2-[(4-Ethoxy-phen-yl)imino-meth-yl]-5-methoxy-phenol.

The title compound, C(16)H(17)NO(3), a Schiff base, is stabilized in the solid state in the phenol-imine tautomeric form, with the H atom located on the hydr-oxy O atom rather than on the N atom. This H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond. The mol-ecule is almost planar, the angle between the benzene rings being 4.43 (13)°. C-H⋯π inter-actions are also present.

Related literature

For the industrial and biological properties of Schiff bases, see: Karia et al. (1999 ▶); Taggi et al. (2002 ▶). For n class="Chemical">Schiff base tautomerism, see: Şahin et al. (2005 ▶); Hadjoudis et al. (1987 ▶).

Experimental

Crystal data

C16H17NO3

M = 271.31

Monoclinic,

a = 7.4609 (7) Å

b = 8.3777 (5) Å

c = 23.016 (2) Å

β = 98.896 (8)°

V = 1421.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.49 × 0.28 × 0.07 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.983, T max = 0.994

8971 measured reflections

2788 independent reflections

971 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.075

S = 0.80

2788 reflections

181 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.06 e Å−3

Δρmin = −0.09 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/S1600536809040240/bh2250sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040240/bh2250Isup2.hkl

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

C16H17NO3	F(000) = 576
Mr = 271.31	Dx = 1.268 Mg m−3
Monoclinic, P21/c	Melting point: 381 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.4609 (7) Å	Cell parameters from 5881 reflections
b = 8.3777 (5) Å	θ = 1.8–27.3°
c = 23.016 (2) Å	µ = 0.09 mm−1
β = 98.896 (8)°	T = 296 K
V = 1421.3 (2) Å3	Plate, yellow
Z = 4	0.49 × 0.28 × 0.07 mm

Stoe IPDS-II diffractometer	2788 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
graphite	Rint = 0.068
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.8°
ω scans	h = −8→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→10
Tmin = 0.983, Tmax = 0.994	l = −28→28
8971 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 0.80	w = 1/[σ2(Fo2) + (0.0187P)2] where P = (Fo2 + 2Fc2)/3
2788 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.06 e Å−3
6 restraints	Δρmin = −0.09 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	−0.6165 (4)	0.5043 (3)	0.57051 (10)	0.1085 (9)
H1A	−0.5696	0.6108	0.5697	0.163*
H1B	−0.6483	0.4828	0.6086	0.163*
H1C	−0.7222	0.4938	0.5411	0.163*
C2	−0.3202 (4)	0.3896 (3)	0.59654 (12)	0.0808 (7)
C3	−0.2831 (4)	0.4771 (3)	0.64744 (12)	0.0856 (8)
H3	−0.3693	0.5465	0.6584	0.103*
C4	−0.1155 (5)	0.4605 (3)	0.68216 (11)	0.0800 (7)
C5	0.0154 (4)	0.3552 (3)	0.66750 (11)	0.0757 (7)
C6	−0.0289 (4)	0.2690 (3)	0.61528 (12)	0.0893 (8)
H6	0.0557	0.1980	0.6044	0.107*
C7	−0.1921 (4)	0.2855 (3)	0.57975 (11)	0.0870 (8)
H7	−0.2173	0.2281	0.5449	0.104*
C8	0.1875 (4)	0.3370 (3)	0.70488 (12)	0.0838 (8)
H8	0.2693	0.2612	0.6953	0.101*
C9	0.3994 (5)	0.4049 (3)	0.78873 (12)	0.0795 (7)
C10	0.4158 (4)	0.4914 (3)	0.84077 (13)	0.0890 (8)
H10	0.3202	0.5556	0.8483	0.107*
C11	0.5712 (5)	0.4833 (3)	0.88123 (12)	0.0910 (8)
H11	0.5793	0.5423	0.9158	0.109*
C12	0.7163 (4)	0.3890 (3)	0.87168 (12)	0.0808 (7)
C13	0.7025 (4)	0.3066 (3)	0.81961 (12)	0.0921 (8)
H13	0.7997	0.2452	0.8117	0.111*
C14	0.5468 (5)	0.3141 (3)	0.77915 (12)	0.0936 (8)
H14	0.5403	0.2564	0.7444	0.112*
O3	0.8627 (3)	0.38748 (19)	0.91485 (8)	0.0937 (5)
C16	1.0174 (4)	0.2954 (3)	0.90641 (11)	0.0995 (8)
H16A	1.0645	0.3324	0.8718	0.119*
H16B	0.9841	0.1839	0.9008	0.119*
C17	1.1580 (4)	0.3138 (3)	0.95957 (11)	0.1148 (10)
H17A	1.2637	0.2532	0.9546	0.172*
H17B	1.1108	0.2758	0.9935	0.172*
H17C	1.1900	0.4245	0.9649	0.172*
N1	0.2308 (3)	0.4230 (2)	0.75114 (10)	0.0830 (6)
O1	−0.0840 (2)	0.55210 (18)	0.73075 (7)	0.1034 (6)
H1	0.0175	0.5328	0.7486	0.155*
O2	−0.4817 (3)	0.39332 (19)	0.55872 (7)	0.0959 (5)

	U11	U22	U33	U12	U13	U23
C1	0.104 (2)	0.111 (2)	0.119 (2)	0.008 (2)	0.0432 (17)	−0.0031 (16)
C2	0.101 (3)	0.0615 (16)	0.086 (2)	0.0006 (18)	0.0332 (17)	0.0117 (15)
C3	0.113 (3)	0.0661 (17)	0.0850 (18)	−0.0012 (17)	0.0390 (17)	−0.0099 (15)
C4	0.110 (2)	0.0633 (16)	0.0734 (18)	−0.0098 (18)	0.0350 (17)	−0.0052 (14)
C5	0.107 (3)	0.0510 (15)	0.0770 (18)	0.0034 (16)	0.0393 (17)	0.0008 (13)
C6	0.128 (3)	0.0612 (16)	0.0856 (19)	0.0098 (17)	0.0385 (17)	0.0017 (15)
C7	0.122 (3)	0.0655 (17)	0.0777 (18)	0.0055 (18)	0.0277 (18)	−0.0040 (13)
C8	0.110 (3)	0.0594 (16)	0.0882 (18)	0.0026 (16)	0.0367 (17)	0.0105 (15)
C9	0.113 (3)	0.0539 (16)	0.0788 (19)	−0.0098 (17)	0.0378 (18)	−0.0004 (14)
C10	0.095 (2)	0.0694 (17)	0.109 (2)	−0.0008 (16)	0.0387 (17)	−0.0109 (16)
C11	0.106 (2)	0.0722 (18)	0.103 (2)	−0.0002 (19)	0.0425 (18)	−0.0223 (15)
C12	0.104 (3)	0.0599 (16)	0.0849 (19)	−0.0066 (17)	0.0352 (18)	−0.0046 (14)
C13	0.107 (3)	0.0849 (19)	0.090 (2)	0.0093 (18)	0.0337 (17)	−0.0042 (16)
C14	0.126 (3)	0.0754 (18)	0.089 (2)	0.009 (2)	0.044 (2)	−0.0130 (15)
O3	0.0995 (16)	0.0828 (12)	0.1030 (13)	0.0054 (11)	0.0288 (12)	−0.0143 (9)
C16	0.106 (3)	0.0844 (18)	0.117 (2)	0.0038 (18)	0.0463 (19)	−0.0041 (15)
C17	0.120 (3)	0.118 (2)	0.107 (2)	0.0166 (19)	0.0188 (19)	0.0062 (16)
N1	0.111 (2)	0.0614 (13)	0.0824 (16)	−0.0081 (13)	0.0317 (14)	−0.0039 (11)
O1	0.1215 (16)	0.0934 (12)	0.0997 (12)	0.0025 (11)	0.0312 (10)	−0.0327 (10)
O2	0.1132 (17)	0.0798 (12)	0.0985 (13)	0.0076 (12)	0.0283 (12)	−0.0057 (9)

