3-Meth-oxy-2-[(E)-(4-meth-oxy-phen-yl)imino-meth-yl]phenol.

The title compound, C(15)H(15)NO(3), adopts the enol-imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intra-molecular O-H⋯N hydrogen bond. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into sheets parallel to (010). These sheets are inter-connected by weak C-H⋯π inter-actions.

Related literature

For background to the properties and uses of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶); Taggi et al. (2002 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For related structures, see: Özdemir Tarı et al. (2010 ▶); Şahin et al. (2005 ▶).

Experimental

Crystal data

C15H15NO3

M = 257.28

Monoclinic,

a = 14.2658 (8) Å

b = 14.1553 (11) Å

c = 6.5893 (17) Å

β = 96.398 (9)°

V = 1322.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.65 × 0.32 × 0.14 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe, 2002) ▶ T min = 0.991, T max = 0.997

7244 measured reflections

2585 independent reflections

1622 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.122

S = 1.04

2585 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe, 2002) ▶; cell refinement: X-AREA ▶; data reduction: X-RED32 (Stoe, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000596/dn2646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000596/dn2646Isup2.hkl

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

C15H15NO3	F(000) = 544
Mr = 257.28	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12079 reflections
a = 14.2658 (8) Å	θ = 1.4–27.2°
b = 14.1553 (11) Å	µ = 0.09 mm−1
c = 6.5893 (17) Å	T = 293 K
β = 96.398 (9)°	Prism, brown
V = 1322.3 (4) Å3	0.65 × 0.32 × 0.14 mm
Z = 4

