#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/20/7712010.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_7712010
loop_
_publ_author_name
'Kumar, Parasar'
'Ghule, Vikas D.'
'Dharavath, Srinivas'
_publ_section_title
;
 Facile synthesis of thermally stable
 tetrazolo[1,5-b][1,2,4]triazine substituted energetic materials:
 synthesis and characterization.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              747
_journal_page_last               753
_journal_paper_doi               10.1039/d2dt03814e
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C4 H3 N7 O2'
_chemical_formula_sum            'C4 H3 N7 O2'
_chemical_formula_weight         181.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-09-29 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                92.6160(10)
_cell_angle_beta                 93.1460(10)
_cell_angle_gamma                99.8180(10)
_cell_formula_units_Z            4
_cell_length_a                   8.5317(3)
_cell_length_b                   8.6151(3)
_cell_length_c                   9.1400(3)
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     659.93(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.979
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10100
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.235
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_description       irregular
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0377
_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)+(0.0326P)²+0.4962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2855
_reflns_number_total             3230
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03814e2.cif
_cod_data_source_block           6julb_0m_a
_cod_depositor_comments
;
Adding full bibliography for 7712010--7712013.cif.

2024-11-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C8 H6 N14 O4'
_cod_original_formula_weight         362.27
_cod_original_formula_moiety         '2(C4 H3 N7 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               7712010
_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_max   0.956
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N25(H25), N4(H4), N22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O21 O 0.36537(12) 0.83606(11) -0.14600(11) 0.0142(2) Uani 1 1 d . . . . .
O5 O 0.57693(12) 0.61309(12) 0.65812(11) 0.0154(2) Uani 1 1 d . . . . .
O1 O 0.37090(12) 0.92237(12) 0.33336(11) 0.0168(2) Uani 1 1 d . . . . .
O24 O 0.07516(13) 1.05565(12) 0.18478(12) 0.0188(2) Uani 1 1 d . . . . .
N26 N 0.13558(14) 0.66528(13) 0.13763(13) 0.0117(2) Uani 1 1 d . . . . .
N3 N 0.76776(14) 0.87524(14) 0.40762(13) 0.0120(2) Uani 1 1 d . . . . .
N14 N 0.23214(14) 0.39072(13) 0.03427(13) 0.0113(2) Uani 1 1 d . . . . .
N15 N 0.30178(14) 0.28719(14) -0.04537(13) 0.0127(2) Uani 1 1 d . . . . .
N17 N 0.36774(14) 0.51000(13) -0.13332(13) 0.0108(2) Uani 1 1 d . . . . .
N2 N 0.63732(14) 0.92605(14) 0.35415(12) 0.0119(2) Uani 1 1 d . . . . .
H2 H 0.651629 1.001701 0.292195 0.014 Uiso 1 1 calc R U . . .
N25 N 0.08217(14) 0.79345(13) 0.18573(13) 0.0120(2) Uani 1 1 d . . . . .
H25 H 0.015058 0.782561 0.255819 0.014 Uiso 1 1 calc R U . . .
N4 N 0.46828(14) 0.75771(13) 0.49023(13) 0.0121(2) Uani 1 1 d . . . . .
H4 H 0.371434 0.716216 0.512119 0.015 Uiso 1 1 calc R U . . .
N7 N 1.13088(14) 0.66693(14) 0.57107(13) 0.0136(2) Uani 1 1 d . . . . .
N8 N 1.06943(14) 0.62001(14) 0.69231(13) 0.0131(2) Uani 1 1 d . . . . .
N9 N 0.91962(14) 0.64774(13) 0.68439(13) 0.0108(2) Uani 1 1 d . . . . .
N6 N 1.02373(14) 0.72584(14) 0.48454(13) 0.0128(2) Uani 1 1 d . . . . .
N22 N 0.22347(14) 0.94931(13) 0.02000(13) 0.0126(2) Uani 1 1 d . . . . .
H22 H 0.253835 1.042262 -0.015282 0.015 Uiso 1 1 calc R U . . .
N16 N 0.38392(14) 0.35729(13) -0.14660(13) 0.0127(2) Uani 1 1 d . . . . .
