#------------------------------------------------------------------------------
#$Date: 2016-06-18 11:59:46 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/54/7055492.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_7055492
loop_
_publ_author_name
'Wu, Jin-Ting'
'Zhang, Jian-Guo'
'Yin, Xin'
'Wu, Le'
_publ_section_title
;
 Energetic salts based on 3-hydrazino-4-amino-1,2,4-triazole (HATr):
 synthesis and properties
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              5414
_journal_paper_doi               10.1039/C6NJ00308G
_journal_volume                  40
_journal_year                    2016
_chemical_formula_sum            'C14 H14 N12 O15'
_chemical_formula_weight         590.37
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_audit_update_record
;
2016-01-28 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                69.469(9)
_cell_angle_beta                 73.214(9)
_cell_angle_gamma                80.053(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0048(18)
_cell_length_b                   11.527(2)
_cell_length_c                   13.178(2)
_cell_measurement_reflns_used    4439
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.507
_cell_measurement_theta_min      2.666
_cell_volume                     1086.7(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15158
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0544
_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)+(0.0695P)²+2.6600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.2111
_reflns_number_gt                5108
_reflns_number_total             6993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6nj00308g1.cif
_cod_data_source_block           bn1886
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7055491--7055495.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7055492
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
O1 O 0.0406(2) 0.19300(15) 0.46234(15) 0.0158(4) Uani 1 1 d .
O2 O 0.3947(3) 0.16199(16) 0.46241(18) 0.0211(4) Uani 1 1 d .
O3 O 0.4140(3) 0.28047(19) 0.55370(19) 0.0260(5) Uani 1 1 d .
O4 O 0.3018(3) 0.71518(18) 0.3443(2) 0.0283(5) Uani 1 1 d .
O5 O 0.0705(3) 0.77043(17) 0.2794(2) 0.0264(5) Uani 1 1 d .
O6 O -0.3281(3) 0.46371(19) 0.36793(19) 0.0254(4) Uani 1 1 d .
O7 O -0.2144(3) 0.28646(18) 0.3476(2) 0.0290(5) Uani 1 1 d .
O8 O 0.4801(3) 0.82877(16) 0.03421(16) 0.0193(4) Uani 1 1 d .
O9 O 0.1539(3) 0.87946(19) -0.0014(2) 0.0336(5) Uani 1 1 d .
O10 O 0.0945(3) 0.7421(2) -0.0599(2) 0.0342(5) Uani 1 1 d .
O11 O 0.1921(3) 0.31536(19) 0.1478(2) 0.0293(5) Uani 1 1 d .
O12 O 0.4311(3) 0.25361(18) 0.2040(2) 0.0282(5) Uani 1 1 d .
O13 O 0.8367(3) 0.55164(19) 0.12729(19) 0.0262(4) Uani 1 1 d .
O14 O 0.7258(3) 0.7277(2) 0.1520(2) 0.0332(5) Uani 1 1 d .
O15 O 0.7062(3) 0.08047(19) 0.28609(17) 0.0207(4) Uani 1 1 d .
N1 N 0.0834(3) 0.02079(18) 0.32338(17) 0.0150(4) Uani 1 1 d .
N2 N 0.0682(3) 0.05281(19) 0.21592(18) 0.0157(4) Uani 1 1 d .
N3 N 0.3370(3) -0.00520(18) 0.20671(17) 0.0141(4) Uani 1 1 d .
N4 N 0.5202(3) -0.0287(2) 0.17316(19) 0.0153(4) Uani 1 1 d .
N5 N 0.3372(3) -0.04709(18) 0.39752(17) 0.0130(4) Uani 1 1 d .
N6 N 0.2212(3) -0.04141(18) 0.50185(17) 0.0131(4) Uani 1 1 d .
N7 N 0.3507(3) 0.25717(18) 0.48890(18) 0.0155(4) Uani 1 1 d .
N8 N 0.1730(3) 0.69128(18) 0.32512(18) 0.0169(4) Uani 1 1 d .
N9 N -0.2041(3) 0.38354(19) 0.36368(19) 0.0167(4) Uani 1 1 d .
N10 N 0.1721(3) 0.7735(2) -0.0063(2) 0.0201(4) Uani 1 1 d .
N11 N 0.3265(3) 0.33663(19) 0.16376(18) 0.0164(4) Uani 1 1 d .
N12 N 0.7155(3) 0.6333(2) 0.1325(2) 0.0189(4) Uani 1 1 d .
C1 C 0.2493(3) -0.0136(2) 0.31441(19) 0.0117(4) Uani 1 1 d .
C2 C 0.2172(4) 0.0371(2) 0.1462(2) 0.0178(5) Uani 1 1 d .
H2 H 0.2368 0.0525 0.0681 0.021 Uiso 1 1 calc R
C3 C 0.0742(3) 0.3057(2) 0.42593(19) 0.0111(4) Uani 1 1 d .
C4 C 0.2241(3) 0.3483(2) 0.4385(2) 0.0130(4) Uani 1 1 d .
C5 C 0.2552(3) 0.4712(2) 0.4089(2) 0.0133(4) Uani 1 1 d .
H5 H 0.3544 0.4935 0.4217 0.016 Uiso 1 1 calc R
C6 C 0.1376(3) 0.5615(2) 0.3601(2) 0.0130(4) Uani 1 1 d .
C7 C -0.0112(3) 0.5315(2) 0.3442(2) 0.0134(4) Uani 1 1 d .
H7 H -0.0912 0.5949 0.3119 0.016 Uiso 1 1 calc R
C8 C -0.0410(3) 0.4080(2) 0.3762(2) 0.0125(4) Uani 1 1 d .
C9 C 0.4399(3) 0.7186(2) 0.0668(2) 0.0139(4) Uani 1 1 d .
C10 C 0.2897(3) 0.6800(2) 0.0514(2) 0.0152(4) Uani 1 1 d .
C11 C 0.2525(3) 0.5584(2) 0.0816(2) 0.0155(4) Uani 1 1 d .
H11 H 0.1518 0.5391 0.0681 0.019 Uiso 1 1 calc R
C12 C 0.3647(3) 0.4644(2) 0.1321(2) 0.0144(4) Uani 1 1 d .
C13 C 0.5153(3) 0.4906(2) 0.1484(2) 0.0142(4) Uani 1 1 d .
H13 H 0.5934 0.4251 0.1803 0.017 Uiso 1 1 calc R
C14 C 0.5510(3) 0.6126(2) 0.1180(2) 0.0142(4) Uani 1 1 d .
H2N H -0.018(5) 0.081(3) 0.201(3) 0.012(8) Uiso 1 1 d .
H4A H 0.554(4) 0.027(3) 0.112(3) 0.009(7) Uiso 1 1 d .
H4B H 0.539(4) -0.099(3) 0.160(3) 0.010(7) Uiso 1 1 d .
H5N H 0.402(5) -0.113(3) 0.403(3) 0.018(8) Uiso 1 1 d .
H6A H 0.143(4) -0.095(3) 0.522(2) 0.006(6) Uiso 1 1 d .
H6B H 0.291(5) -0.061(3) 0.564(3) 0.022(9) Uiso 1 1 d .
H6C H 0.160(5) 0.037(3) 0.492(3) 0.019(8) Uiso 1 1 d .
H15A H 0.653(5) 0.035(3) 0.274(3) 0.021(9) Uiso 1 1 d .
H15B H 0.657(6) 0.145(4) 0.275(4) 0.041(12) 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
H15A O15 H15B 108(4)
C1 N1 N2 103.1(2)
C2 N2 N1 112.5(2)
C2 N2 H2N 127(3)
N1 N2 H2N 121(3)
C2 N3 C1 106.1(2)
C2 N3 N4 130.6(2)
C1 N3 N4 123.0(2)
N3 N4 H4A 106(2)
N3 N4 H4B 107(2)
H4A N4 H4B 108(3)
C1 N5 N6 111.41(19)
C1 N5 H5N 115(2)
N6 N5 H5N 114(2)
N5 N6 H6A 107.9(19)
N5 N6 H6B 111.0(19)
H6A N6 H6B 111(3)
N5 N6 H6C 110(2)
H6A N6 H6C 106(3)
H6B N6 H6C 111(3)
O2 N7 O3 122.8(2)
O2 N7 C4 118.8(2)
O3 N7 C4 118.4(2)
O4 N8 O5 123.9(2)
O4 N8 C6 118.1(2)
O5 N8 C6 118.0(2)
O7 N9 O6 122.5(2)
O7 N9 C8 119.8(2)
O6 N9 C8 117.7(2)
O9 N10 O10 122.4(2)
O9 N10 C10 120.0(2)
O10 N10 C10 117.7(2)
O11 N11 O12 122.9(2)
O11 N11 C12 118.5(2)
O12 N11 C12 118.6(2)
O14 N12 O13 123.5(2)
O14 N12 C14 119.1(2)
O13 N12 C14 117.4(2)
N1 C1 N3 111.8(2)
N1 C1 N5 127.1(2)
N3 C1 N5 121.0(2)
N2 C2 N3 106.4(2)
N2 C2 H2 126.8
N3 C2 H2 126.8
O1 C3 C4 123.7(2)
O1 C3 C8 124.0(2)
C4 C3 C8 112.08(19)
C5 C4 C3 124.8(2)
C5 C4 N7 116.2(2)
C3 C4 N7 118.90(19)
C4 C5 C6 118.2(2)
C4 C5 H5 120.9
C6 C5 H5 120.9
C7 C6 C5 122.0(2)
C7 C6 N8 119.6(2)
C5 C6 N8 118.4(2)
C8 C7 C6 118.7(2)
C8 C7 H7 120.6
C6 C7 H7 120.6
C7 C8 N9 115.8(2)
C7 C8 C3 124.2(2)
N9 C8 C3 119.93(19)
O8 C9 C10 125.3(2)
O8 C9 C14 122.7(2)
C10 C9 C14 111.8(2)
C11 C10 C9 124.8(2)
C11 C10 N10 116.0(2)
C9 C10 N10 119.0(2)
C10 C11 C12 118.8(2)
C10 C11 H11 120.6
C12 C11 H11 120.6
C13 C12 C11 121.3(2)
C13 C12 N11 119.6(2)
C11 C12 N11 119.0(2)
C14 C13 C12 119.3(2)
C14 C13 H13 120.4
C12 C13 H13 120.4
C13 C14 N12 116.4(2)
C13 C14 C9 123.9(2)
N12 C14 C9 119.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.265(3)
O2 N7 1.230(3)
O3 N7 1.231(3)
O4 N8 1.225(3)
O5 N8 1.228(3)
O6 N9 1.237(3)
O7 N9 1.230(3)
O8 C9 1.256(3)
O9 N10 1.227(3)
O10 N10 1.235(3)
O11 N11 1.233(3)
O12 N11 1.234(3)
O13 N12 1.234(3)
O14 N12 1.223(3)
O15 H15A 0.81(4)
O15 H15B 0.77(5)
N1 C1 1.302(3)
N1 N2 1.369(3)
N2 C2 1.307(4)
N2 H2N 0.75(3)
N3 C2 1.342(4)
N3 C1 1.367(3)
N3 N4 1.411(3)
N4 H4A 0.85(3)
