4-[(E)-(5-Chloro-2-hydroxy­benzyl­idene)amino]benzene­sulfonamide

Chohan, Z.H.; Shad, H.A.; Tahir, M.N.

doi:10.1107/S1600536808040853

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o57

doi:10.1107/S1600536808040853

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4-[(E)-(5-Chloro-2-hydroxybenzylidene)amino]benzenesulfonamide

Zahid H. Chohan,^a Hazoor A. Shad ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan-60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 2 December 2008; accepted 3 December 2008; online 10 December 2008)

In the molecule of title compound, C₁₃H₁₁ClN₂O₃S, the aromatic rings are oriented at a dihedral angle of 12.27 (3)°. An intramolecular 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, intermolecular N—H⋯O hydrogen bonds link the molecules.

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_r = 310.76
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.132
S = 1.02
3172 reflections
193 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 1125 Friedel pairs
Flack parameter: 0.09 (13)

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) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040853/hk2593sup1.cif

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

checkCIF report

Comment top

Sulfonamides have gained much attention due to their extensive use in medicine. Many novel sulfonamide derived compounds have been synthesized and reported (Chohan, 2008; Chohan & Shad, 2008; Chohan & Supuran, 2008; Nishimori et al., 2005) that are expected to attack the selective targets. This approach is supportive in controlling undesirable effects and producing distinctive pharmacological and clinical responses. In continuation to synthesize Schiff base ligands of 5-chlorosalicylaldehyde with different sulfonamides (Chohan et al., 2008a, 2008b; Shad et al., 2008), we have synthesized the title compound having the sulfanilamide, which is also a member of sulfonamides, and reported herein its crystal structure. The crystal structures of the individual moieties of δ-sulfanilamide have also been reported (Gelbrich et al., 2008) .

In the molecule of title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C8-C13) are, of course, planar, and the dihedral angle between them is A/B = 12.27 (3)°. The intramolecular O-H···N hydrogen bond (Table 1) results in the formation of a planar six-membered ring C (O1/N1/C1/C2/C7/H1), which is oriented with respect to rings A and B at dihedral angles of A/C = 2.36 (13)° and B/C = 13.22 (13)°. So, rings A and C are also nearly coplanar. In the sulfonamide group, the S1 atom is 0.457 (3) Å away from the plane of (O2/O3/N2).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

For the preparation of the title compound, sulfanilamide (344.4 mg, 2 mmol) in ethanol (20 ml) was mixed with 5-chlorosalicylaldehyde (313.1 mg, 2 mmol) in ethanol (10 ml). The resultant mixture was refluxed for 3 h by monitoring through TLC. During refluxing the solution turned from colorless to bright orange. After completion of reaction, it was cooled to room temperature, filtered and volume reduced to about one-third using rotary evaporator. It was then allowed to stand for 6 d at room temperature. After which, a crystallized product was formed that was filtered, washed with ethanol (2x5 ml), dried and recrystallized in a mixture of methanol/ethanol (1:1) to afford the orange crystals of the title compound (m.p. 469-471 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-[(E)-(5-Chloro-2-hydroxybenzylidene)amino]benzenesulfonamide top

Crystal data top

C₁₃H₁₁ClN₂O₃S	F(000) = 320
M_r = 310.76	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3172 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 7.6 pixels mm^-1	θ_max = 28.5°, θ_min = 0.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.904, T_max = 0.935	l = −31→29
7850 measured reflections

Refinement top

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(F_o²) + (0.0408P)² + 0.3674P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3172 reflections	Δρ_max = 0.25 e Å⁻³
193 parameters	Δρ_min = −0.36 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (13)

Crystal data top

C₁₃H₁₁ClN₂O₃S	V = 659.22 (16) Å³
M_r = 310.76	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.1936 (9) Å	µ = 0.46 mm⁻¹
b = 4.6002 (7) Å	T = 296 K
c = 23.252 (3) Å	0.25 × 0.18 × 0.15 mm
β = 95.699 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3172 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1842 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.935	R_int = 0.053
7850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.132	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.36 e Å⁻³
3172 reflections	Absolute structure: Flack (1983), 1125 Friedel pairs
193 parameters	Absolute structure parameter: 0.09 (13)
4 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁ClN₂O₃S
M_r	310.76
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.1936 (9), 4.6002 (7), 23.252 (3)
β (°)	95.699 (7)
V (Å³)	659.22 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.25 × 0.18 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.904, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	7850, 3172, 1842
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.132, 1.02
No. of reflections	3172
No. of parameters	193
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.36
Absolute structure	Flack (1983), 1125 Friedel pairs
Absolute structure parameter	0.09 (13)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.603 (5)	148.00
N2—H21···O3ⁱ	0.87 (4)	2.16 (4)	2.986 (6)	160 (5)

Symmetry code: (i) −x+1, y−1/2, −z+1.

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

References

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