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

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

doi:10.1107/S1600536814020170

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1120-o1121

doi:10.1107/S1600536814020170

Open

access

ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

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

R. Vishnupriya,^a J. Suresh,^a Marimuthu Sakthi,^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 4 September 2014; accepted 7 September 2014; online 24 September 2014)

In the title compound, C₂₇H₁₉N₃O, the dihedral angles between the plane of the pyridine ring and those of the indole (r.m.s. deviation = 0.018 Å), phenyl and methoxybenzene substituents are 33.60 (6), 25.28 (7) and 49.31 (7)°, respectively. The N atom of the carbonitrile group is significantly displaced [0.288 (2) Å] from the plane of the pyridine ring, perhaps due to steric crowding. In the crystal, inversion dimers linked by pairs of N—H⋯N_n (n = nitrile) hydrogen bonds generate R₂²(16) loops. Aromatic π–π stacking [centroid–centroid separation = 3.6906 (7) Å] and very weak C—H⋯π interactions are also observed".

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

CCDC reference: 1023204

1. Related literature

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983 ).

2. Experimental

2.1. Crystal data

C₂₇H₁₉N₃O
M_r = 401.45
Orthorhombic, P b c a
a = 15.7102 (5) Å
b = 10.7491 (3) Å
c = 24.3648 (7) Å
V = 4114.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.980
27554 measured reflections
4486 independent reflections
3331 reflections with I > 2σ(I)
R_int = 0.025

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.01
4486 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2ⁱ	0.86	2.15	2.9693 (19)	159
C32—H32⋯Cg1ⁱⁱ	0.93	3.00	3.9157 (19)	170
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+1, -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: 1023204

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814020170/hb7280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020170/hb7280Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814020170/hb7280Isup3.cml

checkCIF report

Comment top

Derivatives of 3-cyanopyridine are important and useful intermediates in preparing a varity of heterocyclic compounds (Shishoo et al., 1983). Therefore, the synthesis of 3-cyanopyridine derivatives attracts much interest in organic chemistry. It was in this context that the title compound, was investigated.

The deviation of the nitrile atoms (C41,N2) from the mean plane of the pyridine ring system is -0.1497 (1) Å and -0.2886 (5) Å. The shortening of the C—N distances [1.337 (3) and 1.341 Å] and the opening of the N1–C11–C10 angle [121.15 (2)°] may be attributed to the size of the substituent at C1, correlating well with the values observed in the ortho-substituted derivative. The dihedral angle between the pseudo-axial phenyl substituent and the plane of the pyridine ring is 69.13 (8)°.

The crystal structure features an 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 pyrrole ring of the indole moiety) and by π···π stacking interaction involving adjacent pyridine rings of the symmetry related molecule at (1-X,1-Y,-Z), with a centroid-to-centroid distance of 3.6906 (7) Å·(Fig 2).

Related literature top

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983).

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-methoxy 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 σilica gel (230–400 mesh) using petroleum ether-ethyl acetate mixture (7:3 v/v), which afforded the pure compound.

Melting point:265 °C, Yield: 72%.

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 and π···π stacking interaction (dotted lines; symmetry code: (i) (1-x, 1-y,-z)

4-(1H-Indol-3-yl)-2-(4-methoxyphenyl)-6-phenylpyridine-3-carbonitrile top

Crystal data top

C₂₇H₁₉N₃O	F(000) = 1680
M_r = 401.45	D_x = 1.296 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2000 reflections
a = 15.7102 (5) Å	θ = 2–27°
b = 10.7491 (3) Å	µ = 0.08 mm⁻¹
c = 24.3648 (7) Å	T = 293 K
V = 4114.5 (2) Å³	Block, colourless
Z = 8	0.30 × 0.28 × 0.25 mm

Data collection top

Bruker Kappa APEXII diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.1°
ω and ϕ scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→8
T_min = 0.976, T_max = 0.980	l = −31→31
27554 measured reflections

Refinement top

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0411P)² + 1.0149P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4486 reflections	Δρ_max = 0.15 e Å⁻³
282 parameters	Δρ_min = −0.16 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: 0.0027 (4)

Crystal data top

C₂₇H₁₉N₃O	V = 4114.5 (2) Å³
M_r = 401.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.7102 (5) Å	µ = 0.08 mm⁻¹
b = 10.7491 (3) Å	T = 293 K
c = 24.3648 (7) Å	0.30 × 0.28 × 0.25 mm

