#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056437.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_7056437
loop_
_publ_author_name
'Du, Yao'
'Zhang, Ji-Chuan'
'peng, Panpan'
'Su, Hui'
'Li, Sheng-Hua'
'Pang, Si-Ping'
_publ_section_title
;
 Synthesis and characterization of three pyrazolate inner diazonium salts:
 green, powerful and stable primary explosives
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              9244
_journal_page_last               9249
_journal_paper_doi               10.1039/C7NJ00876G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C3 H N5 O3'
_chemical_formula_sum            'C3 H N5 O3'
_chemical_formula_weight         155.09
_chemical_name_common            NCDAP
_chemical_name_systematic
'3-nitro-5-carbonyl-4-diazopyrazolate zwitterion'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4779)
;
_audit_update_record
;
2014-08-07 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.852(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5357(4)
_cell_length_b                   9.1337(7)
_cell_length_c                   11.5261(8)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5780
_cell_measurement_theta_min      4.4330
_cell_volume                     582.47(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4713
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0578169000
_diffrn_orient_matrix_UB_12      0.0615478000
_diffrn_orient_matrix_UB_13      0.0261147000
_diffrn_orient_matrix_UB_21      -0.0488337000
_diffrn_orient_matrix_UB_22      0.0455049000
_diffrn_orient_matrix_UB_23      -0.0447679000
_diffrn_orient_matrix_UB_31      -0.1035527000
_diffrn_orient_matrix_UB_32      0.0129337000
_diffrn_orient_matrix_UB_33      0.0332280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5344
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_min         3.537
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0456
_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)+(0.0547P)²+0.0045P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                995
_reflns_number_total             1468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj00876g2.cif
_cod_data_source_block           3oh54
_cod_database_code               7056437
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_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.
;
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8)
;
_shelx_res_file
;
TITL 3OH54 in P21/n #14
CELL 0.71073 5.535683 9.133658 11.526133 90 91.8516 90
ZERR 4 0.000397 0.00065 0.000799 0 0.0063 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
 
SFAC C H N O
UNIT 12 4 20 12
 
L.S. 20
PLAN  20
REM reset to P21/n #14
BOND
fmap 2
MORE -1
CONF
ACTA 52
REM <HKL>D:/Data/3OH54/3OH54.hkl</HKL>
 
WGHT    0.054700    0.004500
FVAR      10.15927
O1    4    0.234686    0.805006    0.830043    11.00000    0.05413    0.05479 =
         0.04553    0.00816    0.02120    0.00310
O2    4    1.004823    1.034185    0.650409    11.00000    0.04503    0.05533 =
         0.04259   -0.00088    0.00884   -0.01471
O3    4    0.133613    0.691108    0.670805    11.00000    0.04695    0.05339 =
         0.06928    0.00087    0.00466   -0.01559
N4    3    0.695574    0.947171    0.845570    11.00000    0.03923    0.04545 =
         0.03244    0.00173    0.00755    0.00318
N5    3    0.514664    0.814087    0.567970    11.00000    0.03970    0.04146 =
         0.03711   -0.00047    0.00587   -0.00403
C6    1    0.821886    0.958284    0.645177    11.00000    0.03519    0.03653 =
         0.03356    0.00422    0.00638   -0.00020
N7    3    0.267473    0.768970    0.729531    11.00000    0.03716    0.03570 =
         0.04687    0.00731    0.00911    0.00094
N8    3    0.721571    0.890942    0.549296    11.00000    0.03956    0.04864 =
         0.03027   -0.00003    0.00984   -0.00607
AFIX  43
H8    2    0.784132    0.896539    0.482108    11.00000   -1.20000
AFIX   0
C9    1    0.479504    0.828405    0.677897    11.00000    0.03246    0.03301 =
         0.03537    0.00203    0.00695    0.00134
C10   1    0.659499    0.914423    0.734044    11.00000    0.03780    0.03742 =
         0.02954   -0.00075    0.00660    0.00108
N11   3    0.736453    0.978672    0.936756    11.00000    0.06084    0.07683 =
         0.03779   -0.00627    0.00404   -0.00049
HKLF 4
 
REM  3OH54 in P21/n #14
REM R1 =  0.0456 for     995 Fo > 4sig(Fo)  and  0.0749 for all    1468 data
REM    100 parameters refined using      0 restraints
 
END  
     
WGHT      0.0547      0.0045 

REM Highest difference peak  0.249,  deepest hole -0.364,  1-sigma level  0.086
Q1    1   0.9764  0.7532  0.4625  11.00000  0.05    0.25
Q2    1   0.0047  0.7645  0.5511  11.00000  0.05    0.22
Q3    1   0.5272  1.0285  0.5545  11.00000  0.05    0.22
Q4    1   0.0029  0.6681  0.5430  11.00000  0.05    0.20
Q5    1   0.2804  0.9418  0.6023  11.00000  0.05    0.20
Q6    1   0.5593  0.7986  0.9954  11.00000  0.05    0.20
Q7    1   0.1091  0.7391  0.5410  11.00000  0.05    0.19
Q8    1   0.6358  0.9792  0.4186  11.00000  0.05    0.19
Q9    1   1.0944  0.7671  0.4522  11.00000  0.05    0.19
Q10   1   0.3880  0.9568  0.5238  11.00000  0.05    0.19
Q11   1   1.0242  1.0389  0.9226  11.00000  0.05    0.19
Q12   1   0.7792  0.9890  1.0983  11.00000  0.05    0.18
Q13   1   0.7159  0.9811  0.3821  11.00000  0.05    0.18
Q14   1   1.0667  1.0161  0.8839  11.00000  0.05    0.17
Q15   1   0.9916  1.1023  0.8208  11.00000  0.05    0.17
Q16   1   0.3553  0.5914  0.6252  11.00000  0.05    0.17
Q17   1   0.9048  0.9742  1.0343  11.00000  0.05    0.16
Q18   1   0.5947  0.8325  0.7239  11.00000  0.05    0.16
Q19   1   0.2178  0.9498  0.9066  11.00000  0.05    0.16
Q20   1   0.7452  0.7600  0.7005  11.00000  0.05    0.16

REM The information below was added by Olex2.
REM
REM R1 = 0.0456 for 995 Fo > 4sig(Fo) and 0.0749 for all 5532 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.25, deepest hole -0.36
REM Mean Shift 0, Max Shift 0.

REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0749
REM R1_gt = 0.0456
REM wR_ref = 0.1135
REM GOOF = 1.085
REM Shift_max = 0
REM Shift_mean = 0
REM Reflections_all = 5532
REM Reflections_gt = 995
REM Parameters = n/a
REM Hole = -0.36
REM Peak = 0.25
REM Flack = n/a

;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.2347(2) 0.80501(14) 0.83004(11) 0.0511(4) Uani 1 1 d .
O2 O 1.0048(2) 1.03419(15) 0.65041(10) 0.0475(4) Uani 1 1 d .
O3 O 0.1336(2) 0.69111(15) 0.67080(12) 0.0565(4) Uani 1 1 d .
N4 N 0.6956(2) 0.94717(16) 0.84557(12) 0.0389(4) Uani 1 1 d .
N5 N 0.5147(2) 0.81409(15) 0.56797(11) 0.0393(4) Uani 1 1 d .
C6 C 0.8219(3) 0.95828(18) 0.64518(13) 0.0350(4) Uani 1 1 d .
N7 N 0.2675(2) 0.76897(16) 0.72953(12) 0.0397(4) Uani 1 1 d .
N8 N 0.7216(2) 0.89094(16) 0.54930(11) 0.0393(4) Uani 1 1 d .
H8 H 0.7841 0.8965 0.4821 0.047 Uiso 1 1 calc R
C9 C 0.4795(3) 0.82840(17) 0.67790(13) 0.0335(4) Uani 1 1 d .
C10 C 0.6595(3) 0.91442(18) 0.73404(13) 0.0348(4) Uani 1 1 d .
N11 N 0.7365(3) 0.9787(2) 0.93676(14) 0.0584(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 0.0541(8) 0.0548(8) 0.0455(7) 0.0082(6) 0.0212(6) 0.0031(6)
O2 0.0450(7) 0.0553(8) 0.0426(7) -0.0009(6) 0.0088(5) -0.0147(6)
O3 0.0469(8) 0.0534(8) 0.0693(9) 0.0009(7) 0.0047(6) -0.0156(6)
N4 0.0392(8) 0.0455(9) 0.0324(8) 0.0017(6) 0.0075(6) 0.0032(6)
N5 0.0397(8) 0.0415(8) 0.0371(8) -0.0005(6) 0.0059(6) -0.0040(6)
C6 0.0352(9) 0.0365(9) 0.0336(9) 0.0042(7) 0.0064(6) -0.0002(7)
N7 0.0372(8) 0.0357(8) 0.0469(9) 0.0073(7) 0.0091(6) 0.0009(6)
N8 0.0396(8) 0.0486(9) 0.0303(7) 0.0000(6) 0.0098(5) -0.0061(6)
C9 0.0325(8) 0.0330(8) 0.0354(8) 0.0020(7) 0.0069(6) 0.0013(6)
C10 0.0378(9) 0.0374(9) 0.0295(8) -0.0007(7) 0.0066(6) 0.0011(7)
N11 0.0608(10) 0.0768(13) 0.0378(9) -0.0063(8) 0.0040(7) -0.0005(9)
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
N11 N4 C10 176.14(17)
C9 N5 N8 104.81(12)
O2 C6 N8 127.37(14)
O2 C6 C10 130.90(15)
N8 C6 C10 101.72(13)
O1 N7 C9 115.97(14)
O3 N7 O1 125.29(14)
O3 N7 C9 118.72(14)
N5 N8 C6 115.12(12)
N5 C9 N7 121.13(14)
N5 C9 C10 112.28(13)
C10 C9 N7 126.45(14)
N4 C10 C6 123.18(15)
N4 C10 C9 130.66(14)
C9 C10 C6 106.05(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N7 1.2235(17)
O2 C6 1.2271(19)
O3 N7 1.2168(19)
N4 C10 1.329(2)
N4 N11 1.1060(19)
N5 N8 1.3663(18)
N5 C9 1.2947(19)
C6 N8 1.367(2)
C6 C10 1.441(2)
N7 C9 1.439(2)
C9 C10 1.410(2)
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
O1 N7 C9 N5 -170.49(14)
O1 N7 C9 C10 4.9(2)
O2 C6 N8 N5 -179.25(16)
O2 C6 C10 N4 -3.8(3)
O2 C6 C10 C9 179.53(17)
O3 N7 C9 N5 7.8(2)
O3 N7 C9 C10 -176.81(15)
N5 C9 C10 N4 -175.60(16)
N5 C9 C10 C6 0.67(19)
N7 C9 C10 N4 8.7(3)
N7 C9 C10 C6 -175.02(14)
N8 N5 C9 N7 176.15(14)
N8 N5 C9 C10 0.20(18)
N8 C6 C10 N4 175.41(15)
N8 C6 C10 C9 -1.21(17)
C9 N5 N8 C6 -1.10(18)
C10 C6 N8 N5 1.46(18)
