#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/80/7058018.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_7058018
loop_
_publ_author_name
'Domasevitch, Konstantin V.'
'Gospodinov, Ivan'
'Krautscheid, Harald'
'Klapoetke, Thomas M.'
'Stierstorfer, Joerg'
_publ_section_title
;
 Facile and selective polynitrations at the 4-pyrazolyl dual backbone: A
 straightforward access to a series of high-density energetic materials
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1305
_journal_page_last               1312
_journal_paper_doi               10.1039/C8NJ05266B
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C6 H4 N6 O4'
_chemical_formula_sum            'C6 H4 N6 O4'
_chemical_formula_weight         224.15
_chemical_name_systematic
;
3,3'-Dinitro-4,4'-bipyrazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-11 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.739(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9744(9)
_cell_length_b                   6.5428(8)
_cell_length_c                   8.9414(8)
_cell_measurement_reflns_used    3236
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.031
_cell_measurement_theta_min      2.909
_cell_volume                     819.41(15)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3236
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.031
_diffrn_reflns_theta_min         2.909
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0366
_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)+(0.0698P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                829
_reflns_number_total             986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj05266b2.cif
_cod_data_source_block           2
_cod_database_code               7058018
#BEGIN Tags that were not found in dictionaries:
_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   0.961
_shelx_estimated_absorpt_t_max   0.970
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.06740(6) 0.48068(16) 0.43536(13) 0.0395(3) Uani 1 1 d
O2 O 0.18461(6) 0.56813(15) 0.39244(12) 0.0343(3) Uani 1 1 d
N1 N 0.16833(6) 0.00680(17) 0.22016(13) 0.0272(3) Uani 1 1 d
N2 N 0.19298(6) 0.19333(16) 0.28732(12) 0.0250(3) Uani 1 1 d
N3 N 0.12394(6) 0.44694(16) 0.38240(12) 0.0242(3) Uani 1 1 d
C1 C 0.08247(7) -0.05400(19) 0.19681(14) 0.0246(3) Uani 1 1 d
C2 C 0.04609(7) 0.10353(17) 0.25163(13) 0.0201(3) Uani 1 1 d
C3 C 0.11905(6) 0.25113(17) 0.30625(12) 0.0206(3) Uani 1 1 d
H1N H 0.2117(11) -0.059(3) 0.207(2) 0.042(4) Uiso 1 1 d
H1 H 0.0565(10) -0.184(2) 0.1502(19) 0.029(4) 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_3
N2 N1 C1 113.52(9) .
N2 N1 H1N 115.5(11) .
C1 N1 H1N 130.7(12) .
C3 N2 N1 103.31(9) .
O2 N3 O1 124.13(11) .
O2 N3 C3 118.33(9) .
O1 N3 C3 117.54(9) .
N1 C1 C2 107.19(11) .
N1 C1 H1 122.0(8) .
C2 C1 H1 130.8(8) .
C1 C2 C3 102.43(9) .
C1 C2 C2 125.79(8) 2
C3 C2 C2 131.78(7) 2
N2 C3 C2 113.55(10) .
N2 C3 N3 117.80(9) .
C2 C3 N3 128.61(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N3 1.2248(12) .
O2 N3 1.2217(12) .
N1 N2 1.3334(15) .
N1 C1 1.3444(14) .
N1 H1N 0.869(18) .
N2 C3 1.3261(12) .
N3 C3 1.4352(15) .
C1 C2 1.3835(15) .
C1 H1 0.951(16) .
C2 C3 1.4078(14) .
C2 C2 1.4589(19) 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 N1 N2 C3 -0.11(12) . .
N2 N1 C1 C2 0.26(13) . .
N1 C1 C2 C3 -0.27(12) . .
N1 C1 C2 C2 179.56(12) . 2
N1 N2 C3 C2 -0.08(12) . .
N1 N2 C3 N3 178.00(9) . .
C1 C2 C3 N2 0.22(12) . .
C2 C2 C3 N2 -179.60(12) 2 .
C1 C2 C3 N3 -177.59(10) . .
C2 C2 C3 N3 2.6(2) 2 .
O2 N3 C3 N2 15.42(14) . .
O1 N3 C3 N2 -163.66(10) . .
O2 N3 C3 C2 -166.84(10) . .
O1 N3 C3 C2 14.08(16) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179039
