4-Meth-oxy-2-[(E)-(phenyl-imino)meth-yl]phenol.

In the mol-ecule of the title compound, C(14)H(13)NO(2), the two aromatic rings are oriented at a dihedral angle of 0.78 (20)°; with the exception of two methyl H atoms the mol-ecule is essentially planar. The intra-molecular O-H⋯N hydrogen bond results in the formation of a non-planar, six-membered ring, which adopts a flattened-boat conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules to form parallel networks. There is a C-H⋯π contact between the methyl group and the benzene ring. A π-π contact between the benzene and phenyl rings [centroid-centroid distance = 4.681 (5) Å] is also observed.

Related literature

For general background, see: Hökelek et al. (2004 ▶); Uçan & Mercimek (2005 ▶); Uçan et al. (2005 ▶); Garg & Kumar (2003 ▶); Mokles & Elzaher (2001 ▶); Amirnasr et al. (2002 ▶); Bella et al. (2004 ▶); Chandra & Kumar (2005 ▶); Ray et al. (2003 ▶); Yang et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H13NO2

M = 227.26

Monoclinic,

a = 20.935 (2) Å

b = 4.7151 (10) Å

c = 12.275 (3) Å

β = 106.623 (14)°

V = 1161.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.40 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.971, T max = 0.990

1653 measured reflections

1560 independent reflections

521 reflections with I > 2σ(I)

R int = 0.048

θmax = 23.1°

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.207

S = 0.92

1560 reflections

163 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026883/wn2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026883/wn2275Isup2.hkl

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

C14H13NO2	F000 = 480
Mr = 227.26	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 20.935 (2) Å	θ = 5.2–17.4º
b = 4.7151 (10) Å	µ = 0.09 mm−1
c = 12.276 (3) Å	T = 294 (2) K
β = 106.623 (14)º	Rod-shaped, orange
V = 1161.1 (4) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.048
Radiation source: fine-focus sealed tube	θmax = 23.1º
Monochromator: graphite	θmin = 3.3º
T = 294(2) K	h = −22→21
non–profiled ω scans	k = 0→5
Absorption correction: ψ scan(North et al., 1968)	l = 0→13
Tmin = 0.971, Tmax = 0.990	3 standard reflections
1653 measured reflections	every 120 min
1560 independent reflections	intensity decay: 1%
521 reflections with I > 2σ(I)

