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

Yazıcı, S.; Albayrak, Ç.; Gümrükçüoğlu, I.; Şenel, I.; Büyükgüngör, O.

doi:10.1107/S1600536811004910

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o640

doi:10.1107/S1600536811004910

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

Serap Yazıcı,^a ^* Çiğdem Albayrak,^b Ismail Gümrükçüoğlu,^c Ismet Şenel ^a and Orhan Büyükgüngör ^a

^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 ); 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_r = 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 ) 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[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
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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)

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 ).

Supporting information

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

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

checkCIF report

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 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.

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).

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

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

C₁₇H₁₈N₂O₂	F(000) = 600
M_r = 282.33	D_x = 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

Data collection top

Stoe IPDS II diffractometer	3054 independent reflections
Radiation source: fine-focus sealed tube	2680 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.8°
ω scans	h = −18→18
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.946, T_max = 0.984	l = −16→16
21625 measured reflections

Refinement top

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(F_o²) + (0.0487P)² + 0.2885P] where P = (F_o² + 2F_c²)/3
3054 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³
0 constraints

Crystal data top

C₁₇H₁₈N₂O₂	V = 1477.07 (8) Å³
M_r = 282.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8315 (5) Å	µ = 0.08 mm⁻¹
b = 7.5573 (2) Å	T = 150 K
c = 13.5020 (4) Å	0.75 × 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)
T_min = 0.946, T_max = 0.984	R_int = 0.039
21625 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.21 e Å⁻³
3054 reflections	Δρ_min = −0.16 e Å⁻³
195 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₂
M_r	282.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.8315 (5), 7.5573 (2), 13.5020 (4)
β (°)	102.578 (3)
V (Å³)	1477.07 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.75 × 0.47 × 0.21

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.946, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	21625, 3054, 2680
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.04
No. of reflections	3054
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···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)

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).

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