5-(3-Methoxy-pheneth-yl)-4-(2-methoxy-phen-yl)-4H-1,2,4-triazol-3-ol.

In the mol-ecule of the title compound, C(18)H(19)N(3)O(3), the triazole ring is oriented with respect to the 3-methoxy-phenyl and 2-methoxy-phenyl 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, inter-molecular O-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules. There is a π-π contact between the triazole and 3-methoxy-phenyl rings [centroid-centroid distance = 3.916 (3) Å]. There is a π-π contact between the triazole and one of the 3-methoxy-phenyl 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 = 325.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.146

S = 1.02

4026 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.40 e Å−3

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.

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

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

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

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

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

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(Fo2) + (0.0854P)2 + 0.2782P] where P = (Fo2 + 2Fc2)/3
4026 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.40 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	0.34683 (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*

	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)

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

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···Cg2iv	0.96	3.03	3.400 (3)	105
C18—H18B···Cg2iv	0.96	3.08	3.400 (3)	101

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⋯Cg2iv	0.96	3.03	3.400 (3)	105
C18—H18B⋯Cg2iv	0.96	3.08	3.400 (3)	101

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 and Cg3 are the centroids of the C2–C7 and C C12–C17 rings, respectively.