3-Amino-1H-pyrazol-2-ium tri-fluoro-acetate.

The asymmetric unit of the title salt, C3H6N3 (+)·C2F3O2 (-), contains two independent 3-amino-pyrazolium cations and two independent tri-fluoro-acetate anions. The F atoms of both anions were refined as disordered over two sets of sites, with common occupancy ratios of 0.639 (12):0.361 (12). In the crystal, the cations and anions are linked via N-H⋯O hydrogen bonds, forming chains along [100] and [010].

Related literature

For biological properties of pyrazole derivatives, see: Hall et al. (2008 ▶); Isloor et al. (2009 ▶); Patel et al. (2010 ▶); Samshuddin et al. (2010 ▶). For the chemistry of amino­pyrazoles, see: Giuseppe et al. (1991 ▶). For the medicinal activity of pyrazoles, see: Vinogradov et al. (1994 ▶). For related structures, see: Dobson & Gerkin (1998 ▶); Foces-Foces et al. (1996 ▶); Hemamalini & Fun (2010 ▶); Thanigaimani et al. (2012 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C3H6N3 +·C2F3O2 −

M = 197.13

Monoclinic,

a = 10.9292 (8) Å

b = 10.9332 (6) Å

c = 13.7002 (13) Å

β = 107.939 (9)°

V = 1557.5 (2) Å3

Z = 8

Cu Kα radiation

μ = 1.58 mm−1

T = 173 K

0.16 × 0.14 × 0.06 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.662, T max = 1.000

9227 measured reflections

3031 independent reflections

2343 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.05

3031 reflections

338 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.23 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/S1600536813022204/lh5637sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022204/lh5637Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022204/lh5637Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H6N3+·C2F3O2−	F(000) = 800
Mr = 197.13	Dx = 1.681 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 10.9292 (8) Å	Cell parameters from 2544 reflections
b = 10.9332 (6) Å	θ = 3.4–72.4°
c = 13.7002 (13) Å	µ = 1.58 mm−1
β = 107.939 (9)°	T = 173 K
V = 1557.5 (2) Å3	Irregular, colourless
Z = 8	0.16 × 0.14 × 0.06 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	3031 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 4.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −13→9
Tmin = 0.662, Tmax = 1.000	l = −15→16
9227 measured reflections

