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

In the crystal structure of the title compound, C(14)H(12)ClNO(2)S, the mol-ecules display a trans conformation with respect to the C=N double bond. The dihedral angle between the methyl-sulfonyl benzene and chloro-benzene rings is 59.59 (8)°. The crystal packing is stabilized by weak C-H⋯O inter-actions and by π-π stacking inter-actions between inversion-related methyl-sulfonyl benzene rings [centroid-centroid distance = 3.8579 (11) Å].

Related literature

For background to the pharmacological properties of Schiff base compounds, see: Villar et al. (2004 ▶); Pandey et al. (1999 ▶); Singh & Dash (1988 ▶). For related structures, see: Qian & Cui (2009 ▶); Qian & Liu (2010 ▶).

Experimental

Crystal data

C14H12ClNO2S

M = 293.77

Monoclinic,

a = 8.6206 (10) Å

b = 8.8748 (10) Å

c = 17.799 (2) Å

β = 94.972 (1)°

V = 1356.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 296 K

0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.898, T max = 0.913

11492 measured reflections

3320 independent reflections

2596 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.04

3320 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105361X/pk2372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105361X/pk2372Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105361X/pk2372Isup3.cml

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

C14H12ClNO2S	F(000) = 608
Mr = 293.77	Dx = 1.438 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3320 reflections
a = 8.6206 (10) Å	θ = 2.3–28.3°
b = 8.8748 (10) Å	µ = 0.43 mm−1
c = 17.799 (2) Å	T = 296 K
β = 94.972 (1)°	Block, yellow
V = 1356.6 (3) Å3	0.25 × 0.23 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	3320 independent reflections
Radiation source: fine-focus sealed tube	2596 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→9
Tmin = 0.898, Tmax = 0.913	k = −11→11
11492 measured reflections	l = −23→23

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.4568P] where P = (Fo2 + 2Fc2)/3
3320 reflections	(Δ/σ)max = 0.002
173 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.40 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
Cl1	1.44038 (7)	0.87940 (7)	0.77377 (3)	0.06397 (19)
S1	0.25645 (5)	0.66162 (5)	1.12920 (2)	0.03972 (14)
O1	0.12146 (16)	0.67285 (18)	1.07669 (8)	0.0580 (4)
O2	0.27398 (19)	0.52896 (17)	1.17454 (9)	0.0644 (4)
N1	0.85437 (18)	0.84443 (17)	0.92329 (9)	0.0414 (3)
C1	1.2692 (2)	0.8676 (2)	0.81840 (10)	0.0403 (4)
C2	1.1903 (2)	0.7325 (2)	0.81801 (10)	0.0431 (4)
H2	1.2286	0.6487	0.7943	0.052*
C3	1.0540 (2)	0.7226 (2)	0.85314 (10)	0.0407 (4)
H3	1.0004	0.6316	0.8532	0.049*
C4	0.9963 (2)	0.84819 (19)	0.88855 (9)	0.0370 (4)
C5	1.0771 (2)	0.9831 (2)	0.88774 (10)	0.0431 (4)
H5	1.0384	1.0679	0.9105	0.052*
C6	1.2147 (2)	0.9930 (2)	0.85339 (11)	0.0447 (4)
H6	1.2697	1.0832	0.8539	0.054*
C7	0.8294 (2)	0.7307 (2)	0.96360 (9)	0.0386 (4)
H7	0.9046	0.6554	0.9693	0.046*
C8	0.68621 (19)	0.71368 (19)	1.00167 (9)	0.0358 (4)
C9	0.6839 (2)	0.6093 (2)	1.05955 (11)	0.0475 (4)
H9	0.7711	0.5498	1.0722	0.057*
C10	0.5532 (2)	0.5927 (2)	1.09869 (11)	0.0465 (4)
H10	0.5526	0.5232	1.1378	0.056*
C11	0.42363 (19)	0.68041 (18)	1.07919 (9)	0.0350 (3)
C12	0.4227 (2)	0.7835 (2)	1.02035 (10)	0.0434 (4)
H12	0.3342	0.8404	1.0067	0.052*
C13	0.5543 (2)	0.8005 (2)	0.98253 (10)	0.0431 (4)
H13	0.5551	0.8708	0.9438	0.052*
C14	0.2630 (3)	0.8207 (2)	1.18768 (12)	0.0544 (5)
H14A	0.1760	0.8191	1.2179	0.082*
H14B	0.2586	0.9102	1.1572	0.082*
H14C	0.3582	0.8201	1.2200	0.082*

