(E)-5-Meth-oxy-2-(o-tolyl-imino-meth-yl)phenol.

In the title compound, C(15)H(15)NO(2), the phenol group make dihedral angles of 2.4 (2) and 24.1 (9)° with the imine linkage (-C=N-) and the phenyl group, respectively, and the mol-ecule adopts the enol-imine tautomeric form, so the mol-ecular structure is stabilized by a strong intra-molecular O-H⋯N hydrogen bond. The crystal structure features a weak C-H⋯π inter-action.

Related literature

For the relationships between thermochromism and photochromism and the planarity of mol­ecules, see: Moustakali-Mavridis et al. (1980 ▶). For bond lengths in related structures, see: Tanak & Yavuz (2009 ▶); Koşar et al. (2009 ▶.

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 22.3720 (16) Å

b = 7.3191 (4) Å

c = 22.1704 (14) Å

β = 136.094 (4)°

V = 2517.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.80 × 0.46 × 0.21 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.948, T max = 0.984

17732 measured reflections

2914 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.122

S = 1.03

2914 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (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 global, I. DOI: 10.1107/S1600536809055615/bx2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055615/bx2258Isup2.hkl

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

C15H15NO2	F(000) = 1024
Mr = 241.28	Dx = 1.273 Mg m−3
Monoclinic, C2/c	Melting point: 372 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 22.3720 (16) Å	Cell parameters from 2073 reflections
b = 7.3191 (4) Å	θ = 1.9–28.0°
c = 22.1704 (14) Å	µ = 0.09 mm−1
β = 136.094 (4)°	T = 293 K
V = 2517.5 (3) Å3	Prism, yellow
Z = 8	0.80 × 0.46 × 0.21 mm

Stoe IPDS II diffractometer	2914 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω scan	h = −28→28
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.948, Tmax = 0.984	l = −28→28
17732 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.4484P] where P = (Fo2 + 2Fc2)/3
2914 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.12 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	0.44408 (9)	0.4751 (2)	0.61857 (10)	0.0585 (4)
C2	0.48769 (10)	0.4298 (2)	0.59731 (11)	0.0628 (4)
C3	0.54314 (12)	0.5583 (3)	0.61274 (13)	0.0750 (5)
H3	0.5734	0.5293	0.5998	0.090*
C4	0.55431 (13)	0.7276 (3)	0.64672 (13)	0.0829 (6)
H4	0.5932	0.8101	0.6584	0.100*
C5	0.50793 (15)	0.7743 (3)	0.66328 (13)	0.0839 (6)
H5	0.5141	0.8900	0.6846	0.101*
C6	0.45217 (12)	0.6501 (2)	0.64842 (11)	0.0708 (5)
H6	0.4198	0.6833	0.6584	0.085*
C7	0.47509 (15)	0.2476 (3)	0.55859 (15)	0.0866 (6)
H7A	0.4156	0.2332	0.5044	0.104*
H7B	0.4913	0.1524	0.5979	0.104*
H7C	0.5103	0.2405	0.5486	0.104*
C8	0.37691 (10)	0.3374 (2)	0.65349 (10)	0.0626 (4)
H8	0.3972	0.4336	0.6917	0.075*
C9	0.32840 (9)	0.1941 (2)	0.64692 (9)	0.0556 (4)
C10	0.29831 (9)	0.0417 (2)	0.59225 (10)	0.0543 (4)
C11	0.25453 (10)	−0.0984 (2)	0.58927 (10)	0.0568 (4)
H11	0.2359	−0.1996	0.5539	0.068*
C12	0.23880 (9)	−0.0871 (2)	0.63893 (10)	0.0555 (4)
C13	0.26662 (11)	0.0640 (2)	0.69232 (10)	0.0624 (4)
H13	0.2552	0.0717	0.7251	0.075*
C14	0.31064 (10)	0.2001 (2)	0.69596 (10)	0.0630 (4)
H14	0.3295	0.2999	0.7320	0.076*
C15	0.16589 (13)	−0.3735 (3)	0.58692 (13)	0.0782 (5)
H15A	0.2134	−0.4352	0.6026	0.094*
H15B	0.1254	−0.3358	0.5272	0.094*
H15C	0.1381	−0.4547	0.5946	0.094*
N1	0.39313 (8)	0.33716 (19)	0.60847 (8)	0.0602 (4)
O1	0.31237 (8)	0.02673 (19)	0.54283 (8)	0.0683 (3)
O2	0.19682 (8)	−0.21732 (17)	0.64089 (8)	0.0701 (3)
H16	0.3415 (14)	0.134 (3)	0.5514 (14)	0.102 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0516 (8)	0.0595 (10)	0.0495 (8)	−0.0007 (7)	0.0314 (7)	0.0071 (7)
C2	0.0593 (9)	0.0617 (10)	0.0615 (9)	0.0016 (8)	0.0415 (8)	0.0104 (8)
C3	0.0684 (10)	0.0764 (12)	0.0796 (12)	−0.0016 (9)	0.0531 (10)	0.0124 (10)
C4	0.0808 (12)	0.0762 (14)	0.0748 (12)	−0.0196 (10)	0.0504 (11)	0.0049 (10)
C5	0.1089 (15)	0.0595 (11)	0.0715 (12)	−0.0139 (11)	0.0611 (12)	−0.0009 (9)
C6	0.0797 (11)	0.0627 (11)	0.0640 (10)	0.0004 (9)	0.0498 (10)	0.0056 (8)
C7	0.1093 (15)	0.0689 (12)	0.1185 (17)	−0.0058 (11)	0.0944 (15)	−0.0008 (12)
C8	0.0550 (9)	0.0661 (10)	0.0533 (9)	−0.0033 (7)	0.0346 (8)	−0.0030 (8)
C9	0.0513 (8)	0.0622 (9)	0.0488 (8)	−0.0004 (7)	0.0345 (7)	−0.0003 (7)
C10	0.0511 (8)	0.0643 (10)	0.0499 (8)	0.0035 (7)	0.0371 (7)	0.0020 (7)
C11	0.0560 (8)	0.0620 (10)	0.0525 (8)	−0.0011 (7)	0.0390 (7)	−0.0040 (7)
C12	0.0517 (8)	0.0647 (10)	0.0515 (8)	0.0001 (7)	0.0377 (7)	0.0026 (7)
C13	0.0675 (9)	0.0751 (11)	0.0551 (9)	−0.0014 (9)	0.0476 (8)	−0.0041 (8)
C14	0.0649 (9)	0.0677 (10)	0.0542 (9)	−0.0054 (8)	0.0422 (8)	−0.0093 (8)
C15	0.0935 (13)	0.0710 (12)	0.0880 (13)	−0.0158 (10)	0.0713 (12)	−0.0092 (10)
N1	0.0544 (7)	0.0645 (9)	0.0573 (8)	−0.0016 (6)	0.0387 (7)	0.0034 (7)
O1	0.0801 (8)	0.0751 (8)	0.0744 (8)	−0.0093 (7)	0.0640 (7)	−0.0089 (6)
O2	0.0831 (8)	0.0741 (8)	0.0732 (7)	−0.0146 (6)	0.0630 (7)	−0.0096 (6)

C1—C6	1.392 (2)	C8—H8	0.9300
C1—C2	1.395 (2)	C9—C14	1.402 (2)
C1—N1	1.415 (2)	C9—C10	1.411 (2)
C2—C3	1.389 (2)	C10—O1	1.3445 (18)
C2—C7	1.499 (3)	C10—C11	1.387 (2)
C3—C4	1.376 (3)	C11—C12	1.379 (2)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.370 (3)	C12—O2	1.3604 (18)
C4—H4	0.9300	C12—C13	1.397 (2)
C5—C6	1.378 (3)	C13—C14	1.361 (2)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—H7A	0.9600	C15—O2	1.423 (2)
C7—H7B	0.9600	C15—H15A	0.9600
C7—H7C	0.9600	C15—H15B	0.9600
C8—N1	1.284 (2)	C15—H15C	0.9600
C8—C9	1.439 (2)	O1—H16	0.95 (2)
C6—C1—C2	119.74 (16)	C14—C9—C10	117.70 (15)
C6—C1—N1	123.08 (16)	C14—C9—C8	120.87 (15)
C2—C1—N1	117.18 (15)	C10—C9—C8	121.42 (14)
C3—C2—C1	118.29 (17)	O1—C10—C11	118.22 (15)
C3—C2—C7	120.63 (17)	O1—C10—C9	121.17 (15)
C1—C2—C7	121.08 (15)	C11—C10—C9	120.60 (14)
C4—C3—C2	121.47 (19)	C12—C11—C10	119.71 (15)
C4—C3—H3	119.3	C12—C11—H11	120.1
C2—C3—H3	119.3	C10—C11—H11	120.1
C5—C4—C3	119.85 (18)	O2—C12—C11	124.24 (15)
C5—C4—H4	120.1	O2—C12—C13	115.10 (14)
C3—C4—H4	120.1	C11—C12—C13	120.65 (15)
C4—C5—C6	120.1 (2)	C14—C13—C12	119.43 (15)
C4—C5—H5	120.0	C14—C13—H13	120.3
C6—C5—H5	120.0	C12—C13—H13	120.3
C5—C6—C1	120.39 (19)	C13—C14—C9	121.88 (16)
C5—C6—H6	119.8	C13—C14—H14	119.1
C1—C6—H6	119.8	C9—C14—H14	119.1
C2—C7—H7A	109.5	O2—C15—H15A	109.5
C2—C7—H7B	109.5	O2—C15—H15B	109.5
H7A—C7—H7B	109.5	H15A—C15—H15B	109.5
C2—C7—H7C	109.5	O2—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—C9	122.35 (16)	C8—N1—C1	121.51 (15)
N1—C8—H8	118.8	C10—O1—H16	107.6 (13)
C9—C8—H8	118.8	C12—O2—C15	117.67 (13)
C6—C1—C2—C3	4.6 (2)	C8—C9—C10—C11	177.51 (14)
N1—C1—C2—C3	−175.30 (14)	O1—C10—C11—C12	−179.80 (14)
C6—C1—C2—C7	−175.26 (16)	C9—C10—C11—C12	1.3 (2)
N1—C1—C2—C7	4.9 (2)	C10—C11—C12—O2	−179.71 (14)
C1—C2—C3—C4	−1.1 (3)	C10—C11—C12—C13	−0.1 (2)
C7—C2—C3—C4	178.75 (18)	O2—C12—C13—C14	178.83 (15)
C2—C3—C4—C5	−2.2 (3)	C11—C12—C13—C14	−0.8 (2)
C3—C4—C5—C6	2.0 (3)	C12—C13—C14—C9	0.6 (2)
C4—C5—C6—C1	1.6 (3)	C10—C9—C14—C13	0.6 (2)
C2—C1—C6—C5	−4.9 (2)	C8—C9—C14—C13	−178.44 (15)
N1—C1—C6—C5	174.98 (15)	C9—C8—N1—C1	−177.22 (14)
N1—C8—C9—C14	−178.93 (15)	C6—C1—N1—C8	−25.8 (2)
N1—C8—C9—C10	2.1 (2)	C2—C1—N1—C8	154.04 (15)
C14—C9—C10—O1	179.60 (14)	C11—C12—O2—C15	−1.2 (2)
C8—C9—C10—O1	−1.4 (2)	C13—C12—O2—C15	179.16 (15)
C14—C9—C10—C11	−1.5 (2)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H16···N1	0.95 (2)	1.75 (2)	2.5992 (19)	148.3 (19)
C15—H15B···Cgi	0.96	2.98	3.900 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H16⋯N1	0.95 (2)	1.75 (2)	2.5992 (19)	148.3 (19)
C15—H15B⋯Cgi	0.96	2.98	3.900 (2)	160

Symmetry code: (i) .