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access6-[(E)-2-Phenylvinyl]-1H-indole
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
The title compound, C16H13N, is essentially planar [maximum deviation from the least-squares plane = 0.081 (3) Å], with a dihedral angle of 1.65 (13)° between the planes of the indole and benzene rings. In the crystal, there are no significant intermolecular π–π interactions [minimum ring centroid–centroid separation = 4.217 (5) Å].
Related literature
For background information on indole derivatives as drug intermediates, see: Kunzer & Wendt (2011![[Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.]](../../../../../../logos/arrows/e_arr.gif "Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.")
).
![[Scheme 1]](zs2163scheme1.gif)
Experimental
Crystal data
|
Data collection: CrystalClear (Rigaku, 2005); cell 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 and PLATON (Spek, 2009).
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536811051750/zs2163sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811051750/zs2163Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811051750/zs2163Isup3.cml
Crystals of 6-phenylvinylindole suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.
All H atoms attached to C atoms and the N atom were fixed geometrically and treated as riding with C—H = 0.93 Å and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).
Data collection: CrystalClear (Rigaku, 2005); cell 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) and PLATON (Spek, 2009).
![[Figure 1]](./zs2163fig1thm.gif) | 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. |
![[Figure 2]](./zs2163fig2thm.gif) | Fig. 2. A packing in the unit cell viewed down the a axis. |
| C16H13N | F(000) = 464 |
| Mr = 219.29 | Dx = 1.218 Mg m−3 |
| Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2n | Cell parameters from 1954 reflections |
| a = 8.254 (8) Å | θ = 3.2–25.0° |
| b = 5.626 (6) Å | µ = 0.07 mm−1 |
| c = 25.74 (3) Å | T = 296 K |
| V = 1195 (2) Å3 | Prism, colourless |
| Z = 4 | 0.30 × 0.20 × 0.10 mm |
| Rigaku SCXmini CCD-detector diffractometer | 1954 independent reflections |
| Radiation source: fine-focus sealed tube | 1627 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.022 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 25.0°, θmin = 3.2° |
| CCD profile–fitting scans | h = −9→9 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −6→6 |
| Tmin = 0.982, Tmax = 0.993 | l = −27→30 |
| 7653 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.132 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0665P)2 + 0.2586P] where P = (Fo2 + 2Fc2)/3 |
| 1954 reflections | (Δ/σ)max < 0.001 |
| 154 parameters | Δρmax = 0.27 e Å−3 |
| 19 restraints | Δρmin = −0.21 e Å−3 |
| C16H13N | V = 1195 (2) Å3 |
| Mr = 219.29 | Z = 4 |
| Orthorhombic, Pna21 | Mo Kα radiation |
| a = 8.254 (8) Å | µ = 0.07 mm−1 |
| b = 5.626 (6) Å | T = 296 K |
| c = 25.74 (3) Å | 0.30 × 0.20 × 0.10 mm |
| Rigaku SCXmini CCD-detector diffractometer | 1954 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 1627 reflections with I > 2σ(I) |
| Tmin = 0.982, Tmax = 0.993 | Rint = 0.022 |
| 7653 measured reflections |
| R[F2 > 2σ(F2)] = 0.046 | 19 restraints |
| wR(F2) = 0.132 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 0.27 e Å−3 |
| 1954 reflections | Δρmin = −0.21 e Å−3 |
| 154 parameters |
