4-[(E)-(5-Chloro-2-hydroxy-benzyl-idene)amino]benzene-sulfonamide.

In the mol-ecule of title compound, C(13)H(11)ClN(2)O(3)S, the aromatic rings are oriented at a dihedral angle of 12.27 (3)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar (mean deviation 0.0083 Å) six-membered ring, which is nearly coplanar with the adjacent ring at a dihedral angle of 2.36 (13)°. In the sulfonamide group, the S atom is 0.457 (3) Å from the plane through the O and N atoms. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Chohan (2008 ▶); Chohan & Shad (2008 ▶); Chohan & Supuran (2008 ▶); Nishimori et al. (2005 ▶). For related structures, see: Chohan et al. (2008a ▶,b ▶); Shad et al. (2008 ▶); Gelbrich et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H11ClN2O3S

M = 310.76

Monoclinic,

a = 6.1936 (9) Å

b = 4.6002 (7) Å

c = 23.252 (3) Å

β = 95.699 (7)°

V = 659.22 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 296 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.904, T max = 0.935

7850 measured reflections

3172 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.132

S = 1.02

3172 reflections

193 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 1125 Friedel pairs

Flack parameter: 0.09 (13)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536808040853/hk2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040853/hk2593Isup2.hkl

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

C13H11ClN2O3S	F(000) = 320
Mr = 310.76	Dx = 1.566 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1848 reflections
a = 6.1936 (9) Å	θ = 0.9–26.4°
b = 4.6002 (7) Å	µ = 0.46 mm−1
c = 23.252 (3) Å	T = 296 K
β = 95.699 (7)°	Prism, orange
V = 659.22 (16) Å3	0.25 × 0.18 × 0.15 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	3172 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 7.6 pixels mm-1	θmax = 28.5°, θmin = 0.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.904, Tmax = 0.935	l = −31→29
7850 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3674P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3172 reflections	Δρmax = 0.25 e Å−3
193 parameters	Δρmin = −0.36 e Å−3
4 restraints	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (13)

