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

The mol-ecular geometry of the title compound, C(17)H(18)N(2)O(2), displays an E configuration with respect to the azo group. The dihedral angle between the aromatic rings is 10.39 (4)°. In the mol-ecule, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif.

Related literature

For general background to azo compounds, see: Russ & Tappe (1994 ▶); Tsuda et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶); Deveci et al. (2005 ▶); Karadayı et al., (2006 ▶); El-Ghamry et al. (2008 ▶); Albayrak et al., 2009 ▶; Yazıcı et al. (2010 ▶).

Experimental

Crystal data

C17H18N2O2

M = 282.33

Monoclinic,

a = 14.8315 (5) Å

b = 7.5573 (2) Å

c = 13.5020 (4) Å

β = 102.578 (3)°

V = 1477.07 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.75 × 0.47 × 0.21 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.946, T max = 0.984

21625 measured reflections

3054 independent reflections

2680 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.04

3054 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.16 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004910/bh2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004910/bh2335Isup2.hkl

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

C17H18N2O2	F(000) = 600
Mr = 282.33	Dx = 1.270 Mg m−3
Monoclinic, P21/c	Melting point: 350 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.8315 (5) Å	Cell parameters from 29224 reflections
b = 7.5573 (2) Å	θ = 1.5–28.0°
c = 13.5020 (4) Å	µ = 0.08 mm−1
β = 102.578 (3)°	T = 150 K
V = 1477.07 (8) Å3	Prism, brown
Z = 4	0.75 × 0.47 × 0.21 mm

Stoe IPDS II diffractometer	3054 independent reflections
Radiation source: fine-focus sealed tube	2680 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.8°
ω scans	h = −18→18
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.946, Tmax = 0.984	l = −16→16
21625 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2885P] where P = (Fo2 + 2Fc2)/3
3054 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.16 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.47997 (7)	0.68823 (13)	0.36509 (7)	0.0259 (2)
C2	0.50206 (7)	0.61432 (14)	0.27782 (8)	0.0288 (2)
H2	0.5600	0.5644	0.2815	0.035*
C3	0.43876 (7)	0.61552 (14)	0.18743 (8)	0.0310 (2)
H3	0.4540	0.5670	0.1299	0.037*
C4	0.35131 (7)	0.68914 (14)	0.18103 (8)	0.0293 (2)
C5	0.32685 (7)	0.76156 (13)	0.26807 (7)	0.0264 (2)
C6	0.39293 (7)	0.75846 (13)	0.35970 (7)	0.0260 (2)
H6	0.3780	0.8045	0.4180	0.031*
C7	0.23300 (7)	0.83175 (13)	0.26066 (8)	0.0287 (2)
C8	0.20412 (7)	0.89985 (15)	0.35252 (8)	0.0319 (2)
H8A	0.1425	0.9460	0.3335	0.048*
H8B	0.2455	0.9921	0.3829	0.048*
H8C	0.2058	0.8053	0.4004	0.048*
C9	0.68461 (7)	0.65001 (13)	0.55710 (7)	0.0253 (2)
C10	0.65886 (7)	0.69262 (14)	0.64747 (8)	0.0281 (2)
H10	0.5984	0.7262	0.6467	0.034*
C11	0.72316 (7)	0.68489 (14)	0.73810 (8)	0.0290 (2)
H11	0.7055	0.7149	0.7980	0.035*
C12	0.81431 (7)	0.63289 (13)	0.74182 (8)	0.0277 (2)
C13	0.83931 (7)	0.59345 (15)	0.65066 (8)	0.0310 (2)
H13	0.8999	0.5611	0.6513	0.037*
C14	0.77553 (7)	0.60153 (14)	0.55917 (8)	0.0298 (2)
H14	0.7934	0.5746	0.4991	0.036*
C15	0.88314 (7)	0.61869 (15)	0.84173 (8)	0.0323 (2)
H15A	0.9176	0.5094	0.8424	0.039*
H15B	0.8498	0.6120	0.8959	0.039*
C16	0.95106 (7)	0.77208 (15)	0.86325 (8)	0.0332 (2)
H16A	0.9171	0.8825	0.8588	0.040*
H16B	0.9881	0.7742	0.8122	0.040*
C17	1.01453 (8)	0.75689 (16)	0.96802 (8)	0.0364 (3)
H17A	1.0562	0.8557	0.9791	0.055*
H17B	1.0492	0.6489	0.9722	0.055*
H17C	0.9782	0.7565	1.0188	0.055*
N1	0.54195 (6)	0.69552 (12)	0.46137 (6)	0.0276 (2)
N2	0.62283 (6)	0.64756 (12)	0.45996 (6)	0.0276 (2)
O1	0.29175 (6)	0.68415 (12)	0.09043 (6)	0.0392 (2)
O2	0.17695 (6)	0.83191 (12)	0.17831 (6)	0.0416 (2)
H1	0.2391 (13)	0.734 (2)	0.1040 (13)	0.074 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0254 (5)	0.0280 (5)	0.0231 (5)	−0.0024 (4)	0.0022 (4)	0.0021 (4)
C2	0.0267 (5)	0.0311 (5)	0.0286 (5)	−0.0007 (4)	0.0062 (4)	0.0006 (4)
C3	0.0357 (6)	0.0334 (5)	0.0244 (5)	−0.0029 (4)	0.0076 (4)	−0.0017 (4)
C4	0.0333 (5)	0.0295 (5)	0.0219 (5)	−0.0040 (4)	−0.0010 (4)	0.0019 (4)
C5	0.0271 (5)	0.0260 (5)	0.0240 (5)	−0.0016 (4)	0.0012 (4)	0.0025 (4)
C6	0.0265 (5)	0.0276 (5)	0.0227 (5)	−0.0019 (4)	0.0028 (4)	0.0002 (4)
C7	0.0279 (5)	0.0260 (5)	0.0283 (5)	−0.0010 (4)	−0.0024 (4)	0.0037 (4)
C8	0.0261 (5)	0.0347 (6)	0.0330 (6)	0.0025 (4)	0.0023 (4)	0.0038 (4)
C9	0.0239 (5)	0.0255 (5)	0.0250 (5)	−0.0010 (4)	0.0019 (4)	0.0016 (4)
C10	0.0228 (5)	0.0324 (5)	0.0291 (5)	0.0007 (4)	0.0053 (4)	0.0017 (4)
C11	0.0282 (5)	0.0331 (5)	0.0253 (5)	−0.0022 (4)	0.0050 (4)	0.0013 (4)
C12	0.0266 (5)	0.0254 (5)	0.0285 (5)	−0.0028 (4)	0.0003 (4)	0.0037 (4)
C13	0.0226 (5)	0.0343 (5)	0.0344 (6)	0.0035 (4)	0.0029 (4)	0.0005 (4)
C14	0.0268 (5)	0.0343 (5)	0.0281 (5)	0.0024 (4)	0.0057 (4)	−0.0016 (4)
C15	0.0298 (5)	0.0336 (6)	0.0297 (5)	−0.0012 (4)	−0.0019 (4)	0.0058 (4)
C16	0.0316 (5)	0.0325 (5)	0.0311 (5)	−0.0010 (4)	−0.0032 (4)	0.0037 (4)
C17	0.0321 (6)	0.0419 (6)	0.0311 (6)	−0.0022 (5)	−0.0019 (4)	0.0017 (5)
N1	0.0236 (4)	0.0315 (4)	0.0259 (4)	0.0001 (3)	0.0015 (3)	0.0012 (3)
N2	0.0238 (4)	0.0314 (4)	0.0265 (4)	0.0001 (3)	0.0026 (3)	0.0014 (3)
O1	0.0409 (5)	0.0493 (5)	0.0220 (4)	0.0021 (4)	−0.0050 (3)	−0.0028 (3)
O2	0.0359 (4)	0.0484 (5)	0.0326 (4)	0.0095 (4)	−0.0100 (3)	−0.0021 (4)

