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access(E)-4-[4-(Dimethylamino)benzylideneamino]benzonitrile
aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China, and bJiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology, Nanjing Forestry University, Nanjing 210037, People's Republic of China
*Correspondence e-mail: jczhou@seu.edu.cn
The molecule of the title compound, C16H15N3, displays a trans configuration with respect to the C=N double bond. The molecule is not planar, the dihedral angle between the benzene rings being 57.83 (9)°. The crystal packing is stabilized only by van der Waals interactions.
Related literature
For the pharmacological activity of Schiff base compounds, see: Zhou et al. (2000![[Zhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol. Struct. 524, 241-250.]](../../../../../../logos/arrows/e_arr.gif "Zhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol. Struct. 524, 241-250.")
); Sriram et al. (2006). For reference structural data, see: Allen et al. (1987).
![[Scheme 1]](rz2389scheme1.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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536809047023/rz2389sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536809047023/rz2389Isup2.hkl
A solution of 4-(dimethylamino)benzaldehyde (0.596 g, 4 mmol) in ethanol (20 ml) was added to a solution of 4-aminobenzonitrile (0.472 g, 4 mmol) in methanol (20 ml), and the mixture stirred for 6 h under reflux. The resulting yellow precipitate was filtered off and crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
All the H atoms were located geometrically and treated as riding atoms with C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.
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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./rz2389fig1thm.gif) | Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. |
| C16H15N3 | F(000) = 528 |
| Mr = 249.31 | Dx = 1.236 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3347 reflections |
| a = 9.733 (6) Å | θ = 2.2–27.5° |
| b = 16.159 (9) Å | µ = 0.08 mm−1 |
| c = 9.103 (6) Å | T = 293 K |
| β = 110.644 (12)° | Block, yellow |
| V = 1339.8 (14) Å3 | 0.20 × 0.20 × 0.20 mm |
| Z = 4 |
| Rigaku SCXmini diffractometer | 2610 independent reflections |
| Radiation source: fine-focus sealed tube | 2134 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.043 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 2.2° |
| ω scans | h = −12→12 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −19→19 |
| Tmin = 0.985, Tmax = 0.985 | l = −11→11 |
| 13048 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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.221 | H-atom parameters constrained |
| S = 1.09 | w = 1/[σ2(Fo2) + (0.1227P)2 + 0.7975P] where P = (Fo2 + 2Fc2)/3 |
| 2610 reflections | (Δ/σ)max < 0.001 |
| 172 parameters | Δρmax = 0.53 e Å−3 |
| 0 restraints | Δρmin = −0.36 e Å−3 |
| C16H15N3 | V = 1339.8 (14) Å3 |
| Mr = 249.31 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.733 (6) Å | µ = 0.08 mm−1 |
| b = 16.159 (9) Å | T = 293 K |
| c = 9.103 (6) Å | 0.20 × 0.20 × 0.20 mm |
| β = 110.644 (12)° |
| Rigaku SCXmini diffractometer | 2610 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2134 reflections with I > 2σ(I) |
| Tmin = 0.985, Tmax = 0.985 | Rint = 0.043 |
| 13048 measured reflections |
| R[F2 > 2σ(F2)] = 0.070 | 0 restraints |
| wR(F2) = 0.221 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.53 e Å−3 |
| 2610 reflections | Δρmin = −0.36 e Å−3 |
| 172 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 | ||
| N2 | 0.9054 (2) | 0.11253 (12) | 0.0481 (2) | 0.0259 (5) | |
| N1 | 1.3132 (2) | 0.12345 (13) | 0.7796 (2) | 0.0266 (5) | |
| C4 | 1.2390 (3) | 0.13388 (14) | 0.6221 (3) | 0.0224 (5) | |
| C14 | 0.7447 (3) | 0.19677 (16) | −0.3581 (3) | 0.0279 (6) | |
| H14A | 0.7262 | 0.2472 | −0.4105 | 0.033* | |
| C15 | 0.8167 (3) | 0.19445 (15) | −0.1968 (3) | 0.0254 (5) | |
| H15A | 0.8479 | 0.2435 | −0.1415 | 0.030* | |
| C9 | 1.0202 (3) | 0.15527 (14) | 0.1238 (3) | 0.0246 (5) | |
| H9A | 1.0606 | 0.1897 | 0.0678 | 0.030* | |
| C10 | 0.8427 (2) | 0.11873 (14) | −0.1164 (3) | 0.0222 (5) | |
| C12 | 0.7285 (3) | 0.04706 (15) | −0.3620 (3) | 0.0278 (6) | |
| H12A | 0.7008 | −0.0022 | −0.4174 | 0.033* | |
| C11 | 0.7979 (3) | 0.04566 (15) | −0.2013 (3) | 0.0280 (6) | |
| H11A | 0.8151 | −0.0048 | −0.1487 | 0.034* | |
| C6 | 1.0225 (3) | 0.11201 (14) | 0.3895 (3) | 0.0247 (5) | |
| H6A | 0.9282 | 0.0907 | 0.3439 | 0.030* | |
| C16 | 0.6232 (3) | 0.12454 (17) | −0.6090 (3) | 0.0344 (6) | |
| C13 | 0.7000 (3) | 0.12305 (15) | −0.4417 (3) | 0.0264 (6) | |
| C5 | 1.0934 (3) | 0.10420 (15) | 0.5487 (3) | 0.0249 (5) | |
| H5A | 1.0456 | 0.0792 | 0.6092 | 0.030* | |
| C2 | 1.2299 (3) | 0.18366 (15) | 0.3669 (3) | 0.0260 (6) | |
| H2B | 1.2749 | 0.2115 | 0.3066 | 0.031* | |
| C3 | 1.3042 (3) | 0.17532 (15) | 0.5260 (3) | 0.0265 (6) | |
| H3A | 1.3983 | 0.1971 | 0.5708 | 0.032* | |
| C1 | 1.0889 (3) | 0.15156 (14) | 0.2934 (3) | 0.0235 (5) | |
| N3 | 0.5616 (3) | 0.12575 (18) | −0.7415 (3) | 0.0523 (8) | |
| C8 | 1.2478 (3) | 0.0794 (2) | 0.8776 (3) | 0.0427 (7) | |
| H8A | 1.1447 | 0.0721 | 0.8211 | 0.064* | |
| H8B | 1.2615 | 0.1108 | 0.9713 | 0.064* | |
| H8C | 1.2939 | 0.0263 | 0.9053 | 0.064* | |
| C7 | 1.4701 (3) | 0.14047 (19) | 0.8465 (3) | 0.0350 (6) | |
| H7A | 1.5001 | 0.1699 | 0.7713 | 0.052* | |
| H7B | 1.5231 | 0.0892 | 0.8729 | 0.052* | |
| H7C | 1.4904 | 0.1735 | 0.9395 | 0.052* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N2 | 0.0267 (10) | 0.0271 (10) | 0.0214 (10) | 0.0019 (8) | 0.0054 (9) | 0.0007 (8) |
| N1 | 0.0246 (11) | 0.0340 (12) | 0.0196 (10) | −0.0042 (8) | 0.0058 (8) | −0.0022 (8) |
| C4 | 0.0236 (12) | 0.0212 (11) | 0.0222 (11) | 0.0013 (9) | 0.0078 (9) | −0.0028 (9) |
