Methyl 5-chloro-2-(4-methyl­benzene­sulfonamido)­benzoate

Bin Wang; Song Xia; Ya-Bin Shi; Fei-Fei He; Hai-Bo Wang

doi:10.1107/S1600536810019045

. 2010 May 26;66(Pt 6):o1462. doi: 10.1107/S1600536810019045

Methyl 5-chloro-2-(4-methylbenzenesulfonamido)benzoate

Bin Wang ^a,^b, Song Xia ^a,^b, Ya-Bin Shi ^a,^b, Fei-Fei He ^a,^b, Hai-Bo Wang ^a,^*

PMCID: PMC2979427 PMID: 21579530

Abstract

In the title compound, C₁₅H₁₄ClNO₄S, the benzene rings are oriented at a dihedral angle of 85.42 (1)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a five-membered ring and an intramolecular C—H⋯O interaction also occurs.

Related literature

For general background to the use of the title compound as an intermediate in the synthesis of quinoline, see: Theeraladanon et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄ClNO₄S
M _r = 339.78
Monoclinic,
a = 18.549 (4) Å
b = 9.935 (2) Å
c = 8.5190 (17) Å
β = 97.34 (3)°
V = 1557.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.891, T _max = 0.981
2914 measured reflections
2825 independent reflections
1259 reflections with I > 2σ(I)
R _int = 0.093
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.141
S = 1.00
2825 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019045/bq2211sup1.cif

e-66-o1462-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019045/bq2211Isup2.hkl

e-66-o1462-Isup2.hkl^{(138.7KB, 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
N—H1⋯O4	0.86	2.07	2.615 (6)	120
C9—H9A⋯O2	0.93	2.35	3.022 (6)	129

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supplementary crystallographic information

Comment

Quinolines are a major class of alkaloids and play an important role in the fields of natural products and medicinal chemistry. The title compound, (I), is a useful intermediate. (Theeraladanon et al., 2004) and we report here in the crystal structure of it. In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A(C2-C7) and B(C8-C13) are planar with a dihedral angle of 85.42 (1) ° between them. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a five-membered ring C (C8/C13/C14/O4/N). In the crystal structure, intermolecular C-H···O hydrogen bonds link the molecules into chains along the b axis (Fig. 2).

Experimental

The title compound, (I) was prepared by the literature method (Theeraladanon et al., 2004). Crystals suitable for X-ray analysis were obtained by slow evaporation of an methanol solution.