1-(4-{[(E)-3-Eth-oxy-2-hy-droxy-benzyl-idene]amino}-phen-yl)ethanone oxime.

In the title compound, C(17)H(18)N(2)O(3), the benzene rings form a dihedral angle of 3.34 (2)°. There is a strong intra-molecular O-H⋯N hydrogen bonds (which induces planarity of the structure). In the crystal, mol-ecules are linked by pairs of O-H⋯N hydrogen bonds, forming inversion dimers.

Related literature

For background to oxime-type compounds, see: Dong et al., (2009 ▶); Narasaka & Kitamura (2005 ▶). For their syntheses and structures, see: Dong et al. (2008 ▶); Akine et al. (2002 ▶); Wu et al. (2010 ▶).

Experimental

Crystal data

C17H18N2O3

M = 298.33

Triclinic,

a = 7.0556 (7) Å

b = 7.4852 (9) Å

c = 14.7821 (16) Å

α = 96.890 (1)°

β = 98.762 (1)°

γ = 102.105 (2)°

V = 745.03 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.32 × 0.21 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.988

3664 measured reflections

2561 independent reflections

1376 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.168

S = 1.02

2561 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001213/hg5155sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001213/hg5155Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001213/hg5155Isup3.cml

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

C17H18N2O3	Z = 2
Mr = 298.33	F(000) = 316
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0556 (7) Å	Cell parameters from 818 reflections
b = 7.4852 (9) Å	θ = 2.8–27.5°
c = 14.7821 (16) Å	µ = 0.09 mm−1
α = 96.890 (1)°	T = 298 K
β = 98.762 (1)°	Prismatical, yellow
γ = 102.105 (2)°	0.32 × 0.21 × 0.13 mm
V = 745.03 (14) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	1376 reflections with I > 2σ(I)
graphite	Rint = 0.037
phi and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.971, Tmax = 0.988	k = −8→8
3664 measured reflections	l = −17→9

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.2977P] where P = (Fo2 + 2Fc2)/3
2561 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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	0.3517 (4)	0.5142 (4)	0.91196 (19)	0.0451 (8)
N2	0.4699 (4)	0.7402 (4)	0.51348 (18)	0.0399 (7)
O1	0.2676 (4)	0.4614 (4)	0.98854 (17)	0.0644 (8)
H1	0.3548	0.4525	1.0301	0.097*
O2	0.3342 (3)	0.8040 (3)	0.35234 (16)	0.0518 (7)
H2	0.3308	0.7783	0.4046	0.078*
O3	0.3898 (3)	0.8888 (4)	0.19161 (16)	0.0522 (7)
C1	0.0075 (5)	0.5044 (6)	0.8478 (3)	0.0667 (13)
H1A	−0.0132	0.4861	0.9090	0.100*
H1B	−0.0658	0.3980	0.8041	0.100*
H1C	−0.0362	0.6120	0.8325	0.100*
C2	0.2226 (5)	0.5310 (5)	0.8443 (2)	0.0396 (9)
C3	0.2949 (5)	0.5820 (4)	0.7593 (2)	0.0332 (8)
C4	0.4926 (5)	0.6169 (5)	0.7524 (2)	0.0443 (10)
H4	0.5844	0.6042	0.8020	0.053*
C5	0.5573 (5)	0.6699 (5)	0.6740 (2)	0.0465 (10)
H5	0.6913	0.6937	0.6720	0.056*
C6	0.4246 (5)	0.6879 (4)	0.5984 (2)	0.0351 (8)
C7	0.2268 (5)	0.6483 (5)	0.6030 (2)	0.0446 (10)
H7	0.1352	0.6561	0.5522	0.053*
C8	0.1624 (5)	0.5971 (5)	0.6820 (2)	0.0449 (10)
H8	0.0282	0.5724	0.6836	0.054*
C9	0.6452 (5)	0.7803 (4)	0.4955 (2)	0.0376 (9)
H9	0.7514	0.7766	0.5404	0.045*
C10	0.6814 (5)	0.8313 (4)	0.4067 (2)	0.0344 (8)
C11	0.5221 (5)	0.8398 (4)	0.3389 (2)	0.0355 (8)
C12	0.5558 (5)	0.8854 (5)	0.2518 (2)	0.0382 (9)
C13	0.7458 (5)	0.9199 (5)	0.2339 (2)	0.0412 (9)
H13	0.7682	0.9488	0.1764	0.049*
C14	0.9048 (5)	0.9119 (5)	0.3015 (2)	0.0427 (9)
H14	1.0321	0.9360	0.2890	0.051*
C15	0.8720 (5)	0.8682 (5)	0.3863 (2)	0.0384 (9)
H15	0.9781	0.8630	0.4309	0.046*
C16	0.4125 (5)	0.9423 (5)	0.1031 (2)	0.0506 (10)
H16A	0.4586	0.8501	0.0659	0.061*
H16B	0.5070	1.0601	0.1109	0.061*
C17	0.2127 (6)	0.9575 (7)	0.0572 (3)	0.0781 (15)
H17A	0.1228	0.8383	0.0466	0.117*
H17B	0.2220	1.0006	−0.0009	0.117*
H17C	0.1655	1.0433	0.0966	0.117*

