2-[(4-Ethyl-phen-yl)imino-meth-yl]-3,5-dimethoxy-phenol.

The title compound, C(17)H(19)NO(3), adopts the phenol-imine tautomeric form, with a resonance-assisted O-H⋯N intra-molecular hydrogen bond [O⋯N = 2.551 (3) Å]. The dihedral angle between the two benzene rings is 45.42 (7)°. The two meth-oxy groups are coplanar with the attached benzene ring [C-O-C-C torsion angles = -1.1 (5) and 3.2 (4)°].

Related literature

For the photochromic and thermochromic characteristics of Schiff base compounds, see: Hadjoudis et al. (1987 ▶); Lozier et al. (1975 ▶). For the notation of hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H19NO3

M = 285.33

Orthorhombic,

a = 7.5026 (5) Å

b = 9.4540 (8) Å

c = 21.4408 (13) Å

V = 1520.79 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.46 × 0.35 × 0.11 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.991, T max = 0.998

10094 measured reflections

1831 independent reflections

1036 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.077

S = 0.92

1831 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.11 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/S1600536809004784/ci2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004784/ci2762Isup2.hkl

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

C17H19NO3	F(000) = 608
Mr = 285.33	Dx = 1.246 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10094 reflections
a = 7.5026 (5) Å	θ = 1.9–27.7°
b = 9.4540 (8) Å	µ = 0.09 mm−1
c = 21.4408 (13) Å	T = 296 K
V = 1520.79 (19) Å3	Prism, yellow
Z = 4	0.46 × 0.35 × 0.11 mm

Stoe IPDS II diffractometer	1831 independent reflections
Radiation source: fine-focus sealed tube	1036 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.9°
ω scans	h = −9→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→10
Tmin = 0.991, Tmax = 0.998	l = −26→26
10094 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3
1831 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.11 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
C1	0.2906 (4)	0.3417 (3)	0.70797 (12)	0.0630 (8)
C2	0.2290 (5)	0.3445 (3)	0.76807 (12)	0.0692 (9)
H2	0.1988	0.4295	0.7871	0.083*
C3	0.2128 (4)	0.2174 (3)	0.79972 (12)	0.0635 (8)
C4	0.2526 (4)	0.0871 (3)	0.77182 (11)	0.0566 (7)
C5	0.3141 (4)	0.0911 (3)	0.70914 (12)	0.0610 (8)
C6	0.3354 (4)	0.2165 (3)	0.67808 (12)	0.0630 (8)
H6	0.3794	0.2178	0.6375	0.076*
C7	0.2409 (4)	−0.0436 (3)	0.80628 (12)	0.0601 (7)
H7	0.2663	−0.1284	0.7862	0.072*
C8	0.1874 (4)	−0.1759 (3)	0.89708 (11)	0.0559 (7)
C9	0.2513 (4)	−0.1775 (3)	0.95769 (12)	0.0679 (8)
H9	0.2991	−0.0956	0.9749	0.081*
C10	0.2447 (5)	−0.3000 (3)	0.99269 (12)	0.0699 (8)
H10	0.2930	−0.3004	1.0326	0.084*
C11	0.1679 (4)	−0.4216 (3)	0.96967 (12)	0.0625 (8)
C12	0.1013 (4)	−0.4181 (3)	0.90983 (12)	0.0634 (8)
H12	0.0481	−0.4988	0.8934	0.076*
C13	0.1118 (4)	−0.2971 (3)	0.87352 (11)	0.0604 (8)
H13	0.0675	−0.2980	0.8330	0.072*
C14	0.2705 (5)	0.5932 (3)	0.69842 (14)	0.0878 (10)
H14A	0.2939	0.6663	0.6685	0.132*
H14B	0.3412	0.6091	0.7350	0.132*
H14C	0.1464	0.5944	0.7094	0.132*
C15	0.4190 (5)	−0.0439 (4)	0.62229 (12)	0.0884 (11)
H15A	0.4361	−0.1407	0.6102	0.133*
H15B	0.5311	0.0049	0.6212	0.133*
H15C	0.3372	0.0007	0.5940	0.133*
C16	0.1567 (5)	−0.5544 (3)	1.00901 (14)	0.0857 (10)
H16A	0.1075	−0.5299	1.0494	0.103*
H16B	0.0747	−0.6198	0.9892	0.103*
C17	0.3298 (6)	−0.6273 (4)	1.01865 (17)	0.1268 (16)
H17A	0.3789	−0.6538	0.9790	0.190*
H17B	0.3116	−0.7105	1.0435	0.190*
H17C	0.4108	−0.5648	1.0397	0.190*
N1	0.1964 (3)	−0.0451 (2)	0.86397 (10)	0.0629 (7)
O1	0.3148 (3)	0.4591 (2)	0.67216 (8)	0.0834 (7)
O2	0.3479 (3)	−0.0388 (2)	0.68417 (8)	0.0781 (6)
O3	0.1587 (4)	0.2229 (2)	0.85970 (8)	0.0879 (7)
H3	0.1526	0.1425	0.8738	0.132*

	U11	U22	U33	U12	U13	U23
C1	0.063 (2)	0.060 (2)	0.0665 (18)	−0.0127 (18)	−0.0040 (17)	0.0093 (15)
C2	0.082 (2)	0.0589 (19)	0.0672 (18)	−0.0111 (18)	0.0035 (17)	−0.0034 (15)
C3	0.070 (2)	0.0659 (18)	0.0548 (15)	−0.0106 (19)	0.0023 (15)	−0.0011 (15)
C4	0.0569 (19)	0.0566 (18)	0.0563 (15)	−0.0072 (17)	−0.0013 (14)	0.0015 (14)
C5	0.059 (2)	0.0607 (19)	0.0630 (17)	0.0015 (17)	−0.0005 (14)	−0.0030 (15)
C6	0.062 (2)	0.0680 (19)	0.0586 (15)	−0.0035 (19)	0.0001 (14)	0.0062 (16)
C7	0.0531 (18)	0.0607 (18)	0.0665 (17)	0.0020 (17)	0.0004 (15)	0.0003 (14)
C8	0.0524 (19)	0.062 (2)	0.0534 (15)	0.0002 (17)	0.0044 (14)	0.0009 (14)
C9	0.074 (2)	0.067 (2)	0.0621 (16)	−0.0129 (18)	−0.0080 (16)	−0.0051 (15)
C10	0.075 (2)	0.078 (2)	0.0569 (15)	−0.0050 (19)	−0.0071 (15)	0.0078 (16)
C11	0.061 (2)	0.062 (2)	0.0642 (17)	0.0031 (18)	0.0066 (14)	0.0035 (15)
C12	0.067 (2)	0.0563 (19)	0.0664 (18)	−0.0047 (17)	0.0065 (16)	−0.0045 (15)
C13	0.059 (2)	0.068 (2)	0.0541 (15)	−0.0018 (17)	0.0005 (14)	−0.0004 (16)
C14	0.104 (3)	0.062 (2)	0.097 (2)	−0.006 (2)	−0.009 (2)	0.0148 (18)
C15	0.110 (3)	0.092 (2)	0.0636 (18)	0.001 (2)	0.0264 (18)	−0.0078 (17)
C16	0.100 (3)	0.076 (2)	0.081 (2)	0.003 (2)	0.0076 (19)	0.0194 (18)
C17	0.125 (4)	0.119 (3)	0.137 (3)	0.047 (3)	0.038 (3)	0.058 (3)
N1	0.0689 (18)	0.0643 (15)	0.0554 (14)	−0.0059 (15)	0.0017 (12)	0.0050 (11)
O1	0.1059 (19)	0.0655 (13)	0.0788 (14)	−0.0060 (14)	0.0029 (12)	0.0146 (12)
O2	0.0968 (17)	0.0701 (14)	0.0674 (12)	0.0057 (13)	0.0197 (12)	0.0004 (11)
O3	0.136 (2)	0.0651 (13)	0.0621 (11)	−0.0094 (16)	0.0212 (12)	−0.0037 (9)

