Tri-aqua-(pyrazole-4-carboxyl-ato-κN (1))lithium.

In the monomeric title complex, [Li(C4H3N2O2)(H2O)3], the Li(+) cation is coordinated by a pyrazole N atom and three water mol-ecules in a distorted tetra-hedral geometry. The carboxyl-ate group is deprotonated. The complex mol-ecules are involved in O-H⋯O and N-H⋯O hydrogen bonding, forming layers stacked along the b axis.

Related literature

For the structure of pyrazole-4-carb­oxy­lic acid, see: Foces-Foces et al. (2001 ▶).

Experimental

Crystal data

[Li(C4H3N2O2)(H2O)3]

M = 172.07

Orthorhombic,

a = 7.2817 (15) Å

b = 6.9635 (14) Å

c = 15.186 (3) Å

V = 770.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.25 × 0.18 × 0.12 mm

Data collection

Kuma KM4 four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.967, T max = 0.983

1161 measured reflections

1161 independent reflections

901 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: 5.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.01

1161 reflections

133 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.44 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301831X/kp2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301831X/kp2455Isup2.hkl

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

[Li(C4H3N2O2)(H2O)3]	F(000) = 360
Mr = 172.07	Dx = 1.484 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 7.2817 (15) Å	θ = 6–15°
b = 6.9635 (14) Å	µ = 0.13 mm−1
c = 15.186 (3) Å	T = 293 K
V = 770.0 (3) Å3	Block, colourless
Z = 4	0.25 × 0.18 × 0.12 mm

Kuma KM4 four-circle diffractometer	901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 30.1°, θmin = 2.7°
profile data from ω/2θ scan	h = 0→10
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→9
Tmin = 0.967, Tmax = 0.983	l = 0→21
1161 measured reflections	3 standard reflections every 200 reflections
1161 independent reflections	intensity decay: 5.9%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0972P)2] where P = (Fo2 + 2Fc2)/3
1161 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.34 e Å−3
7 restraints	Δρmin = −0.44 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.5914 (2)	0.4578 (3)	0.32056 (11)	0.0290 (4)
O1	0.7088 (2)	0.5037 (3)	0.18706 (12)	0.0332 (4)
N2	0.1533 (3)	0.4966 (3)	0.10494 (15)	0.0333 (5)
C4	0.3883 (2)	0.4946 (3)	0.20198 (14)	0.0217 (4)
N1	0.0900 (2)	0.5047 (3)	0.18846 (14)	0.0287 (4)
H1	−0.0246	0.5103	0.2019	0.034*
C6	0.5766 (3)	0.4856 (3)	0.23794 (14)	0.0214 (4)
C3	0.3351 (3)	0.4911 (4)	0.11354 (15)	0.0335 (5)
H3	0.4167	0.4856	0.0665	0.040*
C5	0.2250 (3)	0.5030 (3)	0.24788 (17)	0.0281 (4)
H5	0.2115	0.5067	0.3088	0.034*
Li1	0.0107 (6)	0.4846 (6)	−0.0115 (3)	0.0300 (8)
O4	0.1074 (2)	0.6710 (3)	−0.09637 (13)	0.0299 (4)
O3	−0.2382 (2)	0.5471 (3)	0.01447 (13)	0.0319 (4)
O5	0.0491 (3)	0.2401 (3)	−0.06531 (17)	0.0444 (5)
H51	0.121 (4)	0.161 (4)	−0.043 (3)	0.044 (10)*
H31	−0.277 (5)	0.650 (4)	−0.005 (3)	0.044 (10)*
H42	0.043 (4)	0.751 (4)	−0.123 (2)	0.039 (9)*
H52	−0.007 (5)	0.177 (7)	−0.100 (3)	0.073 (14)*
H41	0.192 (4)	0.631 (5)	−0.126 (2)	0.040 (8)*
H32	−0.275 (6)	0.554 (7)	0.0665 (16)	0.055 (12)*

	U11	U22	U33	U12	U13	U23
O2	0.0241 (7)	0.0453 (9)	0.0177 (6)	0.0001 (6)	−0.0027 (6)	0.0022 (6)
O1	0.0169 (7)	0.0595 (11)	0.0230 (8)	0.0000 (6)	0.0001 (6)	0.0051 (7)
N2	0.0198 (8)	0.0599 (13)	0.0203 (8)	0.0004 (8)	−0.0028 (8)	0.0006 (8)
C4	0.0149 (7)	0.0327 (10)	0.0176 (9)	0.0008 (6)	−0.0011 (7)	0.0013 (7)
N1	0.0162 (7)	0.0465 (11)	0.0236 (10)	0.0002 (6)	−0.0010 (7)	0.0021 (7)
C6	0.0160 (7)	0.0279 (8)	0.0203 (9)	0.0007 (6)	−0.0023 (7)	0.0007 (7)
C3	0.0186 (9)	0.0639 (15)	0.0180 (11)	0.0019 (9)	−0.0011 (8)	0.0004 (10)
C5	0.0175 (8)	0.0458 (12)	0.0210 (9)	0.0004 (8)	−0.0010 (8)	0.0012 (8)
Li1	0.0259 (15)	0.0370 (18)	0.0270 (18)	0.0004 (14)	0.0000 (16)	0.0022 (15)
O4	0.0282 (7)	0.0381 (9)	0.0235 (6)	0.0039 (6)	0.0062 (7)	0.0043 (6)
O3	0.0277 (7)	0.0433 (9)	0.0248 (8)	0.0045 (6)	0.0015 (6)	0.0026 (8)
O5	0.0602 (13)	0.0355 (9)	0.0376 (9)	0.0057 (9)	−0.0118 (10)	−0.0080 (8)

O2—C6	1.274 (3)	C5—H5	0.9300
O1—C6	1.240 (3)	Li1—O3	1.905 (5)
N2—C3	1.331 (3)	Li1—O5	1.909 (4)
N2—N1	1.350 (3)	Li1—O4	1.960 (5)
Li1—N2	2.053 (5)	O4—H42	0.835 (19)
C4—C5	1.379 (3)	O4—H41	0.813 (19)
C4—C3	1.398 (3)	O3—H31	0.823 (19)
C4—C6	1.478 (3)	O3—H32	0.84 (2)
N1—C5	1.334 (3)	O5—H51	0.829 (19)
N1—H1	0.8600	O5—H52	0.80 (2)
C3—H3	0.9300
C3—N2—N1	104.39 (18)	C4—C5—H5	126.5
C3—N2—Li1	125.9 (2)	O3—Li1—O5	115.6 (2)
N1—N2—Li1	129.66 (19)	O3—Li1—O4	109.1 (2)
C5—C4—C3	104.33 (18)	O5—Li1—O4	104.9 (2)
C5—C4—C6	128.0 (2)	O3—Li1—N2	107.0 (2)
C3—C4—C6	127.69 (19)	O5—Li1—N2	109.3 (2)
C5—N1—N2	112.55 (18)	O4—Li1—N2	110.9 (2)
C5—N1—H1	123.7	Li1—O4—H42	124 (2)
N2—N1—H1	123.7	Li1—O4—H41	114 (3)
O1—C6—O2	124.3 (2)	H42—O4—H41	112 (4)
O1—C6—C4	119.05 (19)	Li1—O3—H31	117 (3)
O2—C6—C4	116.66 (19)	Li1—O3—H32	121 (3)
N2—C3—C4	111.67 (19)	H31—O3—H32	100 (4)
N2—C3—H3	124.2	Li1—O5—H51	121 (3)
C4—C3—H3	124.2	Li1—O5—H52	134 (4)
N1—C5—C4	107.1 (2)	H51—O5—H52	103 (5)
N1—C5—H5	126.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H32···O1i	0.84 (2)	1.87 (3)	2.666 (3)	159 (4)
O4—H41···O2ii	0.81 (2)	1.88 (2)	2.684 (2)	171 (4)
O5—H52···O2iii	0.80 (2)	2.04 (3)	2.813 (3)	163 (5)
O4—H42···O2iv	0.84 (2)	1.94 (2)	2.770 (3)	174 (4)
O3—H31···O4v	0.82 (2)	2.05 (3)	2.820 (3)	156 (4)
O5—H51···O3vi	0.83 (2)	1.98 (2)	2.804 (3)	172 (4)
N1—H1···O1i	0.86	1.96	2.776 (3)	159

Table 1

Selected bond lengths (Å)

Li1—N2	2.053 (5)
Li1—O3	1.905 (5)
Li1—O5	1.909 (4)
Li1—O4	1.960 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H32⋯O1i	0.84 (2)	1.87 (3)	2.666 (3)	159 (4)
O4—H41⋯O2ii	0.81 (2)	1.88 (2)	2.684 (2)	171 (4)
O5—H52⋯O2iii	0.80 (2)	2.04 (3)	2.813 (3)	163 (5)
O4—H42⋯O2iv	0.84 (2)	1.94 (2)	2.770 (3)	174 (4)
O3—H31⋯O4v	0.82 (2)	2.05 (3)	2.820 (3)	156 (4)
O5—H51⋯O3vi	0.83 (2)	1.98 (2)	2.804 (3)	172 (4)
N1—H1⋯O1i	0.86	1.96	2.776 (3)	159

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