4-(4-Methoxy-phen-yl)-3-[2-(2-methoxy-phen-yl)eth-yl]-1H-1,2,4-triazol-5(4H)-one.

The title compound, C(18)H(19)N(3)O(3), 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 inter-molecular N-H⋯O hydrogen-bond inter-actions between centrosymmetrically related mol-ecules [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 = 325.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.01

3278 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002815/rz2290sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H19N3O3	F(000) = 688
Mr = 325.36	Dx = 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

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

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(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3
3278 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .