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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o725.
Published online 2008 March 20. doi:  10.1107/S1600536808005084
PMCID: PMC2960939

4-{2-[(5-Chloro-2-hydroxy­benzyl­idene)amino]eth­yl}benzene­sulfonamide

Abstract

In the mol­ecule of the title compound, C15H15ClN2O3S, the S atom adopts a distorted tetra­hedral coordination geometry with two O atoms, one N atom of the amide group and one C atom of the aromatic ring. An intra­molecular 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, inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0o725-scheme1.jpg

Experimental

Crystal data

  • C15H15ClN2O3S
  • M r = 338.80
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o725-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

The significance of sulfonamide was realised when sulfanilamide was first time reported as antibacterial drug. Later on, many sulfanilamide derivatives were synthesized, characterized and tested for antibacterial, anti-tumour, anti-carbonic anhydrase (Supuran & Scozzafava 2001), diuretic, hypoglycemic, anti-thyroid or protease inhibitory activity. Thus, sulfanilamide is performing a leading role for the development and expansion of all other types of medicinally important sulfonamides (Chohan & Shad, 2007).

The title compound, (I), is a reaction product of 5-chlorosalicylaldehyde and 4-(2-aminoethyl)benzenesulfonamide. The 4-(2-aminoethyl)benzenesulfonamide moiety is present in 4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolidine-1-carboxamido)- ethyl]benzenesulfonamide (Li, 2006) and 5-chlorosalicylaldehyde exists in 4-[(5-chloro-2-hydroxybenzylidene)amino]-N-(3,4-dimethylisoxazol-5-yl)benzene- sulfonamide (Chohan et al., 2008). In continuation of synthesizing Schiff base ligands of substituted halogen salicylaldehydes and various sulfonamides (Chohan et al., 2008; Shad et al., 2008; Tahir et al., 2008), we report herein the crystal structure of the title compound, (I).

In the molecule of (I), S1 atom has a distorted tetrahedral coordination completed by the two O atoms, one N atom of amide group and one C atom of the adjacent aromatic ring B (C10—C15) (Table 1, Fig. 1). The two aromatic rings A (C1—C6) and B are connected by C=N—C—C group in a zigzag way, in which they are oriented at a dihedral angle of A/B = 23.95 (18)°. The intramolecular O—H···N hydrogen bond (Table 2) results in the formation of a planar six-membered ring C (O1/H1/N1/C7/C1/C2), which is oriented with respect to the aromatic rings at dihedral angles of A/C = 3.38 (11)° and B/C = 22.33 (13)°. So, rings A and C are also nearly coplanar.

In (I), C7—N1 [1.278 (5) Å] bond has double bond character. The C2=O1 [1.343 (5) Å] bond is a little longer than the corresponding value [1.328 (4) Å], as reported by Chohan et al. (2008). All other bonds in 5-chlorosalicylaldehyde moiety remain nearly same. The bond angles around S1 atom of sulfonamide group are a little smaller, having the range of 106.76 (15)° - 118.15 (14)°, compared to the values, in the range of 105.91 (13)°-119.68 (12)°, as reported by Li (2006).

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, an ethanol solution (15 ml) of 4-(2-aminoethyl)benzenesulfonamide (400.5 mg, 2 mmol) was added to an ethanol solution (10 ml) of 5-chlorosalicylaldehyde (313.1 mg, 2 mmol). The reaction mixture was refluxed for 3 h. The colour of the solution gradually changed from colorless to greenish yellow. The solution was cooled to room temperature, filtered and the volume was reduced to about one-third on the rotary evaporator. It was allowed to stand for 10 d, bright yellow crystals of the title compound were obtained (m.p. 441 K).

Refinement

H atoms (for NH2) were located in a difference synthesis and refined isotropically [N—H = 0.77 (4) and 0.78 (4) Å; Uiso(H) = 0.0767 and 0.0613 Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms.

Figures

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

Crystal data

C15H15ClN2O3SF000 = 1408
Mr = 338.80Dx = 1.461 Mg m3
Monoclinic, C2/cMelting point: 497 K
Hall symbol: -C 2ycMo Kα radiation λ = 0.71073 Å
a = 21.069 (2) ÅCell parameters from 2163 reflections
b = 4.8125 (6) Åθ = 1.3–29.2º
c = 30.838 (3) ŵ = 0.40 mm1
β = 99.942 (9)ºT = 296 (2) K
V = 3079.9 (6) Å3Prismatic, yellow
Z = 80.22 × 0.18 × 0.14 mm

Data collection

Bruker KappaAPEXII CCD diffractometer4067 independent reflections
Radiation source: fine-focus sealed tube1851 reflections with I > 3σ(I)
Monochromator: graphiteRint = 0.060
Detector resolution: 7.40 pixels mm-1θmax = 29.2º
T = 296(2) Kθmin = 1.3º
ω scansh = −28→28
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −6→5
Tmin = 0.920, Tmax = 0.940l = −41→42
16002 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H 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 reflectionsΔρmax = 0.36 e Å3
206 parametersΔρmin = −0.28 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
Cl10.32293 (6)0.3434 (3)0.35291 (5)0.1046 (5)
S1−0.14925 (4)0.84474 (16)−0.01326 (3)0.0411 (3)
O10.07158 (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)
N10.06373 (16)0.2662 (6)0.21557 (9)0.0566 (10)
N2−0.18450 (17)0.5984 (6)−0.04399 (11)0.0510 (11)
C10.15618 (18)0.2192 (8)0.27152 (11)0.0494 (11)
C20.12970 (19)−0.0013 (8)0.29194 (12)0.0526 (11)
C30.1641 (2)−0.1103 (9)0.33014 (13)0.0687 (16)
C40.2227 (2)−0.0078 (9)0.34865 (13)0.0677 (16)
C50.24889 (19)0.2059 (9)0.32861 (14)0.0663 (14)
C60.2167 (2)0.3195 (9)0.29034 (13)0.0655 (14)
C70.1197 (2)0.3508 (8)0.23331 (12)0.0590 (12)
C80.0272 (2)0.4227 (8)0.17939 (12)0.0622 (14)
C90.0102 (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)
H10.05445−0.009640.254630.1087*
H2−0.212 (2)0.526 (9)−0.0349 (15)0.0767*
H2A−0.160 (2)0.495 (9)−0.0511 (14)0.0613*
H30.14678−0.258110.343660.0825*
H40.24468−0.082760.374770.0812*
H60.235280.464030.276900.0786*
H70.137390.502800.221100.0710*
H8A0.052520.580260.172610.0746*
H8B−0.011900.493180.188000.0746*
H9A0.049450.178190.130170.0782*
H9B−0.013700.082660.146420.0782*
H11−0.117060.277610.113060.0667*
H12−0.177580.513680.055830.0607*
H14−0.016350.814930.021470.0647*
H150.043860.583890.079560.0747*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0648 (7)0.1294 (11)0.1019 (10)0.0029 (8)−0.0357 (7)−0.0252 (8)
S10.0365 (4)0.0370 (4)0.0461 (5)−0.0006 (4)−0.0030 (3)0.0111 (4)
O10.0634 (17)0.076 (2)0.0685 (19)−0.0105 (16)−0.0151 (14)0.0163 (14)
O20.0434 (14)0.0394 (12)0.0741 (18)0.0078 (11)0.0002 (13)0.0034 (12)
O30.0485 (14)0.0685 (15)0.0621 (16)−0.0062 (14)0.0036 (13)0.0313 (13)
N10.0563 (18)0.0628 (18)0.0439 (17)0.0072 (17)−0.0104 (15)0.0043 (14)
N20.054 (2)0.0502 (19)0.0440 (18)−0.0025 (15)−0.0054 (15)0.0014 (14)
C10.0497 (19)0.058 (2)0.0367 (18)0.0091 (18)−0.0034 (16)−0.0007 (16)
C20.057 (2)0.057 (2)0.0391 (19)0.012 (2)−0.0050 (17)−0.0024 (16)
C30.078 (3)0.069 (3)0.053 (2)0.012 (2)−0.006 (2)0.010 (2)
C40.074 (3)0.076 (3)0.044 (2)0.024 (3)−0.015 (2)−0.002 (2)
C50.051 (2)0.086 (3)0.054 (2)0.015 (2)−0.0134 (19)−0.023 (2)
C60.057 (2)0.081 (3)0.053 (2)0.003 (2)−0.0063 (19)0.001 (2)
C70.061 (2)0.066 (2)0.045 (2)0.001 (2)−0.0047 (18)0.0111 (18)
C80.069 (3)0.055 (2)0.055 (2)0.014 (2)−0.011 (2)0.0057 (18)
C90.083 (3)0.059 (2)0.045 (2)0.021 (2)−0.014 (2)0.0039 (18)
C100.062 (2)0.046 (2)0.0371 (18)0.0077 (19)−0.0063 (17)0.0017 (15)
C110.058 (2)0.061 (2)0.045 (2)−0.005 (2)0.0013 (18)0.0167 (17)
C120.0418 (19)0.061 (2)0.045 (2)−0.0051 (18)−0.0017 (16)0.0101 (17)
C130.0348 (15)0.0331 (16)0.0366 (17)−0.0014 (14)0.0003 (13)0.0030 (13)
C140.0354 (17)0.070 (2)0.054 (2)−0.0030 (19)0.0025 (17)0.0195 (19)
C150.0372 (18)0.088 (3)0.058 (2)0.009 (2)−0.0039 (17)0.012 (2)

