4-(3-Methyl-phen-yl)-3-phenyl-5-(2-pyrid-yl)-4H-1,2,4-triazole.

In the title compound, C(20)H(16)N(4), the m-tolyl and phenyl substituents form dihedral angles of 74.20 (6) and 36.94 (8)°, respectively, with the 1,2,4-triazole ring and the dihedral angle between the triazole and pyridine rings is 36.06 (9)°. In the crystal, mol-ecules are linked by C-H⋯N and C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Klingsberg (1958 ▶). For related structures, see: Wang et al. (2005 ▶); Huang et al. (2008 ▶).

Experimental

Crystal data

C20H16N4

M = 312.37

Monoclinic,

a = 11.246 (3) Å

b = 9.377 (2) Å

c = 18.956 (5) Å

β = 124.655 (16)°

V = 1644.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.65 × 0.50 × 0.27 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.787, T max = 1.000

16277 measured reflections

3751 independent reflections

2691 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.162

S = 1.06

3751 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049174/gk2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049174/gk2238Isup2.hkl

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

C20H16N4	F(000) = 656
Mr = 312.37	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3426 reflections
a = 11.246 (3) Å	θ = 2.3–27.5°
b = 9.377 (2) Å	µ = 0.08 mm−1
c = 18.956 (5) Å	T = 293 K
β = 124.655 (16)°	Block, white
V = 1644.3 (7) Å3	0.65 × 0.50 × 0.27 mm
Z = 4

Rigaku SCXmini diffractometer	3751 independent reflections
Radiation source: fine-focus sealed tube	2691 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scan	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
Tmin = 0.787, Tmax = 1.000	k = −12→12
16277 measured reflections	l = −24→24

