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#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/76/4517676.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_4517676
loop_
_publ_author_name
'Hu, Lu'
'He, Chunlin'
'Zhao, Gang'
'Imler, Gregory H.'
'Parrish, Damon A.'
'Shreeve, Jean’ne M.'
_publ_section_title
;
 Selecting Suitable Substituents for Energetic Materials Based on a Fused
 Triazolo-[1,2,4,5]tetrazine Ring
;
_journal_name_full               'ACS Applied Energy Materials'
_journal_paper_doi               10.1021/acsaem.0c00487
_journal_year                    2020
_chemical_formula_moiety         'C3 H2 N9 O, H4 N'
_chemical_formula_sum            'C3 H6 N10 O'
_chemical_formula_weight         198.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.5425(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.93720(10)
_cell_length_b                   6.0659(2)
_cell_length_c                   33.8775(8)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.526
_cell_measurement_theta_min      2.611
_cell_volume                     808.29(4)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            4574
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.517
_diffrn_reflns_theta_min         2.611
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0131(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1508
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0379
_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)+(0.0342P)²+0.2522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1268
_reflns_number_total             1508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ae0c00487_si_002.cif
_cod_data_source_block           shrv618
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4517676
_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.
;
_shelx_estimated_absorpt_t_min   0.763
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.1698(4) 0.5030(2) 0.26295(3) 0.0468(4) Uani 1 1 d . . . . .
N2 N 0.1735(4) 0.6336(3) 0.29240(4) 0.0397(4) Uani 1 1 d . . . . .
N3 N 0.3262(4) 0.5498(2) 0.32314(4) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.3127(4) 0.6891(3) 0.35507(5) 0.0311(4) Uani 1 1 d . . . . .
N5 N 0.1412(4) 0.8779(2) 0.36006(4) 0.0383(4) Uani 1 1 d . . . . .
N6 N 0.1985(4) 0.9466(2) 0.39814(4) 0.0405(4) Uani 1 1 d . . . . .
C7 C 0.4032(4) 0.8000(3) 0.41546(5) 0.0325(4) Uani 1 1 d . . . . .
N8 N 0.5258(4) 0.7981(2) 0.45350(4) 0.0382(4) Uani 1 1 d . . . . .
N9 N 0.7193(4) 0.6358(2) 0.46393(4) 0.0360(4) Uani 1 1 d . . . . .
C10 C 0.7962(4) 0.4709(3) 0.43575(5) 0.0308(4) Uani 1 1 d . . . . .
N11 N 1.0035(4) 0.3163(3) 0.45045(4) 0.0439(4) Uani 1 1 d . . . . .
H11A H 1.0676 0.2105 0.4356 0.053 Uiso 1 1 calc R U . . .
H11B H 1.0738 0.3217 0.4748 0.053 Uiso 1 1 calc R U . . .
N12 N 0.6889(4) 0.4626(2) 0.39857(4) 0.0313(3) Uani 1 1 d . . . . .
N13 N 0.4799(3) 0.6378(2) 0.38956(4) 0.0290(3) Uani 1 1 d . . . . .
N14 N 0.7356(4) 0.6591(3) 0.20146(5) 0.0415(4) Uani 1 1 d D . . . .
H14A H 0.568(4) 0.731(3) 0.2140(6) 0.075(8) Uiso 1 1 d D . . . .
H14B H 0.878(5) 0.592(4) 0.2200(5) 0.072(7) Uiso 1 1 d D . . . .
H14C H 0.852(5) 0.762(3) 0.1876(6) 0.079(8) Uiso 1 1 d D . . . .
H14D H 0.642(5) 0.557(3) 0.1846(5) 0.059(7) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 N2 N3 112.19(14) . . ?
N2 N3 C4 111.19(14) . . ?
N5 C4 N13 108.40(14) . . ?
N5 C4 N3 131.27(15) . . ?
N13 C4 N3 120.26(14) . . ?
C4 N5 N6 108.43(13) . . ?
C7 N6 N5 106.65(13) . . ?
N6 C7 N8 127.80(15) . . ?
N6 C7 N13 110.41(14) . . ?
N8 C7 N13 121.79(14) . . ?
N9 N8 C7 116.73(14) . . ?
N8 N9 C10 119.65(13) . . ?
N12 C10 N11 120.00(15) . . ?
N12 C10 N9 127.00(14) . . ?
N11 C10 N9 113.00(14) . . ?
C10 N11 H11A 120.0 . . ?
C10 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C10 N12 N13 110.40(13) . . ?
C4 N13 C7 106.11(13) . . ?
C4 N13 N12 129.47(13) . . ?
C7 N13 N12 124.41(13) . . ?
H14A N14 H14B 108.8(16) . . ?
H14A N14 H14C 107.6(17) . . ?
H14B N14 H14C 110(2) . . ?
H14A N14 H14D 109.6(16) . . ?
H14B N14 H14D 110(2) . . ?
H14C N14 H14D 109.8(16) . . ?
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
O1 N2 1.2737(18) . ?
N2 N3 1.2840(19) . ?
N3 C4 1.376(2) . ?
C4 N5 1.344(2) . ?
C4 N13 1.352(2) . ?
N5 N6 1.365(2) . ?
N6 C7 1.320(2) . ?
C7 N8 1.356(2) . ?
C7 N13 1.361(2) . ?
N8 N9 1.284(2) . ?
N9 C10 1.424(2) . ?
C10 N12 1.312(2) . ?
C10 N11 1.326(2) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 N13 1.3703(18) . ?
N14 H14A 0.914(9) . ?
N14 H14B 0.918(10) . ?
N14 H14C 0.914(9) . ?
N14 H14D 0.907(9) . ?
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
N11 H11A N6 0.86 2.12 2.980(2) 177.0 1_645
N11 H11B N9 0.86 2.21 3.0676(19) 174.6 3_766
N14 H14A O1 0.914(9) 2.065(12) 2.920(2) 155.0(19) 2
N14 H14A N2 0.914(9) 2.625(17) 3.310(2) 132.2(17) 2
N14 H14B O1 0.918(10) 1.892(11) 2.800(2) 170(2) 1_655
N14 H14B N2 0.918(10) 2.678(17) 3.467(2) 144.5(19) 1_655
N14 H14C N3 0.914(9) 2.199(12) 3.068(2) 159(2) 2_655
N14 H14D N5 0.907(9) 2.138(11) 3.030(2) 167(2) 2_545
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 N3 C4 -177.05(14) . . . . ?
N2 N3 C4 N5 8.3(3) . . . . ?
N2 N3 C4 N13 -175.21(16) . . . . ?
N13 C4 N5 N6 -0.3(2) . . . . ?
N3 C4 N5 N6 176.51(17) . . . . ?
C4 N5 N6 C7 0.2(2) . . . . ?
N5 N6 C7 N8 -179.06(17) . . . . ?
N5 N6 C7 N13 0.0(2) . . . . ?
N6 C7 N8 N9 179.18(18) . . . . ?
N13 C7 N8 N9 0.2(3) . . . . ?
C7 N8 N9 C10 0.5(2) . . . . ?
N8 N9 C10 N12 -0.1(3) . . . . ?
N8 N9 C10 N11 178.78(16) . . . . ?
N11 C10 N12 N13 -179.71(16) . . . . ?
N9 C10 N12 N13 -0.9(2) . . . . ?
N5 C4 N13 C7 0.31(19) . . . . ?
N3 C4 N13 C7 -176.93(15) . . . . ?
N5 C4 N13 N12 -179.34(15) . . . . ?
N3 C4 N13 N12 3.4(3) . . . . ?
N6 C7 N13 C4 -0.2(2) . . . . ?
N8 C7 N13 C4 178.94(16) . . . . ?
N6 C7 N13 N12 179.48(15) . . . . ?
N8 C7 N13 N12 -1.4(3) . . . . ?
C10 N12 N13 C4 -178.81(16) . . . . ?
C10 N12 N13 C7 1.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346658
