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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o62.
Published online 2009 December 4. doi:  10.1107/S1600536809051630
PMCID: PMC2980218

Methyl 4-chloro-3,5-dinitro­benzoate

Abstract

In the mol­ecule of the title compound, C8H5ClN2O6, the two nitro groups and the ester group make dihedral angles of 29.6 (1)°, 82.3 (1)° and 13.7 (1)°, respectively, with the benzene ring. In the crystal structure weak C—H(...)O inter­actions are present.

Related literature

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

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Object name is e-66-00o62-scheme1.jpg

Experimental

Crystal data

  • C8H5ClN2O6
  • M r = 260.59
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o62-efi1.jpg
  • a = 4.8579 (10) Å
  • b = 9.4438 (19) Å
  • c = 11.369 (2) Å
  • α = 73.36 (3)°
  • β = 88.09 (3)°
  • γ = 87.47 (3)°
  • V = 499.14 (18) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 93 K
  • 0.50 × 0.33 × 0.17 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: multi-scan (North et al., 1968 [triangle]) T min = 0.824, T max = 0.936
  • 3935 measured reflections
  • 2193 independent reflections
  • 1607 reflections with I > 2σ(I)
  • R int = 0.029
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.142
  • S = 1.02
  • 2193 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.85 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: RAPID-AUTO (Rigaku 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051630/xu2697sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051630/xu2697Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from Jiangsu Institute of Nuclear Medicine, China.

supplementary crystallographic information

Comment

The title compound (Fig.1) is useful as a herbicide (Akira et al.,1978; Ferenc et al., 1984). It give good result as seed-dressing fungicide for sunflower, corn and flax. We report here the crystal structure of the title compound. Two nitro groups (O1/N1/O2 and O3/N2/O4) attached at C2 and C4, the ester group(O5/C7/O6) attached at C6 form dihedral angles of 150.4 (1)°, 97.7 (1)° and 166.3 (1)° with the mean plane of the C1-benzene ring, respectively. In the crystal structure, adjacent molecules are linked through weak C—H···O hydrogen interactions (Table 1).

Experimental

A sample of commercial methyl 4-chloro-3,5-dinitrobenzoate (Aldrich) was crystalized by slow evaporation of a solution in methanol: colourless chunk-shaped crystals were formed after several days.

Refinement

H atoms are positioned geometrically, with C—H = 0.95 and 0.98 Å for benzene and methyl H atoms respectively, and are allowed to ride on the C atoms to which they are bonded, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) fot the aromatic H atoms.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C8H5ClN2O6Z = 2
Mr = 260.59F(000) = 264
Triclinic, P1Dx = 1.734 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8579 (10) ÅCell parameters from 1306 reflections
b = 9.4438 (19) Åθ = 3.7–27.5°
c = 11.369 (2) ŵ = 0.40 mm1
α = 73.36 (3)°T = 93 K
β = 88.09 (3)°Chunk, colorless
γ = 87.47 (3)°0.50 × 0.33 × 0.17 mm
V = 499.14 (18) Å3

Data collection

Rigaku SPIDER diffractometer2193 independent reflections
Radiation source: Rotating Anode1607 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (North et al., 1968)h = −6→6
Tmin = 0.824, Tmax = 0.936k = −9→12
3935 measured reflectionsl = −13→14

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3
2193 reflections(Δ/σ)max = 0.001
155 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = −0.32 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
Cl11.27729 (13)1.05900 (7)0.37558 (6)0.0216 (2)
O10.9997 (5)0.6244 (2)0.56066 (17)0.0317 (5)
O21.3643 (4)0.7546 (2)0.51374 (19)0.0345 (5)
O31.1854 (4)1.2028 (2)0.07808 (17)0.0249 (5)
O40.8170 (4)1.2738 (2)0.16400 (18)0.0278 (5)
O50.4877 (4)0.58546 (19)0.21655 (17)0.0220 (4)
O60.3199 (4)0.79731 (19)0.08858 (15)0.0194 (4)
N11.1375 (5)0.7234 (2)0.4913 (2)0.0222 (5)
N20.9797 (5)1.1792 (2)0.1458 (2)0.0191 (5)
C10.8221 (5)0.7323 (3)0.3272 (2)0.0172 (5)
H10.78810.63150.36720.021*
C21.0070 (5)0.8080 (3)0.3755 (2)0.0175 (5)
C31.0622 (5)0.9551 (3)0.3184 (2)0.0164 (5)
C40.9246 (5)1.0237 (3)0.2102 (2)0.0172 (5)
C50.7370 (5)0.9523 (3)0.1612 (2)0.0171 (5)
H50.64321.00330.08840.021*
C60.6874 (5)0.8061 (3)0.2193 (2)0.0168 (5)
C70.4771 (5)0.7304 (3)0.1662 (2)0.0168 (5)
C80.2922 (6)0.5029 (3)0.1694 (3)0.0244 (6)
H8A0.10360.53460.18600.037*
H8B0.31960.39690.21000.037*
H8C0.32210.52190.08070.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0217 (4)0.0228 (4)0.0222 (4)−0.0051 (3)−0.0061 (3)−0.0083 (3)
O10.0396 (13)0.0269 (11)0.0254 (11)−0.0063 (9)−0.0043 (9)−0.0013 (9)
O20.0279 (12)0.0400 (13)0.0325 (12)−0.0039 (10)−0.0142 (10)−0.0035 (10)
O30.0229 (10)0.0239 (10)0.0253 (10)−0.0084 (8)0.0037 (8)−0.0025 (8)
O40.0286 (11)0.0177 (10)0.0380 (12)0.0006 (8)−0.0006 (9)−0.0093 (9)
O50.0251 (10)0.0143 (9)0.0260 (10)−0.0062 (7)−0.0078 (8)−0.0035 (8)
O60.0213 (10)0.0192 (9)0.0165 (9)−0.0052 (7)−0.0055 (8)−0.0017 (8)
N10.0279 (13)0.0192 (12)0.0189 (12)−0.0012 (10)−0.0085 (10)−0.0037 (10)
N20.0213 (12)0.0165 (11)0.0196 (11)−0.0053 (9)−0.0058 (9)−0.0042 (9)
C10.0209 (13)0.0150 (12)0.0145 (13)−0.0007 (10)−0.0014 (10)−0.0020 (10)
C20.0191 (13)0.0188 (13)0.0148 (13)0.0025 (10)−0.0032 (10)−0.0053 (10)
C30.0145 (12)0.0191 (13)0.0174 (13)−0.0022 (10)−0.0033 (10)−0.0074 (11)
C40.0173 (13)0.0136 (12)0.0192 (13)−0.0030 (10)0.0014 (10)−0.0022 (10)
C50.0159 (12)0.0168 (12)0.0179 (13)−0.0018 (10)−0.0025 (10)−0.0035 (10)
C60.0167 (12)0.0152 (12)0.0177 (13)−0.0015 (10)−0.0013 (10)−0.0034 (10)
C70.0166 (12)0.0152 (12)0.0167 (13)−0.0039 (10)0.0009 (11)−0.0012 (10)
C80.0252 (15)0.0154 (13)0.0345 (16)−0.0085 (11)−0.0045 (12)−0.0082 (12)