Refinement on F2	Primary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	All H-atom parameters refined
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.4559P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3031 reflections	Δρmax = 0.24 e Å−3
338 parameters	Δρmin = −0.23 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	Occ. (<1)
C1A	0.56299 (19)	0.93721 (18)	0.25897 (17)	0.0384 (5)
C2A	0.4240 (2)	0.7896 (2)	0.25222 (19)	0.0453 (5)
H2A	0.351 (2)	0.741 (2)	0.2498 (18)	0.050 (7)*
C3A	0.4396 (2)	0.9121 (2)	0.26406 (18)	0.0428 (5)
H3A	0.379 (2)	0.968 (2)	0.2737 (18)	0.050 (7)*
N1A	0.6272 (2)	1.04305 (18)	0.2644 (2)	0.0588 (6)
H1AA	0.593 (3)	1.108 (3)	0.278 (2)	0.057 (8)*
H1AB	0.713 (3)	1.041 (3)	0.272 (2)	0.064 (8)*
N2A	0.61502 (17)	0.83064 (15)	0.24439 (15)	0.0396 (4)
H2AA	0.697 (3)	0.815 (3)	0.240 (2)	0.062 (8)*
N3A	0.52875 (17)	0.73971 (17)	0.23916 (16)	0.0440 (5)
H3AA	0.549 (3)	0.657 (3)	0.236 (2)	0.067 (8)*
C1B	0.28710 (18)	0.17323 (18)	0.48905 (16)	0.0351 (4)
C2B	0.1618 (2)	0.3114 (2)	0.5268 (2)	0.0451 (5)
H2B	0.122 (2)	0.382 (2)	0.5441 (19)	0.050 (7)*
C3B	0.2771 (2)	0.2975 (2)	0.50783 (18)	0.0410 (5)
H3B	0.336 (3)	0.354 (3)	0.508 (2)	0.061 (8)*
N1B	0.37852 (18)	0.11030 (18)	0.46300 (18)	0.0472 (5)
H1BA	0.450 (3)	0.147 (2)	0.476 (2)	0.053 (7)*
H1BB	0.375 (3)	0.029 (3)	0.472 (2)	0.060 (8)*
N2B	0.18060 (15)	0.11865 (16)	0.49623 (14)	0.0372 (4)
H2BA	0.164 (2)	0.034 (3)	0.4985 (19)	0.058 (8)*
N3B	0.10420 (17)	0.20371 (16)	0.52047 (16)	0.0431 (4)
H3BA	0.024 (3)	0.184 (2)	0.5222 (19)	0.051 (7)*
C4A	0.58112 (19)	0.40965 (18)	0.26078 (18)	0.0409 (5)
C5A	0.4574 (2)	0.4142 (2)	0.29303 (18)	0.0422 (5)
F1A1	0.4274 (7)	0.3086 (7)	0.3249 (5)	0.0619 (13)	0.639 (12)
F1A2	0.3945 (12)	0.3073 (14)	0.2818 (12)	0.075 (3)	0.361 (12)
F2A1	0.3589 (8)	0.4515 (8)	0.2173 (6)	0.0681 (17)	0.639 (12)
F2A2	0.3687 (14)	0.4932 (10)	0.2363 (13)	0.067 (3)	0.361 (12)
F3A1	0.4720 (7)	0.4955 (5)	0.3687 (6)	0.0651 (13)	0.639 (12)
F3A2	0.4800 (14)	0.4446 (15)	0.3885 (10)	0.089 (4)	0.361 (12)
O1A	0.63921 (15)	0.31128 (13)	0.27322 (15)	0.0526 (5)
O2A	0.60816 (16)	0.50747 (14)	0.22685 (17)	0.0622 (5)
C4B	0.23375 (19)	0.8115 (2)	0.48329 (18)	0.0413 (5)
C5B	0.2075 (2)	0.6750 (2)	0.45833 (19)	0.0447 (5)
F1B1	0.1329 (4)	0.6255 (3)	0.5045 (6)	0.077 (2)	0.639 (12)
F1B2	0.2028 (16)	0.6103 (8)	0.5367 (6)	0.101 (4)	0.361 (12)
F2B1	0.3162 (3)	0.6097 (3)	0.4866 (5)	0.0669 (13)	0.639 (12)
F2B2	0.2821 (9)	0.6190 (6)	0.4167 (12)	0.089 (4)	0.361 (12)
F3B1	0.1581 (7)	0.6629 (3)	0.3597 (3)	0.090 (2)	0.639 (12)
F3B2	0.0855 (7)	0.6537 (6)	0.3935 (8)	0.079 (3)	0.361 (12)
O1B	0.13834 (14)	0.86991 (13)	0.49109 (15)	0.0530 (5)
O2B	0.34134 (14)	0.84860 (15)	0.48973 (15)	0.0538 (5)

	U11	U22	U33	U12	U13	U23
C1A	0.0374 (10)	0.0299 (10)	0.0508 (12)	0.0050 (8)	0.0177 (9)	0.0021 (8)
C2A	0.0330 (11)	0.0431 (13)	0.0629 (15)	−0.0022 (9)	0.0194 (10)	0.0043 (10)
C3A	0.0351 (10)	0.0382 (12)	0.0595 (14)	0.0072 (9)	0.0208 (10)	0.0022 (10)
N1A	0.0434 (11)	0.0275 (10)	0.113 (2)	0.0008 (8)	0.0358 (12)	−0.0044 (10)
N2A	0.0340 (9)	0.0284 (9)	0.0624 (12)	0.0006 (7)	0.0238 (8)	0.0023 (8)
N3A	0.0385 (9)	0.0281 (9)	0.0701 (13)	−0.0011 (7)	0.0239 (9)	0.0017 (8)
C1B	0.0265 (9)	0.0353 (11)	0.0453 (11)	−0.0029 (7)	0.0138 (8)	0.0041 (8)
C2B	0.0464 (12)	0.0299 (11)	0.0663 (15)	−0.0029 (9)	0.0280 (11)	−0.0050 (10)
C3B	0.0344 (10)	0.0341 (11)	0.0570 (13)	−0.0096 (8)	0.0178 (9)	−0.0010 (9)
N1B	0.0302 (9)	0.0350 (10)	0.0823 (15)	−0.0018 (8)	0.0259 (9)	0.0024 (9)
N2B	0.0288 (8)	0.0279 (9)	0.0588 (11)	−0.0013 (6)	0.0192 (7)	−0.0009 (7)
N3B	0.0345 (9)	0.0330 (9)	0.0709 (13)	−0.0024 (7)	0.0298 (9)	−0.0039 (8)
C4A	0.0354 (10)	0.0301 (11)	0.0639 (14)	−0.0021 (8)	0.0252 (10)	−0.0036 (9)
C5A	0.0363 (11)	0.0397 (12)	0.0549 (13)	−0.0014 (9)	0.0201 (10)	0.0010 (9)
F1A1	0.053 (3)	0.0486 (17)	0.099 (4)	−0.004 (2)	0.045 (3)	0.015 (3)
F1A2	0.046 (5)	0.054 (3)	0.135 (10)	−0.010 (4)	0.044 (5)	0.013 (7)
F2A1	0.0376 (17)	0.094 (5)	0.071 (2)	0.011 (3)	0.0149 (16)	0.019 (3)
F2A2	0.038 (4)	0.058 (5)	0.113 (8)	0.009 (4)	0.035 (5)	0.018 (4)
F3A1	0.061 (2)	0.067 (3)	0.079 (4)	−0.001 (2)	0.039 (2)	−0.027 (2)
F3A2	0.070 (4)	0.137 (11)	0.069 (5)	−0.006 (7)	0.034 (3)	−0.015 (7)
O1A	0.0452 (9)	0.0277 (8)	0.0968 (13)	0.0022 (6)	0.0394 (9)	0.0030 (7)
O2A	0.0526 (10)	0.0302 (8)	0.1222 (16)	0.0029 (7)	0.0538 (11)	0.0110 (9)
C4B	0.0309 (10)	0.0341 (11)	0.0634 (14)	0.0007 (8)	0.0211 (10)	0.0020 (9)
C5B	0.0379 (11)	0.0350 (12)	0.0636 (15)	0.0034 (9)	0.0193 (10)	−0.0015 (10)
F1B1	0.071 (2)	0.0309 (14)	0.151 (6)	−0.0066 (15)	0.068 (3)	0.005 (2)
F1B2	0.174 (11)	0.053 (4)	0.069 (4)	−0.026 (6)	0.025 (6)	0.011 (3)
F2B1	0.0527 (15)	0.0417 (14)	0.107 (3)	0.0162 (11)	0.0249 (19)	−0.0071 (17)
F2B2	0.072 (6)	0.059 (3)	0.163 (11)	−0.002 (3)	0.076 (7)	−0.038 (5)
F3B1	0.113 (5)	0.0658 (19)	0.069 (2)	−0.017 (2)	−0.003 (2)	−0.0142 (14)
F3B2	0.050 (3)	0.060 (3)	0.108 (6)	0.002 (2)	−0.003 (3)	−0.033 (3)
O1B	0.0343 (8)	0.0290 (8)	0.1059 (14)	−0.0020 (6)	0.0366 (8)	−0.0059 (8)
O2B	0.0310 (8)	0.0434 (9)	0.0937 (13)	−0.0013 (6)	0.0290 (8)	0.0035 (8)

C1A—C3A	1.399 (3)	N2B—H2BA	0.95 (3)
C1A—N1A	1.344 (3)	N2B—N3B	1.358 (2)
C1A—N2A	1.338 (3)	N3B—H3BA	0.91 (3)
C2A—H2A	0.96 (3)	C4A—C5A	1.547 (3)
C2A—C3A	1.354 (3)	C4A—O1A	1.234 (2)
C2A—N3A	1.329 (3)	C4A—O2A	1.238 (3)
C3A—H3A	0.94 (3)	C5A—F1A1	1.312 (8)
N1A—H1AA	0.85 (3)	C5A—F1A2	1.341 (14)
N1A—H1AB	0.91 (3)	C5A—F2A1	1.309 (8)
N2A—H2AA	0.94 (3)	C5A—F2A2	1.351 (15)
N2A—N3A	1.357 (2)	C5A—F3A1	1.337 (7)
N3A—H3AA	0.93 (3)	C5A—F3A2	1.298 (14)
C1B—C3B	1.393 (3)	C4B—C5B	1.538 (3)
C1B—N1B	1.349 (3)	C4B—O1B	1.255 (2)
C1B—N2B	1.338 (2)	C4B—O2B	1.221 (2)
C2B—H2B	0.95 (3)	C5B—F1B1	1.295 (5)
C2B—C3B	1.372 (3)	C5B—F1B2	1.299 (8)
C2B—N3B	1.325 (3)	C5B—F2B1	1.337 (4)
C3B—H3B	0.89 (3)	C5B—F2B2	1.284 (6)
N1B—H1BA	0.84 (3)	C5B—F3B1	1.298 (4)
N1B—H1BB	0.90 (3)	C5B—F3B2	1.375 (6)
N1A—C1A—C3A	131.41 (19)	C2B—N3B—N2B	108.01 (17)
N2A—C1A—C3A	107.28 (18)	C2B—N3B—H3BA	130.5 (16)
N2A—C1A—N1A	121.30 (19)	N2B—N3B—H3BA	121.1 (16)
C3A—C2A—H2A	129.0 (15)	O1A—C4A—C5A	116.52 (18)
N3A—C2A—H2A	121.0 (15)	O1A—C4A—O2A	129.27 (19)
N3A—C2A—C3A	109.9 (2)	O2A—C4A—C5A	114.21 (17)
C1A—C3A—H3A	127.7 (15)	F1A1—C5A—C4A	113.4 (4)
C2A—C3A—C1A	106.02 (19)	F1A1—C5A—F3A1	108.0 (4)
C2A—C3A—H3A	126.3 (15)	F1A2—C5A—C4A	113.7 (7)
C1A—N1A—H1AA	118.4 (19)	F1A2—C5A—F2A2	103.9 (7)
C1A—N1A—H1AB	119.1 (18)	F2A1—C5A—C4A	111.2 (4)
H1AA—N1A—H1AB	120 (3)	F2A1—C5A—F1A1	108.0 (4)
C1A—N2A—H2AA	128.8 (18)	F2A1—C5A—F3A1	106.2 (4)
C1A—N2A—N3A	109.00 (17)	F2A2—C5A—C4A	113.1 (7)
N3A—N2A—H2AA	122.2 (18)	F3A1—C5A—C4A	109.7 (3)
C2A—N3A—N2A	107.79 (18)	F3A2—C5A—C4A	112.6 (6)
C2A—N3A—H3AA	129.0 (18)	F3A2—C5A—F1A2	105.7 (7)
N2A—N3A—H3AA	122.6 (18)	F3A2—C5A—F2A2	107.3 (8)
N1B—C1B—C3B	130.75 (19)	O1B—C4B—C5B	114.19 (18)
N2B—C1B—C3B	107.58 (17)	O2B—C4B—C5B	116.60 (19)
N2B—C1B—N1B	121.60 (19)	O2B—C4B—O1B	129.2 (2)
C3B—C2B—H2B	131.0 (15)	F1B1—C5B—C4B	113.5 (3)
N3B—C2B—H2B	119.5 (15)	F1B1—C5B—F2B1	105.8 (3)
N3B—C2B—C3B	109.57 (19)	F1B1—C5B—F3B1	110.1 (3)
C1B—C3B—H3B	125.5 (18)	F1B2—C5B—C4B	113.3 (4)
C2B—C3B—C1B	105.75 (18)	F1B2—C5B—F3B2	99.4 (5)
C2B—C3B—H3B	128.7 (18)	F2B1—C5B—C4B	111.4 (2)
C1B—N1B—H1BA	114.8 (18)	F2B2—C5B—C4B	117.5 (3)
C1B—N1B—H1BB	113.5 (17)	F2B2—C5B—F1B2	107.4 (6)
