2-((E)-{[4-(Hy-droxy-meth-yl)phen-yl]imino}-meth-yl)phenol.

The title compound, C(14)H(13)NO(2), adopts the enol-imine tautomeric form, with an intra-molecular O-H⋯N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the aromatic rings is 7.85 (7)°. The crystal structure is stabilized by O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds, forming a two-dimensional array that stacks along the a axis. In addition, a C-H⋯π inter-action contributes to the stabilization of the crystal packing.

Related literature

For background to Schiff base compounds, see: Elena et al. (2000 ▶); Mohamed et al. (2006 ▶); Rajavel et al. (2008 ▶); Uğraş et al. (2006 ▶); Wadher et al. (2009 ▶). For similar structures, see: Deveci et al. (2008 ▶); Karadayı et al. (2003 ▶); Koşar et al. (2010 ▶); Ünver et al. (2002 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13NO2

M = 227.25

Monoclinic,

a = 19.8172 (14) Å

b = 4.7217 (1) Å

c = 12.3106 (2) Å

β = 104.005 (7)°

V = 1117.67 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.73 mm−1

T = 150 K

0.25 × 0.20 × 0.08 mm

Data collection

Rigaku RAPID II diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ▶) T min = 0.838, T max = 0.944

10711 measured reflections

1958 independent reflections

1641 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.14

1958 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019368/tk5090sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019368/tk5090Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019368/tk5090Isup3.cml

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

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 11657 reflections
a = 19.8172 (14) Å	θ = 2–66°
b = 4.7217 (1) Å	µ = 0.73 mm−1
c = 12.3106 (2) Å	T = 150 K
β = 104.005 (7)°	Plate, yellow
V = 1117.67 (9) Å3	0.25 × 0.20 × 0.08 mm
Z = 4

Rigaku RAPID II diffractometer	1641 reflections with I > 2σ(I)
Confocal optics monochromator	Rint = 0.030
ω scans	θmax = 66.6°, θmin = 4.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	h = −23→23
Tmin = 0.838, Tmax = 0.944	k = −5→5
10711 measured reflections	l = −11→14
1958 independent reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.170P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1958 reflections	Δρmax = 0.23 e Å−3
163 parameters	Δρmin = −0.18 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: 0.0077 (8)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.46733 (5)	0.1618 (2)	0.25819 (8)	0.0330 (3)
O2	0.19567 (6)	1.2380 (2)	0.56950 (8)	0.0408 (4)
N1	0.24780 (5)	0.9636 (2)	0.42590 (9)	0.0258 (3)
C1	0.44786 (7)	0.1429 (3)	0.36158 (11)	0.0285 (4)
C2	0.39457 (6)	0.3581 (3)	0.37420 (11)	0.0252 (4)
C3	0.34633 (7)	0.4685 (3)	0.28219 (11)	0.0278 (4)
C4	0.29742 (7)	0.6676 (3)	0.29556 (11)	0.0279 (4)
C5	0.29508 (6)	0.7592 (3)	0.40265 (11)	0.0245 (4)
C6	0.34194 (7)	0.6431 (3)	0.49448 (11)	0.0279 (4)
C7	0.39100 (7)	0.4468 (3)	0.48021 (11)	0.0287 (4)
C8	0.20820 (6)	1.1083 (3)	0.34759 (11)	0.0257 (4)
C9	0.15921 (6)	1.3145 (3)	0.37087 (11)	0.0259 (4)
C10	0.11604 (6)	1.4634 (3)	0.28242 (11)	0.0296 (4)
C11	0.06849 (7)	1.6600 (3)	0.30125 (13)	0.0340 (4)
C12	0.06377 (7)	1.7098 (3)	0.41032 (13)	0.0371 (5)
C13	0.10585 (7)	1.5687 (3)	0.49924 (12)	0.0375 (5)
C14	0.15422 (7)	1.3713 (3)	0.48079 (11)	0.0299 (4)
H1	0.4926 (14)	0.330 (5)	0.259 (2)	0.099 (8)*
H1A	0.48990	0.16730	0.42350	0.0340*
H1B	0.42910	−0.04890	0.36840	0.0340*
H2	0.2230 (10)	1.115 (5)	0.5393 (17)	0.071 (6)*
H3	0.34690	0.40630	0.20900	0.0330*
H4	0.26540	0.74190	0.23170	0.0330*
H6	0.34030	0.69910	0.56790	0.0340*
H7	0.42280	0.37140	0.54410	0.0340*
H8	0.21100	1.07970	0.27240	0.0310*
H10	0.11950	1.42860	0.20800	0.0360*
H11	0.03950	1.75950	0.24050	0.0410*
H12	0.03090	1.84360	0.42380	0.0440*
H13	0.10190	1.60590	0.57330	0.0450*

