Methyl 4-chloro-3-nitro-benzoate.

In the title compound, C(8)H(6)ClNO(4), the mol-ecules are linked by C-H⋯O inter-actions to form a chain parallel to the a axis. The chains are further connected by slipped π-π stacking between symmetry-related benzene rings, with a centroid-to-centroid distance of 3.646 (2) Å and an inter-planar distance of 3.474 Å, resulting in an offset of 1.106 Å.

Related literature

For related literature, see: de Souza et al. (2006 ▶); Jin & Xiao (2005 ▶); Spiniello & White (2003 ▶); Jönssen et al. (2004 ▶); Andrews & Ladlow (2003 ▶).

Experimental

Crystal data

C8H6ClNO4

M = 215.59

Triclinic,

a = 7.338 (1) Å

b = 7.480 (1) Å

c = 9.715 (2) Å

α = 98.39 (3)°

β = 94.89 (3)°

γ = 118.95 (3)°

V = 454.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 293 (2) K

0.40 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.854, T max = 0.961

1918 measured reflections

1773 independent reflections

1389 reflections with I > 2σ(I)

R int = 0.019

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.142

S = 1.12

1773 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067219/dn2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067219/dn2295Isup2.hkl

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

C8H6ClNO4	Z = 2
Mr = 215.59	F000 = 220
Triclinic, P1	Dx = 1.577 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.338 (1) Å	Cell parameters from 25 reflections
b = 7.480 (1) Å	θ = 9–13º
c = 9.715 (2) Å	µ = 0.41 mm−1
α = 98.39 (3)º	T = 293 (2) K
β = 94.89 (3)º	Box, colourless
γ = 118.95 (3)º	0.40 × 0.10 × 0.10 mm
V = 454.1 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.2º
T = 293(2) K	h = 0→9
ω/2θ scans	k = −9→8
Absorption correction: ψ scan(North et al., 1968)	l = −11→11
Tmin = 0.854, Tmax = 0.961	3 standard reflections
1918 measured reflections	every 200 reflections
1773 independent reflections	intensity decay: none
1389 reflections with I > 2σ(I)

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2181P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
1773 reflections	Δρmax = 0.21 e Å−3
128 parameters	Δρmin = −0.24 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
C1	−0.2034 (5)	0.0805 (6)	0.0613 (3)	0.0722 (9)
H1A	−0.3435	−0.0080	0.0779	0.108*
H1B	−0.1832	0.0171	−0.0248	0.108*
H1C	−0.1857	0.2143	0.0536	0.108*
C2	−0.0585 (4)	0.1907 (4)	0.3056 (3)	0.0454 (6)
C3	0.1131 (4)	0.2225 (4)	0.4166 (3)	0.0417 (6)
C4	0.2701 (4)	0.1747 (4)	0.3866 (3)	0.0502 (7)
H4	0.2672	0.1180	0.2941	0.060*
C5	0.4285 (4)	0.2108 (4)	0.4925 (3)	0.0536 (7)
H5	0.5306	0.1769	0.4709	0.064*
C6	0.4376 (4)	0.2965 (4)	0.6299 (3)	0.0497 (6)
C7	0.2808 (4)	0.3452 (4)	0.6588 (3)	0.0459 (6)
C8	0.1197 (4)	0.3055 (4)	0.5547 (3)	0.0425 (6)
H8	0.0146	0.3344	0.5771	0.051*
Cl	0.63808 (12)	0.33572 (14)	0.75859 (9)	0.0731 (3)
N1	0.2849 (4)	0.4450 (4)	0.8022 (2)	0.0569 (6)
O1	−0.0490 (3)	0.1079 (3)	0.1782 (2)	0.0591 (5)
O2	−0.1910 (3)	0.2373 (3)	0.3279 (2)	0.0626 (6)
O3	0.4525 (4)	0.5930 (4)	0.8665 (2)	0.0838 (7)
O4	0.1169 (4)	0.3786 (4)	0.8445 (2)	0.0801 (7)

