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#$Date: 2025-07-06 20:04:50 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/81/7718181.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_7718181
loop_
_publ_author_name
'Li, Miao'
'Zhang, Yubei'
'Dong, Yaqun'
'Liu, Jing'
'Liu, Yuji'
'Huang, Wei'
'Xiao, Chuan'
'Cheng, Guangbin'
'Tang, Yongxing'
_publ_section_title
;
 A high-density energetic ammonium salt via a polynitropyrazolate
 counteranion.
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4444
_journal_page_last               4448
_journal_paper_doi               10.1039/d5dt00237k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_sum            'C18 H28 N42 O38'
_chemical_formula_weight         1440.82
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V118 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-01-19 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.523(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6521(11)
_cell_length_b                   28.997(2)
_cell_length_c                   21.0931(19)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      68.2815
_cell_measurement_theta_min      3.0475
_cell_volume                     5202.9(9)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS 8.5.0.27 Release/2023-03-20 && ToolAlignment 2023.9-2'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17903
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.399
_diffrn_reflns_theta_min         3.048
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_description       block
_exptl_crystal_F_000             2936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     1342
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0504P)²+36.3128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4464
_reflns_number_total             4711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt00237k2.cif
_cod_data_source_block           cu_XR2024026_02_01_LM_Ay_0m
_cod_depositor_comments          'Adding full bibliography for 7718181.cif.'
_cod_original_cell_volume        5203.0(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7718181
_shelx_shelxl_version_number     2019/2
_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.
;
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6662(4) 0.84551(12) 0.43478(17) 0.0183(7) Uani 1 1 d . U . . .
C2 C 0.9086(4) 0.86346(12) 0.47777(17) 0.0180(7) Uani 1 1 d . U . . .
C3 C 0.7611(4) 0.85531(12) 0.49315(17) 0.0171(7) Uani 1 1 d . U . . .
C4 C 0.5005(4) 0.83248(12) 0.41701(17) 0.0185(7) Uani 1 1 d . U . . .
C5 C 0.4216(4) 0.79251(12) 0.42579(18) 0.0194(7) Uani 1 1 d . U . . .
C6 C 0.2697(4) 0.79886(12) 0.39149(18) 0.0192(7) Uani 1 1 d . U . . .
C7 C 0.3588(4) 0.52416(12) 0.11384(17) 0.0176(7) Uani 1 1 d . U . . .
C8 C 0.4748(4) 0.50705(12) 0.16303(17) 0.0171(7) Uani 1 1 d . U . . .
C9 C 0.4568(4) 0.53211(11) 0.21685(17) 0.0154(7) Uani 1 1 d . U . . .
N1S N 0.7606(4) 0.84787(11) 0.39037(15) 0.0215(6) Uani 1 1 d . U . . .
N2 N 0.9092(4) 0.85927(11) 0.41576(15) 0.0227(7) Uani 1 1 d . U . . .
N3 N 0.2516(4) 0.84008(10) 0.36395(15) 0.0195(6) Uani 1 1 d . U . . .
N4 N 0.3924(3) 0.85952(9) 0.37985(14) 0.0159(6) Uani 1 1 d . U . . .
N5 N 0.7220(4) 0.84282(13) 0.32338(16) 0.0307(8) Uani 1 1 d . U . . .
N6 N 0.6948(4) 0.79817(13) 0.30919(16) 0.0313(8) Uani 1 1 d . U . . .
N7 N 1.0548(3) 0.87854(10) 0.51898(14) 0.0180(6) Uani 1 1 d . U . . .
N8 N 0.7137(3) 0.85211(10) 0.55488(14) 0.0174(6) Uani 1 1 d . U . . .
N9 N 0.4941(4) 0.75222(11) 0.45762(19) 0.0313(8) Uani 1 1 d . U . . .
N10 N 0.1366(4) 0.76853(11) 0.38124(17) 0.0264(7) Uani 1 1 d . U . . .
N11 N 0.4166(4) 0.90160(10) 0.35173(15) 0.0229(7) Uani 1 1 d . U . . .
