#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:36:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180147 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/44/7104405.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7104405
loop_
_publ_author_name
'Wang, Ruihu'
'Guo, Yong'
'Zeng, Zhuo'
'Shreeve, Jean'ne M'
_publ_section_title
;
 Nitrogen-rich nitroguanidyl-functionalized tetrazolate energetic
 salts.
;
_journal_issue                   19
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2697
_journal_page_last               2699
_journal_paper_doi               10.1039/b823157e
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C4 H8 N7 O2 1+, C2 H3 N8 O2 1-, H2 O1'
_chemical_formula_sum            'C6 H13 N15 O5'
_chemical_formula_weight         375.31
_chemical_name_common
;
5-(nitroimino)hexahydroimidazo(4,5)imidazol-2-iminium 5-(2-
nitroguanidino)tetrazol-1-ide hydrate
;
_chemical_name_systematic
;
5-(nitroimino)hexahydroimidazo[4,5]imidazol-2-iminium
5-(2-nitroguanidino)tetrazol-1-ide hydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-07-31
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                102.566(2)
_cell_angle_beta                 98.514(2)
_cell_angle_gamma                108.446(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2741(4)
_cell_length_b                   8.4920(4)
_cell_length_c                   11.3507(8)
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.287
_cell_measurement_theta_min      2.667
_cell_volume                     717.90(7)
_computing_cell_refinement       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_reduction
;
Bruker SAINT v7.34A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7955
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2004/1 (Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.3439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                3173
_reflns_number_total             3522
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b823157e.txt
_cod_data_source_block           shrv07
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.03243(15) 0.29625(15) 0.37750(11) 0.0161(2) Uani 1 1 d . . .
N2 N -0.03658(14) 0.40729(14) 0.34431(9) 0.0194(2) Uani 1 1 d . . .
N3 N -0.07664(14) 0.35343(15) 0.21892(10) 0.0214(2) Uani 1 1 d . . .
N4 N -0.03300(14) 0.21898(15) 0.18158(10) 0.0221(2) Uani 1 1 d . . .
N5 N 0.03854(14) 0.17884(14) 0.28068(9) 0.0205(2) Uani 1 1 d . . .
N6 N 0.09081(14) 0.30810(13) 0.50139(9) 0.0174(2) Uani 1 1 d . . .
H6A H 0.0773 0.3893 0.5577 0.021 Uiso 1 1 calc R . .
N7 N 0.19360(14) 0.08292(14) 0.46286(9) 0.0191(2) Uani 1 1 d . . .
H7A H 0.1620 0.0685 0.3826 0.023 Uiso 1 1 calc R . .
H7B H 0.2432 0.0158 0.4900 0.023 Uiso 1 1 calc R . .
C7 C 0.16678(15) 0.20454(15) 0.54218(11) 0.0159(2) Uani 1 1 d . . .
N8 N 0.20515(14) 0.24601(13) 0.66927(9) 0.0183(2) Uani 1 1 d . . .
N9 N 0.28506(14) 0.15728(14) 0.72335(10) 0.0192(2) Uani 1 1 d . . .
O9A O 0.31761(14) 0.20065(13) 0.83919(8) 0.0263(2) Uani 1 1 d . . .
O9B O 0.32838(13) 0.03966(13) 0.66668(9) 0.0265(2) Uani 1 1 d . . .
C10 C 0.42624(15) 0.45018(15) 1.29863(11) 0.0167(2) Uani 1 1 d . . .
N11 N 0.50290(14) 0.34807(14) 1.33779(10) 0.0197(2) Uani 1 1 d . . .
H11A H 0.5479 0.3618 1.4162 0.024 Uiso 1 1 calc R . .
C12 C 0.50304(15) 0.21255(15) 1.23593(11) 0.0181(2) Uani 1 1 d . . .
H12A H 0.6230 0.2096 1.2364 0.022 Uiso 1 1 calc R . .
N13 N 0.37516(14) 0.04394(13) 1.22550(9) 0.0183(2) Uani 1 1 d . . .
H13A H 0.3776 -0.0123 1.2819 0.022 Uiso 1 1 calc R . .
N14 N 0.12737(15) -0.16654(14) 1.08036(10) 0.0232(2) Uani 1 1 d . . .
H14A H 0.1185 -0.2391 1.1260 0.028 Uiso 1 1 calc R . .
H14B H 0.0516 -0.1963 1.0089 0.028 Uiso 1 1 calc R . .
C14 C 0.25326(16) -0.01436(15) 1.11874(10) 0.0166(2) Uani 1 1 d . . .
N15 N 0.27417(14) 0.10450(13) 1.05592(9) 0.0191(2) Uani 1 1 d . . .