Data collection top

Bruker Kappa APEXII diffractometer	4486 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3331 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.025
27554 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
4486 reflections	Δρ_min = −0.16 e Å⁻³
282 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	0.11716 (8)	1.07304 (12)	0.96916 (5)	0.0400 (3)
C2	0.14114 (9)	1.06339 (12)	1.02373 (5)	0.0436 (3)
H2	0.1574	1.1344	1.0428	0.052*
C3	0.14124 (8)	0.94978 (12)	1.05007 (5)	0.0416 (3)
C4	0.11465 (8)	0.84683 (11)	1.01907 (5)	0.0416 (3)
C5	0.08413 (8)	0.86400 (11)	0.96531 (5)	0.0407 (3)
C11	0.12231 (8)	1.19255 (12)	0.93922 (5)	0.0402 (3)
C12	0.07016 (9)	1.21553 (12)	0.89470 (5)	0.0465 (3)
H12	0.0316	1.1552	0.8833	0.056*
C13	0.07492 (11)	1.32728 (14)	0.86716 (6)	0.0559 (4)
H13	0.0391	1.3420	0.8375	0.067*
C14	0.13180 (11)	1.41679 (14)	0.88303 (7)	0.0605 (4)
H14	0.1350	1.4917	0.8641	0.073*
C15	0.18372 (11)	1.39515 (15)	0.92690 (8)	0.0711 (5)
H15	0.2223	1.4558	0.9380	0.085*
C16	0.17937 (10)	1.28396 (14)	0.95483 (7)	0.0614 (4)
H16	0.2152	1.2701	0.9846	0.074*
C31	0.16647 (9)	0.94381 (12)	1.10856 (5)	0.0430 (3)
C32	0.13218 (10)	1.03013 (13)	1.14465 (6)	0.0515 (4)
H32	0.0935	1.0886	1.1317	0.062*
C33	0.15425 (11)	1.03077 (14)	1.19904 (6)	0.0576 (4)
H33	0.1301	1.0888	1.2227	0.069*
C34	0.21220 (10)	0.94553 (14)	1.21888 (6)	0.0547 (4)
C35	0.24701 (10)	0.85934 (15)	1.18375 (6)	0.0586 (4)
H35	0.2862	0.8015	1.1968	0.070*
C36	0.22377 (10)	0.85875 (14)	1.12909 (6)	0.0532 (4)
H36	0.2473	0.7997	1.1057	0.064*
C37	0.28200 (13)	0.8619 (2)	1.29741 (7)	0.0858 (6)
H37A	0.2574	0.7814	1.2910	0.129*
H37B	0.2861	0.8763	1.3362	0.129*
H37C	0.3378	0.8651	1.2814	0.129*
C41	0.11876 (9)	0.72404 (13)	1.04200 (6)	0.0492 (3)
C51	0.04591 (9)	0.76538 (12)	0.93237 (6)	0.0441 (3)
C52	0.04502 (9)	0.75788 (12)	0.87349 (6)	0.0462 (3)
C53	0.08391 (10)	0.82422 (15)	0.83125 (6)	0.0572 (4)
H53	0.1182	0.8925	0.8390	0.069*
C54	0.07081 (13)	0.78724 (17)	0.77795 (7)	0.0721 (5)
H54	0.0967	0.8311	0.7496	0.087*
C55	0.01956 (14)	0.68547 (18)	0.76559 (8)	0.0784 (6)
H55	0.0120	0.6623	0.7291	0.094*
C56	−0.01989 (12)	0.61900 (15)	0.80601 (8)	0.0704 (5)
H56	−0.0543	0.5511	0.7977	0.085*
C57	−0.00692 (10)	0.65614 (13)	0.85977 (7)	0.0533 (4)
C58	−0.00419 (10)	0.66969 (13)	0.95069 (6)	0.0529 (4)
H58	−0.0145	0.6513	0.9874	0.063*
N1	0.08729 (7)	0.97572 (9)	0.94093 (4)	0.0419 (3)
N2	0.12503 (10)	0.62657 (12)	1.05973 (6)	0.0694 (4)
N3	−0.03648 (9)	0.60601 (11)	0.90767 (6)	0.0597 (4)
H3	−0.0704	0.5435	0.9101	0.072*
O	0.22989 (9)	0.95450 (12)	1.27328 (4)	0.0808 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0366 (7)	0.0401 (7)	0.0433 (7)	0.0005 (5)	0.0008 (5)	0.0017 (5)
C2	0.0461 (8)	0.0390 (7)	0.0457 (7)	−0.0014 (6)	−0.0031 (6)	−0.0012 (6)
C3	0.0385 (7)	0.0436 (7)	0.0427 (7)	0.0036 (5)	0.0014 (5)	0.0027 (6)
C4	0.0398 (7)	0.0374 (7)	0.0477 (7)	0.0027 (5)	0.0046 (6)	0.0030 (6)
C5	0.0383 (7)	0.0384 (7)	0.0453 (7)	0.0021 (5)	0.0043 (6)	−0.0007 (6)
C11	0.0390 (7)	0.0396 (7)	0.0420 (7)	0.0000 (5)	0.0025 (5)	0.0025 (5)
C12	0.0513 (8)	0.0437 (7)	0.0444 (7)	−0.0006 (6)	−0.0023 (6)	−0.0008 (6)
C13	0.0626 (10)	0.0533 (8)	0.0518 (9)	0.0050 (7)	−0.0070 (7)	0.0100 (7)
C14	0.0608 (10)	0.0472 (8)	0.0736 (11)	0.0003 (7)	0.0047 (8)	0.0200 (8)
C15	0.0608 (10)	0.0561 (9)	0.0963 (13)	−0.0219 (8)	−0.0149 (9)	0.0197 (9)
C16	0.0568 (9)	0.0567 (9)	0.0706 (10)	−0.0151 (7)	−0.0196 (8)	0.0164 (8)
C31	0.0436 (7)	0.0424 (7)	0.0429 (7)	0.0017 (6)	0.0001 (6)	0.0037 (6)
C32	0.0586 (9)	0.0455 (8)	0.0504 (8)	0.0109 (7)	−0.0023 (7)	0.0032 (6)
C33	0.0707 (10)	0.0544 (9)	0.0477 (8)	0.0103 (8)	0.0017 (7)	−0.0055 (7)
C34	0.0593 (9)	0.0642 (9)	0.0407 (7)	0.0013 (8)	−0.0038 (7)	0.0020 (7)
C35	0.0568 (9)	0.0660 (10)	0.0528 (8)	0.0164 (7)	−0.0072 (7)	0.0068 (7)
C36	0.0550 (9)	0.0555 (8)	0.0490 (8)	0.0152 (7)	−0.0012 (7)	−0.0019 (7)
C37	0.0742 (12)	0.1313 (17)	0.0517 (10)	0.0134 (12)	−0.0137 (9)	0.0174 (11)
C41	0.0482 (8)	0.0456 (8)	0.0539 (8)	0.0005 (6)	0.0004 (6)	0.0042 (6)
C51	0.0444 (7)	0.0367 (7)	0.0511 (8)	0.0035 (6)	−0.0004 (6)	−0.0023 (6)
C52	0.0466 (7)	0.0389 (7)	0.0531 (8)	0.0107 (6)	−0.0068 (6)	−0.0024 (6)
C53	0.0616 (10)	0.0562 (9)	0.0537 (9)	0.0091 (7)	−0.0037 (7)	0.0016 (7)
C54	0.0878 (13)	0.0767 (12)	0.0519 (9)	0.0216 (10)	−0.0066 (9)	0.0040 (9)
C55	0.1021 (15)	0.0748 (12)	0.0582 (11)	0.0315 (11)	−0.0277 (10)	−0.0137 (9)
C56	0.0829 (13)	0.0511 (9)	0.0773 (12)	0.0176 (9)	−0.0367 (10)	−0.0141 (9)
C57	0.0554 (9)	0.0389 (7)	0.0655 (10)	0.0110 (6)	−0.0160 (7)	−0.0060 (7)
C58	0.0548 (9)	0.0423 (7)	0.0616 (9)	−0.0015 (6)	0.0010 (7)	−0.0032 (7)
N1	0.0427 (6)	0.0382 (6)	0.0447 (6)	−0.0008 (5)	0.0002 (5)	−0.0003 (5)
N2	0.0780 (10)	0.0480 (8)	0.0823 (10)	−0.0025 (7)	−0.0103 (8)	0.0158 (7)
N3	0.0606 (8)	0.0397 (6)	0.0787 (10)	−0.0065 (6)	−0.0109 (7)	−0.0045 (6)
O	0.0949 (10)	0.1018 (10)	0.0457 (6)	0.0184 (8)	−0.0140 (6)	−0.0034 (6)

Geometric parameters (Å, º) top

C1—N1	1.3370 (16)	C33—H33	0.9300
C1—C2	1.3857 (18)	C34—O	1.3577 (17)
C1—C11	1.4795 (17)	C34—C35	1.375 (2)
C2—C3	1.3796 (18)	C35—C36	1.381 (2)
C2—H2	0.9300	C35—H35	0.9300
C3—C4	1.4035 (18)	C36—H36	0.9300
C3—C31	1.4806 (18)	C37—O	1.417 (2)
C4—C5	1.4069 (18)	C37—H37A	0.9600
C4—C41	1.4347 (18)	C37—H37B	0.9600
C5—N1	1.3406 (16)	C37—H37C	0.9600
C5—C51	1.4590 (18)	C41—N2	1.1375 (17)
C11—C12	1.3817 (18)	C51—C58	1.3700 (19)
C11—C16	1.3833 (19)	C51—C52	1.4368 (19)
C12—C13	1.3780 (19)	C52—C53	1.393 (2)
C12—H12	0.9300	C52—C57	1.405 (2)
C13—C14	1.369 (2)	C53—C54	1.374 (2)
C13—H13	0.9300	C53—H53	0.9300
C14—C15	1.365 (2)	C54—C55	1.391 (3)
C14—H14	0.9300	C54—H54	0.9300
C15—C16	1.377 (2)	C55—C56	1.365 (3)
C15—H15	0.9300	C55—H55	0.9300
C16—H16	0.9300	C56—C57	1.384 (2)
C31—C36	1.3771 (19)	C56—H56	0.9300
C31—C32	1.3872 (19)	C57—N3	1.367 (2)
C32—C33	1.370 (2)	C58—N3	1.3507 (19)
C32—H32	0.9300	C58—H58	0.9300
C33—C34	1.379 (2)	N3—H3	0.8600

N1—C1—C2	122.03 (12)	C35—C34—C33	119.47 (13)
N1—C1—C11	116.42 (11)	C34—C35—C36	119.89 (14)
C2—C1—C11	121.55 (12)	C34—C35—H35	120.1
C3—C2—C1	120.85 (12)	C36—C35—H35	120.1
C3—C2—H2	119.6	C31—C36—C35	121.33 (14)
C1—C2—H2	119.6	C31—C36—H36	119.3
C2—C3—C4	116.57 (12)	C35—C36—H36	119.3
C2—C3—C31	119.10 (12)	O—C37—H37A	109.5
C4—C3—C31	124.31 (11)	O—C37—H37B	109.5
C3—C4—C5	119.94 (11)	H37A—C37—H37B	109.5
C3—C4—C41	120.15 (12)	O—C37—H37C	109.5
C5—C4—C41	119.91 (12)	H37A—C37—H37C	109.5
N1—C5—C4	121.15 (12)	H37B—C37—H37C	109.5
N1—C5—C51	114.99 (12)	N2—C41—C4	177.55 (17)
C4—C5—C51	123.85 (12)	C58—C51—C52	106.12 (12)
C12—C11—C16	118.24 (12)	C58—C51—C5	127.06 (13)
C12—C11—C1	120.66 (12)	C52—C51—C5	126.44 (12)
C16—C11—C1	121.11 (12)	C53—C52—C57	118.51 (14)
C13—C12—C11	120.40 (13)	C53—C52—C51	134.80 (14)
C13—C12—H12	119.8	C57—C52—C51	106.67 (13)
C11—C12—H12	119.8	C54—C53—C52	118.99 (16)
C14—C13—C12	120.70 (14)	C54—C53—H53	120.5
C14—C13—H13	119.6	C52—C53—H53	120.5
C12—C13—H13	119.6	C53—C54—C55	121.26 (18)
C15—C14—C13	119.45 (14)	C53—C54—H54	119.4
C15—C14—H14	120.3	C55—C54—H54	119.4
C13—C14—H14	120.3	C56—C55—C54	121.20 (16)
C14—C15—C16	120.36 (15)	C56—C55—H55	119.4
C14—C15—H15	119.8	C54—C55—H55	119.4
C16—C15—H15	119.8	C55—C56—C57	117.69 (17)
C15—C16—C11	120.85 (14)	C55—C56—H56	121.2
C15—C16—H16	119.6	C57—C56—H56	121.2
C11—C16—H16	119.6	N3—C57—C56	130.11 (16)
C36—C31—C32	117.89 (13)	N3—C57—C52	107.52 (13)
C36—C31—C3	123.59 (12)	C56—C57—C52	122.35 (16)
C32—C31—C3	118.50 (12)	N3—C58—C51	110.08 (14)
C33—C32—C31	121.22 (13)	N3—C58—H58	125.0
C33—C32—H32	119.4	C51—C58—H58	125.0
C31—C32—H32	119.4	C1—N1—C5	119.08 (11)
C32—C33—C34	120.19 (14)	C58—N3—C57	109.59 (13)
C32—C33—H33	119.9	C58—N3—H3	125.2
C34—C33—H33	119.9	C57—N3—H3	125.2
O—C34—C35	125.05 (14)	C34—O—C37	118.26 (14)
O—C34—C33	115.48 (14)

