Journal of Chemical and Pharmaceutical Research, 2013, 5(1): Research Article. XRD Data analysis of 1-(2,5-dimethoxyphenylazo)-2-naphtol

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1 Available online Journal of Chemical and Pharmaceutical Research, 2013, 5(1):12-18 Research Article ISSN : CODEN(USA) : JCPRC5 XRD Data analysis of 1-(2,5-dimethoxyphenylazo)-2-naphtol Assia Mili, Ali Benosmane, Souheyla Chetioui and Abdelkader Bouchoul * Unité de recherche de Chimie de l'environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université Constantine 1, Constantine, Algérie. ABSTRACT The present paper reports the synthesis and XRD characterization of 1- (2, 5- diméthoxyphénylazo)-2-naphtol which are prepared by diazotization and copulation reaction using 2, 5- diméthoxyaniline and β-naphtol as a coupling component. After recrystallization in pentane,the azo-compound was isolated as brown reddish crystal plates. XRD data analysis shows that our compound of empirical formula C 18 H 16 N 2 O 3 crystallizes in space group Pbca orthorhombic system with: a = Å; b = Å; c = Å; α =90.00 ; β = ;γ =90.00 ; Z = 8. Keywords: X-Ray Diffraction, azo-dyes, diazotization, copulation, chromophore. INTRODUCTION Azo compounds, which were developed in the mid 1800s, are one of the most common dye materials and are useful synthetic intermediates [1, 2]. They have been widely utilized as dyes and analytic reagents; theyare also used in substrates such as textile fibres, leather, plastics, papers, hair, mineral oils, waxes, foodstuffs and cosmetics [3-5]and considered as the most important class of synthetic dyes and pigments, representing 60-80% of all organic colorants. Hence azo colorants are part of our everyday colourful life, they are all around us and we could not do without them [6-9].They contain the basic structure of Ar-N=N-Ar. Their color is due to the high level of conjugation that extends through N-N double bond to the aryl unit [10-11]. RESULTS AND DISCUSSION The product concerned was prepared according to the classical method of synthesis of an azo dye where an aryl diazonium-cation attacks via electrophilic substitution reaction another aromatic aryl ring ; the reaction is conducted near ice temperatures (0-5 C) at ph mildly acidic or neutral[12-17]. The synthetized azo-compound (scheme 1) is in the form of a red-orange powder; it is not water-soluble, but readily soluble in many organic solvents with a melting point of 156 C. After recrystallization from pentane, reddish brown crystals, stable in air, were obtained. XRD recording data of the title compound provides not only the size of the mesh, but also nature and distance of the chemical bonds that allow us to know the geometry and material properties. 12

2 Scheme 1:1- (2, 5- diméthoxyphénylazo)-2-naphtol The monomer crystal unit, that empirical formula C 18 H 16 N 2 O 3,was then analyzed by X-ray diffraction[18-26];the results of the data analysis are presented below: Table1. Crystal data C 18H 16N 2O 3 M r = D x = Mg m 3 Orthorhombic, Pbca Melting point: 429 K Hall symbol: -P 2ac 2ab Mo Kα radiation, λ = Å a = (5) Å Cellparametersfrom2729reflections b = (5) Å θ = c = (5) Å µ = 0.09 mm 1 V = (19) Å 3 T = 293 K Z = 8 Needle F(000) = mm Table2. Data collection Kappa CCD diffractometer 1506 reflections with I> 2σ(I) Radiation source: fine-focus sealed tube R int = graphite θ max = 25.5, θ min = 2.5 Detector resolution:? pixels mm -1 h = φ scans k = measuredreflections l = independentreflections Table 3.Refinement Refinement onf 2 Secondary atom site location:difference Fourier map Least-squares matrix:full Hydrogen site location:inferred from neighbouring sites R[F 2 > 2σ(F 2 )] = H atoms treated by a mixture of independent and constrained refinement wr(f 2 ) = w = 1/[σ 2 (F 2 o ) + (0.0876P) P] where P = (F 2 o + 2F 2 c )/3 S = 1.00 ( /σ) max = reflections ρ max = 0.18 e Å 3 212parameters ρ min = 0.11 e Å 3 1restraint Extinction correction:none?constraints Extinction coefficient:? Primary atom site location:structure-invariant direct methods 13

