2-Chloro-ethyl 4-nitro-benzoate.

The title compound, C(9)H(8)ClNO(4), crystallizes with two mol-ecules in the asymmetric unit. In each mol-ecule, the carboxyl-ate group is nearly coplanar with the benzene ring, forming dihedral angles of 2.4 (1) and 4.9 (1)°. In the crystal, mol-ecules are linked through weak C-H⋯O and C-H⋯Cl hydrogen bonds. A short O⋯N contact of 2.7660 (19) Å occurs between the nitro groups of adjacent mol-ecules.

Related literature

For benzoates as inter­mediates in the chemistry of pigments and pharmaceuticals, see: Zhang et al. (1995 ▶, 1990 ▶). For a related structure, see: Wu et al. (2009 ▶).

Experimental

Crystal data

C9H8ClNO4

M = 229.61

Monoclinic,

a = 4.9404 (10) Å

b = 21.618 (5) Å

c = 18.325 (4) Å

β = 90.441 (3)°

V = 1957.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.38 mm−1

T = 103 K

0.40 × 0.20 × 0.20 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.862, T max = 0.927

18618 measured reflections

4466 independent reflections

3781 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.00

4466 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038742/xu5038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038742/xu5038Isup2.hkl

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

C9H8ClNO4	F(000) = 944
Mr = 229.61	Dx = 1.559 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5688 reflections
a = 4.9404 (10) Å	θ = 3.0–27.5°
b = 21.618 (5) Å	µ = 0.38 mm−1
c = 18.325 (4) Å	T = 103 K
β = 90.441 (3)°	Prism, colorless
V = 1957.0 (7) Å3	0.40 × 0.20 × 0.20 mm
Z = 8

Rigaku SPIDER diffractometer	4466 independent reflections
Radiation source: Rotating Anode	3781 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.862, Tmax = 0.927	k = −28→28
18618 measured reflections	l = −23→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.680P] where P = (Fo2 + 2Fc2)/3
4466 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.23 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
Cl1	0.58062 (8)	0.615621 (18)	0.60156 (2)	0.02137 (10)
O1	0.5719 (2)	0.70861 (5)	0.72719 (6)	0.0201 (2)
O2	0.4652 (2)	0.80061 (5)	0.77677 (6)	0.0230 (3)
O3	1.4451 (3)	0.74075 (6)	1.03965 (7)	0.0288 (3)
O4	1.5555 (2)	0.65746 (6)	0.98123 (7)	0.0274 (3)
N1	1.4158 (3)	0.70367 (6)	0.98970 (8)	0.0203 (3)
C1	0.8669 (3)	0.78260 (7)	0.88589 (9)	0.0169 (3)
H1	0.7699	0.8205	0.8865	0.020*
C2	1.0633 (3)	0.77121 (7)	0.93827 (9)	0.0176 (3)
H2	1.1025	0.8007	0.9752	0.021*
C3	1.2012 (3)	0.71558 (7)	0.93535 (8)	0.0163 (3)
C4	1.1480 (3)	0.67097 (7)	0.88291 (9)	0.0169 (3)
H4	1.2455	0.6331	0.8825	0.020*
C5	0.9499 (3)	0.68282 (7)	0.83117 (8)	0.0163 (3)
H5	0.9090	0.6528	0.7949	0.020*
C6	0.8102 (3)	0.73879 (7)	0.83215 (8)	0.0143 (3)
C7	0.5974 (3)	0.75381 (7)	0.77687 (8)	0.0155 (3)
C8	0.3759 (3)	0.71808 (7)	0.66929 (9)	0.0193 (3)
H8A	0.4555	0.7434	0.6299	0.023*
H8B	0.2148	0.7399	0.6882	0.023*
C9	0.2977 (3)	0.65561 (7)	0.64066 (9)	0.0183 (3)
H9A	0.1541	0.6605	0.6031	0.022*
H9B	0.2231	0.6305	0.6810	0.022*
Cl1'	0.09925 (8)	0.578510 (18)	0.46926 (2)	0.02083 (10)
O1'	0.0719 (2)	0.53366 (5)	0.30930 (6)	0.0170 (2)
O2'	−0.0224 (2)	0.45272 (5)	0.23673 (6)	0.0203 (2)
O3'	0.9692 (2)	0.56670 (5)	0.00593 (7)	0.0249 (3)
O4'	1.0593 (2)	0.63815 (6)	0.08520 (6)	0.0243 (3)
N1'	0.9309 (3)	0.59294 (6)	0.06415 (7)	0.0176 (3)
C1'	0.3955 (3)	0.49087 (7)	0.13991 (8)	0.0158 (3)
H1'	0.3083	0.4527	0.1291	0.019*
C2'	0.5964 (3)	0.51288 (7)	0.09445 (9)	0.0165 (3)
H2'	0.6497	0.4903	0.0525	0.020*
C3'	0.7174 (3)	0.56882 (7)	0.11200 (8)	0.0150 (3)
C4'	0.6481 (3)	0.60310 (7)	0.17254 (9)	0.0170 (3)
H4'	0.7366	0.6411	0.1831	0.020*
C5'	0.4468 (3)	0.58079 (7)	0.21743 (8)	0.0160 (3)
H5'	0.3941	0.6037	0.2592	0.019*
C6'	0.3209 (3)	0.52453 (7)	0.20138 (8)	0.0139 (3)
C7'	0.1063 (3)	0.49883 (7)	0.24947 (8)	0.0149 (3)
C8'	−0.1343 (3)	0.51265 (7)	0.35872 (8)	0.0168 (3)
H8'1	−0.0718	0.4753	0.3852	0.020*
H8'2	−0.3017	0.5022	0.3314	0.020*
C9'	−0.1878 (3)	0.56394 (8)	0.41134 (9)	0.0211 (3)
H9'1	−0.3454	0.5530	0.4418	0.025*
H9'2	−0.2334	0.6020	0.3839	0.025*

