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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 5| May 2013| Page o671
https://doi.org/10.1107/S1600536813008878

Methyl 2-{2-[(2-methyl­phen­­oxy)meth­yl]phen­yl}-2-oxo­acetate

Manpreet Kaur,a Ray J. Butcher,b Jerry P. Jasinski,c* H. S. Yathirajana and B. P. Siddarajud

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, G. Madegowda Institute of Technology (GMIT), Bharathinagara 571 422, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 27 March 2013; accepted 1 April 2013; online 10 April 2013)

In the title compound, C17H16O4, the dihedral angle between the benzene rings is 4.4 (2)°. In the crystal, weak C—H⋯O hydrogen bonds connect mol­ecules along [001].

Related literature

The title compound is used in organic synthesis as a fungicide inter­mediate. For background to agrochemical fungicidal activity, see: Balba (2007[Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.]); Cash & Cronan (2001[Cash, H. & Cronan, J. M. Jr (2001). US Patent Appl. WO2001-US964920010323.]); Ammermann et al. (2000[Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the Brighton Crop Protection Conference-Pests and Diseases, Vol. 2, pp. 541-548. Alton, Hampshire, England: BCPC Publications.]); For related structures see: Chopra et al. (2004[Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2421-o2423.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C17H16O4

  • Mr = 284.30

  • Monoclinic, C 2/c

  • a = 31.6697 (11) Å

  • b = 7.5883 (2) Å

  • c = 12.5915 (6) Å

  • β = 108.514 (4)°

  • V = 2869.4 (2) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.77 mm−1

  • T = 123 K

  • 0.47 × 0.34 × 0.14 mm
Data collection

  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.921, Tmax = 1.000

  • 5506 measured reflections

  • 2897 independent reflections

  • 2551 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.07

  • 2897 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C17—H17A⋯O2i 0.98 2.44 3.3712 (18) 158
Symmetry code: (i) [x, -y, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008878/lh5601sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008878/lh5601Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008878/lh5601Isup3.cml

checkCIF report


Comment top

The title compound (I) is used in organic synthesis as a fungicide intermediate and mainly used as an intermediate for the preparation of methyl 2(E)-methoxyimino-2-[2-(2-methylphenoxymethyl)phenyl] acetate or kresoxim-methyl, which is an active agrochemical exhibiting fungicidal activity (Ammermann et al., 2000; Balba, 2007; Cash & Cronan, 2001). The crystal structure of kresoxim-methyl (Chopra et al., 2004) and 2-[(E)-methoxyimino]-2-{2-[(2-methylphenoxy) methyl]phenyl}ethanoic acid (Kant et al., 2012) have been reported. In view of the importance of the title compound, this paper reports its crystal structure.

In (I), the dihedral angle between the mean planes of the benzene rings is 4.4 (2)° (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, weak C—H···O hydrogen bonds connect (Table 1) molecules along [001] (Fig. 2).

Related literature top

The title compound is used in organic synthesis as a fungicide intermediate. For background to agrochemical fungicidal activity, see: Balba (2007); Cash & Cronan (2001); Ammermann et al. (2000); For related structures see : Chopra et al. (2004); Kant et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was a gift sample from RL Fine Chem, Bengaluru, India. The compound was recrystallized from methyl t-butyl ether by slow evaporation (M.P.: 322–323 K).

Refinement top

All H atoms were placed in calculated positions and refined using a riding-model approximation with C—H lengths of 0.95Å (CH), 0.99Å (CH2) or 0.98Å (CH3). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2) or 1.5 (CH3) times Ueq of the parent atom. Secondary CH2 refined with riding coordinates: C8(H8A,H8B.). Aromatic H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13). Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C17(H17A,H17B,H17C).

Structure description top

The title compound (I) is used in organic synthesis as a fungicide intermediate and mainly used as an intermediate for the preparation of methyl 2(E)-methoxyimino-2-[2-(2-methylphenoxymethyl)phenyl] acetate or kresoxim-methyl, which is an active agrochemical exhibiting fungicidal activity (Ammermann et al., 2000; Balba, 2007; Cash & Cronan, 2001). The crystal structure of kresoxim-methyl (Chopra et al., 2004) and 2-[(E)-methoxyimino]-2-{2-[(2-methylphenoxy) methyl]phenyl}ethanoic acid (Kant et al., 2012) have been reported. In view of the importance of the title compound, this paper reports its crystal structure.

In (I), the dihedral angle between the mean planes of the benzene rings is 4.4 (2)° (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, weak C—H···O hydrogen bonds connect (Table 1) molecules along [001] (Fig. 2).

The title compound is used in organic synthesis as a fungicide intermediate. For background to agrochemical fungicidal activity, see: Balba (2007); Cash & Cronan (2001); Ammermann et al. (2000); For related structures see : Chopra et al. (2004); Kant et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate weak C—H···O intermolecular interactions. H atoms not involved in these weak intermolecular interactions have been omitted for clarity.
Methyl 2-{2-[(2-methylphenoxy)methyl]phenyl}-2-oxoacetate top
Crystal data top
C17H16O4F(000) = 1200
Mr = 284.30Dx = 1.316 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 31.6697 (11) ÅCell parameters from 3111 reflections
b = 7.5883 (2) Åθ = 2.9–75.3°
c = 12.5915 (6) ŵ = 0.77 mm−1
β = 108.514 (4)°T = 123 K
V = 2869.4 (2) Å3Prism, colorless
Z = 80.47 × 0.34 × 0.14 mm
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer		2551 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm-1Rint = 0.021
ω scansθmax = 75.5°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2012)		h = −39→35
Tmin = 0.921, Tmax = 1.000k = −8→9
5506 measured reflectionsl = −12→15
2897 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0554P)2 + 1.2142P],
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2897 reflectionsΔρmax = 0.23 e Å−3
192 parametersΔρmin = −0.20 e Å−3
Crystal data top
C17H16O4V = 2869.4 (2) Å3
Mr = 284.30Z = 8
Monoclinic, C2/cCu Kα radiation
a = 31.6697 (11) ŵ = 0.77 mm−1
b = 7.5883 (2) ÅT = 123 K
c = 12.5915 (6) Å0.47 × 0.34 × 0.14 mm
β = 108.514 (4)°
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer		2897 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2012)		2551 reflections with I > 2σ(I)
Tmin = 0.921, Tmax = 1.000Rint = 0.021
5506 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.07Δρmax = 0.23 e Å−3
2897 reflectionsΔρmin = −0.20 e Å−3
192 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.15989 (3)0.23976 (12)0.71615 (8)0.0269 (2)
O20.05640 (3)0.09672 (13)0.83488 (8)0.0334 (2)
O3−0.01120 (3)0.31730 (14)0.91715 (8)0.0328 (2)
O40.04621 (3)0.20101 (15)1.05392 (8)0.0345 (3)
C10.17209 (4)0.09964 (17)0.66403 (10)0.0228 (3)
C20.15067 (4)−0.06284 (18)0.64687 (10)0.0257 (3)
H20.1261−0.08290.67340.031*
C30.16520 (4)−0.19597 (18)0.59084 (11)0.0298 (3)
H30.1507−0.30710.57950.036*
C40.20081 (5)−0.16704 (19)0.55151 (11)0.0315 (3)
H40.2105−0.25720.51240.038*
C50.22218 (4)−0.00414 (19)0.57003 (10)0.0286 (3)
H50.24670.01490.54340.034*
C60.20871 (4)0.13107 (18)0.62609 (10)0.0238 (3)
C70.23140 (4)0.30732 (19)0.64563 (12)0.0306 (3)
H7A0.25760.30390.62000.046*
H7B0.24080.33510.72580.046*
H7C0.21070.39790.60390.046*
C80.12311 (4)0.21425 (17)0.75746 (11)0.0243 (3)
H8A0.12930.11450.81090.029*
H8B0.09580.18700.69470.029*
C90.11668 (4)0.38121 (17)0.81511 (10)0.0224 (3)
C100.14305 (4)0.52884 (18)0.81747 (11)0.0267 (3)
H100.16480.52500.78020.032*
C110.13820 (4)0.68171 (18)0.87322 (11)0.0287 (3)
H110.15660.78060.87350.034*
C120.10674 (4)0.69138 (17)0.92858 (11)0.0278 (3)
H120.10330.79640.96620.033*
C130.08042 (4)0.54612 (17)0.92822 (10)0.0247 (3)
H130.05910.55150.96680.030*
C140.08456 (4)0.39122 (17)0.87205 (10)0.0222 (3)
C150.05692 (4)0.23845 (17)0.87950 (10)0.0243 (3)
C160.02595 (4)0.26027 (16)0.95160 (11)0.0240 (3)
C170.02123 (5)0.2110 (2)1.13287 (13)0.0395 (4)
H17A0.03730.14741.20150.059*
H17B−0.00820.15771.09940.059*
H17C0.01770.33471.15090.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0267 (4)0.0268 (5)0.0336 (5)−0.0032 (4)0.0187 (4)−0.0044 (4)
O20.0380 (5)0.0261 (5)0.0447 (6)−0.0063 (4)0.0254 (4)−0.0081 (4)
O30.0250 (5)0.0420 (6)0.0332 (5)0.0060 (4)0.0117 (4)−0.0003 (4)
O40.0296 (5)0.0466 (6)0.0335 (5)0.0129 (4)0.0189 (4)0.0124 (4)
C10.0212 (5)0.0276 (6)0.0205 (5)0.0017 (5)0.0080 (4)−0.0008 (5)
C20.0218 (6)0.0308 (7)0.0260 (6)−0.0019 (5)0.0095 (5)−0.0017 (5)
C30.0296 (7)0.0288 (7)0.0302 (7)−0.0023 (5)0.0084 (5)−0.0042 (5)
C40.0339 (7)0.0340 (7)0.0292 (7)0.0057 (6)0.0138 (5)−0.0046 (6)
C50.0265 (6)0.0366 (7)0.0269 (6)0.0047 (5)0.0143 (5)0.0027 (5)
C60.0211 (5)0.0299 (6)0.0211 (5)0.0011 (5)0.0077 (4)0.0028 (5)
C70.0281 (6)0.0338 (7)0.0345 (7)−0.0043 (5)0.0163 (5)0.0008 (6)
C80.0230 (6)0.0268 (6)0.0278 (6)−0.0016 (5)0.0145 (5)−0.0017 (5)
C90.0218 (5)0.0251 (6)0.0204 (5)0.0013 (5)0.0068 (4)0.0010 (5)
C100.0251 (6)0.0293 (7)0.0277 (6)−0.0015 (5)0.0112 (5)0.0007 (5)
C110.0272 (6)0.0251 (6)0.0329 (7)−0.0035 (5)0.0083 (5)0.0008 (5)
C120.0287 (6)0.0243 (6)0.0285 (6)0.0019 (5)0.0064 (5)−0.0041 (5)
C130.0226 (6)0.0275 (6)0.0247 (6)0.0032 (5)0.0086 (4)−0.0009 (5)
C140.0209 (5)0.0239 (6)0.0222 (5)0.0013 (5)0.0074 (4)0.0006 (5)
C150.0227 (6)0.0264 (6)0.0261 (6)0.0015 (5)0.0109 (5)0.0001 (5)
C160.0241 (6)0.0214 (6)0.0292 (6)−0.0011 (5)0.0124 (5)−0.0006 (5)
C170.0421 (8)0.0485 (9)0.0376 (8)0.0142 (7)0.0265 (6)0.0154 (7)
Geometric parameters (Å, º) top
O1—C11.3681 (15)C7—H7C0.9800
O1—C81.4315 (13)C8—H8A0.9900
O2—C151.2111 (16)C8—H8B0.9900
O3—C161.1981 (16)C8—C91.5058 (17)
O4—C161.3224 (16)C9—C101.3919 (18)
O4—C171.4560 (15)C9—C141.4204 (16)
C1—C21.3907 (18)C10—H100.9500
C1—C61.4078 (16)C10—C111.3894 (19)
C2—H20.9500C11—H110.9500
C2—C31.3915 (18)C11—C121.3876 (18)
C3—H30.9500C12—H120.9500
C3—C41.3855 (19)C12—C131.3810 (19)
C4—H40.9500C13—H130.9500
C4—C51.393 (2)C13—C141.3993 (17)
C5—H50.9500C14—C151.4736 (17)
C5—C61.3871 (18)C15—C161.5423 (16)
C6—C71.5010 (18)C17—H17A0.9800
C7—H7A0.9800C17—H17B0.9800
C7—H7B0.9800C17—H17C0.9800
C1—O1—C8117.10 (10)C9—C8—H8B110.1
C16—O4—C17116.53 (10)C10—C9—C8121.03 (11)
O1—C1—C2124.43 (11)C10—C9—C14117.85 (11)
O1—C1—C6114.82 (11)C14—C9—C8121.09 (11)
C2—C1—C6120.75 (12)C9—C10—H10119.3
C1—C2—H2120.0C11—C10—C9121.40 (12)
C1—C2—C3119.93 (11)C11—C10—H10119.3
C3—C2—H2120.0C10—C11—H11119.7
C2—C3—H3119.9C12—C11—C10120.67 (12)
C4—C3—C2120.26 (13)C12—C11—H11119.7
C4—C3—H3119.9C11—C12—H12120.5
C3—C4—H4120.4C13—C12—C11119.02 (12)
C3—C4—C5119.21 (12)C13—C12—H12120.5
C5—C4—H4120.4C12—C13—H13119.4
C4—C5—H5119.0C12—C13—C14121.25 (11)
C6—C5—C4122.02 (12)C14—C13—H13119.4
C6—C5—H5119.0C9—C14—C15121.69 (11)
C1—C6—C7119.89 (11)C13—C14—C9119.81 (11)
C5—C6—C1117.83 (12)C13—C14—C15118.40 (11)
C5—C6—C7122.28 (11)O2—C15—C14126.15 (11)
C6—C7—H7A109.5O2—C15—C16116.80 (11)
C6—C7—H7B109.5C14—C15—C16117.05 (11)
C6—C7—H7C109.5O3—C16—O4126.33 (12)
H7A—C7—H7B109.5O3—C16—C15124.09 (12)
H7A—C7—H7C109.5O4—C16—C15109.53 (10)
H7B—C7—H7C109.5O4—C17—H17A109.5
O1—C8—H8A110.1O4—C17—H17B109.5
O1—C8—H8B110.1O4—C17—H17C109.5
O1—C8—C9108.15 (10)H17A—C17—H17B109.5
H8A—C8—H8B108.4H17A—C17—H17C109.5
C9—C8—H8A110.1H17B—C17—H17C109.5
O1—C1—C2—C3178.72 (11)C8—C9—C14—C13177.75 (11)
O1—C1—C6—C5−178.46 (11)C8—C9—C14—C151.40 (17)
O1—C1—C6—C70.78 (16)C9—C10—C11—C120.1 (2)
O1—C8—C9—C102.58 (16)C9—C14—C15—O2−4.4 (2)
O1—C8—C9—C14−175.27 (10)C9—C14—C15—C16175.10 (10)
O2—C15—C16—O3−92.56 (17)C10—C9—C14—C13−0.16 (17)
O2—C15—C16—O485.23 (15)C10—C9—C14—C15−176.51 (11)
C1—O1—C8—C9177.79 (10)C10—C11—C12—C130.47 (19)
C1—C2—C3—C4−0.34 (19)C11—C12—C13—C14−0.85 (19)
C2—C1—C6—C50.85 (18)C12—C13—C14—C90.70 (18)
C2—C1—C6—C7−179.91 (12)C12—C13—C14—C15177.17 (11)
C2—C3—C4—C50.8 (2)C13—C14—C15—O2179.20 (12)
C3—C4—C5—C6−0.5 (2)C13—C14—C15—C16−1.30 (17)
C4—C5—C6—C1−0.35 (19)C14—C9—C10—C11−0.21 (18)
C4—C5—C6—C7−179.57 (12)C14—C15—C16—O387.90 (16)
C6—C1—C2—C3−0.51 (19)C14—C15—C16—O4−94.31 (13)
C8—O1—C1—C21.38 (17)C17—O4—C16—O3−1.9 (2)
C8—O1—C1—C6−179.34 (10)C17—O4—C16—C15−179.59 (12)
C8—C9—C10—C11−178.12 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.982.443.3712 (18)158
Symmetry code: (i) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H16O4
Mr284.30
Crystal system, space groupMonoclinic, C2/c
Temperature (K)123
a, b, c (Å)31.6697 (11), 7.5883 (2), 12.5915 (6)
β (°) 108.514 (4)
V (Å3)2869.4 (2)
Z8
Radiation typeCu Kα
µ (mm−1)0.77
Crystal size (mm)0.47 × 0.34 × 0.14
Data collection
DiffractometerAgilent Xcalibur (Ruby, Gemini)
Absorption correctionMulti-scan
(CrysAlis RED; Agilent, 2012)
Tmin, Tmax0.921, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5506, 2897, 2551
Rint0.021
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 1.07
No. of reflections2897
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.20

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2012 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.982.443.3712 (18)157.8
Symmetry code: (i) x, −y, z+1/2.
 

Acknowledgements

MK thanks the UOM for research facilities. RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

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ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page o671
https://doi.org/10.1107/S1600536813008878
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