4-Methyl-3-nitro-benzonitrile.

In the title compound, C(8)H(6)N(2)O(2), the nitro group is rotated by 23.2 (3)° 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 ▶); Liang & Wang, (2008 ▶).

Experimental

Crystal data

C8H6N2O2

M = 162.15

Monoclinic,

a = 3.9088 (8) Å

b = 13.576 (3) Å

c = 14.819 (4) Å

β = 99.13 (3)°

V = 776.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.35 × 0.30 × 0.1 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.965, T max = 0.990

7589 measured reflections

1761 independent reflections

1336 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.208

S = 1.10

1753 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 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/S1600536808027414/wk2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027414/wk2090Isup2.hkl

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

C8H6N2O2	F(000) = 336
Mr = 162.15	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1764 reflections
a = 3.9088 (8) Å	θ = 3.1–27.6°
b = 13.576 (3) Å	µ = 0.10 mm−1
c = 14.819 (4) Å	T = 298 K
β = 99.13 (3)°	Block, colourless
V = 776.4 (3) Å3	0.35 × 0.30 × 0.1 mm
Z = 4

Rigaku Mercury2 diffractometer	1761 independent reflections
Radiation source: fine-focus sealed tube	1336 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −17→17
Tmin = 0.965, Tmax = 0.990	l = −19→19
7589 measured 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1036P)2 + 0.2336P] where P = (Fo2 + 2Fc2)/3
1753 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.28 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
O1	1.0921 (7)	0.79875 (18)	0.59741 (14)	0.1001 (9)
O2	1.3658 (7)	0.89476 (18)	0.52048 (17)	0.0932 (8)
N1	1.1627 (5)	0.82762 (16)	0.52533 (14)	0.0584 (6)
N2	0.5214 (8)	0.45178 (18)	0.38967 (18)	0.0803 (8)
C1	1.0021 (5)	0.77768 (15)	0.44045 (14)	0.0444 (5)
C8	0.6195 (7)	0.53049 (18)	0.38358 (16)	0.0568 (6)
C2	0.9631 (5)	0.82620 (16)	0.35611 (15)	0.0462 (5)
C6	0.8914 (6)	0.68242 (16)	0.45126 (14)	0.0470 (5)
H6	0.9185	0.6535	0.5088	0.056*
C4	0.6963 (6)	0.67560 (17)	0.28898 (15)	0.0530 (6)
H4	0.5942	0.6412	0.2374	0.064*
C5	0.7388 (6)	0.63055 (16)	0.37444 (15)	0.0463 (5)
C3	0.8057 (7)	0.77130 (18)	0.28090 (16)	0.0559 (6)
H3	0.7738	0.8004	0.2234	0.067*
C7	1.0660 (8)	0.93151 (18)	0.3406 (2)	0.0672 (7)
H7A	1.1700	0.9601	0.3976	0.101*
H7B	0.8641	0.9687	0.3157	0.101*
H7C	1.2293	0.9326	0.2985	0.101*

	U11	U22	U33	U12	U13	U23
O1	0.145 (2)	0.1075 (18)	0.0430 (11)	−0.0405 (15)	0.0006 (12)	−0.0087 (11)
O2	0.0966 (17)	0.0881 (15)	0.0906 (16)	−0.0397 (13)	0.0017 (12)	−0.0237 (12)
N1	0.0605 (12)	0.0593 (12)	0.0523 (12)	−0.0039 (10)	−0.0011 (9)	−0.0117 (9)
N2	0.106 (2)	0.0562 (14)	0.0755 (16)	−0.0203 (13)	0.0039 (14)	−0.0061 (11)
C1	0.0410 (10)	0.0476 (12)	0.0436 (11)	0.0013 (9)	0.0041 (8)	−0.0064 (9)
C8	0.0662 (15)	0.0501 (13)	0.0521 (14)	−0.0036 (11)	0.0029 (11)	−0.0063 (10)
C2	0.0447 (11)	0.0456 (11)	0.0496 (12)	0.0061 (9)	0.0119 (9)	0.0026 (9)
C6	0.0517 (12)	0.0478 (12)	0.0402 (11)	0.0010 (9)	0.0034 (9)	0.0011 (9)
C4	0.0619 (14)	0.0521 (13)	0.0417 (12)	0.0062 (10)	−0.0014 (10)	−0.0048 (9)
C5	0.0483 (12)	0.0446 (11)	0.0452 (12)	0.0015 (9)	0.0049 (8)	−0.0036 (9)
C3	0.0708 (16)	0.0543 (13)	0.0415 (12)	0.0083 (11)	0.0058 (10)	0.0059 (9)
C7	0.0707 (17)	0.0504 (14)	0.0807 (19)	−0.0005 (12)	0.0125 (14)	0.0096 (12)

O1—N1	1.210 (3)	C6—C5	1.390 (3)
O2—N1	1.218 (3)	C6—H6	0.9300
N1—C1	1.478 (3)	C4—C3	1.379 (3)
N2—C8	1.144 (3)	C4—C5	1.392 (3)
C1—C6	1.381 (3)	C4—H4	0.9300
C1—C2	1.400 (3)	C3—H3	0.9300
C8—C5	1.450 (3)	C7—H7A	0.9600
C2—C3	1.400 (3)	C7—H7B	0.9600
C2—C7	1.513 (3)	C7—H7C	0.9600
O1—N1—O2	122.4 (2)	C3—C4—H4	120.0
O1—N1—C1	118.5 (2)	C5—C4—H4	120.0
O2—N1—C1	119.1 (2)	C6—C5—C4	119.7 (2)
C6—C1—C2	123.55 (19)	C6—C5—C8	120.1 (2)
C6—C1—N1	115.43 (19)	C4—C5—C8	120.2 (2)
C2—C1—N1	121.0 (2)	C4—C3—C2	122.4 (2)
N2—C8—C5	178.9 (3)	C4—C3—H3	118.8
C3—C2—C1	115.6 (2)	C2—C3—H3	118.8
C3—C2—C7	118.4 (2)	C2—C7—H7A	109.5
C1—C2—C7	125.9 (2)	C2—C7—H7B	109.5
C1—C6—C5	118.75 (19)	H7A—C7—H7B	109.5
C1—C6—H6	120.6	C2—C7—H7C	109.5
C5—C6—H6	120.6	H7A—C7—H7C	109.5
C3—C4—C5	119.9 (2)	H7B—C7—H7C	109.5
O1—N1—C1—C6	−23.2 (3)	N1—C1—C6—C5	−179.76 (19)
O2—N1—C1—C6	155.4 (2)	C1—C6—C5—C4	−0.9 (3)
O1—N1—C1—C2	155.8 (2)	C1—C6—C5—C8	−179.9 (2)
O2—N1—C1—C2	−25.6 (3)	C3—C4—C5—C6	0.0 (3)
C6—C1—C2—C3	−0.8 (3)	C3—C4—C5—C8	179.1 (2)
N1—C1—C2—C3	−179.68 (19)	C5—C4—C3—C2	0.5 (4)
C6—C1—C2—C7	177.4 (2)	C1—C2—C3—C4	−0.1 (3)
N1—C1—C2—C7	−1.4 (3)	C7—C2—C3—C4	−178.5 (2)
C2—C1—C6—C5	1.3 (3)