Stoe IPDS 2 diffractometer	2585 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.4°
φ scan rotation method	h = −16→17
Absorption correction: integration (X-RED32; Stoe, 2002)	k = −17→17
Tmin = 0.991, Tmax = 0.997	l = −8→6
7244 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1038P] where P = (Fo2 + 2Fc2)/3
2585 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.19 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	0.20529 (13)	0.11619 (13)	0.4013 (3)	0.0443 (5)
C2	0.29338 (14)	0.10131 (14)	0.3295 (3)	0.0483 (5)
H2	0.2959	0.0793	0.1972	0.058*
C3	0.37566 (14)	0.11898 (15)	0.4526 (3)	0.0516 (5)
C4	0.37125 (16)	0.15062 (15)	0.6515 (3)	0.0548 (6)
H4	0.4268	0.1626	0.7353	0.066*
C5	0.28635 (16)	0.16440 (15)	0.7254 (3)	0.0542 (6)
H5	0.2848	0.1854	0.8588	0.065*
C6	0.20294 (15)	0.14735 (14)	0.6034 (3)	0.0479 (5)
C7	0.11923 (14)	0.10451 (13)	0.2639 (3)	0.0481 (5)
H7	0.1229	0.0900	0.1274	0.058*
C8	−0.04619 (13)	0.11307 (14)	0.1930 (3)	0.0459 (5)
C9	−0.12676 (15)	0.07751 (15)	0.2668 (4)	0.0544 (6)
H9	−0.1226	0.0522	0.3977	0.065*
C10	−0.21198 (15)	0.07926 (15)	0.1495 (4)	0.0553 (6)
H10	−0.2648	0.0535	0.1995	0.066*
C11	−0.22005 (14)	0.11941 (14)	−0.0446 (4)	0.0512 (5)
C12	−0.14058 (15)	0.15559 (16)	−0.1200 (4)	0.0561 (6)
H12	−0.1452	0.1823	−0.2497	0.067*
C13	−0.05435 (15)	0.15172 (15)	−0.0012 (3)	0.0537 (6)
H13	−0.0010	0.1755	−0.0526	0.064*
C14	−0.3216 (2)	0.1629 (2)	−0.3428 (5)	0.0908 (9)
H14A	−0.3868	0.1590	−0.3970	0.136*
H14B	−0.2837	0.1297	−0.4310	0.136*
H14C	−0.3026	0.2280	−0.3338	0.136*
C15	0.47450 (18)	0.0772 (2)	0.1985 (4)	0.0881 (9)
H15A	0.5402	0.0742	0.1795	0.132*
H15B	0.4427	0.1196	0.1000	0.132*
H15C	0.4472	0.0153	0.1810	0.132*
N1	0.03849 (12)	0.11390 (12)	0.3283 (3)	0.0496 (4)
O1	0.46496 (10)	0.10987 (13)	0.3953 (3)	0.0752 (5)
O2	0.12069 (11)	0.16290 (11)	0.6830 (2)	0.0636 (5)
H2A	0.0763	0.1500	0.5975	0.095*
O3	−0.30930 (10)	0.12168 (12)	−0.1453 (3)	0.0662 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0417 (11)	0.0426 (10)	0.0480 (12)	−0.0004 (9)	0.0020 (9)	−0.0004 (9)
C2	0.0481 (12)	0.0525 (12)	0.0439 (12)	0.0043 (9)	0.0032 (10)	−0.0031 (9)
C3	0.0418 (11)	0.0593 (12)	0.0524 (13)	0.0040 (10)	0.0000 (10)	0.0011 (10)
C4	0.0537 (14)	0.0603 (13)	0.0475 (13)	−0.0011 (10)	−0.0073 (11)	−0.0002 (10)
C5	0.0630 (15)	0.0575 (13)	0.0412 (12)	0.0010 (10)	0.0017 (11)	−0.0042 (10)
C6	0.0494 (13)	0.0472 (11)	0.0487 (13)	0.0010 (9)	0.0117 (10)	0.0013 (9)
C7	0.0468 (12)	0.0484 (11)	0.0494 (12)	0.0000 (9)	0.0059 (10)	−0.0025 (9)
C8	0.0401 (11)	0.0430 (11)	0.0551 (13)	−0.0016 (9)	0.0075 (10)	−0.0027 (9)
C9	0.0480 (13)	0.0570 (13)	0.0586 (14)	−0.0036 (10)	0.0080 (11)	0.0085 (11)
C10	0.0406 (12)	0.0562 (13)	0.0706 (15)	−0.0078 (10)	0.0127 (11)	0.0063 (11)
C11	0.0404 (11)	0.0493 (11)	0.0632 (14)	−0.0021 (9)	0.0025 (10)	−0.0071 (11)
C12	0.0519 (13)	0.0645 (14)	0.0516 (13)	−0.0045 (10)	0.0046 (11)	0.0036 (10)
C13	0.0402 (12)	0.0667 (13)	0.0548 (14)	−0.0061 (10)	0.0086 (10)	0.0042 (11)
C14	0.0623 (17)	0.125 (3)	0.079 (2)	−0.0102 (16)	−0.0186 (15)	0.0173 (18)
C15	0.0519 (15)	0.142 (3)	0.0722 (18)	0.0053 (15)	0.0146 (14)	−0.0252 (18)
N1	0.0409 (10)	0.0518 (10)	0.0561 (11)	−0.0028 (8)	0.0057 (8)	0.0023 (8)
O1	0.0402 (9)	0.1206 (15)	0.0637 (11)	0.0052 (9)	0.0009 (8)	−0.0167 (10)
O2	0.0557 (9)	0.0812 (11)	0.0560 (10)	0.0037 (8)	0.0157 (8)	−0.0081 (8)
O3	0.0417 (9)	0.0795 (11)	0.0749 (11)	−0.0074 (7)	−0.0055 (8)	0.0016 (9)

C1—C6	1.407 (3)	C9—H9	0.9300
C1—C2	1.407 (3)	C10—C11	1.393 (3)
C1—C7	1.451 (3)	C10—H10	0.9300
C2—C3	1.373 (3)	C11—O3	1.369 (2)
C2—H2	0.9300	C11—C12	1.386 (3)
C3—O1	1.375 (3)	C12—C13	1.384 (3)
C3—C4	1.393 (3)	C12—H12	0.9300
C4—C5	1.369 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—O3	1.419 (3)
C5—C6	1.381 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—O2	1.356 (2)	C14—H14C	0.9600
C7—N1	1.278 (3)	C15—O1	1.397 (3)
C7—H7	0.9300	C15—H15A	0.9600
C8—C13	1.385 (3)	C15—H15B	0.9600
C8—C9	1.391 (3)	C15—H15C	0.9600
C8—N1	1.419 (2)	O2—H2A	0.8200
C9—C10	1.366 (3)
C6—C1—C2	118.79 (19)	C9—C10—H10	119.9
C6—C1—C7	121.21 (19)	C11—C10—H10	119.9
C2—C1—C7	119.91 (19)	O3—C11—C12	124.9 (2)
C3—C2—C1	120.7 (2)	O3—C11—C10	115.58 (18)
C3—C2—H2	119.6	C12—C11—C10	119.5 (2)
C1—C2—H2	119.6	C13—C12—C11	119.6 (2)
C2—C3—O1	125.3 (2)	C13—C12—H12	120.2
C2—C3—C4	119.3 (2)	C11—C12—H12	120.2
O1—C3—C4	115.40 (19)	C12—C13—C8	121.1 (2)
C5—C4—C3	121.0 (2)	C12—C13—H13	119.5
C5—C4—H4	119.5	C8—C13—H13	119.5
C3—C4—H4	119.5	O3—C14—H14A	109.5
C4—C5—C6	120.4 (2)	O3—C14—H14B	109.5
C4—C5—H5	119.8	H14A—C14—H14B	109.5
C6—C5—H5	119.8	O3—C14—H14C	109.5
O2—C6—C5	118.21 (18)	H14A—C14—H14C	109.5
O2—C6—C1	122.03 (19)	H14B—C14—H14C	109.5
C5—C6—C1	119.75 (19)	O1—C15—H15A	109.5
N1—C7—C1	120.8 (2)	O1—C15—H15B	109.5
N1—C7—H7	119.6	H15A—C15—H15B	109.5
C1—C7—H7	119.6	O1—C15—H15C	109.5
C13—C8—C9	118.6 (2)	H15A—C15—H15C	109.5
C13—C8—N1	123.71 (18)	H15B—C15—H15C	109.5
C9—C8—N1	117.54 (19)	C7—N1—C8	121.78 (19)
C10—C9—C8	120.9 (2)	C3—O1—C15	118.36 (18)
C10—C9—H9	119.6	C6—O2—H2A	109.5
C8—C9—H9	119.6	C11—O3—C14	117.85 (19)
C9—C10—C11	120.29 (19)
C6—C1—C2—C3	−1.5 (3)	N1—C8—C9—C10	176.32 (19)
C7—C1—C2—C3	175.00 (19)	C8—C9—C10—C11	−1.9 (3)
C1—C2—C3—O1	−177.7 (2)	C9—C10—C11—O3	−176.91 (19)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	1.5 (3)
C2—C3—C4—C5	−0.1 (3)	O3—C11—C12—C13	178.0 (2)
O1—C3—C4—C5	178.7 (2)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—C8	−0.6 (3)
C4—C5—C6—O2	−179.4 (2)	C9—C8—C13—C12	0.3 (3)
C4—C5—C6—C1	−0.4 (3)	N1—C8—C13—C12	−174.7 (2)
C2—C1—C6—O2	−179.81 (18)	C1—C7—N1—C8	172.99 (18)
C7—C1—C6—O2	3.7 (3)	C13—C8—N1—C7	−36.1 (3)
C2—C1—C6—C5	1.2 (3)	C9—C8—N1—C7	148.9 (2)
C7—C1—C6—C5	−175.24 (19)	C2—C3—O1—C15	−2.2 (4)
C6—C1—C7—N1	−6.4 (3)	C4—C3—O1—C15	179.1 (2)
C2—C1—C7—N1	177.11 (18)	C12—C11—O3—C14	0.9 (3)
C13—C8—C9—C10	1.0 (3)	C10—C11—O3—C14	179.2 (2)

Cg1 is the centroid of the C1—C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.93	2.60	3.428 (3)	149
C14—H14A···O1ii	0.96	2.49	3.412 (3)	162
O2—H2A···N1	0.82	1.87	2.590 (2)	146
C5—H5···Cg1iii	0.93	2.80	3.486 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1—C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.93	2.60	3.428 (3)	149
C14—H14A⋯O1ii	0.96	2.49	3.412 (3)	162
O2—H2A⋯N1	0.82	1.87	2.590 (2)	146
C5—H5⋯Cg1iii	0.93	2.80	3.486 (2)	132

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