Crystal structure of 2-(4-chloro-phen-yl)-4-(1H-indol-3-yl)-6-phenyl-pyridine-3-carbo-nitrile.

In the title compound, C26H16ClN3, the dihedral angles between the central pyridine ring and the pendant phenyl, chloro-benzene and indole rings are 18.52 (12), 48.97 (11) and 21.20 (10)°, respectively. An intra-molecular C-H⋯Nc (c = cyanide) hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N-H⋯Nc hydrogen bonds generate R 2 (2)(16) loops.

Related literature

For the biological activity of substituted pyridine derivatives, see: Yao et al. (1994 ▶). For a related structure, see: Vishnupriya et al. (2014 ▶).

Experimental

Crystal data

C26H16ClN3

M = 405.87

Monoclinic,

a = 7.6533 (4) Å

b = 11.4822 (7) Å

c = 23.2906 (14) Å

β = 94.351 (1)°

V = 2040.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.50 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.958, T max = 0.986

15210 measured reflections

4194 independent reflections

3000 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.146

S = 1.04

4194 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814017693/hb7263sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017693/hb7263Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017693/hb7263Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017693/hb7263fig1.tif

The mol­ecular structure of compound showing 30% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814017693/hb7263fig2.tif

Partial packing view of the compound showing mol­ecules linked by a pair of N—H⋯N inter­actions (dotted lines).

