#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:18:48 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266125 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060503.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_7060503
loop_
_publ_author_name
'Gu, Hao'
'Cheng, Guangbin'
'Yang, Hongwei'
_publ_section_title
;
 Tricyclic nitrogen-rich explosives with a planar backbone:
 bis(1,2,4-triazolyl)-1,2,3-triazoles as potential stable green gas
 generants
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7758
_journal_page_last               7765
_journal_paper_doi               10.1039/D1NJ00076D
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C6 H3 N11 O4, 3(H2 O)'
_chemical_formula_sum            'C6 H9 N11 O7'
_chemical_formula_weight         347.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-09 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.805(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.555(5)
_cell_length_b                   4.9529(8)
_cell_length_c                   21.680(4)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.694
_cell_measurement_theta_min      2.917
_cell_volume                     2686.8(8)
_computing_data_collection       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0965
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12282
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.559
_diffrn_reflns_theta_min         2.911
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0968 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.7656. The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0666
_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)+(0.0768P)²+4.1351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1603
_reflns_number_total             2483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00076d2.cif
_cod_data_source_block           22019261GH2_0m
_cod_depositor_comments          'Adding full bibliography for 7060503.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7060503
_shelx_shelxl_version_number     2018/3
_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   0.991
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.43321(11) 1.3667(6) 0.70716(15) 0.0298(7) Uani 1 1 d . . . . .
O4 O 0.38385(10) -0.1044(6) 0.39710(15) 0.0299(7) Uani 1 1 d G . . . .
H4A H 0.391785 -0.242650 0.379122 0.045 Uiso 1 1 d G U . . .
H4B H 0.350082 -0.110097 0.385230 0.045 Uiso 1 1 d G U . . .
O6 O 0.34672(11) 1.3816(6) 0.66206(15) 0.0346(8) Uani 1 1 d . . . . .
O3 O 0.28026(11) -0.0056(7) 0.37270(17) 0.0397(8) Uani 1 1 d G . . . .
H3A H 0.271917 -0.161670 0.383100 0.060 Uiso 1 1 d G U . . .
H3B H 0.258070 0.015448 0.328077 0.060 Uiso 1 1 d G U . . .
O2 O 0.68977(11) 0.5506(7) 0.72259(16) 0.0402(8) Uani 1 1 d . . . . .
O5 O 0.27146(10) 0.4921(6) 0.43752(17) 0.0376(8) Uani 1 1 d G . . . .
H5A H 0.241774 0.474904 0.439123 0.056 Uiso 1 1 d G U . . .
H5B H 0.278524 0.341805 0.422847 0.056 Uiso 1 1 d G U . . .
O1 O 0.69018(11) 0.9059(6) 0.78085(16) 0.0400(8) Uani 1 1 d . . . . .
N3 N 0.53299(11) 0.8212(6) 0.67628(16) 0.0213(7) Uani 1 1 d . . . . .
H3 H 0.504449 0.898311 0.674048 0.026 Uiso 1 1 calc R U . . .
N10 N 0.42549(11) 0.9324(6) 0.62658(16) 0.0210(7) Uani 1 1 d . . . . .
N4 N 0.58160(11) 0.5425(6) 0.65296(16) 0.0217(7) Uani 1 1 d . . . . .
N7 N 0.40085(12) 0.3707(6) 0.50514(17) 0.0234(8) Uani 1 1 d . . . . .
N5 N 0.48747(12) 0.2790(6) 0.54554(16) 0.0234(8) Uani 1 1 d . . . . .
N6 N 0.43697(12) 0.2204(6) 0.50056(16) 0.0229(8) Uani 1 1 d . . . . .
H6 H 0.428206 0.089135 0.469596 0.027 Uiso 1 1 calc R U . . .
N1 N 0.66796(12) 0.7273(7) 0.73845(18) 0.0273(8) Uani 1 1 d . . . . .
N2 N 0.58374(12) 0.8953(6) 0.72065(16) 0.0236(8) Uani 1 1 d . . . . .
N9 N 0.33581(12) 0.9625(7) 0.57737(17) 0.0271(8) Uani 1 1 d . . . . .
N11 N 0.38796(13) 1.2834(7) 0.66783(18) 0.0259(8) Uani 1 1 d . . . . .
N8 N 0.34958(11) 0.7628(7) 0.54787(17) 0.0252(8) Uani 1 1 d . . . . .
H8 H 0.326773 0.657506 0.514018 0.030 Uiso 1 1 calc R U . . .
C1 C 0.60969(14) 0.7221(8) 0.70355(19) 0.0208(9) Uani 1 1 d . . . . .
C2 C 0.53207(14) 0.6144(8) 0.6362(2) 0.0219(9) Uani 1 1 d . . . . .
C4 C 0.42955(14) 0.5462(8) 0.55667(19) 0.0213(9) Uani 1 1 d . . . . .
C5 C 0.40287(14) 0.7447(8) 0.57686(19) 0.0216(9) Uani 1 1 d . . . . .
C6 C 0.38324(14) 1.0560(8) 0.6244(2) 0.0225(9) Uani 1 1 d . . . . .
C3 C 0.48403(14) 0.4869(8) 0.5816(2) 0.0203(9) Uani 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
H4A O4 H4B 109.4 . . ?
H3A O3 H3B 104.5 . . ?
H5A O5 H5B 109.5 . . ?
C2 N3 N2 110.5(3) . . ?
C2 N3 H3 124.7 . . ?
N2 N3 H3 124.7 . . ?
C5 N10 C6 102.4(3) . . ?
C2 N4 C1 100.7(3) . . ?
N6 N7 C4 104.1(3) . . ?
C3 N5 N6 103.9(3) . . ?
N7 N6 N5 115.8(3) . . ?
N7 N6 H6 122.1 . . ?
N5 N6 H6 122.1 . . ?
O1 N1 O2 126.0(3) . . ?
O1 N1 C1 117.1(3) . . ?
O2 N1 C1 116.9(3) . . ?
C1 N2 N3 100.5(3) . . ?
C6 N9 N8 101.5(3) . . ?
O6 N11 O7 125.2(4) . . ?
O6 N11 C6 117.7(3) . . ?
O7 N11 C6 117.1(3) . . ?
N9 N8 C5 110.8(3) . . ?
N9 N8 H8 124.6 . . ?
C5 N8 H8 124.6 . . ?
N2 C1 N4 118.3(3) . . ?
N2 C1 N1 120.4(3) . . ?
N4 C1 N1 121.4(3) . . ?
N4 C2 N3 110.0(3) . . ?
N4 C2 C3 124.7(3) . . ?
N3 C2 C3 125.2(3) . . ?
N7 C4 C3 107.7(3) . . ?
N7 C4 C5 119.8(3) . . ?
C3 C4 C5 132.5(3) . . ?
N10 C5 N8 109.3(3) . . ?
N10 C5 C4 127.1(3) . . ?
N8 C5 C4 123.5(3) . . ?
N9 C6 N10 116.0(4) . . ?
N9 C6 N11 121.2(3) . . ?
N10 C6 N11 122.7(3) . . ?
N5 C3 C4 108.5(3) . . ?
N5 C3 C2 120.5(3) . . ?
C4 C3 C2 131.0(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
O7 N11 1.227(4) . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8704 . ?
O6 N11 1.224(4) . ?
O3 H3A 0.8700 . ?
O3 H3B 0.8704 . ?
O2 N1 1.216(4) . ?
O5 H5A 0.8691 . ?
O5 H5B 0.8704 . ?
O1 N1 1.212(4) . ?
N3 C2 1.336(5) . ?
N3 N2 1.348(4) . ?
N3 H3 0.8800 . ?
N10 C5 1.331(5) . ?
N10 C6 1.334(5) . ?
N4 C2 1.328(5) . ?
N4 C1 1.338(5) . ?
N7 N6 1.314(4) . ?
N7 C4 1.339(5) . ?
N5 C3 1.325(5) . ?
N5 N6 1.327(4) . ?
N6 H6 0.8800 . ?
N1 C1 1.459(5) . ?
N2 C1 1.299(5) . ?
N9 C6 1.326(5) . ?
N9 N8 1.336(5) . ?
N11 C6 1.432(5) . ?
N8 C5 1.341(4) . ?
N8 H8 0.8800 . ?
C2 C3 1.454(5) . ?
C4 C3 1.410(5) . ?
C4 C5 1.435(5) . ?
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
O4 H4B O3 0.87 1.95 2.786(4) 161.1 . yes
O4 H4A N4 0.87 1.94 2.809(4) 173.1 5_656 yes
N3 H3 N10 0.88 1.98 2.775(4) 148.9 . yes
N6 H6 O4 0.88 1.75 2.577(4) 154.8 . yes
N8 H8 O5 0.88 1.84 2.712(4) 169.6 . yes
