 1 1 d . . .
O3 O 0.5033(3) 0.13332(13) 0.5221(2) 0.0320(4) Uani 1 1 d . . .
O4 O 0.4019(3) 0.01776(12) -0.2148(2) 0.0251(4) Uani 1 1 d . . .
N1 N -0.0747(3) 0.17012(14) 0.1797(3) 0.0244(4) Uani 1 1 d . . .
N2 N -0.1792(3) 0.12409(14) -0.1099(3) 0.0247(4) Uani 1 1 d . . .
N3 N 0.3071(3) 0.11598(14) 0.4141(2) 0.0263(5) Uani 1 1 d . . .
N4 N 0.4296(3) 0.19740(14) 0.2039(3) 0.0248(5) Uani 1 1 d . . .
N5 N 0.3079(3) 0.05076(13) -0.0871(2) 0.0214(4) Uani 1 1 d . . .
N6 N 0.0393(3) 0.07897(16) -0.3428(3) 0.0293(5) Uani 1 1 d . . .
C1 C 0.0858(3) 0.14331(15) 0.1335(3) 0.0214(5) Uani 1 1 d . . .
C2 C 0.0163(3) 0.11553(15) -0.0474(3) 0.0205(5) Uani 1 1 d . . .
C3 C 0.2879(3) 0.15082(15) 0.2579(3) 0.0218(5) Uani 1 1 d . . .
C4 C 0.1304(3) 0.08033(15) -0.1675(3) 0.0209(5) Uani 1 1 d . . .
H4B H 0.548(4) 0.1923(16) 0.269(3) 0.016(6) Uiso 1 1 d . . .
H6B H 0.113(5) 0.076(2) -0.423(4) 0.041(8) Uiso 1 1 d . . .
H4A H 0.407(5) 0.201(2) 0.096(5) 0.049(9) Uiso 1 1 d . . .
H6A H -0.072(5) 0.104(2) -0.376(4) 0.038(8) Uiso 1 1 d . . .
H3 H 0.516(5) 0.100(2) 0.616(5) 0.045(9) Uiso 1 1 d . . .
H4 H 0.498(5) -0.004(2) -0.154(4) 0.043(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 N2 1.367(2) . ?
O1 N1 1.446(3) . ?
O2 N1 1.224(2) . ?
O3 N3 1.418(3) . ?
O3 H3 0.86(3) . ?
O4 N5 1.418(2) . ?
O4 H4 0.78(3) . ?
N1 C1 1.325(3) . ?
N2 C2 1.320(3) . ?
N3 C3 1.292(3) . ?
N4 C3 1.354(3) . ?
N4 H4B 0.84(3) . ?
N4 H4A 0.81(3) . ?
N5 C4 1.296(3) . ?
N6 C4 1.341(3) . ?
N6 H6B 0.91(3) . ?
N6 H6A 0.83(3) . ?
C1 C2 1.419(3) . ?
C1 C3 1.478(3) . ?
C2 C4 1.477(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N1 108.00(15) . . ?
N3 O3 H3 105(2) . . ?
N5 O4 H4 101(2) . . ?
O2 N1 C1 136.0(2) . . ?
O2 N1 O1 116.20(18) . . ?
C1 N1 O1 107.81(17) . . ?
C2 N2 O1 106.35(18) . . ?
C3 N3 O3 109.00(19) . . ?
C3 N4 H4B 116.2(16) . . ?
C3 N4 H4A 114(2) . . ?
H4B N4 H4A 121(3) . . ?
C4 N5 O4 109.49(17) . . ?
C4 N6 H6B 120.1(19) . . ?
C4 N6 H6A 117(2) . . ?
H6B N6 H6A 118(3) . . ?
N1 C1 C2 105.71(19) . . ?
N1 C1 C3 121.57(19) . . ?
C2 C1 C3 132.62(19) . . ?
N2 C2 C1 112.13(19) . . ?
N2 C2 C4 118.6(2) . . ?
C1 C2 C4 129.3(2) . . ?
N3 C3 N4 126.3(2) . . ?
N3 C3 C1 115.1(2) . . ?
N4 C3 C1 118.5(2) . . ?
N5 C4 N6 127.6(2) . . ?
N5 C4 C2 114.48(19) . . ?
N6 C4 C2 117.8(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
N2 O1 N1 O2 178.96(18) . . . . ?
N2 O1 N1 C1 0.1(2) . . . . ?
N1 O1 N2 C2 -0.4(2) . . . . ?
O2 N1 C1 C2 -178.3(2) . . . . ?
O1 N1 C1 C2 0.2(2) . . . . ?
O2 N1 C1 C3 -1.6(4) . . . . ?
O1 N1 C1 C3 176.86(18) . . . . ?
O1 N2 C2 C1 0.6(2) . . . . ?
O1 N2 C2 C4 -179.29(18) . . . . ?
N1 C1 C2 N2 -0.5(3) . . . . ?
C3 C1 C2 N2 -176.6(2) . . . . ?
N1 C1 C2 C4 179.3(2) . . . . ?
C3 C1 C2 C4 3.2(4) . . . . ?
O3 N3 C3 N4 -0.6(3) . . . . ?
O3 N3 C3 C1 -176.23(17) . . . . ?
N1 C1 C3 N3 50.5(3) . . . . ?
C2 C1 C3 N3 -133.8(2) . . . . ?
N1 C1 C3 N4 -125.4(2) . . . . ?
C2 C1 C3 N4 50.2(3) . . . . ?
O4 N5 C4 N6 2.1(3) . . . . ?
O4 N5 C4 C2 179.27(17) . . . . ?
N2 C2 C4 N5 -162.5(2) . . . . ?
C1 C2 C4 N5 17.7(3) . . . . ?
N2 C2 C4 N6 15.0(3) . . . . ?
C1 C2 C4 N6 -164.8(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
N4 H4B O2 0.84(3) 2.33(3) 3.095(3) 151(2) 1_655
N6 H6B N3 0.91(3) 2.18(3) 3.054(3) 161(3) 1_554
N4 H4A N5 0.81(3) 2.58(3) 3.047(3) 118(3) .
N4 H4A O2 0.81(3) 2.59(3) 3.319(3) 150(3) 4_665
O3 H3 O4 0.86(3) 2.09(3) 2.880(3) 153(3) 1_556
O3 H3 N2 0.86(3) 2.59(3) 3.110(3) 120(3) 1_656
O4 H4 N5 0.78(3) 2.10(3) 2.828(3) 156(3) 3_655

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988403'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gx547
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Fri Sep 23 17:29:52 2011'
;
_audit_update_record             31.01.2014

_chemical_name_systematic        
'bisammonium 4,5-bis(1-oxidotetrazolyl)furoxane'
_chemical_compound_source        ?
_chemical_name_common            
'bisammonium 4,5-bis(1-oxidotetrazolyl)furoxane'
_chemical_formula_moiety         'C4 N10 O4, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N12 O4'
_chemical_formula_weight         288.22


_cell_length_a                   7.5509(13)
_cell_length_b                   7.8440(15)
_cell_length_c                   18.562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.987(16)
_cell_angle_gamma                90.00
_cell_volume                     1095.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1178
_cell_measurement_theta_min      4.3997
_cell_measurement_theta_max      33.4800
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_T_max  0.9850
_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      293 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            5459
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         25.99
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             2140
_reflns_number_gt                1624
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0525978000
_diffrn_orient_matrix_UB_12      -0.0490808000
_diffrn_orient_matrix_UB_13      0.0259491000
_diffrn_orient_matrix_UB_21      0.0160822000
_diffrn_orient_matrix_UB_22      0.0737489000
_diffrn_orient_matrix_UB_23      0.0215115000
_diffrn_orient_matrix_UB_31      -0.0766196000
_diffrn_orient_matrix_UB_32      -0.0182093000
_diffrn_orient_matrix_UB_33      0.0182690000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2yn

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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.053

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.0714P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O2 O 0.37731(17) 0.07039(18) 0.09087(7) 0.0228(3) Uani 1 1 d . . .
O4 O 0.57685(19) -0.23900(18) 0.13603(7) 0.0289(4) Uani 1 1 d . . .
O1 O 0.77861(17) -0.06735(18) 0.45709(7) 0.0230(3) Uani 1 1 d . . .
O3 O 0.75623(18) -0.22429(18) 0.24085(7) 0.0256(4) Uani 1 1 d . . .
N11 N 0.1123(2) -0.0682(3) 0.40308(10) 0.0206(4) Uani 1 1 d . . .
N5 N 0.2788(2) 0.0436(2) 0.14535(8) 0.0181(4) Uani 1 1 d . . .
N12 N 0.7456(3) 0.0736(3) 0.04389(10) 0.0245(4) Uani 1 1 d . . .
N4 N 0.4436(2) 0.1687(2) 0.36523(9) 0.0232(4) Uani 1 1 d . . .
N3 N 0.4651(2) 0.2396(2) 0.43160(9) 0.0258(4) Uani 1 1 d . . .
N8 N 0.1849(2) -0.0152(2) 0.25002(8) 0.0214(4) Uani 1 1 d . . .
N7 N 0.0517(2) 0.0502(2) 0.20582(9) 0.0232(4) Uani 1 1 d . . .
N1 N 0.6507(2) 0.0366(2) 0.43191(8) 0.0193(4) Uani 1 1 d . . .
N2 N 0.5904(2) 0.1605(2) 0.47275(9) 0.0241(4) Uani 1 1 d . . .
N10 N 0.5961(2) -0.1792(2) 0.19749(9) 0.0213(4) Uani 1 1 d . . .
N6 N 0.1064(2) 0.0873(2) 0.14216(9) 0.0232(4) Uani 1 1 d . . .
N9 N 0.7508(2) -0.1489(2) 0.30715(9) 0.0234(4) Uani 1 1 d . . .
C3 C 0.5018(2) -0.0792(2) 0.23704(10) 0.0175(4) Uani 1 1 d . . .
C1 C 0.5607(2) 0.0417(2) 0.36607(10) 0.0174(4) Uani 1 1 d . . .
C4 C 0.3261(2) -0.0188(2) 0.21146(10) 0.0182(4) Uani 1 1 d . . .
C2 C 0.6016(2) -0.0632(2) 0.30534(10) 0.0180(4) Uani 1 1 d . . .
H11D H -0.008(3) -0.052(3) 0.4099(11) 0.026(6) Uiso 1 1 d . . .
H12C H 0.746(3) 0.193(4) 0.0397(13) 0.044(7) Uiso 1 1 d . . .
H11C H 0.139(3) -0.037(3) 0.3552(13) 0.034(6) Uiso 1 1 d . . .
H11B H 0.132(3) -0.182(4) 0.4081(13) 0.043(7) Uiso 1 1 d . . .
H12D H 0.719(3) 0.025(3) -0.0046(14) 0.042(7) Uiso 1 1 d . . .
H11A H 0.171(4) -0.009(4) 0.4418(16) 0.063(9) Uiso 1 1 d . . .
H12A H 0.849(3) 0.042(3) 0.0627(12) 0.031(6) Uiso 1 1 d . . .
H12B H 0.658(4) 0.043(3) 0.0723(14) 0.045(7) 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
O2 N5 1.323(2) . ?
O4 N10 1.231(2) . ?
O1 N1 1.3187(19) . ?
O3 N9 1.369(2) . ?
O3 N10 1.437(2) . ?
N5 C4 1.340(2) . ?
N5 N6 1.343(2) . ?
N4 C1 1.332(2) . ?
N4 N3 1.348(2) . ?
N3 N2 1.318(2) . ?
N8 C4 1.335(2) . ?
N8 N7 1.344(2) . ?
N7 N6 1.318(2) . ?
N1 N2 1.336(2) . ?
N1 C1 1.346(2) . ?
N10 C3 1.323(2) . ?
N9 C2 1.310(2) . ?
C3 C2 1.423(3) . ?
C3 C4 1.449(3) . ?
C1 C2 1.450(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 O3 N10 107.92(13) . . ?
O2 N5 C4 129.43(16) . . ?
O2 N5 N6 122.20(15) . . ?
C4 N5 N6 108.28(15) . . ?
C1 N4 N3 105.70(15) . . ?
N2 N3 N4 111.04(16) . . ?
C4 N8 N7 105.74(15) . . ?
N6 N7 N8 110.83(15) . . ?
O1 N1 N2 121.58(15) . . ?
O1 N1 C1 129.52(16) . . ?
N2 N1 C1 108.90(15) . . ?
N3 N2 N1 106.01(15) . . ?
O4 N10 C3 135.58(17) . . ?
O4 N10 O3 116.84(15) . . ?
C3 N10 O3 107.59(15) . . ?
N7 N6 N5 106.40(15) . . ?
C2 N9 O3 106.95(15) . . ?
N10 C3 C2 106.13(16) . . ?
N10 C3 C4 122.23(17) . . ?
C2 C3 C4 131.43(17) . . ?
N4 C1 N1 108.35(16) . . ?
N4 C1 C2 126.98(17) . . ?
N1 C1 C2 124.35(17) . . ?
N8 C4 N5 108.75(16) . . ?
N8 C4 C3 125.60(17) . . ?
N5 C4 C3 125.64(17) . . ?
N9 C2 C3 111.42(17) . . ?
N9 C2 C1 120.80(16) . . ?
C3 C2 C1 127.63(17) . . ?

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
? ? ? ? ? ? ? ? ? ?

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
N11 H11D O1 0.94(2) 1.90(2) 2.792(2) 157.5(18) 1_455
N11 H11D N9 0.94(2) 2.63(2) 3.190(2) 118.9(15) 1_455
N12 H12C O1 0.94(3) 1.89(3) 2.822(3) 171(2) 2_655
N11 H11C N8 0.96(2) 2.02(3) 2.969(2) 170(2) .
N11 H11B O2 0.91(3) 1.94(3) 2.838(3) 168(2) 2_545
N11 H11B N5 0.91(3) 2.49(3) 3.300(3) 149(2) 2_545
N12 H12D O2 0.98(3) 1.86(3) 2.827(2) 168(2) 3_655
N12 H12D N5 0.98(3) 2.67(3) 3.620(3) 163.3(19) 3_655
N11 H11A O1 0.93(3) 1.97(3) 2.859(2) 157(3) 3_656
N11 H11A N2 0.93(3) 2.59(3) 3.159(3) 120(2) 3_656
N11 H11A N1 0.93(3) 2.61(3) 3.420(2) 145(2) 3_656
N12 H12A N6 0.87(2) 2.36(2) 3.146(3) 151(2) 1_655
N12 H12B O2 0.91(3) 2.19(3) 2.986(2) 145(2) .
N12 H12B O4 0.91(3) 2.61(3) 3.308(3) 134(2) .

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988404'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gx567

_vrf_PLAT089_gx567               
; 
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) 
RESPONSE: Friedel pairs were merged (MERG3) 
due to non-centrosymmetric space ggroup
;
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Thu Oct 06 14:14:38 2011'
;
_audit_update_record             07.10.2011

_chemical_name_systematic        
'bishydroxyammonium 4,5-bis(1-oxidotetrazolyl)furoxane monohydrate'
_chemical_compound_source        ?
_chemical_name_common            
'bishydroxyammonium 4,5-bis(1-oxidotetrazolyl)furoxane monohydrate'
_chemical_formula_moiety         'C4 N10 O4, 2(H4 N O), H2 O'
_chemical_formula_sum            'C4 H10 N12 O7'
_chemical_formula_weight         338.24


