2-[(2-Meth-oxy-benzyl-idene)amino]-phenol.

In the title compound, C(14)H(13)NO(2), the azomethine double bond adopts an E conformation and the benzene rings form a dihedral angle of 77.70 (7)°. In the crystal, mol-ecules are linked by O-H⋯N and C-H⋯O hydrogen bonds and arranged in a zigzag fashion, forming infinite chains parallel to the c axis, resulting in a graph-set R(2) (2)(9) motif.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ▶); Gerdemann et al. (2002 ▶); Samadhiya & Halve (2001 ▶). For a related structure, see: Liang et al. (2009 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13NO2

M = 227.25

Monoclinic,

a = 9.8709 (5) Å

b = 6.6606 (3) Å

c = 18.6128 (9) Å

β = 105.249 (1)°

V = 1180.63 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.49 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.986

6660 measured reflections

2186 independent reflections

1680 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.04

2186 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016224/pv2528sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016224/pv2528Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016224/pv2528Isup3.cml

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

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 1.279 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1522 reflections
a = 9.8709 (5) Å	θ = 2.7–24.5°
b = 6.6606 (3) Å	µ = 0.09 mm−1
c = 18.6128 (9) Å	T = 273 K
β = 105.249 (1)°	Block, colorless
V = 1180.63 (10) Å3	0.49 × 0.17 × 0.16 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2186 independent reflections
Radiation source: fine-focus sealed tube	1680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.959, Tmax = 0.986	k = −8→8
6660 measured reflections	l = −22→22

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.048P)2 + 0.0868P] where P = (Fo2 + 2Fc2)/3
2186 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 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
O1	0.93139 (12)	0.87882 (18)	0.09546 (8)	0.0651 (4)
O2	0.51633 (11)	0.57038 (17)	0.23910 (6)	0.0461 (3)
H2A	0.479 (2)	0.490 (3)	0.2663 (11)	0.073 (6)*
N1	0.57240 (12)	0.86217 (17)	0.15101 (6)	0.0371 (3)
C1	0.90429 (16)	1.0512 (2)	0.12897 (9)	0.0452 (4)
C2	0.99740 (17)	1.2103 (3)	0.14871 (9)	0.0564 (5)
H2B	1.0849	1.2044	0.1389	0.068*
C3	0.9600 (2)	1.3766 (3)	0.18280 (10)	0.0590 (5)
H3A	1.0232	1.4824	0.1962	0.071*
C4	0.83070 (19)	1.3892 (3)	0.19753 (9)	0.0546 (4)
H4A	0.8062	1.5028	0.2203	0.066*
C5	0.73841 (17)	1.2319 (2)	0.17814 (8)	0.0446 (4)
H5A	0.6511	1.2399	0.1882	0.054*
C6	0.77264 (15)	1.0608 (2)	0.14376 (8)	0.0384 (4)
C7	0.67269 (15)	0.8955 (2)	0.12140 (8)	0.0381 (4)
H7A	0.6830	0.8104	0.0836	0.046*
C8	0.47548 (14)	0.7082 (2)	0.11917 (8)	0.0351 (3)
C9	0.44428 (14)	0.5617 (2)	0.16613 (7)	0.0354 (3)
C10	0.34863 (16)	0.4124 (2)	0.13671 (9)	0.0443 (4)
H10A	0.3288	0.3132	0.1676	0.053*
C11	0.28226 (16)	0.4101 (2)	0.06126 (9)	0.0482 (4)
H11A	0.2182	0.3090	0.0418	0.058*
C12	0.31018 (17)	0.5557 (2)	0.01490 (8)	0.0484 (4)
H12A	0.2643	0.5546	−0.0356	0.058*
C13	0.40674 (16)	0.7036 (2)	0.04392 (8)	0.0441 (4)
H13A	0.4261	0.8018	0.0125	0.053*
C14	1.0695 (2)	0.8464 (3)	0.08734 (13)	0.0799 (6)
H14A	1.0744	0.7162	0.0661	0.120*
H14B	1.1361	0.8538	0.1353	0.120*
H14C	1.0910	0.9474	0.0552	0.120*

	U11	U22	U33	U12	U13	U23
O1	0.0531 (7)	0.0655 (8)	0.0875 (9)	0.0003 (6)	0.0376 (7)	−0.0084 (7)
O2	0.0529 (7)	0.0528 (7)	0.0330 (6)	−0.0114 (5)	0.0120 (5)	0.0027 (5)
N1	0.0413 (7)	0.0361 (7)	0.0367 (7)	−0.0026 (5)	0.0154 (6)	0.0003 (5)
C1	0.0434 (9)	0.0507 (10)	0.0437 (9)	−0.0014 (8)	0.0152 (7)	0.0060 (7)
C2	0.0411 (9)	0.0726 (12)	0.0549 (10)	−0.0129 (9)	0.0116 (8)	0.0120 (9)
C3	0.0628 (12)	0.0566 (11)	0.0502 (10)	−0.0233 (9)	0.0018 (9)	0.0037 (8)
C4	0.0654 (12)	0.0471 (10)	0.0487 (10)	−0.0101 (9)	0.0104 (9)	−0.0033 (8)
C5	0.0466 (9)	0.0450 (9)	0.0427 (9)	−0.0023 (8)	0.0126 (7)	0.0014 (7)
C6	0.0400 (8)	0.0394 (8)	0.0360 (8)	−0.0035 (7)	0.0100 (6)	0.0045 (6)
C7	0.0438 (9)	0.0369 (8)	0.0364 (8)	0.0000 (7)	0.0153 (7)	−0.0015 (6)
C8	0.0365 (8)	0.0357 (8)	0.0366 (8)	−0.0002 (6)	0.0159 (6)	−0.0022 (6)
C9	0.0345 (8)	0.0402 (8)	0.0337 (8)	0.0009 (6)	0.0129 (6)	0.0000 (6)
C10	0.0432 (9)	0.0440 (9)	0.0473 (9)	−0.0070 (7)	0.0145 (7)	0.0054 (7)
C11	0.0424 (9)	0.0505 (9)	0.0496 (9)	−0.0110 (7)	0.0084 (7)	−0.0063 (8)
C12	0.0485 (9)	0.0600 (10)	0.0346 (8)	−0.0048 (8)	0.0069 (7)	−0.0029 (7)
C13	0.0488 (9)	0.0484 (9)	0.0371 (8)	−0.0032 (8)	0.0149 (7)	0.0059 (7)
C14	0.0624 (12)	0.0986 (16)	0.0913 (15)	0.0195 (12)	0.0422 (11)	0.0109 (12)

O1—C1	1.3665 (19)	C6—C7	1.464 (2)
O1—C14	1.427 (2)	C7—H7A	0.9300
O2—C9	1.3586 (16)	C8—C13	1.387 (2)
O2—H2A	0.88 (2)	C8—C9	1.3972 (19)
N1—C7	1.2729 (18)	C9—C10	1.382 (2)
N1—C8	1.4211 (18)	C10—C11	1.385 (2)
C1—C2	1.387 (2)	C10—H10A	0.9300
C1—C6	1.399 (2)	C11—C12	1.373 (2)
C2—C3	1.374 (3)	C11—H11A	0.9300
C2—H2B	0.9300	C12—C13	1.378 (2)
C3—C4	1.377 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.373 (2)	C14—H14A	0.9600
C4—H4A	0.9300	C14—H14B	0.9600
C5—C6	1.391 (2)	C14—H14C	0.9600
C5—H5A	0.9300
C1—O1—C14	118.86 (15)	C13—C8—C9	119.10 (13)
C9—O2—H2A	111.2 (13)	C13—C8—N1	122.29 (12)
C7—N1—C8	117.39 (12)	C9—C8—N1	118.55 (12)
O1—C1—C2	124.55 (15)	O2—C9—C10	123.38 (13)
O1—C1—C6	115.58 (13)	O2—C9—C8	116.88 (12)
C2—C1—C6	119.88 (15)	C10—C9—C8	119.67 (13)
C3—C2—C1	119.88 (16)	C9—C10—C11	120.10 (14)
C3—C2—H2B	120.1	C9—C10—H10A	120.0
C1—C2—H2B	120.1	C11—C10—H10A	120.0
C2—C3—C4	121.09 (16)	C12—C11—C10	120.64 (14)
C2—C3—H3A	119.5	C12—C11—H11A	119.7
C4—C3—H3A	119.5	C10—C11—H11A	119.7
C5—C4—C3	119.15 (16)	C11—C12—C13	119.40 (14)
C5—C4—H4A	120.4	C11—C12—H12A	120.3
C3—C4—H4A	120.4	C13—C12—H12A	120.3
C4—C5—C6	121.41 (15)	C12—C13—C8	121.07 (14)
C4—C5—H5A	119.3	C12—C13—H13A	119.5
C6—C5—H5A	119.3	C8—C13—H13A	119.5
C5—C6—C1	118.58 (14)	O1—C14—H14A	109.5
C5—C6—C7	121.32 (13)	O1—C14—H14B	109.5
C1—C6—C7	120.08 (13)	H14A—C14—H14B	109.5
N1—C7—C6	123.41 (13)	O1—C14—H14C	109.5
N1—C7—H7A	118.3	H14A—C14—H14C	109.5
C6—C7—H7A	118.3	H14B—C14—H14C	109.5
C14—O1—C1—C2	7.6 (2)	C1—C6—C7—N1	158.03 (14)
C14—O1—C1—C6	−171.95 (16)	C7—N1—C8—C13	−53.20 (19)
O1—C1—C2—C3	−179.47 (14)	C7—N1—C8—C9	129.61 (14)
C6—C1—C2—C3	0.1 (2)	C13—C8—C9—O2	178.76 (13)
C1—C2—C3—C4	−0.4 (3)	N1—C8—C9—O2	−3.95 (19)
C2—C3—C4—C5	0.4 (2)	C13—C8—C9—C10	1.6 (2)
C3—C4—C5—C6	−0.2 (2)	N1—C8—C9—C10	178.92 (13)
C4—C5—C6—C1	−0.1 (2)	O2—C9—C10—C11	−178.05 (14)
C4—C5—C6—C7	−178.40 (14)	C8—C9—C10—C11	−1.1 (2)
O1—C1—C6—C5	179.72 (13)	C9—C10—C11—C12	−0.2 (2)
C2—C1—C6—C5	0.1 (2)	C10—C11—C12—C13	0.9 (2)
O1—C1—C6—C7	−1.9 (2)	C11—C12—C13—C8	−0.4 (2)
C2—C1—C6—C7	178.50 (14)	C9—C8—C13—C12	−0.9 (2)
C8—N1—C7—C6	174.21 (12)	N1—C8—C13—C12	−178.09 (14)
C5—C6—C7—N1	−23.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1i	0.88 (2)	1.94 (2)	2.796 (2)	163 (2)
C10—H10A···O2i	0.93	2.56	3.269 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1i	0.88 (2)	1.94 (2)	2.796 (2)	163 (2)
C10—H10A⋯O2i	0.93	2.56	3.269 (2)	133

Symmetry code: (i) .