3-[(E)-2-Phenyl­ethen­yl]-1H-indole-6-carbonitrile

Ge, Y.-H.; Wu, D.-E.; Luo, Y.-H.

doi:10.1107/S1600536811054225

organic compounds

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Volume 68| Part 1| January 2012| Page o207

doi:10.1107/S1600536811054225

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3-[(E)-2-Phenylethenyl]-1H-indole-6-carbonitrile

Yu-Hua Ge,^a ^* Dong-En Wu ^a and Yang-Hui Luo ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: peluoyh@sina.com

(Received 5 November 2011; accepted 16 December 2011; online 21 December 2011)

In the title compound, C₁₇H₁₂N₂, the interplanar angle between the indole mean plane [max.deviation 0.030 (1) Å] and the phenyl ring is 24.32 (7)°. In the crystal, intermolecular N—H⋯N≡C hydrogen bonds form zigzag chains in the a-axis direction augmented by weak C—H⋯N≡C contacts.

Related literature

For indole derivatives as drug intermediates, see: Kunzer & Wendt (2011 ).

Experimental

Crystal data

C₁₇H₁₂N₂
M_r = 244.29
Orthorhombic, P b c a
a = 9.689 (8) Å
b = 7.440 (6) Å
c = 35.53 (3) Å
V = 2561 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.985, T_max = 0.985
16536 measured reflections
2263 independent reflections
1867 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.127
S = 1.16
2263 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.90	2.19	3.043 (3)	158
C5—H5A⋯N2ⁱⁱ	0.93	2.66	3.416 (4)	138
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) -x, -y+2, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054225/gg2065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054225/gg2065Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054225/gg2065Isup3.cml

checkCIF report

Comment top

Derivatives of indole are important chemical materials because they are excellent drug intermediates for many pharmaceutical products (Kunzer, et al.,2011). As part of our interest in these materials, we report here the crystal structure of the title compound C₁₇H₁₂N₂.

The molecular structure of the title compound is shown in Fig. 1. a dihedral angle of 24.32 (7)° between the planes of the indole and benzene rings is observed.

In the crystal, there are intermolecular N—H···O hydrogen bonds and no significant intermolecular π–π interactions [minimum ring centroid separation, 7.440 (5) Å]. (Fig. 2).

Related literature top

For indole derivatives as drug intermediates, see: Kunzer & Wendt (2011).

Experimental top

The title compound E-3-phenyl vinyl-6-cynaindole was obtained economically, Crystals of of it suitable for X-ray diffraction were obstained by slow evaporation of a ethanol solution.

Structure description top

The molecular structure of the title compound is shown in Fig. 1. a dihedral angle of 24.32 (7)° between the planes of the indole and benzene rings is observed.

In the crystal, there are intermolecular N—H···O hydrogen bonds and no significant intermolecular π–π interactions [minimum ring centroid separation, 7.440 (5) Å]. (Fig. 2).

For indole derivatives as drug intermediates, see: Kunzer & Wendt (2011).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. A packing view down the a axis showing the three dimensionnal network. Intermolecular hydrogen bonds are shown as dashed lines.

