Structural chemistry of new lithium bis(oxalato)­borate solvates

Recently lithium bis(oxalato)borate, LiB(C₂O₄)₂, has been proposed as an alternative lithium salt for the electrolyte in rechargeable batteries that do not contain explosive perchlorate, reactive fluoride or toxic arsenic. This lithium salt crystallizes in the form of solvates from such solvents as water, acetonitrile, acetone, dimethoxyethane, 1,3-dioxolane and ethylene carbonate. Their crystal structures were determined in order to explore the crystal chemistry of this lithium salt. It was found that most of the solvents consist of a lithium bis(oxalato)borate dimer in which the ligand acts as both a chelating and a bridging agent. Lithium has octahedral coordination that typically includes one or, less commonly, two solvent molecules. An exception to this rule is the ethylene carbonate solvate where the lithium is tetrahedrally surrounded exclusively by the solvent and bis(oxalato)borate plays the role of counter-ion only. The ethylene carbonate solvates were also studied for LiPF₆ and LiAsF₆ salts and they have similar structures to the bis(oxalato)borate tetrahedral complexes.

Computing details

For all compounds, data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: Materials Studio (2001) for (I), (II), (III), (IV), (V); Materials Studio (2001), ATOMS (Dowty,1999) for (VI). For all compounds, software used to prepare material for publication: SHELXL97.

Figures

(I) Lithium bis(oxalato)borate hydrate

Crystal data

C4H2BLiO9	F(000) = 848
Mr = 211.81	Dx = 1.968 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3095 reflections
a = 16.075 (3) Å	θ = 2.5–30.5°
b = 15.880 (3) Å	µ = 0.20 mm^−1
c = 5.6008 (9) Å	T = 294 K
V = 1429.7 (4) Å^3	Plate, colorless
Z = 8	0.38 × 0.09 × 0.02 mm

Data collection

Three-circle diffractometer	1440 independent reflections
Radiation source: fine-focus sealed tube	1044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 8.33 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −19→20
Absorption correction: multi-scan XPREP (Sheldrick, 1997)	k = −19→19
Tmin = 0.873, Tmax = 0.996	l = −7→6
9124 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 2.51P], P = (max(Fo^2,0) + 2Fc^2)/3
1440 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. XPREP absorption correction for lamina with cut-off angle 8 °.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.4467 (0.0090) x + 2.8591 (0.0148) y + 2.8986 (0.0043) z = 9.1102 (0.0074)

* 0.0008 (0.0025) C3 * 0.0046 (0.0026) C4 * −0.0074 (0.0015) O5 * 0.0045 (0.0015) O6 * 0.0050 (0.0015) O7 * −0.0075 (0.0015) O8 − 0.0636 (0.0046) B1 Rms deviation of fitted atoms = 0.0054

4.7314 (0.0130) x + 9.7343 (0.0128) y − 4.1065 (0.0036) z = 3.0814 (0.0080)

Angle to previous plane (with approximate e.s.d.) = 88.69 (0.07)

* 0.0127 (0.0027) C1 * 0.0149 (0.0026) C2 * −0.0182 (0.0016) O1 * 0.0023 (0.0015) O2 * 0.0062 (0.0015) O3 * −0.0179 (0.0016) O4 − 0.0400 (0.0047) B1 Rms deviation of fitted atoms = 0.0134

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.6555 (3)	0.2483 (4)	0.8774 (12)	0.0306 (13)
B1	0.4103 (2)	0.4425 (2)	0.7811 (7)	0.0223 (9)
C1	0.50447 (19)	0.34586 (19)	0.6476 (6)	0.0222 (8)
C2	0.4211 (2)	0.33274 (19)	0.5199 (6)	0.0211 (7)
C3	0.36667 (18)	0.57436 (19)	0.8757 (6)	0.0209 (7)
C4	0.33841 (19)	0.51274 (19)	1.0689 (6)	0.0209 (7)
O7	0.36703 (13)	0.43764 (12)	1.0103 (4)	0.0241 (5)
O2	0.56587 (13)	0.30409 (13)	0.6219 (5)	0.0275 (6)
O6	0.35228 (13)	0.64869 (12)	0.8704 (4)	0.0261 (6)
O1	0.49551 (12)	0.40936 (13)	0.7953 (4)	0.0240 (6)
O4	0.40447 (14)	0.27839 (13)	0.3799 (4)	0.0305 (6)
O8	0.29696 (14)	0.53018 (14)	1.2398 (4)	0.0283 (6)
O5	0.40957 (14)	0.53234 (12)	0.7153 (4)	0.0247 (6)
O3	0.36915 (12)	0.39059 (13)	0.5993 (4)	0.0238 (5)
O1w	0.73558 (15)	0.20418 (16)	1.1266 (5)	0.0278 (6)
H1	0.786 (3)	0.224 (3)	1.135 (8)	0.072 (15)*
H2	0.740 (2)	0.153 (2)	1.161 (7)	0.049 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.035 (3)	0.034 (3)	0.023 (3)	0.001 (3)	0.003 (3)	0.001 (3)
B1	0.0203 (19)	0.0183 (18)	0.028 (2)	0.0007 (15)	−0.0013 (18)	−0.0028 (17)
C1	0.0241 (17)	0.0195 (17)	0.023 (2)	−0.0014 (14)	0.0053 (16)	0.0032 (15)
C2	0.0252 (18)	0.0187 (16)	0.0193 (19)	0.0003 (14)	0.0011 (15)	0.0057 (15)
C3	0.0185 (16)	0.0218 (16)	0.0223 (18)	−0.0013 (13)	−0.0072 (15)	−0.0003 (15)
C4	0.0201 (16)	0.0226 (17)	0.020 (2)	0.0028 (14)	−0.0033 (15)	−0.0033 (14)
O7	0.0299 (13)	0.0163 (11)	0.0261 (14)	0.0036 (9)	0.0055 (11)	0.0002 (10)
O2	0.0227 (12)	0.0257 (12)	0.0341 (15)	0.0073 (10)	0.0050 (12)	−0.0003 (11)
O6	0.0339 (13)	0.0143 (11)	0.0301 (14)	0.0023 (10)	−0.0008 (12)	0.0005 (10)
O1	0.0203 (11)	0.0242 (12)	0.0275 (15)	−0.0003 (10)	−0.0021 (10)	−0.0092 (10)
O4	0.0357 (13)	0.0276 (12)	0.0281 (14)	0.0022 (11)	−0.0037 (12)	−0.0085 (12)
O8	0.0317 (13)	0.0289 (12)	0.0242 (14)	0.0045 (11)	0.0067 (12)	−0.0026 (11)
O5	0.0322 (13)	0.0185 (11)	0.0234 (14)	0.0023 (10)	0.0068 (11)	−0.0004 (10)
O3	0.0206 (11)	0.0237 (11)	0.0270 (14)	0.0056 (10)	−0.0016 (11)	−0.0039 (10)
O1w	0.0242 (13)	0.0235 (14)	0.0358 (16)	0.0039 (11)	−0.0020 (12)	0.0053 (12)

Geometric parameters (Å, º)

Li1—O1w	2.024 (6)	C1—O2	1.198 (3)
Li1—O1w^i	2.050 (6)	C1—O1	1.312 (4)
Li1—O6^ii	2.108 (7)	C1—C2	1.534 (4)
Li1—O2^iii	2.154 (6)	C2—O4	1.196 (4)
Li1—O6^iv	2.165 (7)	C2—O3	1.319 (4)
Li1—O2	2.216 (7)	C3—O6	1.203 (3)
Li1—Li1^iii	2.801 (5)	C3—O5	1.314 (4)
Li1—Li1^i	2.801 (5)	C3—C4	1.528 (4)
B1—O7	1.463 (4)	C4—O8	1.199 (4)
B1—O3	1.468 (4)	C4—O7	1.320 (3)
B1—O1	1.469 (4)	O1w—H1	0.87 (4)
B1—O5	1.473 (4)	O1w—H2	0.84 (4)
O1w—Li1—O1w^i	101.5 (3)	O4—C2—O3	125.6 (3)
O1w—Li1—O6^ii	103.4 (3)	O4—C2—C1	126.8 (3)
O1w^i—Li1—O6^ii	82.1 (2)	O3—C2—C1	107.5 (3)
O1w—Li1—O2^iii	81.6 (2)	O6—C3—O5	125.6 (3)
O1w^i—Li1—O2^iii	176.2 (4)	O6—C3—C4	126.1 (3)
O6^ii—Li1—O2^iii	95.1 (2)	O5—C3—C4	108.3 (3)
O1w—Li1—O6^iv	81.3 (2)	O8—C4—O7	126.9 (3)
O1w^i—Li1—O6^iv	101.8 (3)	O8—C4—C3	125.6 (3)
O6^ii—Li1—O6^iv	173.3 (3)	O7—C4—C3	107.4 (3)
O2^iii—Li1—O6^iv	80.7 (2)	C4—O7—B1	109.6 (2)
O1w—Li1—O2	176.0 (3)	C1—O2—Li1^i	147.3 (3)
O1w^i—Li1—O2	79.5 (2)	C1—O2—Li1	132.8 (3)
O6^ii—Li1—O2	80.6 (2)	Li1^i—O2—Li1	79.72 (18)
O2^iii—Li1—O2	97.5 (2)	C3—O6—Li1^v	139.8 (3)
O6^iv—Li1—O2	94.7 (2)	C3—O6—Li1^iv	137.4 (3)
Li1^iii—Li1—Li1^i	177.8 (5)	Li1^v—O6—Li1^iv	81.91 (7)
O7—B1—O3	111.4 (3)	C1—O1—B1	110.1 (3)
O7—B1—O1	112.1 (3)	C3—O5—B1	109.0 (3)
O3—B1—O1	104.9 (3)	C2—O3—B1	109.9 (2)
O7—B1—O5	105.5 (3)	Li1—O1w—Li1^iii	86.9 (2)
O3—B1—O5	111.5 (3)	Li1—O1w—H1	120 (3)
O1—B1—O5	111.6 (3)	Li1^iii—O1w—H1	114 (3)
O2—C1—O1	126.3 (3)	Li1—O1w—H2	123 (3)
O2—C1—C2	126.1 (3)	Li1^iii—O1w—H2	105 (3)
O1—C1—C2	107.6 (3)	H1—O1w—H2	105 (4)
O2—C1—C2—O4	1.5 (6)	O6^iv—Li1—O2—Li1^i	140.7 (3)
O1—C1—C2—O4	−176.6 (3)	O5—C3—O6—Li1^v	23.2 (6)
O2—C1—C2—O3	179.0 (3)	C4—C3—O6—Li1^v	−156.8 (3)
O1—C1—C2—O3	1.0 (3)	O5—C3—O6—Li1^iv	−141.6 (3)
O6—C3—C4—O8	1.1 (5)	C4—C3—O6—Li1^iv	38.4 (5)
O5—C3—C4—O8	−178.9 (3)	O2—C1—O1—B1	−178.0 (3)
O6—C3—C4—O7	−179.7 (3)	C2—C1—O1—B1	0.1 (4)
O5—C3—C4—O7	0.3 (3)	O7—B1—O1—C1	120.1 (3)
O8—C4—O7—B1	176.4 (3)	O3—B1—O1—C1	−1.0 (4)
C3—C4—O7—B1	−2.7 (3)	O5—B1—O1—C1	−121.9 (3)
O3—B1—O7—C4	−117.2 (3)	O6—C3—O5—B1	−177.8 (3)
O1—B1—O7—C4	125.7 (3)	C4—C3—O5—B1	2.2 (3)
O5—B1—O7—C4	4.0 (3)	O7—B1—O5—C3	−3.8 (3)
O1—C1—O2—Li1^i	−128.8 (5)	O3—B1—O5—C3	117.3 (3)
C2—C1—O2—Li1^i	53.5 (6)	O1—B1—O5—C3	−125.8 (3)
O1—C1—O2—Li1	43.3 (5)	O4—C2—O3—B1	176.0 (3)
C2—C1—O2—Li1	−134.4 (4)	C1—C2—O3—B1	−1.6 (3)
O1w^i—Li1—O2—C1	−136.1 (3)	O7—B1—O3—C2	−119.9 (3)
O6^ii—Li1—O2—C1	140.3 (3)	O1—B1—O3—C2	1.6 (3)
O2^iii—Li1—O2—C1	46.3 (4)	O5—B1—O3—C2	122.6 (3)
O6^iv—Li1—O2—C1	−34.9 (4)	O1w^i—Li1—O1w—Li1^iii	139.1 (4)
O1w^i—Li1—O2—Li1^i	39.57 (14)	O6^ii—Li1—O1w—Li1^iii	−136.4 (3)
O6^ii—Li1—O2—Li1^i	−44.0 (2)	O2^iii—Li1—O1w—Li1^iii	−43.08 (13)
O2^iii—Li1—O2—Li1^i	−138.0 (3)	O6^iv—Li1—O1w—Li1^iii	38.7 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+2; (v) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H2···O3^vi	0.84 (4)	2.57 (4)	3.039 (3)	117 (3)
O1w—H2···O8^vii	0.84 (4)	2.11 (4)	2.910 (3)	159 (4)
O1w—H1···O4^viii	0.87 (4)	2.09 (4)	2.960 (3)	174 (4)

Symmetry codes: (vi) x+1/2, −y+1/2, −z+2; (vii) −x+1, y−1/2, −z+5/2; (viii) x+1/2, y, −z+3/2.