_cell_length_a                   8.0286(12)
_cell_length_b                   8.0668(11)
_cell_length_c                   9.6666(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.004(12)
_cell_angle_gamma                90.00
_cell_volume                     626.06(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    921
_cell_measurement_theta_min      4.1473
_cell_measurement_theta_max      29.9973
_cell_special_details            ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_T_max  0.9837
_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 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            3382
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         26.48
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             1383
_reflns_number_gt                1208
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      -0.0071486000
_diffrn_orient_matrix_UB_12      0.0861823000
_diffrn_orient_matrix_UB_13      -0.0132189000
_diffrn_orient_matrix_UB_21      -0.0654481000
_diffrn_orient_matrix_UB_22      0.0051350000
_diffrn_orient_matrix_UB_23      0.0489846000
_diffrn_orient_matrix_UB_31      0.0587850000
_diffrn_orient_matrix_UB_32      0.0168043000
_diffrn_orient_matrix_UB_33      0.0530762000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0217P)²+0.0000P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         1383
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0616
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.3449(2) 0.7610(3) -0.2929(2) 0.0223(5) Uani 1 1 d . . .
O2 O 0.1855(3) 0.4280(3) -0.2048(2) 0.0258(5) Uani 1 1 d . . .
O3 O 0.0084(3) 0.4695(2) -0.0228(2) 0.0246(5) Uani 1 1 d . . .
O4 O 0.0030(2) 0.6436(2) 0.3881(2) 0.0212(5) Uani 1 1 d . . .
N1 N 0.4450(3) 0.7326(3) -0.1858(2) 0.0186(5) Uani 1 1 d . . .
N2 N 0.6059(3) 0.7778(3) -0.1878(3) 0.0232(6) Uani 1 1 d . . .
N3 N 0.6676(3) 0.7385(3) -0.0661(3) 0.0239(6) Uani 1 1 d . . .
N4 N 0.5495(3) 0.6679(3) 0.0145(2) 0.0219(6) Uani 1 1 d . . .
N5 N 0.1613(3) 0.5011(3) -0.0956(3) 0.0197(6) Uani 1 1 d . . .
N6 N 0.0100(3) 0.5579(3) 0.0982(3) 0.0231(6) Uani 1 1 d . . .
N7 N 0.1210(3) 0.7447(3) 0.3409(2) 0.0170(5) Uani 1 1 d . . .
N8 N 0.1883(3) 0.8624(3) 0.4212(3) 0.0229(6) Uani 1 1 d . . .
N9 N 0.3017(3) 0.9369(3) 0.3432(3) 0.0278(6) Uani 1 1 d . . .
N10 N 0.3087(3) 0.8675(3) 0.2158(3) 0.0243(6) Uani 1 1 d . . .
C1 C 0.4113(3) 0.6661(4) -0.0620(3) 0.0171(6) Uani 1 1 d . . .
C2 C 0.2484(4) 0.6075(4) -0.0187(3) 0.0172(6) Uani 1 1 d . . .
C3 C 0.1521(3) 0.6387(4) 0.1020(3) 0.0174(6) Uani 1 1 d . . .
C4 C 0.1952(3) 0.7476(4) 0.2164(3) 0.0172(6) Uani 1 1 d . . .
O5 O 0.3886(3) 0.1822(3) 0.5966(2) 0.0301(6) Uani 1 1 d . . .
N11 N 0.3162(4) 0.0996(4) 0.7108(3) 0.0213(6) Uani 1 1 d . . .
O6 O 0.0024(3) 0.2374(3) 0.2746(2) 0.0330(6) Uani 1 1 d . . .
N12 N 0.1059(4) 0.3077(4) 0.3774(3) 0.0228(6) Uani 1 1 d . . .
O7 O 0.6383(3) 0.0166(3) 0.4943(3) 0.0250(5) Uani 1 1 d . . .
H12C H 0.084(6) 0.249(6) 0.470(5) 0.082(15) Uiso 1 1 d . . .
H5A H 0.485(5) 0.119(5) 0.571(4) 0.053(12) Uiso 1 1 d . . .
H12A H 0.082(5) 0.423(6) 0.404(4) 0.064(13) Uiso 1 1 d . . .
H12B H 0.207(4) 0.297(4) 0.347(4) 0.031(10) Uiso 1 1 d . . .
H7A H 0.602(5) -0.065(6) 0.438(4) 0.052(12) Uiso 1 1 d . . .
H11B H 0.209(4) 0.126(4) 0.703(3) 0.029(10) Uiso 1 1 d . . .
H7B H 0.654(5) 0.081(5) 0.430(4) 0.040(12) Uiso 1 1 d . . .
H6 H -0.112(7) 0.248(7) 0.297(5) 0.090(17) Uiso 1 1 d . . .
H11A H 0.369(4) 0.131(5) 0.793(4) 0.039(10) Uiso 1 1 d . . .
H11C H 0.328(4) -0.009(5) 0.694(4) 0.041(11) 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 N1 1.330(3) . ?
O2 N5 1.224(3) . ?
O3 N6 1.370(3) . ?
O3 N5 1.438(3) . ?
O4 N7 1.331(3) . ?
N1 C1 1.339(3) . ?
N1 N2 1.343(3) . ?
N2 N3 1.315(3) . ?
N3 N4 1.353(3) . ?
N4 C1 1.333(4) . ?
N5 C2 1.333(4) . ?
N6 C3 1.314(4) . ?
N7 N8 1.340(3) . ?
N7 C4 1.343(3) . ?
N8 N9 1.326(4) . ?
N9 N10 1.354(4) . ?
N10 C4 1.329(4) . ?
C1 C2 1.452(4) . ?
C2 C3 1.422(4) . ?
C3 C4 1.454(4) . ?
O5 N11 1.414(3) . ?
O5 H5A 0.96(4) . ?
N11 H11B 0.89(3) . ?
N11 H11A 0.93(4) . ?
N11 H11C 0.90(4) . ?
O6 N12 1.414(3) . ?
O6 H6 0.95(5) . ?
N12 H12C 1.03(5) . ?
N12 H12A 0.98(5) . ?
N12 H12B 0.87(4) . ?
O7 H7A 0.90(5) . ?
O7 H7B 0.82(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
N6 O3 N5 108.5(2) . . ?
O1 N1 C1 130.0(2) . . ?
O1 N1 N2 121.5(2) . . ?
C1 N1 N2 108.4(2) . . ?
N3 N2 N1 106.5(2) . . ?
N2 N3 N4 110.7(2) . . ?
C1 N4 N3 105.6(2) . . ?
O2 N5 C2 135.0(3) . . ?
O2 N5 O3 118.1(2) . . ?
C2 N5 O3 106.8(2) . . ?
C3 N6 O3 106.9(2) . . ?
O4 N7 N8 121.5(2) . . ?
O4 N7 C4 129.3(2) . . ?
N8 N7 C4 109.1(2) . . ?
N9 N8 N7 105.6(2) . . ?
N8 N9 N10 111.0(2) . . ?
C4 N10 N9 105.6(2) . . ?
N4 C1 N1 108.8(2) . . ?
N4 C1 C2 126.4(3) . . ?
N1 C1 C2 124.7(2) . . ?
N5 C2 C3 106.6(3) . . ?
N5 C2 C1 121.4(3) . . ?
C3 C2 C1 131.9(3) . . ?
N6 C3 C2 111.2(3) . . ?
N6 C3 C4 121.8(3) . . ?
C2 C3 C4 127.0(2) . . ?
N10 C4 N7 108.7(2) . . ?
N10 C4 C3 126.8(3) . . ?
N7 C4 C3 124.5(2) . . ?
N11 O5 H5A 106(2) . . ?
O5 N11 H11B 103(2) . . ?
O5 N11 H11A 110(2) . . ?
H11B N11 H11A 117(3) . . ?
O5 N11 H11C 106(2) . . ?
H11B N11 H11C 109(3) . . ?
H11A N11 H11C 112(3) . . ?
N12 O6 H6 112(3) . . ?
O6 N12 H12C 109(3) . . ?
O6 N12 H12A 117(2) . . ?
H12C N12 H12A 100(3) . . ?
O6 N12 H12B 106(2) . . ?
H12C N12 H12B 114(3) . . ?
H12A N12 H12B 111(3) . . ?
H7A O7 H7B 94(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
O1 N1 N2 N3 177.6(2) . . . . ?
C1 N1 N2 N3 0.0(3) . . . . ?
N1 N2 N3 N4 0.3(3) . . . . ?
N2 N3 N4 C1 -0.4(3) . . . . ?
N6 O3 N5 O2 177.5(2) . . . . ?
N6 O3 N5 C2 -0.8(3) . . . . ?
N5 O3 N6 C3 0.0(3) . . . . ?
O4 N7 N8 N9 178.9(2) . . . . ?
C4 N7 N8 N9 0.8(3) . . . . ?
N7 N8 N9 N10 -0.7(3) . . . . ?
N8 N9 N10 C4 0.3(3) . . . . ?
N3 N4 C1 N1 0.4(3) . . . . ?
N3 N4 C1 C2 -177.6(3) . . . . ?
O1 N1 C1 N4 -177.7(3) . . . . ?
N2 N1 C1 N4 -0.3(3) . . . . ?
O1 N1 C1 C2 0.4(5) . . . . ?
N2 N1 C1 C2 177.8(3) . . . . ?
O2 N5 C2 C3 -176.7(3) . . . . ?
O3 N5 C2 C3 1.3(3) . . . . ?
O2 N5 C2 C1 1.9(5) . . . . ?
O3 N5 C2 C1 179.8(2) . . . . ?
N4 C1 C2 N5 -130.2(3) . . . . ?
N1 C1 C2 N5 52.1(4) . . . . ?
N4 C1 C2 C3 47.9(5) . . . . ?
N1 C1 C2 C3 -129.8(3) . . . . ?
O3 N6 C3 C2 0.8(3) . . . . ?
O3 N6 C3 C4 179.3(2) . . . . ?
N5 C2 C3 N6 -1.4(3) . . . . ?
C1 C2 C3 N6 -179.7(3) . . . . ?
N5 C2 C3 C4 -179.7(3) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
N9 N10 C4 N7 0.2(3) . . . . ?
N9 N10 C4 C3 178.5(3) . . . . ?
O4 N7 C4 N10 -178.6(3) . . . . ?
N8 N7 C4 N10 -0.6(3) . . . . ?
O4 N7 C4 C3 3.0(4) . . . . ?
N8 N7 C4 C3 -179.0(3) . . . . ?
N6 C3 C4 N10 -160.2(3) . . . . ?
C2 C3 C4 N10 17.9(5) . . . . ?
N6 C3 C4 N7 17.9(4) . . . . ?
C2 C3 C4 N7 -164.0(3) . . . . ?

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
N12 H12C O4 1.03(5) 1.75(5) 2.767(3) 166(4) 2_546
N12 H12C N7 1.03(5) 2.46(5) 3.315(4) 140(4) 2_546
O5 H5A O7 0.96(4) 1.66(4) 2.604(3) 168(3) .
N12 H12A O4 0.98(5) 1.90(5) 2.834(4) 159(3) .
N12 H12A N7 0.98(5) 2.68(5) 3.545(4) 147(3) .
N12 H12B N2 0.87(4) 2.15(4) 2.961(4) 154(3) 2_645
O7 H7A O5 0.90(5) 2.07(5) 2.845(3) 144(4) 2_646
O7 H7A N9 0.90(5) 2.58(4) 3.138(4) 121(3) 1_545
N11 H11B O4 0.89(3) 1.92(3) 2.758(4) 156(3) 2_546
N11 H11B N6 0.89(3) 2.66(3) 3.222(4) 122(2) 2_546
O7 H7B O1 0.82(4) 1.97(4) 2.775(3) 168(4) 2_645
O6 H6 O1 0.95(5) 1.87(5) 2.801(3) 165(4) 2_545
N11 H11A N4 0.93(4) 2.00(4) 2.919(4) 168(3) 2_646
N11 H11C O1 0.90(4) 1.86(4) 2.742(4) 166(3) 1_546
N11 H11C N1 0.90(4) 2.56(4) 3.291(4) 139(3) 1_546

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988405'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix108
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             11.03.2013
_audit_update_record             12.03.2013

_chemical_name_systematic        3,4-Dichloroximidoyl-furoxane
_chemical_compound_source        ?
_chemical_name_common            3,4-Dichloroximidoyl-furoxane
_chemical_formula_moiety         'C4 H2 Cl2 N4 O4'
_chemical_formula_sum            'C4 H2 Cl2 N4 O4'
_chemical_formula_weight         241.00


_cell_length_a                   6.9850(5)
_cell_length_b                   8.4845(5)
_cell_length_c                   13.8574(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     821.25(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2150
_cell_measurement_theta_min      4.7870
_cell_measurement_theta_max      33.1380
_cell_special_details            ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8279
_exptl_absorpt_correction_T_max  0.9693
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            4265
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         25.99
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.992

_reflns_number_total             1607
_reflns_number_gt                1535
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0526101000
_diffrn_orient_matrix_UB_12      -0.0050486000
_diffrn_orient_matrix_UB_13      0.0436861000
_diffrn_orient_matrix_UB_21      0.0844746000
_diffrn_orient_matrix_UB_22      -0.0162957000
_diffrn_orient_matrix_UB_23      -0.0265406000
_diffrn_orient_matrix_UB_31      0.0199992000
_diffrn_orient_matrix_UB_32      0.0818766000
_diffrn_orient_matrix_UB_33      -0.0026213000

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  ' P 2ac 2ab '

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'
Cl Cl 0.1484 0.1585 '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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.062

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0265P)²+0.0000P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_number_reflns         1607
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0616
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.60731(9) 0.76928(7) 0.54373(4) 0.01853(16) Uani 1 1 d . . .
Cl2 Cl 0.79368(8) 0.29618(6) 0.75601(4) 0.01578(15) Uani 1 1 d . . .
O1 O 0.6333(2) 0.73786(19) 0.88844(11) 0.0171(4) Uani 1 1 d . . .
O2 O 0.5974(3) 0.9837(2) 0.82660(12) 0.0219(4) Uani 1 1 d . . .
O3 O 0.7978(3) 1.0617(2) 0.55152(12) 0.0181(4) Uani 1 1 d . . .
O4 O 0.9855(3) 0.3829(2) 0.58491(13) 0.0151(4) Uani 1 1 d . . .
N1 N 0.6467(3) 0.8485(2) 0.80959(14) 0.0141(5) Uani 1 1 d . . .
N2 N 0.6980(3) 0.5936(2) 0.85591(14) 0.0159(5) Uani 1 1 d . . .
N3 N 0.8121(3) 0.9831(2) 0.63964(13) 0.0145(4) Uani 1 1 d . . .
N4 N 0.9151(3) 0.5152(2) 0.63201(14) 0.0129(4) Uani 1 1 d . . .
C1 C 0.7132(3) 0.7712(3) 0.73340(16) 0.0126(5) Uani 1 1 d . . .
C2 C 0.7457(3) 0.6135(3) 0.76460(16) 0.0114(5) Uani 1 1 d . . .
C3 C 0.7268(4) 0.8509(3) 0.63999(16) 0.0130(5) Uani 1 1 d . . .
C4 C 0.8255(3) 0.4818(3) 0.70920(17) 0.0122(5) Uani 1 1 d . . .
H3 H 0.864(5) 1.141(4) 0.561(2) 0.030(9) Uiso 1 1 d . . .
H4 H 1.041(4) 0.415(3) 0.544(2) 0.022(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
Cl1 C3 1.719(2) . ?
Cl2 C4 1.718(2) . ?
O1 N2 1.380(2) . ?
O1 N1 1.444(2) . ?
O2 N1 1.221(3) . ?
O3 N3 1.395(2) . ?
O3 H3 0.83(3) . ?
O4 N4 1.389(3) . ?
O4 H4 0.74(3) . ?
N1 C1 1.327(3) . ?
N2 C2 1.319(3) . ?
N3 C3 1.270(3) . ?
N4 C4 1.271(3) . ?
C1 C2 1.424(3) . ?
C1 C3 1.464(3) . ?
C2 C4 1.466(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N1 107.93(15) . . ?
N3 O3 H3 102(2) . . ?
N4 O4 H4 105(2) . . ?
O2 N1 C1 135.8(2) . . ?
O2 N1 O1 116.51(18) . . ?
C1 N1 O1 107.68(17) . . ?
C2 N2 O1 106.41(19) . . ?
C3 N3 O3 113.1(2) . . ?
C4 N4 O4 112.9(2) . . ?
N1 C1 C2 106.2(2) . . ?
N1 C1 C3 119.9(2) . . ?
C2 C1 C3 133.8(2) . . ?
N2 C2 C1 111.8(2) . . ?
N2 C2 C4 120.0(2) . . ?
C1 C2 C4 128.2(2) . . ?
N3 C3 C1 116.2(2) . . ?
N3 C3 Cl1 125.50(18) . . ?
C1 C3 Cl1 117.93(18) . . ?
N4 C4 C2 117.2(2) . . ?
N4 C4 Cl2 125.88(19) . . ?
C2 C4 Cl2 116.89(18) . . ?

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
N2 O1 N1 O2 -178.9(2) . . . . ?
N2 O1 N1 C1 1.2(2) . . . . ?
N1 O1 N2 C2 -0.5(2) . . . . ?
O2 N1 C1 C2 178.8(3) . . . . ?
O1 N1 C1 C2 -1.3(2) . . . . ?
O2 N1 C1 C3 -5.0(4) . . . . ?
O1 N1 C1 C3 174.9(2) . . . . ?
O1 N2 C2 C1 -0.3(2) . . . . ?
O1 N2 C2 C4 178.41(18) . . . . ?
N1 C1 C2 N2 1.1(3) . . . . ?
C3 C1 C2 N2 -174.4(3) . . . . ?
N1 C1 C2 C4 -177.5(2) . . . . ?
C3 C1 C2 C4 7.0(4) . . . . ?
O3 N3 C3 C1 -172.1(2) . . . . ?
O3 N3 C3 Cl1 1.1(3) . . . . ?
N1 C1 C3 N3 51.0(3) . . . . ?
C2 C1 C3 N3 -134.0(3) . . . . ?
N1 C1 C3 Cl1 -122.7(2) . . . . ?
C2 C1 C3 Cl1 52.3(4) . . . . ?
O4 N4 C4 C2 179.84(18) . . . . ?
O4 N4 C4 Cl2 1.3(3) . . . . ?
N2 C2 C4 N4 -161.7(2) . . . . ?
C1 C2 C4 N4 16.8(3) . . . . ?
N2 C2 C4 Cl2 17.0(3) . . . . ?
C1 C2 C4 Cl2 -164.52(19) . . . . ?

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
O3 H3 O4 0.83(3) 2.25(3) 3.060(3) 168(3) 1_565
O4 H4 O3 0.74(3) 2.24(3) 2.925(3) 155(3) 3_566
O4 H4 Cl1 0.74(3) 2.98(3) 3.551(2) 136(3) 3_566

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988406'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix140
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Sat Mar 23 15:59:20 2013'
;
_audit_update_record             25.03.2013

_chemical_name_systematic        3,4-Bis(chloroximidoyl)furazane
_chemical_compound_source        ?
_chemical_name_common            3,4-Bis(chloroximidoyl)furazane
_chemical_formula_moiety         'C4 H2 Cl2 N4 O3'
_chemical_formula_sum            'C4 H2 Cl2 N4 O3'
_chemical_formula_weight         225.00


_cell_length_a                   8.2678(6)
_cell_length_b                   11.2186(7)
_cell_length_c                   8.5693(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.912(6)
_cell_angle_gamma                90.00
_cell_volume                     782.97(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1967
_cell_measurement_theta_min      4.8040
_cell_measurement_theta_max      31.8270
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_T_max  0.8750
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            5523
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         25.99
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.995

_reflns_number_total             1531
_reflns_number_gt                1315
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0117734000
_diffrn_orient_matrix_UB_12      0.0581189000
_diffrn_orient_matrix_UB_13      -0.0288679000
_diffrn_orient_matrix_UB_21      0.0848519000
_diffrn_orient_matrix_UB_22      -0.0120024000
_diffrn_orient_matrix_UB_23      0.0048154000
_diffrn_orient_matrix_UB_31      -0.0151351000
_diffrn_orient_matrix_UB_32      -0.0220388000
_diffrn_orient_matrix_UB_33      -0.0787582000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2yn

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'
Cl Cl 0.1484 0.1585 '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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.063

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.2638P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1531
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02927(6) 0.33390(5) 0.72723(6) 0.02675(17) Uani 1 1 d . . .
Cl2 Cl 0.07776(6) 0.30723(4) 0.13694(5) 0.01985(15) Uani 1 1 d . . .
O1 O 0.23392(17) 0.01460(13) 0.52826(16) 0.0222(3) Uani 1 1 d . . .
O2 O -0.20730(18) 0.40809(13) 0.46395(18) 0.0222(3) Uani 1 1 d . . .
O3 O -0.13734(19) 0.14312(15) -0.04236(17) 0.0244(4) Uani 1 1 d . . .
N1 N 0.1680(2) 0.10271(15) 0.61157(19) 0.0197(4) Uani 1 1 d . . .
N2 N 0.1877(2) 0.03066(15) 0.36650(19) 0.0199(4) Uani 1 1 d . . .
N3 N -0.1187(2) 0.31203(15) 0.42656(18) 0.0166(4) Uani 1 1 d . . .
N4 N -0.07478(19) 0.09646(15) 0.10576(19) 0.0188(4) Uani 1 1 d . . .
C1 C 0.0840(2) 0.17176(17) 0.5042(2) 0.0155(4) Uani 1 1 d . . .
C2 C 0.0963(2) 0.12521(18) 0.3503(2) 0.0161(4) Uani 1 1 d . . .
C3 C -0.0109(2) 0.27462(18) 0.5401(2) 0.0164(4) Uani 1 1 d . . .
C4 C 0.0216(2) 0.16814(18) 0.1916(2) 0.0154(4) Uani 1 1 d . . .
H2 H -0.263(3) 0.417(2) 0.384(3) 0.038(8) Uiso 1 1 d . . .
H3 H -0.187(3) 0.088(3) -0.084(3) 0.040(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
Cl1 C3 1.7146(19) . ?
Cl2 C4 1.716(2) . ?
O1 N2 1.385(2) . ?
O1 N1 1.385(2) . ?
O2 N3 1.372(2) . ?
O2 H2 0.76(3) . ?
O3 N4 1.388(2) . ?
O3 H3 0.79(3) . ?
N1 C1 1.307(2) . ?
N2 C2 1.296(3) . ?
N3 C3 1.272(2) . ?
N4 C4 1.273(2) . ?
C1 C2 1.438(3) . ?
C1 C3 1.458(3) . ?
C2 C4 1.475(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N1 110.98(13) . . ?
N3 O2 H2 99(2) . . ?
N4 O3 H3 101(2) . . ?
C1 N1 O1 105.58(15) . . ?
C2 N2 O1 105.59(16) . . ?
C3 N3 O2 114.36(16) . . ?
C4 N4 O3 112.80(17) . . ?
N1 C1 C2 108.51(18) . . ?
N1 C1 C3 124.07(18) . . ?
C2 C1 C3 127.36(17) . . ?
N2 C2 C1 109.34(17) . . ?
N2 C2 C4 120.66(18) . . ?
C1 C2 C4 129.99(18) . . ?
N3 C3 C1 115.53(17) . . ?
N3 C3 Cl1 125.78(16) . . ?
C1 C3 Cl1 118.69(14) . . ?
N4 C4 C2 116.60(18) . . ?
N4 C4 Cl2 126.07(16) . . ?
C2 C4 Cl2 117.29(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
N2 O1 N1 C1 -0.31(19) . . . . ?
N1 O1 N2 C2 -0.1(2) . . . . ?
O1 N1 C1 C2 0.6(2) . . . . ?
O1 N1 C1 C3 177.91(16) . . . . ?
O1 N2 C2 C1 0.4(2) . . . . ?
O1 N2 C2 C4 -178.75(16) . . . . ?
N1 C1 C2 N2 -0.6(2) . . . . ?
C3 C1 C2 N2 -177.90(18) . . . . ?
N1 C1 C2 C4 178.43(18) . . . . ?
C3 C1 C2 C4 1.2(3) . . . . ?
O2 N3 C3 C1 179.37(15) . . . . ?
O2 N3 C3 Cl1 -0.3(3) . . . . ?
N1 C1 C3 N3 -161.70(18) . . . . ?
C2 C1 C3 N3 15.2(3) . . . . ?
N1 C1 C3 Cl1 18.0(3) . . . . ?
C2 C1 C3 Cl1 -165.19(16) . . . . ?
O3 N4 C4 C2 -178.97(16) . . . . ?
O3 N4 C4 Cl2 -1.5(2) . . . . ?
N2 C2 C4 N4 59.7(3) . . . . ?
C1 C2 C4 N4 -119.3(2) . . . . ?
N2 C2 C4 Cl2 -118.05(19) . . . . ?
C1 C2 C4 Cl2 63.0(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
O2 H2 N1 0.76(3) 2.32(3) 3.021(2) 154(3) 4_565
O2 H2 N4 0.76(3) 2.43(3) 2.775(2) 109(2) 2_455
O3 H3 O2 0.79(3) 2.49(3) 3.058(2) 130(2) 2_445

