6-(1H-Indol-3-yl)-4-phenyl-2,2'-bi-pyridine-5-carbonitrile.

In the mol-ecule of the title compound, C(25)H(16)N(4), the pyridine rings are oriented at a dihedral angle of 0.92 (3)°, while the dihedral angle between the benzene ring and the adjacent pyridine ring is 56.51 (3)°. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming R(2) (2)(16) ring motifs. π-π contacts between the pyridine ring and the indole ring system and between the pyridine rings [centroid-centroid distances = 3.923 (2) and 3.724 (2) Å] may further stabilize the structure. Two weak C-H⋯π inter-actions are also present.

Related literature

For general background, see: da Silva et al. (2001 ▶); Joshi & Chand (1982 ▶); Namba et al. (2005 ▶). For a related structure, see: Zhu et al., (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H16N4

M = 372.42

Triclinic,

a = 9.7744 (16) Å

b = 9.7927 (11) Å

c = 11.233 (2) Å

α = 73.121 (13)°

β = 86.008 (16)°

γ = 63.853 (10)°

V = 921.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.55 × 0.35 × 0.30 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (ABSCOR; Jacobson, 1998 ▶) T min = 0.966, T max = 0.976

8987 measured reflections

3349 independent reflections

2614 reflections with I > 2/s(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.126

S = 1.12

3349 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016195/hk2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016195/hk2679Isup2.hkl

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

C25H16N4	Z = 2
Mr = 372.42	F(000) = 388
Triclinic, P1	Dx = 1.342 Mg m−3
Hall symbol: -P 1	Melting point = 567–568 K
a = 9.7744 (16) Å	Mo Kα radiation, λ = 0.71070 Å
b = 9.7927 (11) Å	Cell parameters from 3008 reflections
c = 11.233 (2) Å	θ = 3.1–25.3°
α = 73.121 (13)°	µ = 0.08 mm−1
β = 86.008 (16)°	T = 291 K
γ = 63.853 (10)°	Block, yellow
V = 921.5 (3) Å3	0.55 × 0.35 × 0.30 mm

