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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Feb 16;67(Pt 3):o640. doi: 10.1107/S1600536811004910

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

Serap Yazıcı a,*, Çiğdem Albayrak b, Ismail Gümrükçüoğlu c, Ismet Şenel a, Orhan Büyükgüngör a
PMCID: PMC3052044  PMID: 21522393

Abstract

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 ▶); 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 ▶).graphic file with name e-67-0o640-scheme1.jpg

Experimental

Crystal data

  • C17H18N2O2

  • M r = 282.33

  • Monoclinic, Inline graphic

  • 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 ▶).

Supplementary Material

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

e-67-0o640-sup1.cif (17.5KB, cif)

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

e-67-0o640-Isup2.hkl (146.8KB, hkl)

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

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)
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Acknowledgments

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).

supplementary crystallographic information

Comment

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 N═N 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.

Experimental

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

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)

Figures

Fig. 1.

Fig. 1.

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An ORTEP view of the title compound, with the atom-numbering scheme and 30% probability displacement ellipsoids.

Crystal data

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
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Data collection

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
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Refinement

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
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2335).

References

  1. Albayrak, Ç., Gümrükçüoğlu, İ., Odabaşoğlu, M., İskeleli, N. O. & Ağar, E. (2009). J. Mol. Struct. 932, 43–54.
  2. 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.
  3. Deveci, O., Işık, S., Albayrak, C. & Ağar, E. (2005). Acta Cryst. E61, o3226–o3227.
  4. El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673–o1674. [DOI] [PMC free article] [PubMed]
  5. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  6. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  7. Karadayı, N., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3695–o3696.
  8. Russ, H. W. & Tappe, H. (1994). Eur. Patent Appl. EP 629 627.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  10. Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
  11. 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. [DOI] [PubMed]
  12. Yazıcı, S., Albayrak, Ç., Gümrükçüoğlu, İ., Şenel, İ. & Büyükgüngör, O. (2010). Acta Cryst. E66, o559–o560. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-0o640-sup1.cif (17.5KB, cif)

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

e-67-0o640-Isup2.hkl (146.8KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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