catena-Poly[[diaqua-lithium]-μ-[rac-cis-(2-carb-oxy-cyclo-hexane-1-carboxyl-ato-κO:O]].

In the structure of the title compound, [Li(C(8)H(11)O(4))(H(2)O)(2)](n), the distorted tetra-hadral LiO(4) coordination sphere comprises two water mol-ecules and two carboxyl O-atom donors from separate bridging cis-2-carb-oxy-cyclo-hexane-1-carboxyl-ate monoanions [Li-O = 1.887 (4)-1.946 (3) Å], giving chain substructures which extend along [010]. Water-water and water-carboxyl O-H⋯O hydrogen bonds stabilize these chain structures and provide inter-chain links, resulting in a two-dimensional layered structure extending parallel to (100).

Related literature

For the structure of an NiII complex derived from racemic cis-cyclo­hexane-1,2-dicarb­oxy­lic acid, see: Zheng et al. (2008 ▶) and for the structure of the corresponding Sr2+ complex, see: Robertson & Harrison (2010 ▶). For the structure of lithium 3,5-dinitro­benzoate, see: Yang & Ng (2007 ▶) and for lithium hydrogenterephthalate pseudopolymorphs, see: Küppers (1978 ▶); Gonschorek & Küppers (1975 ▶); Adiwidjaja & Küppers (1978 ▶).

Experimental

Crystal data

[Li(C8H11O4)(H2O)2]

M = 214.14

Monoclinic,

a = 16.2749 (5) Å

b = 5.4568 (2) Å

c = 12.0438 (5) Å

β = 97.533 (3)°

V = 1060.37 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.97, T max = 0.99

5758 measured reflections

2084 independent reflections

1550 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.134

S = 1.04

2084 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045077/ng5258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045077/ng5258Isup2.hkl

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

[Li(C8H11O4)(H2O)2]	F(000) = 456
Mr = 214.14	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2836 reflections
a = 16.2749 (5) Å	θ = 3.2–28.7°
b = 5.4568 (2) Å	µ = 0.11 mm−1
c = 12.0438 (5) Å	T = 200 K
β = 97.533 (3)°	Block, colourless
V = 1060.37 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Oxford Diffraction Gemini-S CCD-detector diffractometer	2084 independent reflections
Radiation source: Enhance (Mo) X-ray source	1550 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.97, Tmax = 0.99	l = −13→14
5758 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3
2084 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1W	0.04966 (10)	0.4570 (4)	0.75941 (13)	0.0617 (7)
O2W	0.03531 (8)	0.7437 (3)	0.53796 (16)	0.0527 (6)
O11	0.17016 (8)	−0.0191 (2)	0.43846 (11)	0.0318 (5)
O12	0.13158 (8)	0.2623 (2)	0.55259 (11)	0.0297 (4)
O21	0.19747 (8)	−0.2424 (2)	0.69312 (11)	0.0265 (4)
O22	0.23639 (9)	−0.0915 (2)	0.86385 (11)	0.0366 (5)
C1	0.27299 (10)	0.1392 (3)	0.58486 (14)	0.0208 (5)
C2	0.27190 (10)	0.1422 (3)	0.71265 (14)	0.0198 (5)
C3	0.36052 (11)	0.1758 (3)	0.77421 (16)	0.0270 (6)
C4	0.41960 (11)	−0.0170 (4)	0.73895 (17)	0.0331 (6)
C5	0.42078 (12)	−0.0142 (4)	0.61278 (18)	0.0362 (7)
C6	0.33353 (11)	−0.0509 (3)	0.54969 (16)	0.0265 (6)
C11	0.18554 (11)	0.1254 (3)	0.52073 (14)	0.0211 (5)
C21	0.23163 (10)	−0.0844 (3)	0.75461 (14)	0.0204 (5)
Li1	0.10696 (18)	0.5409 (6)	0.6350 (3)	0.0278 (9)
H1	0.29500	0.29900	0.56620	0.0310*
H2	0.23920	0.28440	0.73030	0.0300*
H11W	0.09160	0.44600	0.82710	0.0930*
H12W	0.02120	0.31460	0.75400	0.0930*
H21W	−0.01870	0.74220	0.50990	0.0790*
H22	0.21350	−0.23120	0.88480	0.0550*
H22W	0.06250	0.85130	0.50340	0.0790*
H31	0.38070	0.33750	0.75810	0.0410*
H32	0.35930	0.16460	0.85440	0.0410*
H41	0.47500	0.01400	0.77660	0.0500*
H42	0.40260	−0.17780	0.76160	0.0500*
H51	0.45690	−0.14350	0.59240	0.0540*
H52	0.44290	0.14110	0.59100	0.0540*
H61	0.33560	−0.03770	0.46980	0.0400*
H62	0.31400	−0.21400	0.56480	0.0400*

	U11	U22	U33	U12	U13	U23
O1W	0.0409 (9)	0.1113 (15)	0.0325 (9)	−0.0244 (10)	0.0032 (7)	0.0115 (9)
O2W	0.0242 (8)	0.0398 (9)	0.0898 (14)	−0.0014 (7)	−0.0090 (7)	0.0226 (9)
O11	0.0366 (8)	0.0306 (8)	0.0258 (8)	0.0077 (6)	−0.0050 (6)	−0.0094 (6)
O12	0.0245 (7)	0.0301 (7)	0.0325 (8)	0.0082 (6)	−0.0034 (5)	−0.0086 (6)
O21	0.0291 (7)	0.0253 (7)	0.0244 (7)	−0.0085 (6)	0.0005 (5)	−0.0021 (5)
O22	0.0573 (10)	0.0320 (8)	0.0197 (8)	−0.0171 (7)	0.0016 (6)	0.0011 (6)
C1	0.0213 (9)	0.0184 (9)	0.0227 (10)	−0.0009 (8)	0.0029 (7)	0.0018 (7)
C2	0.0199 (9)	0.0170 (9)	0.0214 (9)	0.0011 (7)	−0.0018 (7)	−0.0017 (7)
C3	0.0224 (9)	0.0258 (10)	0.0309 (11)	−0.0058 (8)	−0.0038 (7)	−0.0010 (8)
C4	0.0187 (9)	0.0363 (11)	0.0420 (13)	0.0012 (9)	−0.0042 (8)	0.0001 (9)
C5	0.0211 (10)	0.0431 (13)	0.0451 (13)	0.0046 (9)	0.0071 (8)	−0.0002 (10)
C6	0.0239 (9)	0.0295 (10)	0.0268 (10)	0.0048 (8)	0.0061 (7)	−0.0006 (8)
C11	0.0250 (9)	0.0194 (9)	0.0180 (9)	0.0014 (8)	−0.0004 (7)	0.0010 (7)
C21	0.0184 (8)	0.0210 (9)	0.0210 (9)	0.0039 (7)	0.0000 (7)	0.0004 (7)
Li1	0.0223 (15)	0.0305 (17)	0.0303 (17)	−0.0018 (14)	0.0029 (12)	−0.0068 (13)

O1W—Li1	1.921 (4)	C2—C3	1.544 (2)
O2W—Li1	1.896 (4)	C2—C21	1.517 (2)
O12—Li1	1.887 (4)	C3—C4	1.523 (3)
O21—Li1i	1.946 (3)	C4—C5	1.522 (3)
O11—C11	1.265 (2)	C5—C6	1.533 (3)
O12—C11	1.251 (2)	C1—H1	0.9800
O21—C21	1.222 (2)	C2—H2	0.9800
O22—C21	1.308 (2)	C3—H31	0.9700
O1W—H11W	0.9900	C3—H32	0.9700
O1W—H12W	0.9000	C4—H41	0.9700
O2W—H21W	0.9000	C4—H42	0.9700
O2W—H22W	0.8700	C5—H51	0.9700
O22—H22	0.9000	C5—H52	0.9700
C1—C2	1.542 (2)	C6—H61	0.9700
C1—C11	1.530 (2)	C6—H62	0.9700
C1—C6	1.528 (2)
C11—O12—Li1	148.04 (15)	C1—C2—H2	108.00
C21—O21—Li1i	155.44 (16)	C21—C2—H2	108.00
Li1—O1W—H11W	108.00	C2—C3—H32	109.00
Li1—O1W—H12W	116.00	C2—C3—H31	109.00
H11W—O1W—H12W	107.00	C4—C3—H32	109.00
Li1—O2W—H21W	136.00	H31—C3—H32	108.00
Li1—O2W—H22W	112.00	C4—C3—H31	109.00
H21W—O2W—H22W	111.00	C3—C4—H41	109.00
C21—O22—H22	110.00	C5—C4—H41	109.00
C2—C1—C6	112.09 (14)	C5—C4—H42	109.00
C2—C1—C11	111.90 (13)	C3—C4—H42	109.00
C6—C1—C11	114.69 (14)	H41—C4—H42	108.00
C1—C2—C3	110.39 (14)	C6—C5—H52	109.00
C1—C2—C21	112.71 (14)	H51—C5—H52	108.00
C3—C2—C21	110.74 (14)	C6—C5—H51	109.00
C2—C3—C4	111.61 (15)	C4—C5—H51	109.00
C3—C4—C5	111.25 (17)	C4—C5—H52	109.00
C4—C5—C6	111.18 (16)	C1—C6—H61	109.00
C1—C6—C5	111.27 (15)	C1—C6—H62	109.00
O12—C11—C1	117.38 (15)	C5—C6—H61	109.00
O11—C11—O12	122.52 (16)	H61—C6—H62	108.00
O11—C11—C1	120.10 (15)	C5—C6—H62	109.00
O21—C21—C2	123.74 (15)	O1W—Li1—O12	112.12 (18)
O21—C21—O22	123.43 (15)	O1W—Li1—O21ii	106.63 (18)
O22—C21—C2	112.83 (14)	O2W—Li1—O21ii	104.03 (17)
C11—C1—H1	106.00	O12—Li1—O21ii	118.41 (16)
C6—C1—H1	106.00	O2W—Li1—O12	107.57 (19)
C2—C1—H1	106.00	O1W—Li1—O2W	107.32 (16)
C3—C2—H2	108.00
Li1—O12—C11—O11	−161.8 (3)	C11—C1—C6—C5	176.49 (15)
Li1—O12—C11—C1	17.7 (4)	C2—C1—C11—O11	−135.69 (16)
C11—O12—Li1—O1W	−115.3 (3)	C2—C1—C11—O12	44.8 (2)
C11—O12—Li1—O2W	126.9 (3)	C6—C1—C11—O11	−6.6 (2)
C11—O12—Li1—O21ii	9.5 (4)	C6—C1—C11—O12	173.93 (15)
Li1i—O21—C21—O22	51.7 (4)	C1—C2—C3—C4	−54.63 (19)
Li1i—O21—C21—C2	−127.4 (3)	C21—C2—C3—C4	70.90 (19)
C21—O21—Li1i—O1Wi	−32.5 (4)	C1—C2—C21—O21	−5.8 (2)
C21—O21—Li1i—O2Wi	80.8 (4)	C1—C2—C21—O22	174.98 (14)
C21—O21—Li1i—O12i	−159.9 (3)	C3—C2—C21—O21	−130.05 (17)
C6—C1—C2—C3	53.79 (18)	C3—C2—C21—O22	50.76 (19)
C6—C1—C2—C21	−70.61 (18)	C2—C3—C4—C5	56.5 (2)
C11—C1—C2—C3	−175.75 (13)	C3—C4—C5—C6	−56.5 (2)
C11—C1—C2—C21	59.85 (18)	C4—C5—C6—C1	55.4 (2)
C2—C1—C6—C5	−54.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O11iii	0.99	1.77	2.739 (2)	163
O1W—H12W···O1Wiv	0.90	2.26	3.164 (3)	180
O2W—H21W···O12v	0.90	1.89	2.7913 (19)	179
O2W—H22W···O11ii	0.87	2.13	2.936 (2)	153
O2W—H22W···O12ii	0.87	2.54	3.228 (2)	136
O22—H22···O11vi	0.90	1.70	2.5958 (17)	174
C3—H32···O22	0.97	2.45	2.819 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O11i	0.99	1.77	2.739 (2)	163
O1W—H12W⋯O1Wii	0.90	2.26	3.164 (3)	180
O2W—H21W⋯O12iii	0.90	1.89	2.7913 (19)	179
O2W—H22W⋯O11iv	0.87	2.13	2.936 (2)	153
O2W—H22W⋯O12iv	0.87	2.54	3.228 (2)	136
O22—H22⋯O11v	0.90	1.70	2.5958 (17)	174

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