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.207	w = 1/[σ2(Fo2) + (0.0803P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
1560 reflections	Δρmax = 0.20 e Å−3
163 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	0.7505 (3)	0.7726 (12)	1.0014 (4)	0.0656 (17)
H1	0.725 (3)	0.879 (11)	0.951 (4)	0.05 (3)*
O2	0.9196 (2)	0.2785 (11)	0.7864 (4)	0.0649 (16)
N1	0.7019 (3)	1.0588 (12)	0.8146 (5)	0.0452 (17)
C1	0.6566 (3)	1.2627 (15)	0.7496 (6)	0.043 (2)
C2	0.6507 (4)	1.3416 (17)	0.6390 (7)	0.065 (3)
H2	0.6792	1.2622	0.6015	0.078*
C3	0.6041 (4)	1.5335 (18)	0.5837 (7)	0.079 (3)
H3	0.6003	1.5789	0.5083	0.095*
C4	0.5626 (4)	1.6608 (17)	0.6377 (8)	0.066 (3)
H4	0.5314	1.7939	0.5997	0.079*
C5	0.5677 (4)	1.5897 (17)	0.7486 (8)	0.064 (2)
H5	0.5399	1.6744	0.7860	0.076*
C6	0.6144 (4)	1.3919 (15)	0.8039 (6)	0.055 (2)
H6	0.6177	1.3443	0.8789	0.066*
C7	0.7415 (4)	0.9240 (16)	0.7710 (7)	0.043 (2)
H7	0.742 (2)	0.943 (11)	0.688 (5)	0.039 (18)*
C8	0.7886 (3)	0.7208 (15)	0.8350 (6)	0.0397 (19)
C9	0.8325 (3)	0.5868 (15)	0.7860 (6)	0.049 (2)
H9	0.8306	0.6280	0.7111	0.059*
C10	0.8787 (4)	0.3956 (16)	0.8450 (7)	0.048 (2)
C11	0.8823 (4)	0.3314 (16)	0.9555 (7)	0.057 (2)
H11	0.9139	0.2028	0.9962	0.068*
C12	0.8383 (4)	0.4607 (17)	1.0059 (6)	0.056 (2)
H12	0.8402	0.4159	1.0805	0.067*
C13	0.7918 (4)	0.6544 (17)	0.9470 (7)	0.049 (2)
C14	0.9735 (3)	0.1055 (17)	0.8484 (7)	0.077 (3)
H14A	0.9978	0.0375	0.7982	0.115*
H14B	0.9563	−0.0527	0.8805	0.115*
H14C	1.0026	0.2150	0.9082	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.085 (4)	0.070 (4)	0.045 (4)	0.028 (4)	0.023 (3)	0.010 (4)
O2	0.062 (4)	0.072 (4)	0.064 (4)	0.026 (3)	0.025 (3)	0.010 (3)
N1	0.058 (4)	0.033 (4)	0.043 (4)	−0.003 (3)	0.012 (4)	0.001 (3)
C1	0.047 (5)	0.032 (5)	0.046 (5)	−0.010 (4)	0.005 (4)	0.000 (5)
C2	0.067 (6)	0.069 (7)	0.055 (6)	0.028 (5)	0.011 (5)	0.004 (5)
C3	0.089 (7)	0.074 (7)	0.063 (6)	0.034 (6)	0.005 (6)	0.015 (6)
C4	0.071 (7)	0.038 (6)	0.072 (7)	0.007 (5)	−0.008 (5)	0.003 (5)
C5	0.052 (6)	0.048 (6)	0.092 (8)	0.001 (5)	0.023 (5)	−0.006 (5)
C6	0.062 (5)	0.043 (5)	0.068 (6)	0.006 (5)	0.031 (5)	0.006 (5)
C7	0.046 (5)	0.041 (5)	0.040 (5)	−0.003 (4)	0.008 (4)	−0.002 (5)
C8	0.046 (5)	0.033 (5)	0.036 (5)	0.003 (4)	0.007 (4)	0.003 (4)
C9	0.059 (5)	0.043 (5)	0.040 (5)	−0.002 (5)	0.008 (4)	−0.001 (4)
C10	0.052 (5)	0.037 (5)	0.053 (6)	0.001 (4)	0.014 (4)	0.010 (5)
C11	0.058 (5)	0.052 (6)	0.058 (6)	0.013 (5)	0.014 (5)	0.022 (5)
C12	0.068 (6)	0.062 (6)	0.034 (5)	0.000 (5)	0.010 (4)	0.006 (5)
C13	0.054 (5)	0.048 (6)	0.046 (5)	−0.002 (4)	0.014 (4)	−0.005 (5)
C14	0.064 (6)	0.074 (6)	0.093 (7)	0.034 (5)	0.025 (5)	0.011 (6)