N12 N 0.4249(3) 0.93464(10) 0.39515(14) 0.0173(6) Uani 1 1 d . U . . .
N13 N 0.3357(3) 0.56124(10) 0.19641(14) 0.0173(6) Uani 1 1 d . U . . .
N14 N 0.2728(4) 0.55669(10) 0.13437(15) 0.0191(6) Uani 1 1 d . U . . .
N15 N 0.3165(4) 0.50926(11) 0.04754(15) 0.0222(7) Uani 1 1 d . U . . .
N16 N 0.5986(3) 0.47402(10) 0.16122(14) 0.0178(6) Uani 1 1 d . U . . .
N17 N 0.2827(4) 0.59685(10) 0.23208(15) 0.0223(7) Uani 1 1 d . U . . .
N18 N 0.2003(4) 0.57842(11) 0.27360(15) 0.0211(7) Uani 1 1 d . U . . .
O1 O 0.6754(4) 0.78909(14) 0.25046(15) 0.0504(10) Uani 1 1 d . U . . .
O2 O 1.1776(3) 0.86742(10) 0.50370(14) 0.0265(6) Uani 1 1 d . U . . .
O3 O 0.8154(3) 0.84370(9) 0.60218(12) 0.0259(6) Uani 1 1 d . U . . .
O4 O 0.4472(4) 0.71463(10) 0.4361(2) 0.0564(10) Uani 1 1 d . U . . .
O5 O 0.1342(4) 0.73700(11) 0.41918(16) 0.0394(8) Uani 1 1 d . U . . .
O6 O 0.4217(4) 0.92802(10) 0.45205(14) 0.0376(8) Uani 1 1 d . U . . .
O7 O 0.6873(3) 0.76779(10) 0.35028(14) 0.0320(7) Uani 1 1 d . U . . .
O8 O 1.0421(3) 0.90265(9) 0.56539(13) 0.0259(6) Uani 1 1 d . U . . .
O9 O 0.5737(3) 0.85699(10) 0.55645(13) 0.0265(6) Uani 1 1 d . U . . .
O10 O 0.6002(4) 0.75839(12) 0.50451(17) 0.0443(9) Uani 1 1 d . U . . .
O11 O 0.0335(3) 0.77578(10) 0.33399(16) 0.0346(7) Uani 1 1 d . U . . .
O12 O 0.4383(3) 0.97473(8) 0.37313(13) 0.0237(6) Uani 1 1 d . U . . .
O13 O 0.2250(4) 0.53302(10) 0.01063(13) 0.0321(7) Uani 1 1 d . U . . .
O14 O 0.6644(3) 0.47405(10) 0.11495(13) 0.0271(6) Uani 1 1 d . U . . .
O15 O 0.1782(3) 0.53655(9) 0.27904(13) 0.0251(6) Uani 1 1 d . U . . .
O16 O 0.3735(4) 0.47285(10) 0.03338(14) 0.0334(7) Uani 1 1 d . U . . .
O17 O 0.6339(3) 0.44867(8) 0.20842(13) 0.0233(6) Uani 1 1 d . U . . .
O18 O 0.1463(3) 0.60747(9) 0.30820(13) 0.0280(6) Uani 1 1 d . U . . .
