Ethyl 4-chloro-3-nitro-benzoate.

In the mol-ecule of the title compound, C(9)H(8)ClNO(4), an intra-molecular C-H⋯O hydrogen bond results in the formation of a planar five-membered ring, which is nearly coplanar with the adjacent six-membered ring, the rings being oriented at a dihedral angle of 4.40 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For related literature, see: Jönsson et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H8ClNO4

M = 229.61

Monoclinic,

a = 12.930 (3) Å

b = 7.4820 (15) Å

c = 20.945 (4) Å

β = 92.11 (3)°

V = 2024.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.866, T max = 0.964

1984 measured reflections

1984 independent reflections

1449 reflections with I > 2σ(I)

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.06

1984 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Siemens, 1996 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068304/hk2403sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068304/hk2403Isup2.hkl

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

C9H8ClNO4	F000 = 944
Mr = 229.61	Dx = 1.506 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 12.930 (3) Å	θ = 9–14º
b = 7.4820 (15) Å	µ = 0.37 mm−1
c = 20.945 (4) Å	T = 298 (2) K
β = 92.11 (3)º	Block, colorless
V = 2024.9 (7) Å3	0.40 × 0.30 × 0.10 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.0º
T = 298(2) K	h = −15→15
ω/2θ scans	k = 0→9
Absorption correction: ψ scan(North et al., 1968)	l = 0→25
Tmin = 0.866, Tmax = 0.964	3 standard reflections
1984 measured reflections	every 120 min
1984 independent reflections	intensity decay: none
1449 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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.06P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1984 reflections	Δρmax = 0.16 e Å−3
136 parameters	Δρmin = −0.21 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
Cl	1.15365 (6)	0.38995 (10)	0.39251 (4)	0.0722 (3)
O1	0.91716 (14)	0.1218 (3)	0.65000 (8)	0.0663 (6)
O2	0.78374 (14)	0.0870 (3)	0.58085 (9)	0.0627 (5)
O3	0.9430 (2)	0.3802 (4)	0.33433 (11)	0.1031 (9)
O4	0.87451 (19)	0.1219 (3)	0.35272 (10)	0.0825 (7)
N	0.92750 (19)	0.2507 (4)	0.36829 (10)	0.0628 (6)
C1	0.8393 (3)	0.2219 (5)	0.74482 (16)	0.0967 (12)
H1A	0.7999	0.1862	0.7807	0.145*
H1B	0.8023	0.3127	0.7210	0.145*
H1C	0.9051	0.2681	0.7598	0.145*
C2	0.8556 (3)	0.0672 (5)	0.70361 (13)	0.0801 (10)
H2A	0.8912	−0.0264	0.7277	0.096*
H2B	0.7894	0.0207	0.6879	0.096*
C3	0.87120 (18)	0.1287 (3)	0.59279 (11)	0.0427 (5)
C4	0.94310 (16)	0.1938 (3)	0.54379 (10)	0.0387 (5)
C5	0.90841 (17)	0.1923 (3)	0.48080 (10)	0.0408 (5)
H5A	0.8426	0.1492	0.4700	0.049*
C6	0.97087 (18)	0.2546 (3)	0.43393 (11)	0.0444 (5)
C7	1.06993 (18)	0.3170 (3)	0.44914 (11)	0.0459 (6)
C8	1.10485 (18)	0.3167 (3)	0.51210 (12)	0.0489 (6)
H8A	1.1711	0.3576	0.5229	0.059*
C9	1.04200 (17)	0.2561 (3)	0.55916 (11)	0.0446 (5)
H9A	1.0660	0.2569	0.6016	0.054*

	U11	U22	U33	U12	U13	U23
Cl	0.0766 (5)	0.0632 (5)	0.0794 (5)	0.0006 (4)	0.0387 (4)	0.0099 (4)
O1	0.0616 (11)	0.0952 (15)	0.0424 (10)	−0.0104 (10)	0.0052 (8)	0.0096 (9)
O2	0.0497 (10)	0.0774 (13)	0.0612 (11)	−0.0127 (9)	0.0065 (8)	0.0051 (9)
O3	0.130 (2)	0.116 (2)	0.0628 (13)	−0.0096 (17)	0.0003 (14)	0.0378 (14)
O4	0.1026 (17)	0.0833 (16)	0.0601 (12)	0.0024 (14)	−0.0146 (11)	−0.0164 (11)
N	0.0721 (15)	0.0704 (16)	0.0461 (12)	0.0122 (13)	0.0057 (11)	0.0025 (12)
C1	0.109 (3)	0.109 (3)	0.074 (2)	0.028 (2)	0.037 (2)	0.012 (2)
C2	0.088 (2)	0.107 (3)	0.0461 (15)	−0.011 (2)	0.0176 (14)	0.0144 (16)
C3	0.0456 (13)	0.0368 (12)	0.0455 (13)	0.0046 (10)	0.0015 (10)	−0.0005 (10)
C4	0.0422 (11)	0.0301 (11)	0.0441 (12)	0.0041 (9)	0.0044 (9)	−0.0015 (9)
C5	0.0397 (11)	0.0347 (11)	0.0480 (13)	0.0031 (9)	0.0012 (9)	−0.0023 (10)
C6	0.0526 (13)	0.0385 (12)	0.0424 (12)	0.0085 (10)	0.0053 (10)	0.0005 (10)
C7	0.0517 (13)	0.0340 (12)	0.0531 (14)	0.0057 (10)	0.0157 (11)	0.0025 (10)
C8	0.0412 (12)	0.0402 (13)	0.0657 (16)	−0.0015 (10)	0.0054 (11)	−0.0038 (11)
C9	0.0424 (12)	0.0443 (13)	0.0472 (13)	0.0021 (10)	0.0009 (10)	−0.0032 (10)

