(E)-N-[4-(Methyl­sulfon­yl)benzyl­idene]aniline

Qian, S.-S.; Liu, T.

doi:10.1107/S1600536809050983

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o18

doi:10.1107/S1600536809050983

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(E)-N-[4-(Methylsulfonyl)benzylidene]aniline

Shao-Song Qian ^a ^* and Tao Liu ^a

^aSchool of Life Sciences, Shandong University of Technology, ZiBo 255049, People's Republic of China
^*Correspondence e-mail: njuqss@yahoo.com.cn

(Received 21 November 2009; accepted 26 November 2009; online 4 December 2009)

The molecule of the title compound, C₁₄H₁₃NO₂S, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two aromatic ring planes is 62.07 (18)°.

Related literature

For a related structure, see: Qian & Cui (2009 ). For comparitive bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₃NO₂S
M_r = 259.31
Monoclinic, P 2₁ /c
a = 8.2070 (16) Å
b = 5.7750 (12) Å
c = 26.945 (5) Å
β = 94.72 (3)°
V = 1272.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.930, T_max = 0.976
2462 measured reflections
2292 independent reflections
1542 reflections with I > 2σ(I)
R_int = 0.053
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.138
S = 1.03
2292 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050983/rz2398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050983/rz2398Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been of great of interest for many years. and act as important precursors for coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular archtectures. As an extension of work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

In the title compound (Fig. 1), all bond lengths are within normal ranges (Allen et al., 1987) and comparable to the values observed in a closely related compound (Qian et al., 2009). The molecule displays a trans-configuration with respect to the C=N double bond. The dihedral angle between two aromatic ring planes is 62.07 (18)°. The crystal packing is stabilized only by van der Waals interactions.

Related literature top

For a related structure, see: Qian & Cui (2009). For comparitive bond lengths, see: Allen et al. (1987).

Experimental top

4-(Methylsulfonyl)benzaldehyde (0.184 g) and aniline (0.093 g) 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 7 d, yellow block-shaped crystals suitable for X-ray analysis were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

