#------------------------------------------------------------------------------
#$Date: 2026-03-05 13:13:40 +0100 (Thu 05 de Mar de 2026) $
#$Revision: 304864 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/53/7135349.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_7135349
loop_
_publ_author_name
'Kukreja, Sonali'
'Yadav, Abhishek Kumar'
'Dharavath, Srinivas'
_publ_section_title
;
 4,5-Diazido-6-nitropyridazin-3(2H)-one: a versatile nitrogen-rich
 compound for multifaceted energetic applications.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4986
_journal_page_last               4990
_journal_paper_doi               10.1039/d6cc00109b
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         '2(C4 H N9 O3)'
_chemical_formula_sum            'C8 H2 N18 O6'
_chemical_formula_weight         446.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-08-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2025-08-05 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                105.371(9)
_cell_angle_beta                 96.160(10)
_cell_angle_gamma                97.443(10)
_cell_formula_units_Z            2
_cell_length_a                   6.479(3)
_cell_length_b                   11.334(5)
_cell_length_c                   11.614(5)
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.23
_cell_volume                     806.4(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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  0.0711
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.842
_diffrn_reflns_theta_min         2.233
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4412
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1593 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.5917.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0645
_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)+(0.0709P)²+0.8938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             4101
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc00109b2.cif
_cod_data_source_block           7mara_o_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135349.cif.'
_cod_database_code               7135349
_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   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N009(H009)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2678(3) 0.07463(18) -0.00224(18) 0.0200(4) Uani 1 1 d . . . . .
O002 O 0.4515(3) 0.34342(17) 0.90301(18) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.3222(3) 0.2160(2) 0.54818(19) 0.0269(5) Uani 1 1 d . . . . .
O004 O -0.3209(3) 0.5875(2) 0.8555(2) 0.0291(5) Uani 1 1 d . . . . .
N8 N 0.6657(4) 0.1929(2) 0.0531(2) 0.0167(5) Uani 1 1 d . . . . .
O2 O 0.0251(3) 0.2668(2) 0.4911(2) 0.0326(5) Uani 1 1 d . . . . .
O007 O -0.3215(4) 0.4914(2) 0.6680(2) 0.0348(6) Uani 1 1 d . . . . .
N1 N 0.0888(4) 0.0823(2) 0.1563(2) 0.0193(5) Uani 1 1 d . . . . .
H1 H -0.019183 0.034073 0.105912 0.023 Uiso 1 1 calc R U . . .
N009 N 0.2480(3) 0.4936(2) 0.9124(2) 0.0171(5) Uani 1 1 d . . . . .
H009 H 0.351641 0.546866 0.961984 0.021 Uiso 1 1 calc R U . . .
N7 N 0.6366(4) 0.2227(2) 0.1606(2) 0.0196(5) Uani 1 1 d . . . . .
N3 N 0.1889(4) 0.2275(2) 0.4721(2) 0.0200(5) Uani 1 1 d . . . . .
N00C N 0.2783(4) 0.1204(2) 0.7567(2) 0.0182(5) Uani 1 1 d . . . . .
N00D N 0.0737(4) 0.5379(2) 0.8850(2) 0.0176(5) Uani 1 1 d . . . . .
N5 N 0.7080(4) 0.3809(2) 0.3822(2) 0.0223(5) Uani 1 1 d . . . . .
N4 N 0.5732(4) 0.3064(2) 0.4079(2) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.0630(4) 0.1189(2) 0.2725(2) 0.0187(5) Uani 1 1 d . . . . .
N00H N -0.2558(4) 0.5158(2) 0.7744(2) 0.0208(5) Uani 1 1 d . . . . .
N00I N -0.2518(4) 0.1575(2) 0.6161(2) 0.0224(5) Uani 1 1 d . . . . .
N00J N -0.2598(4) 0.2597(2) 0.6887(2) 0.0207(5) Uani 1 1 d . . . . .
N00K N 0.1061(4) 0.1606(2) 0.7532(2) 0.0195(5) Uani 1 1 d . . . . .
N9 N 0.7324(4) 0.1782(2) -0.0339(2) 0.0226(5) Uani 1 1 d . . . . .
N00M N 0.4085(4) 0.0640(2) 0.7493(2) 0.0227(5) Uani 1 1 d . . . . .
