Bis(μ-dimesitylborinato-κ2O:O)bis­[(2-methyl­pyridine-κN)lithium]

Saravana, K.T.P.; Son, J.-H.; Hoefelmeyer, J.D.

doi:10.1107/S1600536808042748

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m179

doi:10.1107/S1600536808042748

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Bis(μ-dimesitylborinato-κ²O:O)bis[(2-methylpyridine-κN)lithium]

K. T. Pillai Saravana,^a Jung-Ho Son ^a and James D. Hoefelmeyer ^a ^*

^aDepartment of Chemistry, The University of South Dakota, 414 E. Clark St, Vermillion, SD 57069, USA
^*Correspondence e-mail: jhoefelm@usd.edu

(Received 28 October 2008; accepted 15 December 2008; online 14 January 2009)

The title compound, [Li₂(C₁₈H₂₂BO)₂(C₆H₇N)₂], is a lithium dimesitylboroxide dimer in which the lithium cation is also coordinated by one molecule of 2-methylpyridine. At the core of the structure is an Li₂O₂ four-membered ring. The structure is centrosymmetric with an inversion centre midway between two Li atoms. Intermolecular C—H⋯π interactions and π–π interactions between the 2-methylpyridine rings exist [centroid–centroid distance = 3.6312 (16) Å].

Related literature

For related structures, see: Weese et al. (1987 ); Gibson et al. (1997 ); Cole et al. (2004 ).

Experimental

Crystal data

[Li₂(C₁₈H₂₂BO)₂(C₆H₇N)₂]
M_r = 730.46
Monoclinic, P 2₁ /n
a = 8.6075 (11) Å
b = 9.1307 (11) Å
c = 26.220 (3) Å
β = 90.124 (2)°
V = 2060.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 (2) K
0.63 × 0.19 × 0.14 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.958, T_max = 0.990
8145 measured reflections
2848 independent reflections
2011 reflections with I > 2σ(I)
R_int = 0.036
θ_max = 23.4°

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.140
S = 1.26
2848 reflections
260 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1ⁱ	0.95	2.96	3.787 (3)	146
Symmetry code: (i) x, y-1, z. Cg1 is the centroid of the C8–C13 ring.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042748/gw2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042748/gw2055Isup2.hkl

checkCIF report

Comment top

The title compound is structurally similar to the compounds reported in the literature (Weese et al., 1987; Gibson et al., 1997; Cole et al., 2004). The molecule contains a staggered conformation of C—B—C planes about the Li₂O₂ core, and pyramidalization about the three coordinate lithium(I).

The title compound consist of a lithium(I) cation coordinated to two dimesitylboroxide anions (Li1—O1 = 1.853 (5) Å and Li1—O1ⁱ = 1.873 (5) Å) [symmetry code: (i) -x + 1, -y + 2, -z] and one molecule of 2-methylpyridine (Li1—N1 = 2.084 (5) Å). The environment around boron is distorted trigonal planar (sum of the angles around B1 = 360.0°). The asymmetric units are joined via planar Li₂O₂ four member ring (Li1···Li1ⁱ = 2.444 (8) Å). The lithium cation is three-coordinate and slightly pyramidalized (sum of the angles around Li1 = 356.03°). The O1—Li1—O1ⁱ and O1ⁱ—Li1—N1 angles deviate from an ideal trigonal planar geometry (98.0 (2) ° and 138.6 (3) °, respectively), with the expanded angle a result of steric repulsion between the methyl group (C7) of 2-methylpyridine and dimesitylboroxide group of the adjoining asymmetric unit. The mean plane of boron triangle forms a 48.96 (16) ° angle against the Li₂O₂ plane. The crystal structure contains intermolecular C5—H5···Cg1ⁱⁱ interaction with H···Cg = 2.96 Å, C—H···Cg angle 146° and C···Cg = 3.787 (3) Å (Cg1 is centroid of C8—C13) [symmetry code: (ii) x, -1 + y, z]. Intermolecular face to face π–π interaction between the 2-methylpyridine rings occurs with Cg2···Cg2ⁱⁱⁱ = 3.6312 (`6) Å (Cg2 is centroid of N1—C6) [symmetry code: (iii) -x + 1, -y + 1, -z].

Related literature top

For related structures, see: Weese et al. (1987); Gibson et al. (1997); Cole et al. (2004). Cg1 is the centroid of the C8–C13 ring.

