#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:40:54 +0300 (Fri, 05 May 2023) $
#$Revision: 283344 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/20/7712012.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_7712012
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 H2 N7 O2, H2 O, C3 H7 N8'
_chemical_formula_sum            'C7 H11 N15 O3'
_chemical_formula_weight         353.31
_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                105.143(6)
_cell_angle_beta                 92.926(7)
_cell_angle_gamma                96.537(7)
_cell_formula_units_Z            2
_cell_length_a                   6.6541(13)
_cell_length_b                   9.5463(18)
_cell_length_c                   10.9893(19)
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.23
_cell_volume                     667.1(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11300
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         1.927
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9037.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0386
_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)+(0.0466P)²+0.2946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2760
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03814e2.cif
_cod_data_source_block           6sepb_o_0m_a
_cod_depositor_comments
'Adding full bibliography for 7712010--7712013.cif.'
_cod_database_code               7712012
_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   0.972
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O002(H00A,H00B)
2.b Rotating group:
 N22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), N11(H11), N18(H18)
2.d X=CH2 refined with riding coordinates:
 N24(H24A,H24B), N17(H17A,H17B)
;
_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
O13 O 0.34495(16) 0.92780(11) 0.70701(9) 0.0178(2) Uani 1 1 d . . . . .
O002 O 0.58482(18) 1.20563(12) 0.54954(10) 0.0207(2) Uani 1 1 d G . . . .
H00A H 0.604939 1.142727 0.482270 0.031 Uiso 1 1 d G U . . .
H00B H 0.631006 1.287487 0.537971 0.031 Uiso 1 1 d G U . . .
O10 O 0.52397(17) 1.42241(11) 0.83682(10) 0.0191(2) Uani 1 1 d . . . . .
N21 N 0.22418(18) 0.28748(13) 0.39723(11) 0.0134(2) Uani 1 1 d . . . . .
N15 N 0.12996(18) 0.33873(13) 0.58678(11) 0.0131(2) Uani 1 1 d . . . . .
N8 N 0.40792(18) 1.30118(13) 0.97770(11) 0.0147(3) Uani 1 1 d . . . . .
H8 H 0.428283 1.383342 1.038662 0.018 Uiso 1 1 calc R U . . .
N11 N 0.42439(19) 1.17562(13) 0.76837(11) 0.0147(2) Uani 1 1 d . . . . .
H11 H 0.449206 1.175825 0.690519 0.018 Uiso 1 1 calc R U . . .
N2 N 0.20573(18) 0.93135(13) 1.08306(11) 0.0139(2) Uani 1 1 d . . . . .
N7 N 0.33108(18) 1.17930(13) 1.00815(11) 0.0138(2) Uani 1 1 d . . . . .
N14 N 0.08506(18) 0.18689(12) 0.54490(11) 0.0140(2) Uani 1 1 d . . . . .
N3 N 0.12314(18) 0.79571(13) 1.08163(11) 0.0149(3) Uani 1 1 d . . . . .
N19 N 0.24979(18) 0.54449(13) 0.53946(11) 0.0143(2) Uani 1 1 d . . . . .
N4 N 0.08907(19) 0.71471(13) 0.96393(11) 0.0163(3) Uani 1 1 d . . . . .
N18 N 0.17929(18) 0.56976(13) 0.66147(11) 0.0139(2) Uani 1 1 d . . . . .
H18 H 0.182773 0.657655 0.713412 0.017 Uiso 1 1 calc R U . . .
N5 N 0.14906(19) 0.79507(13) 0.88437(11) 0.0155(3) Uani 1 1 d . . . . .
N24 N 0.14793(19) 0.03008(13) 0.34998(11) 0.0172(3) Uani 1 1 d . . . . .
H24A H 0.102095 -0.049018 0.372209 0.021 Uiso 1 1 calc R U . . .
H24B H 0.193066 0.022130 0.274901 0.021 Uiso 1 1 calc R U . . .
N17 N 0.0291(2) 0.43043(13) 0.79493(11) 0.0177(3) Uani 1 1 d . . . . .
H17A H 0.020312 0.507859 0.857802 0.021 Uiso 1 1 calc R U . . .
