2-(1H-Benzimidazol-2-yl)-N-[(E)-(dimethyl­amino)­methyl­idene]benzene­sulfonamide

Adnan Ashraf; M Nawaz Tahir; Waseeq Ahmad Siddiqui; Nadia Perveen

doi:10.1107/S1600536812025159

. 2012 Jun 13;68(Pt 7):o2069. doi: 10.1107/S1600536812025159

2-(1H-Benzimidazol-2-yl)-N-[(E)-(dimethylamino)methylidene]benzenesulfonamide

Adnan Ashraf ^a, M Nawaz Tahir ^b,^*, Waseeq Ahmad Siddiqui ^a, Nadia Perveen ^a

PMCID: PMC3393333 PMID: 22807890

Abstract

The asymmetric unit of the title compound, C₁₆H₁₆N₄O₂S, contains two molecules (A and B) with similar conformations: the benzene rings are oriented at dihedral angles of 80.94 (10)° and 84.54 (10)° with their adjacent 1H-benzimidazole groups. In the crystal, the molecules are connected by N—H⋯N hydrogen bonds, forming separate C(4) chains of both the A and B molecules along [010]. The A and B chains are cross-linked by several C—H⋯O interactions involving the benzene rings and the sulfonyl groups, which lead to R ₂ ¹(5) loops in the linkage of the chains.

Related literature

For a related structure, see: Esparza-Ruiz et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₆N₄O₂S
M _r = 328.39
Monoclinic,
a = 15.630 (5) Å
b = 10.003 (4) Å
c = 22.122 (5) Å
β = 110.657 (5)°
V = 3236.3 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.930, T _max = 0.952
26702 measured reflections
6347 independent reflections
3328 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.159
S = 1.01
6347 reflections
419 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025159/hb6832sup1.cif

e-68-o2069-sup1.cif^{(38.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025159/hb6832Isup2.hkl

e-68-o2069-Isup2.hkl^{(304.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025159/hb6832Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.86	2.11	2.964 (3)	174
N5—H5A⋯N6ⁱⁱ	0.86	2.10	2.955 (3)	178
C9—H9⋯O4ⁱ	0.93	2.56	3.153 (4)	122
C10—H10⋯O4ⁱ	0.93	2.57	3.153 (4)	121
C25—H25⋯O2ⁱⁱ	0.93	2.47	3.114 (5)	127

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been prepared in an attempt to attach benzenesulfonyl chloride with 2-(1H-benzimidazol-2-yl) benzenesulfonamide (Crystal structure has been determined) in the dimethylformamide.

The crystal structures of 2-(1H-benzimidazol-3-ium-2-yl)benzenesulfonate dimethylsulfoxide solvate (Esparza-Ruiz et al., 2010) has been published which is related to (I) upto some extent.

In (I), two molecules (M1 and M2) in the asymmetric unit are present, which differ slightly from each other geometrically. In molecule M1, the group A (C1—C7/N1/N2) of 1H-benzimidazole, benzene ring B (C8—C13) and group C (N3/C14/N4/C15/C16) of N,N-dimethylimidoformamide moiety are planar with r. m. s. deviation of 0.0108 Å, 0.0046 Å and 0.0093 Å, respectively. The dihedral angle between A/B, A/C and B/C is 80.94 (10)°, 12.34 (4)° and 83.76 (18)°, respectively. The sulfonyl group D (O1/S1/O2) is of course planar. The dihedral angle between B/D and C/D is 70.86 (14)° and 53.88 (13)°, respectively. In second molecule M2, the similar groups E (C17—C23/N5/N6), F (C24—C29) and G (N7/C30/N8/C31/C32) are also planar with r. m. s. deviation of 0.0160 Å, 0.0054 Å and 0.0122 Å, respectively. The dihedral angle between E/F, E/G and F/G is 84.54 (10)°, 12.68 (8)° and 83.22 (20)°, respectively. In M2, dihedral angle between F/H and G/H is 69.47 (14)° and 54.53 (13)°, respectively where H (O3/S2/O4) is the sulfonyl group. Both molecules are interlinked with themselves with C (4) chains due to classical H–bonding of N—H···N type (Table 1, Fig. 2). These infinte one-dimensional chains exist along [010]. The polymeric chains are interlinked with each other through benzene ring and the sulfonyl groups due to H–bonding of C—H···O type in a different manner. There exist R₂¹(5) ring motif in the linkage of polymeric chains.

Experimental

The 2-[o-(sulfamoyl)phenyl]benzimidazole (0.1 g, 0.37 mmol) in dimethylformamide (2 ml) was disolved to get a clear solution. Benzenesulfonyl chloride (0.065 g, 0.37 mmol) was added with catalytic amount of potassium carbonate to this solution and subjected to reflux for 2 h. The resulting solution was quenched in ice-cold distilled water (100 ml). Extracted the aqueous layer with ethyl acetate (3 × 25 ml) and dried the organic layer over anhydrous sodium sulfate to get light brown powder (0.11 g, 90.5%). The powder was recrystallized in methanol to get the light brown prisms of (I).

m.p. 593–594 K.