5,6-Diphenyl-pyrazine-2,3-dicarbonitrile.

In the title compound, C(18)H(10)N(4), the pyrazine ring is oriented at dihedral angles of 48.08 (7) and 44.80 (7)° with respect to the phenyl rings, while the dihedral angle between the phenyl rings is 49.47 (7)°. In the crystal structure, weak π-π contacts between pyrazine and phenyl rings [centroid-centroid distance = 3.813 (1) Å] may stabilize the structure.

Related literature

For applications of 2,3-dicyano­pyrazine derivatives, see: Hou et al. (1993 ▶); Jaung et al. (1996 ▶); Takematsu et al. (1981 ▶). For a related structure, see: Zhang et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H10N4

M = 282.31

Monoclinic,

a = 9.2195 (2) Å

b = 7.2837 (2) Å

c = 21.5507 (5) Å

β = 101.108 (1)°

V = 1420.06 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 294 K

0.30 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: none

28933 measured reflections

2911 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.145

S = 1.05

2911 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033029/xu2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033029/xu2592Isup2.hkl

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

C18H10N4	F(000) = 584
Mr = 282.31	Dx = 1.320 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4324 reflections
a = 9.2195 (2) Å	θ = 2.3–26.4°
b = 7.2837 (2) Å	µ = 0.08 mm−1
c = 21.5507 (5) Å	T = 294 K
β = 101.108 (1)°	Block, colorless
V = 1420.06 (6) Å3	0.30 × 0.15 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	1708 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.137
graphite	θmax = 26.4°, θmin = 2.3°
ω scans	h = −11→11
28933 measured reflections	k = −9→8
2911 independent reflections	l = −26→26

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) = 0.145	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.1959P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2911 reflections	Δρmax = 0.14 e Å−3
200 parameters	Δρmin = −0.17 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: 0.039 (5)

Experimental. IR (Mattson 1000 F T—IR spectrophotometer, KBr, νmax): 3073 cm-1 (aromatic C—H), 2238 cm-1 (CN), 1515 cm-1 (CC). 1H-NMR (Bruker-Spectrospin Avance DPX 400 MHz Ultra-Shield): (δ, DMSO-d6) 7.40–7.50 p.p.m. (m, 10H, ArH).

