Download citation
Download citation
link to html
A 2:1 organic salt formed from pyrazole and picric acid was obtained from methanol solution. In the crystal, N—H...O hydrogen bonds give rise to a hydrogen-bonded chain along [100]. Adjacent [100] chains are linked by a weak C—H...O inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016008215/lh5810sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016008215/lh5810Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016008215/lh5810Isup3.cml
Supplementary material

CCDC reference: 1480969

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.157
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N3 Check
Author Response: This can be omitted because the structure is determined unambiguously.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0044 Ang.
Author Response: This should be omitted due to some minor potential disorder.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O4      ..       2.61 Ang.
Author Response: This is a weak C-H...O interactions as mentioned in the communication.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     16.836 Check
Author Response: This can be omitted because the structure is determined unambiguously.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.290 Check
Author Response: This can be omitted because the structure is determined unambiguously.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10 Report
Author Response: This can be omitted because the structure is determined unambiguously.

Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C12 H11 N7 O7 Atom count from _chemical_formula_moiety:C12 H11 N43 O7 PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 Note PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 9.48) in Resd. # 2 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 9.52) in Resd. # 3 Check PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 4 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 2 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1H-Pyrazol-2-ium 2,4,6-trinitrophenolate 1H-pyrazole top
Crystal data top
C3H5N2+·C6H2N3O7·C3H4N2F(000) = 752
Mr = 365.28Dx = 1.545 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.2447 (14) ÅCell parameters from 1735 reflections
b = 16.950 (5) Åθ = 2.4–20.5°
c = 21.839 (7) ŵ = 0.13 mm1
β = 92.029 (6)°T = 298 K
V = 1570.3 (9) Å3Needle, yellow
Z = 40.45 × 0.06 × 0.04 mm
Data collection top
Bruker SMART CCD
diffractometer
1787 reflections with I > 2σ(I)
φ and ω scansRint = 0.050
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 26.0°, θmin = 1.5°
Tmin = 0.736, Tmax = 0.875h = 55
12038 measured reflectionsk = 2020
3086 independent reflectionsl = 2624
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.057 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.3803P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.18 e Å3
3086 reflectionsΔρmin = 0.16 e Å3
248 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.2577 (7)0.78567 (15)0.50270 (13)0.0502 (7)
