#------------------------------------------------------------------------------
#$Date: 2025-07-06 18:54:50 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300817 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/84/7718437.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_7718437
loop_
_publ_author_name
'Jiang, Xiu'e'
'Wang, Ruihui'
'Fan, Mingren'
'Song, Siwei'
'Wang, Yi'
'Zhang, Qinghua'
_publ_section_title
;
 Combination of 5-amino-4-nitro-1,2-dihydro-3H-pyrazol-3-one and
 azine frameworks for insensitive, heat-resistant energetic materials.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7056
_journal_page_last               7061
_journal_paper_doi               10.1039/d5dt00488h
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl O3.97, C9 H9 N12 O6'
_chemical_formula_sum            'C9 H9 Cl N12 O9.97'
_chemical_formula_weight         480.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.011(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6357(6)
_cell_length_b                   5.8232(3)
_cell_length_c                   18.7157(9)
_cell_measurement_reflns_used    9063
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      2.210
_cell_volume                     1678.12(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22346
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             975
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.9230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                3462
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5dt00488h2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7718434--7718437.cif.'
_cod_original_cell_volume        1678.12(13)
_cod_database_code               7718437
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N00B(H00B), N00E(H00E)
2.b X=CH2 refined with riding coordinates:
 N00G(H00a,H00c), N00L(H00d,H00f), N00P(H00g,H00h)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl01 Cl 0.54496(4) 0.03667(13) 0.64136(4) 0.03815(19) Uani 1 d . . .
O002 O 0.75949(17) 0.1328(4) 0.28459(13) 0.0448(5) Uani 1 d . . .
O003 O 0.78635(16) -0.1387(4) 0.36546(13) 0.0441(5) Uani 1 d . . .
O004 O 0.35739(17) 0.4270(4) 0.68353(14) 0.0462(6) Uani 1 d . . .
N005 N 0.47612(16) 0.5030(4) 0.46172(13) 0.0284(5) Uani 1 d . . .
H005 H 0.4859 0.3975 0.4943 0.034 Uiso 1 calc . . R
N006 N 0.37354(15) 0.6679(4) 0.51926(13) 0.0293(5) Uani 1 d . . .
N007 N 0.74398(16) 0.0284(4) 0.33965(15) 0.0319(5) Uani 1 d . . .
N008 N 0.39846(16) 0.8387(4) 0.41427(13) 0.0306(5) Uani 1 d . . .
O009 O 0.26178(16) 0.8210(5) 0.71528(13) 0.0468(6) Uani 1 d . . .
N00A N 0.50460(17) 0.6743(4) 0.35216(14) 0.0332(5) Uani 1 d . . .
N00B N 0.39040(16) 0.5013(4) 0.57288(15) 0.0318(5) Uani 1 d . . .
H00B H 0.4224 0.3819 0.5715 0.038 Uiso 1 calc . . R
O00C O 0.6790(2) -0.1349(5) 0.47751(15) 0.0597(8) Uani 1 d . . .
N00D N 0.57770(16) 0.3504(4) 0.40107(14) 0.0308(5) Uani 1 d . . .
N00E N 0.59120(18) 0.1772(4) 0.45308(15) 0.0379(6) Uani 1 d . . .
H00E H 0.5639 0.1650 0.4890 0.046 Uiso 1 calc . . R
N00F N 0.25499(17) 0.8825(5) 0.65166(15) 0.0370(6) Uani 1 d . . .
N00G N 0.28809(19) 1.0052(5) 0.49891(18) 0.0394(6) Uani 1 d . . .
H00A H 0.3041 1.0259 0.4577 0.047 Uiso 1 calc . . R
H00C H 0.2530 1.1006 0.5137 0.047 Uiso 1 calc . . R
O00H O 0.4919(2) 0.1027(6) 0.57309(16) 0.0663(8) Uani 1 d A . .
C00I C 0.41868(16) 0.6701(4) 0.46170(14) 0.0264(5) Uani 1 d . . .
C00J C 0.51707(18) 0.5191(4) 0.40464(16) 0.0275(5) Uani 1 d . . .
C00K C 0.63044(16) 0.3147(5) 0.35010(15) 0.0279(5) Uani 1 d . . .
N00L N 0.63089(19) 0.4462(5) 0.29438(15) 0.0405(6) Uani 1 d . . .
H00D H 0.5970 0.5635 0.2876 0.049 Uiso 1 calc . . R
H00F H 0.6651 0.4163 0.2642 0.049 Uiso 1 calc . . R
O00M O 0.2140(2) 1.0492(5) 0.62664(19) 0.0624(8) Uani 1 d . . .
C00N C 0.31724(17) 0.8277(5) 0.53931(16) 0.0296(5) Uani 1 d . . .
C00O C 0.34887(19) 0.5565(5) 0.62681(17) 0.0305(6) Uani 1 d . . .
N00P N 0.4282(2) 0.9971(5) 0.30975(16) 0.0410(7) Uani 1 d . . .
H00G H 0.4561 1.0004 0.2740 0.049 Uiso 1 calc . . R
H00H H 0.3898 1.1004 0.3133 0.049 Uiso 1 calc . . R
C00Q C 0.67901(18) 0.1165(5) 0.37362(15) 0.0299(5) Uani 1 d . . .
C00R C 0.30180(17) 0.7578(5) 0.60718(15) 0.0293(5) Uani 1 d . . .
C00S C 0.6541(2) 0.0290(5) 0.43891(18) 0.0346(6) Uani 1 d . . .
C00T C 0.44422(18) 0.8339(5) 0.35904(15) 0.0301(6) Uani 1 d . . .