(II) Lithium bis(oxalato)borate acetonitrile

Crystal data

C12H6B2Li2N2O16·3(C2H3N)	F(000) = 1208
Mr = 592.85	Dx = 1.527 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2595 reflections
a = 7.6346 (8) Å	θ = 3.0–28.1°
b = 22.631 (2) Å	µ = 0.13 mm^−1
c = 14.9338 (16) Å	T = 110 K
β = 91.879 (2)°	Prism, colorless
V = 2578.9 (5) Å^3	0.48 × 0.36 × 0.30 mm
Z = 4

Data collection

Three-circle diffractometer	4542 independent reflections
Radiation source: fine-focus sealed tube	3039 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.6°
ω scans	h = −8→9
Absorption correction: multi-scan XPREP (Sheldrick, 1997)	k = −25→26
Tmin = 0.873, Tmax = 0.961	l = −17→17
14456 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0299P)^2], P = (max(Fo^2,0) + 2Fc^2)/3
4542 reflections	(Δ/σ)max = 0.001
393 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.5269 (6)	0.18159 (19)	0.7873 (3)	0.0334 (11)
Li2	0.4930 (6)	0.32406 (19)	0.7433 (3)	0.0354 (11)
B1	1.0175 (3)	0.32099 (12)	0.96650 (17)	0.0193 (6)
C1	1.0338 (3)	0.35140 (10)	1.11137 (15)	0.0190 (5)
C2	1.0179 (3)	0.28490 (10)	1.10787 (15)	0.0182 (5)
O1	1.03503 (18)	0.37135 (6)	1.02875 (9)	0.0201 (4)
O2	1.00830 (19)	0.26797 (7)	1.02395 (9)	0.0198 (4)
O3	1.04189 (19)	0.37985 (7)	1.17977 (10)	0.0230 (4)
O4	1.01478 (19)	0.25428 (7)	1.17424 (10)	0.0214 (4)
C3	0.5208 (3)	0.28880 (10)	0.92046 (15)	0.0189 (5)
C4	0.5060 (3)	0.35533 (10)	0.92363 (15)	0.0197 (5)
O5	0.53100 (18)	0.26836 (6)	1.00289 (9)	0.0195 (4)
O6	0.50574 (18)	0.37175 (6)	1.00851 (9)	0.0194 (4)
O7	0.52210 (19)	0.26085 (7)	0.85195 (10)	0.0214 (4)
O8	0.49627 (19)	0.38634 (7)	0.85840 (10)	0.0238 (4)
B2	0.5219 (3)	0.31891 (12)	1.06549 (17)	0.0195 (6)
C5	1.1072 (3)	0.32066 (10)	0.82119 (15)	0.0205 (5)
C6	0.9071 (3)	0.32700 (10)	0.82206 (15)	0.0192 (5)
O9	1.16448 (18)	0.31646 (6)	0.90618 (9)	0.0198 (4)
O10	0.86137 (18)	0.32661 (7)	0.90749 (9)	0.0207 (4)
O11	1.19590 (19)	0.31860 (7)	0.75675 (10)	0.0243 (4)
O12	0.80822 (19)	0.33108 (7)	0.75829 (10)	0.0248 (4)
C7	0.4322 (3)	0.31248 (10)	1.20998 (15)	0.0209 (5)
C8	0.6329 (3)	0.31866 (10)	1.20997 (15)	0.0207 (5)
O13	0.37498 (18)	0.31193 (7)	1.12504 (9)	0.0201 (4)
O14	0.67897 (18)	0.32111 (7)	1.12514 (9)	0.0204 (4)
O15	0.3435 (2)	0.30791 (7)	1.27424 (10)	0.0258 (4)
O16	0.73046 (19)	0.31975 (7)	1.27476 (10)	0.0245 (4)
N11	0.5279 (3)	0.13306 (9)	0.90490 (14)	0.0309 (5)
C11	0.5012 (3)	0.13301 (11)	0.97909 (17)	0.0271 (6)
C12	0.4634 (4)	0.13395 (12)	1.07412 (15)	0.0414 (7)
H11	0.4051	0.0971	1.0903	0.062*
H12	0.3866	0.1675	1.0865	0.062*
H13	0.5732	0.1379	1.1095	0.062*
N21	0.4772 (3)	0.37373 (9)	0.62578 (14)	0.0313 (5)
C21	0.4812 (3)	0.37551 (11)	0.54945 (17)	0.0271 (6)
C22	0.4861 (3)	0.37588 (12)	0.45255 (14)	0.0336 (7)
H21	0.6052	0.3669	0.4341	0.050*
H22	0.4513	0.4150	0.4300	0.050*
H23	0.4049	0.3460	0.4280	0.050*
N31	0.5786 (3)	0.05329 (10)	0.34944 (14)	0.0370 (6)
C31	0.6552 (3)	0.02783 (11)	0.40301 (18)	0.0289 (6)
C32	0.7526 (3)	−0.00375 (11)	0.47338 (17)	0.0397 (7)
H31N	0.8462	−0.0269	0.4469	0.060*
H32N	0.6733	−0.0303	0.5044	0.060*
H33N	0.8038	0.0247	0.5163	0.060*
N41	1.0028 (3)	0.06373 (11)	0.69941 (15)	0.0463 (7)
C41	0.9059 (3)	0.03063 (12)	0.72521 (17)	0.0297 (6)
C42	0.7835 (3)	−0.01151 (12)	0.75907 (18)	0.0477 (8)
H41	0.8289	−0.0516	0.7509	0.071*
H42	0.6707	−0.0074	0.7265	0.071*
H43	0.7676	−0.0042	0.8230	0.071*
N51	0.7552 (3)	0.49660 (10)	0.51037 (17)	0.0514 (7)
C51	0.7828 (4)	0.49651 (12)	0.4361 (2)	0.0392 (7)
C52	0.8194 (4)	0.49573 (14)	0.34188 (17)	0.0556 (9)
H51	0.7696	0.5311	0.3131	0.083*
H52	0.7669	0.4604	0.3141	0.083*
H53	0.9464	0.4951	0.3345	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.055 (3)	0.029 (3)	0.016 (2)	0.001 (2)	−0.003 (2)	0.0013 (19)
Li2	0.059 (3)	0.030 (3)	0.016 (2)	0.007 (2)	0.001 (2)	0.002 (2)
B1	0.0174 (14)	0.0250 (16)	0.0153 (14)	0.0002 (12)	−0.0024 (12)	0.0008 (12)
C1	0.0116 (12)	0.0305 (15)	0.0148 (14)	0.0010 (10)	−0.0002 (10)	0.0015 (11)
C2	0.0104 (12)	0.0286 (15)	0.0157 (14)	−0.0013 (10)	0.0002 (10)	0.0006 (11)
O1	0.0191 (9)	0.0257 (10)	0.0155 (9)	−0.0005 (7)	0.0007 (7)	0.0024 (7)
O2	0.0212 (9)	0.0266 (9)	0.0116 (9)	−0.0002 (7)	−0.0009 (7)	−0.0013 (7)
O3	0.0229 (9)	0.0295 (10)	0.0165 (9)	−0.0013 (7)	−0.0008 (7)	−0.0047 (8)
O4	0.0198 (9)	0.0291 (10)	0.0153 (9)	−0.0005 (7)	0.0004 (7)	0.0030 (8)
C3	0.0121 (12)	0.0297 (15)	0.0150 (14)	−0.0001 (10)	0.0014 (10)	0.0016 (12)
C4	0.0083 (12)	0.0304 (15)	0.0205 (14)	−0.0011 (10)	0.0022 (10)	−0.0011 (12)
O5	0.0219 (9)	0.0246 (9)	0.0120 (9)	−0.0001 (7)	−0.0012 (7)	0.0000 (7)
O6	0.0206 (8)	0.0239 (9)	0.0137 (9)	−0.0001 (7)	−0.0002 (7)	−0.0013 (7)
O7	0.0202 (9)	0.0296 (10)	0.0142 (9)	0.0002 (7)	−0.0005 (7)	−0.0033 (8)
O8	0.0215 (9)	0.0320 (10)	0.0179 (9)	0.0009 (7)	0.0010 (7)	0.0067 (8)
B2	0.0159 (14)	0.0253 (16)	0.0175 (15)	−0.0025 (12)	0.0010 (12)	0.0003 (13)
C5	0.0253 (14)	0.0217 (14)	0.0145 (13)	0.0007 (11)	−0.0012 (11)	0.0022 (11)
C6	0.0221 (13)	0.0215 (14)	0.0140 (13)	−0.0020 (10)	0.0018 (11)	−0.0003 (10)
O9	0.0177 (8)	0.0289 (9)	0.0128 (8)	0.0015 (7)	−0.0010 (7)	0.0018 (7)
O10	0.0169 (8)	0.0321 (10)	0.0129 (9)	0.0009 (7)	−0.0016 (7)	0.0013 (7)
O11	0.0247 (9)	0.0353 (10)	0.0129 (9)	0.0050 (8)	0.0031 (7)	0.0014 (8)
O12	0.0228 (9)	0.0348 (11)	0.0164 (9)	−0.0011 (7)	−0.0046 (8)	0.0016 (8)
C7	0.0230 (13)	0.0235 (14)	0.0162 (14)	−0.0018 (10)	−0.0003 (11)	−0.0030 (11)
C8	0.0219 (13)	0.0219 (13)	0.0183 (14)	0.0026 (10)	0.0011 (11)	−0.0022 (11)
O13	0.0178 (8)	0.0308 (10)	0.0117 (8)	−0.0022 (7)	−0.0014 (7)	−0.0008 (7)
O14	0.0171 (8)	0.0323 (10)	0.0118 (9)	0.0005 (7)	−0.0005 (7)	−0.0021 (7)
O15	0.0269 (10)	0.0368 (11)	0.0139 (9)	−0.0057 (8)	0.0024 (8)	−0.0012 (8)
O16	0.0245 (9)	0.0338 (10)	0.0151 (9)	0.0022 (7)	−0.0040 (8)	−0.0018 (8)
N11	0.0358 (13)	0.0349 (14)	0.0218 (13)	0.0016 (10)	−0.0021 (10)	0.0039 (10)
C11	0.0302 (15)	0.0292 (15)	0.0216 (15)	−0.0028 (11)	−0.0049 (12)	0.0000 (12)
C12	0.0510 (19)	0.0504 (19)	0.0229 (15)	−0.0161 (14)	0.0051 (14)	−0.0012 (13)
N21	0.0372 (13)	0.0343 (13)	0.0222 (13)	0.0023 (10)	−0.0011 (10)	0.0049 (10)
C21	0.0238 (14)	0.0273 (15)	0.0299 (16)	0.0002 (11)	−0.0024 (12)	0.0022 (12)
C22	0.0397 (16)	0.0453 (18)	0.0158 (14)	0.0012 (13)	−0.0005 (12)	−0.0005 (12)
N31	0.0403 (14)	0.0366 (14)	0.0339 (14)	0.0008 (11)	−0.0033 (12)	−0.0057 (11)
C31	0.0270 (14)	0.0281 (15)	0.0321 (16)	−0.0040 (12)	0.0072 (13)	−0.0095 (13)
C32	0.0317 (15)	0.0398 (17)	0.0474 (18)	0.0012 (13)	0.0006 (14)	0.0054 (14)
N41	0.0529 (17)	0.0400 (16)	0.0461 (16)	−0.0025 (12)	0.0035 (13)	0.0080 (12)
C41	0.0315 (15)	0.0309 (16)	0.0266 (15)	0.0042 (13)	−0.0011 (13)	−0.0007 (12)
C42	0.0393 (17)	0.055 (2)	0.0485 (19)	−0.0088 (15)	0.0021 (15)	0.0002 (16)
N51	0.0638 (18)	0.0436 (16)	0.0469 (16)	0.0055 (13)	0.0047 (14)	0.0003 (14)
C51	0.0372 (17)	0.0399 (18)	0.0402 (19)	−0.0008 (13)	−0.0030 (15)	0.0031 (15)
C52	0.050 (2)	0.081 (3)	0.0354 (19)	−0.0081 (17)	−0.0018 (16)	0.0045 (17)