Rigaku Mercury diffractometer	3349 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2/s(I)
graphite	Rint = 0.027
Detector resolution: 7.31 pixels mm-1	θmax = 25.3°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Jacobson, 1998)	k = −10→11
Tmin = 0.966, Tmax = 0.976	l = −13→13
8987 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.1499P] where P = (Fo2 + 2Fc2)/3
3349 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.94201 (16)	0.20772 (17)	0.54741 (13)	0.0355 (4)
N2	1.20413 (18)	0.3774 (2)	0.44026 (14)	0.0455 (4)
N3	0.5855 (2)	0.1895 (2)	0.28547 (16)	0.0606 (5)
N4	0.64100 (17)	−0.04598 (18)	0.69177 (14)	0.0422 (4)
H4	0.5936	−0.1043	0.7025	0.051*
C1	1.01436 (19)	0.2799 (2)	0.46717 (16)	0.0347 (4)
C2	0.98275 (19)	0.3310 (2)	0.33960 (16)	0.0371 (4)
H2	1.0382	0.3776	0.2873	0.045*
C3	0.86846 (19)	0.3126 (2)	0.28960 (16)	0.0353 (4)
C4	0.79281 (19)	0.2362 (2)	0.37308 (16)	0.0348 (4)
C5	0.83308 (19)	0.1829 (2)	0.50305 (16)	0.0334 (4)
C6	1.13427 (19)	0.3032 (2)	0.52184 (16)	0.0354 (4)
C7	1.1727 (2)	0.2494 (2)	0.64913 (18)	0.0449 (5)
H7	1.1226	0.1981	0.7039	0.054*
C8	1.2862 (2)	0.2731 (3)	0.6929 (2)	0.0519 (5)
H8	1.3135	0.2383	0.7779	0.062*
C9	1.3586 (2)	0.3482 (2)	0.6104 (2)	0.0494 (5)
H9	1.4361	0.3648	0.6378	0.059*
C10	1.3136 (2)	0.3981 (3)	0.4861 (2)	0.0521 (5)
H10	1.3625	0.4497	0.4302	0.063*
C11	0.8284 (2)	0.3777 (2)	0.15322 (16)	0.0379 (4)
C12	0.9407 (2)	0.3356 (2)	0.07066 (17)	0.0445 (5)
H12	1.0400	0.2617	0.1010	0.053*
C13	0.9065 (3)	0.4026 (3)	−0.05660 (18)	0.0529 (6)
H13	0.9823	0.3725	−0.1114	0.063*
C14	0.7602 (3)	0.5140 (3)	−0.10229 (19)	0.0555 (6)
H14	0.7376	0.5599	−0.1878	0.067*
C15	0.6484 (3)	0.5570 (3)	−0.02151 (19)	0.0532 (6)
H15	0.5498	0.6323	−0.0525	0.064*
C16	0.6809 (2)	0.4891 (2)	0.10587 (18)	0.0460 (5)
H16	0.6039	0.5181	0.1600	0.055*
C17	0.6772 (2)	0.2108 (2)	0.32443 (17)	0.0423 (5)
C18	0.7603 (2)	0.1025 (2)	0.59690 (16)	0.0352 (4)
C19	0.6856 (2)	0.0176 (2)	0.58127 (17)	0.0385 (4)
H19	0.6682	0.0056	0.5054	0.046*
C20	0.6833 (2)	−0.0028 (2)	0.78422 (17)	0.0380 (4)
C21	0.6582 (2)	−0.0376 (2)	0.90989 (18)	0.0476 (5)
H21	0.6081	−0.1001	0.9444	0.057*
C22	0.7105 (3)	0.0240 (3)	0.98141 (19)	0.0568 (6)
H22	0.6957	0.0029	1.0663	0.068*
C23	0.7851 (3)	0.1175 (3)	0.92946 (19)	0.0601 (6)
H23	0.8188	0.1581	0.9803	0.072*
C24	0.8104 (2)	0.1515 (3)	0.80452 (18)	0.0507 (5)