Experimental top

To a solution of 2-methylpyridine (0.45 ml, 3.8 mmol), n-butyllithium (1.6 M, 2.5 ml, 4.2 mmol) in 10 ml hexane was added dropwise through an addition funnel at -78 °C under inert atmosphere. The resulting red color solution was stirred for 30 minutes at -78 °C. Meanwhile, dimesitylboronfluoride (1.0 g, 3.8 mmol) was dissolved in hexane (10 ml) in a round bottom flask and kept under nitrogen atmosphere. The dimesitylboronfluoride solution was transferred to the organolithium by cannula. The resultant yellow color solution was stirred (18 h) under nitrogen atmosphere. The product was filtered through a frit and a yellowish precipitate formed upon exposure to air. The product was dissolved in toluene, and crystals were recovered upon slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP drawing of Bis-µ₂-[(2-methylpyridine)lithium(I)]-bis(dimesitylboroxide). Unlabled atoms are related with labeled part by inversion symmetry. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
	Fig. 2. Packing diagram of Bis-µ₂-[(2-methylpyridine)lithium(I)]-bis(dimesitylboroxide) viewed along a axis. Dotted lines show C— H···π and π–π interactions.

Bis(µ-dimesitylborinato-κ²O:O)bis[(2-methylpyridine-κN)lithium] top

Crystal data top

[Li₂(C₁₈H₂₂BO)₂(C₆H₇N)₂]	F(000) = 784
M_r = 730.46	D_x = 1.177 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1946 reflections
a = 8.6075 (11) Å	θ = 2.5–23.1°
b = 9.1307 (11) Å	µ = 0.07 mm⁻¹
c = 26.220 (3) Å	T = 100 K
β = 90.124 (2)°	Needle, colorless
V = 2060.7 (4) Å³	0.63 × 0.19 × 0.14 mm
Z = 2

Data collection top

Bruker SMART APEXII diffractometer	2848 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 23.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
T_min = 0.958, T_max = 0.990	k = −10→9
8145 measured reflections	l = −28→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.26	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2848 reflections	(Δ/σ)_max = 0.001
260 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Li₂(C₁₈H₂₂BO)₂(C₆H₇N)₂]	V = 2060.7 (4) Å³
M_r = 730.46	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6075 (11) Å	µ = 0.07 mm⁻¹
b = 9.1307 (11) Å	T = 100 K
c = 26.220 (3) Å	0.63 × 0.19 × 0.14 mm
β = 90.124 (2)°

Data collection top

Bruker SMART APEXII diffractometer	2848 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2011 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.990	R_int = 0.036
8145 measured reflections	θ_max = 23.4°

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.26	Δρ_max = 0.30 e Å⁻³
2848 reflections	Δρ_min = −0.24 e Å⁻³
260 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.7338 (3)	0.5897 (3)	−0.00706 (10)	0.0223 (6)
C3	0.7904 (3)	0.4572 (3)	0.01163 (10)	0.0263 (7)
H3	0.8696	0.4059	−0.0062	0.032*
C4	0.7299 (3)	0.4011 (3)	0.05639 (10)	0.0282 (7)
H4	0.7681	0.3114	0.0699	0.034*
C5	0.6140 (3)	0.4763 (3)	0.08128 (10)	0.0281 (7)
H5	0.5699	0.4395	0.1119	0.034*
C6	0.5637 (3)	0.6068 (3)	0.06045 (10)	0.0253 (7)
H6	0.4831	0.6584	0.0774	0.030*
C7	0.7948 (3)	0.6533 (3)	−0.05569 (10)	0.0297 (7)
H7A	0.8423	0.5755	−0.0762	0.045*
H7B	0.8730	0.7281	−0.0478	0.045*
H7C	0.7092	0.6979	−0.0749	0.045*
C8	0.4570 (3)	1.0810 (3)	0.13862 (9)	0.0197 (6)
C9	0.3566 (3)	1.1589 (3)	0.17090 (9)	0.0208 (6)
C10	0.4168 (3)	1.2560 (3)	0.20712 (9)	0.0236 (6)
H10	0.3469	1.3111	0.2275	0.028*
C11	0.5757 (3)	1.2744 (3)	0.21418 (10)	0.0218 (6)
C12	0.6750 (3)	1.1964 (3)	0.18272 (10)	0.0232 (7)
H12	0.7841	1.2070	0.1869	0.028*
C13	0.6178 (3)	1.1022 (3)	0.14482 (10)	0.0222 (6)
C14	0.1828 (3)	1.1379 (3)	0.16953 (10)	0.0276 (7)
H14A	0.1558	1.0466	0.1870	0.041*
H14B	0.1475	1.1331	0.1340	0.041*
H14C	0.1322	1.2204	0.1867	0.041*
C15	0.6359 (3)	1.3743 (3)	0.25549 (10)	0.0304 (7)
H15A	0.7469	1.3562	0.2608	0.046*
H15B	0.5796	1.3552	0.2872	0.046*
H15C	0.6202	1.4765	0.2453	0.046*
C16	0.7350 (3)	1.0196 (3)	0.11262 (10)	0.0272 (7)
H16A	0.7170	0.9141	0.1160	0.041*
H16B	0.8403	1.0431	0.1243	0.041*
H16C	0.7233	1.0483	0.0768	0.041*
C17	0.2773 (3)	0.8374 (3)	0.11617 (9)	0.0214 (6)
C18	0.3143 (3)	0.7485 (3)	0.15886 (9)	0.0227 (6)
C19	0.2096 (3)	0.6436 (3)	0.17580 (10)	0.0230 (7)
H19	0.2383	0.5830	0.2037	0.028*
C20	0.0641 (3)	0.6238 (3)	0.15342 (10)	0.0235 (7)
C21	0.0300 (3)	0.7095 (3)	0.11096 (10)	0.0228 (6)
H21	−0.0675	0.6971	0.0945	0.027*
C22	0.1331 (3)	0.8122 (3)	0.09178 (9)	0.0212 (6)
C23	0.4655 (3)	0.7641 (3)	0.18735 (10)	0.0312 (7)
H23A	0.4646	0.8554	0.2070	0.047*
H23B	0.5517	0.7662	0.1630	0.047*
H23C	0.4787	0.6809	0.2106	0.047*
C24	−0.0507 (3)	0.5159 (3)	0.17434 (11)	0.0358 (8)
H24A	−0.0458	0.4250	0.1545	0.054*
H24B	−0.1556	0.5571	0.1721	0.054*
H24C	−0.0256	0.4951	0.2101	0.054*
C25	0.0840 (3)	0.8989 (3)	0.04561 (10)	0.0276 (7)
H25A	−0.0198	0.8675	0.0348	0.041*
H25B	0.1581	0.8824	0.0179	0.041*
H25C	0.0817	1.0034	0.0542	0.041*
Li1	0.5311 (5)	0.8695 (5)	−0.00153 (16)	0.0253 (10)
B1	0.3913 (3)	0.9657 (3)	0.09683 (11)	0.0203 (7)
N1	0.6228 (3)	0.6653 (2)	0.01732 (8)	0.0236 (6)
O1	0.43136 (19)	0.97903 (18)	0.04806 (6)	0.0246 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0251 (16)	0.0196 (15)	0.0222 (15)	0.0003 (12)	0.0001 (13)	−0.0035 (12)
C3	0.0253 (16)	0.0231 (15)	0.0306 (16)	0.0050 (13)	0.0003 (13)	−0.0029 (13)
C4	0.0328 (17)	0.0207 (15)	0.0312 (17)	0.0029 (13)	−0.0033 (14)	0.0031 (13)
C5	0.0326 (17)	0.0260 (16)	0.0258 (16)	−0.0022 (13)	−0.0004 (14)	0.0043 (13)
C6	0.0231 (16)	0.0281 (16)	0.0246 (16)	0.0015 (13)	0.0027 (13)	−0.0027 (13)
C7	0.0296 (16)	0.0274 (16)	0.0320 (17)	0.0042 (13)	0.0060 (13)	0.0009 (13)
C8	0.0238 (15)	0.0167 (13)	0.0186 (14)	0.0002 (12)	0.0031 (12)	0.0072 (11)
C9	0.0209 (15)	0.0236 (15)	0.0181 (14)	0.0007 (12)	0.0018 (12)	0.0030 (12)
C10	0.0266 (16)	0.0229 (14)	0.0214 (15)	0.0038 (13)	0.0047 (12)	0.0024 (12)
C11	0.0233 (16)	0.0215 (15)	0.0205 (14)	−0.0017 (12)	0.0001 (13)	0.0046 (12)
C12	0.0225 (15)	0.0219 (14)	0.0253 (15)	−0.0031 (12)	0.0009 (13)	0.0088 (12)
C13	0.0244 (16)	0.0186 (14)	0.0235 (15)	0.0014 (12)	0.0053 (12)	0.0068 (12)
C14	0.0252 (16)	0.0308 (16)	0.0267 (16)	0.0022 (13)	0.0037 (13)	−0.0041 (13)
C15	0.0308 (17)	0.0310 (16)	0.0293 (16)	−0.0039 (13)	0.0005 (14)	0.0018 (13)
C16	0.0207 (15)	0.0257 (15)	0.0352 (16)	0.0009 (12)	0.0047 (13)	0.0008 (13)
C17	0.0276 (16)	0.0188 (14)	0.0176 (14)	0.0042 (12)	0.0042 (12)	−0.0023 (11)
C18	0.0299 (17)	0.0207 (14)	0.0175 (14)	0.0030 (13)	0.0042 (12)	0.0014 (12)
C19	0.0289 (16)	0.0201 (14)	0.0200 (14)	0.0028 (13)	0.0040 (13)	0.0026 (11)
C20	0.0256 (16)	0.0204 (15)	0.0245 (15)	−0.0010 (12)	0.0083 (13)	−0.0031 (12)
C21	0.0199 (15)	0.0243 (15)	0.0243 (15)	0.0031 (12)	0.0026 (12)	−0.0041 (12)
C22	0.0275 (16)	0.0195 (14)	0.0167 (14)	0.0034 (12)	0.0045 (12)	−0.0047 (11)
C23	0.0387 (18)	0.0306 (16)	0.0242 (15)	−0.0017 (14)	−0.0066 (14)	0.0074 (13)
C24	0.0365 (18)	0.0321 (17)	0.0387 (17)	−0.0080 (14)	0.0045 (15)	0.0021 (14)
C25	0.0262 (16)	0.0302 (16)	0.0264 (15)	0.0024 (13)	−0.0014 (13)	−0.0006 (13)
Li1	0.026 (3)	0.025 (2)	0.025 (2)	−0.003 (2)	0.005 (2)	−0.0003 (19)
B1	0.0181 (17)	0.0217 (16)	0.0211 (17)	0.0092 (13)	0.0021 (14)	0.0010 (13)
N1	0.0270 (13)	0.0230 (12)	0.0208 (13)	0.0008 (10)	0.0007 (11)	−0.0012 (10)
O1	0.0290 (11)	0.0235 (10)	0.0212 (11)	0.0030 (8)	0.0036 (9)	0.0023 (8)