| C14 | 0.0284 (13) | 0.0287 (13) | 0.0262 (13) | 0.0007 (10) | 0.0090 (10) | 0.0048 (10) |
| C15 | 0.0266 (12) | 0.0251 (12) | 0.0238 (12) | −0.0028 (9) | 0.0080 (10) | −0.0008 (9) |
| C9 | 0.0244 (12) | 0.0227 (12) | 0.0263 (12) | 0.0026 (9) | 0.0084 (10) | 0.0023 (9) |
| C10 | 0.0184 (11) | 0.0278 (12) | 0.0203 (11) | 0.0004 (9) | 0.0067 (9) | 0.0014 (9) |
| C12 | 0.0284 (13) | 0.0276 (13) | 0.0268 (13) | 0.0012 (10) | 0.0091 (10) | −0.0042 (10) |
| C11 | 0.0308 (13) | 0.0245 (12) | 0.0275 (13) | 0.0066 (10) | 0.0087 (10) | 0.0037 (9) |
| C6 | 0.0199 (11) | 0.0263 (12) | 0.0269 (12) | −0.0012 (9) | 0.0071 (10) | −0.0025 (9) |
| C16 | 0.0346 (14) | 0.0389 (15) | 0.0283 (15) | 0.0001 (11) | 0.0093 (12) | −0.0003 (11) |
| C13 | 0.0234 (12) | 0.0340 (14) | 0.0220 (12) | 0.0031 (10) | 0.0083 (10) | 0.0018 (9) |
| C5 | 0.0251 (12) | 0.0266 (12) | 0.0246 (12) | −0.0018 (9) | 0.0109 (10) | −0.0020 (9) |
| C2 | 0.0261 (12) | 0.0252 (12) | 0.0276 (12) | −0.0024 (10) | 0.0103 (10) | 0.0031 (9) |
| C3 | 0.0232 (12) | 0.0279 (12) | 0.0258 (12) | −0.0052 (9) | 0.0055 (10) | −0.0016 (9) |
| C1 | 0.0244 (12) | 0.0211 (11) | 0.0237 (12) | 0.0017 (9) | 0.0066 (10) | −0.0011 (9) |
| N3 | 0.0589 (18) | 0.0662 (19) | 0.0246 (13) | −0.0025 (14) | 0.0058 (12) | −0.0003 (11) |
| C8 | 0.0412 (16) | 0.063 (2) | 0.0232 (13) | −0.0160 (14) | 0.0105 (12) | 0.0014 (12) |
| C7 | 0.0250 (13) | 0.0527 (17) | 0.0237 (12) | −0.0017 (11) | 0.0042 (10) | −0.0014 (11) |
| N2—C9 | 1.288 (3) | C11—H11A | 0.9300 |
| N2—C10 | 1.408 (3) | C6—C5 | 1.374 (3) |
| N1—C4 | 1.370 (3) | C6—C1 | 1.411 (3) |
| N1—C8 | 1.452 (3) | C6—H6A | 0.9300 |
| N1—C7 | 1.457 (3) | C16—N3 | 1.143 (4) |
| C4—C3 | 1.417 (3) | C16—C13 | 1.441 (3) |
| C4—C5 | 1.420 (3) | C5—H5A | 0.9300 |
| C14—C15 | 1.387 (3) | C2—C3 | 1.379 (3) |
| C14—C13 | 1.398 (4) | C2—C1 | 1.397 (3) |
| C14—H14A | 0.9300 | C2—H2B | 0.9300 |
| C15—C10 | 1.402 (3) | C3—H3A | 0.9300 |
| C15—H15A | 0.9300 | C8—H8A | 0.9600 |
| C9—C1 | 1.451 (3) | C8—H8B | 0.9600 |
| C9—H9A | 0.9300 | C8—H8C | 0.9600 |
| C10—C11 | 1.394 (3) | C7—H7A | 0.9600 |
| C12—C11 | 1.378 (3) | C7—H7B | 0.9600 |
| C12—C13 | 1.403 (3) | C7—H7C | 0.9600 |
| C12—H12A | 0.9300 | ||
| C9—N2—C10 | 120.0 (2) | N3—C16—C13 | 179.6 (3) |
| C4—N1—C8 | 121.3 (2) | C14—C13—C12 | 119.8 (2) |
| C4—N1—C7 | 120.2 (2) | C14—C13—C16 | 120.5 (2) |
| C8—N1—C7 | 117.2 (2) | C12—C13—C16 | 119.7 (2) |
| N1—C4—C3 | 121.3 (2) | C6—C5—C4 | 120.8 (2) |
| N1—C4—C5 | 121.4 (2) | C6—C5—H5A | 119.6 |
| C3—C4—C5 | 117.3 (2) | C4—C5—H5A | 119.6 |
| C15—C14—C13 | 119.8 (2) | C3—C2—C1 | 122.0 (2) |
| C15—C14—H14A | 120.1 | C3—C2—H2B | 119.0 |
| C13—C14—H14A | 120.1 | C1—C2—H2B | 119.0 |
| C14—C15—C10 | 120.4 (2) | C2—C3—C4 | 120.7 (2) |
| C14—C15—H15A | 119.8 | C2—C3—H3A | 119.6 |
| C10—C15—H15A | 119.8 | C4—C3—H3A | 119.6 |
| N2—C9—C1 | 122.3 (2) | C2—C1—C6 | 117.3 (2) |
