Lithium bis-(2-methyl-lactato)borate monohydrate.

The title compound {systematic name: poly[[aqua-lithium]-μ-3,3,8,8-tetra-methyl-1,4,6,9-tetra-oxa-5λ(4)-borataspiro-[4.4]nonane-2,7-dione]}, [Li(C(8)H(12)BO(6))(H(2)O)](n) (LiBMLB), forms a 12-membered macrocycle, which lies across a crystallographic inversion center. The lithium cations are pseudo-tetra-hedrally coordinated by three methyl-lactate ligands and a water mol-ecule. The asymmetric units couple across crystallographic inversion centers, forming the 12-membered macrocycles. These macrocycles, in turn, cross-link through the Li(+) cations, forming an infinite polymeric structure in two dimensions parallel to (101).

Related literature

For the synthesis and purification of HBMLB [BMLB is bis­(2-methyl­lactato)borate], see: Lamande et al. (1987 ▶). For the synthesis and properties of LiBMLB and BMLB−-based ionic liquids, see: Xu et al. (2003 ▶). For crystallographic data of similar lithium salts, see: Zavalij et al. (2004 ▶); Allen et al. (2011 ▶).

Experimental

Crystal data

[Li(C8H12BO6)(H2O)]

M = 239.94

Orthorhombic,

a = 12.7034 (4) Å

b = 11.3939 (4) Å

c = 15.8258 (5) Å

V = 2290.65 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 110 K

0.34 × 0.23 × 0.18 mm

Data collection

Bruker–Nonius Kappa X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.961, T max = 0.979

97648 measured reflections

5663 independent reflections

4436 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.05

5663 reflections

210 parameters

All H-atom parameters refined

Δρmax = 0.51 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: XL (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: cif2tables.py (Boyle, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017540/vn2036sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017540/vn2036Isup2.hkl

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

[Li(C8H12BO6)(H2O)]	F(000) = 1008
Mr = 239.94	Dx = 1.392 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9969 reflections
a = 12.7034 (4) Å	θ = 2.7–35.0°
b = 11.3939 (4) Å	µ = 0.12 mm−1
c = 15.8258 (5) Å	T = 110 K
V = 2290.65 (13) Å3	Prism, colourless
Z = 8	0.34 × 0.23 × 0.18 mm

Bruker–Nonius Kappa X8 APEXII diffractometer	5663 independent reflections
Radiation source: fine-focus sealed tube	4436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scans	θmax = 37.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→21
Tmin = 0.961, Tmax = 0.979	k = −19→19
97648 measured reflections	l = −24→26