N00N N -0.2760(4) 0.0656(3) 0.5454(3) 0.0347(7) Uani 1 1 d . . . . .
C3 C 0.4221(4) 0.2290(2) 0.3128(2) 0.0175(6) Uani 1 1 d . . . . .
N6 N 0.8371(5) 0.4549(3) 0.3783(2) 0.0358(7) Uani 1 1 d . . . . .
C2 C 0.4429(4) 0.1883(2) 0.1937(3) 0.0178(6) Uani 1 1 d . . . . .
C00R C -0.0746(4) 0.3299(2) 0.7594(2) 0.0170(5) Uani 1 1 d . . . . .
C00S C 0.2820(4) 0.3734(2) 0.8714(2) 0.0170(5) Uani 1 1 d . . . . .
C4 C 0.2248(4) 0.1887(2) 0.3453(3) 0.0181(6) Uani 1 1 d . . . . .
C1 C 0.2657(4) 0.1117(2) 0.1069(2) 0.0163(5) Uani 1 1 d . . . . .
C00V C 0.1059(4) 0.2877(2) 0.7928(2) 0.0167(5) Uani 1 1 d . . . . .
C00W C -0.0756(4) 0.4585(2) 0.8100(2) 0.0169(5) Uani 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
_geom_angle_publ_flag
N9 N8 N7 165.8(3) . . ?
N2 N1 H1 116.4 . . ?
N2 N1 C1 127.2(2) . . ?
C1 N1 H1 116.4 . . ?
N00D N009 H009 116.6 . . ?
N00D N009 C00S 126.7(2) . . ?
C00S N009 H009 116.6 . . ?
N8 N7 C2 121.4(2) . . ?
O3 N3 O2 125.6(3) . . ?
O3 N3 C4 117.5(2) . . ?
O2 N3 C4 116.9(2) . . ?
N00M N00C N00K 167.0(3) . . ?
C00W N00D N009 115.7(2) . . ?
N6 N5 N4 169.1(3) . . ?
N5 N4 C3 117.4(2) . . ?
C4 N2 N1 115.4(2) . . ?
O004 N00H C00W 116.8(2) . . ?
O007 N00H O004 125.5(3) . . ?
O007 N00H C00W 117.7(2) . . ?
N00N N00I N00J 169.4(3) . . ?
N00I N00J C00R 118.9(2) . . ?
N00C N00K C00V 119.4(2) . . ?
N4 C3 C4 115.8(2) . . ?
C2 C3 N4 127.6(2) . . ?
C2 C3 C4 116.6(3) . . ?
N7 C2 C1 122.6(2) . . ?
C3 C2 N7 117.5(2) . . ?
C3 C2 C1 119.9(2) . . ?
N00J C00R C00W 116.8(2) . . ?
C00V C00R N00J 127.4(2) . . ?
C00V C00R C00W 115.7(2) . . ?
O002 C00S N009 120.8(2) . . ?
O002 C00S C00V 124.1(2) . . ?
N009 C00S C00V 115.1(2) . . ?
N2 C4 N3 113.5(2) . . ?
N2 C4 C3 126.3(3) . . ?
C3 C4 N3 120.2(2) . . ?
O1 C1 N1 121.0(2) . . ?
O1 C1 C2 124.3(2) . . ?
N1 C1 C2 114.7(2) . . ?
N00K C00V C00S 122.5(2) . . ?
C00R C00V N00K 117.3(2) . . ?
C00R C00V C00S 120.2(2) . . ?
N00D C00W N00H 112.9(2) . . ?
N00D C00W C00R 126.6(2) . . ?
C00R C00W N00H 120.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.228(3) . ?
O002 C00S 1.238(3) . ?
O3 N3 1.212(3) . ?
O004 N00H 1.222(3) . ?
N8 N7 1.246(3) . ?
N8 N9 1.121(3) . ?
O2 N3 1.223(3) . ?
O007 N00H 1.208(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.338(3) . ?
N1 C1 1.377(3) . ?
N009 H009 0.8800 . ?
N009 N00D 1.335(3) . ?
N009 C00S 1.374(3) . ?
N7 C2 1.389(3) . ?
N3 C4 1.474(4) . ?
