5-Amino-1H-pyrazol-2-ium hydrogen succinate.

In the cation of the title salt, C3H6N3 (+)·C4H5O4 (-), the protonated pyrazolium ring is planar (r.m.s. deviation = 0.012 Å). An intra-molecular C-H⋯O hydrogen bond occurs in the anion. In the crystal, N-H⋯O hydrogen bonds and a weak C-H⋯O inter-action between the cations and anions form two sets of R 2 (2)(8) graph-set ring motifs. Inter-molecular O-H⋯O hydrogen bonds between these lead to a criss-cross pattern along the b axis. In addition to the classical hydrogen bonds, a weak C-H⋯π(pyrazolium) inter-action is observed and contributes to crystal packing. All of these inter-actions link the mol-ecules into a two-dimensional supra-molecular framework parallel to (10-1).

Related literature

For the broad spectrum of biological properties of pyrazoles, see: Hall et al. (2009 ▶) and for their biological and medicinal activities, see: Vinogradov et al. (1994 ▶). For succinic acid derivatives used in chemicals, food and pharmaceuticals, see: Sauer et al. (2008 ▶). For related structures, see: Kavitha et al. (2013 ▶); Kettmann et al. (2005 ▶); Koziol et al. (2006 ▶); Parvez et al. (2001 ▶); Yamuna et al. (2013 ▶).

Experimental

Crystal data

C3H6N3 +·C4H5O4 −

M = 201.19

Monoclinic,

a = 18.525 (3) Å

b = 6.7872 (9) Å

c = 14.564 (3) Å

β = 108.900 (18)°

V = 1732.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 173 K

0.32 × 0.24 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.591, T max = 1.000

5745 measured reflections

2922 independent reflections

1925 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.212

S = 1.08

2922 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001615/tk5290sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001615/tk5290Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001615/tk5290Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C3H6N3+·C4H5O4−	F(000) = 848
Mr = 201.19	Dx = 1.543 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.525 (3) Å	Cell parameters from 1155 reflections
b = 6.7872 (9) Å	θ = 3.2–32.9°
c = 14.564 (3) Å	µ = 0.13 mm−1
β = 108.900 (18)°	T = 173 K
V = 1732.4 (5) Å3	Irregular, colorless
Z = 8	0.32 × 0.24 × 0.12 mm

Agilent Eos Gemini diffractometer	2922 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1925 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.053
ω scans	θmax = 33.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −11→27
Tmin = 0.591, Tmax = 1.000	k = −9→9
5745 measured reflections	l = −22→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212	w = 1/[σ2(Fo2) + (0.1004P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2922 reflections	Δρmax = 0.36 e Å−3
136 parameters	Δρmin = −0.40 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
O1B	0.43675 (7)	−0.1627 (2)	0.31692 (11)	0.0344 (4)
H1B	0.3996	−0.1991	0.2719	0.052*
O2B	0.49764 (7)	0.1136 (2)	0.36893 (11)	0.0333 (4)
O3B	0.32006 (7)	0.6651 (2)	0.19603 (10)	0.0272 (3)
O4B	0.26029 (7)	0.3890 (2)	0.13537 (12)	0.0363 (4)
C1B	0.44071 (9)	0.0315 (3)	0.31702 (12)	0.0229 (4)
C2B	0.37281 (9)	0.1414 (3)	0.25149 (13)	0.0218 (4)
H2BA	0.3292	0.1173	0.2729	0.026*
H2BB	0.3608	0.0904	0.1860	0.026*
C3B	0.38592 (9)	0.3623 (3)	0.24999 (13)	0.0230 (4)
H3BA	0.4014	0.4112	0.3161	0.028*
H3BB	0.4276	0.3861	0.2248	0.028*
C4B	0.31721 (9)	0.4781 (3)	0.18995 (12)	0.0228 (4)
N1A	0.63879 (8)	0.9224 (2)	0.48607 (12)	0.0309 (4)
H1AA	0.6782	0.9940	0.5136	0.037*
H1AB	0.5988	0.9745	0.4456	0.037*
N2A	0.70115 (8)	0.6414 (2)	0.56897 (12)	0.0253 (4)
H2A	0.7424 (17)	0.704 (4)	0.617 (2)	0.057 (8)*
N3A	0.68467 (8)	0.4473 (2)	0.57546 (12)	0.0266 (4)
H3A	0.7227 (16)	0.354 (4)	0.603 (2)	0.051 (8)*
C1A	0.63984 (9)	0.7296 (3)	0.50616 (12)	0.0230 (4)
C2A	0.58387 (9)	0.5854 (3)	0.46966 (13)	0.0258 (4)
H2AA	0.5358	0.6031	0.4241	0.031*
C3A	0.61415 (10)	0.4134 (3)	0.51456 (14)	0.0272 (4)
H3AA	0.5897	0.2918	0.5044	0.033*

	U11	U22	U33	U12	U13	U23
O1B	0.0265 (7)	0.0171 (7)	0.0430 (8)	0.0006 (5)	−0.0117 (6)	0.0017 (6)
O2B	0.0216 (6)	0.0230 (7)	0.0404 (8)	−0.0020 (5)	−0.0107 (5)	0.0005 (6)
O3B	0.0237 (6)	0.0148 (7)	0.0323 (7)	0.0010 (5)	−0.0057 (5)	−0.0003 (5)
O4B	0.0230 (6)	0.0186 (7)	0.0476 (9)	−0.0014 (5)	−0.0157 (6)	0.0001 (6)
C1B	0.0182 (7)	0.0179 (9)	0.0261 (8)	0.0013 (6)	−0.0019 (6)	0.0017 (6)
C2B	0.0158 (7)	0.0180 (9)	0.0250 (8)	0.0008 (6)	−0.0021 (5)	−0.0006 (6)
C3B	0.0171 (7)	0.0163 (9)	0.0289 (9)	−0.0003 (6)	−0.0019 (6)	0.0020 (6)
C4B	0.0195 (7)	0.0182 (9)	0.0247 (8)	0.0015 (6)	−0.0012 (6)	0.0018 (6)
N1A	0.0221 (7)	0.0196 (9)	0.0387 (9)	−0.0001 (6)	−0.0073 (6)	0.0024 (7)
N2A	0.0186 (7)	0.0175 (8)	0.0306 (8)	0.0012 (5)	−0.0047 (5)	0.0002 (6)
N3A	0.0215 (7)	0.0175 (8)	0.0319 (8)	0.0009 (6)	−0.0037 (5)	0.0007 (6)
C1A	0.0188 (7)	0.0194 (9)	0.0245 (8)	0.0032 (6)	−0.0018 (5)	−0.0012 (6)
C2A	0.0176 (7)	0.0218 (9)	0.0300 (9)	0.0007 (6)	−0.0033 (6)	−0.0021 (7)
C3A	0.0227 (8)	0.0206 (10)	0.0313 (9)	−0.0025 (6)	−0.0011 (6)	−0.0025 (7)

O1B—H1B	0.8200	N1A—H1AA	0.8600
O1B—C1B	1.320 (2)	N1A—H1AB	0.8600
O2B—C1B	1.216 (2)	N1A—C1A	1.339 (2)
O3B—C4B	1.272 (2)	N2A—H2A	0.95 (3)
O4B—C4B	1.252 (2)	N2A—N3A	1.362 (2)
C1B—C2B	1.507 (2)	N2A—C1A	1.346 (2)
C2B—H2BA	0.9700	N3A—H3A	0.94 (3)
C2B—H2BB	0.9700	N3A—C3A	1.340 (2)
C2B—C3B	1.520 (2)	C1A—C2A	1.399 (2)
C3B—H3BA	0.9700	C2A—H2AA	0.9300
C3B—H3BB	0.9700	C2A—C3A	1.367 (3)
C3B—C4B	1.510 (2)	C3A—H3AA	0.9300
C1B—O1B—H1B	109.5	H1AA—N1A—H1AB	120.0
O1B—C1B—C2B	117.32 (14)	C1A—N1A—H1AA	120.0
O2B—C1B—O1B	119.68 (15)	C1A—N1A—H1AB	120.0
O2B—C1B—C2B	123.00 (17)	N3A—N2A—H2A	121.7 (17)
C1B—C2B—H2BA	109.0	C1A—N2A—H2A	126.8 (17)
C1B—C2B—H2BB	109.0	C1A—N2A—N3A	108.58 (14)
C1B—C2B—C3B	113.14 (14)	N2A—N3A—H3A	122.1 (17)
H2BA—C2B—H2BB	107.8	C3A—N3A—N2A	108.22 (15)
C3B—C2B—H2BA	109.0	C3A—N3A—H3A	127.1 (17)
C3B—C2B—H2BB	109.0	N1A—C1A—N2A	122.17 (15)
C2B—C3B—H3BA	108.7	N1A—C1A—C2A	130.06 (15)
C2B—C3B—H3BB	108.7	N2A—C1A—C2A	107.76 (16)
H3BA—C3B—H3BB	107.6	C1A—C2A—H2AA	127.0
C4B—C3B—C2B	114.39 (14)	C3A—C2A—C1A	106.08 (15)
C4B—C3B—H3BA	108.7	C3A—C2A—H2AA	127.0
C4B—C3B—H3BB	108.7	N3A—C3A—C2A	109.32 (17)
O3B—C4B—C3B	118.07 (14)	N3A—C3A—H3AA	125.3
O4B—C4B—O3B	122.26 (15)	C2A—C3A—H3AA	125.3
O4B—C4B—C3B	119.66 (16)
O1B—C1B—C2B—C3B	−174.71 (17)	N2A—N3A—C3A—C2A	−1.2 (2)
O2B—C1B—C2B—C3B	5.4 (3)	N2A—C1A—C2A—C3A	1.1 (2)
C1B—C2B—C3B—C4B	−176.32 (15)	N3A—N2A—C1A—N1A	178.99 (17)
C2B—C3B—C4B—O3B	170.20 (17)	N3A—N2A—C1A—C2A	−1.9 (2)
C2B—C3B—C4B—O4B	−10.8 (3)	C1A—N2A—N3A—C3A	1.9 (2)
N1A—C1A—C2A—C3A	−179.8 (2)	C1A—C2A—C3A—N3A	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O3Bi	0.82	1.79	2.5832 (18)	164
N1A—H1AA···O4Bii	0.86	2.08	2.874 (2)	153
N1A—H1AB···O2Biii	0.86	2.07	2.923 (2)	170
N2A—H2A···O3Bii	0.95 (3)	1.76 (3)	2.7132 (19)	174 (3)
N3A—H3A···O4Biv	0.94 (3)	1.79 (3)	2.672 (2)	156 (3)
C2A—H2AA···O1Biii	0.93	2.54	3.372 (2)	148
C3A—H3AA···O2B	0.93	2.47	3.214 (2)	138
C3B—H3BA···Cg1v	0.97	2.69	3.511 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrazolium ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1B—H1B⋯O3B i	0.82	1.79	2.5832 (18)	164
N1A—H1AA⋯O4B ii	0.86	2.08	2.874 (2)	153
N1A—H1AB⋯O2B iii	0.86	2.07	2.923 (2)	170
N2A—H2A⋯O3B ii	0.95 (3)	1.76 (3)	2.7132 (19)	174 (3)
N3A—H3A⋯O4B iv	0.94 (3)	1.79 (3)	2.672 (2)	156 (3)
C2A—H2AA⋯O1B iii	0.93	2.54	3.372 (2)	148
C3A—H3AA⋯O2B	0.93	2.47	3.214 (2)	138
C3B—H3BA⋯Cg1v	0.97	2.69	3.511 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .