2-[(E)-Meth-oxy-imino]-2-{2-[(2-methyl-phen-oxy)meth-yl]phen-yl}ethanoic acid.

In the title compound, C(17)H(17)NO(4), the dihedral angle between the two aromatic rings is 59.64 (5)°. The (meth-oxy-imino)-ethanoic acid fragment is nearly perpendicular to the attached benzene ring [dihedral angle = 81.07 (4)°]. In the crystal, pairs of O-H⋯O hydrogen bonds between carb-oxy groups link mol-ecules into inversion dimers. In addition, π-π stacking inter-actions between inversion-related benzene rings are observed [centroid-centroid distance = 3.702 (1) Å].

Related literature

For the biological activities of kresoxim-methyl, see: Balba (2007 ▶); Cash & Cronan (2001 ▶); Ammermann et al. (2000 ▶). For a related structure, see: Chopra et al. (2004 ▶).

Experimental

Crystal data

C17H17NO4

M = 299.32

Triclinic,

a = 7.8993 (3) Å

b = 8.5720 (3) Å

c = 12.6080 (5) Å

α = 88.013 (3)°

β = 82.270 (3)°

γ = 65.717 (4)°

V = 770.92 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.947, T max = 1.000

18021 measured reflections

3016 independent reflections

2446 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.05

3016 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030711/gk2509sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030711/gk2509Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030711/gk2509Isup3.cml

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

C17H17NO4	Z = 2
Mr = 299.32	F(000) = 316
Triclinic, P1	Dx = 1.289 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8993 (3) Å	Cell parameters from 8697 reflections
b = 8.5720 (3) Å	θ = 4.0–29.0°
c = 12.6080 (5) Å	µ = 0.09 mm−1
α = 88.013 (3)°	T = 293 K
β = 82.270 (3)°	Block, colourless
γ = 65.717 (4)°	0.3 × 0.2 × 0.1 mm
V = 770.92 (5) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3016 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 4.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→10
Tmin = 0.947, Tmax = 1.000	l = −15→15
18021 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.1581P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3016 reflections	Δρmax = 0.21 e Å−3
202 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.129 (7)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
N1	−0.04205 (15)	0.76501 (15)	0.14263 (9)	0.0411 (3)
O1	0.26565 (15)	0.52466 (14)	0.04947 (10)	0.0627 (4)
H1	0.3655	0.4611	0.0157	0.094*
O2	0.41631 (14)	0.69280 (13)	0.05567 (9)	0.0545 (3)
O3	−0.19671 (13)	0.89490 (14)	0.19809 (9)	0.0537 (3)
O4	0.29418 (13)	0.65865 (12)	0.32961 (7)	0.0470 (3)
C1	0.10574 (17)	0.79233 (16)	0.14043 (10)	0.0343 (3)
C2	0.27728 (18)	0.66279 (17)	0.07790 (11)	0.0389 (3)
C3	−0.3626 (2)	0.8742 (3)	0.18052 (16)	0.0714 (5)
H3A	−0.3753	0.8841	0.1056	0.107*
H3B	−0.4704	0.9612	0.2203	0.107*
H3C	−0.3529	0.7634	0.2039	0.107*
C4	0.11852 (16)	0.94464 (16)	0.18597 (10)	0.0343 (3)
C5	0.1139 (2)	1.07741 (19)	0.11881 (13)	0.0481 (4)
H5	0.1053	1.0687	0.0466	0.058*
C6	0.1217 (2)	1.2226 (2)	0.15794 (16)	0.0593 (5)
H6	0.1148	1.3126	0.1128	0.071*
C7	0.1399 (2)	1.2330 (2)	0.26406 (16)	0.0589 (5)
H7	0.1464	1.3299	0.2908	0.071*
C8	0.14853 (19)	1.10001 (19)	0.33090 (13)	0.0489 (4)
H8	0.1627	1.1077	0.4023	0.059*
C9	0.13653 (16)	0.95487 (16)	0.29377 (11)	0.0364 (3)
C10	0.14079 (19)	0.81417 (17)	0.36887 (11)	0.0418 (3)
H10A	0.1558	0.8422	0.4399	0.050*
H10B	0.0240	0.8006	0.3734	0.050*
C11	0.33196 (19)	0.51830 (17)	0.39422 (11)	0.0400 (3)
C12	0.4895 (2)	0.37100 (18)	0.35617 (12)	0.0447 (3)
C13	0.5341 (2)	0.22787 (19)	0.41993 (14)	0.0551 (4)
H13	0.6382	0.1285	0.3965	0.066*
C14	0.4296 (3)	0.2281 (2)	0.51667 (15)	0.0596 (4)
H14	0.4637	0.1305	0.5579	0.072*
C15	0.2752 (2)	0.3729 (2)	0.55158 (14)	0.0568 (4)
H15	0.2033	0.3736	0.6165	0.068*
C16	0.2255 (2)	0.5189 (2)	0.49049 (12)	0.0486 (4)
H16	0.1205	0.6172	0.5144	0.058*
C17	0.6052 (2)	0.3689 (2)	0.25175 (15)	0.0647 (5)
H17A	0.7198	0.2672	0.2458	0.097*
H17B	0.6334	0.4679	0.2484	0.097*
H17C	0.5369	0.3702	0.1940	0.097*

