(E)-2-[(4-Ethoxy-phen-yl)imino-meth-yl]-4-methoxy-phenol.

In the mol-ecule of the title compound, C(16)H(17)NO(3), the aromatic rings are oriented at a dihedral angle of 29.25 (8)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a nearly planar [maximum deviation 0.034 (13) Å] six-membered ring, which is oriented at dihedral angles of 0.91 (1) and 28.91 (12)° with respect to the aromatic rings. The title mol-ecule is a phenol-imine tautomer, as evidenced by C-O, C-N and C-C bond lengths. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds that generate C(8) chains.

Related literature

For background to this study, see: Özek et al., 2007 ▶. For related structures, see: Özek et al. (2009 ▶); Özek et al. (2008 ▶).

Experimental

Crystal data

C16H17NO3

M = 271.31

Monoclinic,

a = 14.8558 (7) Å

b = 13.7669 (7) Å

c = 6.9042 (3) Å

β = 90.287 (4)°

V = 1412.02 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.77 × 0.51 × 0.28 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.943, T max = 0.973

14704 measured reflections

2938 independent reflections

2014 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.04

2938 reflections

250 parameters

All H-atom parameters refined

Δρmax = 0.11 e Å−3

Δρmin = −0.12 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040586/ez2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040586/ez2189Isup2.hkl

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

C16H17NO3	F(000) = 576
Mr = 271.31	Dx = 1.276 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14704 reflections
a = 14.8558 (7) Å	θ = 2.0–28.0°
b = 13.7669 (7) Å	µ = 0.09 mm−1
c = 6.9042 (3) Å	T = 296 K
β = 90.287 (4)°	Prism, brown
V = 1412.02 (11) Å3	0.77 × 0.51 × 0.28 mm
Z = 4

Stoe IPDS II diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
plane graphite	Rint = 0.051
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω scans	h = −18→18
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −17→17
Tmin = 0.943, Tmax = 0.973	l = −8→7
14704 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)] = 0.044	All H-atom parameters refined
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0671P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2938 reflections	Δρmax = 0.11 e Å−3
250 parameters	Δρmin = −0.12 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: 0.0043 (13)

Experimental. 260 frames, detector distance = 100 mm

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
C1	0.67303 (10)	0.38075 (10)	0.1954 (2)	0.0592 (4)
C2	0.66776 (11)	0.36315 (11)	−0.0041 (2)	0.0644 (4)
C3	0.74627 (12)	0.35280 (13)	−0.1091 (2)	0.0738 (5)
C4	0.82841 (13)	0.35935 (13)	−0.0201 (2)	0.0743 (5)
C5	0.83522 (11)	0.37538 (12)	0.1785 (2)	0.0677 (4)
C6	0.75803 (10)	0.38680 (12)	0.2840 (2)	0.0633 (4)
C7	0.93120 (15)	0.38888 (19)	0.4548 (3)	0.0868 (6)
C8	0.59256 (11)	0.38970 (11)	0.3128 (2)	0.0635 (4)
C9	0.43564 (10)	0.38370 (11)	0.3529 (2)	0.0587 (4)
C10	0.43263 (11)	0.35185 (12)	0.5428 (2)	0.0663 (4)
C11	0.35242 (11)	0.34958 (13)	0.6444 (2)	0.0669 (4)
C12	0.27310 (10)	0.37865 (10)	0.5544 (2)	0.0593 (4)
C13	0.27591 (11)	0.41068 (12)	0.3634 (2)	0.0658 (4)
C14	0.35554 (10)	0.41219 (12)	0.2639 (2)	0.0647 (4)
C15	0.18545 (13)	0.35600 (18)	0.8412 (3)	0.0808 (5)
C16	0.08889 (15)	0.3588 (2)	0.8994 (4)	0.1001 (7)
N1	0.51409 (8)	0.38318 (9)	0.23737 (18)	0.0634 (3)
O1	0.58802 (9)	0.35510 (10)	−0.09793 (18)	0.0830 (4)
O2	0.92111 (8)	0.37741 (11)	0.25288 (18)	0.0904 (4)
O3	0.19015 (7)	0.37712 (8)	0.63865 (15)	0.0709 (3)
H1	0.5439 (17)	0.3668 (16)	−0.006 (3)	0.116 (8)*
H3	0.7423 (13)	0.3381 (14)	−0.243 (3)	0.100 (6)*
H4	0.8816 (14)	0.3471 (14)	−0.091 (3)	0.093 (6)*
H6	0.7613 (11)	0.3976 (13)	0.421 (3)	0.083 (5)*
H7A	0.9038 (14)	0.4477 (18)	0.503 (3)	0.105 (7)*
H7B	0.8999 (13)	0.3335 (15)	0.528 (3)	0.093 (6)*
H7C	0.9976 (15)	0.3864 (13)	0.473 (3)	0.096 (6)*
H8	0.6036 (11)	0.4006 (12)	0.449 (3)	0.080 (5)*
H10	0.4858 (12)	0.3266 (13)	0.606 (2)	0.082 (5)*
H11	0.3521 (11)	0.3218 (13)	0.777 (3)	0.084 (5)*
H13	0.2221 (11)	0.4322 (12)	0.307 (2)	0.073 (5)*
H14	0.3585 (10)	0.4324 (13)	0.130 (2)	0.077 (5)*
H15A	0.2218 (13)	0.4035 (14)	0.913 (3)	0.090 (6)*
H15B	0.2105 (13)	0.2887 (16)	0.862 (3)	0.112 (7)*
H16A	0.0524 (19)	0.304 (2)	0.825 (4)	0.158 (11)*
H16B	0.0618 (16)	0.4162 (19)	0.873 (4)	0.128 (9)*
H16C	0.0829 (14)	0.3476 (15)	1.038 (4)	0.105 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0603 (8)	0.0579 (8)	0.0594 (8)	0.0004 (6)	0.0039 (6)	−0.0015 (6)
C2	0.0680 (9)	0.0663 (10)	0.0589 (8)	−0.0002 (7)	−0.0019 (7)	0.0026 (7)
C3	0.0824 (12)	0.0850 (12)	0.0542 (9)	0.0049 (8)	0.0085 (8)	0.0022 (8)
C4	0.0714 (11)	0.0849 (12)	0.0666 (10)	0.0082 (8)	0.0157 (8)	0.0059 (8)
C5	0.0598 (9)	0.0752 (10)	0.0682 (9)	0.0016 (7)	0.0055 (7)	0.0066 (7)
C6	0.0619 (9)	0.0718 (10)	0.0561 (8)	−0.0011 (7)	0.0043 (7)	−0.0025 (7)
C7	0.0665 (12)	0.1075 (17)	0.0864 (13)	−0.0070 (11)	−0.0097 (9)	−0.0061 (12)
C8	0.0634 (9)	0.0665 (10)	0.0605 (9)	0.0000 (7)	0.0005 (7)	−0.0065 (7)
C9	0.0577 (8)	0.0580 (8)	0.0604 (8)	0.0005 (6)	−0.0006 (6)	−0.0042 (6)
C10	0.0574 (8)	0.0769 (10)	0.0645 (9)	0.0066 (7)	−0.0065 (7)	0.0038 (7)
C11	0.0627 (9)	0.0768 (10)	0.0610 (9)	0.0051 (7)	−0.0026 (7)	0.0078 (8)
C12	0.0546 (8)	0.0601 (9)	0.0633 (8)	0.0009 (6)	0.0002 (6)	−0.0028 (7)
C13	0.0580 (9)	0.0769 (10)	0.0625 (9)	0.0070 (7)	−0.0078 (7)	0.0016 (7)
C14	0.0651 (9)	0.0737 (10)	0.0554 (8)	0.0031 (7)	−0.0026 (7)	0.0020 (7)
C15	0.0702 (11)	0.1014 (15)	0.0707 (11)	0.0031 (10)	0.0062 (8)	0.0190 (10)
C16	0.0712 (13)	0.139 (2)	0.0902 (15)	0.0020 (13)	0.0187 (11)	0.0247 (15)
N1	0.0595 (8)	0.0655 (8)	0.0651 (7)	−0.0001 (6)	0.0016 (6)	−0.0029 (6)
O1	0.0742 (8)	0.1130 (10)	0.0616 (7)	−0.0007 (6)	−0.0088 (6)	−0.0047 (6)
O2	0.0576 (7)	0.1344 (12)	0.0794 (8)	0.0014 (6)	0.0047 (6)	0.0062 (7)
O3	0.0564 (6)	0.0901 (8)	0.0661 (6)	0.0021 (5)	0.0011 (5)	0.0055 (5)

C1—C2	1.401 (2)	C9—C14	1.393 (2)
C1—C6	1.403 (2)	C9—N1	1.4154 (19)
C1—C8	1.453 (2)	C10—C11	1.386 (2)
C2—O1	1.3518 (19)	C10—H10	0.965 (18)
C2—C3	1.384 (2)	C11—C12	1.388 (2)
C3—C4	1.367 (3)	C11—H11	0.990 (17)
C3—H3	0.94 (2)	C12—O3	1.3653 (18)
C4—C5	1.392 (2)	C12—C13	1.392 (2)
C4—H4	0.95 (2)	C13—C14	1.371 (2)
C5—C6	1.371 (2)	C13—H13	0.936 (17)
C5—O2	1.373 (2)	C14—H14	0.966 (17)
C6—H6	0.957 (18)	C15—O3	1.431 (2)
C7—O2	1.410 (2)	C15—C16	1.492 (3)
C7—H7A	0.97 (2)	C15—H15A	0.98 (2)
C7—H7B	1.03 (2)	C15—H15B	1.01 (2)
C7—H7C	0.99 (2)	C16—H16A	1.06 (3)
C8—N1	1.277 (2)	C16—H16B	0.90 (3)
C8—H8	0.963 (18)	C16—H16C	0.98 (2)
C9—C10	1.384 (2)	O1—H1	0.93 (3)
C2—C1—C6	119.01 (14)	C9—C10—H10	120.8 (10)
C2—C1—C8	121.41 (14)	C11—C10—H10	117.9 (10)
C6—C1—C8	119.55 (13)	C10—C11—C12	119.84 (15)
O1—C2—C3	118.65 (14)	C10—C11—H11	118.9 (10)
O1—C2—C1	122.00 (14)	C12—C11—H11	121.1 (10)
C3—C2—C1	119.35 (15)	O3—C12—C11	124.83 (14)
C4—C3—C2	120.70 (16)	O3—C12—C13	116.10 (13)
C4—C3—H3	120.3 (12)	C11—C12—C13	119.06 (14)
C2—C3—H3	119.0 (12)	C14—C13—C12	120.63 (15)
C3—C4—C5	120.92 (16)	C14—C13—H13	121.6 (10)
C3—C4—H4	120.2 (12)	C12—C13—H13	117.7 (10)
C5—C4—H4	118.7 (12)	C13—C14—C9	120.83 (15)
C6—C5—O2	125.23 (15)	C13—C14—H14	121.8 (9)
C6—C5—C4	119.02 (16)	C9—C14—H14	117.4 (9)
O2—C5—C4	115.75 (14)	O3—C15—C16	108.04 (16)
C5—C6—C1	120.99 (15)	O3—C15—H15A	109.3 (11)
C5—C6—H6	120.3 (10)	C16—C15—H15A	111.9 (11)
C1—C6—H6	118.7 (10)	O3—C15—H15B	107.7 (12)
O2—C7—H7A	113.0 (12)	C16—C15—H15B	109.9 (12)
O2—C7—H7B	110.8 (11)	H15A—C15—H15B	109.9 (17)
H7A—C7—H7B	105.2 (17)	C15—C16—H16A	109.9 (15)
O2—C7—H7C	103.0 (11)	C15—C16—H16B	113.3 (16)
H7A—C7—H7C	113.8 (16)	H16A—C16—H16B	107 (2)
H7B—C7—H7C	111.3 (15)	C15—C16—H16C	110.6 (13)
N1—C8—C1	121.24 (14)	H16A—C16—H16C	108 (2)
N1—C8—H8	123.9 (10)	H16B—C16—H16C	107 (2)
C1—C8—H8	114.9 (10)	C8—N1—C9	121.49 (13)
C10—C9—C14	118.40 (14)	C2—O1—H1	106.1 (14)
C10—C9—N1	124.26 (13)	C5—O2—C7	117.78 (14)
C14—C9—N1	117.20 (13)	C12—O3—C15	117.91 (12)
C9—C10—C11	121.23 (14)
C6—C1—C2—O1	179.03 (14)	C9—C10—C11—C12	0.7 (3)
C8—C1—C2—O1	1.0 (2)	C10—C11—C12—O3	178.28 (15)
C6—C1—C2—C3	−0.4 (2)	C10—C11—C12—C13	−0.7 (2)
C8—C1—C2—C3	−178.42 (15)	O3—C12—C13—C14	−178.05 (15)
O1—C2—C3—C4	−179.32 (15)	C11—C12—C13—C14	1.0 (2)
C1—C2—C3—C4	0.2 (3)	C12—C13—C14—C9	−1.3 (3)
C2—C3—C4—C5	0.8 (3)	C10—C9—C14—C13	1.3 (2)
C3—C4—C5—C6	−1.5 (3)	N1—C9—C14—C13	177.16 (14)
C3—C4—C5—O2	177.91 (16)	C1—C8—N1—C9	174.64 (13)
O2—C5—C6—C1	−178.13 (15)	C10—C9—N1—C8	−27.7 (2)
C4—C5—C6—C1	1.2 (2)	C14—C9—N1—C8	156.79 (15)
C2—C1—C6—C5	−0.3 (2)	C6—C5—O2—C7	2.3 (3)
C8—C1—C6—C5	177.78 (14)	C4—C5—O2—C7	−177.08 (18)
C2—C1—C8—N1	−1.0 (2)	C11—C12—O3—C15	8.4 (2)
C6—C1—C8—N1	−179.00 (14)	C13—C12—O3—C15	−172.62 (16)
C14—C9—C10—C11	−1.0 (2)	C16—C15—O3—C12	179.78 (18)
N1—C9—C10—C11	−176.53 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (3)	1.75 (3)	2.5962 (18)	149 (2)
C10—H10···O1i	0.965 (18)	2.571 (18)	3.3801 (19)	141.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93 (3)	1.75 (3)	2.5962 (18)	149 (2)
C10—H10⋯O1i	0.965 (18)	2.571 (18)	3.3801 (19)	141.5 (13)

Symmetry code: (i) .