#------------------------------------------------------------------------------
#$Date: 2019-11-26 00:15:43 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/71/4517128.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_4517128
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, H10 N4'
_chemical_formula_sum            'C6 H10 N18 O4'
_chemical_formula_weight         398.32
_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             2019-09-04
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.827(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1689(4)
_cell_length_b                   5.5698(2)
_cell_length_c                   14.9671(7)
_cell_measurement_reflns_used    2256
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      26.845
_cell_measurement_theta_min      2.261
_cell_volume                     750.75(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8798
_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         27.497
_diffrn_reflns_theta_min         2.771
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1121 before and 0.0640 after correction. The Ratio of minimum to maximum transmission is 0.9236. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0443
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1239
_reflns_number_total             1711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b17384_si_004.cif
_cod_data_source_block           xhl
_cod_database_code               4517128
_shelx_shelxl_version_number     2018/3
_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   0.988
_shelx_estimated_absorpt_t_min   0.965
_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 0.79564(16) 1.1956(3) 0.25021(9) 0.0259(4) Uani 1 1 d
O2 O 0.98252(19) 1.4080(3) 0.31748(12) 0.0381(5) Uani 1 1 d
N2 N 0.82304(19) 0.9047(3) 0.39155(11) 0.0194(4) Uani 1 1 d
N8 N 0.4621(2) 0.0015(3) 0.33177(12) 0.0202(4) Uani 1 1 d
N3 N 0.85638(18) 0.8006(3) 0.47452(10) 0.0175(4) Uani 1 1 d
N1 N 0.89899(19) 1.2367(3) 0.31295(12) 0.0210(4) Uani 1 1 d
N7 N 0.7155(2) 0.4492(3) 0.42703(11) 0.0223(4) Uani 1 1 d
N4 N 0.7259(2) 0.5656(3) 0.57053(11) 0.0231(4) Uani 1 1 d
N9 N 0.3820(2) 0.1836(3) 0.27349(13) 0.0225(4) Uani 1 1 d
N5 N 0.6460(2) 0.3620(3) 0.55456(11) 0.0233(4) Uani 1 1 d
N6 N 0.6388(2) 0.2952(3) 0.46982(11) 0.0233(4) Uani 1 1 d
C1 C 0.9780(2) 0.9107(3) 0.52641(13) 0.0168(4) Uani 1 1 d
C2 C 0.9209(2) 1.0776(3) 0.39041(13) 0.0174(4) Uani 1 1 d
C3 C 0.7667(2) 0.6064(4) 0.49177(13) 0.0181(5) Uani 1 1 d
H8A H 0.403(3) -0.113(4) 0.3557(16) 0.029(6) Uiso 1 1 d
H8B H 0.518(3) 0.077(4) 0.3776(17) 0.028(7) Uiso 1 1 d
H9A H 0.327(3) 0.261(5) 0.3025(16) 0.029(7) Uiso 1 1 d
H8C H 0.514(3) -0.096(5) 0.2974(17) 0.033(7) Uiso 1 1 d
H9B H 0.322(3) 0.107(5) 0.2309(18) 0.031(7) 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
C2 N2 N3 106.72(16) . .
N2 N3 C1 110.29(15) . .
N2 N3 C3 117.22(16) . .
C1 N3 C3 132.49(16) . .
O1 N1 C2 118.20(17) . .
O2 N1 O1 125.29(18) . .
O2 N1 C2 116.44(17) . .
C3 N7 N6 102.62(16) . .
C3 N4 N5 102.82(16) . .
N6 N5 N4 109.76(16) . .
N5 N6 N7 110.06(16) . .
N3 C1 C1 106.9(2) . 3_776
N3 C1 C2 148.06(18) . 3_776
C1 C1 C2 105.0(2) 3_776 3_776
N2 C2 N1 117.80(17) . .
N2 C2 C1 111.05(17) . 3_776
C1 C2 N1 130.67(18) 3_776 .
N7 C3 N3 120.75(17) . .
N4 C3 N3 124.54(18) . .
N4 C3 N7 114.70(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.224(2) .
O2 N1 1.218(2) .
N2 N3 1.352(2) .
N2 C2 1.319(3) .
N8 N9 1.445(3) .
N3 C1 1.377(3) .
N3 C3 1.412(3) .
N1 C2 1.443(2) .
N7 N6 1.346(2) .
N7 C3 1.325(3) .
N4 N5 1.346(2) .
N4 C3 1.322(3) .
N5 N6 1.312(2) .
C1 C1 1.378(4) 3_776
C1 C2 1.407(3) 3_776
