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access2-(4-Methylphenyl)benzonitrile
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C14H11N, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7)°. The crystal packing is stabilized by weak intermolecular π–π stacking interactions, the centroid–centroid distances being 3.8172 (12) and 3.9349 (12) Å.
Related literature
For the synthesis of pharmaceutically active compounds, see: Gillis & Markham (1997![[Gillis, J. C. & Markham, A. (1997). Drugs, 54, 885-902.]](../../../../../../logos/arrows/e_arr.gif "Gillis, J. C. & Markham, A. (1997). Drugs, 54, 885-902.")
); Markham & Goa (1997). For related structures, see: Gerkin (1998); Narasegowda et al. (2005); Yathirajan et al. (2005). For standard bond lengths, see Allen et al. (1987).
![[Scheme 1]](xu5222scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
contains datablocks global, I. DOI: 10.1107/S160053681101988X/xu5222sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S160053681101988X/xu5222Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681101988X/xu5222Isup3.cml
The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of methanol solution (m.p.: 323-325 K).
All of the H atoms were placed in their calculated positions and then refined using the riding model with C—H = 0.95 Å (aromatic) or 0.98 Å (CH3). Isotropic displacement parameters for these atoms were set to 1.19-1.21 (aromatic) or 1.50 (CH3) times Ueq of the parent atom.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./xu5222fig1thm.gif) | Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids. |
![[Figure 2]](./xu5222fig2thm.gif) | Fig. 2. Packing diagram of the title compound viewed down the a axis. |
| C14H11N | F(000) = 408 |
| Mr = 193.24 | Dx = 1.198 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 2201 reflections |
| a = 7.6726 (4) Å | θ = 3.3–32.3° |
| b = 11.4037 (5) Å | µ = 0.07 mm−1 |
| c = 12.2426 (5) Å | T = 173 K |
| V = 1071.18 (9) Å3 | Block, colorless |
| Z = 4 | 0.30 × 0.25 × 0.20 mm |
| Oxford Diffraction Xcalibur Eos Gemini diffractometer | 1546 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 1322 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.017 |
| Detector resolution: 16.1500 pixels mm-1 | θmax = 28.3°, θmin = 3.3° |
| ω scans | h = −10→10 |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −7→15 |
| Tmin = 0.979, Tmax = 0.986 | l = −16→16 |
| 3786 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1272P] where P = (Fo2 + 2Fc2)/3 |
| 1546 reflections | (Δ/σ)max = 0.008 |
| 137 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.14 e Å−3 |
| C14H11N | V = 1071.18 (9) Å3 |
| Mr = 193.24 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 7.6726 (4) Å | µ = 0.07 mm−1 |
| b = 11.4037 (5) Å | T = 173 K |
