Acta Cryst. (2009). E65, o945 [ doi:10.1107/S1600536809011568 ]
The molecule of the title Schiff base, C16H15N3, is non-planar and displays a trans configuration with respect to the C=N double bond. The two benzene rings make a dihedral angle of 49.24 (3)°.
All chemicals were obtained from commercial sources and directly used without further purification. 3-aminobenzonitrile (1.18 g, 10 mmol) and 4-(dimethylamino)benzaldehyde (1.49 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 6 h, then cooled to room temperature overnight and large amounts of a yellow precipitate were formed. Yellow crystals were obtained by recrystallization from ethanol(yield:2.04,82%). 1H-NMR(CDCl3, 300 MHz): δ3.10 (s, 6 H), 6.73–6.76(d, 2 H), 7.45–7.50 (m, 4 H), 7.84–7.87 (d, 2 H), 8.27 (s, 1 H). Esi-MS: calcd for C16H15N3 m/z 249.31, found 250.18[M+1]. For the X-ray diffraction analysis, suitable single crystals of compound (I) were obtained after two weeks by slow evaporation from an ethanol solution.
All H atoms attached to C were positioned geometrically and treated as riding, with C—H = 0.93 (aromatic), 0.93 (methine) or 0.96 Å (methyl) with Uiso(H) = 1.2Ueq(C).
Data collection: SMART(Bruker, 2000); cell refinement: SAINT(Bruker, 2000); data reduction: SAINT(Bruker, 2000); 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]](./dn2436fig1thm.gif)
| Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| C16H15N3 | F(000) = 528 |
| Mr = 249.31 | Dx = 1.267 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2559 reflections |
| a = 6.0924 (6) Å | θ = 2.8–26.0° |
| b = 29.127 (3) Å | µ = 0.08 mm−1 |
| c = 7.3768 (7) Å | T = 293 K |
| β = 92.924 (1)° | Block, yellow |
| V = 1307.3 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2559 independent reflections |
| Radiation source: fine-focus sealed tube | 2241 reflections with I > 2σ(I) |
| graphite | Rint = 0.064 |
| φ and ω scans | θmax = 26.0°, θmin = 2.8° |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | h = −7→7 |
| Tmin = 0.961, Tmax = 1.000 | k = −35→25 |
| 7018 measured reflections | l = −9→8 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.110 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1755P] where P = (Fo2 + 2Fc2)/3 |
| 2559 reflections | (Δ/σ)max < 0.001 |
| 174 parameters | Δρmax = 0.19 e Å−3 |
| 0 restraints | Δρmin = −0.25 e Å−3 |
| C16H15N3 | V = 1307.3 (2) Å3 |
| Mr = 249.31 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 6.0924 (6) Å | µ = 0.08 mm−1 |
| b = 29.127 (3) Å | T = 293 K |
| c = 7.3768 (7) Å | 0.30 × 0.20 × 0.20 mm |
| β = 92.924 (1)° |
| Bruker SMART CCD area-detector diffractometer | 2559 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2241 reflections with I > 2σ(I) |
| Tmin = 0.961, Tmax = 1.000 | Rint = 0.064 |
| 7018 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.110 | Δρmax = 0.19 e Å−3 |
| S = 1.05 | Δρmin = −0.25 e Å−3 |
| 2559 reflections | Absolute structure: ? |
| 174 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| N1 | 0.61108 (15) | 0.27979 (3) | 0.59956 (13) | 0.0190 (2) | |
| N2 | 0.28428 (16) | 0.47022 (3) | 0.70360 (14) | 0.0263 (3) | |
| N3 | 0.14557 (15) | 0.08098 (3) | 0.61116 (13) | 0.0189 (2) | |
| C1 | 0.65373 (17) | 0.32723 (4) | 0.58571 (14) | 0.0171 (2) | |
