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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/7/24/99/7249966.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_7249966
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(H2 O), C4 H2 N6 O4'
_chemical_formula_sum            'C4 H6 N6 O6'
_chemical_formula_weight         234.15
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lx3c0
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-14 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.007(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.45260(10)
_cell_length_b                   14.0930(6)
_cell_length_c                   9.0501(4)
_cell_measurement_reflns_used    1927
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.173
_cell_measurement_theta_min      5.821
_cell_volume                     439.28(3)
_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      223.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3842
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.420
_diffrn_reflns_theta_min         5.820
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.8383.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0440
_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)+(0.0688P)²+0.2786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                710
_reflns_number_total             800
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01286k2.cif
_cod_data_source_block           cu_202404112_wq_nlg_nh4_0m
_cod_database_code               7249966
_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   0.867
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_shelx_res_file
;
TITL cu_202404112_wq_nlg_nh4_0m_a.res in P2(1)/c
    cu_202404112_wq_nlg_nh4_0m.res
    created by SHELXL-2018/3 at 10:01:00 on 15-Apr-2024
REM Old TITL cu_202404112_WQ_NLG_NH4_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.143, Rweak 0.005, Alpha 0.013
REM <I/s> 0.327 for 43 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N O
CELL 1.54178 3.4526 14.093 9.0501 90 94.007 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 8 12 12 12

L.S. 4 0 0
PLAN  5
SIZE 0.1 0.12 0.13
TEMP -50.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\cu_202404112_WQ_NLG_NH4_0m.hkl">
REM </olex2.extras>

WGHT    0.068800    0.278600
FVAR       1.12156
O1    4    0.041495    0.328883    0.136568    11.00000    0.09406    0.03539 =
         0.03477   -0.00133   -0.00846    0.01122
H1A   2    0.120511    0.264482    0.102030    11.00000    0.06724
H1B   2   -0.010730    0.376750    0.062299    11.00000    0.07862
O2    4    0.503591    0.315619    0.834731    11.00000    0.06128    0.03030 =
         0.03380    0.00757   -0.00490   -0.01159
O3    4    0.773674    0.453570    0.871698    11.00000    0.04729    0.03225 =
         0.02754   -0.00423   -0.00856   -0.00540
N1    3    0.291915    0.401681    0.413674    11.00000    0.02576    0.02347 =
         0.01975   -0.00266   -0.00222   -0.00059
AFIX  43
H1    2    0.191465    0.376140    0.332269    11.00000   -1.20000
AFIX   0
N2    3    0.334838    0.358524    0.545888    11.00000    0.02393    0.02349 =
         0.02522   -0.00079    0.00127   -0.00013
N3    3    0.595255    0.394675    0.791008    11.00000    0.02934    0.02607 =
         0.02593    0.00003   -0.00002    0.00035
C1    1    0.430791    0.491855    0.427364    11.00000    0.01778    0.02364 =
         0.02413   -0.00393    0.00065    0.00194
C2    1    0.500402    0.421317    0.642294    11.00000    0.02121    0.02388 =
         0.02556   -0.00167    0.00117    0.00172
HKLF 4




REM  cu_202404112_wq_nlg_nh4_0m_a.res in P2(1)/c
REM wR2 = 0.1254, GooF = S = 1.102, Restrained GooF = 1.102 for all data
REM R1 = 0.0440 for 710 Fo > 4sig(Fo) and 0.0487 for all 800 data
REM 81 parameters refined using 0 restraints

END

WGHT      0.0688      0.2786

REM Highest difference peak  0.337,  deepest hole -0.440,  1-sigma level  0.060
Q1    1   0.1377  0.3442  0.2442  11.00000  0.05    0.34
Q2    1  -0.3394  0.3204  0.1391  11.00000  0.05    0.25
Q3    1   0.4742  0.5255  0.3735  11.00000  0.05    0.25
Q4    1   0.5000  0.5000  0.5000  10.50000  0.05    0.23
Q5    1   0.3051  0.3387  0.1159  11.00000  0.05    0.21
;
_shelx_res_checksum              88677
_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 0.0415(7) 0.32888(14) 0.1366(2) 0.0553(6) Uani 1 1 d . . . . .
H1A H 0.121(10) 0.264(3) 0.102(3) 0.067(9) Uiso 1 1 d . . . . .
H1B H -0.011(10) 0.377(3) 0.062(4) 0.079(11) Uiso 1 1 d . . . . .
O2 O 0.5036(5) 0.31562(11) 0.83473(17) 0.0422(5) Uani 1 1 d . . . . .
O3 O 0.7737(5) 0.45357(11) 0.87170(16) 0.0362(5) Uani 1 1 d . . . . .
N1 N 0.2919(4) 0.40168(11) 0.41367(17) 0.0232(4) Uani 1 1 d . . . . .
H1 H 0.191465 0.376140 0.332269 0.028 Uiso 1 1 calc R U . . .
N2 N 0.3348(4) 0.35852(12) 0.54589(17) 0.0242(4) Uani 1 1 d . . . . .
N3 N 0.5953(5) 0.39468(12) 0.79101(18) 0.0272(5) Uani 1 1 d . . . . .
C1 C 0.4308(5) 0.49185(14) 0.4274(2) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.5004(5) 0.42132(14) 0.6423(2) 0.0236(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 0.0941(16) 0.0354(10) 0.0348(10) -0.0013(7) -0.0085(9) 0.0112(10)
O2 0.0613(11) 0.0303(9) 0.0338(9) 0.0076(6) -0.0049(7) -0.0116(7)
O3 0.0473(9) 0.0323(9) 0.0275(8) -0.0042(6) -0.0086(6) -0.0054(7)
N1 0.0258(8) 0.0235(9) 0.0198(8) -0.0027(6) -0.0022(6) -0.0006(6)
N2 0.0239(8) 0.0235(9) 0.0252(9) -0.0008(6) 0.0013(6) -0.0001(6)
N3 0.0293(9) 0.0261(9) 0.0259(9) 0.0000(7) 0.0000(7) 0.0003(7)
C1 0.0178(9) 0.0236(10) 0.0241(10) -0.0039(7) 0.0006(7) 0.0019(7)
C2 0.0212(9) 0.0239(10) 0.0256(10) -0.0017(7) 0.0012(7) 0.0017(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 O1 H1B 117(3) . . ?
N2 N1 H1 125.5 . . ?
N2 N1 C1 109.03(15) . . ?
C1 N1 H1 125.5 . . ?
N1 N2 C2 107.24(15) . . ?
O2 N3 O3 123.00(17) . . ?
O2 N3 C2 119.92(17) . . ?
O3 N3 C2 117.08(17) . . ?
N1 C1 C1 109.7(2) . 3_666 ?
N1 C1 C2 147.40(18) . 3_666 ?
C1 C1 C2 102.9(2) 3_666 3_666 ?
N2 C2 N3 120.24(17) . . ?
N2 C2 C1 111.13(17) . 3_666 ?
C1 C2 N3 128.58(17) 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 H1A 1.00(4) . ?
O1 H1B 0.96(4) . ?
O2 N3 1.231(2) . ?
O3 N3 1.240(2) . ?
N1 H1 0.8700 . ?
N1 N2 1.341(2) . ?
N1 C1 1.361(3) . ?
N2 C2 1.342(2) . ?
N3 C2 1.414(3) . ?
C1 C1 1.386(4) 3_666 ?
C1 C2 1.404(3) 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 N3 C2 N2 -4.6(3) . . . . ?
O2 N3 C2 C1 178.14(19) . . . 3_666 ?
O3 N3 C2 N2 174.76(17) . . . . ?
O3 N3 C2 C1 -2.5(3) . . . 3_666 ?
N1 N2 C2 N3 -177.70(16) . . . . ?
N1 N2 C2 C1 0.0(2) . . . 3_666 ?
N2 N1 C1 C1 0.1(2) . . . 3_666 ?
N2 N1 C1 C2 179.9(3) . . . 3_666 ?
C1 N1 N2 C2 -0.05(19) . . . . ?