| c = 12.2426 (5) Å | 0.30 × 0.25 × 0.20 mm |
| Oxford Diffraction Xcalibur Eos Gemini diffractometer | 1546 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 1322 reflections with I > 2σ(I) |
| Tmin = 0.979, Tmax = 0.986 | Rint = 0.017 |
| 3786 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.22 e Å−3 |
| 1546 reflections | Δρmin = −0.14 e Å−3 |
| 137 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| N1 | 0.2954 (3) | 0.53397 (15) | 0.51932 (16) | 0.0599 (5) | |
| C1 | 0.2409 (3) | 0.45620 (16) | 0.56640 (15) | 0.0403 (4) | |
| C2 | 0.1730 (2) | 0.36058 (15) | 0.62994 (15) | 0.0350 (4) | |
| C3 | 0.1706 (3) | 0.37476 (16) | 0.74343 (15) | 0.0413 (4) | |
| H3A | 0.2117 | 0.4456 | 0.7751 | 0.050* | |
| C4 | 0.1091 (3) | 0.28649 (19) | 0.80918 (16) | 0.0484 (5) | |
| H4A | 0.1060 | 0.2963 | 0.8862 | 0.058* | |
| C5 | 0.0518 (3) | 0.1835 (2) | 0.76255 (16) | 0.0498 (5) | |
| H5A | 0.0090 | 0.1223 | 0.8079 | 0.060* | |
| C6 | 0.0559 (3) | 0.16831 (18) | 0.65050 (16) | 0.0427 (5) | |
| H6A | 0.0171 | 0.0962 | 0.6202 | 0.051* | |
| C7 | 0.1155 (2) | 0.25620 (15) | 0.58127 (13) | 0.0331 (4) | |
| C8 | 0.1185 (2) | 0.23705 (15) | 0.46123 (13) | 0.0333 (4) | |
| C9 | 0.1780 (3) | 0.13095 (16) | 0.41890 (16) | 0.0412 (4) | |
| H9A | 0.2178 | 0.0715 | 0.4672 | 0.049* | |
| C10 | 0.1798 (3) | 0.11109 (17) | 0.30733 (16) | 0.0459 (5) | |
| H10A | 0.2211 | 0.0381 | 0.2804 | 0.055* | |
| C11 | 0.1230 (3) | 0.19495 (18) | 0.23447 (15) | 0.0441 (5) | |
| C12 | 0.0627 (3) | 0.30048 (18) | 0.27609 (16) | 0.0432 (5) | |
| H12A | 0.0224 | 0.3595 | 0.2275 | 0.052* | |
| C13 | 0.0604 (2) | 0.32112 (16) | 0.38739 (15) | 0.0383 (4) | |
| H13A | 0.0183 | 0.3941 | 0.4139 | 0.046* | |
| C14 | 0.1238 (4) | 0.1727 (2) | 0.11270 (17) | 0.0671 (7) | |
| H14A | 0.1788 | 0.2391 | 0.0753 | 0.101* | |
| H14B | 0.0038 | 0.1637 | 0.0867 | 0.101* | |
| H14C | 0.1895 | 0.1009 | 0.0972 | 0.101* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0834 (14) | 0.0413 (9) | 0.0550 (10) | −0.0116 (10) | 0.0026 (11) | 0.0037 (8) |
| C1 | 0.0460 (10) | 0.0356 (8) | 0.0393 (9) | 0.0018 (9) | −0.0010 (9) | −0.0051 (8) |
| C2 | 0.0344 (9) | 0.0356 (8) | 0.0349 (8) | 0.0027 (8) | 0.0011 (7) | 0.0004 (7) |
| C3 | 0.0423 (10) | 0.0424 (9) | 0.0391 (10) | 0.0009 (9) | −0.0028 (8) | −0.0043 (8) |
| C4 | 0.0542 (12) | 0.0583 (12) | 0.0328 (8) | −0.0027 (11) | 0.0002 (9) | 0.0020 (9) |
| C5 | 0.0559 (12) | 0.0539 (11) | 0.0395 (9) | −0.0100 (11) | 0.0019 (9) | 0.0107 (9) |
| C6 | 0.0454 (10) | 0.0414 (9) | 0.0414 (10) | −0.0099 (9) | −0.0005 (8) | 0.0031 (8) |
| C7 | 0.0298 (8) | 0.0367 (8) | 0.0329 (8) | 0.0023 (8) | −0.0003 (7) | 0.0009 (7) |
| C8 | 0.0303 (8) | 0.0358 (8) | 0.0337 (8) | −0.0045 (7) | −0.0004 (7) | 0.0000 (7) |
