(E)-2-Methyl-N-[4-(methyl-sulfon-yl)benzyl-idene]aniline.

Mol-ecules of the title compound, C(15)H(15)NO(2)S, 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 = 273.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.151

S = 1.00

2607 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

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 .

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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)

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

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) .