2-[4-(4-Methoxy-phen-yl)-5-(2-pyrid-yl)-4H-1,2,4-triazol-3-yl]phenol.

In the title compound, C(20)H(16)N(4)O(2), the benzene rings of the 2-hydroxy-phenyl and 4-methoxy-lphenyl groups form dihedral angles of 64.02 (8) and 77.39 (7)°, respectively, with the mean plane of the triazole ring. The dihedral angle between the triazole ring mean plane and the pyridyl ring is 9.61 (8)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains propagating in [010].

Related literature

For the potential anti­fungal and anti­bacterial properties of 1,2,4-triazoles, see: Collin, et al. (2003 ▶); Papakonstanti­nou-Garoufalias, et al. (2002 ▶). For the synthesis of the title compound, see: Zhang et al. (2004 ▶). For related structures, see: Zhang et al. (2004 ▶); Zhang, Liu, Ma et al. (2005 ▶); Zhang, Liu, Yang et al. (2005 ▶); Zhu et al. (2000 ▶).

Experimental

Crystal data

C20H16N4O2

M = 344.37

Monoclinic,

a = 10.0842 (9) Å

b = 10.4903 (9) Å

c = 16.7214 (14) Å

β = 94.658 (2)°

V = 1763.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.991, T max = 0.993

8997 measured reflections

3278 independent reflections

2734 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.04

3278 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809022223/su2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022223/su2120Isup2.hkl

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

C20H16N4O2	F(000) = 720
Mr = 344.37	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2.3 reflections
a = 10.0842 (9) Å	θ = 15–532°
b = 10.4903 (9) Å	µ = 0.09 mm−1
c = 16.7214 (14) Å	T = 293 K
β = 94.658 (2)°	Block, colourless
V = 1763.1 (3) Å3	0.10 × 0.10 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3278 independent reflections
Radiation source: fine-focus sealed tube	2734 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→9
Tmin = 0.991, Tmax = 0.993	k = −12→12
8997 measured reflections	l = −20→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.2618P] where P = (Fo2 + 2Fc2)/3
3278 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.13 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	0.25887 (10)	0.88801 (10)	0.27051 (6)	0.0540 (3)
H1O	0.2548 (16)	0.8171 (17)	0.3044 (10)	0.065*
O2	0.57961 (12)	0.52684 (10)	0.08768 (7)	0.0657 (3)
N3	0.30394 (11)	0.98466 (10)	0.09726 (6)	0.0413 (3)
N1	0.26339 (12)	1.17680 (11)	0.13995 (7)	0.0495 (3)
N2	0.20046 (12)	1.16372 (11)	0.06409 (7)	0.0502 (3)
C10	0.07912 (15)	1.07145 (17)	−0.08501 (9)	0.0592 (4)
H10	0.0505	1.1495	−0.0664	0.071*
C1	0.32455 (13)	1.06948 (12)	0.15894 (8)	0.0430 (3)
C2	0.22553 (13)	1.04857 (13)	0.03920 (8)	0.0430 (3)
C3	0.40733 (14)	1.04578 (12)	0.23412 (8)	0.0459 (3)
C4	0.37258 (14)	0.95349 (12)	0.28844 (8)	0.0448 (3)
C5	0.45291 (16)	0.93499 (15)	0.35907 (10)	0.0595 (4)
H5	0.4300	0.8741	0.3959	0.071*
C6	0.5664 (2)	1.00676 (19)	0.37443 (12)	0.0780 (6)
H6	0.6202	0.9934	0.4215	0.094*
C7	0.6009 (2)	1.0981 (2)	0.32077 (13)	0.0868 (6)
H7	0.6778	1.1462	0.3315	0.104*
C8	0.52135 (18)	1.11758 (16)	0.25158 (11)	0.0686 (5)
H8	0.5442	1.1800	0.2157	0.082*
C9	0.17333 (13)	1.00019 (14)	−0.03971 (8)	0.0450 (3)
C11	0.02873 (17)	1.0247 (2)	−0.15797 (10)	0.0722 (5)
H11	−0.0347	1.0707	−0.1895	0.087*
C12	0.07285 (19)	0.9101 (2)	−0.18364 (10)	0.0733 (5)
H12	0.0396	0.8760	−0.2326	0.088*
C13	0.1670 (2)	0.84634 (19)	−0.13575 (11)	0.0738 (5)
H13	0.1972	0.7686	−0.1539	0.089*
N4	0.21866 (15)	0.88858 (13)	−0.06456 (8)	0.0636 (4)
C14	0.37019 (13)	0.86290 (12)	0.09457 (8)	0.0405 (3)
C15	0.50296 (14)	0.86186 (13)	0.08103 (9)	0.0490 (3)
H15	0.5472	0.9380	0.0730	0.059*
C16	0.57011 (15)	0.74766 (14)	0.07936 (9)	0.0537 (4)
H16	0.6597	0.7466	0.0697	0.064*
C17	0.50458 (15)	0.63460 (13)	0.09194 (8)	0.0473 (3)
C18	0.37133 (16)	0.63626 (13)	0.10599 (9)	0.0517 (4)
H18	0.3269	0.5604	0.1145	0.062*
C19	0.30437 (14)	0.75134 (13)	0.10732 (9)	0.0487 (3)
H19	0.2148	0.7530	0.1169	0.058*
C20	0.5210 (2)	0.40928 (15)	0.10653 (11)	0.0757 (5)
H20A	0.5837	0.3416	0.1011	0.114*
H20B	0.4433	0.3947	0.0706	0.114*
H20C	0.4962	0.4117	0.1607	0.114*

