#------------------------------------------------------------------------------
#$Date: 2023-05-09 01:50:28 +0300 (Tue, 09 May 2023) $
#$Revision: 283603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/29/7712978.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_7712978
loop_
_publ_author_name
'Epishina, Margarita'
'Kulikov, Alexander'
'Ananyev, Ivan V.'
'Anisimov, Aleksei A.'
'Monogarov, Konstantin Alexandrovich'
'Fershtat, Leonid'
_publ_section_title
;
 Impact of regiochemistry in energetic materials science: a case of
 (nitratomethyl-1,2,3-triazolyl)furazans
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00917C
_journal_year                    2023
_chemical_formula_moiety         'C5 H3 N7 O6'
_chemical_formula_sum            'C5 H3 N7 O6'
_chemical_formula_weight         257.14
_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   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2782(3)
_cell_length_b                   6.3430(2)
_cell_length_c                   13.7366(4)
_cell_measurement_reflns_used    333
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     950.90(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11887
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_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)+(0.0461P)²+0.3569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2374
_reflns_number_total             2533
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d3dt00917c2.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7712978
_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   0.977
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014/6
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 0.58094(7) 0.82012(12) 0.14641(6) 0.02128(17) Uani 1 1 d . . . . .
O2 O 0.62376(7) 0.27708(13) 0.29901(6) 0.02462(18) Uani 1 1 d . . . . .
O3 O 0.53510(7) 0.44512(12) 0.39982(5) 0.02065(16) Uani 1 1 d . . . . .
O4 O 0.13363(6) 1.04648(11) 0.47824(5) 0.01675(15) Uani 1 1 d . . . . .
O5 O 0.19076(9) 1.34890(14) 0.54866(7) 0.0318(2) Uani 1 1 d . . . . .
O6 O 0.33031(7) 1.10852(13) 0.55620(6) 0.02270(17) Uani 1 1 d . . . . .
N1 N 0.62228(8) 0.63650(15) 0.19616(7) 0.01934(18) Uani 1 1 d . . . . .
N2 N 0.48425(8) 0.90525(14) 0.17755(6) 0.01805(18) Uani 1 1 d . . . . .
N3 N 0.57183(7) 0.42864(14) 0.32377(6) 0.01614(17) Uani 1 1 d . . . . .
N4 N 0.36742(7) 0.80472(12) 0.28855(6) 0.01249(16) Uani 1 1 d . . . . .
N5 N 0.25294(7) 0.83085(13) 0.22511(6) 0.01417(16) Uani 1 1 d . . . . .
N6 N 0.17771(7) 0.84375(13) 0.28213(6) 0.01430(16) Uani 1 1 d . . . . .
N7 N 0.22725(8) 1.17754(14) 0.53231(6) 0.01936(18) Uani 1 1 d . . . . .
C1 C 0.55265(8) 0.60939(15) 0.25704(7) 0.01420(18) Uani 1 1 d . . . . .
C2 C 0.46627(8) 0.77607(15) 0.24618(7) 0.01326(18) Uani 1 1 d . . . . .
C3 C 0.36214(8) 0.80133(15) 0.38621(7) 0.01350(18) Uani 1 1 d . . . . .
H3 H 0.4325(13) 0.783(2) 0.4392(11) 0.019(3) Uiso 1 1 d . . . . .
C4 C 0.24052(8) 0.82733(14) 0.38123(7) 0.01311(18) Uani 1 1 d . . . . .
C5 C 0.17563(9) 0.83391(15) 0.46258(7) 0.01516(19) Uani 1 1 d . . . . .
H5B H 0.0991(12) 0.757(2) 0.4447(9) 0.013(3) Uiso 1 1 d . . . . .
H5A H 0.2243(12) 0.780(2) 0.5260(10) 0.018(3) 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
N1 O1 N2 111.98(7) . . ?
N7 O4 C5 113.35(7) . . ?
C1 N1 O1 104.43(8) . . ?
C2 N2 O1 104.95(8) . . ?
O2 N3 O3 126.66(9) . . ?
O2 N3 C1 116.95(8) . . ?
O3 N3 C1 116.38(8) . . ?
C3 N4 N5 111.12(7) . . ?
C3 N4 C2 130.52(8) . . ?
