#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/65/7236572.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_7236572
loop_
_publ_author_name
'Sun, Qi'
'Shen, Cheng'
'Li, Xin'
'Lin, Qiuhan'
'Lu, Ming'
_publ_section_title
;
 Combination of four oxadiazole rings for the generation of energetic
 materials with high detonation performance, low sensitivity and excellent
 thermal stability
;
_journal_issue                   22
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              11063
_journal_paper_doi               10.1039/C7TA02209C
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         '2(H4 N), C8 N10 O6'
_chemical_formula_sum            'C8 H8 N12 O6'
_chemical_formula_weight         368.26
_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-2014/7
_audit_update_record
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.185(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7289(6)
_cell_length_b                   10.5845(12)
_cell_length_c                   14.3425(19)
_cell_measurement_reflns_used    1046
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.84
_cell_volume                     717.88(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4148
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0494
_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)+(0.0439P)²+0.3627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                947
_reflns_number_total             1312
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ta02209c2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7236572
_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   0.964
_shelx_estimated_absorpt_t_max   0.975
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
C1 C 0.6483(5) 0.5274(2) 0.89019(18) 0.0135(6) Uani 1 1 d . .
C2 C 0.6048(5) 0.5079(2) 0.79301(18) 0.0122(6) Uani 1 1 d . .
C3 C 0.3977(5) 0.4324(2) 0.74220(17) 0.0118(6) Uani 1 1 d . .
C4 C 0.1705(5) 0.3547(2) 0.62918(18) 0.0137(6) Uani 1 1 d . .
N1 N 0.4887(5) 0.4706(2) 0.96241(14) 0.0173(6) Uani 1 1 d . .
N2 N 0.8631(5) 0.6027(2) 0.90315(16) 0.0198(6) Uani 1 1 d . .
N3 N 0.7909(5) 0.5751(2) 0.74709(15) 0.0172(5) Uani 1 1 d . .
N4 N 0.2193(4) 0.3580(2) 0.78558(15) 0.0155(5) Uani 1 1 d . .
N5 N 0.3782(4) 0.4363(2) 0.64795(14) 0.0133(5) Uani 1 1 d . .
N6 N -0.4174(5) 0.3181(2) 0.44419(15) 0.0161(5) Uani 1 1 d D .
H6A H -0.272(4) 0.315(2) 0.4871(13) 0.019 Uiso 1 1 d D U
H6B H -0.587(4) 0.308(2) 0.4739(14) 0.019 Uiso 1 1 d D U
H6C H -0.415(5) 0.3953(16) 0.4153(14) 0.019 Uiso 1 1 d D U
H6D H -0.390(4) 0.2559(18) 0.4010(13) 0.019 Uiso 1 1 d D U
O1 O 0.9543(4) 0.63334(17) 0.81495(13) 0.0208(5) Uani 1 1 d . .
O2 O 0.0616(4) 0.30523(17) 0.71057(12) 0.0162(5) Uani 1 1 d . .
O3 O 0.0762(4) 0.31875(19) 0.55315(12) 0.0214(5) 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
N2 C1 N1 124.9(2) .
N2 C1 C2 109.8(2) .
N1 C1 C2 125.3(2) .
N3 C2 C1 108.5(2) .
N3 C2 C3 119.8(2) .
C1 C2 C3 131.6(2) .
N4 C3 N5 116.7(2) .
N4 C3 C2 121.6(2) .
N5 C3 C2 121.7(2) .
O3 C4 N5 129.8(2) .
O3 C4 O2 119.6(2) .
N5 C4 O2 110.5(2) .
N1 N1 C1 112.0(3) 3_667
C1 N2 O1 105.0(2) .
C2 N3 O1 105.2(2) .
C3 N4 O2 102.32(19) .
C4 N5 C3 103.3(2) .
H6A N6 H6B 109.6(14) .
H6A N6 H6C 108.9(15) .
H6B N6 H6C 109.3(14) .
H6A N6 H6D 108.7(14) .
H6B N6 H6D 110.7(15) .
H6C N6 H6D 109.6(15) .
N2 O1 N3 111.44(18) .
C4 O2 N4 107.16(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.304(3) .
C1 N1 1.418(3) .
C1 C2 1.423(3) .
C2 N3 1.311(3) .
C2 C3 1.457(3) .
C3 N4 1.313(3) .
C3 N5 1.355(3) .
C4 O3 1.237(3) .
C4 N5 1.334(3) .
C4 O2 1.381(3) .
N1 N1 1.250(4) 3_667
N2 O1 1.376(3) .
N3 O1 1.385(3) .
N4 O2 1.421(3) .
N6 H6A 0.921(15) .
N6 H6B 0.915(15) .
N6 H6C 0.917(15) .
N6 H6D 0.913(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339742
