#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:37:30 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240221.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_7240221
loop_
_publ_author_name
'Xu, Xin'
'Chen, Dong'
'Li, Hongzhen'
'Yan, Mi'
'Xiong, Ying'
'Zhao, Haixia'
'Xu, Rong'
_publ_section_title
;
 Crystal structure evolution of an energetic compound dihydroxylammonium
 5,5′-bistetrazole-1,1′-diolate induced by solvents
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              11939
_journal_page_last               11944
_journal_paper_doi               10.1039/D0RA01182G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         '[NH(CH3CCH3)OH+] [C2HO2N4-].H2O'
_chemical_formula_sum            'C5 H11 N9 O4'
_chemical_formula_weight         261.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-01-18 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                73.627(2)
_cell_angle_beta                 82.716(2)
_cell_angle_gamma                83.323(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8110(5)
_cell_length_b                   7.3961(5)
_cell_length_c                   11.6431(9)
_cell_measurement_reflns_used    4209
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.810
_cell_measurement_theta_min      5.762
_cell_volume                     556.19(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7339
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.881
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: AC/MT'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0464P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1758
_reflns_number_total             2180
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01182g2.cif
_cod_data_source_block           mo_d8v19308_0m
_cod_depositor_comments
'Adding full bibliography for 7240219--7240221.cif.'
_cod_database_code               7240221
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7706(3) 0.51003(17) 0.60577(12) 0.0625(5) Uani 1 1 d . . . . .
O2 O 0.8007(3) 1.23025(17) 0.53324(12) 0.0553(4) Uani 1 1 d D . . . .
N1 N 0.7433(2) 0.66422(19) 0.51479(13) 0.0387(4) Uani 1 1 d . . . . .
N2 N 0.7172(3) 0.6576(2) 0.40465(14) 0.0475(4) Uani 1 1 d . . . . .
N3 N 0.6979(3) 0.8326(2) 0.33983(14) 0.0491(4) Uani 1 1 d . . . . .
N4 N 0.7118(2) 0.9515(2) 0.40668(13) 0.0426(4) Uani 1 1 d . . . . .
N5 N 0.7904(2) 1.07596(19) 0.62465(13) 0.0369(4) Uani 1 1 d . . . . .
N6 N 0.8094(3) 1.0765(2) 0.73719(14) 0.0464(4) Uani 1 1 d . . . . .
N7 N 0.7951(3) 0.9030(2) 0.80242(14) 0.0491(4) Uani 1 1 d . . . . .
N8 N 0.7681(2) 0.7911(2) 0.73360(13) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.7406(3) 0.8438(2) 0.51662(15) 0.0329(4) Uani 1 1 d . . . . .
C2 C 0.7658(2) 0.9012(2) 0.62219(14) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.794(5) 1.336(4) 0.565(3) 0.125(12) Uiso 1 1 d D . . . .
O3 O 0.4604(2) 0.4254(2) 0.89037(13) 0.0598(4) Uani 1 1 d D . . . .
N9 N 0.6609(2) 0.4347(2) 0.87076(13) 0.0408(4) Uani 1 1 d . . . . .
C3 C 0.7783(3) 0.3113(2) 0.93344(15) 0.0398(5) Uani 1 1 d . . . . .
C4 C 0.9928(4) 0.3343(4) 0.9047(2) 0.0592(6) Uani 1 1 d . . . . .
C5 C 0.7035(5) 0.1496(3) 1.0290(2) 0.0576(6) Uani 1 1 d . . . . .
H5A H 0.776(5) 0.131(4) 1.094(3) 0.096(10) Uiso 1 1 d . . . . .
H5B H 0.722(5) 0.040(5) 1.001(3) 0.110(11) Uiso 1 1 d . . . . .
H5C H 0.570(5) 0.176(4) 1.050(3) 0.088(10) Uiso 1 1 d . . . . .
H4A H 1.017(4) 0.464(4) 0.853(2) 0.080(8) Uiso 1 1 d . . . . .
H4B H 1.061(4) 0.308(4) 0.980(2) 0.079(8) Uiso 1 1 d . . . . .
H4C H 1.049(5) 0.239(4) 0.872(3) 0.098(10) Uiso 1 1 d . . . . .
H9 H 0.710(4) 0.539(4) 0.814(2) 0.074(7) Uiso 1 1 d . . . . .
H3 H 0.409(4) 0.504(3) 0.829(2) 0.084(9) Uiso 1 1 d D . . . .
O4 O 0.3030(3) 0.6498(2) 0.71348(14) 0.0616(5) Uani 1 1 d . . . . .
H4D H 0.303(4) 0.770(5) 0.673(3) 0.088(9) Uiso 1 1 d . . . . .
H4E H 0.283(5) 0.585(5) 0.664(3) 0.111(11) Uiso 1 1 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 O2 H2 108(2) . . ?
N2 N1 O1 123.11(14) . . ?
N2 N1 C1 109.57(14) . . ?
O1 N1 C1 127.32(15) . . ?
N3 N2 N1 106.16(14) . . ?
N2 N3 N4 110.50(14) . . ?
C1 N4 N3 106.31(14) . . ?
O2 N5 C2 128.10(14) . . ?
O2 N5 N6 122.49(14) . . ?