| C2 | 0.50894 (17) | 0.36071 (4) | 0.64200 (14) | 0.0169 (2) | |
| H2A | 0.3790 | 0.3523 | 0.6941 | 0.020* | |
| C3 | 0.56051 (17) | 0.40708 (4) | 0.61955 (14) | 0.0175 (3) | |
| C4 | 0.75672 (18) | 0.42049 (4) | 0.54437 (14) | 0.0190 (3) | |
| H4A | 0.7889 | 0.4514 | 0.5285 | 0.023* | |
| C5 | 0.90207 (18) | 0.38678 (4) | 0.49403 (15) | 0.0207 (3) | |
| H5A | 1.0341 | 0.3951 | 0.4452 | 0.025* | |
| C6 | 0.85265 (17) | 0.34081 (4) | 0.51572 (15) | 0.0197 (3) | |
| H6A | 0.9532 | 0.3186 | 0.4833 | 0.024* | |
| C7 | 0.40682 (18) | 0.44200 (4) | 0.66975 (15) | 0.0198 (3) | |
| C8 | 0.42252 (17) | 0.26531 (4) | 0.53867 (14) | 0.0174 (3) | |
| H8A | 0.3245 | 0.2863 | 0.4847 | 0.021* | |
| C9 | 0.35526 (17) | 0.21769 (4) | 0.55017 (14) | 0.0171 (3) | |
| C10 | 0.14627 (17) | 0.20363 (4) | 0.48467 (15) | 0.0188 (3) | |
| H10A | 0.0515 | 0.2251 | 0.4298 | 0.023* | |
| C11 | 0.07713 (17) | 0.15861 (4) | 0.49941 (15) | 0.0187 (3) | |
| H11A | −0.0617 | 0.1502 | 0.4526 | 0.022* | |
| C12 | 0.21502 (17) | 0.12527 (4) | 0.58471 (14) | 0.0162 (2) | |
| C13 | 0.42785 (17) | 0.13953 (4) | 0.64815 (14) | 0.0176 (3) | |
| H13A | 0.5238 | 0.1182 | 0.7028 | 0.021* | |
| C14 | 0.49460 (17) | 0.18430 (4) | 0.63022 (14) | 0.0175 (2) | |
| H14A | 0.6355 | 0.1926 | 0.6722 | 0.021* | |
| C15 | 0.30017 (19) | 0.04552 (4) | 0.67163 (16) | 0.0229 (3) | |
| H15A | 0.3783 | 0.0553 | 0.7812 | 0.034* | |
| H15B | 0.4027 | 0.0401 | 0.5793 | 0.034* | |
| H15C | 0.2218 | 0.0177 | 0.6943 | 0.034* | |
| C16 | −0.06638 (18) | 0.06583 (4) | 0.53393 (16) | 0.0222 (3) | |
| H16A | −0.1766 | 0.0881 | 0.5599 | 0.033* | |
| H16B | −0.1035 | 0.0368 | 0.5860 | 0.033* | |
| H16C | −0.0590 | 0.0626 | 0.4049 | 0.033* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0189 (5) | 0.0166 (5) | 0.0216 (5) | 0.0000 (4) | 0.0009 (4) | 0.0003 (4) |
| N2 | 0.0295 (5) | 0.0194 (5) | 0.0304 (6) | −0.0017 (4) | 0.0058 (4) | −0.0035 (4) |
| N3 | 0.0188 (5) | 0.0154 (5) | 0.0224 (5) | −0.0007 (4) | 0.0011 (4) | 0.0008 (4) |
| C1 | 0.0179 (5) | 0.0166 (5) | 0.0162 (5) | −0.0016 (4) | −0.0034 (4) | 0.0017 (4) |
| C2 | 0.0150 (5) | 0.0187 (6) | 0.0170 (5) | −0.0024 (4) | 0.0005 (4) | 0.0002 (4) |
| C3 | 0.0190 (5) | 0.0182 (6) | 0.0151 (5) | −0.0014 (4) | −0.0010 (4) | −0.0016 (4) |
| C4 | 0.0211 (5) | 0.0184 (6) | 0.0172 (5) | −0.0060 (4) | −0.0022 (4) | 0.0005 (4) |
| C5 | 0.0161 (5) | 0.0262 (6) | 0.0196 (6) | −0.0049 (5) | 0.0002 (4) | 0.0005 (5) |
| C6 | 0.0149 (5) | 0.0231 (6) | 0.0209 (5) | 0.0023 (4) | −0.0010 (4) | −0.0014 (4) |
| C7 | 0.0225 (6) | 0.0170 (6) | 0.0199 (5) | −0.0056 (5) | 0.0009 (4) | −0.0009 (4) |
| C8 | 0.0165 (5) | 0.0171 (6) | 0.0187 (5) | 0.0033 (4) | 0.0027 (4) | 0.0015 (4) |
| C9 | 0.0171 (5) | 0.0170 (5) | 0.0174 (6) | 0.0012 (4) | 0.0039 (4) | 0.0001 (4) |
| C10 | 0.0164 (5) | 0.0180 (6) | 0.0221 (6) | 0.0042 (4) | 0.0013 (4) | 0.0018 (4) |
| C11 | 0.0147 (5) | 0.0196 (6) | 0.0219 (6) | −0.0004 (4) | 0.0014 (4) | −0.0001 (4) |
| C12 | 0.0181 (5) | 0.0162 (5) | 0.0148 (5) | 0.0015 (4) | 0.0046 (4) | −0.0003 (4) |
| C13 | 0.0186 (5) | 0.0176 (5) | 0.0167 (5) | 0.0041 (4) | 0.0013 (4) | 0.0013 (4) |
| C14 | 0.0162 (5) | 0.0189 (5) | 0.0175 (5) | 0.0008 (4) | 0.0012 (4) | −0.0007 (4) |
