(E)-4-Meth-oxy-2-(p-tolyl-imino-meth-yl)phenol.

The mol-ecule of the title compound, C(15)H(15)NO(2), adopts the enol-imine tautomeric form and has a strong intra-molecular O-H⋯N hydrogen bond as a result. The mol-ecule is almost planar, with a maximum deviation of 0.1038 (15) Å for the meth-oxy C atom. A weak C-H⋯π inter-action and a weak C-H⋯O hydrogen bond are present in the crystal.

Related literature

For background to thermochromic Schiff bases, see: Moustakali-Mavridis et al. (1980 ▶). For related structures, see: Koşar et al. (2009 ▶); Tanak & Yavuz (2010 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 21.1680 (9) Å

b = 4.7844 (2) Å

c = 12.2759 (4) Å

β = 92.859 (3)°

V = 1241.71 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.76 × 0.52 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.947, T max = 0.984

16465 measured reflections

2627 independent reflections

2223 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.08

2627 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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/S1600536810003028/is2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003028/is2517Isup2.hkl

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

C15H15NO2	F(000) = 512
Mr = 241.28	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16465 reflections
a = 21.1680 (9) Å	θ = 1.7–27.3°
b = 4.7844 (2) Å	µ = 0.09 mm−1
c = 12.2759 (4) Å	T = 296 K
β = 92.859 (3)°	Prism, brown
V = 1241.71 (8) Å3	0.76 × 0.52 × 0.19 mm
Z = 4

Stoe IPDS 2 diffractometer	2627 independent reflections
Radiation source: fine-focus sealed tube	2223 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 6.67 pixels mm-1	θmax = 26.8°, θmin = 1.9°
ω scans	h = −26→26
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.947, Tmax = 0.984	l = −15→15
16465 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.1706P] where P = (Fo2 + 2Fc2)/3
2627 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. 331 frames, detector distance = 120 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	0.30136 (5)	0.2222 (2)	0.54620 (9)	0.0391 (3)
C2	0.30433 (6)	0.1581 (3)	0.43466 (9)	0.0450 (3)
C3	0.34823 (7)	−0.0358 (3)	0.40249 (10)	0.0548 (4)
H3	0.3503	−0.0789	0.3289	0.066*
C4	0.38887 (6)	−0.1658 (3)	0.47753 (11)	0.0512 (3)
H4	0.4183	−0.2941	0.4543	0.061*
C5	0.38594 (6)	−0.1055 (3)	0.58806 (10)	0.0454 (3)
C6	0.34203 (6)	0.0854 (3)	0.62107 (10)	0.0442 (3)
H6	0.3395	0.1235	0.6950	0.053*
C7	0.47395 (8)	−0.3961 (4)	0.63806 (15)	0.0720 (5)
H7A	0.4571	−0.5564	0.5996	0.108*
H7B	0.4985	−0.4560	0.7017	0.108*
H7C	0.5004	−0.2923	0.5913	0.108*
C8	0.25662 (5)	0.4249 (3)	0.58486 (9)	0.0420 (3)
H8	0.2549	0.4552	0.6595	0.050*
C9	0.17663 (5)	0.7627 (2)	0.55871 (9)	0.0400 (3)
C10	0.17533 (6)	0.8537 (3)	0.66634 (10)	0.0491 (3)
H10	0.2043	0.7827	0.7187	0.059*
C11	0.13125 (6)	1.0488 (3)	0.69553 (11)	0.0503 (3)
H11	0.1312	1.1069	0.7678	0.060*
C12	0.08726 (6)	1.1606 (3)	0.62089 (11)	0.0450 (3)
C13	0.08968 (6)	1.0724 (3)	0.51344 (11)	0.0518 (3)
H13	0.0610	1.1455	0.4610	0.062*
C14	0.13368 (6)	0.8786 (3)	0.48282 (10)	0.0488 (3)
H14	0.1345	0.8250	0.4101	0.059*
C15	0.03942 (7)	1.3726 (3)	0.65439 (13)	0.0572 (4)
H15A	0.0372	1.3706	0.7323	0.086*
H15B	−0.0013	1.3271	0.6211	0.086*
H15C	0.0519	1.5551	0.6311	0.086*
N1	0.21955 (5)	0.5626 (2)	0.51970 (8)	0.0419 (3)
O1	0.26517 (5)	0.2806 (3)	0.35863 (7)	0.0651 (3)
O2	0.42372 (5)	−0.2245 (2)	0.66971 (8)	0.0639 (3)
H1	0.2419 (10)	0.410 (5)	0.3970 (18)	0.103 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0390 (6)	0.0401 (6)	0.0385 (6)	−0.0012 (5)	0.0060 (4)	−0.0015 (5)
C2	0.0475 (6)	0.0508 (7)	0.0370 (6)	0.0051 (5)	0.0050 (5)	0.0012 (5)
C3	0.0614 (8)	0.0640 (9)	0.0398 (6)	0.0124 (7)	0.0105 (6)	−0.0048 (6)
C4	0.0478 (7)	0.0540 (8)	0.0527 (7)	0.0110 (6)	0.0108 (6)	−0.0052 (6)
C5	0.0430 (6)	0.0469 (7)	0.0463 (6)	0.0032 (5)	0.0009 (5)	0.0010 (5)
C6	0.0461 (6)	0.0484 (7)	0.0382 (6)	0.0032 (5)	0.0028 (5)	−0.0037 (5)
C7	0.0635 (9)	0.0716 (10)	0.0799 (10)	0.0261 (8)	−0.0057 (8)	−0.0009 (8)
C8	0.0441 (6)	0.0438 (6)	0.0384 (6)	0.0015 (5)	0.0045 (5)	−0.0033 (5)
C9	0.0389 (6)	0.0384 (6)	0.0429 (6)	−0.0010 (5)	0.0049 (4)	−0.0010 (5)
C10	0.0505 (7)	0.0535 (7)	0.0430 (6)	0.0096 (6)	−0.0008 (5)	−0.0044 (5)
C11	0.0550 (7)	0.0505 (7)	0.0458 (6)	0.0047 (6)	0.0063 (5)	−0.0074 (6)
C12	0.0427 (6)	0.0358 (6)	0.0573 (7)	−0.0022 (5)	0.0104 (5)	0.0002 (5)
C13	0.0520 (7)	0.0495 (7)	0.0535 (7)	0.0096 (6)	−0.0026 (6)	0.0037 (6)
C14	0.0541 (7)	0.0499 (7)	0.0422 (6)	0.0067 (6)	0.0017 (5)	−0.0014 (5)
C15	0.0541 (7)	0.0439 (7)	0.0748 (9)	0.0063 (6)	0.0152 (7)	−0.0006 (6)
N1	0.0421 (5)	0.0425 (5)	0.0416 (5)	0.0025 (4)	0.0053 (4)	−0.0013 (4)
O1	0.0743 (7)	0.0839 (8)	0.0369 (5)	0.0305 (6)	−0.0001 (4)	−0.0002 (5)
O2	0.0612 (6)	0.0753 (7)	0.0545 (6)	0.0256 (5)	−0.0038 (5)	0.0009 (5)

C1—C6	1.3914 (17)	C8—H8	0.9300
C1—C2	1.4077 (16)	C9—C14	1.3846 (17)
C1—C8	1.4514 (16)	C9—C10	1.3928 (17)
C2—O1	1.3509 (15)	C9—N1	1.4194 (15)
C2—C3	1.3843 (18)	C10—C11	1.3798 (18)
C3—C4	1.3772 (19)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.3811 (18)
C4—C5	1.3917 (18)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.3882 (19)
C5—O2	1.3741 (15)	C12—C15	1.5050 (17)
C5—C6	1.3782 (17)	C13—C14	1.3796 (18)
C6—H6	0.9300	C13—H13	0.9300
C7—O2	1.4130 (17)	C14—H14	0.9300
C7—H7A	0.9600	C15—H15A	0.9600
C7—H7B	0.9600	C15—H15B	0.9600
C7—H7C	0.9600	C15—H15C	0.9600
C8—N1	1.2757 (15)	O1—H1	0.93 (2)
C6—C1—C2	118.93 (11)	C14—C9—C10	118.01 (11)
C6—C1—C8	119.39 (10)	C14—C9—N1	116.94 (10)
C2—C1—C8	121.68 (11)	C10—C9—N1	125.04 (11)
O1—C2—C3	119.41 (11)	C11—C10—C9	120.23 (12)
O1—C2—C1	121.45 (11)	C11—C10—H10	119.9
C3—C2—C1	119.13 (11)	C9—C10—H10	119.9
C4—C3—C2	121.17 (12)	C10—C11—C12	122.14 (12)
C4—C3—H3	119.4	C10—C11—H11	118.9
C2—C3—H3	119.4	C12—C11—H11	118.9
C3—C4—C5	120.12 (12)	C11—C12—C13	117.20 (11)
C3—C4—H4	119.9	C11—C12—C15	121.35 (12)
C5—C4—H4	119.9	C13—C12—C15	121.44 (12)
O2—C5—C6	115.88 (11)	C14—C13—C12	121.37 (12)
O2—C5—C4	124.94 (11)	C14—C13—H13	119.3
C6—C5—C4	119.18 (12)	C12—C13—H13	119.3
C5—C6—C1	121.45 (11)	C13—C14—C9	121.02 (12)
C5—C6—H6	119.3	C13—C14—H14	119.5
C1—C6—H6	119.3	C9—C14—H14	119.5
O2—C7—H7A	109.5	C12—C15—H15A	109.5
O2—C7—H7B	109.5	C12—C15—H15B	109.5
H7A—C7—H7B	109.5	H15A—C15—H15B	109.5
O2—C7—H7C	109.5	C12—C15—H15C	109.5
H7A—C7—H7C	109.5	H15A—C15—H15C	109.5
H7B—C7—H7C	109.5	H15B—C15—H15C	109.5
N1—C8—C1	122.08 (11)	C8—N1—C9	121.40 (10)
N1—C8—H8	119.0	C2—O1—H1	105.0 (13)
C1—C8—H8	119.0	C5—O2—C7	117.30 (11)
C6—C1—C2—O1	178.73 (12)	C14—C9—C10—C11	1.5 (2)
C8—C1—C2—O1	−0.64 (19)	N1—C9—C10—C11	−179.72 (11)
C6—C1—C2—C3	−1.02 (19)	C9—C10—C11—C12	0.0 (2)
C8—C1—C2—C3	179.61 (12)	C10—C11—C12—C13	−1.2 (2)
O1—C2—C3—C4	−179.83 (13)	C10—C11—C12—C15	179.81 (12)
C1—C2—C3—C4	−0.1 (2)	C11—C12—C13—C14	0.8 (2)
C2—C3—C4—C5	0.6 (2)	C15—C12—C13—C14	179.82 (12)
C3—C4—C5—O2	179.39 (13)	C12—C13—C14—C9	0.7 (2)
C3—C4—C5—C6	0.0 (2)	C10—C9—C14—C13	−1.9 (2)
O2—C5—C6—C1	179.43 (11)	N1—C9—C14—C13	179.26 (12)
C4—C5—C6—C1	−1.1 (2)	C1—C8—N1—C9	−179.19 (10)
C2—C1—C6—C5	1.62 (19)	C14—C9—N1—C8	−173.10 (11)
C8—C1—C6—C5	−179.00 (11)	C10—C9—N1—C8	8.12 (19)
C6—C1—C8—N1	177.85 (11)	C6—C5—O2—C7	−172.88 (13)
C2—C1—C8—N1	−2.79 (19)	C4—C5—O2—C7	7.7 (2)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (2)	1.76 (2)	2.6178 (14)	151 (2)
C15—H15C···Cg1i	0.96	2.66	3.5535 (16)	156
C7—H7B···O2ii	0.96	2.57	3.496 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93 (2)	1.76 (2)	2.6178 (14)	151 (2)
C15—H15C⋯Cg1i	0.96	2.66	3.5535 (16)	156
C7—H7B⋯O2ii	0.96	2.57	3.496 (2)	163

Symmetry codes: (i) ; (ii) .