#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:02:18 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230025 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/73/7047311.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_7047311
loop_
_publ_author_name
'Zhang, Guojie'
'Chen, Ya'
'Liao, Longyu'
'Lu, Huanchang'
'Zhang, Zhenqi'
'Ma, Qing'
'Yang, Hongwei'
'Fan, Guijuan'
_publ_section_title
;
 5-Amino-1H-1,2,4-triazole-3-carbohydrazide and its applications in the
 synthesis of energetic salts: a new strategy for constructing the
 nitrogen-rich cation based on the energetic moiety combination.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13391
_journal_page_last               13401
_journal_paper_doi               10.1039/c8dt01760c
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C3 H8 N6 O, 2(Cl)'
_chemical_formula_sum            'C3 H8 Cl2 N6 O'
_chemical_formula_weight         215.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0906(3)
_cell_length_b                   4.70700(10)
_cell_length_c                   14.6257(4)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.041
_cell_measurement_theta_min      6.428
_cell_volume                     831.98(4)
_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-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_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  0.0476
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12363
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.214
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1597
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0298P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1552
_reflns_number_total             1597
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01760c2.cif
_cod_data_source_block           DH-ATCH
_cod_depositor_comments
'Adding full bibliography for 7047309--7047314.cif.'
_cod_database_code               7047311
_shelx_shelxl_version_number     2017/1
_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   0.872
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 0.35004(3) 0.01350(7) 0.41972(2) 0.01756(13) Uani 1 1 d .
Cl2 Cl 0.10534(3) 0.79058(7) 0.58253(2) 0.01571(13) Uani 1 1 d .
N1 N 0.27940(10) 0.1139(3) 0.16799(8) 0.0127(2) Uani 1 1 d .
N2 N 0.43673(10) 0.3209(3) 0.18001(8) 0.0154(3) Uani 1 1 d D
N3 N 0.36809(10) 0.4724(3) 0.23559(8) 0.0148(3) Uani 1 1 d .
N4 N 0.17369(10) 0.6300(3) 0.32864(8) 0.0138(3) Uani 1 1 d .
N5 N 0.07605(10) 0.6952(3) 0.37577(8) 0.0135(3) Uani 1 1 d .
N6 N 0.42614(12) -0.0791(3) 0.08169(9) 0.0184(3) Uani 1 1 d .
O1 O 0.09152(8) 0.2408(2) 0.26579(7) 0.0143(2) Uani 1 1 d .
C1 C 0.38349(11) 0.1064(3) 0.13849(9) 0.0130(3) Uani 1 1 d .
C2 C 0.27453(11) 0.3393(3) 0.22656(9) 0.0117(3) Uani 1 1 d .
C3 C 0.17138(11) 0.3980(3) 0.27571(9) 0.0115(3) Uani 1 1 d .
H5C H 0.0922(16) 0.728(4) 0.4364(15) 0.029(5) Uiso 1 1 d .
H6B H 0.3879(17) -0.193(4) 0.0532(14) 0.025(5) Uiso 1 1 d .
H4 H 0.2293(17) 0.721(4) 0.3434(13) 0.024(5) Uiso 1 1 d .
H5B H 0.0434(16) 0.846(5) 0.3525(13) 0.026(5) Uiso 1 1 d .
H1 H 0.2282(17) 0.005(4) 0.1510(13) 0.024(5) Uiso 1 1 d .
H5A H 0.0301(19) 0.553(5) 0.3739(15) 0.035(6) Uiso 1 1 d .
H2 H 0.4966(13) 0.379(4) 0.1656(12) 0.023(5) Uiso 1 1 d D
H6A H 0.493(2) -0.086(5) 0.0795(15) 0.037(6) 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'
Cl Cl 0.1484 0.1585 '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 C2 106.28(12)
C1 N1 H1 125.5(13)
C2 N1 H1 128.2(13)
C1 N2 N3 111.68(12)
C1 N2 H2 124.3(14)
N3 N2 H2 122.5(14)
C2 N3 N2 103.24(11)
C3 N4 N5 117.03(12)
C3 N4 H4 125.5(14)
N5 N4 H4 116.5(14)
N4 N5 H5C 110.5(12)
N4 N5 H5B 111.0(13)
H5C N5 H5B 108.7(18)
N4 N5 H5A 111.1(14)
H5C N5 H5A 106.1(18)
H5B N5 H5A 109.4(18)
C1 N6 H6B 122.1(14)
C1 N6 H6A 117.3(16)
H6B N6 H6A 120(2)
N6 C1 N2 126.49(14)
N6 C1 N1 127.36(14)
N2 C1 N1 106.13(12)
N3 C2 N1 112.66(12)
N3 C2 C3 127.17(13)
N1 C2 C3 120.07(12)
O1 C3 N4 124.45(13)
O1 C3 C2 120.15(12)
N4 C3 C2 115.39(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3430(18)
N1 C2 1.3659(18)
N1 H1 0.84(2)
N2 C1 1.3339(19)
N2 N3 1.3777(17)
N2 H2 0.808(15)
N3 C2 1.2963(18)
N4 C3 1.3382(18)
N4 N5 1.4182(16)
N4 H4 0.82(2)
N5 H5C 0.91(2)
N5 H5B 0.88(2)
N5 H5A 0.87(2)
N6 C1 1.3206(19)
N6 H6B 0.82(2)
N6 H6A 0.82(2)
O1 C3 1.2217(17)
C2 C3 1.4840(19)
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
_geom_hbond_publ_flag
N6 H6A Cl1 0.82(2) 2.67(2) 3.3171(14) 137(2) 2_645 yes
N2 H2 Cl1 0.808(15) 2.352(15) 3.1338(13) 163.0(17) 2_655 yes
N5 H5A Cl2 0.87(2) 2.40(2) 3.2387(13) 161.9(19) 3_566 yes
N1 H1 Cl2 0.84(2) 2.25(2) 3.0756(13) 170.3(18) 4_565 yes
N5 H5B O1 0.88(2) 2.39(2) 2.8613(16) 113.6(16) 2 yes
N5 H5B O1 0.88(2) 2.33(2) 3.0392(17) 137.8(16) 1_565 yes
N5 H5B Cl2 0.88(2) 2.68(2) 3.3348(13) 132.8(16) 3_576 yes
N4 H4 Cl1 0.82(2) 2.28(2) 3.0676(13) 162.5(18) 1_565 yes
N6 H6B Cl1 0.82(2) 2.50(2) 3.2418(15) 152.3(18) 4 yes
N5 H5C Cl2 0.91(2) 2.16(2) 3.0671(13) 171.6(17) . yes
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 N2 N3 C2 0.89(15)
N3 N2 C1 N6 -179.38(13)
N3 N2 C1 N1 -0.91(15)
C2 N1 C1 N6 179.01(14)
C2 N1 C1 N2 0.56(15)
N2 N3 C2 N1 -0.51(15)
N2 N3 C2 C3 175.77(13)
C1 N1 C2 N3 -0.01(16)
C1 N1 C2 C3 -176.59(12)
N5 N4 C3 O1 -0.2(2)
N5 N4 C3 C2 179.17(11)
N3 C2 C3 O1 -174.13(13)
N1 C2 C3 O1 1.9(2)
N3 C2 C3 N4 6.5(2)
N1 C2 C3 N4 -177.47(11)
