5,6-Diphenyl-3-(3-pyrid-yl)-1,2,4-triazine.

In the mol-ecule of the title compound, C(20)H(14)N(4), the triazine ring is attached to two phenyl rings and one pyridine ring. In the crystal, mol-ecules are linked by inter-molecular C-H⋯N hydrogen bonds. The crystal packing is also stabilized by C-H⋯π inter-actions.

Related literature

For applications of substituted 1,2,4-triazines, see: Denecke et al. (2005 ▶); Maheshwari et al. (2006 ▶): Zhao et al. (2003 ▶).

Experimental

Crystal data

C20H14N4

M = 310.35

Monoclinic,

a = 14.4775 (16) Å

b = 7.0923 (8) Å

c = 18.5786 (15) Å

β = 125.587 (6)°

V = 1551.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.31 × 0.28 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

9802 measured reflections

3770 independent reflections

2184 reflections with I > 2σ(I)

R int = 0.033

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.125

S = 1.04

3770 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002187/hg2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002187/hg2609Isup2.hkl

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

C20H14N4	F(000) = 648
Mr = 310.35	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Melting point: 444 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.4775 (16) Å	Cell parameters from 25 reflections
b = 7.0923 (8) Å	θ = 1.7–28.3°
c = 18.5786 (15) Å	µ = 0.08 mm−1
β = 125.587 (6)°	T = 293 K
V = 1551.3 (3) Å3	Block, yellow
Z = 4	0.31 × 0.28 × 0.26 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 28.3°, θmin = 1.7°
graphite	h = −16→19
ω scans	k = −7→9
9802 measured reflections	l = −24→20
3770 independent reflections	3 standard reflections every 200 reflections
2184 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3770 reflections	Δρmax = 0.16 e Å−3
218 parameters	Δρmin = −0.15 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: 0.0105 (17)