H17B H -0.013648 0.342338 0.801758 0.021 Uiso 1 1 calc R U . . .
N22 N 0.3098(2) 0.29817(14) 0.28591(11) 0.0176(3) Uani 1 1 d . . . . .
H22A H 0.414633 0.251216 0.275804 0.021 Uiso 1 1 d R U . . .
H22B H 0.222174 0.260289 0.220985 0.021 Uiso 1 1 d R U . . .
C20 C 0.2138(2) 0.40184(15) 0.50060(13) 0.0131(3) Uani 1 1 d . . . . .
C6 C 0.3020(2) 1.05599(15) 0.92080(12) 0.0120(3) Uani 1 1 d . . . . .
C23 C 0.1490(2) 0.16095(15) 0.42943(13) 0.0130(3) Uani 1 1 d . . . . .
C16 C 0.1065(2) 0.44642(15) 0.69029(13) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.4570(2) 1.30776(15) 0.85956(13) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.2197(2) 0.92729(15) 0.96062(12) 0.0123(3) Uani 1 1 d . . . . .
C12 C 0.3561(2) 1.04370(15) 0.78975(13) 0.0135(3) 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
H00A O002 H00B 104.6 . . ?
C20 N21 N22 125.42(12) . . ?
C20 N21 C23 106.56(11) . . ?
C23 N21 N22 127.83(11) . . ?
C20 N15 N14 114.30(11) . . ?
C16 N15 N14 137.70(12) . . ?
C16 N15 C20 107.94(12) . . ?
N7 N8 H8 117.3 . . ?
N7 N8 C9 125.35(12) . . ?
C9 N8 H8 117.3 . . ?
C9 N11 H11 117.5 . . ?
C12 N11 H11 117.5 . . ?
C12 N11 C9 124.94(12) . . ?
N3 N2 C1 104.79(11) . . ?
C6 N7 N8 118.84(12) . . ?
C23 N14 N15 101.15(11) . . ?
N4 N3 N2 109.41(11) . . ?
C20 N19 N18 100.77(11) . . ?
N3 N4 N5 109.75(11) . . ?
N19 N18 H18 123.3 . . ?
C16 N18 N19 113.34(11) . . ?
C16 N18 H18 123.3 . . ?
C1 N5 N4 104.38(11) . . ?
H24A N24 H24B 120.0 . . ?
C23 N24 H24A 120.0 . . ?
C23 N24 H24B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C16 N17 H17A 120.0 . . ?
C16 N17 H17B 120.0 . . ?
N21 N22 H22A 110.0 . . ?
N21 N22 H22B 110.3 . . ?
H22A N22 H22B 108.4 . . ?
N15 C20 N21 104.54(12) . . ?
N19 C20 N21 141.62(13) . . ?
N19 C20 N15 113.78(12) . . ?
N7 C6 C1 116.03(12) . . ?
N7 C6 C12 122.35(13) . . ?
C1 C6 C12 121.57(12) . . ?
N14 C23 N21 113.43(12) . . ?
N24 C23 N21 121.02(12) . . ?
N24 C23 N14 125.54(13) . . ?
N18 C16 N15 104.17(12) . . ?
N17 C16 N15 126.70(13) . . ?
N17 C16 N18 129.13(13) . . ?
O10 C9 N8 122.56(13) . . ?
O10 C9 N11 122.69(13) . . ?
N8 C9 N11 114.75(12) . . ?
N2 C1 C6 122.11(12) . . ?
N5 C1 N2 111.67(12) . . ?
N5 C1 C6 126.21(12) . . ?
O13 C12 N11 122.08(13) . . ?
O13 C12 C6 124.32(13) . . ?
N11 C12 C6 113.59(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
O13 C12 1.2269(17) . ?
O002 H00A 0.8494 . ?
O002 H00B 0.8500 . ?
O10 C9 1.2255(18) . ?
N21 N22 1.3980(16) . ?
N21 C20 1.3654(18) . ?
N21 C23 1.3922(18) . ?
N15 N14 1.3932(16) . ?
N15 C20 1.3589(18) . ?
N15 C16 1.3486(17) . ?
N8 H8 0.8800 . ?