Geometric parameters (Å, º) top

C2—N1	1.342 (3)	C15—H15C	0.9800
C2—C3	1.393 (4)	C16—H16A	0.9800
C2—C7	1.497 (4)	C16—H16B	0.9800
C3—C4	1.383 (4)	C16—H16C	0.9800
C3—H3	0.9500	C17—C22	1.414 (4)
C4—C5	1.377 (4)	C17—C18	1.419 (3)
C4—H4	0.9500	C17—B1	1.611 (4)
C5—C6	1.380 (4)	C18—C19	1.389 (3)
C5—H5	0.9500	C18—C23	1.506 (4)
C6—N1	1.351 (3)	C19—C20	1.393 (4)
C6—H6	0.9500	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.392 (4)
C7—H7B	0.9800	C20—C24	1.500 (4)
C7—H7C	0.9800	C21—C22	1.386 (4)
C8—C9	1.405 (3)	C21—H21	0.9500
C8—C13	1.406 (3)	C22—C25	1.506 (3)
C8—B1	1.620 (4)	C23—H23A	0.9800
C9—C10	1.398 (3)	C23—H23B	0.9800
C9—C14	1.509 (4)	C23—H23C	0.9800
C10—C11	1.390 (4)	C24—H24A	0.9800
C10—H10	0.9500	C24—H24B	0.9800
C11—C12	1.386 (4)	C24—H24C	0.9800
C11—C15	1.507 (4)	C25—H25A	0.9800
C12—C13	1.403 (4)	C25—H25B	0.9800
C12—H12	0.9500	C25—H25C	0.9800
C13—C16	1.517 (4)	Li1—O1	1.853 (5)
C14—H14A	0.9800	Li1—O1ⁱ	1.873 (5)
C14—H14B	0.9800	Li1—N1	2.084 (5)
C14—H14C	0.9800	Li1—Li1ⁱ	2.444 (8)
C15—H15A	0.9800	B1—O1	1.331 (3)
C15—H15B	0.9800	O1—Li1ⁱ	1.873 (5)

