Gliquidone

Thomas Gelbrich; Mairi F Haddow; Ulrich J Griesser

doi:10.1107/S1600536811016680

. 2011 May 7;67(Pt 6):o1343. doi: 10.1107/S1600536811016680

Gliquidone

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

PMCID: PMC3120417 PMID: 21754738

Abstract

The title compound {systematic name: N-cyclohexylcarbamoyl-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide}, C₂₇H₃₃N₃O₆S, displays an intramolecular N—H⋯O=S interaction, as well as intermolecular N—H⋯O=C hydrogen bonds. The latter interactions lead to the formation of hydrogen-bonded chains parallel to the c axis. The conformation of the sulfonylurea fragment is in agreement with a recent theoretical study [Kasetti et al. (2010 ▶). J. Phys. Chem. B, 114, 11603–11610].

Related literature

For theoretical studies of the molecular structure, see Lins et al. (1996 ▶); Kasetti et al. (2010 ▶). For thermomicroscopy, see Kuhnert-Brandstätter et al. (1982 ▶). For related crystal structures, see: Kobelt & Paulus (1972 ▶); Iwata et al. (1997 ▶); Grell et al. (1998 ▶); Endo et al. (2003 ▶).

Experimental

Crystal data

C₂₇H₃₃N₃O₆S
M _r = 527.62
Monoclinic,
a = 19.1494 (4) Å
b = 10.7253 (3) Å
c = 13.8024 (2) Å
β = 106.691 (1)°
V = 2715.34 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.937, T _max = 0.984
28737 measured reflections
5325 independent reflections
4361 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.101
S = 1.03
5325 reflections
376 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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 (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016680/jh2285sup1.cif

e-67-o1343-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016680/jh2285Isup2.hkl

e-67-o1343-Isup2.hkl^{(260.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016680/jh2285Isup3.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
N1—H1N⋯O5ⁱ	0.86 (1)	2.03 (2)	2.8702 (17)	167 (2)
N2—H2N⋯O1	0.87 (1)	2.15 (2)	2.8404 (17)	136 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Gliquidone is an anti-diabetic drug in the sulfonylurea class. It is used in the treatment of diabetes mellitus type 2. The conformation of the sulfonyl urea fragment is in agreement with the SLU-1 geometry discussed in a recent theoretical study [Kasetti et al. (2010)]. The same conformation was previously found in polymorph I of glimepiride (Iwata et al., 1997).

In the sulfonyl urea part, the molecule displays an intramolecular N–H···O=S bond. The second NH group is N–H···O=C bonded to the imide part of a neighbouring molecule. As a result of this interaction, H-bonded chains are formed, which possess glide symmetry and propagate parallel to the c-axis.

Experimental

The investigated sample of gliquidone was obtained from Boehriger Ingelheim.