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#$Date: 2025-02-20 01:40:21 +0200 (Thu, 20 Feb 2025) $
#$Revision: 297773 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/99/7249965.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_7249965
loop_
_publ_author_name
'Shi, Lei'
'Liu, Bangxiang'
'Wang, Pengfei'
'Hu, Bingcheng'
'Sun, Chengguo'
'du, yang'
'Gao, Chao'
'zhang, chong'
_publ_section_title
;
 Ionization treatment of pyrazolo[4,3-c]pyrazole derivatives to achieve
 the low sensitivity of high-energy materials
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE01286K
_journal_year                    2025
_chemical_formula_moiety         '2(H4 N O), C4 N6 O4'
_chemical_formula_sum            'C4 H8 N8 O6'
_chemical_formula_weight         264.18
_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.cc2lpt59
_audit_creation_date             2024-05-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-21 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.909(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.6899(7)
_cell_length_b                   13.747(3)
_cell_length_c                   9.3323(13)
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    233.00
_cell_measurement_theta_max      27.225
_cell_measurement_theta_min      2.963
_cell_volume                     470.87(15)
_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      233.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9659
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.648
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0814 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1076
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0858P)²+0.7887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.1925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                893
_reflns_number_total             1076
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01286k2.cif
_cod_data_source_block           mo_20240428_wq_nlg_nh3oh_0m
_cod_original_cell_volume        470.88(14)
_cod_database_code               7249965
_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. Restrained distances
 O1-H1
 0.9 with sigma of 0.01
 H4C-H1
 2.1 with sigma of 0.01
2.a Everything fixed:
 H4A, H4B, H4C
;
_shelx_res_file
;
TITL mo_20240428_wq_nlg_nh3oh_0m_a.res in P2(1)/c
    mo_20240428_wq_nlg_nh3oh_0m.res
    created by SHELXL-2018/3 at 11:26:11 on 07-May-2024
REM Old TITL mo_20240428_WQ_NLG_NH3OH_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.143, Rweak 0.017, Alpha 0.025
REM <I/s> 1.230 for 49 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N O2
CELL 0.71073 3.6899 13.7474 9.3323 90 95.909 90
ZERR 2 0.0007 0.0025 0.0013 0 0.01 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 8 16 16 12
DFIX 0.9 0.01 O1 H1
DFIX 2.1 0.01 H4c H1

L.S. 4 0 0
PLAN  4
SIZE 0.1 0.11 0.12
TEMP -40.15
CONF
BOND
list 4
fmap 2 53
ACTA
MORE -1
BOND $H
OMIT -1 0 2
OMIT 0 2 1
OMIT 1 2 1
REM <olex2.extras>
REM <HklSrc "%.\\mo_20240428_WQ_NLG_NH3OH_0m.hkl">
REM </olex2.extras>

WGHT    0.085800    0.788700
FVAR       0.98985
O1    4    1.156046    0.337971    0.802242    11.00000    0.04580    0.06783 =
         0.05517   -0.00143   -0.01158    0.00411
H1    2    1.057770    0.345979    0.709436    11.00000    0.14085
O2    4    0.583577    0.324054    0.164818    11.00000    0.06490    0.03454 =
         0.03530   -0.00874    0.00582    0.00430
O3    4    0.260194    0.455661    0.134610    11.00000    0.05747    0.03742 =
         0.02739    0.00091   -0.00567    0.00127
N1    3    0.457630    0.398945    0.211425    11.00000    0.03495    0.03220 =
         0.02562   -0.00068    0.00506   -0.00759
N2    3    0.723200    0.363352    0.450551    11.00000    0.03093    0.03236 =
         0.02535   -0.00077    0.00220   -0.00174
N3    3    0.747869    0.404545    0.582647    11.00000    0.03361    0.02940 =
         0.02495    0.00107   -0.00136   -0.00007
N4    3    0.919194    0.331087    0.895413    11.00000    0.06346    0.04180 =
         0.04058    0.00191   -0.01061   -0.00329
AFIX   1
H4A   2    1.015500    0.373000    0.970200    11.00000    0.05000
AFIX   1
H4B   2    0.895700    0.261100    0.923100    11.00000    0.05000
AFIX   1
H4C   2    0.665200    0.356500    0.855400    11.00000    0.05000
AFIX   0
C1    1    0.572987    0.492206    0.570431    11.00000    0.02495    0.03022 =
         0.02472    0.00001    0.00125   -0.00556
C2    1    0.532281    0.424088    0.358438    11.00000    0.02772    0.02992 =
         0.02479   -0.00225    0.00249   -0.00607
HKLF 4




REM  mo_20240428_wq_nlg_nh3oh_0m_a.res in P2(1)/c
REM wR2 = 0.1925, GooF = S = 1.097, Restrained GooF = 1.097 for all data
REM R1 = 0.0689 for 893 Fo > 4sig(Fo) and 0.0799 for all 1076 data
REM 86 parameters refined using 2 restraints

