4-(4-Methoxy­phen­yl)-3-[2-(2-methoxy­phen­yl)eth­yl]-1H-1,2,4-triazol-5(4H)-one

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

doi:10.1107/S1600536809002815

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o429

doi:10.1107/S1600536809002815

Open

access

4-(4-Methoxyphenyl)-3-[2-(2-methoxyphenyl)ethyl]-1H-1,2,4-triazol-5(4H)-one

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

^aDepartment of Chemistry, Quaid-i-Azam University, 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 22 January 2009; online 31 January 2009)

The title compound, C₁₈H₁₉N₃O₃, is a biologically active triazole derivative. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 51.59 (4) and 61.37 (4)°. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen-bond interactions between centrosymmetrically related molecules [the dihedral angle between the benzene rings is 47.44 (5)°].

Related literature

For the biological activities of triazole derivatives, see: Demirbas et al. (2002 ); Holla et al. (1998 ); Omar et al. (1986 ); Paulvannan et al. (2000 ); Turan-Zitouni et al. (1999 ); Kritsanida et al. (2002 ). For related structures, see: Öztürk et al. (2004a ,b ). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ); Etter (1990 ).

Experimental

Crystal data

C₁₈H₁₉N₃O₃
M_r = 325.36
Monoclinic, P 2₁ /c
a = 12.5396 (19) Å
b = 9.1840 (14) Å
c = 14.041 (2) Å
β = 96.613 (3)°
V = 1606.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.50 × 0.50 × 0.50 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8654 measured reflections
3278 independent reflections
2631 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.083
S = 1.01
3278 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 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	0.913 (13)	1.870 (13)	2.7787 (12)	172.7 (12)
Symmetry code: (i) -x+1, -y, -z.

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 global, I. DOI: 10.1107/S1600536809002815/rz2290sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002815/rz2290Isup2.hkl

checkCIF report

Comment top

Substituted triazole derivatives display significant biological activity including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). 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 synthesis and biological activity of aryloxyacetyl hydrazide derivatives and report here the synthesis and crystal structure of the title compound (Fig. 1).

In the crystal structure of the title molecule, the bond lengths and angles are within normal range and comparable with those observed in related structures (Öztürk et al., 2004a,b). In the triazole ring, the N3═C11 (1.2970 (14) Å) bond shows double bond character. The rings A (N1—N3/ C1/ C2), B (C5—C10) and C (C12—C17) are planar and the dihedral angles between them are A/B = 78.11 (3)°, A/C = 56.04 (3)° and B/C = 33.23 (3)°. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1) generating a ring of graph-set R²₂(8) (Etter, 1990; Bernstein et al., 1995).

Related literature top

For the biological activities of triazole derivatives, see: Demirbas et al. (2002); Holla et al. (1998); Omar et al. (1986); Paulvannan et al. (2000); Turan-Zitouni et al. (1999); Kritsanida et al. (2002). For related structures, see: Öztürk et al. (2004a,b). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995); Etter (1990).

Experimental top

The synthesis of the title compound was carried out by refluxing a solution of 4-(4-methoxyphenyl)-1-(3-(2-methoxyphenyl)propanoyl)semicarbazide (3.43 g, 10 mmol) in 2M NaOH for 5 h. Single crystals suitable for X-ray measurements were obtained on slow evaporation of an aqeous ethanol solution at room temperature (yield: 84%; m.p. 431–432 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 compound with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).
	Fig. 2. Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dotted lines.