	U11	U22	U33	U12	U13	U23
N1	0.0459 (19)	0.059 (2)	0.0336 (18)	0.0094 (15)	0.0162 (14)	0.0153 (14)
N2	0.0371 (18)	0.0485 (19)	0.0364 (18)	0.0112 (14)	0.0100 (13)	0.0084 (14)
O1	0.0549 (18)	0.103 (2)	0.0438 (17)	0.0163 (16)	0.0224 (13)	0.0324 (15)
O2	0.0305 (15)	0.085 (2)	0.0447 (16)	0.0123 (13)	0.0110 (11)	0.0243 (13)
O3	0.0358 (15)	0.085 (2)	0.0345 (15)	0.0073 (13)	0.0001 (11)	0.0229 (13)
C1	0.043 (3)	0.111 (4)	0.048 (3)	0.014 (2)	0.0157 (19)	0.018 (2)
C2	0.038 (2)	0.046 (2)	0.033 (2)	0.0060 (17)	0.0095 (16)	0.0061 (17)
C3	0.033 (2)	0.037 (2)	0.031 (2)	0.0085 (15)	0.0097 (14)	0.0051 (15)
C4	0.034 (2)	0.071 (3)	0.032 (2)	0.0155 (18)	0.0049 (15)	0.0166 (19)
C5	0.031 (2)	0.071 (3)	0.043 (2)	0.0136 (19)	0.0118 (17)	0.0162 (19)
C6	0.042 (2)	0.038 (2)	0.030 (2)	0.0128 (17)	0.0108 (15)	0.0097 (16)
C7	0.037 (2)	0.063 (3)	0.038 (2)	0.0144 (19)	0.0075 (16)	0.0171 (19)
C8	0.032 (2)	0.062 (3)	0.044 (2)	0.0126 (18)	0.0096 (16)	0.0113 (19)
C9	0.038 (2)	0.043 (2)	0.032 (2)	0.0111 (17)	0.0029 (15)	0.0089 (16)
C10	0.035 (2)	0.039 (2)	0.030 (2)	0.0110 (16)	0.0047 (14)	0.0077 (15)
C11	0.030 (2)	0.044 (2)	0.035 (2)	0.0091 (16)	0.0106 (15)	0.0081 (16)
C12	0.032 (2)	0.045 (2)	0.034 (2)	0.0044 (17)	0.0019 (15)	0.0063 (16)
C13	0.038 (2)	0.046 (2)	0.040 (2)	0.0087 (17)	0.0090 (16)	0.0100 (17)
C14	0.031 (2)	0.051 (2)	0.047 (2)	0.0067 (17)	0.0134 (16)	0.0093 (18)
C15	0.031 (2)	0.049 (2)	0.036 (2)	0.0109 (17)	0.0047 (15)	0.0102 (17)
C16	0.054 (3)	0.060 (3)	0.037 (2)	0.009 (2)	0.0047 (17)	0.0163 (19)
C17	0.064 (3)	0.110 (4)	0.059 (3)	0.013 (3)	−0.003 (2)	0.038 (3)