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.3146P] where P = (Fo2 + 2Fc2)/3
5663 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.26 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
Li1	0.50924 (9)	0.90999 (11)	0.30769 (8)	0.0141 (2)
O1	0.36589 (3)	0.97594 (4)	0.31383 (3)	0.01110 (9)
O2	0.21632 (3)	1.07434 (4)	0.36227 (3)	0.01158 (9)
O3	0.09643 (4)	1.00827 (4)	0.27079 (3)	0.01399 (9)
O4	0.38947 (4)	1.16989 (4)	0.37533 (3)	0.01216 (9)
O5	0.34797 (4)	1.01520 (4)	0.46522 (3)	0.01186 (9)
O6	0.42797 (4)	1.07518 (5)	0.58279 (3)	0.01560 (10)
B1	0.33286 (5)	1.05967 (6)	0.37751 (4)	0.01016 (11)
C1	0.28304 (4)	0.95743 (5)	0.25349 (4)	0.00955 (10)
C2	0.18775 (5)	1.01423 (5)	0.29565 (4)	0.01021 (10)
C3	0.30791 (5)	1.02291 (6)	0.17184 (4)	0.01333 (11)
H3A	0.3167 (9)	1.1064 (10)	0.1823 (7)	0.024 (3)*
H3B	0.2509 (10)	1.0133 (10)	0.1323 (7)	0.023 (3)*
H3C	0.3744 (9)	0.9899 (9)	0.1465 (7)	0.020 (2)*
C4	0.26552 (5)	0.82752 (5)	0.23795 (4)	0.01314 (11)
H4A	0.3291 (9)	0.7933 (10)	0.2120 (7)	0.025 (3)*
H4B	0.2057 (9)	0.8176 (9)	0.1987 (7)	0.020 (2)*
H4C	0.2505 (8)	0.7861 (9)	0.2889 (7)	0.019 (2)*
C5	0.42313 (5)	1.20239 (5)	0.45830 (4)	0.01192 (11)
C6	0.40175 (5)	1.09179 (5)	0.50964 (4)	0.01110 (11)
C7	0.35561 (7)	1.30226 (7)	0.49223 (5)	0.02424 (16)
H7A	0.3687 (10)	1.3751 (11)	0.4564 (8)	0.033 (3)*
H7B	0.3770 (11)	1.3184 (12)	0.5514 (9)	0.041 (3)*
H7C	0.2815 (11)	1.2823 (12)	0.4919 (8)	0.036 (3)*
C8	0.53960 (6)	1.23386 (7)	0.45795 (5)	0.01929 (13)
H8A	0.5830 (10)	1.1701 (11)	0.4330 (8)	0.032 (3)*
H8B	0.5636 (9)	1.2482 (10)	0.5166 (8)	0.030 (3)*
H8C	0.5506 (9)	1.3071 (10)	0.4247 (7)	0.026 (3)*
O1W	0.51220 (4)	0.74779 (4)	0.26871 (3)	0.01548 (10)
H1WA	0.5426 (12)	0.7243 (12)	0.2236 (10)	0.046 (4)*
H1WB	0.4774 (11)	0.6878 (12)	0.2863 (9)	0.041 (3)*

	U11	U22	U33	U12	U13	U23
Li1	0.0132 (5)	0.0162 (5)	0.0128 (5)	0.0010 (4)	−0.0010 (4)	0.0001 (4)
O1	0.00863 (17)	0.0148 (2)	0.00990 (19)	0.00106 (14)	−0.00213 (14)	−0.00282 (15)
O2	0.00987 (18)	0.01454 (19)	0.0103 (2)	0.00099 (14)	−0.00098 (14)	−0.00277 (15)
O3	0.00931 (18)	0.0180 (2)	0.0147 (2)	0.00129 (15)	−0.00238 (16)	−0.00252 (17)
O4	0.0154 (2)	0.01258 (19)	0.00853 (18)	−0.00325 (15)	−0.00187 (15)	0.00066 (15)
O5	0.01270 (19)	0.01361 (19)	0.00925 (19)	−0.00208 (15)	−0.00121 (15)	0.00105 (15)
O6	0.0148 (2)	0.0233 (2)	0.0087 (2)	0.00015 (17)	−0.00136 (16)	0.00053 (17)
B1	0.0099 (2)	0.0121 (3)	0.0085 (3)	−0.0002 (2)	−0.0005 (2)	−0.0001 (2)
C1	0.0085 (2)	0.0109 (2)	0.0092 (2)	−0.00022 (17)	−0.00104 (18)	−0.00056 (19)
C2	0.0104 (2)	0.0109 (2)	0.0094 (2)	0.00061 (18)	−0.00024 (18)	0.00053 (18)
C3	0.0150 (3)	0.0149 (3)	0.0101 (2)	−0.0014 (2)	0.0006 (2)	0.0015 (2)
C4	0.0122 (2)	0.0107 (2)	0.0166 (3)	−0.00059 (18)	−0.0002 (2)	−0.0010 (2)
C5	0.0137 (2)	0.0123 (2)	0.0098 (2)	−0.00051 (19)	−0.00179 (19)	−0.00122 (19)
C6	0.0093 (2)	0.0145 (2)	0.0095 (2)	0.00077 (18)	0.00041 (18)	−0.0008 (2)
C7	0.0333 (4)	0.0180 (3)	0.0214 (3)	0.0094 (3)	0.0012 (3)	−0.0049 (3)
C8	0.0167 (3)	0.0213 (3)	0.0198 (3)	−0.0076 (2)	−0.0040 (2)	0.0027 (3)
O1W	0.0147 (2)	0.0146 (2)	0.0172 (2)	−0.00084 (16)	0.00323 (17)	−0.00317 (17)

Li1—O1	1.9725 (13)	C1—C2	1.5263 (8)
Li1—O1W	1.9487 (13)	C3—H3A	0.972 (11)
Li1—O3i	2.0059 (13)	C3—H3B	0.963 (12)
Li1—O6ii	1.9155 (13)	C3—H3C	1.007 (11)
O1—C1	1.4366 (7)	C4—H4A	0.987 (12)
O1—B1	1.4498 (8)	C4—H4B	0.988 (11)
O2—C2	1.3086 (7)	C4—H4C	0.953 (11)
O2—B1	1.5094 (8)	C5—C8	1.5223 (9)
O3—C2	1.2268 (7)	C5—C7	1.5228 (10)
O3—Li1iii	2.0059 (13)	C5—C6	1.5238 (9)
O4—C5	1.4297 (8)	C7—H7A	1.019 (13)
O4—B1	1.4476 (8)	C7—H7B	0.993 (14)
O5—C6	1.3125 (8)	C7—H7C	0.968 (13)
O5—B1	1.4901 (8)	C8—H8A	0.994 (13)
O6—C6	1.2193 (8)	C8—H8B	0.990 (12)
O6—Li1ii	1.9155 (13)	C8—H8C	0.997 (12)
C1—C4	1.5169 (8)	O1W—H1WA	0.854 (16)
C1—C3	1.5251 (9)	O1W—H1WB	0.861 (14)
O6ii—Li1—O1W	111.23 (6)	H3A—C3—H3C	109.7 (9)
O6ii—Li1—O1	107.84 (6)	H3B—C3—H3C	109.3 (10)
O1W—Li1—O1	113.25 (6)	C1—C4—H4A	109.4 (7)
O6ii—Li1—O3i	106.33 (6)	C1—C4—H4B	109.1 (6)
O1W—Li1—O3i	108.83 (6)	H4A—C4—H4B	108.8 (9)
O1—Li1—O3i	109.12 (6)	C1—C4—H4C	112.0 (6)
C1—O1—B1	110.28 (5)	H4A—C4—H4C	108.7 (9)
C1—O1—Li1	125.99 (5)	H4B—C4—H4C	108.7 (9)
B1—O1—Li1	123.51 (5)	O4—C5—C8	110.39 (5)
C2—O2—B1	110.05 (5)	O4—C5—C7	110.42 (6)
C2—O3—Li1iii	138.72 (6)	C8—C5—C7	111.88 (6)
C5—O4—B1	110.58 (5)	O4—C5—C6	102.84 (5)
C6—O5—B1	109.87 (5)	C8—C5—C6	111.71 (5)
C6—O6—Li1ii	163.55 (6)	C7—C5—C6	109.24 (6)
O4—B1—O1	114.25 (5)	O6—C6—O5	123.19 (6)
O4—B1—O5	104.66 (5)	O6—C6—C5	125.87 (6)
O1—B1—O5	112.74 (5)	O5—C6—C5	110.92 (5)
O4—B1—O2	112.80 (5)	C5—C7—H7A	108.7 (7)
O1—B1—O2	104.22 (5)	C5—C7—H7B	108.4 (8)
O5—B1—O2	108.23 (5)	H7A—C7—H7B	109.3 (11)
O1—C1—C4	111.01 (5)	C5—C7—H7C	111.7 (8)
O1—C1—C3	109.85 (5)	H7A—C7—H7C	110.3 (11)
C4—C1—C3	111.74 (5)	H7B—C7—H7C	108.4 (11)
O1—C1—C2	103.20 (5)	C5—C8—H8A	111.6 (7)
C4—C1—C2	111.60 (5)	C5—C8—H8B	109.5 (7)
C3—C1—C2	109.10 (5)	H8A—C8—H8B	108.8 (10)
O3—C2—O2	123.33 (6)	C5—C8—H8C	109.6 (7)
O3—C2—C1	125.90 (6)	H8A—C8—H8C	109.0 (10)
O2—C2—C1	110.74 (5)	H8B—C8—H8C	108.3 (9)
C1—C3—H3A	111.0 (7)	Li1—O1W—H1WA	124.8 (9)
C1—C3—H3B	109.8 (7)	Li1—O1W—H1WB	129.9 (9)
H3A—C3—H3B	107.9 (9)	H1WA—O1W—H1WB	104.7 (13)
C1—C3—H3C	109.2 (6)
O6ii—Li1—O1—C1	−163.76 (5)	B1—O1—C1—C2	−12.51 (6)
O1W—Li1—O1—C1	−40.24 (9)	Li1—O1—C1—C2	172.64 (6)
O3i—Li1—O1—C1	81.15 (8)	Li1iii—O3—C2—O2	−164.56 (7)
O6ii—Li1—O1—B1	22.04 (9)	Li1iii—O3—C2—C1	17.31 (12)
O1W—Li1—O1—B1	145.56 (6)	B1—O2—C2—O3	177.79 (6)
O3i—Li1—O1—B1	−93.05 (7)	B1—O2—C2—C1	−3.83 (7)
C5—O4—B1—O1	−132.62 (5)	O1—C1—C2—O3	−171.56 (6)
C5—O4—B1—O5	−8.84 (6)	C4—C1—C2—O3	−52.29 (8)
C5—O4—B1—O2	108.60 (6)	C3—C1—C2—O3	71.68 (8)
C1—O1—B1—O4	−112.92 (6)	O1—C1—C2—O2	10.11 (6)
Li1—O1—B1—O4	62.07 (8)	C4—C1—C2—O2	129.38 (5)
C1—O1—B1—O5	127.75 (5)	C3—C1—C2—O2	−106.65 (6)
Li1—O1—B1—O5	−57.25 (8)	B1—O4—C5—C8	130.06 (6)
C1—O1—B1—O2	10.61 (6)	B1—O4—C5—C7	−105.70 (6)
Li1—O1—B1—O2	−174.39 (5)	B1—O4—C5—C6	10.76 (6)
C6—O5—B1—O4	2.75 (6)	Li1ii—O6—C6—O5	172.88 (18)
C6—O5—B1—O1	127.49 (5)	Li1ii—O6—C6—C5	−8.8 (2)
C6—O5—B1—O2	−117.77 (5)	B1—O5—C6—O6	−177.52 (6)
C2—O2—B1—O4	120.53 (5)	B1—O5—C6—C5	3.98 (7)
C2—O2—B1—O1	−3.95 (6)	O4—C5—C6—O6	172.41 (6)
C2—O2—B1—O5	−124.16 (5)	C8—C5—C6—O6	54.03 (8)
B1—O1—C1—C4	−132.19 (5)	C7—C5—C6—O6	−70.29 (8)
Li1—O1—C1—C4	52.96 (8)	O4—C5—C6—O5	−9.14 (6)
B1—O1—C1—C3	103.72 (6)	C8—C5—C6—O5	−127.51 (6)
Li1—O1—C1—C3	−71.13 (7)	C7—C5—C6—O5	108.16 (6)

Table 1

Selected bond lengths (Å)

Li1—O1	1.9725 (13)
Li1—O1W	1.9487 (13)
Li1—O3i	2.0059 (13)
Li1—O6ii	1.9155 (13)

Symmetry codes: (i) ; (ii) .