Methyl 2-{2-[(2-methyl-phen-oxy)meth-yl]phen-yl}-2-oxoacetate.

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 mol-ecules 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 ▶); 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

Crystal data

C17H16O4

M = 284.30

Monoclinic,

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 ▶) T min = 0.921, T max = 1.000

5506 measured reflections

2897 independent reflections

2551 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 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

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008878/lh5601sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008878/lh5601Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008878/lh5601Isup3.cml

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

C17H16O4	F(000) = 1200
Mr = 284.30	Dx = 1.316 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 31.6697 (11) Å	Cell parameters from 3111 reflections
b = 7.5883 (2) Å	θ = 2.9–75.3°
c = 12.5915 (6) Å	µ = 0.77 mm−1
β = 108.514 (4)°	T = 123 K
V = 2869.4 (2) Å3	Prism, colorless
Z = 8	0.47 × 0.34 × 0.14 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	2551 reflections with I > 2σ(I)
Detector resolution: 10.5081 pixels mm-1	Rint = 0.021
ω scans	θmax = 75.5°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −39→35
Tmin = 0.921, Tmax = 1.000	k = −8→9
5506 measured reflections	l = −12→15
2897 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-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 reflections	Δρmax = 0.23 e Å−3
192 parameters	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.15989 (3)	0.23976 (12)	0.71615 (8)	0.0269 (2)
O2	0.05640 (3)	0.09672 (13)	0.83488 (8)	0.0334 (2)
O3	−0.01120 (3)	0.31730 (14)	0.91715 (8)	0.0328 (2)
O4	0.04621 (3)	0.20101 (15)	1.05392 (8)	0.0345 (3)
C1	0.17209 (4)	0.09964 (17)	0.66403 (10)	0.0228 (3)
C2	0.15067 (4)	−0.06284 (18)	0.64687 (10)	0.0257 (3)
H2	0.1261	−0.0829	0.6734	0.031*
C3	0.16520 (4)	−0.19597 (18)	0.59084 (11)	0.0298 (3)
H3	0.1507	−0.3071	0.5795	0.036*
C4	0.20081 (5)	−0.16704 (19)	0.55151 (11)	0.0315 (3)
H4	0.2105	−0.2572	0.5124	0.038*
C5	0.22218 (4)	−0.00414 (19)	0.57003 (10)	0.0286 (3)
H5	0.2467	0.0149	0.5434	0.034*
C6	0.20871 (4)	0.13107 (18)	0.62609 (10)	0.0238 (3)
C7	0.23140 (4)	0.30732 (19)	0.64563 (12)	0.0306 (3)
H7A	0.2576	0.3039	0.6200	0.046*
H7B	0.2408	0.3351	0.7258	0.046*
H7C	0.2107	0.3979	0.6039	0.046*
C8	0.12311 (4)	0.21425 (17)	0.75746 (11)	0.0243 (3)
H8A	0.1293	0.1145	0.8109	0.029*
H8B	0.0958	0.1870	0.6947	0.029*
C9	0.11668 (4)	0.38121 (17)	0.81511 (10)	0.0224 (3)
C10	0.14305 (4)	0.52884 (18)	0.81747 (11)	0.0267 (3)
H10	0.1648	0.5250	0.7802	0.032*
C11	0.13820 (4)	0.68171 (18)	0.87322 (11)	0.0287 (3)
H11	0.1566	0.7806	0.8735	0.034*
C12	0.10674 (4)	0.69138 (17)	0.92858 (11)	0.0278 (3)
H12	0.1033	0.7964	0.9662	0.033*
C13	0.08042 (4)	0.54612 (17)	0.92822 (10)	0.0247 (3)
H13	0.0591	0.5515	0.9668	0.030*
C14	0.08456 (4)	0.39122 (17)	0.87205 (10)	0.0222 (3)
C15	0.05692 (4)	0.23845 (17)	0.87950 (10)	0.0243 (3)
C16	0.02595 (4)	0.26027 (16)	0.95160 (11)	0.0240 (3)
C17	0.02123 (5)	0.2110 (2)	1.13287 (13)	0.0395 (4)
H17A	0.0373	0.1474	1.2015	0.059*
H17B	−0.0082	0.1577	1.0994	0.059*
H17C	0.0177	0.3347	1.1509	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0267 (4)	0.0268 (5)	0.0336 (5)	−0.0032 (4)	0.0187 (4)	−0.0044 (4)
O2	0.0380 (5)	0.0261 (5)	0.0447 (6)	−0.0063 (4)	0.0254 (4)	−0.0081 (4)
O3	0.0250 (5)	0.0420 (6)	0.0332 (5)	0.0060 (4)	0.0117 (4)	−0.0003 (4)
O4	0.0296 (5)	0.0466 (6)	0.0335 (5)	0.0129 (4)	0.0189 (4)	0.0124 (4)
C1	0.0212 (5)	0.0276 (6)	0.0205 (5)	0.0017 (5)	0.0080 (4)	−0.0008 (5)
C2	0.0218 (6)	0.0308 (7)	0.0260 (6)	−0.0019 (5)	0.0095 (5)	−0.0017 (5)
C3	0.0296 (7)	0.0288 (7)	0.0302 (7)	−0.0023 (5)	0.0084 (5)	−0.0042 (5)
C4	0.0339 (7)	0.0340 (7)	0.0292 (7)	0.0057 (6)	0.0138 (5)	−0.0046 (6)
C5	0.0265 (6)	0.0366 (7)	0.0269 (6)	0.0047 (5)	0.0143 (5)	0.0027 (5)
C6	0.0211 (5)	0.0299 (6)	0.0211 (5)	0.0011 (5)	0.0077 (4)	0.0028 (5)
C7	0.0281 (6)	0.0338 (7)	0.0345 (7)	−0.0043 (5)	0.0163 (5)	0.0008 (6)
C8	0.0230 (6)	0.0268 (6)	0.0278 (6)	−0.0016 (5)	0.0145 (5)	−0.0017 (5)
C9	0.0218 (5)	0.0251 (6)	0.0204 (5)	0.0013 (5)	0.0068 (4)	0.0010 (5)
C10	0.0251 (6)	0.0293 (7)	0.0277 (6)	−0.0015 (5)	0.0112 (5)	0.0007 (5)
C11	0.0272 (6)	0.0251 (6)	0.0329 (7)	−0.0035 (5)	0.0083 (5)	0.0008 (5)
C12	0.0287 (6)	0.0243 (6)	0.0285 (6)	0.0019 (5)	0.0064 (5)	−0.0041 (5)
C13	0.0226 (6)	0.0275 (6)	0.0247 (6)	0.0032 (5)	0.0086 (4)	−0.0009 (5)
C14	0.0209 (5)	0.0239 (6)	0.0222 (5)	0.0013 (5)	0.0074 (4)	0.0006 (5)
C15	0.0227 (6)	0.0264 (6)	0.0261 (6)	0.0015 (5)	0.0109 (5)	0.0001 (5)
C16	0.0241 (6)	0.0214 (6)	0.0292 (6)	−0.0011 (5)	0.0124 (5)	−0.0006 (5)
C17	0.0421 (8)	0.0485 (9)	0.0376 (8)	0.0142 (7)	0.0265 (6)	0.0154 (7)

O1—C1	1.3681 (15)	C7—H7C	0.9800
O1—C8	1.4315 (13)	C8—H8A	0.9900
O2—C15	1.2111 (16)	C8—H8B	0.9900
O3—C16	1.1981 (16)	C8—C9	1.5058 (17)
O4—C16	1.3224 (16)	C9—C10	1.3919 (18)
O4—C17	1.4560 (15)	C9—C14	1.4204 (16)
C1—C2	1.3907 (18)	C10—H10	0.9500
C1—C6	1.4078 (16)	C10—C11	1.3894 (19)
C2—H2	0.9500	C11—H11	0.9500
C2—C3	1.3915 (18)	C11—C12	1.3876 (18)
C3—H3	0.9500	C12—H12	0.9500
C3—C4	1.3855 (19)	C12—C13	1.3810 (19)
C4—H4	0.9500	C13—H13	0.9500
C4—C5	1.393 (2)	C13—C14	1.3993 (17)
C5—H5	0.9500	C14—C15	1.4736 (17)
C5—C6	1.3871 (18)	C15—C16	1.5423 (16)
C6—C7	1.5010 (18)	C17—H17A	0.9800
C7—H7A	0.9800	C17—H17B	0.9800
C7—H7B	0.9800	C17—H17C	0.9800
C1—O1—C8	117.10 (10)	C9—C8—H8B	110.1
C16—O4—C17	116.53 (10)	C10—C9—C8	121.03 (11)
O1—C1—C2	124.43 (11)	C10—C9—C14	117.85 (11)
O1—C1—C6	114.82 (11)	C14—C9—C8	121.09 (11)
C2—C1—C6	120.75 (12)	C9—C10—H10	119.3
C1—C2—H2	120.0	C11—C10—C9	121.40 (12)
C1—C2—C3	119.93 (11)	C11—C10—H10	119.3
C3—C2—H2	120.0	C10—C11—H11	119.7
C2—C3—H3	119.9	C12—C11—C10	120.67 (12)
C4—C3—C2	120.26 (13)	C12—C11—H11	119.7
C4—C3—H3	119.9	C11—C12—H12	120.5
C3—C4—H4	120.4	C13—C12—C11	119.02 (12)
C3—C4—C5	119.21 (12)	C13—C12—H12	120.5
C5—C4—H4	120.4	C12—C13—H13	119.4
C4—C5—H5	119.0	C12—C13—C14	121.25 (11)
C6—C5—C4	122.02 (12)	C14—C13—H13	119.4
C6—C5—H5	119.0	C9—C14—C15	121.69 (11)
C1—C6—C7	119.89 (11)	C13—C14—C9	119.81 (11)
C5—C6—C1	117.83 (12)	C13—C14—C15	118.40 (11)
C5—C6—C7	122.28 (11)	O2—C15—C14	126.15 (11)
C6—C7—H7A	109.5	O2—C15—C16	116.80 (11)
C6—C7—H7B	109.5	C14—C15—C16	117.05 (11)
C6—C7—H7C	109.5	O3—C16—O4	126.33 (12)
H7A—C7—H7B	109.5	O3—C16—C15	124.09 (12)
H7A—C7—H7C	109.5	O4—C16—C15	109.53 (10)
H7B—C7—H7C	109.5	O4—C17—H17A	109.5
O1—C8—H8A	110.1	O4—C17—H17B	109.5
O1—C8—H8B	110.1	O4—C17—H17C	109.5
O1—C8—C9	108.15 (10)	H17A—C17—H17B	109.5
H8A—C8—H8B	108.4	H17A—C17—H17C	109.5
C9—C8—H8A	110.1	H17B—C17—H17C	109.5
O1—C1—C2—C3	178.72 (11)	C8—C9—C14—C13	177.75 (11)
O1—C1—C6—C5	−178.46 (11)	C8—C9—C14—C15	1.40 (17)
O1—C1—C6—C7	0.78 (16)	C9—C10—C11—C12	0.1 (2)
O1—C8—C9—C10	2.58 (16)	C9—C14—C15—O2	−4.4 (2)
O1—C8—C9—C14	−175.27 (10)	C9—C14—C15—C16	175.10 (10)
O2—C15—C16—O3	−92.56 (17)	C10—C9—C14—C13	−0.16 (17)
O2—C15—C16—O4	85.23 (15)	C10—C9—C14—C15	−176.51 (11)
C1—O1—C8—C9	177.79 (10)	C10—C11—C12—C13	0.47 (19)
C1—C2—C3—C4	−0.34 (19)	C11—C12—C13—C14	−0.85 (19)
C2—C1—C6—C5	0.85 (18)	C12—C13—C14—C9	0.70 (18)
C2—C1—C6—C7	−179.91 (12)	C12—C13—C14—C15	177.17 (11)
C2—C3—C4—C5	0.8 (2)	C13—C14—C15—O2	179.20 (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—O3	87.90 (16)
C6—C1—C2—C3	−0.51 (19)	C14—C15—C16—O4	−94.31 (13)
C8—O1—C1—C2	1.38 (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)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O2i	0.98	2.44	3.3712 (18)	158

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) .