N1—C2	1.283 (4)	C7—C8	1.383 (5)
N1—O1	1.416 (3)	C7—H7	0.9300
N2—C9	1.286 (4)	C8—H8	0.9300
N2—C6	1.420 (4)	C9—C10	1.454 (4)
O1—H1	0.8200	C9—H9	0.9300
O2—C11	1.346 (4)	C10—C15	1.401 (4)
O2—H2	0.8200	C10—C11	1.406 (4)
O3—C12	1.366 (4)	C11—C12	1.411 (4)
O3—C16	1.435 (4)	C12—C13	1.384 (4)
C1—C2	1.498 (5)	C13—C14	1.400 (4)
C1—H1A	0.9600	C13—H13	0.9300
C1—H1B	0.9600	C14—C15	1.374 (4)
C1—H1C	0.9600	C14—H14	0.9300
C2—C3	1.488 (4)	C15—H15	0.9300
C3—C4	1.387 (4)	C16—C17	1.502 (5)
C3—C8	1.393 (4)	C16—H16A	0.9700
C4—C5	1.379 (5)	C16—H16B	0.9700
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.384 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.378 (5)
C2—N1—O1	112.6 (3)	N2—C9—H9	119.2
C9—N2—C6	124.4 (3)	C10—C9—H9	119.2
N1—O1—H1	109.5	C15—C10—C11	119.0 (3)
C11—O2—H2	109.5	C15—C10—C9	121.4 (3)
C12—O3—C16	118.0 (3)	C11—C10—C9	119.6 (3)
C2—C1—H1A	109.5	O2—C11—C10	122.8 (3)
C2—C1—H1B	109.5	O2—C11—C12	117.3 (3)
H1A—C1—H1B	109.5	C10—C11—C12	119.9 (3)
C2—C1—H1C	109.5	O3—C12—C13	125.9 (3)
H1A—C1—H1C	109.5	O3—C12—C11	114.6 (3)
H1B—C1—H1C	109.5	C13—C12—C11	119.5 (3)
N1—C2—C3	117.0 (3)	C12—C13—C14	120.7 (3)
N1—C2—C1	123.4 (3)	C12—C13—H13	119.7
C3—C2—C1	119.5 (3)	C14—C13—H13	119.7
C4—C3—C8	116.9 (3)	C15—C14—C13	119.8 (3)
C4—C3—C2	122.9 (3)	C15—C14—H14	120.1
C8—C3—C2	120.2 (3)	C13—C14—H14	120.1
C5—C4—C3	122.0 (3)	C14—C15—C10	121.1 (3)
C5—C4—H4	119.0	C14—C15—H15	119.4
C3—C4—H4	119.0	C10—C15—H15	119.4
C4—C5—C6	120.6 (3)	O3—C16—C17	106.4 (3)
C4—C5—H5	119.7	O3—C16—H16A	110.5
C6—C5—H5	119.7	C17—C16—H16A	110.5
C7—C6—C5	118.2 (3)	O3—C16—H16B	110.5
C7—C6—N2	115.2 (3)	C17—C16—H16B	110.5
C5—C6—N2	126.6 (3)	H16A—C16—H16B	108.7
C6—C7—C8	121.1 (3)	C16—C17—H17A	109.5
C6—C7—H7	119.4	C16—C17—H17B	109.5
C8—C7—H7	119.4	H17A—C17—H17B	109.5
C7—C8—C3	121.2 (3)	C16—C17—H17C	109.5
C7—C8—H8	119.4	H17A—C17—H17C	109.5
C3—C8—H8	119.4	H17B—C17—H17C	109.5
N2—C9—C10	121.7 (3)
O1—N1—C2—C3	−178.6 (3)	N2—C9—C10—C15	−177.6 (3)
O1—N1—C2—C1	2.1 (5)	N2—C9—C10—C11	0.9 (5)
N1—C2—C3—C4	−2.2 (5)	C15—C10—C11—O2	179.1 (3)
C1—C2—C3—C4	177.1 (3)	C9—C10—C11—O2	0.6 (5)
N1—C2—C3—C8	178.0 (3)	C15—C10—C11—C12	−0.1 (5)
C1—C2—C3—C8	−2.7 (5)	C9—C10—C11—C12	−178.6 (3)
C8—C3—C4—C5	2.0 (5)	C16—O3—C12—C13	−3.5 (5)
C2—C3—C4—C5	−177.8 (3)	C16—O3—C12—C11	177.2 (3)
C3—C4—C5—C6	−0.8 (6)	O2—C11—C12—O3	0.6 (4)
C4—C5—C6—C7	−1.2 (5)	C10—C11—C12—O3	179.8 (3)
C4—C5—C6—N2	−179.7 (3)	O2—C11—C12—C13	−178.8 (3)
C9—N2—C6—C7	−179.2 (3)	C10—C11—C12—C13	0.5 (5)
C9—N2—C6—C5	−0.6 (5)	O3—C12—C13—C14	−179.9 (3)
C5—C6—C7—C8	1.9 (5)	C11—C12—C13—C14	−0.6 (5)
N2—C6—C7—C8	−179.4 (3)	C12—C13—C14—C15	0.4 (5)
C6—C7—C8—C3	−0.7 (5)	C13—C14—C15—C10	0.0 (5)
C4—C3—C8—C7	−1.3 (5)	C11—C10—C15—C14	−0.1 (5)
C2—C3—C8—C7	178.6 (3)	C9—C10—C15—C14	178.4 (3)
C6—N2—C9—C10	179.5 (3)	C12—O3—C16—C17	−172.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.07	2.817 (4)	152
O2—H2···N2	0.82	1.84	2.567 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.07	2.817 (4)	152
O2—H2⋯N2	0.82	1.84	2.567 (3)	147

Symmetry code: (i) .