| N2—C9—H9A | 118.9 | C2—C1—C9 | 120.0 (2) |
| C1—C9—H9A | 118.9 | C6—C1—C9 | 122.6 (2) |
| C11—C10—C15 | 119.1 (2) | N1—C8—H8A | 109.5 |
| C11—C10—N2 | 117.6 (2) | N1—C8—H8B | 109.5 |
| C15—C10—N2 | 123.2 (2) | H8A—C8—H8B | 109.5 |
| C11—C12—C13 | 119.8 (2) | N1—C8—H8C | 109.5 |
| C11—C12—H12A | 120.1 | H8A—C8—H8C | 109.5 |
| C13—C12—H12A | 120.1 | H8B—C8—H8C | 109.5 |
| C12—C11—C10 | 121.0 (2) | N1—C7—H7A | 109.5 |
| C12—C11—H11A | 119.5 | N1—C7—H7B | 109.5 |
| C10—C11—H11A | 119.5 | H7A—C7—H7B | 109.5 |
| C5—C6—C1 | 121.7 (2) | N1—C7—H7C | 109.5 |
| C5—C6—H6A | 119.1 | H7A—C7—H7C | 109.5 |
| C1—C6—H6A | 119.1 | H7B—C7—H7C | 109.5 |
Experimental details
| Crystal data | |
| Chemical formula | C16H15N3 |
| Mr | 249.31 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 293 |
| a, b, c (Å) | 9.733 (6), 16.159 (9), 9.103 (6) |
| β (°) | 110.644 (12) |
| V (Å3) | 1339.8 (14) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.08 |
| Crystal size (mm) | 0.20 × 0.20 × 0.20 |
| Data collection | |
| Diffractometer | Rigaku SCXmini diffractometer |
| Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
| Tmin, Tmax | 0.985, 0.985 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 13048, 2610, 2134 |
| Rint | 0.043 |
| (sin θ/λ)max (Å−1) | 0.617 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.221, 1.09 |
| No. of reflections | 2610 |
| No. of parameters | 172 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.53, −0.36 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported financially by the Jiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology (fund No. 200813).
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
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
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129. Web of Science CrossRef PubMed CAS Google Scholar
Zhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol. Struct. 524, 241–250. Web of Science CSD CrossRef Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Schiff bases compounds are of great interest in many fields of chemistry and biochemistry, primarily due to significant pharmacological activities, e. g. anticancer (Zhou et al., 2000) and anti-HIV (Sriram et al., 2006) activities. In addition, Schiff base compounds play an important role in the development of coordination chemistry related to magnetism and catalysis. Here, we report the synthesis and crystal structure of the title compound.
The molecular structure of the the title compound is shown in Fig. 1. All bond lengths (Allen et al., 1987) and angles in the molecule are normal. The N=C bond distance is 1.288 (3) Å. The structure displays a trans configuration about the central C9=N2 double bond. The molecule is not planar, as indicated by the dihedral angle between the two benzene rings of 57.83 (9)°. The crystal packing is stabilized only by van der Waals interactions.