Isopropyl 4-nitro-benzoate.

In the mol-ecule of the title compound, C(10)H(11)NO(4), the nitro group is approximately coplanar with the benzene ring [dihedral angle = 4.57 (10)°], while the carboxyl-ate group is slightly twisted, making an angle of 12.16 (8)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonding and π-π stacking inter-actions [centroid-centroid distances = 3.670 (2) and 3.665 (2) Å] are observed.

Related literature

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

Experimental

Crystal data

C10H11NO4

M = 209.20

Triclinic,

a = 6.729 (4) Å

b = 7.192 (4) Å

c = 10.388 (6) Å

α = 94.751 (9)°

β = 92.503 (7)°

γ = 95.901 (10)°

V = 497.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 153 K

0.37 × 0.33 × 0.10 mm

Data collection

Rigaku SPIDER diffractometer

6626 measured reflections

2862 independent reflections

1947 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.150

S = 1.00

2862 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.29 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 datablock(s) I, global. DOI: 10.1107/S1600536811039407/xu5329sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039407/xu5329Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039407/xu5329Isup3.cml

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

C10H11NO4	Z = 2
Mr = 209.20	F(000) = 220
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.729 (4) Å	Cell parameters from 1490 reflections
b = 7.192 (4) Å	θ = 2.9–30.0°
c = 10.388 (6) Å	µ = 0.11 mm−1
α = 94.751 (9)°	T = 153 K
β = 92.503 (7)°	Platelet, colorless
γ = 95.901 (10)°	0.37 × 0.33 × 0.10 mm
V = 497.6 (5) Å3

Rigaku SPIDER diffractometer	1947 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.023
graphite	θmax = 30.0°, θmin = 2.0°
ω scans	h = −9→9
6626 measured reflections	k = −10→9
2862 independent reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.071P)2 + 0.196P] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.29 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	0.24504 (18)	0.35230 (15)	0.12880 (10)	0.0258 (3)
O2	0.3016 (2)	0.12996 (17)	0.26213 (12)	0.0375 (3)
O3	0.2023 (2)	0.79014 (18)	0.77175 (11)	0.0381 (3)
O4	0.2382 (3)	1.00939 (19)	0.64283 (13)	0.0513 (4)
N1	0.2278 (2)	0.8444 (2)	0.66434 (13)	0.0288 (3)
C1	0.2535 (2)	0.3845 (2)	0.47750 (14)	0.0226 (3)
H1	0.2540	0.2559	0.4922	0.027*
C2	0.2421 (2)	0.5176 (2)	0.58075 (14)	0.0233 (3)
H2	0.2325	0.4818	0.6665	0.028*
C3	0.2450 (2)	0.7032 (2)	0.55569 (14)	0.0221 (3)
C4	0.2586 (2)	0.7627 (2)	0.43241 (14)	0.0234 (3)
H4	0.2618	0.8919	0.4186	0.028*
C5	0.2672 (2)	0.6275 (2)	0.32976 (14)	0.0223 (3)
H5	0.2752	0.6638	0.2441	0.027*
C6	0.2642 (2)	0.4393 (2)	0.35198 (14)	0.0207 (3)
C7	0.2732 (2)	0.2890 (2)	0.24432 (14)	0.0225 (3)
C8	0.2391 (2)	0.2167 (2)	0.01385 (15)	0.0252 (3)
H8	0.2027	0.0870	0.0392	0.030*
C9	0.4432 (3)	0.2293 (3)	−0.04028 (18)	0.0374 (4)
H9A	0.4766	0.3551	−0.0682	0.056*
H9B	0.4435	0.1358	−0.1145	0.056*
H9C	0.5424	0.2052	0.0265	0.056*
C10	0.0769 (3)	0.2689 (3)	−0.07652 (17)	0.0376 (4)
H10A	−0.0497	0.2638	−0.0331	0.056*
H10B	0.0624	0.1806	−0.1543	0.056*
H10C	0.1125	0.3963	−0.1010	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0401 (7)	0.0214 (5)	0.0164 (5)	0.0043 (4)	0.0039 (4)	0.0014 (4)
O2	0.0614 (9)	0.0256 (6)	0.0276 (6)	0.0129 (6)	0.0017 (6)	0.0047 (5)
O3	0.0533 (8)	0.0423 (7)	0.0184 (6)	0.0022 (6)	0.0076 (5)	0.0014 (5)
O4	0.0989 (13)	0.0302 (7)	0.0272 (7)	0.0169 (7)	0.0103 (7)	0.0003 (5)
N1	0.0359 (8)	0.0324 (7)	0.0185 (6)	0.0060 (6)	0.0028 (5)	0.0004 (5)
C1	0.0229 (7)	0.0240 (7)	0.0218 (7)	0.0027 (6)	0.0012 (5)	0.0071 (5)
C2	0.0234 (7)	0.0296 (8)	0.0174 (6)	0.0024 (6)	0.0014 (5)	0.0061 (5)
C3	0.0223 (7)	0.0275 (7)	0.0165 (6)	0.0035 (6)	0.0021 (5)	0.0006 (5)
C4	0.0290 (8)	0.0229 (7)	0.0191 (7)	0.0046 (6)	0.0025 (6)	0.0035 (5)
C5	0.0265 (8)	0.0257 (7)	0.0158 (6)	0.0043 (6)	0.0036 (5)	0.0047 (5)
C6	0.0197 (7)	0.0245 (7)	0.0183 (6)	0.0030 (5)	0.0021 (5)	0.0034 (5)
C7	0.0245 (7)	0.0234 (7)	0.0201 (7)	0.0030 (6)	0.0030 (5)	0.0041 (5)
C8	0.0341 (9)	0.0198 (7)	0.0209 (7)	0.0016 (6)	0.0039 (6)	−0.0021 (5)
C9	0.0406 (10)	0.0350 (9)	0.0352 (9)	0.0023 (7)	0.0103 (8)	−0.0087 (7)
C10	0.0462 (11)	0.0389 (10)	0.0276 (8)	0.0134 (8)	−0.0034 (7)	−0.0064 (7)