C1—O2	1.426 (3)	C9—C10	1.389 (3)
C1—H1A	0.9600	C9—N1	1.420 (3)
C1—H1B	0.9600	C10—C11	1.372 (3)
C1—H1C	0.9600	C10—H10	0.9300
C2—O2	1.374 (3)	C11—C12	1.385 (3)
C2—C3	1.374 (3)	C11—H11	0.9300
C2—C7	1.392 (3)	C12—O3	1.358 (3)
C3—C4	1.383 (3)	C12—C13	1.373 (3)
C3—H3	0.9300	C13—C14	1.373 (3)
C4—O1	1.347 (2)	C13—H13	0.9300
C4—C5	1.396 (3)	C14—H14	0.9300
C5—C6	1.398 (3)	O3—C16	1.426 (3)
C5—C8	1.439 (3)	C16—C17	1.492 (3)
C6—C7	1.364 (3)	C16—H16A	0.9700
C6—H6	0.9300	C16—H16B	0.9700
C7—H7	0.9300	C17—H17A	0.9600
C8—N1	1.285 (3)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C14	1.383 (3)	O1—H1	0.8200
O2—C1—H1A	109.5	C11—C10—H10	119.6
O2—C1—H1B	109.5	C9—C10—H10	119.6
H1A—C1—H1B	109.5	C10—C11—C12	121.3 (3)
O2—C1—H1C	109.5	C10—C11—H11	119.3
H1A—C1—H1C	109.5	C12—C11—H11	119.3
H1B—C1—H1C	109.5	O3—C12—C13	125.3 (3)
O2—C2—C3	124.7 (3)	O3—C12—C11	116.7 (3)
O2—C2—C7	114.3 (3)	C13—C12—C11	118.1 (3)
C3—C2—C7	121.0 (3)	C12—C13—C14	120.7 (3)
C2—C3—C4	118.9 (3)	C12—C13—H13	119.6
C2—C3—H3	120.5	C14—C13—H13	119.6
C4—C3—H3	120.5	C13—C14—C9	121.8 (3)
O1—C4—C3	116.6 (3)	C13—C14—H14	119.1
O1—C4—C5	121.5 (3)	C9—C14—H14	119.1
C3—C4—C5	121.9 (3)	C12—O3—C16	118.8 (2)
C4—C5—C6	116.9 (3)	O3—C16—C17	108.3 (2)
C4—C5—C8	121.1 (3)	O3—C16—H16A	110.0
C6—C5—C8	122.0 (3)	C17—C16—H16A	110.0
C7—C6—C5	122.3 (3)	O3—C16—H16B	110.0
C7—C6—H6	118.9	C17—C16—H16B	110.0
C5—C6—H6	118.9	H16A—C16—H16B	108.4
C6—C7—C2	119.0 (3)	C16—C17—H17A	109.5
C6—C7—H7	120.5	C16—C17—H17B	109.5
C2—C7—H7	120.5	H17A—C17—H17B	109.5
N1—C8—C5	121.5 (3)	C16—C17—H17C	109.5
N1—C8—H8	119.2	H17A—C17—H17C	109.5
C5—C8—H8	119.2	H17B—C17—H17C	109.5
C14—C9—C10	117.3 (3)	C8—N1—C9	122.1 (2)
C14—C9—N1	127.8 (3)	C4—O1—H1	109.5
C10—C9—N1	114.9 (3)	C2—O2—C1	118.0 (2)
C11—C10—C9	120.8 (3)
O2—C2—C3—C4	179.0 (2)	C9—C10—C11—C12	−0.1 (4)
C7—C2—C3—C4	0.0 (3)	C10—C11—C12—O3	−179.1 (2)
C2—C3—C4—O1	178.26 (19)	C10—C11—C12—C13	1.8 (4)
C2—C3—C4—C5	−1.2 (3)	O3—C12—C13—C14	178.9 (2)
O1—C4—C5—C6	−178.2 (2)	C11—C12—C13—C14	−2.0 (4)
C3—C4—C5—C6	1.2 (3)	C12—C13—C14—C9	0.6 (4)
O1—C4—C5—C8	1.9 (3)	C10—C9—C14—C13	1.1 (3)
C3—C4—C5—C8	−178.6 (2)	N1—C9—C14—C13	−179.7 (2)
C4—C5—C6—C7	0.0 (3)	C13—C12—O3—C16	0.7 (3)
C8—C5—C6—C7	179.8 (2)	C11—C12—O3—C16	−178.4 (2)
C5—C6—C7—C2	−1.2 (4)	C12—O3—C16—C17	179.9 (2)
O2—C2—C7—C6	−178.0 (2)	C5—C8—N1—C9	179.3 (2)
C3—C2—C7—C6	1.2 (3)	C14—C9—N1—C8	8.9 (3)
C4—C5—C8—N1	−4.0 (3)	C10—C9—N1—C8	−171.8 (2)
C6—C5—C8—N1	176.2 (2)	C3—C2—O2—C1	4.8 (3)
C14—C9—C10—C11	−1.3 (3)	C7—C2—O2—C1	−176.0 (2)
N1—C9—C10—C11	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.563 (3)	148
C1—H1A···Cg2i	0.96	3.32	4.000 (3)	129
C3—H3···Cg2i	0.93	3.30	4.155 (3)	155
C8—H8···Cg2ii	0.93	3.39	4.269 (3)	159
C10—H10···Cg1i	0.93	3.00	3.849 (3)	153
C16—H16B···Cg1ii	0.97	3.04	3.822 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.563 (3)	148
C1—H1A⋯Cg2i	0.96	3.32	4.000 (3)	129
C3—H3⋯Cg2i	0.93	3.30	4.155 (3)	155
C8—H8⋯Cg2ii	0.93	3.39	4.269 (3)	159
C10—H10⋯Cg1i	0.93	3.00	3.849 (3)	153
C16—H16B⋯Cg1ii	0.97	3.04	3.822 (3)	139

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the [please define] and [please define] rings, respectively.