Figures top

Fig. 1. The structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

(E)-N-[4-(Methylsulfonyl)benzylidene]aniline top

Crystal data top

C₁₄H₁₃NO₂S	F(000) = 544
M_r = 259.31	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.2070 (16) Å	θ = 9–13°
b = 5.7750 (12) Å	µ = 0.25 mm⁻¹
c = 26.945 (5) Å	T = 293 K
β = 94.72 (3)°	Block, yellow
V = 1272.7 (4) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 25.3°, θ_min = 1.5°
ω/2θ scans	h = 0→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = 0→6
T_min = 0.930, T_max = 0.976	l = −32→32
2462 measured reflections	3 standard reflections every 200 reflections
2292 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0501P)² + 1.018P] where P = (F_o² + 2F_c²)/3
2292 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂S	V = 1272.7 (4) Å³
M_r = 259.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2070 (16) Å	µ = 0.25 mm⁻¹
b = 5.7750 (12) Å	T = 293 K
c = 26.945 (5) Å	0.30 × 0.20 × 0.10 mm
β = 94.72 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1542 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	R_int = 0.053
T_min = 0.930, T_max = 0.976	3 standard reflections every 200 reflections
2462 measured reflections	intensity decay: 1%
2292 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
2292 reflections	Δρ_min = −0.34 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.80688 (10)	0.31400 (15)	0.45864 (3)	0.0473 (3)
N	0.1198 (3)	−0.1536 (5)	0.34256 (10)	0.0474 (7)
O1	0.9360 (3)	0.2295 (5)	0.43114 (9)	0.0609 (7)
C1	−0.3341 (4)	−0.2970 (7)	0.26535 (15)	0.0635 (11)
H1B	−0.4331	−0.3326	0.2477	0.076*
O2	0.8001 (3)	0.5582 (4)	0.46914 (11)	0.0680 (8)
C2	−0.2463 (5)	−0.1064 (7)	0.25292 (15)	0.0592 (10)
H2B	−0.2866	−0.0125	0.2267	0.071*
C3	−0.0992 (4)	−0.0518 (6)	0.27874 (13)	0.0488 (9)
H3A	−0.0420	0.0793	0.2701	0.059*
C4	−0.0363 (4)	−0.1919 (6)	0.31746 (12)	0.0426 (8)
C5	−0.1259 (4)	−0.3852 (6)	0.32996 (14)	0.0537 (9)
H5A	−0.0857	−0.4813	0.3558	0.064*
C6	−0.2737 (5)	−0.4344 (7)	0.30415 (16)	0.0632 (11)
H6A	−0.3334	−0.5624	0.3131	0.076*
C7	0.1609 (4)	0.0524 (6)	0.35336 (12)	0.0467 (8)
H7A	0.0855	0.1699	0.3458	0.056*
C8	0.3215 (4)	0.1149 (6)	0.37721 (12)	0.0433 (8)
C9	0.3412 (4)	0.3236 (6)	0.40197 (15)	0.0586 (10)
H9A	0.2534	0.4255	0.4017	0.070*
C10	0.4877 (4)	0.3840 (6)	0.42707 (14)	0.0564 (10)
H10A	0.4982	0.5241	0.4441	0.068*
C11	0.6192 (4)	0.2351 (6)	0.42680 (12)	0.0435 (8)
C12	0.6034 (4)	0.0265 (6)	0.40118 (14)	0.0549 (10)
H12A	0.6925	−0.0726	0.4004	0.066*
C13	0.4555 (4)	−0.0325 (6)	0.37695 (14)	0.0537 (9)
H13A	0.4447	−0.1729	0.3601	0.064*
C14	0.8121 (4)	0.1617 (7)	0.51489 (13)	0.0603 (10)
H14A	0.9119	0.1963	0.5346	0.090*
H14B	0.8065	−0.0015	0.5082	0.090*
H14C	0.7206	0.2067	0.5327	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0448 (5)	0.0432 (5)	0.0537 (6)	0.0085 (4)	0.0032 (4)	0.0064 (4)
N	0.0488 (16)	0.0410 (17)	0.0523 (17)	0.0068 (14)	0.0040 (13)	0.0032 (14)
O1	0.0459 (13)	0.0773 (19)	0.0610 (16)	0.0114 (13)	0.0130 (11)	0.0111 (14)
C1	0.053 (2)	0.066 (3)	0.071 (3)	−0.004 (2)	−0.0011 (19)	−0.007 (2)
O2	0.0654 (16)	0.0407 (14)	0.094 (2)	0.0054 (13)	−0.0148 (15)	−0.0008 (14)
C2	0.058 (2)	0.060 (3)	0.059 (2)	0.010 (2)	−0.0002 (19)	0.007 (2)
C3	0.053 (2)	0.0402 (19)	0.054 (2)	0.0019 (17)	0.0059 (17)	0.0059 (17)
C4	0.0486 (19)	0.0355 (18)	0.0449 (19)	0.0070 (16)	0.0099 (15)	−0.0033 (16)
C5	0.062 (2)	0.040 (2)	0.060 (2)	0.0055 (18)	0.0112 (19)	0.0028 (17)
C6	0.064 (2)	0.047 (2)	0.081 (3)	−0.008 (2)	0.015 (2)	−0.001 (2)
C7	0.050 (2)	0.043 (2)	0.047 (2)	0.0093 (16)	0.0067 (16)	−0.0008 (17)
C8	0.0459 (19)	0.0406 (19)	0.0437 (19)	0.0078 (15)	0.0044 (15)	0.0014 (15)
C9	0.050 (2)	0.045 (2)	0.079 (3)	0.0195 (18)	−0.0019 (19)	−0.008 (2)
C10	0.052 (2)	0.042 (2)	0.074 (3)	0.0153 (17)	−0.0066 (19)	−0.0130 (19)
C11	0.0469 (18)	0.0373 (19)	0.047 (2)	0.0096 (15)	0.0088 (15)	0.0063 (15)
C12	0.048 (2)	0.044 (2)	0.073 (3)	0.0183 (17)	0.0069 (19)	−0.0034 (19)
C13	0.054 (2)	0.039 (2)	0.068 (2)	0.0087 (17)	0.0065 (18)	−0.0107 (18)
C14	0.061 (2)	0.066 (3)	0.054 (2)	0.018 (2)	0.0050 (18)	0.008 (2)