Cl—C7	1.724 (2)	C2—H2B	0.9700
O1—C3	1.319 (3)	C3—C4	1.492 (3)
O1—C2	1.459 (3)	C4—C5	1.378 (3)
O2—C3	1.191 (3)	C4—C9	1.388 (3)
N—O3	1.222 (3)	C5—C6	1.375 (3)
N—O4	1.220 (3)	C5—H5A	0.9300
N—C6	1.466 (3)	C6—C7	1.389 (3)
C1—C2	1.463 (5)	C7—C8	1.378 (4)
C1—H1A	0.9600	C8—C9	1.377 (3)
C1—H1B	0.9600	C8—H8A	0.9300
C1—H1C	0.9600	C9—H9A	0.9300
C2—H2A	0.9700
C3—O1—C2	118.0 (2)	C5—C4—C9	119.3 (2)
O4—N—O3	124.9 (3)	C5—C4—C3	117.84 (19)
O4—N—C6	117.3 (2)	C9—C4—C3	122.8 (2)
O3—N—C6	117.7 (3)	C6—C5—C4	120.1 (2)
C2—C1—H1A	109.5	C6—C5—H5A	119.9
C2—C1—H1B	109.5	C4—C5—H5A	119.9
H1A—C1—H1B	109.5	C5—C6—C7	120.7 (2)
C2—C1—H1C	109.5	C5—C6—N	116.6 (2)
H1A—C1—H1C	109.5	C7—C6—N	122.6 (2)
H1B—C1—H1C	109.5	C8—C7—C6	119.1 (2)
O1—C2—C1	109.1 (3)	C8—C7—Cl	117.85 (19)
O1—C2—H2A	109.9	C6—C7—Cl	123.07 (19)
C1—C2—H2A	109.9	C9—C8—C7	120.3 (2)
O1—C2—H2B	109.9	C9—C8—H8A	119.9
C1—C2—H2B	109.9	C7—C8—H8A	119.9
H2A—C2—H2B	108.3	C8—C9—C4	120.5 (2)
O2—C3—O1	125.0 (2)	C8—C9—H9A	119.8
O2—C3—C4	123.5 (2)	C4—C9—H9A	119.8
O1—C3—C4	111.5 (2)
C3—O1—C2—C1	−109.8 (3)	C3—C4—C5—C6	178.6 (2)
C2—O1—C3—O2	−3.0 (4)	C5—C4—C9—C8	0.3 (3)
C2—O1—C3—C4	177.6 (2)	C3—C4—C9—C8	−179.2 (2)
O4—N—C6—C5	−38.6 (3)	C4—C5—C6—C7	1.0 (3)
O3—N—C6—C5	138.0 (3)	C4—C5—C6—N	−179.2 (2)
O4—N—C6—C7	141.2 (3)	C5—C6—C7—C8	−0.3 (3)
O3—N—C6—C7	−42.2 (3)	N—C6—C7—C8	179.8 (2)
O2—C3—C4—C5	−5.1 (3)	C5—C6—C7—Cl	177.82 (17)
O1—C3—C4—C5	174.2 (2)	N—C6—C7—Cl	−2.0 (3)
O2—C3—C4—C9	174.4 (2)	C6—C7—C8—C9	−0.3 (3)
O1—C3—C4—C9	−6.2 (3)	Cl—C7—C8—C9	−178.58 (18)
C9—C4—C5—C6	−1.0 (3)	C7—C8—C9—C4	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2	0.97	2.29	2.706 (3)	104
C8—H8A···O2i	0.93	2.53	3.357 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2	0.97	2.29	2.706 (3)	104
C8—H8A⋯O2i	0.93	2.53	3.357 (3)	148

Symmetry code: (i) .