CCDC reference: 1017501

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H16ClN3	F(000) = 840
Mr = 405.87	Dx = 1.321 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 7.6533 (4) Å	θ = 2–27°
b = 11.4822 (7) Å	µ = 0.21 mm−1
c = 23.2906 (14) Å	T = 293 K
β = 94.351 (1)°	Block, colourless
V = 2040.8 (2) Å3	0.50 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4194 independent reflections
Radiation source: fine-focus sealed tube	3000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 0 pixels mm-1	θmax = 26.5°, θmin = 1.8°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→13
Tmin = 0.958, Tmax = 0.986	l = −29→19
15210 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.054P)2 + 0.8601P] where P = (Fo2 + 2Fc2)/3
4194 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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	0.2617 (3)	0.54731 (16)	−0.00655 (10)	0.0574 (5)
C2	0.2444 (3)	0.53305 (18)	−0.06568 (10)	0.0627 (5)
H2	0.2589	0.5966	−0.0896	0.075*
C3	0.2057 (3)	0.42467 (17)	−0.08943 (10)	0.0603 (5)
C4	0.1803 (3)	0.33296 (17)	−0.05109 (10)	0.0605 (5)
C5	0.1900 (3)	0.35418 (17)	0.00869 (10)	0.0598 (5)
C11	0.3096 (3)	0.66136 (17)	0.02012 (10)	0.0580 (5)
C12	0.2778 (3)	0.6854 (2)	0.07626 (11)	0.0704 (6)
H12	0.2292	0.6283	0.0985	0.085*
C13	0.3173 (4)	0.7936 (2)	0.10002 (12)	0.0806 (7)
H13	0.2941	0.8091	0.1379	0.097*
C14	0.3902 (4)	0.8774 (2)	0.06809 (14)	0.0895 (8)
H14	0.4130	0.9510	0.0835	0.107*
C15	0.4297 (5)	0.8525 (2)	0.01292 (14)	0.1014 (10)
H15	0.4846	0.9085	−0.0083	0.122*
C16	0.3893 (4)	0.74587 (19)	−0.01150 (12)	0.0785 (7)
H16	0.4153	0.7305	−0.0491	0.094*
C31	0.1913 (3)	0.41209 (18)	−0.15290 (10)	0.0613 (5)
C32	0.0952 (3)	0.49362 (19)	−0.18691 (11)	0.0721 (6)
H32	0.0370	0.5533	−0.1692	0.087*
C33	0.0853 (3)	0.4870 (2)	−0.24595 (12)	0.0762 (7)
H33	0.0199	0.5413	−0.2680	0.091*
C34	0.1727 (3)	0.3996 (2)	−0.27214 (11)	0.0714 (6)
C35	0.2690 (3)	0.3182 (2)	−0.23988 (12)	0.0763 (7)
H35	0.3275	0.2592	−0.2579	0.092*
C36	0.2779 (3)	0.3248 (2)	−0.18073 (11)	0.0707 (6)
H36	0.3430	0.2698	−0.1590	0.085*
C41	0.1423 (3)	0.21813 (19)	−0.07380 (11)	0.0692 (6)
C51	0.1586 (3)	0.26723 (17)	0.05255 (11)	0.0630 (6)
C52	0.2163 (3)	0.27513 (18)	0.11280 (11)	0.0674 (6)
C53	0.3179 (3)	0.3535 (2)	0.14722 (12)	0.0778 (7)
H53	0.3638	0.4198	0.1311	0.093*
C54	0.3493 (4)	0.3314 (3)	0.20519 (13)	0.0965 (9)
H54	0.4174	0.3830	0.2281	0.116*
C55	0.2800 (5)	0.2320 (3)	0.23029 (15)	0.1080 (11)
H55	0.3005	0.2198	0.2697	0.130*
C56	0.1834 (5)	0.1534 (3)	0.19779 (15)	0.1012 (10)
H56	0.1402	0.0867	0.2144	0.121*
C57	0.1506 (4)	0.1750 (2)	0.13923 (13)	0.0793 (8)