H1BA—N1B—H1BB	121 (2)	F2B2—C5B—F3B2	104.7 (5)
C1B—N2B—H2BA	128.4 (16)	F3B1—C5B—C4B	108.6 (2)
C1B—N2B—N3B	109.08 (17)	F3B1—C5B—F2B1	107.2 (3)
N3B—N2B—H2BA	121.5 (16)	F3B2—C5B—C4B	112.7 (3)
C1A—N2A—N3A—C2A	−1.0 (3)	O1A—C4A—C5A—F3A2	88.7 (8)
C3A—C1A—N2A—N3A	0.6 (3)	O2A—C4A—C5A—F1A1	177.4 (4)
C3A—C2A—N3A—N2A	1.1 (3)	O2A—C4A—C5A—F1A2	149.4 (7)
N1A—C1A—C3A—C2A	178.8 (3)	O2A—C4A—C5A—F2A1	55.5 (5)
N1A—C1A—N2A—N3A	−178.3 (2)	O2A—C4A—C5A—F2A2	31.3 (7)
N2A—C1A—C3A—C2A	0.1 (3)	O2A—C4A—C5A—F3A1	−61.7 (4)
N3A—C2A—C3A—C1A	−0.7 (3)	O2A—C4A—C5A—F3A2	−90.5 (8)
C1B—N2B—N3B—C2B	1.0 (3)	O1B—C4B—C5B—F1B1	−38.2 (4)
C3B—C1B—N2B—N3B	−0.9 (2)	O1B—C4B—C5B—F1B2	−76.1 (9)
C3B—C2B—N3B—N2B	−0.6 (3)	O1B—C4B—C5B—F2B1	−157.5 (3)
N1B—C1B—C3B—C2B	177.5 (2)	O1B—C4B—C5B—F2B2	157.7 (8)
N1B—C1B—N2B—N3B	−178.2 (2)	O1B—C4B—C5B—F3B1	84.6 (5)
N2B—C1B—C3B—C2B	0.5 (3)	O1B—C4B—C5B—F3B2	35.9 (7)
N3B—C2B—C3B—C1B	0.1 (3)	O2B—C4B—C5B—F1B1	143.9 (4)
O1A—C4A—C5A—F1A1	−3.4 (4)	O2B—C4B—C5B—F1B2	106.0 (9)
O1A—C4A—C5A—F1A2	−31.4 (7)	O2B—C4B—C5B—F2B1	24.5 (4)
O1A—C4A—C5A—F2A1	−125.3 (4)	O2B—C4B—C5B—F2B2	−20.3 (9)
O1A—C4A—C5A—F2A2	−149.5 (6)	O2B—C4B—C5B—F3B1	−93.3 (5)
O1A—C4A—C5A—F3A1	117.5 (4)	O2B—C4B—C5B—F3B2	−142.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1Ai	0.85 (3)	2.28 (3)	2.936 (3)	134 (2)
N1A—H1AB···O2Aii	0.91 (3)	1.99 (3)	2.884 (3)	169 (3)
N2A—H2AA···O1Aii	0.94 (3)	1.85 (3)	2.778 (2)	171 (3)
N3A—H3AA···O2A	0.93 (3)	1.78 (3)	2.705 (2)	172 (3)
N1B—H1BA···O2Biii	0.84 (3)	2.18 (3)	2.962 (2)	153 (2)
N1B—H1BB···O2Biv	0.90 (3)	2.03 (3)	2.929 (3)	173 (2)
N2B—H2BA···O1Biv	0.95 (3)	1.81 (3)	2.756 (2)	174 (2)
N3B—H3BA···O1Bv	0.91 (3)	1.82 (3)	2.728 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯O1A i	0.85 (3)	2.28 (3)	2.936 (3)	134 (2)
N1A—H1AB⋯O2A ii	0.91 (3)	1.99 (3)	2.884 (3)	169 (3)
N2A—H2AA⋯O1A ii	0.94 (3)	1.85 (3)	2.778 (2)	171 (3)
N3A—H3AA⋯O2A	0.93 (3)	1.78 (3)	2.705 (2)	172 (3)
N1B—H1BA⋯O2B iii	0.84 (3)	2.18 (3)	2.962 (2)	153 (2)
N1B—H1BB⋯O2B iv	0.90 (3)	2.03 (3)	2.929 (3)	173 (2)
N2B—H2BA⋯O1B iv	0.95 (3)	1.81 (3)	2.756 (2)	174 (2)
N3B—H3BA⋯O1B v	0.91 (3)	1.82 (3)	2.728 (2)	171 (2)

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