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988407'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix157
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Sun Apr 07 08:05:47 2013'
;
_audit_update_record             18.04.2013

_chemical_name_systematic        3,4-(Dicarboxamidoxyl)furazane
_chemical_compound_source        ?
_chemical_name_common            3,4-(Dicarboxamidoxyl)furazane
_chemical_formula_moiety         'C4 H6 N6 O3'
_chemical_formula_sum            'C4 H6 N6 O3'
_chemical_formula_weight         186.15


_cell_length_a                   12.844(3)
_cell_length_b                   8.919(5)
_cell_length_c                   6.988(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.147(5)
_cell_angle_gamma                90.00
_cell_volume                     741.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    709
_cell_measurement_theta_min      4.5600
_cell_measurement_theta_max      29.1280
_cell_special_details            ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_T_max  0.9859
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            2426
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.57
_diffrn_reflns_theta_max         25.97
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.990

_reflns_number_total             725
_reflns_number_gt                588
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0428443000
_diffrn_orient_matrix_UB_12      -0.0069476000
_diffrn_orient_matrix_UB_13      0.0574911000
_diffrn_orient_matrix_UB_21      -0.0866095000
_diffrn_orient_matrix_UB_22      -0.0334019000
_diffrn_orient_matrix_UB_23      0.0113377000
_diffrn_orient_matrix_UB_31      0.0359646000
_diffrn_orient_matrix_UB_32      -0.0719058000
_diffrn_orient_matrix_UB_33      -0.0108626000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  ' -C 2yc '

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+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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.058

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.0571P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         725
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.5000 0.10144(18) 0.7500 0.0184(5) Uani 1 2 d S . .
O2 O 0.63092(10) -0.46493(14) 0.5470(2) 0.0202(4) Uani 1 1 d . . .
N3 N 0.56213(12) -0.36575(15) 0.6066(2) 0.0172(4) Uani 1 1 d . . .
N2 N 0.72743(13) -0.22093(19) 0.7243(3) 0.0235(5) Uani 1 1 d . . .
N1 N 0.58328(12) 0.01326(15) 0.7294(2) 0.0174(4) Uani 1 1 d . . .
C2 C 0.61827(14) -0.24697(18) 0.6904(3) 0.0164(4) Uani 1 1 d . . .
C1 C 0.55273(14) -0.12558(17) 0.7359(3) 0.0150(4) Uani 1 1 d . . .
H2A H 0.7560(17) -0.135(2) 0.766(3) 0.018(5) Uiso 1 1 d . . .
H2B H 0.7681(17) -0.294(2) 0.686(3) 0.027(6) Uiso 1 1 d . . .
H2 H 0.582(2) -0.525(3) 0.489(5) 0.052(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
O1 N1 1.3784(17) 2_656 ?
O1 N1 1.3784(17) . ?
O2 N3 1.4194(18) . ?
O2 H2 0.81(3) . ?
N3 C2 1.291(2) . ?
N2 C2 1.351(2) . ?
N2 H2A 0.86(2) . ?
N2 H2B 0.94(2) . ?
N1 C1 1.305(2) . ?
C2 C1 1.478(2) . ?
C1 C1 1.440(3) 2_656 ?

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
N1 O1 N1 110.42(16) 2_656 . ?
N3 O2 H2 96.7(19) . . ?
C2 N3 O2 109.96(14) . . ?
C2 N2 H2A 119.9(13) . . ?
C2 N2 H2B 119.0(12) . . ?
H2A N2 H2B 120.7(18) . . ?
C1 N1 O1 106.40(14) . . ?
N3 C2 N2 125.88(16) . . ?
N3 C2 C1 115.64(15) . . ?
N2 C2 C1 118.28(15) . . ?
N1 C1 C1 108.39(10) . 2_656 ?
N1 C1 C2 118.97(16) . . ?
C1 C1 C2 132.13(10) 2_656 . ?

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
N1 O1 N1 C1 0.29(9) 2_656 . . . ?
O2 N3 C2 N2 -2.2(2) . . . . ?
O2 N3 C2 C1 172.56(14) . . . . ?
O1 N1 C1 C1 -0.7(2) . . . 2_656 ?
O1 N1 C1 C2 172.11(13) . . . . ?
N3 C2 C1 N1 -149.17(17) . . . . ?
N2 C2 C1 N1 26.0(2) . . . . ?
N3 C2 C1 C1 21.6(3) . . . 2_656 ?
N2 C2 C1 C1 -163.2(2) . . . 2_656 ?

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
N2 H2A O2 0.86(2) 2.16(2) 2.981(2) 159.9(18) 4_656
N2 H2B N1 0.94(2) 2.47(2) 3.323(2) 151.9(18) 4_646
O2 H2 N3 0.81(3) 1.98(3) 2.752(2) 161(3) 5_646
O2 H2 O2 0.81(3) 2.66(3) 3.236(3) 130(2) 5_646

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988408'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix165
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Fri Apr 12 09:37:49 2013'
;
_audit_update_record             17.04.2013

_chemical_name_systematic        'dipotassium bis(1-oxido-tetrazolyl)-furoxane'
_chemical_compound_source        ?
_chemical_name_common            'dipotassium bis(1-oxido-tetrazolyl)-furoxane'
_chemical_formula_moiety         ' C4 N10 O4, 2(K) '
_chemical_formula_sum            'C4 K2 N10 O4'
_chemical_formula_weight         330.34


_cell_length_a                   7.1412(6)
_cell_length_b                   7.2056(8)
_cell_length_c                   11.4980(9)
_cell_angle_alpha                89.658(7)
_cell_angle_beta                 73.514(7)
_cell_angle_gamma                64.814(9)
_cell_volume                     508.88(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2881
_cell_measurement_theta_min      4.1400
_cell_measurement_theta_max      32.1510
_cell_special_details            ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8294
_exptl_absorpt_correction_T_max  0.9177
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            7459
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         26.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             1985
_reflns_number_gt                1708
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.1015040000
_diffrn_orient_matrix_UB_12      -0.0469924000
_diffrn_orient_matrix_UB_13      -0.0470040000
_diffrn_orient_matrix_UB_21      0.0121662000
_diffrn_orient_matrix_UB_22      0.0922539000
_diffrn_orient_matrix_UB_23      0.0038621000
_diffrn_orient_matrix_UB_31      0.0537039000
_diffrn_orient_matrix_UB_32      -0.0363935000
_diffrn_orient_matrix_UB_33      0.0445903000

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  -P1

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'
K K 0.2009 0.2494 '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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.062

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0257P)²+0.0561P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1985
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 1.0549(2) 0.2566(2) -0.20163(11) 0.0166(3) Uani 1 1 d . . .
O2 O 1.1506(2) 0.0462(2) 0.12823(11) 0.0124(3) Uani 1 1 d . . .
O3 O 1.0031(2) 0.1026(2) 0.33479(11) 0.0147(3) Uani 1 1 d . . .
O4 O 0.5312(2) 0.1544(2) 0.38036(11) 0.0134(3) Uani 1 1 d . . .
N1 N 0.8806(3) 0.4059(2) -0.12933(14) 0.0116(3) Uani 1 1 d . . .
N2 N 0.7489(3) 0.5694(3) -0.17028(14) 0.0136(4) Uani 1 1 d . . .
N3 N 0.5920(3) 0.6911(3) -0.07272(14) 0.0137(4) Uani 1 1 d . . .
N4 N 0.6187(3) 0.6108(2) 0.03049(14) 0.0120(3) Uani 1 1 d . . .
N5 N 1.0959(3) 0.1419(2) 0.03018(14) 0.0113(3) Uani 1 1 d . . .
N6 N 0.9745(3) 0.1575(2) 0.23682(14) 0.0113(3) Uani 1 1 d . . .
N7 N 0.4896(3) 0.3487(2) 0.37269(13) 0.0102(3) Uani 1 1 d . . .
N8 N 0.3069(3) 0.5041(3) 0.44352(14) 0.0130(3) Uani 1 1 d . . .
N9 N 0.3151(3) 0.6771(3) 0.40949(14) 0.0137(4) Uani 1 1 d . . .
N10 N 0.4987(3) 0.6358(3) 0.31849(14) 0.0134(3) Uani 1 1 d . . .
C1 C 0.7982(3) 0.4328(3) -0.00521(16) 0.0096(4) Uani 1 1 d . . .
C2 C 0.8999(3) 0.2937(3) 0.07392(16) 0.0101(4) Uani 1 1 d . . .
C3 C 0.8154(3) 0.3046(3) 0.20442(16) 0.0106(4) Uani 1 1 d . . .
C4 C 0.6073(3) 0.4297(3) 0.29579(16) 0.0103(4) Uani 1 1 d . . .
K1 K 0.54394(7) 0.94696(6) 0.18742(4) 0.01159(11) Uani 1 1 d . . .
K2 K 0.15580(7) 0.16393(7) 0.54984(4) 0.01510(12) Uani 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 N1 1.297(2) . ?
O1 K1 2.6592(14) 2_765 ?
O1 K2 2.7525(13) 1_654 ?
O2 N5 1.3822(19) . ?
O2 N6 1.430(2) . ?
O2 K1 2.8695(13) 1_645 ?
O3 N6 1.2343(19) . ?
O3 K2 2.7760(14) 2_656 ?
O3 K2 3.0742(13) 1_655 ?
O3 K1 3.4156(15) 1_645 ?
O4 N7 1.310(2) . ?
O4 K1 2.6407(13) 1_545 ?
O4 K2 2.7448(14) 2_656 ?
O4 K2 2.8051(14) . ?
N1 N2 1.340(2) . ?
N1 C1 1.360(2) . ?
N2 N3 1.321(2) . ?
N2 K1 3.2528(18) 2_675 ?
N3 N4 1.344(2) . ?
N3 K1 2.8310(16) 2_675 ?
N3 K1 3.3777(16) . ?
N4 C1 1.329(2) . ?
N4 K1 2.7955(16) . ?
N5 C2 1.309(2) . ?
N5 K1 2.8724(16) 2_765 ?
N6 C3 1.328(2) . ?
N7 N8 1.336(2) . ?
N7 C4 1.349(2) . ?
N7 K2 3.3935(16) . ?
N7 K1 3.4228(16) 1_545 ?
N8 N9 1.325(2) . ?
N8 K2 3.1271(17) 2_566 ?
N8 K2 3.1833(17) . ?
N9 N10 1.340(2) . ?
N9 K2 2.9455(17) 2_566 ?
N9 K2 3.4396(17) 1_565 ?
N10 C4 1.336(2) . ?
N10 K1 2.7753(16) . ?
C1 C2 1.450(2) . ?
C2 C3 1.438(2) . ?
C3 C4 1.452(3) . ?
K1 O4 2.6407(13) 1_565 ?
K1 O1 2.6592(14) 2_765 ?
K1 N3 2.8310(16) 2_675 ?
K1 O2 2.8695(13) 1_465 ?
K1 N5 2.8724(16) 2_765 ?
K1 N2 3.2528(18) 2_675 ?
K1 O3 3.4156(15) 1_465 ?
K1 N7 3.4228(16) 1_565 ?
K2 O4 2.7448(14) 2_656 ?
K2 O1 2.7525(13) 1_456 ?
K2 O3 2.7760(14) 2_656 ?
K2 N9 2.9455(17) 2_566 ?
K2 O3 3.0742(13) 1_455 ?
K2 N8 3.1271(17) 2_566 ?
K2 N9 3.4396(17) 1_545 ?

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
N1 O1 K1 132.01(10) . 2_765 ?
N1 O1 K2 127.03(10) . 1_654 ?
K1 O1 K2 97.48(4) 2_765 1_654 ?
N5 O2 N6 107.74(12) . . ?
N5 O2 K1 126.91(10) . 1_645 ?
N6 O2 K1 106.49(9) . 1_645 ?
N6 O3 K2 120.58(10) . 2_656 ?
N6 O3 K2 146.87(11) . 1_655 ?
K2 O3 K2 92.16(4) 2_656 1_655 ?
N6 O3 K1 86.05(10) . 1_645 ?
K2 O3 K1 122.41(5) 2_656 1_645 ?
K2 O3 K1 79.60(3) 1_655 1_645 ?
N7 O4 K1 115.95(10) . 1_545 ?
N7 O4 K2 132.75(10) . 2_656 ?
K1 O4 K2 98.11(5) 1_545 2_656 ?
N7 O4 K2 105.25(10) . . ?
K1 O4 K2 99.65(4) 1_545 . ?
K2 O4 K2 99.75(4) 2_656 . ?
O1 N1 N2 122.72(14) . . ?
O1 N1 C1 129.52(16) . . ?
N2 N1 C1 107.75(15) . . ?
N3 N2 N1 106.47(14) . . ?
N3 N2 K1 59.89(9) . 2_675 ?
N1 N2 K1 158.04(11) . 2_675 ?
N2 N3 N4 111.23(15) . . ?
N2 N3 K1 96.30(10) . 2_675 ?
N4 N3 K1 146.82(12) . 2_675 ?
N2 N3 K1 138.03(11) . . ?
N4 N3 K1 53.50(9) . . ?
K1 N3 K1 93.65(5) 2_675 . ?
C1 N4 N3 105.65(15) . . ?
C1 N4 K1 126.70(11) . . ?
N3 N4 K1 103.77(11) . . ?
C2 N5 O2 106.98(14) . . ?
C2 N5 K1 134.56(12) . 2_765 ?
O2 N5 K1 115.09(10) . 2_765 ?
O3 N6 C3 135.26(17) . . ?
O3 N6 O2 116.46(14) . . ?
C3 N6 O2 108.25(14) . . ?
O4 N7 N8 122.31(15) . . ?
O4 N7 C4 129.28(16) . . ?
N8 N7 C4 108.38(15) . . ?
O4 N7 K2 52.89(8) . . ?
N8 N7 K2 69.56(9) . . ?
C4 N7 K2 174.07(12) . . ?
N8 N7 K1 128.42(11) . 1_545 ?
C4 N7 K1 102.72(11) . 1_545 ?
K2 N7 K1 75.27(3) . 1_545 ?
N9 N8 N7 106.38(14) . . ?
N9 N8 K2 69.82(10) . 2_566 ?
N7 N8 K2 143.78(11) . 2_566 ?
N9 N8 K2 165.19(12) . . ?
N7 N8 K2 87.29(10) . . ?
K2 N8 K2 95.82(4) 2_566 . ?
N8 N9 N10 110.90(15) . . ?
N8 N9 K2 85.21(10) . 2_566 ?
N10 N9 K2 139.70(11) . 2_566 ?
N8 N9 K2 136.71(11) . 1_565 ?
N10 N9 K2 105.22(11) . 1_565 ?
K2 N9 K2 82.32(4) 2_566 1_565 ?
C4 N10 N9 105.81(15) . . ?
C4 N10 K1 132.31(12) . . ?
N9 N10 K1 120.27(11) . . ?
N4 C1 N1 108.90(16) . . ?
N4 C1 C2 126.33(16) . . ?
N1 C1 C2 124.68(17) . . ?
N5 C2 C3 111.36(16) . . ?
N5 C2 C1 120.90(16) . . ?
C3 C2 C1 127.66(17) . . ?
N6 C3 C2 105.51(16) . . ?
N6 C3 C4 120.15(16) . . ?
C2 C3 C4 134.30(17) . . ?
N10 C4 N7 108.53(16) . . ?
N10 C4 C3 128.12(17) . . ?
N7 C4 C3 123.34(17) . . ?
O4 K1 O1 77.08(4) 1_565 2_765 ?
O4 K1 N10 92.78(4) 1_565 . ?
O1 K1 N10 80.07(5) 2_765 . ?
O4 K1 N4 159.29(4) 1_565 . ?
O1 K1 N4 89.45(5) 2_765 . ?
N10 K1 N4 69.16(5) . . ?
O4 K1 N3 91.62(4) 1_565 2_675 ?
O1 K1 N3 123.35(5) 2_765 2_675 ?
N10 K1 N3 156.54(5) . 2_675 ?
N4 K1 N3 108.99(5) . 2_675 ?
O4 K1 O2 119.64(4) 1_565 1_465 ?
O1 K1 O2 162.04(4) 2_765 1_465 ?
N10 K1 O2 91.90(4) . 1_465 ?
N4 K1 O2 72.65(4) . 1_465 ?
N3 K1 O2 66.04(4) 2_675 1_465 ?
O4 K1 N5 116.86(4) 1_565 2_765 ?
O1 K1 N5 61.71(4) 2_765 2_765 ?
N10 K1 N5 121.58(5) . 2_765 ?
N4 K1 N5 68.16(5) . 2_765 ?
N3 K1 N5 76.16(5) 2_675 2_765 ?
O2 K1 N5 110.92(4) 1_465 2_765 ?
O4 K1 N2 74.95(4) 1_565 2_675 ?
O1 K1 N2 132.39(4) 2_765 2_675 ?
N10 K1 N2 138.51(5) . 2_675 ?
N4 K1 N2 125.27(4) . 2_675 ?
N3 K1 N2 23.81(4) 2_675 2_675 ?
O2 K1 N2 62.96(4) 1_465 2_675 ?
N5 K1 N2 98.88(4) 2_765 2_675 ?
O4 K1 N3 175.42(4) 1_565 . ?
O1 K1 N3 100.62(4) 2_765 . ?
N10 K1 N3 90.70(4) . . ?
N4 K1 N3 22.73(4) . . ?
N3 K1 N3 86.35(5) 2_675 . ?
O2 K1 N3 63.17(4) 1_465 . ?
N5 K1 N3 58.66(4) 2_765 . ?
N2 K1 N3 104.28(4) 2_675 . ?
O4 K1 O3 84.65(4) 1_565 1_465 ?
O1 K1 O3 145.32(4) 2_765 1_465 ?
N10 K1 O3 71.57(4) . 1_465 ?
N4 K1 O3 98.44(4) . 1_465 ?
N3 K1 O3 85.94(4) 2_675 1_465 ?
O2 K1 O3 41.16(3) 1_465 1_465 ?
N5 K1 O3 151.92(4) 2_765 1_465 ?
N2 K1 O3 67.97(4) 2_675 1_465 ?
N3 K1 O3 99.29(4) . 1_465 ?
O4 K1 N7 20.12(4) 1_565 1_565 ?
O1 K1 N7 87.10(4) 2_765 1_565 ?
N10 K1 N7 111.91(4) . 1_565 ?
N4 K1 N7 176.12(4) . 1_565 ?
N3 K1 N7 71.60(4) 2_675 1_565 ?
O2 K1 N7 110.84(4) 1_465 1_565 ?
N5 K1 N7 108.55(4) 2_765 1_565 ?
N2 K1 N7 56.61(4) 2_675 1_565 ?
N3 K1 N7 157.14(4) . 1_565 ?
O3 K1 N7 85.42(4) 1_465 1_565 ?
O4 K1 K2 41.90(3) 1_565 2_666 ?
O1 K1 K2 42.13(3) 2_765 2_666 ?
N10 K1 K2 67.57(3) . 2_666 ?
N4 K1 K2 118.57(4) . 2_666 ?
N3 K1 K2 127.56(3) 2_675 2_666 ?
O2 K1 K2 147.52(3) 1_465 2_666 ?
N5 K1 K2 101.39(3) 2_765 2_666 ?
N2 K1 K2 116.09(3) 2_675 2_666 ?
N3 K1 K2 137.75(3) . 2_666 ?
O3 K1 K2 106.68(2) 1_465 2_666 ?
N7 K1 K2 59.49(3) 1_565 2_666 ?
O4 K2 O1 73.84(4) 2_656 1_456 ?
O4 K2 O3 68.68(4) 2_656 2_656 ?
O1 K2 O3 71.90(4) 1_456 2_656 ?
O4 K2 O4 80.25(4) 2_656 . ?
O1 K2 O4 122.95(4) 1_456 . ?
O3 K2 O4 140.34(4) 2_656 . ?
O4 K2 N9 136.52(4) 2_656 2_566 ?
O1 K2 N9 87.06(4) 1_456 2_566 ?
O3 K2 N9 68.32(4) 2_656 2_566 ?
O4 K2 N9 140.76(4) . 2_566 ?
O4 K2 O3 122.62(4) 2_656 1_455 ?
O1 K2 O3 147.61(4) 1_456 1_455 ?
O3 K2 O3 87.84(4) 2_656 1_455 ?
O4 K2 O3 88.80(4) . 1_455 ?
N9 K2 O3 61.63(4) 2_566 1_455 ?
O4 K2 N8 158.84(4) 2_656 2_566 ?
O1 K2 N8 90.87(4) 1_456 2_566 ?
O3 K2 N8 92.96(4) 2_656 2_566 ?
O4 K2 N8 120.78(4) . 2_566 ?
N9 K2 N8 24.97(4) 2_566 2_566 ?
O3 K2 N8 64.57(4) 1_455 2_566 ?
O4 K2 N8 113.00(4) 2_656 . ?
O1 K2 N8 102.64(4) 1_456 . ?
O3 K2 N8 173.85(4) 2_656 . ?
O4 K2 N8 44.98(4) . . ?
N9 K2 N8 109.10(4) 2_566 . ?
O3 K2 N8 95.80(4) 1_455 . ?
N8 K2 N8 84.18(4) 2_566 . ?
O4 K2 N7 97.00(4) 2_656 . ?
O1 K2 N7 115.47(4) 1_456 . ?
O3 K2 N7 162.17(4) 2_656 . ?
O4 K2 N7 21.86(4) . . ?
N9 K2 N7 126.45(4) 2_566 . ?
O3 K2 N7 91.50(4) 1_455 . ?
N8 K2 N7 102.85(4) 2_566 . ?
N8 K2 N7 23.15(4) . . ?
O4 K2 N9 64.35(4) 2_656 1_545 ?
O1 K2 N9 123.23(4) 1_456 1_545 ?
O3 K2 N9 58.37(4) 2_656 1_545 ?
O4 K2 N9 86.52(4) . 1_545 ?
N9 K2 N9 97.68(4) 2_566 1_545 ?
O3 K2 N9 58.85(4) 1_455 1_545 ?
N8 K2 N9 115.73(4) 2_566 1_545 ?
N8 K2 N9 127.78(4) . 1_545 ?
N7 K2 N9 106.44(4) . 1_545 ?
O4 K2 K1 39.98(3) 2_656 2_666 ?
O1 K2 K1 40.39(3) 1_456 2_666 ?
O3 K2 K1 82.19(3) 2_656 2_666 ?
O4 K2 K1 89.69(3) . 2_666 ?
N9 K2 K1 126.36(3) 2_566 2_666 ?
O3 K2 K1 162.41(3) 1_455 2_666 ?
N8 K2 K1 130.15(3) 2_566 2_666 ?
N8 K2 K1 95.48(3) . 2_666 ?
N7 K2 K1 93.59(3) . 2_666 ?
N9 K2 K1 103.57(3) 1_545 2_666 ?
O4 K2 K1 88.59(3) 2_656 1_545 ?
O1 K2 K1 158.04(3) 1_456 1_545 ?
O3 K2 K1 114.33(3) 2_656 1_545 ?
O4 K2 K1 38.72(3) . 1_545 ?
N9 K2 K1 114.89(3) 2_566 1_545 ?
O3 K2 K1 53.81(3) 1_455 1_545 ?
N8 K2 K1 109.24(3) 2_566 1_545 ?
N8 K2 K1 71.80(3) . 1_545 ?
N7 K2 K1 52.68(3) . 1_545 ?
N9 K2 K1 56.25(3) 1_545 1_545 ?
K1 K2 K1 117.935(14) 2_666 1_545 ?

