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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2986.
Published online 2010 October 30. doi:  10.1107/S160053681004359X
PMCID: PMC3009116

Isopropyl 4-chloro-3,5-dinitro­benzoate

Abstract

In the title compound, C10H9ClN2O6, the two nitro groups and the ester group are oriented with respect to the benzene ring at dihedral angles of 49.42 (13)/87.61 (13) and 9.10 (10)°, respectively. In the crystal structure, a weak C—H(...)O inter­action is present. A short Cl(...)O contact of 2.972 (2) Å is also observed in the crystal structure.

Related literature

For the application of the title compound as a herbicide and fungicide, see: Akira et al. (1978 [triangle]); Ferenc et al. (1984 [triangle]).

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Object name is e-66-o2986-scheme1.jpg

Experimental

Crystal data

  • C10H9ClN2O6
  • M r = 288.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2986-efi1.jpg
  • a = 4.703 (2) Å
  • b = 10.783 (5) Å
  • c = 12.734 (5) Å
  • α = 69.483 (12)°
  • β = 87.75 (2)°
  • γ = 89.61 (2)°
  • V = 604.3 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 103 K
  • 0.57 × 0.22 × 0.10 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.830, T max = 0.967
  • 5643 measured reflections
  • 2689 independent reflections
  • 1756 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.114
  • S = 1.00
  • 2689 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.27 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004359X/xu5065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004359X/xu5065Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from Guangdong Food and Drug Vocational College, China.

supplementary crystallographic information

Comment

Isopropyl 4-chloro-3,5-dinitrobenzoate (Fig. 1) is a useful herbicide and fungicide (Akira et al., 1978; Ferenc et al., 1984). It was used as the acid compounds to combat fungal diseases and weeds. We report here the crystal structure of the title compound. Two nitro groups (O3/ N1/O4 and O5/N2/O6) attached at C2 and C4, the ester group (O1/C7/O2) attached at C6 form dihedral angles of 49.4 (1)°, 87.6 (1)° and 9.1 (1)° with the mean plane of the C1-benzene ring, respectively. In the crystal structure, adjacent molecules are linked together by the weak C—H···O hydrogen bonds (Table 1).

Experimental

Commercial isopropyl 4-chloro-3,5-dinitrobenzoate was recrystallized by slow evaporation of methanol solution. Colourless single crystals were formed after several weeks.

Refinement

H atoms were placed in calculated positions and were allowed to ride on the parent C atoms with C—H distances of 0.95 (aromatic), 0.98 (methyl) and 1.00 Å (methine); Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level.

Crystal data

C10H9ClN2O6Z = 2
Mr = 288.64F(000) = 296
Triclinic, P1Dx = 1.586 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.703 (2) ÅCell parameters from 1327 reflections
b = 10.783 (5) Åθ = 3.1–27.5°
c = 12.734 (5) ŵ = 0.34 mm1
α = 69.483 (12)°T = 103 K
β = 87.75 (2)°Prism, colourless
γ = 89.61 (2)°0.57 × 0.22 × 0.10 mm
V = 604.3 (5) Å3

Data collection

Rigaku SPIDER diffractometer2689 independent reflections
Radiation source: Rotating Anode1756 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −6→6
Tmin = 0.830, Tmax = 0.967k = −14→13
5643 measured reflectionsl = −16→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0496P)2 + 0.219P] where P = (Fo2 + 2Fc2)/3
2689 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl11.35262 (13)0.43193 (6)0.65836 (5)0.02487 (18)
O10.4518 (3)0.85871 (15)0.76139 (13)0.0185 (4)
O20.3137 (3)0.67501 (15)0.90566 (13)0.0208 (4)
O31.2776 (4)0.83028 (19)0.51714 (14)0.0338 (5)
O41.1930 (4)0.66488 (19)0.46231 (15)0.0359 (5)
O51.2157 (4)0.31097 (18)0.93908 (16)0.0343 (5)
O60.8756 (4)0.24121 (18)0.86381 (17)0.0364 (5)
N11.1805 (4)0.7201 (2)0.53094 (17)0.0240 (5)
N21.0218 (4)0.3277 (2)0.87522 (18)0.0226 (5)
C10.8350 (5)0.7223 (2)0.67783 (18)0.0170 (5)
H10.79690.81190.63420.020*
C21.0341 (5)0.6512 (2)0.64011 (18)0.0182 (5)
C31.1009 (5)0.5203 (2)0.7020 (2)0.0187 (5)
C40.9569 (5)0.4649 (2)0.80468 (19)0.0170 (5)
C50.7538 (5)0.5317 (2)0.8453 (2)0.0177 (5)
H50.65900.48980.91610.021*
C60.6914 (5)0.6612 (2)0.78022 (19)0.0165 (5)
C70.4638 (5)0.7312 (2)0.82410 (19)0.0160 (5)
C80.2407 (5)0.9393 (2)0.7970 (2)0.0188 (5)
H80.06650.88480.83020.023*
C90.3717 (6)0.9834 (3)0.8837 (2)0.0288 (6)
H9A0.43200.90570.94610.043*
H9B0.23161.03320.91170.043*
H9C0.53721.04010.85000.043*
C100.1679 (6)1.0513 (2)0.6922 (2)0.0290 (6)
H10A0.33991.10340.65910.043*
H10B0.02611.10820.71080.043*
H10C0.09021.01550.63830.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0219 (3)0.0263 (3)0.0289 (3)0.0080 (2)−0.0003 (2)−0.0129 (3)
O10.0203 (9)0.0125 (8)0.0194 (8)0.0043 (6)0.0027 (7)−0.0019 (7)
O20.0215 (9)0.0166 (8)0.0197 (9)0.0035 (7)0.0035 (7)−0.0011 (7)
O30.0334 (11)0.0378 (12)0.0238 (10)−0.0102 (9)0.0041 (8)−0.0030 (9)
O40.0432 (12)0.0413 (12)0.0239 (10)0.0147 (9)0.0041 (9)−0.0130 (9)
O50.0284 (11)0.0266 (10)0.0409 (11)0.0075 (8)−0.0108 (9)−0.0020 (9)
O60.0382 (12)0.0172 (9)0.0545 (13)−0.0016 (8)−0.0044 (10)−0.0131 (9)
N10.0205 (11)0.0307 (12)0.0175 (10)0.0076 (9)−0.0001 (8)−0.0049 (9)
N20.0201 (11)0.0172 (11)0.0291 (11)0.0044 (8)0.0030 (9)−0.0068 (9)
C10.0176 (12)0.0161 (12)0.0170 (12)0.0022 (9)−0.0039 (9)−0.0050 (10)
C20.0174 (12)0.0212 (12)0.0155 (12)0.0012 (9)−0.0005 (9)−0.0057 (10)
C30.0149 (11)0.0200 (12)0.0248 (13)0.0037 (9)−0.0022 (10)−0.0122 (10)
C40.0172 (12)0.0125 (11)0.0210 (12)0.0014 (9)−0.0049 (9)−0.0049 (9)
C50.0182 (12)0.0155 (12)0.0193 (12)0.0002 (9)0.0000 (9)−0.0059 (10)
C60.0155 (11)0.0169 (11)0.0184 (12)−0.0007 (9)−0.0007 (9)−0.0078 (10)
C70.0183 (12)0.0128 (11)0.0162 (11)0.0021 (9)−0.0039 (9)−0.0041 (9)
C80.0190 (12)0.0140 (11)0.0243 (13)0.0043 (9)0.0013 (10)−0.0081 (10)
C90.0336 (15)0.0229 (14)0.0324 (14)0.0073 (11)−0.0029 (12)−0.0128 (12)
C100.0358 (16)0.0197 (13)0.0272 (14)0.0096 (11)−0.0017 (12)−0.0029 (11)

Geometric parameters (Å, °)

