#------------------------------------------------------------------------------
#$Date: 2025-04-05 04:35:26 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298842 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/99/7249960.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_7249960
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(C H6 N3)'
_chemical_formula_sum            'C6 H12 N12 O4'
_chemical_formula_weight         316.28
_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   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2j4fgl
_audit_creation_date             2023-12-21
_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                 94.393(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.55870(10)
_cell_length_b                   17.1844(6)
_cell_length_c                   10.0828(4)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.195
_cell_measurement_theta_min      5.097
_cell_volume                     614.79(4)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6855
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.393
_diffrn_reflns_theta_min         5.097
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.6897.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0036(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0383
_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)+(0.0585P)²+0.0657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                929
_reflns_number_total             1132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01286k2.cif
_cod_data_source_block           cu_20231219_wq_nlg_dg_0m
_cod_depositor_comments
'Adding full bibliography for 7249960--7249966.cif.'
_cod_database_code               7249960
_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   0.885
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B)
;
_shelx_res_file
;
TITL cu_20231219_wq_nlg_dg_0m_a.res in P2(1)/c
    cu_20231219_wq_nlg_dg_0m.res
    created by SHELXL-2018/3 at 13:59:44 on 21-Dec-2023
REM Old TITL cu_20231219_WQ_NLG_DG_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.127, Rweak 0.006, Alpha 0.013
REM <I/s> 0.806 for 53 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 N O
CELL 1.54178 3.5587 17.1844 10.0828 90 94.393 90
ZERR 2 0.0001 0.0006 0.0004 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 12 24 24 8

L.S. 4 0 0
PLAN  2
SIZE 0.1 0.12 0.13
TEMP -80.15
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT 0 0 2
OMIT 0 3 2
REM <olex2.extras>
REM <HklSrc "%.\\cu_20231219_WQ_NLG_DG_0m.hkl">
REM </olex2.extras>

WGHT    0.058500    0.065700
EXTI    0.003571
FVAR       0.91676
O1    4    0.293141    0.459442    0.827566    11.00000    0.05102    0.02998 =
         0.03477   -0.00025    0.01207    0.00788
N1    3    0.425389    0.410199    0.752549    11.00000    0.03131    0.02754 =
         0.03255    0.00145    0.00408    0.00195
O2    4    0.481765    0.341429    0.789562    11.00000    0.05627    0.02854 =
         0.03970    0.00794    0.01532    0.01003
N2    3    0.637677    0.382335    0.537417    11.00000    0.03469    0.02600 =
         0.03196   -0.00019    0.00695    0.00125
N3    3    0.670638    0.418025    0.420701    11.00000    0.03360    0.02347 =
         0.03096   -0.00007    0.00572    0.00086
C3    1    0.503863    0.433532    0.625279    11.00000    0.02767    0.02466 =
         0.02941    0.00008    0.00415    0.00011
N4    3    0.858058    0.303722    0.221992    11.00000    0.03938    0.02848 =
         0.03612    0.00151    0.00843   -0.00033
AFIX  93
H4A   2    0.820847    0.338704    0.283367    11.00000   -1.20000
H4B   2    0.798723    0.254721    0.234767    11.00000   -1.20000
AFIX   0

C4    1    0.554136    0.493424    0.436387    11.00000    0.02490    0.02345 =
         0.02890   -0.00195    0.00374   -0.00065
N5    3    1.065708    0.272062    0.018018    11.00000    0.04334    0.03031 =
         0.03181   -0.00172    0.00667   -0.00050
AFIX  93
H5A   2    1.165802    0.286215   -0.055399    11.00000   -1.20000
H5B   2    1.006800    0.222995    0.030367    11.00000   -1.20000
AFIX   0
C5    1    1.003452    0.324836    0.110327    11.00000    0.02720    0.02817 =
         0.03169    0.00014   -0.00067    0.00233
N6    3    1.092313    0.398669    0.091560    11.00000    0.04813    0.02749 =
         0.03957   -0.00049    0.01174   -0.00214
AFIX  93
H6A   2    1.054748    0.433507    0.153132    11.00000   -1.20000
H6B   2    1.188908    0.412879    0.017522    11.00000   -1.20000
AFIX   0
HKLF 4




REM  cu_20231219_wq_nlg_dg_0m_a.res in P2(1)/c
REM wR2 = 0.1018, GooF = S = 1.123, Restrained GooF = 1.123 for all data
REM R1 = 0.0383 for 929 Fo > 4sig(Fo) and 0.0477 for all 1132 data
REM 101 parameters refined using 0 restraints