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
















K1 O1 N1 N2 136.20(14) 2_765 . . . ?
K2 O1 N1 N2 -17.8(2) 1_654 . . . ?
K1 O1 N1 C1 -42.5(2) 2_765 . . . ?
K2 O1 N1 C1 163.49(13) 1_654 . . . ?
O1 N1 N2 N3 -178.79(15) . . . . ?
C1 N1 N2 N3 0.16(18) . . . . ?
O1 N1 N2 K1 -130.5(3) . . . 2_675 ?
C1 N1 N2 K1 48.4(4) . . . 2_675 ?
N1 N2 N3 N4 0.04(19) . . . . ?
K1 N2 N3 N4 -161.13(15) 2_675 . . . ?
N1 N2 N3 K1 161.18(11) . . . 2_675 ?
N1 N2 N3 K1 58.6(2) . . . . ?
K1 N2 N3 K1 -102.62(15) 2_675 . . . ?
N2 N3 N4 C1 -0.23(19) . . . . ?
K1 N3 N4 C1 -144.27(18) 2_675 . . . ?
K1 N3 N4 C1 -135.04(15) . . . . ?
N2 N3 N4 K1 134.81(12) . . . . ?
K1 N3 N4 K1 -9.2(2) 2_675 . . . ?
N6 O2 N5 C2 -2.20(18) . . . . ?
K1 O2 N5 C2 -130.01(12) 1_645 . . . ?
N6 O2 N5 K1 160.16(9) . . . 2_765 ?
K1 O2 N5 K1 32.36(15) 1_645 . . 2_765 ?
K2 O3 N6 C3 84.5(2) 2_656 . . . ?
K2 O3 N6 C3 -85.7(3) 1_655 . . . ?
K1 O3 N6 C3 -149.8(2) 1_645 . . . ?
K2 O3 N6 O2 -97.54(14) 2_656 . . . ?
K2 O3 N6 O2 92.2(2) 1_655 . . . ?
K1 O3 N6 O2 28.14(12) 1_645 . . . ?
N5 O2 N6 O3 -174.52(14) . . . . ?
K1 O2 N6 O3 -35.73(15) 1_645 . . . ?
N5 O2 N6 C3 3.94(18) . . . . ?
K1 O2 N6 C3 142.72(11) 1_645 . . . ?
K1 O4 N7 N8 113.78(14) 1_545 . . . ?
K2 O4 N7 N8 -114.65(15) 2_656 . . . ?
K2 O4 N7 N8 4.76(17) . . . . ?
K1 O4 N7 C4 -64.0(2) 1_545 . . . ?
K2 O4 N7 C4 67.6(2) 2_656 . . . ?
K2 O4 N7 C4 -172.98(15) . . . . ?
K1 O4 N7 K2 109.02(9) 1_545 . . . ?
K2 O4 N7 K2 -119.41(13) 2_656 . . . ?
K2 O4 N7 K1 131.57(16) 2_656 . . 1_545 ?
K2 O4 N7 K1 -109.02(9) . . . 1_545 ?
O4 N7 N8 N9 -178.25(14) . . . . ?
C4 N7 N8 N9 -0.09(18) . . . . ?
K2 N7 N8 N9 -174.20(13) . . . . ?
K1 N7 N8 N9 -124.13(12) 1_545 . . . ?
O4 N7 N8 K2 -100.2(2) . . . 2_566 ?
C4 N7 N8 K2 78.0(2) . . . 2_566 ?
K2 N7 N8 K2 -96.15(17) . . . 2_566 ?
K1 N7 N8 K2 -46.1(2) 1_545 . . 2_566 ?
O4 N7 N8 K2 -4.05(14) . . . . ?
C4 N7 N8 K2 174.11(12) . . . . ?
K1 N7 N8 K2 50.06(11) 1_545 . . . ?
N7 N8 N9 N10 0.06(19) . . . . ?
K2 N8 N9 N10 -141.92(14) 2_566 . . . ?
K2 N8 N9 N10 -156.7(4) . . . . ?
N7 N8 N9 K2 141.99(11) . . . 2_566 ?
K2 N8 N9 K2 -14.8(4) . . . 2_566 ?
N7 N8 N9 K2 -144.54(13) . . . 1_565 ?
K2 N8 N9 K2 73.47(13) 2_566 . . 1_565 ?
K2 N8 N9 K2 58.7(5) . . . 1_565 ?
N8 N9 N10 C4 0.00(19) . . . . ?
K2 N9 N10 C4 -108.18(18) 2_566 . . . ?
K2 N9 N10 C4 155.69(11) 1_565 . . . ?
N8 N9 N10 K1 167.27(10) . . . . ?
K2 N9 N10 K1 59.1(2) 2_566 . . . ?
K2 N9 N10 K1 -37.04(12) 1_565 . . . ?
N3 N4 C1 N1 0.32(19) . . . . ?
K1 N4 C1 N1 -120.82(14) . . . . ?
N3 N4 C1 C2 176.87(17) . . . . ?
K1 N4 C1 C2 55.7(2) . . . . ?
O1 N1 C1 N4 178.54(16) . . . . ?
N2 N1 C1 N4 -0.31(19) . . . . ?
O1 N1 C1 C2 1.9(3) . . . . ?
N2 N1 C1 C2 -176.92(16) . . . . ?
O2 N5 C2 C3 -0.2(2) . . . . ?
K1 N5 C2 C3 -157.53(12) 2_765 . . . ?
O2 N5 C2 C1 176.75(15) . . . . ?
K1 N5 C2 C1 19.4(3) 2_765 . . . ?
N4 C1 C2 N5 -167.80(17) . . . . ?
N1 C1 C2 N5 8.2(3) . . . . ?
N4 C1 C2 C3 8.6(3) . . . . ?
N1 C1 C2 C3 -175.38(17) . . . . ?
O3 N6 C3 C2 174.17(18) . . . . ?
O2 N6 C3 C2 -3.87(18) . . . . ?
O3 N6 C3 C4 -7.8(3) . . . . ?
O2 N6 C3 C4 174.21(15) . . . . ?
N5 C2 C3 N6 2.6(2) . . . . ?
C1 C2 C3 N6 -174.03(17) . . . . ?
N5 C2 C3 C4 -175.0(2) . . . . ?
C1 C2 C3 C4 8.3(3) . . . . ?
N9 N10 C4 N7 -0.05(19) . . . . ?
K1 N10 C4 N7 -165.14(11) . . . . ?
N9 N10 C4 C3 179.18(17) . . . . ?
K1 N10 C4 C3 14.1(3) . . . . ?
O4 N7 C4 N10 178.08(15) . . . . ?
N8 N7 C4 N10 0.09(19) . . . . ?
K1 N7 C4 N10 138.36(11) 1_545 . . . ?
O4 N7 C4 C3 -1.2(3) . . . . ?
N8 N7 C4 C3 -179.19(15) . . . . ?
K1 N7 C4 C3 -40.91(19) 1_545 . . . ?
N6 C3 C4 N10 127.6(2) . . . . ?
C2 C3 C4 N10 -55.0(3) . . . . ?
N6 C3 C4 N7 -53.3(3) . . . . ?
C2 C3 C4 N7 124.2(2) . . . . ?
C4 N10 K1 O4 -131.61(16) . . . 1_565 ?
N9 N10 K1 O4 65.05(13) . . . 1_565 ?
C4 N10 K1 O1 -55.25(15) . . . 2_765 ?
N9 N10 K1 O1 141.41(13) . . . 2_765 ?
C4 N10 K1 N4 37.97(15) . . . . ?
N9 N10 K1 N4 -125.37(13) . . . . ?
C4 N10 K1 N3 127.84(16) . . . 2_675 ?
N9 N10 K1 N3 -35.5(2) . . . 2_675 ?
C4 N10 K1 O2 108.59(15) . . . 1_465 ?
N9 N10 K1 O2 -54.75(13) . . . 1_465 ?
C4 N10 K1 N5 -7.50(17) . . . 2_765 ?
N9 N10 K1 N5 -170.84(11) . . . 2_765 ?
C4 N10 K1 N2 158.12(14) . . . 2_675 ?
N9 N10 K1 N2 -5.22(16) . . . 2_675 ?
C4 N10 K1 N3 45.41(16) . . . . ?
N9 N10 K1 N3 -117.93(13) . . . . ?
C4 N10 K1 O3 144.97(16) . . . 1_465 ?
N9 N10 K1 O3 -18.37(12) . . . 1_465 ?
C4 N10 K1 N7 -138.02(15) . . . 1_565 ?
N9 N10 K1 N7 58.64(13) . . . 1_565 ?
C4 N10 K1 K2 -97.32(16) . . . 2_666 ?
N9 N10 K1 K2 99.34(13) . . . 2_666 ?
C1 N4 K1 O4 -46.9(2) . . . 1_565 ?
N3 N4 K1 O4 -168.87(12) . . . 1_565 ?
C1 N4 K1 O1 1.95(15) . . . 2_765 ?
N3 N4 K1 O1 -120.00(11) . . . 2_765 ?
C1 N4 K1 N10 -77.63(15) . . . . ?
N3 N4 K1 N10 160.42(12) . . . . ?
C1 N4 K1 N3 127.27(14) . . . 2_675 ?
N3 N4 K1 N3 5.32(14) . . . 2_675 ?
C1 N4 K1 O2 -176.61(15) . . . 1_465 ?
N3 N4 K1 O2 61.45(11) . . . 1_465 ?
C1 N4 K1 N5 61.51(14) . . . 2_765 ?
N3 N4 K1 N5 -60.44(11) . . . 2_765 ?
C1 N4 K1 N2 146.93(13) . . . 2_675 ?
N3 N4 K1 N2 24.99(13) . . . 2_675 ?
C1 N4 K1 N3 121.9(2) . . . . ?
C1 N4 K1 O3 -144.15(14) . . . 1_465 ?
N3 N4 K1 O3 93.91(11) . . . 1_465 ?
C1 N4 K1 K2 -29.86(16) . . . 2_666 ?
N3 N4 K1 K2 -151.81(9) . . . 2_666 ?
N2 N3 K1 O1 -19.65(17) . . . 2_765 ?
N4 N3 K1 O1 61.78(11) . . . 2_765 ?
K1 N3 K1 O1 -123.26(5) 2_675 . . 2_765 ?
N2 N3 K1 N10 -99.68(17) . . . . ?
N4 N3 K1 N10 -18.25(11) . . . . ?
K1 N3 K1 N10 156.71(5) 2_675 . . . ?
N2 N3 K1 N4 -81.43(19) . . . . ?
K1 N3 K1 N4 174.96(13) 2_675 . . . ?
N2 N3 K1 N3 103.61(18) . . . 2_675 ?
N4 N3 K1 N3 -174.96(13) . . . 2_675 ?
K1 N3 K1 N3 0.0 2_675 . . 2_675 ?
N2 N3 K1 O2 168.55(18) . . . 1_465 ?
N4 N3 K1 O2 -110.03(11) . . . 1_465 ?
K1 N3 K1 O2 64.93(4) 2_675 . . 1_465 ?
N2 N3 K1 N5 27.61(16) . . . 2_765 ?
N4 N3 K1 N5 109.04(12) . . . 2_765 ?
K1 N3 K1 N5 -76.01(5) 2_675 . . 2_765 ?
N2 N3 K1 N2 119.42(16) . . . 2_675 ?
N4 N3 K1 N2 -159.15(11) . . . 2_675 ?
K1 N3 K1 N2 15.80(5) 2_675 . . 2_675 ?
N2 N3 K1 O3 -171.11(17) . . . 1_465 ?
N4 N3 K1 O3 -89.68(11) . . . 1_465 ?
K1 N3 K1 O3 85.28(4) 2_675 . . 1_465 ?
N2 N3 K1 N7 88.5(2) . . . 1_565 ?
N4 N3 K1 N7 169.97(12) . . . 1_565 ?
K1 N3 K1 N7 -15.07(12) 2_675 . . 1_565 ?
N2 N3 K1 K2 -43.33(19) . . . 2_666 ?
N4 N3 K1 K2 38.10(12) . . . 2_666 ?
K1 N3 K1 K2 -146.94(3) 2_675 . . 2_666 ?
N7 O4 K2 O4 -139.52(11) . . . 2_656 ?
K1 O4 K2 O4 100.05(5) 1_545 . . 2_656 ?
K2 O4 K2 O4 0.0 2_656 . . 2_656 ?
N7 O4 K2 O1 -76.14(10) . . . 1_456 ?
K1 O4 K2 O1 163.43(4) 1_545 . . 1_456 ?
K2 O4 K2 O1 63.39(6) 2_656 . . 1_456 ?
N7 O4 K2 O3 -177.78(8) . . . 2_656 ?
K1 O4 K2 O3 61.79(7) 1_545 . . 2_656 ?
K2 O4 K2 O3 -38.25(7) 2_656 . . 2_656 ?
N7 O4 K2 N9 58.04(12) . . . 2_566 ?
K1 O4 K2 N9 -62.39(8) 1_545 . . 2_566 ?
K2 O4 K2 N9 -162.44(6) 2_656 . . 2_566 ?
N7 O4 K2 O3 97.06(9) . . . 1_455 ?
K1 O4 K2 O3 -23.37(4) 1_545 . . 1_455 ?
K2 O4 K2 O3 -123.42(4) 2_656 . . 1_455 ?
N7 O4 K2 N8 37.88(11) . . . 2_566 ?
K1 O4 K2 N8 -82.55(5) 1_545 . . 2_566 ?
K2 O4 K2 N8 177.41(4) 2_656 . . 2_566 ?
N7 O4 K2 N8 -2.39(8) . . . . ?
K1 O4 K2 N8 -122.82(6) 1_545 . . . ?
K2 O4 K2 N8 137.14(6) 2_656 . . . ?
K1 O4 K2 N7 -120.43(11) 1_545 . . . ?
K2 O4 K2 N7 139.52(11) 2_656 . . . ?
N7 O4 K2 N9 155.92(10) . . . 1_545 ?
K1 O4 K2 N9 35.49(4) 1_545 . . 1_545 ?
K2 O4 K2 N9 -64.55(4) 2_656 . . 1_545 ?
N7 O4 K2 K1 -100.47(9) . . . 2_666 ?
K1 O4 K2 K1 139.10(3) 1_545 . . 2_666 ?
K2 O4 K2 K1 39.06(3) 2_656 . . 2_666 ?
N7 O4 K2 K1 120.43(11) . . . 1_545 ?
K2 O4 K2 K1 -100.05(5) 2_656 . . 1_545 ?
N9 N8 K2 O4 -153.3(4) . . . 2_656 ?
N7 N8 K2 O4 49.01(10) . . . 2_656 ?
K2 N8 K2 O4 -167.19(4) 2_566 . . 2_656 ?
N9 N8 K2 O1 -75.7(4) . . . 1_456 ?
N7 N8 K2 O1 126.61(9) . . . 1_456 ?
K2 N8 K2 O1 -89.58(4) 2_566 . . 1_456 ?
N7 N8 K2 O4 2.26(8) . . . . ?
K2 N8 K2 O4 146.07(7) 2_566 . . . ?
N9 N8 K2 N9 15.6(5) . . . 2_566 ?
N7 N8 K2 N9 -142.13(9) . . . 2_566 ?
K2 N8 K2 N9 1.68(5) 2_566 . . 2_566 ?
N7 N8 K2 O3 -80.18(9) . . . 1_455 ?
K2 N8 K2 O3 63.63(4) 2_566 . . 1_455 ?
N9 N8 K2 N8 13.9(4) . . . 2_566 ?
N7 N8 K2 N8 -143.81(11) . . . 2_566 ?
K2 N8 K2 N8 0.0 2_566 . . 2_566 ?
N9 N8 K2 N7 157.7(5) . . . . ?
K2 N8 K2 N7 143.81(11) 2_566 . . . ?
N9 N8 K2 N9 132.1(4) . . . 1_545 ?
N7 N8 K2 N9 -25.56(11) . . . 1_545 ?
K2 N8 K2 N9 118.24(5) 2_566 . . 1_545 ?
N9 N8 K2 K1 -116.0(4) . . . 2_666 ?
N7 N8 K2 K1 86.30(9) . . . 2_666 ?
K2 N8 K2 K1 -129.89(3) 2_566 . . 2_666 ?
N9 N8 K2 K1 126.4(4) . . . 1_545 ?
N7 N8 K2 K1 -31.33(8) . . . 1_545 ?
K2 N8 K2 K1 112.47(4) 2_566 . . 1_545 ?
O4 N7 K2 O4 40.13(11) . . . 2_656 ?
N8 N7 K2 O4 -135.57(9) . . . 2_656 ?
K1 N7 K2 O4 82.83(4) 1_545 . . 2_656 ?
O4 N7 K2 O1 115.53(10) . . . 1_456 ?
N8 N7 K2 O1 -60.18(10) . . . 1_456 ?
K1 N7 K2 O1 158.23(4) 1_545 . . 1_456 ?
O4 N7 K2 O3 4.63(17) . . . 2_656 ?
N8 N7 K2 O3 -171.07(12) . . . 2_656 ?
K1 N7 K2 O3 47.33(13) 1_545 . . 2_656 ?
N8 N7 K2 O4 -175.71(15) . . . . ?
K1 N7 K2 O4 42.70(8) 1_545 . . . ?
O4 N7 K2 N9 -138.15(9) . . . 2_566 ?
N8 N7 K2 N9 46.15(11) . . . 2_566 ?
K1 N7 K2 N9 -95.45(5) 1_545 . . 2_566 ?
O4 N7 K2 O3 -83.00(10) . . . 1_455 ?
N8 N7 K2 O3 101.30(9) . . . 1_455 ?
K1 N7 K2 O3 -40.30(3) 1_545 . . 1_455 ?
O4 N7 K2 N8 -147.24(9) . . . 2_566 ?
N8 N7 K2 N8 37.05(11) . . . 2_566 ?
K1 N7 K2 N8 -104.54(4) 1_545 . . 2_566 ?
O4 N7 K2 N8 175.71(15) . . . . ?
K1 N7 K2 N8 -141.60(10) 1_545 . . . ?
O4 N7 K2 N9 -25.13(10) . . . 1_545 ?
N8 N7 K2 N9 159.17(9) . . . 1_545 ?
K1 N7 K2 N9 17.57(4) 1_545 . . 1_545 ?
O4 N7 K2 K1 80.15(9) . . . 2_666 ?
N8 N7 K2 K1 -95.55(9) . . . 2_666 ?
K1 N7 K2 K1 122.85(2) 1_545 . . 2_666 ?
O4 N7 K2 K1 -42.70(8) . . . 1_545 ?
N8 N7 K2 K1 141.60(10) . . . 1_545 ?


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            ?



_database_code_depnum_ccdc_archive 'CCDC 988409'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix185
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Mon Apr 22 17:08:06 2013'
;
_audit_update_record             06.05.2013

_chemical_name_systematic        
'bisguanidinium bis(1-oxido-tetrazolyl)-furoxane'
_chemical_compound_source        ?
_chemical_name_common            
'bisguanidinium bis(1-oxido-tetrazolyl)-furoxane'
_chemical_formula_moiety         ' C4 N10 O4, 2(C H6 N3) '
_chemical_formula_sum            'C6 H12 N16 O4'
_chemical_formula_weight         372.32


_cell_length_a                   14.7455(8)
_cell_length_b                   11.7557(6)
_cell_length_c                   10.6941(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.904(5)
_cell_angle_gamma                90.00
_cell_volume                     1422.05(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1627
_cell_measurement_theta_min      4.4240
_cell_measurement_theta_max      31.9260
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  0.9812
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            5356
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         26.74
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.993

_reflns_number_total             1503
_reflns_number_gt                1254
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0070566000
_diffrn_orient_matrix_UB_12      0.0560855000
_diffrn_orient_matrix_UB_13      -0.0223623000
_diffrn_orient_matrix_UB_21      0.0422861000
_diffrn_orient_matrix_UB_22      0.0113208000
_diffrn_orient_matrix_UB_23      0.0522900000
_diffrn_orient_matrix_UB_31      0.0457912000
_diffrn_orient_matrix_UB_32      -0.0190993000
_diffrn_orient_matrix_UB_33      -0.0348857000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_Int_Tables_number      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'
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'


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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0345P)²+1.0219P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1503
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
N3 N 0.21320(11) 0.49788(11) 0.08586(16) 0.0217(3) Uani 1 1 d . . .
O3 O 0.32574(17) 0.14602(19) 0.1871(3) 0.0203(5) Uani 0.50 1 d P . .
O2 O 0.5000 0.12233(13) 0.2500 0.0287(4) Uani 1 2 d S . .
N4 N 0.26913(10) 0.40047(11) 0.16551(15) 0.0196(3) Uani 1 1 d . . .
N2 N 0.26333(11) 0.54786(11) 0.03397(16) 0.0225(3) Uani 1 1 d . . .
C2 C 0.44059(12) 0.29919(13) 0.21976(18) 0.0171(3) Uani 1 1 d . . .
N5 N 0.40580(11) 0.19314(11) 0.20538(18) 0.0235(3) Uani 1 1 d . . .
O1 O 0.42218(10) 0.50141(9) 0.04432(15) 0.0274(3) Uani 1 1 d . . .
C1 C 0.35818(12) 0.39169(13) 0.16291(18) 0.0165(3) Uani 1 1 d . . .
N1 N 0.35452(10) 0.48106(11) 0.08120(16) 0.0191(3) Uani 1 1 d . . .
N6 N -0.08576(12) 0.23835(13) 0.02672(17) 0.0224(3) Uani 1 1 d . . .
N7 N 0.10737(13) 0.21584(13) 0.13400(18) 0.0245(3) Uani 1 1 d . . .
N8 N 0.03767(13) 0.39294(12) 0.12732(18) 0.0221(3) Uani 1 1 d . . .
C3 C 0.01953(12) 0.28228(13) 0.09572(17) 0.0169(3) Uani 1 1 d . . .
H7B H 0.1761(19) 0.2513(19) 0.169(3) 0.047(6) Uiso 1 1 d . . .
H8A H 0.1042(19) 0.4212(19) 0.168(3) 0.041(6) Uiso 1 1 d . . .
H6B H -0.0927(16) 0.1634(19) 0.016(2) 0.031(5) Uiso 1 1 d . . .
H7A H 0.0884(17) 0.1488(19) 0.102(2) 0.034(6) Uiso 1 1 d . . .
H6A H -0.1425(16) 0.2802(16) 0.005(2) 0.027(5) Uiso 1 1 d . . .
H8B H -0.0230(18) 0.4356(19) 0.089(2) 0.037(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
N3 N2 1.3137(19) . ?
N3 N4 1.3475(18) . ?
O3 N5 1.201(2) . ?
O2 N5 1.4141(16) 2_655 ?
O2 N5 1.4141(16) . ?
N4 C1 1.3351(18) . ?
N2 N1 1.3447(17) . ?
C2 N5 1.319(2) . ?
C2 C2 1.426(3) 2_655 ?
C2 C1 1.443(2) . ?
O1 N1 1.3088(15) . ?
C1 N1 1.345(2) . ?
N6 C3 1.3235(19) . ?
N6 H6B 0.89(2) . ?
N6 H6A 0.863(19) . ?
N7 C3 1.332(2) . ?
N7 H7B 0.92(2) . ?
N7 H7A 0.83(2) . ?
N8 C3 1.327(2) . ?
N8 H8A 0.84(2) . ?
N8 H8B 0.87(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
N2 N3 N4 111.41(12) . . ?
N5 O2 N5 107.87(15) 2_655 . ?
C1 N4 N3 105.29(12) . . ?
N3 N2 N1 106.15(12) . . ?
N5 C2 C2 109.00(8) . 2_655 ?
N5 C2 C1 120.26(13) . . ?
C2 C2 C1 130.45(8) 2_655 . ?
O3 N5 C2 136.30(16) . . ?
O3 N5 O2 115.69(15) . . ?
C2 N5 O2 107.02(12) . . ?
N4 C1 N1 108.84(13) . . ?
N4 C1 C2 128.56(14) . . ?
N1 C1 C2 122.31(13) . . ?
O1 N1 N2 123.50(13) . . ?
O1 N1 C1 128.15(12) . . ?
N2 N1 C1 108.29(12) . . ?
C3 N6 H6B 117.1(12) . . ?
C3 N6 H6A 121.0(12) . . ?
H6B N6 H6A 121.4(17) . . ?
C3 N7 H7B 117.2(13) . . ?
C3 N7 H7A 115.2(13) . . ?
H7B N7 H7A 125.7(19) . . ?
C3 N8 H8A 119.6(15) . . ?
C3 N8 H8B 118.0(14) . . ?
H8A N8 H8B 121(2) . . ?
N6 C3 N8 119.81(14) . . ?
N6 C3 N7 120.27(15) . . ?
N8 C3 N7 119.92(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
N2 N3 N4 C1 0.58(16) . . . . ?
N4 N3 N2 N1 0.00(16) . . . . ?
C2 C2 N5 O3 165.2(2) 2_655 . . . ?
C1 C2 N5 O3 -20.3(3) . . . . ?
C2 C2 N5 O2 -2.4(2) 2_655 . . . ?
C1 C2 N5 O2 172.06(11) . . . . ?
N5 O2 N5 O3 -169.58(19) 2_655 . . . ?
N5 O2 N5 C2 0.95(8) 2_655 . . . ?
N3 N4 C1 N1 -0.94(16) . . . . ?
N3 N4 C1 C2 -174.75(14) . . . . ?
N5 C2 C1 N4 35.1(2) . . . . ?
C2 C2 C1 N4 -151.8(2) 2_655 . . . ?
N5 C2 C1 N1 -138.00(16) . . . . ?
C2 C2 C1 N1 35.1(3) 2_655 . . . ?
N3 N2 N1 O1 176.82(14) . . . . ?
N3 N2 N1 C1 -0.59(16) . . . . ?
N4 C1 N1 O1 -176.29(14) . . . . ?
C2 C1 N1 O1 -2.0(2) . . . . ?
N4 C1 N1 N2 0.97(17) . . . . ?
C2 C1 N1 N2 175.25(13) . . . . ?

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
N7 H7B N4 0.92(2) 2.24(2) 3.079(2) 150.5(18) .
N7 H7B O3 0.92(2) 2.43(2) 3.003(2) 120.5(17) .
N8 H8A N3 0.84(2) 2.45(2) 3.1449(19) 140.4(18) .
N8 H8A N4 0.84(2) 2.46(2) 3.1678(19) 141.5(19) .
N6 H6B O1 0.89(2) 1.92(2) 2.7891(19) 167.0(18) 3_445
N6 H6B N1 0.89(2) 2.53(2) 3.3048(19) 146.8(16) 3_445
N6 H6B N2 0.89(2) 2.631(19) 3.1927(19) 122.2(14) 3_445
N7 H7A O1 0.83(2) 2.29(2) 3.047(2) 150.3(18) 7
N6 H6A N2 0.863(19) 2.55(2) 3.378(2) 162.0(16) 5_565
N8 H8B N3 0.87(2) 2.29(2) 3.116(2) 159.6(18) 5_565
N8 H8B O2 0.87(2) 2.67(2) 3.1994(19) 120.3(16) 3_455

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988410'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix202
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Thu May 02 13:26:24 2013'
;
_audit_update_record             14.05.2013

_chemical_name_systematic        
'bis-aminoguanidinium bis-(1-oxidotetrazolyl)-furoxane'
_chemical_compound_source        ?
_chemical_name_common            
'bis-aminoguanidinium bis-(1-oxidotetrazolyl)-furoxane'
_chemical_formula_moiety         ' 	C4 N10 O4, 2(C H7 N4) '
_chemical_formula_sum            'C6 H14 N18 O4'
_chemical_formula_weight         402.35


_cell_length_a                   7.0135(7)
_cell_length_b                   31.347(2)
_cell_length_c                   7.9795(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.793(12)
_cell_angle_gamma                90.00
_cell_volume                     1579.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2231
_cell_measurement_theta_min      4.5710
_cell_measurement_theta_max      32.8610
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9722
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            8257
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         26.25
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.25
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             3158
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      -0.0564410000
_diffrn_orient_matrix_UB_12      -0.0120270000
_diffrn_orient_matrix_UB_13      0.0389602000
_diffrn_orient_matrix_UB_21      -0.0912383000
_diffrn_orient_matrix_UB_22      0.0126435000
_diffrn_orient_matrix_UB_23      -0.0495408000
_diffrn_orient_matrix_UB_31      -0.0331194000
_diffrn_orient_matrix_UB_32      -0.0144082000
_diffrn_orient_matrix_UB_33      -0.0761194000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2yn

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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.3564P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.20903(19) 0.08495(4) 0.75528(17) 0.0180(3) Uani 1 1 d . . .
O2 O 0.0662(2) 0.23407(4) 0.69221(17) 0.0175(3) Uani 1 1 d . . .
O3 O -0.0617(2) 0.20593(4) 0.40083(17) 0.0200(3) Uani 1 1 d . . .
O4 O 0.29855(19) 0.19948(4) 1.25731(17) 0.0168(3) Uani 1 1 d . . .
N1 N 0.0123(2) 0.08920(5) 0.6285(2) 0.0140(3) Uani 1 1 d . . .
N2 N -0.1018(2) 0.05652(5) 0.5244(2) 0.0180(3) Uani 1 1 d . . .
N3 N -0.2879(2) 0.07279(5) 0.4103(2) 0.0197(4) Uani 1 1 d . . .
N4 N -0.2954(2) 0.11510(5) 0.4385(2) 0.0170(3) Uani 1 1 d . . .
N5 N -0.0218(2) 0.19903(5) 0.5639(2) 0.0143(3) Uani 1 1 d . . .
N6 N 0.1068(2) 0.21992(5) 0.8686(2) 0.0170(3) Uani 1 1 d . . .
N7 N 0.1822(2) 0.16522(4) 1.1886(2) 0.0130(3) Uani 1 1 d . . .
N8 N 0.1637(2) 0.13418(5) 1.2966(2) 0.0160(3) Uani 1 1 d . . .
N9 N 0.0361(2) 0.10533(5) 1.1819(2) 0.0169(3) Uani 1 1 d . . .
N10 N -0.0270(2) 0.11691(5) 1.0029(2) 0.0154(3) Uani 1 1 d . . .
C1 C -0.1074(3) 0.12451(5) 0.5761(2) 0.0130(4) Uani 1 1 d . . .
C2 C -0.0331(3) 0.16578(5) 0.6628(2) 0.0128(4) Uani 1 1 d . . .
C3 C 0.0480(3) 0.17961(5) 0.8501(2) 0.0134(4) Uani 1 1 d . . .
C4 C 0.0665(3) 0.15435(5) 1.0094(2) 0.0130(4) Uani 1 1 d . . .
N11 N 0.6197(2) 0.19858(5) 0.9475(2) 0.0161(3) Uani 1 1 d . . .
N12 N 0.5706(3) 0.16932(5) 1.0586(2) 0.0178(4) Uani 1 1 d . . .
N13 N 0.4390(3) 0.15498(5) 0.6968(2) 0.0174(4) Uani 1 1 d . . .
N14 N 0.5550(3) 0.22070(5) 0.6511(2) 0.0181(4) Uani 1 1 d . . .
C5 C 0.5355(3) 0.19158(5) 0.7640(2) 0.0130(4) Uani 1 1 d . . .
N15 N 0.6745(2) 0.03831(5) 0.8487(2) 0.0162(3) Uani 1 1 d . . .
N16 N 0.5076(3) 0.03009(5) 0.6713(2) 0.0177(4) Uani 1 1 d . . .
N17 N 0.6505(3) -0.03156(5) 0.9273(2) 0.0161(3) Uani 1 1 d . . .
N18 N 0.8890(3) 0.01434(5) 1.1440(2) 0.0169(3) Uani 1 1 d . . .
C6 C 0.7375(3) 0.00664(6) 0.9740(2) 0.0141(4) Uani 1 1 d . . .
H14A H 0.498(4) 0.2142(7) 0.532(4) 0.037(7) Uiso 1 1 d . . .
H17B H 0.695(3) -0.0499(7) 1.017(3) 0.019(5) Uiso 1 1 d . . .
H17A H 0.544(4) -0.0348(7) 0.810(3) 0.039(7) Uiso 1 1 d . . .
H16B H 0.550(3) 0.0359(7) 0.584(3) 0.026(6) Uiso 1 1 d . . .
H16A H 0.400(4) 0.0466(7) 0.656(3) 0.030(6) Uiso 1 1 d . . .
H11 H 0.658(4) 0.2240(8) 0.988(3) 0.034(6) Uiso 1 1 d . . .
H13B H 0.420(3) 0.1377(7) 0.773(3) 0.025(6) Uiso 1 1 d . . .
H13A H 0.382(3) 0.1506(7) 0.577(3) 0.026(6) Uiso 1 1 d . . .
H12B H 0.689(4) 0.1597(7) 1.143(3) 0.026(6) Uiso 1 1 d . . .
H18B H 0.938(3) 0.0394(8) 1.174(3) 0.027(6) Uiso 1 1 d . . .
H14B H 0.622(4) 0.2443(8) 0.694(3) 0.031(6) Uiso 1 1 d . . .
H15 H 0.739(3) 0.0621(8) 0.880(3) 0.031(6) Uiso 1 1 d . . .
H12A H 0.503(4) 0.1841(7) 1.119(3) 0.034(6) Uiso 1 1 d . . .
H18A H 0.924(3) -0.0041(7) 1.234(3) 0.023(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
O1 N1 1.3151(18) . ?
O2 N6 1.3819(18) . ?
O2 N5 1.4442(18) . ?
O3 N5 1.2254(18) . ?
O4 N7 1.3156(18) . ?
N1 C1 1.341(2) . ?
N1 N2 1.342(2) . ?
N2 N3 1.326(2) . ?
N3 N4 1.350(2) . ?
N4 C1 1.331(2) . ?
N5 C2 1.330(2) . ?
N6 C3 1.317(2) . ?
N7 N8 1.343(2) . ?
N7 C4 1.345(2) . ?
N8 N9 1.321(2) . ?
N9 N10 1.349(2) . ?
N10 C4 1.334(2) . ?
C1 C2 1.453(2) . ?
C2 C3 1.416(2) . ?
C3 C4 1.455(2) . ?
N11 C5 1.337(2) . ?
N11 N12 1.418(2) . ?
N11 H11 0.86(2) . ?
N12 H12B 0.86(2) . ?
N12 H12A 0.94(2) . ?
N13 C5 1.322(2) . ?
N13 H13B 0.86(2) . ?
N13 H13A 0.87(2) . ?
N14 C5 1.331(2) . ?
N14 H14A 0.88(2) . ?
N14 H14B 0.86(2) . ?
N15 C6 1.340(2) . ?
N15 N16 1.413(2) . ?
N15 H15 0.85(2) . ?
N16 H16B 0.89(2) . ?
N16 H16A 0.88(2) . ?
N17 C6 1.322(2) . ?
N17 H17B 0.87(2) . ?
N17 H17A 0.92(2) . ?
N18 C6 1.332(2) . ?
N18 H18B 0.85(2) . ?
N18 H18A 0.87(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 O2 N5 108.24(12) . . ?
O1 N1 C1 128.91(14) . . ?
O1 N1 N2 122.84(14) . . ?
C1 N1 N2 108.23(14) . . ?
N3 N2 N1 105.98(14) . . ?
N2 N3 N4 111.19(14) . . ?
C1 N4 N3 104.99(14) . . ?
O3 N5 C2 136.31(15) . . ?
O3 N5 O2 116.64(13) . . ?
C2 N5 O2 107.03(13) . . ?
C3 N6 O2 106.14(14) . . ?
O4 N7 N8 122.65(14) . . ?
O4 N7 C4 128.87(14) . . ?
N8 N7 C4 108.47(14) . . ?
N9 N8 N7 106.07(13) . . ?
N8 N9 N10 111.15(14) . . ?
C4 N10 N9 105.46(14) . . ?
N4 C1 N1 109.59(15) . . ?
N4 C1 C2 127.69(16) . . ?
N1 C1 C2 122.71(15) . . ?
N5 C2 C3 106.61(15) . . ?
N5 C2 C1 121.13(15) . . ?
C3 C2 C1 132.17(16) . . ?
N6 C3 C2 111.98(15) . . ?
N6 C3 C4 121.31(15) . . ?
C2 C3 C4 126.71(16) . . ?
N10 C4 N7 108.84(14) . . ?
N10 C4 C3 126.11(15) . . ?
N7 C4 C3 125.05(15) . . ?
C5 N11 N12 117.81(15) . . ?
C5 N11 H11 118.8(15) . . ?
N12 N11 H11 119.1(15) . . ?
N11 N12 H12B 107.6(14) . . ?
N11 N12 H12A 108.6(14) . . ?
H12B N12 H12A 108(2) . . ?
C5 N13 H13B 117.9(14) . . ?
C5 N13 H13A 119.3(14) . . ?
H13B N13 H13A 122(2) . . ?
C5 N14 H14A 116.1(15) . . ?
C5 N14 H14B 121.0(15) . . ?
H14A N14 H14B 123(2) . . ?
N13 C5 N14 120.40(17) . . ?
N13 C5 N11 119.41(16) . . ?
N14 C5 N11 120.15(17) . . ?
C6 N15 N16 118.20(15) . . ?
C6 N15 H15 118.0(15) . . ?
N16 N15 H15 123.8(15) . . ?
N15 N16 H16B 109.5(14) . . ?
N15 N16 H16A 108.7(14) . . ?
H16B N16 H16A 109(2) . . ?
C6 N17 H17B 114.4(13) . . ?
C6 N17 H17A 117.4(15) . . ?
H17B N17 H17A 128(2) . . ?
C6 N18 H18B 120.1(14) . . ?
C6 N18 H18A 122.2(14) . . ?
H18B N18 H18A 117(2) . . ?
N17 C6 N18 121.13(17) . . ?
N17 C6 N15 119.92(17) . . ?
N18 C6 N15 118.94(17) . . ?