N8 N7 1.3463(16) . ?
N8 C9 1.3703(18) . ?
N11 H11 0.8800 . ?
N11 C9 1.3775(18) . ?
N11 C12 1.3722(19) . ?
N2 N3 1.3437(17) . ?
N2 C1 1.3442(17) . ?
N7 C6 1.2975(18) . ?
N14 C23 1.3295(18) . ?
N3 N4 1.3152(17) . ?
N19 N18 1.4131(16) . ?
N19 C20 1.3060(19) . ?
N4 N5 1.3523(17) . ?
N18 H18 0.8800 . ?
N18 C16 1.3424(18) . ?
N5 C1 1.3372(18) . ?
N24 H24A 0.8800 . ?
N24 H24B 0.8800 . ?
N24 C23 1.3231(18) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N17 C16 1.3209(18) . ?
N22 H22A 0.8677 . ?
N22 H22B 0.8686 . ?
C6 C1 1.4675(19) . ?
C6 C12 1.4803(19) . ?
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
N15 N14 C23 N21 -1.79(15) . . . . ?
N15 N14 C23 N24 177.12(14) . . . . ?
N8 N7 C6 C1 179.47(11) . . . . ?
N8 N7 C6 C12 1.9(2) . . . . ?
N2 N3 N4 N5 0.16(15) . . . . ?
N7 N8 C9 O10 178.93(13) . . . . ?
N7 N8 C9 N11 -0.8(2) . . . . ?
N7 C6 C1 N2 -10.4(2) . . . . ?
N7 C6 C1 N5 169.05(13) . . . . ?
N7 C6 C12 O13 174.42(14) . . . . ?
N7 C6 C12 N11 -4.60(19) . . . . ?
N14 N15 C20 N21 0.26(16) . . . . ?
N14 N15 C20 N19 178.11(12) . . . . ?
N14 N15 C16 N18 -177.20(15) . . . . ?
N14 N15 C16 N17 2.9(3) . . . . ?
N3 N2 C1 N5 0.03(15) . . . . ?
N3 N2 C1 C6 179.56(12) . . . . ?
N3 N4 N5 C1 -0.13(15) . . . . ?
N19 N18 C16 N15 0.30(16) . . . . ?
N19 N18 C16 N17 -179.82(14) . . . . ?
N4 N5 C1 N2 0.06(15) . . . . ?
N4 N5 C1 C6 -179.44(13) . . . . ?
N18 N19 C20 N21 176.33(19) . . . . ?
N18 N19 C20 N15 -0.31(15) . . . . ?
N22 N21 C20 N15 -176.65(12) . . . . ?
N22 N21 C20 N19 6.5(3) . . . . ?
N22 N21 C23 N14 177.27(13) . . . . ?
N22 N21 C23 N24 -1.7(2) . . . . ?
C20 N21 C23 N14 2.07(16) . . . . ?
C20 N21 C23 N24 -176.89(13) . . . . ?
C20 N15 N14 C23 0.93(15) . . . . ?
C20 N15 C16 N18 -0.47(15) . . . . ?
C20 N15 C16 N17 179.64(14) . . . . ?
C20 N19 N18 C16 0.00(15) . . . . ?
C23 N21 C20 N15 -1.30(15) . . . . ?
C23 N21 C20 N19 -178.13(19) . . . . ?
C16 N15 N14 C23 177.51(16) . . . . ?
C16 N15 C20 N21 -177.32(11) . . . . ?
C16 N15 C20 N19 0.53(17) . . . . ?
C9 N8 N7 C6 1.0(2) . . . . ?
C9 N11 C12 O13 -174.13(14) . . . . ?
C9 N11 C12 C6 4.9(2) . . . . ?
C1 N2 N3 N4 -0.12(14) . . . . ?
C1 C6 C12 O13 -3.0(2) . . . . ?
C1 C6 C12 N11 177.95(12) . . . . ?
C12 N11 C9 O10 177.77(13) . . . . ?
C12 N11 C9 N8 -2.5(2) . . . . ?
C12 C6 C1 N2 167.21(12) . . . . ?
C12 C6 C1 N5 -13.3(2) . . . . ?