Geometric parameters (Å, º) top

S—O1	1.428 (2)	C6—H6A	0.9300
S—O2	1.440 (3)	C7—C8	1.463 (5)
S—C14	1.750 (4)	C7—H7A	0.9300
S—C11	1.760 (4)	C8—C9	1.381 (5)
N—C7	1.264 (4)	C8—C13	1.391 (4)
N—C4	1.416 (4)	C9—C10	1.375 (5)
C1—C2	1.372 (5)	C9—H9A	0.9300
C1—C6	1.372 (5)	C10—C11	1.380 (4)
C1—H1B	0.9300	C10—H10A	0.9300
C2—C3	1.379 (5)	C11—C12	1.389 (5)
C2—H2B	0.9300	C12—C13	1.373 (5)
C3—C4	1.386 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.393 (5)	C14—H14A	0.9600
C5—C6	1.377 (5)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600

O1—S—O2	118.61 (17)	N—C7—H7A	118.4
O1—S—C14	108.15 (16)	C8—C7—H7A	118.4
O2—S—C14	108.70 (19)	C9—C8—C13	118.4 (3)
O1—S—C11	108.39 (15)	C9—C8—C7	119.6 (3)
O2—S—C11	107.63 (15)	C13—C8—C7	122.1 (3)
C14—S—C11	104.47 (17)	C10—C9—C8	121.5 (3)
C7—N—C4	118.1 (3)	C10—C9—H9A	119.3
C2—C1—C6	119.1 (4)	C8—C9—H9A	119.3
C2—C1—H1B	120.5	C9—C10—C11	119.4 (3)
C6—C1—H1B	120.5	C9—C10—H10A	120.3
C1—C2—C3	121.0 (4)	C11—C10—H10A	120.3
C1—C2—H2B	119.5	C10—C11—C12	120.1 (3)
C3—C2—H2B	119.5	C10—C11—S	119.3 (3)
C2—C3—C4	120.1 (3)	C12—C11—S	120.6 (2)
C2—C3—H3A	119.9	C13—C12—C11	119.6 (3)
C4—C3—H3A	119.9	C13—C12—H12A	120.2
C3—C4—C5	118.6 (3)	C11—C12—H12A	120.2
C3—C4—N	122.3 (3)	C12—C13—C8	121.0 (3)
C5—C4—N	119.0 (3)	C12—C13—H13A	119.5
C6—C5—C4	120.2 (4)	C8—C13—H13A	119.5
C6—C5—H5A	119.9	S—C14—H14A	109.5
C4—C5—H5A	119.9	S—C14—H14B	109.5
C1—C6—C5	120.9 (4)	H14A—C14—H14B	109.5
C1—C6—H6A	119.6	S—C14—H14C	109.5
C5—C6—H6A	119.6	H14A—C14—H14C	109.5
N—C7—C8	123.2 (3)	H14B—C14—H14C	109.5

C6—C1—C2—C3	0.1 (6)	C8—C9—C10—C11	1.2 (6)
C1—C2—C3—C4	1.0 (6)	C9—C10—C11—C12	0.3 (6)
C2—C3—C4—C5	−1.0 (5)	C9—C10—C11—S	179.6 (3)
C2—C3—C4—N	175.0 (3)	O1—S—C11—C10	−144.6 (3)
C7—N—C4—C3	42.2 (5)	O2—S—C11—C10	−15.2 (3)
C7—N—C4—C5	−141.8 (3)	C14—S—C11—C10	100.2 (3)
C3—C4—C5—C6	0.0 (5)	O1—S—C11—C12	34.7 (3)
N—C4—C5—C6	−176.1 (3)	O2—S—C11—C12	164.1 (3)
C2—C1—C6—C5	−1.0 (6)	C14—S—C11—C12	−80.5 (3)
C4—C5—C6—C1	1.0 (6)	C10—C11—C12—C13	−1.3 (5)
C4—N—C7—C8	−177.2 (3)	S—C11—C12—C13	179.5 (3)
N—C7—C8—C9	−159.4 (4)	C11—C12—C13—C8	0.7 (6)
N—C7—C8—C13	18.9 (5)	C9—C8—C13—C12	0.7 (6)
C13—C8—C9—C10	−1.7 (6)	C7—C8—C13—C12	−177.6 (3)
C7—C8—C9—C10	176.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂S
M_r	259.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.2070 (16), 5.7750 (12), 26.945 (5)
β (°)	94.72 (3)
V (Å³)	1272.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.930, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	2462, 2292, 1542
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.138, 1.03
No. of reflections	2292
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was sponsored by the Shandong Province Science & Technology Innovation Foundation (People's Republic of China).

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
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Qian, S.-S. & Cui, H.-Y. (2009). Acta Cryst. E65, o3072. 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