Crystal structure of 2-(4-chloro­phen­yl)-4-(1H-indol-3-yl)-6-phenyl­pyridine-3-carbo­nitrile

Vishnupriya, R.; Suresh, J.; Gunasekaran, P.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S1600536814017693

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Page o978

doi:10.1107/S1600536814017693

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ADDENDA AND ERRATA

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Crystal structure of 2-(4-chlorophenyl)-4-(1H-indol-3-yl)-6-phenylpyridine-3-carbonitrile

R. Vishnupriya,^a J. Suresh,^a Pethaiah Gunasekaran,^b Subbu Perumal ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 31 July 2014; accepted 1 August 2014; online 6 August 2014)

In the title compound, C₂₆H₁₆ClN₃, the dihedral angles between the central pyridine ring and the pendant phenyl, chlorobenzene and indole rings are 18.52 (12), 48.97 (11) and 21.20 (10)°, respectively. An intramolecular C—H⋯N_c (c = cyanide) hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N—H⋯N_c hydrogen bonds generate R₂²(16) loops.

Keywords: crystal structure; pyridine-3-carbonitrile; hydrogen bonding.

CCDC reference: 1017501

1. Related literature

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

2. Experimental

2.1. Crystal data

C₂₆H₁₆ClN₃
M_r = 405.87
Monoclinic, P 2₁ /n
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.146
S = 1.04
4194 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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) -x, -y, -z.

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.

Supporting information

CCDC reference: 1017501

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814017693/hb7263sup1.cif

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

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

checkCIF report

Comment top

Thienopyridines have been used as antithrombotic agents (Yao et al., 1994) against platelet aggregation. As part of our ongoing studies in this area (Vishnupriya et al., 2014) the title compound was investigated.

The deviation of the nitrile atoms (C41,N2) from the mean plane of the pyridine ring system is 0.0579 (5) and 0.0826 (2) Å. The shortening of the C—N distances [1.340 (3) and 1.348 (3) Å] and the opening of the N1–C4–C5 angle [120.83 (2)°] may be attributed to the size of the substituent at C1, correlating well with the values observed in the ortho-substituted derivative. The carbonitrile group lies almost in the plane of the attached planar pyridine ring system.

The crystal structure features a N3—H3···N2⁽ⁱ⁾ [symmetry code: (i) 2 - x, 2 - y, -z] hydrogen bonded R₂² (16) motif (Fig. 2). No significant π—π stacking interaction between neighboring aromatic rings or C—H···π interaction towards them are observed.

Related literature top

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

Experimental top

A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 1 (1 mmol), 4,4,4-trifluoro-1-phenylbutane-1,3-dione 2 (1 mmol) and 4-chloro benzaldehyde 3 (1 mmol) in the presence of ammonium acetate (400 mmol) under solvent-free condition was heated at 110 °C for 6 h. After completion of the reaction (TLC), the reaction mixture was poured into water and extracted with dichloromethane. After removal of the solvent, the residue was chromatographed over silica gel (230–400 mesh) using petroleum ether-ethyl acetate mixture (7:3 v/v), which afforded the pure compound. Melting point:273 °C, Yield: 70%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound showing 30% probability displacement ellipsoids.
	Fig. 2. Partial packing view of the compound showing molecules linked by a pair of N—H···N interactions (dotted lines).

2-(4-Chlorophenyl)-4-(1H-indol-3-yl)-6-phenylpyridine-3-carbonitrile top

Crystal data top

C₂₆H₁₆ClN₃	F(000) = 840
M_r = 405.87	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	4194 independent reflections
Radiation source: fine-focus sealed tube	3000 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 26.5°, θ_min = 1.8°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→13
T_min = 0.958, T_max = 0.986	l = −29→19
15210 measured reflections

Refinement top

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(F_o²) + (0.054P)² + 0.8601P] where P = (F_o² + 2F_c²)/3
4194 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₆H₁₆ClN₃	V = 2040.8 (2) Å³
M_r = 405.87	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6533 (4) Å	µ = 0.21 mm⁻¹
b = 11.4822 (7) Å	T = 293 K
c = 23.2906 (14) Å	0.50 × 0.25 × 0.20 mm
β = 94.351 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4194 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3000 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.986	R_int = 0.028
15210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	Δρ_max = 0.38 e Å⁻³
4194 reflections	Δρ_min = −0.40 e Å⁻³
271 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z.

Acknowledgements

JS and RV thank the management of the Madura College for their encouragement and support. SP thanks the Department of Science and Technology, New Delhi, for a major research project (SR/S1/OC/-50/2011) and the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vishnupriya, R., Suresh, J., Bharkavi, S., Perumal, S. & Lakshman, P. L. N. (2014). Acta Cryst. E70, o968–o969. CSD CrossRef IUCr Journals Google Scholar
Yao, S. K., Ober, J. C., Ferguson, J. J., Maffrand, J. P., Anderson, H. V., Buja, L. M. & Willerson, J. T. (1994). Am. J. Physiol. pp. H488–H493. Google Scholar

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Volume 70| Part 9| September 2014| Page o978

doi:10.1107/S1600536814017693

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-(4-chloro­phen­yl)-4-(1H-indol-3-yl)-6-phenyl­pyridine-3-carbo­nitrile

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-(4-chlorophenyl)-4-(1H-indol-3-yl)-6-phenylpyridine-3-carbonitrile