organic compounds
(E)-2-Methyl-N-[4-(methylsulfonyl)benzylidene]aniline
aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China, and bSchool of Chemical Engineering, ShanDong University of Technology, ZiBo 255049, People's Republic of China
*Correspondence e-mail: njuqss@yahoo.com.cn
Molecules of the title compound, C15H15NO2S, display an E configuration with respect to the C=N double bond. The is stabilized by weak C—H⋯O hydrogen bonds. The dihedral angle between the two aromatic ring planes is 50.41 (12)°.
Related literature
For background to Schiff base compounds in coordination chemistry, see: Shao et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: CAD-4 Software; 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
10.1107/S1600536809047199/fj2256sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047199/fj2256Isup2.hkl
4-(methylsulfonyl)benzaldehyde (0.184g) and o-toluidine (0.107g) were dissolved in acetonitrile (20 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. After keeping the solution in air for 10 d, yellow block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.
All the H atoms attached to C atoms were placed in geometrical positions and constrained to ride on their parent atoms with C-H distance in the range 0.93-0.98 Å, They were treated as riding atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: CAD-4 Software (Enraf–Nonius, 1989); 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).Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C15H15NO2S | F(000) = 576 |
Mr = 273.34 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 11.445 (2) Å | θ = 9–14° |
b = 7.8770 (16) Å | µ = 0.22 mm−1 |
c = 16.132 (3) Å | T = 293 K |
β = 98.65 (3)° | Block, yellow |
V = 1437.8 (5) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1898 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.3°, θmin = 1.8° |
ω/2θ scans | h = 0→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = 0→9 |
Tmin = 0.936, Tmax = 0.957 | l = −19→19 |
2745 measured reflections | 3 standard reflections every 200 reflections |
2607 independent reflections | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.09P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2607 reflections | Δρmax = 0.28 e Å−3 |
173 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.052 (5) |
C15H15NO2S | V = 1437.8 (5) Å3 |
Mr = 273.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.445 (2) Å | µ = 0.22 mm−1 |
b = 7.8770 (16) Å | T = 293 K |
c = 16.132 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 98.65 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1898 reflections with I > 2σ(I) |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | Rint = 0.026 |
Tmin = 0.936, Tmax = 0.957 | 3 standard reflections every 200 reflections |