C18 C 0.27474(15) 0.52909(15) -0.02337(14) 0.0097(2) Uani 1 1 d . . . . .
C19 C 0.22565(16) 0.67572(15) 0.02720(14) 0.0099(2) Uani 1 1 d . . . . .
C10 C 0.89354(16) 0.71475(15) 0.55846(14) 0.0100(2) Uani 1 1 d . . . . .
C12 C 0.59336(16) 0.70577(15) 0.56051(14) 0.0109(3) Uani 1 1 d . . . . .
C20 C 0.27893(16) 0.82419(15) -0.04291(14) 0.0105(2) Uani 1 1 d . . . . .
C13 C 0.48323(16) 0.87089(16) 0.38715(15) 0.0118(3) Uani 1 1 d . . . . .
C11 C 0.74909(15) 0.77038(15) 0.50568(14) 0.0102(2) Uani 1 1 d . . . . .
C23 C 0.12367(17) 0.94218(16) 0.13443(15) 0.0130(3) Uani 1 1 d . . . . .
H17 H 0.416(2) 0.578(2) -0.193(2) 0.023(5) Uiso 1 1 d . . . . .
H9 H 0.861(3) 0.632(3) 0.761(2) 0.030(5) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N26 N25 118.60(11) . . ?
C11 N3 N2 117.51(12) . . ?
C18 N14 N15 105.41(11) . . ?
N16 N15 N14 111.15(11) . . ?
N16 N17 H17 119.6(13) . . ?
C18 N17 N16 108.86(11) . . ?
C18 N17 H17 131.6(13) . . ?
N3 N2 H2 117.0 . . ?
N3 N2 C13 125.99(11) . . ?
C13 N2 H2 117.0 . . ?
N26 N25 H25 117.4 . . ?
N26 N25 C23 125.18(12) . . ?
C23 N25 H25 117.4 . . ?
C12 N4 H4 117.7 . . ?
C12 N4 C13 124.55(12) . . ?
C13 N4 H4 117.7 . . ?
N8 N7 N6 110.82(11) . . ?
N7 N8 N9 106.28(11) . . ?
N8 N9 H9 119.6(14) . . ?
C10 N9 N8 108.70(11) . . ?
C10 N9 H9 131.2(14) . . ?
C10 N6 N7 105.55(11) . . ?
C20 N22 H22 117.3 . . ?
C20 N22 C23 125.45(11) . . ?
C23 N22 H22 117.3 . . ?
N15 N16 N17 106.01(11) . . ?
N14 C18 N17 108.57(11) . . ?
N14 C18 C19 124.61(12) . . ?
N17 C18 C19 126.82(12) . . ?
N26 C19 C18 115.62(12) . . ?
N26 C19 C20 123.36(12) . . ?
C18 C19 C20 121.01(12) . . ?
N9 C10 C11 127.90(12) . . ?
N6 C10 N9 108.63(12) . . ?
N6 C10 C11 123.47(12) . . ?
O5 C12 N4 123.02(12) . . ?
O5 C12 C11 123.47(12) . . ?
N4 C12 C11 113.50(11) . . ?
O21 C20 N22 123.03(12) . . ?
O21 C20 C19 124.04(12) . . ?
N22 C20 C19 112.92(11) . . ?
O1 C13 N2 122.13(13) . . ?
O1 C13 N4 123.22(13) . . ?
N2 C13 N4 114.59(12) . . ?
N3 C11 C10 115.89(12) . . ?
N3 C11 C12 123.53(12) . . ?
C10 C11 C12 120.56(11) . . ?
O24 C23 N25 122.54(13) . . ?
O24 C23 N22 123.13(13) . . ?
N25 C23 N22 114.33(12) . . ?
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
O21 C20 1.2254(17) . ?
O5 C12 1.2222(17) . ?
O1 C13 1.2124(17) . ?
O24 C23 1.2069(17) . ?
N26 N25 1.3302(16) . ?
N26 C19 1.2990(18) . ?
N3 N2 1.3397(16) . ?
N3 C11 1.2982(17) . ?
N14 N15 1.3592(16) . ?