Geometric parameters (Å, °)

Cl1—C51.741 (4)C9—C101.499 (5)
S1—O21.430 (2)C10—C151.380 (5)
S1—O31.423 (3)C10—C111.395 (6)
S1—N21.616 (3)C11—C121.370 (5)
S1—C131.752 (3)C12—C131.375 (5)
O1—C21.343 (5)C13—C141.384 (5)
O1—H10.8200C14—C151.374 (5)
N1—C71.278 (5)C3—H30.9300
N1—C81.452 (5)C4—H40.9300
N2—H20.77 (4)C6—H60.9300
N2—H2A0.78 (4)C7—H70.9300
C1—C71.438 (5)C8—H8A0.9700
C1—C21.398 (5)C8—H8B0.9700
C1—C61.393 (6)C9—H9A0.9700
C2—C31.376 (6)C9—H9B0.9700
C3—C41.360 (6)C11—H110.9300
C4—C51.365 (6)C12—H120.9300
C5—C61.369 (6)C14—H140.9300
C8—C91.499 (5)C15—H150.9300
O2—S1—O3118.15 (14)S1—C13—C12119.8 (2)
O2—S1—N2105.67 (16)C12—C13—C14119.9 (3)
O2—S1—C13109.21 (15)S1—C13—C14120.2 (2)
O3—S1—N2108.20 (17)C13—C14—C15119.7 (3)
O3—S1—C13108.29 (15)C10—C15—C14121.5 (4)
N2—S1—C13106.76 (15)C2—C3—H3119.00
C2—O1—H1109.00C4—C3—H3119.00
C7—N1—C8119.4 (3)C3—C4—H4120.00
S1—N2—H2115 (3)C5—C4—H4120.00
S1—N2—H2A112 (3)C1—C6—H6120.00
H2—N2—H2A113 (5)C5—C6—H6120.00
C2—C1—C7120.3 (3)N1—C7—H7119.00
C6—C1—C7120.7 (4)C1—C7—H7119.00
C2—C1—C6118.9 (3)N1—C8—H8A109.00
O1—C2—C1121.4 (3)N1—C8—H8B110.00
O1—C2—C3119.7 (4)C9—C8—H8A109.00
C1—C2—C3118.9 (4)C9—C8—H8B110.00
C2—C3—C4121.8 (4)H8A—C8—H8B108.00
C3—C4—C5119.5 (4)C8—C9—H9A109.00
Cl1—C5—C4119.6 (3)C8—C9—H9B109.00
Cl1—C5—C6119.5 (3)C10—C9—H9A109.00
C4—C5—C6120.8 (4)C10—C9—H9B109.00
C1—C6—C5120.2 (4)H9A—C9—H9B108.00
N1—C7—C1122.3 (4)C10—C11—H11119.00
N1—C8—C9110.8 (3)C12—C11—H11119.00
C8—C9—C10111.4 (3)C11—C12—H12120.00
C9—C10—C15121.1 (4)C13—C12—H12120.00
C11—C10—C15117.8 (3)C13—C14—H14120.00
C9—C10—C11121.1 (3)C15—C14—H14120.00
C10—C11—C12121.3 (3)C10—C15—H15119.00
C11—C12—C13119.9 (3)C14—C15—H15119.00
O2—S1—C13—C1252.8 (3)C2—C3—C4—C5−1.1 (6)
O2—S1—C13—C14−131.0 (3)C3—C4—C5—Cl1178.4 (3)
O3—S1—C13—C12−177.3 (3)C3—C4—C5—C60.5 (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—C10.6 (6)
N2—S1—C13—C14115.2 (3)N1—C8—C9—C10178.1 (3)
C8—N1—C7—C1174.7 (3)C8—C9—C10—C11−95.0 (4)
C7—N1—C8—C9122.1 (4)C8—C9—C10—C1584.1 (5)
C6—C1—C2—O1−180.0 (4)C9—C10—C11—C12−179.5 (3)
C6—C1—C2—C30.5 (6)C15—C10—C11—C121.5 (5)
C7—C1—C2—O13.9 (6)C9—C10—C15—C14178.9 (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—C130.0 (5)
C7—C1—C6—C5175.1 (4)C11—C12—C13—S1175.4 (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—C150.3 (5)
C1—C2—C3—C40.6 (6)C13—C14—C15—C101.2 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.82001.83002.554 (4)147.00
N2—H2···O2i0.77 (4)2.30 (4)3.016 (4)156 (4)

Symmetry codes: (i) −x−1/2, −y+3/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2428).

References

  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 (Version 1.27) and SAINT (Version 7.12a). Bruker AXS Inc., Madison, Wisconsin, USA.
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  • Shad, H. A., Chohan, Z. H., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o635. [PMC free article] [PubMed]
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