N5 N4 C2 118.27(7) . . ?
N6 N5 N4 106.17(7) . . ?
N5 N6 C4 110.04(8) . . ?
O5 N7 O6 128.90(10) . . ?
O5 N7 O4 112.80(9) . . ?
O6 N7 O4 118.30(8) . . ?
N1 C1 C2 110.19(9) . . ?
N1 C1 N3 119.69(9) . . ?
C2 C1 N3 130.12(8) . . ?
N2 C2 N4 120.47(9) . . ?
N2 C2 C1 108.45(8) . . ?
N4 C2 C1 130.78(8) . . ?
N4 C3 C4 104.03(8) . . ?
N4 C3 H3 121.9(9) . . ?
C4 C3 H3 134.0(9) . . ?
C3 C4 N6 108.65(8) . . ?
C3 C4 C5 130.24(9) . . ?
N6 C4 C5 121.10(8) . . ?
O4 C5 C4 112.11(8) . . ?
O4 C5 H5B 101.5(8) . . ?
C4 C5 H5B 111.9(8) . . ?
O4 C5 H5A 109.0(8) . . ?
C4 C5 H5A 113.2(8) . . ?
H5B C5 H5A 108.5(11) . . ?
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 N1 1.3712(12) . ?
O1 N2 1.3781(11) . ?
O2 N3 1.2179(11) . ?
O3 N3 1.2216(11) . ?
O4 N7 1.4007(11) . ?
O4 C5 1.4629(11) . ?
O5 N7 1.2033(12) . ?
O6 N7 1.2074(12) . ?
N1 C1 1.2950(12) . ?
N2 C2 1.3029(12) . ?
N3 C1 1.4497(13) . ?
N4 C3 1.3579(11) . ?
N4 N5 1.3734(11) . ?
N4 C2 1.3936(12) . ?
N5 N6 1.2945(11) . ?
N6 C4 1.3709(12) . ?
C1 C2 1.4198(13) . ?
C3 C4 1.3659(12) . ?
C3 H3 0.939(14) . ?
C4 C5 1.4828(13) . ?
C5 H5B 0.966(13) . ?
C5 H5A 0.968(14) . ?
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
N2 O1 N1 C1 -0.20(11) . . . . ?
N1 O1 N2 C2 0.25(11) . . . . ?
C3 N4 N5 N6 0.07(10) . . . . ?
C2 N4 N5 N6 176.98(8) . . . . ?
N4 N5 N6 C4 0.19(10) . . . . ?
C5 O4 N7 O5 -176.88(9) . . . . ?
C5 O4 N7 O6 2.94(12) . . . . ?
O1 N1 C1 C2 0.08(11) . . . . ?
O1 N1 C1 N3 -179.11(8) . . . . ?
O2 N3 C1 N1 -23.02(13) . . . . ?
O3 N3 C1 N1 156.29(9) . . . . ?
O2 N3 C1 C2 157.97(10) . . . . ?
O3 N3 C1 C2 -22.71(14) . . . . ?
O1 N2 C2 N4 -174.58(8) . . . . ?
O1 N2 C2 C1 -0.19(10) . . . . ?
C3 N4 C2 N2 -133.24(11) . . . . ?
N5 N4 C2 N2 50.56(12) . . . . ?
C3 N4 C2 C1 53.79(16) . . . . ?
N5 N4 C2 C1 -122.41(11) . . . . ?
N1 C1 C2 N2 0.07(12) . . . . ?
N3 C1 C2 N2 179.15(9) . . . . ?
N1 C1 C2 N4 173.69(9) . . . . ?
N3 C1 C2 N4 -7.24(17) . . . . ?
N5 N4 C3 C4 -0.30(10) . . . . ?
C2 N4 C3 C4 -176.71(9) . . . . ?
N4 C3 C4 N6 0.41(10) . . . . ?
N4 C3 C4 C5 178.91(9) . . . . ?
N5 N6 C4 C3 -0.39(11) . . . . ?
N5 N6 C4 C5 -179.06(8) . . . . ?
N7 O4 C5 C4 -77.63(10) . . . . ?
C3 C4 C5 O4 108.04(11) . . . . ?
N6 C4 C5 O4 -73.61(11) . . . . ?
