4-[(E)-(4-Methyl-phen-yl)imino-meth-yl]phenol.

In the title compound, C(14)H(13)NO, the two rings show significant deviation from coplanarity, with a dihedral angle between the two planes of 49.40 (5)°. The hy-droxy group is involved in an inter-molecular O-H⋯N hydrogen bond, forming an extended one-dimensional zigzag chain along (001).

Related literature

For the applications of Schiff bases, see: Qian & Cui (2009 ▶). For related structures, see: Burgess et al. (1999 ▶); Kaitner & Pavlovic (1995 ▶); Li (2010 ▶); Li et al. (2008 ▶); Yeap et al. (1993 ▶); Zhang (2010 ▶). For bond geometry, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H13NO

M = 211.25

Orthorhombic,

a = 21.618 (1) Å

b = 11.0561 (6) Å

c = 9.3318 (5) Å

V = 2230.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.977, T max = 0.984

11344 measured reflections

1961 independent reflections

1559 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.08

1961 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007635/zs2179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007635/zs2179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007635/zs2179Isup3.cml

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

C14H13NO	F(000) = 896
Mr = 211.25	Dx = 1.258 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2333 reflections
a = 21.618 (1) Å	θ = 2.5–24.3°
b = 11.0561 (6) Å	µ = 0.08 mm−1
c = 9.3318 (5) Å	T = 296 K
V = 2230.4 (2) Å3	Needle, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	1961 independent reflections
Radiation source: fine-focus sealed tube	1559 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −25→22
Tmin = 0.977, Tmax = 0.984	k = −13→13
11344 measured reflections	l = −9→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.5906P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1961 reflections	Δρmax = 0.19 e Å−3
148 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (10)

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	0.98404 (9)	−0.3138 (2)	0.5166 (2)	0.0696 (6)
H1A	1.0178	−0.2713	0.5605	0.104*
H1B	0.9999	−0.3738	0.4519	0.104*
H1C	0.9597	−0.3525	0.5894	0.104*
C2	0.94434 (7)	−0.22573 (15)	0.43514 (19)	0.0463 (4)
C3	0.93867 (8)	−0.10700 (16)	0.47974 (19)	0.0480 (4)
H3	0.9599	−0.0814	0.5610	0.058*
C4	0.90213 (7)	−0.02566 (14)	0.40601 (18)	0.0424 (4)
H4	0.9001	0.0544	0.4363	0.051*
C5	0.86863 (7)	−0.06207 (13)	0.28760 (16)	0.0344 (4)
C6	0.87510 (8)	−0.18013 (14)	0.23975 (18)	0.0425 (4)
H6	0.8543	−0.2055	0.1578	0.051*
C7	0.91231 (8)	−0.25992 (15)	0.31352 (19)	0.0484 (5)
H7	0.9160	−0.3390	0.2805	0.058*
C8	0.78057 (7)	−0.01218 (13)	0.15734 (16)	0.0364 (4)
H8	0.7683	−0.0915	0.1744	0.044*
C9	0.74169 (7)	0.06129 (13)	0.06518 (16)	0.0343 (4)
C10	0.76120 (7)	0.17174 (13)	0.00844 (16)	0.0348 (4)
H10	0.7993	0.2033	0.0359	0.042*
C11	0.72512 (7)	0.23468 (12)	−0.08724 (16)	0.0350 (4)
H11	0.7389	0.3083	−0.1234	0.042*
C12	0.66836 (7)	0.18910 (13)	−0.13011 (16)	0.0344 (4)
C13	0.64808 (7)	0.07966 (13)	−0.07395 (18)	0.0407 (4)
H13	0.6099	0.0486	−0.1011	0.049*
C14	0.68428 (7)	0.01724 (13)	0.02146 (18)	0.0402 (4)
H14	0.6702	−0.0561	0.0578	0.048*
N1	0.83053 (6)	0.02412 (11)	0.21682 (13)	0.0350 (3)
O1	0.63156 (5)	0.24423 (10)	−0.22698 (13)	0.0457 (3)
H1	0.6475	0.3149	−0.2500	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.0601 (12)	0.0750 (14)	0.0738 (14)	0.0191 (11)	−0.0089 (11)	0.0190 (11)
C2	0.0391 (9)	0.0503 (10)	0.0494 (10)	0.0064 (7)	0.0030 (8)	0.0115 (8)
C3	0.0432 (9)	0.0570 (11)	0.0438 (10)	−0.0041 (8)	−0.0069 (8)	0.0037 (8)
C4	0.0452 (9)	0.0386 (9)	0.0434 (9)	−0.0012 (7)	0.0005 (8)	−0.0019 (7)
C5	0.0370 (8)	0.0334 (8)	0.0330 (8)	0.0014 (6)	0.0036 (7)	0.0037 (6)
C6	0.0498 (9)	0.0379 (9)	0.0398 (9)	0.0047 (7)	−0.0027 (7)	−0.0021 (7)
C7	0.0541 (10)	0.0376 (9)	0.0535 (11)	0.0108 (8)	0.0018 (9)	0.0014 (8)
C8	0.0428 (8)	0.0282 (8)	0.0382 (9)	0.0015 (6)	0.0069 (7)	0.0025 (6)
C9	0.0389 (8)	0.0289 (7)	0.0350 (8)	0.0042 (6)	0.0044 (7)	−0.0007 (6)
C10	0.0367 (8)	0.0317 (8)	0.0360 (9)	−0.0007 (6)	0.0015 (7)	−0.0011 (6)
C11	0.0424 (8)	0.0260 (7)	0.0365 (9)	−0.0006 (6)	0.0034 (7)	0.0015 (6)
C12	0.0387 (8)	0.0301 (8)	0.0345 (9)	0.0066 (6)	0.0013 (7)	−0.0032 (6)
C13	0.0361 (8)	0.0322 (8)	0.0536 (11)	−0.0024 (7)	−0.0016 (8)	0.0000 (7)
C14	0.0424 (9)	0.0278 (8)	0.0503 (10)	−0.0011 (6)	0.0041 (8)	0.0045 (7)
N1	0.0403 (7)	0.0316 (7)	0.0332 (7)	0.0040 (5)	0.0017 (6)	0.0007 (5)
O1	0.0480 (7)	0.0368 (6)	0.0522 (7)	−0.0011 (5)	−0.0115 (6)	0.0080 (5)

