2-[1-(3-Amino-phenyl-imino)-eth-yl]phenol.

The title compound, C(14)H(14)N(2)O, exists as the enol-imine tautomer. A strong intra-molecular hydrogen bond between O and N atoms forms a six-membered ring with an S(6) graph-set motif, which is approximately coplanar with the phenol ring, the inter-planar angle being 3.4 (3)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds and N-H⋯π inter-actions link the mol-ecules into infinite chains along [100].

Related literature

For background to Schiff base compounds, see: Blagus & Kaitner (2007 ▶); Blagus et al. (2010 ▶). For the photochromic and thermochromic characteristics of Schiff bases, see: Hadjoudis & Mavridis (2004 ▶). For graph-set notation of hydrogen bonds, see Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H14N2O

M = 226.27

Orthorhombic,

a = 9.0625 (2) Å

b = 5.5777 (2) Å

c = 23.2349 (6) Å

V = 1174.48 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.6 × 0.5 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

6829 measured reflections

1317 independent reflections

1145 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.10

1317 reflections

165 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; 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: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017624/fy2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017624/fy2009Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811017624/fy2009Isup3.cml

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

C14H14N2O	F(000) = 480
Mr = 226.27	Dx = 1.280 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 1145 reflections
a = 9.0625 (2) Å	θ = 4–27°
b = 5.5777 (2) Å	µ = 0.08 mm−1
c = 23.2349 (6) Å	T = 298 K
V = 1174.48 (6) Å3	Prism, yellow
Z = 4	0.6 × 0.5 × 0.4 mm

Oxford Diffraction Xcalibur CCD diffractometer	1145 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 27.0°, θmin = 4.1°
ω scans	h = −11→11
6829 measured reflections	k = −7→5
1317 independent reflections	l = −29→28

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.130P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1317 reflections	Δρmax = 0.15 e Å−3
165 parameters	Δρmin = −0.11 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (5)