| C9 | 0.0448 (10) | 0.0347 (9) | 0.0441 (10) | −0.0005 (8) | −0.0020 (9) | 0.0007 (8) |
| C10 | 0.0526 (11) | 0.0380 (9) | 0.0472 (11) | −0.0031 (9) | 0.0032 (10) | −0.0092 (8) |
| C11 | 0.0489 (11) | 0.0468 (10) | 0.0366 (8) | −0.0151 (10) | 0.0036 (9) | −0.0039 (8) |
| C12 | 0.0477 (11) | 0.0449 (10) | 0.0370 (8) | −0.0057 (9) | −0.0049 (8) | 0.0056 (8) |
| C13 | 0.0391 (9) | 0.0359 (8) | 0.0397 (9) | 0.0017 (8) | −0.0019 (8) | −0.0009 (8) |
| C14 | 0.0991 (19) | 0.0644 (13) | 0.0378 (10) | −0.0186 (16) | 0.0036 (13) | −0.0095 (11) |
| N1—C1 | 1.137 (2) | C8—C9 | 1.393 (2) |
| C1—C2 | 1.437 (2) | C9—C10 | 1.385 (3) |
| C2—C3 | 1.399 (2) | C9—H9A | 0.9500 |
| C2—C7 | 1.402 (2) | C10—C11 | 1.378 (3) |
| C3—C4 | 1.373 (3) | C10—H10A | 0.9500 |
| C3—H3A | 0.9500 | C11—C12 | 1.386 (3) |
| C4—C5 | 1.378 (3) | C11—C14 | 1.512 (3) |
| C4—H4A | 0.9500 | C12—C13 | 1.383 (3) |
| C5—C6 | 1.383 (3) | C12—H12A | 0.9500 |
| C5—H5A | 0.9500 | C13—H13A | 0.9500 |
| C6—C7 | 1.390 (2) | C14—H14A | 0.9800 |
| C6—H6A | 0.9500 | C14—H14B | 0.9800 |
| C7—C8 | 1.486 (2) | C14—H14C | 0.9800 |
| C8—C13 | 1.391 (2) | ||
| N1—C1—C2 | 177.67 (19) | C10—C9—C8 | 120.81 (17) |
| C3—C2—C7 | 121.07 (17) | C10—C9—H9A | 119.6 |
| C3—C2—C1 | 117.04 (16) | C8—C9—H9A | 119.6 |
| C7—C2—C1 | 121.87 (15) | C11—C10—C9 | 121.45 (18) |
| C4—C3—C2 | 120.14 (18) | C11—C10—H10A | 119.3 |
| C4—C3—H3A | 119.9 | C9—C10—H10A | 119.3 |
| C2—C3—H3A | 119.9 | C10—C11—C12 | 118.03 (17) |
| C3—C4—C5 | 119.46 (17) | C10—C11—C14 | 121.3 (2) |
| C3—C4—H4A | 120.3 | C12—C11—C14 | 120.6 (2) |
| C5—C4—H4A | 120.3 | C13—C12—C11 | 120.95 (18) |
| C4—C5—C6 | 120.7 (2) | C13—C12—H12A | 119.5 |
| C4—C5—H5A | 119.6 | C11—C12—H12A | 119.5 |
| C6—C5—H5A | 119.6 | C12—C13—C8 | 121.25 (17) |
| C5—C6—C7 | 121.45 (19) | C12—C13—H13A | 119.4 |
| C5—C6—H6A | 119.3 | C8—C13—H13A | 119.4 |
| C7—C6—H6A | 119.3 | C11—C14—H14A | 109.5 |
| C6—C7—C2 | 117.15 (15) | C11—C14—H14B | 109.5 |
| C6—C7—C8 | 120.14 (16) | H14A—C14—H14B | 109.5 |
| C2—C7—C8 | 122.70 (15) | C11—C14—H14C | 109.5 |
| C13—C8—C9 | 117.51 (16) | H14A—C14—H14C | 109.5 |
| C13—C8—C7 | 122.45 (16) | H14B—C14—H14C | 109.5 |
| C9—C8—C7 | 120.03 (16) | ||
| C7—C2—C3—C4 | −1.0 (3) | C6—C7—C8—C9 | −43.5 (2) |
| C1—C2—C3—C4 | −179.36 (18) | C2—C7—C8—C9 | 135.8 (2) |
| C2—C3—C4—C5 | 0.8 (3) | C13—C8—C9—C10 | 0.4 (3) |
| C3—C4—C5—C6 | 0.1 (3) | C7—C8—C9—C10 | 179.27 (18) |
| C4—C5—C6—C7 | −0.8 (3) | C8—C9—C10—C11 | −0.1 (3) |
| C5—C6—C7—C2 | 0.6 (3) | C9—C10—C11—C12 | −0.3 (3) |
| C5—C6—C7—C8 | 179.9 (2) | C9—C10—C11—C14 | −179.5 (2) |
| C3—C2—C7—C6 | 0.3 (3) | C10—C11—C12—C13 | 0.3 (3) |
| C1—C2—C7—C6 | 178.58 (18) | C14—C11—C12—C13 | 179.5 (2) |
| C3—C2—C7—C8 | −179.05 (18) | C11—C12—C13—C8 | 0.1 (3) |
| C1—C2—C7—C8 | −0.7 (3) | C9—C8—C13—C12 | −0.5 (3) |
| C6—C7—C8—C13 | 135.2 (2) | C7—C8—C13—C12 | −179.24 (17) |
| C2—C7—C8—C13 | −45.5 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C14H11N |
| Mr | 193.24 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 173 |
| a, b, c (Å) | 7.6726 (4), 11.4037 (5), 12.2426 (5) |
| V (Å3) | 1071.18 (9) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.07 |
| Crystal size (mm) | 0.30 × 0.25 × 0.20 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur Eos Gemini diffractometer |
| Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2010) |
| Tmin, Tmax | 0.979, 0.986 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3786, 1546, 1322 |
| Rint | 0.017 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.105, 1.07 |
| No. of reflections | 1546 |
| No. of parameters | 137 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.22, −0.14 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
| CgI···CgJ | Cg···Cg (Å) | CgI Perp (Å) | Cgj Perp (Å) |
| Cg1···Cg2i | 3.8172 (12) | 3.5763 (8) | -3.5789 (8) |
| Cg2···Cg1ii | 3.9349 (12) | -3.5230 (8) | 3.5154 (8) |
Acknowledgements
MSS thanks the University of Mysore for the research facilities and R. L. Fine Chem, Bangalore, India, for the gift of the sample. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Gerkin, R. E. (1998). Acta Cryst. C54, 1887–1889. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gillis, J. C. & Markham, A. (1997). Drugs, 54, 885–902. CrossRef CAS PubMed Web of Science Google Scholar
Markham, A. & Goa, K. L. (1997). Drugs, 54, 299–311. CrossRef CAS PubMed Web of Science Google Scholar
Narasegowda, R. S., Yathirajan, H. S. & Bolte, M. (2005). Acta Cryst. E61, o939–o940. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yathirajan, H. S., Nagaraj, B., Narasegowda, R. S., Nagaraja, P. & Bolte, M. (2005). Acta Cryst. E61, o1193–o1195. Web of Science CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound, C14H11N, (I), is used to synthesize various biologically active and pharmaceutical compounds viz., losartan, valsartan, candesartan, etc. (Gillis & Markham, 1997; Markham & Goa, 1997). The crystal structures of 4,4'-dimethylbiphenyl-2,2'-dicarboxylic acid (Gerkin, 1998), 4'-methylbiphenyl-2-carboxylic acid (Narasegowda et al., 2005) and 4'-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)biphenyl-2-carbonitrile (Yathirajan et al., 2005) have been reported. In view of its importance in order to determine the conformation of this molecule, a crystal structure determination of (I) is reported.
In the title compound, C14H11N,, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7)° (Fig. 1). Bond lengths and angles are in normal positions (Allen et al., 1987). Crystal packing is stabilized by weak π-π stacking interactions (Fig. 2, Table 1).