C20.0904 (7)0.85715 (15)0.51570 (12)0.0478 (7)
C30.0496 (7)0.88621 (16)0.57336 (13)0.0565 (8)
H30.06670.93200.57890.068*
C40.1825 (8)0.84691 (17)0.62309 (13)0.0577 (8)
C50.3503 (7)0.77808 (17)0.61557 (13)0.0573 (8)
H50.44230.75250.64940.069*
C60.3802 (7)0.74780 (15)0.55807 (13)0.0506 (7)
C70.7321 (8)0.56590 (19)0.33757 (15)0.0683 (9)
H70.59020.56010.30450.082*
C80.8600 (8)0.50504 (18)0.37140 (16)0.0689 (9)
H80.82290.45140.36600.083*
C91.0517 (8)0.53966 (19)0.41426 (15)0.0679 (9)
H91.17310.51370.44430.082*
C100.8031 (8)0.80992 (19)0.26399 (14)0.0675 (9)
H100.93740.78620.23670.081*
C110.6789 (9)0.88402 (19)0.25746 (15)0.0698 (9)
H110.71140.91970.22600.084*
C120.4981 (8)0.89415 (18)0.30687 (15)0.0648 (9)
H120.38090.93880.31570.078*
N10.0457 (6)0.90430 (13)0.46540 (12)0.0532 (6)
N20.1422 (9)0.87879 (19)0.68408 (13)0.0815 (9)
N30.5497 (7)0.67352 (16)0.55396 (14)0.0645 (7)
N40.8395 (7)0.63381 (15)0.35881 (12)0.0613 (7)
H4A0.808 (16)0.6815 (15)0.346 (3)0.074*0.48 (5)
N51.0360 (7)0.61758 (14)0.40591 (12)0.0617 (7)
H5A1.133 (7)0.6554 (14)0.4254 (13)0.074*
N60.7043 (7)0.77681 (14)0.31469 (12)0.0600 (7)
H6A0.761 (15)0.7321 (19)0.330 (3)0.072*0.52 (5)
N70.5183 (6)0.82915 (14)0.34019 (11)0.0553 (6)
H7A0.434 (7)0.8196 (18)0.3747 (8)0.066*
O10.2919 (6)0.75921 (11)0.44959 (9)0.0668 (6)
O20.0820 (5)0.90477 (13)0.41655 (9)0.0709 (7)
O30.2780 (5)0.94352 (13)0.47569 (11)0.0756 (7)
O40.0220 (9)0.93651 (17)0.68985 (11)0.1281 (13)
O50.2766 (8)0.84518 (17)0.72727 (12)0.1047 (10)
O60.4897 (7)0.62868 (15)0.51168 (12)0.0976 (9)
O70.7405 (7)0.65737 (15)0.59511 (13)0.0968 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0571 (19)0.0411 (15)0.0529 (18)0.0044 (13)0.0093 (14)0.0021 (13)
C20.0536 (18)0.0405 (14)0.0496 (17)0.0054 (13)0.0070 (14)0.0018 (12)
C30.069 (2)0.0407 (15)0.0609 (19)0.0060 (14)0.0160 (16)0.0012 (14)
C40.083 (2)0.0481 (17)0.0431 (17)0.0152 (16)0.0113 (16)0.0028 (13)
C50.067 (2)0.0531 (17)0.0517 (18)0.0163 (15)0.0001 (15)0.0063 (14)
C60.0516 (18)0.0417 (15)0.0586 (19)0.0056 (13)0.0047 (14)0.0059 (13)
C70.081 (2)0.0542 (19)0.070 (2)0.0002 (17)0.0032 (18)0.0008 (16)
C80.082 (2)0.0443 (17)0.081 (2)0.0001 (17)0.011 (2)0.0028 (17)
C90.079 (2)0.0543 (19)0.072 (2)0.0136 (17)0.0130 (19)0.0148 (16)
C100.082 (2)0.064 (2)0.057 (2)0.0059 (18)0.0108 (17)0.0026 (16)
C110.084 (2)0.062 (2)0.064 (2)0.0043 (18)0.0063 (18)0.0165 (16)
C120.071 (2)0.0494 (17)0.074 (2)0.0102 (15)0.0029 (18)0.0093 (16)
N10.0543 (16)0.0428 (13)0.0625 (17)0.0019 (12)0.0015 (13)0.0003 (12)
N20.136 (3)0.0584 (18)0.0513 (18)0.0198 (18)0.0169 (18)0.0022 (15)
N30.0695 (19)0.0586 (16)0.0659 (18)0.0079 (14)0.0087 (15)0.0137 (15)
N40.080 (2)0.0445 (15)0.0593 (17)0.0116 (14)0.0079 (15)0.0077 (13)
N50.075 (2)0.0482 (16)0.0624 (18)0.0046 (13)0.0103 (15)0.0023 (13)
N60.0765 (19)0.0439 (14)0.0593 (17)0.0071 (13)0.0008 (14)0.0020 (13)
N70.0655 (17)0.0490 (14)0.0513 (15)0.0082 (12)0.0033 (12)0.0009 (12)
O10.1065 (18)0.0453 (11)0.0493 (13)0.0069 (11)0.0120 (12)0.0007 (9)
O20.0857 (17)0.0755 (15)0.0519 (14)0.0201 (12)0.0063 (12)0.0082 (11)