H15A H 0.2046 0.0903 0.9847 0.023 Uiso 1 1 calc R . .
C16 C 0.42567(16) 0.25924(15) 1.11992(11) 0.0181(2) Uani 1 1 d . . .
H16A H 0.5114 0.2874 1.0672 0.022 Uiso 1 1 calc R . .
N17 N 0.38186(14) 0.40795(13) 1.17507(10) 0.0185(2) Uani 1 1 d . . .
H17A H 0.3326 0.4625 1.1324 0.022 Uiso 1 1 calc R . .
N18 N 0.40955(14) 0.57332(13) 1.38899(10) 0.0191(2) Uani 1 1 d . . .
N19 N 0.33859(14) 0.68264(14) 1.35440(10) 0.0209(2) Uani 1 1 d . . .
O20 O 0.32381(15) 0.78987(13) 1.44077(10) 0.0332(3) Uani 1 1 d . . .
O21 O 0.29330(14) 0.67859(13) 1.24363(9) 0.0282(2) Uani 1 1 d . . .
O1S O 0.21659(15) 0.47763(14) 0.95262(9) 0.0296(2) Uani 1 1 d D . .
H1SA H 0.236(2) 0.3973(18) 0.9031(11) 0.045(6) Uiso 1 1 d D . .
H1SB H 0.168(2) 0.524(2) 0.9044(12) 0.044(5) Uiso 1 1 d D . .
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_
_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 C1 N2 113.01(10) . . ?
N5 C1 N6 125.46(11) . . ?
N2 C1 N6 121.53(11) . . ?
C1 N2 N3 103.64(10) . . ?
N4 N3 N2 109.78(10) . . ?
N3 N4 N5 109.97(10) . . ?
C1 N5 N4 103.60(10) . . ?
C7 N6 C1 125.00(10) . . ?
C7 N6 H6A 117.5 . . ?
C1 N6 H6A 117.5 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N7 C7 N6 120.43(11) . . ?
N7 C7 N8 128.66(11) . . ?
N6 C7 N8 110.91(10) . . ?
N9 N8 C7 117.77(10) . . ?
O9B N9 O9A 120.09(10) . . ?
O9B N9 N8 124.73(10) . . ?
O9A N9 N8 115.17(10) . . ?
N17 C10 N11 111.36(10) . . ?
N17 C10 N18 133.04(11) . . ?
N11 C10 N18 115.60(10) . . ?
C10 N11 C12 111.86(10) . . ?
C10 N11 H11A 124.1 . . ?
C12 N11 H11A 124.1 . . ?
N11 C12 N13 113.23(10) . . ?
N11 C12 C16 102.63(9) . . ?
N13 C12 C16 102.96(9) . . ?
N11 C12 H12A 112.4 . . ?
N13 C12 H12A 112.4 . . ?
C16 C12 H12A 112.4 . . ?
C14 N13 C12 111.05(10) . . ?
C14 N13 H13A 124.5 . . ?
C12 N13 H13A 124.5 . . ?
C14 N14 H14A 120.0 . . ?
C14 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N14 C14 N13 124.92(11) . . ?
N14 C14 N15 123.73(11) . . ?
N13 C14 N15 111.34(11) . . ?
C14 N15 C16 111.48(10) . . ?
C14 N15 H15A 124.3 . . ?
C16 N15 H15A 124.3 . . ?
N15 C16 N17 113.82(10) . . ?
N15 C16 C12 102.82(9) . . ?
N17 C16 C12 102.83(9) . . ?
N15 C16 H16A 112.2 . . ?
N17 C16 H16A 112.2 . . ?
C12 C16 H16A 112.2 . . ?
C10 N17 C16 111.07(10) . . ?
C10 N17 H17A 124.5 . . ?
C16 N17 H17A 124.5 . . ?
N19 N18 C10 117.85(10) . . ?
O20 N19 O21 122.34(11) . . ?
O20 N19 N18 114.86(11) . . ?
O21 N19 N18 122.79(11) . . ?
H1SA O1S H1SB 104.47(17) . . ?
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
C1 N5 1.3327(15) . ?
C1 N2 1.3375(15) . ?
C1 N6 1.3884(15) . ?
N2 N3 1.3512(14) . ?
N3 N4 1.3074(16) . ?
N4 N5 1.3526(14) . ?
N6 C7 1.3504(15) . ?
N6 H6A 0.8800 . ?
N7 C7 1.3138(15) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
C7 N8 1.3705(15) . ?
N8 N9 1.3335(14) . ?
N9 O9B 1.2470(14) . ?
N9 O9A 1.2485(13) . ?
C10 N17 1.3325(15) . ?
C10 N11 1.3357(15) . ?
C10 N18 1.3532(16) . ?
