#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:44:35 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 233328 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/57/7235793.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_7235793
loop_
_publ_author_name
'Bian, Chengming'
'Zhang, Man'
'Li, Chuan'
'Zhou, Zhiming'
_publ_section_title
;
 3-Nitro-1-(2H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine (HANTT) and its
 energetic salts: highly thermally stable energetic materials with low
 sensitivity
;
_journal_issue                   1
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              163
_journal_paper_doi               10.1039/C4TA04107K
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C3 H5 N9 O3'
_chemical_formula_weight         215.16
_chemical_name_systematic        HANTT
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.122(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.830(4)
_cell_length_b                   5.0641(18)
_cell_length_c                   15.865(6)
_cell_measurement_reflns_used    2855
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.123
_cell_measurement_theta_min      2.659
_cell_volume                     835.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8220
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_type   Multi-scans
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0671P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1916
_reflns_number_total             2245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ta04107k2.cif
_cod_data_source_block           bo2979
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7235793
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'
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
O1 O 0.44264(11) 0.3517(2) 0.28998(7) 0.0358(3) Uani 1 1 d
O2 O 0.29507(11) 0.6529(2) 0.26381(7) 0.0402(3) Uani 1 1 d
N1 N 0.26959(10) 0.4518(2) 0.50264(7) 0.0213(3) Uani 1 1 d
N2 N 0.25678(10) 0.5696(2) 0.42227(7) 0.0222(3) Uani 1 1 d
N3 N 0.41016(10) 0.2482(2) 0.44805(7) 0.0220(3) Uani 1 1 d
N4 N 0.39890(13) 0.1108(3) 0.58860(8) 0.0297(3) Uani 1 1 d
N5 N 0.36125(11) 0.4853(2) 0.31016(8) 0.0253(3) Uani 1 1 d
N6 N 0.18900(11) 0.3844(2) 0.62649(7) 0.0236(3) Uani 1 1 d
N7 N 0.10351(10) 0.5094(2) 0.65783(7) 0.0239(3) Uani 1 1 d
N8 N 0.06075(10) 0.7096(2) 0.60553(7) 0.0232(3) Uani 1 1 d
N9 N 0.11294(11) 0.7304(2) 0.53877(8) 0.0231(3) Uani 1 1 d
C1 C 0.36223(12) 0.2585(3) 0.51728(8) 0.0210(3) Uani 1 1 d
C2 C 0.34215(12) 0.4367(3) 0.39611(8) 0.0211(3) Uani 1 1 d
C3 C 0.19121(12) 0.5237(3) 0.55526(8) 0.0203(3) Uani 1 1 d
O3 O -0.11192(11) 0.9749(2) 0.65608(8) 0.0306(3) Uani 1 1 d
H3A H -0.105(2) 0.984(4) 0.7098(16) 0.052(6) Uiso 1 1 d
H3B H -0.146(2) 1.121(5) 0.6313(14) 0.054(6) Uiso 1 1 d