O30.0627 (15)0.0675 (14)0.0969 (18)0.0187 (12)0.0090 (13)0.0079 (12)
O40.244 (4)0.0713 (18)0.0722 (18)0.027 (2)0.046 (2)0.0084 (14)
O50.153 (3)0.106 (2)0.0549 (16)0.0167 (19)0.0024 (17)0.0058 (14)
O60.148 (3)0.0690 (15)0.0753 (17)0.0389 (16)0.0009 (16)0.0061 (14)
O70.095 (2)0.0828 (18)0.111 (2)0.0201 (15)0.0245 (17)0.0184 (15)
Geometric parameters (Å, º) top
C1—O11.257 (3)C10—N61.323 (4)
C1—C21.438 (4)C10—C111.368 (4)
C1—C61.449 (4)C10—H100.9300
C2—C31.369 (4)C11—C121.357 (4)
C2—N11.461 (4)C11—H110.9300
C3—C41.378 (4)C12—N71.321 (4)
C3—H30.9300C12—H120.9300
C4—C51.380 (4)N1—O21.214 (3)
C4—N21.453 (4)N1—O31.216 (3)
C5—C61.367 (4)N2—O41.210 (4)
C5—H50.9300N2—O51.225 (4)
C6—N31.454 (4)N3—O61.216 (3)
C7—N41.316 (4)N3—O71.219 (3)
C7—C81.370 (4)N4—N51.330 (4)
C7—H70.9300N4—H4A0.862 (10)
C8—C91.352 (5)N5—H5A0.865 (10)
C8—H80.9300N6—N71.323 (3)
C9—N51.335 (4)N6—H6A0.861 (10)
C9—H90.9300N7—H7A0.861 (10)
O1—C1—C2123.9 (3)C11—C10—H10124.9
O1—C1—C6124.2 (3)C12—C11—C10105.1 (3)
C2—C1—C6111.9 (2)C12—C11—H11127.5
C3—C2—C1124.4 (3)C10—C11—H11127.5
C3—C2—N1115.8 (2)N7—C12—C11107.7 (3)
C1—C2—N1119.8 (2)N7—C12—H12126.1
C2—C3—C4119.3 (3)C11—C12—H12126.1
C2—C3—H3120.3O2—N1—O3123.3 (3)
C4—C3—H3120.3O2—N1—C2119.2 (2)
C3—C4—C5120.9 (3)O3—N1—C2117.5 (3)
C3—C4—N2119.0 (3)O4—N2—O5123.3 (3)
C5—C4—N2120.1 (3)O4—N2—C4118.9 (3)
C6—C5—C4119.5 (3)O5—N2—C4117.8 (3)
C6—C5—H5120.3O6—N3—O7122.3 (3)
C4—C5—H5120.3O6—N3—C6119.8 (3)
C5—C6—C1123.9 (3)O7—N3—C6117.8 (3)
C5—C6—N3116.4 (3)C7—N4—N5106.9 (3)
C1—C6—N3119.7 (3)C7—N4—H4A131 (5)
N4—C7—C8110.1 (3)N5—N4—H4A122 (5)
N4—C7—H7125.0N4—N5—C9109.7 (3)
C8—C7—H7125.0N4—N5—H5A120 (2)
C9—C8—C7105.3 (3)C9—N5—H5A130 (2)
C9—C8—H8127.3C10—N6—N7106.2 (2)
C7—C8—H8127.3C10—N6—H6A127 (4)
N5—C9—C8108.0 (3)N7—N6—H6A126 (4)
N5—C9—H9126.0C12—N7—N6110.8 (3)
C8—C9—H9126.0C12—N7—H7A128 (2)
N6—C10—C11110.2 (3)N6—N7—H7A121 (2)
N6—C10—H10124.9
O1—C1—C2—C3179.5 (3)C10—C11—C12—N70.2 (4)
C6—C1—C2—C30.3 (4)C3—C2—N1—O2148.3 (3)
O1—C1—C2—N11.3 (4)C1—C2—N1—O231.0 (4)
C6—C1—C2—N1179.0 (2)C3—C2—N1—O329.2 (4)
C1—C2—C3—C42.0 (4)C1—C2—N1—O3151.5 (3)
N1—C2—C3—C4177.3 (2)C3—C4—N2—O44.1 (5)
C2—C3—C4—C51.3 (4)C5—C4—N2—O4175.5 (3)
C2—C3—C4—N2179.1 (3)C3—C4—N2—O5176.2 (3)
C3—C4—C5—C61.1 (4)C5—C4—N2—O54.2 (5)
N2—C4—C5—C6178.5 (3)C5—C6—N3—O6152.3 (3)
C4—C5—C6—C13.1 (4)C1—C6—N3—O628.5 (4)
C4—C5—C6—N3177.7 (3)C5—C6—N3—O724.9 (4)
O1—C1—C6—C5178.0 (3)C1—C6—N3—O7154.4 (3)
C2—C1—C6—C52.3 (4)C8—C7—N4—N50.1 (4)
O1—C1—C6—N31.3 (4)C7—N4—N5—C90.1 (3)
C2—C1—C6—N3178.5 (2)C8—C9—N5—N40.0 (4)
N4—C7—C8—C90.2 (4)C11—C10—N6—N70.2 (4)
C7—C8—C9—N50.1 (4)C11—C12—N7—N60.1 (4)
N6—C10—C11—C120.2 (4)C10—N6—N7—C120.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N60.86 (1)1.81 (1)2.663 (3)173 (7)
N5—H5A···O1i0.87 (1)1.95 (1)2.789 (3)163 (3)
N5—H5A···O6i0.87 (1)2.42 (3)2.961 (4)121 (3)
N6—H6A···N40.86 (1)1.81 (1)2.663 (3)174 (7)
N7—H7A···O10.86 (1)2.04 (2)2.864 (3)160 (3)
N7—H7A···O20.86 (1)2.29 (3)2.841 (3)122 (3)
C12—H12···O4ii0.932.613.512 (5)165
Symmetry codes: (i) x+1, y, z; (ii) x, y+2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds