Poly[μ6-(naphthalene-2,6-di-carboxyl-ato)-bis-(aqua-lithium)].

The title compound, [Li2(C12H6O4)(H2O)2] n , crystallizes with one half of the molecular entities in the asymmetric unit. The second half is gererated by inversion symmetry. The crystal structure has a layered arrangement built from distorted edge-sharing LiO3(OH)2 tetra-hedra parallel to (100), with naphthalenedi-carboxyl-ate bridging the LiO3(OH)2 layers along the [100] direction. Hydrogen bonding between the water molecule and adjacent carboxylate groups consolidates the packing.

Related literature

For the synthesis and crystal structure of 2,6-naphthalenedi­carb­oxy­lic acid, see Kaduk & Golab (1999 ▶). For the synthesis and crystal structure of dilithium-2,6-naphthalene di­carboxyl­ate [Li2(2,6-NDC)], see: Banerjee et al. (2009a ▶). For related compounds, see: Banerjee et al. (2009b ▶). [Li2(2,6-NDC)] was recently reported to exhibit good electrochemical performance, see: Fédèle et al. (2014 ▶).

Experimental

Crystal data

[Li2(C12H6O4)(H2O)2]

M = 132.04

Monoclinic,

a = 23.5695 (18) Å

b = 6.8115 (5) Å

c = 7.5327 (6) Å

β = 90.325 (3)°

V = 1209.31 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.12 × 0.05 × 0.03 mm

Data collection

Bruker D8 Venture diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.707, T max = 0.746

12848 measured reflections

1388 independent reflections

1032 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.06

1388 reflections

99 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXLE (Hübschle et al., 2011 ▶); molecular graphics: VESTA (Momma & Izumi, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013130/pj2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013130/pj2011Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013130/pj2011Isup3.mol

CCDC reference: 1006973

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

[Li2(C12H6O4)(H2O)2]	Z = 8
Mr = 132.04	F(000) = 544
Monoclinic, C2/c	Dx = 1.450 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.5695 (18) Å	µ = 0.11 mm−1
b = 6.8115 (5) Å	T = 293 K
c = 7.5327 (6) Å	Prism, colourless
β = 90.325 (3)°	0.12 × 0.05 × 0.03 mm
V = 1209.31 (16) Å3

Bruker D8 Venture diffractometer	1388 independent reflections
Radiation source: fine-focus sealed tube	1032 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.050
phi scan	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −30→29
Tmin = 0.707, Tmax = 0.746	k = −8→8
12848 measured reflections	l = −9→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0452P)2 + 1.0165P] where P = (Fo2 + 2Fc2)/3
1388 reflections	(Δ/σ)max = 0.010
99 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 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·A single gross outlier (reflection 3 3 3)was omitted from the final refinement.

	x	y	z	Uiso*/Ueq
O1	0.06322 (5)	0.42265 (18)	0.41860 (17)	0.0357 (3)
H1W	0.0611 (12)	0.761 (5)	0.695 (4)	0.082 (10)*
H2W	0.0553 (11)	0.949 (5)	0.635 (4)	0.089 (10)*
O2	0.05985 (7)	0.8245 (3)	0.6045 (2)	0.0496 (4)
O3	−0.05040 (4)	0.75789 (19)	0.34106 (15)	0.0323 (3)
C1	0.08206 (6)	0.3193 (2)	0.5432 (2)	0.0252 (4)
C2	0.14481 (6)	0.2809 (2)	0.5548 (2)	0.0251 (4)
C3	0.17876 (6)	0.3237 (2)	0.4137 (2)	0.0261 (4)
H3	0.1627	0.3764	0.3112	0.031*
C4	0.23825 (6)	0.2893 (2)	0.4209 (2)	0.0245 (4)
C5	0.22574 (7)	0.1697 (3)	0.7239 (2)	0.0300 (4)
H4	0.2412	0.1206	0.8288	0.036*
C6	0.16892 (7)	0.2010 (3)	0.7120 (2)	0.0303 (4)
H5	0.1457	0.1700	0.8074	0.036*
Li1	0.03075 (12)	0.6849 (4)	0.4040 (4)	0.0305 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0262 (6)	0.0378 (7)	0.0432 (7)	0.0097 (5)	−0.0039 (5)	0.0041 (6)
O2	0.0714 (11)	0.0404 (9)	0.0367 (8)	−0.0102 (8)	−0.0102 (7)	−0.0003 (7)
O3	0.0197 (5)	0.0452 (7)	0.0322 (6)	−0.0007 (5)	0.0075 (5)	−0.0052 (6)
C1	0.0190 (7)	0.0253 (8)	0.0313 (9)	0.0018 (6)	0.0016 (6)	−0.0084 (7)
C2	0.0180 (7)	0.0241 (8)	0.0333 (9)	0.0019 (6)	0.0022 (6)	−0.0009 (7)
C3	0.0208 (8)	0.0285 (8)	0.0290 (8)	0.0037 (7)	−0.0011 (6)	0.0035 (7)
C4	0.0215 (8)	0.0236 (8)	0.0283 (8)	0.0021 (6)	0.0010 (6)	0.0023 (7)
C5	0.0241 (8)	0.0365 (9)	0.0293 (9)	0.0035 (7)	0.0005 (6)	0.0096 (8)
C6	0.0239 (8)	0.0366 (9)	0.0304 (9)	0.0016 (7)	0.0063 (6)	0.0053 (7)
Li1	0.0275 (14)	0.0337 (15)	0.0302 (14)	0.0016 (12)	−0.0007 (11)	0.0021 (12)

O1—C1	1.253 (2)	C3—C4	1.422 (2)
O1—Li1	1.946 (3)	C3—H3	0.9300
O2—Li1	1.910 (3)	C4—C5iii	1.414 (2)
O2—H1W	0.81 (3)	C4—C4iii	1.417 (3)
O2—H2W	0.89 (3)	C5—C6	1.359 (2)
O3—C1i	1.265 (2)	C5—C4iii	1.414 (2)
O3—Li1ii	1.969 (3)	C5—H4	0.9300
O3—Li1	2.030 (3)	C6—H5	0.9300
C1—O3i	1.265 (2)	Li1—O3ii	1.969 (3)
C1—C2	1.504 (2)	Li1—C1i	2.691 (3)
C1—Li1i	2.691 (3)	Li1—Li1ii	2.728 (6)
C2—C3	1.365 (2)	Li1—Li1i	3.250 (6)
C2—C6	1.419 (2)
C1—O1—Li1	134.09 (14)	C5—C6—C2	120.35 (15)
Li1—O2—H1W	114 (2)	C5—C6—H5	119.8
Li1—O2—H2W	129.8 (19)	C2—C6—H5	119.8
H1W—O2—H2W	107 (3)	O2—Li1—O1	105.84 (15)
C1i—O3—Li1ii	133.11 (14)	O2—Li1—O3ii	122.04 (16)
C1i—O3—Li1	107.22 (13)	O1—Li1—O3ii	100.98 (14)
Li1ii—O3—Li1	86.02 (13)	O2—Li1—O3	113.35 (15)
O1—C1—O3i	122.81 (14)	O1—Li1—O3	127.43 (16)
O1—C1—C2	119.05 (14)	O3ii—Li1—O3	86.88 (12)
O3i—C1—C2	118.13 (14)	O2—Li1—C1i	103.83 (13)
O1—C1—Li1i	76.73 (11)	O1—Li1—C1i	111.74 (13)
O3i—C1—Li1i	46.09 (10)	O3ii—Li1—C1i	112.28 (13)
C2—C1—Li1i	164.10 (13)	O3—Li1—C1i	26.69 (6)
C3—C2—C6	119.84 (14)	O2—Li1—Li1ii	149.25 (11)
C3—C2—C1	119.89 (14)	O1—Li1—Li1ii	104.78 (10)
C6—C2—C1	120.27 (14)	O3ii—Li1—Li1ii	47.92 (9)
C2—C3—C4	121.15 (15)	O3—Li1—Li1ii	46.06 (9)
C2—C3—H3	119.4	C1i—Li1—Li1ii	66.74 (11)
C4—C3—H3	119.4	O2—Li1—Li1i	101.12 (15)
C5iii—C4—C4iii	119.35 (17)	O1—Li1—Li1i	55.92 (10)
C5iii—C4—C3	122.30 (14)	O3ii—Li1—Li1i	136.12 (18)
C4iii—C4—C3	118.35 (17)	O3—Li1—Li1i	82.63 (12)
C6—C5—C4iii	120.93 (15)	C1i—Li1—Li1i	58.82 (9)
C6—C5—H4	119.5	Li1ii—Li1—Li1i	98.18 (13)
C4iii—C5—H4	119.5
Li1—O1—C1—O3i	71.7 (2)	C1—O1—Li1—O2	24.8 (2)
Li1—O1—C1—C2	−109.69 (19)	C1—O1—Li1—O3ii	152.87 (15)
Li1—O1—C1—Li1i	72.46 (19)	C1—O1—Li1—O3	−112.6 (2)
O1—C1—C2—C3	−13.1 (2)	C1—O1—Li1—C1i	−87.6 (2)
O3i—C1—C2—C3	165.63 (15)	C1—O1—Li1—Li1ii	−158.04 (16)
Li1i—C1—C2—C3	159.3 (4)	C1—O1—Li1—Li1i	−68.08 (18)
O1—C1—C2—C6	166.67 (15)	C1i—O3—Li1—O2	−73.79 (18)
O3i—C1—C2—C6	−14.6 (2)	Li1ii—O3—Li1—O2	152.12 (13)
Li1i—C1—C2—C6	−21.0 (5)	C1i—O3—Li1—O1	61.0 (2)
C6—C2—C3—C4	0.2 (3)	Li1ii—O3—Li1—O1	−73.05 (18)
C1—C2—C3—C4	179.88 (14)	C1i—O3—Li1—O3ii	162.48 (11)
C2—C3—C4—C5iii	179.28 (16)	Li1ii—O3—Li1—O3ii	28.40 (17)
C2—C3—C4—C4iii	−0.5 (3)	Li1ii—O3—Li1—C1i	−134.08 (16)
C4iii—C5—C6—C2	−1.7 (3)	C1i—O3—Li1—Li1ii	134.08 (16)
C3—C2—C6—C5	1.0 (3)	C1i—O3—Li1—Li1i	25.18 (15)
C1—C2—C6—C5	−178.74 (15)	Li1ii—O3—Li1—Li1i	−108.90 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1W···O1iv	0.81 (3)	2.10 (3)	2.905 (2)	176 (3)
O2—H2W···O3v	0.89 (3)	2.01 (3)	2.883 (2)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1W⋯O1i	0.81 (3)	2.10 (3)	2.905 (2)	176 (3)
O2—H2W⋯O3ii	0.89 (3)	2.01 (3)	2.883 (2)	169 (3)

Symmetry codes: (i) ; (ii) .