Crystal structure of 2-(2-bromo­phen­yl)-4-(1H-indol-3-yl)-6-(thio­phen-2-yl)pyridine-3-carbo­nitrile

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

doi:10.1107/S1600536814017188

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o968-o969

doi:10.1107/S1600536814017188

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ADDENDA AND ERRATA

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Crystal structure of 2-(2-bromophenyl)-4-(1H-indol-3-yl)-6-(thiophen-2-yl)pyridine-3-carbonitrile

R. Vishnupriya,^a J. Suresh,^a Shanmugavel Bharkavi,^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 24 July 2014; accepted 25 July 2014; online 1 August 2014)

In the title compound, C₂₄H₁₄BrN₃S, the dihedral angles between the planes of the pyridine ring and the pendant thiophene ring, the indole ring system (r.m.s. deviation = 0.022 Å) and the bromobenzene ring are 9.37 (17), 21.90 (12) and 69.01 (15)°, respectively. The approximate coplanarity of the central ring and the indole ring system is supported by two intramolecular C—H⋯N interactions. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(16) loops and the dimers are linked by C—H⋯π and aromatic π–π stacking [shortest centroid–centroid separation = 3.729 (3) Å] into a three-dimensional network.

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

CCDC reference: 1015962

1. Related literature

For the biological activity of pyridine-3-carbonitrile derivatives, see: Kim et al. (2005 ); Ji et al. (2007 ); Brandt et al. (2010 ); El-Sayed et al. (2011 ).

2. Experimental

2.1. Crystal data

C₂₄H₁₄BrN₃S
M_r = 456.35
Monoclinic, P 2₁ /c
a = 10.470 (5) Å
b = 21.353 (5) Å
c = 9.292 (5) Å
β = 107.710 (5)°
V = 1978.9 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.20 mm⁻¹
T = 293 K
0.52 × 0.23 × 0.17 mm

2.2. Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.986
17079 measured reflections
4305 independent reflections
2837 reflections with I > 2σ(I)
R_int = 0.041

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
4305 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring of the indole moiety.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C53—H53⋯N1	0.93	2.58	3.069 (4)	114
C58—H58⋯N2	0.93	2.55	3.278 (4)	135
N3—H3⋯N2ⁱ	0.86	2.17	3.008 (4)	165
C32—H32⋯Cg1ⁱⁱ	0.93	2.89	3.761 (4)	157
Symmetry codes: (i) -x, -y+1, -z; (ii) -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: 1015962

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814017188/hb7260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017188/hb7260Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814017188/hb7260Isup3.cml

checkCIF report

Comment top

3-Cyanopyridine derivatives have been reported for their wide range of applications such as in antimicrobial, analgesic, anti-hyperglycemic, antiproliferative and antitumor activities (Brandt et al., 2010; El-Sayed et al., 2011; Ji et al., 2007; Kim et al., 2005). As part of our studies in this area, the title compound was investigated.

The deviation of the nitrile atoms (C41,N2) from the mean plane of the pyridine ring system is -0.013 (1) Å and -0.020 (5) Å. The shortening of the C—N distances [1.346 (3) and 1.345 (3) Å] and the opening of the N1–C11–C10 angle [122.83 (2)°] may be attributed to the size of the substituent at C1, correlating well with the values observed in the ortho-substituted derivative.

The crystal structure features a intermolecular N—H···N interaction between inverse related molecules generating a graph set ring motif R₂² (16) which are linked into chains through C—H···Cg1 interation (Cg1 is the centroid of the benzene ring of the indole moiety) and by π···π stacking interaction involving adjacent pyridine and pyrrole rings of the symmetry related molecule at (-x, -y, -z), with a centroid-to-centroid distance of 3.729 (3) Å·(Fig 2).

Related literature top

For the biological activity of pyridine-3-carbonitrile derivatives, see: Kim et al. (2005); Ji et al. (2007); Brandt et al. (2010); El-Sayed et al. (2011).

Experimental top

A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 1 (1 mmol), 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione 2 (1 mmol) and 2-bromo benzaldehyde 3 (1 mmol) in the presence of ammonium acetate (400 mmol) under solvent-free condition was heated at 110 °C for 7 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 282°C, yield: 67%.

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 interconnected through a C—H···π stacking interaction (dotted lines; symmetry code: (i) 1/2 - x, 1/2 + y, 1/2 - z)

2-(2-Bromophenyl)-4-(1H-indol-3-yl)-6-(thiophen-2-yl)pyridine-3-carbonitrile top

Crystal data top

C₂₄H₁₄BrN₃S	F(000) = 920
M_r = 456.35	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 10.470 (5) Å	θ = 2–27°
b = 21.353 (5) Å	µ = 2.20 mm⁻¹
c = 9.292 (5) Å	T = 293 K
β = 107.710 (5)°	Block, colourless
V = 1978.9 (15) Å³	0.52 × 0.23 × 0.17 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4305 independent reflections
Radiation source: fine-focus sealed tube	2837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ω and ϕ scans	h = −12→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −27→27
T_min = 0.958, T_max = 0.986	l = −11→11
17079 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0618P)² + 0.4334P] where P = (F_o² + 2F_c²)/3
4305 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₁₄BrN₃S	V = 1978.9 (15) Å³
M_r = 456.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.470 (5) Å	µ = 2.20 mm⁻¹
b = 21.353 (5) Å	T = 293 K
c = 9.292 (5) Å	0.52 × 0.23 × 0.17 mm
β = 107.710 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	4305 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2837 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.986	R_int = 0.041
17079 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.48 e Å⁻³
4305 reflections	Δρ_min = −0.35 e Å⁻³
262 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	0.2640 (3)	0.50193 (12)	0.7417 (3)	0.0386 (7)
C2	0.3077 (3)	0.44165 (13)	0.7289 (3)	0.0425 (7)
H2	0.3543	0.4194	0.8149	0.051*
C3	0.2818 (3)	0.41458 (12)	0.5880 (3)	0.0390 (7)
C4	0.2078 (3)	0.45002 (12)	0.4630 (3)	0.0368 (6)
C5	0.1664 (3)	0.51133 (12)	0.4822 (3)	0.0371 (6)
C11	0.2890 (3)	0.53182 (14)	0.8898 (3)	0.0432 (7)
C12	0.3376 (3)	0.50426 (15)	1.0315 (3)	0.0481 (8)
H12	0.3625	0.4624	1.0484	0.058*
C13	0.3439 (4)	0.54874 (19)	1.1471 (3)	0.0622 (9)
H13	0.3745	0.5393	1.2496	0.075*
C14	0.3011 (4)	0.60608 (18)	1.0930 (4)	0.0651 (10)
H14	0.2995	0.6405	1.1538	0.078*
C31	0.3330 (3)	0.35097 (13)	0.5742 (3)	0.0402 (7)
C32	0.2810 (4)	0.30034 (14)	0.6331 (3)	0.0555 (8)
H32	0.2108	0.3068	0.6733	0.067*
C33	0.3322 (4)	0.24105 (16)	0.6326 (4)	0.0697 (11)
H33	0.2958	0.2078	0.6716	0.084*
C34	0.4351 (5)	0.23060 (17)	0.5759 (4)	0.0736 (11)
H34	0.4695	0.1904	0.5774	0.088*
C35	0.4892 (4)	0.27918 (16)	0.5159 (4)	0.0650 (10)
H35	0.5597	0.2721	0.4766	0.078*
C36	0.4366 (3)	0.33884 (13)	0.5151 (3)	0.0466 (7)
C41	0.1792 (3)	0.42163 (13)	0.3172 (3)	0.0451 (7)
C51	0.0943 (3)	0.55225 (13)	0.3593 (3)	0.0380 (6)
C52	0.0877 (3)	0.61968 (13)	0.3648 (3)	0.0404 (7)
C53	0.1419 (3)	0.66595 (14)	0.4726 (3)	0.0497 (8)
H53	0.1932	0.6550	0.5699	0.060*
C54	0.1186 (4)	0.72736 (15)	0.4329 (4)	0.0614 (9)
H54	0.1561	0.7581	0.5041	0.074*
C55	0.0405 (4)	0.74537 (17)	0.2892 (4)	0.0657 (10)
H55	0.0253	0.7877	0.2669	0.079*
C56	−0.0136 (4)	0.70208 (16)	0.1814 (4)	0.0581 (9)
H56	−0.0650	0.7140	0.0849	0.070*
C57	0.0104 (3)	0.63913 (14)	0.2198 (3)	0.0451 (7)
C58	0.0214 (3)	0.53562 (14)	0.2152 (3)	0.0452 (7)
H58	0.0082	0.4948	0.1791	0.054*
N1	0.1961 (2)	0.53636 (10)	0.6215 (2)	0.0386 (6)
N2	0.1568 (3)	0.39821 (12)	0.2015 (3)	0.0630 (8)
N3	−0.0283 (3)	0.58711 (12)	0.1335 (3)	0.0500 (7)
H3	−0.0773	0.5870	0.0405	0.060*
S	0.25060 (12)	0.60852 (4)	0.90204 (10)	0.0706 (3)
Br	0.51614 (4)	0.404354 (16)	0.43368 (4)	0.06285 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0378 (18)	0.0460 (16)	0.0330 (14)	−0.0027 (13)	0.0123 (13)	0.0018 (13)
C2	0.049 (2)	0.0473 (17)	0.0288 (14)	0.0025 (14)	0.0084 (13)	0.0054 (12)
C3	0.0397 (18)	0.0415 (15)	0.0365 (15)	−0.0016 (13)	0.0128 (13)	0.0067 (12)
C4	0.0403 (18)	0.0393 (14)	0.0298 (14)	−0.0037 (13)	0.0094 (12)	0.0000 (12)
C5	0.0362 (17)	0.0420 (15)	0.0330 (14)	−0.0041 (13)	0.0103 (12)	0.0019 (12)
C11	0.0382 (18)	0.0517 (17)	0.0380 (16)	−0.0058 (14)	0.0093 (13)	−0.0024 (13)
C12	0.054 (2)	0.0600 (18)	0.0271 (14)	−0.0014 (15)	0.0083 (14)	−0.0045 (14)
C13	0.059 (2)	0.088 (3)	0.0347 (17)	−0.005 (2)	0.0078 (16)	−0.0043 (17)
C14	0.076 (3)	0.075 (2)	0.0419 (18)	−0.001 (2)	0.0139 (18)	−0.0232 (17)
C31	0.0467 (19)	0.0402 (15)	0.0285 (14)	0.0000 (13)	0.0038 (13)	0.0009 (12)
C32	0.062 (2)	0.0500 (19)	0.0537 (19)	−0.0032 (16)	0.0163 (17)	0.0094 (15)
C33	0.087 (3)	0.0421 (19)	0.071 (2)	−0.0048 (19)	0.012 (2)	0.0172 (17)
C34	0.086 (3)	0.046 (2)	0.080 (3)	0.011 (2)	0.013 (2)	0.0019 (18)
C35	0.070 (3)	0.057 (2)	0.066 (2)	0.0158 (18)	0.0176 (19)	−0.0031 (18)
C36	0.051 (2)	0.0464 (17)	0.0392 (16)	−0.0005 (15)	0.0082 (15)	0.0002 (13)
C41	0.054 (2)	0.0375 (15)	0.0383 (17)	0.0044 (14)	0.0051 (14)	0.0058 (14)
C51	0.0384 (18)	0.0446 (15)	0.0318 (14)	−0.0001 (13)	0.0119 (13)	0.0035 (12)
C52	0.0407 (18)	0.0457 (15)	0.0389 (16)	0.0046 (14)	0.0182 (14)	0.0090 (13)
C53	0.056 (2)	0.0463 (17)	0.0477 (18)	0.0001 (15)	0.0179 (16)	0.0005 (14)
C54	0.072 (3)	0.0451 (18)	0.073 (2)	−0.0003 (17)	0.031 (2)	0.0008 (17)
C55	0.076 (3)	0.0490 (19)	0.078 (3)	0.0099 (18)	0.032 (2)	0.0204 (19)
C56	0.057 (2)	0.061 (2)	0.058 (2)	0.0113 (18)	0.0199 (17)	0.0262 (18)
C57	0.0436 (19)	0.0540 (18)	0.0409 (16)	0.0052 (15)	0.0177 (14)	0.0119 (14)
C58	0.045 (2)	0.0494 (17)	0.0402 (16)	0.0037 (14)	0.0111 (14)	0.0024 (14)
N1	0.0424 (15)	0.0416 (13)	0.0316 (12)	−0.0021 (11)	0.0107 (11)	0.0006 (10)
N2	0.089 (2)	0.0508 (16)	0.0405 (15)	0.0127 (14)	0.0065 (15)	−0.0049 (12)
N3	0.0488 (18)	0.0617 (17)	0.0330 (13)	0.0058 (13)	0.0024 (12)	0.0085 (12)
S	0.0982 (9)	0.0602 (5)	0.0497 (5)	0.0089 (5)	0.0167 (5)	−0.0073 (4)
Br	0.0616 (3)	0.0661 (3)	0.0687 (3)	−0.00767 (17)	0.0314 (2)	0.00167 (16)