H24	0.8605	0.2143	0.7711	0.061*
C25	0.7595 (2)	0.0901 (2)	0.72879 (16)	0.0366 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0353 (8)	0.0367 (9)	0.0374 (8)	−0.0191 (7)	0.0027 (7)	−0.0097 (7)
N2	0.0430 (9)	0.0583 (11)	0.0475 (9)	−0.0321 (8)	0.0058 (8)	−0.0173 (8)
N3	0.0675 (12)	0.0748 (13)	0.0507 (10)	−0.0502 (11)	−0.0130 (9)	0.0006 (9)
N4	0.0439 (9)	0.0449 (9)	0.0476 (9)	−0.0298 (8)	0.0052 (7)	−0.0109 (7)
C1	0.0320 (9)	0.0349 (10)	0.0378 (10)	−0.0153 (8)	0.0024 (8)	−0.0102 (8)
C2	0.0336 (9)	0.0415 (11)	0.0369 (10)	−0.0206 (8)	0.0024 (8)	−0.0058 (8)
C3	0.0354 (10)	0.0346 (10)	0.0355 (10)	−0.0159 (8)	0.0005 (8)	−0.0081 (8)
C4	0.0346 (9)	0.0346 (10)	0.0362 (10)	−0.0172 (8)	0.0001 (8)	−0.0082 (8)
C5	0.0329 (9)	0.0314 (9)	0.0385 (10)	−0.0157 (8)	0.0034 (8)	−0.0114 (8)
C6	0.0319 (9)	0.0355 (10)	0.0407 (10)	−0.0152 (8)	0.0036 (8)	−0.0134 (8)
C7	0.0452 (11)	0.0490 (12)	0.0415 (11)	−0.0237 (10)	−0.0025 (9)	−0.0083 (9)
C8	0.0514 (12)	0.0575 (13)	0.0492 (12)	−0.0256 (11)	−0.0101 (10)	−0.0131 (10)
C9	0.0334 (10)	0.0567 (13)	0.0663 (14)	−0.0199 (10)	−0.0016 (10)	−0.0281 (11)
C10	0.0458 (12)	0.0661 (14)	0.0611 (13)	−0.0364 (11)	0.0121 (10)	−0.0249 (11)
C11	0.0418 (10)	0.0419 (11)	0.0360 (10)	−0.0255 (9)	0.0003 (8)	−0.0080 (8)
C12	0.0459 (11)	0.0509 (12)	0.0399 (11)	−0.0266 (10)	0.0016 (9)	−0.0089 (9)
C13	0.0668 (14)	0.0664 (15)	0.0398 (11)	−0.0420 (13)	0.0114 (10)	−0.0171 (10)
C14	0.0770 (16)	0.0650 (15)	0.0357 (11)	−0.0472 (13)	−0.0048 (11)	−0.0026 (10)
C15	0.0566 (13)	0.0545 (13)	0.0463 (12)	−0.0306 (11)	−0.0118 (11)	0.0018 (10)
C16	0.0448 (11)	0.0539 (12)	0.0410 (10)	−0.0260 (10)	−0.0005 (9)	−0.0085 (9)
C17	0.0457 (11)	0.0469 (12)	0.0382 (10)	−0.0283 (10)	0.0001 (9)	−0.0042 (9)
C18	0.0334 (9)	0.0345 (10)	0.0388 (10)	−0.0164 (8)	0.0030 (8)	−0.0098 (8)
C19	0.0408 (10)	0.0398 (11)	0.0387 (10)	−0.0215 (9)	0.0030 (8)	−0.0109 (8)
C20	0.0339 (10)	0.0373 (10)	0.0436 (11)	−0.0174 (8)	0.0041 (8)	−0.0105 (8)
C21	0.0476 (12)	0.0545 (13)	0.0449 (11)	−0.0305 (10)	0.0111 (9)	−0.0091 (10)
C22	0.0709 (15)	0.0729 (15)	0.0377 (11)	−0.0436 (13)	0.0129 (10)	−0.0146 (11)
C23	0.0815 (16)	0.0805 (16)	0.0432 (12)	−0.0570 (14)	0.0122 (11)	−0.0205 (11)
C24	0.0656 (14)	0.0626 (13)	0.0424 (11)	−0.0457 (12)	0.0096 (10)	−0.0145 (10)
C25	0.0356 (10)	0.0374 (10)	0.0394 (10)	−0.0199 (8)	0.0033 (8)	−0.0091 (8)

