(E)-1-{2-Hy-droxy-5-[(4-methyl-phen-yl)diazen-yl]phen-yl}ethanone.

The structure of the title compound, C(15)H(14)N(2)O(2), an azo dye, displays a trans configuration with respect to the N=N bridge. The dihedral angle between the aromatic rings is 5.06 (8)°. The mol-ecular conformation is stabilized by a strong intra-molecular O-H⋯O hydrogen bond. In the crystal, inter-molecular C-H⋯O hydrogen bonds occur.

Related literature

For general backgrond to azo compounds, see: Klaus (2003 ▶); Bahatti & Seshadri (2004 ▶); Catino & Farris (1985 ▶); Fadda et al. (1994 ▶);Taniike et al. (1996 ▶); Zollinger (2003 ▶); For bond-length data, see: El-Ghamry et al. 2008 ▶; Petek et al. 2006 ▶.

Experimental

Crystal data

C15H14N2O2

M = 254.28

Triclinic,

a = 7.0919 (7) Å

b = 7.0842 (7) Å

c = 13.4094 (13) Å

α = 92.722 (8)°

β = 93.045 (8)°

γ = 101.926 (9)°

V = 657.04 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.42 × 0.34 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.974, T max = 0.991

8340 measured reflections

2542 independent reflections

791 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.100

S = 0.82

2542 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.11 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001802/hg2784sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001802/hg2784Isup2.hkl

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

C15H14N2O2	Z = 2
Mr = 254.28	F(000) = 268
Triclinic, P1	Dx = 1.285 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0919 (7) Å	Cell parameters from 4309 reflections
b = 7.0842 (7) Å	θ = 2.9–27.7°
c = 13.4094 (13) Å	µ = 0.09 mm−1
α = 92.722 (8)°	T = 296 K
β = 93.045 (8)°	Prism, brown
γ = 101.926 (9)°	0.42 × 0.34 × 0.19 mm
V = 657.04 (11) Å3

Stoe IPDS 2 diffractometer	2542 independent reflections
Radiation source: fine-focus sealed tube	791 reflections with I > 2σ(I)
graphite	Rint = 0.090
Detector resolution: 6.67 pixels mm-1	θmax = 27.6°, θmin = 2.9°
rotation method scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.974, Tmax = 0.991	l = −17→17
8340 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 0.82	w = 1/[σ2(Fo2) + (0.0254P)2] where P = (Fo2 + 2Fc2)/3
2542 reflections	(Δ/σ)max = 0.002
173 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.11 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
C1	0.5890 (6)	0.1644 (5)	0.6539 (3)	0.0626 (10)
H1	0.5339	0.1331	0.5892	0.075*
C2	0.4713 (5)	0.1621 (5)	0.7323 (3)	0.0613 (10)
H2	0.3380	0.1268	0.7201	0.074*
C3	0.5494 (5)	0.2116 (5)	0.8289 (2)	0.0498 (9)
C4	0.7472 (5)	0.2595 (5)	0.8461 (3)	0.0565 (10)
H4	0.8021	0.2911	0.9108	0.068*
C5	0.8635 (5)	0.2602 (5)	0.7668 (3)	0.0615 (10)
H5	0.9969	0.2939	0.7788	0.074*
C6	0.7860 (5)	0.2119 (5)	0.6695 (3)	0.0569 (9)
C7	0.3481 (5)	0.2497 (5)	1.0644 (3)	0.0513 (9)
C8	0.1491 (5)	0.2170 (5)	1.0434 (3)	0.0637 (10)
H8	0.0991	0.1991	0.9773	0.076*
C9	0.0274 (5)	0.2111 (5)	1.1187 (3)	0.0699 (11)
H9	−0.1053	0.1879	1.1040	0.084*
C11	0.3008 (5)	0.2802 (4)	1.2409 (2)	0.0455 (9)
C12	0.4198 (5)	0.2828 (4)	1.1621 (3)	0.0535 (10)
H12	0.5529	0.3079	1.1759	0.064*
C13	0.3760 (5)	0.3186 (5)	1.3452 (3)	0.0553 (9)
C14	0.5883 (5)	0.3741 (5)	1.3698 (3)	0.0698 (10)
H14A	0.6130	0.3940	1.4410	0.105*
H14B	0.6403	0.4913	1.3387	0.105*
H14C	0.6484	0.2728	1.3456	0.105*
C15	0.9185 (6)	0.2152 (5)	0.5837 (3)	0.0842 (13)
H15A	1.0252	0.1579	0.6031	0.126*
H15B	0.9660	0.3464	0.5676	0.126*
H15C	0.8477	0.1434	0.5262	0.126*
C10	0.1004 (5)	0.2396 (5)	1.2172 (3)	0.0604 (10)
N1	0.4117 (4)	0.2099 (4)	0.9032 (2)	0.0546 (8)
N2	0.4863 (4)	0.2508 (4)	0.9904 (2)	0.0511 (8)
O1	−0.0261 (3)	0.2310 (3)	1.2899 (2)	0.0836 (8)
H16	0.0334	0.2494	1.3448	0.125*
O2	0.2651 (4)	0.3054 (4)	1.41403 (18)	0.0814 (8)