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0823P)2 + 0.1727P] where P = (Fo2 + 2Fc2)/3
3751 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.91724 (18)	−0.14398 (19)	0.88581 (11)	0.0461 (4)
C2	0.74890 (17)	−0.02378 (18)	0.77576 (11)	0.0447 (4)
C3	1.05742 (18)	−0.1952 (2)	0.95950 (11)	0.0481 (4)
C4	1.0759 (2)	−0.3404 (2)	0.97830 (14)	0.0603 (5)
H4	1.0017	−0.4038	0.9427	0.072*
C5	1.2038 (2)	−0.3906 (2)	1.04945 (15)	0.0703 (6)
H5	1.2151	−0.4876	1.0619	0.084*
C6	1.3143 (2)	−0.2978 (3)	1.10189 (14)	0.0684 (6)
H6	1.4005	−0.3317	1.1498	0.082*
C7	1.2969 (2)	−0.1545 (2)	1.08313 (12)	0.0618 (5)
H7	1.3719	−0.0917	1.1186	0.074*
C8	1.16981 (19)	−0.1029 (2)	1.01265 (11)	0.0513 (4)
H8	1.1594	−0.0058	1.0007	0.062*
C9	0.67146 (17)	0.07496 (19)	0.70258 (10)	0.0457 (4)
C10	0.6617 (2)	0.1881 (3)	0.59246 (13)	0.0687 (6)
H10	0.7040	0.2101	0.5636	0.082*
C11	0.5267 (2)	0.2440 (2)	0.56156 (13)	0.0679 (6)
H11	0.4792	0.3009	0.5127	0.081*
C12	0.4644 (2)	0.2140 (2)	0.60434 (13)	0.0625 (5)
H12	0.3740	0.2507	0.5852	0.075*
C13	0.53747 (18)	0.1287 (2)	0.67597 (12)	0.0529 (5)
H13	0.4973	0.1074	0.7062	0.063*
C14	1.00456 (17)	0.05403 (19)	0.83598 (10)	0.0445 (4)
C15	1.08632 (18)	−0.0030 (2)	0.80966 (11)	0.0510 (4)
H15	1.0713	−0.0967	0.7903	0.061*
C16	1.19103 (19)	0.0793 (2)	0.81200 (13)	0.0595 (5)
C17	1.2116 (2)	0.2171 (3)	0.84272 (14)	0.0676 (6)
H17	1.2815	0.2735	0.8447	0.081*
C18	1.1320 (2)	0.2735 (2)	0.87042 (13)	0.0693 (6)
H18	1.1494	0.3660	0.8917	0.083*
C19	1.0255 (2)	0.1913 (2)	0.86644 (12)	0.0583 (5)
H19	0.9695	0.2283	0.8840	0.070*
C20	1.2756 (3)	0.0194 (3)	0.7795 (2)	0.1004 (10)
H20A	1.2660	0.0814	0.7363	0.151*
H20B	1.2390	−0.0734	0.7555	0.151*
H20C	1.3757	0.0120	0.8262	0.151*
N1	0.68517 (15)	−0.12089 (17)	0.79297 (10)	0.0527 (4)
N2	0.79217 (16)	−0.19790 (17)	0.86336 (10)	0.0536 (4)
N3	0.89575 (14)	−0.03337 (15)	0.83260 (9)	0.0441 (3)
N4	0.73453 (16)	0.1044 (2)	0.66152 (10)	0.0615 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0450 (9)	0.0508 (9)	0.0478 (9)	−0.0015 (8)	0.0295 (8)	0.0013 (8)
C2	0.0375 (9)	0.0539 (9)	0.0450 (9)	−0.0015 (7)	0.0247 (8)	−0.0039 (8)
C3	0.0455 (9)	0.0578 (10)	0.0489 (9)	0.0031 (8)	0.0316 (8)	0.0057 (8)
C4	0.0523 (11)	0.0593 (12)	0.0703 (12)	−0.0002 (9)	0.0354 (10)	0.0096 (10)
C5	0.0653 (13)	0.0683 (13)	0.0807 (15)	0.0140 (11)	0.0436 (12)	0.0243 (12)
C6	0.0563 (12)	0.0908 (16)	0.0562 (11)	0.0201 (11)	0.0308 (10)	0.0193 (11)
C7	0.0533 (11)	0.0786 (14)	0.0473 (10)	0.0022 (10)	0.0250 (9)	−0.0035 (10)
C8	0.0529 (10)	0.0559 (10)	0.0445 (9)	0.0026 (8)	0.0273 (9)	0.0014 (8)
C9	0.0408 (9)	0.0534 (10)	0.0433 (9)	−0.0030 (7)	0.0242 (8)	−0.0071 (7)
C10	0.0587 (12)	0.0980 (16)	0.0542 (11)	0.0093 (12)	0.0349 (10)	0.0124 (11)
C11	0.0525 (12)	0.0875 (15)	0.0519 (11)	0.0106 (10)	0.0226 (10)	0.0141 (11)
C12	0.0395 (10)	0.0748 (13)	0.0626 (12)	0.0098 (9)	0.0227 (9)	0.0021 (10)
C13	0.0409 (9)	0.0652 (11)	0.0542 (10)	−0.0010 (8)	0.0280 (8)	−0.0045 (9)
C14	0.0375 (9)	0.0542 (10)	0.0400 (8)	−0.0046 (7)	0.0210 (7)	0.0040 (7)
C15	0.0403 (9)	0.0629 (11)	0.0487 (10)	−0.0006 (8)	0.0245 (8)	0.0053 (8)
C16	0.0403 (10)	0.0791 (14)	0.0584 (11)	0.0024 (9)	0.0277 (9)	0.0208 (10)
C17	0.0481 (11)	0.0823 (15)	0.0605 (12)	−0.0146 (10)	0.0237 (10)	0.0190 (11)
C18	0.0746 (14)	0.0596 (12)	0.0589 (12)	−0.0203 (10)	0.0292 (11)	−0.0003 (10)
C19	0.0645 (12)	0.0581 (11)	0.0536 (11)	−0.0049 (9)	0.0344 (10)	0.0005 (9)
C20	0.0799 (17)	0.123 (2)	0.132 (2)	0.0221 (16)	0.0802 (18)	0.047 (2)
N1	0.0420 (8)	0.0610 (9)	0.0584 (9)	−0.0034 (7)	0.0304 (7)	−0.0005 (8)
N2	0.0450 (8)	0.0583 (9)	0.0599 (9)	−0.0028 (7)	0.0314 (8)	0.0045 (7)
N3	0.0379 (7)	0.0515 (8)	0.0450 (7)	−0.0017 (6)	0.0249 (6)	0.0015 (6)
N4	0.0491 (9)	0.0881 (12)	0.0516 (9)	0.0111 (8)	0.0313 (8)	0.0086 (8)

