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

Hanif, M.; Qadeer, G.; Rama, N.H.; Akhtar, J.; Helliwell, M.

doi:10.1107/S1600536809001482

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o329

doi:10.1107/S1600536809001482

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

Muhammad Hanif,^a Ghulam Qadeer,^a ^* Nasim Hasan Rama,^a Javeed Akhtar ^b and Madeleine Helliwell ^b

^aDepartment of Chemistry, Quaid-I-Azam Univeristy, Islamabad 45320, Pakistan, and ^bThe Manchester Materials Science Centre and Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England
^*Correspondence e-mail: qadeerqau@yahoo.com

(Received 11 January 2009; accepted 12 January 2009; online 17 January 2009)

In the molecule of the title compound, C₁₇H₁₇N₃O₃, the triazole ring is oriented at dihedral angles of 88.09 (3) and 83.72 (3)° with respect to the 2-methoxybenzyl and 2-methoxyphenyl rings, respectively. The dihedral angle between the 2-methoxybenzyl and 2-methoxyphenyl rings is 52.95 (3)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. There is a π–π contact between the 2-methoxyphenyl rings [centroid–centroid distance = 3.811 (3) Å].

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

C₁₇H₁₇N₃O₃
M_r = 311.34
Monoclinic, P 2₁ /c
a = 7.4941 (12) Å
b = 8.3730 (13) Å
c = 24.770 (4) Å
β = 97.455 (2)°
V = 1541.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
11912 measured reflections
3160 independent reflections
2888 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.091
S = 1.06
3160 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.890 (17)	1.911 (18)	2.7958 (14)	172.6 (15)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001482/hk2613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001482/hk2613Isup2.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 and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), 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,b). In the triazole ring, the N2=C1 [1.2960 (16) Å] bond has double bond character. Rings A (N1/N2/N3/C1/C2), B (C4-C9) and C (C11-C16) are, of course, planar and the dihedral angles between them are A/B = 88.09 (3)°, A/C = 83.72 (3)° and B/C = 52.95 (3)°.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π—π contact between the 2-methoxyphenyl rings, Cg1···Cg1ⁱ [symmetry code: (i) -x, 2 - y, -z, where Cg1 is the centroid of the ring C (C11-C16)] may further stabilize the structure, with centroid-centroid distance of 3.811 (3) Å.

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

Experimental top

The synthesis of the title compound was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(2-(2-methoxyphenyl)acetyl)semicarbazide (3.29 g, 10 mmol) in NaOH (2M) for 5 h. Crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield; 79%; m.p. 444–445 K).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Reaction scheme.

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

Crystal data top

C₁₇H₁₇N₃O₃	F(000) = 656
M_r = 311.34	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 444(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.4941 (12) Å	Cell parameters from 912 reflections
b = 8.3730 (13) Å	θ = 2.7–26.4°
c = 24.770 (4) Å	µ = 0.09 mm⁻¹
β = 97.455 (2)°	T = 100 K
V = 1541.2 (4) Å³	Block, colorless
Z = 4	0.50 × 0.40 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2888 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 26.4°, θ_min = 2.6°
ϕ and ω scans	h = −9→9
11912 measured reflections	k = −10→10
3160 independent reflections	l = −30→30

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0403P)² + 0.586P] where P = (F_o² + 2F_c²)/3
3160 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₇N₃O₃	V = 1541.2 (4) Å³
M_r = 311.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4941 (12) Å	µ = 0.09 mm⁻¹
b = 8.3730 (13) Å	T = 100 K
c = 24.770 (4) Å	0.50 × 0.40 × 0.30 mm
β = 97.455 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2888 reflections with I > 2σ(I)
11912 measured reflections	R_int = 0.039
3160 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.28 e Å⁻³
3160 reflections	Δρ_min = −0.17 e Å⁻³
214 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	0.29433 (12)	0.86489 (10)	0.48842 (3)	0.0211 (2)
O2	0.00410 (12)	1.09258 (11)	0.66422 (4)	0.0245 (2)
O3	0.28378 (12)	0.51980 (10)	0.59145 (4)	0.0232 (2)
N1	0.22479 (14)	0.83390 (12)	0.57791 (4)	0.0170 (2)
N2	0.43854 (14)	0.98640 (12)	0.62165 (4)	0.0191 (2)
N3	0.44636 (14)	0.98655 (12)	0.56595 (4)	0.0186 (2)
H3N	0.533 (2)	1.0380 (19)	0.5514 (7)	0.029 (4)*
C1	0.30443 (16)	0.89290 (14)	0.62733 (5)	0.0171 (2)
C2	0.32018 (16)	0.89290 (14)	0.53796 (5)	0.0171 (3)
C3	0.24258 (17)	0.84679 (15)	0.68016 (5)	0.0198 (3)
H3A	0.3194	0.7587	0.6966	0.024*
H3B	0.1177	0.8061	0.6729	0.024*
C4	0.24810 (16)	0.98237 (14)	0.72050 (5)	0.0186 (3)
C5	0.12083 (16)	1.10515 (15)	0.71152 (5)	0.0200 (3)
C6	0.11769 (18)	1.22880 (16)	0.74885 (5)	0.0244 (3)
H6	0.0328	1.3131	0.7421	0.029*
C7	0.23959 (19)	1.22812 (17)	0.79612 (5)	0.0265 (3)
H7	0.2370	1.3118	0.8219	0.032*
C8	0.36460 (18)	1.10676 (17)	0.80600 (5)	0.0253 (3)
H8	0.4467	1.1061	0.8386	0.030*
C9	0.36928 (17)	0.98536 (16)	0.76775 (5)	0.0221 (3)
H9	0.4570	0.9033	0.7742	0.027*
C10	−0.15902 (18)	1.18333 (18)	0.66085 (6)	0.0296 (3)
H10A	−0.2236	1.1557	0.6915	0.044*
H10B	−0.2348	1.1588	0.6266	0.044*
H10C	−0.1303	1.2976	0.6622	0.044*
C11	0.07604 (16)	0.72543 (14)	0.56880 (5)	0.0170 (3)
C12	0.10903 (16)	0.56170 (14)	0.57578 (5)	0.0185 (3)
C13	−0.03451 (18)	0.45580 (15)	0.56618 (5)	0.0218 (3)
H13	−0.0146	0.3441	0.5702	0.026*
C14	−0.20681 (18)	0.51395 (16)	0.55077 (5)	0.0245 (3)
H14	−0.3045	0.4412	0.5442	0.029*
C15	−0.23904 (17)	0.67620 (17)	0.54470 (6)	0.0253 (3)
H15	−0.3580	0.7145	0.5345	0.030*
C16	−0.09601 (17)	0.78260 (16)	0.55360 (5)	0.0217 (3)
H16	−0.1164	0.8941	0.5492	0.026*
C17	0.3195 (2)	0.35431 (15)	0.60309 (6)	0.0278 (3)
H17A	0.2530	0.3200	0.6326	0.042*
H17B	0.4488	0.3392	0.6142	0.042*
H17C	0.2813	0.2906	0.5704	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0264 (5)	0.0198 (4)	0.0175 (4)	−0.0037 (4)	0.0046 (4)	−0.0005 (3)
O2	0.0214 (5)	0.0280 (5)	0.0231 (5)	0.0027 (4)	−0.0005 (4)	−0.0034 (4)
O3	0.0224 (5)	0.0155 (4)	0.0309 (5)	0.0022 (3)	0.0004 (4)	0.0022 (4)
N1	0.0198 (5)	0.0142 (5)	0.0177 (5)	0.0001 (4)	0.0048 (4)	0.0000 (4)
N2	0.0221 (5)	0.0177 (5)	0.0179 (5)	−0.0004 (4)	0.0045 (4)	−0.0004 (4)
N3	0.0218 (5)	0.0170 (5)	0.0180 (5)	−0.0029 (4)	0.0066 (4)	0.0000 (4)
C1	0.0195 (6)	0.0131 (6)	0.0189 (6)	0.0021 (4)	0.0034 (5)	−0.0008 (4)
C2	0.0189 (6)	0.0127 (6)	0.0202 (6)	0.0021 (4)	0.0047 (5)	0.0008 (4)
C3	0.0236 (6)	0.0175 (6)	0.0190 (6)	−0.0016 (5)	0.0062 (5)	−0.0001 (5)
C4	0.0206 (6)	0.0187 (6)	0.0176 (6)	−0.0042 (5)	0.0070 (5)	0.0000 (5)
C5	0.0187 (6)	0.0232 (6)	0.0186 (6)	−0.0027 (5)	0.0048 (5)	−0.0004 (5)
C6	0.0234 (6)	0.0236 (7)	0.0274 (7)	0.0016 (5)	0.0076 (5)	−0.0034 (5)
C7	0.0304 (7)	0.0265 (7)	0.0238 (7)	−0.0056 (6)	0.0079 (6)	−0.0088 (5)
C8	0.0260 (7)	0.0298 (7)	0.0198 (6)	−0.0076 (5)	0.0018 (5)	−0.0014 (5)
C9	0.0209 (6)	0.0237 (7)	0.0221 (6)	−0.0013 (5)	0.0045 (5)	0.0024 (5)
C10	0.0217 (7)	0.0337 (8)	0.0326 (8)	0.0036 (6)	0.0007 (6)	0.0025 (6)
C11	0.0201 (6)	0.0164 (6)	0.0153 (6)	−0.0029 (5)	0.0050 (5)	−0.0011 (4)
C12	0.0215 (6)	0.0183 (6)	0.0160 (6)	0.0009 (5)	0.0036 (5)	−0.0002 (5)
C13	0.0280 (7)	0.0168 (6)	0.0214 (6)	−0.0029 (5)	0.0059 (5)	−0.0014 (5)
C14	0.0234 (6)	0.0262 (7)	0.0246 (7)	−0.0080 (5)	0.0062 (5)	−0.0047 (5)
C15	0.0190 (6)	0.0302 (7)	0.0267 (7)	0.0021 (5)	0.0028 (5)	−0.0031 (5)
C16	0.0252 (7)	0.0192 (6)	0.0211 (6)	0.0030 (5)	0.0043 (5)	−0.0009 (5)
C17	0.0322 (7)	0.0172 (7)	0.0328 (7)	0.0055 (5)	0.0003 (6)	0.0029 (5)

