organic compounds
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
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 ); 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).
see: Russ & Tappe (1994Experimental
Crystal data
|
Refinement
|
|
Data collection: X-AREA (Stoe & Cie, 2002); cell 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
10.1107/S1600536811004910/bh2335sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811004910/bh2335Isup2.hkl
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).
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)
Data collection: X-AREA (Stoe & Cie, 2002); cell
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).Fig. 1. An ORTEP view of the title compound, with the atom-numbering scheme and 30% probability displacement ellipsoids. |
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 monochromator | 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 |
C17H18N2O2 | V = 1477.07 (8) Å3 |
Mr = 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)° |
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 = 0.984 | Rint = 0.039 |
21625 measured reflections |
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 | Δρmax = 0.21 e Å−3 |
3054 reflections | Δρmin = −0.16 e Å−3 |
195 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C17H18N2O2 |
Mr | 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) |
Tmin, Tmax | 0.946, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21625, 3054, 2680 |
Rint | 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 |
Δρmax, Δρmin (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).
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).
References
Albayrak, 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
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. CrossRef Google Scholar
Deveci, O., Işık, S., Albayrak, C. & Ağar, E. (2005). Acta Cryst. E61, o3226–o3227. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673–o1674. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Karadayı, N., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o3695–o3696. Web of Science CSD CrossRef IUCr Journals Google Scholar
Russ, H. W. & Tappe, H. (1994). Eur. Patent Appl. EP 629 627. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
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. Web of Science CrossRef CAS Google Scholar
Yazıcı, S., Albayrak, Ç., Gümrükçüoğlu, İ., Şenel, İ. & Büyükgüngör, O. (2010). Acta Cryst. E66, o559–o560. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.