END

WGHT      0.0858      0.7887

REM Highest difference peak  0.321,  deepest hole -0.599,  1-sigma level  0.083
Q1    1   0.8567  0.3810  0.6463  11.00000  0.05    0.32
Q2    1   0.5414  0.5245  0.6169  11.00000  0.05    0.30
Q3    1   0.5000  0.5000  0.5000  10.50000  0.05    0.26
Q4    1   0.5172  0.4133  0.2950  11.00000  0.05    0.26
;
_shelx_res_checksum              56828
_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 1.1560(8) 0.3380(2) 0.8022(3) 0.0574(8) Uani 1 1 d D . . . .
H1 H 1.058(5) 0.346(6) 0.7094(12) 0.14(3) Uiso 1 1 d D . . . .
O2 O 0.5836(8) 0.32405(18) 0.1648(3) 0.0449(7) Uani 1 1 d . . . . .
O3 O 0.2602(7) 0.45566(17) 0.1346(2) 0.0415(6) Uani 1 1 d . . . . .
N1 N 0.4576(7) 0.39894(19) 0.2114(3) 0.0308(6) Uani 1 1 d . . . . .
N2 N 0.7232(7) 0.36335(19) 0.4506(3) 0.0296(6) Uani 1 1 d . . . . .
N3 N 0.7479(7) 0.40454(18) 0.5826(3) 0.0296(6) Uani 1 1 d . . . . .
N4 N 0.9192(10) 0.3311(2) 0.8954(3) 0.0497(8) Uani 1 1 d . . . . .
H4A H 1.015500 0.373000 0.970200 0.050 Uiso 1 1 d . . . . .
H4B H 0.895700 0.261100 0.923100 0.050 Uiso 1 1 d . . . . .
H4C H 0.665200 0.356500 0.855400 0.050 Uiso 1 1 d D . . . .
C1 C 0.5730(7) 0.4922(2) 0.5704(3) 0.0267(6) Uani 1 1 d . . . . .
C2 C 0.5323(8) 0.4241(2) 0.3584(3) 0.0275(6) 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 0.0458(16) 0.068(2) 0.0552(18) -0.0014(15) -0.0116(13) 0.0041(13)
O2 0.0649(17) 0.0345(13) 0.0353(13) -0.0087(10) 0.0058(11) 0.0043(11)
O3 0.0575(15) 0.0374(12) 0.0274(11) 0.0009(9) -0.0057(10) 0.0013(11)
N1 0.0349(13) 0.0322(13) 0.0256(13) -0.0007(10) 0.0051(10) -0.0076(10)
N2 0.0309(13) 0.0324(13) 0.0254(12) -0.0008(10) 0.0022(9) -0.0017(10)
N3 0.0336(13) 0.0294(13) 0.0249(12) 0.0011(9) -0.0014(10) -0.0001(10)
N4 0.063(2) 0.0418(17) 0.0406(17) 0.0019(13) -0.0106(15) -0.0033(15)
C1 0.0249(13) 0.0302(14) 0.0247(14) 0.0000(11) 0.0012(10) -0.0056(11)
C2 0.0277(14) 0.0299(14) 0.0248(14) -0.0023(11) 0.0025(11) -0.0061(11)
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
N4 O1 H1 114.6(12) . . ?
O2 N1 O3 122.9(3) . . ?
O2 N1 C2 120.4(3) . . ?
O3 N1 C2 116.8(3) . . ?
C2 N2 N3 107.7(2) . . ?
N2 N3 C1 107.9(2) . . ?
O1 N4 H4A 102.8 . . ?
O1 N4 H4B 108.9 . . ?
O1 N4 H4C 112.4 . . ?
H4A N4 H4B 115.5 . . ?
H4A N4 H4C 108.6 . . ?
H4B N4 H4C 108.6 . . ?
N3 C1 C1 110.5(3) . 3_666 ?
N3 C1 C2 146.6(3) . 3_666 ?
C1 C1 C2 102.9(3) 3_666 3_666 ?
N2 C2 N1 120.4(3) . . ?
N2 C2 C1 111.0(2) . 3_666 ?
C1 C2 N1 128.6(3) 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 H1 0.911(10) . ?
O1 N4 1.298(5) . ?
O2 N1 1.227(4) . ?
O3 N1 1.243(3) . ?
N1 C2 1.414(4) . ?
N2 N3 1.351(3) . ?
N2 C2 1.345(4) . ?
N3 C1 1.366(4) . ?
N4 H4A 0.9457 . ?
N4 H4B 1.0023 . ?
N4 H4C 1.0333 . ?
C1 C1 1.385(5) 3_666 ?
C1 C2 1.403(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
O2 N1 C2 N2 -4.1(4) . . . . ?
O2 N1 C2 C1 177.0(3) . . . 3_666 ?
O3 N1 C2 N2 175.5(3) . . . . ?
O3 N1 C2 C1 -3.4(4) . . . 3_666 ?
N2 N3 C1 C1 1.1(4) . . . 3_666 ?
N2 N3 C1 C2 179.4(4) . . . 3_666 ?
N3 N2 C2 N1 -178.9(2) . . . . ?
N3 N2 C2 C1 0.1(3) . . . 3_666 ?
C2 N2 N3 C1 -0.7(3) . . . . ?