Geometric parameters (Å, º)

Li1—O7	2.038 (4)	C5—C6	1.535 (3)
Li1—N11	2.072 (4)	C6—O12	1.199 (2)
Li1—O3^i	2.130 (4)	C6—O10	1.334 (2)
Li1—O4^i	2.225 (4)	C7—O15	1.197 (2)
Li1—O16^i	2.265 (5)	C7—O13	1.328 (2)
Li1—O15^ii	2.443 (5)	C7—C8	1.538 (3)
Li1—Li2	3.299 (6)	C8—O16	1.202 (2)
Li2—O4^i	2.061 (4)	C8—O14	1.327 (3)
Li2—N21	2.085 (4)	N11—C11	1.133 (3)
Li2—O7	2.169 (4)	C11—C12	1.458 (3)
Li2—O8	2.222 (4)	C12—H11	0.9800
Li2—O11^iii	2.287 (5)	C12—H12	0.9800
Li2—O12	2.415 (5)	C12—H13	0.9800
B1—O10	1.465 (3)	N21—C21	1.142 (3)
B1—O9	1.465 (3)	C21—C22	1.449 (3)
B1—O1	1.474 (3)	C22—H21	0.9800
B1—O2	1.478 (3)	C22—H22	0.9800
C1—O3	1.207 (2)	C22—H23	0.9800
C1—O1	1.314 (2)	N31—C31	1.133 (3)
C1—C2	1.511 (3)	C31—C32	1.455 (3)
C2—O4	1.210 (2)	C32—H31N	0.9800
C2—O2	1.310 (2)	C32—H32N	0.9800
C3—O7	1.203 (2)	C32—H33N	0.9800
C3—O5	1.315 (2)	N41—C41	1.129 (3)
C3—C4	1.511 (3)	C41—C42	1.439 (4)
C4—O8	1.201 (2)	C42—H41	0.9800
C4—O6	1.321 (3)	C42—H42	0.9800
O5—B2	1.480 (3)	C42—H43	0.9800
O6—B2	1.470 (3)	N51—C51	1.136 (3)
B2—O13	1.462 (3)	C51—C52	1.443 (4)
B2—O14	1.471 (3)	C52—H51	0.9800
C5—O11	1.195 (2)	C52—H52	0.9800
C5—O9	1.332 (2)	C52—H53	0.9800
O7—Li1—N11	93.68 (17)	O6—B2—O14	111.96 (19)
O7—Li1—O3^i	159.1 (2)	O13—B2—O5	110.69 (18)
N11—Li1—O3^i	107.1 (2)	O6—B2—O5	105.54 (18)
O7—Li1—O4^i	77.56 (15)	O14—B2—O5	110.74 (19)
N11—Li1—O4^i	171.0 (2)	O11—C5—O9	126.0 (2)
O3^i—Li1—O4^i	81.73 (14)	O11—C5—C6	126.9 (2)
O7—Li1—O16^i	90.99 (18)	O9—C5—C6	107.11 (19)
N11—Li1—O16^i	92.22 (18)	O12—C6—O10	125.6 (2)
O3^i—Li1—O16^i	90.42 (16)	O12—C6—C5	127.0 (2)
O4^i—Li1—O16^i	85.96 (15)	O10—C6—C5	107.43 (18)
O7—Li1—O15^ii	89.16 (17)	C5—O9—B1	110.30 (17)
N11—Li1—O15^ii	98.21 (17)	C6—O10—B1	110.02 (18)
O3^i—Li1—O15^ii	85.75 (16)	C5—O11—Li2^v	131.13 (17)
O4^i—Li1—O15^ii	83.85 (15)	C6—O12—Li2	131.91 (17)
O16^i—Li1—O15^ii	169.5 (2)	O15—C7—O13	126.0 (2)
O4^i—Li2—N21	92.61 (17)	O15—C7—C8	126.7 (2)
O4^i—Li2—O7	78.41 (16)	O13—C7—C8	107.30 (19)
N21—Li2—O7	170.8 (2)	O16—C8—O14	126.2 (2)
O4^i—Li2—O8	159.1 (2)	O16—C8—C7	126.3 (2)
N21—Li2—O8	107.94 (19)	O14—C8—C7	107.40 (19)
O7—Li2—O8	80.90 (15)	C7—O13—B2	110.17 (17)
O4^i—Li2—O11^iii	95.39 (18)	C8—O14—B2	109.89 (18)
N21—Li2—O11^iii	94.16 (17)	C7—O15—Li1^vi	130.00 (17)
O7—Li2—O11^iii	88.65 (17)	C8—O16—Li1^iv	131.09 (18)
O8—Li2—O11^iii	87.28 (16)	C11—N11—Li1	146.5 (2)
O4^i—Li2—O12	90.37 (17)	N11—C11—C12	178.7 (3)
N21—Li2—O12	94.15 (18)	C11—C12—H11	109.5
O7—Li2—O12	84.08 (15)	C11—C12—H12	109.5
O8—Li2—O12	84.32 (15)	H11—C12—H12	109.5
O11^iii—Li2—O12	169.7 (2)	C11—C12—H13	109.5
O10—B1—O9	105.12 (18)	H11—C12—H13	109.5
O10—B1—O1	111.56 (19)	H12—C12—H13	109.5
O9—B1—O1	112.74 (18)	C21—N21—Li2	149.0 (2)
O10—B1—O2	111.48 (19)	N21—C21—C22	178.3 (3)
O9—B1—O2	110.62 (18)	C21—C22—H21	109.5
O1—B1—O2	105.46 (18)	C21—C22—H22	109.5
O3—C1—O1	127.5 (2)	H21—C22—H22	109.5
O3—C1—C2	124.2 (2)	C21—C22—H23	109.5
O1—C1—C2	108.23 (19)	H21—C22—H23	109.5
O4—C2—O2	127.9 (2)	H22—C22—H23	109.5
O4—C2—C1	123.1 (2)	N31—C31—C32	178.6 (3)
O2—C2—C1	109.05 (19)	C31—C32—H31N	109.5
C1—O1—B1	108.86 (18)	C31—C32—H32N	109.5
C2—O2—B1	108.40 (18)	H31N—C32—H32N	109.5
C1—O3—Li1^iv	106.67 (19)	C31—C32—H33N	109.5
C2—O4—Li2^iv	155.05 (19)	H31N—C32—H33N	109.5
C2—O4—Li1^iv	104.26 (18)	H32N—C32—H33N	109.5
Li2^iv—O4—Li1^iv	100.57 (17)	N41—C41—C42	179.3 (3)
O7—C3—O5	127.5 (2)	C41—C42—H41	109.5
O7—C3—C4	123.6 (2)	C41—C42—H42	109.5
O5—C3—C4	108.9 (2)	H41—C42—H42	109.5
O8—C4—O6	127.7 (2)	C41—C42—H43	109.5
O8—C4—C3	124.0 (2)	H41—C42—H43	109.5
O6—C4—C3	108.24 (19)	H42—C42—H43	109.5
C3—O5—B2	108.46 (18)	N51—C51—C52	179.2 (3)
C4—O6—B2	108.89 (18)	C51—C52—H51	109.5
C3—O7—Li1	150.05 (19)	C51—C52—H52	109.5
C3—O7—Li2	106.61 (19)	H51—C52—H52	109.5
Li1—O7—Li2	103.24 (17)	C51—C52—H53	109.5
C4—O8—Li2	104.80 (19)	H51—C52—H53	109.5
O13—B2—O6	112.86 (19)	H52—C52—H53	109.5
O13—B2—O14	105.17 (18)
O3—C1—C2—O4	−1.2 (3)	O11^iii—Li2—O8—C4	86.71 (17)
O1—C1—C2—O4	179.41 (19)	O12—Li2—O8—C4	−87.26 (17)
O3—C1—C2—O2	178.6 (2)	C4—O6—B2—O13	−121.26 (19)
O1—C1—C2—O2	−0.7 (2)	C4—O6—B2—O14	120.3 (2)
O3—C1—O1—B1	−178.4 (2)	C4—O6—B2—O5	−0.3 (2)
C2—C1—O1—B1	0.9 (2)	C3—O5—B2—O13	122.15 (19)
O10—B1—O1—C1	120.4 (2)	C3—O5—B2—O6	−0.3 (2)
O9—B1—O1—C1	−121.62 (19)	C3—O5—B2—O14	−121.6 (2)
O2—B1—O1—C1	−0.8 (2)	O11—C5—C6—O12	−0.2 (4)
O4—C2—O2—B1	−180.0 (2)	O9—C5—C6—O12	−178.9 (2)
C1—C2—O2—B1	0.2 (2)	O11—C5—C6—O10	179.1 (2)
O10—B1—O2—C2	−120.9 (2)	O9—C5—C6—O10	0.5 (2)
O9—B1—O2—C2	122.52 (19)	O11—C5—O9—B1	179.9 (2)
O1—B1—O2—C2	0.3 (2)	C6—C5—O9—B1	−1.4 (2)
O1—C1—O3—Li1^iv	178.7 (2)	O10—B1—O9—C5	1.8 (2)
C2—C1—O3—Li1^iv	−0.5 (3)	O1—B1—O9—C5	−120.0 (2)
O2—C2—O4—Li2^iv	−3.6 (6)	O2—B1—O9—C5	122.24 (19)
C1—C2—O4—Li2^iv	176.2 (4)	O12—C6—O10—B1	180.0 (2)
O2—C2—O4—Li1^iv	−177.8 (2)	C5—C6—O10—B1	0.6 (2)
C1—C2—O4—Li1^iv	2.0 (3)	O9—B1—O10—C6	−1.4 (2)
O7—C3—C4—O8	−0.9 (3)	O1—B1—O10—C6	121.1 (2)
O5—C3—C4—O8	179.2 (2)	O2—B1—O10—C6	−121.3 (2)
O7—C3—C4—O6	179.1 (2)	O9—C5—O11—Li2^v	−12.8 (4)
O5—C3—C4—O6	−0.8 (2)	C6—C5—O11—Li2^v	168.9 (2)
O7—C3—C4—Li2	1.1 (2)	O10—C6—O12—Li2	−11.8 (4)
O5—C3—C4—Li2	−178.74 (19)	C5—C6—O12—Li2	167.5 (2)
O7—C3—O5—B2	−179.2 (2)	O4^i—Li2—O12—C6	−111.1 (2)
C4—C3—O5—B2	0.6 (2)	N21—Li2—O12—C6	156.2 (2)
O8—C4—O6—B2	−179.4 (2)	O7—Li2—O12—C6	−32.8 (3)
C3—C4—O6—B2	0.6 (2)	O8—Li2—O12—C6	48.6 (3)
O5—C3—O7—Li1	3.5 (5)	O11^iii—Li2—O12—C6	12.8 (13)
C4—C3—O7—Li1	−176.4 (3)	O15—C7—C8—O16	0.1 (4)
O5—C3—O7—Li2	178.4 (2)	O13—C7—C8—O16	−178.7 (2)
C4—C3—O7—Li2	−1.5 (3)	O15—C7—C8—O14	178.6 (2)
N11—Li1—O7—C3	0.7 (5)	O13—C7—C8—O14	−0.2 (2)
O3^i—Li1—O7—C3	−173.3 (5)	O15—C7—O13—B2	179.7 (2)
O4^i—Li1—O7—C3	178.6 (3)	C8—C7—O13—B2	−1.5 (2)
O16^i—Li1—O7—C3	93.0 (4)	O6—B2—O13—C7	−119.8 (2)
O15^ii—Li1—O7—C3	−97.5 (4)	O14—B2—O13—C7	2.5 (2)
N11—Li1—O7—Li2	−174.36 (17)	O5—B2—O13—C7	122.18 (19)
O3^i—Li1—O7—Li2	11.7 (7)	O16—C8—O14—B2	−179.7 (2)
O4^i—Li1—O7—Li2	3.58 (19)	C7—C8—O14—B2	1.8 (2)
O16^i—Li1—O7—Li2	−82.07 (18)	O13—B2—O14—C8	−2.6 (2)
O15^ii—Li1—O7—Li2	87.47 (17)	O6—B2—O14—C8	120.3 (2)
O4^i—Li2—O7—C3	178.74 (16)	O5—B2—O14—C8	−122.3 (2)
O8—Li2—O7—C3	2.0 (2)	O13—C7—O15—Li1^vi	−15.9 (4)
O11^iii—Li2—O7—C3	−85.48 (18)	C8—C7—O15—Li1^vi	165.6 (2)
O12—Li2—O7—C3	87.15 (17)	O14—C8—O16—Li1^iv	−5.9 (4)
O4^i—Li2—O7—Li1	−3.8 (2)	C7—C8—O16—Li1^iv	172.4 (2)
O8—Li2—O7—Li1	179.39 (16)	O7—Li1—N11—C11	18.4 (5)
O11^iii—Li2—O7—Li1	91.93 (18)	O3^i—Li1—N11—C11	−163.9 (4)
O12—Li2—O7—Li1	−95.44 (17)	O16^i—Li1—N11—C11	−72.7 (4)
O6—C4—O8—Li2	−177.4 (2)	O15^ii—Li1—N11—C11	108.1 (4)
C3—C4—O8—Li2	2.5 (3)	O4^i—Li2—N21—C21	−4.1 (5)
O4^i—Li2—O8—C4	−11.3 (7)	O8—Li2—N21—C21	171.9 (4)
N21—Li2—O8—C4	−179.8 (2)	O11^iii—Li2—N21—C21	−99.7 (4)
O7—Li2—O8—C4	−2.36 (19)	O12—Li2—N21—C21	86.5 (5)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x−1, y, z; (iv) x+1/2, −y+1/2, z+1/2; (v) x+1, y, z; (vi) x−1/2, −y+1/2, z+1/2.

