3-Methyl-4-(3-methyl­phen­yl)-5-(2-pyridyl)-4H-1,2,4-triazole

Xie, D.-J.; Lu, W.; Wang, Z.-X.; Zhu, D.-R.

doi:10.1107/S1600536809015712

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1177-o1178

doi:10.1107/S1600536809015712

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3-Methyl-4-(3-methylphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole

Da-Jing Xie,^a Wei Lu,^a Zuo-Xiang Wang ^b and Dun-Ru Zhu ^a ^*

^aCollege of Chemistry and Chemical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhudr@njut.edu.cn

(Received 4 April 2009; accepted 27 April 2009; online 30 April 2009)

In the molecule of the title compound, C₁₅H₁₄N₄, 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 interactions, forming chains of molecules along [ $[\overline{1}]$ 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_r = 250.30
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.163
S = 1.30
2386 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015712/rz2308sup1.cif

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

checkCIF report

Comment top

In recent years, 1,2,4-triazole derivatives have attracted much attention (Haasnoot 2000; Klingele et al., 2005; Moliner et al., 2001), mainly because of the fact that these molecules can act as flexible bridging ligands and spacers between transition metal ions. For instance, some iron(II) triazole complexes have spin-crossover properties which can be used in molecular electronics (Kröber et al., 1993), as information storage (Kahn & Martinez, 1998) and switching materials (Zhu et al., 2002). Recently, some substituted 1,2,4-triazoles (Wang et al., 2005; Liu et al., 2005; Zhu et al., 2000; Zhang et al., 2004; Zhang et al., 2005) and their metal complexes (Schneider et al., 2007; Wu et al., 2007; Zhu et al., 2004; Matouzenko et al., 2004; Zhu et al., 2005; Nakano et al., 2004; Qi et al., 2008;) have been prepared by us and other groups. We report herein the crystal structure of the title compound, in order to elucidate its molecular conformation.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angle formed by the 1,2,4-triazole ring with the pyridyl and methylphenyl ring is 30.8 (2)° and 67.4 (2)°, respectively. The N3—C5—C6—N4 torsion angle including the N4 atom of the 1,2,4-triazole ring and the N3 atom of the pyridyl ring is 32.0 (3)°. In the crystal packing, chains of molecules running parallel to the [10 1] direction are formed through intermolecular C—H···N hydrogen bonds (Table 1).

Related literature top

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 top

The title compoud was synthesized by the reaction of 3,3'-dimethylphenylphosphazoanilide and N'-acetyl- N-(2-pyridoyl)hydrazine in o-dichlorobenzene at 463–473 K according to the literature method (Grimmel, et al. 1946; Klingsberg, et al. 1958). Single crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield 60%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atomic labelling. Displacement ellipsoids are shown at the 30% probability level

3-Methyl-4-(3-methylphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole top

Crystal data top

C₁₅H₁₄N₄	F(000) = 528
M_r = 250.30	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2386 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.963, T_max = 0.981	k = −12→12
10962 measured reflections	l = −16→16

Refinement top

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(F_o²) + (0.0801P)²] where P = (F_o² + 2F_c²)/3
S = 1.30	(Δ/σ)_max < 0.001
2386 reflections	Δρ_max = 0.15 e Å⁻³
173 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₄N₄	V = 1355.1 (4) Å³
M_r = 250.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.568 (1) Å	µ = 0.08 mm⁻¹
b = 10.519 (2) Å	T = 293 K
c = 13.555 (2) Å	0.50 × 0.50 × 0.25 mm
β = 96.64 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2386 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1937 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.981	R_int = 0.051
10962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.30	Δρ_max = 0.15 e Å⁻³
2386 reflections	Δρ_min = −0.14 e Å⁻³
173 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄
M_r	250.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.568 (1), 10.519 (2), 13.555 (2)
β (°)	96.64 (3)
V (Å³)	1355.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.50 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	10962, 2386, 1937
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.163, 1.30
No. of reflections	2386
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z+1/2.

Acknowledgements

This work was funded by the National Natural Science Foundation of China (No. 20771059) and the Natural Science Foundation of Jiangsu Province (BK2008371).

References

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