4-(4-Methoxyphenyl)-3-[2-(2-methoxyphenyl)ethyl]-1H-1,2,4-triazol- 5(4H)-one top

Crystal data top

C₁₈H₁₉N₃O₃	F(000) = 688
M_r = 325.36	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 431(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.5396 (19) Å	Cell parameters from 975 reflections
b = 9.1840 (14) Å	θ = 2.7–26.3°
c = 14.041 (2) Å	µ = 0.09 mm⁻¹
β = 96.613 (3)°	T = 100 K
V = 1606.3 (4) Å³	Irregular, colourless
Z = 4	0.50 × 0.50 × 0.50 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2631 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
ϕ and ω scans	h = −15→14
8654 measured reflections	k = −7→11
3278 independent reflections	l = −17→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
3278 reflections	(Δ/σ)_max = 0.001
223 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₉N₃O₃	V = 1606.3 (4) Å³
M_r = 325.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5396 (19) Å	µ = 0.09 mm⁻¹
b = 9.1840 (14) Å	T = 100 K
c = 14.041 (2) Å	0.50 × 0.50 × 0.50 mm
β = 96.613 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2631 reflections with I > 2σ(I)
8654 measured reflections	R_int = 0.031
3278 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
3278 reflections	Δρ_min = −0.17 e Å⁻³
223 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	0.48159 (6)	0.03096 (9)	0.13337 (5)	0.0255 (2)
O2	1.08680 (6)	−0.01642 (9)	0.16392 (5)	0.0249 (2)
O3	0.62644 (6)	0.09499 (10)	0.58898 (5)	0.0306 (2)
N1	0.65632 (7)	−0.02461 (11)	0.20442 (6)	0.0205 (2)
N2	0.72808 (7)	−0.09381 (11)	0.07470 (6)	0.0227 (2)
N3	0.62158 (7)	−0.05346 (11)	0.05209 (7)	0.0224 (2)
H3N	0.5916 (10)	−0.0520 (14)	−0.0104 (9)	0.029 (3)*
C1	0.74701 (9)	−0.07600 (12)	0.16673 (8)	0.0210 (3)
C2	0.57538 (9)	−0.01011 (13)	0.12919 (8)	0.0209 (3)
C3	0.85367 (9)	−0.09907 (14)	0.22308 (8)	0.0249 (3)
H3A	0.9001	−0.1548	0.1837	0.030*
H3B	0.8442	−0.1579	0.2806	0.030*
C4	0.90982 (9)	0.04491 (14)	0.25474 (8)	0.0260 (3)
H4A	0.8621	0.1023	0.2919	0.031*
H4B	0.9762	0.0230	0.2976	0.031*
C5	0.93810 (8)	0.13522 (13)	0.17195 (7)	0.0224 (3)
C6	1.02928 (9)	0.10111 (13)	0.12649 (7)	0.0209 (3)
C7	1.05663 (9)	0.18328 (13)	0.05035 (8)	0.0226 (3)
H7	1.1184	0.1591	0.0202	0.027*
C8	0.99314 (9)	0.30150 (13)	0.01822 (9)	0.0262 (3)
H8	1.0122	0.3589	−0.0335	0.031*
C9	0.90262 (9)	0.33607 (14)	0.06091 (9)	0.0284 (3)
H9	0.8588	0.4160	0.0381	0.034*
C10	0.87625 (9)	0.25331 (13)	0.13719 (8)	0.0264 (3)
H10	0.8141	0.2780	0.1666	0.032*
C11	1.17827 (9)	−0.05778 (13)	0.11798 (8)	0.0252 (3)
