5-(3-Methoxy­pheneth­yl)-4-(2-methoxy­phen­yl)-4H-1,2,4-triazol-3-ol

Hanif, M.; Qadeer, G.; Rama, N.H.; Wong, W.-Y.

doi:10.1107/S1600536808033990

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2180

doi:10.1107/S1600536808033990

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5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol

Muhammad Hanif,^a Ghulam Qadeer,^a Nasim Hasan Rama ^a ^* and Wai-Yeung Wong ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong
^*Correspondence e-mail: nasimhrama@yahoo.com

(Received 6 October 2008; accepted 17 October 2008; online 25 October 2008)

In the molecule of the title compound, C₁₈H₁₉N₃O₃, the triazole ring is oriented with respect to the 3-methoxyphenyl and 2-methoxyphenyl rings at dihedral angles of 11.79 (3) and 89.22 (3)°, respectively. The dihedral angle between the two benzene rings is 85.95 (3)°. In the crystal structure, intermolecular O—H⋯N and C—H⋯O hydrogen bonds link the molecules. There is a π–π contact between the triazole and 3-methoxyphenyl rings [centroid–centroid distance = 3.916 (3) Å]. There is a π–π contact between the triazole and one of the 3-methoxyphenyl rings [centroid–centroid distance = 3.916 (3) Å ]. C—H⋯π 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

C₁₈H₁₉N₃O₃
M_r = 325.36
Monoclinic, P 2₁ /n
a = 10.5030 (11) Å
b = 14.1172 (14) Å
c = 11.3226 (11) Å
β = 98.192 (2)°
V = 1661.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.902, T_max = 1.000 (expected range = 0.884–0.980)
9949 measured reflections
4026 independent reflections
3212 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.146
S = 1.02
4026 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N3ⁱ	0.82	1.94	2.7569 (15)	173
C5—H5A⋯O1ⁱⁱ	0.93	2.59	3.406 (2)	147
C8—H8A⋯O2	0.97	2.57	3.485 (2)	157
C4—H4A⋯Cg3ⁱⁱⁱ	0.93	3.25	4.004 (3)	140
C7—H7A⋯Cg3	0.93	3.16	4.067 (3)	165
C18—H18A⋯Cg2^iv	0.96	3.03	3.400 (3)	105
C18—H18B⋯Cg2^iv	0.96	3.08	3.400 (3)	101
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033990/hk2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033990/hk2549Isup2.hkl

checkCIF report

Comment top

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 [1.3459 (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 = 11.79 (3)°, A/C = 89.22 (3)° and B/C = 85.95 (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···Cg2ⁱ [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 3.916 (3) Å. There also exist C—H···π contacts (Table 1) between the phenyl rings and the methyl group and the 3-methoxyphenyl ring.

Related literature top

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 literature, see: Öztürk et al. (2004a, 2004b). For bond-length data, see: Allen et al. (1987).

Experimental top

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. 454-455 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Spek, 2003).

Figures top

	Fig. 1. The formation of the title compound.
	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 top

Crystal data top

C₁₈H₁₉N₃O₃	F(000) = 688
M_r = 325.36	D_x = 1.301 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 454(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.5030 (11) Å	Cell parameters from 9949 reflections
b = 14.1172 (14) Å	θ = 2.4–28.3°
c = 11.3226 (11) Å	µ = 0.09 mm⁻¹
β = 98.192 (2)°	T = 294 K
V = 1661.7 (3) Å³	Block, yellow
Z = 4	0.32 × 0.24 × 0.22 mm

Data collection top

Bruker SMART CCD diffractometer	4026 independent reflections
Radiation source: fine-focus sealed tube	3212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→14
T_min = 0.902, T_max = 1.000	k = −18→18
9949 measured reflections	l = −14→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0854P)² + 0.2782P] where P = (F_o² + 2F_c²)/3
4026 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₈H₁₉N₃O₃	V = 1661.7 (3) Å³
M_r = 325.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5030 (11) Å	µ = 0.09 mm⁻¹
b = 14.1172 (14) Å	T = 294 K
c = 11.3226 (11) Å	0.32 × 0.24 × 0.22 mm
β = 98.192 (2)°

Data collection top

Bruker SMART CCD diffractometer	4026 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3212 reflections with I > 2σ(I)
T_min = 0.902, T_max = 1.000	R_int = 0.018
9949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	Δρ_max = 0.56 e Å⁻³
4026 reflections	Δρ_min = −0.40 e Å⁻³
218 parameters

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.34683 (13)	0.50242 (9)	0.80167 (14)	0.0726 (4)
O2	0.76819 (12)	0.19899 (8)	0.72362 (9)	0.0538 (3)
O3	0.99935 (9)	0.12807 (7)	0.96442 (12)	0.0554 (3)
H3	1.0436	0.0800	0.9720	0.083*
N1	0.78261 (10)	0.16861 (7)	0.95758 (10)	0.0367 (2)
N2	0.70357 (11)	0.02988 (8)	1.00087 (11)	0.0439 (3)
N3	0.83555 (11)	0.02434 (8)	0.99977 (11)	0.0439 (3)
C1	0.4774 (2)	0.53003 (16)	0.8160 (3)	0.0908 (8)
H1A	0.4829	0.5979	0.8133	0.136*
H1B	0.5180	0.5033	0.7529	0.136*
H1C	0.5200	0.5077	0.8915	0.136*
C2	0.31961 (15)	0.40769 (11)	0.80274 (13)	0.0485 (3)
C3	0.18992 (15)	0.38405 (12)	0.79300 (14)	0.0525 (4)
H3A	0.1277	0.4313	0.7837	0.063*
C4	0.15417 (14)	0.29079 (12)	0.79721 (14)	0.0512 (4)
H4A	0.0675	0.2751	0.7909	0.061*
C5	0.24656 (13)	0.21925 (11)	0.81085 (13)	0.0447 (3)
H5A	0.2216	0.1563	0.8151	0.054*
C6	0.37517 (13)	0.24212 (10)	0.81805 (12)	0.0401 (3)
C7	0.41200 (14)	0.33670 (11)	0.81434 (13)	0.0463 (3)
H7A	0.4986	0.3523	0.8196	0.056*
C8	0.47827 (14)	0.16657 (11)	0.83435 (14)	0.0480 (3)
H8A	0.5424	0.1807	0.7831	0.058*
H8B	0.4400	0.1059	0.8100	0.058*
C9	0.54420 (13)	0.15956 (10)	0.96390 (13)	0.0440 (3)
H9A	0.5505	0.2225	0.9987	0.053*
H9B	0.4913	0.1214	1.0090	0.053*
C10	0.67491 (12)	0.11732 (9)	0.97478 (11)	0.0378 (3)
C11	0.88697 (13)	0.10760 (9)	0.97304 (12)	0.0390 (3)
C12	0.79093 (12)	0.26338 (9)	0.91477 (12)	0.0374 (3)
C13	0.80818 (19)	0.33857 (12)	0.99299 (15)	0.0583 (4)
H13A	0.8117	0.3284	1.0746	0.070*
C14	0.8202 (2)	0.42943 (12)	0.94939 (19)	0.0751 (6)
H14A	0.8323	0.4805	1.0017	0.090*
C15	0.8143 (2)	0.44367 (11)	0.82921 (18)	0.0652 (5)
H15A	0.8226	0.5048	0.8006	0.078*
C16	0.79629 (15)	0.36961 (11)	0.74987 (14)	0.0504 (4)
H16A	0.7918	0.3806	0.6684	0.061*
C17	0.78478 (12)	0.27786 (9)	0.79249 (12)	0.0386 (3)
C18	0.7433 (3)	0.21156 (16)	0.59719 (16)	0.0767 (6)
H18A	0.7335	0.1508	0.5590	0.115*
H18B	0.8140	0.2447	0.5708	0.115*
H18C	0.6659	0.2477	0.5769	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0682 (8)	0.0439 (6)	0.1023 (10)	0.0042 (5)	0.0004 (7)	0.0152 (6)
O2	0.0795 (8)	0.0433 (5)	0.0401 (5)	0.0046 (5)	0.0140 (5)	0.0015 (4)
O3	0.0367 (5)	0.0395 (5)	0.0911 (8)	0.0079 (4)	0.0121 (5)	0.0164 (5)
N1	0.0359 (5)	0.0333 (5)	0.0410 (5)	0.0062 (4)	0.0063 (4)	0.0081 (4)
N2	0.0369 (6)	0.0378 (6)	0.0574 (7)	0.0038 (5)	0.0083 (5)	0.0089 (5)
N3	0.0366 (6)	0.0354 (6)	0.0596 (7)	0.0049 (4)	0.0067 (5)	0.0105 (5)
C1	0.0816 (15)	0.0595 (11)	0.1215 (19)	−0.0176 (10)	−0.0199 (13)	0.0270 (12)
C2	0.0502 (8)	0.0443 (7)	0.0498 (8)	0.0048 (6)	0.0030 (6)	0.0096 (6)
C3	0.0448 (8)	0.0574 (9)	0.0541 (8)	0.0171 (7)	0.0023 (6)	0.0060 (7)
C4	0.0336 (7)	0.0659 (10)	0.0532 (8)	0.0044 (6)	0.0030 (6)	0.0014 (7)
C5	0.0388 (7)	0.0483 (7)	0.0459 (7)	−0.0014 (6)	0.0020 (5)	−0.0004 (6)
C6	0.0360 (6)	0.0455 (7)	0.0381 (6)	0.0050 (5)	0.0025 (5)	−0.0013 (5)
C7	0.0360 (7)	0.0498 (8)	0.0527 (8)	0.0015 (6)	0.0055 (6)	0.0075 (6)
C8	0.0408 (7)	0.0482 (8)	0.0536 (8)	0.0086 (6)	0.0022 (6)	−0.0071 (6)
C9	0.0372 (7)	0.0454 (7)	0.0508 (7)	0.0086 (5)	0.0106 (6)	0.0068 (6)
C10	0.0355 (6)	0.0390 (6)	0.0392 (6)	0.0041 (5)	0.0066 (5)	0.0066 (5)
C11	0.0361 (6)	0.0347 (6)	0.0461 (7)	0.0064 (5)	0.0053 (5)	0.0075 (5)
C12	0.0374 (6)	0.0317 (6)	0.0435 (7)	0.0055 (5)	0.0070 (5)	0.0069 (5)
C13	0.0829 (12)	0.0440 (8)	0.0467 (8)	0.0023 (8)	0.0046 (8)	−0.0013 (6)
C14	0.1112 (16)	0.0392 (8)	0.0729 (12)	−0.0050 (9)	0.0063 (11)	−0.0075 (8)
C15	0.0784 (12)	0.0353 (7)	0.0836 (12)	−0.0019 (7)	0.0172 (9)	0.0135 (8)
C16	0.0552 (8)	0.0438 (7)	0.0547 (8)	0.0058 (6)	0.0159 (7)	0.0167 (6)
C17	0.0380 (6)	0.0356 (6)	0.0435 (7)	0.0057 (5)	0.0102 (5)	0.0057 (5)
C18	0.1174 (18)	0.0713 (12)	0.0423 (9)	0.0071 (12)	0.0147 (10)	0.0014 (8)

Geometric parameters (Å, º) top

O3—H3	0.8200	C9—H9B	0.9700
N2—N3	1.3902 (16)	C10—N2	1.2946 (17)
C1—O1	1.413 (3)	C10—N1	1.3801 (17)
C1—H1A	0.9600	C11—O3	1.2325 (16)
C1—H1B	0.9600	C11—N3	1.3459 (17)
C1—H1C	0.9600	C11—N1	1.3854 (16)
C2—O1	1.3680 (19)	C12—C13	1.378 (2)
C2—C7	1.388 (2)	C12—C17	1.3919 (18)
C2—C3	1.391 (2)	C12—N1	1.4299 (15)
C3—C4	1.372 (2)	C13—C14	1.387 (2)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.394 (2)	C14—C15	1.368 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.3798 (19)	C15—C16	1.374 (3)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.393 (2)	C16—C17	1.3934 (19)
C6—C8	1.5123 (19)	C16—H16A	0.9300
C7—H7A	0.9300	C17—O2	1.3563 (17)
C8—C9	1.533 (2)	C18—O2	1.429 (2)
C8—H8A	0.9700	C18—H18A	0.9600
C8—H8B	0.9700	C18—H18B	0.9600
C9—C10	1.4857 (18)	C18—H18C	0.9600
C9—H9A	0.9700