	U11	U22	U33	U12	U13	U23
O1	0.0524 (6)	0.0530 (6)	0.0546 (6)	−0.0087 (5)	−0.0074 (5)	0.0118 (5)
O2	0.0727 (7)	0.0476 (6)	0.0768 (8)	0.0185 (5)	0.0054 (6)	0.0077 (5)
N3	0.0447 (6)	0.0357 (6)	0.0428 (6)	0.0005 (5)	−0.0015 (5)	0.0027 (5)
N1	0.0594 (7)	0.0384 (6)	0.0495 (7)	0.0038 (5)	−0.0027 (5)	0.0024 (5)
N2	0.0566 (7)	0.0435 (7)	0.0494 (7)	0.0054 (5)	−0.0018 (5)	0.0059 (5)
C10	0.0550 (9)	0.0737 (11)	0.0482 (9)	0.0099 (8)	−0.0007 (7)	0.0109 (7)
C1	0.0468 (7)	0.0357 (7)	0.0459 (7)	−0.0020 (6)	0.0001 (6)	0.0013 (6)
C2	0.0428 (7)	0.0424 (7)	0.0434 (7)	0.0009 (6)	0.0010 (6)	0.0079 (6)
C3	0.0521 (8)	0.0375 (7)	0.0467 (8)	−0.0003 (6)	−0.0047 (6)	−0.0016 (6)
C4	0.0483 (7)	0.0374 (7)	0.0475 (8)	0.0017 (6)	−0.0040 (6)	−0.0023 (6)
C5	0.0697 (10)	0.0540 (9)	0.0518 (9)	−0.0031 (8)	−0.0131 (7)	0.0063 (7)
C6	0.0815 (12)	0.0758 (12)	0.0699 (12)	−0.0116 (10)	−0.0351 (10)	0.0067 (9)
C7	0.0815 (13)	0.0816 (13)	0.0905 (14)	−0.0333 (11)	−0.0346 (11)	0.0112 (11)
C8	0.0723 (11)	0.0572 (10)	0.0732 (11)	−0.0205 (8)	−0.0137 (9)	0.0104 (8)
C9	0.0423 (7)	0.0515 (8)	0.0412 (7)	−0.0030 (6)	0.0028 (6)	0.0075 (6)
C11	0.0587 (10)	0.1077 (15)	0.0486 (9)	0.0108 (10)	−0.0058 (7)	0.0141 (9)
C12	0.0701 (11)	0.1032 (15)	0.0449 (9)	−0.0093 (11)	−0.0068 (8)	−0.0029 (9)
C13	0.0857 (12)	0.0764 (12)	0.0565 (10)	0.0041 (10)	−0.0109 (9)	−0.0122 (9)
N4	0.0733 (9)	0.0618 (8)	0.0530 (8)	0.0076 (7)	−0.0120 (6)	−0.0052 (6)
C14	0.0457 (7)	0.0363 (7)	0.0383 (7)	0.0027 (5)	−0.0030 (5)	0.0008 (5)
C15	0.0461 (8)	0.0426 (7)	0.0572 (9)	−0.0031 (6)	−0.0017 (6)	0.0079 (6)
C16	0.0435 (8)	0.0528 (9)	0.0644 (10)	0.0047 (6)	0.0018 (7)	0.0079 (7)
C17	0.0565 (8)	0.0433 (8)	0.0413 (7)	0.0106 (6)	−0.0003 (6)	0.0035 (6)
C18	0.0645 (9)	0.0361 (7)	0.0550 (9)	−0.0045 (6)	0.0089 (7)	0.0023 (6)
C19	0.0475 (8)	0.0430 (8)	0.0561 (9)	−0.0011 (6)	0.0077 (6)	−0.0005 (6)
C20	0.1210 (16)	0.0431 (9)	0.0652 (11)	0.0185 (9)	0.0206 (10)	0.0094 (8)