C58	0.0637 (3)	0.16548 (19)	0.04622 (12)	0.0762 (7)
H58	0.0101	0.1382	0.0116	0.091*
N1	0.2322 (2)	0.46053 (14)	0.02994 (8)	0.0597 (4)
N2	0.1113 (3)	0.12741 (17)	−0.09152 (11)	0.0913 (7)
N3	0.0600 (3)	0.11130 (17)	0.09728 (11)	0.0870 (7)
H3	0.0083	0.0462	0.1027	0.104*
Cl1	0.15880 (11)	0.38830 (8)	−0.34663 (3)	0.0995 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0505 (11)	0.0401 (10)	0.0811 (15)	−0.0067 (8)	0.0018 (10)	0.0034 (10)
C2	0.0666 (13)	0.0441 (10)	0.0768 (15)	−0.0091 (9)	0.0018 (11)	0.0061 (10)
C3	0.0532 (11)	0.0453 (10)	0.0819 (15)	−0.0039 (9)	0.0027 (10)	0.0022 (10)
C4	0.0544 (12)	0.0409 (10)	0.0863 (16)	−0.0055 (8)	0.0065 (10)	−0.0016 (10)
C5	0.0513 (11)	0.0407 (10)	0.0880 (16)	−0.0045 (8)	0.0090 (10)	0.0050 (10)
C11	0.0540 (11)	0.0424 (10)	0.0765 (14)	−0.0055 (8)	−0.0023 (10)	0.0028 (10)
C12	0.0736 (15)	0.0545 (12)	0.0825 (16)	−0.0103 (11)	0.0020 (12)	0.0030 (11)
C13	0.0880 (18)	0.0691 (15)	0.0830 (17)	−0.0071 (13)	−0.0048 (13)	−0.0115 (13)
C14	0.107 (2)	0.0522 (13)	0.107 (2)	−0.0207 (13)	−0.0058 (17)	−0.0129 (14)
C15	0.143 (3)	0.0541 (14)	0.108 (2)	−0.0385 (16)	0.016 (2)	−0.0021 (15)
C16	0.1008 (19)	0.0495 (12)	0.0855 (17)	−0.0226 (12)	0.0087 (14)	−0.0010 (11)
C31	0.0568 (12)	0.0474 (11)	0.0789 (15)	−0.0062 (9)	0.0001 (10)	−0.0001 (10)
C32	0.0752 (15)	0.0486 (11)	0.0911 (18)	0.0061 (11)	−0.0034 (13)	−0.0035 (11)
C33	0.0784 (16)	0.0579 (13)	0.0899 (18)	0.0005 (12)	−0.0088 (13)	0.0089 (13)
C34	0.0670 (14)	0.0670 (14)	0.0799 (16)	−0.0088 (11)	0.0040 (12)	0.0073 (12)
C35	0.0735 (15)	0.0711 (15)	0.0862 (18)	0.0094 (12)	0.0172 (13)	0.0007 (13)
C36	0.0646 (14)	0.0624 (13)	0.0848 (17)	0.0105 (11)	0.0036 (12)	0.0076 (12)
C41	0.0672 (14)	0.0488 (12)	0.0929 (17)	−0.0070 (10)	0.0150 (12)	−0.0013 (11)
C51	0.0625 (13)	0.0426 (10)	0.0856 (16)	−0.0006 (9)	0.0168 (11)	0.0055 (10)
C52	0.0669 (14)	0.0478 (11)	0.0909 (17)	0.0106 (10)	0.0283 (12)	0.0071 (11)
C53	0.0870 (17)	0.0637 (14)	0.0839 (17)	0.0159 (13)	0.0157 (13)	0.0010 (13)
C54	0.111 (2)	0.087 (2)	0.092 (2)	0.0328 (17)	0.0149 (17)	−0.0087 (17)
C55	0.136 (3)	0.109 (3)	0.084 (2)	0.050 (2)	0.041 (2)	0.0164 (19)
C56	0.119 (2)	0.0805 (19)	0.111 (2)	0.0301 (18)	0.054 (2)	0.0272 (19)
C57	0.0857 (17)	0.0566 (13)	0.101 (2)	0.0170 (12)	0.0415 (15)	0.0166 (14)
C58	0.0781 (16)	0.0486 (12)	0.1046 (19)	−0.0086 (11)	0.0249 (14)	0.0076 (12)
N1	0.0576 (10)	0.0422 (8)	0.0795 (12)	−0.0059 (7)	0.0059 (8)	0.0044 (8)
N2	0.1034 (17)	0.0503 (11)	0.1236 (19)	−0.0162 (11)	0.0313 (14)	−0.0159 (12)
N3	0.0934 (15)	0.0496 (11)	0.1231 (19)	−0.0065 (10)	0.0430 (14)	0.0156 (12)
Cl1	0.1063 (6)	0.1147 (6)	0.0785 (5)	−0.0048 (4)	0.0132 (4)	0.0148 (4)

