organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
1959). We report here the syntheses and crystal structures of
two new benzenesulfonamides, namely 2-[N-(2-chlorophenyl)-
carbamoyl]benzenesulfonamide, (I), and 2-[N-(4-chloro-
phenyl)carbamoyl]benzenesulfonamide, (II).
ISSN 0108-2701
2-[N-(X-Chlorophenyl)carbamoyl]-
benzenesulfonamide (with X = 2
and 4)
Waseeq Ahmad Siddiqui,a Saeed Ahmad,b Islam Ullah
Khan,c Hamid Latif Siddiquid and Masood Parveze*
The molecular structure of (I) is presented in Fig. 1. The
mean planes of the C1–C6 and C8–C13 benzene rings are
inclined at 48.83 (8)ꢀ with respect to each other, while the
carbamoyl group (O1/N2/C7) is inclined at 70.51 (13) and
29.6 (2)ꢀ, respectively, with respect to these benzene rings. The
structure contains two distinct patterns of hydrogen bonds
involving intermolecular N—Hꢁ ꢁ ꢁO interactions (Fig. 2). The
sulfonamide groups are hydrogen bonded via atoms N1 and
O3, forming chains of molecules. The carbamoyl groups are
also hydrogen bonded, via atoms O1 and N2, resulting in two
parallel hydrogen-bonding patterns and affording stability to
the polymeric chains running parallel to the c axis. There are
two nonclassical intermolecular C—Hꢁ ꢁ ꢁO hydrogen bonds
and the structure is further stabilized by four additional
intramolecular interactions, viz. N1—H1NAꢁ ꢁ ꢁO1, C13—
H13ꢁ ꢁ ꢁO1, C2—H2ꢁ ꢁ ꢁO3 and N2—H2Nꢁ ꢁ ꢁCl1, resulting in
seven-, six-, five- and five-membered rings with S(7), S(6), S(5)
and S(5) motifs, respectively (Bernstein et al., 1994); details of
the hydrogen-bonding geometry are given in Table 1.
The molecular structure of (II) is presented in Fig. 3. The
mean planes of the C1–C6 and C8–C13 benzene rings are
inclined at 42.92 (6)ꢀ with respect to each other, while the
carbamoyl group (O1/N2/C7) is inclined at 57.10 (11) and
17.96 (18)ꢀ, respectively, with respect to these benzene rings.
The structure of (II) also contains two patterns of hydrogen
bonds (Fig. 4), similar to those observed in (I). The sulfona-
mide groups in (II) are hydrogen bonded via atoms N1 and
O3, forming chains of molecules. The carbamoyl groups are
also hydrogen bonded, via atoms O1 and N2, resulting in two
parallel hydrogen-bonding patterns and affording stability to
the polymeric chains running parallel to the a axis. There are
two nonclassical C—Hꢁ ꢁ ꢁO hydrogen bonds and the structure
is further stabilized by three additional intramolecular inter-
actions, viz. N1—H1NAꢁ ꢁ ꢁO1, C13—H13ꢁ ꢁ ꢁO1 and C2—
H2ꢁ ꢁ ꢁO3, resulting in seven-, six- and five-membered rings
with S(7), S(6) and S(5) motifs, respectively; details of the
hydrogen-bonding geometry are given in Table 2.
aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, bDepartment
of Chemistry, University of Science and Technology, Bannu, Pakistan, cDepartment
of Chemistry, Government College University, Lahore, Pakistan, dInstitute of
Chemistry, University of the Punjab, Lahore, Pakistan, and eDepartment of
Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta,
Canada T2N 1N4
Correspondence e-mail: parvez@ucalgary.ca
Received 4 March 2008
Accepted 7 April 2008
Online 19 April 2008
The structures of 2-[N-(2-chlorophenyl)carbamoyl]benzene-
sulfonamide and 2-[N-(4-chlorophenyl)carbamoyl]benzene-
sulfonamide, both C13H11ClN2O3S, are stabilized by
extensive intra- and intermolecular hydrogen bonds. In both
structures, sulfonamide groups are hydrogen bonded via the N
and O atoms and form chains of molecules. The carbamoyl
groups are also hydrogen bonded, involving the O and N
atoms, further strengthening the polymeric chains running
along the c and a axes in the 2- and 4-chloro derivatives,
respectively. Carbamoylsulfonamide derivatives are novel
compounds with a great potential for medicinal applications.
Comment
Benzenesulfonamide derivatives are well known in the
biological sciences for their antibacterial, anticancer and anti-
HIV activities (Brzozowski, 1996; Stawinski, 1997; Alovero et
al., 2001). In the field of catalysis, their chloro derivatives are
particularly important for carrying out a large number of
oxidation reactions wherein the reaction kinetics are very
important (Shashikala & Rangappa, 2002; Puttaswamy, 2001).
The crystal structures of a number of interesting derivatives of
benzenesulfonamide have been reported recently (Clark et al.,
2003; Vyas et al., 2003; Singh et al., 2004; Bocelli et al., 1995;
Sutton & Cody, 1989; Furuya et al., 1989). While continuing
our research on the synthesis of biologically important 1,2-
benzothiazine derivatives (Siddiqui et al., 2007, 2008), we have
devised a simple and straightforward route for the synthesis of
2-[(chlorophenyl)carbamoyl]benzenesulfonamide derivatives
directly from saccharin as starting material. The syntheses of
only two unsubstituted 2-cyclohexyl and 2-phenylcarbamoyl-
benzenesulfonamide derivatives have been reported to date,
utilizing N-vinylsulfobenzimide as starting material (Kiyoshi,
In both molecules, the conformation about the S—N bond is
in agreement with the conformation of a handful of structures
containing an 2-C-substituted benzenesulfonamide fragment;
there were 14 hits in the Cambridge Structural Database
(CSD, Version 5.29; Allen, 2002). The N1 atoms in both
structures are tetrahedral, with angles at N1 in the ranges
105 (3)–120 (3) (sum 338ꢀ) and 112 (2)–116 (3)ꢀ (sum 342ꢀ)
o286 # 2008 International Union of Crystallography
doi:10.1107/S0108270108009530
Acta Cryst. (2008). C64, o286–o289
Siddiqui, Waseeq Ahmad