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 | ||
| C2 | −0.0689 (4) | 0.5222 (6) | 0.31498 (14) | 0.0656 (8) | |
| H2A | −0.0588 | 0.6242 | 0.2867 | 0.079* | |
| C8 | 0.0968 (4) | 0.4941 (5) | 0.46948 (12) | 0.0597 (6) | |
| C7 | 0.1442 (3) | 0.6940 (5) | 0.43984 (13) | 0.0623 (8) | |
| H7A | 0.2102 | 0.8076 | 0.4553 | 0.075* | |
| C15 | 0.4035 (4) | 0.4885 (6) | 0.70717 (14) | 0.0687 (9) | |
| H15A | 0.4359 | 0.4764 | 0.7417 | 0.082* | |
| C5 | −0.0018 (3) | 0.3276 (5) | 0.44626 (11) | 0.0538 (7) | |
| H5A | −0.0369 | 0.1955 | 0.4648 | 0.065* | |
| C3 | 0.0004 (3) | 0.5547 (5) | 0.36510 (11) | 0.0510 (6) | |
| N1 | −0.1423 (3) | 0.2156 (4) | 0.36424 (10) | 0.0594 (6) | |
| H1A | −0.1875 | 0.0850 | 0.3738 | 0.071* | |
| C6 | 0.0972 (3) | 0.7280 (5) | 0.38924 (13) | 0.0613 (8) | |
| H6A | 0.1289 | 0.8635 | 0.3712 | 0.074* | |
| C10 | 0.2538 (4) | 0.5725 (6) | 0.55023 (12) | 0.0658 (5) | |
| H10A | 0.3012 | 0.7004 | 0.5331 | 0.079* | |
| C4 | −0.0482 (3) | 0.3585 (4) | 0.39512 (11) | 0.0471 (6) | |
| C9 | 0.1498 (4) | 0.4487 (6) | 0.52418 (13) | 0.0636 (5) | |
| H9A | 0.1036 | 0.3191 | 0.5410 | 0.076* | |
| C12 | 0.4050 (4) | 0.6954 (6) | 0.62754 (15) | 0.0720 (9) | |
| H12A | 0.4403 | 0.8245 | 0.6080 | 0.086* | |
| C13 | 0.2544 (4) | 0.3359 (6) | 0.63444 (13) | 0.0709 (9) | |
| H13A | 0.1880 | 0.2199 | 0.6200 | 0.085* | |
| C11 | 0.3047 (4) | 0.5306 (6) | 0.60460 (13) | 0.0640 (6) | |
| C14 | 0.3045 (4) | 0.3175 (6) | 0.68583 (14) | 0.0716 (9) | |
| H14A | 0.2710 | 0.1891 | 0.7059 | 0.086* | |
| C16 | 0.4541 (4) | 0.6758 (7) | 0.67764 (14) | 0.0745 (9) | |
| H16A | 0.5223 | 0.7901 | 0.6919 | 0.089* | |
| C1 | −0.1528 (4) | 0.3136 (6) | 0.31610 (14) | 0.0672 (8) | |
| H1B | −0.2087 | 0.2483 | 0.2882 | 0.081* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.0589 (17) | 0.074 (2) | 0.0634 (19) | 0.0063 (16) | 0.0072 (14) | 0.0118 (17) |
| C8 | 0.0534 (11) | 0.0637 (12) | 0.0620 (12) | 0.0073 (10) | 0.0089 (9) | −0.0038 (11) |
| C7 | 0.0517 (15) | 0.0564 (17) | 0.079 (2) | −0.0009 (13) | 0.0019 (15) | −0.0132 (16) |
| C15 | 0.0648 (19) | 0.078 (2) | 0.063 (2) | 0.0144 (17) | −0.0019 (16) | −0.0018 (18) |
| C5 | 0.0495 (14) | 0.0506 (14) | 0.0612 (19) | 0.0012 (12) | 0.0077 (13) | 0.0047 (14) |
| C3 | 0.0395 (12) | 0.0517 (14) | 0.0618 (17) | 0.0039 (11) | 0.0095 (13) | 0.0058 (13) |
| N1 | 0.0490 (12) | 0.0554 (13) | 0.0739 (18) | −0.0070 (10) | 0.0006 (12) | −0.0002 (13) |
| C6 | 0.0507 (14) | 0.0428 (13) | 0.090 (2) | 0.0006 (12) | 0.0138 (16) | 0.0090 (16) |
| C10 | 0.0604 (10) | 0.0708 (11) | 0.0661 (10) | 0.0047 (9) | 0.0093 (8) | −0.0033 (9) |
| C4 | 0.0389 (12) | 0.0474 (13) | 0.0550 (16) | 0.0029 (10) | 0.0045 (12) | 0.0009 (12) |
| C9 | 0.0579 (9) | 0.0675 (11) | 0.0654 (10) | 0.0049 (9) | 0.0093 (8) | −0.0047 (9) |
| C12 | 0.0658 (19) | 0.074 (2) | 0.077 (2) | −0.0057 (16) | 0.0101 (18) | 0.0082 (19) |
| C13 | 0.0671 (19) | 0.071 (2) | 0.074 (2) | −0.0016 (16) | −0.0065 (18) | −0.0103 (18) |
| C11 | 0.0590 (11) | 0.0707 (12) | 0.0624 (12) | 0.0082 (11) | 0.0107 (10) | −0.0022 (11) |
| C14 | 0.073 (2) | 0.070 (2) | 0.072 (2) | 0.0003 (16) | 0.0026 (17) | 0.0096 (17) |
| C16 | 0.067 (2) | 0.078 (2) | 0.078 (3) | −0.0089 (17) | −0.0027 (18) | −0.0035 (19) |
| C1 | 0.0569 (17) | 0.082 (2) | 0.0630 (19) | 0.0074 (16) | −0.0034 (15) | −0.0041 (18) |
| C2—C1 | 1.363 (5) | N1—C4 | 1.372 (4) |
| C2—C3 | 1.423 (5) | N1—H1A | 0.8600 |