C2—O1—C1	118.00 (14)	H8A—C8—H8B	107.9
C17—O2—C18	117.66 (13)	C10—C9—C8	113.03 (11)
C11—O3—H3	109.5	C10—C9—H9A	109.0
C10—N1—C11	107.79 (10)	C8—C9—H9A	109.0
C10—N1—C12	129.03 (10)	C10—C9—H9B	109.0
C11—N1—C12	122.62 (11)	C8—C9—H9B	109.0
C10—N2—N3	104.56 (11)	H9A—C9—H9B	107.8
C11—N3—N2	112.67 (11)	N2—C10—N1	111.34 (11)
O1—C1—H1A	109.5	N2—C10—C9	125.71 (12)
O1—C1—H1B	109.5	N1—C10—C9	122.95 (11)
H1A—C1—H1B	109.5	O3—C11—N3	129.95 (12)
O1—C1—H1C	109.5	O3—C11—N1	126.41 (12)
H1A—C1—H1C	109.5	N3—C11—N1	103.64 (11)
H1B—C1—H1C	109.5	C13—C12—C17	120.63 (12)
O1—C2—C7	124.22 (15)	C13—C12—N1	120.78 (13)
O1—C2—C3	115.93 (14)	C17—C12—N1	118.57 (12)
C7—C2—C3	119.85 (14)	C12—C13—C14	119.61 (16)
C4—C3—C2	119.81 (14)	C12—C13—H13A	120.2
C4—C3—H3A	120.1	C14—C13—H13A	120.2
C2—C3—H3A	120.1	C15—C14—C13	119.77 (17)
C3—C4—C5	120.63 (14)	C15—C14—H14A	120.1
C3—C4—H4A	119.7	C13—C14—H14A	120.1
C5—C4—H4A	119.7	C14—C15—C16	121.40 (15)
C6—C5—C4	119.82 (14)	C14—C15—H15A	119.3
C6—C5—H5A	120.1	C16—C15—H15A	119.3
C4—C5—H5A	120.1	C15—C16—C17	119.44 (15)
C5—C6—C7	119.76 (13)	C15—C16—H16A	120.3
C5—C6—C8	121.34 (13)	C17—C16—H16A	120.3
C7—C6—C8	118.86 (13)	O2—C17—C12	115.80 (11)
C2—C7—C6	120.11 (13)	O2—C17—C16	125.05 (13)
C2—C7—H7A	119.9	C12—C17—C16	119.14 (13)
C6—C7—H7A	119.9	O2—C18—H18A	109.5
C6—C8—C9	112.34 (11)	O2—C18—H18B	109.5
C6—C8—H8A	109.1	H18A—C18—H18B	109.5
C9—C8—H8A	109.1	O2—C18—H18C	109.5
C6—C8—H8B	109.1	H18A—C18—H18C	109.5
C9—C8—H8B	109.1	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.82	1.94	2.7569 (15)	173
C5—H5A···O1ⁱⁱ	0.93	2.59	3.406 (2)	147
C8—H8A···O2	0.97	2.57	3.485 (2)	157
C4—H4A···Cg3ⁱⁱⁱ	0.93	3.25	4.004 (3)	140
C7—H7A···Cg3	0.93	3.16	4.067 (3)	165
C18—H18A···Cg2^iv	0.96	3.03	3.400 (3)	105
C18—H18B···Cg2^iv	0.96	3.08	3.400 (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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₃O₃
M_r	325.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	10.5030 (11), 14.1172 (14), 11.3226 (11)
β (°)	98.192 (2)
V (Å³)	1661.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.902, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9949, 4026, 3212
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.02
No. of reflections	4026
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.40

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.82	1.94	2.7569 (15)	173
C5—H5A···O1ⁱⁱ	0.93	2.59	3.406 (2)	147
C8—H8A···O2	0.97	2.57	3.485 (2)	157
C4—H4A···Cg3ⁱⁱⁱ	0.93	3.25	4.004 (3)	140
C7—H7A···Cg3	0.93	3.16	4.067 (3)	165
C18—H18A···Cg2^iv	0.96	3.03	3.400 (3)	105
C18—H18B···Cg2^iv	0.96	3.08	3.400 (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.

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

References

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