3-Methyl-4-(3-methyl-phen-yl)-5-(2-pyridyl)-4H-1,2,4-triazole.

In the mol-ecule of the title compound, C(15)H(14)N(4), the triazole ring is oriented at dihedral angles of 30.8 (2) and 67.4 (2)° with respect to the pyridine and benzene rings, respectively. The crystal structure is stabilized by C-H⋯N hydrogen-bonding inter-actions, forming chains of mol-ecules along [01].

Related literature

For general background to the chemistry of 1,2,4-triazole derivatives, see: Haasnoot (2000 ▶); Klingele et al. (2005 ▶); Moliner et al. (2001 ▶). For the applications of iron(II)–triazole complexes in electronics, see: Kröber et al. (1993 ▶); Kahn & Martinez (1998 ▶); Zhu et al. (2002 ▶). For the synthesis of the title compound, see: Grimmel et al. (1946 ▶); Klingsberg et al. (1958 ▶). For the synthesis and structures of related triazole ligands and complexes, see: Wang et al. (2005 ▶); Liu et al. (2005 ▶); Zhu et al. (2000 ▶, 2004 ▶, 2005 ▶); Zhang et al. (2004 ▶, 2005 ▶); Schneider et al. (2007 ▶); Wu et al. (2007 ▶); Matouzenko et al. (2004 ▶); Nakano et al. (2004 ▶); Qi et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N4

M = 250.30

Monoclinic,

a = 9.568 (1) Å

b = 10.519 (2) Å

c = 13.555 (2) Å

β = 96.64 (3)°

V = 1355.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.50 × 0.50 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.981

10962 measured reflections

2386 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.163

S = 1.30

2386 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809015712/rz2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015712/rz2308Isup2.hkl

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

C15H14N4	F(000) = 528
Mr = 250.30	Dx = 1.227 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2955 reflections
a = 9.568 (1) Å	θ = 2.8–27.5°
b = 10.519 (2) Å	µ = 0.08 mm−1
c = 13.555 (2) Å	T = 293 K
β = 96.64 (3)°	Prism, colorless
V = 1355.1 (4) Å3	0.50 × 0.50 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	2386 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.963, Tmax = 0.981	k = −12→12
10962 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0801P)2] where P = (Fo2 + 2Fc2)/3
S = 1.30	(Δ/σ)max < 0.001
2386 reflections	Δρmax = 0.15 e Å−3
173 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (8)

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
N1	0.1372 (2)	0.8645 (2)	0.47665 (12)	0.0792 (6)
N2	0.05623 (19)	0.76334 (17)	0.50563 (11)	0.0725 (5)
N3	−0.09930 (17)	0.73930 (15)	0.73296 (12)	0.0658 (5)
N4	0.11155 (15)	0.88829 (15)	0.63546 (10)	0.0561 (4)
C1	−0.1707 (2)	0.6566 (2)	0.78336 (17)	0.0793 (7)
H1B	−0.2143	0.6876	0.8363	0.095*
C2	−0.1837 (2)	0.5290 (2)	0.76202 (19)	0.0819 (7)
H2B	−0.2362	0.4761	0.7985	0.098*
C3	−0.1172 (3)	0.4818 (2)	0.68567 (18)	0.0845 (7)
H3B	−0.1237	0.3959	0.6694	0.101*
C4	−0.0409 (2)	0.5632 (2)	0.63355 (15)	0.0731 (6)
H4A	0.0058	0.5328	0.5819	0.088*
C5	−0.03405 (18)	0.69079 (18)	0.65844 (12)	0.0537 (5)
C6	0.04303 (19)	0.77911 (17)	0.60035 (13)	0.0559 (5)
C7	0.1694 (2)	0.9368 (2)	0.55513 (15)	0.0680 (6)
C8	0.12918 (18)	0.93671 (17)	0.73586 (13)	0.0527 (5)
C9	0.06763 (19)	1.05012 (18)	0.75777 (13)	0.0571 (5)
H9A	0.0163	1.0962	0.7074	0.069*
C10	0.0816 (2)	1.09668 (18)	0.85510 (14)	0.0608 (5)
C11	0.1585 (2)	1.0247 (2)	0.92840 (15)	0.0719 (6)
H11A	0.1680	1.0531	0.9938	0.086*
C12	0.2210 (2)	0.9120 (2)	0.90560 (16)	0.0793 (7)
H12A	0.2728	0.8657	0.9557	0.095*
C13	0.2075 (2)	0.86690 (19)	0.80930 (14)	0.0673 (6)
H13A	0.2501	0.7911	0.7940	0.081*
C14	0.0136 (3)	1.2195 (2)	0.88081 (18)	0.0886 (7)
H14A	0.0346	1.2357	0.9507	0.133*
H14B	−0.0864	1.2134	0.8642	0.133*
H14C	0.0493	1.2879	0.8440	0.133*
C15	0.2596 (3)	1.0526 (2)	0.55930 (19)	0.0941 (8)
H15A	0.2877	1.0689	0.4948	0.141*
H15B	0.3416	1.0395	0.6061	0.141*
H15C	0.2075	1.1240	0.5797	0.141*

	U11	U22	U33	U12	U13	U23
N1	0.0814 (13)	0.1051 (15)	0.0546 (11)	0.0076 (11)	0.0229 (9)	0.0042 (9)
N2	0.0765 (11)	0.0929 (13)	0.0501 (10)	0.0047 (9)	0.0158 (8)	−0.0068 (8)
N3	0.0660 (10)	0.0654 (10)	0.0701 (11)	−0.0030 (8)	0.0257 (8)	−0.0060 (8)
N4	0.0555 (9)	0.0664 (10)	0.0474 (9)	0.0024 (7)	0.0109 (7)	0.0019 (7)
C1	0.0745 (14)	0.0799 (16)	0.0892 (16)	−0.0026 (11)	0.0344 (12)	0.0051 (11)
C2	0.0766 (15)	0.0713 (15)	0.0959 (18)	−0.0122 (11)	0.0024 (12)	0.0183 (12)
C3	0.1042 (19)	0.0598 (13)	0.0850 (17)	−0.0060 (13)	−0.0078 (14)	−0.0009 (12)
C4	0.0935 (16)	0.0646 (13)	0.0602 (13)	0.0125 (11)	0.0040 (11)	−0.0104 (10)
C5	0.0512 (10)	0.0624 (11)	0.0466 (10)	0.0045 (8)	0.0022 (7)	−0.0059 (8)
C6	0.0544 (10)	0.0672 (12)	0.0466 (10)	0.0076 (9)	0.0084 (8)	−0.0056 (8)
C7	0.0651 (12)	0.0856 (14)	0.0556 (12)	0.0039 (10)	0.0173 (9)	0.0108 (10)
C8	0.0508 (10)	0.0598 (11)	0.0477 (10)	−0.0027 (8)	0.0060 (8)	−0.0003 (8)
C9	0.0549 (11)	0.0626 (11)	0.0541 (11)	0.0017 (9)	0.0075 (8)	0.0057 (8)
C10	0.0599 (11)	0.0611 (12)	0.0616 (12)	−0.0053 (9)	0.0067 (9)	−0.0054 (9)
C11	0.0791 (14)	0.0800 (14)	0.0534 (12)	−0.0072 (11)	−0.0057 (10)	−0.0088 (10)
C12	0.0842 (15)	0.0839 (15)	0.0633 (14)	0.0113 (12)	−0.0186 (11)	−0.0015 (11)
C13	0.0692 (13)	0.0658 (12)	0.0637 (13)	0.0106 (10)	−0.0053 (10)	−0.0023 (9)
C14	0.1013 (18)	0.0802 (16)	0.0844 (16)	0.0122 (13)	0.0109 (13)	−0.0157 (12)
C15	0.0968 (18)	0.0993 (18)	0.0908 (17)	−0.0152 (14)	0.0309 (14)	0.0164 (13)

N1—C7	1.315 (3)	C8—C9	1.378 (3)
N1—N2	1.399 (3)	C8—C13	1.385 (3)
N2—C6	1.315 (3)	C9—C10	1.399 (3)
N3—C1	1.341 (3)	C9—H9A	0.9300
N3—C5	1.348 (2)	C10—C11	1.390 (3)
N4—C7	1.375 (3)	C10—C14	1.506 (3)
N4—C6	1.380 (3)	C11—C12	1.379 (3)
N4—C8	1.445 (3)	C11—H11A	0.9300
C1—C2	1.376 (4)	C12—C13	1.381 (3)
C1—H1B	0.9300	C12—H12A	0.9300
C2—C3	1.369 (3)	C13—H13A	0.9300
C2—H2B	0.9300	C14—H14A	0.9600
C3—C4	1.373 (3)	C14—H14B	0.9600
C3—H3B	0.9300	C14—H14C	0.9600
C4—C5	1.384 (3)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.470 (3)	C15—H15C	0.9600
C7—C15	1.490 (4)
C7—N1—N2	107.35 (17)	C13—C8—N4	118.98 (18)
C6—N2—N1	107.28 (17)	C8—C9—C10	120.65 (17)
C1—N3—C5	116.33 (19)	C8—C9—H9A	119.7
C7—N4—C6	104.75 (17)	C10—C9—H9A	119.7
C7—N4—C8	126.95 (19)	C11—C10—C9	117.9 (2)
C6—N4—C8	128.13 (15)	C11—C10—C14	120.6 (2)
N3—C1—C2	124.4 (2)	C9—C10—C14	121.47 (19)
N3—C1—H1B	117.8	C12—C11—C10	121.0 (2)
C2—C1—H1B	117.8	C12—C11—H11A	119.5
C3—C2—C1	118.3 (2)	C10—C11—H11A	119.5
C3—C2—H2B	120.9	C11—C12—C13	120.76 (19)
C1—C2—H2B	120.9	C11—C12—H12A	119.6
C2—C3—C4	119.0 (2)	C13—C12—H12A	119.6
C2—C3—H3B	120.5	C12—C13—C8	118.8 (2)
C4—C3—H3B	120.5	C12—C13—H13A	120.6
C3—C4—C5	119.5 (2)	C8—C13—H13A	120.6
C3—C4—H4A	120.2	C10—C14—H14A	109.5
C5—C4—H4A	120.2	C10—C14—H14B	109.5
N3—C5—C4	122.48 (18)	H14A—C14—H14B	109.5
N3—C5—C6	117.83 (18)	C10—C14—H14C	109.5
C4—C5—C6	119.66 (18)	H14A—C14—H14C	109.5
N2—C6—N4	110.26 (17)	H14B—C14—H14C	109.5
N2—C6—C5	123.65 (18)	C7—C15—H15A	109.5
N4—C6—C5	126.10 (17)	C7—C15—H15B	109.5
N1—C7—N4	110.4 (2)	H15A—C15—H15B	109.5
N1—C7—C15	125.7 (2)	C7—C15—H15C	109.5
N4—C7—C15	123.9 (2)	H15A—C15—H15C	109.5
C9—C8—C13	120.88 (18)	H15B—C15—H15C	109.5
C9—C8—N4	120.14 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1i	0.93	2.56	3.377 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N1i	0.93	2.56	3.377 (3)	147

Symmetry code: (i) .