| C2—H2A | 0.9300 | C6—H6A | 0.9300 |
| C8—C5 | 1.377 (4) | C10—C9 | 1.293 (4) |
| C8—C7 | 1.415 (4) | C10—C11 | 1.480 (5) |
| C8—C9 | 1.497 (5) | C10—H10A | 0.9300 |
| C7—C6 | 1.372 (5) | C9—H9A | 0.9300 |
| C7—H7A | 0.9300 | C12—C16 | 1.356 (5) |
| C15—C16 | 1.365 (5) | C12—C11 | 1.376 (5) |
| C15—C14 | 1.377 (5) | C12—H12A | 0.9300 |
| C15—H15A | 0.9300 | C13—C14 | 1.390 (5) |
| C5—C4 | 1.382 (4) | C13—C11 | 1.401 (4) |
| C5—H5A | 0.9300 | C13—H13A | 0.9300 |
| C3—C4 | 1.406 (4) | C14—H14A | 0.9300 |
| C3—C6 | 1.405 (4) | C16—H16A | 0.9300 |
| N1—C1 | 1.359 (4) | C1—H1B | 0.9300 |
| C1—C2—C3 | 107.2 (3) | C11—C10—H10A | 116.8 |
| C1—C2—H2A | 126.4 | N1—C4—C5 | 129.5 (2) |
| C3—C2—H2A | 126.4 | N1—C4—C3 | 107.7 (3) |
| C5—C8—C7 | 118.0 (3) | C5—C4—C3 | 122.9 (3) |
| C5—C8—C9 | 117.7 (3) | C10—C9—C8 | 126.2 (3) |
| C7—C8—C9 | 124.2 (3) | C10—C9—H9A | 116.9 |
| C6—C7—C8 | 123.0 (3) | C8—C9—H9A | 116.9 |
| C6—C7—H7A | 118.5 | C16—C12—C11 | 122.2 (3) |
| C8—C7—H7A | 118.5 | C16—C12—H12A | 118.9 |
| C16—C15—C14 | 119.9 (3) | C11—C12—H12A | 118.9 |
| C16—C15—H15A | 120.0 | C14—C13—C11 | 119.5 (3) |
| C14—C15—H15A | 120.0 | C14—C13—H13A | 120.3 |
| C8—C5—C4 | 119.5 (3) | C11—C13—H13A | 120.3 |
| C8—C5—H5A | 120.3 | C12—C11—C13 | 118.0 (3) |
| C4—C5—H5A | 120.3 | C12—C11—C10 | 118.0 (3) |
| C4—C3—C6 | 117.7 (3) | C13—C11—C10 | 124.0 (3) |
| C4—C3—C2 | 106.4 (3) | C15—C14—C13 | 120.3 (3) |
| C6—C3—C2 | 135.9 (3) | C15—C14—H14A | 119.9 |
| C1—N1—C4 | 109.1 (2) | C13—C14—H14A | 119.9 |
| C1—N1—H1A | 125.5 | C12—C16—C15 | 120.1 (3) |
| C4—N1—H1A | 125.5 | C12—C16—H16A | 120.0 |
| C7—C6—C3 | 118.9 (3) | C15—C16—H16A | 120.0 |
| C7—C6—H6A | 120.5 | N1—C1—C2 | 109.7 (3) |
| C3—C6—H6A | 120.5 | N1—C1—H1B | 125.2 |
| C9—C10—C11 | 126.4 (3) | C2—C1—H1B | 125.2 |
| C9—C10—H10A | 116.8 |
Experimental details
| Crystal data | |
| Chemical formula | C16H13N |
| Mr | 219.29 |
| Crystal system, space group | Orthorhombic, Pna21 |
| Temperature (K) | 296 |
| a, b, c (Å) | 8.254 (8), 5.626 (6), 25.74 (3) |
| V (Å3) | 1195 (2) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.07 |
| Crystal size (mm) | 0.30 × 0.20 × 0.10 |
| Data collection | |
| Diffractometer | Rigaku SCXmini CCD-detector diffractometer |
| Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
| Tmin, Tmax | 0.982, 0.993 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7653, 1954, 1627 |
| Rint | 0.022 |
| (sin θ/λ)max (Å−1) | 0.594 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.132, 1.08 |
| No. of reflections | 1954 |
| No. of parameters | 154 |
| No. of restraints | 19 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.27, −0.21 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The derivatives of indole are important chemical materials, because they are excellent drug intermediates for many pharmaceutical products (Kunzer & Wendt, 2011). As part of our interest in these materials, we report here the crystal structure of the title compound C16H13N (Fig. 1).
This compound is essentially planar [maximum deviation from the least-squares plane 0.081 (3) Å (for C1)], with a dihedral angle of 1.65 (13)° between the planes of the indole and benzene ring systems. With the absence of no acceptor atoms in the molecule, no intermolecular hydrogen bonds are found in the crystal packing. Also, there are no significant intermolecular π–π interactions [minimum ring centroid separation, 4.217 (5) Å].