C1—C6	1.3830 (14)	C10—C11	1.3792 (14)
C1—C2	1.4057 (14)	C10—H10	0.9300
C1—N1	1.4203 (12)	C11—C12	1.3982 (14)
C2—C3	1.3682 (14)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3930 (15)
C3—C4	1.3965 (15)	C12—C15	1.5079 (13)
C3—H3	0.9300	C13—C14	1.3840 (14)
C4—O1	1.3444 (12)	C13—H13	0.9300
C4—C5	1.4135 (15)	C14—H14	0.9300
C5—C6	1.4013 (13)	C15—C16	1.5217 (15)
C5—C7	1.4725 (14)	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—O2	1.2349 (12)	C16—C17	1.5233 (14)
C7—C8	1.4893 (15)	C16—H16A	0.9700
C8—H8A	0.9600	C16—H16B	0.9700
C8—H8B	0.9600	C17—H17A	0.9600
C8—H8C	0.9600	C17—H17B	0.9600
C9—C14	1.3917 (14)	C17—H17C	0.9600
C9—C10	1.3933 (14)	N1—N2	1.2572 (12)
C9—N2	1.4271 (12)	O1—H1	0.919 (19)
C6—C1—C2	119.58 (9)	C10—C11—C12	121.34 (10)
C6—C1—N1	116.35 (9)	C10—C11—H11	119.3
C2—C1—N1	124.06 (9)	C12—C11—H11	119.3
C3—C2—C1	120.34 (10)	C13—C12—C11	118.02 (9)
C3—C2—H2	119.8	C13—C12—C15	121.11 (9)
C1—C2—H2	119.8	C11—C12—C15	120.87 (9)
C2—C3—C4	120.37 (10)	C14—C13—C12	121.16 (9)
C2—C3—H3	119.8	C14—C13—H13	119.4
C4—C3—H3	119.8	C12—C13—H13	119.4
O1—C4—C3	117.55 (9)	C13—C14—C9	120.04 (10)
O1—C4—C5	122.04 (10)	C13—C14—H14	120.0
C3—C4—C5	120.39 (9)	C9—C14—H14	120.0
C6—C5—C4	118.09 (9)	C12—C15—C16	114.06 (8)
C6—C5—C7	122.34 (9)	C12—C15—H15A	108.7
C4—C5—C7	119.54 (9)	C16—C15—H15A	108.7
C1—C6—C5	121.21 (9)	C12—C15—H15B	108.7
C1—C6—H6	119.4	C16—C15—H15B	108.7
C5—C6—H6	119.4	H15A—C15—H15B	107.6
O2—C7—C5	120.17 (10)	C15—C16—C17	111.68 (9)
O2—C7—C8	119.36 (9)	C15—C16—H16A	109.3
C5—C7—C8	120.46 (9)	C17—C16—H16A	109.3
C7—C8—H8A	109.5	C15—C16—H16B	109.3
C7—C8—H8B	109.5	C17—C16—H16B	109.3
H8A—C8—H8B	109.5	H16A—C16—H16B	107.9
C7—C8—H8C	109.5	C16—C17—H17A	109.5
H8A—C8—H8C	109.5	C16—C17—H17B	109.5
H8B—C8—H8C	109.5	H17A—C17—H17B	109.5
C14—C9—C10	119.50 (9)	C16—C17—H17C	109.5
C14—C9—N2	116.13 (9)	H17A—C17—H17C	109.5
C10—C9—N2	124.35 (9)	H17B—C17—H17C	109.5
C11—C10—C9	119.92 (9)	N2—N1—C1	113.86 (8)
C11—C10—H10	120.0	N1—N2—C9	113.96 (8)
C9—C10—H10	120.0	C4—O1—H1	103.0 (11)
C6—C1—C2—C3	1.58 (15)	N2—C9—C10—C11	177.63 (9)
N1—C1—C2—C3	−178.81 (9)	C9—C10—C11—C12	−0.73 (15)
C1—C2—C3—C4	−0.41 (15)	C10—C11—C12—C13	1.73 (15)
C2—C3—C4—O1	−179.12 (9)	C10—C11—C12—C15	−177.81 (9)
C2—C3—C4—C5	−0.68 (16)	C11—C12—C13—C14	−1.41 (15)
O1—C4—C5—C6	178.96 (9)	C15—C12—C13—C14	178.13 (9)
C3—C4—C5—C6	0.59 (15)	C12—C13—C14—C9	0.11 (16)
O1—C4—C5—C7	0.93 (15)	C10—C9—C14—C13	0.93 (15)
C3—C4—C5—C7	−177.43 (9)	N2—C9—C14—C13	−177.46 (9)
C2—C1—C6—C5	−1.67 (15)	C13—C12—C15—C16	77.33 (13)
N1—C1—C6—C5	178.69 (9)	C11—C12—C15—C16	−103.14 (12)
C4—C5—C6—C1	0.59 (15)	C12—C15—C16—C17	176.16 (9)
C7—C5—C6—C1	178.56 (9)	C6—C1—N1—N2	−172.82 (9)
C6—C5—C7—O2	180.00 (10)	C2—C1—N1—N2	7.55 (14)
C4—C5—C7—O2	−2.06 (15)	C1—N1—N2—C9	−178.33 (8)
C6—C5—C7—C8	−1.21 (15)	C14—C9—N2—N1	−178.69 (9)
C4—C5—C7—C8	176.72 (9)	C10—C9—N2—N1	3.01 (14)
C14—C9—C10—C11	−0.62 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.921 (19)	1.675 (18)	2.5365 (13)	154.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.921 (19)	1.675 (18)	2.5365 (13)	154.3 (16)