	U11	U22	U33	U12	U13	U23
O1	0.0382 (6)	0.0280 (5)	0.0374 (6)	0.0013 (4)	0.0182 (4)	0.0000 (4)
O2	0.0522 (7)	0.0451 (7)	0.0276 (6)	0.0127 (5)	0.0147 (5)	0.0002 (5)
N1	0.0276 (6)	0.0231 (6)	0.0285 (6)	−0.0012 (4)	0.0104 (5)	−0.0012 (4)
C1	0.0317 (7)	0.0239 (7)	0.0317 (7)	−0.0005 (5)	0.0113 (6)	0.0021 (5)
C2	0.0270 (7)	0.0198 (6)	0.0305 (7)	−0.0041 (5)	0.0102 (6)	0.0012 (5)
C3	0.0331 (7)	0.0266 (7)	0.0255 (7)	−0.0008 (5)	0.0105 (6)	−0.0023 (5)
C4	0.0301 (7)	0.0283 (7)	0.0248 (7)	0.0021 (5)	0.0059 (6)	0.0010 (5)
C5	0.0272 (7)	0.0209 (6)	0.0275 (7)	−0.0034 (5)	0.0110 (6)	−0.0013 (5)
C6	0.0354 (7)	0.0264 (7)	0.0236 (7)	−0.0019 (5)	0.0102 (6)	−0.0013 (5)
C7	0.0319 (7)	0.0256 (7)	0.0277 (7)	−0.0006 (6)	0.0054 (6)	0.0025 (5)
C8	0.0289 (7)	0.0235 (7)	0.0263 (7)	−0.0042 (5)	0.0101 (6)	−0.0025 (5)
C9	0.0265 (7)	0.0212 (6)	0.0323 (7)	−0.0041 (5)	0.0116 (6)	−0.0025 (5)
C10	0.0303 (7)	0.0279 (7)	0.0315 (7)	−0.0024 (5)	0.0090 (6)	−0.0015 (6)
C11	0.0291 (7)	0.0275 (7)	0.0451 (9)	0.0001 (6)	0.0085 (6)	0.0008 (6)
C12	0.0326 (8)	0.0302 (8)	0.0528 (10)	0.0022 (6)	0.0189 (7)	−0.0049 (7)
C13	0.0445 (8)	0.0356 (8)	0.0383 (8)	0.0005 (7)	0.0213 (7)	−0.0063 (7)
C14	0.0329 (7)	0.0283 (7)	0.0311 (7)	−0.0018 (5)	0.0130 (6)	−0.0010 (6)

O1—C1	1.4193 (17)	C10—C11	1.382 (2)
O2—C14	1.3525 (17)	C11—C12	1.388 (2)
O1—H1	0.94 (3)	C12—C13	1.377 (2)
O2—H2	0.93 (2)	C13—C14	1.395 (2)
N1—C5	1.4216 (17)	C1—H1A	0.9900
N1—C8	1.2829 (17)	C1—H1B	0.9900
C1—C2	1.5004 (19)	C3—H3	0.9500
C2—C7	1.3886 (19)	C4—H4	0.9500
C2—C3	1.3945 (19)	C6—H6	0.9500
C3—C4	1.388 (2)	C7—H7	0.9500
C4—C5	1.3989 (19)	C8—H8	0.9500
C5—C6	1.3902 (19)	C10—H10	0.9500
C6—C7	1.385 (2)	C11—H11	0.9500
C8—C9	1.4516 (19)	C12—H12	0.9500
C9—C14	1.4063 (19)	C13—H13	0.9500
C9—C10	1.4003 (19)
C1—O1—H1	107.7 (15)	O2—C14—C13	119.12 (12)
C14—O2—H2	105.4 (13)	O1—C1—H1A	109.00
C5—N1—C8	121.56 (11)	O1—C1—H1B	109.00
O1—C1—C2	113.65 (11)	C2—C1—H1A	109.00
C1—C2—C7	119.92 (12)	C2—C1—H1B	109.00
C3—C2—C7	118.02 (12)	H1A—C1—H1B	108.00
C1—C2—C3	122.03 (12)	C2—C3—H3	119.00
C2—C3—C4	121.19 (12)	C4—C3—H3	119.00
C3—C4—C5	120.29 (12)	C3—C4—H4	120.00
N1—C5—C4	124.99 (12)	C5—C4—H4	120.00
C4—C5—C6	118.46 (12)	C5—C6—H6	120.00
N1—C5—C6	116.56 (12)	C7—C6—H6	120.00
C5—C6—C7	120.80 (12)	C2—C7—H7	119.00
C2—C7—C6	121.20 (12)	C6—C7—H7	119.00
N1—C8—C9	121.70 (12)	N1—C8—H8	119.00
C10—C9—C14	118.72 (12)	C9—C8—H8	119.00
C8—C9—C10	119.68 (12)	C9—C10—H10	119.00
C8—C9—C14	121.60 (12)	C11—C10—H10	119.00
C9—C10—C11	121.33 (13)	C10—C11—H11	120.00
C10—C11—C12	118.97 (13)	C12—C11—H11	121.00
C11—C12—C13	121.15 (13)	C11—C12—H12	119.00
C12—C13—C14	120.12 (13)	C13—C12—H12	119.00
C9—C14—C13	119.70 (13)	C12—C13—H13	120.00
O2—C14—C9	121.19 (12)	C14—C13—H13	120.00
C5—N1—C8—C9	179.17 (12)	C5—C6—C7—C2	−0.6 (2)
C8—N1—C5—C4	−8.8 (2)	N1—C8—C9—C10	−178.71 (12)
C8—N1—C5—C6	171.49 (12)	N1—C8—C9—C14	1.8 (2)
O1—C1—C2—C7	−153.49 (12)	C8—C9—C10—C11	179.61 (13)
O1—C1—C2—C3	28.42 (18)	C14—C9—C10—C11	−0.9 (2)
C3—C2—C7—C6	−1.2 (2)	C8—C9—C14—O2	0.9 (2)
C1—C2—C3—C4	−179.98 (14)	C8—C9—C14—C13	−179.25 (13)
C1—C2—C7—C6	−179.38 (13)	C10—C9—C14—O2	−178.60 (12)
C7—C2—C3—C4	1.9 (2)	C10—C9—C14—C13	1.3 (2)
C2—C3—C4—C5	−0.8 (2)	C9—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	−1.0 (2)	C10—C11—C12—C13	0.5 (2)
C3—C4—C5—N1	179.32 (13)	C11—C12—C13—C14	−0.1 (2)
C4—C5—C6—C7	1.7 (2)	C12—C13—C14—O2	179.11 (13)
N1—C5—C6—C7	−178.61 (12)	C12—C13—C14—C9	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2—H2···N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7—H7···O1ii	0.95	2.57	3.4288 (16)	150
C8—H8···O2iii	0.95	2.59	3.4492 (16)	151
C1—H1B···Cg1iv	0.99	2.56	3.5050 (15)	160

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2—H2⋯N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7—H7⋯O1ii	0.95	2.57	3.4288 (16)	150
C8—H8⋯O2iii	0.95	2.59	3.4492 (16)	151
C1—H1B⋯Cg1iv	0.99	2.56	3.5050 (15)	160

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