	U11	U22	U33	U12	U13	U23
Cl1	0.01863 (19)	0.0242 (2)	0.0213 (2)	−0.00012 (15)	0.00069 (15)	−0.00381 (16)
O1	0.0238 (6)	0.0183 (5)	0.0182 (6)	0.0036 (5)	−0.0087 (5)	−0.0042 (4)
O2	0.0287 (6)	0.0174 (5)	0.0228 (6)	0.0070 (5)	−0.0078 (5)	−0.0007 (5)
O3	0.0304 (7)	0.0329 (7)	0.0229 (7)	−0.0062 (5)	−0.0103 (6)	0.0002 (5)
O4	0.0203 (6)	0.0359 (7)	0.0259 (7)	0.0089 (5)	0.0000 (5)	0.0089 (5)
N1	0.0156 (6)	0.0272 (7)	0.0182 (7)	−0.0039 (6)	−0.0011 (5)	0.0071 (6)
C1	0.0191 (8)	0.0141 (7)	0.0174 (8)	0.0020 (6)	0.0006 (6)	−0.0007 (6)
C2	0.0209 (8)	0.0178 (7)	0.0142 (8)	−0.0020 (6)	0.0001 (6)	−0.0011 (6)
C3	0.0131 (7)	0.0215 (7)	0.0144 (7)	−0.0020 (6)	−0.0004 (6)	0.0050 (6)
C4	0.0165 (7)	0.0150 (7)	0.0191 (8)	0.0026 (6)	0.0021 (6)	0.0020 (6)
C5	0.0199 (8)	0.0142 (7)	0.0148 (7)	−0.0005 (6)	0.0013 (6)	−0.0012 (6)
C6	0.0157 (7)	0.0146 (7)	0.0127 (7)	−0.0006 (6)	0.0015 (6)	0.0016 (6)
C7	0.0179 (7)	0.0155 (7)	0.0131 (7)	−0.0016 (6)	0.0009 (6)	0.0005 (6)
C8	0.0217 (8)	0.0192 (7)	0.0168 (8)	0.0010 (6)	−0.0071 (6)	−0.0008 (6)
C9	0.0152 (7)	0.0209 (7)	0.0189 (8)	−0.0011 (6)	0.0006 (6)	−0.0018 (6)
Cl1'	0.0243 (2)	0.02306 (19)	0.01513 (19)	−0.00621 (15)	0.00131 (15)	−0.00093 (15)
O1'	0.0212 (6)	0.0176 (5)	0.0123 (5)	−0.0048 (4)	0.0038 (4)	−0.0015 (4)
O2'	0.0235 (6)	0.0157 (5)	0.0216 (6)	−0.0044 (5)	0.0024 (5)	−0.0019 (5)
O3'	0.0313 (7)	0.0233 (6)	0.0203 (6)	0.0061 (5)	0.0107 (5)	0.0013 (5)
O4'	0.0200 (6)	0.0302 (6)	0.0225 (6)	−0.0072 (5)	−0.0001 (5)	0.0030 (5)
N1'	0.0154 (6)	0.0206 (7)	0.0167 (7)	0.0054 (5)	0.0004 (5)	0.0052 (5)
C1'	0.0183 (7)	0.0139 (7)	0.0153 (8)	0.0010 (6)	−0.0024 (6)	−0.0015 (6)
C2'	0.0184 (7)	0.0178 (7)	0.0134 (7)	0.0047 (6)	−0.0009 (6)	−0.0025 (6)
C3'	0.0125 (7)	0.0181 (7)	0.0144 (7)	0.0026 (6)	−0.0001 (6)	0.0048 (6)
C4'	0.0183 (8)	0.0164 (7)	0.0164 (8)	−0.0014 (6)	−0.0022 (6)	0.0002 (6)
C5'	0.0195 (8)	0.0154 (7)	0.0130 (7)	0.0000 (6)	0.0002 (6)	−0.0021 (6)
C6'	0.0146 (7)	0.0145 (7)	0.0127 (7)	0.0014 (6)	−0.0021 (6)	0.0013 (6)
C7'	0.0164 (7)	0.0144 (7)	0.0138 (7)	0.0031 (6)	−0.0026 (6)	0.0006 (6)
C8'	0.0170 (7)	0.0200 (7)	0.0134 (8)	−0.0038 (6)	0.0032 (6)	0.0012 (6)
C9'	0.0172 (8)	0.0261 (8)	0.0202 (8)	0.0018 (6)	0.0014 (6)	−0.0025 (7)

