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

In the mol-ecule of the title compound, C(17)H(17)N(3)O(3), the triazole ring is oriented at dihedral angles of 88.09 (3) and 83.72 (3)° with respect to the 2-methoxy-benzyl and 2-methoxy-phenyl rings, respectively. The dihedral angle between the 2-methoxy-benzyl and 2-methoxy-phenyl rings is 52.95 (3)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. There is a π-π contact between the 2-methoxy-phenyl 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 = 311.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.091

S = 1.06

3160 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 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 I, global. DOI: 10.1107/S1600536809001482/hk2613sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001482/hk2613Isup2.hkl

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

C17H17N3O3	F(000) = 656
Mr = 311.34	Dx = 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

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

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(Fo2) + (0.0403P)2 + 0.586P] where P = (Fo2 + 2Fc2)/3
3160 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.28 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	0.29433 (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*

	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)

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)

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)

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) .