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	0.40833 (10)	0.74465 (17)	0.84881 (7)	0.0422 (3)
N2	0.48148 (11)	0.5785 (2)	0.75648 (8)	0.0554 (4)
N3	0.55312 (11)	0.5984 (2)	0.84483 (8)	0.0546 (4)
C20	0.69841 (13)	0.6021 (2)	1.03161 (9)	0.0505 (4)
H20A	0.7215	0.5456	0.9993	0.061*
C1	0.19450 (14)	0.9625 (2)	0.65096 (9)	0.0512 (4)
H1B	0.2415	0.9897	0.6334	0.061*
C2	0.09076 (15)	1.0535 (2)	0.61123 (10)	0.0598 (5)
H2B	0.0688	1.1431	0.5674	0.072*
C3	0.02025 (14)	1.0123 (3)	0.63613 (10)	0.0608 (5)
H3B	−0.0496	1.0727	0.6087	0.073*
C4	0.05291 (13)	0.8823 (2)	0.70138 (10)	0.0555 (4)
H4B	0.0050	0.8541	0.7180	0.067*
C5	0.15676 (12)	0.7931 (2)	0.74260 (9)	0.0475 (4)
H5A	0.1793	0.7073	0.7879	0.057*
C6	0.22752 (12)	0.8308 (2)	0.71683 (9)	0.0410 (4)
C7	0.33957 (11)	0.7350 (2)	0.76126 (8)	0.0398 (4)
C8	0.37453 (12)	0.6390 (2)	0.71427 (9)	0.0430 (4)
C9	0.29850 (13)	0.5980 (2)	0.61817 (9)	0.0437 (4)
C10	0.19430 (15)	0.5132 (3)	0.58174 (10)	0.0625 (5)
H10A	0.1710	0.4833	0.6176	0.075*
C11	0.12424 (16)	0.4725 (3)	0.49224 (11)	0.0692 (5)
H11A	0.0546	0.4141	0.4684	0.083*
C12	0.15742 (15)	0.5181 (2)	0.43853 (10)	0.0581 (5)
H12A	0.1102	0.4912	0.3783	0.070*
C13	0.25980 (15)	0.6030 (2)	0.47375 (10)	0.0578 (5)
H13A	0.2819	0.6354	0.4373	0.069*
C14	0.33114 (14)	0.6412 (2)	0.56364 (10)	0.0531 (4)
H14A	0.4016	0.6964	0.5874	0.064*
C15	0.51278 (12)	0.6718 (2)	0.88740 (9)	0.0410 (4)
C16	0.59002 (12)	0.6778 (2)	0.98515 (9)	0.0400 (4)
C17	0.55691 (13)	0.7604 (2)	1.03439 (9)	0.0506 (4)
H17A	0.4845	0.8112	1.0062	0.061*
C18	0.63165 (14)	0.7668 (2)	1.12525 (10)	0.0569 (5)
H18A	0.6111	0.8231	1.1592	0.068*
C19	0.73715 (14)	0.6882 (2)	1.16431 (10)	0.0575 (5)
H19A	0.7876	0.6932	1.2257	0.069*
N4	0.77171 (11)	0.6048 (2)	1.11941 (8)	0.0585 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0368 (7)	0.0495 (8)	0.0368 (6)	0.0013 (6)	0.0193 (5)	−0.0009 (6)
N2	0.0498 (9)	0.0713 (10)	0.0462 (8)	0.0062 (7)	0.0285 (7)	−0.0046 (7)
N3	0.0434 (8)	0.0729 (10)	0.0452 (8)	0.0091 (7)	0.0244 (7)	−0.0038 (7)
C20	0.0439 (9)	0.0556 (10)	0.0456 (9)	0.0041 (7)	0.0223 (8)	0.0010 (8)
C1	0.0526 (10)	0.0574 (10)	0.0405 (8)	−0.0012 (8)	0.0254 (7)	0.0024 (8)
C2	0.0567 (11)	0.0541 (11)	0.0424 (9)	0.0059 (8)	0.0138 (8)	0.0065 (8)
C3	0.0386 (9)	0.0666 (12)	0.0519 (10)	0.0081 (8)	0.0119 (8)	−0.0059 (9)
C4	0.0402 (9)	0.0705 (12)	0.0524 (10)	−0.0002 (8)	0.0249 (8)	−0.0068 (9)
C5	0.0436 (9)	0.0577 (10)	0.0378 (8)	0.0035 (7)	0.0217 (7)	0.0029 (7)
C6	0.0372 (8)	0.0486 (9)	0.0319 (7)	−0.0006 (7)	0.0171 (6)	−0.0040 (6)
C7	0.0375 (8)	0.0436 (9)	0.0371 (8)	−0.0029 (6)	0.0210 (7)	−0.0006 (6)
C8	0.0421 (8)	0.0484 (9)	0.0400 (8)	−0.0013 (7)	0.0248 (7)	−0.0011 (7)
C9	0.0477 (9)	0.0442 (9)	0.0414 (8)	0.0003 (7)	0.0271 (7)	−0.0027 (7)
C10	0.0674 (12)	0.0758 (13)	0.0490 (10)	−0.0227 (10)	0.0366 (9)	−0.0126 (9)
C11	0.0671 (12)	0.0810 (14)	0.0546 (11)	−0.0240 (10)	0.0326 (10)	−0.0166 (9)
C12	0.0664 (12)	0.0608 (11)	0.0397 (9)	0.0004 (9)	0.0267 (8)	−0.0065 (8)
C13	0.0681 (12)	0.0670 (12)	0.0479 (10)	0.0031 (9)	0.0392 (9)	0.0005 (8)
C14	0.0526 (10)	0.0626 (11)	0.0492 (9)	−0.0026 (8)	0.0325 (8)	−0.0038 (8)
C15	0.0363 (8)	0.0439 (9)	0.0407 (8)	0.0005 (7)	0.0211 (7)	−0.0006 (7)
C16	0.0349 (8)	0.0403 (8)	0.0420 (8)	−0.0022 (6)	0.0206 (7)	−0.0005 (7)
C17	0.0409 (9)	0.0596 (10)	0.0455 (9)	0.0058 (7)	0.0220 (7)	0.0009 (8)
C18	0.0576 (11)	0.0638 (11)	0.0452 (9)	0.0006 (9)	0.0276 (8)	−0.0052 (8)
C19	0.0502 (10)	0.0636 (11)	0.0412 (9)	−0.0057 (8)	0.0167 (8)	0.0005 (8)
N4	0.0426 (8)	0.0701 (10)	0.0471 (8)	0.0048 (7)	0.0173 (7)	0.0048 (7)