(III) Lithium bis(oxalato)borate acetone

Crystal data

C7H6BLiO9·0.33(C3H6O)	F(000) = 555
Mr = 271.21	Dx = 1.531 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 2604 reflections
a = 16.3987 (16) Å	θ = 2.6–31.1°
b = 7.6308 (7) Å	µ = 0.14 mm^−1
c = 10.9904 (11) Å	T = 110 K
β = 121.201 (2)°	Needle, colorless
V = 1176.4 (2) Å^3	0.50 × 0.16 × 0.11 mm
Z = 4

Data collection

Three-circle diffractometer	1437 independent reflections
Radiation source: fine-focus sealed tube	1116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −20→19
Absorption correction: multi-scan XPREP (Sheldrick, 1997)	k = −9→9
Tmin = 0.914, Tmax = 0.985	l = −14→14
4923 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 0.94P], P = (max(Fo^2,0) + 2Fc^2)/3
1437 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.40 e Å^−3
38 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Li1	0.4553 (3)	0.5000	0.3184 (5)	0.0353 (12)
B1	0.1970 (2)	0.5000	0.4670 (3)	0.0199 (6)
C1	0.04544 (12)	0.3988 (3)	0.38430 (18)	0.0213 (4)
O1	0.13486 (8)	0.34723 (16)	0.43429 (13)	0.0229 (3)
O2	−0.02221 (9)	0.30551 (19)	0.34642 (14)	0.0284 (4)
C2	0.33668 (17)	0.5000	0.4698 (3)	0.0175 (5)
O3	0.24415 (12)	0.5000	0.38254 (17)	0.0184 (4)
O4	0.39806 (12)	0.5000	0.44008 (19)	0.0211 (4)
C3	0.35768 (18)	0.5000	0.6224 (3)	0.0205 (6)
O5	0.27568 (12)	0.5000	0.61686 (18)	0.0236 (5)
O6	0.43586 (13)	0.5000	0.72712 (19)	0.0255 (5)
O7	0.34606 (14)	0.5000	0.1240 (2)	0.0383 (6)
C4	0.3209 (3)	0.4491 (5)	0.0033 (4)	0.0378 (12)	0.50
C5	0.2275 (3)	0.5302 (12)	−0.1198 (5)	0.059 (2)	0.50
H5A	0.1813	0.5442	−0.0893	0.088*	0.50
H5B	0.2008	0.4527	−0.2028	0.088*	0.50
H5C	0.2414	0.6450	−0.1449	0.088*	0.50
C6	0.3752 (4)	0.3209 (7)	−0.0274 (5)	0.0482 (13)	0.50
H6A	0.4065	0.3811	−0.0710	0.072*	0.50
H6B	0.3317	0.2315	−0.0929	0.072*	0.50
H6C	0.4235	0.2650	0.0614	0.072*	0.50
O8	0.4733 (4)	0.0000	−0.1384 (6)	0.0348 (18)	0.334 (4)
C7	0.4232 (6)	0.0000	−0.0894 (7)	0.053 (3)	0.334 (4)
C8	0.3905 (7)	0.1639 (13)	−0.0577 (9)	0.069 (3)	0.334 (4)
H8A	0.3921	0.2587	−0.1166	0.104*	0.334 (4)
H8B	0.4325	0.1934	0.0431	0.104*	0.334 (4)
H8C	0.3252	0.1488	−0.0783	0.104*	0.334 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.016 (2)	0.065 (4)	0.025 (2)	0.000	0.0100 (19)	0.000
B1	0.0147 (15)	0.0199 (14)	0.0261 (14)	0.000	0.0114 (12)	0.000
C1	0.0138 (9)	0.0270 (10)	0.0235 (9)	0.0005 (7)	0.0099 (7)	0.0030 (7)
O1	0.0119 (7)	0.0209 (7)	0.0356 (7)	0.0007 (5)	0.0121 (5)	0.0044 (6)
O2	0.0145 (7)	0.0313 (8)	0.0370 (8)	−0.0039 (6)	0.0117 (6)	0.0061 (6)
C2	0.0137 (13)	0.0116 (11)	0.0260 (12)	0.000	0.0094 (10)	0.000
O3	0.0118 (9)	0.0206 (9)	0.0230 (9)	0.000	0.0091 (7)	0.000
O4	0.0172 (10)	0.0172 (9)	0.0351 (10)	0.000	0.0179 (8)	0.000
C3	0.0146 (13)	0.0198 (13)	0.0275 (13)	0.000	0.0111 (11)	0.000
O5	0.0140 (10)	0.0338 (11)	0.0254 (9)	0.000	0.0119 (8)	0.000
O6	0.0139 (10)	0.0321 (11)	0.0253 (9)	0.000	0.0064 (8)	0.000
O7	0.0217 (11)	0.0629 (16)	0.0254 (11)	0.000	0.0087 (9)	0.000
C4	0.029 (2)	0.051 (3)	0.0341 (19)	−0.0023 (17)	0.0171 (16)	0.0042 (16)
C5	0.049 (2)	0.075 (5)	0.041 (2)	0.022 (3)	0.0151 (18)	−0.002 (3)
C6	0.054 (3)	0.052 (3)	0.039 (2)	−0.002 (2)	0.025 (2)	0.001 (2)
O8	0.035 (4)	0.039 (4)	0.029 (3)	0.000	0.015 (3)	0.000
C7	0.077 (7)	0.046 (6)	0.043 (5)	0.000	0.036 (5)	0.000
C8	0.089 (6)	0.057 (5)	0.069 (5)	0.002 (5)	0.047 (5)	−0.006 (4)

Geometric parameters (Å, º)

Li1—O7	1.951 (5)	C3—O6	1.200 (3)
Li1—O4	1.993 (5)	C3—O5	1.314 (3)
Li1—O6^i	2.087 (5)	O7—C4	1.230 (4)
Li1—O2^ii	2.3554 (17)	C4—C6	1.475 (7)
Li1—O2^iii	2.3554 (17)	C4—C5	1.553 (7)
Li1—O4^i	2.493 (5)	C5—H5A	0.9800
Li1—Li1^i	3.468 (9)	C5—H5B	0.9800
B1—O1	1.465 (2)	C5—H5C	0.9800
B1—O1^iv	1.465 (2)	C6—H6A	0.9800
B1—O5	1.475 (3)	C6—H6B	0.9800
B1—O3	1.485 (3)	C6—H6C	0.9800
C1—O2	1.197 (2)	O8—C7	1.193 (13)
C1—O1	1.331 (2)	C7—C8	1.472 (11)
C1—C1^iv	1.544 (4)	C7—C8^v	1.472 (11)
C2—O4	1.208 (3)	C8—H8A	0.9800
C2—O3	1.309 (3)	C8—H8B	0.9800
C2—C3	1.527 (4)	C8—H8C	0.9800
O7—Li1—O4	104.5 (2)	Li1—O4—Li1^i	100.66 (17)
O7—Li1—O6^i	98.8 (2)	O6—C3—O5	127.1 (2)
O4—Li1—O6^i	156.8 (3)	O6—C3—C2	125.1 (2)
O7—Li1—O2^ii	97.81 (12)	O5—C3—C2	107.8 (2)
O4—Li1—O2^ii	90.47 (12)	C3—O5—B1	109.54 (19)
O6^i—Li1—O2^ii	86.35 (12)	C3—O6—Li1^i	113.0 (2)
O7—Li1—O2^iii	97.81 (12)	C4—O7—Li1	141.7 (3)
O4—Li1—O2^iii	90.47 (12)	O7—C4—C6	123.4 (4)
O6^i—Li1—O2^iii	86.35 (12)	O7—C4—C5	116.2 (4)
O2^ii—Li1—O2^iii	163.6 (2)	C6—C4—C5	120.3 (4)
O7—Li1—O4^i	176.2 (3)	C4—C5—H5A	109.5
O4—Li1—O4^i	79.34 (17)	C4—C5—H5B	109.5
O6^i—Li1—O4^i	77.45 (16)	H5A—C5—H5B	109.5
O2^ii—Li1—O4^i	82.04 (12)	C4—C5—H5C	109.5
O2^iii—Li1—O4^i	82.04 (12)	H5A—C5—H5C	109.5
O1—B1—O1^iv	105.5 (2)	H5B—C5—H5C	109.5
O1—B1—O5	111.68 (14)	C4—C6—H6A	109.5
O1^iv—B1—O5	111.68 (14)	C4—C6—H6B	109.5
O1—B1—O3	111.55 (14)	H6A—C6—H6B	109.5
O1^iv—B1—O3	111.55 (14)	C4—C6—H6C	109.5
O5—B1—O3	105.1 (2)	H6A—C6—H6C	109.5
O2—C1—O1	126.29 (18)	H6B—C6—H6C	109.5
O2—C1—C1^iv	126.51 (11)	O8—C7—C8	121.8 (6)
O1—C1—C1^iv	107.20 (10)	O8—C7—C8^v	121.8 (6)
C1—O1—B1	110.06 (15)	C8—C7—C8^v	116.4 (11)
C1—O2—Li1^vi	133.49 (17)	C7—C8—H8A	109.5
O4—C2—O3	127.8 (2)	C7—C8—H8B	109.5
O4—C2—C3	123.5 (2)	H8A—C8—H8B	109.5
O3—C2—C3	108.7 (2)	C7—C8—H8C	109.5
C2—O3—B1	108.87 (19)	H8A—C8—H8C	109.5
C2—O4—Li1	158.3 (2)	H8B—C8—H8C	109.5
C2—O4—Li1^i	101.00 (19)
O2—C1—O1—B1	179.07 (19)	O2^ii—Li1—O4—Li1^i	−81.81 (12)
C1^iv—C1—O1—B1	−0.88 (16)	O2^iii—Li1—O4—Li1^i	81.81 (12)
O1^iv—B1—O1—C1	1.4 (3)	O4^i—Li1—O4—Li1^i	0.000 (1)
O5—B1—O1—C1	122.88 (17)	C3^i—Li1—O4—Li1^i	0.000 (1)
O3—B1—O1—C1	−119.87 (17)	O4—C2—C3—O6	0.0
O1—C1—O2—Li1^vi	−5.6 (3)	O3—C2—C3—O6	180.0
C1^iv—C1—O2—Li1^vi	174.36 (17)	O4—C2—C3—O5	180.0
O4—C2—O3—B1	180.0	O3—C2—C3—O5	0.0
C3—C2—O3—B1	0.0	O4—C2—C3—Li1^i	0.0
O1—B1—O3—C2	−121.17 (15)	O3—C2—C3—Li1^i	180.0
O1^iv—B1—O3—C2	121.17 (15)	O6—C3—O5—B1	180.000 (1)
O5—B1—O3—C2	0.0	C2—C3—O5—B1	0.0
O3—C2—O4—Li1	0.000 (2)	O1—B1—O5—C3	121.09 (15)
C3—C2—O4—Li1	180.000 (1)	O1^iv—B1—O5—C3	−121.09 (15)
O3—C2—O4—Li1^i	180.0	O3—B1—O5—C3	0.0
C3—C2—O4—Li1^i	0.0	O5—C3—O6—Li1^i	180.0
O7—Li1—O4—C2	0.000 (1)	C2—C3—O6—Li1^i	0.0
O6^i—Li1—O4—C2	180.000 (2)	O4—Li1—O7—C4	−149.3 (3)
O2^ii—Li1—O4—C2	98.19 (12)	O6^i—Li1—O7—C4	30.7 (3)
O2^iii—Li1—O4—C2	−98.19 (12)	O2^ii—Li1—O7—C4	118.1 (2)
O4^i—Li1—O4—C2	180.000 (1)	O2^iii—Li1—O7—C4	−56.8 (3)
C3^i—Li1—O4—C2	180.000 (1)	Li1—O7—C4—C6	13.2 (4)
O7—Li1—O4—Li1^i	180.0	Li1—O7—C4—C5	−165.7 (4)
O6^i—Li1—O4—Li1^i	0.000 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, y+1/2, z; (iii) x+1/2, −y+1/2, z; (iv) x, −y+1, z; (v) x, −y, z; (vi) x−1/2, y−1/2, z.

