organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-{5-[(E)-(4-Propyl­phen­yl)diazen­yl]-2-hy­dr­oxy­phen­yl}ethanone

aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey, bSinop Faculty of Education, Sinop University, TR-57000 Sinop, Turkey, and cDepartment of Chemistry, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey
*Correspondence e-mail: yserap@omu.edu.tr

(Received 20 January 2011; accepted 9 February 2011; online 16 February 2011)

The mol­ecular geometry of the title compound, C17H18N2O2, displays an E configuration with respect to the azo group. The dihedral angle between the aromatic rings is 10.39 (4)°. In the mol­ecule, an intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif.

Related literature

For general background to azo compounds, see: Russ & Tappe (1994[Russ, H. W. & Tappe, H. (1994). Eur. Patent Appl. EP 629 627.]); Tsuda et al. (2000[Tsuda, S., Matsusaka, N., Madarame, H., Ueno, S., Susa, N., Ishida, K., Kawamura, N., Sekihashi, K. & Sasaki, Y. E. (2000). Mutat. Res. Genet. Toxicol. Environ. Mutagen. 465, 11-26.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Open, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Deveci et al. (2005[Deveci, O., Işık, S., Albayrak, C. & Ağar, E. (2005). Acta Cryst. E61, o3226-o3227.]); Karadayı et al., (2006[Karadayı, N., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3695-o3696.]); El-Ghamry et al. (2008[El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673-o1674.]); Albayrak et al., 2009[Albayrak, Ç., Gümrükçüoğlu, İ., Odabaşoğlu, M., İskeleli, N. O. & Ağar, E. (2009). J. Mol. Struct. 932, 43-54.]; Yazıcı et al. (2010[Yazıcı, S., Albayrak, Ç., Gümrükçüoğlu, İ., Şenel, İ. & Büyükgüngör, O. (2010). Acta Cryst. E66, o559-o560.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N2O2

  • Mr = 282.33

  • Monoclinic, P 21 /c

  • 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.946, Tmax = 0.984

  • 21625 measured reflections

  • 3054 independent reflections

  • 2680 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Azo colorants, which are characterized by one or more azo bonds, are the most versatile class of dyes. They are used in textiles, printing, cosmetics, drugs and other consumer goods (Russ & Tappe, 1994; Tsuda et al., 2000).

A view of a molecule of the title compound, together with the atom-numbering scheme, is shown in Fig. 1. The title molecule adopts the E configuration with respect to NN bridge and the C1—N1—N2—C9 torsion angle is -178.33 (8)°. The A/B and B/C dihedral angles between the A (C1···C6), B (C9···14) and C (C12/C15/C16/C17) fragments are 10.39 (4) and 76.04 (8)°, respectively.

The N1—C1 and N2—C9 bond lengths of 1.4203 (12) and 1.4271 (12) Å, respectively, indicate single-bond character, whereas the N1—N2 bond length of 1.2572 (12) Å indicates double-bond character. In the molecule, all bond lengths are in good agreement with those reported for other azo compounds (Allen et al., 1987; Deveci et al., 2005; El-Ghamry et al., 2008; Albayrak et al., 2009; Yazıcı et al., 2010; Karadayı et al., 2006). There is a strong intra-molecular hydrogen bond of 2.5365 (13) Å between atoms O1 and O2. The crystal packing is controlled by dipole-dipole and van der Waals interactions, and molecules are stacked along crystallographic [010] direction.

Related literature top

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 top

A mixture of 4-propylaniline (1.05 g, 7.8 mmol), water (20 ml) and concentrated hydrochloric acid (1.97 ml, 23.4 mmol) was stirred until a clear solution was obtained. This solution was cooled down to 0–5 °C and a solution of sodium nitrite (0.75 g 7.8 mmol) in water was added dropwise while the temperature was maintained below 5 °C. The resulting mixture was stirred for 30 min in an ice bath. 2-Hydroxyacetophenone (1.067 g, 7.8 mmol, solution at pH 9) was gradually added to a cooled solution of 4-propylbenzenediazonium chloride, prepared as described above, and the resulting mixture was stirred at 0–5 °C for 2 h in an ice bath. The product was recrystallized from ethanol to obtain solid (E)-2-acetyl-4-(4-propylphenyldiazenyl)phenol. Crystals were obtained after one day by slow evaporation from acetic acid (yield 45%, m.p. = 350–352 K).

Refinement top

All C-bonded H atoms were positioned with idealized geometry using a riding model, with C—H = 0.93–0.97 Å. Hydroxyl H atom H1 was found in a difference map and refined freely. All H atoms were refined with Uiso=1.2Ueq(parent atom) or Uiso=1.5Ueq(parent atom)

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the title compound, with the atom-numbering scheme and 30% probability displacement ellipsoids.
1-{5-[(E)-(4-Propylphenyl)diazenyl]-2-hydroxyphenyl}ethanone top
Crystal data top
C17H18N2O2F(000) = 600
Mr = 282.33Dx = 1.270 Mg m3
Monoclinic, P21/cMelting point: 350 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.8315 (5) ÅCell parameters from 29224 reflections
b = 7.5573 (2) Åθ = 1.5–28.0°
c = 13.5020 (4) ŵ = 0.08 mm1
β = 102.578 (3)°T = 150 K
V = 1477.07 (8) Å3Prism, brown
Z = 40.75 × 0.47 × 0.21 mm
Data collection top
Stoe IPDS II
diffractometer
3054 independent reflections
Radiation source: fine-focus sealed tube2680 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.8°
ω scansh = 1818
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.946, Tmax = 0.984l = 1616
21625 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H 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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.16 e Å3
0 constraints
Crystal data top
C17H18N2O2V = 1477.07 (8) Å3
Mr = 282.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.8315 (5) ŵ = 0.08 mm1
b = 7.5573 (2) ÅT = 150 K
c = 13.5020 (4) Å0.75 × 0.47 × 0.21 mm
β = 102.578 (3)°
Data collection top
Stoe IPDS II
diffractometer
3054 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
2680 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.984Rint = 0.039
21625 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å3
3054 reflectionsΔρmin = 0.16 e Å3
195 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.47997 (7)0.68823 (13)0.36509 (7)0.0259 (2)
C20.50206 (7)0.61432 (14)0.27782 (8)0.0288 (2)
H20.56000.56440.28150.035*
C30.43876 (7)0.61552 (14)0.18743 (8)0.0310 (2)
H30.45400.56700.12990.037*
C40.35131 (7)0.68914 (14)0.18103 (8)0.0293 (2)
C50.32685 (7)0.76156 (13)0.26807 (7)0.0264 (2)
C60.39293 (7)0.75846 (13)0.35970 (7)0.0260 (2)
H60.37800.80450.41800.031*
C70.23300 (7)0.83175 (13)0.26066 (8)0.0287 (2)
C80.20412 (7)0.89985 (15)0.35252 (8)0.0319 (2)
H8A0.14250.94600.33350.048*
H8B0.24550.99210.38290.048*
H8C0.20580.80530.40040.048*
C90.68461 (7)0.65001 (13)0.55710 (7)0.0253 (2)
C100.65886 (7)0.69262 (14)0.64747 (8)0.0281 (2)
H100.59840.72620.64670.034*
C110.72316 (7)0.68489 (14)0.73810 (8)0.0290 (2)
H110.70550.71490.79800.035*
C120.81431 (7)0.63289 (13)0.74182 (8)0.0277 (2)
C130.83931 (7)0.59345 (15)0.65066 (8)0.0310 (2)
H130.89990.56110.65130.037*
C140.77553 (7)0.60153 (14)0.55917 (8)0.0298 (2)
H140.79340.57460.49910.036*