H11A	1.1559	−0.0769	0.0499	0.038*
H11B	1.2104	−0.1460	0.1484	0.038*
H11C	1.2312	0.0212	0.1242	0.038*
C12	0.64536 (8)	0.00320 (13)	0.30338 (8)	0.0202 (3)
C13	0.62172 (8)	0.14267 (13)	0.33266 (8)	0.0232 (3)
H13	0.6103	0.2192	0.2871	0.028*
C14	0.61483 (9)	0.16956 (14)	0.42864 (8)	0.0260 (3)
H14	0.5978	0.2646	0.4490	0.031*
C15	0.63274 (8)	0.05796 (14)	0.49543 (8)	0.0236 (3)
C16	0.65578 (9)	−0.08137 (14)	0.46578 (8)	0.0256 (3)
H16	0.6684	−0.1578	0.5113	0.031*
C17	0.66031 (9)	−0.10809 (13)	0.36918 (8)	0.0251 (3)
H17	0.6738	−0.2040	0.3482	0.030*
C18	0.64879 (10)	−0.01663 (16)	0.65935 (8)	0.0344 (3)
H18A	0.6017	−0.1002	0.6428	0.052*
H18B	0.6362	0.0209	0.7224	0.052*
H18C	0.7239	−0.0471	0.6610	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0190 (4)	0.0342 (5)	0.0238 (4)	0.0022 (3)	0.0042 (3)	−0.0020 (4)
O2	0.0212 (4)	0.0306 (5)	0.0238 (4)	0.0073 (3)	0.0060 (3)	0.0039 (4)
O3	0.0274 (5)	0.0434 (6)	0.0213 (4)	−0.0008 (4)	0.0043 (3)	−0.0082 (4)
N1	0.0190 (5)	0.0238 (5)	0.0192 (5)	0.0008 (4)	0.0046 (4)	0.0017 (4)
N2	0.0199 (5)	0.0247 (5)	0.0238 (5)	0.0026 (4)	0.0041 (4)	0.0012 (4)
N3	0.0199 (5)	0.0281 (6)	0.0193 (5)	0.0018 (4)	0.0029 (4)	−0.0001 (4)
C1	0.0223 (6)	0.0192 (6)	0.0226 (6)	0.0008 (5)	0.0068 (5)	0.0027 (5)
C2	0.0215 (6)	0.0196 (6)	0.0219 (6)	−0.0022 (5)	0.0040 (5)	0.0015 (5)
C3	0.0223 (6)	0.0308 (7)	0.0223 (6)	0.0062 (5)	0.0058 (5)	0.0052 (5)
C4	0.0190 (6)	0.0409 (8)	0.0181 (5)	0.0052 (5)	0.0018 (4)	−0.0032 (5)
C5	0.0183 (6)	0.0277 (6)	0.0204 (5)	−0.0006 (5)	−0.0008 (4)	−0.0076 (5)
C6	0.0187 (6)	0.0232 (6)	0.0199 (5)	0.0011 (5)	−0.0018 (4)	−0.0034 (5)
C7	0.0199 (6)	0.0254 (7)	0.0222 (6)	−0.0017 (5)	0.0017 (4)	−0.0043 (5)
C8	0.0268 (6)	0.0235 (6)	0.0274 (6)	−0.0042 (5)	−0.0010 (5)	0.0002 (5)
C9	0.0244 (6)	0.0227 (6)	0.0365 (7)	0.0036 (5)	−0.0031 (5)	−0.0026 (6)
C10	0.0200 (6)	0.0285 (7)	0.0305 (6)	0.0025 (5)	0.0013 (5)	−0.0092 (6)
C11	0.0203 (6)	0.0290 (7)	0.0269 (6)	0.0054 (5)	0.0056 (5)	0.0001 (5)
C12	0.0164 (5)	0.0249 (6)	0.0200 (6)	−0.0015 (5)	0.0043 (4)	−0.0010 (5)
C13	0.0185 (6)	0.0230 (6)	0.0280 (6)	0.0003 (5)	0.0018 (5)	0.0025 (5)
C14	0.0216 (6)	0.0254 (6)	0.0307 (6)	0.0020 (5)	0.0024 (5)	−0.0065 (5)
C15	0.0153 (6)	0.0336 (7)	0.0222 (6)	−0.0039 (5)	0.0037 (4)	−0.0064 (5)
C16	0.0288 (6)	0.0265 (7)	0.0222 (6)	−0.0030 (5)	0.0052 (5)	0.0036 (5)
C17	0.0294 (6)	0.0219 (6)	0.0252 (6)	−0.0011 (5)	0.0074 (5)	−0.0010 (5)
C18	0.0325 (7)	0.0503 (9)	0.0207 (6)	−0.0115 (6)	0.0048 (5)	−0.0026 (6)