(IV) Lithium bis(oxalato)borate dimethoxyethylene

Crystal data

C8H10BLiO10	Z = 2
Mr = 283.91	F(000) = 292
Triclinic, P1	Dx = 1.545 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6690 (7) Å	Cell parameters from 2770 reflections
b = 8.8519 (7) Å	θ = 2.7–31.1°
c = 9.3328 (8) Å	µ = 0.14 mm^−1
α = 114.159 (2)°	T = 110 K
β = 94.764 (2)°	Prism, colorless
γ = 106.412 (2)°	0.51 × 0.36 × 0.26 mm
V = 610.45 (9) Å^3

Data collection

Three-circle diffractometer	3509 independent reflections
Radiation source: fine-focus sealed tube	3051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.5°
ω scans	h = −12→12
Absorption correction: multi-scan XPREP (Sheldrick, 1997)	k = −12→12
Tmin = 0.841, Tmax = 0.964	l = −13→13
7526 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0661P)^2], P = (max(Fo^2,0) + 2Fc^2)/3
3509 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.9908 (2)	0.4673 (2)	0.66495 (19)	0.0229 (3)
B1	0.40189 (12)	0.22735 (12)	0.35914 (12)	0.01674 (19)
C1	0.64402 (10)	0.21424 (11)	0.46098 (10)	0.01740 (17)
C2	0.52292 (10)	0.02575 (11)	0.34779 (10)	0.01819 (17)
O1	0.57021 (7)	0.32714 (8)	0.46203 (8)	0.01825 (14)
O2	0.78055 (8)	0.25042 (9)	0.53412 (8)	0.02201 (15)
O3	0.38654 (7)	0.04142 (8)	0.28830 (8)	0.01931 (14)
O4	0.54796 (9)	−0.10880 (9)	0.31981 (9)	0.02514 (16)
C3	0.24817 (10)	0.34638 (12)	0.25628 (10)	0.01801 (17)
C4	0.19216 (10)	0.33526 (11)	0.40392 (10)	0.01550 (16)
O5	0.37064 (8)	0.28348 (9)	0.23412 (8)	0.01965 (14)
O6	0.18617 (8)	0.40082 (10)	0.17704 (8)	0.02549 (16)
O7	0.27791 (7)	0.26145 (8)	0.45761 (7)	0.01679 (14)
O8	0.08443 (7)	0.38691 (8)	0.45699 (8)	0.01888 (14)
C5	1.20340 (14)	0.86761 (13)	0.88249 (13)	0.0280 (2)
H51	1.1326 (16)	0.8849 (17)	0.9588 (16)	0.032 (3)*
H52	1.1604 (16)	0.8882 (17)	0.7965 (16)	0.030 (3)*
H53	1.3164 (17)	0.9499 (18)	0.9335 (16)	0.031 (3)*
O9	1.20013 (8)	0.69028 (8)	0.81689 (7)	0.02184 (15)
C6	1.26904 (12)	0.65323 (13)	0.93876 (11)	0.0250 (2)
H61	1.2022 (15)	0.6723 (16)	1.0206 (15)	0.029 (3)*
H62	1.3850 (17)	0.7268 (18)	0.9867 (16)	0.035 (3)*
C7	1.25813 (11)	0.46405 (13)	0.85966 (11)	0.02255 (19)
H71	1.3247 (14)	0.4436 (15)	0.7803 (14)	0.019 (3)*
H72	1.2981 (15)	0.4322 (16)	0.9414 (15)	0.024 (3)*
O10	1.08761 (8)	0.35962 (9)	0.78452 (8)	0.02237 (15)
C8	1.05617 (14)	0.17565 (13)	0.73139 (14)	0.0273 (2)
H81	1.0806 (17)	0.1551 (18)	0.8241 (17)	0.037 (3)*
H82	1.1243 (16)	0.1343 (18)	0.6584 (17)	0.034 (3)*
H83	0.9404 (18)	0.1152 (19)	0.6741 (17)	0.038 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.0208 (7)	0.0228 (8)	0.0251 (8)	0.0083 (6)	0.0034 (6)	0.0107 (7)
B1	0.0144 (4)	0.0164 (4)	0.0178 (4)	0.0060 (3)	0.0034 (3)	0.0059 (4)
C1	0.0154 (4)	0.0183 (4)	0.0197 (4)	0.0070 (3)	0.0054 (3)	0.0087 (3)
C2	0.0162 (4)	0.0188 (4)	0.0190 (4)	0.0074 (3)	0.0043 (3)	0.0071 (3)
O1	0.0139 (3)	0.0160 (3)	0.0228 (3)	0.0057 (2)	0.0020 (2)	0.0070 (2)
O2	0.0142 (3)	0.0243 (3)	0.0268 (3)	0.0061 (3)	0.0022 (2)	0.0118 (3)
O3	0.0157 (3)	0.0159 (3)	0.0213 (3)	0.0060 (2)	0.0007 (2)	0.0040 (2)
O4	0.0255 (3)	0.0193 (3)	0.0298 (4)	0.0111 (3)	0.0048 (3)	0.0085 (3)
C3	0.0159 (4)	0.0190 (4)	0.0171 (4)	0.0055 (3)	0.0029 (3)	0.0069 (3)
C4	0.0132 (4)	0.0142 (4)	0.0157 (4)	0.0031 (3)	0.0009 (3)	0.0052 (3)
O5	0.0191 (3)	0.0243 (3)	0.0188 (3)	0.0108 (3)	0.0068 (2)	0.0103 (3)
O6	0.0258 (4)	0.0321 (4)	0.0244 (3)	0.0130 (3)	0.0041 (3)	0.0167 (3)
O7	0.0152 (3)	0.0184 (3)	0.0187 (3)	0.0077 (2)	0.0048 (2)	0.0088 (2)
O8	0.0147 (3)	0.0199 (3)	0.0212 (3)	0.0075 (2)	0.0047 (2)	0.0075 (2)
C5	0.0311 (5)	0.0184 (5)	0.0265 (5)	0.0051 (4)	0.0038 (4)	0.0054 (4)
O9	0.0236 (3)	0.0193 (3)	0.0177 (3)	0.0062 (3)	0.0002 (2)	0.0053 (3)
C6	0.0240 (5)	0.0284 (5)	0.0165 (4)	0.0062 (4)	−0.0006 (3)	0.0074 (4)
C7	0.0189 (4)	0.0286 (5)	0.0201 (4)	0.0082 (4)	0.0008 (3)	0.0117 (4)
O10	0.0191 (3)	0.0217 (3)	0.0262 (3)	0.0064 (3)	0.0013 (3)	0.0120 (3)
C8	0.0293 (5)	0.0232 (5)	0.0333 (5)	0.0104 (4)	0.0065 (4)	0.0159 (4)

Geometric parameters (Å, º)

Li1—O10	2.0059 (17)	C3—C4	1.5294 (12)
Li1—O2	2.0574 (17)	C4—O8	1.2081 (10)
Li1—O8^i	2.0949 (17)	C4—O7	1.3081 (10)
Li1—O9	2.1112 (17)	C5—O9	1.4231 (11)
Li1—O8^ii	2.2229 (17)	C5—H51	0.972 (13)
Li1—O6^ii	2.4232 (18)	C5—H52	0.962 (13)
Li1—Li1^iii	3.366 (3)	C5—H53	0.976 (14)
B1—O3	1.4611 (11)	O9—C6	1.4356 (11)
B1—O1	1.4751 (11)	C6—C7	1.4984 (14)
B1—O5	1.4765 (11)	C6—H61	0.986 (13)
B1—O7	1.4870 (11)	C6—H62	0.976 (14)
C1—O2	1.2009 (10)	C7—O10	1.4340 (11)
C1—O1	1.3277 (10)	C7—H71	0.967 (12)
C1—C2	1.5444 (12)	C7—H72	0.984 (12)
C2—O4	1.1978 (10)	O10—C8	1.4276 (12)
C2—O3	1.3311 (10)	C8—H81	0.973 (14)
C3—O6	1.2001 (11)	C8—H82	0.965 (14)
C3—O5	1.3252 (10)	C8—H83	0.976 (15)
O10—Li1—O2	96.17 (7)	O8—C4—O7	127.70 (8)
O10—Li1—O8^i	100.87 (7)	O8—C4—C3	123.38 (8)
O2—Li1—O8^i	86.83 (7)	O7—C4—C3	108.92 (7)
O10—Li1—O9	81.46 (6)	C3—O5—B1	109.10 (7)
O2—Li1—O9	175.18 (9)	C3—O6—Li1^ii	104.28 (7)
O8^i—Li1—O9	97.73 (7)	C4—O7—B1	108.76 (6)
O10—Li1—O8^ii	172.64 (9)	C4—O8—Li1^iv	142.70 (7)
O2—Li1—O8^ii	90.94 (6)	C4—O8—Li1^ii	110.73 (7)
O8^i—Li1—O8^ii	77.61 (6)	Li1^iv—O8—Li1^ii	102.39 (6)
O9—Li1—O8^ii	91.57 (7)	O9—C5—H51	109.6 (7)
O10—Li1—O6^ii	106.28 (7)	O9—C5—H52	108.7 (8)
O2—Li1—O6^ii	86.16 (6)	H51—C5—H52	108.1 (10)
O8^i—Li1—O6^ii	152.52 (8)	O9—C5—H53	110.4 (8)
O9—Li1—O6^ii	90.46 (6)	H51—C5—H53	111.2 (11)
O8^ii—Li1—O6^ii	75.98 (5)	H52—C5—H53	108.9 (11)
O10—Li1—Li1^iii	140.56 (10)	C5—O9—C6	111.40 (7)
O2—Li1—Li1^iii	88.65 (7)	C5—O9—Li1	124.38 (7)
O8^i—Li1—Li1^iii	40.17 (4)	C6—O9—Li1	107.55 (7)
O9—Li1—Li1^iii	95.84 (8)	O9—C6—C7	107.67 (7)
O8^ii—Li1—Li1^iii	37.44 (4)	O9—C6—H61	107.5 (7)
O6^ii—Li1—Li1^iii	113.09 (8)	C7—C6—H61	110.4 (7)
O3—B1—O1	106.01 (6)	O9—C6—H62	111.8 (8)
O3—B1—O5	111.68 (7)	C7—C6—H62	108.1 (8)
O1—B1—O5	112.24 (7)	H61—C6—H62	111.3 (11)
O3—B1—O7	111.55 (7)	O10—C7—C6	106.92 (7)
O1—B1—O7	110.05 (7)	O10—C7—H71	110.3 (7)
O5—B1—O7	105.41 (7)	C6—C7—H71	111.5 (7)
O2—C1—O1	126.66 (8)	O10—C7—H72	110.4 (7)
O2—C1—C2	125.50 (8)	C6—C7—H72	109.7 (7)
O1—C1—C2	107.83 (7)	H71—C7—H72	108.0 (9)
O4—C2—O3	126.78 (8)	C8—O10—C7	112.18 (7)
O4—C2—C1	126.00 (8)	C8—O10—Li1	126.24 (8)
O3—C2—C1	107.22 (7)	C7—O10—Li1	110.05 (7)
C1—O1—B1	109.08 (7)	O10—C8—H81	109.4 (8)
C1—O2—Li1	139.52 (8)	O10—C8—H82	111.2 (8)
C2—O3—B1	109.71 (7)	H81—C8—H82	108.4 (11)
O6—C3—O5	128.35 (8)	O10—C8—H83	106.2 (8)
O6—C3—C4	123.92 (8)	H81—C8—H83	112.7 (12)
O5—C3—C4	107.72 (7)	H82—C8—H83	109.0 (12)
O2—C1—C2—O4	1.14 (14)	O8—C4—O7—B1	−177.41 (9)
O1—C1—C2—O4	−178.99 (8)	C3—C4—O7—B1	3.18 (9)
O2—C1—C2—O3	−179.05 (8)	O3—B1—O7—C4	−124.26 (7)
O1—C1—C2—O3	0.82 (9)	O1—B1—O7—C4	118.36 (7)
O2—C1—O1—B1	−178.51 (8)	O5—B1—O7—C4	−2.88 (9)
C2—C1—O1—B1	1.62 (9)	O7—C4—O8—Li1^iv	21.13 (17)
O3—B1—O1—C1	−3.32 (9)	C3—C4—O8—Li1^iv	−159.55 (10)
O5—B1—O1—C1	−125.50 (7)	O7—C4—O8—Li1^ii	172.26 (8)
O7—B1—O1—C1	117.44 (7)	C3—C4—O8—Li1^ii	−8.41 (11)
O1—C1—O2—Li1	−11.63 (17)	O10—Li1—O9—C5	−145.33 (8)
C2—C1—O2—Li1	168.21 (9)	O8^i—Li1—O9—C5	114.76 (8)
O10—Li1—O2—C1	159.67 (10)	O8^ii—Li1—O9—C5	37.06 (10)
O8^i—Li1—O2—C1	−99.73 (11)	O6^ii—Li1—O9—C5	−38.94 (10)
O8^ii—Li1—O2—C1	−22.20 (13)	O10—Li1—O9—C6	−12.48 (8)
O6^ii—Li1—O2—C1	53.68 (12)	O8^i—Li1—O9—C6	−112.38 (7)
O4—C2—O3—B1	176.89 (9)	O8^ii—Li1—O9—C6	169.91 (6)
C1—C2—O3—B1	−2.92 (9)	O6^ii—Li1—O9—C6	93.92 (7)
O1—B1—O3—C2	3.89 (9)	C5—O9—C6—C7	179.15 (8)
O5—B1—O3—C2	126.43 (7)	Li1—O9—C6—C7	39.68 (9)
O7—B1—O3—C2	−115.90 (8)	O9—C6—C7—O10	−56.72 (10)
O6—C3—C4—O8	−2.95 (14)	C6—C7—O10—C8	−168.80 (8)
O5—C3—C4—O8	178.17 (8)	C6—C7—O10—Li1	45.27 (9)
O6—C3—C4—O7	176.49 (8)	O2—Li1—O10—C8	25.70 (11)
O5—C3—C4—O7	−2.39 (9)	O8^i—Li1—O10—C8	−62.25 (11)
O6—C3—O5—B1	−178.34 (9)	O9—Li1—O10—C8	−158.54 (8)
C4—C3—O5—B1	0.48 (9)	O6^ii—Li1—O10—C8	113.48 (9)
O3—B1—O5—C3	122.62 (7)	O2—Li1—O10—C7	165.67 (7)
O1—B1—O5—C3	−118.47 (8)	O8^i—Li1—O10—C7	77.72 (8)
O7—B1—O5—C3	1.32 (9)	O9—Li1—O10—C7	−18.57 (8)
O5—C3—O6—Li1^ii	−170.36 (9)	O6^ii—Li1—O10—C7	−106.55 (8)
C4—C3—O6—Li1^ii	10.99 (11)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x−1, y, z.