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
O1 N1 N2 N3 -178.40(14) . . . . ?
C1 N1 N2 N3 0.38(18) . . . . ?
N1 N2 N3 N4 0.18(18) . . . . ?
N2 N3 N4 C1 -0.66(19) . . . . ?
N6 O2 N5 O3 -178.06(13) . . . . ?
N6 O2 N5 C2 0.43(17) . . . . ?
N5 O2 N6 C3 -0.19(17) . . . . ?
O4 N7 N8 N9 179.82(14) . . . . ?
C4 N7 N8 N9 -0.59(18) . . . . ?
N7 N8 N9 N10 0.34(18) . . . . ?
N8 N9 N10 C4 0.04(18) . . . . ?
N3 N4 C1 N1 0.89(19) . . . . ?
N3 N4 C1 C2 -179.02(16) . . . . ?
O1 N1 C1 N4 177.87(15) . . . . ?
N2 N1 C1 N4 -0.81(19) . . . . ?
O1 N1 C1 C2 -2.2(3) . . . . ?
N2 N1 C1 C2 179.10(15) . . . . ?
O3 N5 C2 C3 177.57(18) . . . . ?
O2 N5 C2 C3 -0.48(18) . . . . ?
O3 N5 C2 C1 0.6(3) . . . . ?
O2 N5 C2 C1 -177.47(14) . . . . ?
N4 C1 C2 N5 -60.0(3) . . . . ?
N1 C1 C2 N5 120.10(19) . . . . ?
N4 C1 C2 C3 123.9(2) . . . . ?
N1 C1 C2 C3 -56.0(3) . . . . ?
O2 N6 C3 C2 -0.12(19) . . . . ?
O2 N6 C3 C4 -179.42(14) . . . . ?
N5 C2 C3 N6 0.4(2) . . . . ?
C1 C2 C3 N6 176.92(18) . . . . ?
N5 C2 C3 C4 179.65(16) . . . . ?
C1 C2 C3 C4 -3.8(3) . . . . ?
N9 N10 C4 N7 -0.41(18) . . . . ?
N9 N10 C4 C3 179.53(16) . . . . ?
O4 N7 C4 N10 -179.82(15) . . . . ?
N8 N7 C4 N10 0.63(19) . . . . ?
O4 N7 C4 C3 0.2(3) . . . . ?
N8 N7 C4 C3 -179.30(15) . . . . ?
N6 C3 C4 N10 164.86(17) . . . . ?
C2 C3 C4 N10 -14.3(3) . . . . ?
N6 C3 C4 N7 -15.2(3) . . . . ?
C2 C3 C4 N7 165.59(17) . . . . ?
N12 N11 C5 N13 -10.5(2) . . . . ?
N12 N11 C5 N14 171.75(16) . . . . ?
N16 N15 C6 N17 3.1(2) . . . . ?
N16 N15 C6 N18 -177.43(16) . . . . ?

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
N14 H14A O4 0.88(2) 2.07(3) 2.938(2) 167(2) 1_554
N17 H17B O1 0.87(2) 1.97(2) 2.831(2) 171.5(19) 3_657
N17 H17A N3 0.92(2) 2.23(2) 3.071(2) 152(2) 3_556
N16 H16B N3 0.89(2) 2.43(2) 3.285(2) 160.8(19) 1_655
N16 H16A O1 0.88(2) 2.19(2) 3.002(2) 153.5(19) .
N11 H11 O2 0.86(2) 2.39(2) 3.008(2) 129.4(19) 4_666
N11 H11 O3 0.86(2) 2.60(2) 3.210(2) 129.2(19) 4_666
N13 H13B O1 0.86(2) 2.19(2) 2.880(2) 137.4(19) .
N13 H13A N8 0.87(2) 2.15(2) 2.997(2) 163.0(19) 1_554
N12 H12B O3 0.86(2) 2.50(2) 3.049(2) 121.9(18) 1_656
N18 H18B N9 0.85(2) 2.17(2) 3.003(2) 166.7(19) 1_655
N14 H14B O4 0.86(2) 2.08(2) 2.939(2) 169(2) 4_665
N15 H15 N10 0.85(2) 2.28(2) 3.119(2) 168(2) 1_655
N12 H12A O4 0.94(2) 2.21(2) 3.112(2) 162.3(19) .
N12 H12A N7 0.94(2) 2.61(2) 3.313(2) 132.6(17) .
N12 H12A O2 0.94(2) 2.62(2) 3.215(2) 121.5(17) 4_666
N18 H18A N2 0.87(2) 2.43(2) 3.275(2) 165.8(18) 3_657

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988411'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ix536
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Tue Nov 12 07:29:56 2013'
;
_audit_update_record             21.11.2013

_chemical_name_systematic        
'dipotassium bis(1-oxidotetrazolyl)furazane dihydrate'
_chemical_compound_source        ?
_chemical_name_common            
'dipotassium bis(1-oxidotetrazolyl)furazane dihydrate'
_chemical_formula_moiety         'C4 N10 O3, 2(H2 O), 2(K)'
_chemical_formula_sum            'C4 H4 K2 N10 O5'
_chemical_formula_weight         350.37


_cell_length_a                   7.4337(4)
_cell_length_b                   21.6146(9)
_cell_length_c                   7.5901(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.741(5)
_cell_angle_gamma                90.00
_cell_volume                     1208.44(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4377
_cell_measurement_theta_min      4.5760
_cell_measurement_theta_max      32.1970
_cell_special_details            ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_T_max  0.9070
_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      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            9113
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         26.00
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995

_reflns_number_total             2362
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      -0.0551068000
_diffrn_orient_matrix_UB_12      0.0268892000
_diffrn_orient_matrix_UB_13      -0.0055135000
_diffrn_orient_matrix_UB_21      0.0205550000
_diffrn_orient_matrix_UB_22      0.0041219000
_diffrn_orient_matrix_UB_23      0.0932229000
_diffrn_orient_matrix_UB_31      0.0763172000
_diffrn_orient_matrix_UB_32      0.0183490000
_diffrn_orient_matrix_UB_33      -0.0129252000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P  21/c '
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2ybc

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'
K K 0.2009 0.2494 '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'


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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0245P)²+0.6830P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2362
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.59234(16) 0.32319(5) 0.67058(17) 0.0155(3) Uani 1 1 d . . .
O2 O 0.17632(16) 0.24067(5) 0.91325(16) 0.0147(3) Uani 1 1 d . . .
O3 O 0.19726(16) 0.05585(5) 1.07854(16) 0.0147(3) Uani 1 1 d . . .
N1 N 0.64817(18) 0.26624(6) 0.66472(19) 0.0120(3) Uani 1 1 d . . .
N2 N 0.80079(19) 0.25211(6) 0.59575(19) 0.0136(3) Uani 1 1 d . . .
N3 N 0.8174(2) 0.19162(6) 0.6066(2) 0.0159(3) Uani 1 1 d . . .
N4 N 0.68010(19) 0.16604(6) 0.6796(2) 0.0152(3) Uani 1 1 d . . .
N5 N 0.32613(19) 0.26030(6) 0.83849(19) 0.0131(3) Uani 1 1 d . . .
N6 N 0.16658(19) 0.17728(6) 0.9151(2) 0.0140(3) Uani 1 1 d . . .
N7 N 0.27771(18) 0.04787(6) 0.93691(19) 0.0111(3) Uani 1 1 d . . .
N8 N 0.31757(19) -0.00844(6) 0.87891(19) 0.0141(3) Uani 1 1 d . . .
N9 N 0.3991(2) 0.00056(6) 0.7369(2) 0.0149(3) Uani 1 1 d . . .
N10 N 0.4123(2) 0.06121(6) 0.7028(2) 0.0144(3) Uani 1 1 d . . .
C1 C 0.5740(2) 0.21318(7) 0.7152(2) 0.0111(3) Uani 1 1 d . . .
C2 C 0.4076(2) 0.20990(7) 0.7953(2) 0.0108(3) Uani 1 1 d . . .
C3 C 0.3067(2) 0.15706(7) 0.8446(2) 0.0115(3) Uani 1 1 d . . .
C4 C 0.3356(2) 0.09058(7) 0.8288(2) 0.0116(3) Uani 1 1 d . . .
O4 O 0.03901(19) 0.10859(7) 0.42420(19) 0.0218(3) Uani 1 1 d . . .
O5 O 0.8760(2) 0.04577(7) 0.7164(2) 0.0253(3) Uani 1 1 d . . .
K1 K 0.40211(5) 0.106541(15) 0.35799(5) 0.01371(10) Uani 1 1 d . . .
K2 K 0.88342(5) 0.115825(16) 0.05928(5) 0.01565(11) Uani 1 1 d . . .
H5B H 0.843(3) 0.0161(12) 0.776(4) 0.043(7) Uiso 1 1 d . . .
H4B H -0.012(3) 0.1372(12) 0.470(3) 0.037(7) Uiso 1 1 d . . .
H4A H 0.019(4) 0.0784(13) 0.477(4) 0.044(8) Uiso 1 1 d . . .
H5A H 0.775(4) 0.0640(12) 0.687(4) 0.044(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
O1 N1 1.3018(17) . ?
O2 N6 1.3723(17) . ?
O2 N5 1.3828(17) . ?
O3 N7 1.3100(17) . ?
N1 N2 1.3470(19) . ?
N1 C1 1.350(2) . ?
N2 N3 1.3149(19) . ?
N3 N4 1.344(2) . ?
N4 C1 1.338(2) . ?
N4 K1 3.2442(16) . ?
N5 C2 1.309(2) . ?
N6 C3 1.309(2) . ?
N7 N8 1.3409(19) . ?
N7 C4 1.344(2) . ?
N8 N9 1.320(2) . ?
N9 N10 1.342(2) . ?
N10 C4 1.338(2) . ?
N10 K1 2.7860(15) . ?
C1 C2 1.452(2) . ?
C2 C3 1.443(2) . ?
C3 C4 1.460(2) . ?
O4 K1 2.8117(14) . ?




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
N1 O1 K1 139.83(9) . 4_566 ?
N1 O1 K2 100.04(8) . 4_566 ?
K1 O1 K2 113.06(4) 4_566 4_566 ?
N6 O2 N5 110.92(11) . . ?
N7 O3 K2 120.92(9) . 1_456 ?
N7 O3 K1 115.52(9) . 1_556 ?
K2 O3 K1 104.24(4) 1_456 1_556 ?
O1 N1 N2 121.11(13) . . ?
O1 N1 C1 130.49(13) . . ?
N2 N1 C1 108.37(13) . . ?
O1 N1 K2 56.74(7) . 4_566 ?
N2 N1 K2 64.73(8) . 4_566 ?
C1 N1 K2 171.65(11) . 4_566 ?
N3 N2 N1 106.13(13) . . ?
N3 N2 K2 162.21(11) . 4_566 ?
N1 N2 K2 90.80(9) . 4_566 ?
N2 N3 N4 111.41(13) . . ?
C1 N4 N3 105.72(13) . . ?
C1 N4 K1 96.94(10) . . ?
N3 N4 K1 107.16(10) . . ?
C1 N4 K2 106.93(10) . 1_556 ?
N3 N4 K2 102.38(10) . 1_556 ?
K1 N4 K2 134.97(5) . 1_556 ?
C2 N5 O2 105.83(12) . . ?
C2 N5 K1 137.44(11) . 4_566 ?
O2 N5 K1 116.14(9) . 4_566 ?
C3 N6 O2 106.46(13) . . ?
C3 N6 K2 132.50(11) . 1_456 ?
O2 N6 K2 121.03(9) . 1_456 ?
O3 N7 N8 122.31(13) . . ?
O3 N7 C4 129.03(13) . . ?
N8 N7 C4 108.66(13) . . ?
N8 N7 K1 126.49(10) . 1_556 ?
C4 N7 K1 104.21(10) . 1_556 ?
N9 N8 N7 106.28(12) . . ?
N9 N8 K2 124.48(10) . 3_656 ?
N7 N8 K2 122.98(10) . 3_656 ?
N8 N9 N10 110.78(13) . . ?
N8 N9 K1 113.08(9) . 3_656 ?
N10 N9 K1 132.94(10) . 3_656 ?
C4 N10 N9 106.05(13) . . ?
C4 N10 K1 122.97(11) . . ?
N9 N10 K1 122.08(10) . . ?
N4 C1 N1 108.37(14) . . ?
N4 C1 C2 127.31(14) . . ?
N1 C1 C2 124.32(14) . . ?
N5 C2 C3 108.63(14) . . ?
N5 C2 C1 120.88(14) . . ?
C3 C2 C1 130.47(15) . . ?
N6 C3 C2 108.16(14) . . ?
N6 C3 C4 119.75(14) . . ?
C2 C3 C4 132.09(15) . . ?
N10 C4 N7 108.23(14) . . ?
N10 C4 C3 127.40(15) . . ?
N7 C4 C3 124.27(14) . . ?
K1 O4 K2 95.77(4) . 1_455 ?
K1 O4 H4B 126.4(17) . . ?
K2 O4 H4B 102.7(17) 1_455 . ?
K1 O4 H4A 109.1(19) . . ?
K2 O4 H4A 117(2) 1_455 . ?
H4B O4 H4A 106(3) . . ?
K2 O5 H5B 83.8(17) 1_556 . ?
K2 O5 H5A 84.4(18) 1_556 . ?
H5B O5 H5A 101(2) . . ?
O1 K1 O3 95.63(4) 4_565 1_554 ?
O1 K1 N10 139.92(4) 4_565 . ?
O3 K1 N10 122.80(4) 1_554 . ?
O1 K1 O4 133.54(4) 4_565 . ?
O3 K1 O4 71.96(4) 1_554 . ?
N10 K1 O4 75.11(4) . . ?
O1 K1 N9 89.86(4) 4_565 3_656 ?
O3 K1 N9 74.32(4) 1_554 3_656 ?
N10 K1 N9 90.13(4) . 3_656 ?
O4 K1 N9 126.35(4) . 3_656 ?
O1 K1 N5 61.21(4) 4_565 4_565 ?
O3 K1 N5 106.07(4) 1_554 4_565 ?
N10 K1 N5 111.92(4) . 4_565 ?
O4 K1 N5 79.08(4) . 4_565 ?
N9 K1 N5 151.06(4) 3_656 4_565 ?
O1 K1 N4 80.97(4) 4_565 . ?
O3 K1 N4 175.16(4) 1_554 . ?
N10 K1 N4 59.91(4) . . ?
O4 K1 N4 112.88(4) . . ?
N9 K1 N4 102.11(4) 3_656 . ?
N5 K1 N4 75.39(4) 4_565 . ?
O1 K1 N7 78.87(4) 4_565 1_554 ?
O3 K1 N7 20.06(3) 1_554 1_554 ?
N10 K1 N7 135.36(4) . 1_554 ?
O4 K1 N7 91.57(4) . 1_554 ?
N9 K1 N7 63.67(4) 3_656 1_554 ?
N5 K1 N7 106.76(4) 4_565 1_554 ?
N4 K1 N7 155.19(3) . 1_554 ?
O1 K1 K2 101.67(3) 4_565 1_455 ?
O3 K1 K2 37.73(2) 1_554 1_455 ?
N10 K1 K2 115.47(3) . 1_455 ?
O4 K1 K2 42.54(3) . 1_455 ?
N9 K1 K2 111.49(3) 3_656 1_455 ?
N5 K1 K2 76.68(3) 4_565 1_455 ?
N4 K1 K2 146.25(3) . 1_455 ?
N7 K1 K2 53.55(2) 1_554 1_455 ?
O1 K1 K2 34.46(2) 4_565 . ?
O3 K1 K2 91.44(3) 1_554 . ?
N10 K1 K2 124.56(3) . . ?
O4 K1 K2 159.86(3) . . ?
N9 K1 K2 56.01(3) 3_656 . ?
N5 K1 K2 95.27(3) 4_565 . ?
N4 K1 K2 83.81(3) . . ?
N7 K1 K2 71.39(2) 1_554 . ?
K2 K1 K2 117.423(13) 1_455 . ?
O3 K2 O1 159.21(4) 1_654 4_565 ?
O3 K2 N6 63.70(4) 1_654 1_654 ?
O1 K2 N6 123.26(4) 4_565 1_654 ?
O3 K2 N8 94.01(4) 1_654 3_656 ?
O1 K2 N8 83.57(4) 4_565 3_656 ?
N6 K2 N8 152.19(4) 1_654 3_656 ?
O3 K2 O4 71.47(4) 1_654 1_655 ?
O1 K2 O4 87.77(4) 4_565 1_655 ?
N6 K2 O4 100.10(4) 1_654 1_655 ?
N8 K2 O4 87.04(4) 3_656 1_655 ?
O3 K2 N2 131.43(4) 1_654 4_565 ?
O1 K2 N2 47.60(3) 4_565 4_565 ?
N6 K2 N2 75.91(4) 1_654 4_565 ?
N8 K2 N2 131.15(4) 3_656 4_565 ?
O4 K2 N2 91.39(4) 1_655 4_565 ?
O3 K2 O5 73.45(4) 1_654 1_554 ?
O1 K2 O5 125.57(4) 4_565 1_554 ?
N6 K2 O5 80.18(4) 1_654 1_554 ?
N8 K2 O5 77.42(4) 3_656 1_554 ?
O4 K2 O5 140.31(4) 1_655 1_554 ?
N2 K2 O5 126.22(4) 4_565 1_554 ?
O3 K2 N1 150.07(4) 1_654 4_565 ?
O1 K2 N1 23.22(3) 4_565 4_565 ?
N6 K2 N1 100.36(4) 1_654 4_565 ?
N8 K2 N1 106.76(4) 3_656 4_565 ?
O4 K2 N1 88.01(4) 1_655 4_565 ?
N2 K2 N1 24.47(4) 4_565 4_565 ?
O5 K2 N1 131.33(4) 1_554 4_565 ?
O3 K2 N4 120.75(4) 1_654 1_554 ?
O1 K2 N4 79.75(4) 4_565 1_554 ?
N6 K2 N4 77.41(4) 1_654 1_554 ?
N8 K2 N4 103.15(4) 3_656 1_554 ?
O4 K2 N4 162.78(4) 1_655 1_554 ?
N2 K2 N4 71.44(4) 4_565 1_554 ?
O5 K2 N4 56.57(4) 1_554 1_554 ?
N1 K2 N4 75.85(4) 4_565 1_554 ?
O3 K2 K1 38.03(3) 1_654 1_655 ?
O1 K2 K1 123.85(3) 4_565 1_655 ?
N6 K2 K1 63.60(3) 1_654 1_655 ?
N8 K2 K1 109.71(3) 3_656 1_655 ?
O4 K2 K1 41.69(3) 1_655 1_655 ?
N2 K2 K1 100.57(3) 4_565 1_655 ?
O5 K2 K1 110.57(3) 1_554 1_655 ?
N1 K2 K1 112.90(3) 4_565 1_655 ?
N4 K2 K1 140.88(3) 1_554 1_655 ?
O3 K2 K1 134.76(3) 1_654 . ?
O1 K2 K1 32.49(2) 4_565 . ?
N6 K2 K1 154.24(3) 1_654 . ?
N8 K2 K1 53.56(3) 3_656 . ?
O4 K2 K1 75.77(3) 1_655 . ?
N2 K2 K1 78.76(3) 4_565 . ?
O5 K2 K1 119.46(3) 1_554 . ?
N1 K2 K1 54.50(2) 4_565 . ?
N4 K2 K1 98.94(3) 1_554 . ?
K1 K2 K1 117.423(13) 1_655 . ?

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


K1 O1 N1 N2 -152.88(12) 4_566 . . . ?
K2 O1 N1 N2 -7.14(16) 4_566 . . . ?
K1 O1 N1 C1 29.0(3) 4_566 . . . ?
K2 O1 N1 C1 174.79(16) 4_566 . . . ?
K1 O1 N1 K2 -145.74(16) 4_566 . . 4_566 ?
O1 N1 N2 N3 -178.94(14) . . . . ?
C1 N1 N2 N3 -0.48(19) . . . . ?
K2 N1 N2 N3 174.46(14) 4_566 . . . ?
O1 N1 N2 K2 6.60(15) . . . 4_566 ?
C1 N1 N2 K2 -174.94(11) . . . 4_566 ?
N1 N2 N3 N4 0.29(19) . . . . ?
K2 N2 N3 N4 161.9(3) 4_566 . . . ?
N2 N3 N4 C1 0.02(19) . . . . ?
N2 N3 N4 K1 102.63(13) . . . . ?
N2 N3 N4 K2 -111.78(12) . . . 1_556 ?
N6 O2 N5 C2 -0.14(18) . . . . ?
N6 O2 N5 K1 -172.88(9) . . . 4_566 ?
N5 O2 N6 C3 0.37(18) . . . . ?
N5 O2 N6 K2 179.39(9) . . . 1_456 ?
K2 O3 N7 N8 -121.76(13) 1_456 . . . ?
K1 O3 N7 N8 111.11(14) 1_556 . . . ?
K2 O3 N7 C4 59.2(2) 1_456 . . . ?
K1 O3 N7 C4 -67.94(19) 1_556 . . . ?
K2 O3 N7 K1 127.13(11) 1_456 . . 1_556 ?
O3 N7 N8 N9 -179.15(14) . . . . ?
C4 N7 N8 N9 0.07(18) . . . . ?
K1 N7 N8 N9 -124.83(11) 1_556 . . . ?
O3 N7 N8 K2 27.6(2) . . . 3_656 ?
C4 N7 N8 K2 -153.13(11) . . . 3_656 ?
K1 N7 N8 K2 81.96(13) 1_556 . . 3_656 ?
N7 N8 N9 N10 0.01(18) . . . . ?
K2 N8 N9 N10 152.71(11) 3_656 . . . ?
N7 N8 N9 K1 162.50(9) . . . 3_656 ?
K2 N8 N9 K1 -44.80(14) 3_656 . . 3_656 ?
N8 N9 N10 C4 -0.09(19) . . . . ?
K1 N9 N10 C4 -157.88(12) 3_656 . . . ?
N8 N9 N10 K1 -148.16(11) . . . . ?
K1 N9 N10 K1 54.05(18) 3_656 . . . ?
N3 N4 C1 N1 -0.33(18) . . . . ?
K1 N4 C1 N1 -110.38(12) . . . . ?
K2 N4 C1 N1 108.24(12) 1_556 . . . ?
N3 N4 C1 C2 -179.91(17) . . . . ?
K1 N4 C1 C2 70.03(18) . . . . ?
K2 N4 C1 C2 -71.35(18) 1_556 . . . ?
O1 N1 C1 N4 178.77(16) . . . . ?
N2 N1 C1 N4 0.51(19) . . . . ?
O1 N1 C1 C2 -1.6(3) . . . . ?
N2 N1 C1 C2 -179.89(15) . . . . ?
O2 N5 C2 C3 -0.13(18) . . . . ?
K1 N5 C2 C3 170.22(12) 4_566 . . . ?
O2 N5 C2 C1 -178.93(14) . . . . ?
K1 N5 C2 C1 -8.6(3) 4_566 . . . ?
N4 C1 C2 N5 173.37(17) . . . . ?
N1 C1 C2 N5 -6.2(3) . . . . ?
N4 C1 C2 C3 -5.1(3) . . . . ?
N1 C1 C2 C3 175.33(17) . . . . ?
O2 N6 C3 C2 -0.43(18) . . . . ?
K2 N6 C3 C2 -179.29(11) 1_456 . . . ?
O2 N6 C3 C4 179.52(14) . . . . ?
K2 N6 C3 C4 0.7(2) 1_456 . . . ?
N5 C2 C3 N6 0.4(2) . . . . ?
C1 C2 C3 N6 179.02(17) . . . . ?
N5 C2 C3 C4 -179.57(17) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
N9 N10 C4 N7 0.13(19) . . . . ?
K1 N10 C4 N7 147.85(11) . . . . ?
N9 N10 C4 C3 -176.31(16) . . . . ?
K1 N10 C4 C3 -28.6(2) . . . . ?
O3 N7 C4 N10 179.02(15) . . . . ?
N8 N7 C4 N10 -0.13(19) . . . . ?
K1 N7 C4 N10 137.02(11) 1_556 . . . ?
O3 N7 C4 C3 -4.4(3) . . . . ?
N8 N7 C4 C3 176.45(15) . . . . ?
K1 N7 C4 C3 -46.40(18) 1_556 . . . ?
N6 C3 C4 N10 148.63(18) . . . . ?
C2 C3 C4 N10 -31.4(3) . . . . ?
N6 C3 C4 N7 -27.3(3) . . . . ?
C2 C3 C4 N7 152.66(18) . . . . ?
C4 N10 K1 O1 91.01(14) . . . 4_565 ?
N9 N10 K1 O1 -126.28(11) . . . 4_565 ?
C4 N10 K1 O3 -107.73(13) . . . 1_554 ?
N9 N10 K1 O3 34.99(13) . . . 1_554 ?
C4 N10 K1 O4 -51.27(13) . . . . ?
N9 N10 K1 O4 91.45(12) . . . . ?
C4 N10 K1 N9 -179.06(13) . . . 3_656 ?
N9 N10 K1 N9 -36.34(13) . . . 3_656 ?
C4 N10 K1 N5 20.17(14) . . . 4_565 ?
N9 N10 K1 N5 162.88(11) . . . 4_565 ?
C4 N10 K1 N4 76.98(13) . . . . ?
N9 N10 K1 N4 -140.30(13) . . . . ?
C4 N10 K1 N7 -128.03(12) . . . 1_554 ?
N9 N10 K1 N7 14.68(15) . . . 1_554 ?
C4 N10 K1 K2 -65.05(13) . . . 1_455 ?
N9 N10 K1 K2 77.67(12) . . . 1_455 ?
C4 N10 K1 K2 133.58(12) . . . . ?
N9 N10 K1 K2 -83.71(12) . . . . ?
K2 O4 K1 O1 51.46(7) 1_455 . . 4_565 ?
K2 O4 K1 O3 -28.92(4) 1_455 . . 1_554 ?
K2 O4 K1 N10 -161.45(5) 1_455 . . . ?
K2 O4 K1 N9 -82.57(6) 1_455 . . 3_656 ?
K2 O4 K1 N5 82.14(4) 1_455 . . 4_565 ?
K2 O4 K1 N4 151.03(4) 1_455 . . . ?
K2 O4 K1 N7 -24.63(4) 1_455 . . 1_554 ?
K2 O4 K1 K2 6.89(12) 1_455 . . . ?
C1 N4 K1 O1 93.69(10) . . . 4_565 ?
N3 N4 K1 O1 -15.17(9) . . . 4_565 ?
K2 N4 K1 O1 -143.89(7) 1_556 . . 4_565 ?
C1 N4 K1 N10 -95.40(10) . . . . ?
N3 N4 K1 N10 155.74(11) . . . . ?
K2 N4 K1 N10 27.02(6) 1_556 . . . ?
C1 N4 K1 O4 -39.94(10) . . . . ?
N3 N4 K1 O4 -148.80(9) . . . . ?
K2 N4 K1 O4 82.48(7) 1_556 . . . ?
C1 N4 K1 N9 -178.41(9) . . . 3_656 ?
N3 N4 K1 N9 72.73(10) . . . 3_656 ?
K2 N4 K1 N9 -55.99(7) 1_556 . . 3_656 ?
C1 N4 K1 N5 31.24(9) . . . 4_565 ?
N3 N4 K1 N5 -77.62(10) . . . 4_565 ?
K2 N4 K1 N5 153.67(7) 1_556 . . 4_565 ?
C1 N4 K1 N7 129.67(10) . . . 1_554 ?
N3 N4 K1 N7 20.81(15) . . . 1_554 ?
K2 N4 K1 N7 -107.91(9) 1_556 . . 1_554 ?
C1 N4 K1 K2 -3.82(12) . . . 1_455 ?
N3 N4 K1 K2 -112.68(9) . . . 1_455 ?
K2 N4 K1 K2 118.60(6) 1_556 . . 1_455 ?
C1 N4 K1 K2 128.35(9) . . . . ?
N3 N4 K1 K2 19.49(9) . . . . ?
K2 N4 K1 K2 -109.23(6) 1_556 . . . ?
O1 K1 K2 O3 153.38(7) 4_565 . . 1_654 ?
O3 K1 K2 O3 -108.75(5) 1_554 . . 1_654 ?
N10 K1 K2 O3 23.72(6) . . . 1_654 ?
O4 K1 K2 O3 -142.57(10) . . . 1_654 ?
N9 K1 K2 O3 -38.82(5) 3_656 . . 1_654 ?
N5 K1 K2 O3 144.96(5) 4_565 . . 1_654 ?
N4 K1 K2 O3 70.32(5) . . . 1_654 ?
N7 K1 K2 O3 -109.10(5) 1_554 . . 1_654 ?
K2 K1 K2 O3 -137.32(4) 1_455 . . 1_654 ?
O3 K1 K2 O1 97.86(6) 1_554 . . 4_565 ?
N10 K1 K2 O1 -129.66(6) . . . 4_565 ?
O4 K1 K2 O1 64.05(10) . . . 4_565 ?
N9 K1 K2 O1 167.80(6) 3_656 . . 4_565 ?
N5 K1 K2 O1 -8.42(6) 4_565 . . 4_565 ?
N4 K1 K2 O1 -83.07(6) . . . 4_565 ?
N7 K1 K2 O1 97.52(6) 1_554 . . 4_565 ?
K2 K1 K2 O1 69.29(5) 1_455 . . 4_565 ?
O1 K1 K2 N6 25.14(9) 4_565 . . 1_654 ?
O3 K1 K2 N6 123.00(8) 1_554 . . 1_654 ?
N10 K1 K2 N6 -104.53(8) . . . 1_654 ?
O4 K1 K2 N6 89.18(12) . . . 1_654 ?
N9 K1 K2 N6 -167.06(8) 3_656 . . 1_654 ?
N5 K1 K2 N6 16.71(8) 4_565 . . 1_654 ?
N4 K1 K2 N6 -57.93(8) . . . 1_654 ?
N7 K1 K2 N6 122.65(8) 1_554 . . 1_654 ?
K2 K1 K2 N6 94.43(8) 1_455 . . 1_654 ?
O1 K1 K2 N8 -154.18(6) 4_565 . . 3_656 ?
O3 K1 K2 N8 -56.31(5) 1_554 . . 3_656 ?
N10 K1 K2 N8 76.16(5) . . . 3_656 ?
O4 K1 K2 N8 -90.13(10) . . . 3_656 ?
N9 K1 K2 N8 13.62(5) 3_656 . . 3_656 ?
N5 K1 K2 N8 -162.60(5) 4_565 . . 3_656 ?
N4 K1 K2 N8 122.76(5) . . . 3_656 ?
N7 K1 K2 N8 -56.66(4) 1_554 . . 3_656 ?
K2 K1 K2 N8 -84.89(4) 1_455 . . 3_656 ?
O1 K1 K2 O4 108.88(6) 4_565 . . 1_655 ?
O3 K1 K2 O4 -153.26(4) 1_554 . . 1_655 ?
N10 K1 K2 O4 -20.79(5) . . . 1_655 ?
O4 K1 K2 O4 172.92(12) . . . 1_655 ?
N9 K1 K2 O4 -83.32(5) 3_656 . . 1_655 ?
N5 K1 K2 O4 100.45(4) 4_565 . . 1_655 ?
N4 K1 K2 O4 25.81(4) . . . 1_655 ?
N7 K1 K2 O4 -153.61(4) 1_554 . . 1_655 ?
K2 K1 K2 O4 178.17(3) 1_455 . . 1_655 ?
O1 K1 K2 N2 14.52(6) 4_565 . . 4_565 ?
O3 K1 K2 N2 112.39(4) 1_554 . . 4_565 ?
N10 K1 K2 N2 -115.14(5) . . . 4_565 ?
O4 K1 K2 N2 78.57(10) . . . 4_565 ?
N9 K1 K2 N2 -177.68(5) 3_656 . . 4_565 ?
N5 K1 K2 N2 6.10(4) 4_565 . . 4_565 ?
N4 K1 K2 N2 -68.54(4) . . . 4_565 ?
N7 K1 K2 N2 112.04(4) 1_554 . . 4_565 ?
K2 K1 K2 N2 83.82(3) 1_455 . . 4_565 ?
O1 K1 K2 O5 -110.90(6) 4_565 . . 1_554 ?
O3 K1 K2 O5 -13.04(4) 1_554 . . 1_554 ?
N10 K1 K2 O5 119.43(5) . . . 1_554 ?
O4 K1 K2 O5 -46.86(10) . . . 1_554 ?
N9 K1 K2 O5 56.90(5) 3_656 . . 1_554 ?
N5 K1 K2 O5 -119.33(5) 4_565 . . 1_554 ?
N4 K1 K2 O5 166.03(4) . . . 1_554 ?
N7 K1 K2 O5 -13.39(4) 1_554 . . 1_554 ?
K2 K1 K2 O5 -41.61(4) 1_455 . . 1_554 ?
O1 K1 K2 N1 11.02(6) 4_565 . . 4_565 ?
O3 K1 K2 N1 108.88(4) 1_554 . . 4_565 ?
N10 K1 K2 N1 -118.65(5) . . . 4_565 ?
O4 K1 K2 N1 75.06(10) . . . 4_565 ?
N9 K1 K2 N1 178.82(5) 3_656 . . 4_565 ?
N5 K1 K2 N1 2.59(4) 4_565 . . 4_565 ?
N4 K1 K2 N1 -72.05(4) . . . 4_565 ?
N7 K1 K2 N1 108.53(4) 1_554 . . 4_565 ?
K2 K1 K2 N1 80.31(3) 1_455 . . 4_565 ?
O1 K1 K2 N4 -54.39(6) 4_565 . . 1_554 ?
O3 K1 K2 N4 43.48(4) 1_554 . . 1_554 ?
N10 K1 K2 N4 175.95(4) . . . 1_554 ?
O4 K1 K2 N4 9.66(10) . . . 1_554 ?
N9 K1 K2 N4 113.41(5) 3_656 . . 1_554 ?
N5 K1 K2 N4 -62.81(4) 4_565 . . 1_554 ?
N4 K1 K2 N4 -137.45(5) . . . 1_554 ?
N7 K1 K2 N4 43.13(4) 1_554 . . 1_554 ?
K2 K1 K2 N4 14.91(3) 1_455 . . 1_554 ?
O1 K1 K2 K1 110.71(5) 4_565 . . 1_655 ?
O3 K1 K2 K1 -151.43(3) 1_554 . . 1_655 ?
N10 K1 K2 K1 -18.96(4) . . . 1_655 ?
O4 K1 K2 K1 174.75(9) . . . 1_655 ?
N9 K1 K2 K1 -81.49(4) 3_656 . . 1_655 ?
N5 K1 K2 K1 102.28(3) 4_565 . . 1_655 ?
N4 K1 K2 K1 27.64(3) . . . 1_655 ?
N7 K1 K2 K1 -151.78(3) 1_554 . . 1_655 ?
K2 K1 K2 K1 180.0 1_455 . . 1_655 ?

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
O5 H5B O3 0.84(3) 1.95(3) 2.7882(18) 172(2) 3_657
O4 H4B N3 0.83(3) 2.10(3) 2.910(2) 165(2) 1_455
O4 H4A O5 0.79(3) 2.34(3) 2.992(2) 141(2) 1_455
O5 H5A N4 0.85(3) 2.31(3) 2.974(2) 135(2) .

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988412'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jx001
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Fri Jan 03 15:59:05 2014'
;
_audit_update_record             07.01.2014

_chemical_name_systematic        
'bishydrazinium bis(1-oxidotetrazolyl)-furazane'
_chemical_compound_source        ?
_chemical_name_common            
'bishydrazinium bis(1-oxidotetrazolyl)-furazane'
_chemical_formula_moiety         'C4 N10 O3, 2(H5 N2)'
_chemical_formula_sum            'C4 H10 N14 O3'
_chemical_formula_weight         302.26


_cell_length_a                   3.7659(3)
_cell_length_b                   11.0046(14)
_cell_length_c                   14.3912(16)
_cell_angle_alpha                97.056(10)
_cell_angle_beta                 95.040(8)
_cell_angle_gamma                98.978(9)
_cell_volume                     581.14(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    236
_cell_measurement_reflns_used    877
_cell_measurement_theta_min      4.9220
_cell_measurement_theta_max      29.2110
_cell_special_details            ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_T_max  0.9924
_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      236 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            4048
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         27.00
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992

_reflns_number_total             2518
_reflns_number_gt                1735
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      -0.0189991000
_diffrn_orient_matrix_UB_12      -0.0565070000
_diffrn_orient_matrix_UB_13      0.0195040000
_diffrn_orient_matrix_UB_21      0.0398349000
_diffrn_orient_matrix_UB_22      0.0338568000
_diffrn_orient_matrix_UB_23      0.0459440000
_diffrn_orient_matrix_UB_31      -0.1866872000
_diffrn_orient_matrix_UB_32      0.0015483000
_diffrn_orient_matrix_UB_33      0.0022141000

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  -P1

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'