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	0.76662 (18)	1.3639 (2)	0.57243 (4)	0.0351 (3)
Cl1	0.7848 (2)	−0.1726 (4)	0.96987 (6)	0.0659 (4)
O1	0.1496 (5)	0.3015 (9)	0.79117 (14)	0.0554 (10)
H1	0.2062	0.4241	0.7719	0.083*
O2	0.9594 (5)	1.5110 (7)	0.59629 (14)	0.0498 (9)
O3	0.5902 (5)	1.5306 (7)	0.54481 (14)	0.0472 (9)
N1	0.4614 (6)	0.6117 (9)	0.75542 (16)	0.0365 (9)
N2	0.8345 (8)	1.1435 (9)	0.52410 (19)	0.0431 (11)
H21	0.726 (6)	1.068 (12)	0.5029 (19)	0.07 (2)*
H22	0.929 (8)	1.022 (12)	0.541 (2)	0.08 (2)*
C1	0.5139 (7)	0.2913 (9)	0.83587 (19)	0.0344 (11)
C2	0.2983 (8)	0.1959 (11)	0.8319 (2)	0.0394 (12)
C3	0.2389 (8)	−0.0151 (12)	0.8696 (2)	0.0490 (13)
H3	0.0970	−0.0837	0.8659	0.059*
C4	0.3850 (8)	−0.1254 (15)	0.91213 (19)	0.0501 (12)
H4	0.3418	−0.2638	0.9378	0.060*
C5	0.5997 (8)	−0.0272 (11)	0.91650 (19)	0.0430 (12)
C6	0.6617 (8)	0.1767 (11)	0.8793 (2)	0.0420 (12)
H6	0.8048	0.2409	0.8827	0.050*
C7	0.5892 (8)	0.4971 (11)	0.7953 (2)	0.0391 (12)
H7	0.742 (7)	0.545 (10)	0.8017 (17)	0.040 (13)*
C8	0.5381 (7)	0.8040 (10)	0.71469 (17)	0.0335 (11)
C9	0.7445 (7)	0.9293 (10)	0.72084 (19)	0.0425 (13)
H9	0.8379	0.8935	0.7539	0.051*
C10	0.8097 (8)	1.1053 (10)	0.67816 (19)	0.0385 (12)
H10	0.9476	1.1875	0.6824	0.046*
C11	0.6728 (7)	1.1609 (9)	0.62919 (18)	0.0312 (10)
C12	0.4655 (7)	1.0440 (11)	0.6241 (2)	0.0422 (12)
H12	0.3702	1.0855	0.5916	0.051*
C13	0.4006 (7)	0.8677 (14)	0.66654 (18)	0.0411 (11)
H13	0.2612	0.7903	0.6627	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0380 (7)	0.0288 (5)	0.0380 (6)	−0.0026 (6)	0.0009 (5)	−0.0002 (6)
Cl1	0.0711 (9)	0.0698 (10)	0.0545 (8)	0.0074 (9)	−0.0056 (7)	0.0153 (8)
O1	0.0333 (18)	0.065 (3)	0.066 (2)	−0.0079 (19)	−0.0044 (17)	0.012 (2)
O2	0.049 (2)	0.048 (2)	0.051 (2)	−0.0232 (18)	−0.0069 (17)	0.0015 (17)
O3	0.050 (2)	0.0369 (19)	0.053 (2)	0.0081 (17)	−0.0039 (17)	0.0064 (16)
N1	0.035 (2)	0.037 (2)	0.038 (2)	−0.0014 (18)	0.0037 (19)	0.0012 (18)
N2	0.047 (3)	0.040 (3)	0.043 (3)	−0.003 (2)	0.011 (2)	−0.010 (2)
C1	0.031 (3)	0.033 (3)	0.040 (3)	0.002 (2)	0.007 (2)	−0.003 (2)
C2	0.032 (3)	0.040 (3)	0.046 (3)	−0.002 (2)	0.007 (2)	−0.003 (2)
C3	0.042 (3)	0.052 (3)	0.056 (3)	−0.007 (3)	0.018 (3)	−0.002 (3)
C4	0.060 (3)	0.052 (3)	0.042 (3)	−0.006 (4)	0.021 (2)	0.000 (3)
C5	0.054 (3)	0.044 (3)	0.031 (3)	0.007 (3)	0.005 (2)	−0.001 (2)
C6	0.037 (3)	0.042 (3)	0.047 (3)	0.001 (2)	0.003 (2)	−0.004 (2)
C7	0.028 (3)	0.038 (3)	0.052 (3)	−0.004 (2)	0.005 (3)	−0.002 (2)
C8	0.033 (3)	0.035 (3)	0.034 (2)	0.003 (2)	0.008 (2)	−0.003 (2)
C9	0.034 (3)	0.054 (4)	0.038 (3)	−0.003 (2)	−0.006 (2)	0.007 (2)
C10	0.030 (3)	0.045 (3)	0.039 (3)	−0.006 (2)	−0.002 (2)	0.002 (2)
C11	0.028 (3)	0.030 (2)	0.036 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C12	0.029 (3)	0.049 (3)	0.046 (3)	0.000 (2)	−0.008 (2)	0.008 (2)
C13	0.024 (2)	0.049 (3)	0.050 (3)	−0.003 (3)	0.005 (2)	0.008 (3)

Cl1—C5	1.738 (5)	C6—C5	1.358 (7)
S1—O2	1.435 (3)	C6—H6	0.9300
S1—O3	1.434 (3)	C7—N1	1.272 (6)
S1—N2	1.600 (4)	C7—C1	1.446 (6)
S1—C11	1.762 (5)	C7—H7	0.97 (4)
O1—H1	0.8200	C8—N1	1.412 (5)
N2—H21	0.87 (4)	C9—C8	1.397 (6)
N2—H22	0.87 (5)	C9—C10	1.372 (6)
C2—O1	1.344 (5)	C9—H9	0.9300
C2—C3	1.381 (7)	C10—H10	0.9300
C2—C1	1.400 (6)	C11—C10	1.375 (6)
C3—C4	1.370 (7)	C11—C12	1.386 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—H4	0.9300	C13—C8	1.370 (6)
C5—C4	1.398 (7)	C13—C12	1.369 (7)
C6—C1	1.397 (6)	C13—H13	0.9300
O2—S1—N2	107.7 (2)	C6—C5—C4	120.3 (5)
O2—S1—C11	106.48 (19)	C1—C6—H6	119.5
O3—S1—O2	119.3 (2)	C5—C6—C1	121.0 (5)
O3—S1—N2	105.4 (2)	C5—C6—H6	119.5
O3—S1—C11	109.0 (2)	N1—C7—C1	121.9 (4)
N2—S1—C11	108.6 (2)	N1—C7—H7	123 (3)
C2—O1—H1	109.5	C1—C7—H7	115 (3)
C7—N1—C8	121.4 (4)	C9—C8—N1	123.7 (4)
S1—N2—H21	114 (4)	C13—C8—C9	118.9 (4)
S1—N2—H22	108 (4)	C13—C8—N1	117.3 (4)
H21—N2—H22	117 (6)	C8—C9—H9	119.9
C2—C1—C7	122.0 (4)	C10—C9—C8	120.1 (4)
C6—C1—C2	118.8 (4)	C10—C9—H9	119.9
C6—C1—C7	119.2 (4)	C9—C10—C11	120.5 (4)
O1—C2—C1	121.0 (4)	C9—C10—H10	119.8
O1—C2—C3	119.6 (5)	C11—C10—H10	119.8
C3—C2—C1	119.4 (5)	C10—C11—C12	119.3 (4)
C2—C3—H3	119.3	C10—C11—S1	119.8 (4)
C4—C3—C2	121.3 (5)	C12—C11—S1	120.8 (3)
C4—C3—H3	119.3	C11—C12—H12	119.9
C3—C4—C5	119.2 (5)	C13—C12—C11	120.2 (4)
C3—C4—H4	120.4	C13—C12—H12	119.9
C5—C4—H4	120.4	C8—C13—H13	119.6
C4—C5—Cl1	118.9 (4)	C12—C13—C8	120.9 (4)
C6—C5—Cl1	120.9 (4)	C12—C13—H13	119.6
O2—S1—C11—C10	−17.2 (4)	C1—C6—C5—C4	−0.3 (7)
O2—S1—C11—C12	165.9 (4)	C1—C6—C5—Cl1	179.2 (4)
O3—S1—C11—C10	−147.1 (4)	N1—C7—C1—C6	−179.0 (5)
O3—S1—C11—C12	36.0 (4)	N1—C7—C1—C2	3.1 (7)
N2—S1—C11—C10	98.5 (4)	C1—C7—N1—C8	−177.6 (4)
N2—S1—C11—C12	−78.4 (4)	C9—C8—N1—C7	−13.3 (7)
O1—C2—C1—C6	179.5 (4)	C13—C8—N1—C7	166.4 (5)
O1—C2—C1—C7	−2.6 (7)	C10—C9—C8—N1	177.4 (4)
C3—C2—C1—C6	−2.1 (7)	C10—C9—C8—C13	−2.2 (7)
C3—C2—C1—C7	175.8 (4)	C8—C9—C10—C11	0.3 (7)
O1—C2—C3—C4	−179.1 (5)	S1—C11—C10—C9	−175.1 (4)
C1—C2—C3—C4	2.4 (8)	C12—C11—C10—C9	1.8 (7)
C2—C3—C4—C5	−1.6 (8)	S1—C11—C12—C13	174.8 (4)
C6—C5—C4—C3	0.5 (8)	C10—C11—C12—C13	−2.0 (7)
Cl1—C5—C4—C3	−179.0 (4)	C12—C13—C8—N1	−177.6 (5)
C5—C6—C1—C2	1.1 (7)	C12—C13—C8—C9	2.0 (8)
C5—C6—C1—C7	−176.9 (4)	C8—C13—C12—C11	0.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.603 (5)	148
N2—H21···O3i	0.87 (4)	2.16 (4)	2.986 (6)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.603 (5)	148
N2—H21⋯O3i	0.87 (4)	2.16 (4)	2.986 (6)	160 (5)

Symmetry code: (i) .