(E)-2-Methyl-N-[4-(methyl­sulfon­yl)benzyl­idene]aniline

Qian, S.-S.; Cui, H.-Y.

doi:10.1107/S1600536809047199

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3072

doi:10.1107/S1600536809047199

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(E)-2-Methyl-N-[4-(methylsulfonyl)benzylidene]aniline

Shao-Song Qian ^a ^* and Hong-You Cui ^b

^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

(Received 1 November 2009; accepted 9 November 2009; online 14 November 2009)

Molecules of the title compound, C₁₅H₁₅NO₂S, display an E configuration with respect to the C=N double bond. The crystal structure 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

C₁₅H₁₅NO₂S
M_r = 273.34
Monoclinic, P 2₁ /c
a = 11.445 (2) Å
b = 7.8770 (16) Å
c = 16.132 (3) Å
β = 98.65 (3)°
V = 1437.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.936, T_max = 0.957
2745 measured reflections
2607 independent reflections
1898 reflections with I > 2σ(I)
R_int = 0.026
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.151
S = 1.00
2607 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047199/fj2256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047199/fj2256Isup2.hkl

checkCIF report

Comment top

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)°.

Related literature top

For background to Schiff base compounds in coordination chemistry, see: Shao et al. (2004).

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: 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).

Figures top

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

(E)-2-Methyl-N-[4-(methylsulfonyl)benzylidene]aniline top

Crystal data top

C₁₅H₁₅NO₂S	F(000) = 576
M_r = 273.34	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1898 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = 0→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = 0→9
T_min = 0.936, T_max = 0.957	l = −19→19
2745 measured reflections	3 standard reflections every 200 reflections
2607 independent reflections	intensity decay: 1%

Refinement top

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(F_o²) + (0.1P)² + 0.09P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2607 reflections	Δρ_max = 0.28 e Å⁻³
173 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₅NO₂S	V = 1437.8 (5) Å³
M_r = 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)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1898 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	R_int = 0.026
T_min = 0.936, T_max = 0.957	3 standard reflections every 200 reflections
2745 measured reflections	intensity decay: 1%
2607 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.00	Δρ_max = 0.28 e Å⁻³
2607 reflections	Δρ_min = −0.24 e Å⁻³
173 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.936, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	2745, 2607, 1898
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

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

Hydrogen-bond geometry (Å, º) top

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