Geometric parameters (Å, º) top

O1—C2	1.2429 (13)	C7—H7	0.9500
O2—C6	1.3690 (14)	C8—C9	1.3802 (16)
O2—C11	1.4305 (13)	C8—H8	0.9500
O3—C15	1.3679 (13)	C9—C10	1.3840 (17)
O3—C18	1.4290 (16)	C9—H9	0.9500
N1—C2	1.3844 (14)	C10—H10	0.9500
N1—C1	1.3909 (14)	C11—H11A	0.9800
N1—C12	1.4348 (14)	C11—H11B	0.9800
N2—C1	1.2970 (14)	C11—H11C	0.9800
N2—N3	1.3870 (13)	C12—C17	1.3761 (16)
N3—C2	1.3455 (14)	C12—C13	1.3877 (17)
N3—H3N	0.913 (13)	C13—C14	1.3825 (16)
C1—C3	1.4886 (15)	C13—H13	0.9500
C3—C4	1.5394 (17)	C14—C15	1.3899 (17)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—C16	1.3862 (17)
C4—C5	1.5033 (16)	C16—C17	1.3859 (16)
C4—H4A	0.9900	C16—H16	0.9500
C4—H4B	0.9900	C17—H17	0.9500
C5—C10	1.3888 (16)	C18—H18A	0.9800
C5—C6	1.4074 (15)	C18—H18B	0.9800
C6—C7	1.3836 (16)	C18—H18C	0.9800
C7—C8	1.3906 (17)

C6—O2—C11	116.79 (8)	C7—C8—H8	119.8
C15—O3—C18	117.21 (10)	C8—C9—C10	119.44 (11)
C2—N1—C1	107.58 (9)	C8—C9—H9	120.3
C2—N1—C12	125.32 (9)	C10—C9—H9	120.3
C1—N1—C12	127.05 (9)	C9—C10—C5	121.82 (11)
C1—N2—N3	104.79 (9)	C9—C10—H10	119.1
C2—N3—N2	112.79 (9)	C5—C10—H10	119.1
C2—N3—H3N	126.9 (8)	O2—C11—H11A	109.5
N2—N3—H3N	120.1 (8)	O2—C11—H11B	109.5
N2—C1—N1	110.97 (10)	H11A—C11—H11B	109.5
N2—C1—C3	124.18 (10)	O2—C11—H11C	109.5
N1—C1—C3	124.75 (10)	H11A—C11—H11C	109.5
O1—C2—N3	128.70 (10)	H11B—C11—H11C	109.5
O1—C2—N1	127.42 (10)	C17—C12—C13	120.26 (11)
N3—C2—N1	103.87 (9)	C17—C12—N1	119.81 (10)
C1—C3—C4	112.60 (10)	C13—C12—N1	119.92 (10)
C1—C3—H3A	109.1	C14—C13—C12	119.55 (11)
C4—C3—H3A	109.1	C14—C13—H13	120.2
C1—C3—H3B	109.1	C12—C13—H13	120.2
C4—C3—H3B	109.1	C13—C14—C15	120.17 (11)
H3A—C3—H3B	107.8	C13—C14—H14	119.9
C5—C4—C3	113.04 (9)	C15—C14—H14	119.9
C5—C4—H4A	109.0	O3—C15—C16	123.70 (11)
C3—C4—H4A	109.0	O3—C15—C14	116.22 (11)
C5—C4—H4B	109.0	C16—C15—C14	120.08 (11)
C3—C4—H4B	109.0	C17—C16—C15	119.39 (11)
H4A—C4—H4B	107.8	C17—C16—H16	120.3
C10—C5—C6	117.67 (11)	C15—C16—H16	120.3
C10—C5—C4	122.05 (10)	C12—C17—C16	120.52 (11)
C6—C5—C4	120.28 (10)	C12—C17—H17	119.7
O2—C6—C7	124.06 (10)	C16—C17—H17	119.7
O2—C6—C5	114.90 (10)	O3—C18—H18A	109.5
C7—C6—C5	121.04 (11)	O3—C18—H18B	109.5
C6—C7—C8	119.53 (11)	H18A—C18—H18B	109.5
C6—C7—H7	120.2	O3—C18—H18C	109.5
C8—C7—H7	120.2	H18A—C18—H18C	109.5
C9—C8—C7	120.49 (12)	H18B—C18—H18C	109.5
C9—C8—H8	119.8