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	0.41349 (19)	0.5690 (3)	0.29685 (8)	0.0596 (5)
H1	0.468 (4)	0.505 (6)	0.2607 (17)	0.089*
N1	0.5638 (2)	0.3031 (3)	0.23025 (7)	0.0440 (4)
N2	0.8305 (3)	0.5261 (4)	0.05762 (11)	0.0656 (6)
C1	0.5491 (2)	0.2236 (4)	0.33034 (9)	0.0402 (4)
C2	0.4534 (2)	0.4203 (4)	0.33965 (9)	0.0448 (5)
C3	0.3969 (3)	0.4621 (5)	0.39453 (11)	0.0588 (6)
H3	0.3360	0.5937	0.4008	0.071*
C4	0.4300 (3)	0.3117 (5)	0.43923 (11)	0.0638 (7)
H4	0.3891	0.3393	0.4753	0.077*
C5	0.5235 (3)	0.1192 (5)	0.43119 (10)	0.0619 (6)
H5	0.5473	0.0195	0.4619	0.074*
C6	0.5814 (3)	0.0761 (4)	0.37718 (10)	0.0515 (5)
H6	0.6435	−0.0548	0.3719	0.062*
C7	0.60706 (19)	0.1706 (4)	0.27231 (9)	0.0395 (4)
C8	0.7137 (2)	−0.0334 (4)	0.26549 (11)	0.0510 (5)
H8A	0.6640	−0.1821	0.2730	0.076*
H8B	0.7937	−0.0141	0.2922	0.076*
H8C	0.7516	−0.0344	0.2269	0.076*
C9	0.6061 (2)	0.2535 (4)	0.17224 (9)	0.0426 (4)
C10	0.6998 (2)	0.4088 (4)	0.14395 (9)	0.0452 (5)
H10	0.7375	0.5414	0.1633	0.054*
C11	0.7386 (2)	0.3685 (4)	0.08652 (9)	0.0458 (4)
C12	0.6800 (2)	0.1690 (4)	0.05828 (10)	0.0509 (5)
H12	0.7045	0.1396	0.0201	0.061*
C13	0.5863 (3)	0.0158 (5)	0.08685 (10)	0.0548 (5)
H13	0.5486	−0.1172	0.0677	0.066*
C14	0.5470 (3)	0.0563 (4)	0.14380 (11)	0.0514 (5)
H14	0.4823	−0.0468	0.1626	0.062*
H1N2	0.874 (4)	0.635 (7)	0.0803 (14)	0.077*
H2N2	0.864 (4)	0.481 (6)	0.0229 (18)	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0719 (11)	0.0573 (10)	0.0494 (9)	0.0216 (8)	0.0010 (8)	0.0010 (8)
N1	0.0465 (9)	0.0483 (9)	0.0371 (8)	0.0038 (8)	−0.0003 (7)	−0.0028 (7)
N2	0.0719 (14)	0.0692 (14)	0.0558 (12)	−0.0132 (12)	0.0135 (11)	0.0016 (11)
C1	0.0351 (8)	0.0468 (10)	0.0388 (9)	−0.0034 (8)	−0.0023 (8)	−0.0033 (9)
C2	0.0452 (10)	0.0489 (11)	0.0403 (10)	0.0001 (9)	−0.0012 (9)	−0.0043 (9)
C3	0.0604 (13)	0.0658 (15)	0.0501 (13)	0.0077 (12)	0.0057 (11)	−0.0125 (11)
C4	0.0667 (15)	0.0847 (19)	0.0399 (11)	−0.0016 (14)	0.0037 (11)	−0.0071 (12)
C5	0.0690 (15)	0.0746 (16)	0.0422 (12)	−0.0035 (13)	−0.0036 (11)	0.0072 (12)
C6	0.0516 (12)	0.0554 (12)	0.0476 (12)	0.0028 (10)	−0.0052 (10)	0.0019 (10)
C7	0.0344 (8)	0.0432 (10)	0.0408 (10)	−0.0028 (8)	−0.0019 (8)	−0.0030 (8)
C8	0.0471 (11)	0.0523 (11)	0.0535 (12)	0.0087 (9)	0.0006 (10)	−0.0015 (10)
C9	0.0435 (9)	0.0474 (10)	0.0369 (9)	0.0052 (9)	−0.0014 (8)	−0.0037 (8)
C10	0.0480 (10)	0.0438 (10)	0.0439 (10)	−0.0002 (9)	−0.0042 (9)	−0.0038 (9)
C11	0.0429 (9)	0.0512 (10)	0.0435 (10)	0.0038 (9)	−0.0001 (8)	0.0014 (9)
C12	0.0527 (12)	0.0614 (13)	0.0385 (10)	0.0034 (11)	0.0016 (9)	−0.0074 (10)
C13	0.0600 (13)	0.0576 (12)	0.0467 (12)	−0.0058 (11)	−0.0009 (10)	−0.0142 (11)
C14	0.0517 (12)	0.0537 (12)	0.0489 (11)	−0.0068 (10)	0.0020 (10)	−0.0039 (10)

