4-{2-[(5-Chloro-2-hydroxy-benzyl-idene)amino]eth-yl}benzene-sulfonamide.

In the mol-ecule of the title compound, C(15)H(15)ClN(2)O(3)S, the S atom adopts a distorted tetra-hedral coordination geometry with two O atoms, one N atom of the amide group and one C atom of the aromatic ring. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the adjacent aromatic ring at a dihedral angle of 3.38 (11)°. Thus, the two rings are nearly coplanar. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Supuran & Scozzafava (2001 ▶); Chohan & Shad (2007 ▶). For related literature, see: Chohan et al. (2008 ▶); Shad et al. (2008 ▶); Tahir et al. (2008 ▶); Li (2006 ▶).

Experimental

Crystal data

C15H15ClN2O3S

M = 338.80

Monoclinic,

a = 21.069 (2) Å

b = 4.8125 (6) Å

c = 30.838 (3) Å

β = 99.942 (9)°

V = 3079.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 296 (2) K

0.22 × 0.18 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.920, T max = 0.940

16002 measured reflections

4067 independent reflections

1851 reflections with I > 3σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.185

S = 1.02

4067 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005084/hk2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005084/hk2428Isup2.hkl

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

C15H15ClN2O3S	F000 = 1408
Mr = 338.80	Dx = 1.461 Mg m−3
Monoclinic, C2/c	Melting point: 497 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 21.069 (2) Å	Cell parameters from 2163 reflections
b = 4.8125 (6) Å	θ = 1.3–29.2º
c = 30.838 (3) Å	µ = 0.40 mm−1
β = 99.942 (9)º	T = 296 (2) K
V = 3079.9 (6) Å3	Prismatic, yellow
Z = 8	0.22 × 0.18 × 0.14 mm

Bruker KappaAPEXII CCD diffractometer	4067 independent reflections
Radiation source: fine-focus sealed tube	1851 reflections with I > 3σ(I)
Monochromator: graphite	Rint = 0.060
Detector resolution: 7.40 pixels mm-1	θmax = 29.2º
T = 296(2) K	θmin = 1.3º
ω scans	h = −28→28
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −6→5
Tmin = 0.920, Tmax = 0.940	l = −41→42
16002 measured reflections

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.185	w = 1/[σ2(Fo2) + (0.0.0962P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4067 reflections	Δρmax = 0.36 e Å−3
206 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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	0.32293 (6)	0.3434 (3)	0.35291 (5)	0.1046 (5)
S1	−0.14925 (4)	0.84474 (16)	−0.01326 (3)	0.0411 (3)
O1	0.07158 (14)	−0.1064 (6)	0.27525 (10)	0.0724 (11)
O2	−0.19990 (11)	1.0016 (4)	0.00047 (8)	0.0535 (9)
O3	−0.10664 (12)	0.9849 (5)	−0.03704 (8)	0.0604 (9)
N1	0.06373 (16)	0.2662 (6)	0.21557 (9)	0.0566 (10)
N2	−0.18450 (17)	0.5984 (6)	−0.04399 (11)	0.0510 (11)
C1	0.15618 (18)	0.2192 (8)	0.27152 (11)	0.0494 (11)
C2	0.12970 (19)	−0.0013 (8)	0.29194 (12)	0.0526 (11)
C3	0.1641 (2)	−0.1103 (9)	0.33014 (13)	0.0687 (16)
C4	0.2227 (2)	−0.0078 (9)	0.34865 (13)	0.0677 (16)
C5	0.24889 (19)	0.2059 (9)	0.32861 (14)	0.0663 (14)
C6	0.2167 (2)	0.3195 (9)	0.29034 (13)	0.0655 (14)
C7	0.1197 (2)	0.3508 (8)	0.23331 (12)	0.0590 (12)
C8	0.0272 (2)	0.4227 (8)	0.17939 (12)	0.0622 (14)
C9	0.0102 (2)	0.2436 (8)	0.13928 (12)	0.0653 (14)
C10	−0.02942 (19)	0.3998 (7)	0.10209 (11)	0.0501 (11)
C11	−0.09656 (19)	0.3851 (7)	0.09454 (12)	0.0556 (12)
C12	−0.13287 (17)	0.5259 (7)	0.06036 (11)	0.0504 (11)
C13	−0.10314 (14)	0.6854 (6)	0.03276 (10)	0.0355 (9)
C14	−0.03664 (16)	0.7064 (8)	0.03996 (12)	0.0538 (11)
C15	−0.00076 (18)	0.5662 (9)	0.07457 (13)	0.0625 (13)
H1	0.05445	−0.00964	0.25463	0.1087*
H2	−0.212 (2)	0.526 (9)	−0.0349 (15)	0.0767*
H2A	−0.160 (2)	0.495 (9)	−0.0511 (14)	0.0613*
H3	0.14678	−0.25811	0.34366	0.0825*
H4	0.24468	−0.08276	0.37477	0.0812*
H6	0.23528	0.46403	0.27690	0.0786*
H7	0.13739	0.50280	0.22110	0.0710*
H8A	0.05252	0.58026	0.17261	0.0746*
H8B	−0.01190	0.49318	0.18800	0.0746*
H9A	0.04945	0.17819	0.13017	0.0782*
H9B	−0.01370	0.08266	0.14642	0.0782*
H11	−0.11706	0.27761	0.11306	0.0667*
H12	−0.17758	0.51368	0.05583	0.0607*
H14	−0.01635	0.81493	0.02147	0.0647*
H15	0.04386	0.58389	0.07956	0.0747*

