4-Amino-N-(6-chloro-5-methoxy­pyrimidin-4-yl)benzene­sulfonamide

Hoong-Kun Fun; Jia Hao Goh; C S Chidan Kumar; H S Yathirajan; B Narayana

doi:10.1107/S1600536810001121

. 2010 Jan 16;66(Pt 2):o372–o373. doi: 10.1107/S1600536810001121

4-Amino-N-(6-chloro-5-methoxypyrimidin-4-yl)benzenesulfonamide

Hoong-Kun Fun ^a,^*,^‡, Jia Hao Goh ^a,^§, C S Chidan Kumar ^b, H S Yathirajan ^b, B Narayana ^c

PMCID: PMC2979666 PMID: 21579795

Abstract

In the title compound, C₁₁H₁₁ClN₄O₃S, the S atom is bonded in a distorted tetrahedral geometry, by two O atoms, a C atom of the benzene ring and an amino N atom. The essentially planar pyrimidine ring [maximum deviation = 0.020 (1) Å] forms a dihedral angle of 87.57 (5)° with the benzene ring. In the crystal structure, pairs of molecules are linked by intermolecular N—H⋯O hydrogen bonds to generate centrosymmetric R ₂ ²(8) ring motifs. In addition, molecules are linked into a three-dimensional extended network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to and applications of the title compound, see: Amir et al. (2007 ▶); Calabresi et al. (1975 ▶); El-Hashash et al. (1993 ▶); Nagaraja et al. (2003 ▶); Townsend & Drach (2002 ▶). For a related structure, see: Chohan et al. (2008 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₁H₁₁ClN₄O₃S
M _r = 314.75
Monoclinic,
a = 12.8792 (6) Å
b = 13.3557 (6) Å
c = 8.0867 (4) Å
β = 102.396 (1)°
V = 1358.57 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 100 K
0.44 × 0.33 × 0.12 mm

Data collection

Bruker SMART APEX DUO area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.829, T _max = 0.950
20122 measured reflections
4863 independent reflections
4292 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.089
S = 1.04
4863 reflections
225 parameters
All H-atom parameters refined
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001121/lh2975sup1.cif

e-66-0o372-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001121/lh2975Isup2.hkl

e-66-0o372-Isup2.hkl^{(238.2KB, 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
N1—H1N1⋯N4ⁱ	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1⋯O1ⁱⁱ	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2⋯O2ⁱⁱⁱ	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A⋯O1ⁱⁱ	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)

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

Acknowledgments

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. CSC thanks the University of Mysore for research facilities.

supplementary crystallographic information

Comment

The importance of pyrimidines and analogous compounds in pharmaceutical and biological fields is well known (Townsend et al., 2002). Some substituted pyrimidines and their derivaties have been reported to possess anti-microbial and anti-fungal activities (El-Hashash et al., 1993). Pyrimidines have incidental anti-viral activity against herpes and vaccinia infections (Calabresi et al., 1975). A review on pyrimidines as anti-inflammatory agent is described by Amir et al. (2007). Sulfonamides are an important class of anti-bacterial drugs used in medicine and veterinary practice. Sulfa drugs are widely used in the treatment of infections, especially for patients intolerant to antibiotics. The vast commercial success of these medicinal agents has made the chemistry of sulfonamides to become a major area of research and an important branch of commercial importance in pharmaceutical sciences (Nagaraja et al., 2003). In view of the importance of the title compound possessing potential anti-bacterial properties, its crystal structure is reported herein.

In the title sulfonamide compound (Fig. 1), the geometry around the S1 atom is a distorted tetrahedron, comprising of atoms O1 and O2 of the sulfonyl group, C6 atom of benzene ring and the amino atom N2. The O1–S1–O2 and O2–S1–N2 angles are 119.20 (5) and 102.20 (4)°, respectively, and the C6–S1–N2–C7 torsion angle is -68.95 (9)°. The pyrimidine ring is essentially planar, with r.m.s. deviation of -0.020 (1) Å, and is almost perpendicular to the benzene ring (C1-C6), as indicated by the dihedral angle of 87.57 (5)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Chohan et al., 2008). In the crystal structure, pairs of intermolecular N2—H1N2···O2ⁱⁱⁱ hydrogen bonds (see Table 1 for symmetry code) generate R²₂(8) ring motifs (Bernstein et al., 1995). Neighbouring molecules are linked into a three-dimensional extended network by intermolecular N1—H1N1···N4, N1—H2N1···O1 and C4—H4A···O1 hydrogen bonds (Fig. 2).

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. The compound was used without further purification. Single crystals of good quality were obtained from slow evaporation of an acetonitrile solution. M.p. 447–450 K.