| C15 | 0.0292 (6) | 0.0158 (6) | 0.0233 (6) | 0.0000 (5) | −0.0039 (5) | 0.0009 (4) |
| C16 | 0.0198 (6) | 0.0184 (6) | 0.0285 (6) | −0.0020 (4) | 0.0035 (5) | −0.0007 (5) |
| N1—C8 | 1.2833 (14) | C8—H8A | 0.9300 |
| N1—C1 | 1.4105 (14) | C9—C10 | 1.3998 (15) |
| N2—C7 | 1.1466 (15) | C9—C14 | 1.4013 (15) |
| N3—C12 | 1.3746 (14) | C10—C11 | 1.3834 (16) |
| N3—C15 | 1.4526 (14) | C10—H10A | 0.9300 |
| N3—C16 | 1.4531 (14) | C11—C12 | 1.4109 (15) |
| C1—C2 | 1.3924 (15) | C11—H11A | 0.9300 |
| C1—C6 | 1.3984 (15) | C12—C13 | 1.4181 (15) |
| C2—C3 | 1.3986 (15) | C13—C14 | 1.3743 (15) |
| C2—H2A | 0.9300 | C13—H13A | 0.9300 |
| C3—C4 | 1.3988 (15) | C14—H14A | 0.9300 |
| C3—C7 | 1.4434 (16) | C15—H15A | 0.9600 |
| C4—C5 | 1.3854 (16) | C15—H15B | 0.9600 |
| C4—H4A | 0.9300 | C15—H15C | 0.9600 |
| C5—C6 | 1.3836 (16) | C16—H16A | 0.9600 |
| C5—H5A | 0.9300 | C16—H16B | 0.9600 |
| C6—H6A | 0.9300 | C16—H16C | 0.9600 |
| C8—C9 | 1.4501 (15) | ||
| C8—N1—C1 | 117.49 (9) | C14—C9—C8 | 121.43 (10) |
| C12—N3—C15 | 120.76 (9) | C11—C10—C9 | 121.69 (10) |
| C12—N3—C16 | 120.20 (9) | C11—C10—H10A | 119.2 |
| C15—N3—C16 | 116.99 (9) | C9—C10—H10A | 119.2 |
| C2—C1—C6 | 119.09 (10) | C10—C11—C12 | 120.71 (10) |
| C2—C1—N1 | 122.86 (10) | C10—C11—H11A | 119.6 |
| C6—C1—N1 | 118.04 (10) | C12—C11—H11A | 119.6 |
| C1—C2—C3 | 119.44 (10) | N3—C12—C11 | 121.91 (9) |
| C1—C2—H2A | 120.3 | N3—C12—C13 | 120.73 (10) |
| C3—C2—H2A | 120.3 | C11—C12—C13 | 117.33 (10) |
| C2—C3—C4 | 121.21 (10) | C14—C13—C12 | 121.08 (10) |
| C2—C3—C7 | 119.83 (10) | C14—C13—H13A | 119.5 |
| C4—C3—C7 | 118.94 (10) | C12—C13—H13A | 119.5 |
| C5—C4—C3 | 118.64 (10) | C13—C14—C9 | 121.54 (10) |
| C5—C4—H4A | 120.7 | C13—C14—H14A | 119.2 |
| C3—C4—H4A | 120.7 | C9—C14—H14A | 119.2 |
| C6—C5—C4 | 120.59 (10) | N3—C15—H15A | 109.5 |
| C6—C5—H5A | 119.7 | N3—C15—H15B | 109.5 |
| C4—C5—H5A | 119.7 | H15A—C15—H15B | 109.5 |
| C5—C6—C1 | 120.95 (10) | N3—C15—H15C | 109.5 |
| C5—C6—H6A | 119.5 | H15A—C15—H15C | 109.5 |
| C1—C6—H6A | 119.5 | H15B—C15—H15C | 109.5 |
| N2—C7—C3 | 177.67 (13) | N3—C16—H16A | 109.5 |
| N1—C8—C9 | 123.00 (10) | N3—C16—H16B | 109.5 |
| N1—C8—H8A | 118.5 | H16A—C16—H16B | 109.5 |
| C9—C8—H8A | 118.5 | N3—C16—H16C | 109.5 |
| C10—C9—C14 | 117.61 (10) | H16A—C16—H16C | 109.5 |
| C10—C9—C8 | 120.95 (10) | H16B—C16—H16C | 109.5 |
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69.
Gong, X.-X. & Xu, H.-J. (2008). Acta Cryst. E64, o1188.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Schiff base compounds have attracted great attention and been extensively investigated in terms of their crystallography and coordination chemistry (Garnovskii et al., 1993). As a continuation of our studies on Schiff-base compounds, we here report the synthesis and crystal structure of the title compound (I).
The molecule displays a trans configuration with respect to the C=N double bond (Fig. 1). The values of the C—C, C=C, C—N and C=N bond distances in (I) are similar to the corresponding bond lengths in 4-(2-Hydroxybenzylideneamino)benzonitrile(Gong & Xu, 2008). The molecule is nonplanar and the dihedral angle between the planes of the two benzene rings is 49.24 (0.03) °.