Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006773/cf6157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006773/cf6157Isup2.hkl |
CCDC reference: 185752
The title compound was prepared by mixing 1.847 g (0.025 M) of lithium carbonate, 3.09 g (0.05 M) of boric acid and 9.08 g (0.1 M) of racemic lactic acid. The components were thoroughly dissolved in 100 ml of distilled water and the solution was evaporated to dryness by heating at 323 K for 8 h. The yield was around 60%. Single crystals were obtained by slow evaporation of a saturated aqueous solution at 298 K. Crystals of size up to 5 × 4 × 3 mm were obtained in 15–20 d. The UV–Vis spectrum of a crystal was recorded using a Varian Cary 5E UV-Vis-NIR spectrophotometer. The crystal has a transmittance window in the range 240–1250 nm. The optical second harmonic generation of this crystal has been tested with the Kurtz powder technique, using a Q-switched Nd–YAG laser (1064 nm, pulse width 8 ns). Green radiation (532 nm) was observed, which confirms the second-order NLO activity.
All H atoms were fixed geometrically and made to ride on their parent atoms. There are four chiral C atoms (C12, C15, C22 and C25) in the two dilactate moieties. The absolute configuration of the lactate anions could not be established unambiguously in the present study, because the structure contains only light atoms (Flack, 1983). However, the reported coordinates correspond, arbitrarily, to an R configuration.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.
Li+·C6H8BO6− | F(000) = 400 |
Mr = 193.88 | Dx = 1.448 Mg m−3 Dm = 1.40 Mg m−3 Dm measured by flotation in bromoform and glacial acetic acid |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7089 (16) Å | Cell parameters from 25 reflections |
b = 12.0650 (15) Å | θ = 20–30° |
c = 11.0782 (16) Å | µ = 0.13 mm−1 |
β = 97.472 (17)° | T = 293 K |
V = 889.1 (3) Å3 | Prisma, white |
Z = 4 | 0.23 × 0.15 × 0.10 mm |
Enraf-Nonius CAD-4 diffractometer | 1496 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ω–2θ scans | h = 0→7 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.972, Tmax = 0.988 | l = −13→13 |
1801 measured reflections | 2 standard reflections every 100 min |
1655 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.079 | Calculated w = 1/[σ2(Fo2) + (0.0558P)2 + 0.114P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1655 reflections | Δρmax = 0.18 e Å−3 |
258 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (4) |
Li+·C6H8BO6− | V = 889.1 (3) Å3 |
Mr = 193.88 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.7089 (16) Å | µ = 0.13 mm−1 |
b = 12.0650 (15) Å | T = 293 K |
c = 11.0782 (16) Å | 0.23 × 0.15 × 0.10 mm |
β = 97.472 (17)° |
Enraf-Nonius CAD-4 diffractometer | 1496 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.020 |
Tmin = 0.972, Tmax = 0.988 | 2 standard reflections every 100 min |
1801 measured reflections | intensity decay: none |
1655 independent reflections |
R[F2 > 2σ(F2)] = 0.028 | 1 restraint |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.18 e Å−3 |
1655 reflections | Δρmin = −0.19 e Å−3 |
258 parameters |
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 | −0.4341 (6) | 0.0733 (4) | 0.0959 (4) | 0.0325 (9) | |
B1 | 0.2839 (4) | −0.1164 (3) | 0.1516 (3) | 0.0297 (6) | |
O11 | 0.4128 (3) | −0.14247 (15) | 0.26104 (15) | 0.0316 (4) | |
O12 | 0.3199 (3) | −0.20686 (18) | 0.06477 (15) | 0.0357 (4) | |
O13 | 0.4807 (3) | −0.36792 (18) | 0.07402 (18) | 0.0458 (5) | |
O14 | 0.0641 (3) | −0.12026 (17) | 0.16668 (16) | 0.0362 (5) | |
O15 | 0.3107 (2) | −0.00737 (17) | 0.10269 (16) | 0.0331 (4) | |
O16 | −0.2081 (3) | −0.0230 (2) | 0.0997 (2) | 0.0501 (6) | |
C11 | 0.4271 (4) | −0.2840 (2) | 0.1223 (2) | 0.0320 (6) | |
C12 | 0.4737 (4) | −0.2559 (2) | 0.2562 (2) | 0.0334 (6) | |
H12 | 0.3896 | −0.3014 | 0.3026 | 0.040* | |
C13 | 0.6905 (5) | −0.2732 (3) | 0.3053 (3) | 0.0486 (8) | |
H13A | 0.7736 | −0.2291 | 0.2597 | 0.073* | |
H13B | 0.7243 | −0.3501 | 0.2982 | 0.073* | |
H13C | 0.7125 | −0.2516 | 0.3894 | 0.073* | |
C14 | −0.0292 (4) | −0.0386 (2) | 0.1048 (2) | 0.0342 (6) | |
C15 | 0.1189 (4) | 0.0293 (2) | 0.0436 (2) | 0.0369 (6) | |
H15 | 0.1068 | 0.0082 | −0.0425 | 0.044* | |
C16 | 0.0907 (5) | 0.1521 (3) | 0.0517 (3) | 0.0561 (9) | |
H16A | 0.1099 | 0.1744 | 0.1355 | 0.084* | |
H16B | −0.0428 | 0.1714 | 0.0158 | 0.084* | |
H16C | 0.1869 | 0.1892 | 0.0088 | 0.084* | |
Li2 | −0.4752 (6) | 0.4567 (4) | 0.5990 (4) | 0.0312 (9) | |
B2 | −0.2459 (4) | 0.1439 (3) | 0.3577 (3) | 0.0298 (6) | |
O21 | −0.2642 (3) | 0.03134 (15) | 0.39894 (16) | 0.0334 (4) | |
O22 | −0.0291 (3) | 0.15737 (16) | 0.34584 (17) | 0.0355 (4) | |
O23 | 0.2542 (3) | 0.06181 (18) | 0.39764 (18) | 0.0421 (5) | |
O24 | −0.2973 (3) | 0.22676 (16) | 0.45056 (15) | 0.0349 (4) | |
O25 | −0.3783 (3) | 0.17125 (15) | 0.24773 (14) | 0.0327 (4) | |
O26 | −0.5079 (3) | 0.36935 (19) | 0.45402 (17) | 0.0465 (5) | |
C21 | 0.0722 (4) | 0.0708 (2) | 0.3926 (2) | 0.0296 (6) | |
C22 | −0.0696 (4) | −0.0112 (2) | 0.4400 (2) | 0.0353 (6) | |
H22 | −0.0539 | −0.0839 | 0.4030 | 0.042* | |
C23 | −0.0298 (5) | −0.0215 (3) | 0.5771 (3) | 0.0544 (9) | |
H23A | −0.0554 | 0.0484 | 0.6137 | 0.082* | |
H23B | 0.1079 | −0.0423 | 0.6008 | 0.082* | |
H23C | −0.1165 | −0.0770 | 0.6040 | 0.082* | |
C24 | −0.4384 (4) | 0.2931 (2) | 0.4016 (2) | 0.0318 (6) | |
C25 | −0.5032 (4) | 0.2633 (2) | 0.2708 (2) | 0.0348 (6) | |
H25 | −0.6437 | 0.2390 | 0.2616 | 0.042* | |
C26 | −0.4840 (7) | 0.3598 (3) | 0.1873 (3) | 0.0669 (11) | |
H26A | −0.3458 | 0.3825 | 0.1938 | 0.100* | |
H26B | −0.5644 | 0.4204 | 0.2098 | 0.100* | |
H26C | −0.5295 | 0.3383 | 0.1049 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Li1 | 0.030 (2) | 0.031 (2) | 0.037 (2) | 0.0008 (17) | 0.0083 (17) | 0.0023 (18) |
B1 | 0.0263 (14) | 0.0320 (15) | 0.0315 (13) | −0.0004 (12) | 0.0061 (11) | −0.0013 (12) |
O11 | 0.0368 (10) | 0.0277 (9) | 0.0298 (8) | 0.0036 (8) | 0.0026 (7) | −0.0025 (8) |
O12 | 0.0370 (10) | 0.0415 (11) | 0.0286 (9) | 0.0014 (9) | 0.0039 (7) | −0.0042 (9) |
O13 | 0.0520 (13) | 0.0405 (12) | 0.0457 (11) | 0.0052 (10) | 0.0091 (9) | −0.0127 (10) |
O14 | 0.0286 (9) | 0.0386 (11) | 0.0430 (10) | −0.0006 (8) | 0.0108 (7) | 0.0039 (9) |
O15 | 0.0224 (8) | 0.0371 (10) | 0.0399 (9) | 0.0025 (7) | 0.0046 (7) | 0.0082 (8) |
O16 | 0.0254 (10) | 0.0550 (14) | 0.0700 (13) | 0.0051 (9) | 0.0070 (9) | −0.0088 (11) |
C11 | 0.0294 (13) | 0.0313 (14) | 0.0367 (12) | −0.0012 (11) | 0.0098 (11) | −0.0014 (12) |
C12 | 0.0393 (15) | 0.0291 (13) | 0.0328 (13) | 0.0009 (11) | 0.0082 (11) | 0.0002 (11) |
C13 | 0.0518 (19) | 0.0457 (17) | 0.0456 (15) | 0.0113 (15) | −0.0039 (13) | −0.0028 (14) |
C14 | 0.0247 (13) | 0.0403 (16) | 0.0376 (14) | 0.0041 (11) | 0.0041 (10) | −0.0088 (12) |
C15 | 0.0310 (13) | 0.0421 (16) | 0.0366 (13) | 0.0051 (12) | 0.0001 (10) | 0.0058 (12) |
C16 | 0.0425 (17) | 0.052 (2) | 0.074 (2) | 0.0076 (15) | 0.0091 (15) | 0.0143 (17) |
Li2 | 0.028 (2) | 0.030 (2) | 0.037 (2) | −0.0002 (17) | 0.0100 (17) | −0.0007 (17) |
B2 | 0.0266 (14) | 0.0316 (16) | 0.0324 (14) | −0.0042 (11) | 0.0082 (11) | −0.0019 (12) |
O21 | 0.0252 (9) | 0.0311 (10) | 0.0436 (10) | −0.0030 (7) | 0.0036 (7) | 0.0053 (8) |
O22 | 0.0289 (9) | 0.0328 (10) | 0.0465 (10) | −0.0010 (8) | 0.0107 (7) | 0.0052 (8) |
O23 | 0.0259 (10) | 0.0436 (12) | 0.0587 (12) | 0.0031 (8) | 0.0127 (8) | −0.0029 (10) |
O24 | 0.0349 (10) | 0.0380 (11) | 0.0316 (9) | 0.0061 (9) | 0.0030 (7) | −0.0052 (8) |
O25 | 0.0368 (10) | 0.0305 (9) | 0.0309 (9) | 0.0065 (8) | 0.0053 (7) | −0.0053 (8) |
O26 | 0.0548 (12) | 0.0463 (13) | 0.0395 (10) | 0.0139 (10) | 0.0109 (9) | −0.0126 (10) |
C21 | 0.0292 (14) | 0.0299 (13) | 0.0305 (12) | 0.0017 (11) | 0.0074 (10) | −0.0063 (11) |
C22 | 0.0267 (12) | 0.0296 (13) | 0.0489 (15) | −0.0004 (11) | 0.0027 (11) | 0.0000 (13) |
C23 | 0.0351 (15) | 0.076 (2) | 0.0506 (17) | −0.0070 (16) | 0.0001 (13) | 0.0212 (17) |
C24 | 0.0309 (13) | 0.0334 (13) | 0.0326 (12) | 0.0004 (11) | 0.0105 (10) | −0.0029 (12) |
C25 | 0.0366 (14) | 0.0357 (15) | 0.0321 (13) | 0.0085 (12) | 0.0047 (11) | −0.0028 (11) |
C26 | 0.120 (3) | 0.0429 (18) | 0.0413 (16) | 0.025 (2) | 0.0232 (18) | 0.0075 (15) |
Li1—O16 | 1.907 (5) | Li2—O26 | 1.910 (5) |
Li1—O15i | 1.979 (5) | Li2—O23vi | 1.948 (5) |
Li1—O13ii | 1.997 (4) | Li2—O11vi | 1.960 (5) |
Li1—O25 | 2.050 (5) | Li2—O21vii | 1.969 (5) |
B1—O11 | 1.430 (3) | B2—O21 | 1.443 (4) |
B1—O15 | 1.443 (4) | B2—O25 | 1.450 (3) |