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	0.9159 (2)	0.0899 (3)	0.77849 (9)	0.0548 (5)
N2	1.1240 (2)	−0.0919 (3)	0.72267 (8)	0.0541 (5)
N3	1.1092 (3)	0.1454 (3)	0.92857 (11)	0.0803 (7)
N4	1.4193 (3)	−0.1142 (3)	0.84155 (11)	0.0843 (8)
C1	0.6099 (3)	0.0462 (3)	0.70896 (11)	0.0558 (6)
H1	0.6212	0.0037	0.7503	0.067*
C2	0.4703 (3)	0.0730 (3)	0.67328 (13)	0.0642 (7)
H2	0.3876	0.0446	0.6903	0.077*
C3	0.4526 (3)	0.1412 (3)	0.61287 (13)	0.0677 (7)
H3	0.3582	0.1564	0.5888	0.081*
C4	0.5738 (3)	0.1870 (4)	0.58798 (12)	0.0688 (7)
H4	0.5615	0.2378	0.5477	0.083*
C5	0.7134 (3)	0.1579 (3)	0.62258 (11)	0.0617 (7)
H5	0.7954	0.1887	0.6054	0.074*
C6	0.7335 (2)	0.0829 (3)	0.68285 (10)	0.0508 (6)
C7	0.9497 (3)	−0.1528 (3)	0.62762 (10)	0.0517 (6)
C8	0.8195 (3)	−0.2521 (3)	0.60918 (11)	0.0625 (7)
H8	0.7527	−0.2615	0.6363	0.075*
C9	0.7894 (3)	−0.3364 (4)	0.55095 (13)	0.0717 (7)
H9	0.7027	−0.4035	0.5390	0.086*
C10	0.8868 (3)	−0.3215 (4)	0.51061 (12)	0.0755 (8)
H10	0.8650	−0.3765	0.4709	0.091*
C11	1.0169 (3)	−0.2254 (4)	0.52857 (12)	0.0746 (8)
H11	1.0829	−0.2163	0.5011	0.090*
C12	1.0494 (3)	−0.1427 (3)	0.58728 (11)	0.0631 (7)
H12	1.1382	−0.0803	0.5997	0.076*
C13	0.9860 (2)	−0.0659 (3)	0.69065 (10)	0.0496 (6)
C14	0.8827 (2)	0.0355 (3)	0.71825 (10)	0.0490 (5)
C15	1.1567 (2)	−0.0300 (3)	0.78196 (10)	0.0526 (6)
C16	1.0523 (2)	0.0551 (3)	0.81061 (10)	0.0521 (6)
C17	1.3043 (3)	−0.0720 (3)	0.81610 (11)	0.0617 (7)
C18	1.0848 (3)	0.1071 (3)	0.87641 (12)	0.0592 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0558 (12)	0.0556 (12)	0.0531 (12)	0.0020 (9)	0.0111 (9)	−0.0003 (9)
N2	0.0506 (12)	0.0585 (12)	0.0535 (12)	0.0001 (9)	0.0109 (9)	0.0005 (9)
N3	0.0844 (17)	0.0934 (18)	0.0607 (14)	0.0033 (13)	0.0083 (12)	−0.0100 (12)
N4	0.0646 (16)	0.0988 (19)	0.0842 (17)	0.0087 (13)	0.0009 (13)	−0.0086 (13)
C1	0.0601 (15)	0.0541 (14)	0.0556 (14)	0.0004 (12)	0.0168 (11)	−0.0013 (11)
C2	0.0530 (15)	0.0619 (16)	0.0793 (18)	0.0008 (12)	0.0171 (13)	−0.0019 (13)
C3	0.0542 (16)	0.0680 (17)	0.0765 (18)	0.0112 (12)	0.0012 (13)	0.0025 (14)
C4	0.0691 (18)	0.0709 (17)	0.0646 (16)	0.0123 (14)	0.0083 (14)	0.0117 (13)
C5	0.0588 (16)	0.0685 (17)	0.0595 (15)	0.0057 (12)	0.0160 (12)	0.0069 (12)
C6	0.0518 (14)	0.0493 (13)	0.0519 (13)	0.0046 (10)	0.0112 (10)	−0.0019 (10)
C7	0.0533 (14)	0.0545 (14)	0.0472 (13)	0.0067 (11)	0.0096 (11)	−0.0007 (10)
C8	0.0597 (15)	0.0671 (17)	0.0614 (15)	0.0027 (13)	0.0134 (12)	−0.0081 (13)
C9	0.0681 (18)	0.0721 (18)	0.0709 (18)	0.0028 (13)	0.0032 (14)	−0.0142 (14)
C10	0.088 (2)	0.0764 (19)	0.0560 (16)	0.0228 (16)	−0.0024 (15)	−0.0127 (13)
C11	0.087 (2)	0.083 (2)	0.0592 (16)	0.0206 (17)	0.0273 (15)	0.0004 (14)
C12	0.0651 (16)	0.0658 (16)	0.0602 (16)	0.0054 (12)	0.0167 (12)	−0.0008 (12)
C13	0.0503 (13)	0.0514 (14)	0.0480 (13)	−0.0014 (11)	0.0118 (10)	0.0014 (10)
C14	0.0489 (13)	0.0492 (13)	0.0500 (13)	−0.0002 (10)	0.0126 (10)	0.0016 (10)
C15	0.0490 (13)	0.0574 (14)	0.0505 (14)	−0.0016 (11)	0.0072 (10)	0.0011 (11)
C16	0.0556 (15)	0.0526 (14)	0.0476 (13)	−0.0013 (11)	0.0090 (11)	−0.0002 (10)
C17	0.0594 (16)	0.0664 (17)	0.0586 (15)	−0.0014 (13)	0.0095 (13)	−0.0045 (12)
C18	0.0599 (16)	0.0619 (16)	0.0559 (16)	0.0034 (12)	0.0111 (12)	−0.0023 (12)

