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

Zhao, P.-L.; Zhou, Z.-Z.

doi:10.1107/S1600536809029572

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o2030-o2031

doi:10.1107/S1600536809029572

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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 and Zhong-Zhen Zhou ^a ^*

^aDepartment of Chemistry, Pharmaceutical Sciences, Southern Medical Universtiy, Guangzhou 510515, People's Republic of China
^*Correspondence e-mail: zzz_100600@163.com

(Received 18 July 2009; accepted 24 July 2009; online 29 July 2009)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 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

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
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1; (v) -x+1, -y+1, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title molecule with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The packing of the title molecule, showing one layer of molecules connected by strong N—H···O, and weak C—H···O intermolecular hydrogen bonds, and weak π-π stacking interactions.

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

Crystal data top

C₁₈H₁₄N₂O₅S·C₃H₇NO	Z = 2
M_r = 443.48	F(000) = 464
Triclinic, P1	D_x = 1.384 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4141 (1) Å	Cell parameters from 2421 reflections
b = 11.5676 (14) Å	θ = 2.5–26.7°
c = 11.8382 (14) Å	µ = 0.20 mm⁻¹
α = 87.138 (1)°	T = 292 K
β = 70.503 (2)°	Block, colorless
γ = 78.419 (2)°	0.30 × 0.20 × 0.20 mm
V = 1063.86 (18) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4568 independent reflections
Radiation source: fine-focus sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −10→10
T_min = 0.934, T_max = 0.962	k = −13→14
7900 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0676P)²] where P = (F_o² + 2F_c²)/3
4568 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O₅S·C₃H₇NO	γ = 78.419 (2)°
M_r = 443.48	V = 1063.86 (18) Å³
Triclinic, P1	Z = 2
a = 8.4141 (1) Å	Mo Kα radiation
b = 11.5676 (14) Å	µ = 0.20 mm⁻¹
c = 11.8382 (14) Å	T = 292 K
α = 87.138 (1)°	0.30 × 0.20 × 0.20 mm
β = 70.503 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4568 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	3163 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.962	R_int = 0.043
7900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.25 e Å⁻³
4568 reflections	Δρ_min = −0.17 e Å⁻³
289 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2135 (3)	0.19985 (18)	0.1714 (2)	0.0722 (7)
H1A	0.1411	0.1794	0.1309	0.108*
H1B	0.2338	0.1381	0.2251	0.108*
H1C	0.3210	0.2097	0.1135	0.108*
C2	0.1263 (3)	0.31350 (16)	0.24164 (17)	0.0519 (5)
C3	−0.0211 (3)	0.31675 (18)	0.34263 (19)	0.0580 (6)
H3	−0.0598	0.2469	0.3680	0.070*
C4	−0.1099 (3)	0.41904 (17)	0.40512 (18)	0.0542 (5)
H4	−0.2082	0.4192	0.4713	0.065*
C5	−0.0502 (2)	0.52272 (16)	0.36769 (16)	0.0445 (4)
C6	0.0963 (2)	0.52416 (15)	0.26977 (15)	0.0420 (4)
C7	0.1832 (3)	0.41704 (16)	0.20822 (16)	0.0484 (5)
H7	0.2825	0.4164	0.1427	0.058*
C8	0.1533 (2)	0.63617 (16)	0.22977 (15)	0.0427 (4)
C9	0.0433 (2)	0.73858 (15)	0.30060 (15)	0.0414 (4)
C10	−0.0936 (2)	0.72643 (16)	0.39626 (16)	0.0467 (5)
H10	−0.1573	0.7941	0.4410	0.056*
C11	0.0758 (2)	0.86128 (16)	0.26908 (16)	0.0443 (4)
H11	−0.005	0.9161	0.3323	0.053*
C12	0.3611 (3)	0.89041 (15)	0.14565 (16)	0.0469 (5)
C13	0.2766 (3)	0.90147 (18)	0.05140 (17)	0.0573 (5)
H13A	0.3236	0.8335	−0.0027	0.069*
H13B	0.2968	0.9719	0.0052	0.069*
C14	0.2690 (2)	0.93551 (16)	0.43651 (15)	0.0415 (4)
C15	0.3436 (2)	0.89915 (16)	0.53174 (15)	0.0430 (4)
