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

In the title compound, C(17)H(19)NO(3), the dihedral angle between the benzene rings is 68.0 (1)°. The C-O-C-C torsion angle of the atoms joining these rings is 179.7 (2)°. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hy-droxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H⋯H contacts. In the crystal, O-H⋯N and O-H⋯O hydrogen bonds connect mol-ecules into chains along [001].

Related literature

The title compound was derived from kresoxim-methyl. For the biological activity of n class="Chemical">kresoxim-methyl, see: Anke et al. (1977 ▶); Clinton et al. (2011 ▶); Balba (2007 ▶); Sudisha et al. (2005 ▶). For related structures, see: Chopra et al. (2004 ▶); Kant et al. (2012a ▶,b ▶).

Experimental

Crystal data

C17H19NO3

M = 285.33

Monoclinic,

a = 21.0394 (14) Å

b = 20.4128 (10) Å

c = 7.6711 (5) Å

β = 105.729 (6)°

V = 3171.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 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 = 0.790, T max = 1.000

11340 measured reflections

2788 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.212

S = 1.08

2788 reflections

204 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.22 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 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203499X/lh5508sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203499X/lh5508Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203499X/lh5508Isup3.cml

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

C17H19NO3	F(000) = 1216
Mr = 285.33	Dx = 1.195 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2909 reflections
a = 21.0394 (14) Å	θ = 3.6–29.0°
b = 20.4128 (10) Å	µ = 0.08 mm−1
c = 7.6711 (5) Å	T = 293 K
β = 105.729 (6)°	Block, colourless
V = 3171.2 (3) Å3	0.3 × 0.2 × 0.1 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2788 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.6°
ω scans	h = −23→24
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −23→24
Tmin = 0.790, Tmax = 1.000	l = −9→9
11340 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0921P)2] where P = (Fo2 + 2Fc2)/3
2788 reflections	(Δ/σ)max = 0.002
204 parameters	Δρmax = 0.39 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

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	Occ. (<1)
O4	0.36797 (11)	0.16370 (9)	0.4565 (3)	0.0749 (7)
O13	0.24680 (10)	0.14485 (9)	0.7894 (3)	0.0689 (7)
N3	0.37326 (13)	0.10321 (12)	0.5462 (4)	0.0709 (8)
C2	0.38302 (15)	0.11036 (14)	0.7167 (4)	0.0638 (8)
C5	0.3638 (2)	0.1523 (2)	0.2722 (5)	0.1041 (13)
H5A	0.3630	0.1934	0.2110	0.156*
H5B	0.3242	0.1283	0.2174	0.156*
H5C	0.4014	0.1273	0.2629	0.156*
C6	0.39179 (15)	0.17396 (14)	0.8143 (3)	0.0544 (8)
C7	0.45455 (16)	0.19128 (17)	0.9162 (4)	0.0736 (9)
H7A	0.4898	0.1630	0.9228	0.088*
C8	0.4652 (2)	0.2500 (2)	1.0079 (5)	0.0912 (12)
H8A	0.5077	0.2616	1.0736	0.109*
C9	0.4141 (3)	0.2911 (2)	1.0029 (5)	0.0943 (12)
H9A	0.4216	0.3307	1.0653	0.113*
C10	0.3504 (2)	0.27400 (16)	0.9042 (5)	0.0785 (10)
H10A	0.3155	0.3022	0.9023	0.094*
C11	0.33831 (16)	0.21524 (14)	0.8083 (4)	0.0577 (8)
C12	0.27043 (14)	0.19845 (14)	0.7035 (4)	0.0635 (9)
H12A	0.2418	0.2361	0.6974	0.076*
H12B	0.2701	0.1864	0.5810	0.076*
C14	0.18363 (16)	0.12314 (14)	0.7087 (4)	0.0596 (8)
C15	0.16296 (18)	0.06974 (15)	0.7930 (5)	0.0722 (9)
C16	0.0989 (2)	0.04775 (18)	0.7189 (6)	0.0901 (12)
H16A	0.0832	0.0129	0.7735	0.108*
C17	0.0578 (2)	0.0762 (2)	0.5666 (7)	0.0991 (13)
H17A	0.0152	0.0604	0.5195	0.119*
C18	0.07975 (19)	0.1270 (2)	0.4858 (5)	0.0902 (12)
H18A	0.0523	0.1457	0.3820	0.108*
C19	0.14248 (17)	0.15098 (15)	0.5562 (5)	0.0737 (9)
H19A	0.1572	0.1862	0.5006	0.088*
C20	0.2088 (2)	0.03868 (18)	0.9558 (5)	0.1147 (15)
H20A	0.2484	0.0250	0.9269	0.172*
H20B	0.1877	0.0013	0.9919	0.172*
H20C	0.2197	0.0698	1.0532	0.172*
O11A	0.4567 (3)	0.0312 (2)	0.8725 (8)	0.253 (3)	0.86
H11Y	0.4837	0.0106	0.9553	0.380*	0.86
H11Z	0.4806	0.0312	0.8007	0.380*	0.86
C11A	0.3946 (2)	0.0467 (2)	0.8269 (7)	0.0952 (17)	0.86
H11A	0.3796	0.0522	0.9351	0.114*	0.43
H11B	0.3691	0.0116	0.7556	0.114*	0.43
O11B	0.3776 (10)	−0.0022 (7)	0.757 (2)	0.107 (7)	0.14
H11X	0.3746	−0.0298	0.8361	0.161*	0.14
C11B	0.3637 (19)	0.0532 (6)	0.822 (4)	0.0952 (17)	0.14
H11C	0.3875	0.0566	0.9491	0.114*	0.14
H11D	0.3168	0.0552	0.8123	0.114*	0.14