C1—O1	1.362 (3)	C11—C12	1.377 (3)
C1—C2	1.369 (3)	C11—C16	1.515 (4)
C1—C6	1.387 (4)	C12—C13	1.386 (4)
C2—C3	1.385 (4)	C12—H12	0.93
C2—H2	0.93	C13—H13	0.93
C3—O3	1.350 (3)	C14—O1	1.426 (3)
C3—C4	1.401 (3)	C14—H14A	0.96
C4—C5	1.421 (3)	C14—H14B	0.96
C4—C7	1.442 (3)	C14—H14C	0.96
C5—O2	1.364 (3)	C15—O2	1.430 (3)
C5—C6	1.370 (4)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—N1	1.281 (3)	C15—H15C	0.96
C7—H7	0.93	C16—C17	1.485 (5)
C8—C13	1.375 (4)	C16—H16A	0.97
C8—C9	1.385 (3)	C16—H16B	0.97
C8—N1	1.428 (3)	C17—H17A	0.96
C9—C10	1.381 (4)	C17—H17B	0.96
C9—H9	0.93	C17—H17C	0.96
C10—C11	1.377 (4)	O3—H3	0.82
C10—H10	0.93
O1—C1—C2	124.0 (3)	C11—C12—H12	119.2
O1—C1—C6	113.7 (2)	C13—C12—H12	119.2
C2—C1—C6	122.2 (3)	C8—C13—C12	120.3 (2)
C1—C2—C3	118.3 (3)	C8—C13—H13	119.8
C1—C2—H2	120.9	C12—C13—H13	119.8
C3—C2—H2	120.9	O1—C14—H14A	109.5
O3—C3—C2	117.4 (3)	O1—C14—H14B	109.5
O3—C3—C4	120.3 (3)	H14A—C14—H14B	109.5
C2—C3—C4	122.3 (2)	O1—C14—H14C	109.5
C3—C4—C5	116.7 (3)	H14A—C14—H14C	109.5
C3—C4—C7	121.4 (2)	H14B—C14—H14C	109.5
C5—C4—C7	121.8 (3)	O2—C15—H15A	109.5
O2—C5—C6	124.5 (2)	O2—C15—H15B	109.5
O2—C5—C4	114.1 (2)	H15A—C15—H15B	109.5
C6—C5—C4	121.4 (3)	O2—C15—H15C	109.5
C5—C6—C1	119.0 (3)	H15A—C15—H15C	109.5
C5—C6—H6	120.5	H15B—C15—H15C	109.5
C1—C6—H6	120.5	C17—C16—C11	114.4 (3)
N1—C7—C4	121.3 (3)	C17—C16—H16A	108.7
N1—C7—H7	119.3	C11—C16—H16A	108.7
C4—C7—H7	119.3	C17—C16—H16B	108.7
C13—C8—C9	118.6 (3)	C11—C16—H16B	108.7
C13—C8—N1	124.0 (2)	H16A—C16—H16B	107.6
C9—C8—N1	117.3 (3)	C16—C17—H17A	109.5
C10—C9—C8	120.4 (3)	C16—C17—H17B	109.5
C10—C9—H9	119.8	H17A—C17—H17B	109.5
C8—C9—H9	119.8	C16—C17—H17C	109.5
C11—C10—C9	121.4 (3)	H17A—C17—H17C	109.5
C11—C10—H10	119.3	H17B—C17—H17C	109.5
C9—C10—H10	119.3	C7—N1—C8	120.1 (2)
C10—C11—C12	117.8 (3)	C1—O1—C14	118.1 (2)
C10—C11—C16	121.0 (3)	C5—O2—C15	117.6 (2)
C12—C11—C16	121.2 (3)	C3—O3—H3	109.5
C11—C12—C13	121.5 (3)
O1—C1—C2—C3	−179.1 (3)	N1—C8—C9—C10	179.2 (3)
C6—C1—C2—C3	0.5 (5)	C8—C9—C10—C11	−2.9 (5)
C1—C2—C3—O3	177.4 (3)	C9—C10—C11—C12	1.5 (5)
C1—C2—C3—C4	−1.8 (5)	C9—C10—C11—C16	−178.3 (3)
O3—C3—C4—C5	−178.1 (3)	C10—C11—C12—C13	0.4 (4)
C2—C3—C4—C5	1.1 (4)	C16—C11—C12—C13	−179.7 (3)
O3—C3—C4—C7	−1.4 (4)	C9—C8—C13—C12	−0.4 (4)
C2—C3—C4—C7	177.8 (3)	N1—C8—C13—C12	−177.1 (3)
C3—C4—C5—O2	−179.0 (3)	C11—C12—C13—C8	−1.0 (4)
C7—C4—C5—O2	4.3 (4)	C10—C11—C16—C17	−71.9 (4)
C3—C4—C5—C6	0.8 (4)	C12—C11—C16—C17	108.2 (4)
C7—C4—C5—C6	−175.8 (3)	C4—C7—N1—C8	−179.5 (3)
O2—C5—C6—C1	177.8 (3)	C13—C8—N1—C7	−43.7 (4)
C4—C5—C6—C1	−2.1 (4)	C9—C8—N1—C7	139.6 (3)
O1—C1—C6—C5	−179.0 (3)	C2—C1—O1—C14	−1.1 (5)
C2—C1—C6—C5	1.4 (5)	C6—C1—O1—C14	179.3 (3)
C3—C4—C7—N1	−1.1 (4)	C6—C5—O2—C15	3.2 (4)
C5—C4—C7—N1	175.4 (3)	C4—C5—O2—C15	−176.9 (3)
C13—C8—C9—C10	2.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.82	2.551 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	1.82	2.551 (3)	149