C150.88314 (7)0.61869 (15)0.84173 (8)0.0323 (2)
H15A0.91760.50940.84240.039*
H15B0.84980.61200.89590.039*
C160.95106 (7)0.77208 (15)0.86325 (8)0.0332 (2)
H16A0.91710.88250.85880.040*
H16B0.98810.77420.81220.040*
C171.01453 (8)0.75689 (16)0.96802 (8)0.0364 (3)
H17A1.05620.85570.97910.055*
H17B1.04920.64890.97220.055*
H17C0.97820.75651.01880.055*
N10.54195 (6)0.69552 (12)0.46137 (6)0.0276 (2)
N20.62283 (6)0.64756 (12)0.45996 (6)0.0276 (2)
O10.29175 (6)0.68415 (12)0.09043 (6)0.0392 (2)
O20.17695 (6)0.83191 (12)0.17831 (6)0.0416 (2)
H10.2391 (13)0.734 (2)0.1040 (13)0.074 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0254 (5)0.0280 (5)0.0231 (5)0.0024 (4)0.0022 (4)0.0021 (4)
C20.0267 (5)0.0311 (5)0.0286 (5)0.0007 (4)0.0062 (4)0.0006 (4)
C30.0357 (6)0.0334 (5)0.0244 (5)0.0029 (4)0.0076 (4)0.0017 (4)
C40.0333 (5)0.0295 (5)0.0219 (5)0.0040 (4)0.0010 (4)0.0019 (4)
C50.0271 (5)0.0260 (5)0.0240 (5)0.0016 (4)0.0012 (4)0.0025 (4)
C60.0265 (5)0.0276 (5)0.0227 (5)0.0019 (4)0.0028 (4)0.0002 (4)
C70.0279 (5)0.0260 (5)0.0283 (5)0.0010 (4)0.0024 (4)0.0037 (4)
C80.0261 (5)0.0347 (6)0.0330 (6)0.0025 (4)0.0023 (4)0.0038 (4)
C90.0239 (5)0.0255 (5)0.0250 (5)0.0010 (4)0.0019 (4)0.0016 (4)
C100.0228 (5)0.0324 (5)0.0291 (5)0.0007 (4)0.0053 (4)0.0017 (4)
C110.0282 (5)0.0331 (5)0.0253 (5)0.0022 (4)0.0050 (4)0.0013 (4)
C120.0266 (5)0.0254 (5)0.0285 (5)0.0028 (4)0.0003 (4)0.0037 (4)
C130.0226 (5)0.0343 (5)0.0344 (6)0.0035 (4)0.0029 (4)0.0005 (4)
C140.0268 (5)0.0343 (5)0.0281 (5)0.0024 (4)0.0057 (4)0.0016 (4)
C150.0298 (5)0.0336 (6)0.0297 (5)0.0012 (4)0.0019 (4)0.0058 (4)
C160.0316 (5)0.0325 (5)0.0311 (5)0.0010 (4)0.0032 (4)0.0037 (4)
C170.0321 (6)0.0419 (6)0.0311 (6)0.0022 (5)0.0019 (4)0.0017 (5)
N10.0236 (4)0.0315 (4)0.0259 (4)0.0001 (3)0.0015 (3)0.0012 (3)
N20.0238 (4)0.0314 (4)0.0265 (4)0.0001 (3)0.0026 (3)0.0014 (3)
O10.0409 (5)0.0493 (5)0.0220 (4)0.0021 (4)0.0050 (3)0.0028 (3)
O20.0359 (4)0.0484 (5)0.0326 (4)0.0095 (4)0.0100 (3)0.0021 (4)
Geometric parameters (Å, º) top
C1—C61.3830 (14)C10—C111.3792 (14)
C1—C21.4057 (14)C10—H100.9300
C1—N11.4203 (12)C11—C121.3982 (14)
C2—C31.3682 (14)C11—H110.9300
C2—H20.9300C12—C131.3930 (15)
C3—C41.3965 (15)C12—C151.5079 (13)
C3—H30.9300C13—C141.3840 (14)
C4—O11.3444 (12)C13—H130.9300
C4—C51.4135 (15)C14—H140.9300
C5—C61.4013 (13)C15—C161.5217 (15)
C5—C71.4725 (14)C15—H15A0.9700
C6—H60.9300C15—H15B0.9700
C7—O21.2349 (12)C16—C171.5233 (14)
C7—C81.4893 (15)C16—H16A0.9700
C8—H8A0.9600C16—H16B0.9700
C8—H8B0.9600C17—H17A0.9600
C8—H8C0.9600C17—H17B0.9600
C9—C141.3917 (14)C17—H17C0.9600
C9—C101.3933 (14)N1—N21.2572 (12)
C9—N21.4271 (12)O1—H10.919 (19)
C6—C1—C2119.58 (9)C10—C11—C12121.34 (10)
C6—C1—N1116.35 (9)C10—C11—H11119.3
C2—C1—N1124.06 (9)C12—C11—H11119.3
C3—C2—C1120.34 (10)C13—C12—C11118.02 (9)
C3—C2—H2119.8C13—C12—C15121.11 (9)
C1—C2—H2119.8C11—C12—C15120.87 (9)
C2—C3—C4120.37 (10)C14—C13—C12121.16 (9)
C2—C3—H3119.8C14—C13—H13119.4
C4—C3—H3119.8C12—C13—H13119.4
O1—C4—C3117.55 (9)C13—C14—C9120.04 (10)
O1—C4—C5122.04 (10)C13—C14—H14120.0
C3—C4—C5120.39 (9)C9—C14—H14120.0
C6—C5—C4118.09 (9)C12—C15—C16114.06 (8)
C6—C5—C7122.34 (9)C12—C15—H15A108.7
C4—C5—C7119.54 (9)C16—C15—H15A108.7
C1—C6—C5121.21 (9)C12—C15—H15B108.7
C1—C6—H6119.4C16—C15—H15B108.7
C5—C6—H6119.4H15A—C15—H15B107.6
O2—C7—C5120.17 (10)C15—C16—C17111.68 (9)
O2—C7—C8119.36 (9)C15—C16—H16A109.3
C5—C7—C8120.46 (9)C17—C16—H16A109.3
C7—C8—H8A109.5C15—C16—H16B109.3
C7—C8—H8B109.5C17—C16—H16B109.3
H8A—C8—H8B109.5H16A—C16—H16B107.9
C7—C8—H8C109.5C16—C17—H17A109.5
H8A—C8—H8C109.5C16—C17—H17B109.5
H8B—C8—H8C109.5H17A—C17—H17B109.5
C14—C9—C10119.50 (9)C16—C17—H17C109.5
C14—C9—N2116.13 (9)H17A—C17—H17C109.5
C10—C9—N2124.35 (9)H17B—C17—H17C109.5
C11—C10—C9119.92 (9)N2—N1—C1113.86 (8)
C11—C10—H10120.0N1—N2—C9113.96 (8)
C9—C10—H10120.0C4—O1—H1103.0 (11)
C6—C1—C2—C31.58 (15)N2—C9—C10—C11177.63 (9)
N1—C1—C2—C3178.81 (9)C9—C10—C11—C120.73 (15)
C1—C2—C3—C40.41 (15)C10—C11—C12—C131.73 (15)
C2—C3—C4—O1179.12 (9)C10—C11—C12—C15177.81 (9)
C2—C3—C4—C50.68 (16)C11—C12—C13—C141.41 (15)
O1—C4—C5—C6178.96 (9)C15—C12—C13—C14178.13 (9)
C3—C4—C5—C60.59 (15)C12—C13—C14—C90.11 (16)
O1—C4—C5—C70.93 (15)C10—C9—C14—C130.93 (15)
C3—C4—C5—C7177.43 (9)N2—C9—C14—C13177.46 (9)
C2—C1—C6—C51.67 (15)C13—C12—C15—C1677.33 (13)
N1—C1—C6—C5178.69 (9)C11—C12—C15—C16103.14 (12)
C4—C5—C6—C10.59 (15)C12—C15—C16—C17176.16 (9)
C7—C5—C6—C1178.56 (9)C6—C1—N1—N2172.82 (9)
C6—C5—C7—O2180.00 (10)C2—C1—N1—N27.55 (14)
C4—C5—C7—O22.06 (15)C1—N1—N2—C9178.33 (8)
C6—C5—C7—C81.21 (15)C14—C9—N2—N1178.69 (9)
C4—C5—C7—C8176.72 (9)C10—C9—N2—N13.01 (14)
C14—C9—C10—C110.62 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.921 (19)1.675 (18)2.5365 (13)154.3 (16)

Experimental details

Crystal data
Chemical formulaC17H18N2O2
Mr282.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)14.8315 (5), 7.5573 (2), 13.5020 (4)
β (°) 102.578 (3)
V3)1477.07 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.75 × 0.47 × 0.21
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.946, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
21625, 3054, 2680
Rint0.039
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.097, 1.04
No. of reflections3054
No. of parameters195
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.16

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.921 (19)1.675 (18)2.5365 (13)154.3 (16)
 

Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

First citationAlbayrak, Ç., Gümrükçüoğlu, İ., Odabaşoğlu, M., İskeleli, N. O. & Ağar, E. (2009). J. Mol. Struct. 932, 43–54.  Web of Science CSD CrossRef CAS Google Scholar
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