N1—C2—C3	121.8 (2)	C13—C16—H16C	109.5
N1—C2—C7	117.2 (2)	H16A—C16—H16C	109.5
C3—C2—C7	120.9 (3)	H16B—C16—H16C	109.5
C4—C3—C2	119.3 (3)	C22—C17—C18	117.3 (2)
C4—C3—H3	120.4	C22—C17—B1	120.7 (2)
C2—C3—H3	120.4	C18—C17—B1	121.9 (2)
C5—C4—C3	119.5 (2)	C19—C18—C17	120.2 (2)
C5—C4—H4	120.3	C19—C18—C23	117.9 (2)
C3—C4—H4	120.3	C17—C18—C23	122.0 (2)
C4—C5—C6	118.0 (3)	C18—C19—C20	122.6 (2)
C4—C5—H5	121.0	C18—C19—H19	118.7
C6—C5—H5	121.0	C20—C19—H19	118.7
N1—C6—C5	123.7 (3)	C21—C20—C19	116.8 (2)
N1—C6—H6	118.2	C21—C20—C24	121.6 (2)
C5—C6—H6	118.2	C19—C20—C24	121.6 (2)
C2—C7—H7A	109.5	C22—C21—C20	122.5 (2)
C2—C7—H7B	109.5	C22—C21—H21	118.8
H7A—C7—H7B	109.5	C20—C21—H21	118.8
C2—C7—H7C	109.5	C21—C22—C17	120.5 (2)
H7A—C7—H7C	109.5	C21—C22—C25	118.0 (2)
H7B—C7—H7C	109.5	C17—C22—C25	121.5 (2)
C9—C8—C13	117.9 (2)	C18—C23—H23A	109.5
C9—C8—B1	121.5 (2)	C18—C23—H23B	109.5
C13—C8—B1	120.6 (2)	H23A—C23—H23B	109.5
C10—C9—C8	120.2 (2)	C18—C23—H23C	109.5
C10—C9—C14	117.6 (2)	H23A—C23—H23C	109.5
C8—C9—C14	122.2 (2)	H23B—C23—H23C	109.5
C11—C10—C9	122.0 (3)	C20—C24—H24A	109.5
C11—C10—H10	119.0	C20—C24—H24B	109.5
C9—C10—H10	119.0	H24A—C24—H24B	109.5
C12—C11—C10	117.8 (2)	C20—C24—H24C	109.5
C12—C11—C15	121.8 (2)	H24A—C24—H24C	109.5
C10—C11—C15	120.3 (2)	H24B—C24—H24C	109.5
C11—C12—C13	121.4 (2)	C22—C25—H25A	109.5
C11—C12—H12	119.3	C22—C25—H25B	109.5
C13—C12—H12	119.3	H25A—C25—H25B	109.5
C12—C13—C8	120.7 (2)	C22—C25—H25C	109.5
C12—C13—C16	117.8 (2)	H25A—C25—H25C	109.5
C8—C13—C16	121.5 (2)	H25B—C25—H25C	109.5
C9—C14—H14A	109.5	O1—Li1—O1ⁱ	98.0 (2)
C9—C14—H14B	109.5	O1—Li1—N1	119.5 (2)
H14A—C14—H14B	109.5	O1ⁱ—Li1—N1	138.6 (3)
C9—C14—H14C	109.5	O1—Li1—Li1ⁱ	49.36 (16)
H14A—C14—H14C	109.5	O1ⁱ—Li1—Li1ⁱ	48.66 (16)
H14B—C14—H14C	109.5	N1—Li1—Li1ⁱ	161.4 (3)
C11—C15—H15A	109.5	O1—B1—C17	121.9 (2)
C11—C15—H15B	109.5	O1—B1—C8	120.0 (2)
H15A—C15—H15B	109.5	C17—B1—C8	118.1 (2)
C11—C15—H15C	109.5	C2—N1—C6	117.7 (2)
H15A—C15—H15C	109.5	C2—N1—Li1	128.1 (2)
H15B—C15—H15C	109.5	C6—N1—Li1	114.2 (2)
C13—C16—H16A	109.5	B1—O1—Li1	138.3 (2)
C13—C16—H16B	109.5	B1—O1—Li1ⁱ	137.6 (2)
H16A—C16—H16B	109.5	Li1—O1—Li1ⁱ	82.0 (2)