B1—O12 | 1.495 (4) | B2—O22 | 1.486 (3) |
B1—O14 | 1.507 (3) | B2—O24 | 1.506 (3) |
O11—C12 | 1.431 (3) | O21—C22 | 1.421 (3) |
O11—Li2iii | 1.960 (5) | O21—Li2viii | 1.969 (5) |
O12—C11 | 1.292 (3) | O22—C21 | 1.315 (3) |
O13—C11 | 1.220 (3) | O23—C21 | 1.220 (3) |
O13—Li1iv | 1.997 (4) | O23—Li2iii | 1.948 (5) |
O14—C14 | 1.311 (3) | O24—C24 | 1.303 (3) |
O15—C15 | 1.436 (3) | O25—C25 | 1.434 (3) |
O15—Li1v | 1.979 (5) | O26—C24 | 1.213 (3) |
O16—C14 | 1.209 (3) | C21—C22 | 1.514 (4) |
C11—C12 | 1.514 (3) | C22—C23 | 1.512 (4) |
C12—C13 | 1.500 (4) | C24—C25 | 1.502 (3) |
C14—C15 | 1.514 (4) | C25—C26 | 1.503 (4) |
C15—C16 | 1.498 (5) | ||
O16—Li1—O15i | 112.9 (2) | O26—Li2—O23vi | 112.3 (2) |
O16—Li1—O13ii | 105.3 (2) | O26—Li2—O11vi | 108.5 (2) |
O15i—Li1—O13ii | 100.4 (2) | O23vi—Li2—O11vi | 107.4 (2) |
O16—Li1—O25 | 105.9 (2) | O26—Li2—O21vii | 104.9 (2) |
O15i—Li1—O25 | 108.6 (2) | O23vi—Li2—O21vii | 112.1 (2) |
O13ii—Li1—O25 | 123.9 (2) | O11vi—Li2—O21vii | 111.7 (2) |
O11—B1—O15 | 115.3 (2) | O21—B2—O25 | 114.4 (2) |
O11—B1—O12 | 104.7 (2) | O21—B2—O22 | 104.8 (2) |
O15—B1—O12 | 112.7 (2) | O25—B2—O22 | 113.6 (2) |
O11—B1—O14 | 113.0 (2) | O21—B2—O24 | 111.9 (2) |
O15—B1—O14 | 104.0 (2) | O25—B2—O24 | 104.7 (2) |
O12—B1—O14 | 106.9 (2) | O22—B2—O24 | 107.5 (2) |
B1—O11—C12 | 108.8 (2) | C22—O21—B2 | 109.2 (2) |
B1—O11—Li2iii | 125.5 (2) | C22—O21—Li2viii | 127.6 (2) |
C12—O11—Li2iii | 125.5 (2) | B2—O21—Li2viii | 123.1 (2) |
C11—O12—B1 | 109.58 (19) | C21—O22—B2 | 109.9 (2) |
C11—O13—Li1iv | 133.5 (2) | C21—O23—Li2iii | 144.5 (2) |
C14—O14—B1 | 109.0 (2) | C24—O24—B2 | 110.02 (19) |
C15—O15—B1 | 107.7 (2) | C25—O25—B2 | 109.57 (19) |
C15—O15—Li1v | 124.0 (2) | C25—O25—Li1 | 122.95 (19) |
B1—O15—Li1v | 127.8 (2) | B2—O25—Li1 | 125.8 (2) |
C14—O16—Li1 | 151.4 (3) | C24—O26—Li2 | 144.3 (2) |
O13—C11—O12 | 123.9 (2) | O23—C21—O22 | 123.5 (2) |
O13—C11—C12 | 125.5 (2) | O23—C21—C22 | 126.6 (2) |
O12—C11—C12 | 110.6 (2) | O22—C21—C22 | 109.9 (2) |
O11—C12—C13 | 112.8 (2) | O21—C22—C23 | 112.7 (2) |
O11—C12—C11 | 103.2 (2) | O21—C22—C21 | 104.2 (2) |
C13—C12—C11 | 113.0 (2) | C23—C22—C21 | 111.4 (2) |
O16—C14—O14 | 123.0 (3) | O26—C24—O24 | 124.8 (2) |
O16—C14—C15 | 126.8 (3) | O26—C24—C25 | 124.2 (2) |
O14—C14—C15 | 110.1 (2) | O24—C24—C25 | 111.0 (2) |
O15—C15—C16 | 112.9 (3) | O25—C25—C24 | 104.8 (2) |
O15—C15—C14 | 103.3 (2) | O25—C25—C26 | 113.0 (2) |
C16—C15—C14 | 114.4 (3) | C24—C25—C26 | 111.8 (3) |
O15—B1—O11—C12 | −141.5 (2) | O25—B2—O21—Li2viii | −42.9 (3) |
O12—B1—O11—C12 | −17.0 (3) | O22—B2—O21—Li2viii | −167.9 (2) |
O14—B1—O11—C12 | 99.1 (2) | O24—B2—O21—Li2viii | 75.9 (3) |
O15—B1—O11—Li2iii | 43.7 (3) | O21—B2—O22—C21 | −9.1 (3) |
O12—B1—O11—Li2iii | 168.2 (2) | O25—B2—O22—C21 | −134.6 (2) |
O14—B1—O11—Li2iii | −75.8 (3) | O24—B2—O22—C21 | 110.1 (2) |
