N-(Cyano-meth-yl)benzamide.

In the structure of the title compound, C(9)H(8)N(2)O, the amide group is twisted by a dihedral angle of 21.86 (7)° with respect to the benzene ring, while the planes of the benzene ring and cyano-methyl group form a dihedral angle of 53.13 (11)°. In the crystal structure, mol-ecules are linked via N-H⋯O hydrogen bonds, forming a chain running parallel to the a axis.

Related literature

For the biological activity and medicinal properties of tetra­zole derivatives, see: Smissman et al. (1976 ▶); McGuire et al. (1990 ▶); Lunn et al. (1992 ▶); Itoh et al. (1995 ▶); Upadhayaya et al. (2004 ▶); Wu et al. (2008 ▶); Rostom et al. (2009 ▶); Burger (1991 ▶); Singh et al. (1980 ▶). For the synthetic procedure, see: Adams & Langley (1941a ▶,b ▶).

Experimental

Crystal data

C9H8N2O

M = 160.17

Orthorhombic,

a = 9.8623 (5) Å

b = 8.0576 (4) Å

c = 20.9268 (9) Å

V = 1662.98 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.33 × 0.28 × 0.22 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

11132 measured reflections

1920 independent reflections

1433 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.02

1920 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003557/dn2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003557/dn2533Isup2.hkl

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

C9H8N2O	Dx = 1.280 Mg m−3
Mr = 160.17	Melting point: 413 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3689 reflections
a = 9.8623 (5) Å	θ = 2.5–27.2°
b = 8.0576 (4) Å	µ = 0.09 mm−1
c = 20.9268 (9) Å	T = 296 K
V = 1662.98 (14) Å3	Block, colourless
Z = 8	0.33 × 0.28 × 0.22 mm
F(000) = 672

Bruker X8 APEXII CCD area-detector diffractometer	1433 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 27.6°, θmin = 2.8°
φ and ω scans	h = −12→12
11132 measured reflections	k = −10→10
1920 independent reflections	l = −26→27

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2439P] where P = (Fo2 + 2Fc2)/3
1920 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.24170 (14)	0.39220 (16)	0.13675 (7)	0.0488 (3)
C2	0.25299 (17)	0.43033 (18)	0.07283 (7)	0.0591 (4)
C3	0.36704 (17)	0.38418 (18)	0.03941 (7)	0.0592 (4)
C4	0.47054 (16)	0.30131 (19)	0.06980 (7)	0.0552 (4)
C5	0.46079 (13)	0.26308 (16)	0.13418 (6)	0.0448 (3)
C6	0.34534 (11)	0.30793 (14)	0.16810 (6)	0.0387 (3)
C7	0.32434 (11)	0.26377 (15)	0.23629 (6)	0.0415 (3)
C8	0.41628 (14)	0.17663 (17)	0.33761 (6)	0.0498 (3)
C9	0.37055 (14)	0.31427 (19)	0.37822 (6)	0.0529 (3)
O1	0.21031 (8)	0.25889 (15)	0.26031 (5)	0.0645 (3)
N1	0.43271 (11)	0.22652 (14)	0.27184 (5)	0.0456 (3)
N2	0.33580 (17)	0.4211 (2)	0.40988 (7)	0.0792 (4)
H1	0.1646 (16)	0.4224 (18)	0.1609 (7)	0.064 (4)*
H2	0.1826 (17)	0.489 (2)	0.0525 (8)	0.075 (5)*
H3	0.3723 (16)	0.410 (2)	−0.0064 (8)	0.073 (5)*
H4	0.5496 (17)	0.267 (2)	0.0484 (8)	0.067 (5)*
H5	0.5302 (16)	0.2004 (18)	0.1546 (7)	0.054 (4)*
H6	0.5098 (18)	0.2419 (17)	0.2585 (7)	0.053 (4)*
H7	0.5037 (17)	0.1326 (19)	0.3548 (8)	0.065 (4)*
H8	0.3480 (15)	0.0870 (17)	0.3409 (7)	0.057 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0411 (7)	0.0482 (7)	0.0571 (8)	0.0051 (6)	−0.0007 (6)	0.0009 (6)
C2	0.0638 (9)	0.0554 (8)	0.0581 (8)	0.0075 (7)	−0.0087 (7)	0.0066 (7)
C3	0.0733 (11)	0.0587 (8)	0.0457 (7)	−0.0087 (8)	−0.0014 (7)	0.0005 (6)
C4	0.0508 (8)	0.0631 (8)	0.0517 (7)	−0.0064 (7)	0.0110 (6)	−0.0100 (6)
C5	0.0333 (6)	0.0512 (7)	0.0500 (7)	−0.0016 (5)	0.0015 (5)	−0.0043 (5)
C6	0.0290 (5)	0.0400 (5)	0.0470 (6)	−0.0038 (5)	−0.0013 (5)	−0.0023 (5)
C7	0.0240 (5)	0.0503 (6)	0.0502 (7)	−0.0016 (5)	0.0027 (5)	0.0016 (5)
C8	0.0373 (7)	0.0564 (8)	0.0558 (7)	0.0041 (6)	0.0010 (6)	0.0149 (6)
C9	0.0435 (7)	0.0665 (8)	0.0487 (7)	0.0021 (6)	0.0020 (6)	0.0156 (7)
O1	0.0224 (4)	0.1126 (9)	0.0586 (6)	−0.0004 (5)	0.0037 (4)	0.0142 (5)
N1	0.0236 (5)	0.0632 (7)	0.0500 (6)	−0.0002 (5)	0.0027 (4)	0.0093 (5)
N2	0.0867 (11)	0.0836 (9)	0.0675 (8)	0.0108 (8)	0.0100 (8)	−0.0003 (7)

