#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:35:26 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/99/7249961.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_7249961
loop_
_publ_author_name
'Shi, Lei'
'Liu, Bangxiang'
'Wang, Pengfei'
'Gao, Chao'
'Zhang, Chong'
'Du, Yang'
'Sun, Chengguo'
'Hu, Bingcheng'
_publ_section_title
;
 Ionization treatment of pyrazolo[4,3-c]pyrazole derivatives to achieve
 the low sensitivity of high-energy materials
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1918
_journal_page_last               1926
_journal_paper_doi               10.1039/D4CE01286K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C4 N6 O4, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N8 O4'
_chemical_formula_weight         232.18
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2j4fhm
_audit_creation_date             2023-11-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.842(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.4551(3)
_cell_length_b                   14.0564(9)
_cell_length_c                   9.0385(6)
_cell_measurement_reflns_used    1510
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.236
_cell_measurement_theta_min      5.830
_cell_volume                     437.98(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.507
_diffrn_reflns_theta_min         5.829
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.354
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1282 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.7650.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         808
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0522
_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
'w=1/[σ²(Fo²)+(0.0625P)²+0.3052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                674
_reflns_number_total             808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01286k2.cif
_cod_data_source_block           cu_20231122_ys_nlg_dadnpp_0m
_cod_depositor_comments
'Adding full bibliography for 7249960--7249966.cif.'
_cod_database_code               7249961
_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   0.911
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups
2. Restrained distances
 N1-H1B = N1-H1A = N1-H1D = N1-H1C
 0.9 with sigma of 0.02
3.a Free rotating group:
 N1(H1A,H1B)
;
_shelx_res_file
;
TITL cu_20231122_ys_nlg_dadnpp_0m_a.res in P2(1)/c
    cu_20231122_ys_nlg_dadnpp_0m.res
    created by SHELXL-2018/3 at 14:09:05 on 22-Nov-2023
REM Old TITL cu_20231122_YS_NLG_DADNPP_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.156, Rweak 0.006, Alpha 0.014
REM <I/s> 0.242 for 44 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N O
CELL 1.54178 3.4551 14.0564 9.0385 90 93.842 90
ZERR 2 0.0003 0.0009 0.0006 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 8 16 16 8
DFIX 0.9 N1 H1b N1 H1a N1 H1d N1 H1c

L.S. 4
PLAN  10
SIZE 0.07 0.1 0.13
TEMP -80.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\cu_20231122_YS_NLG_DADNPP_0m.hkl">
REM </olex2.extras>

WGHT    0.062500    0.305200
FVAR       1.12529
O1    4    0.503510    0.315250    0.835280    11.00000    0.06097    0.02361 =
         0.03139    0.00699   -0.00429   -0.01119
O2    4    0.773326    0.453447    0.872427    11.00000    0.04805    0.02626 =
         0.02631   -0.00387   -0.00895   -0.00430
AFIX   6
N1    3    0.038064    0.171230    0.636082    11.00000    0.07927    0.01763 =
         0.01625    0.00187   -0.01054   -0.01065
H1A   2    0.122708    0.162049    0.727813    11.00000   -1.50000
H1B   2    0.133414    0.226150    0.613154    11.00000   -1.50000
AFIX   0
H1C   2    0.013171    0.131994    0.566693    11.00000    0.07098
H1D   2   -0.218331    0.166887    0.634111    11.00000    0.15278
N2    3    0.289247    0.401230    0.412945    11.00000    0.02804    0.01620 =
         0.02232   -0.00101   -0.00029    0.00056
N3    3    0.333978    0.358547    0.546256    11.00000    0.02759    0.01831 =
         0.02193    0.00032   -0.00083    0.00072
N4    3    0.595640    0.394597    0.791551    11.00000    0.03050    0.02060 =
         0.02402   -0.00144   -0.00165   -0.00068
C1    1    0.500631    0.421360    0.642874    11.00000    0.02306    0.01793 =
         0.02343   -0.00261   -0.00145    0.00117
C2    1    0.430813    0.492002    0.427167    11.00000    0.02116    0.01724 =
         0.02305   -0.00333   -0.00080    0.00291
HKLF 4




REM  cu_20231122_ys_nlg_dadnpp_0m_a.res in P2(1)/c
REM wR2 = 0.1182, GooF = S = 1.030, Restrained GooF = 1.037 for all data
REM R1 = 0.0436 for 674 Fo > 4sig(Fo) and 0.0522 for all 808 data
REM 84 parameters refined using 4 restraints

END

WGHT      0.0625      0.3052

REM Highest difference peak  0.402,  deepest hole -0.301,  1-sigma level  0.060
Q1    1   0.2212  0.3666  0.3265  11.00000  0.05    0.40
Q2    1   0.2612  0.1634  0.6204  11.00000  0.05    0.32
Q3    1   0.4203  0.5047  0.5044  11.00000  0.05    0.23
Q4    1   0.3977  0.4451  0.4020  11.00000  0.05    0.22
Q5    1   0.3893  0.5344  0.3820  11.00000  0.05    0.21
Q6    1   0.0102  0.2018  0.6408  11.00000  0.05    0.18
Q7    1  -0.0595  0.1480  0.5979  11.00000  0.05    0.15
Q8    1   1.1274  0.4653  0.8223  11.00000  0.05    0.15
Q9    1   0.2470  0.3114  0.5860  11.00000  0.05    0.14
Q10   1   0.7686  0.4623  0.9928  11.00000  0.05    0.14
;
_shelx_res_checksum              15509
_olex2_submission_special_instructions 'No special instructions were received'
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
_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 0.5035(5) 0.31525(11) 0.83528(18) 0.0390(5) Uani 1 1 d . . . . .
O2 O 0.7733(5) 0.45345(11) 0.87243(17) 0.0341(5) Uani 1 1 d . . . . .
N1 N 0.0381(8) 0.17123(14) 0.6361(2) 0.0383(6) Uani 1 1 d DG . . . .
H1A H 0.122708 0.162049 0.727813 0.057 Uiso 1 1 d DG U . . .
H1B H 0.133414 0.226150 0.613154 0.057 Uiso 1 1 d DG U . . .
H1C H 0.013(11) 0.132(2) 0.567(3) 0.071(11) Uiso 1 1 d D . . . .
H1D H -0.218(6) 0.167(5) 0.634(7) 0.15(2) Uiso 1 1 d D . . . .
N2 N 0.2892(5) 0.40123(12) 0.41294(18) 0.0223(4) Uani 1 1 d . . . . .
N3 N 0.3340(5) 0.35855(12) 0.54626(19) 0.0227(4) Uani 1 1 d . . . . .
N4 N 0.5956(5) 0.39460(13) 0.79155(19) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.5006(6) 0.42136(14) 0.6429(2) 0.0216(5) Uani 1 1 d . . . . .
C2 C 0.4308(5) 0.49200(14) 0.4272(2) 0.0206(5) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0610(12) 0.0236(9) 0.0314(9) 0.0070(7) -0.0043(8) -0.0112(7)
O2 0.0481(10) 0.0263(9) 0.0263(9) -0.0039(6) -0.0090(7) -0.0043(7)
N1 0.0793(18) 0.0176(10) 0.0162(10) 0.0019(8) -0.0105(10) -0.0107(10)
N2 0.0280(9) 0.0162(9) 0.0223(9) -0.0010(7) -0.0003(7) 0.0006(6)
N3 0.0276(9) 0.0183(9) 0.0219(9) 0.0003(7) -0.0008(7) 0.0007(6)
N4 0.0305(10) 0.0206(10) 0.0240(9) -0.0014(8) -0.0016(7) -0.0007(7)
C1 0.0231(10) 0.0179(10) 0.0234(11) -0.0026(8) -0.0014(8) 0.0012(7)
C2 0.0212(10) 0.0172(10) 0.0231(10) -0.0033(8) -0.0008(8) 0.0029(7)
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
H1A N1 H1B 104.5 . . ?
H1A N1 H1C 129.0 . . ?
H1A N1 H1D 106.3 . . ?
H1B N1 H1C 115.4 . . ?
H1B N1 H1D 116.7 . . ?
H1C N1 H1D 84(4) . . ?
N3 N2 C2 108.21(16) . . ?
C1 N3 N2 107.90(16) . . ?
O1 N4 O2 122.92(18) . . ?
O1 N4 C1 119.84(17) . . ?
O2 N4 C1 117.24(17) . . ?
N3 C1 N4 120.35(18) . . ?
N3 C1 C2 110.84(18) . 3_666 ?
C2 C1 N4 128.77(18) 3_666 . ?
N2 C2 C1 146.95(19) . 3_666 ?
N2 C2 C2 109.8(2) . 3_666 ?
C2 C2 C1 103.3(2) 3_666 3_666 ?
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 N4 1.232(2) . ?
O2 N4 1.239(2) . ?
N1 H1A 0.8701 . ?
N1 H1B 0.8698 . ?
N1 H1C 0.835(19) . ?
N1 H1D 0.89(2) . ?
N2 N3 1.346(2) . ?
N2 C2 1.369(3) . ?
N3 C1 1.344(3) . ?
N4 C1 1.413(3) . ?
C1 C2 1.400(3) 3_666 ?
C2 C2 1.389(4) 3_666 ?
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
O1 N4 C1 N3 -4.5(3) . . . . ?
O1 N4 C1 C2 178.2(2) . . . 3_666 ?
O2 N4 C1 N3 175.02(18) . . . . ?
O2 N4 C1 C2 -2.2(3) . . . 3_666 ?
N2 N3 C1 N4 -177.71(17) . . . . ?
N2 N3 C1 C2 0.0(2) . . . 3_666 ?
N3 N2 C2 C1 -180.0(3) . . . 3_666 ?
N3 N2 C2 C2 -0.1(3) . . . 3_666 ?
C2 N2 N3 C1 0.0(2) . . . . ?
