2-Methyl-5-nitro-benzonitrile.

In the title compound, C(8)H(6)N(2)O(2), the nitro group is rotated by 10.2 (2)° out of the plane of the benzene ring. The crystal structure is stabilized by van der Waals inter-actions.

Related literature

For the chemistry of nitrile derivatives, see: Xiong et al. (2002 ▶); Jin et al. (1994 ▶); Brewis et al. (2003 ▶); Dunica et al. (1991 ▶). For related literature, see: Fu & Zhao (2007 ▶).

Experimental

Crystal data

C8H6N2O2

M = 162.15

Monoclinic,

a = 3.8946 (8) Å

b = 7.6350 (15) Å

c = 26.180 (5) Å

β = 91.65 (3)°

V = 778.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.4 × 0.35 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.93, T max = 0.98

7390 measured reflections

1761 independent reflections

1273 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.04

1761 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010982/bx2137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010982/bx2137Isup2.hkl

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

C8H6N2O2	F000 = 336
Mr = 162.15	Dx = 1.384 Mg m−3
Monoclinic, P21/n	Melting point = 349–350 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 3.8946 (8) Å	Cell parameters from 1763 reflections
b = 7.6350 (15) Å	θ = 3.1–27.7º
c = 26.180 (5) Å	µ = 0.10 mm−1
β = 91.65 (3)º	T = 293 (2) K
V = 778.1 (3) Å3	Block, colourless
Z = 4	0.4 × 0.35 × 0.2 mm

Rigaku Mercury2 diffractometer	1761 independent reflections
Radiation source: fine-focus sealed tube	1273 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −5→4
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −9→9
Tmin = 0.93, Tmax = 0.98	l = −33→33
7390 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.1332P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1761 reflections	Δρmax = 0.14 e Å−3
109 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.8171 (4)	0.3298 (2)	0.18614 (5)	0.0590 (4)
C3	0.8617 (4)	0.6612 (2)	0.08273 (6)	0.0450 (4)
C2	0.7935 (4)	0.5051 (2)	0.10776 (5)	0.0451 (4)
H2A	0.6877	0.4120	0.0907	0.054*
C7	0.7618 (5)	0.6787 (2)	0.02938 (6)	0.0534 (4)
C4	1.0183 (4)	0.8045 (2)	0.10793 (6)	0.0489 (4)
C1	0.8882 (4)	0.4929 (2)	0.15883 (6)	0.0469 (4)
N2	0.6808 (5)	0.6958 (2)	−0.01239 (6)	0.0745 (5)
C5	1.1068 (4)	0.7835 (2)	0.15941 (7)	0.0569 (5)
H5A	1.2101	0.8762	0.1770	0.068*
O1	0.9413 (5)	0.3114 (2)	0.22899 (6)	0.0954 (6)
O2	0.6345 (4)	0.2205 (2)	0.16517 (6)	0.0838 (5)
C6	1.0461 (4)	0.6299 (2)	0.18501 (6)	0.0550 (5)
H6A	1.1100	0.6182	0.2193	0.066*
C8	1.0878 (5)	0.9721 (2)	0.08010 (7)	0.0636 (5)
H8A	1.1998	1.0535	0.1030	0.095*
H8B	0.8748	1.0213	0.0676	0.095*
H8C	1.2333	0.9487	0.0519	0.095*