Geometric parameters (Å, º) top

C1—N1	1.345 (3)	C33—H33	0.9300
C1—C2	1.383 (4)	C34—C35	1.378 (5)
C1—C11	1.466 (4)	C34—H34	0.9300
C2—C3	1.380 (4)	C35—C36	1.387 (4)
C2—H2	0.9300	C35—H35	0.9300
C3—C4	1.405 (4)	C36—Br	1.899 (3)
C3—C31	1.480 (4)	C41—N2	1.143 (4)
C4—C5	1.408 (4)	C51—C58	1.371 (4)
C4—C41	1.431 (4)	C51—C52	1.443 (4)
C5—N1	1.346 (3)	C52—C53	1.399 (4)
C5—C51	1.454 (4)	C52—C57	1.407 (4)
C11—C12	1.390 (4)	C53—C54	1.364 (4)
C11—S	1.698 (3)	C53—H53	0.9300
C12—C13	1.420 (4)	C54—C55	1.391 (5)
C12—H12	0.9300	C54—H54	0.9300
C13—C14	1.347 (5)	C55—C56	1.354 (5)
C13—H13	0.9300	C55—H55	0.9300
C14—S	1.691 (4)	C56—C57	1.394 (4)
C14—H14	0.9300	C56—H56	0.9300
C31—C36	1.381 (4)	C57—N3	1.358 (4)
C31—C32	1.395 (4)	C58—N3	1.347 (4)
C32—C33	1.376 (5)	C58—H58	0.9300
C32—H32	0.9300	N3—H3	0.8600
C33—C34	1.354 (6)