O1—C13	1.355 (8)	C6—H6	0.9300
O1—H1	0.86 (5)	C7—C8	1.437 (9)
O2—C10	1.381 (8)	C7—H7	1.03 (5)
O2—C14	1.423 (7)	C8—C13	1.393 (8)
N1—C1	1.424 (8)	C9—C8	1.387 (9)
N1—C7	1.277 (8)	C9—C10	1.368 (8)
C1—C2	1.379 (9)	C9—H9	0.9300
C2—C3	1.362 (9)	C11—C10	1.370 (8)
C2—H2	0.9300	C11—C12	1.390 (9)
C3—H3	0.9300	C11—H11	0.9300
C4—C3	1.372 (10)	C12—C13	1.378 (9)
C4—C5	1.376 (9)	C12—H12	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C1	1.390 (9)	C14—H14C	0.9600
C6—C5	1.381 (9)
C13—O1—H1	104 (5)	C9—C8—C13	118.3 (7)
C10—O2—C14	117.7 (6)	C9—C8—C7	120.2 (7)
C7—N1—C1	120.6 (7)	C13—C8—C7	121.5 (7)
C2—C1—C6	117.7 (7)	C10—C9—C8	121.8 (7)
C2—C1—N1	126.2 (7)	C10—C9—H9	119.1
C6—C1—N1	116.1 (7)	C8—C9—H9	119.1
C3—C2—C1	121.3 (8)	C9—C10—C11	120.1 (8)
C3—C2—H2	119.3	C9—C10—O2	115.9 (7)
C1—C2—H2	119.3	C11—C10—O2	124.0 (7)
C2—C3—C4	120.8 (9)	C10—C11—C12	119.2 (7)
C2—C3—H3	119.6	C10—C11—H11	120.4
C4—C3—H3	119.6	C12—C11—H11	120.4
C3—C4—C5	119.4 (9)	C13—C12—C11	121.0 (8)
C3—C4—H4	120.3	C13—C12—H12	119.5
C5—C4—H4	120.3	C11—C12—H12	119.5
C4—C5—C6	119.7 (8)	O1—C13—C12	117.9 (8)
C4—C5—H5	120.2	O1—C13—C8	122.5 (7)
C6—C5—H5	120.2	C12—C13—C8	119.6 (8)
C5—C6—C1	121.2 (8)	O2—C14—H14A	109.5
C5—C6—H6	119.4	O2—C14—H14B	109.5
C1—C6—H6	119.4	H14A—C14—H14B	109.5
N1—C7—C8	121.9 (8)	O2—C14—H14C	109.5
N1—C7—H7	125 (3)	H14A—C14—H14C	109.5
C8—C7—H7	113 (3)	H14B—C14—H14C	109.5
C7—N1—C1—C2	−1.5 (10)	N1—C7—C8—C13	2.1 (10)
C7—N1—C1—C6	178.3 (7)	C9—C8—C13—O1	−179.3 (7)
C1—N1—C7—C8	178.8 (6)	C7—C8—C13—O1	1.1 (11)
C14—O2—C10—C9	172.5 (6)	C9—C8—C13—C12	0.4 (10)
C14—O2—C10—C11	−7.3 (10)	C7—C8—C13—C12	−179.2 (7)
N1—C1—C2—C3	178.0 (7)	C10—C9—C8—C13	−0.6 (10)
C6—C1—C2—C3	−1.8 (11)	C10—C9—C8—C7	179.0 (6)
C1—C2—C3—C4	1.9 (12)	C8—C9—C10—C11	0.1 (11)
C5—C4—C3—C2	−1.0 (12)	C8—C9—C10—O2	−179.7 (6)
C3—C4—C5—C6	0.1 (12)	C12—C11—C10—C9	0.6 (11)
C5—C6—C1—C2	0.8 (10)	C12—C11—C10—O2	−179.6 (7)
C5—C6—C1—N1	−179.0 (6)	C10—C11—C12—C13	−0.8 (11)
C1—C6—C5—C4	0.0 (11)	C11—C12—C13—O1	−179.9 (7)
N1—C7—C8—C9	−177.5 (7)	C11—C12—C13—C8	0.4 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (5)	1.82 (5)	2.604 (7)	152 (5)
C7—H7···O1i	1.03 (5)	2.55 (6)	3.493 (10)	151 (4)
C14—H14A···O2ii	0.96	2.57	3.500 (6)	164
C14—H14B···Cg2iii	0.96	3.27	4.142 (8)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (5)	1.82 (5)	2.604 (7)	152 (5)
C7—H7⋯O1i	1.03 (5)	2.55 (6)	3.493 (10)	151 (4)
C14—H14A⋯O2ii	0.96	2.57	3.500 (6)	164
C14—H14B⋯Cg2iii	0.96	3.27	4.142 (8)	152

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of ring C8–C13.