N1—C1	1.339 (2)	C11—C12	1.385 (3)
N1—C5	1.347 (2)	C11—C16	1.391 (3)
N2—C10	1.334 (2)	C12—C13	1.384 (3)
N2—C6	1.341 (2)	C12—H12	0.9300
N3—C17	1.144 (2)	C13—C14	1.378 (3)
N4—C19	1.354 (2)	C13—H13	0.9300
N4—C20	1.377 (2)	C14—C15	1.369 (3)
N4—H4	0.8600	C14—H14	0.9300
C1—C2	1.381 (2)	C15—C16	1.384 (3)
C1—C6	1.490 (2)	C15—H15	0.9300
C2—C3	1.385 (2)	C16—H16	0.9300
C2—H2	0.9300	C18—C19	1.375 (2)
C3—C4	1.404 (2)	C18—C25	1.451 (2)
C3—C11	1.484 (2)	C19—H19	0.9300
C4—C5	1.420 (2)	C20—C21	1.384 (3)
C4—C17	1.432 (2)	C20—C25	1.405 (2)
C5—C18	1.465 (2)	C21—C22	1.372 (3)
C6—C7	1.388 (2)	C21—H21	0.9300
C7—C8	1.377 (3)	C22—C23	1.389 (3)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.368 (3)	C23—C24	1.376 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.371 (3)	C24—C25	1.398 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—H10	0.9300
C1—N1—C5	119.18 (15)	C13—C12—H12	119.7
C10—N2—C6	117.30 (17)	C11—C12—H12	119.7
C19—N4—C20	109.41 (15)	C14—C13—C12	120.1 (2)
C19—N4—H4	125.3	C14—C13—H13	119.9
C20—N4—H4	125.3	C12—C13—H13	119.9
N1—C1—C2	123.09 (15)	C15—C14—C13	119.85 (19)
N1—C1—C6	116.67 (15)	C15—C14—H14	120.1
C2—C1—C6	120.24 (16)	C13—C14—H14	120.1
C1—C2—C3	119.94 (16)	C14—C15—C16	120.5 (2)
C1—C2—H2	120.0	C14—C15—H15	119.8
C3—C2—H2	120.0	C16—C15—H15	119.8
C2—C3—C4	117.25 (16)	C15—C16—C11	120.2 (2)
C2—C3—C11	119.47 (16)	C15—C16—H16	119.9
C4—C3—C11	123.25 (15)	C11—C16—H16	119.9
C3—C4—C5	120.12 (15)	N3—C17—C4	179.5 (2)
C3—C4—C17	118.82 (15)	C19—C18—C25	105.64 (15)
C5—C4—C17	121.05 (16)	C19—C18—C5	128.12 (16)
N1—C5—C4	120.37 (15)	C25—C18—C5	126.18 (15)
N1—C5—C18	115.71 (15)	N4—C19—C18	110.50 (16)
C4—C5—C18	123.91 (15)	N4—C19—H19	124.7
N2—C6—C7	122.15 (16)	C18—C19—H19	124.7
N2—C6—C1	115.83 (15)	N4—C20—C21	129.29 (17)
C7—C6—C1	122.01 (16)	N4—C20—C25	107.56 (15)
C8—C7—C6	118.82 (18)	C21—C20—C25	123.15 (17)
C8—C7—H7	120.6	C22—C21—C20	117.15 (18)
C6—C7—H7	120.6	C22—C21—H21	121.4
C9—C8—C7	119.50 (19)	C20—C21—H21	121.4
C9—C8—H8	120.2	C21—C22—C23	121.23 (19)
C7—C8—H8	120.2	C21—C22—H22	119.4
C8—C9—C10	118.03 (18)	C23—C22—H22	119.4
C8—C9—H9	121.0	C24—C23—C22	121.5 (2)
C10—C9—H9	121.0	C24—C23—H23	119.2
N2—C10—C9	124.20 (19)	C22—C23—H23	119.2
N2—C10—H10	117.9	C23—C24—C25	118.88 (18)
C9—C10—H10	117.9	C23—C24—H24	120.6
C12—C11—C16	118.78 (17)	C25—C24—H24	120.6
C12—C11—C3	119.99 (16)	C24—C25—C20	118.06 (17)
C16—C11—C3	121.11 (17)	C24—C25—C18	135.01 (17)
C13—C12—C11	120.51 (19)	C20—C25—C18	106.88 (15)
C5—N1—C1—C2	0.0 (3)	C16—C11—C12—C13	−0.3 (3)
C5—N1—C1—C6	−179.68 (15)	C3—C11—C12—C13	−176.21 (17)
N1—C1—C2—C3	2.0 (3)	C11—C12—C13—C14	1.0 (3)
C6—C1—C2—C3	−178.34 (16)	C12—C13—C14—C15	−0.7 (3)
C1—C2—C3—C4	−2.2 (3)	C13—C14—C15—C16	−0.1 (3)
C1—C2—C3—C11	175.87 (17)	C14—C15—C16—C11	0.8 (3)
C2—C3—C4—C5	0.7 (3)	C12—C11—C16—C15	−0.5 (3)
C11—C3—C4—C5	−177.30 (16)	C3—C11—C16—C15	175.28 (17)
C2—C3—C4—C17	−178.14 (16)	N1—C5—C18—C19	−157.15 (17)
C11—C3—C4—C17	3.8 (3)	C4—C5—C18—C19	24.1 (3)
C1—N1—C5—C4	−1.6 (2)	N1—C5—C18—C25	19.5 (3)
C1—N1—C5—C18	179.67 (15)	C4—C5—C18—C25	−159.21 (17)
C3—C4—C5—N1	1.2 (3)	C20—N4—C19—C18	0.8 (2)
C17—C4—C5—N1	−179.95 (17)	C25—C18—C19—N4	−0.5 (2)
C3—C4—C5—C18	179.84 (16)	C5—C18—C19—N4	176.68 (17)
C17—C4—C5—C18	−1.3 (3)	C19—N4—C20—C21	178.41 (19)
C10—N2—C6—C7	0.0 (3)	C19—N4—C20—C25	−0.8 (2)
C10—N2—C6—C1	−179.08 (16)	N4—C20—C21—C22	−178.64 (19)
N1—C1—C6—N2	−179.21 (15)	C25—C20—C21—C22	0.5 (3)
C2—C1—C6—N2	1.1 (3)	C20—C21—C22—C23	0.1 (3)
N1—C1—C6—C7	1.7 (3)	C21—C22—C23—C24	−0.3 (4)
C2—C1—C6—C7	−178.01 (17)	C22—C23—C24—C25	0.0 (4)
N2—C6—C7—C8	0.0 (3)	C23—C24—C25—C20	0.6 (3)
C1—C6—C7—C8	179.07 (17)	C23—C24—C25—C18	177.8 (2)
C6—C7—C8—C9	−0.3 (3)	N4—C20—C25—C24	178.46 (16)
C7—C8—C9—C10	0.4 (3)	C21—C20—C25—C24	−0.8 (3)
C6—N2—C10—C9	0.2 (3)	N4—C20—C25—C18	0.5 (2)
C8—C9—C10—N2	−0.4 (3)	C21—C20—C25—C18	−178.79 (17)
C2—C3—C11—C12	54.4 (2)	C19—C18—C25—C24	−177.5 (2)
C4—C3—C11—C12	−127.63 (19)	C5—C18—C25—C24	5.3 (3)
C2—C3—C11—C16	−121.39 (19)	C19—C18—C25—C20	0.0 (2)
C4—C3—C11—C16	56.6 (3)	C5—C18—C25—C20	−177.27 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3i	0.86	2.23	3.066 (2)	164
C12—H12···Cg5ii	0.93	2.84	3.649 (3)	146
C23—H23···Cg4iii	0.93	2.91	3.711 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N3i	0.86	2.23	3.066 (2)	164
C12—H12⋯Cg5ii	0.93	2.84	3.649 (3)	146
C23—H23⋯Cg4iii	0.93	2.91	3.711 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) . Cg4 and Cg5 are the centroids of the C11–C16 and C20–C25 rings, respectively.