	U11	U22	U33	U12	U13	U23
N1	0.0358 (6)	0.0487 (7)	0.0405 (6)	−0.0196 (5)	−0.0022 (5)	−0.0041 (5)
O1	0.0494 (6)	0.0518 (6)	0.0893 (9)	−0.0285 (5)	0.0166 (6)	−0.0286 (6)
O2	0.0408 (6)	0.0539 (6)	0.0715 (7)	−0.0260 (5)	0.0106 (5)	−0.0200 (5)
O3	0.0315 (5)	0.0610 (7)	0.0665 (7)	−0.0183 (5)	0.0021 (5)	−0.0155 (5)
O4	0.0466 (6)	0.0382 (5)	0.0395 (5)	−0.0021 (4)	−0.0011 (4)	0.0007 (4)
C1	0.0342 (7)	0.0385 (7)	0.0324 (6)	−0.0170 (6)	−0.0055 (5)	0.0023 (5)
C2	0.0377 (7)	0.0420 (7)	0.0407 (7)	−0.0207 (6)	−0.0020 (6)	−0.0044 (6)
C3	0.0362 (8)	0.0977 (14)	0.0844 (13)	−0.0323 (9)	−0.0035 (8)	−0.0062 (11)
C4	0.0262 (6)	0.0339 (7)	0.0411 (7)	−0.0112 (5)	−0.0026 (5)	−0.0007 (5)
C5	0.0460 (8)	0.0499 (8)	0.0516 (9)	−0.0235 (7)	−0.0062 (6)	0.0095 (7)
C6	0.0512 (9)	0.0417 (8)	0.0876 (13)	−0.0241 (7)	−0.0038 (9)	0.0121 (8)
C7	0.0440 (8)	0.0402 (8)	0.0953 (14)	−0.0206 (7)	−0.0037 (8)	−0.0142 (8)
C8	0.0375 (7)	0.0466 (8)	0.0590 (9)	−0.0127 (6)	−0.0045 (6)	−0.0178 (7)
C9	0.0252 (6)	0.0352 (7)	0.0426 (7)	−0.0063 (5)	−0.0023 (5)	−0.0067 (5)
C10	0.0391 (7)	0.0404 (7)	0.0357 (7)	−0.0061 (6)	−0.0033 (6)	−0.0044 (6)
C11	0.0402 (7)	0.0380 (7)	0.0421 (8)	−0.0139 (6)	−0.0136 (6)	0.0015 (6)
C12	0.0412 (7)	0.0398 (7)	0.0526 (8)	−0.0133 (6)	−0.0149 (6)	−0.0030 (6)
C13	0.0567 (9)	0.0359 (8)	0.0712 (11)	−0.0129 (7)	−0.0236 (8)	−0.0008 (7)
C14	0.0768 (12)	0.0452 (9)	0.0666 (11)	−0.0306 (9)	−0.0266 (9)	0.0139 (8)
C15	0.0678 (11)	0.0583 (10)	0.0534 (9)	−0.0341 (9)	−0.0124 (8)	0.0092 (8)
C16	0.0478 (8)	0.0471 (8)	0.0485 (9)	−0.0165 (7)	−0.0082 (7)	0.0018 (7)
C17	0.0535 (10)	0.0515 (10)	0.0675 (11)	−0.0022 (8)	0.0010 (8)	−0.0043 (8)

N1—C1	1.2784 (16)	C7—H7	0.9300
N1—O3	1.3880 (14)	C8—C9	1.3875 (19)
O1—C2	1.2910 (16)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.4994 (19)
O2—C2	1.2228 (16)	C10—H10A	0.9700
O3—C3	1.4391 (18)	C10—H10B	0.9700
O4—C11	1.3791 (16)	C11—C16	1.379 (2)
O4—C10	1.4305 (15)	C11—C12	1.4006 (19)
C1—C4	1.4901 (17)	C12—C13	1.388 (2)
C1—C2	1.4921 (18)	C12—C17	1.495 (2)
C3—H3A	0.9600	C13—C14	1.378 (2)
C3—H3B	0.9600	C13—H13	0.9300
C3—H3C	0.9600	C14—C15	1.368 (2)
C4—C5	1.3859 (19)	C14—H14	0.9300
C4—C9	1.3948 (18)	C15—C16	1.387 (2)
C5—C6	1.383 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.374 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—C8	1.378 (2)	C17—H17C	0.9600
C1—N1—O3	111.46 (11)	C8—C9—C10	120.26 (13)
C2—O1—H1	109.5	C4—C9—C10	121.31 (11)
N1—O3—C3	108.63 (11)	O4—C10—C9	108.75 (10)
C11—O4—C10	116.98 (10)	O4—C10—H10A	109.9
N1—C1—C4	126.66 (12)	C9—C10—H10A	109.9
N1—C1—C2	115.03 (11)	O4—C10—H10B	109.9
C4—C1—C2	118.13 (10)	C9—C10—H10B	109.9
O2—C2—O1	124.35 (12)	H10A—C10—H10B	108.3
O2—C2—C1	119.61 (11)	O4—C11—C16	123.67 (12)
O1—C2—C1	116.04 (11)	O4—C11—C12	115.46 (12)
O3—C3—H3A	109.5	C16—C11—C12	120.87 (13)
O3—C3—H3B	109.5	C13—C12—C11	117.19 (14)
H3A—C3—H3B	109.5	C13—C12—C17	121.54 (14)
O3—C3—H3C	109.5	C11—C12—C17	121.27 (13)
H3A—C3—H3C	109.5	C14—C13—C12	122.24 (15)
H3B—C3—H3C	109.5	C14—C13—H13	118.9
C5—C4—C9	119.87 (12)	C12—C13—H13	118.9
C5—C4—C1	118.75 (12)	C15—C14—C13	119.49 (15)
C9—C4—C1	121.37 (11)	C15—C14—H14	120.3
C6—C5—C4	120.78 (15)	C13—C14—H14	120.3
C6—C5—H5	119.6	C14—C15—C16	120.20 (16)
C4—C5—H5	119.6	C14—C15—H15	119.9
C7—C6—C5	119.48 (15)	C16—C15—H15	119.9
C7—C6—H6	120.3	C11—C16—C15	120.01 (14)
C5—C6—H6	120.3	C11—C16—H16	120.0
C6—C7—C8	120.08 (14)	C15—C16—H16	120.0
C6—C7—H7	120.0	C12—C17—H17A	109.5
C8—C7—H7	120.0	C12—C17—H17B	109.5
C7—C8—C9	121.32 (15)	H17A—C17—H17B	109.5
C7—C8—H8	119.3	C12—C17—H17C	109.5
C9—C8—H8	119.3	H17A—C17—H17C	109.5
C8—C9—C4	118.43 (13)	H17B—C17—H17C	109.5
C1—N1—O3—C3	169.20 (13)	C1—C4—C9—C8	179.72 (11)
O3—N1—C1—C4	−2.39 (18)	C5—C4—C9—C10	179.60 (12)
O3—N1—C1—C2	−177.26 (11)	C1—C4—C9—C10	−0.97 (18)
N1—C1—C2—O2	167.44 (13)	C11—O4—C10—C9	173.59 (11)
C4—C1—C2—O2	−7.90 (19)	C8—C9—C10—O4	−121.94 (13)
N1—C1—C2—O1	−11.62 (19)	C4—C9—C10—O4	58.76 (15)
C4—C1—C2—O1	173.04 (12)	C10—O4—C11—C16	3.11 (19)
N1—C1—C4—C5	−96.47 (16)	C10—O4—C11—C12	−176.49 (11)
C2—C1—C4—C5	78.27 (16)	O4—C11—C12—C13	178.86 (12)
N1—C1—C4—C9	84.09 (17)	C16—C11—C12—C13	−0.8 (2)
C2—C1—C4—C9	−101.17 (14)	O4—C11—C12—C17	−0.6 (2)
C9—C4—C5—C6	−1.8 (2)	C16—C11—C12—C17	179.77 (14)
C1—C4—C5—C6	178.77 (13)	C11—C12—C13—C14	0.1 (2)
C4—C5—C6—C7	1.9 (2)	C17—C12—C13—C14	179.57 (15)
C5—C6—C7—C8	−0.6 (2)	C12—C13—C14—C15	0.6 (2)
C6—C7—C8—C9	−0.9 (2)	C13—C14—C15—C16	−0.6 (2)
C7—C8—C9—C4	1.1 (2)	O4—C11—C16—C15	−178.85 (13)
C7—C8—C9—C10	−178.26 (13)	C12—C11—C16—C15	0.7 (2)
C5—C4—C9—C8	0.29 (18)	C14—C15—C16—C11	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.82	2.640 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.82	2.640 (2)	176

Symmetry code: (i) .