Crystal structure of the bora-benzene-2,6-lutidine adduct.

In the title compound, C12H14BN, the complete mol-ecule is generated by a crystallographic twofold axis, with two C atoms, the B atom and the N atom lying on the rotation axis. The dihedral angle between the bora-benzene and pyridine rings is 81.20 (6)°. As well as dative electron donation from the N atom to the B atom [B-N = 1.5659 (18) Å], the methyl substituents on the lutidine ring shield the B atom, which further stabilizes the mol-ecule. In the crystal, weak aromatic π-π stacking between the pyridine rings [centroid-centroid separation = 3.6268 (9) Å] is observed, which generates [001] columns of mol-ecules.

Related literature

For the synthesis of the title compound, see: Hoic et al. (1996 ▸). For a related structure, see: Boese et al. (1985 ▸). For bora­benzene adducts as analogues of cyclo­penta­dienyl anions (Cp), see: Bazan et al. (2000 ▸); Wang et al. (2002 ▸); Cui et al. (2010 ▸). For the uses of bora­benzenes and their metal complexes, see: Wang et al. (2002 ▸; Jaska et al. (2006 ▸).

Experimental

Crystal data

C12H14BN

M = 183.05

Monoclinic,

a = 10.008 (2) Å

b = 14.447 (3) Å

c = 7.1360 (14) Å

β = 90.16 (3)°

V = 1031.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.24 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▸) T min = 0.646, T max = 0.746

7258 measured reflections

1482 independent reflections

1280 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.06

1482 reflections

67 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Bruker, 2008 ▸); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▸); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: CHIMERA (Pettersen et al., 2004 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020599/hb7526sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020599/hb7526Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020599/hb7526Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020599/hb7526Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020599/hb7526fig1.tif

The mol­ecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

CCDC reference: 1434350

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

C12H14BN	F(000) = 392
Mr = 183.05	Dx = 1.178 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.008 (2) Å	Cell parameters from 10098 reflections
b = 14.447 (3) Å	θ = 1.0–28.7°
c = 7.1360 (14) Å	µ = 0.07 mm−1
β = 90.16 (3)°	T = 120 K
V = 1031.8 (4) Å3	Needle, yellow
Z = 4	0.24 × 0.18 × 0.16 mm

Bruker Kappa APEXII CCD diffractometer	1482 independent reflections
Radiation source: fine-focus sealed tube	1280 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.028
Detector resolution: 16 pixels mm-1	θmax = 30.0°, θmin = 4.0°
φ scans and ω scans with κ offset	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −16→20
Tmin = 0.646, Tmax = 0.746	l = −9→9
7258 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6142P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1482 reflections	Δρmax = 0.30 e Å−3
67 parameters	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
N1	0.5000	0.38254 (7)	0.7500	0.0182 (2)
C1	0.43941 (9)	0.22210 (7)	0.59114 (13)	0.0229 (2)
H1	0.3993	0.2534	0.4883	0.028*
C2	0.44362 (10)	0.12556 (7)	0.59879 (14)	0.0246 (2)
H2	0.4069	0.0910	0.4977	0.030*
C3	0.5000	0.07806 (9)	0.7500	0.0254 (3)
H3	0.5000	0.0123	0.7500	0.031*
C4	0.38816 (9)	0.42921 (7)	0.80474 (12)	0.0197 (2)
C5	0.38693 (9)	0.52523 (7)	0.80370 (13)	0.0225 (2)
H5	0.3086	0.5578	0.8398	0.027*
C6	0.5000	0.57352 (9)	0.7500	0.0241 (3)
H6	0.5000	0.6393	0.7500	0.029*
C7	0.26941 (10)	0.37460 (7)	0.86747 (15)	0.0258 (2)
H7A	0.2957	0.3332	0.9699	0.039*
H7B	0.2351	0.3379	0.7624	0.039*
H7C	0.1996	0.4169	0.9112	0.039*
B1	0.5000	0.27415 (10)	0.7500	0.0195 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0180 (5)	0.0187 (5)	0.0179 (5)	0.000	−0.0021 (4)	0.000
C1	0.0222 (4)	0.0228 (5)	0.0239 (5)	−0.0022 (3)	−0.0018 (3)	0.0003 (3)
C2	0.0222 (4)	0.0235 (5)	0.0282 (5)	−0.0047 (3)	0.0024 (4)	−0.0045 (4)
C3	0.0230 (6)	0.0179 (6)	0.0355 (7)	0.000	0.0068 (5)	0.000
C4	0.0183 (4)	0.0224 (4)	0.0183 (4)	0.0011 (3)	−0.0013 (3)	0.0003 (3)
C5	0.0237 (5)	0.0221 (5)	0.0218 (5)	0.0042 (3)	0.0006 (3)	−0.0004 (3)
C6	0.0309 (7)	0.0193 (6)	0.0220 (6)	0.000	−0.0004 (5)	0.000
C7	0.0195 (4)	0.0268 (5)	0.0312 (5)	−0.0010 (3)	0.0025 (4)	−0.0003 (4)
B1	0.0177 (6)	0.0177 (6)	0.0230 (6)	0.000	−0.0002 (5)	0.000

