= 0.09 mm 1 T = 294 (2) K. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN (3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol = 0.09 mm 1 T = 294 (2) K Data collection Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.902, T max = (expected range = ) mm 9949 measured reflections 4026 independent reflections 3212 reflections with I > 2(I) R int = Muhammad Hanif, a Ghulam Qadeer, a Nasim Hasan Rama a * and Wai-Yeung Wong b a Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and b Department of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong Correspondence nasimhrama@yahoo.com Received 6 October 2008; accepted 17 October 2008 Key indicators: single-crystal X-ray study; T = 294 K; mean (C C) = Å; R factor = 0.048; wr factor = 0.146; data-to-parameter ratio = In the molecule of the title compound, C 18 H 19 N 3 O 3, the triazole ring is oriented with respect to the 3-methoxyphenyl and 2-methoxyphenyl rings at dihedral angles of (3) and (3), respectively. The dihedral angle between the two benzene rings is (3). In the crystal structure, intermolecular O HN and C HO hydrogen bonds link the molecules. There is a contact between the triazole and 3- methoxyphenyl rings [centroid centroid distance = (3) Å]. There is a contact between the triazole and one of the 3-methoxyphenyl rings [centroid centroid distance = (3) Å ]. C H contacts are also found between the benzene ring and the methyl groups of their 3- methoxy-substituents. Related literature For general background, see: Demirbas et al. (2002); Holla et al. (1998); Kritsanida et al. (2002); Omar et al. (1986); Paulvannan et al. (2000); Turan-Zitouni et al. (1999). For related structures, see: Öztürk et al. (2004a,b). For bond-length data, see: Allen et al. (1987). Experimental Crystal data C 18 H 19 N 3 O 3 M r = Monoclinic, P2 1 =n a = (11) Å b = (14) Å c = (11) Å = (2) V = (3) Å 3 Z =4 Mo K radiation Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Hydrogen-bond geometry (Å, ). 218 parameters H-atom parameters constrained max = 0.56 e Å 3 min = 0.40 e Å 3 D HA D H HA DA D HA O3 H3N3 i (15) 173 C5 H5AO1 ii (2) 147 C8 H8AO (2) 157 C4 H4ACg3 iii (3) 140 C7 H7ACg (3) 165 C18 H18ACg2 iv (3) 105 C18 H18BCg2 iv (3) 101 Symmetry codes: (i) x þ 2; y; z þ 2; (ii) x þ 1 2 ; y 1 2 ; z þ 3 2 ; (iii) x 1; y; z; (iv) x 1 2 ; y 1 2 ; z 3 2. Cg2 and Cg3 are the centroids of the C2 C7 and C C12 C17 rings, respectively. Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON. The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2549). References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1 19. Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Holla, B. S., Gonsalves, R. & Shenoy, S. (1998). Il Farmaco, 53, Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou- Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Il Farmaco, 57, Omar, A., Mohsen, M. E. & Wafa, O. A. (1986). Heterocycl. Chem. 23, Öztürk, S., Akkurt, M., Cansız, A., Koparır, M., Şekerci, M. & Heinemann, F. W. (2004a). Acta Cryst. E60, o425 o427. Öztürk, S., Akkurt, M., Cansız, A., Koparır, M., Şekerci, M. & Heinemann, F. W. (2004b). Acta Cryst. E60, o642 o644. Paulvannan, K., Chen, T. & Hale, R. (2000). Tetrahedron, 56, Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Spek, A. L. (2003). J. Appl. Cryst. 36, Turan-Zitouni, G., Kaplancikli, Z. A., Erol, K. & Kilic, F. S. (1999). Il Farmaco, 54, o2180 Hanif et al. doi: /s Acta Cryst. (2008). E64, o2180