N14 C18 1.3271(17) . ?
N15 N16 1.2999(17) . ?
N17 N16 1.3468(16) . ?
N17 C18 1.3354(17) . ?
N17 H17 0.89(2) . ?
N2 H2 0.8800 . ?
N2 C13 1.3743(18) . ?
N25 H25 0.8800 . ?
N25 C23 1.3804(18) . ?
N4 H4 0.8800 . ?
N4 C12 1.3659(18) . ?
N4 C13 1.3818(17) . ?
N7 N8 1.3032(17) . ?
N7 N6 1.3544(16) . ?
N8 N9 1.3384(16) . ?
N9 C10 1.3357(17) . ?
N9 H9 0.88(2) . ?
N6 C10 1.3233(17) . ?
N22 H22 0.8800 . ?
N22 C20 1.3651(17) . ?
N22 C23 1.3815(18) . ?
C18 C19 1.4606(18) . ?
C19 C20 1.4703(18) . ?
C10 C11 1.4624(18) . ?
C12 C11 1.4740(18) . ?
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
O5 C12 C11 N3 -176.15(13) . . . . ?
O5 C12 C11 C10 5.3(2) . . . . ?
N26 N25 C23 O24 -177.86(13) . . . . ?
N26 N25 C23 N22 2.8(2) . . . . ?
N26 C19 C20 O21 179.12(13) . . . . ?
N26 C19 C20 N22 -0.16(19) . . . . ?
N3 N2 C13 O1 -179.52(13) . . . . ?
N3 N2 C13 N4 2.99(19) . . . . ?
N14 N15 N16 N17 -0.08(15) . . . . ?
N14 C18 C19 N26 0.84(19) . . . . ?
N14 C18 C19 C20 179.83(12) . . . . ?
N15 N14 C18 N17 -0.40(14) . . . . ?
N15 N14 C18 C19 179.41(12) . . . . ?
N17 C18 C19 N26 -179.38(13) . . . . ?
N17 C18 C19 C20 -0.4(2) . . . . ?
N2 N3 C11 C10 178.41(11) . . . . ?
N2 N3 C11 C12 -0.17(19) . . . . ?
N25 N26 C19 C18 -177.69(11) . . . . ?
N25 N26 C19 C20 3.35(19) . . . . ?
N4 C12 C11 N3 4.73(19) . . . . ?
N4 C12 C11 C10 -173.78(11) . . . . ?
N7 N8 N9 C10 -1.28(15) . . . . ?
N7 N6 C10 N9 -1.41(14) . . . . ?
N7 N6 C10 C11 178.03(12) . . . . ?
N8 N7 N6 C10 0.63(15) . . . . ?
N8 N9 C10 N6 1.71(15) . . . . ?
N8 N9 C10 C11 -177.70(12) . . . . ?
N9 C10 C11 N3 158.01(13) . . . . ?
N9 C10 C11 C12 -23.4(2) . . . . ?
N6 N7 N8 N9 0.40(15) . . . . ?
N6 C10 C11 N3 -21.32(19) . . . . ?
N6 C10 C11 C12 157.30(13) . . . . ?
N16 N17 C18 N14 0.37(15) . . . . ?
N16 N17 C18 C19 -179.44(12) . . . . ?
C18 N14 N15 N16 0.30(15) . . . . ?
C18 N17 N16 N15 -0.17(14) . . . . ?
C18 C19 C20 O21 0.2(2) . . . . ?
C18 C19 C20 N22 -179.07(12) . . . . ?
C19 N26 N25 C23 -4.9(2) . . . . ?
C12 N4 C13 O1 -175.04(13) . . . . ?
C12 N4 C13 N2 2.42(19) . . . . ?
C20 N22 C23 O24 -178.54(14) . . . . ?
C20 N22 C23 N25 0.7(2) . . . . ?
C13 N4 C12 O5 175.06(13) . . . . ?
C13 N4 C12 C11 -5.82(18) . . . . ?
C11 N3 N2 C13 -4.0(2) . . . . ?
C23 N22 C20 O21 178.78(13) . . . . ?
C23 N22 C20 C19 -1.93(19) . . . . ?