	U11	U22	U33	U12	U13	U23
C1	0.066 (3)	0.076 (3)	0.044 (2)	0.015 (2)	0.003 (2)	−0.0022 (18)
C2	0.053 (2)	0.074 (3)	0.055 (2)	0.0093 (19)	0.0023 (19)	0.0057 (19)
C3	0.065 (3)	0.047 (2)	0.041 (2)	0.0192 (19)	0.0056 (19)	0.0092 (17)
C4	0.047 (2)	0.074 (3)	0.049 (2)	0.0155 (19)	−0.0025 (18)	0.0000 (18)
C5	0.049 (2)	0.071 (3)	0.065 (3)	0.0132 (18)	0.008 (2)	0.0025 (19)
C6	0.068 (3)	0.060 (2)	0.045 (2)	0.0181 (19)	0.0076 (19)	0.0055 (17)
C7	0.044 (2)	0.056 (3)	0.053 (2)	0.0100 (18)	0.0088 (18)	0.0016 (19)
C8	0.056 (2)	0.080 (3)	0.054 (2)	0.0128 (19)	0.0020 (19)	−0.0057 (19)
C9	0.043 (2)	0.098 (3)	0.067 (3)	0.0132 (19)	0.002 (2)	−0.006 (2)
C11	0.046 (2)	0.049 (2)	0.043 (2)	0.0108 (18)	0.0100 (18)	0.0006 (16)
C12	0.050 (2)	0.051 (3)	0.060 (3)	0.0096 (18)	0.003 (2)	0.0026 (19)
C13	0.058 (2)	0.059 (2)	0.050 (2)	0.0145 (18)	0.0114 (19)	−0.0050 (16)
C14	0.068 (2)	0.087 (3)	0.053 (2)	0.0194 (19)	−0.0019 (17)	−0.0088 (18)
C15	0.088 (3)	0.108 (3)	0.065 (3)	0.031 (2)	0.031 (2)	0.013 (2)
C10	0.050 (2)	0.065 (3)	0.067 (3)	0.0109 (18)	0.022 (2)	−0.0025 (19)
N1	0.060 (2)	0.062 (2)	0.0427 (18)	0.0132 (15)	0.0040 (15)	0.0017 (15)
N2	0.053 (2)	0.0559 (19)	0.046 (2)	0.0132 (15)	0.0055 (16)	0.0022 (14)
O1	0.0542 (17)	0.119 (2)	0.0733 (18)	0.0082 (14)	0.0229 (14)	−0.0091 (14)
O2	0.078 (2)	0.109 (2)	0.0548 (17)	0.0120 (15)	0.0216 (15)	−0.0074 (14)

