#------------------------------------------------------------------------------
#$Date: 2019-11-26 00:14:39 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/71/4517125.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_4517125
loop_
_publ_author_name
'Xia, Honglei'
'Zhang, Wenquan'
'Jin, Yunhe'
'Song, Siwei'
'Wang, Kangcai'
'Zhang, Qinghua'
_publ_section_title
;
 Synthesis of Thermally Stable and Insensitive Energetic Materials by
 Incorporating the Tetrazole Functionality into Fused Ring
 3,6-Dinitropyrazolo-[4,3-c]Pyrazole Framework.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.9b17384
_journal_year                    2019
_chemical_formula_moiety         'C6 N14 O4, 2(C H7 N4)'
_chemical_formula_sum            'C8 H14 N22 O4'
_chemical_formula_weight         482.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.146(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9219(9)
_cell_length_b                   10.2466(12)
_cell_length_c                   11.8205(14)
_cell_measurement_reflns_used    1503
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.64
_cell_volume                     952.05(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7650
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.591
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0697 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.9223. The λ/2 correction factor is 0.00150.'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       cube
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0582P)²+0.1517P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1687
_reflns_number_total             2176
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b17384_si_006.cif
_cod_data_source_block           ng
_cod_database_code               4517125
_shelxl_version_number           2013-2
_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_max   0.973
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.2027(2) 0.40158(14) 0.26458(11) 0.0384(4) Uani 1 1 d
O2 O 0.43686(18) 0.41013(15) 0.38200(12) 0.0399(4) Uani 1 1 d
N5 N 0.12127(18) 0.44921(14) 0.62135(11) 0.0212(3) Uani 1 1 d
N6 N 0.24382(19) 0.41655(14) 0.55586(12) 0.0235(3) Uani 1 1 d
N1 N 0.29079(19) 0.41418(14) 0.80126(12) 0.0243(3) Uani 1 1 d
N7 N 0.2823(2) 0.41830(14) 0.35932(13) 0.0269(4) Uani 1 1 d
N3 N 0.0869(2) 0.35110(16) 0.89659(13) 0.0282(4) Uani 1 1 d
N9 N 0.5541(2) 0.32028(15) 1.06156(13) 0.0257(4) Uani 1 1 d
N11 N 0.8430(2) 0.30124(17) 1.06095(14) 0.0296(4) Uani 1 1 d
N2 N 0.2512(2) 0.37308(15) 0.90284(12) 0.0268(4) Uani 1 1 d
N4 N 0.01243(19) 0.37604(15) 0.79018(13) 0.0274(4) Uani 1 1 d
N10 N 0.6738(2) 0.38256(17) 0.90383(14) 0.0311(4) Uani 1 1 d
N8 N 0.5723(2) 0.2597(2) 1.16854(14) 0.0324(4) Uani 1 1 d
C2 C -0.0177(2) 0.50050(16) 0.55570(13) 0.0202(4) Uani 1 1 d
C00F C 0.6904(2) 0.33387(17) 1.00830(14) 0.0230(4) Uani 1 1 d
C1 C 0.1826(2) 0.44758(16) 0.45003(14) 0.0216(4) Uani 1 1 d
C3 C 0.1417(2) 0.41480(16) 0.73731(14) 0.0206(4) Uani 1 1 d
H H 0.761(3) 0.394(2) 0.8658(19) 0.035(6) Uiso 1 1 d
HA H 0.571(3) 0.398(2) 0.8704(18) 0.031(6) Uiso 1 1 d
HB H 0.944(3) 0.320(2) 1.0219(18) 0.039(6) Uiso 1 1 d
HC H 0.851(3) 0.263(3) 1.131(2) 0.058(8) Uiso 1 1 d
HD H 0.492(4) 0.198(3) 1.165(2) 0.067(9) Uiso 1 1 d
HE H 0.459(3) 0.334(2) 1.0246(19) 0.035(6) Uiso 1 1 d
HF H 0.546(3) 0.321(2) 1.219(2) 0.040(6) 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
N6 N5 C2 110.67(13) . .
N6 N5 C3 119.42(14) . .
C2 N5 C3 129.45(14) . .
C1 N6 N5 106.04(14) . .
C3 N1 N2 102.78(14) . .
O1 N7 C1 116.23(16) . .
O2 N7 O1 125.23(16) . .
O2 N7 C1 118.53(15) . .
N2 N3 N4 109.65(14) . .
N8 N9 HE 122.3(15) . .
C00F N9 N8 118.59(16) . .
C00F N9 HE 118.0(15) . .
C00F N11 HB 118.1(13) . .
C00F N11 HC 119.2(16) . .
HB N11 HC 123(2) . .
N3 N2 N1 110.03(14) . .
C3 N4 N3 102.89(14) . .
C00F N10 H 122.4(15) . .
C00F N10 HA 117.9(14) . .
H N10 HA 120(2) . .
N9 N8 HD 106.0(18) . .
N9 N8 HF 106.5(15) . .
HD N8 HF 108(2) . .
N5 C2 C2 107.05(19) . 3_566
N5 C2 C1 148.16(15) . 3_566
C2 C2 C1 104.77(18) 3_566 3_566
N9 C00F N11 119.88(16) . .
N9 C00F N10 119.46(17) . .
N10 C00F N11 120.64(17) . .
N6 C1 N7 118.92(15) . .
N6 C1 C2 111.47(14) . 3_566
C2 C1 N7 129.48(15) 3_566 .
N1 C3 N5 123.06(15) . .
N1 C3 N4 114.66(15) . .
N4 C3 N5 122.25(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N7 1.227(2) .
O2 N7 1.223(2) .
N5 N6 1.3568(19) .
N5 C2 1.370(2) .
N5 C3 1.405(2) .
N6 C1 1.323(2) .
N1 N2 1.346(2) .
N1 C3 1.321(2) .
N7 C1 1.440(2) .
N3 N2 1.314(2) .
N3 N4 1.346(2) .
N9 N8 1.400(2) .
N9 C00F 1.323(2) .
N9 HE 0.83(2) .
N11 C00F 1.332(2) .
N11 HB 0.99(2) .
N11 HC 0.91(3) .
N4 C3 1.325(2) .
N10 C00F 1.323(2) .
N10 H 0.88(2) .
N10 HA 0.87(2) .
N8 HD 0.89(3) .
N8 HF 0.91(2) .
C2 C2 1.380(3) 3_566
C2 C1 1.404(2) 3_566
C1 C2 1.404(2) 3_566