N1—C7	1.3253 (16)	C8—C9	1.4823 (19)
N1—C15	1.3440 (18)	C9—C14	1.379 (2)
N2—C8	1.3356 (19)	C9—C10	1.381 (2)
N2—N3	1.3448 (17)	C10—C11	1.383 (2)
N3—C15	1.3322 (18)	C10—H10A	0.9300
C20—N4	1.3313 (18)	C11—C12	1.375 (2)
C20—C16	1.385 (2)	C11—H11A	0.9300
C20—H20A	0.9300	C12—C13	1.363 (2)
C1—C6	1.385 (2)	C12—H12A	0.9300
C1—C2	1.388 (2)	C13—C14	1.386 (2)
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.375 (2)	C14—H14A	0.9300
C2—H2B	0.9300	C15—C16	1.4788 (19)
C3—C4	1.370 (2)	C16—C17	1.386 (2)
C3—H3B	0.9300	C17—C18	1.377 (2)
C4—C5	1.381 (2)	C17—H17A	0.9300
C4—H4B	0.9300	C18—C19	1.371 (2)
C5—C6	1.386 (2)	C18—H18A	0.9300
C5—H5A	0.9300	C19—N4	1.335 (2)
C6—C7	1.4887 (19)	C19—H19A	0.9300
C7—C8	1.4126 (19)
C7—N1—C15	116.31 (12)	C10—C9—C8	120.64 (13)
C8—N2—N3	119.33 (12)	C9—C10—C11	120.51 (15)
C15—N3—N2	118.20 (13)	C9—C10—H10A	119.7
N4—C20—C16	124.33 (15)	C11—C10—H10A	119.7
N4—C20—H20A	117.8	C12—C11—C10	120.12 (17)
C16—C20—H20A	117.8	C12—C11—H11A	119.9
C6—C1—C2	119.60 (16)	C10—C11—H11A	119.9
C6—C1—H1B	120.2	C13—C12—C11	119.82 (15)
C2—C1—H1B	120.2	C13—C12—H12A	120.1
C3—C2—C1	120.50 (16)	C11—C12—H12A	120.1
C3—C2—H2B	119.8	C12—C13—C14	120.27 (15)
C1—C2—H2B	119.8	C12—C13—H13A	119.9
C4—C3—C2	119.95 (16)	C14—C13—H13A	119.9
C4—C3—H3B	120.0	C9—C14—C13	120.54 (16)
C2—C3—H3B	120.0	C9—C14—H14A	119.7
C3—C4—C5	120.19 (16)	C13—C14—H14A	119.7
C3—C4—H4B	119.9	N3—C15—N1	125.41 (13)
C5—C4—H4B	119.9	N3—C15—C16	117.45 (13)
C4—C5—C6	120.33 (15)	N1—C15—C16	117.13 (12)
C4—C5—H5A	119.8	C20—C16—C17	117.00 (13)
C6—C5—H5A	119.8	C20—C16—C15	121.79 (13)
C1—C6—C5	119.42 (14)	C17—C16—C15	121.21 (13)
C1—C6—C7	120.15 (13)	C18—C17—C16	119.76 (15)
C5—C6—C7	120.41 (13)	C18—C17—H17A	120.1
N1—C7—C8	120.00 (13)	C16—C17—H17A	120.1
N1—C7—C6	117.05 (12)	C19—C18—C17	118.28 (15)
C8—C7—C6	122.95 (12)	C19—C18—H18A	120.9
N2—C8—C7	120.14 (13)	C17—C18—H18A	120.9
N2—C8—C9	116.00 (13)	N4—C19—C18	123.81 (15)
C7—C8—C9	123.86 (13)	N4—C19—H19A	118.1
C14—C9—C10	118.71 (14)	C18—C19—H19A	118.1
C14—C9—C8	120.64 (14)	C20—N4—C19	116.80 (14)

Cg1 and Cg2 are the centroids of the N4,C16–C20 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···N3	0.93	2.49	2.824 (4)	102
C13—H13A···Cg1i	0.93	3.49	3.345 (4)	91
C19—H19A···Cg2ii	0.93	3.67	3.109 (4)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4,C16–C20 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20A⋯N3	0.93	2.49	2.824 (4)	102
C13—H13A⋯Cg1i	0.93	3.49	3.345 (4)	91
C19—H19A⋯Cg2ii	0.93	3.67	3.109 (4)	121

Symmetry codes: (i) ; (ii) .