N4 H4B 0.86(3)
N5 C1 1.378(3)
N5 N6 1.436(3)
N5 H5N 0.83(3)
N6 H6A 0.88(3)
N6 H6B 1.06(4)
N6 H6C 0.93(3)
N7 C4 1.450(3)
N8 C6 1.455(3)
N9 C8 1.448(3)
N10 C10 1.454(3)
N11 C12 1.445(3)
N12 C14 1.454(3)
C2 H2 0.9500
C3 C4 1.443(3)
C3 C8 1.450(3)
C4 C5 1.379(3)
C5 C6 1.387(3)
C5 H5 0.9500
C6 C7 1.386(3)
C7 C8 1.379(3)
C7 H7 0.9500
C9 C10 1.440(4)
C9 C14 1.460(3)
C10 C11 1.378(3)
C11 C12 1.388(3)
C11 H11 0.9500
C12 C13 1.382(4)
C13 C14 1.378(3)
C13 H13 0.9500
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 0.7(3)
N2 N1 C1 N3 -0.5(2)
N2 N1 C1 N5 175.2(2)
C2 N3 C1 N1 0.1(3)
N4 N3 C1 N1 175.44(19)
C2 N3 C1 N5 -175.9(2)
N4 N3 C1 N5 -0.5(3)
N6 N5 C1 N1 0.6(3)
N6 N5 C1 N3 175.92(19)
N1 N2 C2 N3 -0.7(3)
C1 N3 C2 N2 0.3(3)
N4 N3 C2 N2 -174.5(2)
O1 C3 C4 C5 -173.7(2)
C8 C3 C4 C5 1.0(3)
O1 C3 C4 N7 4.2(3)
C8 C3 C4 N7 178.9(2)
O2 N7 C4 C5 -139.9(2)
O3 N7 C4 C5 37.7(3)
O2 N7 C4 C3 42.0(3)
O3 N7 C4 C3 -140.4(2)
C3 C4 C5 C6 -2.2(4)
N7 C4 C5 C6 179.8(2)
C4 C5 C6 C7 2.3(4)
C4 C5 C6 N8 -177.8(2)
O4 N8 C6 C7 177.1(2)
O5 N8 C6 C7 -1.9(3)
O4 N8 C6 C5 -2.7(3)
O5 N8 C6 C5 178.2(2)
C5 C6 C7 C8 -1.2(4)
N8 C6 C7 C8 178.9(2)
C6 C7 C8 N9 176.3(2)
C6 C7 C8 C3 -0.1(4)
O7 N9 C8 C7 151.9(2)
O6 N9 C8 C7 -26.9(3)
O7 N9 C8 C3 -31.6(3)
O6 N9 C8 C3 149.6(2)
O1 C3 C8 C7 174.8(2)
C4 C3 C8 C7 0.2(3)
O1 C3 C8 N9 -1.4(4)
C4 C3 C8 N9 -176.1(2)
O8 C9 C10 C11 175.9(2)
C14 C9 C10 C11 0.5(3)
O8 C9 C10 N10 0.0(4)
C14 C9 C10 N10 -175.4(2)
O9 N10 C10 C11 154.1(3)
O10 N10 C10 C11 -26.4(3)
O9 N10 C10 C9 -29.6(4)
O10 N10 C10 C9 149.9(3)
C9 C10 C11 C12 0.9(4)
N10 C10 C11 C12 176.9(2)
C10 C11 C12 C13 -2.5(4)
C10 C11 C12 N11 -179.9(2)
O11 N11 C12 C13 -179.5(2)
O12 N11 C12 C13 -0.6(4)
O11 N11 C12 C11 -2.1(3)
O12 N11 C12 C11 176.8(2)
C11 C12 C13 C14 2.6(4)
N11 C12 C13 C14 180.0(2)
C12 C13 C14 N12 -177.2(2)
C12 C13 C14 C9 -1.1(4)
O14 N12 C14 C13 -150.4(3)
O13 N12 C14 C13 27.8(3)
O14 N12 C14 C9 33.4(4)
O13 N12 C14 C9 -148.5(2)
O8 C9 C14 C13 -176.0(2)
C10 C9 C14 C13 -0.4(3)
O8 C9 C14 N12 0.0(4)
C10 C9 C14 N12 175.5(2)