	U11	U22	U33	U12	U13	U23
Cl1	0.0648 (7)	0.1294 (11)	0.1019 (10)	0.0029 (8)	−0.0357 (7)	−0.0252 (8)
S1	0.0365 (4)	0.0370 (4)	0.0461 (5)	−0.0006 (4)	−0.0030 (3)	0.0111 (4)
O1	0.0634 (17)	0.076 (2)	0.0685 (19)	−0.0105 (16)	−0.0151 (14)	0.0163 (14)
O2	0.0434 (14)	0.0394 (12)	0.0741 (18)	0.0078 (11)	0.0002 (13)	0.0034 (12)
O3	0.0485 (14)	0.0685 (15)	0.0621 (16)	−0.0062 (14)	0.0036 (13)	0.0313 (13)
N1	0.0563 (18)	0.0628 (18)	0.0439 (17)	0.0072 (17)	−0.0104 (15)	0.0043 (14)
N2	0.054 (2)	0.0502 (19)	0.0440 (18)	−0.0025 (15)	−0.0054 (15)	0.0014 (14)
C1	0.0497 (19)	0.058 (2)	0.0367 (18)	0.0091 (18)	−0.0034 (16)	−0.0007 (16)
C2	0.057 (2)	0.057 (2)	0.0391 (19)	0.012 (2)	−0.0050 (17)	−0.0024 (16)
C3	0.078 (3)	0.069 (3)	0.053 (2)	0.012 (2)	−0.006 (2)	0.010 (2)
C4	0.074 (3)	0.076 (3)	0.044 (2)	0.024 (3)	−0.015 (2)	−0.002 (2)
C5	0.051 (2)	0.086 (3)	0.054 (2)	0.015 (2)	−0.0134 (19)	−0.023 (2)
C6	0.057 (2)	0.081 (3)	0.053 (2)	0.003 (2)	−0.0063 (19)	0.001 (2)
C7	0.061 (2)	0.066 (2)	0.045 (2)	0.001 (2)	−0.0047 (18)	0.0111 (18)
C8	0.069 (3)	0.055 (2)	0.055 (2)	0.014 (2)	−0.011 (2)	0.0057 (18)
C9	0.083 (3)	0.059 (2)	0.045 (2)	0.021 (2)	−0.014 (2)	0.0039 (18)
C10	0.062 (2)	0.046 (2)	0.0371 (18)	0.0077 (19)	−0.0063 (17)	0.0017 (15)
C11	0.058 (2)	0.061 (2)	0.045 (2)	−0.005 (2)	0.0013 (18)	0.0167 (17)
C12	0.0418 (19)	0.061 (2)	0.045 (2)	−0.0051 (18)	−0.0017 (16)	0.0101 (17)
C13	0.0348 (15)	0.0331 (16)	0.0366 (17)	−0.0014 (14)	0.0003 (13)	0.0030 (13)
C14	0.0354 (17)	0.070 (2)	0.054 (2)	−0.0030 (19)	0.0025 (17)	0.0195 (19)
C15	0.0372 (18)	0.088 (3)	0.058 (2)	0.009 (2)	−0.0039 (17)	0.012 (2)