N00C N00K 1.259(3) . ?
N00C N00M 1.120(3) . ?
N00D C00W 1.297(4) . ?
N5 N4 1.251(3) . ?
N5 N6 1.119(3) . ?
N4 C3 1.407(4) . ?
N2 C4 1.296(4) . ?
N00H C00W 1.480(3) . ?
N00I N00J 1.250(3) . ?
N00I N00N 1.123(4) . ?
N00J C00R 1.394(4) . ?
N00K C00V 1.392(3) . ?
C3 C2 1.365(4) . ?
C3 C4 1.424(4) . ?
C2 C1 1.455(4) . ?
C00R C00V 1.376(4) . ?
C00R C00W 1.421(4) . ?
C00S C00V 1.448(4) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O002 C00S C00V N00K 5.2(4) . . . . ?
O002 C00S C00V C00R -178.1(3) . . . . ?
O3 N3 C4 N2 132.0(3) . . . . ?
O3 N3 C4 C3 -48.5(3) . . . . ?
O004 N00H C00W N00D -46.4(3) . . . . ?
O004 N00H C00W C00R 136.0(3) . . . . ?
N8 N7 C2 C3 -177.4(2) . . . . ?
N8 N7 C2 C1 2.7(4) . . . . ?
O2 N3 C4 N2 -47.0(3) . . . . ?
O2 N3 C4 C3 132.5(3) . . . . ?
O007 N00H C00W N00D 131.2(3) . . . . ?
O007 N00H C00W C00R -46.4(3) . . . . ?
N1 N2 C4 N3 179.6(2) . . . . ?
N1 N2 C4 C3 0.2(4) . . . . ?
N009 N00D C00W N00H -174.6(2) . . . . ?
N009 N00D C00W C00R 2.8(4) . . . . ?
N009 C00S C00V N00K -173.4(2) . . . . ?
N009 C00S C00V C00R 3.3(4) . . . . ?
N7 C2 C1 O1 -2.8(4) . . . . ?
N7 C2 C1 N1 177.3(2) . . . . ?
N00C N00K C00V C00R 163.7(2) . . . . ?
N00C N00K C00V C00S -19.6(4) . . . . ?
N00D N009 C00S O002 179.7(2) . . . . ?
N00D N009 C00S C00V -1.7(4) . . . . ?
N5 N4 C3 C2 27.5(4) . . . . ?
N5 N4 C3 C4 -152.5(3) . . . . ?
N4 C3 C2 N7 2.3(4) . . . . ?
N4 C3 C2 C1 -177.8(2) . . . . ?
N4 C3 C4 N3 -0.4(4) . . . . ?
N4 C3 C4 N2 179.0(3) . . . . ?
N2 N1 C1 O1 -178.1(2) . . . . ?
N2 N1 C1 C2 1.8(4) . . . . ?
N00I N00J C00R C00V -24.6(4) . . . . ?
N00I N00J C00R C00W 160.1(3) . . . . ?
N00J C00R C00V N00K -0.5(4) . . . . ?
N00J C00R C00V C00S -177.4(3) . . . . ?
N00J C00R C00W N00D 174.6(2) . . . . ?
N00J C00R C00W N00H -8.1(4) . . . . ?
N9 N8 N7 C2 -178.3(9) . . . . ?
N00M N00C N00K C00V -175.1(11) . . . . ?
N00N N00I N00J C00R -174.1(16) . . . . ?
C3 C2 C1 O1 177.3(2) . . . . ?
C3 C2 C1 N1 -2.6(4) . . . . ?
N6 N5 N4 C3 171.3(16) . . . . ?
C2 C3 C4 N3 179.6(2) . . . . ?
C2 C3 C4 N2 -1.0(4) . . . . ?
C00S N009 N00D C00W -1.3(4) . . . . ?
C4 C3 C2 N7 -177.7(2) . . . . ?
C4 C3 C2 C1 2.2(4) . . . . ?
C1 N1 N2 C4 -0.7(4) . . . . ?
C00V C00R C00W N00D -1.2(4) . . . . ?
C00V C00R C00W N00H 176.0(2) . . . . ?
C00W C00R C00V N00K 174.8(2) . . . . ?
C00W C00R C00V C00S -2.1(4) . . . . ?