C16	0.4445 (3)	0.80082 (19)	0.55371 (19)	0.0593 (5)
H16	0.4843	0.7310	0.5086	0.071*
C17	0.4781 (3)	0.8243 (2)	0.6579 (2)	0.0678 (6)
H17	0.5443	0.7728	0.6952	0.081*
C18	0.3975 (3)	0.9337 (2)	0.69290 (19)	0.0650 (6)
H18	0.3986	0.9716	0.7600	0.078*
C19	0.7238 (4)	0.6242 (3)	0.1424 (3)	0.1048 (10)
H19A	0.6655	0.6544	0.0867	0.157*
H19B	0.8457	0.6078	0.1013	0.157*
H19C	0.6968	0.6818	0.2050	0.157*
C20	0.7468 (4)	0.4095 (3)	0.1255 (3)	0.1092 (11)
H20A	0.7150	0.3444	0.1756	0.164*
H20B	0.8696	0.4012	0.0976	0.164*
H20C	0.7074	0.4105	0.0581	0.164*
C21	0.5459 (3)	0.5218 (2)	0.2970 (2)	0.0710 (6)
H21	0.5136	0.4507	0.3256	0.085*
N1	0.2489 (2)	0.87432 (13)	0.25530 (13)	0.0442 (4)
N2	0.3049 (2)	0.85021 (14)	0.35237 (14)	0.0476 (4)
H2	0.361 (3)	0.7885 (19)	0.351 (2)	0.057*
N3	0.6696 (3)	0.51810 (17)	0.19314 (17)	0.0676 (5)
O1	0.28274 (17)	0.64100 (11)	0.14324 (11)	0.0563 (4)
O2	−0.14547 (16)	0.62410 (11)	0.43227 (11)	0.0507 (3)
O3	0.51047 (19)	0.89574 (13)	0.12709 (12)	0.0630 (4)
O4	0.18311 (18)	1.03252 (11)	0.43361 (11)	0.0534 (4)
O5	0.31260 (18)	0.98314 (12)	0.61700 (12)	0.0576 (4)
O6	0.4692 (2)	0.60997 (13)	0.35973 (14)	0.0764 (5)
S1	0.04994 (8)	0.91011 (5)	0.12526 (5)	0.0628 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.1061 (19)	0.0405 (12)	0.0708 (15)	−0.0139 (12)	−0.0301 (14)	−0.0033 (11)
C2	0.0703 (14)	0.0380 (11)	0.0530 (11)	−0.0120 (10)	−0.0274 (10)	0.0036 (9)
C3	0.0755 (15)	0.0429 (12)	0.0618 (13)	−0.0232 (11)	−0.0255 (11)	0.0115 (10)
C4	0.0597 (13)	0.0518 (12)	0.0518 (11)	−0.0213 (10)	−0.0150 (10)	0.0116 (10)
C5	0.0506 (11)	0.0418 (10)	0.0418 (10)	−0.0112 (9)	−0.0154 (8)	0.0037 (8)
C6	0.0508 (11)	0.0376 (10)	0.0395 (9)	−0.0110 (8)	−0.0163 (8)	0.0027 (8)
C7	0.0585 (12)	0.0419 (10)	0.0436 (10)	−0.0105 (9)	−0.0152 (9)	0.0012 (8)
C8	0.0508 (11)	0.0412 (10)	0.0370 (9)	−0.0129 (9)	−0.0136 (8)	0.0021 (8)
C9	0.0510 (11)	0.0369 (10)	0.0365 (9)	−0.0107 (8)	−0.0134 (8)	0.0014 (8)
C10	0.0516 (11)	0.0379 (10)	0.0460 (10)	−0.0071 (9)	−0.0109 (9)	−0.0015 (8)
C11	0.0529 (11)	0.0358 (10)	0.0403 (10)	−0.0075 (9)	−0.0110 (9)	−0.0008 (8)
C12	0.0619 (13)	0.0316 (10)	0.0436 (10)	−0.0142 (9)	−0.0098 (9)	0.0003 (8)
C13	0.0808 (15)	0.0505 (12)	0.0415 (10)	−0.0224 (11)	−0.0167 (10)	0.0060 (9)
C14	0.0460 (10)	0.0384 (10)	0.0368 (9)	−0.0152 (8)	−0.0053 (8)	−0.0005 (8)
C15	0.0456 (10)	0.0449 (11)	0.0371 (9)	−0.0163 (9)	−0.0071 (8)	−0.0004 (8)
C16	0.0659 (14)	0.0550 (13)	0.0594 (13)	−0.0103 (11)	−0.0244 (11)	−0.0015 (10)
C17	0.0738 (16)	0.0729 (16)	0.0672 (14)	−0.0154 (13)	−0.0374 (12)	0.0094 (12)
C18	0.0711 (15)	0.0889 (18)	0.0464 (12)	−0.0280 (14)	−0.0270 (11)	0.0023 (12)
C19	0.118 (3)	0.101 (2)	0.0788 (19)	−0.0156 (19)	−0.0172 (18)	0.0177 (17)
C20	0.137 (3)	0.094 (2)	0.0798 (19)	0.016 (2)	−0.0315 (19)	−0.0293 (17)
C21	0.0858 (18)	0.0557 (15)	0.0702 (16)	−0.0094 (13)	−0.0262 (14)	−0.0010 (12)
N1	0.0563 (10)	0.0408 (9)	0.0377 (8)	−0.0143 (7)	−0.0156 (7)	0.0006 (7)
N2	0.0655 (11)	0.0351 (9)	0.0426 (8)	−0.0052 (8)	−0.0206 (8)	−0.0017 (7)
N3	0.0767 (13)	0.0657 (12)	0.0566 (11)	0.0029 (10)	−0.0263 (10)	−0.0027 (10)
O1	0.0622 (9)	0.0481 (8)	0.0469 (7)	−0.0175 (7)	0.0017 (7)	−0.0035 (6)
O2	0.0532 (8)	0.0426 (8)	0.0469 (7)	−0.0117 (6)	−0.0030 (6)	0.0020 (6)
O3	0.0613 (10)	0.0649 (10)	0.0587 (9)	−0.0208 (8)	−0.0099 (7)	0.0031 (7)
O4	0.0688 (9)	0.0368 (7)	0.0531 (8)	−0.0047 (7)	−0.0206 (7)	−0.0056 (6)
O5	0.0661 (9)	0.0616 (9)	0.0465 (7)	−0.0110 (7)	−0.0197 (7)	−0.0101 (7)
O6	0.0965 (13)	0.0516 (9)	0.0663 (10)	0.0032 (9)	−0.0167 (9)	−0.0069 (8)
S1	0.0733 (4)	0.0633 (4)	0.0590 (3)	−0.0192 (3)	−0.0307 (3)	0.0198 (3)

Geometric parameters (Å, º) top

C1—C2	1.508 (3)	C13—S1	1.797 (2)
C1—H1A	0.9600	C13—H13A	0.9700
C1—H1B	0.9600	C13—H13B	0.9700
C1—H1C	0.9600	C14—O4	1.212 (2)
C2—C7	1.370 (2)	C14—N2	1.354 (2)
C2—C3	1.401 (3)	C14—C15	1.470 (3)
C3—C4	1.367 (3)	C15—C16	1.347 (3)
C3—H3	0.9300	C15—O5	1.361 (2)
C4—C5	1.388 (2)	C16—C17	1.404 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—O2	1.380 (2)	C17—C18	1.325 (3)
C5—C6	1.384 (2)	C17—H17	0.9300
C6—C7	1.404 (3)	C18—O5	1.363 (2)
C6—C8	1.473 (2)	C18—H18	0.9300
C7—H7	0.9300	C19—N3	1.430 (3)
C8—O1	1.230 (2)	C19—H19A	0.9600
C8—C9	1.450 (2)	C19—H19B	0.9600
C9—C10	1.344 (2)	C19—H19C	0.9600
C9—C11	1.504 (2)	C20—N3	1.438 (3)
C10—O2	1.344 (2)	C20—H20A	0.9600
C10—H10	0.9300	C20—H20B	0.9600
C11—N1	1.448 (2)	C20—H20C	0.9600
C11—S1	1.8349 (19)	C21—O6	1.224 (3)
C11—H11	0.9800	C21—N3	1.315 (3)
C12—O3	1.216 (2)	C21—H21	0.9300
C12—N1	1.356 (2)	N1—N2	1.378 (2)
C12—C13	1.498 (3)	N2—H2	0.77 (2)

C2—C1—H1A	109.5	C12—C13—H13B	110.1
C2—C1—H1B	109.5	S1—C13—H13B	110.1
H1A—C1—H1B	109.5	H13A—C13—H13B	108.4
C2—C1—H1C	109.5	O4—C14—N2	123.15 (17)
H1A—C1—H1C	109.5	O4—C14—C15	123.24 (16)
H1B—C1—H1C	109.5	N2—C14—C15	113.61 (17)
C7—C2—C3	117.65 (18)	C16—C15—O5	109.77 (17)
C7—C2—C1	122.10 (19)	C16—C15—C14	134.79 (17)
C3—C2—C1	120.22 (18)	O5—C15—C14	115.37 (16)
C4—C3—C2	122.26 (18)	C15—C16—C17	106.6 (2)
C4—C3—H3	118.9	C15—C16—H16	126.7
C2—C3—H3	118.9	C17—C16—H16	126.7
C3—C4—C5	118.60 (18)	C18—C17—C16	106.9 (2)
C3—C4—H4	120.7	C18—C17—H17	126.5
C5—C4—H4	120.7	C16—C17—H17	126.5
O2—C5—C6	121.90 (15)	C17—C18—O5	110.6 (2)
O2—C5—C4	116.58 (16)	C17—C18—H18	124.7
C6—C5—C4	121.52 (18)	O5—C18—H18	124.7
C5—C6—C7	117.91 (16)	N3—C19—H19A	109.5
C5—C6—C8	120.29 (16)	N3—C19—H19B	109.5
C7—C6—C8	121.76 (16)	H19A—C19—H19B	109.5
C2—C7—C6	122.04 (18)	N3—C19—H19C	109.5
C2—C7—H7	119.0	H19A—C19—H19C	109.5
C6—C7—H7	119.0	H19B—C19—H19C	109.5
O1—C8—C9	123.67 (16)	N3—C20—H20A	109.5
O1—C8—C6	122.18 (17)	N3—C20—H20B	109.5
C9—C8—C6	114.14 (15)	H20A—C20—H20B	109.5
C10—C9—C8	120.52 (16)	N3—C20—H20C	109.5
C10—C9—C11	117.78 (16)	H20A—C20—H20C	109.5
C8—C9—C11	121.69 (15)	H20B—C20—H20C	109.5
O2—C10—C9	125.11 (17)	O6—C21—N3	126.2 (2)
O2—C10—H10	117.4	O6—C21—H21	116.9
C9—C10—H10	117.4	N3—C21—H21	116.9
N1—C11—C9	113.96 (16)	C12—N1—N2	120.45 (16)
N1—C11—S1	103.67 (11)	C12—N1—C11	120.75 (16)
C9—C11—S1	113.20 (12)	N2—N1—C11	117.91 (14)
N1—C11—H11	109.0	C14—N2—N1	119.57 (15)
C9—C11—H11	109.0	C14—N2—H2	125.4 (17)
S1—C11—H11	109.0	N1—N2—H2	114.9 (17)
O3—C12—N1	124.01 (19)	C21—N3—C19	120.1 (2)
O3—C12—C13	124.74 (17)	C21—N3—C20	121.3 (2)
N1—C12—C13	111.25 (17)	C19—N3—C20	118.6 (2)
C12—C13—S1	108.00 (13)	C10—O2—C5	117.98 (14)
C12—C13—H13A	110.1	C15—O5—C18	106.03 (16)
S1—C13—H13A	110.1	C13—S1—C11	93.51 (9)