O1—C7	1.3309 (18)	C4—H4	0.9500
O1—C8	1.4741 (18)	C5—C6	1.390 (2)
O2—C7	1.2067 (19)	C5—H5	0.9500
O3—N1	1.2255 (18)	C6—C7	1.497 (2)
O4—N1	1.221 (2)	C8—C9	1.503 (2)
N1—C3	1.471 (2)	C8—C10	1.506 (2)
C1—C2	1.387 (2)	C8—H8	1.0000
C1—C6	1.396 (2)	C9—H9A	0.9800
C1—H1	0.9500	C9—H9B	0.9800
C2—C3	1.380 (2)	C9—H9C	0.9800
C2—H2	0.9500	C10—H10A	0.9800
C3—C4	1.387 (2)	C10—H10B	0.9800
C4—C5	1.390 (2)	C10—H10C	0.9800
C7—O1—C8	117.82 (12)	O2—C7—O1	124.91 (14)
O4—N1—O3	123.35 (14)	O2—C7—C6	123.18 (14)
O4—N1—C3	118.42 (13)	O1—C7—C6	111.91 (13)
O3—N1—C3	118.23 (14)	O1—C8—C9	108.43 (13)
C2—C1—C6	120.08 (14)	O1—C8—C10	105.50 (13)
C2—C1—H1	120.0	C9—C8—C10	114.14 (15)
C6—C1—H1	120.0	O1—C8—H8	109.5
C3—C2—C1	118.24 (14)	C9—C8—H8	109.5
C3—C2—H2	120.9	C10—C8—H8	109.5
C1—C2—H2	120.9	C8—C9—H9A	109.5
C2—C3—C4	123.15 (14)	C8—C9—H9B	109.5
C2—C3—N1	118.50 (13)	H9A—C9—H9B	109.5
C4—C3—N1	118.34 (14)	C8—C9—H9C	109.5
C3—C4—C5	117.92 (14)	H9A—C9—H9C	109.5
C3—C4—H4	121.0	H9B—C9—H9C	109.5
C5—C4—H4	121.0	C8—C10—H10A	109.5
C4—C5—C6	120.24 (13)	C8—C10—H10B	109.5
C4—C5—H5	119.9	H10A—C10—H10B	109.5
C6—C5—H5	119.9	C8—C10—H10C	109.5
C5—C6—C1	120.35 (13)	H10A—C10—H10C	109.5
C5—C6—C7	122.02 (13)	H10B—C10—H10C	109.5
C1—C6—C7	117.62 (14)
C6—C1—C2—C3	−1.0 (2)	C4—C5—C6—C7	179.97 (14)
C1—C2—C3—C4	0.1 (2)	C2—C1—C6—C5	1.2 (2)
C1—C2—C3—N1	178.46 (13)	C2—C1—C6—C7	−179.10 (14)
O4—N1—C3—C2	177.20 (16)	C8—O1—C7—O2	2.8 (2)
O3—N1—C3—C2	−3.3 (2)	C8—O1—C7—C6	−176.78 (12)
O4—N1—C3—C4	−4.3 (2)	C5—C6—C7—O2	168.27 (16)
O3—N1—C3—C4	175.17 (15)	C1—C6—C7—O2	−11.5 (2)
C2—C3—C4—C5	0.8 (2)	C5—C6—C7—O1	−12.1 (2)
N1—C3—C4—C5	−177.64 (14)	C1—C6—C7—O1	168.17 (13)
C3—C4—C5—C6	−0.6 (2)	C7—O1—C8—C9	−96.71 (16)
C4—C5—C6—C1	−0.3 (2)	C7—O1—C8—C10	140.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4i	0.95	2.46	3.311 (3)	149
C4—H4···O2ii	0.95	2.46	3.294 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.95	2.46	3.311 (3)	149
C4—H4⋯O2ii	0.95	2.46	3.294 (3)	147

Symmetry codes: (i) ; (ii) .