Geometric parameters (Å, °)

Cl1—C31.725 (3)C1—C61.393 (4)
O1—N11.242 (3)C1—H10.9500
O2—N11.207 (3)C2—C31.388 (4)
O3—N21.229 (3)C3—C41.393 (4)
O4—N21.224 (3)C4—C51.377 (3)
O5—C71.323 (3)C5—C61.378 (3)
O5—C81.461 (3)C5—H50.9500
O6—C71.202 (3)C6—C71.507 (3)
N1—C21.477 (3)C8—H8A0.9800
N2—C41.473 (3)C8—H8B0.9800
C1—C21.390 (3)C8—H8C0.9800
C7—O5—C8115.43 (19)C5—C4—N2118.5 (2)
O2—N1—O1124.3 (2)C3—C4—N2118.8 (2)
O2—N1—C2119.4 (2)C4—C5—C6119.1 (2)
O1—N1—C2116.3 (2)C4—C5—H5120.4
O4—N2—O3125.6 (2)C6—C5—H5120.4
O4—N2—C4117.4 (2)C5—C6—C1120.3 (2)
O3—N2—C4117.0 (2)C5—C6—C7118.5 (2)
C2—C1—C6119.2 (2)C1—C6—C7121.1 (2)
C2—C1—H1120.4O6—C7—O5125.7 (2)
C6—C1—H1120.4O6—C7—C6122.5 (2)
C3—C2—C1121.6 (2)O5—C7—C6111.8 (2)
C3—C2—N1122.3 (2)O5—C8—H8A109.5
C1—C2—N1116.1 (2)O5—C8—H8B109.5
C2—C3—C4117.0 (2)H8A—C8—H8B109.5
C2—C3—Cl1124.5 (2)O5—C8—H8C109.5
C4—C3—Cl1118.43 (19)H8A—C8—H8C109.5
C5—C4—C3122.7 (2)H8B—C8—H8C109.5
C6—C1—C2—C3−0.5 (4)O3—N2—C4—C5−98.0 (3)
C6—C1—C2—N1178.8 (2)O4—N2—C4—C3−97.7 (3)
O2—N1—C2—C3−29.5 (4)O3—N2—C4—C382.5 (3)
O1—N1—C2—C3149.4 (3)C3—C4—C5—C6−1.7 (4)
O2—N1—C2—C1151.2 (3)N2—C4—C5—C6178.8 (2)
O1—N1—C2—C1−29.9 (3)C4—C5—C6—C11.0 (4)
C1—C2—C3—C4−0.1 (4)C4—C5—C6—C7178.7 (2)
N1—C2—C3—C4−179.4 (2)C2—C1—C6—C50.1 (4)
C1—C2—C3—Cl1177.2 (2)C2—C1—C6—C7−177.6 (2)
N1—C2—C3—Cl1−2.1 (4)C8—O5—C7—O61.4 (4)
C2—C3—C4—C51.3 (4)C8—O5—C7—C6−179.4 (2)
Cl1—C3—C4—C5−176.2 (2)C5—C6—C7—O6−12.6 (4)
C2—C3—C4—N2−179.3 (2)C1—C6—C7—O6165.0 (2)
Cl1—C3—C4—N23.2 (3)C5—C6—C7—O5168.2 (2)
O4—N2—C4—C581.8 (3)C1—C6—C7—O5−14.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.513.329 (3)145
C5—H5···O6ii0.952.343.143 (3)142

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2697).

References

  • Akira, S., Shoji, K. & Kenichi, S. (1978). Japan Patent No. 53101528
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Ferenc, B., Gyoery, K. & Mihaly, N. (1984). German Patent No. 3410566
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography