N-[2-(6-Methyl-4-oxo-4H-chromen-3-yl)-4-oxothia­zolidin-3-yl]furan-2-carbox­amide N,N-dimethyl­formamide solvate

Pei-Liang Zhao; Zhong-Zhen Zhou

doi:10.1107/S1600536809029572

. 2009 Jul 29;65(Pt 8):o2030–o2031. doi: 10.1107/S1600536809029572

N-[2-(6-Methyl-4-oxo-4H-chromen-3-yl)-4-oxothiazolidin-3-yl]furan-2-carboxamide N,N-dimethylformamide solvate

Pei-Liang Zhao ^a, Zhong-Zhen Zhou ^a,^*

PMCID: PMC2977248 PMID: 21583697

Abstract

The title molecule, C₁₈H₁₄N₂O₅S·C₃H₇NO, comprises of a carboxamide group bonded to a furan ring and a distorted envelope-shaped 4-oxothiazolidin-3-yl group which is connected to a substituted 6-methyl-4-oxo-4H-chromen-3-yl group. Extensive strong N—H⋯O and weak C—H⋯O intermolecular hydrogen-bonding interactions occur between dimethylformamide (DMF), the crystallizing solvent, and the various heterocyclic groups within the compound, as well as additional weak C—H⋯O interactions between the heterocyclic groups themselves. The carboxyl group of the DMF solvent molecule forms a trifurcated (four-center) acceptor hydrogen-bond interaction with the carboxamide, furan and 6-methyl-4-oxo-4H-chromen-3-yl groups. The dihedral angles between the planar chromone group [maximum deviation = 0.0377 (18)°] and those of the furan and 4-oxothiazolidin-3-yl groups are 89.4 (6) and 78.5 (1)°, respectively.

Related literature

For related structures, see: Zhou et al. (2005 ▶). For the preparation of the title compound, see: Zhou et al. (2008 ▶). For general background to glycoluril and its derivatives, see: Maliar et al. (2004 ▶), Zhou et al. (2007 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₈H₁₄N₂O₅S·C₃H₇NO
M _r = 443.48
Triclinic,
a = 8.4141 (1) Å
b = 11.5676 (14) Å
c = 11.8382 (14) Å
α = 87.138 (1)°
β = 70.503 (2)°
γ = 78.419 (2)°
V = 1063.86 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.934, T _max = 0.962
7900 measured reflections
4568 independent reflections
3163 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.130
S = 0.96
4568 reflections
289 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029572/jj2002sup1.cif

e-65-o2030-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029572/jj2002Isup2.hkl

e-65-o2030-Isup2.hkl^{(223.8KB, 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⋯O6	0.77 (2)	2.10 (2)	2.856 (2)	169 (2)
C4—H4⋯O6ⁱ	0.93	2.50	3.421 (3)	172
C10—H10⋯O4ⁱⁱ	0.93	2.49	3.332 (2)	151
C11—H11⋯O5ⁱⁱ	0.98	2.50	3.267 (2)	135 (1)
C13—H13B⋯O3ⁱⁱⁱ	0.97	2.55	3.441 (2)	153
C16—H16⋯O6	0.93	2.36	3.193 (3)	150
C18—H18⋯O3^iv	0.93	2.47	3.342 (3)	157
C20—H20C⋯O1^v	0.96	2.46	3.361 (3)	157

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

Acknowledgments

The authors thank Professor Guang-Fu Yang for technical assistance and Dr Meng Xiang-Gao for the data collection. The authors acknowledge financial support from the National Natural Science Foundation of Hubei Province (grant No. 7300452) and the Medical Research Fundation of Science and Technology of Guangdong Province (grant No. B2008103)

supplementary crystallographic information

Comment

The tri-substituted chromone (1,4-benzopyrone) pharmacophore is an important structural element in medicinal chemistry, and shows a broad spectrum of pharmacological activities (Maliar et al. (2004), Zhou et al. (2007)). Hence, we were curious to explore the family of biheterocyclic compounds that contain both the thiazolidinone and chromone pharmacophores, with a view to discovering novel lead structures for the development of antifungal agents.

The title molecule is comprised of a carboxamide group bonded to a furan ring and a distorted envelope shaped (Cremer & Pople, 1975) 4-oxothiazolidin-3-yl group (Q(2) = 0.1878 (18) Å, Phi(2) = 188.3 (6)°; for an ideal envelope Phi(2) = k x 36) which is connected to a substituted 6-methyl-4-oxo-4H-chromen-3-yl group (Fig. 1). Extensive strong N2—H2···O6 and weak C16—H16···O6, C20—H20···O6, hydrogen bonding intermolecular interactions occur between dimethylformamide (DMF), the crystallizing solvent, and the various heterocyclic groups within the compound as well as additional weak C—H···O interactions between the heterocyclic groups themselves (Table 1, Fig. 2). The carboxyl group of the DMF solvent forms a trifurcated (4-center) acceptor hydrogen bond interaction with the carboxamide, furan and 6-methyl-4-oxo-4H-chromen-3-yl groups. The dihedral angle between the planar chromone group (max deviation = 0.0377 (18)°) and that of the furan and 4-oxothiazolidin-3-yl groups is 89.4 (6)° and 78.5 (1)°, respectively. Crystal packing is also stabilized by π-π stacking interactions (Cg2—Cg2 = 3.8378 (14) Å; 1 - x, 2 - y, 1 - z; Cg2 is the centroid of the O5/C15—C18 ring).

Experimental

The title compound was synthesized according to the procedure reported (Zhou et al., 2008). Crystals appropriate for X-ray data collection were obtained by slow evaporation of the DMF solution at 293 K.