C1—C2	1.377 (2)	C5—H5	0.952 (16)
C1—C6	1.3915 (17)	C6—C7	1.4852 (17)
C1—H1	0.945 (16)	C7—O1	1.2324 (13)
C2—C3	1.376 (2)	C7—N1	1.3364 (15)
C2—H2	0.940 (18)	C8—N1	1.4430 (17)
C3—H3	0.984 (16)	C8—C9	1.468 (2)
C4—C3	1.376 (2)	C8—H8	0.990 (15)
C4—H4	0.940 (17)	C8—H7	0.999 (17)
C5—C4	1.3854 (19)	C9—N2	1.1389 (19)
C5—C6	1.3896 (17)	N1—H6	0.820 (17)
C5—C6—C1	119.21 (12)	N1—C8—H8	110.2 (8)
C5—C6—C7	122.87 (11)	C9—C8—H8	107.6 (8)
C1—C6—C7	117.86 (11)	N1—C8—H7	110.2 (9)
O1—C7—N1	119.70 (11)	C9—C8—H7	109.0 (9)
O1—C7—C6	121.79 (11)	H8—C8—H7	107.6 (12)
N1—C7—C6	118.50 (10)	N2—C9—C8	179.61 (18)
C4—C5—C6	119.72 (13)	C3—C2—C1	119.98 (14)
C4—C5—H5	120.3 (9)	C3—C2—H2	120.6 (10)
C6—C5—H5	119.9 (9)	C1—C2—H2	119.4 (10)
C3—C4—C5	120.40 (14)	C4—C3—C2	120.20 (14)
C3—C4—H4	122.4 (10)	C4—C3—H3	121.1 (10)
C5—C4—H4	117.2 (10)	C2—C3—H3	118.7 (9)
C2—C1—C6	120.49 (13)	C7—N1—C8	120.25 (11)
C2—C1—H1	121.8 (9)	C7—N1—H6	121.2 (11)
C6—C1—H1	117.7 (9)	C8—N1—H6	118.2 (11)
N1—C8—C9	112.10 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···O1i	0.819 (17)	2.021 (18)	2.8313 (14)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H6⋯O1i	0.819 (17)	2.021 (18)	2.8313 (14)	169

Symmetry code: (i) .