81 ( E)-5-[(3-Bromophenyl)diazenyl]-2-hydroxy-3-methoxybenz

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81 ( E)-5-[(3-Bromophenyl)diazenyl]-2-hydroxy-3-methoxybenz
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson ( E  )-5-[(3-Bromophenyl)diazenyl]-2-hydroxy-3-methoxybenzaldehyde Onur S¸ahin, C¸i ˇgdem Albayrak, Mustafa Odabas¸o ˇglu and Orhan B¨uy¨ukg¨ung  ¨or Copyright © International Union of CrystallographyAuthor(s) of this paper may load this reprint on their own web site provided that this cover page is retained. Republication of this article or itsstorage in electronic databases or the like is not permitted without prior permission in writing from the IUCr. Acta Cryst. (2005). E 61 , o4276–o4278 S¸ahin et al. ¯ C 14 H 11 BrN 2 O 3  organic papers o4276 S¸ahin et al.  C 14 H 11 BrN 2 O 3 doi:10.1107/S1600536805038365 Acta Cryst. (2005). E 61 , o4276–o4278 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 ( E  )-5-[(3-Bromophenyl)diazenyl]-2-hydroxy-3-methoxybenzaldehyde Onur S¸ahin, a * C¸igˇdemAlbayrak, b Mustafa Odabas¸ogˇlu b and Orhan Bu¨yu¨kgu¨ngo¨r a a Department of Physics, Ondokuz MayısUniversity, TR-55139 Samsun, Turkey, and b Department of Chemistry, Ondokuz MayısUniversity, TR-55139 Samsun, TurkeyCorrespondence e-mail: onurs@omu.edu.tr Key indicators Single-crystal X-ray study T  = 296 KMean   (C–C) = 0.004 A˚ R factor = 0.037 wR factor = 0.091Data-to-parameter ratio = 18.2For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e. # 2005 International Union of CrystallographyPrinted in Great Britain – all rights reserved The title structure, C 14 H 11 BrN 2 O 3 , displays the characteristicfeatures of azobenzene derivatives. The two aromatic rings arenearly coplanar, forming a dihedral angle of 8.71 (12)  . Thereis a strong intramolecular O—H ÁÁÁ O bond, and weak  –  andC—H ÁÁÁ  interactions stabilize the structure. Comment Azo compounds have been the most widely used class of dyesowing to their versatile applications in various fields, such asdyeing textile fibres, colouring different materials, plastics,biological medical studies, lasers, liquid crystalline displays,electrooptical devices and ink-jet printers in high-technologyareas (Catino & Farris, 1985). In azo compounds, conversionfrom the trans to the cis form can lead to photochromism.Photochromic compounds are of great interest for the controland measurement of radiation intensity, optical computers anddisplay systems (Du ¨ rr & Bouas-Laurent, 1990), and forpotential applications in molecular electronic devices (Martin et al. , 1995).An ORTEP-3 (Farrugia, 1997) view of the molecule of thetitle compound, (I), and the molecular packing are shown inFigs. 1 and 2, respectively. Selected bond distances and angles Received 14 November 2005Accepted 21 November 2005Online 26 November 2005 Figure 1 The molecular structure of (I), showing the atom-numbering scheme.Displacement ellipsoids are drawn at the 30% probability level. The O–H ÁÁÁ O intramolecular hydrogen bond is indicated by a dashed line. electronic reprint  are given in Table 1. The aromatic rings are in a trans configuration with respect to the azo double bond.The dihedral angle  1 between the mean planes of thebenzene ring (C1–C6) and the C1–N1 N2—C7 azo bridge is10.95 (21)  , and the angle  2 between the C1–N1 N2–C7 azogroup and the multiply substituted benzene ring (C7–C12) is175.64 (6)  . The angle  3 between the planes of the twoaromatic rings is 8.71 (12)  . The N1—C1 and N2—C7 bondlengths of 1.435 (3) A˚and 1.415 (3) A˚, respectively, indicatesingle-bond character and the N N bond length of 1.257 (3) A˚is indicative of significant double-bond character.In the extended structure of (I), shown in Fig. 2, there areweak  –  and C—H ÁÁÁ  interactions. An intermolecular  –  contact occurs between the two symmetry-related C7–C12rings of neighbouring molecules. Ring A (C7–C12) is orientedin such a way that the perpendicular distance from A to A i is3.500 (13) A˚[symmetry code: (i) 1 À x , y , 12 À z ]. The distancebetween the ring centroids is 3.6594 (14) A˚. In the crystalstructure of (I), there is also a weak C–H ÁÁÁ  interactionbetween C2–H1 and the C7–C12 ring. The C—H ÁÁÁ CgA contact distance is 3.38 A˚, where CgA is the centroid of ring A .The perpendicular distance between atom H1 and the plane of phenyl ring is 3.28 A˚and the C—H ÁÁÁ CgA angle is 84  [symmetry code: (ii) 1 À x , 1 À y , À z ]. Compound (I) also hasintramolecular O—H ÁÁÁ O hydrogen bonds (see Table 2 fordetails). Experimental A mixture of 3-bromoaniline (1.51 g, 8.8 mmol), water (50 ml) andconcentrated hydrochloric acid (2.2 ml, 26.4 mmol) was heated withstirring until a clear solution was obtained. This solution was cooledto 273–278 K, and a solution of sodium nitrite (0.85 g, 12.3 mmol) inwater was added dropwise while the temperature was maintainedbelow 278 K. The resulting mixture was stirred for 30 min in an icebath. An o -vanillin (1.19 g, 8.8 mmol) solution (pH 9) was addedgradually to the solution of cooled 3-bromobenzenediazoniumchloride, prepared as described above, and the resulting mixture wasstirred at 273–278 K for 60 min in an ice bath. The product wasrecrystallized from glacial acetic acid to obtain solid ( E  )-5-[(3-bromophenyl)diazenyl]-2-hydroxy-3-methoxybenzaldehyde. Theproduct, (I), was recrystallized from acetic acid (yield 84%; m.p. 424–425 K). Crystal data C 14 H 11 BrN 2 O 3 M  r  = 335.16Orthorhombic, Pbcna = 12.5131 (6) A˚ b = 13.2636 (6) A˚ c = 16.5594 (7) A˚ V  = 2748.3 (2) A˚ 3 Z  = 8 D  x = 1.620 Mg m À 3 Mo K   radiationCell parameters from 23001reflections   = 2.2–28.0   = 3.00 mm À 1 T  = 296 KPrism, brown0.50  0.36  0.13 mm Data collection Stoe IPDS-2 diffractometer ! scansAbsorption correction: integration(  X-RED32 ; Stoe & Cie, 2002) T  min = 0.275, T  max = 0.69228648 measured reflections3300 independent reflections2374 reflections with I  > 2   (  I  ) R int = 0.108   max = 28.0  h = À 16 ! 16 k = À 17 ! 17 l  = À 21 ! 21 Refinement  Refinement on F  2 R [ F  2 > 2   ( F  2 )] = 0.037 wR ( F  2 ) = 0.091 S = 1.033300 reflections181 parametersH-atom parameters constrained w = 1/[   2 ( F  o2 ) + (0.0362 P ) 2 + 1.1485 P ]where P = ( F  o2 + 2 F  c2 )/3( Á /   ) max < 0.001 Á  max = 0.29 e A˚ À 3 Á  min = À 0.41 e A˚ À 3 Table 1 Selected geometric parameters (A˚,  ). C3—Br1 1.893 (3)C1—N1 1.435 (3)C7—N2 1.415 (3)C10—O2 1.343 (3)C13—O3 1.221 (3)N1—N2 1.257 (3)O3—C13—C9 124.3 (3)C13—C9—C10—O2 0.4 (4) C1—N1—N2—C7 À 177.6 (2) Table 2 Hydrogen-bond geometry (A˚,  ). D —H ÁÁÁ  A D —H H ÁÁÁ  A D ÁÁÁ  A D —H ÁÁÁ  A O2—H2 ÁÁÁ O3 0.82 1.92 2.632 (3) 145 organic papers Acta Cryst. (2005). E 61 , o4276–o4278 S¸ahin et al.  C 14 H 11 BrN 2 O 3 o4277 Figure 2 Part of the crystal structure of (I). Dashed lines indicate stacking  –  andC—H ÁÁÁ  interactions [symmetry codes: (i) 1 À x , y , 12 À z ; (ii) 1 À x ,1 À y , À z ]. H atoms not involved in these interactions have been omittedfor clarity. electronic reprint  All H atoms bound to carbon were refined using a riding modelwith C—H = 0.93 A˚[ U  iso (H) = 1.2 U  eq (parent atom)] for aromatic andC—H = 0.96 A˚[ U  iso (H) = 1.5 U  eq (parent atom)] for methyl C atoms.The H atom of the hydroxyl O atom was refined with O—H = 0.82 A˚[ U  iso (H) = 1.5 U  eq (O)].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, 1997); program(s)used to refine structure: SHELXL97  (Sheldrick, 1997); moleculargraphics: ORTEP-3 for Windows (Farrugia, 1997); software used toprepare material for publication: WinGX  (Farrugia, 1999). The authors acknowledge the Faculty of Arts and Sciences,Ondokuz Mayıs University, Turkey, for the use of the StoeIPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund). References Catino, S. C. & Farris R. E. (1985). Azo Dyes. In Kirk–Othmer ConciseEncyclopaedia of Chemical Technology , edited by M. Grayson. New York:John Wiley and Sons.Du ¨ rr, H. & Bouas-Laurent, H. (1990). Photochromism: Molecules andSystems . Amsterdam: Elsevier.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837–838.Martin, P. J., Petty, M. C., Bryce, M. R. & Bloor, D. (1995). An Introduction toMolecular Electronics , ch. 6. New York: Oxford University Press.Sheldrick, G. M. (1997). SHELXS97  and SHELXL97  . University of Go ¨ ttingen, Germany.Stoe & Cie (2002). X-AREA and X-RED32 . Stoe & Cie, Darmstadt, Germany. organic papers o4278 S¸ahin et al.  C 14 H 11 BrN 2 O 3 Acta Cryst. (2005). E 61 , o4276–o4278 electronic reprint
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