#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:37:30 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240220.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_7240220
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         '[NH2(CH3CH2) 2+]2[C2O2N8 2 -]'
_chemical_formula_sum            'C10 H24 N10 O2'
_chemical_formula_weight         316.39
_chemical_name_common            DEA-BTO
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 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                90
_cell_angle_beta                 105.393(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3308(10)
_cell_length_b                   12.0024(16)
_cell_length_c                   9.2986(12)
_cell_measurement_reflns_used    3997
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.620
_cell_measurement_theta_min      4.103
_cell_volume                     896.4(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7344
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.052
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             340
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DEF'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.028(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0402
_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)+(0.0604P)²+0.2653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                776
_reflns_number_total             924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01182g2.cif
_cod_data_source_block           mo_d8v19707_0m
_cod_depositor_comments
'Adding full bibliography for 7240219--7240221.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7240220
_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   0.984
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.67679(15) 0.5000 0.44283(16) 0.0774(6) Uani 1 2 d S T P . .
N1 N 0.79047(18) 0.5000 0.36931(17) 0.0495(5) Uani 1 2 d S T P . .
N2 N 0.7513(2) 0.5000 0.22000(18) 0.0579(5) Uani 1 2 d S T P . .
N3 N 0.8927(2) 0.5000 0.18374(19) 0.0631(6) Uani 1 2 d S T P . .
N4 N 1.02173(19) 0.5000 0.30648(18) 0.0586(5) Uani 1 2 d S T P . .
C1 C 0.9564(2) 0.5000 0.4218(2) 0.0445(5) Uani 1 2 d S T P . .
N5 N 0.3575(2) 0.5000 0.26156(19) 0.0511(5) Uani 1 2 d S T P . .
C2 C 0.3276(3) 0.39731(18) 0.1708(2) 0.0790(6) Uani 1 1 d . . . . .
C3 C 0.3585(5) 0.2970(2) 0.2680(5) 0.1214(11) Uani 1 1 d . . . . .
H5A H 0.296(3) 0.5000 0.327(3) 0.065(7) Uiso 1 2 d S . P . .
H2A H 0.210(3) 0.3968(18) 0.113(3) 0.102(7) Uiso 1 1 d . . . . .
H5B H 0.473(3) 0.5000 0.321(3) 0.062(6) Uiso 1 2 d S . P . .
H2B H 0.406(3) 0.394(2) 0.108(3) 0.108(7) Uiso 1 1 d . . . . .
H3A H 0.478(5) 0.298(3) 0.329(4) 0.149(11) Uiso 1 1 d . . . . .
H3B H 0.346(4) 0.228(3) 0.201(4) 0.164(12) Uiso 1 1 d . . . . .
H3C H 0.290(5) 0.297(4) 0.332(5) 0.185(18) 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
O1 N1 C1 129.13(16) . . ?
O1 N1 N2 122.09(14) . . ?
C1 N1 N2 108.78(15) . . ?
N3 N2 N1 106.18(15) . . ?
N2 N3 N4 110.66(16) . . ?
C1 N4 N3 106.25(15) . . ?
N4 C1 N1 108.13(16) . . ?
N4 C1 C1 127.67(19) . 5_766 ?
N1 C1 C1 124.2(2) . 5_766 ?
C2 N5 C2 113.1(2) 6_565 . ?
C2 N5 H5A 110.3(7) 6_565 . ?
C2 N5 H5A 110.3(7) . . ?
C2 N5 H5B 108.5(6) 6_565 . ?
C2 N5 H5B 108.5(6) . . ?
H5A N5 H5B 106(2) . . ?
N5 C2 C3 110.7(2) . . ?
N5 C2 H2A 108.0(13) . . ?
C3 C2 H2A 108.3(13) . . ?
N5 C2 H2B 109.8(14) . . ?
C3 C2 H2B 106.9(14) . . ?
H2A C2 H2B 113(2) . . ?
C2 C3 H3A 108.6(18) . . ?
C2 C3 H3B 108.2(19) . . ?
H3A C3 H3B 106(2) . . ?
C2 C3 H3C 110(3) . . ?
H3A C3 H3C 109(3) . . ?
H3B C3 H3C 114(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 1.307(2) . ?
N1 C1 1.338(2) . ?
N1 N2 1.339(2) . ?
N2 N3 1.309(2) . ?
N3 N4 1.344(2) . ?
N4 C1 1.325(2) . ?
C1 C1 1.443(4) 5_766 ?
N5 C2 1.477(2) 6_565 ?
N5 C2 1.477(2) . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.97(2) . ?
C2 C3 1.487(4) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.99(2) . ?
C3 H3A 1.00(4) . ?
C3 H3B 1.02(4) . ?
C3 H3C 0.93(4) . ?
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 180.000(0) . . . . ?
C1 N1 N2 N3 0.000(0) . . . . ?
N1 N2 N3 N4 0.000(0) . . . . ?
N2 N3 N4 C1 0.000(0) . . . . ?
N3 N4 C1 N1 0.000(0) . . . . ?
N3 N4 C1 C1 180.000(0) . . . 5_766 ?
O1 N1 C1 N4 180.000(0) . . . . ?
N2 N1 C1 N4 0.000(0) . . . . ?
O1 N1 C1 C1 0.000(1) . . . 5_766 ?
N2 N1 C1 C1 180.000(0) . . . 5_766 ?
C2 N5 C2 C3 -179.6(2) 6_565 . . . ?