C1—N2—N3—C2	0.48 (13)	O2—C6—C7—C8	−179.48 (10)
N3—N2—C1—N1	−0.33 (12)	C5—C6—C7—C8	0.05 (17)
N3—N2—C1—C3	−176.87 (11)	C6—C7—C8—C9	−0.81 (17)
C2—N1—C1—N2	0.10 (13)	C7—C8—C9—C10	0.98 (17)
C12—N1—C1—N2	177.68 (10)	C8—C9—C10—C5	−0.40 (18)
C2—N1—C1—C3	176.61 (11)	C6—C5—C10—C9	−0.34 (17)
C12—N1—C1—C3	−5.81 (18)	C4—C5—C10—C9	−179.98 (11)
N2—N3—C2—O1	−179.17 (11)	C2—N1—C12—C17	117.56 (13)
N2—N3—C2—N1	−0.41 (12)	C1—N1—C12—C17	−59.61 (15)
C1—N1—C2—O1	178.97 (11)	C2—N1—C12—C13	−63.64 (15)
C12—N1—C2—O1	1.34 (19)	C1—N1—C12—C13	119.18 (13)
C1—N1—C2—N3	0.19 (12)	C17—C12—C13—C14	0.94 (17)
C12—N1—C2—N3	−177.45 (10)	N1—C12—C13—C14	−177.85 (10)
N2—C1—C3—C4	105.59 (13)	C12—C13—C14—C15	0.76 (17)
N1—C1—C3—C4	−70.47 (14)	C18—O3—C15—C16	2.24 (16)
C1—C3—C4—C5	−64.75 (13)	C18—O3—C15—C14	−177.56 (10)
C3—C4—C5—C10	100.59 (13)	C13—C14—C15—O3	178.71 (10)
C3—C4—C5—C6	−79.05 (13)	C13—C14—C15—C16	−1.10 (17)
C11—O2—C6—C7	−2.34 (15)	O3—C15—C16—C17	179.96 (10)
C11—O2—C6—C5	178.10 (9)	C14—C15—C16—C17	−0.26 (17)
C10—C5—C6—O2	−179.92 (9)	C13—C12—C17—C16	−2.32 (17)
C4—C5—C6—O2	−0.27 (15)	N1—C12—C17—C16	176.47 (10)
C10—C5—C6—C7	0.51 (16)	C15—C16—C17—C12	1.96 (17)
C4—C5—C6—C7	−179.84 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.913 (13)	1.870 (13)	2.7787 (12)	172.7 (12)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₃O₃
M_r	325.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.5396 (19), 9.1840 (14), 14.041 (2)
β (°)	96.613 (3)
V (Å³)	1606.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.50 × 0.50

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8654, 3278, 2631
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.01
No. of reflections	3278
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −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	0.913 (13)	1.870 (13)	2.7787 (12)	172.7 (12)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573. CrossRef CAS 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
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o429

doi:10.1107/S1600536809002815

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Meth­oxy­phen­yl)-3-[2-(2-meth­oxy­phen­yl)eth­yl]-1H-1,2,4-triazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Methoxyphenyl)-3-[2-(2-methoxyphenyl)ethyl]-1H-1,2,4-triazol-5(4H)-one