4-{[4-(Di­methyl­amino)­benzyl­idene]amino}­benzene­sulfonamide

Mustafa Durgun; Hasan Türkmen; Tuncay Tunç; Tuncer Hökelek

doi:10.1107/S1600536814012136

. 2014 May 31;70(Pt 6):o726–o727. doi: 10.1107/S1600536814012136

4-{[4-(Dimethylamino)benzylidene]amino}benzenesulfonamide

Mustafa Durgun ^a, Hasan Türkmen ^a, Tuncay Tunç ^b, Tuncer Hökelek ^c,^*

PMCID: PMC4051049 PMID: 24940295

Abstract

The title Schiff base compound, C₁₅H₁₇N₃O₂S, is non-planar with a dihedral angle of 69.88 (4)° between the planes of the benzene rings. In the crystal, pairs of N—H⋯N hydrogen bonds, between the sulfonamide nitrogen-H atom and the azomethine N atom, link the molecules into inversion dimers, forming R ₂ ²(16) ring motifs. These dimers are linked by N—H⋯O hydrogen bonds, between the sulfonamide nitrogen-H atom and one sulfonamide O atom, forming sheets lying parallel to (100). Within the sheets there are weak parallel slipped π–π interactions involving inversion-related benzenesulfonamide rings [centroid–centroid distance = 3.8800 (9) Å; normal distance = 3.4796 (6) Å; slippage = 1.717 Å].

Related literature

For the biological and physical properties of sulfonamides and their derivatives and for their pharmacological applications, see: Chohan & Shad (2012 ▶); Domagk (1935 ▶); Khalil et al. (2009 ▶); Sharaby (2007 ▶); Lin et al. (2008 ▶); Maren (1967 ▶); Mohamed et al. (2013 ▶); Saluja et al. (2014 ▶); Supuran et al. (1996 ▶); Türkmen et al. (2005 ▶). For related structures, see: Idemudia et al. (2012 ▶); Loughrey et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶). graphic file with name e-70-0o726-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₇N₃O₂S
M _r = 303.38
Monoclinic,
a = 16.8982 (5) Å
b = 9.0273 (3) Å
c = 9.8405 (3) Å
β = 101.552 (3)°
V = 1470.71 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.35 × 0.22 × 0.15 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T _min = 0.924, T _max = 0.987
19398 measured reflections
3644 independent reflections
3133 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.116
S = 1.08
3644 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814012136/su2738sup1.cif

e-70-0o726-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012136/su2738Isup2.hkl

e-70-0o726-Isup2.hkl^{(175.1KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814012136/su2738Isup3.cml

CCDC reference: 1005250

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N2ⁱ	0.80 (3)	2.18 (3)	2.981 (2)	177 (2)
N3—H32⋯O2ⁱⁱ	0.832 (19)	2.494 (19)	3.321 (2)	174 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization), and the Unit of Scientific Research Projects of Harran University, Şanlıurfa, Turkey for a research grant (HUBAK grant No. 12040).

supplementary crystallographic information

1. Comment

Many Schiff bases are prepared by condensation reactions of a sulfonamide with a substituted benzaldehyde derivative. Such compounds contain both azomethine (-HC═N-) and sulfonamide (-SO₂NH₂) groups. Sulfonamide derivatives are very important because of their varied structures and biological activities (Domagk, 1935). This type of derivative displays interesting enzymatic inhibition towards the carbonic anhydrase (CA) isozymes CA I, II, IV, IX and XII (Supuran et al., 1996; Türkmen et al., 2005; Saluja et al., 2014) and the cyclo-oxygenase (COX) enzymes COX-1 and COX-2 (Lin et al., 2008) are still widely used as antimicrobial drugs, antithyroid agents, antibacterial, antifungal, antitumor, antibiotics, acid-base indicator, potential anticancer agents (Maren, 1967; Khalil et al., 2009; Sharaby, 2007; Mohamed et al., 2013; Chohan & Shad, 2012). The title compound was synthesized and its crystal structure is reported on herein.

In the molecule of the title compound (Fig. 1) the bond lengths are within normal ranges (Allen et al., 1987). The azomethine (-HC═N-) group is rotated out of the plane of the dimethylamino benzaldehyde and benzenesulfonamide benzene rings with torsion angles C5–C6–C9–N2 = -15.4 (2)° and C11–C10–N2–c9 = -53.6 (2)°. The two benzene rings A (C3—C8) and B (C10—C15) are oriented at a dihedral angle of 69.88 (4)°. Atoms N1, N2, C1, C2, C9 and C10 atoms are displaced from the plane of ring A by 0.034 (2), -0.302 (1), -0.045 (2), 0.106 (2), -0.018 (2) and -0.146 (2) Å, respectively, while atoms S1 and N2 are displaced from ring B by -0.0181 (4) and 0.026 (1) Å, respectively.

In the crystal, pairs of N—H···N hydrogen bonds link the molecules into inversion dimers forming R²₂(16) ring motifs (Table 1 and Fig. 2; Bernstein et al., 1995). These dimers are linked by N—H···O hydrogen bonds (Table 1) forming sheets lying parallel to (100). A π···π contact between inversion related the benzenesulfonamide benzene rings in the sheet, Cg2—Cg2ⁱ [symmetry code: (i) - x+1, - y+ 2, - z; where Cg2 is the centroid of ring B] may further stabilize the structure, with a centroid-centroid distance of 3.8800 (9) Å.

2. Experimental

The title compound was synthesized according to the literature method with some modifications (Khalil et al., 2009; Sharaby, 2007; Lin et al., 2008; Supuran et al., 1996; Mohamed et al., 2013). Sulfonamide (0.172 g, 1.0 mmol) in absolute ethanol (20 ml) was added to 4-(dimethylamino)benzaldehyde (0.149 g, 1.0 mmol) in absolute ethanol (20 ml), and 2 drops of formic acid were added as catalyst. The mixture was refluxed for 3-4 h, followed by cooling to room temperature. The resulting crystals were filtered in vacuum (yield: 85%). Crystals suitable for X-ray analysis were grown by slow evaporation of a methanol/ethanol/chloroform (3:1:1) solution, giving yellow prismatic crystals.