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#$Date: 2022-02-09 00:53:52 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272856 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129683.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_7129683
loop_
_publ_author_name
'Chen, Peng'
'Qiu, Lili'
'Yin, Ping'
'He, Chunlin'
'Pang, Siping'
'Shreeve, Jean’ne M.'
_publ_section_title
;
 Unraveling the reactivity of the azo bridge in
 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate
 in the synthesis of energetic compounds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00215A
_journal_year                    2022
_chemical_formula_sum            'C14 H6 N14 O16'
_chemical_formula_weight         626.33
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                87.865(6)
_cell_angle_beta                 88.438(6)
_cell_angle_gamma                80.502(6)
_cell_formula_units_Z            1
_cell_length_a                   5.843(3)
_cell_length_b                   7.177(3)
_cell_length_c                   14.405(6)
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.83
_cell_volume                     595.2(5)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.970
_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  0.0160
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3668
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_min         1.415
_exptl_absorpt_coefficient_mu    0.161
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2188
_reflns_number_total             2632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00215a2.cif
_cod_data_source_block           c103
_cod_original_cell_volume        595.2(4)
_cod_database_code               7129683
_shelx_shelxl_version_number     2016/6
_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   0.981
_shelx_estimated_absorpt_t_max   0.986
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
O1 O 0.8220(2) 0.47888(19) 0.86753(9) 0.0489(4) Uani 1 1 d . . . . .
O2 O 0.4502(3) 0.4435(2) 0.89367(11) 0.0612(4) Uani 1 1 d . . . . .
O3 O 0.6558(4) 0.8528(3) 0.92337(11) 0.0754(5) Uani 1 1 d . U . . .
O4 O 0.6622(3) 0.9974(2) 0.78954(12) 0.0694(5) Uani 1 1 d . . . . .
O5 O 0.1845(3) 0.8560(2) 0.85554(10) 0.0667(5) Uani 1 1 d . . . . .
O6 O 0.1786(2) 0.6808(2) 0.73806(11) 0.0577(4) Uani 1 1 d . . . . .
O7 O 0.7459(2) 0.50364(15) 0.67972(8) 0.0396(3) Uani 1 1 d . . . . .
O8 O 0.7156(3) 0.7478(2) 0.31435(9) 0.0567(4) Uani 1 1 d . . . . .
N2 N 0.6264(3) 0.8721(2) 0.84125(10) 0.0423(4) Uani 1 1 d . U . . .
N3 N 0.2733(3) 0.7533(2) 0.79616(10) 0.0420(4) Uani 1 1 d . . . . .
N4 N 0.6033(2) 0.79089(19) 0.62788(10) 0.0397(4) Uani 1 1 d . . . . .
N5 N 0.8034(3) 0.5114(2) 0.58497(10) 0.0415(4) Uani 1 1 d . . . . .
N6 N 0.6518(3) 0.6633(2) 0.39588(11) 0.0507(4) Uani 1 1 d . . . . .
N7 N 0.8429(3) 0.8854(2) 0.33008(10) 0.0472(4) Uani 1 1 d . . . . .
N8 N 0.9877(3) 1.01368(19) 0.45705(9) 0.0407(4) Uani 1 1 d . . . . .
C1 C 0.9117(4) 0.3077(3) 0.92165(16) 0.0576(5) Uani 1 1 d . . . . .
H1A H 1.076732 0.277762 0.912122 0.086 Uiso 1 1 calc R U . . .
H1B H 0.840343 0.204888 0.902046 0.086 Uiso 1 1 calc R U . . .
H1C H 0.877027 0.327886 0.986383 0.086 Uiso 1 1 calc R U . . .
C2 C 0.5976(3) 0.5216(2) 0.86031(11) 0.0397(4) Uani 1 1 d . . . . .
C3 C 0.5402(3) 0.7021(2) 0.79645(11) 0.0360(4) Uani 1 1 d . . . . .
C4 C 0.6292(3) 0.6742(2) 0.69828(11) 0.0327(3) Uani 1 1 d . . . . .
C5 C 0.7161(3) 0.6818(2) 0.55922(11) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.7389(3) 0.7463(2) 0.46194(11) 0.0356(4) Uani 1 1 d . . . . .
C7 C 0.8602(3) 0.8861(2) 0.41997(11) 0.0368(4) 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
C2 O1 C1 117.18(15) . . ?
C4 O7 N5 105.53(12) . . ?
N7 O8 N6 111.56(13) . . ?
O4 N2 O3 129.27(17) . . ?
O4 N2 C3 116.23(15) . . ?
O3 N2 C3 114.42(15) . . ?
O6 N3 O5 127.58(17) . . ?
O6 N3 C3 115.71(14) . . ?
O5 N3 C3 116.67(15) . . ?
C4 N4 C5 101.21(13) . . ?
C5 N5 O7 103.42(12) . . ?
C6 N6 O8 105.96(15) . . ?
C7 N7 O8 105.22(15) . . ?
N8 N8 C7 111.77(17) 2_776 . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 129.36(16) . . ?
O2 C2 C3 121.82(16) . . ?
O1 C2 C3 108.82(14) . . ?
C4 C3 N3 109.00(12) . . ?
C4 C3 C2 113.37(13) . . ?
N3 C3 C2 106.36(13) . . ?
C4 C3 N2 112.21(13) . . ?
N3 C3 N2 105.47(12) . . ?
C2 C3 N2 109.94(13) . . ?
N4 C4 O7 114.55(14) . . ?
N4 C4 C3 129.10(14) . . ?
O7 C4 C3 116.32(13) . . ?
N5 C5 N4 115.29(14) . . ?
N5 C5 C6 120.21(14) . . ?
N4 C5 C6 124.50(14) . . ?
N6 C6 C7 107.86(15) . . ?
N6 C6 C5 120.51(16) . . ?
C7 C6 C5 131.48(15) . . ?
N7 C7 N8 118.11(15) . . ?
N7 C7 C6 109.39(16) . . ?
N8 C7 C6 132.49(15) . . ?
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 C2 1.302(2) . ?
O1 C1 1.459(2) . ?
O2 C2 1.185(2) . ?
O3 N2 1.200(2) . ?
O4 N2 1.188(2) . ?
O5 N3 1.200(2) . ?
O6 N3 1.196(2) . ?
O7 C4 1.3316(19) . ?
O7 N5 1.3981(19) . ?
O8 N7 1.360(2) . ?
O8 N6 1.372(2) . ?
N2 C3 1.561(2) . ?
N3 C3 1.542(2) . ?
N4 C4 1.287(2) . ?
N4 C5 1.370(2) . ?
N5 C5 1.290(2) . ?
N6 C6 1.299(2) . ?
N7 C7 1.302(2) . ?
N8 N8 1.254(3) 2_776 ?
N8 C7 1.401(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.556(2) . ?
C3 C4 1.502(2) . ?
C5 C6 1.469(2) . ?
C6 C7 1.428(2) . ?
