#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:43:11 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236314 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/65/7236574.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_7236574
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         'C8 H8 N12 O7'
_chemical_formula_sum            'C8 H8 N12 O7'
_chemical_formula_weight         384.26
_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                 91.645(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5880(4)
_cell_length_b                   11.0597(10)
_cell_length_c                   14.3951(11)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      25.22
_cell_measurement_theta_min      3.95
_cell_volume                     730.13(11)
_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 0.998
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_description       column
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1340
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0440
_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)+(0.0324P)²+0.4685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1025
_reflns_number_total             1340
_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               7236574
_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   0.957
_shelx_estimated_absorpt_t_max   0.977
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
C1 C 0.6653(5) -0.0354(2) 0.11070(15) 0.0214(5) Uani 1 1 d . . .
C2 C 0.6068(5) -0.02066(19) 0.20627(15) 0.0173(5) Uani 1 1 d . . .
C3 C 0.3953(4) 0.05425(19) 0.25387(14) 0.0171(5) Uani 1 1 d . . .
C4 C 0.1584(5) 0.1277(2) 0.36355(16) 0.0240(5) Uani 1 1 d . . .
N1 N 0.5385(4) 0.03103(18) 0.03551(12) 0.0257(5) Uani 1 1 d . . .
N2 N 0.8746(4) -0.11275(19) 0.10013(14) 0.0288(5) Uani 1 1 d . . .
N3 N 0.7821(4) -0.09231(17) 0.25381(13) 0.0234(5) Uani 1 1 d . . .
N4 N 0.2160(4) 0.12683(18) 0.20857(12) 0.0218(5) Uani 1 1 d . . .
N5 N 0.3719(4) 0.04872(17) 0.34709(12) 0.0217(5) Uani 1 1 d . . .
N6 N 0.0751(4) 0.32184(18) 0.05328(13) 0.0226(5) Uani 1 1 d D . .
H6A H 0.106(4) 0.2585(15) 0.0934(12) 0.027 Uiso 1 1 d D U .
H6B H 0.086(4) 0.3925(14) 0.0879(12) 0.027 Uiso 1 1 d D U .
H6C H 0.217(4) 0.3241(18) 0.0101(12) 0.027 Uiso 1 1 d D U .
H6D H -0.104(3) 0.3155(18) 0.0249(13) 0.027 Uiso 1 1 d D U .
O1 O 0.5466(8) 0.1387(3) 0.0471(2) 0.0328(8) Uani 0.5 1 d . . P
O2 O 0.9505(3) -0.14916(15) 0.18863(11) 0.0294(4) Uani 1 1 d . . .
O3 O 0.0524(3) 0.17728(14) 0.28137(10) 0.0241(4) Uani 1 1 d . . .
O4 O 0.0580(4) 0.16097(18) 0.43767(11) 0.0381(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
_geom_angle_site_symmetry_3
N2 C1 C2 110.5(2) . .
N2 C1 N1 122.7(2) . .
C2 C1 N1 126.5(2) . .
N3 C2 C1 107.88(19) . .
N3 C2 C3 120.31(19) . .
C1 C2 C3 131.8(2) . .
N4 C3 N5 117.12(19) . .
N4 C3 C2 122.00(19) . .
N5 C3 C2 120.86(19) . .
O4 C4 N5 130.0(2) . .
O4 C4 O3 119.5(2) . .
N5 C4 O3 110.45(18) . .
O1 N1 N1 130.7(3) . 3_655
O1 N1 C1 113.4(2) . .
N1 N1 C1 115.6(2) 3_655 .
C1 N2 O2 104.68(18) . .
C2 N3 O2 105.51(18) . .
C3 N4 O3 102.19(16) . .
C4 N5 C3 103.04(18) . .
H6A N6 H6B 107.5(13) . .
H6A N6 H6C 110.4(14) . .
H6B N6 H6C 108.3(14) . .
H6A N6 H6D 110.3(14) . .
H6B N6 H6D 109.9(14) . .
H6C N6 H6D 110.4(14) . .
N2 O2 N3 111.39(16) . .
C4 O3 N4 107.19(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.298(3) .
C1 C2 1.419(3) .
C1 N1 1.419(3) .
C2 N3 1.308(3) .
C2 C3 1.461(3) .
C3 N4 1.310(3) .
C3 N5 1.351(3) .
C4 O4 1.231(3) .
C4 N5 1.339(3) .
C4 O3 1.380(3) .
N1 O1 1.203(4) .
N1 N1 1.273(4) 3_655
N2 O2 1.371(3) .
N3 O2 1.383(2) .
N4 O3 1.421(2) .
N6 H6A 0.916(14) .
N6 H6B 0.927(14) .
N6 H6C 0.914(14) .
N6 H6D 0.910(14) .