3 Table 4.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso*/u eq O (2) (17) (13) (10) O (18) (16) (16) (10) O (2) (15) (15) (9) N (18) (15) (16) (9) N (16) (14) (13) (8) C (2) (16) (19) (10) C (2) (19) (2) (11) C (2) (19) (3) (13) C (2) (2) (2) (14) C (2) (18) (2) (11) C (2) (17) (18) (10) C (2) (17) (16) (9) C (3) (2) (19) (12) C (3) (3) (2) (16) C (3) (2) (3) (16) C (2) (19) (2) (13) C (2) (17) (19) (10) C (2) (18) (2) (11) C (3) (2) (2) (14) C (3) (2) (3) (18) C (3) (2) (3) (16) C (3) (3) (3) (19) C (3) (2) (2) (16) H (3) (2) (5) (13)* H * H * H * H * H * H * H * H * H * H17A * H17B * H17C * H18A * H18B * H18C * Table 5.Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (17) (2) (15) (15) (12) (13) O (16) (18) (19) (12) (13) (14) O (16) (16) (17) (12) (12) (13) N (14) (15) (17) (11) (11) (13) N (12) (13) (15) (10) (10) (11) C (15) (16) (2) (12) (13) (14) C (17) (19) (2) (13) (16) (17) C (17) (2) (3) (13) (17) (19) C (19) (2) (3) (15) (18) (19) C (18) (18) (2) (14) (14) (16) C (15) (16) (2) (12) (13) (14) C (15) (17) (17) (12) (12) (14) C (2) (2) (2) (16) (16) (18) C (3) (3) (2) (2) (18) (2) C (2) (3) (3) (19) (2) (2) C (18) (19) (3) (14) (16) (17) C (14) (16) (2) (11) (12) (14) C (17) (2) (2) (14) (14) (15) C (2) (2) (3) (16) (19) (2) C (2) (3) (4) (16) (2) (3) C (2) (2) (4) (16) (2) (2) C (3) (3) (4) (2) (2) (3) C (3) (3) (2) (2) (2) (19) 14

4 Table 6.Geometricparameters (Å, ) O1 C (4) C11 C (4) O2 C (4) C12 C (5) O2 C (5) C13 C (4) O3 C (4) C14 C (5) O3 C (4) C15 C (7) N1 N (3) C3 H N1 C (4) C4 H N2 C (3) C6 H N1 H (11) C9 H C1 C (4) C10 H C1 C (4) C13 H C2 C (5) C14 H C3 C (6) C15 H C4 C (4) C16 H C5 C (4) C17 H17A C7 C (4) C17 H17B C7 C (4) C17 H17C C8 C (5) C18 H18A C9 C (5) C18 H18B C10 C (6) C18 H18C C11 C (5) O1 N (4) C10 H18C v O1 N (3) C14 H3 x O2 N (3) C15 H3 x O3 C18 i (4) C17 H O3 C17 ii (5) C18 H O1 H (2) C18 H14 xi O1 H10 iii H1 O (2) O2 H (3) H1 O (3) O3 H17A ii H1 C (3) O3 H18B i H3 C N1 O (4) H3 H17B N1 O (3) H3 H17C N1 C14 iv (4) H3 C14 xii N2 O (3) H3 C15 xii N2 H H6 N N2 H H6 C C1 C13 iv (4) H6 H18B C1 C14 iv (4) H6 H18C C4 C7 iv (4) H10 H C5 C7 iv (4) H10 O1 xiii C6 C12 iv (4) H13 N C7 C5 v (4) H14 C18 xiv C7 C4 v (4) H14 H18A xiv C8 C18 vi (5) H15 C2 xv C9 C18 vi (5) H15 C3 xv C12 C6 v (4) H16 H C13 C1 v (4) H17A O3 vii C14 N1 v (4) H17B C C14 C1 v (4) H17B H C17 O3 vii (5) H17C C C18 C8 viii (5) H17C H C18 O3 i (4) H17C H18B iv C18 C9 viii (5) H18A H14 xi C2 H15 ix H18B C C3 H17C H18B H C3 H17B H18B O3 i C3 H15 ix H18B H17C v C6 H18B H18C C C6 H18C H18C H C8 H (3) H18C C10 iv C2 O2 C (3) C13 C14 C (3) C5 O3 C (2) C14 C15 C (3) N2 N1 C (2) C11 C16 C (4) N1 N2 C (2) C2 C3 H C1 N1 H1 121 (2) C4 C3 H N2 N1 H1 120 (2) C3 C4 H C2 C1 C (3) C5 C4 H N1 C1 C (3) C1 C6 H

5 N1 C1 C (2) C5 C6 H O2 C2 C (3) C8 C9 H O2 C2 C (3) C10 C9 H C1 C2 C (3) C9 C10 H C2 C3 C (3) C11 C10 H C3 C4 C (3) C12 C13 H C4 C5 C (3) C14 C13 H O3 C5 C (3) C13 C14 H O3 C5 C (2) C15 C14 H C1 C6 C (2) C14 C15 H C8 C7 C (3) C16 C15 H N2 C7 C (2) C11 C16 H N2 C7 C (2) C15 C16 H C7 C8 C (3) O2 C17 H17A O1 C8 C (3) O2 C17 H17B O1 C8 C (3) O2 C17 H17C C8 C9 C (3) H17A C17 H17B C9 C10 C (4) H17A C17 H17C C12 C11 C (3) H17B C17 H17C C10 C11 C (3) O3 C18 H18A C10 C11 C (3) O3 C18 H18B C11 C12 C (2) O3 C18 H18C C7 C12 C (3) H18A C18 H18B C7 C12 C (2) H18A C18 H18C C12 C13 C (3) H18B C18 H18C C17 O2 C2 C (3) N2 C7 C8 C (3) C17 O2 C2 C3 5.7 (4) C12 C7 C8 O (3) C18 O3 C5 C (3) C12 C7 C8 C9 1.5 (4) C18 O3 C5 C6 2.2 (4) N2 C7 C12 C (2) C1 N1 N2 C (2) N2 C7 C12 C (4) N2 N1 C1 C (2) C8 C7 C12 C (4) N2 N1 C1 C6 0.1 (4) C8 C7 C12 C (3) N1 N2 C7 C8 2.7 (4) O1 C8 C9 C (4) N1 N2 C7 C (2) C7 C8 C9 C (5) N1 C1 C2 O2 0.5 (4) C8 C9 C10 C (6) N1 C1 C2 C (2) C9 C10 C11 C (5) C6 C1 C2 O (2) C9 C10 C11 C (4) C6 C1 C2 C3 0.5 (4) C10 C11 C12 C7 0.0 (4) N1 C1 C6 C (2) C10 C11 C12 C (3) C2 C1 C6 C5 0.2 (4) C16 C11 C12 C (3) O2 C2 C3 C (3) C16 C11 C12 C (4) C1 C2 C3 C4 0.6 (4) C10 C11 C16 C (3) C2 C3 C4 C5 0.1 (4) C12 C11 C16 C (5) C3 C4 C5 O (3) C7 C12 C13 C (3) C3 C4 C5 C6 0.8 (4) C11 C12 C13 C (4) O3 C5 C6 C (3) C12 C13 C14 C (5) C4 C5 C6 C1 0.9 (4) C13 C14 C15 C (5) N2 C7 C8 O1 3.2 (5) C14 C15 C16 C (5) Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y, z+1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y, z+1/2; (v) x 1/2, y, z+1/2; (vi) x, y+1/2, z 1/2; (vii) x+1/2, y, z 1/2; (viii) x, y+1/2, z+1/2; (ix) x 1/2, y 1/2, z; (x) x, y+1/2, z+1/2; (xi) x+1/2, y+1/2, z+1; (xii) x, y 1/2, z+1/2; (xiii) x 1/2, y+1/2, z; (xiv) x 1/2, y+1/2, z+1; (xv) x 1/2, y+1/2, z. Table 7.Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A N1 H1 O (11) 1.85 (2) (4) 134 (3) N1 H1 O (11) 2.28 (3) (3) 103 (2) Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles. The structure of the title compound in the single crystal is given in figure 1. 16