N1—C14	1.335 (3)	C7—C12	1.383 (3)
N1—C16	1.338 (3)	C8—C9	1.376 (3)
N2—C13	1.339 (3)	C8—H8	0.9300
N2—C15	1.334 (3)	C9—C10	1.369 (4)
C1—C2	1.380 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.378 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.371 (4)	C11—H11	0.9300
C3—C2	1.374 (3)	C12—C11	1.381 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—H4	0.9300	C13—C7	1.477 (3)
C5—C4	1.374 (3)	C14—C13	1.422 (3)
C5—H5	0.9300	C15—C16	1.386 (3)
C6—C1	1.391 (3)	C15—C17	1.450 (3)
C6—C5	1.388 (3)	C17—N4	1.138 (3)
C6—C14	1.480 (3)	C18—N3	1.138 (3)
C7—C8	1.393 (3)	C18—C16	1.442 (3)
C14—N1—C16	117.58 (19)	C8—C9—H9	119.9
C15—N2—C13	117.57 (19)	C10—C9—C8	120.1 (3)
C2—C1—C6	119.8 (2)	C10—C9—H9	119.9
C2—C1—H1	120.1	C9—C10—C11	120.2 (2)
C6—C1—H1	120.1	C9—C10—H10	119.9
C1—C2—H2	119.8	C11—C10—H10	119.9
C3—C2—C1	120.5 (2)	C10—C11—C12	120.1 (3)
C3—C2—H2	119.8	C10—C11—H11	119.9
C2—C3—H3	119.9	C12—C11—H11	119.9
C4—C3—C2	120.1 (2)	C7—C12—H12	120.0
C4—C3—H3	119.9	C11—C12—C7	120.0 (3)
C3—C4—C5	119.9 (2)	C11—C12—H12	120.0
C3—C4—H4	120.0	N2—C13—C7	115.93 (19)
C5—C4—H4	120.0	N2—C13—C14	120.28 (19)
C4—C5—C6	120.7 (2)	C14—C13—C7	123.8 (2)
C4—C5—H5	119.6	N1—C14—C6	116.61 (19)
C6—C5—H5	119.6	N1—C14—C13	120.96 (19)
C1—C6—C14	120.0 (2)	C13—C14—C6	122.43 (19)
C5—C6—C1	118.8 (2)	N2—C15—C16	122.0 (2)
C5—C6—C14	121.2 (2)	N2—C15—C17	115.6 (2)
C8—C7—C13	121.0 (2)	C16—C15—C17	122.2 (2)
C12—C7—C8	119.2 (2)	N1—C16—C15	121.2 (2)
C12—C7—C13	119.7 (2)	N1—C16—C18	117.1 (2)
C7—C8—H8	119.9	C15—C16—C18	121.7 (2)
C9—C8—C7	120.2 (2)	N4—C17—C15	176.3 (3)
C9—C8—H8	119.9	N3—C18—C16	178.8 (3)
C16—N1—C14—C6	−177.30 (19)	C12—C7—C8—C9	−1.2 (4)
C16—N1—C14—C13	3.9 (3)	C13—C7—C8—C9	−178.2 (2)
C14—N1—C16—C15	1.6 (3)	C8—C7—C12—C11	2.2 (4)
C14—N1—C16—C18	−177.3 (2)	C13—C7—C12—C11	179.3 (2)
C15—N2—C13—C14	4.2 (3)	C7—C8—C9—C10	−0.6 (4)
C15—N2—C13—C7	−174.0 (2)	C8—C9—C10—C11	1.4 (4)
C13—N2—C15—C16	1.3 (3)	C9—C10—C11—C12	−0.3 (4)
C13—N2—C15—C17	176.1 (2)	C7—C12—C11—C10	−1.4 (4)
C6—C1—C2—C3	−2.1 (4)	N2—C13—C7—C12	−43.6 (3)
C4—C3—C2—C1	−1.4 (4)	N2—C13—C7—C8	133.4 (2)
C2—C3—C4—C5	2.6 (4)	C14—C13—C7—C8	−44.7 (3)
C6—C5—C4—C3	−0.2 (4)	C14—C13—C7—C12	138.3 (2)
C5—C6—C1—C2	4.3 (3)	N1—C14—C13—N2	−7.0 (3)
C14—C6—C1—C2	−173.3 (2)	N1—C14—C13—C7	171.0 (2)
C1—C6—C5—C4	−3.2 (4)	C6—C14—C13—N2	174.2 (2)
C14—C6—C5—C4	174.5 (2)	C6—C14—C13—C7	−7.8 (3)
C1—C6—C14—N1	−49.0 (3)	N2—C15—C16—N1	−4.4 (4)
C1—C6—C14—C13	129.8 (2)	N2—C15—C16—C18	174.4 (2)
C5—C6—C14—N1	133.4 (2)	C17—C15—C16—N1	−178.9 (2)
C5—C6—C14—C13	−47.8 (3)	C17—C15—C16—C18	0.0 (4)