Geometric parameters (Å, º) top

O1—C2	1.2397 (15)	C7—C8	1.382 (2)
O2—C5	1.3724 (15)	C7—H7	0.9500
O2—C10	1.4326 (16)	C8—C9	1.3931 (19)
O3—C12	1.3627 (15)	C8—H8	0.9500
O3—C17	1.4335 (15)	C9—H9	0.9500
N1—C1	1.3817 (16)	C10—H10A	0.9800
N1—C2	1.3848 (15)	C10—H10B	0.9800
N1—C11	1.4329 (15)	C10—H10C	0.9800
N2—C1	1.2960 (16)	C11—C16	1.3811 (18)
N2—N3	1.3884 (15)	C11—C12	1.3998 (17)
N3—C2	1.3489 (16)	C12—C13	1.3905 (18)
N3—H3N	0.890 (17)	C13—C14	1.3865 (19)
C1—C3	1.4947 (17)	C13—H13	0.9500
C3—C4	1.5093 (17)	C14—C15	1.385 (2)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—C16	1.3892 (19)
C4—C9	1.3854 (18)	C15—H15	0.9500
C4—C5	1.4004 (18)	C16—H16	0.9500
C5—C6	1.3903 (18)	C17—H17A	0.9800
C6—C7	1.3887 (19)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800

C5—O2—C10	116.97 (10)	C9—C8—H8	120.3
C12—O3—C17	116.99 (10)	C4—C9—C8	121.08 (12)
C1—N1—C2	107.57 (10)	C4—C9—H9	119.5
C1—N1—C11	127.15 (10)	C8—C9—H9	119.5
C2—N1—C11	125.22 (10)	O2—C10—H10A	109.5
C1—N2—N3	103.99 (10)	O2—C10—H10B	109.5
C2—N3—N2	113.14 (10)	H10A—C10—H10B	109.5
C2—N3—H3N	124.8 (10)	O2—C10—H10C	109.5
N2—N3—H3N	121.9 (10)	H10A—C10—H10C	109.5
N2—C1—N1	111.82 (11)	H10B—C10—H10C	109.5
N2—C1—C3	125.74 (11)	C16—C11—C12	121.12 (11)
N1—C1—C3	122.41 (11)	C16—C11—N1	120.19 (11)
O1—C2—N3	128.89 (11)	C12—C11—N1	118.68 (11)
O1—C2—N1	127.66 (11)	O3—C12—C13	125.32 (11)
N3—C2—N1	103.45 (10)	O3—C12—C11	115.79 (11)
C1—C3—C4	113.60 (10)	C13—C12—C11	118.89 (11)
C1—C3—H3A	108.8	C14—C13—C12	119.69 (12)
C4—C3—H3A	108.8	C14—C13—H13	120.2
C1—C3—H3B	108.8	C12—C13—H13	120.2
C4—C3—H3B	108.8	C15—C14—C13	121.17 (12)
H3A—C3—H3B	107.7	C15—C14—H14	119.4
C9—C4—C5	118.63 (12)	C13—C14—H14	119.4
C9—C4—C3	122.11 (11)	C14—C15—C16	119.46 (12)
C5—C4—C3	119.17 (11)	C14—C15—H15	120.3
O2—C5—C6	124.12 (12)	C16—C15—H15	120.3
O2—C5—C4	115.15 (11)	C11—C16—C15	119.65 (12)
C6—C5—C4	120.73 (12)	C11—C16—H16	120.2
C7—C6—C5	119.45 (12)	C15—C16—H16	120.2
C7—C6—H6	120.3	O3—C17—H17A	109.5
C5—C6—H6	120.3	O3—C17—H17B	109.5
C8—C7—C6	120.59 (12)	H17A—C17—H17B	109.5
C8—C7—H7	119.7	O3—C17—H17C	109.5
C6—C7—H7	119.7	H17A—C17—H17C	109.5
C7—C8—C9	119.49 (12)	H17B—C17—H17C	109.5
C7—C8—H8	120.3

