#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:58:32 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/66/7236632.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_7236632
loop_
_publ_author_name
'Wang, Binshen'
'Qi, Xiujuan'
'Zhang, Wenquan'
'Wang, Kangcai'
'Li, Wei'
'Zhang, Qinghua'
_publ_section_title
;
 Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its
 derivatives from 5-aminotetrazole and cyanogen azide: a promising
 strategy towards the development of C--N linked bistetrazolate energetic
 materials
;
_journal_issue                   39
_journal_name_full               'J. Mater. Chem. A'
_journal_page_first              20867
_journal_paper_doi               10.1039/C7TA05905A
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         '2(H2 O), C H6 N5 O2, C2 H N10 O2'
_chemical_formula_sum            'C3 H11 N15 O6'
_chemical_formula_weight         353.27
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.272(3)
_cell_angle_beta                 91.229(3)
_cell_angle_gamma                105.997(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6274(11)
_cell_length_b                   9.3787(14)
_cell_length_c                   11.2469(18)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.62
_cell_volume                     654.25(18)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5908
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.841
_diffrn_reflns_theta_min         1.860
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0526 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.8722. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0641
_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)+(0.1346P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2315
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ta05905a2.cif
_cod_data_source_block           mo_2017060_0m
_cod_database_code               7236632
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O2W O 0.2157(3) 0.4926(2) 0.08702(18) 0.0380(5) Uani 1 1 d
N14 N 0.3227(3) 0.2778(2) 0.88740(17) 0.0290(4) Uani 1 1 d
O1W O 0.1392(3) 0.7629(2) 0.9345(2) 0.0398(5) Uani 1 1 d
O4 O 0.1981(4) 0.0191(2) 0.82903(18) 0.0525(6) Uani 1 1 d
O3 O 0.3406(4) 0.1308(2) 1.01142(17) 0.0501(6) Uani 1 1 d
O2 O 0.2431(3) 0.3365(2) 0.46633(17) 0.0441(5) Uani 1 1 d
O1 O 0.2881(3) 0.30288(19) 0.27309(16) 0.0387(5) Uani 1 1 d
N15 N 0.2865(3) 0.1363(2) 0.90826(18) 0.0312(5) Uani 1 1 d
N6 N 0.2525(3) 0.7653(2) 0.47646(17) 0.0258(4) Uani 1 1 d
N2 N 0.2741(3) 0.5275(2) 0.36823(18) 0.0297(5) Uani 1 1 d
N1 N 0.2684(3) 0.3870(2) 0.37239(18) 0.0279(4) Uani 1 1 d
N7 N 0.2689(3) 0.9897(2) 0.40800(18) 0.0314(5) Uani 1 1 d
N8 N 0.2617(3) 1.0131(2) 0.29572(19) 0.0308(5) Uani 1 1 d
N11 N 0.3723(4) 0.5550(2) 0.87430(19) 0.0299(5) Uani 1 1 d
N12 N 0.2905(3) 0.4361(2) 0.76849(19) 0.0299(5) Uani 1 1 d
C3 C 0.2847(3) 0.2921(2) 0.7738(2) 0.0251(5) Uani 1 1 d
N13 N 0.2434(3) 0.1888(2) 0.6695(2) 0.0311(5) Uani 1 1 d
N9 N 0.2462(3) 0.8921(2) 0.20905(19) 0.0335(5) Uani 1 1 d
N10 N 0.2411(3) 0.7792(2) 0.26432(18) 0.0311(5) Uani 1 1 d
