Isobutyl 3,5-dinitro-benzoate.

In the structure of the title compound, C(11)H(12)N(2)O(6), the mol-ecules are stacked along the b axis without any π-π inter-actions. The stacked columns are linked together by non-classical inter-molecular C-H⋯O inter-actions,. In the molecule, the nitro groups make dihedral angles of 9.4 (5) and 10.3 (5)° with the benzene ring.

Related literature

For the properties and applications of dinitro­benzoate derivatives, see: Huang et al. (2004 ▶); Kagitani et al. (1984 ▶); Olive (1979 ▶). For the anti-creatinine effects of a series of 3,5-dinitro­benzoic acid esters, see: Yu & Yang (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12N2O6

M = 268.23

Monoclinic,

a = 16.666 (3) Å

b = 4.776 (1) Å

c = 16.678 (3) Å

β = 110.30 (3)°

V = 1245.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.988

2348 measured reflections

2266 independent reflections

1402 reflections with I > 2σ(I)

R int = 0.061

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.225

S = 1.11

2266 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010381/pv2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010381/pv2148Isup2.hkl

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

C11H12N2O6	F(000) = 560
Mr = 268.23	Dx = 1.431 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 16.666 (3) Å	θ = 9–12°
b = 4.776 (1) Å	µ = 0.12 mm−1
c = 16.678 (3) Å	T = 293 K
β = 110.30 (3)°	Needle, colourless
V = 1245.1 (5) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1402 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = 0→20
Absorption correction: ψ scan (North et al., 1968)	k = 0→5
Tmin = 0.965, Tmax = 0.988	l = −20→18
2348 measured reflections	3 standard reflections every 200 reflections
2266 independent reflections	intensity decay: 1%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1P)2 + P] where P = (Fo2 + 2Fc2)/3
2266 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.30 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	−0.17180 (16)	−0.2811 (6)	0.58690 (17)	0.0567 (8)
O2	−0.08913 (17)	−0.4218 (7)	0.51387 (18)	0.0616 (8)
O3	−0.0648 (2)	0.3897 (9)	0.8166 (2)	0.0933 (13)
O4	0.0522 (2)	0.6102 (7)	0.8340 (2)	0.0767 (10)
O5	0.23983 (17)	0.2979 (6)	0.68814 (18)	0.0603 (8)
O6	0.20462 (18)	−0.0604 (6)	0.60527 (19)	0.0637 (9)
N1	−0.0004 (2)	0.4291 (8)	0.8000 (2)	0.0542 (9)
N2	0.18975 (19)	0.1116 (7)	0.6515 (2)	0.0463 (8)