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0336P)²+0.0000P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2518
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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
O2 O 0.6160(4) 0.41544(14) 0.43717(10) 0.0351(4) Uani 1 1 d . . .
O1 O 0.8654(4) 0.05227(15) 0.37904(11) 0.0431(4) Uani 1 1 d . . .
O3 O 0.8641(4) 0.66431(13) 0.22688(10) 0.0298(4) Uani 1 1 d . . .
N5 N 0.5650(4) 0.29143(16) 0.40053(12) 0.0299(4) Uani 1 1 d . . .
N1 N 0.7557(4) 0.06697(16) 0.29273(12) 0.0272(4) Uani 1 1 d . . .
N2 N 0.7156(5) -0.02577(17) 0.22086(13) 0.0355(5) Uani 1 1 d . . .
N3 N 0.6067(5) 0.02055(17) 0.14511(13) 0.0362(5) Uani 1 1 d . . .
N4 N 0.5762(4) 0.14077(17) 0.16641(12) 0.0314(4) Uani 1 1 d . . .
N6 N 0.7673(4) 0.48914(16) 0.37471(12) 0.0302(4) Uani 1 1 d . . .
N7 N 0.9883(4) 0.56563(15) 0.19132(11) 0.0225(4) Uani 1 1 d . . .
N8 N 1.1478(4) 0.56259(16) 0.11165(11) 0.0269(4) Uani 1 1 d . . .
N9 N 1.2285(4) 0.45047(17) 0.09408(11) 0.0277(4) Uani 1 1 d . . .
N10 N 1.1216(4) 0.38040(16) 0.16005(11) 0.0251(4) Uani 1 1 d . . .
C1 C 0.6695(5) 0.16872(18) 0.25920(14) 0.0222(4) Uani 1 1 d . . .
C2 C 0.6819(5) 0.28753(18) 0.31754(13) 0.0213(4) Uani 1 1 d . . .
C3 C 0.8100(5) 0.41252(18) 0.30131(13) 0.0217(4) Uani 1 1 d . . .
C4 C 0.9699(5) 0.45262(18) 0.22013(13) 0.0211(4) Uani 1 1 d . . .
N11 N 0.8571(5) 0.1646(2) 0.61915(14) 0.0287(4) Uani 1 1 d . . .
N12 N 1.1267(5) 0.2123(2) 0.56091(14) 0.0287(4) Uani 1 1 d . . .
N13 N 0.9484(4) 0.82518(18) 0.01731(15) 0.0254(4) Uani 1 1 d . . .
N14 N 0.6516(4) 0.74475(18) 0.04787(14) 0.0247(4) Uani 1 1 d . . .
H11A H 0.910(6) 0.076(3) 0.6244(18) 0.059(8) Uiso 1 1 d . . .
H12A H 1.061(6) 0.180(2) 0.4995(19) 0.051(8) Uiso 1 1 d . . .
H14C H 0.708(6) 0.735(2) 0.1133(19) 0.046(7) Uiso 1 1 d . . .
H11B H 0.624(6) 0.165(2) 0.5949(16) 0.045(7) Uiso 1 1 d . . .
H14B H 0.426(6) 0.775(2) 0.0421(15) 0.038(6) Uiso 1 1 d . . .
H13B H 0.932(6) 0.900(3) 0.0429(18) 0.046(7) Uiso 1 1 d . . .
H12B H 1.123(6) 0.292(3) 0.5663(17) 0.045(7) Uiso 1 1 d . . .
H13A H 0.902(5) 0.820(2) -0.0469(19) 0.045(7) Uiso 1 1 d . . .
H14A H 0.633(6) 0.665(3) 0.0107(18) 0.051(8) Uiso 1 1 d . . .
H11C H 0.907(6) 0.212(3) 0.6748(19) 0.045(7) 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
O2 N5 1.379(2) . ?
O2 N6 1.384(2) . ?
O1 N1 1.312(2) . ?
O3 N7 1.313(2) . ?
N5 C2 1.307(3) . ?
N1 N2 1.341(2) . ?
N1 C1 1.346(2) . ?
N2 N3 1.319(2) . ?
N3 N4 1.346(2) . ?
N4 C1 1.336(2) . ?
N6 C3 1.306(2) . ?
N7 N8 1.339(2) . ?
N7 C4 1.352(2) . ?
N8 N9 1.316(2) . ?
N9 N10 1.345(2) . ?
N10 C4 1.329(2) . ?
C1 C2 1.456(3) . ?
C2 C3 1.439(3) . ?
C3 C4 1.445(3) . ?
N11 N12 1.449(3) . ?
N11 H11A 1.03(3) . ?
N11 H11B 0.92(2) . ?
N11 H11C 0.89(3) . ?
N12 H12A 0.91(3) . ?
N12 H12B 0.87(3) . ?
N13 N14 1.449(2) . ?
N13 H13B 0.87(3) . ?
N13 H13A 0.92(3) . ?
N14 H14C 0.97(3) . ?
N14 H14B 0.96(2) . ?
N14 H14A 0.96(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
N5 O2 N6 110.99(14) . . ?
C2 N5 O2 105.90(16) . . ?
O1 N1 N2 121.95(17) . . ?
O1 N1 C1 129.51(17) . . ?
N2 N1 C1 108.55(16) . . ?
N3 N2 N1 106.15(17) . . ?
N2 N3 N4 111.11(17) . . ?
C1 N4 N3 105.62(17) . . ?
C3 N6 O2 105.72(16) . . ?
O3 N7 N8 121.82(16) . . ?
O3 N7 C4 130.03(17) . . ?
N8 N7 C4 108.07(16) . . ?
N9 N8 N7 106.48(16) . . ?
N8 N9 N10 110.97(16) . . ?
C4 N10 N9 105.81(16) . . ?
N4 C1 N1 108.57(18) . . ?
N4 C1 C2 127.65(18) . . ?
N1 C1 C2 123.78(17) . . ?
N5 C2 C3 108.65(18) . . ?
N5 C2 C1 120.27(18) . . ?
C3 C2 C1 131.08(18) . . ?
N6 C3 C2 108.74(17) . . ?
N6 C3 C4 123.27(18) . . ?
C2 C3 C4 127.97(18) . . ?
N10 C4 N7 108.66(17) . . ?
N10 C4 C3 124.07(18) . . ?
N7 C4 C3 127.26(18) . . ?
N12 N11 H11A 102.8(13) . . ?
N12 N11 H11B 113.7(15) . . ?
H11A N11 H11B 113(2) . . ?
N12 N11 H11C 106.4(15) . . ?
H11A N11 H11C 110(2) . . ?
H11B N11 H11C 110(2) . . ?
N11 N12 H12A 110.4(15) . . ?
N11 N12 H12B 104.8(16) . . ?
H12A N12 H12B 108(2) . . ?
N14 N13 H13B 105.0(16) . . ?
N14 N13 H13A 106.5(14) . . ?
H13B N13 H13A 109(2) . . ?
N13 N14 H14C 109.7(13) . . ?
N13 N14 H14B 113.5(13) . . ?
H14C N14 H14B 108.0(18) . . ?
N13 N14 H14A 106.5(14) . . ?
H14C N14 H14A 108(2) . . ?
H14B N14 H14A 110.9(18) . . ?

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
N6 O2 N5 C2 0.1(2) . . . . ?
O1 N1 N2 N3 -179.41(17) . . . . ?
C1 N1 N2 N3 0.1(2) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N2 N3 N4 C1 -0.2(2) . . . . ?
N5 O2 N6 C3 -0.2(2) . . . . ?
O3 N7 N8 N9 -177.93(14) . . . . ?
C4 N7 N8 N9 -1.01(18) . . . . ?
N7 N8 N9 N10 0.64(19) . . . . ?
N8 N9 N10 C4 -0.01(19) . . . . ?
N3 N4 C1 N1 0.2(2) . . . . ?
N3 N4 C1 C2 -179.97(18) . . . . ?
O1 N1 C1 N4 179.23(18) . . . . ?
N2 N1 C1 N4 -0.2(2) . . . . ?
O1 N1 C1 C2 -0.6(3) . . . . ?
N2 N1 C1 C2 -179.99(17) . . . . ?
O2 N5 C2 C3 0.0(2) . . . . ?
O2 N5 C2 C1 179.56(15) . . . . ?
N4 C1 C2 N5 138.8(2) . . . . ?
N1 C1 C2 N5 -41.5(3) . . . . ?
N4 C1 C2 C3 -41.8(3) . . . . ?
N1 C1 C2 C3 138.0(2) . . . . ?
O2 N6 C3 C2 0.18(19) . . . . ?
O2 N6 C3 C4 -178.49(16) . . . . ?
N5 C2 C3 N6 -0.1(2) . . . . ?
C1 C2 C3 N6 -179.63(18) . . . . ?
N5 C2 C3 C4 178.49(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
N9 N10 C4 N7 -0.63(19) . . . . ?
N9 N10 C4 C3 178.57(16) . . . . ?
O3 N7 C4 N10 177.61(15) . . . . ?
N8 N7 C4 N10 1.03(19) . . . . ?
O3 N7 C4 C3 -1.6(3) . . . . ?
N8 N7 C4 C3 -178.13(17) . . . . ?
N6 C3 C4 N10 157.41(17) . . . . ?
C2 C3 C4 N10 -21.0(3) . . . . ?
N6 C3 C4 N7 -23.5(3) . . . . ?
C2 C3 C4 N7 158.05(17) . . . . ?

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
N11 H11A O1 1.03(3) 1.76(3) 2.753(3) 161(2) 2_756
N11 H11A N1 1.03(3) 2.51(3) 3.444(3) 149.7(19) 2_756
N11 H11A N2 1.03(3) 2.69(3) 3.348(3) 121.2(18) 2_756
N12 H12A O1 0.91(3) 2.09(3) 2.966(3) 161(2) .
N14 H14C O3 0.97(3) 1.98(3) 2.912(2) 161(2) .
N14 H14C N7 0.97(3) 2.60(2) 3.328(2) 131.8(18) .
N11 H11B N12 0.92(2) 2.05(2) 2.949(3) 165(2) 1_455
N14 H14B N13 0.96(2) 1.98(2) 2.935(2) 173.8(19) 1_455
N13 H13B N3 0.87(3) 2.40(3) 3.157(3) 145(2) 1_565
N12 H12B N6 0.87(3) 2.41(3) 3.254(3) 162(2) 2_766
N13 H13A N4 0.92(3) 2.50(2) 3.254(2) 139.3(18) 2_665
N13 H13A N10 0.92(3) 2.56(3) 3.159(3) 123.0(19) 2_765
N14 H14A N9 0.96(3) 2.01(3) 2.895(3) 153(2) 2_765
N11 H11C O3 0.89(3) 1.88(3) 2.740(3) 161(2) 2_766

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988413'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jx020
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Thu Jan 23 19:12:07 2014'
;
_audit_update_record             24.01.2014

_chemical_name_systematic        
'bisammonium 4,5-bis(1-oxido-tetrazolyl)furazane'
_chemical_compound_source        ?
_chemical_name_common            
'bisammonium 4,5-bis(1-oxido-tetrazolyl)furazane'
_chemical_formula_moiety         'C4 N10 O3, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N12 O3'
_chemical_formula_weight         272.22


_cell_length_a                   14.5573(13)
_cell_length_b                   7.5523(7)
_cell_length_c                   19.5093(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2144.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    927
_cell_measurement_theta_min      4.3880
_cell_measurement_theta_max      24.5920
_cell_special_details            ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_T_max  0.9943
_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      293 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            5832
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         27.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996

_reflns_number_total             2335
_reflns_number_gt                1518
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0165914000
_diffrn_orient_matrix_UB_12      0.0637218000
_diffrn_orient_matrix_UB_13      -0.0236381000
_diffrn_orient_matrix_UB_21      0.0393465000
_diffrn_orient_matrix_UB_22      -0.0531950000
_diffrn_orient_matrix_UB_23      -0.0061277000
_diffrn_orient_matrix_UB_31      -0.0234853000
_diffrn_orient_matrix_UB_32      -0.0439348000
_diffrn_orient_matrix_UB_33      -0.0269275000

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  ' -P 2ac 2ab'

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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0230P)²+0.0000P] where P=(Fo²+2Fc²)/3'


_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2335
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.18115(12) 0.0635(2) 0.49699(7) 0.0342(4) Uani 1 1 d . . .
O2 O 0.25735(12) 0.2400(2) 0.29856(7) 0.0384(5) Uani 1 1 d . . .
O3 O 0.14600(12) -0.0560(2) 0.12929(7) 0.0344(4) Uani 1 1 d . . .
N1 N 0.12097(14) -0.0305(2) 0.46114(8) 0.0266(5) Uani 1 1 d . . .
N2 N 0.06659(15) -0.1514(3) 0.49092(9) 0.0352(5) Uani 1 1 d . . .
N3 N 0.01410(16) -0.2161(3) 0.44178(9) 0.0388(5) Uani 1 1 d . . .
N4 N 0.03371(15) -0.1383(3) 0.38090(8) 0.0333(5) Uani 1 1 d . . .
N5 N 0.22540(15) 0.1687(3) 0.35948(8) 0.0341(5) Uani 1 1 d . . .
N6 N 0.20054(14) 0.1950(3) 0.24496(8) 0.0330(5) Uani 1 1 d . . .
N7 N 0.06968(13) -0.0289(2) 0.16500(8) 0.0258(4) Uani 1 1 d . . .
N8 N -0.01364(15) -0.0702(3) 0.14034(9) 0.0328(5) Uani 1 1 d . . .
N9 N -0.07311(14) -0.0291(3) 0.18861(9) 0.0352(5) Uani 1 1 d . . .
N10 N -0.02993(14) 0.0359(3) 0.24412(9) 0.0321(5) Uani 1 1 d . . .
C1 C 0.10085(16) -0.0231(3) 0.39388(9) 0.0238(5) Uani 1 1 d . . .
C2 C 0.15071(16) 0.0816(3) 0.34353(10) 0.0232(5) Uani 1 1 d . . .
C3 C 0.13492(16) 0.0988(3) 0.27137(10) 0.0247(5) Uani 1 1 d . . .
C4 C 0.05950(17) 0.0349(3) 0.22899(10) 0.0249(5) Uani 1 1 d . . .
N12 N 0.63901(18) 0.4328(3) 0.01108(11) 0.0319(5) Uani 1 1 d . . .
N11 N 0.16207(17) 0.5659(3) 0.13689(11) 0.0324(5) Uani 1 1 d . . .
H11C H 0.162(2) 0.692(4) 0.1303(11) 0.055(8) Uiso 1 1 d . . .
H12D H 0.648(2) 0.308(4) 0.0073(12) 0.064(9) Uiso 1 1 d . . .
H12B H 0.623(2) 0.474(4) -0.0301(14) 0.059(9) Uiso 1 1 d . . .
H11A H 0.154(2) 0.518(4) 0.0902(15) 0.078(10) Uiso 1 1 d . . .
H11B H 0.116(2) 0.536(4) 0.1706(15) 0.079(10) Uiso 1 1 d . . .
H12A H 0.591(2) 0.459(4) 0.0453(14) 0.073(10) Uiso 1 1 d . . .
H11D H 0.220(2) 0.528(4) 0.1518(12) 0.061(9) Uiso 1 1 d . . .
H12C H 0.696(3) 0.490(4) 0.0245(14) 0.077(11) 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 N1 1.327(2) . ?
O2 N6 1.376(2) . ?
O2 N5 1.385(2) . ?
O3 N7 1.327(2) . ?
N1 N2 1.341(3) . ?
N1 C1 1.346(2) . ?
N2 N3 1.320(3) . ?
N3 N4 1.356(2) . ?
N4 C1 1.333(3) . ?
N5 C2 1.308(3) . ?
N6 C3 1.306(3) . ?
N7 N8 1.342(3) . ?
N7 C4 1.346(3) . ?
N8 N9 1.316(3) . ?
N9 N10 1.345(2) . ?
N10 C4 1.335(3) . ?
C1 C2 1.455(3) . ?
C2 C3 1.432(3) . ?
C3 C4 1.457(3) . ?
N12 H12D 0.95(3) . ?
N12 H12B 0.89(3) . ?
N12 H12A 0.99(3) . ?
N12 H12C 0.97(4) . ?
N11 H11C 0.96(3) . ?
N11 H11A 0.99(3) . ?
N11 H11B 0.97(3) . ?
N11 H11D 0.94(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
N6 O2 N5 110.75(16) . . ?
O1 N1 N2 121.72(17) . . ?
O1 N1 C1 129.45(19) . . ?
N2 N1 C1 108.80(19) . . ?
N3 N2 N1 106.20(16) . . ?
N2 N3 N4 110.75(19) . . ?
C1 N4 N3 105.71(17) . . ?
C2 N5 O2 105.69(16) . . ?
C3 N6 O2 106.09(16) . . ?
O3 N7 N8 122.18(16) . . ?
O3 N7 C4 129.36(19) . . ?
N8 N7 C4 108.43(19) . . ?
N9 N8 N7 106.44(16) . . ?
N8 N9 N10 110.78(19) . . ?
C4 N10 N9 106.00(18) . . ?
N4 C1 N1 108.54(19) . . ?
N4 C1 C2 126.32(18) . . ?
N1 C1 C2 124.9(2) . . ?
N5 C2 C3 108.74(19) . . ?
N5 C2 C1 121.83(18) . . ?
C3 C2 C1 129.3(2) . . ?
N6 C3 C2 108.7(2) . . ?
N6 C3 C4 120.78(19) . . ?
C2 C3 C4 130.4(2) . . ?
N10 C4 N7 108.3(2) . . ?
N10 C4 C3 127.40(19) . . ?
N7 C4 C3 124.2(2) . . ?
H12D N12 H12B 108(2) . . ?
H12D N12 H12A 110(2) . . ?
H12B N12 H12A 111(2) . . ?
H12D N12 H12C 111(3) . . ?
H12B N12 H12C 108(2) . . ?
H12A N12 H12C 109(2) . . ?
H11C N11 H11A 104(2) . . ?
H11C N11 H11B 109(2) . . ?
H11A N11 H11B 117(2) . . ?
H11C N11 H11D 110(2) . . ?
H11A N11 H11D 107(2) . . ?
H11B N11 H11D 110(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
O1 N1 N2 N3 178.32(18) . . . . ?
C1 N1 N2 N3 0.0(2) . . . . ?
N1 N2 N3 N4 -0.2(2) . . . . ?
N2 N3 N4 C1 0.3(3) . . . . ?
N6 O2 N5 C2 0.1(2) . . . . ?
N5 O2 N6 C3 0.1(2) . . . . ?
O3 N7 N8 N9 179.12(18) . . . . ?
C4 N7 N8 N9 1.0(2) . . . . ?
N7 N8 N9 N10 -0.7(2) . . . . ?
N8 N9 N10 C4 0.2(2) . . . . ?
N3 N4 C1 N1 -0.3(2) . . . . ?
N3 N4 C1 C2 174.3(2) . . . . ?
O1 N1 C1 N4 -177.95(19) . . . . ?
N2 N1 C1 N4 0.2(2) . . . . ?
O1 N1 C1 C2 7.3(4) . . . . ?
N2 N1 C1 C2 -174.5(2) . . . . ?
O2 N5 C2 C3 -0.3(2) . . . . ?
O2 N5 C2 C1 175.41(19) . . . . ?
N4 C1 C2 N5 -168.4(2) . . . . ?
N1 C1 C2 N5 5.4(4) . . . . ?
N4 C1 C2 C3 6.4(4) . . . . ?
N1 C1 C2 C3 -179.9(2) . . . . ?
O2 N6 C3 C2 -0.3(2) . . . . ?
O2 N6 C3 C4 177.10(18) . . . . ?
N5 C2 C3 N6 0.4(3) . . . . ?
C1 C2 C3 N6 -174.9(2) . . . . ?
N5 C2 C3 C4 -176.7(2) . . . . ?
C1 C2 C3 C4 8.1(4) . . . . ?
N9 N10 C4 N7 0.4(3) . . . . ?
N9 N10 C4 C3 177.5(2) . . . . ?
O3 N7 C4 N10 -178.85(19) . . . . ?
N8 N7 C4 N10 -0.9(3) . . . . ?
O3 N7 C4 C3 4.0(4) . . . . ?
N8 N7 C4 C3 -178.0(2) . . . . ?
N6 C3 C4 N10 -135.4(2) . . . . ?
C2 C3 C4 N10 41.3(4) . . . . ?
N6 C3 C4 N7 41.1(3) . . . . ?
C2 C3 C4 N7 -142.1(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
N11 H11C O3 0.96(3) 1.91(3) 2.869(3) 170(2) 1_565
N11 H11C N7 0.96(3) 2.59(3) 3.388(3) 141(2) 1_565
N12 H12D O1 0.95(3) 1.91(3) 2.860(3) 173(3) 6_656
N12 H12D N1 0.95(3) 2.66(3) 3.551(3) 156(2) 6_656
N12 H12B O3 0.89(3) 2.06(3) 2.894(3) 155(3) 3
N11 H11A O1 0.99(3) 1.96(3) 2.912(3) 161(3) 8_565
N11 H11A N2 0.99(3) 2.52(3) 3.234(3) 129(2) 8_565
N11 H11A N1 0.99(3) 2.56(3) 3.491(3) 156(2) 8_565
N11 H11B N10 0.97(3) 2.08(3) 3.023(3) 164(2) 4
N12 H12A N8 0.99(3) 2.18(3) 3.113(3) 157(2) 7_665
N11 H11D O3 0.94(3) 2.10(3) 2.945(3) 150(2) 7_665
N11 H11D N6 0.94(3) 2.50(3) 3.065(3) 119(2) 7_665
N12 H12C O1 0.97(4) 1.92(4) 2.802(3) 150(2) 4_655
N12 H12C N1 0.97(4) 2.69(4) 3.547(3) 148(2) 4_655

_geom_special_details            ?



_database_code_depnum_ccdc_archive 'CCDC 988414'