C2 C 0.2554(3) 0.8431(2) 0.3832(2) 0.0240(5) Uani 1 1 d
C1 C 0.2586(3) 0.6202(2) 0.4763(2) 0.0249(5) Uani 1 1 d
N5 N 0.2406(4) 0.8384(2) 0.59358(19) 0.0343(5) Uani 1 1 d
N4 N 0.2390(4) 0.7421(2) 0.65972(19) 0.0383(5) Uani 1 1 d
N3 N 0.2500(3) 0.6058(2) 0.59125(18) 0.0326(5) Uani 1 1 d
H11A H 0.513(4) 0.578(3) 0.881(2) 0.029(7) Uiso 1 1 d
H2WA H 0.115(5) 0.417(4) 0.084(3) 0.048(9) Uiso 1 1 d
H11B H 0.324(5) 0.520(4) 0.941(3) 0.042(8) Uiso 1 1 d
H13A H 0.247(6) 0.105(4) 0.668(3) 0.058(10) Uiso 1 1 d
H12 H 0.276(5) 0.459(4) 0.694(3) 0.052(9) Uiso 1 1 d
H13B H 0.232(5) 0.209(4) 0.591(3) 0.058(10) Uiso 1 1 d
H1WA H 0.193(6) 0.813(5) 1.002(4) 0.076(14) Uiso 1 1 d
H2WB H 0.212(5) 0.553(4) 0.153(3) 0.057(10) Uiso 1 1 d
H11C H 0.306(6) 0.645(4) 0.874(3) 0.069(10) Uiso 1 1 d
H1WB H 0.156(8) 0.833(6) 0.885(5) 0.114(18) Uiso 1 1 d
H8 H 0.267(6) 1.114(5) 0.282(4) 0.074(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
H2WA O2W H2WB 106(3)
C3 N14 N15 118.79(19)
H1WA O1W H1WB 105(4)
O4 N15 N14 122.45(19)
O3 N15 N14 115.64(19)
O3 N15 O4 121.9(2)
C1 N6 C2 132.4(2)
N5 N6 C2 119.00(18)
N5 N6 C1 108.56(18)
N1 N2 C1 115.82(18)
O2 N1 O1 120.43(19)
O2 N1 N2 123.9(2)
O1 N1 N2 115.61(18)
C2 N7 N8 100.39(19)
N7 N8 H8 121(2)
N9 N8 N7 114.29(18)
N9 N8 H8 124(2)
N12 N11 H11A 109.1(17)
N12 N11 H11B 108(2)
N12 N11 H11C 110(2)
H11A N11 H11B 108(2)
H11A N11 H11C 117(3)
H11B N11 H11C 104(3)
N11 N12 H12 120(2)
C3 N12 N11 118.33(18)
C3 N12 H12 119(2)
N14 C3 N12 113.0(2)
N13 C3 N14 130.0(2)
N13 C3 N12 117.0(2)
C3 N13 H13A 120(3)
C3 N13 H13B 125(2)
H13A N13 H13B 114(3)
N8 N9 N10 106.36(19)
N9 N10 C2 104.58(18)
N7 C2 N6 121.0(2)
N7 C2 N10 114.4(2)
N10 C2 N6 124.57(19)
N2 C1 N6 118.39(19)
N3 C1 N6 106.97(19)
N3 C1 N2 134.6(2)
N4 N5 N6 106.21(19)
N5 N4 N3 111.7(2)
C1 N3 N4 106.60(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2W H2WA 0.82(4)
O2W H2WB 0.84(4)
N14 N15 1.354(2)
N14 C3 1.339(3)
O1W H1WA 0.81(5)
O1W H1WB 0.93(6)
O4 N15 1.246(3)
O3 N15 1.223(3)
O2 N1 1.243(3)
O1 N1 1.255(3)
N6 C2 1.398(3)
N6 C1 1.372(3)
N6 N5 1.365(3)
N2 N1 1.319(2)
N2 C1 1.360(3)
N7 N8 1.329(3)
N7 C2 1.320(3)
N8 N9 1.307(3)
N8 H8 0.98(4)
N11 N12 1.424(3)
N11 H11A 0.90(3)
N11 H11B 0.91(3)
N11 H11C 1.05(4)
N12 C3 1.354(3)
N12 H12 0.92(4)
C3 N13 1.321(3)
N13 H13A 0.79(4)
N13 H13B 0.95(4)
N9 N10 1.331(3)
N10 C2 1.333(3)
C1 N3 1.329(3)
N5 N4 1.285(3)
N4 N3 1.366(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
N15 N14 C3 N12 168.9(2)
N15 N14 C3 N13 -11.1(4)
N6 C1 N3 N4 0.0(2)
N6 N5 N4 N3 0.2(3)
N2 C1 N3 N4 178.9(3)
N1 N2 C1 N6 -176.65(18)
N1 N2 C1 N3 4.5(4)
N7 N8 N9 N10 0.4(3)
N8 N7 C2 N6 -178.67(19)
N8 N7 C2 N10 0.1(3)
N8 N9 N10 C2 -0.3(2)
N11 N12 C3 N14 11.6(3)
N11 N12 C3 N13 -168.5(2)
C3 N14 N15 O4 -7.9(3)
C3 N14 N15 O3 174.2(2)
N9 N10 C2 N6 178.8(2)
N9 N10 C2 N7 0.1(3)
C2 N6 C1 N2 1.3(4)
C2 N6 C1 N3 -179.6(2)
C2 N6 N5 N4 179.56(19)
C2 N7 N8 N9 -0.3(3)
C1 N6 C2 N7 -173.2(2)
C1 N6 C2 N10 8.1(4)
C1 N6 N5 N4 -0.2(3)
C1 N2 N1 O2 2.5(3)
C1 N2 N1 O1 -178.3(2)
N5 N6 C2 N7 7.1(3)
N5 N6 C2 N10 -171.5(2)
N5 N6 C1 N2 -178.96(19)
N5 N6 C1 N3 0.1(2)
N5 N4 N3 C1 -0.1(3)