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3 Acta Cryst. (2008). E64, o2180 [ doi: /s ] 5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol M. Hanif, G. Qadeer, N. H. Rama and W.-Y. Wong Comment Substituted triazole derivatives display significant biological activities including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral (Kritsanida et al., 2002) activities. The biological activity is closely related to the structure, possibly being due to the presence of the N C S unit (Omar et al., 1986). We are interested in the syntheses and biological activities of the aryloxyacetyl hydrazide derivatives and report herein the synthesis (Fig. 1) and crystal structure of the title compound. In the molecule of the title compound (Fig. 2), the bond lengths (Allen et al., 1987) and angles are within normal ranges, and they are comparable with those observed in related structures (Öztürk et al., 2004a, 2004b). In the triazole ring, the N3=C11 [ (17) Å] bond has double bond character. Rings A (C2-C7), B (N1/N2/N3/C10/C11) and C (C12-C17) are, of course, planar and the dihedral angles between them are A/B = (3), A/C = (3) and B/C = (3). In the crystal structure, intramolecular C-H O and intermolecular O-H N and C-H O hydrogen bonds (Table 1) link the molecules (Fig. 3), in which they may be effective in the stabilization of the structure. The π π contact between the triazole and 3-methoxyphenyl rings, Cg1 Cg2 i [symmetry code: (i) 1/2 + x, 1/2 - y, 1/2 + z, where Cg1 and Cg2 are the centroids of the rings B (N1/N2/N3/C10/C11) and A (C2-C7), respectively] may further stabilize the structure, with centroid-centroid distance of (3) Å. There also exist C H π contacts (Table 1) between the phenyl rings and the methyl group and the 3-methoxyphenyl ring. Experimental The synthesis of the title compound (Fig. 1) was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(3-(3- methoxyphenyl)propanoyl)semicarbazide (3.43 g, 10 mmol) in NaOH (2M) for 5 h. Single crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield; 71%, m.p K). Refinement H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with U iso (H) = xu eq (C,O), where x = 1.2 for aromatic and methylene H and x = 1.5 for all other H atoms. Figures Fig. 1. The formation of the title compound. sup-1

4 Fig. 2. The molecular structure of the title molecule, with the atom-numbering scheme. Fig. 3. A partial packing diagram. Hydrogen bonds are shown as dashed lines. 5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol Crystal data C 18 H 19 N 3 O 3 F 000 = 688 M r = Monoclinic, P2 1 /n Hall symbol: -P 2yn a = (11) Å D x = Mg m 3 Melting point: 454(1) K Mo Kα radiation λ = Å b = (14) Å θ = º c = (11) Å β = (2)º V = (3) Å 3 Z = 4 Cell parameters from 9949 reflections µ = 0.09 mm 1 T = 294 (2) K Block, yellow mm Data collection Bruker SMART CCD diffractometer Radiation source: fine-focus sealed tube Monochromator: graphite R int = T = 294(2) K θ max = 28.3º φ and ω scans θ min = 2.4º Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.902, T max = independent reflections 3212 reflections with I > 2σ(I) h = 8 14 k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites sup-2

5 R[F 2 > 2σ(F 2 )] = H-atom parameters constrained wr(f 2 ) = w = 1/[σ 2 (F 2 o ) + (0.0854P) P] where P = (F 2 o + 2F 2 c )/3 S = 1.02 (Δ/σ) max < reflections Δρ max = 0.56 e Å parameters Δρ min = 0.40 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (13) (9) (14) (4) O (12) (8) (9) (3) O (9) (7) (12) (3) H * N (10) (7) (10) (2) N (11) (8) (11) (3) N (11) (8) (11) (3) C (2) (16) (3) (8) H1A * H1B * H1C * C (15) (11) (13) (3) C (15) (12) (14) (4) H3A * C (14) (12) (14) (4) H4A * C (13) (11) (13) (3) H5A * C (13) (10) (12) (3) C (14) (11) (13) (3) H7A * C (14) (11) (14) (3) H8A * H8B * sup-3