C1	−0.2813 (3)	−0.6160 (11)	0.6546 (3)	0.0745 (14)
H1A	−0.2346	−0.5124	0.6936	0.112*
H1B	−0.2629	−0.8031	0.6491	0.112*
H1C	−0.3278	−0.6224	0.6761	0.112*
C2	−0.3856 (3)	−0.6279 (12)	0.5060 (3)	0.0864 (17)
H2A	−0.4308	−0.6444	0.5289	0.130*
H2B	−0.3680	−0.8112	0.4951	0.130*
H2C	−0.4055	−0.5237	0.4535	0.130*
C3	−0.3102 (3)	−0.4769 (9)	0.5697 (3)	0.0593 (11)
H3A	−0.3289	−0.2870	0.5771	0.071*
C4	−0.2420 (3)	−0.4536 (10)	0.5323 (3)	0.0645 (12)
H4A	−0.2208	−0.6386	0.5264	0.077*
H4B	−0.2651	−0.3702	0.4759	0.077*
C5	−0.1000 (2)	−0.2845 (8)	0.5687 (2)	0.0418 (8)
C6	−0.0337 (2)	−0.0901 (7)	0.6262 (2)	0.0363 (8)
C7	0.0447 (2)	−0.0816 (7)	0.6143 (2)	0.0388 (8)
H7A	0.0553	−0.1948	0.5736	0.047*
C8	0.1063 (2)	0.0988 (7)	0.6641 (2)	0.0381 (8)
C9	0.0934 (2)	0.2683 (7)	0.7252 (2)	0.0406 (8)
H9A	0.1356	0.3901	0.7578	0.049*
C10	0.0157 (2)	0.2503 (7)	0.7359 (2)	0.0407 (8)
C11	−0.0482 (2)	0.0730 (8)	0.6876 (2)	0.0430 (9)
H11A	−0.1002	0.0641	0.6965	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (15)	0.0679 (19)	0.0601 (17)	−0.0169 (14)	0.0283 (13)	−0.0232 (14)
O2	0.0559 (17)	0.070 (2)	0.0611 (17)	−0.0124 (15)	0.0226 (14)	−0.0231 (16)
O3	0.072 (2)	0.123 (3)	0.096 (3)	0.002 (2)	0.043 (2)	−0.047 (2)
O4	0.093 (2)	0.066 (2)	0.070 (2)	−0.0068 (19)	0.0260 (18)	−0.0222 (18)
O5	0.0550 (16)	0.0615 (19)	0.0638 (18)	−0.0203 (15)	0.0200 (14)	−0.0124 (15)
O6	0.0572 (17)	0.067 (2)	0.075 (2)	−0.0002 (15)	0.0328 (15)	−0.0174 (17)
N1	0.056 (2)	0.053 (2)	0.0485 (19)	0.0094 (18)	0.0128 (16)	−0.0119 (17)
N2	0.0420 (17)	0.048 (2)	0.0478 (18)	0.0002 (15)	0.0143 (14)	0.0031 (16)
C1	0.073 (3)	0.085 (4)	0.069 (3)	−0.020 (3)	0.029 (2)	−0.008 (3)
C2	0.051 (3)	0.100 (4)	0.090 (4)	−0.023 (3)	0.001 (2)	0.023 (3)
C3	0.052 (2)	0.054 (3)	0.073 (3)	−0.004 (2)	0.022 (2)	0.006 (2)
C4	0.056 (2)	0.081 (3)	0.057 (2)	−0.024 (2)	0.020 (2)	−0.020 (2)
C5	0.048 (2)	0.040 (2)	0.0394 (19)	−0.0065 (17)	0.0181 (16)	0.0011 (17)
C6	0.0414 (18)	0.0324 (18)	0.0320 (17)	−0.0024 (15)	0.0088 (14)	−0.0001 (15)
C7	0.0446 (19)	0.0347 (18)	0.0377 (18)	0.0001 (16)	0.0151 (15)	0.0015 (15)
C8	0.0384 (18)	0.0371 (19)	0.0378 (18)	0.0030 (15)	0.0118 (15)	0.0040 (15)
C9	0.047 (2)	0.0325 (19)	0.0378 (18)	−0.0016 (16)	0.0091 (15)	−0.0001 (15)
C10	0.0456 (19)	0.038 (2)	0.0352 (18)	0.0048 (16)	0.0095 (15)	−0.0036 (15)
C11	0.0422 (19)	0.048 (2)	0.0387 (18)	0.0011 (17)	0.0134 (16)	0.0060 (17)

O1—C5	1.332 (4)	C2—H2C	0.9600
O1—C4	1.462 (5)	C3—C4	1.479 (5)
O2—C5	1.190 (4)	C3—H3A	0.9800
O3—N1	1.213 (4)	C4—H4A	0.9700
O4—N1	1.222 (4)	C4—H4B	0.9700
O5—N2	1.228 (4)	C5—C6	1.505 (5)
O6—N2	1.210 (4)	C6—C11	1.373 (5)
N1—C10	1.463 (5)	C6—C7	1.390 (5)
N2—C8	1.478 (4)	C7—C8	1.377 (5)
C1—C3	1.485 (6)	C7—H7A	0.9300
C1—H1A	0.9600	C8—C9	1.375 (5)
C1—H1B	0.9600	C9—C10	1.369 (5)
C1—H1C	0.9600	C9—H9A	0.9300
C2—C3	1.517 (6)	C10—C11	1.381 (5)
C2—H2A	0.9600	C11—H11A	0.9300
C2—H2B	0.9600
C5—O1—C4	116.0 (3)	O1—C4—H4A	109.6
O3—N1—O4	123.5 (4)	C3—C4—H4A	109.6
O3—N1—C10	118.5 (4)	O1—C4—H4B	109.6
O4—N1—C10	117.9 (3)	C3—C4—H4B	109.6
O6—N2—O5	123.7 (3)	H4A—C4—H4B	108.1
O6—N2—C8	118.3 (3)	O2—C5—O1	124.8 (3)
O5—N2—C8	118.0 (3)	O2—C5—C6	123.7 (3)
C3—C1—H1A	109.5	O1—C5—C6	111.5 (3)
C3—C1—H1B	109.5	C11—C6—C7	120.5 (3)
H1A—C1—H1B	109.5	C11—C6—C5	123.0 (3)
C3—C1—H1C	109.5	C7—C6—C5	116.5 (3)
H1A—C1—H1C	109.5	C8—C7—C6	118.2 (3)
H1B—C1—H1C	109.5	C8—C7—H7A	120.9
C3—C2—H2A	109.5	C6—C7—H7A	120.9
C3—C2—H2B	109.5	C7—C8—C9	122.7 (3)
H2A—C2—H2B	109.5	C7—C8—N2	118.8 (3)
C3—C2—H2C	109.5	C9—C8—N2	118.6 (3)
H2A—C2—H2C	109.5	C10—C9—C8	117.3 (3)
H2B—C2—H2C	109.5	C10—C9—H9A	121.4
C4—C3—C1	113.2 (4)	C8—C9—H9A	121.4
C4—C3—C2	108.1 (4)	C9—C10—C11	122.3 (3)
C1—C3—C2	111.8 (4)	C9—C10—N1	118.7 (3)
C4—C3—H3A	107.9	C11—C10—N1	119.0 (3)
C1—C3—H3A	107.9	C6—C11—C10	118.9 (3)
C2—C3—H3A	107.9	C6—C11—H11A	120.5
O1—C4—C3	110.2 (3)	C10—C11—H11A	120.5
C5—O1—C4—C3	168.4 (4)	O6—N2—C8—C9	171.3 (3)
C1—C3—C4—O1	−62.2 (5)	O5—N2—C8—C9	−9.2 (5)
C2—C3—C4—O1	173.4 (4)	C7—C8—C9—C10	0.6 (5)
C4—O1—C5—O2	−2.2 (6)	N2—C8—C9—C10	−179.5 (3)
C4—O1—C5—C6	177.4 (3)	C8—C9—C10—C11	−0.6 (5)
O2—C5—C6—C11	178.1 (4)	C8—C9—C10—N1	−179.6 (3)
O1—C5—C6—C11	−1.5 (5)	O3—N1—C10—C9	−171.3 (4)
O2—C5—C6—C7	−1.8 (5)	O4—N1—C10—C9	8.5 (5)
O1—C5—C6—C7	178.6 (3)	O3—N1—C10—C11	9.7 (5)
C11—C6—C7—C8	−1.5 (5)	O4—N1—C10—C11	−170.5 (3)
C5—C6—C7—C8	178.4 (3)	C7—C6—C11—C10	1.5 (5)
C6—C7—C8—C9	0.4 (5)	C5—C6—C11—C10	−178.4 (3)
C6—C7—C8—N2	−179.5 (3)	C9—C10—C11—C6	−0.4 (5)
O6—N2—C8—C7	−8.8 (5)	N1—C10—C11—C6	178.5 (3)
O5—N2—C8—C7	170.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.93	2.52	3.441 (5)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.93	2.52	3.441 (5)	168

Symmetry code: (i) .