O11—B1—O12—C11 | 9.8 (3) | O21—B2—O24—C24 | −124.6 (2) |
O15—B1—O12—C11 | 135.9 (2) | O25—B2—O24—C24 | −0.2 (3) |
O14—B1—O12—C11 | −110.5 (2) | O22—B2—O24—C24 | 120.9 (2) |
O11—B1—O14—C14 | 140.9 (2) | O21—B2—O25—C25 | 122.3 (2) |
O15—B1—O14—C14 | 15.1 (3) | O22—B2—O25—C25 | −117.5 (2) |
O12—B1—O14—C14 | −104.3 (2) | O24—B2—O25—C25 | −0.5 (3) |
O11—B1—O15—C15 | −148.2 (2) | O21—B2—O25—Li1 | −43.3 (3) |
O12—B1—O15—C15 | 91.6 (2) | O22—B2—O25—Li1 | 77.0 (3) |
O14—B1—O15—C15 | −23.8 (2) | O24—B2—O25—Li1 | −166.0 (2) |
O11—B1—O15—Li1v | 39.3 (3) | O16—Li1—O25—C25 | 172.9 (2) |
O12—B1—O15—Li1v | −80.9 (3) | O15i—Li1—O25—C25 | −65.7 (3) |
O14—B1—O15—Li1v | 163.6 (2) | O13ii—Li1—O25—C25 | 51.5 (3) |
O15i—Li1—O16—C14 | −173.8 (4) | O16—Li1—O25—B2 | −23.4 (3) |
O13ii—Li1—O16—C14 | 77.7 (5) | O15i—Li1—O25—B2 | 98.1 (3) |
O25—Li1—O16—C14 | −55.1 (6) | O13ii—Li1—O25—B2 | −144.8 (2) |
Li1iv—O13—C11—O12 | −1.6 (4) | O23vi—Li2—O26—C24 | 74.6 (5) |
Li1iv—O13—C11—C12 | 177.9 (3) | O11vi—Li2—O26—C24 | −43.9 (5) |
B1—O12—C11—O13 | −179.5 (2) | O21vii—Li2—O26—C24 | −163.4 (3) |
B1—O12—C11—C12 | 1.0 (3) | Li2iii—O23—C21—O22 | −152.2 (3) |
B1—O11—C12—C13 | 139.6 (2) | Li2iii—O23—C21—C22 | 29.3 (5) |
Li2iii—O11—C12—C13 | −45.6 (3) | B2—O22—C21—O23 | −178.1 (2) |
B1—O11—C12—C11 | 17.2 (2) | B2—O22—C21—C22 | 0.6 (3) |
Li2iii—O11—C12—C11 | −167.9 (2) | B2—O21—C22—C23 | 107.1 (3) |
O13—C11—C12—O11 | 169.2 (2) | Li2viii—O21—C22—C23 | −70.5 (3) |
O12—C11—C12—O11 | −11.3 (3) | B2—O21—C22—C21 | −13.8 (3) |
O13—C11—C12—C13 | 47.0 (4) | Li2viii—O21—C22—C21 | 168.5 (2) |
O12—C11—C12—C13 | −133.5 (3) | O23—C21—C22—O21 | −173.2 (2) |
Li1—O16—C14—O14 | 141.6 (4) | O22—C21—C22—O21 | 8.2 (3) |
Li1—O16—C14—C15 | −38.6 (6) | O23—C21—C22—C23 | 65.0 (3) |
B1—O14—C14—O16 | 178.9 (3) | O22—C21—C22—C23 | −113.7 (3) |
B1—O14—C14—C15 | −0.9 (3) | Li2—O26—C24—O24 | 10.0 (6) |
B1—O15—C15—C16 | 147.3 (3) | Li2—O26—C24—C25 | −169.4 (3) |
Li1v—O15—C15—C16 | −39.8 (4) | B2—O24—C24—O26 | −178.7 (3) |
B1—O15—C15—C14 | 23.2 (3) | B2—O24—C24—C25 | 0.8 (3) |
Li1v—O15—C15—C14 | −164.0 (2) | B2—O25—C25—C24 | 0.9 (3) |
O16—C14—C15—O15 | 166.4 (3) | Li1—O25—C25—C24 | 166.9 (2) |
O14—C14—C15—O15 | −13.8 (3) | B2—O25—C25—C26 | 122.9 (3) |
O16—C14—C15—C16 | 43.2 (4) | Li1—O25—C25—C26 | −71.1 (3) |
O14—C14—C15—C16 | −137.0 (3) | O26—C24—C25—O25 | 178.4 (3) |
O25—B2—O21—C22 | 139.4 (2) | O24—C24—C25—O25 | −1.1 (3) |
O22—B2—O21—C22 | 14.3 (2) | O26—C24—C25—C26 | 55.6 (4) |
O24—B2—O21—C22 | −101.9 (2) | O24—C24—C25—C26 | −123.9 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z; (iii) −x, y−1/2, −z+1; (iv) −x, y−1/2, −z; (v) x+1, y, z; (vi) −x, y+1/2, −z+1; (vii) −x−1, y+1/2, −z+1; (viii) −x−1, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | Li+·C6H8BO6− |
Mr | 193.88 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 6.7089 (16), 12.0650 (15), 11.0782 (16) |
