Benzyl­sulfamide

Thomas Gelbrich; Mairi F Haddow; Ulrich J Griesser

doi:10.1107/S1600536811019490

. 2011 May 28;67(Pt 6):o1551–o1552. doi: 10.1107/S1600536811019490

Benzylsulfamide

Thomas Gelbrich ^a,^*, Mairi F Haddow ^a,^‡, Ulrich J Griesser ^a

PMCID: PMC3120398 PMID: 21754910

Abstract

The crystal of the title compound [systematic name: 4-(benzylamino)benzenesulfonamide], C₁₃H₁₄N₂O₂S, displays a hydrogen-bonded framework structure. Molecules are doubly N—H⋯O hydrogen bonded to one another via their NH₂ groups and sulfonyl O atoms. These interactions generate a hydrogen-bonded ladder structure parallel to the a axis, which contains fused R ₂ ²(8) rings. The NH group serves as the hydrogen-bond donor for a second set of intermolecular N—H⋯O=S interactions.

Related literature

For the pharmacology and synthesis of the title compound, see Goissedet et al. (1936 ▶); Goissedet & Despois (1938 ▶); Mellon et al. (1938 ▶); Long & Bliss (1939 ▶). For related structures, see: Hursthouse et al. (1998 ▶, 1999a ▶,b ▶); Gelbrich et al. (2008 ▶); Davis et al. (1996 ▶); Costanzo et al. (1999 ▶); Kubicki & Codding (2001 ▶);Yathirajan et al. (2005 ▶); Denehy et al. (2006 ▶); Toumieux et al. (2006 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₄N₂O₂S
M _r = 262.32
Orthorhombic,
a = 7.8426 (1) Å
b = 10.5549 (11) Å
c = 14.6694 (3) Å
V = 1214.30 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.950, T _max = 0.962
11460 measured reflections
2364 independent reflections
2312 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.061
S = 1.06
2364 reflections
176 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 972 Friedel pairs
Flack parameter: −0.01 (5)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019490/ez2246sup1.cif

e-67-o1551-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019490/ez2246Isup2.hkl

e-67-o1551-Isup2.hkl^{(116.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019490/ez2246Isup3.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
N2—H3N⋯O2ⁱ	0.87 (2)	2.20 (2)	3.0264 (16)	160 (2)
N1—H2N⋯O1ⁱⁱ	0.89 (2)	2.09 (2)	2.9613 (16)	168 (2)
N1—H1N⋯O2ⁱⁱⁱ	0.86 (1)	2.18 (1)	3.0281 (16)	172 (2)

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

Acknowledgments

TG gratefully acknowledges funding by the Austrian Science Fund (FWF), project M1135-N17.

supplementary crystallographic information

Comment

The title compound (synonyms: proseptazine, septazine, benzylsulfanilamide, chemodyn; CAS No. 104–22–3), first marketed in 1936, was one of the early antibacterial agents of the sulfonamide class (Goissedet et al., 1936; Goissedet & Despois, 1938; Mellon et al., 1938; Long & Bliss, 1939). The C–N–(C₆H₄)–S fragment of the molecule (see Fig. 1) is essentially planar, and the molecular geometry is characterized by the torsion angles N1–S1–C1–C2 and N2–C7–C8–C9 of 43.6 (1)° and -65.9 (2)°, respectively.

The crystal structure contains three independent intermolecular N—H···O=S bonds which lead to the formation of an H-bonded framework. Each molecule is doubly H-bonded, via its NH₂ and sulfonyl groups, to two neighbouring molecules. These interactions generate an N—H···O=S-bonded ladder structure parallel to [100], which consists of fused R²₂(8) rings (Bernstein et al., 1995) and displays a 2₁ symmetry. This situation is illustrated in Fig. 2. The same one-dimensional structure has been found previously in only a few other compounds of the sulfonamide class, see Davis et al. (1996); Costanzo et al. (1999); Kubicki & Codding (2001);Yathirajan et al. (2005); Denehy et al. (2006); Toumieux et al. (2006).

The sulfonyl oxygen atom O2 accepts an additional H-bond from the NH group of a neighbouring molecule. This interaction links molecules which are related to one another by a 2₁ operation parallel to the c-axis (see Fig. 3).