C1—N2	1.317 (2)	C11—C12	1.368 (3)
C1—N3	1.369 (2)	C11—H11	0.9300
C1—C3	1.470 (2)	C12—C13	1.375 (3)
C2—N1	1.310 (2)	C12—H12	0.9300
C2—N3	1.368 (2)	C13—H13	0.9300
C2—C9	1.472 (2)	C14—C19	1.375 (3)
C3—C8	1.383 (3)	C14—C15	1.379 (2)
C3—C4	1.393 (3)	C14—N3	1.444 (2)
C4—C5	1.379 (3)	C15—C16	1.388 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.373 (3)	C16—C17	1.381 (3)
C5—H5	0.9300	C16—C20	1.504 (3)
C6—C7	1.375 (3)	C17—C18	1.375 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.375 (3)	C18—C19	1.390 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—N4	1.346 (2)	C20—H20A	0.9600
C9—C13	1.384 (2)	C20—H20B	0.9600
C10—N4	1.335 (3)	C20—H20C	0.9600
C10—C11	1.383 (3)	N1—N2	1.387 (2)
C10—H10	0.9300
N2—C1—N3	110.12 (15)	C13—C12—H12	120.5
N2—C1—C3	123.56 (16)	C12—C13—C9	119.16 (18)
N3—C1—C3	126.29 (15)	C12—C13—H13	120.4
N1—C2—N3	110.15 (15)	C9—C13—H13	120.4
N1—C2—C9	123.91 (15)	C19—C14—C15	121.67 (16)
N3—C2—C9	125.86 (15)	C19—C14—N3	119.22 (16)
C8—C3—C4	118.92 (17)	C15—C14—N3	119.10 (16)
C8—C3—C1	122.00 (17)	C14—C15—C16	120.07 (19)
C4—C3—C1	119.04 (17)	C14—C15—H15	120.0
C5—C4—C3	120.3 (2)	C16—C15—H15	120.0
C5—C4—H4	119.9	C17—C16—C15	117.99 (19)
C3—C4—H4	119.9	C17—C16—C20	121.9 (2)
C6—C5—C4	120.2 (2)	C15—C16—C20	120.1 (2)
C6—C5—H5	119.9	C18—C17—C16	122.09 (18)
C4—C5—H5	119.9	C18—C17—H17	119.0
C5—C6—C7	119.64 (19)	C16—C17—H17	119.0
C5—C6—H6	120.2	C17—C18—C19	119.6 (2)
C7—C6—H6	120.2	C17—C18—H18	120.2
C8—C7—C6	120.8 (2)	C19—C18—H18	120.2
C8—C7—H7	119.6	C14—C19—C18	118.5 (2)
C6—C7—H7	119.6	C14—C19—H19	120.7
C7—C8—C3	120.15 (19)	C18—C19—H19	120.7
C7—C8—H8	119.9	C16—C20—H20A	109.5
C3—C8—H8	119.9	C16—C20—H20B	109.5
N4—C9—C13	122.49 (17)	H20A—C20—H20B	109.5
N4—C9—C2	116.73 (15)	C16—C20—H20C	109.5
C13—C9—C2	120.72 (16)	H20A—C20—H20C	109.5
N4—C10—C11	123.52 (19)	H20B—C20—H20C	109.5
N4—C10—H10	118.2	C2—N1—N2	107.66 (14)
C11—C10—H10	118.2	C1—N2—N1	107.09 (14)
C12—C11—C10	118.65 (19)	C2—N3—C1	104.97 (13)
C12—C11—H11	120.7	C2—N3—C14	127.64 (14)
C10—C11—H11	120.7	C1—N3—C14	127.40 (13)
C11—C12—C13	119.03 (18)	C10—N4—C9	117.14 (16)
C11—C12—H12	120.5

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2i	0.93	2.60	3.375 (3)	142
C20—H20A···N2ii	0.96	2.62	3.549 (4)	163
C10—H10···Cg1ii	0.93	2.72	3.646 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N2i	0.93	2.60	3.375 (3)	142
C20—H20A⋯N2ii	0.96	2.62	3.549 (4)	163
C10—H10⋯Cg1ii	0.93	2.72	3.646 (3)	175

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C3–C8 ring.