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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1206
doi:10.1107/S1600536813018266

Bifenox: methyl 5-(2,4-di­chloro­phen­­oxy)-2-nitro­benzoate

Youngeun Jeon,a Jineun Kim,a* Seonghwa Choa and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

(Received 25 June 2013; accepted 2 July 2013; online 6 July 2013)

In the title compound, the herbicide bifenox, C14H9Cl2NO5, the dihedral angle between the dichlorobenzene and nitro­benzene rings is 78.79 (14)°. In the crystal, C—H⋯O hydrogen bonds give rise to a three-dimensional network structure in which there are both a π–π inter­action [ring centroid separation = 3.6212 (16) Å] and a C—Cl⋯π inter­action [Cl⋯ring centroid = 3.4754 (8) Å]. In addition, short Cl⋯Cl contacts [3.3767 (11) and 3.3946 (11) Å] are present.

Related literature

For information on the insecticidal activity of the title compound, see: Jinno et al. (1999[Jinno, H., Hatakeyama, N., Hanioka, N., Yoda, R., Nishimura, T. & Ando, M. (1999). Food Chem. Toxicol. 37, 69-74.]); O'Neil (2001[O'Neil, M. J. (2001). The Merck Index, 13th ed., p. 206. Whitehouse Station, NJ, USA: Merck & Co. Inc.]). For a related crystal structure, see: Smith et al. (1981[Smith, G., Kennard, C. H. L., White, A. H. & Skelton, B. W. (1981). J. Agric. Food Chem. 29, 1046-1049.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9Cl2NO5

  • Mr = 342.12

  • Triclinic, [P \overline 1]

  • a = 8.4945 (7) Å

  • b = 9.9610 (8) Å

  • c = 10.3969 (8) Å

  • α = 64.601 (1)°

  • β = 68.720 (1)°

  • γ = 70.421 (1)°

  • V = 723.48 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 173 K

  • 0.20 × 0.10 × 0.10 mm
Data collection

  • Bruker APEXII CCD-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.912, Tmax = 0.954

  • 5707 measured reflections

  • 2830 independent reflections

  • 2217 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.098

  • S = 1.06

  • 2830 reflections

  • 200 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O4i 0.95 2.41 3.290 (3) 153
C6—H6⋯O5ii 0.95 2.43 3.243 (3) 143
C8—H8⋯O2iii 0.95 2.58 3.435 (3) 151
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018266/zs2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018266/zs2269Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018266/zs2269Isup3.cml

checkCIF report


Comment top

The title compound bifenox, C14H9Cl2NO5, is commonly used as a photobleaching herbicide for the control of many types of weeds (Jinno et al., 1999; O'Neil, 2001) and its crystal structure is reported herein. In this compound (Fig. 1), the dihedral angle between the dichlorophenyl ring and the nitrobenzene ring is 78.79 (14)°. All bond lengths and bond angles are normal and comparable to those observed in a similar phenoxy herbicide structure, methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propionate (diclofop methyl) (Smith et al., 1981).

In the crystal structure (Fig. 2), intermolecular C—H···O hydrogen bonds are observed (Table 1), giving a three-dimensional network structure (Fig. 2). In this structure there are both a π–π interaction between the dichlorophenyl rings [ring centroid separation = 3.6212 (16) Å] and a C3—Cl2···π interaction with the nitrobenzene ring [Cl2···Cgiv = 3.4754 (8) Å]. In addition, short Cl···Cl contacts [Cl1···Cl1v, 3.3767 (11) Å and Cl2···Cl2iv3.3946 (11) Å] are present [for symmetry codes: (iv), -x+2, -y, -z+1 and (v), -x+3, -y, -z+2].

Related literature top

For information on the insecticidal activity of the title compound, see: Jinno et al. (1999); O'Neil (2001). For a related crystal structure, see: Smith et al. (1981).

Experimental top

The title compound was purchased from Wako Pure Chemicals. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for Csp2—H and d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound with weak intermolecular Cl···Cl interactions and C—H···O hydrogen bonds shown as dashed lines.
Methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate top
Crystal data top
C14H9Cl2NO5Z = 2
Mr = 342.12F(000) = 348
Triclinic, P1Dx = 1.570 Mg m−3
Hall symbol: -P 1Melting point = 357–359 K
a = 8.4945 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9610 (8) ÅCell parameters from 2834 reflections
c = 10.3969 (8) Åθ = 2.3–27.4°
α = 64.601 (1)°µ = 0.47 mm−1
β = 68.720 (1)°T = 173 K
γ = 70.421 (1)°Block, colourless
V = 723.48 (10) Å30.20 × 0.10 × 0.10 mm
Data collection top
Bruker APEXII CCD-detector
diffractometer		2830 independent reflections
Radiation source: fine-focus sealed tube2217 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		h = −10→10
Tmin = 0.912, Tmax = 0.954k = −12→12
5707 measured reflectionsl = −12→12
Refinement top
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) = 0.098H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0274P)2 + 0.5552P]
where P = (Fo2 + 2Fc2)/3
2830 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C14H9Cl2NO5γ = 70.421 (1)°
Mr = 342.12V = 723.48 (10) Å3
Triclinic, P1Z = 2
a = 8.4945 (7) ÅMo Kα radiation
b = 9.9610 (8) ŵ = 0.47 mm−1
c = 10.3969 (8) ÅT = 173 K
α = 64.601 (1)°0.20 × 0.10 × 0.10 mm
β = 68.720 (1)°
Data collection top
Bruker APEXII CCD-detector
diffractometer		2830 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		2217 reflections with I > 2σ(I)
Tmin = 0.912, Tmax = 0.954Rint = 0.029
5707 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å−3
2830 reflectionsΔρmin = −0.33 e Å−3
200 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl11.32195 (8)0.11710 (8)0.94482 (7)0.03459 (19)
Cl21.02470 (9)−0.03963 (9)0.66832 (8)0.0410 (2)
O10.7224 (2)0.2017 (2)0.74018 (19)0.0329 (5)
O20.2690 (2)0.3461 (3)0.4414 (2)0.0493 (6)
O30.4770 (2)0.2201 (2)0.3023 (2)0.0379 (5)
O40.5339 (3)0.5178 (3)0.1364 (2)0.0515 (6)
O50.8081 (2)0.5119 (2)0.0585 (2)0.0371 (5)
N10.6782 (3)0.4819 (2)0.1575 (2)0.0301 (5)
C11.1456 (3)0.1440 (3)0.8819 (3)0.0256 (6)
C21.1569 (3)0.0548 (3)0.8061 (3)0.0266 (6)
H21.2589−0.01930.78800.032*
C31.0159 (3)0.0761 (3)0.7571 (3)0.0256 (6)
C40.8694 (3)0.1865 (3)0.7802 (3)0.0267 (6)
C50.8603 (3)0.2739 (3)0.8570 (3)0.0285 (6)
H50.75880.34870.87420.034*
C60.9992 (3)0.2526 (3)0.9092 (3)0.0281 (6)
H60.99350.31170.96270.034*
C70.7221 (3)0.2709 (3)0.5937 (3)0.0264 (6)
C80.8489 (3)0.3448 (3)0.4844 (3)0.0272 (6)
H80.94500.34930.50760.033*
C90.8337 (3)0.4121 (3)0.3410 (3)0.0267 (6)
H90.91910.46380.26480.032*
C100.6932 (3)0.4035 (3)0.3092 (3)0.0244 (5)
C110.5659 (3)0.3277 (3)0.4177 (3)0.0254 (6)
C120.5811 (3)0.2624 (3)0.5610 (3)0.0260 (6)
H120.49510.21160.63750.031*
C130.4188 (3)0.3035 (3)0.3881 (3)0.0273 (6)
C140.3450 (4)0.1934 (4)0.2634 (4)0.0501 (9)
H14A0.26580.14090.35330.075*
H14B0.39990.13040.20130.075*
H14C0.28020.29090.20930.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0281 (3)0.0478 (4)0.0343 (4)−0.0092 (3)−0.0157 (3)−0.0130 (3)
Cl20.0433 (4)0.0470 (5)0.0498 (5)−0.0054 (3)−0.0189 (3)−0.0297 (4)
O10.0243 (9)0.0494 (12)0.0270 (10)−0.0116 (9)−0.0117 (8)−0.0081 (9)
O20.0217 (10)0.0761 (16)0.0698 (15)−0.0060 (10)−0.0101 (10)−0.0478 (13)
O30.0288 (10)0.0505 (13)0.0516 (13)−0.0017 (9)−0.0186 (9)−0.0315 (11)
O40.0353 (12)0.0652 (15)0.0457 (13)−0.0094 (11)−0.0264 (10)0.0000 (11)
O50.0334 (11)0.0450 (12)0.0299 (10)−0.0096 (9)−0.0056 (9)−0.0117 (9)
N10.0298 (12)0.0278 (12)0.0343 (13)−0.0021 (10)−0.0161 (10)−0.0090 (10)
C10.0240 (13)0.0306 (14)0.0216 (13)−0.0088 (11)−0.0088 (10)−0.0040 (11)
C20.0234 (13)0.0279 (14)0.0264 (14)−0.0032 (11)−0.0087 (11)−0.0073 (11)
C30.0269 (13)0.0272 (14)0.0245 (13)−0.0073 (11)−0.0082 (11)−0.0083 (11)
C40.0234 (13)0.0334 (15)0.0247 (13)−0.0110 (11)−0.0108 (10)−0.0040 (11)
C50.0256 (13)0.0281 (14)0.0316 (14)−0.0012 (11)−0.0099 (11)−0.0115 (12)
C60.0324 (14)0.0276 (14)0.0273 (14)−0.0085 (11)−0.0081 (11)−0.0106 (12)
C70.0226 (13)0.0278 (14)0.0295 (14)−0.0024 (11)−0.0123 (11)−0.0083 (12)
C80.0231 (13)0.0272 (14)0.0355 (15)−0.0045 (11)−0.0151 (11)−0.0093 (12)
C90.0246 (13)0.0230 (13)0.0310 (15)−0.0057 (11)−0.0106 (11)−0.0046 (11)
C100.0240 (13)0.0201 (13)0.0287 (14)−0.0009 (10)−0.0115 (11)−0.0074 (11)
C110.0194 (12)0.0238 (13)0.0351 (15)−0.0006 (10)−0.0104 (11)−0.0126 (12)
C120.0215 (12)0.0315 (14)0.0267 (14)−0.0052 (11)−0.0083 (11)−0.0103 (12)
C130.0233 (14)0.0287 (14)0.0304 (14)−0.0042 (11)−0.0098 (11)−0.0096 (12)
C140.0442 (18)0.063 (2)0.067 (2)−0.0051 (16)−0.0316 (17)−0.0349 (19)
Geometric parameters (Å, º) top
Cl1—C11.743 (2)C5—C61.389 (3)
Cl2—C31.729 (3)C5—H50.9500
O1—C71.377 (3)C6—H60.9500
O1—C41.397 (3)C7—C81.386 (3)
O2—C131.198 (3)C7—C121.394 (3)
O3—C131.331 (3)C8—C91.383 (3)
O3—C141.454 (3)C8—H80.9500
O4—N11.230 (3)C9—C101.386 (3)
O5—N11.224 (3)C9—H90.9500
N1—C101.462 (3)C10—C111.393 (3)
C1—C61.379 (4)C11—C121.383 (3)
C1—C21.381 (4)C11—C131.504 (3)
C2—C31.386 (3)C12—H120.9500
C2—H20.9500C14—H14A0.9800
C3—C41.382 (4)C14—H14B0.9800
C4—C51.381 (4)C14—H14C0.9800
C7—O1—C4118.65 (19)C8—C7—C12121.1 (2)
C13—O3—C14115.5 (2)C9—C8—C7119.1 (2)
O5—N1—O4123.3 (2)C9—C8—H8120.5
O5—N1—C10118.8 (2)C7—C8—H8120.5
O4—N1—C10117.9 (2)C8—C9—C10119.6 (2)
C6—C1—C2121.9 (2)C8—C9—H9120.2
C6—C1—Cl1119.5 (2)C10—C9—H9120.2
C2—C1—Cl1118.61 (19)C9—C10—C11121.9 (2)
C1—C2—C3118.4 (2)C9—C10—N1117.7 (2)
C1—C2—H2120.8C11—C10—N1120.3 (2)
C3—C2—H2120.8C12—C11—C10118.1 (2)
C4—C3—C2120.7 (2)C12—C11—C13117.5 (2)
C4—C3—Cl2120.33 (19)C10—C11—C13124.3 (2)
C2—C3—Cl2118.96 (19)C11—C12—C7120.2 (2)
C5—C4—C3120.0 (2)C11—C12—H12119.9
C5—C4—O1118.7 (2)C7—C12—H12119.9
C3—C4—O1121.0 (2)O2—C13—O3124.4 (2)
C4—C5—C6120.1 (2)O2—C13—C11124.5 (2)
C4—C5—H5119.9O3—C13—C11111.0 (2)
C6—C5—H5119.9O3—C14—H14A109.5
C1—C6—C5118.8 (2)O3—C14—H14B109.5
C1—C6—H6120.6H14A—C14—H14B109.5
C5—C6—H6120.6O3—C14—H14C109.5
O1—C7—C8124.2 (2)H14A—C14—H14C109.5
O1—C7—C12114.7 (2)H14B—C14—H14C109.5
C6—C1—C2—C3−0.2 (4)C8—C9—C10—C11−0.5 (4)
Cl1—C1—C2—C3179.62 (19)C8—C9—C10—N1177.3 (2)
C1—C2—C3—C41.6 (4)O5—N1—C10—C921.5 (3)
C1—C2—C3—Cl2−177.51 (19)O4—N1—C10—C9−156.8 (2)
C2—C3—C4—C5−2.1 (4)O5—N1—C10—C11−160.7 (2)
Cl2—C3—C4—C5177.1 (2)O4—N1—C10—C1121.0 (3)
C2—C3—C4—O1−175.6 (2)C9—C10—C11—C121.2 (4)
Cl2—C3—C4—O13.6 (3)N1—C10—C11—C12−176.5 (2)
C7—O1—C4—C5109.5 (3)C9—C10—C11—C13−174.7 (2)
C7—O1—C4—C3−77.0 (3)N1—C10—C11—C137.6 (4)
C3—C4—C5—C61.0 (4)C10—C11—C12—C7−1.1 (4)
O1—C4—C5—C6174.6 (2)C13—C11—C12—C7175.1 (2)
C2—C1—C6—C5−0.9 (4)O1—C7—C12—C11180.0 (2)
Cl1—C1—C6—C5179.32 (19)C8—C7—C12—C110.3 (4)
C4—C5—C6—C10.5 (4)C14—O3—C13—O25.6 (4)
C4—O1—C7—C8−8.8 (4)C14—O3—C13—C11−178.4 (2)
C4—O1—C7—C12171.5 (2)C12—C11—C13—O261.9 (4)
O1—C7—C8—C9−179.2 (2)C10—C11—C13—O2−122.1 (3)
C12—C7—C8—C90.5 (4)C12—C11—C13—O3−114.1 (3)
C7—C8—C9—C10−0.4 (4)C10—C11—C13—O361.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.413.290 (3)153
C6—H6···O5ii0.952.433.243 (3)143
C8—H8···O2iii0.952.583.435 (3)151
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H9Cl2NO5
Mr342.12
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.4945 (7), 9.9610 (8), 10.3969 (8)
α, β, γ (°)64.601 (1), 68.720 (1), 70.421 (1)
V (Å3)723.48 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.47
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII CCD-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.912, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections		5707, 2830, 2217
Rint0.029
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.098, 1.06
No. of reflections2830
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.29, −0.33

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.413.290 (3)153
C6—H6···O5ii0.952.433.243 (3)143
C8—H8···O2iii0.952.583.435 (3)151
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x+1, y, z.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1206
doi:10.1107/S1600536813018266
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