N1—C1—C2—C3	5.0 (2)	C33—C34—C35—C36	0.0 (3)
C11—C1—C2—C3	−175.75 (12)	C32—C31—C36—C35	−0.4 (2)
C1—C2—C3—C4	−1.04 (19)	C3—C31—C36—C35	178.13 (14)
C1—C2—C3—C31	−179.38 (12)	C34—C35—C36—C31	0.5 (3)
C2—C3—C4—C5	−4.40 (19)	N1—C5—C51—C58	−143.80 (14)
C31—C3—C4—C5	173.84 (12)	C4—C5—C51—C58	35.2 (2)
C2—C3—C4—C41	175.41 (13)	N1—C5—C51—C52	28.20 (19)
C31—C3—C4—C41	−6.3 (2)	C4—C5—C51—C52	−152.85 (13)
C3—C4—C5—N1	6.38 (19)	C58—C51—C52—C53	−178.06 (16)
C41—C4—C5—N1	−173.43 (12)	C5—C51—C52—C53	8.6 (3)
C3—C4—C5—C51	−172.52 (12)	C58—C51—C52—C57	0.18 (15)
C41—C4—C5—C51	7.7 (2)	C5—C51—C52—C57	−173.18 (13)
N1—C1—C11—C12	24.87 (18)	C57—C52—C53—C54	−0.6 (2)
C2—C1—C11—C12	−154.39 (13)	C51—C52—C53—C54	177.47 (15)
N1—C1—C11—C16	−154.96 (14)	C52—C53—C54—C55	0.1 (2)
C2—C1—C11—C16	25.8 (2)	C53—C54—C55—C56	0.3 (3)
C16—C11—C12—C13	−0.5 (2)	C54—C55—C56—C57	−0.2 (3)
C1—C11—C12—C13	179.65 (13)	C55—C56—C57—N3	−178.46 (16)
C11—C12—C13—C14	0.6 (2)	C55—C56—C57—C52	−0.3 (2)
C12—C13—C14—C15	−0.6 (3)	C53—C52—C57—N3	179.24 (13)
C13—C14—C15—C16	0.4 (3)	C51—C52—C57—N3	0.66 (15)
C14—C15—C16—C11	−0.3 (3)	C53—C52—C57—C56	0.7 (2)
C12—C11—C16—C15	0.3 (2)	C51—C52—C57—C56	−177.84 (14)
C1—C11—C16—C15	−179.83 (15)	C52—C51—C58—N3	−0.98 (16)
C2—C3—C31—C36	−132.13 (15)	C5—C51—C58—N3	172.33 (13)
C4—C3—C31—C36	49.7 (2)	C2—C1—N1—C5	−3.18 (19)
C2—C3—C31—C32	46.38 (19)	C11—C1—N1—C5	177.56 (11)
C4—C3—C31—C32	−131.82 (14)	C4—C5—N1—C1	−2.49 (18)
C36—C31—C32—C33	−0.2 (2)	C51—C5—N1—C1	176.49 (11)
C3—C31—C32—C33	−178.80 (14)	C51—C58—N3—C57	1.44 (17)
C31—C32—C33—C34	0.7 (2)	C56—C57—N3—C58	177.06 (16)
C32—C33—C34—O	179.74 (15)	C52—C57—N3—C58	−1.28 (16)
C32—C33—C34—C35	−0.6 (3)	C35—C34—O—C37	−6.1 (3)
O—C34—C35—C36	179.65 (16)	C33—C34—O—C37	173.55 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱ	0.86	2.15	2.9693 (19)	159
C32—H32···Cg1ⁱⁱ	0.93	3.00	3.9157 (19)	170

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱ	0.86	2.15	2.9693 (19)	159
C32—H32···Cg1ⁱⁱ	0.93	3.00	3.9157 (19)	170

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z.

Acknowledgements

JS and RV thank the management of 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 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Shishoo, C. J., Devani, M. B., Bhadti, V. S., Ananthan, S. & Ullas, G. V. (1983). Tetrahedron Lett. pp. 4611–4612. CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1120-o1121

doi:10.1107/S1600536814020170

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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