	U11	U22	U33	U12	U13	U23
Cl1	0.0498 (3)	0.0688 (4)	0.0779 (4)	−0.0003 (2)	0.0313 (3)	0.0035 (3)
S1	0.0346 (2)	0.0412 (2)	0.0442 (2)	−0.00697 (17)	0.00761 (17)	−0.00031 (17)
O1	0.0350 (7)	0.0783 (10)	0.0600 (8)	−0.0089 (7)	0.0000 (6)	−0.0115 (7)
O2	0.0652 (10)	0.0534 (9)	0.0780 (10)	−0.0046 (7)	0.0263 (8)	0.0217 (8)
N1	0.0337 (8)	0.0431 (8)	0.0484 (8)	−0.0006 (6)	0.0101 (6)	−0.0019 (6)
C1	0.0345 (9)	0.0471 (10)	0.0403 (9)	0.0007 (7)	0.0079 (7)	0.0022 (7)
C2	0.0439 (10)	0.0415 (9)	0.0452 (9)	0.0039 (8)	0.0104 (8)	−0.0045 (8)
C3	0.0399 (10)	0.0380 (9)	0.0447 (9)	−0.0031 (7)	0.0065 (7)	−0.0027 (7)
C4	0.0315 (9)	0.0407 (9)	0.0389 (8)	0.0007 (7)	0.0037 (7)	−0.0004 (7)
C5	0.0433 (10)	0.0391 (9)	0.0479 (10)	0.0000 (7)	0.0102 (8)	−0.0064 (7)
C6	0.0448 (10)	0.0403 (9)	0.0498 (10)	−0.0082 (8)	0.0093 (8)	−0.0007 (8)
C7	0.0324 (9)	0.0427 (9)	0.0406 (8)	0.0014 (7)	0.0033 (7)	−0.0034 (7)
C8	0.0331 (9)	0.0368 (8)	0.0377 (8)	−0.0001 (7)	0.0046 (7)	−0.0026 (7)
C9	0.0393 (10)	0.0498 (11)	0.0540 (11)	0.0126 (8)	0.0065 (8)	0.0127 (8)
C10	0.0436 (10)	0.0471 (10)	0.0496 (10)	0.0074 (8)	0.0090 (8)	0.0161 (8)
C11	0.0323 (8)	0.0356 (8)	0.0371 (8)	−0.0016 (6)	0.0037 (6)	0.0003 (6)
C12	0.0333 (9)	0.0470 (10)	0.0500 (10)	0.0062 (7)	0.0047 (7)	0.0123 (8)
C13	0.0387 (9)	0.0458 (10)	0.0451 (9)	0.0040 (7)	0.0060 (7)	0.0130 (8)
C14	0.0500 (12)	0.0614 (13)	0.0531 (11)	−0.0075 (9)	0.0120 (9)	−0.0155 (10)

Cl1—C1	1.7389 (18)	C6—H6	0.9300
S1—O2	1.4281 (15)	C7—C8	1.467 (2)
S1—O1	1.4315 (15)	C7—H7	0.9300
S1—C14	1.752 (2)	C8—C9	1.387 (2)
S1—C11	1.7662 (17)	C8—C13	1.391 (2)
N1—C7	1.267 (2)	C9—C10	1.383 (3)
N1—C4	1.418 (2)	C9—H9	0.9300
C1—C2	1.377 (3)	C10—C11	1.381 (3)
C1—C6	1.378 (3)	C10—H10	0.9300
C2—C3	1.382 (2)	C11—C12	1.390 (2)
C2—H2	0.9300	C12—C13	1.377 (2)
C3—C4	1.393 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.386 (2)	C14—H14A	0.9600
C5—C6	1.384 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O2—S1—O1	117.81 (10)	N1—C7—H7	118.8
O2—S1—C14	109.41 (11)	C8—C7—H7	118.8
O1—S1—C14	108.32 (10)	C9—C8—C13	119.20 (16)
O2—S1—C11	108.16 (9)	C9—C8—C7	118.61 (15)
O1—S1—C11	108.49 (8)	C13—C8—C7	122.18 (15)
C14—S1—C11	103.73 (9)	C10—C9—C8	120.66 (17)
C7—N1—C4	117.42 (15)	C10—C9—H9	119.7
C2—C1—C6	121.20 (17)	C8—C9—H9	119.7
C2—C1—Cl1	119.21 (14)	C11—C10—C9	119.35 (16)
C6—C1—Cl1	119.59 (14)	C11—C10—H10	120.3
C1—C2—C3	119.48 (16)	C9—C10—H10	120.3
C1—C2—H2	120.3	C10—C11—C12	120.79 (16)
C3—C2—H2	120.3	C10—C11—S1	119.85 (13)
C2—C3—C4	120.29 (16)	C12—C11—S1	119.36 (13)
C2—C3—H3	119.9	C13—C12—C11	119.31 (16)
C4—C3—H3	119.9	C13—C12—H12	120.3
C5—C4—C3	119.17 (16)	C11—C12—H12	120.3
C5—C4—N1	118.56 (15)	C12—C13—C8	120.67 (16)
C3—C4—N1	122.23 (15)	C12—C13—H13	119.7
C6—C5—C4	120.69 (17)	C8—C13—H13	119.7
C6—C5—H5	119.7	S1—C14—H14A	109.5
C4—C5—H5	119.7	S1—C14—H14B	109.5
C1—C6—C5	119.14 (17)	H14A—C14—H14B	109.5
C1—C6—H6	120.4	S1—C14—H14C	109.5
C5—C6—H6	120.4	H14A—C14—H14C	109.5
N1—C7—C8	122.31 (16)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.56	3.126 (2)	120.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.56	3.126 (2)	120

Symmetry code: (i) .