	U11	U22	U33	U12	U13	U23
N1	0.0639 (9)	0.0679 (10)	0.0450 (8)	0.0035 (8)	−0.0017 (7)	0.0075 (7)
C3	0.0453 (8)	0.0507 (9)	0.0387 (8)	−0.0026 (7)	−0.0039 (6)	−0.0050 (6)
C2	0.0460 (8)	0.0481 (9)	0.0407 (8)	−0.0017 (7)	−0.0045 (6)	−0.0051 (6)
C7	0.0660 (11)	0.0465 (9)	0.0473 (9)	−0.0131 (8)	−0.0079 (8)	−0.0006 (7)
C4	0.0438 (8)	0.0519 (9)	0.0509 (9)	−0.0024 (7)	−0.0011 (7)	−0.0091 (7)
C1	0.0445 (8)	0.0559 (10)	0.0401 (8)	0.0037 (7)	−0.0011 (6)	−0.0006 (7)
N2	0.1069 (14)	0.0667 (10)	0.0486 (9)	−0.0268 (9)	−0.0196 (9)	0.0072 (7)
C5	0.0547 (10)	0.0629 (11)	0.0525 (10)	−0.0062 (8)	−0.0072 (8)	−0.0186 (8)
O1	0.1169 (13)	0.1119 (13)	0.0559 (8)	−0.0133 (10)	−0.0234 (8)	0.0294 (8)
O2	0.1135 (13)	0.0681 (9)	0.0688 (9)	−0.0226 (9)	−0.0121 (9)	0.0108 (7)
C6	0.0540 (10)	0.0721 (12)	0.0385 (8)	0.0022 (8)	−0.0078 (7)	−0.0093 (7)
C8	0.0640 (11)	0.0545 (10)	0.0721 (12)	−0.0136 (9)	−0.0039 (9)	−0.0046 (9)

N1—O2	1.217 (2)	C4—C5	1.391 (2)
N1—O1	1.2168 (19)	C4—C8	1.501 (2)
N1—C1	1.467 (2)	C1—C6	1.385 (2)
C3—C4	1.407 (2)	C5—C6	1.375 (3)
C3—C2	1.390 (2)	C5—H5A	0.9300
C3—C7	1.445 (2)	C6—H6A	0.9300
C2—C1	1.380 (2)	C8—H8A	0.9600
C2—H2A	0.9300	C8—H8B	0.9600
C7—N2	1.137 (2)	C8—H8C	0.9600
O2—N1—O1	123.27 (16)	C2—C1—N1	118.73 (14)
O2—N1—C1	118.58 (14)	C6—C1—N1	119.18 (14)
O1—N1—C1	118.15 (15)	C6—C5—C4	121.98 (15)
C4—C3—C2	122.14 (14)	C6—C5—H5A	119.0
C4—C3—C7	118.83 (14)	C4—C5—H5A	119.0
C2—C3—C7	119.02 (13)	C5—C6—C1	118.89 (15)
C1—C2—C3	117.73 (14)	C5—C6—H6A	120.6
C1—C2—H2A	121.1	C1—C6—H6A	120.6
C3—C2—H2A	121.1	C4—C8—H8A	109.5
N2—C7—C3	178.63 (19)	C4—C8—H8B	109.5
C5—C4—C3	117.16 (15)	H8A—C8—H8B	109.5
C5—C4—C8	121.71 (15)	C4—C8—H8C	109.5
C3—C4—C8	121.12 (15)	H8A—C8—H8C	109.5
C2—C1—C6	122.09 (15)	H8B—C8—H8C	109.5
C4—C3—C2—C1	−0.7 (2)	O1—N1—C1—C2	170.40 (16)
C7—C3—C2—C1	−179.26 (14)	O2—N1—C1—C6	169.28 (16)
C2—C3—C4—C5	0.6 (2)	O1—N1—C1—C6	−9.9 (2)
C7—C3—C4—C5	179.19 (15)	C3—C4—C5—C6	0.2 (2)
C2—C3—C4—C8	−179.73 (15)	C8—C4—C5—C6	−179.50 (16)
C7—C3—C4—C8	−1.1 (2)	C4—C5—C6—C1	−0.8 (3)
C3—C2—C1—C6	0.0 (2)	C2—C1—C6—C5	0.7 (3)
C3—C2—C1—N1	179.64 (13)	N1—C1—C6—C5	−178.91 (15)
O2—N1—C1—C2	−10.4 (2)