N1—C1—C2	122.8 (2)	C35—C34—H34	119.8
N1—C1—C11	116.1 (2)	C34—C35—C36	118.8 (4)
C2—C1—C11	121.1 (2)	C34—C35—H35	120.6
C3—C2—C1	119.8 (3)	C36—C35—H35	120.6
C3—C2—H2	120.1	C31—C36—C35	121.9 (3)
C1—C2—H2	120.1	C31—C36—Br	120.9 (2)
C2—C3—C4	117.3 (3)	C35—C36—Br	117.2 (3)
C2—C3—C31	119.7 (2)	N2—C41—C4	179.1 (3)
C4—C3—C31	123.1 (2)	C58—C51—C52	105.9 (2)
C3—C4—C5	120.6 (2)	C58—C51—C5	127.8 (3)
C3—C4—C41	117.3 (2)	C52—C51—C5	126.2 (2)
C5—C4—C41	122.0 (2)	C53—C52—C57	117.9 (3)
N1—C5—C4	120.1 (2)	C53—C52—C51	135.8 (3)
N1—C5—C51	115.4 (2)	C57—C52—C51	106.3 (2)
C4—C5—C51	124.5 (2)	C54—C53—C52	119.0 (3)
C12—C11—C1	127.9 (3)	C54—C53—H53	120.5
C12—C11—S	111.8 (2)	C52—C53—H53	120.5
C1—C11—S	120.3 (2)	C53—C54—C55	122.0 (3)
C11—C12—C13	110.6 (3)	C53—C54—H54	119.0
C11—C12—H12	124.7	C55—C54—H54	119.0
C13—C12—H12	124.7	C56—C55—C54	120.9 (3)
C14—C13—C12	113.1 (3)	C56—C55—H55	119.6
C14—C13—H13	123.5	C54—C55—H55	119.6
C12—C13—H13	123.5	C55—C56—C57	117.8 (3)
C13—C14—S	112.5 (3)	C55—C56—H56	121.1
C13—C14—H14	123.8	C57—C56—H56	121.1
S—C14—H14	123.8	N3—C57—C56	129.7 (3)
C36—C31—C32	117.3 (3)	N3—C57—C52	107.8 (3)
C36—C31—C3	123.8 (3)	C56—C57—C52	122.4 (3)
C32—C31—C3	118.8 (3)	N3—C58—C51	110.1 (3)
C33—C32—C31	120.8 (3)	N3—C58—H58	124.9
C33—C32—H32	119.6	C51—C58—H58	124.9
C31—C32—H32	119.6	C1—N1—C5	119.4 (2)
C34—C33—C32	120.7 (3)	C58—N3—C57	109.9 (3)
C34—C33—H33	119.7	C58—N3—H3	125.1
C32—C33—H33	119.7	C57—N3—H3	125.1
C33—C34—C35	120.5 (3)	C14—S—C11	92.04 (16)
C33—C34—H34	119.8

N1—C1—C2—C3	0.0 (5)	C34—C35—C36—C31	0.8 (5)
C11—C1—C2—C3	179.6 (3)	C34—C35—C36—Br	179.2 (3)
C1—C2—C3—C4	−1.7 (4)	N1—C5—C51—C58	−161.3 (3)
C1—C2—C3—C31	177.8 (3)	C4—C5—C51—C58	20.3 (5)
C2—C3—C4—C5	2.1 (4)	N1—C5—C51—C52	20.1 (4)
C31—C3—C4—C5	−177.3 (3)	C4—C5—C51—C52	−158.3 (3)
C2—C3—C4—C41	−179.0 (3)	C58—C51—C52—C53	−177.4 (3)
C31—C3—C4—C41	1.6 (4)	C5—C51—C52—C53	1.5 (5)
C3—C4—C5—N1	−0.8 (4)	C58—C51—C52—C57	−0.4 (3)
C41—C4—C5—N1	−179.7 (3)	C5—C51—C52—C57	178.4 (3)
C3—C4—C5—C51	177.5 (3)	C57—C52—C53—C54	−0.4 (4)
C41—C4—C5—C51	−1.4 (4)	C51—C52—C53—C54	176.3 (3)
N1—C1—C11—C12	169.4 (3)	C52—C53—C54—C55	1.2 (5)
C2—C1—C11—C12	−10.2 (5)	C53—C54—C55—C56	−1.3 (5)
N1—C1—C11—S	−7.5 (4)	C54—C55—C56—C57	0.7 (5)
C2—C1—C11—S	172.9 (2)	C55—C56—C57—N3	−178.0 (3)
C1—C11—C12—C13	−178.3 (3)	C55—C56—C57—C52	0.0 (5)
S—C11—C12—C13	−1.2 (4)	C53—C52—C57—N3	178.3 (3)
C11—C12—C13—C14	0.5 (4)	C51—C52—C57—N3	0.7 (3)
C12—C13—C14—S	0.5 (4)	C53—C52—C57—C56	−0.2 (4)
C2—C3—C31—C36	−108.6 (3)	C51—C52—C57—C56	−177.8 (3)
C4—C3—C31—C36	70.8 (4)	C52—C51—C58—N3	0.1 (3)
C2—C3—C31—C32	66.9 (4)	C5—C51—C58—N3	−178.8 (3)
C4—C3—C31—C32	−113.7 (3)	C2—C1—N1—C5	1.3 (4)
C36—C31—C32—C33	0.4 (5)	C11—C1—N1—C5	−178.3 (2)
C3—C31—C32—C33	−175.3 (3)	C4—C5—N1—C1	−0.9 (4)
C31—C32—C33—C34	0.5 (5)	C51—C5—N1—C1	−179.3 (2)
C32—C33—C34—C35	−0.8 (6)	C51—C58—N3—C57	0.4 (4)
C33—C34—C35—C36	0.2 (6)	C56—C57—N3—C58	177.6 (3)
C32—C31—C36—C35	−1.1 (4)	C52—C57—N3—C58	−0.6 (4)
C3—C31—C36—C35	174.4 (3)	C13—C14—S—C11	−1.0 (3)
C32—C31—C36—Br	−179.4 (2)	C12—C11—S—C14	1.3 (3)
C3—C31—C36—Br	−3.9 (4)	C1—C11—S—C14	178.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring of the indole moiety.

D—H···A	D—H	H···A	D···A	D—H···A
C53—H53···N1	0.93	2.58	3.069 (4)	114
C58—H58···N2	0.93	2.55	3.278 (4)	135
N3—H3···N2ⁱ	0.86	2.17	3.008 (4)	165
C32—H32···Cg1ⁱⁱ	0.93	2.89	3.761 (4)	157

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the benzene ring of the indole moiety.

D—H···A	D—H	H···A	D···A	D—H···A
C53—H53···N1	0.93	2.58	3.069 (4)	114
C58—H58···N2	0.93	2.55	3.278 (4)	135
N3—H3···N2ⁱ	0.86	2.17	3.008 (4)	165
C32—H32···Cg1ⁱⁱ	0.93	2.89	3.761 (4)	157

Symmetry codes: (i) −x, −y+1, −z; (ii) −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

Brandt, W., Mologni, L., Preu, L., Lemcke, T., Gambacorti-Passerini, C. & Kunick, C. (2010). Eur. J. Med. Chem. 45, 2919–2927. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El-Sayed, H. A., Moustafa, A. H., Haikal, A. E.-F. Z., Abu-El-Halawa, R. & Ashry, E. S. H. E. (2011). Eur. J. Med. Chem. 46, 2948–2954. Web of Science CAS PubMed Google Scholar
Ji, J., Bunnelle, W. H., Anderson, D. J., Faltynek, C., Dyhring, T., Ahring, P. K., Rueter, L. E., Curzon, P., Buckley, M. J., Marsh, K. C., Kempf-Grote, A. & Meyer, M. D. (2007). Biochem. Pharmacol. 74, 1253–1262. Web of Science CrossRef PubMed CAS Google Scholar
Kim, K.-R., Rhee, S.-D., Kim, H. Y., Jung, W. H., Yang, S.-D., Kim, S. S., Ahn, J. H. & Cheon, H. G. (2005). Eur. J. Pharmacol. 518, 63–70. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. 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

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Volume 70| Part 9| September 2014| Pages o968-o969

doi:10.1107/S1600536814017188

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

Crystal structure of 2-(2-bromo­phen­yl)-4-(1H-indol-3-yl)-6-(thio­phen-2-yl)pyridine-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-(2-bromophenyl)-4-(1H-indol-3-yl)-6-(thiophen-2-yl)pyridine-3-carbonitrile