(V) Lithium bis(oxalato)borate 1,3-dioxolane hydrate

Crystal data

C17H20B2Li2O23	Z = 2
Mr = 627.83	F(000) = 644
Triclinic, P1	Dx = 1.735 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1327 (14) Å	Cell parameters from 2243 reflections
b = 9.6378 (15) Å	θ = 2.5–27.5°
c = 14.812 (2) Å	µ = 0.16 mm^−1
α = 80.640 (3)°	T = 110 K
β = 79.414 (3)°	Prism, colorles
γ = 70.642 (3)°	0.27 × 0.14 × 0.08 mm
V = 1201.8 (3) Å^3

Data collection

Three-circle diffractometer	4074 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 8.33 pixels mm^-1	θmax = 24.7°, θmin = 1.4°
ω scans	h = −10→10
Absorption correction: multi-scan XPREP (Sheldrick, 1997)	k = −11→11
Tmin = 0.881, Tmax = 0.987	l = −17→17
9591 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.005P)^2], P = (max(Fo^2,0) + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
4074 reflections	Δρmax = 0.38 e Å^−3
398 parameters	Δρmin = −0.36 e Å^−3
282 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (17)

Special details

Experimental. Crystal was split and only major part was integrated.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	1.1028 (10)	0.8227 (9)	−0.0353 (6)	0.027 (2)
Li2	0.3957 (10)	0.4003 (8)	0.5058 (5)	0.022 (2)
B1	0.5272 (6)	0.8893 (6)	0.1303 (4)	0.0165 (13)
C1	0.7596 (6)	0.9301 (5)	0.0783 (3)	0.0162 (11)
C2	0.6465 (5)	1.0653 (5)	0.1213 (3)	0.0159 (11)
C3	0.3905 (5)	0.7319 (5)	0.2027 (3)	0.0131 (11)
C4	0.3296 (6)	0.8048 (5)	0.1118 (3)	0.0149 (11)
O1	0.6915 (3)	0.8301 (3)	0.08320 (19)	0.0166 (8)
O2	0.8944 (4)	0.9228 (3)	0.0445 (2)	0.0198 (8)
O3	0.5134 (3)	1.0338 (3)	0.15269 (19)	0.0167 (8)
O4	0.6728 (4)	1.1783 (3)	0.1245 (2)	0.0184 (8)
O5	0.5005 (3)	0.7875 (3)	0.21389 (19)	0.0151 (8)
O6	0.3480 (4)	0.6410 (3)	0.2576 (2)	0.0192 (8)
O7	0.4129 (4)	0.8932 (3)	0.0722 (2)	0.0167 (8)
O8	0.2263 (4)	0.7830 (3)	0.0820 (2)	0.0176 (8)
B2	0.0924 (6)	0.9593 (6)	0.3683 (4)	0.0123 (12)
C5	0.1887 (6)	0.7379 (5)	0.4518 (3)	0.0161 (11)
C6	0.2941 (6)	0.8323 (5)	0.4497 (3)	0.0166 (11)
C7	0.0118 (5)	1.0917 (5)	0.2326 (3)	0.0167 (11)
C8	−0.1001 (6)	1.1625 (5)	0.3159 (3)	0.0174 (11)
O9	0.0727 (3)	0.8176 (3)	0.40509 (19)	0.0167 (8)
O10	0.2077 (4)	0.6138 (3)	0.4880 (2)	0.0185 (8)
O11	0.2304 (3)	0.9639 (3)	0.40495 (19)	0.0162 (8)
O12	0.4151 (4)	0.7968 (3)	0.4821 (2)	0.0188 (8)
O13	0.1232 (3)	0.9779 (3)	0.26550 (19)	0.0168 (8)
O14	0.0019 (4)	1.1346 (3)	0.1526 (2)	0.0212 (8)
O15	−0.0493 (3)	1.0832 (3)	0.39216 (19)	0.0162 (8)
O16	−0.2143 (4)	1.2697 (3)	0.3116 (2)	0.0216 (8)
O1W	0.5365 (3)	0.4941 (3)	0.40200 (19)	0.0165 (8)
H1W	0.4761	0.5648	0.3556	0.025*
H2W	0.6260	0.4188	0.3711	0.025*
C9	0.1557 (6)	0.3283 (5)	0.4152 (3)	0.0240 (13)
H9A	0.0859	0.4252	0.4340	0.029*
H9B	0.1316	0.2494	0.4613	0.029*
C10	0.3967 (5)	0.2434 (5)	0.3315 (3)	0.0232 (12)
H10A	0.4237	0.1348	0.3469	0.028*
H10B	0.4933	0.2695	0.3059	0.028*
C11	0.2767 (6)	0.3004 (5)	0.2659 (3)	0.0262 (13)
H11A	0.2776	0.3984	0.2334	0.031*
H11B	0.2951	0.2307	0.2197	0.031*
O17	0.3143 (4)	0.3204 (3)	0.4110 (2)	0.0226 (8)
O18	0.1310 (4)	0.3107 (3)	0.3265 (2)	0.0242 (8)
C12	1.2452 (6)	0.5233 (5)	−0.1015 (3)	0.0207 (12)
H12A	1.1945	0.4572	−0.1189	0.025*
H12B	1.2638	0.5924	−0.1563	0.025*
C13	1.1763 (5)	0.4946 (5)	0.0509 (3)	0.0224 (12)
H13A	1.1083	0.4311	0.0578	0.027*
H13B	1.1564	0.5424	0.1082	0.027*
C14	1.3479 (5)	0.4052 (5)	0.0303 (3)	0.0165 (11)
H14A	1.4132	0.4347	0.0653	0.020*
H14B	1.3630	0.2980	0.0462	0.020*
O19	0.2522 (4)	0.3053 (3)	0.6116 (2)	0.0204 (8)
O20	0.1837 (4)	0.1345 (3)	0.7242 (2)	0.0209 (8)
C15	0.2878 (6)	0.1522 (5)	0.6399 (3)	0.0192 (12)
H15A	0.3984	0.1097	0.6510	0.023*
H15B	0.2719	0.1009	0.5915	0.023*
C16	0.1723 (6)	0.3795 (5)	0.6919 (3)	0.0219 (12)
H16A	0.1029	0.4802	0.6746	0.026*
H16B	0.2474	0.3861	0.7302	0.026*
C17	0.0797 (5)	0.2806 (4)	0.7412 (3)	0.0168 (11)
H17A	0.0551	0.2911	0.8081	0.020*
H17B	−0.0192	0.3024	0.7154	0.020*
O21	1.1491 (4)	0.6030 (3)	−0.0277 (2)	0.0187 (8)
O22	1.3872 (4)	0.4402 (3)	−0.0685 (2)	0.0195 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.025 (3)	0.028 (3)	0.025 (3)	−0.0060 (19)	−0.0018 (19)	−0.0029 (19)
Li2	0.018 (3)	0.023 (3)	0.022 (3)	−0.0065 (19)	−0.0016 (19)	−0.0012 (19)
B1	0.011 (2)	0.019 (2)	0.016 (2)	−0.0031 (16)	0.0015 (16)	−0.0017 (17)
C1	0.0150 (19)	0.0177 (18)	0.0148 (19)	−0.0040 (16)	−0.0011 (15)	−0.0018 (15)
C2	0.0114 (16)	0.0186 (16)	0.0156 (16)	−0.0019 (13)	−0.0022 (13)	−0.0009 (13)
C3	0.0079 (18)	0.0148 (18)	0.0122 (18)	0.0013 (15)	0.0007 (15)	−0.0021 (15)
C4	0.0129 (19)	0.0156 (18)	0.0136 (19)	−0.0014 (15)	0.0008 (16)	−0.0034 (15)
O1	0.0109 (15)	0.0191 (14)	0.0161 (15)	−0.0018 (12)	0.0028 (12)	−0.0035 (12)
O2	0.0126 (15)	0.0247 (15)	0.0186 (15)	−0.0036 (13)	0.0019 (12)	−0.0020 (13)
O3	0.0114 (15)	0.0203 (14)	0.0159 (15)	−0.0053 (12)	0.0038 (12)	−0.0011 (12)
O4	0.0127 (15)	0.0207 (14)	0.0188 (15)	−0.0030 (12)	0.0020 (12)	−0.0035 (12)
O5	0.0103 (15)	0.0197 (14)	0.0126 (14)	−0.0024 (12)	0.0000 (12)	−0.0006 (12)
O6	0.0128 (15)	0.0211 (15)	0.0182 (15)	−0.0021 (13)	0.0007 (12)	0.0033 (13)
O7	0.0137 (15)	0.0191 (14)	0.0159 (15)	−0.0056 (12)	0.0005 (12)	0.0000 (12)
O8	0.0134 (15)	0.0221 (15)	0.0153 (14)	−0.0038 (12)	0.0000 (12)	−0.0027 (12)
B2	0.009 (2)	0.014 (2)	0.011 (2)	0.0001 (16)	−0.0016 (16)	−0.0008 (16)
C5	0.0118 (19)	0.0203 (19)	0.0118 (18)	−0.0002 (15)	0.0028 (15)	−0.0043 (16)
C6	0.0151 (19)	0.0205 (19)	0.0116 (18)	−0.0028 (16)	0.0005 (15)	−0.0030 (15)
C7	0.0132 (19)	0.0189 (18)	0.0153 (19)	−0.0031 (15)	−0.0004 (15)	−0.0004 (16)
C8	0.0157 (19)	0.0178 (18)	0.0168 (19)	−0.0038 (16)	−0.0012 (16)	−0.0006 (16)
O9	0.0081 (15)	0.0216 (15)	0.0145 (14)	0.0005 (12)	0.0012 (12)	0.0004 (12)
O10	0.0119 (15)	0.0199 (14)	0.0181 (15)	−0.0016 (12)	0.0039 (12)	−0.0002 (13)
O11	0.0115 (15)	0.0188 (14)	0.0139 (14)	−0.0014 (12)	0.0008 (12)	0.0007 (12)
O12	0.0123 (15)	0.0246 (15)	0.0157 (15)	−0.0020 (12)	0.0001 (12)	−0.0015 (12)
O13	0.0106 (15)	0.0200 (14)	0.0125 (14)	0.0027 (12)	0.0012 (12)	0.0000 (12)
O14	0.0175 (15)	0.0251 (15)	0.0148 (15)	−0.0002 (12)	−0.0003 (12)	−0.0011 (13)
O15	0.0112 (15)	0.0195 (14)	0.0120 (14)	0.0007 (12)	0.0013 (12)	−0.0003 (12)
O16	0.0141 (15)	0.0248 (15)	0.0191 (15)	0.0009 (13)	0.0007 (12)	−0.0013 (13)
O1W	0.0070 (18)	0.0229 (18)	0.0103 (17)	0.0031 (15)	0.0037 (14)	0.0023 (14)
C9	0.014 (3)	0.038 (3)	0.023 (3)	−0.010 (2)	−0.002 (2)	−0.008 (2)
C10	0.009 (3)	0.035 (3)	0.021 (3)	−0.002 (2)	0.007 (2)	−0.012 (2)
C11	0.015 (3)	0.040 (3)	0.020 (3)	−0.007 (2)	0.007 (2)	−0.006 (2)
O17	0.0129 (15)	0.0322 (15)	0.0206 (15)	−0.0044 (12)	0.0006 (12)	−0.0060 (13)
O18	0.0164 (15)	0.0327 (15)	0.0189 (15)	−0.0018 (13)	0.0002 (12)	−0.0048 (13)
C12	0.017 (3)	0.026 (3)	0.014 (3)	0.000 (2)	−0.004 (2)	−0.001 (2)
C13	0.015 (3)	0.025 (3)	0.019 (3)	0.001 (2)	0.002 (2)	0.002 (2)
C14	0.012 (2)	0.020 (2)	0.014 (2)	0.000 (2)	0.000 (2)	−0.002 (2)
O19	0.0166 (19)	0.0212 (17)	0.0168 (18)	−0.0033 (15)	0.0083 (15)	−0.0016 (15)
O20	0.0173 (15)	0.0226 (14)	0.0162 (14)	−0.0026 (12)	0.0060 (12)	−0.0003 (12)
C15	0.015 (3)	0.023 (3)	0.016 (3)	−0.007 (2)	0.009 (2)	−0.003 (2)
C16	0.021 (3)	0.022 (2)	0.017 (3)	−0.002 (2)	0.006 (2)	−0.006 (2)
C17	0.009 (2)	0.023 (2)	0.014 (2)	0.001 (2)	0.003 (2)	−0.006 (2)
O21	0.0130 (18)	0.0243 (18)	0.0118 (17)	−0.0005 (15)	0.0050 (14)	−0.0017 (14)
O22	0.0085 (18)	0.0303 (19)	0.0123 (17)	0.0000 (15)	0.0037 (14)	−0.0001 (15)