H4A H 0.4605(18) -0.017(4) 0.5908(12) 0.038(5) Uiso 1 1 d
H4B H 0.3654(17) 0.129(4) 0.6291(12) 0.036(5) Uiso 1 1 d
H8 H -0.0044(19) 0.832(4) 0.6212(13) 0.053(6) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0440(6) 0.0439(6) 0.0269(6) 0.0063(5) 0.0223(5) 0.0181(5)
O2 0.0465(6) 0.0505(7) 0.0272(6) 0.0172(5) 0.0162(5) 0.0231(6)
N1 0.0240(5) 0.0259(6) 0.0169(5) 0.0017(4) 0.0101(4) 0.0079(4)
N2 0.0256(5) 0.0261(6) 0.0173(5) 0.0031(4) 0.0098(4) 0.0065(4)
N3 0.0234(5) 0.0270(6) 0.0177(5) 0.0013(4) 0.0094(4) 0.0072(4)
N4 0.0359(6) 0.0377(7) 0.0197(6) 0.0073(5) 0.0147(5) 0.0183(6)
N5 0.0290(6) 0.0304(6) 0.0191(5) 0.0034(4) 0.0109(4) 0.0074(5)
N6 0.0258(5) 0.0274(6) 0.0207(6) -0.0013(4) 0.0118(4) 0.0044(5)
N7 0.0245(5) 0.0273(6) 0.0227(6) -0.0039(4) 0.0114(4) 0.0013(4)
N8 0.0211(5) 0.0289(6) 0.0220(6) -0.0042(4) 0.0101(4) 0.0027(4)
N9 0.0233(5) 0.0272(6) 0.0216(6) -0.0024(4) 0.0109(4) 0.0059(4)
C1 0.0217(6) 0.0248(6) 0.0183(6) -0.0004(5) 0.0088(5) 0.0056(5)
C2 0.0230(6) 0.0249(6) 0.0168(6) 0.0010(5) 0.0081(5) 0.0050(5)
C3 0.0198(6) 0.0242(6) 0.0186(6) -0.0035(5) 0.0079(5) 0.0023(5)
O3 0.0389(6) 0.0323(6) 0.0260(6) 0.0048(5) 0.0177(5) 0.0145(5)
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
C1 N1 N2 110.21(10)
C1 N1 C3 128.46(12)
N2 N1 C3 121.27(11)
C2 N2 N1 99.98(10)
C1 N3 C2 101.78(10)
C1 N4 H4A 118.1(11)
C1 N4 H4B 120.7(13)
H4A N4 H4B 121.2(17)
O2 N5 O1 125.05(12)
O2 N5 C2 118.07(11)
O1 N5 C2 116.88(11)
N7 N6 C3 104.06(11)
N8 N7 N6 107.00(10)
N7 N8 N9 114.22(11)
N7 N8 H8 117.5(11)
N9 N8 H8 128.3(11)
C3 N9 N8 99.73(11)
N4 C1 N3 125.92(12)
N4 C1 N1 125.40(11)
N3 C1 N1 108.67(11)
N2 C2 N3 119.36(12)
N2 C2 N5 120.64(11)
N3 C2 N5 119.97(11)
N9 C3 N6 114.99(11)
N9 C3 N1 123.36(12)
N6 C3 N1 121.65(12)
H3A O3 H3B 108.5(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2222(15)
O2 N5 1.2176(16)
N1 C1 1.3746(16)
N1 N2 1.3793(15)
N1 C3 1.3939(15)
N2 C2 1.3013(16)
N3 C1 1.3399(16)
N3 C2 1.3400(17)
N4 C1 1.3220(18)
N4 H4A 0.924(19)
N4 H4B 0.827(18)
N5 C2 1.4558(17)
N6 N7 1.3270(15)
N6 C3 1.3381(17)
N7 N8 1.3105(17)
N8 N9 1.3360(15)
N8 H8 1.02(2)
N9 C3 1.3267(17)
O3 H3A 0.84(2)
O3 H3B 0.87(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
C1 N1 N2 C2 0.13(14)
C3 N1 N2 C2 -177.22(12)
C3 N6 N7 N8 0.00(14)
N6 N7 N8 N9 -0.10(15)
N7 N8 N9 C3 0.16(14)
C2 N3 C1 N4 -179.26(14)
C2 N3 C1 N1 -0.23(14)
N2 N1 C1 N4 179.10(14)
C3 N1 C1 N4 -3.8(2)
N2 N1 C1 N3 0.07(15)
C3 N1 C1 N3 177.17(13)
N1 N2 C2 N3 -0.31(16)
N1 N2 C2 N5 177.73(12)
C1 N3 C2 N2 0.36(16)
C1 N3 C2 N5 -177.70(12)
O2 N5 C2 N2 -0.1(2)
O1 N5 C2 N2 -179.59(13)
O2 N5 C2 N3 177.92(13)
O1 N5 C2 N3 -1.6(2)
N8 N9 C3 N6 -0.16(15)
N8 N9 C3 N1 179.15(12)
N7 N6 C3 N9 0.11(15)
N7 N6 C3 N1 -179.21(12)
C1 N1 C3 N9 173.46(13)
N2 N1 C3 N9 -9.7(2)
C1 N1 C3 N6 -7.3(2)
N2 N1 C3 N6 169.55(12)