N1—C2—C3—C4	0.4 (4)	C18—C17—C22—C21	3.3 (4)
C7—C2—C3—C4	−179.3 (2)	B1—C17—C22—C21	−174.9 (2)
C2—C3—C4—C5	0.7 (4)	C18—C17—C22—C25	−179.0 (2)
C3—C4—C5—C6	−0.7 (4)	B1—C17—C22—C25	2.8 (4)
C4—C5—C6—N1	−0.5 (4)	C22—C17—B1—O1	−50.9 (3)
C13—C8—C9—C10	1.2 (3)	C18—C17—B1—O1	131.0 (3)
B1—C8—C9—C10	179.0 (2)	C22—C17—B1—C8	128.9 (3)
C13—C8—C9—C14	−176.5 (2)	C18—C17—B1—C8	−49.2 (3)
B1—C8—C9—C14	1.4 (3)	C9—C8—B1—O1	125.9 (3)
C8—C9—C10—C11	−2.9 (4)	C13—C8—B1—O1	−56.3 (3)
C14—C9—C10—C11	174.9 (2)	C9—C8—B1—C17	−53.9 (3)
C9—C10—C11—C12	2.2 (4)	C13—C8—B1—C17	123.9 (3)
C9—C10—C11—C15	−176.8 (2)	C3—C2—N1—C6	−1.6 (3)
C10—C11—C12—C13	0.2 (4)	C7—C2—N1—C6	178.1 (2)
C15—C11—C12—C13	179.1 (2)	C3—C2—N1—Li1	176.2 (2)
C11—C12—C13—C8	−1.8 (4)	C7—C2—N1—Li1	−4.1 (3)
C11—C12—C13—C16	−179.2 (2)	C5—C6—N1—C2	1.7 (4)
C9—C8—C13—C12	1.1 (3)	C5—C6—N1—Li1	−176.4 (2)
B1—C8—C13—C12	−176.8 (2)	O1—Li1—N1—C2	−159.0 (2)
C9—C8—C13—C16	178.4 (2)	O1ⁱ—Li1—N1—C2	−7.0 (5)
B1—C8—C13—C16	0.5 (3)	Li1ⁱ—Li1—N1—C2	−110.7 (10)
C22—C17—C18—C19	−1.2 (4)	O1—Li1—N1—C6	18.8 (3)
B1—C17—C18—C19	177.0 (2)	O1ⁱ—Li1—N1—C6	170.8 (3)
C22—C17—C18—C23	179.1 (2)	Li1ⁱ—Li1—N1—C6	67.1 (11)
B1—C17—C18—C23	−2.7 (4)	C17—B1—O1—Li1	−60.0 (4)
C17—C18—C19—C20	−2.1 (4)	C8—B1—O1—Li1	120.2 (3)
C23—C18—C19—C20	177.6 (2)	C17—B1—O1—Li1ⁱ	143.1 (3)
C18—C19—C20—C21	3.3 (4)	C8—B1—O1—Li1ⁱ	−36.6 (4)
C18—C19—C20—C24	−176.3 (2)	O1ⁱ—Li1—O1—B1	−164.5 (3)
C19—C20—C21—C22	−1.1 (4)	N1—Li1—O1—B1	−2.8 (5)
C24—C20—C21—C22	178.4 (2)	Li1ⁱ—Li1—O1—B1	−164.5 (3)
C20—C21—C22—C17	−2.1 (4)	O1ⁱ—Li1—O1—Li1ⁱ	0.0
C20—C21—C22—C25	−180.0 (2)	N1—Li1—O1—Li1ⁱ	161.7 (4)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1ⁱⁱ	0.95	2.96	3.787 (3)	146

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Li₂(C₁₈H₂₂BO)₂(C₆H₇N)₂]
M_r	730.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.6075 (11), 9.1307 (11), 26.220 (3)
β (°)	90.124 (2)
V (Å³)	2060.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.63 × 0.19 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.958, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	8145, 2848, 2011
R_int	0.036
θ_max (°)	23.4
(sin θ/λ)_max (Å⁻¹)	0.558

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.140, 1.26
No. of reflections	2848
No. of parameters	260
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1ⁱ	0.95	2.96	3.787 (3)	146

Symmetry code: (i) x, y−1, z.

Acknowledgements

This work was supported by funding from the South Dakota 2010 Initiative, Center for Research and Development of Light-Activated Materials. Purchase of the X-ray diffractometer was made possible with funds from the National Science Foundation (EPS-0554609).

References

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