Geometric parameters (Å, º)

Li1—O21	2.006 (8)	B2—O11	1.476 (6)
Li1—O14^i	2.055 (9)	B2—O13	1.489 (6)
Li1—O2	2.068 (9)	C5—O10	1.198 (5)
Li1—O8^ii	2.158 (9)	C5—O9	1.322 (5)
Li1—O4^iii	2.223 (9)	C5—C6	1.522 (6)
Li1—O2^iii	2.443 (8)	C6—O12	1.208 (5)
Li1—Li1^iii	3.534 (16)	C6—O11	1.329 (5)
Li2—O17	2.057 (8)	C7—O14	1.199 (5)
Li2—O1W	2.104 (8)	C7—O13	1.321 (5)
Li2—O12^iv	2.110 (8)	C7—C8	1.543 (6)
Li2—O1W^iv	2.113 (8)	C8—O16	1.203 (5)
Li2—O19	2.141 (8)	C8—O15	1.323 (5)
Li2—O10	2.214 (8)	C9—O17	1.416 (5)
Li2—Li2^iv	3.091 (15)	C9—O18	1.418 (5)
B1—O3	1.444 (6)	C10—O17	1.446 (5)
B1—O7	1.458 (6)	C10—C11	1.505 (6)
B1—O5	1.486 (6)	C11—O18	1.445 (5)
B1—O1	1.497 (6)	C12—O22	1.406 (5)
C1—O2	1.224 (5)	C12—O21	1.424 (5)
C1—O1	1.295 (5)	C13—O21	1.431 (5)
C1—C2	1.519 (6)	C13—C14	1.519 (6)
C2—O4	1.201 (5)	C14—O22	1.453 (5)
C2—O3	1.333 (5)	O19—C15	1.411 (5)
C3—O6	1.207 (5)	O19—C16	1.440 (5)
C3—O5	1.331 (5)	O20—C17	1.446 (5)
C3—C4	1.525 (6)	O20—C15	1.447 (5)
C4—O8	1.201 (5)	C16—C17	1.495 (6)
C4—O7	1.325 (5)	O1W—H1W	0.99
B2—O9	1.443 (5)	O1W—H2W	0.99
B2—O15	1.474 (6)
O21—Li1—O14^i	94.0 (3)	C2—O4—Li1^iii	109.3 (4)
O21—Li1—O2	112.4 (4)	C3—O5—B1	108.6 (3)
O14^i—Li1—O2	92.6 (4)	C4—O7—B1	110.4 (4)
O21—Li1—O8^ii	87.5 (3)	C4—O8—Li1^v	145.4 (4)
O14^i—Li1—O8^ii	175.9 (5)	O9—B2—O15	112.2 (4)
O2—Li1—O8^ii	90.3 (3)	O9—B2—O11	105.6 (4)
O21—Li1—O4^iii	93.9 (4)	O15—B2—O11	112.9 (4)
O14^i—Li1—O4^iii	88.6 (3)	O9—B2—O13	112.8 (4)
O2—Li1—O4^iii	153.4 (4)	O15—B2—O13	104.8 (3)
O8^ii—Li1—O4^iii	87.4 (3)	O11—B2—O13	108.7 (4)
O21—Li1—O2^iii	168.0 (5)	O10—C5—O9	126.1 (4)
O14^i—Li1—O2^iii	92.7 (3)	O10—C5—C6	126.6 (4)
O2—Li1—O2^iii	77.2 (3)	O9—C5—C6	107.3 (4)
O8^ii—Li1—O2^iii	85.1 (3)	O12—C6—O11	124.8 (4)
O4^iii—Li1—O2^iii	76.3 (3)	O12—C6—C5	127.3 (4)
O17—Li2—O1W	92.4 (3)	O11—C6—C5	107.9 (4)
O17—Li2—O12^iv	91.4 (3)	O14—C7—O13	126.2 (4)
O1W—Li2—O12^iv	90.1 (3)	O14—C7—C8	126.3 (4)
O17—Li2—O1W^iv	173.6 (4)	O13—C7—C8	107.5 (4)
O1W—Li2—O1W^iv	85.7 (3)	O16—C8—O15	126.5 (4)
O12^iv—Li2—O1W^iv	94.7 (3)	O16—C8—C7	125.7 (4)
O17—Li2—O19	87.7 (3)	O15—C8—C7	107.9 (4)
O1W—Li2—O19	179.9 (4)	C5—O9—B2	110.3 (4)
O12^iv—Li2—O19	90.0 (3)	C5—O10—Li2	140.6 (4)
O1W^iv—Li2—O19	94.2 (3)	C6—O11—B2	108.5 (3)
O17—Li2—O10	89.6 (3)	C6—O12—Li2^iv	134.4 (4)
O1W—Li2—O10	86.4 (3)	C7—O13—B2	109.8 (3)
O12^iv—Li2—O10	176.4 (4)	C7—O14—Li1^i	154.0 (4)
O1W^iv—Li2—O10	84.3 (3)	C8—O15—B2	109.9 (4)
O19—Li2—O10	93.5 (3)	Li2—O1W—Li2^iv	94.3 (3)
O3—B1—O7	112.9 (4)	H1W—O1W—H2W	110.3
O3—B1—O5	112.2 (4)	O17—C9—O18	108.5 (4)
O7—B1—O5	105.2 (4)	O17—C10—C11	101.5 (4)
O3—B1—O1	105.6 (4)	H10A—C10—H10B	109.3
O7—B1—O1	111.5 (4)	O18—C11—C10	102.8 (4)
O5—B1—O1	109.5 (4)	C9—O17—C10	105.4 (3)
O2—C1—O1	127.4 (4)	C9—O17—Li2	123.8 (3)
O2—C1—C2	122.5 (4)	C10—O17—Li2	130.7 (4)
O1—C1—C2	110.1 (4)	C9—O18—C11	106.7 (4)
O4—C2—O3	127.5 (4)	O22—C12—O21	106.2 (3)
O4—C2—C1	126.1 (4)	O21—C13—C14	104.1 (4)
O3—C2—C1	106.4 (4)	O22—C14—C13	104.1 (3)
O6—C3—O5	124.0 (4)	C15—O19—C16	106.6 (3)
O6—C3—C4	127.7 (4)	C15—O19—Li2	123.7 (3)
O5—C3—C4	108.2 (4)	C16—O19—Li2	121.0 (3)
O8—C4—O7	127.1 (4)	C17—O20—C15	106.8 (3)
O8—C4—C3	125.5 (4)	O19—C15—O20	107.2 (3)
O7—C4—C3	107.4 (4)	O19—C16—C17	102.1 (3)
C1—O1—B1	107.9 (4)	O20—C17—C16	103.1 (3)
C1—O2—Li1	151.0 (4)	C12—O21—C13	102.5 (3)
C1—O2—Li1^iii	103.5 (3)	C12—O21—Li1	120.4 (4)
Li1—O2—Li1^iii	102.8 (3)	C13—O21—Li1	128.9 (3)
C2—O3—B1	110.0 (4)	C12—O22—C14	106.1 (3)
O2—C1—C2—O4	2.6 (8)	O13—B2—O11—C6	−115.0 (4)
O1—C1—C2—O4	−177.2 (4)	O11—C6—O12—Li2^iv	−142.7 (5)
O2—C1—C2—O3	−178.5 (4)	C5—C6—O12—Li2^iv	37.0 (8)
O1—C1—C2—O3	1.6 (5)	O14—C7—O13—B2	−179.1 (4)
O6—C3—C4—O8	1.3 (8)	C8—C7—O13—B2	2.6 (5)
O5—C3—C4—O8	−177.7 (4)	O9—B2—O13—C7	119.6 (4)
O6—C3—C4—O7	−177.7 (4)	O15—B2—O13—C7	−2.8 (5)
O5—C3—C4—O7	3.3 (5)	O11—B2—O13—C7	−123.7 (4)
O2—C1—O1—B1	180.0 (5)	O13—C7—O14—Li1^i	115.4 (9)
C2—C1—O1—B1	−0.2 (5)	C8—C7—O14—Li1^i	−66.7 (10)
O3—B1—O1—C1	−1.2 (5)	O16—C8—O15—B2	179.0 (4)
O7—B1—O1—C1	121.8 (4)	C7—C8—O15—B2	−0.2 (5)
O5—B1—O1—C1	−122.2 (4)	O9—B2—O15—C8	−121.0 (4)
O1—C1—O2—Li1	13.2 (11)	O11—B2—O15—C8	119.9 (4)
C2—C1—O2—Li1	−166.6 (6)	O13—B2—O15—C8	1.7 (5)
O1—C1—O2—Li1^iii	167.6 (4)	O17—Li2—O1W—Li2^iv	173.9 (4)
C2—C1—O2—Li1^iii	−12.2 (5)	O12^iv—Li2—O1W—Li2^iv	−94.7 (3)
O21—Li1—O2—C1	−33.2 (10)	O1W^iv—Li2—O1W—Li2^iv	0.0
O14^i—Li1—O2—C1	62.3 (9)	O10—Li2—O1W—Li2^iv	84.5 (3)
O8^ii—Li1—O2—C1	−120.6 (7)	O17—C10—C11—O18	−37.4 (4)
O4^iii—Li1—O2—C1	154.5 (8)	O18—C9—O17—C10	−21.2 (5)
O2^iii—Li1—O2—C1	154.5 (8)	O18—C9—O17—Li2	160.6 (4)
Li1^iii—Li1—O2—C1	154.5 (8)	C11—C10—O17—C9	35.9 (4)
O21—Li1—O2—Li1^iii	172.4 (5)	C11—C10—O17—Li2	−146.1 (4)
O14^i—Li1—O2—Li1^iii	−92.2 (3)	O1W—Li2—O17—C9	−137.0 (4)
O8^ii—Li1—O2—Li1^iii	84.9 (3)	O12^iv—Li2—O17—C9	132.9 (4)
O4^iii—Li1—O2—Li1^iii	0.0 (9)	O19—Li2—O17—C9	42.9 (5)
O2^iii—Li1—O2—Li1^iii	0.0	O10—Li2—O17—C9	−50.6 (5)
O4—C2—O3—B1	176.5 (5)	Li2^iv—Li2—O17—C9	−131.2 (6)
C1—C2—O3—B1	−2.3 (5)	O1W—Li2—O17—C10	45.3 (5)
O7—B1—O3—C2	−119.8 (4)	O12^iv—Li2—O17—C10	−44.8 (5)
O5—B1—O3—C2	121.5 (4)	O19—Li2—O17—C10	−134.8 (4)
O1—B1—O3—C2	2.2 (5)	O10—Li2—O17—C10	131.7 (4)
O3—C2—O4—Li1^iii	−168.3 (4)	Li2^iv—Li2—O17—C10	51.2 (9)
C1—C2—O4—Li1^iii	10.3 (6)	O17—C9—O18—C11	−3.4 (5)
O6—C3—O5—B1	176.9 (4)	C10—C11—O18—C9	25.4 (5)
C4—C3—O5—B1	−4.1 (5)	O21—C13—C14—O22	−17.4 (4)
O3—B1—O5—C3	126.7 (4)	O17—Li2—O19—C15	74.0 (4)
O7—B1—O5—C3	3.5 (5)	O12^iv—Li2—O19—C15	−17.4 (5)
O1—B1—O5—C3	−116.4 (4)	O1W^iv—Li2—O19—C15	−112.1 (4)
O8—C4—O7—B1	−180.0 (5)	O10—Li2—O19—C15	163.4 (3)
C3—C4—O7—B1	−1.0 (5)	Li2^iv—Li2—O19—C15	−112.2 (7)
O3—B1—O7—C4	−124.1 (4)	O17—Li2—O19—C16	−142.7 (3)
O5—B1—O7—C4	−1.4 (5)	O12^iv—Li2—O19—C16	126.0 (4)
O1—B1—O7—C4	117.2 (4)	O1W^iv—Li2—O19—C16	31.3 (5)
O7—C4—O8—Li1^v	7.4 (9)	O10—Li2—O19—C16	−53.2 (4)
C3—C4—O8—Li1^v	−171.5 (5)	Li2^iv—Li2—O19—C16	31.2 (9)
O10—C5—C6—O12	1.8 (8)	C16—O19—C15—O20	20.4 (5)
O9—C5—C6—O12	−177.4 (4)	Li2—O19—C15—O20	168.1 (4)
O10—C5—C6—O11	−178.4 (4)	C17—O20—C15—O19	3.6 (5)
O9—C5—C6—O11	2.3 (5)	C15—O19—C16—C17	−35.3 (5)
O14—C7—C8—O16	1.0 (8)	Li2—O19—C16—C17	175.9 (4)
O13—C7—C8—O16	179.2 (4)	C15—O20—C17—C16	−24.9 (4)
O14—C7—C8—O15	−179.8 (4)	O19—C16—C17—O20	36.5 (4)
O13—C7—C8—O15	−1.6 (5)	O22—C12—O21—C13	−42.2 (4)
O10—C5—O9—B2	−177.5 (4)	O22—C12—O21—Li1	109.0 (4)
C6—C5—O9—B2	1.7 (5)	C14—C13—O21—C12	35.6 (4)
O15—B2—O9—C5	−128.1 (4)	C14—C13—O21—Li1	−112.1 (5)
O11—B2—O9—C5	−4.8 (5)	O14^i—Li1—O21—C12	59.8 (5)
O13—B2—O9—C5	113.8 (4)	O2—Li1—O21—C12	154.3 (4)
O9—C5—O10—Li2	136.8 (5)	O8^ii—Li1—O21—C12	−116.4 (4)
C6—C5—O10—Li2	−42.3 (8)	O4^iii—Li1—O21—C12	−29.1 (5)
O17—Li2—O10—C5	−104.5 (6)	O2^iii—Li1—O21—C12	−64 (2)
O1W—Li2—O10—C5	−12.1 (6)	O14^i—Li1—O21—C13	−157.4 (4)
O1W^iv—Li2—O10—C5	74.0 (6)	O2—Li1—O21—C13	−62.9 (6)
O19—Li2—O10—C5	167.8 (5)	O8^ii—Li1—O21—C13	26.4 (5)
Li2^iv—Li2—O10—C5	31.0 (7)	O4^iii—Li1—O21—C13	113.7 (4)
O12—C6—O11—B2	174.5 (4)	O2^iii—Li1—O21—C13	79 (2)
C5—C6—O11—B2	−5.3 (5)	O21—C12—O22—C14	31.0 (4)
O9—B2—O11—C6	6.2 (5)	C13—C14—O22—C12	−7.9 (4)
O15—B2—O11—C6	129.2 (4)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y, z; (iii) −x+2, −y+2, −z; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O6	0.99	1.93	2.880 (4)	160
O1W—H2W···O16^vi	0.99	1.88	2.865 (4)	176

