2-(m-Tolyl-imino-meth-yl)phenol.

The title compound, C(14)H(13)NO, is non-planar with a dihedral angle of 47.00 (6)° between the planes of the two aromatic rings. Intra-molecular hydrogen bonding is observed between the O-H group and the N atom, resulting in a phenol-imine tautomeric form.

Related literature

For related structures, see: Elmali et al. (1998 ▶); Cheng et al. (2005 ▶); Arod et al. (2005 ▶); Bingöl et al. (2007 ▶); Zhang et al. (2007 ▶). For macromolecules containing Schiff base–metal complexes see: Leung et al. (2007 ▶). For related structures with non-linear optical properties, magnetic, oxygen transport and catalytic properties: see Karakas et al. (2004 ▶); Miyasaka et al. (2003 ▶); Bailes et al. (1947 ▶); Zhang et al. (1994 ▶). For photo-physical properties such as thermochromism and photochromism, see: Gakias et al. (2005 ▶). For N-Salicylideneaniline, which displays reversible photoreactivity and crystallizes as both non-planar and planar polymorphs, see: Arod et al. (2005 ▶, 2007 ▶)

Experimental

Crystal data

C14H13NO

M = 211.25

Orthorhombic,

a = 7.4946 (4) Å

b = 11.8669 (6) Å

c = 12.2970 (6) Å

V = 1093.67 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.35 × 0.22 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.972, T max = 0.994

11186 measured reflections

1532 independent reflections

1210 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 1.08

1532 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049307/bg2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049307/bg2304Isup2.hkl

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

C14H13NO	F(000) = 448
Mr = 211.25	Dx = 1.283 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1942 reflections
a = 7.4946 (4) Å	θ = 3.2–22.3°
b = 11.8669 (6) Å	µ = 0.08 mm−1
c = 12.2970 (6) Å	T = 100 K
V = 1093.67 (10) Å3	Cuboid, red
Z = 4	0.35 × 0.22 × 0.08 mm

Bruker X8 APEXII 4K Kappa CCD diffractometer	1532 independent reflections
Radiation source: sealed tube	1210 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 512 pixels mm-1	θmax = 28.0°, θmin = 2.4°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −15→12
Tmin = 0.972, Tmax = 0.994	l = −13→16
11186 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0939P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.20 e Å−3
1532 reflections	Δρmin = −0.21 e Å−3
146 parameters

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 60 s/frame. A total of 1032 frames were collected with a frame width of 0.5° covering up to θ = 27.99° with 100.0% completeness accomplized.

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.

	x	y	z	Uiso*/Ueq
C1	0.4954 (3)	0.32440 (17)	0.70887 (17)	0.0219 (5)
H1	0.4568	0.2514	0.6877	0.026*
C231	0.5244 (3)	0.15389 (17)	0.30941 (18)	0.0272 (5)
H2A	0.584	0.1037	0.3612	0.041*
H2B	0.6073	0.1733	0.2507	0.041*
H2C	0.4198	0.1158	0.2789	0.041*
C11	0.5390 (3)	0.34554 (16)	0.82153 (17)	0.0209 (5)
C12	0.6066 (3)	0.45064 (17)	0.85663 (18)	0.0223 (5)
C13	0.6401 (3)	0.46927 (19)	0.96612 (18)	0.0257 (5)
H13	0.6882	0.5393	0.9893	0.031*
C14	0.6037 (3)	0.38626 (18)	1.0414 (2)	0.0281 (5)
H14	0.6248	0.4004	1.1163	0.034*
C15	0.5364 (3)	0.28196 (18)	1.00924 (18)	0.0290 (6)
H15	0.5114	0.2252	1.0616	0.035*
C16	0.5066 (3)	0.26242 (17)	0.90006 (17)	0.0242 (5)
H16	0.4631	0.1909	0.8776	0.029*
C21	0.4611 (3)	0.37863 (16)	0.52673 (17)	0.0207 (5)
C22	0.5118 (3)	0.27911 (17)	0.47524 (17)	0.0214 (5)
H22	0.5779	0.224	0.5142	0.026*
C23	0.4662 (3)	0.25991 (17)	0.36708 (18)	0.0214 (5)
C24	0.3690 (3)	0.34139 (17)	0.31147 (18)	0.0237 (5)
H24	0.3362	0.329	0.2378	0.028*
C25	0.3195 (3)	0.44076 (17)	0.36278 (19)	0.0258 (5)
H25	0.2525	0.4956	0.3241	0.031*
C26	0.3668 (3)	0.46058 (17)	0.46985 (18)	0.0240 (5)
H26	0.3351	0.5295	0.5042	0.029*
N1	0.5078 (2)	0.40260 (13)	0.63674 (14)	0.0213 (4)
O1	0.6371 (2)	0.53517 (12)	0.78487 (12)	0.0274 (4)
H1A	0.6018	0.5156	0.7228	0.041*

	U11	U22	U33	U12	U13	U23
C1	0.0191 (12)	0.0190 (10)	0.0276 (12)	0.0004 (9)	0.0021 (11)	−0.0022 (9)
C231	0.0276 (13)	0.0287 (11)	0.0253 (11)	0.0035 (10)	−0.0034 (11)	−0.0028 (10)
C11	0.0200 (11)	0.0176 (10)	0.0251 (11)	0.0030 (9)	0.0013 (10)	−0.0020 (9)
C12	0.0176 (11)	0.0205 (11)	0.0287 (13)	0.0023 (9)	0.0018 (10)	−0.0013 (10)
C13	0.0202 (12)	0.0232 (10)	0.0338 (13)	−0.0003 (10)	−0.0021 (11)	−0.0064 (10)
C14	0.0272 (13)	0.0303 (12)	0.0267 (12)	0.0029 (11)	−0.0032 (11)	−0.0054 (10)
C15	0.0341 (14)	0.0269 (12)	0.0260 (12)	0.0025 (11)	0.0013 (11)	0.0023 (10)
C16	0.0276 (13)	0.0208 (10)	0.0242 (12)	0.0002 (10)	0.0021 (10)	−0.0015 (8)
C21	0.0174 (11)	0.0218 (10)	0.0227 (12)	−0.0051 (9)	0.0036 (10)	0.0035 (9)
C22	0.0191 (11)	0.0213 (10)	0.0238 (12)	0.0013 (9)	0.0002 (10)	0.0031 (9)
C23	0.0161 (11)	0.0235 (10)	0.0247 (11)	−0.0032 (9)	0.0010 (10)	0.0018 (9)
C24	0.0182 (11)	0.0325 (12)	0.0203 (11)	−0.0023 (10)	0.0003 (10)	0.0060 (10)
C25	0.0222 (12)	0.0245 (12)	0.0305 (13)	0.0001 (9)	0.0006 (11)	0.0100 (10)
C26	0.0202 (12)	0.0187 (10)	0.0331 (13)	0.0002 (10)	0.0029 (11)	0.0032 (10)
N1	0.0208 (10)	0.0213 (9)	0.0219 (9)	0.0016 (8)	0.0019 (9)	0.0001 (7)
O1	0.0315 (9)	0.0207 (7)	0.0300 (8)	−0.0036 (7)	−0.0004 (8)	−0.0007 (7)

C1—N1	1.287 (3)	C15—C16	1.381 (3)
C1—C11	1.445 (3)	C15—H15	0.95
C1—H1	0.95	C16—H16	0.95
C231—C23	1.509 (3)	C21—C26	1.391 (3)
C231—H2A	0.98	C21—C22	1.393 (3)
C231—H2B	0.98	C21—N1	1.426 (3)
C231—H2C	0.98	C22—C23	1.392 (3)
C11—C16	1.402 (3)	C22—H22	0.95
C11—C12	1.414 (3)	C23—C24	1.390 (3)
C12—O1	1.355 (2)	C24—C25	1.388 (3)
C12—C13	1.387 (3)	C24—H24	0.95
C13—C14	1.379 (3)	C25—C26	1.384 (3)
C13—H13	0.95	C25—H25	0.95
C14—C15	1.394 (3)	C26—H26	0.95
C14—H14	0.95	O1—H1A	0.84
N1—C1—C11	121.27 (18)	C15—C16—C11	121.6 (2)
N1—C1—H1	119.4	C15—C16—H16	119.2
C11—C1—H1	119.4	C11—C16—H16	119.2
C23—C231—H2A	109.5	C26—C21—C22	120.19 (19)
C23—C231—H2B	109.5	C26—C21—N1	117.55 (18)
H2A—C231—H2B	109.5	C22—C21—N1	122.22 (18)
C23—C231—H2C	109.5	C23—C22—C21	120.40 (19)
H2A—C231—H2C	109.5	C23—C22—H22	119.8
H2B—C231—H2C	109.5	C21—C22—H22	119.8
C16—C11—C12	118.21 (19)	C24—C23—C22	119.0 (2)
C16—C11—C1	119.93 (18)	C24—C23—C231	120.03 (19)
C12—C11—C1	121.80 (18)	C22—C23—C231	121.0 (2)
O1—C12—C13	118.91 (19)	C25—C24—C23	120.5 (2)
O1—C12—C11	120.96 (19)	C25—C24—H24	119.8
C13—C12—C11	120.1 (2)	C23—C24—H24	119.8
C14—C13—C12	120.1 (2)	C26—C25—C24	120.6 (2)
C14—C13—H13	119.9	C26—C25—H25	119.7
C12—C13—H13	119.9	C24—C25—H25	119.7
C13—C14—C15	121.0 (2)	C25—C26—C21	119.3 (2)
C13—C14—H14	119.5	C25—C26—H26	120.3
C15—C14—H14	119.5	C21—C26—H26	120.3
C16—C15—C14	118.9 (2)	C1—N1—C21	119.49 (16)
C16—C15—H15	120.5	C12—O1—H1A	109.5
C14—C15—H15	120.5
N1—C1—C11—C16	173.3 (2)	C26—C21—C22—C23	−1.1 (3)
N1—C1—C11—C12	−3.6 (3)	N1—C21—C22—C23	−178.81 (19)
C16—C11—C12—O1	−178.59 (19)	C21—C22—C23—C24	−0.2 (3)
C1—C11—C12—O1	−1.6 (3)	C21—C22—C23—C231	178.35 (19)
C16—C11—C12—C13	0.4 (3)	C22—C23—C24—C25	0.5 (3)
C1—C11—C12—C13	177.4 (2)	C231—C23—C24—C25	−178.0 (2)
O1—C12—C13—C14	177.47 (19)	C23—C24—C25—C26	0.3 (3)
C11—C12—C13—C14	−1.5 (3)	C24—C25—C26—C21	−1.5 (3)
C12—C13—C14—C15	1.3 (3)	C22—C21—C26—C25	1.9 (3)
C13—C14—C15—C16	0.1 (4)	N1—C21—C26—C25	179.75 (19)
C14—C15—C16—C11	−1.3 (4)	C11—C1—N1—C21	−179.12 (19)
C12—C11—C16—C15	1.0 (3)	C26—C21—N1—C1	139.4 (2)
C1—C11—C16—C15	−176.0 (2)	C22—C21—N1—C1	−42.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84	1.85	2.595 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.84	1.85	2.595 (2)	147