#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/80/7058019.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_7058019
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 H3 N7 O6'
_chemical_formula_sum            'C6 H3 N7 O6'
_chemical_formula_weight         269.15
_chemical_name_systematic
;
3,5,3'-Trinitro-4,4'-bipyrazole
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 114.148(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6064(8)
_cell_length_b                   11.9636(9)
_cell_length_c                   10.1200(9)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.009
_cell_measurement_theta_min      2.594
_cell_volume                     950.81(16)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.009
_diffrn_reflns_theta_min         2.594
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.814
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0384
_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)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1365
_reflns_number_total             2294
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj05266b2.cif
_cod_data_source_block           4
_cod_database_code               7058019
_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   0.964
_shelx_estimated_absorpt_t_max   0.972
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 0.01647(17) -0.07801(13) 0.21340(18) 0.0503(4) Uani 1 1 d
O2 O 0.29130(16) -0.06404(12) 0.31299(15) 0.0434(4) Uani 1 1 d
O3 O 0.08881(15) 0.40657(11) -0.03365(16) 0.0394(3) Uani 1 1 d
O4 O 0.34954(15) 0.35051(12) 0.05652(17) 0.0424(4) Uani 1 1 d
O5 O 0.59504(18) 0.12765(15) -0.07928(17) 0.0547(4) Uani 1 1 d
O6 O 0.33470(16) 0.15007(14) -0.10764(16) 0.0483(4) Uani 1 1 d
N1 N -0.01771(18) 0.12984(14) 0.11804(17) 0.0317(4) Uani 1 1 d
N2 N -0.01070(16) 0.22826(14) 0.06117(16) 0.0304(4) Uani 1 1 d
N3 N 0.7082(2) 0.11033(14) 0.33647(19) 0.0354(4) Uani 1 1 d
N4 N 0.70137(17) 0.11789(13) 0.20220(18) 0.0337(4) Uani 1 1 d
N5 N 0.14951(18) -0.02899(13) 0.23919(16) 0.0320(4) Uani 1 1 d
N6 N 0.20012(17) 0.33797(13) 0.03135(16) 0.0289(3) Uani 1 1 d
N7 N 0.48542(19) 0.13702(14) -0.03235(18) 0.0361(4) Uani 1 1 d
C1 C 0.1352(2) 0.07971(15) 0.17561(18) 0.0260(4) Uani 1 1 d
C2 C 0.25363(18) 0.14707(15) 0.15459(18) 0.0242(4) Uani 1 1 d
C3 C 0.15095(19) 0.23727(15) 0.08198(18) 0.0248(4) Uani 1 1 d
C4 C 0.5559(2) 0.11664(17) 0.3408(2) 0.0336(4) Uani 1 1 d
C5 C 0.43758(19) 0.13053(15) 0.20140(19) 0.0261(4) Uani 1 1 d
C6 C 0.5370(2) 0.13023(15) 0.1204(2) 0.0278(4) Uani 1 1 d
H1N H -0.100(3) 0.1112(19) 0.126(2) 0.048(7) Uiso 1 1 d
H2N H 0.797(3) 0.1046(17) 0.408(2) 0.036(6) Uiso 1 1 d
H4 H 0.542(2) 0.1094(16) 0.427(2) 0.028(5) 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
N2 N1 C1 112.04(14)
N2 N1 H1N 120.5(17)
C1 N1 H1N 126.7(17)
N1 N2 C3 103.61(14)
C4 N3 N4 113.25(16)
C4 N3 H2N 123.9(15)
N4 N3 H2N 122.8(15)
C6 N4 N3 103.55(14)
O2 N5 O1 125.88(16)
O2 N5 C1 117.97(14)
O1 N5 C1 116.16(15)
O4 N6 O3 123.85(16)
O4 N6 C3 118.00(14)
O3 N6 C3 118.15(13)
O6 N7 O5 124.28(17)
O6 N7 C6 117.78(15)
O5 N7 C6 117.93(15)
N1 C1 C2 109.04(16)
N1 C1 N5 119.25(15)
C2 C1 N5 131.66(15)
C1 C2 C3 100.58(13)
C1 C2 C5 129.59(16)
C3 C2 C5 129.78(15)
N2 C3 C2 114.71(15)
N2 C3 N6 117.04(15)
C2 C3 N6 128.23(14)
N3 C4 C5 107.42(17)
N3 C4 H4 122.2(11)
C5 C4 H4 130.3(11)
C4 C5 C6 103.10(14)
C4 C5 C2 126.66(15)
C6 C5 C2 130.18(16)
N4 C6 C5 112.66(17)
N4 C6 N7 117.66(15)
C5 C6 N7 129.63(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2159(19)
O2 N5 1.2154(18)
O3 N6 1.2282(19)
O4 N6 1.2138(18)
O5 N7 1.2226(19)
O6 N7 1.216(2)
N1 N2 1.323(2)
N1 C1 1.343(2)
N1 H1N 0.78(2)
N2 C3 1.324(2)
N3 C4 1.331(2)
N3 N4 1.339(2)
N3 H2N 0.81(2)
N4 C6 1.323(2)
N5 C1 1.434(2)
N6 C3 1.439(2)
N7 C6 1.425(2)
C1 C2 1.382(2)
C2 C3 1.398(2)
C2 C5 1.468(2)
C4 C5 1.371(3)
C4 H4 0.93(2)
C5 C6 1.407(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
C1 N1 N2 C3 1.4(2)
C4 N3 N4 C6 0.5(2)
N2 N1 C1 C2 -1.1(2)
N2 N1 C1 N5 -178.68(15)
O2 N5 C1 N1 -167.00(16)
O1 N5 C1 N1 13.1(2)
O2 N5 C1 C2 16.1(3)
O1 N5 C1 C2 -163.78(19)
N1 C1 C2 C3 0.36(19)
N5 C1 C2 C3 177.51(18)
N1 C1 C2 C5 177.95(17)
N5 C1 C2 C5 -4.9(3)
N1 N2 C3 C2 -1.1(2)
N1 N2 C3 N6 -179.70(15)
C1 C2 C3 N2 0.5(2)
C5 C2 C3 N2 -177.08(17)
C1 C2 C3 N6 178.86(17)
C5 C2 C3 N6 1.3(3)
O4 N6 C3 N2 176.02(16)
O3 N6 C3 N2 -3.4(2)
O4 N6 C3 C2 -2.3(3)
O3 N6 C3 C2 178.30(17)
N4 N3 C4 C5 -0.7(2)
N3 C4 C5 C6 0.5(2)
N3 C4 C5 C2 -176.74(18)
C1 C2 C5 C4 -58.2(3)
C3 C2 C5 C4 118.7(2)
C1 C2 C5 C6 125.2(2)
C3 C2 C5 C6 -57.8(3)
N3 N4 C6 C5 -0.1(2)
N3 N4 C6 N7 -177.89(16)
C4 C5 C6 N4 -0.3(2)
C2 C5 C6 N4 176.86(17)
C4 C5 C6 N7 177.19(19)
C2 C5 C6 N7 -5.7(3)
O6 N7 C6 N4 -178.91(17)
O5 N7 C6 N4 2.2(3)
O6 N7 C6 C5 3.7(3)
O5 N7 C6 C5 -175.19(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179040