6 Figure 1:Structure of (1-(2,5-diméthoxyphénylazo)-2-naphtol ) CONCLUSION XRD data analysis of the structure shows a crystal monomer unit of empirical formula C 18 H 16 N 2 O 3 witch crystallizes in space group P bca orthorhombic system.the packing diagram of the compound is given in figure 2. Figure 2:The packing diagram of thecompound withinteratomic interactions bonds. Figure 3:Angle between naphthalene and benzene ring systems The angle between the naphthalene and the benzene ring systems is Therefore this deviation shows that the structure is not completely planar. 17

7 Computing details Data collection: Collect (Bruker AXS BV, ); cell refinement: HKLDENZO and SCALEPACK (Otwinowski& Minor 1997); data reduction: HKLDENZO and SCALEPACK (Otwinowski& Minor 1997); program(s) used to solve structure:shelxl97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2010); software used to prepare material for publication: PLATON (Spek, 2003). Acknowledgements The author would like to thanks Mr. L. OUAHAB,University of Rennes (France), for his valuable collaboration in the recording and interpretation of XRD data and Professor S.E. BOUAOUD, University of Constantine (Algeria) for providing laboratory facilities and encouragements. REFERENCES [1]. M. Jarman, S. E. Barrie, J. J. Deadman, J. Houghton,R. McCague,M. G. Rowlands, J. Med. Chem.,1990, 33(9), [2].E.N. Abrahart, «Dyes and their Intermediates», 1976, Ed., Edward Arnold, pp and pp [3]. H. W. Russ, H. Tappe, Eur. Pat. Appl. EP. 1994, 629, 667 [4].H.Z. Shams, M.H. Helal, I.M. Samir, R.M. Mohareb, Pigment & Resin Technology, 2008, 37 (5), [5].F. Mohamed, Y.A. Youssef, Pigment & Resin Technology, 2012, 41 (1), [6] P. S. Patel, M. V. Hathi, J. Chem. Pharm. Res., 2010, 2(6), [7] L.A. Saghatforoush, R. Mehdizadeha and F. Chalabian, J. Chem. Pharm. Res., 2011, 3(2), [8] J. R. Patel, K. S. Nimavat and K. B. Vyas, J. Chem. Pharm. Res., 2011, 3(6), [9] A. J. M. Xavier, M. Thakur, J. Margaret Marie, J. Chem. Pharm. Res., 2012, 4(2), [10]. C.L. Hsueh, Y.H. Huang, C.C. Wang, C.Y. Chen, Chemosphere, 2005, 58, (10), [11].Y.M. ElKholy, S.A. Abd El-Hafiz, Pigment &ResinTechnology, 1994, 23, (4), 3 5 [12]. A. Bouchoul, Thèse de Doctorat d Etat, 2002, Université Mentouri Constantine [13]. M. Hedayatullah, «Les Colorants Synthétiques», P.U.F Edition, Paris,1976, pp [14]. M. Hedayatullah,Bull. Soc. Chim. France, 1972, [15]. P.F. Gordon and P. Gregory, «Organic Chemistry in Colour», Springer-Verlag, Berlin, 1983, pp [16]. S. H. Lee, J. Y. Kim, J. Ko, J. Y. Lee and J. S. Kim, J. Org. Chem., , [17].C. Wang, Y. Wang, X. Wang, X. Wang, H. Wang, J. Chem. Educ., 2000, 77, 903 [18].R. Gup, B. Kirkan, Turkish. J. Chem. 2008, 32, [19]. S. Wang, S. Shen, H. Xu, Dyes and Pigments, 2000, 44, [20]. X. Ji-Jun,L. Jun, P.Min and J. Chuan-Ming,ActaCryst., 2010, E66, o1752 [21]. L. J. Farrugia, J.Appl.Cryst.,1997, 30, 565 [22]. G. M. Sheldrick, ActaCryst.,2008, A64, [23]. M. Wang, K. Funabikiand M. Matsui,Dyes and Pigments, , [24]. F. Oueslati, I. Dumazet-Bonnamour and R. Lamartine, New.J. Chem.,2004, 28, [25]. T. Steiner, Angew. Chem. Int. Ed., 2002, 41, [26]. A. Benosmane, H. Bouguerria, A. Bouchoul and S. E. Bouaoud,J. Chem. Bio. Phy. Sci.Sec. A,2012, 2, (1),