END

WGHT      0.0585      0.0657

REM Highest difference peak  0.234,  deepest hole -0.201,  1-sigma level  0.053
Q1    1   0.5544  0.4793  0.6211  11.00000  0.05    0.23
Q2    1   0.3747  0.4686  0.6095  11.00000  0.05    0.19
;
_shelx_res_checksum              60698
_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 0.2931(4) 0.45944(7) 0.82757(12) 0.0381(4) Uani 1 1 d . . . . .
N1 N 0.4254(4) 0.41020(8) 0.75255(15) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.4818(4) 0.34143(7) 0.78956(13) 0.0409(4) Uani 1 1 d . . . . .
N2 N 0.6377(4) 0.38234(8) 0.53742(14) 0.0307(4) Uani 1 1 d . . . . .
N3 N 0.6706(4) 0.41802(8) 0.42070(14) 0.0292(4) Uani 1 1 d . . . . .
C3 C 0.5039(4) 0.43353(9) 0.62528(16) 0.0271(4) Uani 1 1 d . . . . .
N4 N 0.8581(4) 0.30372(9) 0.22199(15) 0.0344(4) Uani 1 1 d . . . . .
H4A H 0.820847 0.338704 0.283367 0.041 Uiso 1 1 calc R U . . .
H4B H 0.798723 0.254721 0.234767 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5541(4) 0.49342(9) 0.43639(16) 0.0257(4) Uani 1 1 d . . . . .
N5 N 1.0657(4) 0.27206(9) 0.01802(15) 0.0350(4) Uani 1 1 d . . . . .
H5A H 1.165802 0.286215 -0.055399 0.042 Uiso 1 1 calc R U . . .
H5B H 1.006800 0.222995 0.030367 0.042 Uiso 1 1 calc R U . . .
C5 C 1.0035(4) 0.32484(10) 0.11033(17) 0.0292(4) Uani 1 1 d . . . . .
N6 N 1.0923(4) 0.39867(9) 0.09156(16) 0.0380(4) Uani 1 1 d . . . . .
H6A H 1.054748 0.433507 0.153132 0.046 Uiso 1 1 calc R U . . .
H6B H 1.188908 0.412879 0.017522 0.046 Uiso 1 1 calc R U . . .
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 0.0510(8) 0.0300(7) 0.0348(7) -0.0002(5) 0.0121(6) 0.0079(5)
N1 0.0313(8) 0.0275(8) 0.0325(8) 0.0015(6) 0.0041(6) 0.0020(6)
O2 0.0563(8) 0.0285(7) 0.0397(7) 0.0079(5) 0.0153(6) 0.0100(6)
N2 0.0347(8) 0.0260(7) 0.0320(8) -0.0002(6) 0.0069(6) 0.0012(6)
N3 0.0336(8) 0.0235(7) 0.0310(7) -0.0001(5) 0.0057(6) 0.0009(5)
C3 0.0277(9) 0.0247(8) 0.0294(8) 0.0001(7) 0.0041(7) 0.0001(6)
N4 0.0394(9) 0.0285(8) 0.0361(8) 0.0015(6) 0.0084(6) -0.0003(6)
C4 0.0249(8) 0.0234(9) 0.0289(8) -0.0019(6) 0.0037(6) -0.0007(6)
N5 0.0433(9) 0.0303(8) 0.0318(8) -0.0017(6) 0.0067(6) -0.0005(6)
C5 0.0272(8) 0.0282(9) 0.0317(8) 0.0001(7) -0.0007(6) 0.0023(6)
N6 0.0481(9) 0.0275(8) 0.0396(9) -0.0005(6) 0.0117(7) -0.0021(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
O1 N1 O2 121.20(14) . . ?
O1 N1 C3 118.27(14) . . ?
O2 N1 C3 120.52(14) . . ?
N3 N2 C3 109.54(13) . . ?
N2 N3 C4 106.45(13) . . ?
N1 C3 C4 129.05(15) . 3_666 ?
N2 C3 N1 121.25(15) . . ?
N2 C3 C4 109.61(14) . 3_666 ?
H4A N4 H4B 120.0 . . ?
C5 N4 H4A 120.0 . . ?
C5 N4 H4B 120.0 . . ?
N3 C4 C3 145.60(15) . 3_666 ?
N3 C4 C4 111.61(18) . 3_666 ?
C4 C4 C3 102.80(17) 3_666 3_666 ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
N4 C5 N5 120.30(16) . . ?
N6 C5 N4 119.77(16) . . ?
N6 C5 N5 119.91(16) . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
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 N1 1.2507(19) . ?
N1 O2 1.2509(18) . ?
N1 C3 1.393(2) . ?
N2 N3 1.340(2) . ?
N2 C3 1.360(2) . ?
N3 C4 1.373(2) . ?
C3 C4 1.409(2) 3_666 ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C5 1.325(2) . ?
C4 C4 1.386(3) 3_666 ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.330(2) . ?
C5 N6 1.325(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
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 N1 C3 N2 -178.06(15) . . . . ?
O1 N1 C3 C4 -2.0(3) . . . 3_666 ?
O2 N1 C3 N2 1.0(2) . . . . ?
O2 N1 C3 C4 177.10(16) . . . 3_666 ?
N2 N3 C4 C3 179.9(2) . . . 3_666 ?
N2 N3 C4 C4 0.1(2) . . . 3_666 ?
N3 N2 C3 N1 176.74(14) . . . . ?
N3 N2 C3 C4 -0.04(18) . . . 3_666 ?
C3 N2 N3 C4 -0.01(18) . . . . ?