	U11	U22	U33	U12	U13	U23
O4	0.1028 (18)	0.0737 (14)	0.0500 (13)	−0.0026 (12)	0.0234 (11)	0.0048 (10)
O13	0.0712 (15)	0.0688 (13)	0.0615 (13)	−0.0153 (11)	0.0090 (11)	0.0183 (10)
N3	0.091 (2)	0.0592 (15)	0.0623 (18)	0.0014 (13)	0.0212 (14)	−0.0015 (13)
C2	0.080 (2)	0.0564 (18)	0.0553 (19)	−0.0021 (16)	0.0193 (15)	0.0060 (15)
C5	0.141 (4)	0.120 (3)	0.050 (2)	−0.007 (3)	0.023 (2)	−0.008 (2)
C6	0.067 (2)	0.0615 (18)	0.0362 (16)	−0.0124 (16)	0.0163 (14)	0.0013 (12)
C7	0.074 (2)	0.095 (2)	0.054 (2)	−0.0094 (19)	0.0206 (17)	−0.0034 (18)
C8	0.088 (3)	0.118 (3)	0.070 (2)	−0.043 (3)	0.026 (2)	−0.019 (2)
C9	0.128 (4)	0.081 (3)	0.083 (3)	−0.043 (3)	0.045 (3)	−0.030 (2)
C10	0.110 (3)	0.063 (2)	0.075 (2)	−0.004 (2)	0.046 (2)	−0.0010 (17)
C11	0.071 (2)	0.0549 (17)	0.0504 (17)	−0.0103 (17)	0.0220 (15)	0.0061 (13)
C12	0.073 (2)	0.0567 (18)	0.0632 (19)	−0.0037 (15)	0.0227 (16)	0.0184 (15)
C14	0.067 (2)	0.0572 (18)	0.0570 (19)	−0.0061 (16)	0.0201 (16)	−0.0041 (14)
C15	0.082 (3)	0.0623 (19)	0.078 (2)	−0.0110 (19)	0.0319 (19)	−0.0012 (17)
C16	0.094 (3)	0.073 (2)	0.115 (3)	−0.025 (2)	0.050 (3)	−0.016 (2)
C17	0.070 (3)	0.096 (3)	0.130 (4)	−0.011 (2)	0.026 (3)	−0.035 (3)
C18	0.071 (3)	0.092 (3)	0.101 (3)	0.004 (2)	0.011 (2)	−0.012 (2)
C19	0.068 (2)	0.075 (2)	0.076 (2)	0.0006 (19)	0.0161 (18)	0.0016 (17)
C20	0.145 (4)	0.092 (3)	0.110 (3)	−0.029 (2)	0.038 (3)	0.036 (2)
O11A	0.166 (5)	0.175 (4)	0.355 (9)	0.019 (4)	−0.040 (4)	0.159 (5)
C11A	0.089 (5)	0.075 (3)	0.113 (4)	0.026 (3)	0.012 (3)	0.024 (3)
O11B	0.20 (2)	0.031 (8)	0.083 (12)	0.001 (11)	0.026 (12)	−0.011 (8)
C11B	0.089 (5)	0.075 (3)	0.113 (4)	0.026 (3)	0.012 (3)	0.024 (3)