O1—C2	1.345 (3)	C5—H5	0.9300
O1—H1	1.04 (4)	C6—H6	0.9300
N1—C7	1.286 (3)	C7—C8	1.501 (3)
N1—C9	1.428 (3)	C8—H8A	0.9600
N2—C11	1.385 (3)	C8—H8B	0.9600
N2—H1N2	0.89 (4)	C8—H8C	0.9600
N2—H2N2	0.90 (4)	C9—C10	1.380 (3)
C1—C6	1.395 (3)	C9—C14	1.391 (3)
C1—C2	1.415 (3)	C10—C11	1.398 (3)
C1—C7	1.477 (3)	C10—H10	0.9300
C2—C3	1.394 (3)	C11—C12	1.397 (3)
C3—C4	1.368 (4)	C12—C13	1.376 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.380 (4)	C13—C14	1.389 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.381 (4)	C14—H14	0.9300
C2—O1—H1	105 (2)	C1—C7—C8	118.49 (18)
C7—N1—C9	121.61 (17)	C7—C8—H8A	109.5
C11—N2—H1N2	114 (2)	C7—C8—H8B	109.5
C11—N2—H2N2	117 (2)	H8A—C8—H8B	109.5
H1N2—N2—H2N2	125 (3)	C7—C8—H8C	109.5
C6—C1—C2	117.80 (19)	H8A—C8—H8C	109.5
C6—C1—C7	121.29 (18)	H8B—C8—H8C	109.5
C2—C1—C7	120.85 (18)	C10—C9—C14	120.5 (2)
O1—C2—C3	118.3 (2)	C10—C9—N1	119.53 (18)
O1—C2—C1	122.01 (19)	C14—C9—N1	119.9 (2)
C3—C2—C1	119.7 (2)	C9—C10—C11	120.56 (19)
C4—C3—C2	120.7 (2)	C9—C10—H10	119.7
C4—C3—H3	119.6	C11—C10—H10	119.7
C2—C3—H3	119.6	N2—C11—C12	120.4 (2)
C3—C4—C5	120.6 (2)	N2—C11—C10	120.8 (2)
C3—C4—H4	119.7	C12—C11—C10	118.8 (2)
C5—C4—H4	119.7	C13—C12—C11	120.2 (2)
C4—C5—C6	119.5 (2)	C13—C12—H12	119.9
C4—C5—H5	120.3	C11—C12—H12	119.9
C6—C5—H5	120.3	C12—C13—C14	121.1 (2)
C5—C6—C1	121.7 (2)	C12—C13—H13	119.4
C5—C6—H6	119.1	C14—C13—H13	119.4
C1—C6—H6	119.1	C13—C14—C9	118.9 (2)
N1—C7—C1	118.05 (17)	C13—C14—H14	120.6
N1—C7—C8	123.46 (19)	C9—C14—H14	120.6
C6—C1—C2—O1	−178.5 (2)	C6—C1—C7—C8	−5.7 (3)
C7—C1—C2—O1	−1.2 (3)	C2—C1—C7—C8	177.18 (17)
C6—C1—C2—C3	0.9 (3)	C7—N1—C9—C10	−111.9 (2)
C7—C1—C2—C3	178.1 (2)	C7—N1—C9—C14	71.2 (3)
O1—C2—C3—C4	177.8 (2)	C14—C9—C10—C11	−0.9 (3)
C1—C2—C3—C4	−1.6 (4)	N1—C9—C10—C11	−177.75 (19)
C2—C3—C4—C5	1.9 (4)	C9—C10—C11—N2	178.9 (2)
C3—C4—C5—C6	−1.4 (4)	C9—C10—C11—C12	0.3 (3)
C4—C5—C6—C1	0.7 (4)	N2—C11—C12—C13	−178.6 (2)
C2—C1—C6—C5	−0.4 (3)	C10—C11—C12—C13	−0.1 (3)
C7—C1—C6—C5	−177.7 (2)	C11—C12—C13—C14	0.5 (4)
C9—N1—C7—C1	−175.40 (18)	C12—C13—C14—C9	−1.0 (4)
C9—N1—C7—C8	5.0 (3)	C10—C9—C14—C13	1.3 (3)
C6—C1—C7—N1	174.69 (19)	N1—C9—C14—C13	178.1 (2)
C2—C1—C7—N1	−2.5 (3)

Cg is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.04 (4)	1.59 (4)	2.540 (2)	150 (3)
C8—H8B···O1i	0.96	2.71	3.243 (3)	116
N2—H1N2···Cgi	0.90 (4)	2.71 (4)	3.457 (3)	142 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.04 (4)	1.59 (4)	2.540 (2)	150 (3)
C8—H8B⋯O1i	0.96	2.71	3.243 (3)	116
N2—H1N2⋯Cgi	0.90 (4)	2.71 (4)	3.457 (3)	142 (3)

Symmetry code: (i) .