N1—C4i	1.3647 (11)	C4—C5	1.3874 (13)
N1—C4	1.3647 (11)	C4—C7	1.4961 (13)
N1—B1	1.5659 (18)	C5—C6	1.3843 (12)
C1—C2	1.3964 (14)	C5—H5	0.9500
C1—B1	1.4881 (12)	C6—C5i	1.3843 (12)
C1—H1	0.9500	C6—H6	0.9500
C2—C3	1.3965 (13)	C7—H7A	0.9800
C2—H2	0.9500	C7—H7B	0.9800
C3—C2i	1.3966 (13)	C7—H7C	0.9800
C3—H3	0.9500	B1—C1i	1.4881 (12)
C4i—N1—C4	120.78 (11)	C6—C5—C4	119.88 (9)
C4i—N1—B1	119.61 (6)	C6—C5—H5	120.1
C4—N1—B1	119.61 (6)	C4—C5—H5	120.1
C2—C1—B1	117.56 (9)	C5i—C6—C5	119.48 (13)
C2—C1—H1	121.2	C5i—C6—H6	120.3
B1—C1—H1	121.2	C5—C6—H6	120.3
C1—C2—C3	122.22 (9)	C4—C7—H7A	109.5
C1—C2—H2	118.9	C4—C7—H7B	109.5
C3—C2—H2	118.9	H7A—C7—H7B	109.5
C2—C3—C2i	121.13 (13)	C4—C7—H7C	109.5
C2—C3—H3	119.4	H7A—C7—H7C	109.5
C2i—C3—H3	119.4	H7B—C7—H7C	109.5
N1—C4—C5	119.99 (9)	C1—B1—C1i	119.30 (12)
N1—C4—C7	118.55 (9)	C1—B1—N1	120.35 (6)
C5—C4—C7	121.46 (8)	C1i—B1—N1	120.35 (6)
B1—C1—C2—C3	1.10 (12)	C4—C5—C6—C5i	0.52 (6)
C1—C2—C3—C2i	−0.59 (7)	C2—C1—B1—C1i	−0.53 (6)
C4i—N1—C4—C5	0.52 (6)	C2—C1—B1—N1	179.47 (6)
B1—N1—C4—C5	−179.47 (6)	C4i—N1—B1—C1	−98.80 (6)
C4i—N1—C4—C7	−178.65 (9)	C4—N1—B1—C1	81.20 (6)
B1—N1—C4—C7	1.35 (9)	C4i—N1—B1—C1i	81.20 (6)
N1—C4—C5—C6	−1.05 (12)	C4—N1—B1—C1i	−98.80 (6)
C7—C4—C5—C6	178.10 (7)