C2 N5 N6 109.39(14) . . ?
N7 N6 N5 106.10(14) . . ?
N6 N7 N8 110.51(14) . . ?
C2 N8 N7 106.42(14) . . ?
N4 C1 N1 107.47(15) . . ?
N4 C1 C2 128.63(15) . . ?
N1 C1 C2 123.91(15) . . ?
N8 C2 N5 107.58(15) . . ?
N8 C2 C1 126.59(14) . . ?
N5 C2 C1 125.83(15) . . ?
N9 O3 H3 107.3(18) . . ?
C3 N9 O3 121.40(16) . . ?
C3 N9 H9 120.3(16) . . ?
O3 N9 H9 118.2(16) . . ?
N9 C3 C5 121.4(2) . . ?
N9 C3 C4 117.07(18) . . ?
C5 C3 C4 121.6(2) . . ?
C3 C4 H4A 111.3(15) . . ?
C3 C4 H4B 110.8(15) . . ?
H4A C4 H4B 110(2) . . ?
C3 C4 H4C 107.9(19) . . ?
H4A C4 H4C 114(2) . . ?
H4B C4 H4C 103(2) . . ?
C3 C5 H5A 107.7(19) . . ?
C3 C5 H5B 109.8(19) . . ?
H5A C5 H5B 109(3) . . ?
C3 C5 H5C 109.4(17) . . ?
H5A C5 H5C 111(3) . . ?
H5B C5 H5C 110(3) . . ?
H4D O4 H4E 108(3) . . ?
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 1.3330(18) . ?
O2 N5 1.3247(18) . ?
O2 H2 0.946(18) . ?
N1 N2 1.332(2) . ?
N1 C1 1.332(2) . ?
N2 N3 1.303(2) . ?
N3 N4 1.347(2) . ?
N4 C1 1.328(2) . ?
N5 C2 1.331(2) . ?
N5 N6 1.334(2) . ?
N6 N7 1.301(2) . ?
N7 N8 1.344(2) . ?
N8 C2 1.324(2) . ?
C1 C2 1.444(2) . ?
O3 N9 1.362(2) . ?
O3 H3 0.870(17) . ?
N9 C3 1.268(2) . ?
N9 H9 0.93(3) . ?
C3 C5 1.475(3) . ?
C3 C4 1.476(3) . ?
C4 H4A 0.99(3) . ?
C4 H4B 1.01(3) . ?
C4 H4C 0.91(3) . ?
C5 H5A 0.92(3) . ?
C5 H5B 0.94(4) . ?
C5 H5C 0.93(3) . ?
O4 H4D 0.88(3) . ?
O4 H4E 0.88(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.946(18) 1.481(19) 2.4248(18) 175(3) 1_565
O2 H2 N1 0.946(18) 2.33(2) 3.1371(18) 143(3) 1_565
O2 H2 N2 0.946(18) 2.62(3) 3.112(2) 113(2) 1_565
C4 H4A O4 0.99(3) 2.63(3) 3.448(3) 140(2) 1_655
N9 H9 O1 0.93(3) 2.47(3) 2.989(2) 115.6(19) .
N9 H9 N8 0.93(3) 1.90(3) 2.795(2) 162(2) .
O3 H3 O4 0.870(17) 1.653(18) 2.523(2) 178(3) .
O4 H4D N4 0.88(3) 2.00(3) 2.881(2) 175(3) 2_676
O4 H4E O2 0.88(4) 2.42(3) 2.910(2) 116(3) 2_676
O4 H4E N2 0.88(4) 2.16(4) 2.994(2) 158(3) 2_666
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 -179.25(17) . . . . ?
C1 N1 N2 N3 -0.2(2) . . . . ?
N1 N2 N3 N4 0.2(2) . . . . ?
N2 N3 N4 C1 -0.1(2) . . . . ?
O2 N5 N6 N7 -178.92(16) . . . . ?
C2 N5 N6 N7 -0.4(2) . . . . ?
N5 N6 N7 N8 0.3(2) . . . . ?
N6 N7 N8 C2 -0.1(2) . . . . ?
N3 N4 C1 N1 -0.1(2) . . . . ?
N3 N4 C1 C2 179.80(18) . . . . ?
N2 N1 C1 N4 0.2(2) . . . . ?
O1 N1 C1 N4 179.16(17) . . . . ?
N2 N1 C1 C2 -179.69(16) . . . . ?
O1 N1 C1 C2 -0.7(3) . . . . ?
N7 N8 C2 N5 -0.2(2) . . . . ?
N7 N8 C2 C1 179.99(17) . . . . ?
O2 N5 C2 N8 178.78(17) . . . . ?
N6 N5 C2 N8 0.4(2) . . . . ?
O2 N5 C2 C1 -1.4(3) . . . . ?
N6 N5 C2 C1 -179.81(16) . . . . ?
N4 C1 C2 N8 170.46(18) . . . . ?
N1 C1 C2 N8 -9.7(3) . . . . ?
N4 C1 C2 N5 -9.3(3) . . . . ?
N1 C1 C2 N5 170.52(17) . . . . ?
O3 N9 C3 C5 1.2(3) . . . . ?
O3 N9 C3 C4 179.87(18) . . . . ?