3-[(E)-2-Phenylethenyl]-1H-indole-6-carbonitrile top

Crystal data top

C₁₇H₁₂N₂	F(000) = 1024
M_r = 244.29	D_x = 1.267 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2263 reflections
a = 9.689 (8) Å	θ = 1.2–25.0°
b = 7.440 (6) Å	µ = 0.08 mm⁻¹
c = 35.53 (3) Å	T = 293 K
V = 2561 (4) Å³	Prism, blue
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2263 independent reflections
Radiation source: fine-focus sealed tube	1867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 1.2°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→8
T_min = 0.985, T_max = 0.985	l = −42→42
16536 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.069P)² + 0.3176P] where P = (F_o² + 2F_c²)/3
2263 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₂N₂	V = 2561 (4) Å³
M_r = 244.29	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.689 (8) Å	µ = 0.08 mm⁻¹
b = 7.440 (6) Å	T = 293 K
c = 35.53 (3) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2263 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1867 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.985	R_int = 0.027
16536 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.16	Δρ_max = 0.13 e Å⁻³
2263 reflections	Δρ_min = −0.20 e Å⁻³
172 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
N1	−0.14124 (13)	0.36176 (18)	0.04780 (4)	0.0497 (4)
H1A	−0.1933	0.3603	0.0268	0.060*
N2	0.17232 (16)	1.0338 (2)	0.01757 (4)	0.0620 (4)
C1	−0.13711 (17)	0.2312 (2)	0.07463 (5)	0.0515 (4)
H1B	−0.1876	0.1250	0.0738	0.062*
C2	−0.04867 (15)	0.2774 (2)	0.10301 (4)	0.0437 (4)
C3	0.00642 (14)	0.4503 (2)	0.09281 (4)	0.0388 (4)
C4	0.09969 (16)	0.5690 (2)	0.10937 (4)	0.0448 (4)
H4A	0.1368	0.5438	0.1329	0.054*
C5	−0.01787 (14)	0.6535 (2)	0.03886 (4)	0.0426 (4)
H5A	−0.0577	0.6824	0.0158	0.051*
C6	0.07849 (15)	0.7645 (2)	0.05558 (4)	0.0435 (4)
C7	0.13635 (17)	0.7231 (2)	0.09078 (4)	0.0477 (4)
H7A	0.2001	0.8010	0.1016	0.057*
C8	0.12868 (16)	0.9173 (2)	0.03509 (4)	0.0486 (4)
C9	−0.00992 (16)	0.1678 (2)	0.13506 (4)	0.0470 (4)
H9A	0.0605	0.2106	0.1504	0.056*
C10	−0.06676 (17)	0.0115 (2)	0.14427 (5)	0.0508 (4)
H10A	−0.1435	−0.0224	0.1302	0.061*
C11	−0.02405 (17)	−0.1135 (2)	0.17358 (4)	0.0469 (4)
C12	0.10257 (18)	−0.1029 (2)	0.19183 (5)	0.0534 (4)
H12A	0.1627	−0.0094	0.1861	0.064*
C13	0.1402 (2)	−0.2282 (3)	0.21825 (5)	0.0649 (5)
H13A	0.2253	−0.2186	0.2302	0.078*
C14	0.0534 (2)	−0.3680 (3)	0.22722 (6)	0.0756 (6)
H14A	0.0794	−0.4527	0.2451	0.091*
C15	−0.0719 (2)	−0.3811 (3)	0.20954 (6)	0.0795 (7)
H15A	−0.1315	−0.4749	0.2155	0.095*
C16	−0.1100 (2)	−0.2561 (3)	0.18295 (5)	0.0639 (5)
H16A	−0.1949	−0.2673	0.1710	0.077*
C34	−0.05265 (14)	0.4975 (2)	0.05786 (4)	0.0403 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0468 (7)	0.0499 (8)	0.0525 (8)	−0.0053 (6)	−0.0124 (6)	0.0016 (6)
N2	0.0596 (9)	0.0647 (10)	0.0618 (9)	−0.0127 (8)	−0.0015 (7)	0.0148 (8)
C1	0.0481 (9)	0.0448 (10)	0.0616 (10)	−0.0067 (7)	−0.0061 (8)	0.0041 (8)
C2	0.0403 (8)	0.0420 (9)	0.0487 (9)	0.0003 (7)	−0.0001 (7)	0.0007 (7)
C3	0.0354 (7)	0.0397 (8)	0.0412 (8)	0.0043 (6)	0.0014 (6)	−0.0011 (6)
C4	0.0484 (9)	0.0457 (9)	0.0402 (8)	0.0001 (7)	−0.0032 (7)	−0.0013 (7)
C5	0.0398 (8)	0.0457 (9)	0.0423 (8)	0.0066 (7)	0.0012 (6)	0.0023 (7)
C6	0.0417 (8)	0.0417 (9)	0.0472 (8)	0.0023 (7)	0.0076 (7)	0.0019 (7)
C7	0.0490 (9)	0.0466 (9)	0.0476 (9)	−0.0072 (7)	−0.0015 (7)	−0.0044 (7)
C8	0.0459 (9)	0.0509 (10)	0.0491 (9)	−0.0018 (8)	0.0015 (7)	0.0021 (8)
C9	0.0457 (8)	0.0454 (9)	0.0498 (9)	−0.0013 (7)	−0.0007 (7)	0.0016 (7)
C10	0.0488 (9)	0.0495 (10)	0.0540 (9)	−0.0028 (8)	−0.0021 (7)	0.0032 (8)
C11	0.0532 (9)	0.0432 (9)	0.0443 (9)	0.0014 (7)	0.0061 (7)	−0.0008 (7)
C12	0.0602 (10)	0.0498 (10)	0.0503 (9)	0.0006 (8)	0.0041 (8)	−0.0005 (8)
C13	0.0706 (12)	0.0697 (13)	0.0543 (10)	0.0150 (10)	−0.0015 (9)	0.0040 (9)
C14	0.0897 (15)	0.0720 (15)	0.0653 (12)	0.0171 (12)	0.0135 (11)	0.0233 (10)
C15	0.0866 (15)	0.0673 (14)	0.0845 (15)	−0.0052 (11)	0.0183 (12)	0.0279 (12)
C16	0.0609 (11)	0.0588 (12)	0.0722 (12)	−0.0072 (9)	0.0046 (9)	0.0116 (10)
C34	0.0347 (7)	0.0417 (8)	0.0446 (8)	0.0037 (6)	0.0009 (6)	−0.0016 (7)

Geometric parameters (Å, º) top

N1—C1	1.361 (2)	C7—H7A	0.9300
N1—C34	1.372 (2)	C9—C10	1.328 (2)
N1—H1A	0.8999	C9—H9A	0.9300
N2—C8	1.148 (2)	C10—C11	1.457 (2)
C1—C2	1.367 (2)	C10—H10A	0.9300
C1—H1B	0.9300	C11—C12	1.390 (3)
C2—C3	1.439 (2)	C11—C16	1.389 (3)
C2—C9	1.450 (2)	C12—C13	1.373 (3)
C3—C34	1.412 (2)	C12—H12A	0.9300
C3—C4	1.394 (2)	C13—C14	1.375 (3)
C4—C7	1.370 (2)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.370 (3)
C5—C34	1.385 (2)	C14—H14A	0.9300
C5—C6	1.380 (2)	C15—C16	1.376 (3)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.405 (2)	C16—H16A	0.9300
C6—C8	1.435 (2)

C1—N1—C34	108.91 (14)	C10—C9—H9A	117.3
C1—N1—H1A	126.0	C2—C9—H9A	117.3
C34—N1—H1A	125.1	C9—C10—C11	128.16 (16)
N1—C1—C2	110.82 (15)	C9—C10—H10A	115.9
N1—C1—H1B	124.6	C11—C10—H10A	115.9
C2—C1—H1B	124.6	C12—C11—C16	117.45 (16)
C1—C2—C3	105.76 (14)	C12—C11—C10	123.22 (15)
C1—C2—C9	126.88 (16)	C16—C11—C10	119.26 (16)
C3—C2—C9	127.18 (14)	C13—C12—C11	120.99 (18)
C34—C3—C4	118.45 (14)	C13—C12—H12A	119.5
C34—C3—C2	107.06 (13)	C11—C12—H12A	119.5
C4—C3—C2	134.49 (14)	C12—C13—C14	120.6 (2)
C7—C4—C3	119.67 (15)	C12—C13—H13A	119.7
C7—C4—H4A	120.2	C14—C13—H13A	119.7
C3—C4—H4A	120.2	C15—C14—C13	119.32 (19)
C34—C5—C6	117.15 (14)	C15—C14—H14A	120.3
C34—C5—H5A	121.4	C13—C14—H14A	120.3
C6—C5—H5A	121.4	C16—C15—C14	120.3 (2)
C5—C6—C7	121.46 (15)	C16—C15—H15A	119.9
C5—C6—C8	119.00 (15)	C14—C15—H15A	119.9
C7—C6—C8	119.34 (15)	C15—C16—C11	121.3 (2)
C4—C7—C6	120.61 (15)	C15—C16—H16A	119.3
C4—C7—H7A	119.7	C11—C16—H16A	119.3
C6—C7—H7A	119.7	N1—C34—C5	129.96 (14)
N2—C8—C6	176.59 (18)	N1—C34—C3	107.43 (14)
C10—C9—C2	125.35 (16)	C5—C34—C3	122.59 (14)

C34—N1—C1—C2	0.90 (19)	C9—C10—C11—C16	169.56 (17)
N1—C1—C2—C3	−0.13 (18)	C16—C11—C12—C13	−0.4 (2)
N1—C1—C2—C9	−175.44 (15)	C10—C11—C12—C13	−177.41 (16)
C1—C2—C3—C34	−0.66 (16)	C11—C12—C13—C14	0.2 (3)
C9—C2—C3—C34	174.63 (14)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C3—C4	179.82 (17)	C13—C14—C15—C16	0.3 (3)
C9—C2—C3—C4	−4.9 (3)	C14—C15—C16—C11	−0.6 (3)
C34—C3—C4—C7	−3.0 (2)	C12—C11—C16—C15	0.6 (3)
C2—C3—C4—C7	176.51 (15)	C10—C11—C16—C15	177.75 (18)
C34—C5—C6—C7	−1.5 (2)	C1—N1—C34—C5	177.01 (15)
C34—C5—C6—C8	173.32 (13)	C1—N1—C34—C3	−1.29 (17)
C3—C4—C7—C6	1.4 (2)	C6—C5—C34—N1	−178.20 (15)
C5—C6—C7—C4	0.9 (2)	C6—C5—C34—C3	−0.1 (2)
C8—C6—C7—C4	−173.94 (15)	C4—C3—C34—N1	−179.20 (13)
C1—C2—C9—C10	−8.2 (3)	C2—C3—C34—N1	1.20 (16)
C3—C2—C9—C10	177.49 (15)	C4—C3—C34—C5	2.3 (2)
C2—C9—C10—C11	173.21 (15)	C2—C3—C34—C5	−177.26 (13)
C9—C10—C11—C12	−13.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.90	2.19	3.043 (3)	158
C5—H5A···N2ⁱⁱ	0.93	2.66	3.416 (4)	138

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₂
M_r	244.29
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.689 (8), 7.440 (6), 35.53 (3)
V (Å³)	2561 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.985, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	16536, 2263, 1867
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.127, 1.16
No. of reflections	2263
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.90	2.19	3.043 (3)	158
C5—H5A···N2ⁱⁱ	0.93	2.66	3.416 (4)	138

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x, −y+2, −z.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815–1818. CrossRef CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S1600536811054225

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