Cl1—C5	1.741 (4)	C9—C10	1.499 (5)
S1—O2	1.430 (2)	C10—C15	1.380 (5)
S1—O3	1.423 (3)	C10—C11	1.395 (6)
S1—N2	1.616 (3)	C11—C12	1.370 (5)
S1—C13	1.752 (3)	C12—C13	1.375 (5)
O1—C2	1.343 (5)	C13—C14	1.384 (5)
O1—H1	0.8200	C14—C15	1.374 (5)
N1—C7	1.278 (5)	C3—H3	0.9300
N1—C8	1.452 (5)	C4—H4	0.9300
N2—H2	0.77 (4)	C6—H6	0.9300
N2—H2A	0.78 (4)	C7—H7	0.9300
C1—C7	1.438 (5)	C8—H8A	0.9700
C1—C2	1.398 (5)	C8—H8B	0.9700
C1—C6	1.393 (6)	C9—H9A	0.9700
C2—C3	1.376 (6)	C9—H9B	0.9700
C3—C4	1.360 (6)	C11—H11	0.9300
C4—C5	1.365 (6)	C12—H12	0.9300
C5—C6	1.369 (6)	C14—H14	0.9300
C8—C9	1.499 (5)	C15—H15	0.9300
O2—S1—O3	118.15 (14)	S1—C13—C12	119.8 (2)
O2—S1—N2	105.67 (16)	C12—C13—C14	119.9 (3)
O2—S1—C13	109.21 (15)	S1—C13—C14	120.2 (2)
O3—S1—N2	108.20 (17)	C13—C14—C15	119.7 (3)
O3—S1—C13	108.29 (15)	C10—C15—C14	121.5 (4)
N2—S1—C13	106.76 (15)	C2—C3—H3	119.00
C2—O1—H1	109.00	C4—C3—H3	119.00
C7—N1—C8	119.4 (3)	C3—C4—H4	120.00
S1—N2—H2	115 (3)	C5—C4—H4	120.00
S1—N2—H2A	112 (3)	C1—C6—H6	120.00
H2—N2—H2A	113 (5)	C5—C6—H6	120.00
C2—C1—C7	120.3 (3)	N1—C7—H7	119.00
C6—C1—C7	120.7 (4)	C1—C7—H7	119.00
C2—C1—C6	118.9 (3)	N1—C8—H8A	109.00
O1—C2—C1	121.4 (3)	N1—C8—H8B	110.00
O1—C2—C3	119.7 (4)	C9—C8—H8A	109.00
C1—C2—C3	118.9 (4)	C9—C8—H8B	110.00
C2—C3—C4	121.8 (4)	H8A—C8—H8B	108.00
C3—C4—C5	119.5 (4)	C8—C9—H9A	109.00
Cl1—C5—C4	119.6 (3)	C8—C9—H9B	109.00
Cl1—C5—C6	119.5 (3)	C10—C9—H9A	109.00
C4—C5—C6	120.8 (4)	C10—C9—H9B	109.00
C1—C6—C5	120.2 (4)	H9A—C9—H9B	108.00
N1—C7—C1	122.3 (4)	C10—C11—H11	119.00
N1—C8—C9	110.8 (3)	C12—C11—H11	119.00
C8—C9—C10	111.4 (3)	C11—C12—H12	120.00
C9—C10—C15	121.1 (4)	C13—C12—H12	120.00
C11—C10—C15	117.8 (3)	C13—C14—H14	120.00
C9—C10—C11	121.1 (3)	C15—C14—H14	120.00
C10—C11—C12	121.3 (3)	C10—C15—H15	119.00
C11—C12—C13	119.9 (3)	C14—C15—H15	119.00
O2—S1—C13—C12	52.8 (3)	C2—C3—C4—C5	−1.1 (6)
O2—S1—C13—C14	−131.0 (3)	C3—C4—C5—Cl1	178.4 (3)
O3—S1—C13—C12	−177.3 (3)	C3—C4—C5—C6	0.5 (6)
O3—S1—C13—C14	−1.1 (3)	Cl1—C5—C6—C1	−177.3 (3)
N2—S1—C13—C12	−61.0 (3)	C4—C5—C6—C1	0.6 (6)
N2—S1—C13—C14	115.2 (3)	N1—C8—C9—C10	178.1 (3)
C8—N1—C7—C1	174.7 (3)	C8—C9—C10—C11	−95.0 (4)
C7—N1—C8—C9	122.1 (4)	C8—C9—C10—C15	84.1 (5)
C6—C1—C2—O1	−180.0 (4)	C9—C10—C11—C12	−179.5 (3)
C6—C1—C2—C3	0.5 (6)	C15—C10—C11—C12	1.5 (5)
C7—C1—C2—O1	3.9 (6)	C9—C10—C15—C14	178.9 (4)
C7—C1—C2—C3	−175.7 (4)	C11—C10—C15—C14	−2.0 (6)
C2—C1—C6—C5	−1.1 (6)	C10—C11—C12—C13	0.0 (5)
C7—C1—C6—C5	175.1 (4)	C11—C12—C13—S1	175.4 (3)
C2—C1—C7—N1	−3.0 (6)	C11—C12—C13—C14	−0.9 (5)
C6—C1—C7—N1	−179.1 (4)	S1—C13—C14—C15	−175.9 (3)
O1—C2—C3—C4	−179.0 (4)	C12—C13—C14—C15	0.3 (5)
C1—C2—C3—C4	0.6 (6)	C13—C14—C15—C10	1.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.8200	1.8300	2.554 (4)	147.00
N2—H2···O2i	0.77 (4)	2.30 (4)	3.016 (4)	156 (4)

S1—O2	1.430 (2)
S1—O3	1.423 (3)
S1—N2	1.616 (3)
S1—C13	1.752 (3)

O2—S1—O3	118.15 (14)
O2—S1—N2	105.67 (16)
O2—S1—C13	109.21 (15)
O3—S1—N2	108.20 (17)
O3—S1—C13	108.29 (15)
N2—S1—C13	106.76 (15)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.554 (4)	147.00
N2—H2⋯O2i	0.77 (4)	2.30 (4)	3.016 (4)	156 (4)

Symmetry code: (i) .