6 C (13) (10) (13) (3) H9A * H9B * C (12) (9) (11) (3) C (13) (9) (12) (3) C (12) (9) (12) (3) C (19) (12) (15) (4) H13A * C (2) (12) (19) (6) H14A * C (2) (11) (18) (5) H15A * C (15) (11) (14) (4) H16A * C (12) (9) (12) (3) C (3) (16) (16) (6) H18A * H18B * H18C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (8) (6) (10) (5) (7) (6) O (8) (5) (5) (5) (5) (4) O (5) (5) (8) (4) (5) (5) N (5) (5) (5) (4) (4) (4) N (6) (6) (7) (5) (5) (5) N (6) (6) (7) (4) (5) (5) C (15) (11) (19) (10) (13) (12) C (8) (7) (8) (6) (6) (6) C (8) (9) (8) (7) (6) (7) C (7) (10) (8) (6) (6) (7) C (7) (7) (7) (6) (5) (6) C (6) (7) (6) (5) (5) (5) C (7) (8) (8) (6) (6) (6) C (7) (8) (8) (6) (6) (6) C (7) (7) (7) (5) (6) (6) C (6) (6) (6) (5) (5) (5) C (6) (6) (7) (5) (5) (5) C (6) (6) (7) (5) (5) (5) C (12) (8) (8) (8) (8) (6) C (16) (8) (12) (9) (11) (8) C (12) (7) (12) (7) (9) (8) C (8) (7) (8) (6) (7) (6) C (6) (6) (7) (5) (5) (5) C (18) (12) (9) (12) (10) (8) sup-4

7 Geometric parameters (Å, ) O3 H C9 H9B N2 N (16) C10 N (17) C1 O (3) C10 N (17) C1 H1A C11 O (16) C1 H1B C11 N (17) C1 H1C C11 N (16) C2 O (19) C12 C (2) C2 C (2) C12 C (18) C2 C (2) C12 N (15) C3 C (2) C13 C (2) C3 H3A C13 H13A C4 C (2) C14 C (3) C4 H4A C14 H14A C5 C (19) C15 C (3) C5 H5A C15 H15A C6 C (2) C16 C (19) C6 C (19) C16 H16A C7 H7A C17 O (17) C8 C (2) C18 O (2) C8 H8A C18 H18A C8 H8B C18 H18B C9 C (18) C18 H18C C9 H9A C2 O1 C (14) H8A C8 H8B C17 O2 C (13) C10 C9 C (11) C11 O3 H C10 C9 H9A C10 N1 C (10) C8 C9 H9A C10 N1 C (10) C10 C9 H9B C11 N1 C (11) C8 C9 H9B C10 N2 N (11) H9A C9 H9B C11 N3 N (11) N2 C10 N (11) O1 C1 H1A N2 C10 C (12) O1 C1 H1B N1 C10 C (11) H1A C1 H1B O3 C11 N (12) O1 C1 H1C O3 C11 N (12) H1A C1 H1C N3 C11 N (11) H1B C1 H1C C13 C12 C (12) O1 C2 C (15) C13 C12 N (13) O1 C2 C (14) C17 C12 N (12) C7 C2 C (14) C12 C13 C (16) C4 C3 C (14) C12 C13 H13A C4 C3 H3A C14 C13 H13A C2 C3 H3A C15 C14 C (17) C3 C4 C (14) C15 C14 H14A C3 C4 H4A C13 C14 H14A C5 C4 H4A C14 C15 C (15) sup-5

8 C6 C5 C (14) C14 C15 H15A C6 C5 H5A C16 C15 H15A C4 C5 H5A C15 C16 C (15) C5 C6 C (13) C15 C16 H16A C5 C6 C (13) C17 C16 H16A C7 C6 C (13) O2 C17 C (11) C2 C7 C (13) O2 C17 C (13) C2 C7 H7A C12 C17 C (13) C6 C7 H7A O2 C18 H18A C6 C8 C (11) O2 C18 H18B C6 C8 H8A H18A C18 H18B C9 C8 H8A O2 C18 H18C C6 C8 H8B H18A C18 H18C C9 C8 H8B H18B C18 H18C Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A O3 H3 N3 i (15) 173 C5 H5A O1 ii (2) 147 C8 H8A O (2) 157 C4 H4A Cg3 iii (3) 140 C7 H7A Cg (3) 165 C18 H18A Cg2 iv (3) 105 C18 H18B Cg2 iv (3) 101 Symmetry codes: (i) x+2, y, z+2; (ii) x+1/2, y 1/2, z+3/2; (iii) x 1, y, z; (iv) x 1/2, y 1/2, z 3/2. sup-6

9 Fig. 1 sup-7

10 Fig. 2 sup-8

11 Fig. 3 sup-9