C7—C2—C3—C4	1.8 (3)	N2—C14—C15—C16	2.3 (3)
C1—C2—C3—C4	−176.30 (19)	O4—C14—C15—O5	−1.2 (2)
C2—C3—C4—C5	−0.8 (3)	N2—C14—C15—O5	178.98 (14)
C3—C4—C5—O2	178.99 (17)	O5—C15—C16—C17	0.1 (2)
C3—C4—C5—C6	−0.3 (3)	C14—C15—C16—C17	177.0 (2)
O2—C5—C6—C7	−178.88 (16)	C15—C16—C17—C18	−0.1 (2)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—O5	0.1 (3)
O2—C5—C6—C8	−1.3 (3)	O3—C12—N1—N2	−7.0 (3)
C4—C5—C6—C8	178.01 (17)	C13—C12—N1—N2	173.40 (15)
C3—C2—C7—C6	−1.7 (3)	O3—C12—N1—C11	−175.98 (17)
C1—C2—C7—C6	176.35 (18)	C13—C12—N1—C11	4.4 (2)
C5—C6—C7—C2	0.6 (3)	C9—C11—N1—C12	109.33 (18)
C8—C6—C7—C2	−176.91 (17)	S1—C11—N1—C12	−14.16 (19)
C5—C6—C8—O1	180.00 (18)	C9—C11—N1—N2	−59.9 (2)
C7—C6—C8—O1	−2.5 (3)	S1—C11—N1—N2	176.57 (11)
C5—C6—C8—C9	−0.4 (2)	O4—C14—N2—N1	2.9 (3)
C7—C6—C8—C9	177.10 (16)	C15—C14—N2—N1	−177.28 (14)
O1—C8—C9—C10	−178.07 (19)	C12—N1—N2—C14	105.6 (2)
C6—C8—C9—C10	2.3 (3)	C11—N1—N2—C14	−85.1 (2)
O1—C8—C9—C11	3.0 (3)	O6—C21—N3—C19	−1.2 (4)
C6—C8—C9—C11	−176.62 (16)	O6—C21—N3—C20	−178.0 (2)
C8—C9—C10—O2	−2.8 (3)	C9—C10—O2—C5	1.0 (3)
C11—C9—C10—O2	176.18 (16)	C6—C5—O2—C10	1.1 (3)
C10—C9—C11—N1	127.95 (18)	C4—C5—O2—C10	−178.26 (16)
C8—C9—C11—N1	−53.1 (2)	C16—C15—O5—C18	−0.1 (2)
C10—C9—C11—S1	−113.90 (17)	C14—C15—O5—C18	−177.62 (15)
C8—C9—C11—S1	65.1 (2)	C17—C18—O5—C15	0.0 (2)
O3—C12—C13—S1	−171.45 (16)	C12—C13—S1—C11	−13.78 (14)
N1—C12—C13—S1	8.17 (19)	N1—C11—S1—C13	15.17 (13)
O4—C14—C15—C16	−177.9 (2)	C9—C11—S1—C13	−108.82 (14)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₅S·C₃H₇NO
M_r	443.48
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.4141 (1), 11.5676 (14), 11.8382 (14)
α, β, γ (°)	87.138 (1), 70.503 (2), 78.419 (2)
V (Å³)	1063.86 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.934, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	7900, 4568, 3163
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.130, 0.96
No. of reflections	4568
No. of parameters	289
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	171.9
C10—H10···O4ⁱⁱ	0.93	2.49	3.332 (2)	151.4
C11—H11···O5ⁱⁱ	0.98	2.500	3.267 (2)	135.4 (14)
C13—H13B···O3ⁱⁱⁱ	0.97	2.55	3.441 (2)	153.3
C16—H16···O6	0.93	2.36	3.193 (3)	149.6
C18—H18···O3^iv	0.93	2.47	3.342 (3)	156.9
C20—H20C···O1^v	0.96	2.46	3.361 (3)	157.1

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z.

Acknowledgements

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)

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Maliar, T., Jedinak, A., Kadrabova, J. & Sturdik, E. (2004). Eur. J. Med. Chem. 39, 241–248. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, Z. Z., Chen, Q. & Yang, G. F. (2008). Chin. J. Org. Chem. 28, 1385–1392. Web of Science CrossRef CAS Google Scholar
Zhou, Z. Z., Ding, M. W. & Yang, G. F. (2007). Heteroat. Chem. 18, 381–389. Web of Science CrossRef CAS Google Scholar
Zhou, Z.-Z., Huang, W., Zhao, P.-L., Chen, Q. & Yang, G.-F. (2005). Acta Cryst. E61, o2261–o2262. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Pages o2030-o2031

doi:10.1107/S1600536809029572

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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