	U11	U22	U33	U12	U13	U23
C1	0.075 (2)	0.089 (2)	0.0466 (17)	0.0412 (19)	0.0021 (15)	0.0024 (15)
C2	0.0449 (14)	0.0383 (13)	0.0488 (15)	0.0175 (11)	0.0148 (11)	0.0063 (11)
C3	0.0406 (13)	0.0343 (12)	0.0489 (14)	0.0170 (10)	0.0144 (11)	0.0086 (10)
C4	0.0533 (15)	0.0490 (15)	0.0560 (16)	0.0298 (13)	0.0225 (13)	0.0108 (12)
C5	0.0475 (15)	0.0572 (16)	0.0691 (18)	0.0328 (13)	0.0226 (13)	0.0198 (14)
C6	0.0412 (13)	0.0462 (14)	0.0633 (17)	0.0207 (12)	0.0122 (12)	0.0191 (12)
C7	0.0466 (14)	0.0388 (13)	0.0491 (15)	0.0187 (11)	0.0126 (11)	0.0085 (11)
C8	0.0399 (13)	0.0363 (12)	0.0532 (15)	0.0199 (10)	0.0147 (11)	0.0084 (10)
Cl	0.0564 (5)	0.0836 (6)	0.0821 (6)	0.0363 (4)	0.0021 (4)	0.0278 (4)
N1	0.0682 (16)	0.0606 (15)	0.0451 (13)	0.0349 (13)	0.0112 (12)	0.0106 (11)
O1	0.0626 (12)	0.0725 (13)	0.0444 (10)	0.0400 (11)	0.0080 (9)	−0.0024 (9)
O2	0.0584 (12)	0.0832 (15)	0.0574 (12)	0.0468 (11)	0.0118 (9)	0.0049 (10)
O3	0.0794 (16)	0.0785 (16)	0.0661 (15)	0.0294 (13)	−0.0085 (12)	−0.0115 (12)
O4	0.0839 (17)	0.0938 (18)	0.0647 (14)	0.0446 (14)	0.0324 (13)	0.0128 (12)

C1—O1	1.450 (4)	C4—H4	0.9300
C1—H1A	0.9600	C5—C6	1.375 (4)
C1—H1B	0.9600	C5—H5	0.9300
C1—H1C	0.9600	C6—C7	1.402 (4)
C2—O2	1.207 (3)	C6—Cl	1.725 (3)
C2—O1	1.324 (3)	C7—C8	1.370 (4)
C2—C3	1.486 (4)	C7—N1	1.471 (3)
C3—C8	1.380 (4)	C8—H8	0.9300
C3—C4	1.402 (3)	N1—O3	1.215 (3)
C4—C5	1.376 (4)	N1—O4	1.220 (3)
O1—C1—H1A	109.5	C6—C5—H5	119.6
O1—C1—H1B	109.5	C4—C5—H5	119.6
H1A—C1—H1B	109.5	C5—C6—C7	118.1 (3)
O1—C1—H1C	109.5	C5—C6—Cl	118.7 (2)
H1A—C1—H1C	109.5	C7—C6—Cl	123.1 (2)
H1B—C1—H1C	109.5	C8—C7—C6	121.6 (2)
O2—C2—O1	123.3 (3)	C8—C7—N1	117.2 (2)
O2—C2—C3	124.1 (2)	C6—C7—N1	121.2 (2)
O1—C2—C3	112.7 (2)	C7—C8—C3	120.1 (2)
C8—C3—C4	118.7 (2)	C7—C8—H8	120.0
C8—C3—C2	118.5 (2)	C3—C8—H8	120.0
C4—C3—C2	122.8 (2)	O3—N1—O4	125.0 (3)
C5—C4—C3	120.7 (2)	O3—N1—C7	117.8 (2)
C5—C4—H4	119.6	O4—N1—C7	117.1 (2)
C3—C4—H4	119.6	C2—O1—C1	116.9 (2)
C6—C5—C4	120.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.47	3.272 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.47	3.272 (3)	145

Symmetry code: (i) .