#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:22:41 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229080 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/10/7231063.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_7231063
loop_
_publ_author_name
'Sun, Qi'
'Lin, Qiuhan'
'Lu, Ming'
_publ_section_title
;
 Nitramino-functionalized tetracyclic oxadiazoles as energetic materials
 with high performance and high stability: crystal structures and
 energetic properties
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4321
_journal_paper_doi               10.1039/C8CE00857D
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         '2(C2 H6 N5), C8 N12 O8, 2(H2 O)'
_chemical_formula_sum            'C12 H16 N22 O10'
_chemical_formula_weight         628.47
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-15 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.758(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0523(7)
_cell_length_b                   19.0738(19)
_cell_length_c                   9.4159(12)
_cell_measurement_reflns_used    1610
_cell_measurement_temperature    171(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      3.16
_cell_volume                     1176.3(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      171(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.0612
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5741
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_min         3.289
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       column
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0486
_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)+(0.0412P)²+0.0231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1508
_reflns_number_total             2139
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00857d2.cif
_cod_data_source_block           1_CCDC6
_cod_depositor_comments
'Adding full bibliography for 7231057--7231063.cif.'
_cod_database_code               7231063
_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   0.960
_shelx_estimated_absorpt_t_max   0.980
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 -0.1285(4) 0.92987(13) 0.5980(3) 0.0131(6) Uani 1 1 d . .
C2 C -0.3958(4) 0.98680(13) 0.5288(3) 0.0138(6) Uani 1 1 d . .
C3 C 0.2251(4) 0.86351(13) 0.6967(3) 0.0152(6) Uani 1 1 d . .
C4 C 0.0066(4) 0.86938(12) 0.6226(3) 0.0137(6) Uani 1 1 d . .
C5 C 0.6859(4) 0.19513(12) 0.6997(3) 0.0148(6) Uani 1 1 d . .
C6 C 0.8623(4) 0.12683(12) 0.8878(3) 0.0133(6) Uani 1 1 d . .
N1 N -0.0639(3) 0.99318(11) 0.6453(2) 0.0176(5) Uani 1 1 d . .
N2 N -0.3367(3) 0.92324(10) 0.5236(2) 0.0138(5) Uani 1 1 d . .
N3 N 0.2731(3) 0.79707(11) 0.6928(2) 0.0195(5) Uani 1 1 d . .
N4 N -0.0719(3) 0.80832(10) 0.5730(3) 0.0197(5) Uani 1 1 d . .
N5 N 0.3446(3) 0.92189(10) 0.7516(2) 0.0170(5) Uani 1 1 d . .
N6 N 0.5442(3) 0.91011(11) 0.8116(2) 0.0169(5) Uani 1 1 d . .
N7 N 1.0000(3) 0.16144(11) 0.8545(2) 0.0171(5) Uani 1 1 d . .
N8 N 0.8831(3) 0.20360(11) 0.7307(2) 0.0175(5) Uani 1 1 d D .
H8A H 0.939(4) 0.2383(12) 0.712(3) 0.021 Uiso 1 1 d D U
N9 N 0.6684(3) 0.14525(11) 0.7951(2) 0.0146(5) Uani 1 1 d D .
H9A H 0.559(3) 0.1306(13) 0.797(3) 0.017 Uiso 1 1 d D U
N10 N 0.5350(3) 0.23041(12) 0.5970(3) 0.0212(6) Uani 1 1 d D .
H10A H 0.414(3) 0.2139(13) 0.563(3) 0.025 Uiso 1 1 d D U
H10B H 0.565(4) 0.2590(13) 0.540(3) 0.025 Uiso 1 1 d D U
N11 N 0.9017(3) 0.08150(12) 1.0051(3) 0.0196(5) Uani 1 1 d D .
H11A H 0.808(3) 0.0532(12) 1.001(3) 0.024 Uiso 1 1 d D U
H11B H 1.028(3) 0.0716(14) 1.053(3) 0.024 Uiso 1 1 d D U
O1 O -0.2456(2) 1.03261(8) 0.59778(19) 0.0169(4) Uani 1 1 d . .
O2 O 0.0887(3) 0.76226(9) 0.6146(2) 0.0224(5) Uani 1 1 d . .
O3 O 0.6549(3) 0.96404(9) 0.8469(2) 0.0212(5) Uani 1 1 d . .
O4 O 0.6222(3) 0.85090(9) 0.8310(2) 0.0255(5) Uani 1 1 d . .
O5 O 0.3420(3) 0.08669(11) 0.8242(3) 0.0320(5) Uani 1 1 d D .
H5C H 0.249(4) 0.1089(15) 0.840(4) 0.038 Uiso 1 1 d D U
H5D H 0.303(5) 0.0464(10) 0.802(3) 0.038 Uiso 1 1 d D U
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_3
N1 C1 N2 115.4(2) .
N1 C1 C4 123.4(2) .
N2 C1 C4 121.2(2) .
N2 C2 O1 115.0(2) .
N2 C2 C2 127.4(3) 3_476
O1 C2 C2 117.6(3) 3_476
N3 C3 N5 131.4(2) .
N3 C3 C4 107.6(2) .
N5 C3 C4 121.0(2) .
N4 C4 C3 109.9(2) .
N4 C4 C1 119.0(2) .
C3 C4 C1 131.0(2) .
N8 C5 N10 126.4(2) .
N8 C5 N9 106.8(2) .
N10 C5 N9 126.8(2) .
N7 C6 N11 125.1(2) .
N7 C6 N9 112.0(2) .
N11 C6 N9 122.8(2) .
C1 N1 O1 102.92(18) .
C2 N2 C1 101.1(2) .
C3 N3 O2 105.81(19) .
C4 N4 O2 105.94(19) .
N6 N5 C3 115.34(19) .
O4 N6 O3 120.5(2) .
O4 N6 N5 124.0(2) .
O3 N6 N5 115.48(19) .
C6 N7 N8 103.24(19) .
C5 N8 N7 111.0(2) .
C5 N8 H8A 126.7(19) .
N7 N8 H8A 117.5(19) .
C5 N9 C6 106.9(2) .
C5 N9 H9A 124.9(18) .
C6 N9 H9A 128.2(18) .
C5 N10 H10A 120.4(18) .
C5 N10 H10B 117.8(19) .
H10A N10 H10B 117(3) .
C6 N11 H11A 116.9(18) .
C6 N11 H11B 115.7(19) .
H11A N11 H11B 122(3) .
C2 O1 N1 105.56(17) .
N4 O2 N3 110.74(17) .
H5C O5 H5D 108(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.309(3) .
C1 N2 1.378(3) .
C1 C4 1.459(3) .
C2 N2 1.289(3) .
C2 O1 1.341(3) .
C2 C2 1.455(5) 3_476
C3 N3 1.316(3) .
C3 N5 1.376(3) .
C3 C4 1.441(3) .
C4 N4 1.300(3) .
C5 N8 1.321(3) .
C5 N10 1.326(3) .
C5 N9 1.345(3) .
C6 N7 1.305(3) .
C6 N11 1.348(3) .
C6 N9 1.368(3) .
N1 O1 1.408(3) .
N3 O2 1.402(3) .
N4 O2 1.371(3) .
N5 N6 1.328(3) .
N6 O4 1.240(2) .
N6 O3 1.259(3) .
N7 N8 1.405(3) .
N8 H8A 0.82(2) .
N9 H9A 0.83(2) .
N10 H10A 0.854(17) .
N10 H10B 0.846(18) .
N11 H11A 0.844(17) .
N11 H11B 0.856(18) .
O5 H5C 0.837(18) .
O5 H5D 0.817(17) .