Cl1—C9	1.7971 (16)	Cl1'—C9'	1.7927 (17)
O1—C7	1.3408 (18)	O1'—C7'	1.3419 (18)
O1—C8	1.4454 (19)	O1'—C8'	1.4416 (18)
O2—C7	1.2043 (18)	O2'—C7'	1.2041 (18)
O3—N1	1.2245 (19)	O3'—N1'	1.2243 (18)
O4—N1	1.2247 (18)	O4'—N1'	1.2258 (17)
N1—C3	1.472 (2)	N1'—C3'	1.4725 (19)
C1—C2	1.382 (2)	C1'—C2'	1.385 (2)
C1—C6	1.393 (2)	C1'—C6'	1.393 (2)
C1—H1	0.9500	C1'—H1'	0.9500
C2—C3	1.383 (2)	C2'—C3'	1.386 (2)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.385 (2)	C3'—C4'	1.380 (2)
C4—C5	1.381 (2)	C4'—C5'	1.382 (2)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.393 (2)	C5'—C6'	1.396 (2)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.490 (2)	C6'—C7'	1.491 (2)
C8—C9	1.498 (2)	C8'—C9'	1.494 (2)
C8—H8A	0.9900	C8'—H8'1	0.9900
C8—H8B	0.9900	C8'—H8'2	0.9900
C9—H9A	0.9900	C9'—H9'1	0.9900
C9—H9B	0.9900	C9'—H9'2	0.9900
C7—O1—C8	117.01 (12)	C7'—O1'—C8'	115.53 (11)
O3—N1—O4	124.40 (14)	O3'—N1'—O4'	124.11 (14)
O3—N1—C3	118.16 (14)	O3'—N1'—C3'	118.11 (13)
O4—N1—C3	117.44 (14)	O4'—N1'—C3'	117.79 (13)
C2—C1—C6	120.41 (14)	C2'—C1'—C6'	120.14 (14)
C2—C1—H1	119.8	C2'—C1'—H1'	119.9
C6—C1—H1	119.8	C6'—C1'—H1'	119.9
C1—C2—C3	118.13 (14)	C1'—C2'—C3'	118.03 (14)
C1—C2—H2	120.9	C1'—C2'—H2'	121.0
C3—C2—H2	120.9	C3'—C2'—H2'	121.0
C2—C3—C4	122.76 (14)	C4'—C3'—C2'	123.12 (14)
C2—C3—N1	118.58 (14)	C4'—C3'—N1'	118.16 (13)
C4—C3—N1	118.65 (14)	C2'—C3'—N1'	118.72 (14)
C5—C4—C3	118.48 (14)	C3'—C4'—C5'	118.36 (14)
C5—C4—H4	120.8	C3'—C4'—H4'	120.8
C3—C4—H4	120.8	C5'—C4'—H4'	120.8
C4—C5—C6	120.04 (14)	C4'—C5'—C6'	120.00 (14)
C4—C5—H5	120.0	C4'—C5'—H5'	120.0
C6—C5—H5	120.0	C6'—C5'—H5'	120.0
C1—C6—C5	120.18 (14)	C1'—C6'—C5'	120.34 (14)
C1—C6—C7	118.00 (13)	C1'—C6'—C7'	118.48 (13)
C5—C6—C7	121.83 (14)	C5'—C6'—C7'	121.17 (14)
O2—C7—O1	124.27 (14)	O2'—C7'—O1'	123.57 (14)
O2—C7—C6	124.32 (14)	O2'—C7'—C6'	124.79 (14)
O1—C7—C6	111.41 (12)	O1'—C7'—C6'	111.64 (12)
O1—C8—C9	107.38 (12)	O1'—C8'—C9'	107.52 (12)
O1—C8—H8A	110.2	O1'—C8'—H8'1	110.2
C9—C8—H8A	110.2	C9'—C8'—H8'1	110.2