2745 measured reflections | intensity decay: 1% |
2607 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.28 e Å−3 |
2607 reflections | Δρmin = −0.24 e Å−3 |
173 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 > 2sigma(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 | ||
S1 | 0.43428 (5) | 0.25210 (8) | 0.34889 (3) | 0.0539 (3) | |
N1 | 0.01690 (16) | 0.3139 (2) | 0.60356 (12) | 0.0527 (5) | |
O1 | 0.35995 (19) | 0.2305 (3) | 0.27085 (11) | 0.0941 (8) | |
C1 | 0.5014 (3) | 0.4515 (4) | 0.3496 (2) | 0.1056 (12) | |
H1B | 0.5521 | 0.4550 | 0.3074 | 0.158* | |
H1C | 0.5472 | 0.4715 | 0.4036 | 0.158* | |
H1D | 0.4417 | 0.5375 | 0.3383 | 0.158* | |
C2 | 0.3445 (2) | 0.2644 (3) | 0.42882 (13) | 0.0447 (5) | |
O2 | 0.52410 (16) | 0.1283 (3) | 0.37209 (12) | 0.0867 (7) | |
C3 | 0.38513 (18) | 0.1981 (3) | 0.50701 (13) | 0.0487 (5) | |
H3A | 0.4603 | 0.1507 | 0.5183 | 0.058* | |
C4 | 0.31293 (19) | 0.2031 (3) | 0.56824 (13) | 0.0503 (6) | |
H4A | 0.3397 | 0.1583 | 0.6210 | 0.060* | |
C5 | 0.20111 (19) | 0.2740 (3) | 0.55184 (13) | 0.0463 (5) | |
C6 | 0.1612 (2) | 0.3412 (3) | 0.47238 (14) | 0.0569 (6) | |
H6A | 0.0865 | 0.3898 | 0.4610 | 0.068* | |
C7 | 0.2329 (2) | 0.3353 (3) | 0.41107 (14) | 0.0569 (6) | |
H7A | 0.2064 | 0.3788 | 0.3580 | 0.068* | |
C8 | 0.12384 (19) | 0.2695 (3) | 0.61761 (14) | 0.0499 (6) | |
H8A | 0.1553 | 0.2328 | 0.6711 | 0.060* | |
C9 | −0.05118 (19) | 0.3031 (3) | 0.67002 (15) | 0.0504 (6) | |
C10 | −0.0096 (2) | 0.3600 (3) | 0.75031 (16) | 0.0617 (6) | |
H10A | 0.0659 | 0.4057 | 0.7623 | 0.074* | |
C11 | −0.0797 (3) | 0.3492 (4) | 0.81250 (18) | 0.0807 (9) | |
H11A | −0.0511 | 0.3865 | 0.8664 | 0.097* | |
C12 | −0.1918 (3) | 0.2837 (4) | 0.7949 (2) | 0.0881 (10) | |
H12A | −0.2392 | 0.2764 | 0.8367 | 0.106* | |
C13 | −0.2333 (2) | 0.2291 (4) | 0.7156 (2) | 0.0805 (9) | |
H13A | −0.3090 | 0.1833 | 0.7047 | 0.097* | |
C14 | −0.1664 (2) | 0.2396 (3) | 0.65064 (18) | 0.0613 (7) | |
C15 | −0.2132 (3) | 0.1814 (4) | 0.5632 (2) | 0.0894 (9) | |
H15A | −0.2931 | 0.1428 | 0.5611 | 0.134* | |
H15B | −0.1652 | 0.0901 | 0.5478 | 0.134* | |
H15C | −0.2111 | 0.2741 | 0.5248 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0647 (4) | 0.0564 (4) | 0.0429 (4) | 0.0082 (3) | 0.0156 (3) | 0.0032 (2) |
N1 | 0.0492 (11) | 0.0500 (11) | 0.0603 (12) | 0.0039 (9) | 0.0122 (9) | 0.0041 (9) |
O1 | 0.0922 (14) | 0.147 (2) | 0.0427 (10) | 0.0062 (13) | 0.0097 (10) | −0.0103 (11) |
C1 | 0.122 (3) | 0.078 (2) | 0.135 (3) | −0.0203 (19) | 0.078 (2) | −0.001 (2) |
C2 | 0.0524 (12) | 0.0402 (11) | 0.0421 (11) | 0.0007 (9) | 0.0093 (9) | 0.0013 (9) |
O2 | 0.0940 (13) | 0.0980 (16) | 0.0764 (12) | 0.0453 (12) | 0.0395 (11) | 0.0257 (11) |
C3 | 0.0436 (11) | 0.0587 (13) | 0.0426 (11) | 0.0065 (10) | 0.0019 (9) | −0.0034 (10) |
C4 | 0.0516 (13) | 0.0598 (14) | 0.0382 (11) | 0.0046 (10) | 0.0027 (9) | 0.0003 (10) |
C5 | 0.0489 (12) | 0.0460 (13) | 0.0444 (11) | 0.0005 (9) | 0.0078 (9) | −0.0020 (9) |
C6 | 0.0546 (13) | 0.0590 (15) | 0.0575 (13) | 0.0161 (11) | 0.0097 (11) | 0.0139 (11) |
C7 | 0.0635 (14) | 0.0605 (15) | 0.0470 (12) | 0.0131 (12) | 0.0099 (11) | 0.0144 (11) |
C8 | 0.0501 (13) | 0.0504 (13) | 0.0490 (12) | 0.0003 (10) | 0.0069 (10) | −0.0014 (10) |
C9 | 0.0466 (12) | 0.0421 (11) | 0.0642 (14) | 0.0031 (9) | 0.0140 (10) | 0.0026 (10) |
C10 | 0.0569 (13) | 0.0595 (15) | 0.0708 (15) | 0.0010 (12) | 0.0159 (11) | −0.0064 (12) |
C11 | 0.087 (2) | 0.085 (2) | 0.0760 (19) | 0.0097 (17) | 0.0301 (15) | −0.0102 (15) |
C12 | 0.082 (2) | 0.096 (2) | 0.098 (2) | 0.0081 (18) | 0.0495 (19) | 0.0055 (19) |
C13 | 0.0546 (16) | 0.0719 (19) | 0.121 (3) | −0.0029 (13) | 0.0317 (17) | 0.0098 (18) |
C14 | 0.0500 (13) | 0.0496 (14) | 0.0848 (18) | 0.0007 (11) | 0.0124 (12) | 0.0043 (12) |
C15 | 0.0661 (17) | 0.091 (2) | 0.106 (2) | −0.0196 (16) | −0.0010 (16) | −0.0162 (19) |
S1—O1 | 1.420 (2) | C6—H6A | 0.9300 |
S1—O2 | 1.4257 (18) | C7—H7A | 0.9300 |
S1—C1 | 1.747 (3) | C8—H8A | 0.9300 |
S1—C2 | 1.768 (2) | C9—C10 | 1.385 (3) |
N1—C8 | 1.260 (3) | C9—C14 | 1.401 (3) |
N1—C9 | 1.420 (3) | C10—C11 | 1.378 (3) |
C1—H1B | 0.9600 | C10—H10A | 0.9300 |
C1—H1C | 0.9600 | C11—C12 | 1.372 (4) |
C1—H1D | 0.9600 | C11—H11A | 0.9300 |
C2—C3 | 1.380 (3) | C12—C13 | 1.364 (5) |
C2—C7 | 1.384 (3) | C12—H12A | 0.9300 |
C3—C4 | 1.380 (3) | C13—C14 | 1.391 (4) |
C3—H3A | 0.9300 | C13—H13A | 0.9300 |
C4—C5 | 1.385 (3) | C14—C15 | 1.503 (4) |
C4—H4A | 0.9300 | C15—H15A | 0.9600 |
C5—C6 | 1.398 (3) | C15—H15B | 0.9600 |
C5—C8 | 1.480 (3) | C15—H15C | 0.9600 |
C6—C7 | 1.377 (3) | ||
O1—S1—O2 | 117.58 (13) | C6—C7—H7A | 120.1 |
O1—S1—C1 | 108.53 (17) | C2—C7—H7A | 120.1 |
O2—S1—C1 | 108.33 (16) | N1—C8—C5 | 122.2 (2) |
O1—S1—C2 | 108.46 (12) | N1—C8—H8A | 118.9 |
O2—S1—C2 | 108.73 (10) | C5—C8—H8A | 118.9 |
C1—S1—C2 | 104.42 (12) | C10—C9—C14 | 120.2 (2) |
C8—N1—C9 | 118.4 (2) | C10—C9—N1 | 122.4 (2) |
S1—C1—H1B | 109.5 | C14—C9—N1 | 117.3 (2) |
S1—C1—H1C | 109.5 | C11—C10—C9 | 120.3 (2) |
H1B—C1—H1C | 109.5 | C11—C10—H10A | 119.8 |
S1—C1—H1D | 109.5 | C9—C10—H10A | 119.8 |
H1B—C1—H1D | 109.5 | C12—C11—C10 | 120.0 (3) |
H1C—C1—H1D | 109.5 | C12—C11—H11A | 120.0 |
C3—C2—C7 | 121.0 (2) | C10—C11—H11A | 120.0 |
C3—C2—S1 | 119.54 (17) | C13—C12—C11 | 119.7 (3) |
C7—C2—S1 | 119.39 (16) | C13—C12—H12A | 120.1 |
C2—C3—C4 | 119.2 (2) | C11—C12—H12A | 120.1 |
C2—C3—H3A | 120.4 | C12—C13—C14 | 122.2 (3) |
C4—C3—H3A | 120.4 | C12—C13—H13A | 118.9 |
C3—C4—C5 | 120.7 (2) | C14—C13—H13A | 118.9 |
C3—C4—H4A | 119.7 | C13—C14—C9 | 117.4 (3) |
C5—C4—H4A | 119.7 | C13—C14—C15 | 122.0 (3) |
C4—C5—C6 | 119.5 (2) | C9—C14—C15 | 120.6 (2) |
C4—C5—C8 | 119.21 (19) | C14—C15—H15A | 109.5 |
C6—C5—C8 | 121.2 (2) | C14—C15—H15B | 109.5 |
C7—C6—C5 | 119.9 (2) | H15A—C15—H15B | 109.5 |
C7—C6—H6A | 120.1 | C14—C15—H15C | 109.5 |
C5—C6—H6A | 120.1 | H15A—C15—H15C | 109.5 |
C6—C7—C2 | 119.7 (2) | H15B—C15—H15C | 109.5 |
O1—S1—C2—C3 | 145.99 (19) | C9—N1—C8—C5 | 179.03 (19) |
O2—S1—C2—C3 | 17.0 (2) | C4—C5—C8—N1 | −171.7 (2) |
C1—S1—C2—C3 | −98.4 (2) | C6—C5—C8—N1 | 5.3 (3) |
O1—S1—C2—C7 | −31.9 (2) | C8—N1—C9—C10 | 45.4 (3) |
O2—S1—C2—C7 | −160.84 (19) | C8—N1—C9—C14 | −137.8 (2) |
C1—S1—C2—C7 | 83.7 (2) | C14—C9—C10—C11 | 2.2 (4) |
C7—C2—C3—C4 | 0.0 (3) | N1—C9—C10—C11 | 179.0 (2) |
S1—C2—C3—C4 | −177.84 (16) | C9—C10—C11—C12 | −0.7 (4) |
C2—C3—C4—C5 | −0.2 (3) | C10—C11—C12—C13 | 0.1 (5) |
C3—C4—C5—C6 | 0.0 (3) | C11—C12—C13—C14 | −1.0 (5) |
C3—C4—C5—C8 | 177.0 (2) | C12—C13—C14—C9 | 2.4 (4) |
C4—C5—C6—C7 | 0.5 (4) | C12—C13—C14—C15 | −179.1 (3) |
C8—C5—C6—C7 | −176.5 (2) | C10—C9—C14—C13 | −3.0 (3) |
C5—C6—C7—C2 | −0.7 (4) | N1—C9—C14—C13 | −179.9 (2) |
C3—C2—C7—C6 | 0.4 (4) | C10—C9—C14—C15 | 178.5 (2) |
S1—C2—C7—C6 | 178.29 (19) | N1—C9—C14—C15 | 1.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.55 | 3.274 (3) | 135 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO2S |
Mr | 273.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.445 (2), 7.8770 (16), 16.132 (3) |
β (°) | 98.65 (3) |
V (Å3) | 1437.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.936, 0.957 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2745, 2607, 1898 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.151, 1.00 |
No. of reflections | 2607 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.24 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.55 | 3.274 (3) | 135 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
This project was sponsored by ShanDong province Science & Technology Innovation Foundation.
References
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Shao, S.-C., You, Z.-L., Fan, S.-H., Tang, L.-L., Xiong, Z.-D. & Zhu, H.-L. (2004). Acta Cryst. E60, o2183–o2184. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Schiff base compounds have attracted attention for the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular archtectures(Shao et al., 2004). As an extension of work on the structural characterization of Schiff base compounds, the crystal structure of the title compound(I), Figure 1, is reported here. The molecule displays a trans-configuration with respect to the C=N double bond. the crystal structure is stabilized by weak C—H···O hydrogen bonds(Figure 2). The dihedral angle between two aromatic ring planes is 50.41 (12)°.