N′-(4-Bromo­phenyl­sulfon­yl)isonicotino­hydrazide

Islam Ullah Khan; Muhammad Ashfaq; Muhammad Nadeem Arshad; Hamad Ahmad; Ghulam Mustafa

doi:10.1107/S1600536809028475

. 2009 Jul 25;65(Pt 8):o1991. doi: 10.1107/S1600536809028475

N′-(4-Bromophenylsulfonyl)isonicotinohydrazide

Islam Ullah Khan ^a, Muhammad Ashfaq ^a, Muhammad Nadeem Arshad ^a,^*, Hamad Ahmad ^a, Ghulam Mustafa ^b

PMCID: PMC2977211 PMID: 21583665

Abstract

The title compound, C₁₂H₁₀BrN₃O₃S, crystallizes with two crystallographically independent molecules in the asymmetric unit. The dihedral angles between the two six-membered rings in the molecules are 34.1 (3) and 45.1 (2)°. In the crystal structure, molecules are connected via N—H⋯O and N—H⋯N hydrogen bonding.

Related literature

For general background to isonicotinic acid hydrazides, see: Carlton (1967 ▶). For a related structure, see: Wang et al. (2008 ▶). For the synthesis and biological activity of isoniazid and hydrazide derivatives, see: Lourenco et al. (2008 ▶); Kucukguzel et al. (2003 ▶); Carvalho et al. (2008 ▶), For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₁₀BrN₃O₃S
M _r = 356.20
Monoclinic,
a = 10.1229 (6) Å
b = 19.0440 (12) Å
c = 15.0640 (7) Å
β = 96.862 (2)°
V = 2883.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 3.01 mm⁻¹
T = 296 K
0.36 × 0.30 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.349, T _max = 0.641
29398 measured reflections
6601 independent reflections
3473 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.146
S = 1.01
6601 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809028475/nc2151sup1.cif

e-65-o1991-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028475/nc2151Isup2.hkl

e-65-o1991-Isup2.hkl^{(323.1KB, hkl)}

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—H2⋯O4ⁱ	0.76 (4)	2.15 (4)	2.882 (4)	165.09
N3—H3⋯N4ⁱⁱ	0.78 (4)	2.10 (4)	2.868 (5)	168.21
N6—H6⋯O6ⁱⁱⁱ	0.83 (4)	2.26 (4)	2.998 (4)	147.35
N5—H5⋯N1^iv	0.83 (4)	2.03 (4)	2.847 (4)	168.32
N3—H3⋯O1	0.78 (4)	2.49 (4)	2.732 (4)	100 (3)

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

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project of strengthening the Materials Chemistry Laboratory at GC University, Lahore, Pakistan.

supplementary crystallographic information

Comment

Isonicotinic acid hydrazide(INH) commonly known as isoniazid is a drug being used for the treatment of tuberclosis (TB) for long time (Carlton, 1967). Different approaches have been made for the synthesis of biologically active derivatives of isoniazid (Lourenco et al., 2008), (Kucukguzel et al., 2007), (Carvalho, et al.. 2008) and their crystallographic studies (Wang et al., 2008). In this context we report the crystal structure of title compound (N'-[(4-bromophenyl)sulfonyl]pyridine-4-carbohydrazide) a sulfonamide derivative of Isoniazid.

The title compound crystallizes with two crystallographically independent molecules in the asymmetric unit. The dihedral angle in each of these molecules amount to 34.1 (3) ° in molecule A, while it is 45.1 (2) ° (Fig. 1).

In the crystal structure the molecules are connected via intermolecular and intramolecular N–H···O and N–H···N hydrogen bonding (Fig. 2 and Tab. 1). One of the two indpenendent molecules is connected into dimers via N–H···O hydrogen bonding of the sulfonamide group into R₂²(8) rings (Bernstein et al., 1995). These dimers are further linked by additional N–H···O and N–H···N hydrogen bonding.

Experimental

To the solution of Isoniazid (0.5 g, 3.646 mmol) in distilled water (10 ml), 4-Bromobenzenesulfonyl chloride(0.9316 g, 3.65 mmol) was suspended. The reaction mixture was stirred at room temperature for 4 hrs at constant pH 8–9, which was adjusted by 1M sodium carbonate solution. After completion of the reaction which was observed by the consumption of suspended 4-Bromobenzenesulfonyl chloride, the pH was adjusted at 2–3 using 1 N HCl solution, which results the formation of a light yellow coloured precipitate, which was filtered off and dried. The prodcut was recrystallized from methanol.