Propyl-amine-borane.

The title compound, C(3)H(12)BN, was solved using data collected from a multiple crystal (note incomplete data shell). The cell packing is dominated by bifurcated attractive N-H(δ+)⋯(δ-)H-B inter-actions.

Related literature

For background to our studies of hydrogen storage materials and the synthesis: see Bowden et al. (2007 ▶, 2008 ▶). For other H3B–N-containing boranes, see: Alston et al. (1985 ▶); Spielmann et al. (2008 ▶). For bond lengths and angles in boranes, see: Ting et al. (1972 ▶); Klooster et al. (1999 ▶); For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C3H12BN

M = 72.95

Monoclinic,

a = 9.173 (4) Å

b = 8.638 (3) Å

c = 7.360 (3) Å

β = 97.892 (8)°

V = 577.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.05 mm−1

T = 93 K

0.45 × 0.25 × 0.03 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer

Absorption correction: none

846 measured reflections

846 independent reflections

503 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.138

S = 1.00

846 reflections

57 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: RLATT (Bruker, 2004 ▶) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901887X/bt2953sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901887X/bt2953Isup2.hkl

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

C3H12BN	F(000) = 168
Mr = 72.95	Dx = 0.839 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1112 reflections
a = 9.173 (4) Å	θ = 3.3–26.4°
b = 8.638 (3) Å	µ = 0.05 mm−1
c = 7.360 (3) Å	T = 93 K
β = 97.892 (8)°	Plate, colourless
V = 577.7 (4) Å3	0.45 × 0.25 × 0.03 mm
Z = 4

Bruker–Nonius APEXII CCD area-detector diffractometer	503 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
graphite	θmax = 25.1°, θmin = 3.7°
Detector resolution: 8.192 pixels mm-1	h = −10→10
φ and ω scans	k = 0→10
846 measured reflections	l = 0→8
846 independent reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1469P] where P = (Fo2 + 2Fc2)/3
846 reflections	(Δ/σ)max < 0.001
57 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.57394 (18)	0.52001 (19)	0.2744 (2)	0.0238 (5)
H8	0.5692	0.5971	0.1940	0.029*
H9	0.5954	0.5610	0.386	0.029*
C1	0.6964 (2)	0.4155 (2)	0.2415 (3)	0.0257 (6)
H6	0.6737	0.3705	0.1238	0.031*
H7	0.7038	0.3345	0.3288	0.031*
C2	0.8429 (2)	0.4958 (3)	0.2528 (3)	0.0322 (7)
H4	0.8675	0.5373	0.370	0.039*
H5	0.8353	0.5779	0.1690	0.039*
C3	0.9647 (3)	0.3874 (3)	0.2123 (4)	0.0451 (8)
H1	0.9727	0.3009	0.2992	0.068*
H2	1.0582	0.4439	0.2245	0.068*
H3	0.9418	0.3475	0.0870	0.068*
B1	0.4156 (3)	0.4415 (3)	0.2603 (3)	0.0270 (6)
H10	0.3330	0.5297	0.2937	0.038 (4)*
H11	0.4196	0.3425	0.3603	0.038 (4)*
H12	0.3825	0.3969	0.1169	0.038 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0366 (11)	0.0151 (9)	0.0210 (10)	−0.0006 (7)	0.0080 (8)	−0.0003 (7)
C1	0.0373 (13)	0.0181 (11)	0.0223 (12)	0.0025 (9)	0.0066 (9)	0.0006 (8)
C2	0.0389 (15)	0.0311 (13)	0.0268 (13)	0.0016 (11)	0.0053 (10)	0.0013 (10)
C3	0.0395 (16)	0.0542 (17)	0.0432 (16)	0.0078 (13)	0.0109 (12)	0.0059 (12)
B1	0.0372 (15)	0.0226 (13)	0.0216 (13)	−0.0017 (11)	0.0056 (10)	−0.0002 (9)

N1—C1	1.487 (3)	C2—H4	0.9359
N1—B1	1.593 (3)	C2—H5	0.9359
N1—H8	0.8880	C3—H1	0.9800
N1—H9	0.8880	C3—H2	0.9800
C1—C2	1.504 (3)	C3—H3	0.9800
C1—H6	0.9465	B1—H10	1.1255
C1—H7	0.9465	B1—H11	1.1255
C2—C3	1.518 (3)	B1—H12	1.1255
C1—N1—B1	115.68 (17)	C1—C2—H5	109.1
C1—N1—H8	108.4	C3—C2—H5	109.1
B1—N1—H8	108.4	H4—C2—H5	107.9
C1—N1—H9	108.4	C2—C3—H1	109.5
B1—N1—H9	108.4	C2—C3—H2	109.5
H8—N1—H9	107.4	H1—C3—H2	109.5
N1—C1—C2	113.60 (17)	C2—C3—H3	109.5
N1—C1—H6	108.8	H1—C3—H3	109.5
C2—C1—H6	108.8	H2—C3—H3	109.5
N1—C1—H7	108.8	N1—B1—H10	109.5
C2—C1—H7	108.8	N1—B1—H11	109.5
H6—C1—H7	107.7	H10—B1—H11	109.5
C1—C2—C3	112.4 (2)	N1—B1—H12	109.5
C1—C2—H4	109.1	H10—B1—H12	109.5
C3—C2—H4	109.1	H11—B1—H12	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···H11i	0.89	2.16	2.96	149
N1—H9···H11ii	0.89	2.07	2.93	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H8⋯H11i	0.89	2.16	2.96	149
N1—H9⋯H11ii	0.89	2.07	2.93	163

Symmetry codes: (i) ; (ii) .