Symmetry code: (vi) x+1, y−1, z.

(VI) Lithium tetrakis-ethylenecarbonate bis(oxalato)borate

Crystal data

C12H16LiO12·C4BO8	Dx = 1.599 Mg m^−3
Mr = 546.04	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 3376 reflections
Hall symbol: I -4	θ = 2.7–31.5°
a = 10.2343 (5) Å	µ = 0.15 mm^−1
c = 10.8245 (7) Å	T = 110 K
V = 1133.77 (11) Å^3	Prism, colorless
Z = 2	0.51 × 0.46 × 0.38 mm
F(000) = 560

Data collection

Three-circle diffractometer	876 independent reflections
Radiation source: fine-focus sealed tube	871 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.7°
ω scans	h = −13→14
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −10→14
Tmin = 0.905, Tmax = 0.945	l = −15→15
7169 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 0.921P], P = (max(Fo^2,0) + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
876 reflections	Δρmax = 0.29 e Å^−3
103 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0190 (12)

Special details

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.

Friedel pairs have been averaged during the refinement using MERG 3 instruction because of absence the atoms with noticeable anoumalous scatering.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.5000	0.5000	0.0000	0.0192 (10)
C1	0.17553 (16)	0.26669 (18)	0.28798 (16)	0.0257 (3)
H11	0.099 (2)	0.320 (2)	0.293 (2)	0.035 (6)*
H12	0.199 (2)	0.232 (2)	0.366 (2)	0.029 (5)*
C2	0.17070 (15)	0.16338 (15)	0.18697 (16)	0.0220 (3)
H21	0.0943 (19)	0.1690 (18)	0.1376 (18)	0.017 (5)*
H22	0.183 (2)	0.077 (2)	0.219 (2)	0.028 (5)*
O1	0.27950 (11)	0.35363 (11)	0.24743 (12)	0.0229 (2)
O2	0.28314 (10)	0.19381 (10)	0.11039 (10)	0.0184 (2)
C3	0.33366 (14)	0.30701 (14)	0.14573 (13)	0.0178 (3)
O3	0.42228 (11)	0.35924 (12)	0.09178 (13)	0.0286 (3)
B1	0.5000	0.0000	0.2500	0.0138 (5)
C4	0.44843 (13)	0.05450 (13)	0.44948 (13)	0.0164 (3)
O4	0.42176 (10)	0.08350 (10)	0.33220 (9)	0.0159 (2)
O5	0.40114 (12)	0.10327 (12)	0.53880 (10)	0.0255 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.0182 (14)	0.0182 (14)	0.021 (2)	0.000	0.000	0.000
C1	0.0211 (7)	0.0367 (9)	0.0193 (7)	0.0035 (6)	0.0040 (6)	0.0033 (6)
C2	0.0176 (6)	0.0216 (7)	0.0268 (8)	−0.0027 (5)	0.0006 (6)	0.0073 (6)
O1	0.0242 (5)	0.0223 (5)	0.0222 (5)	0.0011 (4)	−0.0042 (5)	−0.0033 (5)
O2	0.0185 (5)	0.0180 (5)	0.0187 (5)	0.0010 (4)	0.0010 (4)	0.0009 (4)
C3	0.0162 (6)	0.0172 (6)	0.0200 (6)	0.0026 (5)	−0.0047 (5)	0.0055 (5)
O3	0.0193 (5)	0.0304 (6)	0.0360 (7)	−0.0036 (4)	−0.0007 (5)	0.0157 (5)
B1	0.0136 (7)	0.0136 (7)	0.0141 (12)	0.000	0.000	0.000
C4	0.0154 (6)	0.0170 (6)	0.0168 (6)	0.0016 (5)	0.0005 (5)	−0.0004 (5)
O4	0.0160 (5)	0.0171 (5)	0.0145 (4)	0.0045 (3)	−0.0003 (4)	−0.0002 (4)
O5	0.0285 (6)	0.0298 (6)	0.0181 (5)	0.0068 (5)	0.0034 (5)	−0.0051 (5)

Geometric parameters (Å, º)

Li1—O3^i	1.9222 (11)	O1—C3	1.3216 (19)
Li1—O3^ii	1.9222 (11)	O2—C3	1.3251 (18)
Li1—O3	1.9222 (11)	C3—O3	1.2039 (18)
Li1—O3^iii	1.9222 (11)	B1—O4^iv	1.4707 (10)
C1—O1	1.455 (2)	B1—O4^v	1.4707 (10)
C1—C2	1.522 (2)	B1—O4	1.4707 (10)
C1—H11	0.96 (2)	B1—O4^vi	1.4707 (10)
C1—H12	0.95 (2)	C4—O5	1.1908 (17)
C2—O2	1.4520 (18)	C4—O4	1.3320 (17)
C2—H21	0.949 (19)	C4—C4^v	1.536 (3)
C2—H22	0.96 (2)
O3^i—Li1—O3^ii	105.49 (4)	H21—C2—H22	111.6 (17)
O3^i—Li1—O3	117.76 (8)	C3—O1—C1	109.71 (12)
O3^ii—Li1—O3	105.49 (4)	C3—O2—C2	109.39 (11)
O3^i—Li1—O3^iii	105.49 (4)	O3—C3—O1	124.03 (15)
O3^ii—Li1—O3^iii	117.76 (8)	O3—C3—O2	122.83 (15)
O3—Li1—O3^iii	105.49 (4)	O1—C3—O2	113.11 (12)
O1—C1—C2	103.41 (12)	C3—O3—Li1	153.53 (11)
O1—C1—H11	105.4 (14)	O4^iv—B1—O4^v	111.47 (4)
C2—C1—H11	114.1 (14)	O4^iv—B1—O4	111.47 (4)
O1—C1—H12	108.3 (12)	O4^v—B1—O4	105.55 (8)
C2—C1—H12	113.0 (13)	O4^iv—B1—O4^vi	105.55 (8)
H11—C1—H12	111.9 (18)	O4^v—B1—O4^vi	111.47 (4)
O2—C2—C1	103.61 (12)	O4—B1—O4^vi	111.47 (4)
O2—C2—H21	108.5 (12)	O5—C4—O4	126.67 (13)
C1—C2—H21	112.9 (11)	O5—C4—C4^v	125.72 (9)
O2—C2—H22	107.6 (13)	O4—C4—C4^v	107.62 (7)
C1—C2—H22	112.1 (13)	C4—O4—B1	109.61 (8)
O1—C1—C2—O2	7.34 (15)	O3^i—Li1—O3—C3	86.6 (3)
C2—C1—O1—C3	−3.68 (16)	O3^ii—Li1—O3—C3	−156.0 (3)
C1—C2—O2—C3	−8.92 (15)	O3^iii—Li1—O3—C3	−30.7 (3)
C1—O1—C3—O3	179.93 (14)	O5—C4—O4—B1	−179.35 (14)
C1—O1—C3—O2	−2.02 (17)	C4^v—C4—O4—B1	0.40 (17)
C2—O2—C3—O3	−174.69 (13)	O4^iv—B1—O4—C4	121.00 (8)
C2—O2—C3—O1	7.23 (16)	O4^v—B1—O4—C4	−0.17 (7)
O1—C3—O3—Li1	−63.0 (3)	O4^vi—B1—O4—C4	−121.34 (8)
O2—C3—O3—Li1	119.1 (3)

Symmetry codes: (i) −x+1, −y+1, z; (ii) −y+1, x, −z; (iii) y, −x+1, −z; (iv) −y+1/2, x−1/2, −z+1/2; (v) −x+1, −y, z; (vi) y+1/2, −x+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H11···O1^vii	0.96 (2)	2.74 (2)	3.350 (2)	121.8 (17)
C1—H12···O2^viii	0.95 (2)	2.76 (2)	3.539 (2)	140.4 (17)
C2—H21···O1^vii	0.949 (19)	2.810 (19)	3.3728 (19)	118.9 (14)
C2—H22···O3^iv	0.96 (2)	2.62 (2)	3.452 (2)	144.9 (17)
C2—H22···O4^iv	0.96 (2)	2.92 (2)	3.5335 (19)	122.6 (16)

Symmetry codes: (iv) −y+1/2, x−1/2, −z+1/2; (vii) y−1/2, −x+1/2, −z+1/2; (viii) −x+1/2, −y+1/2, z+1/2.