O4—N3	1.403 (3)	C14—C19	1.375 (4)
O4—C5	1.412 (4)	C14—C15	1.396 (4)
O13—C14	1.378 (3)	C15—C16	1.388 (5)
O13—C12	1.434 (3)	C15—C20	1.497 (5)
N3—C2	1.277 (3)	C16—C17	1.379 (5)
C2—C6	1.485 (4)	C16—H16A	0.9300
C2—C11A	1.533 (5)	C17—C18	1.352 (5)
C2—C11B	1.535 (7)	C17—H17A	0.9300
C5—H5A	0.9600	C18—C19	1.374 (4)
C5—H5B	0.9600	C18—H18A	0.9300
C5—H5C	0.9600	C19—H19A	0.9300
C6—C7	1.386 (4)	C20—H20A	0.9600
C6—C11	1.396 (4)	C20—H20B	0.9600
C7—C8	1.378 (5)	C20—H20C	0.9600
C7—H7A	0.9300	O11A—C11A	1.298 (6)
C8—C9	1.355 (5)	O11A—H11Y	0.8400
C8—H8A	0.9300	O11A—H11Z	0.8399
C9—C10	1.394 (5)	C11A—H11A	0.9700
C9—H9A	0.9300	C11A—H11B	0.9700
C10—C11	1.394 (4)	O11B—C11B	1.300 (8)
C10—H10A	0.9300	O11B—H11X	0.8400
C11—C12	1.477 (4)	C11B—H11C	0.9700
C12—H12A	0.9700	C11B—H11D	0.9700
C12—H12B	0.9700
N3—O4—C5	108.7 (2)	C19—C14—C15	120.9 (3)
C14—O13—C12	116.8 (2)	O13—C14—C15	115.2 (3)
C2—N3—O4	111.8 (2)	C16—C15—C14	116.9 (3)
N3—C2—C6	125.5 (3)	C16—C15—C20	122.6 (3)
N3—C2—C11A	115.2 (3)	C14—C15—C20	120.4 (3)
C6—C2—C11A	118.9 (3)	C17—C16—C15	121.8 (4)
N3—C2—C11B	117.4 (12)	C17—C16—H16A	119.1
C6—C2—C11B	114.4 (9)	C15—C16—H16A	119.1
O4—C5—H5A	109.5	C18—C17—C16	119.9 (4)
O4—C5—H5B	109.5	C18—C17—H17A	120.1
H5A—C5—H5B	109.5	C16—C17—H17A	120.1
O4—C5—H5C	109.5	C17—C18—C19	120.3 (4)
H5A—C5—H5C	109.5	C17—C18—H18A	119.9
H5B—C5—H5C	109.5	C19—C18—H18A	119.9
C7—C6—C11	120.1 (3)	C18—C19—C14	120.2 (3)
C7—C6—C2	118.5 (3)	C18—C19—H19A	119.9
C11—C6—C2	121.5 (3)	C14—C19—H19A	119.9
C8—C7—C6	120.5 (3)	C15—C20—H20A	109.5
C8—C7—H7A	119.7	C15—C20—H20B	109.5
C6—C7—H7A	119.7	H20A—C20—H20B	109.5
C9—C8—C7	120.4 (4)	C15—C20—H20C	109.5
C9—C8—H8A	119.8	H20A—C20—H20C	109.5
C7—C8—H8A	119.8	H20B—C20—H20C	109.5
C8—C9—C10	119.9 (3)	C11A—O11A—H11Y	138.5
C8—C9—H9A	120.0	C11A—O11A—H11Z	124.1
C10—C9—H9A	120.0	H11Y—O11A—H11Z	95.5
C9—C10—C11	120.9 (3)	O11A—C11A—C2	110.6 (4)
C9—C10—H10A	119.6	O11A—C11A—H11A	109.5
