1-Chloro-2-methyl-3-nitro-benzene.

In the title compound, C(7)H(6)ClNO(2), the chloro, methyl and nitro substituents are situated next to each other in this order on the benzene ring, with the mean plane of the nitro group twisted away from the mean plane of the benzene ring by 38.81 (5)°.

Related literature

For information on industrial chemicals, see: Chloro­nitro­toluenes (2010 ▶). For the use of the title compound as a starting material in the synthesis of 7-chlorovasicine (pyrrolo[2,1-b]quinazolin-3-ol, 8-chloro-1,2,3,9-tetrahydro), see: Southwick & Cremer (1959 ▶). For the toxic effects of the title compound on D. magna, see: Ramos et al. (2001 ▶) and on T. pyriformis, see: Schultz (1999 ▶); Katritzky et al. (2003 ▶). For a related structure, see: Liu & Du (2008 ▶).

Experimental

Crystal data

C7H6ClNO2

M = 171.58

Orthorhombic,

a = 7.3061 (5) Å

b = 13.8392 (9) Å

c = 14.6799 (10) Å

V = 1484.29 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.46 mm−1

T = 125 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.868, T max = 0.956

22310 measured reflections

2271 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.05

2271 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536811004466/jj2075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004466/jj2075Isup2.hkl

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

C7H6ClNO2	F(000) = 704
Mr = 171.58	Dx = 1.536 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9979 reflections
a = 7.3061 (5) Å	θ = 2.8–30.5°
b = 13.8392 (9) Å	µ = 0.46 mm−1
c = 14.6799 (10) Å	T = 125 K
V = 1484.29 (17) Å3	Block, colorless
Z = 8	0.32 × 0.20 × 0.10 mm

Bruker APEXII CCD diffractometer	2271 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.868, Tmax = 0.956	k = −19→19
22310 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.4184P] where P = (Fo2 + 2Fc2)/3
2271 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.38 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
Cl	0.02248 (4)	0.79411 (2)	0.19541 (2)	0.02921 (10)
O1	0.18412 (16)	0.46030 (7)	0.46513 (7)	0.0383 (2)
O2	0.27741 (17)	0.60583 (8)	0.49519 (6)	0.0414 (3)
N	0.21538 (15)	0.54450 (7)	0.44328 (7)	0.0269 (2)
C1	0.09994 (14)	0.68212 (7)	0.23325 (8)	0.0200 (2)
C2	0.11332 (14)	0.66404 (7)	0.32692 (7)	0.0202 (2)
C3	0.18229 (14)	0.57217 (8)	0.34792 (7)	0.0198 (2)
C4	0.22965 (15)	0.50274 (8)	0.28388 (8)	0.0207 (2)
H4A	0.2734	0.4412	0.3026	0.025*
C5	0.21212 (15)	0.52466 (8)	0.19236 (7)	0.0218 (2)
H5A	0.2439	0.4783	0.1474	0.026*
C6	0.14754 (15)	0.61522 (8)	0.16681 (7)	0.0218 (2)
H6A	0.1360	0.6313	0.1041	0.026*
C7	0.05257 (18)	0.73682 (9)	0.39679 (9)	0.0294 (3)
H7A	−0.0502	0.7744	0.3725	0.044*
H7B	0.1544	0.7804	0.4111	0.044*
H7C	0.0139	0.7032	0.4523	0.044*

	U11	U22	U33	U12	U13	U23
Cl	0.02669 (16)	0.01774 (15)	0.04320 (19)	−0.00006 (9)	−0.00430 (11)	0.00518 (11)
O1	0.0576 (6)	0.0269 (5)	0.0303 (5)	−0.0020 (4)	0.0027 (4)	0.0077 (4)
O2	0.0613 (7)	0.0399 (6)	0.0232 (4)	−0.0141 (5)	−0.0070 (4)	−0.0023 (4)
N	0.0321 (5)	0.0269 (5)	0.0218 (4)	−0.0029 (4)	0.0012 (4)	0.0015 (4)
C1	0.0176 (4)	0.0150 (4)	0.0274 (5)	−0.0011 (4)	−0.0013 (4)	0.0010 (4)
C2	0.0185 (5)	0.0174 (5)	0.0248 (5)	−0.0030 (4)	0.0024 (4)	−0.0032 (4)
C3	0.0208 (5)	0.0197 (5)	0.0189 (5)	−0.0033 (4)	0.0009 (4)	0.0007 (4)
C4	0.0207 (5)	0.0159 (4)	0.0256 (5)	−0.0006 (4)	0.0003 (4)	−0.0015 (4)
C5	0.0221 (5)	0.0202 (5)	0.0232 (5)	−0.0012 (4)	0.0013 (4)	−0.0054 (4)
C6	0.0222 (5)	0.0226 (5)	0.0207 (5)	−0.0027 (4)	−0.0013 (4)	−0.0003 (4)
C7	0.0326 (6)	0.0234 (5)	0.0324 (6)	−0.0011 (5)	0.0074 (5)	−0.0095 (5)

Cl—C1	1.7410 (11)	C4—C5	1.3832 (16)
O1—N	1.2300 (13)	C4—H4A	0.9500
O2—N	1.2275 (14)	C5—C6	1.3907 (16)
N—C3	1.4713 (14)	C5—H5A	0.9500
C1—C6	1.3891 (15)	C6—H6A	0.9500
C1—C2	1.4010 (15)	C7—H7A	0.9800
C2—C3	1.4018 (15)	C7—H7B	0.9800
C2—C7	1.5045 (15)	C7—H7C	0.9800
C3—C4	1.3882 (15)
O2—N—O1	124.17 (11)	C3—C4—H4A	120.6
O2—N—C3	118.13 (10)	C4—C5—C6	119.41 (10)
O1—N—C3	117.66 (10)	C4—C5—H5A	120.3
C6—C1—C2	123.55 (10)	C6—C5—H5A	120.3
C6—C1—Cl	116.78 (8)	C1—C6—C5	119.74 (10)
C2—C1—Cl	119.66 (8)	C1—C6—H6A	120.1
C1—C2—C3	113.76 (10)	C5—C6—H6A	120.1
C1—C2—C7	121.93 (10)	C2—C7—H7A	109.5
C3—C2—C7	124.29 (10)	C2—C7—H7B	109.5
C4—C3—C2	124.64 (10)	H7A—C7—H7B	109.5
C4—C3—N	115.04 (10)	C2—C7—H7C	109.5
C2—C3—N	120.29 (10)	H7A—C7—H7C	109.5
C5—C4—C3	118.87 (10)	H7B—C7—H7C	109.5
C5—C4—H4A	120.6
C6—C1—C2—C3	0.94 (15)	O1—N—C3—C4	−38.35 (15)
Cl—C1—C2—C3	−178.30 (7)	O2—N—C3—C2	−38.54 (16)
C6—C1—C2—C7	−177.26 (11)	O1—N—C3—C2	143.61 (12)
Cl—C1—C2—C7	3.50 (15)	C2—C3—C4—C5	1.31 (17)
C1—C2—C3—C4	−1.68 (15)	N—C3—C4—C5	−176.63 (10)
C7—C2—C3—C4	176.46 (11)	C3—C4—C5—C6	−0.09 (17)
C1—C2—C3—N	176.17 (9)	C2—C1—C6—C5	0.13 (17)
C7—C2—C3—N	−5.69 (16)	Cl—C1—C6—C5	179.39 (8)
O2—N—C3—C4	139.50 (12)	C4—C5—C6—C1	−0.59 (17)