C1—C2	1.504 (2)	C8—N1	1.279 (2)
C1—H1A	0.9600	C8—C9	1.451 (2)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C14	1.394 (2)
C2—C7	1.382 (2)	C9—C10	1.396 (2)
C2—C3	1.383 (2)	C10—C11	1.375 (2)
C3—C4	1.381 (2)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.386 (2)
C4—C5	1.381 (2)	C11—H11	0.9300
C4—H4	0.9300	C12—O1	1.3496 (18)
C5—C6	1.387 (2)	C12—C13	1.390 (2)
C5—N1	1.4221 (19)	C13—C14	1.372 (2)
C6—C7	1.378 (2)	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—H7	0.9300	O1—H1	0.8811
C2—C1—H1A	109.5	N1—C8—C9	124.80 (14)
C2—C1—H1B	109.5	N1—C8—H8	117.6
H1A—C1—H1B	109.5	C9—C8—H8	117.6
C2—C1—H1C	109.5	C14—C9—C10	117.61 (14)
H1A—C1—H1C	109.5	C14—C9—C8	119.57 (13)
H1B—C1—H1C	109.5	C10—C9—C8	122.63 (13)
C7—C2—C3	117.54 (15)	C11—C10—C9	121.17 (13)
C7—C2—C1	121.59 (17)	C11—C10—H10	119.4
C3—C2—C1	120.87 (17)	C9—C10—H10	119.4
C4—C3—C2	121.28 (16)	C10—C11—C12	120.39 (14)
C4—C3—H3	119.4	C10—C11—H11	119.8
C2—C3—H3	119.4	C12—C11—H11	119.8
C3—C4—C5	120.58 (15)	O1—C12—C11	123.45 (14)
C3—C4—H4	119.7	O1—C12—C13	117.38 (13)
C5—C4—H4	119.7	C11—C12—C13	119.16 (14)
C4—C5—C6	118.63 (14)	C14—C13—C12	120.19 (14)
C4—C5—N1	118.68 (13)	C14—C13—H13	119.9
C6—C5—N1	122.66 (14)	C12—C13—H13	119.9
C7—C6—C5	120.04 (16)	C13—C14—C9	121.47 (14)
C7—C6—H6	120.0	C13—C14—H14	119.3
C5—C6—H6	120.0	C9—C14—H14	119.3
C6—C7—C2	121.84 (16)	C8—N1—C5	118.71 (13)
C6—C7—H7	119.1	C12—O1—H1	109.5
C2—C7—H7	119.1
C7—C2—C3—C4	0.3 (3)	C8—C9—C10—C11	174.95 (14)
C1—C2—C3—C4	−179.72 (16)	C9—C10—C11—C12	−0.3 (2)
C2—C3—C4—C5	2.0 (2)	C10—C11—C12—O1	−177.82 (13)
C3—C4—C5—C6	−3.5 (2)	C10—C11—C12—C13	0.7 (2)
C3—C4—C5—N1	178.62 (14)	O1—C12—C13—C14	177.90 (14)
C4—C5—C6—C7	2.7 (2)	C11—C12—C13—C14	−0.7 (2)
N1—C5—C6—C7	−179.48 (14)	C12—C13—C14—C9	0.3 (2)
C5—C6—C7—C2	−0.4 (3)	C10—C9—C14—C13	0.1 (2)
C3—C2—C7—C6	−1.1 (3)	C8—C9—C14—C13	−175.12 (14)
C1—C2—C7—C6	178.95 (17)	C9—C8—N1—C5	−171.11 (13)
N1—C8—C9—C14	−171.69 (15)	C4—C5—N1—C8	−147.79 (14)
N1—C8—C9—C10	13.4 (2)	C6—C5—N1—C8	34.4 (2)
C14—C9—C10—C11	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.88	1.87	2.7397 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.88	1.87	2.7397 (17)	170

Symmetry code: (i) .