C11—C10—H10A	119.6	C2—C11A—H11A	109.5
C10—C11—C6	118.1 (3)	O11A—C11A—H11B	109.5
C10—C11—C12	119.9 (3)	C2—C11A—H11B	109.5
C6—C11—C12	122.0 (3)	H11A—C11A—H11B	108.1
O13—C12—C11	109.4 (2)	C11B—O11B—H11X	104.0
O13—C12—H12A	109.8	O11B—C11B—C2	109.9 (12)
C11—C12—H12A	109.8	O11B—C11B—H11C	109.7
O13—C12—H12B	109.8	C2—C11B—H11C	109.7
C11—C12—H12B	109.8	O11B—C11B—H11D	109.7
H12A—C12—H12B	108.2	C2—C11B—H11D	109.7
C19—C14—O13	123.9 (3)	H11C—C11B—H11D	108.2
C5—O4—N3—C2	174.3 (3)	C10—C11—C12—O13	−110.4 (3)
O4—N3—C2—C6	−3.3 (4)	C6—C11—C12—O13	69.9 (3)
O4—N3—C2—C11A	−175.6 (3)	C12—O13—C14—C19	−1.9 (4)
O4—N3—C2—C11B	157.0 (14)	C12—O13—C14—C15	178.2 (2)
N3—C2—C6—C7	−105.8 (4)	C19—C14—C15—C16	−1.8 (5)
C11A—C2—C6—C7	66.3 (4)	O13—C14—C15—C16	178.0 (3)
C11B—C2—C6—C7	93.5 (16)	C19—C14—C15—C20	178.3 (3)
N3—C2—C6—C11	75.6 (4)	O13—C14—C15—C20	−1.8 (4)
C11A—C2—C6—C11	−112.3 (3)	C14—C15—C16—C17	1.5 (5)
C11B—C2—C6—C11	−85.1 (16)	C20—C15—C16—C17	−178.6 (4)
C11—C6—C7—C8	−1.9 (4)	C15—C16—C17—C18	−0.2 (6)
C2—C6—C7—C8	179.5 (3)	C16—C17—C18—C19	−0.9 (6)
C6—C7—C8—C9	1.5 (5)	C17—C18—C19—C14	0.5 (5)
C7—C8—C9—C10	−0.1 (5)	O13—C14—C19—C18	−179.0 (3)
C8—C9—C10—C11	−0.7 (5)	C15—C14—C19—C18	0.9 (5)
C9—C10—C11—C6	0.2 (4)	N3—C2—C11A—O11A	87.9 (5)
C9—C10—C11—C12	−179.5 (3)	C6—C2—C11A—O11A	−85.0 (5)
C7—C6—C11—C10	1.1 (4)	C11B—C2—C11A—O11A	−171 (3)
C2—C6—C11—C10	179.6 (3)	N3—C2—C11B—O11B	38 (3)
C7—C6—C11—C12	−179.2 (2)	C6—C2—C11B—O11B	−160 (2)
C2—C6—C11—C12	−0.6 (4)	C11A—C2—C11B—O11B	−53.1 (15)
C14—O13—C12—C11	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11Y···O11Ai	0.84	1.77	2.614 (8)	178
O11A—H11Z···O11Aii	0.84	2.11	2.950 (14)	178
O11B—H11X···N3iii	0.84	2.21	3.046 (18)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11A—H11Y⋯O11A i	0.84	1.77	2.614 (8)	178
O11A—H11Z⋯O11A ii	0.84	2.11	2.950 (14)	178
O11B—H11X⋯N3iii	0.84	2.21	3.046 (18)	177

Symmetry codes: (i) ; (ii) ; (iii) .