C1—C6	1.370 (5)	C9—C10	1.383 (5)
C1—C2	1.375 (5)	C9—H9	0.9300
C1—H1	0.9300	C11—C12	1.385 (5)
C2—C3	1.382 (4)	C11—C10	1.406 (4)
C2—H2	0.9300	C11—C13	1.463 (4)
C3—C4	1.377 (4)	C12—H12	0.9300
C3—N1	1.430 (4)	C13—O2	1.239 (4)
C4—C5	1.380 (5)	C13—C14	1.490 (4)
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.386 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—C15	1.522 (5)	C15—H15A	0.9600
C7—C12	1.371 (5)	C15—H15B	0.9600
C7—C8	1.393 (4)	C15—H15C	0.9600
C7—N2	1.431 (4)	C10—O1	1.354 (4)
C8—C9	1.360 (5)	N1—N2	1.253 (3)
C8—H8	0.9300	O1—H16	0.8200
C6—C1—C2	121.1 (4)	C12—C11—C10	117.3 (3)
C6—C1—H1	119.4	C12—C11—C13	122.6 (3)
C2—C1—H1	119.4	C10—C11—C13	120.1 (3)
C1—C2—C3	120.6 (4)	C7—C12—C11	122.2 (4)
C1—C2—H2	119.7	C7—C12—H12	118.9
C3—C2—H2	119.7	C11—C12—H12	118.9
C4—C3—C2	119.1 (4)	O2—C13—C11	120.8 (3)
C4—C3—N1	125.8 (3)	O2—C13—C14	119.2 (3)
C2—C3—N1	115.1 (3)	C11—C13—C14	120.1 (3)
C3—C4—C5	119.7 (4)	C13—C14—H14A	109.5
C3—C4—H4	120.2	C13—C14—H14B	109.5
C5—C4—H4	120.2	H14A—C14—H14B	109.5
C4—C5—C6	121.5 (4)	C13—C14—H14C	109.5
C4—C5—H5	119.3	H14A—C14—H14C	109.5
C6—C5—H5	119.3	H14B—C14—H14C	109.5
C1—C6—C5	118.0 (4)	C6—C15—H15A	109.5
C1—C6—C15	121.8 (4)	C6—C15—H15B	109.5
C5—C6—C15	120.1 (4)	H15A—C15—H15B	109.5
C12—C7—C8	119.0 (4)	C6—C15—H15C	109.5
C12—C7—N2	116.6 (3)	H15A—C15—H15C	109.5
C8—C7—N2	124.4 (3)	H15B—C15—H15C	109.5
C9—C8—C7	120.5 (4)	O1—C10—C9	118.2 (3)
C9—C8—H8	119.7	O1—C10—C11	121.1 (4)
C7—C8—H8	119.7	C9—C10—C11	120.7 (3)
C8—C9—C10	120.2 (4)	N2—N1—C3	113.8 (3)
C8—C9—H9	119.9	N1—N2—C7	113.7 (3)
C10—C9—H9	119.9	C10—O1—H16	109.5
C6—C1—C2—C3	1.3 (5)	C13—C11—C12—C7	−178.9 (3)
C1—C2—C3—C4	−1.4 (5)	C12—C11—C13—O2	−176.3 (4)
C1—C2—C3—N1	177.9 (4)	C10—C11—C13—O2	4.0 (5)
C2—C3—C4—C5	1.1 (5)	C12—C11—C13—C14	3.6 (4)
N1—C3—C4—C5	−178.2 (4)	C10—C11—C13—C14	−176.1 (3)
C3—C4—C5—C6	−0.6 (5)	C8—C9—C10—O1	−179.5 (4)
C2—C1—C6—C5	−0.8 (5)	C8—C9—C10—C11	1.8 (5)
C2—C1—C6—C15	180.0 (4)	C12—C11—C10—O1	178.9 (3)
C4—C5—C6—C1	0.5 (5)	C13—C11—C10—O1	−1.4 (5)
C4—C5—C6—C15	179.7 (4)	C12—C11—C10—C9	−2.5 (5)
C12—C7—C8—C9	−2.3 (5)	C13—C11—C10—C9	177.2 (3)
N2—C7—C8—C9	177.4 (4)	C4—C3—N1—N2	−2.4 (4)
C7—C8—C9—C10	0.7 (5)	C2—C3—N1—N2	178.4 (3)
C8—C7—C12—C11	1.6 (5)	C3—N1—N2—C7	179.7 (3)
N2—C7—C12—C11	−178.2 (3)	C12—C7—N2—N1	176.5 (3)
C10—C11—C12—C7	0.8 (5)	C8—C7—N2—N1	−3.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H16···O2	0.82	1.80	2.533 (4)	147
C14—H14C···O1i	0.96	2.53	3.318 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H16⋯O2	0.82	1.80	2.533 (4)	147
C14—H14C⋯O1i	0.96	2.53	3.318 (4)	139

Symmetry code: (i) .