Cl1—C31.709 (2)C3—C41.384 (3)
O1—C71.328 (3)C4—C51.382 (3)
O1—C81.475 (3)C5—C61.388 (3)
O2—C71.205 (3)C5—H50.9500
O3—N11.227 (3)C6—C71.505 (3)
O4—N11.217 (3)C8—C91.500 (3)
O5—N21.216 (3)C8—C101.503 (3)
O6—N21.215 (3)C8—H81.0000
N1—C21.472 (3)C9—H9A0.9800
N2—C41.474 (3)C9—H9B0.9800
C1—C21.382 (3)C9—H9C0.9800
C1—C61.388 (3)C10—H10A0.9800
C1—H10.9500C10—H10B0.9800
C2—C31.395 (3)C10—H10C0.9800
C7—O1—C8116.83 (18)C1—C6—C7121.8 (2)
O4—N1—O3125.7 (2)C5—C6—C7117.9 (2)
O4—N1—C2118.2 (2)O2—C7—O1125.9 (2)
O3—N1—C2116.1 (2)O2—C7—C6122.6 (2)
O6—N2—O5125.8 (2)O1—C7—C6111.5 (2)
O6—N2—C4116.5 (2)O1—C8—C9107.98 (19)
O5—N2—C4117.61 (19)O1—C8—C10105.83 (19)
C2—C1—C6119.1 (2)C9—C8—C10113.8 (2)
C2—C1—H1120.4O1—C8—H8109.7
C6—C1—H1120.4C9—C8—H8109.7
C1—C2—C3122.5 (2)C10—C8—H8109.7
C1—C2—N1117.2 (2)C8—C9—H9A109.5
C3—C2—N1120.3 (2)C8—C9—H9B109.5
C4—C3—C2116.1 (2)H9A—C9—H9B109.5
C4—C3—Cl1120.62 (18)C8—C9—H9C109.5
C2—C3—Cl1123.26 (19)H9A—C9—H9C109.5
C5—C4—C3123.4 (2)H9B—C9—H9C109.5
C5—C4—N2117.8 (2)C8—C10—H10A109.5
C3—C4—N2118.8 (2)C8—C10—H10B109.5
C4—C5—C6118.5 (2)H10A—C10—H10B109.5
C4—C5—H5120.7C8—C10—H10C109.5
C6—C5—H5120.7H10A—C10—H10C109.5
C1—C6—C5120.3 (2)H10B—C10—H10C109.5
C6—C1—C2—C3−1.1 (3)O6—N2—C4—C3−92.1 (3)
C6—C1—C2—N1179.8 (2)O5—N2—C4—C387.7 (3)
O4—N1—C2—C1−131.1 (2)C3—C4—C5—C6−0.3 (3)
O3—N1—C2—C148.2 (3)N2—C4—C5—C6179.6 (2)
O4—N1—C2—C349.9 (3)C2—C1—C6—C52.0 (3)
O3—N1—C2—C3−130.8 (2)C2—C1—C6—C7−177.5 (2)
C1—C2—C3—C4−0.4 (3)C4—C5—C6—C1−1.3 (3)
N1—C2—C3—C4178.6 (2)C4—C5—C6—C7178.3 (2)
C1—C2—C3—Cl1−178.36 (18)C8—O1—C7—O21.9 (3)
N1—C2—C3—Cl10.6 (3)C8—O1—C7—C6−178.73 (17)
C2—C3—C4—C51.2 (3)C1—C6—C7—O2170.8 (2)
Cl1—C3—C4—C5179.18 (18)C5—C6—C7—O2−8.8 (3)
C2—C3—C4—N2−178.78 (19)C1—C6—C7—O1−8.7 (3)
Cl1—C3—C4—N2−0.8 (3)C5—C6—C7—O1171.78 (19)
O6—N2—C4—C587.9 (3)C7—O1—C8—C984.7 (2)
O5—N2—C4—C5−92.3 (3)C7—O1—C8—C10−153.16 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.353.178 (3)146

Symmetry codes: (i) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5065).

References

  • Akira, S., Shoji, K. & Kenichi, S. (1978). Jpn. Patent No. 53101528.
  • Ferenc, B., Gyoery, K. & Mihaly, N. (1984). Ger. Patent No. 3410566.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2004). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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