O00U O 0.6316(2) 0.0028(8) 0.6304(2) 0.0878(12) Uani 1 d A . .
O00V O 0.5432(3) 0.2087(12) 0.6934(3) 0.121(3) Uani 0.968(14) d A 1 .
O2 O 0.5103(4) -0.1593(11) 0.6666(4) 0.150(3) Uani 1 d A 1 .
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'
Cl Cl 0.1484 0.1585 '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
O00U Cl01 O00H 108.9(2) . . ?
O00V Cl01 O00H 110.2(3) . . ?
O00V Cl01 O00U 109.5(3) . . ?
O2 Cl01 O00H 108.8(3) . . ?
O2 Cl01 O00U 112.1(4) . . ?
O2 Cl01 O00V 107.3(5) . . ?
C00I N005 H005 124.3 . . ?
C00I N005 C00J 111.5(2) . . ?
C00J N005 H005 124.3 . . ?
C00I N006 N00B 120.6(2) . . ?
C00N N006 N00B 109.0(2) . . ?
C00N N006 C00I 129.9(2) . . ?
O002 N007 C00Q 117.3(2) . . ?
O003 N007 O002 122.6(2) . . ?
O003 N007 C00Q 120.1(3) . . ?
C00I N008 C00T 113.6(2) . . ?
C00J N00A C00T 114.5(2) . . ?
N006 N00B H00B 125.6 . . ?
C00O N00B N006 108.9(2) . . ?
C00O N00B H00B 125.6 . . ?
C00J N00D N00E 120.4(2) . . ?
C00J N00D C00K 129.8(2) . . ?
C00K N00D N00E 109.7(2) . . ?
N00D N00E H00E 124.8 . . ?
C00S N00E N00D 110.4(2) . . ?
C00S N00E H00E 124.8 . . ?
O009 N00F C00R 117.2(3) . . ?
O00M N00F O009 123.9(3) . . ?
O00M N00F C00R 118.7(3) . . ?
H00A N00G H00C 120.0 . . ?
C00N N00G H00A 120.0 . . ?
C00N N00G H00C 120.0 . . ?
N005 C00I N006 115.5(2) . . ?
N005 C00I N008 128.9(3) . . ?
N008 C00I N006 115.7(2) . . ?
N005 C00J N00D 114.7(2) . . ?
N00A C00J N005 127.6(2) . . ?
N00A C00J N00D 117.7(2) . . ?
N00D C00K C00Q 105.2(2) . . ?
N00L C00K N00D 123.7(2) . . ?
N00L C00K C00Q 131.1(2) . . ?
C00K N00L H00D 120.0 . . ?
C00K N00L H00F 120.0 . . ?
H00D N00L H00F 120.0 . . ?
N006 C00N C00R 105.7(2) . . ?
N00G C00N N006 123.3(3) . . ?
N00G C00N C00R 131.0(3) . . ?
O004 C00O N00B 119.3(3) . . ?
O004 C00O C00R 132.9(3) . . ?
N00B C00O C00R 107.9(2) . . ?
H00G N00P H00H 120.0 . . ?
C00T N00P H00G 120.0 . . ?
C00T N00P H00H 120.0 . . ?
N007 C00Q C00K 123.9(3) . . ?
N007 C00Q C00S 125.9(3) . . ?
C00K C00Q C00S 110.2(2) . . ?
C00N C00R N00F 125.5(3) . . ?
C00N C00R C00O 108.5(2) . . ?
C00O C00R N00F 125.6(3) . . ?
O00C C00S N00E 123.0(3) . . ?
O00C C00S C00Q 132.4(3) . . ?
N00E C00S C00Q 104.5(2) . . ?
N00A C00T N008 124.0(2) . . ?
N00P C00T N008 117.2(2) . . ?
N00P C00T N00A 118.8(3) . . ?
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
Cl01 O00H 1.449(3) . ?
Cl01 O00U 1.419(4) . ?
Cl01 O00V 1.400(4) . ?
Cl01 O2 1.382(4) . ?
O002 N007 1.256(4) . ?
O003 N007 1.228(4) . ?
O004 C00O 1.290(4) . ?
N005 H005 0.8600 . ?
N005 C00I 1.324(3) . ?
N005 C00J 1.341(4) . ?
N006 N00B 1.388(3) . ?
N006 C00I 1.387(3) . ?
N006 C00N 1.377(3) . ?
N007 C00Q 1.387(3) . ?
N008 C00I 1.324(3) . ?
N008 C00T 1.356(4) . ?
O009 N00F 1.230(4) . ?
N00A C00J 1.324(4) . ?
N00A C00T 1.347(3) . ?
N00B H00B 0.8600 . ?
N00B C00O 1.331(4) . ?
O00C C00S 1.219(4) . ?
N00D N00E 1.392(3) . ?
N00D C00J 1.375(3) . ?
N00D C00K 1.381(3) . ?
N00E H00E 0.8600 . ?
N00E C00S 1.369(4) . ?
N00F O00M 1.212(4) . ?
N00F C00R 1.403(3) . ?
N00G H00A 0.8600 . ?
N00G H00C 0.8600 . ?
N00G C00N 1.314(4) . ?
C00K N00L 1.295(4) . ?
C00K C00Q 1.409(4) . ?
N00L H00D 0.8600 . ?
N00L H00F 0.8600 . ?
C00N C00R 1.394(4) . ?
C00O C00R 1.399(4) . ?
N00P H00G 0.8600 . ?
N00P H00H 0.8600 . ?
N00P C00T 1.318(4) . ?
C00Q C00S 1.439(4) . ?