N1_1 N 0.3956(4) 0.94460(10) 0.57978(14) 0.0196(6) Uani 1 1 d D U . A -1
H1A_1 H 0.440(3) 0.9275(8) 0.5557(12) 0.029 Uiso 1 1 d D U . B -1
H1B_1 H 0.394(4) 0.9307(9) 0.6153(8) 0.029 Uiso 1 1 d D U . C -1
H1C_1 H 0.447(3) 0.9697(6) 0.5875(14) 0.029 Uiso 1 1 d D U . D -1
H1D_1 H 0.3018(15) 0.9505(10) 0.5612(13) 0.029 Uiso 1 1 d D U . E -1
O1_2 O 0.6051(4) 0.81230(11) 0.70608(17) 0.0425(8) Uani 1 1 d D . . F -1
H1A_2 H 0.651(7) 0.8371(12) 0.699(2) 0.064 Uiso 1 1 d D U . G -1
H1B_2 H 0.561(7) 0.8031(18) 0.6689(12) 0.064 Uiso 1 1 d D U . H -1
N1_5 N -0.008(6) 0.86038(19) 0.252(2) 0.022(3) Uani 0.5 1 d DG U P I -1
H1A_5 H -0.042330 0.849811 0.214809 0.034 Uiso 0.5 1 d DG U P I -1
H1B_5 H 0.033526 0.886669 0.249671 0.034 Uiso 0.5 1 d DG U P I -1
H1C_5 H -0.083795 0.862814 0.272911 0.034 Uiso 0.5 1 d DG U P I -1
H1D_5 H 0.060506 0.841833 0.272602 0.034 Uiso 0.5 1 d DG U P I -1
N1_8 N 0.4497(10) 0.6998(3) 0.2663(4) 0.0301(19) Uani 0.453(8) 1 d DG U P J -1
H1A_8 H 0.381798 0.679299 0.270490 0.045 Uiso 0.453(8) 1 d DG U P J -1
H1B_8 H 0.504402 0.706230 0.302900 0.045 Uiso 0.453(8) 1 d DG U P J -1
H1C_8 H 0.509359 0.689777 0.241426 0.045 Uiso 0.453(8) 1 d DG U P J -1
H1D_8 H 0.402558 0.724044 0.249792 0.045 Uiso 0.453(8) 1 d DG U P J -1
N1_7 N 0.3402(8) 0.6845(2) 0.3182(3) 0.0272(16) Uani 0.547(8) 1 d DG U P J -2
H1A_7 H 0.343763 0.655693 0.310822 0.041 Uiso 0.547(8) 1 d DG U P J -2
H1B_7 H 0.245071 0.693211 0.313913 0.041 Uiso 0.547(8) 1 d DG U P J -2
H1C_7 H 0.387665 0.690112 0.356455 0.041 Uiso 0.547(8) 1 d DG U P J -2
H1D_7 H 0.385544 0.699123 0.291581 0.041 Uiso 0.547(8) 1 d DG U P J -2
N1_6 N 0.505(6) 0.9492(2) 0.2549(18) 0.019(3) Uani 0.5 1 d DG U P K -1
H1A_6 H 0.596081 0.938097 0.268547 0.029 Uiso 0.5 1 d DG U P K -1
H1B_6 H 0.470585 0.962032 0.285804 0.029 Uiso 0.5 1 d DG U P K -1
H1C_6 H 0.509878 0.968949 0.225511 0.029 Uiso 0.5 1 d DG U P K -1
H1D_6 H 0.442804 0.927452 0.239347 0.029 Uiso 0.5 1 d DG U P K -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1S C1 C3 105.8(3) . . ?
N1S C1 C4 121.5(3) . . ?
C3 C1 C4 132.6(3) . . ?
N2 C2 C3 112.7(3) . . ?
N2 C2 N7 117.3(3) . . ?
C3 C2 N7 129.8(3) . . ?
C1 C3 C2 104.4(3) . . ?
C1 C3 N8 125.0(3) . . ?
C2 C3 N8 130.3(3) . . ?
N4 C4 C5 105.0(3) . . ?
N4 C4 C1 122.6(3) . . ?
C5 C4 C1 132.1(3) . . ?
C4 C5 C6 105.3(3) . . ?
C4 C5 N9 124.4(3) . . ?
C6 C5 N9 129.9(3) . . ?
N3 C6 C5 111.8(3) . . ?
N3 C6 N10 117.4(3) . . ?
C5 C6 N10 130.8(3) . . ?
N14 C7 C8 112.4(3) . . ?
N14 C7 N15 118.1(3) . . ?
C8 C7 N15 129.3(3) . . ?
C9 C8 C7 104.5(3) . . ?
C9 C8 N16 124.5(3) . . ?
C7 C8 N16 130.7(3) . . ?
N13 C9 C8 105.3(3) . . ?