β (°) | 97.472 (17) |
V (Å3) | 889.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.23 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.972, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1801, 1655, 1496 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.079, 0.99 |
No. of reflections | 1655 |
No. of parameters | 258 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.19 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97.
Li1—O16 | 1.907 (5) | Li2—O26 | 1.910 (5) |
Li1—O15i | 1.979 (5) | Li2—O23iii | 1.948 (5) |
Li1—O13ii | 1.997 (4) | Li2—O11iii | 1.960 (5) |
Li1—O25 | 2.050 (5) | Li2—O21iv | 1.969 (5) |
B1—O11 | 1.430 (3) | B2—O21 | 1.443 (4) |
B1—O15 | 1.443 (4) | B2—O25 | 1.450 (3) |
B1—O12 | 1.495 (4) | B2—O22 | 1.486 (3) |
B1—O14 | 1.507 (3) | B2—O24 | 1.506 (3) |
O16—Li1—O13ii | 105.3 (2) | O26—Li2—O23iii | 112.3 (2) |
O15i—Li1—O13ii | 100.4 (2) | O23iii—Li2—O11iii | 107.4 (2) |
O16—Li1—O25 | 105.9 (2) | O26—Li2—O21iv | 104.9 (2) |
O13ii—Li1—O25 | 123.9 (2) | O11iii—Li2—O21iv | 111.7 (2) |
O11—B1—O12 | 104.7 (2) | O21—B2—O22 | 104.8 (2) |
O15—B1—O12 | 112.7 (2) | O25—B2—O22 | 113.6 (2) |
O11—B1—O14 | 113.0 (2) | O21—B2—O24 | 111.9 (2) |
O15—B1—O14 | 104.0 (2) | O25—B2—O24 | 104.7 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) −x−1, y+1/2, −z+1. |
The present work is part of a study aimed at developing potential semiorganic NLO (non-linear optical) materials for optoelectronic applications, such as optical computing, optical data storage and optical communication. In a previous communication (Angeli Mary et al., 2002), the crystal structure of ammonium borodilactate, an NLO material, has been reported. The title compound, (I), crystallizes in the noncentrosymmetric space group P21 with Z = 4. The asymmetric unit consists of two borodilactate moieties linked through two Li+ cations. The Li—O distances range from 1.907 (5) to 2.049 (5) Å. In this structure, both lithium cations are tetracoordinated by four O atoms of the borodilactate anions. The Li+ cations and borodilactate anions form a ploymeric network. Similar arrangements have been reported in the literature (He et al., 2001). The lithium tetrahedra are slightly distorted, with the bond angles ranging from 105 to 112°. In both anions, boron forms two short and two long covalent bonds with O atoms. The bond angles around boron range from 104 to 115°, indicating a distorted tetrahedral environment. Similar bond lengths and deviations from tetrahedral values of bond angles around boron have been reported (Stibrany & Brant, 2001; Hill et al., 1997) in related boron derivatives. A short intermolecular C—H···O contact is observed between C16 and O12, with an H16B···O12 distance of 2.45 Å. The crystal structure is additionally stabilized by van der Waals interactions.