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

The mol-ecule of the title compound, C(14)H(13)NO(2)S, 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 = 259.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.138

S = 1.03

2292 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −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.

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

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

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

C14H13NO2S	F(000) = 544
Mr = 259.31	Dx = 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

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

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(Fo2) + (0.0501P)2 + 1.018P] where P = (Fo2 + 2Fc2)/3
2292 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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
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*

	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)

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)