N11 C12 1.4434(15) . ?
N11 H11A 0.8800 . ?
C12 N13 1.4540(16) . ?
C12 C16 1.5618(16) . ?
C12 H12A 1.0000 . ?
N13 C14 1.3386(15) . ?
N13 H13A 0.8800 . ?
N14 C14 1.3091(16) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
C14 N15 1.3403(15) . ?
N15 C16 1.4486(16) . ?
N15 H15A 0.8800 . ?
C16 N17 1.4598(15) . ?
C16 H16A 1.0000 . ?
N17 H17A 0.8800 . ?
N18 N19 1.3402(14) . ?
N19 O20 1.2340(15) . ?
N19 O21 1.2473(14) . ?
O1S H1SA 0.8601(10) . ?
O1S H1SB 0.8601(10) . ?
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
N6 H6A N2 0.88 1.99 2.8613(15) 168.1 2_566
N7 H7B O9B 0.88 1.97 2.5683(14) 124.2 .
N7 H7B O20 0.88 2.21 2.9869(14) 146.7 1_544
N11 H11A N18 0.88 2.11 2.9524(15) 161.3 2_668
N11 H11A O20 0.88 2.59 3.3201(15) 141.6 2_668
N13 H13A O21 0.88 2.41 3.0193(14) 126.5 1_545
N13 H13A O9B 0.88 2.51 2.9343(14) 110.2 2_657
N14 H14A O21 0.88 2.20 2.9152(15) 138.2 1_545
N14 H14B N4 0.88 2.11 2.8573(16) 142.7 2_556
N15 H15A O9A 0.88 2.25 2.7924(13) 119.8 .
N15 H15A N4 0.88 2.68 3.2421(15) 123.0 2_556
N17 H17A O21 0.88 2.14 2.6231(14) 114.3 .
N17 H17A O1S 0.88 2.17 2.9555(14) 148.2 .
O1S H1SA O9A 0.8601(10) 2.023(5) 2.8520(15) 161.6(15) .
O1S H1SA N8 0.8601(10) 2.620(9) 3.3558(14) 144.2(13) .
O1S H1SB N3 0.8601(10) 2.108(3) 2.9647(14) 173.8(19) 2_566
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
N5 C1 N2 N3 0.51(14) . . . . ?
N6 C1 N2 N3 -179.84(11) . . . . ?
C1 N2 N3 N4 -0.11(13) . . . . ?
N2 N3 N4 N5 -0.30(14) . . . . ?
N2 C1 N5 N4 -0.68(14) . . . . ?
N6 C1 N5 N4 179.69(11) . . . . ?
N3 N4 N5 C1 0.59(13) . . . . ?
N5 C1 N6 C7 1.8(2) . . . . ?
N2 C1 N6 C7 -177.83(11) . . . . ?
C1 N6 C7 N7 1.25(19) . . . . ?
C1 N6 C7 N8 -178.33(11) . . . . ?
N7 C7 N8 N9 2.16(19) . . . . ?
N6 C7 N8 N9 -178.32(10) . . . . ?
C7 N8 N9 O9B 0.40(18) . . . . ?
C7 N8 N9 O9A 179.72(10) . . . . ?
N17 C10 N11 C12 -4.73(15) . . . . ?
N18 C10 N11 C12 175.52(10) . . . . ?
C10 N11 C12 N13 -104.92(12) . . . . ?
C10 N11 C12 C16 5.33(13) . . . . ?
N11 C12 N13 C14 116.08(11) . . . . ?
C16 C12 N13 C14 6.02(13) . . . . ?
C12 N13 C14 N14 175.83(11) . . . . ?
C12 N13 C14 N15 -5.17(14) . . . . ?
N14 C14 N15 C16 -179.21(11) . . . . ?
N13 C14 N15 C16 1.78(14) . . . . ?
C14 N15 C16 N17 -108.44(11) . . . . ?
C14 N15 C16 C12 2.00(13) . . . . ?
N11 C12 C16 N15 -122.42(10) . . . . ?
N13 C12 C16 N15 -4.62(11) . . . . ?
N11 C12 C16 N17 -3.95(11) . . . . ?
N13 C12 C16 N17 113.84(10) . . . . ?
N11 C10 N17 C16 1.76(14) . . . . ?
N18 C10 N17 C16 -178.55(12) . . . . ?
N15 C16 N17 C10 112.02(11) . . . . ?
C12 C16 N17 C10 1.58(13) . . . . ?
N17 C10 N18 N19 -1.8(2) . . . . ?
N11 C10 N18 N19 177.88(11) . . . . ?
C10 N18 N19 O20 178.70(11) . . . . ?
C10 N18 N19 O21 -2.38(18) . . . . ?