O1—C4	1.3494 (17)	C7—H7	0.9300
O1—H1O	0.938 (18)	C8—H8	0.9300
O2—C17	1.3654 (16)	C9—N4	1.3354 (19)
O2—C20	1.414 (2)	C11—C12	1.364 (3)
N3—C1	1.3653 (17)	C11—H11	0.9300
N3—C2	1.3757 (16)	C12—C13	1.366 (3)
N3—C14	1.4439 (16)	C12—H12	0.9300
N1—C1	1.3103 (17)	C13—N4	1.335 (2)
N1—N2	1.3783 (16)	C13—H13	0.9300
N2—C2	1.3089 (18)	C14—C19	1.3706 (18)
C10—C11	1.373 (2)	C14—C15	1.3759 (19)
C10—C9	1.385 (2)	C15—C16	1.378 (2)
C10—H10	0.9300	C15—H15	0.9300
C1—C3	1.4725 (19)	C16—C17	1.382 (2)
C2—C9	1.4708 (19)	C16—H16	0.9300
C3—C8	1.386 (2)	C17—C18	1.383 (2)
C3—C4	1.3918 (19)	C18—C19	1.3843 (19)
C4—C5	1.390 (2)	C18—H18	0.9300
C5—C6	1.376 (2)	C19—H19	0.9300
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.377 (3)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600
C7—C8	1.369 (2)
C4—O1—H1O	110.4 (10)	C10—C9—C2	118.95 (14)
C17—O2—C20	117.84 (13)	C12—C11—C10	119.19 (16)
C1—N3—C2	105.01 (11)	C12—C11—H11	120.4
C1—N3—C14	123.90 (11)	C10—C11—H11	120.4
C2—N3—C14	130.54 (11)	C11—C12—C13	118.43 (17)
C1—N1—N2	108.06 (11)	C11—C12—H12	120.8
C2—N2—N1	107.35 (11)	C13—C12—H12	120.8
C11—C10—C9	118.76 (17)	N4—C13—C12	124.21 (18)
C11—C10—H10	120.6	N4—C13—H13	117.9
C9—C10—H10	120.6	C12—C13—H13	117.9
N1—C1—N3	109.70 (12)	C9—N4—C13	116.73 (14)
N1—C1—C3	125.10 (12)	C19—C14—C15	120.59 (12)
N3—C1—C3	125.16 (12)	C19—C14—N3	121.29 (12)
N2—C2—N3	109.89 (12)	C15—C14—N3	118.10 (11)
N2—C2—C9	122.65 (12)	C14—C15—C16	119.78 (13)
N3—C2—C9	127.46 (12)	C14—C15—H15	120.1
C8—C3—C4	119.28 (13)	C16—C15—H15	120.1
C8—C3—C1	119.43 (13)	C15—C16—C17	120.08 (13)
C4—C3—C1	121.29 (12)	C15—C16—H16	120.0
O1—C4—C5	122.93 (13)	C17—C16—H16	120.0
O1—C4—C3	117.61 (12)	O2—C17—C16	115.38 (13)
C5—C4—C3	119.43 (13)	O2—C17—C18	124.72 (13)
C6—C5—C4	120.02 (15)	C16—C17—C18	119.89 (12)
C6—C5—H5	120.0	C17—C18—C19	119.72 (13)
C4—C5—H5	120.0	C17—C18—H18	120.1
C5—C6—C7	120.64 (16)	C19—C18—H18	120.1
C5—C6—H6	119.7	C14—C19—C18	119.94 (13)
C7—C6—H6	119.7	C14—C19—H19	120.0
C8—C7—C6	119.54 (16)	C18—C19—H19	120.0
C8—C7—H7	120.2	O2—C20—H20A	109.5
C6—C7—H7	120.2	O2—C20—H20B	109.5
C7—C8—C3	121.08 (16)	H20A—C20—H20B	109.5
C7—C8—H8	119.5	O2—C20—H20C	109.5
C3—C8—H8	119.5	H20A—C20—H20C	109.5
N4—C9—C10	122.68 (14)	H20B—C20—H20C	109.5
N4—C9—C2	118.37 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1i	0.938 (18)	1.759 (19)	2.6937 (16)	174.2 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1i	0.938 (18)	1.759 (19)	2.6937 (16)	174.2 (16)

Symmetry code: (i) .