O1—C8—H8B	110.2	O1'—C8'—H8'2	110.2
C9—C8—H8B	110.2	C9'—C8'—H8'2	110.2
H8A—C8—H8B	108.5	H8'1—C8'—H8'2	108.5
C8—C9—Cl1	111.97 (11)	C8'—C9'—Cl1'	111.67 (11)
C8—C9—H9A	109.2	C8'—C9'—H9'1	109.3
Cl1—C9—H9A	109.2	Cl1'—C9'—H9'1	109.3
C8—C9—H9B	109.2	C8'—C9'—H9'2	109.3
Cl1—C9—H9B	109.2	Cl1'—C9'—H9'2	109.3
H9A—C9—H9B	107.9	H9'1—C9'—H9'2	107.9
C6—C1—C2—C3	0.3 (2)	C6'—C1'—C2'—C3'	−0.3 (2)
C1—C2—C3—C4	−0.8 (2)	C1'—C2'—C3'—C4'	0.4 (2)
C1—C2—C3—N1	178.39 (13)	C1'—C2'—C3'—N1'	−179.86 (13)
O3—N1—C3—C2	7.2 (2)	O3'—N1'—C3'—C4'	−171.12 (13)
O4—N1—C3—C2	−171.95 (14)	O4'—N1'—C3'—C4'	8.8 (2)
O3—N1—C3—C4	−173.58 (14)	O3'—N1'—C3'—C2'	9.1 (2)
O4—N1—C3—C4	7.3 (2)	O4'—N1'—C3'—C2'	−170.90 (13)
C2—C3—C4—C5	0.4 (2)	C2'—C3'—C4'—C5'	−0.6 (2)
N1—C3—C4—C5	−178.79 (13)	N1'—C3'—C4'—C5'	179.68 (13)
C3—C4—C5—C6	0.5 (2)	C3'—C4'—C5'—C6'	0.6 (2)
C2—C1—C6—C5	0.5 (2)	C2'—C1'—C6'—C5'	0.4 (2)
C2—C1—C6—C7	−179.66 (14)	C2'—C1'—C6'—C7'	−179.20 (13)
C4—C5—C6—C1	−0.9 (2)	C4'—C5'—C6'—C1'	−0.5 (2)
C4—C5—C6—C7	179.26 (14)	C4'—C5'—C6'—C7'	179.00 (14)
C8—O1—C7—O2	1.3 (2)	C8'—O1'—C7'—O2'	−0.4 (2)
C8—O1—C7—C6	−178.60 (13)	C8'—O1'—C7'—C6'	179.34 (12)
C1—C6—C7—O2	−2.3 (2)	C1'—C6'—C7'—O2'	−5.3 (2)
C5—C6—C7—O2	177.53 (15)	C5'—C6'—C7'—O2'	175.17 (15)
C1—C6—C7—O1	177.65 (13)	C1'—C6'—C7'—O1'	174.96 (13)
C5—C6—C7—O1	−2.5 (2)	C5'—C6'—C7'—O1'	−4.60 (19)
C7—O1—C8—C9	−156.81 (13)	C7'—O1'—C8'—C9'	−166.85 (12)
O1—C8—C9—Cl1	−62.71 (15)	O1'—C8'—C9'—Cl1'	−66.44 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1'i	0.95	2.79	3.6234 (18)	147
C2'—H2'···O3'ii	0.95	2.50	3.318 (2)	145
C4'—H4'···O2iii	0.95	2.40	3.223 (2)	144
C5—H5···O2'iv	0.95	2.42	3.205 (2)	140
C5'—H5'···O1'	0.95	2.39	2.7112 (19)	100
C9—H9B···O2'v	0.99	2.55	3.526 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1′	0.95	2.79	3.6234 (18)	147
C2′—H2′⋯O3′i	0.95	2.50	3.318 (2)	145
C4′—H4′⋯O2	0.95	2.40	3.223 (2)	144
C5—H5⋯O2′ii	0.95	2.42	3.205 (2)	140
C9—H9B⋯O2′iii	0.99	2.55	3.526 (2)	167

Symmetry codes: (i) ; (ii) ; (iii) .