C1—N1	1.340 (3)	C32—H32	0.9300
C1—C2	1.383 (3)	C33—C34	1.375 (3)
C1—C11	1.483 (3)	C33—H33	0.9300
C2—C3	1.385 (3)	C34—C35	1.377 (3)
C2—H2	0.9300	C34—Cl1	1.735 (3)
C3—C4	1.404 (3)	C35—C36	1.376 (3)
C3—C31	1.481 (3)	C35—H35	0.9300
C4—C5	1.410 (3)	C36—H36	0.9300
C4—C41	1.442 (3)	C41—N2	1.139 (3)
C5—N1	1.348 (3)	C51—C58	1.378 (3)
C5—C51	1.461 (3)	C51—C52	1.441 (3)
C11—C12	1.376 (3)	C52—C53	1.401 (4)
C11—C16	1.387 (3)	C52—C57	1.414 (3)
C12—C13	1.384 (3)	C53—C54	1.377 (4)
C12—H12	0.9300	C53—H53	0.9300
C13—C14	1.361 (4)	C54—C55	1.404 (5)
C13—H13	0.9300	C54—H54	0.9300
C14—C15	1.373 (4)	C55—C56	1.360 (5)
C14—H14	0.9300	C55—H55	0.9300
C15—C16	1.375 (3)	C56—C57	1.390 (4)
C15—H15	0.9300	C56—H56	0.9300
C16—H16	0.9300	C57—N3	1.367 (4)
C31—C36	1.389 (3)	C58—N3	1.344 (3)
C31—C32	1.399 (3)	C58—H58	0.9300
C32—C33	1.374 (3)	N3—H3	0.8600
N1—C1—C2	122.37 (18)	C32—C33—H33	120.2
N1—C1—C11	116.05 (19)	C34—C33—H33	120.2
C2—C1—C11	121.56 (18)	C33—C34—C35	120.8 (2)
C1—C2—C3	120.38 (19)	C33—C34—Cl1	120.2 (2)
C1—C2—H2	119.8	C35—C34—Cl1	119.0 (2)
C3—C2—H2	119.8	C36—C35—C34	119.5 (2)
C2—C3—C4	117.1 (2)	C36—C35—H35	120.2
C2—C3—C31	118.94 (19)	C34—C35—H35	120.2
C4—C3—C31	123.95 (19)	C35—C36—C31	121.2 (2)
C3—C4—C5	119.94 (18)	C35—C36—H36	119.4
C3—C4—C41	119.1 (2)	C31—C36—H36	119.4
C5—C4—C41	120.95 (19)	N2—C41—C4	179.6 (3)
N1—C5—C4	120.84 (18)	C58—C51—C52	106.1 (2)
N1—C5—C51	114.2 (2)	C58—C51—C5	128.2 (2)
C4—C5—C51	124.97 (18)	C52—C51—C5	125.68 (19)
C12—C11—C16	118.8 (2)	C53—C52—C57	118.2 (3)
C12—C11—C1	121.25 (19)	C53—C52—C51	135.5 (2)
C16—C11—C1	120.0 (2)	C57—C52—C51	106.3 (2)
C11—C12—C13	120.7 (2)	C54—C53—C52	119.4 (3)
C11—C12—H12	119.7	C54—C53—H53	120.3
C13—C12—H12	119.7	C52—C53—H53	120.3
C14—C13—C12	120.2 (3)	C53—C54—C55	121.0 (3)
C14—C13—H13	119.9	C53—C54—H54	119.5
C12—C13—H13	119.9	C55—C54—H54	119.5
C13—C14—C15	119.5 (2)	C56—C55—C54	120.9 (3)
C13—C14—H14	120.3	C56—C55—H55	119.5
C15—C14—H14	120.3	C54—C55—H55	119.5
C14—C15—C16	121.0 (3)	C55—C56—C57	118.5 (3)
C14—C15—H15	119.5	C55—C56—H56	120.7
C16—C15—H15	119.5	C57—C56—H56	120.7
C15—C16—C11	119.8 (3)	N3—C57—C56	130.5 (3)
C15—C16—H16	120.1	N3—C57—C52	107.6 (2)
C11—C16—H16	120.1	C56—C57—C52	121.9 (3)
C36—C31—C32	117.9 (2)	N3—C58—C51	110.1 (3)
C36—C31—C3	122.3 (2)	N3—C58—H58	124.9
C32—C31—C3	119.7 (2)	C51—C58—H58	124.9
C33—C32—C31	121.1 (2)	C1—N1—C5	119.22 (19)
C33—C32—H32	119.4	C58—N3—C57	109.9 (2)
C31—C32—H32	119.4	C58—N3—H3	125.0
C32—C33—C34	119.5 (2)	C57—N3—H3	125.0
N1—C1—C2—C3	−4.0 (3)	Cl1—C34—C35—C36	−178.62 (19)
C11—C1—C2—C3	177.71 (19)	C34—C35—C36—C31	0.1 (4)
C1—C2—C3—C4	1.8 (3)	C32—C31—C36—C35	−0.3 (3)
C1—C2—C3—C31	−178.89 (19)	C3—C31—C36—C35	−176.9 (2)
C2—C3—C4—C5	1.7 (3)	C3—C4—C41—N2	−129 (52)
C31—C3—C4—C5	−177.53 (19)	C5—C4—C41—N2	50 (52)
C2—C3—C4—C41	−179.1 (2)	N1—C5—C51—C58	157.8 (2)
C31—C3—C4—C41	1.7 (3)	C4—C5—C51—C58	−22.7 (4)
C3—C4—C5—N1	−3.4 (3)	N1—C5—C51—C52	−19.0 (3)
C41—C4—C5—N1	177.4 (2)	C4—C5—C51—C52	160.4 (2)
C3—C4—C5—C51	177.2 (2)	C58—C51—C52—C53	178.6 (2)
C41—C4—C5—C51	−2.0 (3)	C5—C51—C52—C53	−4.0 (4)
N1—C1—C11—C12	−17.6 (3)	C58—C51—C52—C57	0.1 (2)
C2—C1—C11—C12	160.8 (2)	C5—C51—C52—C57	177.5 (2)
N1—C1—C11—C16	161.9 (2)	C57—C52—C53—C54	−0.5 (3)
C2—C1—C11—C16	−19.7 (3)	C51—C52—C53—C54	−178.9 (2)
C16—C11—C12—C13	2.8 (4)	C52—C53—C54—C55	−0.4 (4)
C1—C11—C12—C13	−177.7 (2)	C53—C54—C55—C56	1.6 (4)
C11—C12—C13—C14	−0.7 (4)	C54—C55—C56—C57	−1.6 (4)
C12—C13—C14—C15	−2.3 (5)	C55—C56—C57—N3	179.5 (3)
C13—C14—C15—C16	3.1 (5)	C55—C56—C57—C52	0.7 (4)
C14—C15—C16—C11	−0.9 (5)	C53—C52—C57—N3	−178.6 (2)
C12—C11—C16—C15	−2.0 (4)	C51—C52—C57—N3	0.2 (2)
C1—C11—C16—C15	178.5 (3)	C53—C52—C57—C56	0.4 (3)
C2—C3—C31—C36	130.6 (2)	C51—C52—C57—C56	179.2 (2)
C4—C3—C31—C36	−50.2 (3)	C52—C51—C58—N3	−0.3 (3)
C2—C3—C31—C32	−46.0 (3)	C5—C51—C58—N3	−177.6 (2)
C4—C3—C31—C32	133.2 (2)	C2—C1—N1—C5	2.4 (3)
C36—C31—C32—C33	0.6 (3)	C11—C1—N1—C5	−179.26 (18)
C3—C31—C32—C33	177.3 (2)	C4—C5—N1—C1	1.3 (3)
C31—C32—C33—C34	−0.7 (4)	C51—C5—N1—C1	−179.23 (18)
C32—C33—C34—C35	0.4 (4)	C51—C58—N3—C57	0.4 (3)
C32—C33—C34—Cl1	178.91 (19)	C56—C57—N3—C58	−179.3 (3)
C33—C34—C35—C36	−0.1 (4)	C52—C57—N3—C58	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C58—H58···N2	0.93	2.58	3.285 (4)	133
N3—H3···N2i	0.86	2.20	3.037 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C58—H58⋯N2	0.93	2.58	3.285 (4)	133
N3—H3⋯N2i	0.86	2.20	3.037 (3)	164

Symmetry code: (i) .