C1—N2—N3—C2	−0.75 (13)	C4—C5—C6—C7	−1.53 (19)
N3—N2—C1—N1	−0.47 (13)	C5—C6—C7—C8	0.7 (2)
N3—N2—C1—C3	177.59 (11)	C6—C7—C8—C9	0.8 (2)
C2—N1—C1—N2	1.47 (13)	C5—C4—C9—C8	0.56 (19)
C11—N1—C1—N2	178.77 (11)	C3—C4—C9—C8	−176.01 (12)
C2—N1—C1—C3	−176.66 (11)	C7—C8—C9—C4	−1.4 (2)
C11—N1—C1—C3	0.64 (18)	C1—N1—C11—C16	97.89 (15)
N2—N3—C2—O1	−178.27 (12)	C2—N1—C11—C16	−85.26 (15)
N2—N3—C2—N1	1.60 (13)	C1—N1—C11—C12	−81.92 (15)
C1—N1—C2—O1	178.09 (12)	C2—N1—C11—C12	94.93 (14)
C11—N1—C2—O1	0.72 (19)	C17—O3—C12—C13	−5.25 (18)
C1—N1—C2—N3	−1.78 (12)	C17—O3—C12—C11	175.20 (11)
C11—N1—C2—N3	−179.14 (11)	C16—C11—C12—O3	−179.25 (11)
N2—C1—C3—C4	39.80 (17)	N1—C11—C12—O3	0.56 (16)
N1—C1—C3—C4	−142.34 (11)	C16—C11—C12—C13	1.16 (18)
C1—C3—C4—C9	−111.02 (13)	N1—C11—C12—C13	−179.03 (11)
C1—C3—C4—C5	72.42 (15)	O3—C12—C13—C14	179.51 (11)
C10—O2—C5—C6	−18.72 (18)	C11—C12—C13—C14	−0.95 (18)
C10—O2—C5—C4	161.34 (11)	C12—C13—C14—C15	0.01 (19)
C9—C4—C5—O2	−179.15 (11)	C13—C14—C15—C16	0.8 (2)
C3—C4—C5—O2	−2.47 (16)	C12—C11—C16—C15	−0.41 (19)
C9—C4—C5—C6	0.92 (18)	N1—C11—C16—C15	179.78 (11)
C3—C4—C5—C6	177.59 (11)	C14—C15—C16—C11	−0.54 (19)
O2—C5—C6—C7	178.54 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.890 (17)	1.911 (18)	2.7958 (14)	172.6 (15)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₃
M_r	311.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.4941 (12), 8.3730 (13), 24.770 (4)
β (°)	97.455 (2)
V (Å³)	1541.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11912, 3160, 2888
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.06
No. of reflections	3160
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.890 (17)	1.911 (18)	2.7958 (14)	172.6 (15)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

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

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. CrossRef Web of Science Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717–3723. Web of Science CrossRef PubMed CAS Google Scholar
Holla, B. S., Gonsalves, R. & Shenoy, S. (1998). Farmaco, 53, 574–578. CrossRef PubMed CAS Google Scholar
Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou-Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Farmaco, 57, 253–257. Web of Science CrossRef PubMed CAS Google Scholar
Omar, A., Mohsen, M. E. & Wafa, O. A. (1986). Heterocycl. Chem. 23, 1339–1341. CrossRef CAS Google Scholar
Öztürk, S., Akkurt, M., Cansız, A., Koparır, M., Şekerci, M. & Heinemann, F. W. (2004a). Acta Cryst. E60, o425–o427. Web of Science CSD CrossRef IUCr Journals Google Scholar
Öztürk, S., Akkurt, M., Cansız, A., Koparır, M., Şekerci, M. & Heinemann, F. W. (2004b). Acta Cryst. E60, o642–o644. Web of Science CSD CrossRef IUCr Journals Google Scholar
Paulvannan, K., Chen, T. & Hale, R. (2000). Tetrahedron, 56, 8071–8076. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turan-Zitouni, G., Kaplancikli, Z. A., Erol, K. & Kilic, F. S. (1999). Farmaco, 54, 218–223. Web of Science CrossRef PubMed CAS Google Scholar