N13 C9 C9 122.4(3) . 2_655 ?
C8 C9 C9 132.3(3) . 2_655 ?
N2 N1S C1 113.1(3) . . ?
N2 N1S N5 117.6(3) . . ?
C1 N1S N5 129.2(3) . . ?
C2 N2 N1S 104.0(3) . . ?
C6 N3 N4 104.0(3) . . ?
N3 N4 C4 113.9(3) . . ?
N3 N4 N11 117.9(3) . . ?
C4 N4 N11 127.8(3) . . ?
N6 N5 N1S 109.1(3) . . ?
O7 N6 O1 121.8(4) . . ?
O7 N6 N5 123.9(3) . . ?
O1 N6 N5 114.3(3) . . ?
O2 N7 O8 125.2(3) . . ?
O2 N7 C2 117.9(3) . . ?
O8 N7 C2 116.8(3) . . ?
O9 N8 O3 124.5(3) . . ?
O9 N8 C3 117.6(3) . . ?
O3 N8 C3 117.9(3) . . ?
O4 N9 O10 125.1(4) . . ?
O4 N9 C5 117.8(4) . . ?
O10 N9 C5 117.1(4) . . ?
O5 N10 O11 124.3(3) . . ?
O5 N10 C6 118.1(3) . . ?
O11 N10 C6 117.5(3) . . ?
N12 N11 N4 109.6(3) . . ?
O6 N12 O12 121.7(3) . . ?
O6 N12 N11 124.1(3) . . ?
O12 N12 N11 114.2(3) . . ?
N14 N13 C9 113.9(3) . . ?
N14 N13 N17 119.1(3) . . ?
C9 N13 N17 126.7(3) . . ?
C7 N14 N13 103.9(3) . . ?
O13 N15 O16 125.1(3) . . ?
O13 N15 C7 118.0(3) . . ?
O16 N15 C7 116.8(3) . . ?
O14 N16 O17 124.5(3) . . ?
O14 N16 C8 118.6(3) . . ?
O17 N16 C8 116.8(3) . . ?
N18 N17 N13 108.8(3) . . ?
O15 N18 O18 121.5(3) . . ?
O15 N18 N17 124.2(3) . . ?
O18 N18 N17 114.3(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
C1 N1S 1.352(5) . ?
C1 C3 1.379(5) . ?
C1 C4 1.463(5) . ?
C2 N2 1.314(5) . ?
C2 C3 1.394(5) . ?
C2 N7 1.464(5) . ?
C3 N8 1.438(5) . ?
C4 N4 1.355(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.392(5) . ?
C5 N9 1.434(5) . ?
C6 N3 1.326(5) . ?
C6 N10 1.433(5) . ?
C7 N14 1.322(5) . ?
C7 C8 1.396(5) . ?
C7 N15 1.446(5) . ?
C8 C9 1.380(5) . ?
C8 N16 1.443(5) . ?
C9 N13 1.354(5) . ?
C9 C9 1.460(7) 2_655 ?
N1S N2 1.341(4) . ?
N1S N5 1.399(5) . ?
N3 N4 1.329(4) . ?
N4 N11 1.389(4) . ?
N5 N6 1.340(5) . ?
N6 O7 1.246(4) . ?
N6 O1 1.248(4) . ?
N7 O2 1.210(4) . ?
N7 O8 1.224(4) . ?
N8 O9 1.226(4) . ?
N8 O3 1.228(4) . ?
N9 O4 1.221(5) . ?
N9 O10 1.234(5) . ?
N10 O5 1.218(5) . ?
N10 O11 1.229(5) . ?
N11 N12 1.318(4) . ?
N12 O6 1.221(4) . ?
N12 O12 1.265(4) . ?
N13 N14 1.329(4) . ?
N13 N17 1.403(4) . ?
N15 O13 1.217(4) . ?
N15 O16 1.225(4) . ?
N16 O14 1.216(4) . ?
N16 O17 1.230(4) . ?
N17 N18 1.338(4) . ?
N18 O15 1.238(4) . ?
N18 O18 1.259(4) . ?
