3-Methyl-5-(4-oxo-4H-chromen-3-ylmethyl­ene)-1,3-thia­zolidine-2,4-dione

In the title compound, C₁₄H₉NO₄S, the benzopyran and thia­zolidine ring systems are each planar. The thia­zolidine ring makes a dihedral angle of 3.84 (4)° with the benzopyran ring system. The mol­ecular structure is stabilized by intra­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.069
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         20 Ang.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C13     ..       5.38 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Methyl-5-(4-oxo-4H-chromen-3-ylmethylene)-1,3-thiazolidine-2,4-dione

Crystal data

C14H9NO4S	F(000) = 592
Mr = 287.28	Dx = 1.642 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14348 reflections
a = 5.5926 (3) Å	θ = 1.5–26.0°
b = 27.0630 (2) Å	µ = 0.29 mm^−1
c = 7.6829 (4) Å	T = 295 K
β = 92.439 (4)°	Prism, colorless
V = 1161.77 (9) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	1802 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→6
Tmin = 0.918, Tmax = 0.971	k = −33→33
15165 measured reflections	l = −9→9
2261 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0455P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.25 e Å^−3
2261 reflections	Δρmin = −0.26 e Å^−3
197 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H10	−0.043 (3)	0.6966 (7)	0.668 (2)	0.025 (5)*
H14A	0.317 (3)	0.5093 (7)	0.869 (2)	0.032 (5)*
H14C	0.210 (3)	0.5173 (7)	0.676 (3)	0.032 (5)*
H14B	0.041 (3)	0.5255 (7)	0.842 (2)	0.027 (5)*
S1	0.51183 (7)	0.661110 (13)	0.88619 (5)	0.01623 (11)
O1	0.50675 (19)	0.76199 (4)	0.89828 (14)	0.0211 (2)
O2	−0.05283 (18)	0.83655 (4)	0.66032 (13)	0.0177 (2)
O4	0.63974 (19)	0.56829 (4)	0.95235 (14)	0.0224 (3)
C5	0.5024 (3)	0.86750 (5)	0.90701 (19)	0.0172 (3)
H5	0.6323	0.8524	0.9649	0.021*
C10	0.1012 (3)	0.70632 (6)	0.72428 (19)	0.0159 (3)
C9	0.1334 (3)	0.75944 (5)	0.73908 (19)	0.0156 (3)
O3	−0.05127 (18)	0.60832 (4)	0.65060 (13)	0.0199 (2)
N1	0.2752 (2)	0.58055 (4)	0.80895 (16)	0.0161 (3)
C6	0.3231 (2)	0.83846 (6)	0.82685 (18)	0.0155 (3)
C1	0.1312 (3)	0.86252 (5)	0.74296 (18)	0.0161 (3)
C4	0.4888 (3)	0.91826 (6)	0.9012 (2)	0.0192 (3)
H4	0.609	0.9373	0.9553	0.023*
C12	0.1319 (3)	0.61705 (5)	0.73502 (19)	0.0161 (3)
C2	0.1134 (3)	0.91365 (6)	0.7344 (2)	0.0185 (3)
H2	−0.0166	0.9288	0.6768	0.022*
C3	0.2942 (3)	0.94137 (6)	0.8138 (2)	0.0202 (3)
H3	0.2868	0.9757	0.8093	0.024*
C11	0.2328 (3)	0.66691 (5)	0.77530 (18)	0.0153 (3)
C7	0.3370 (3)	0.78422 (5)	0.82809 (18)	0.0159 (3)
C13	0.4889 (3)	0.59569 (5)	0.88882 (19)	0.0169 (3)
C8	−0.0439 (3)	0.78720 (5)	0.66353 (19)	0.0169 (3)
H8	−0.1711	0.7704	0.6088	0.02*
C14	0.2053 (3)	0.52879 (6)	0.7975 (2)	0.0211 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01454 (19)	0.01441 (18)	0.01935 (19)	0.00005 (14)	−0.00403 (13)	0.00088 (15)
O1	0.0182 (5)	0.0176 (6)	0.0270 (6)	0.0030 (4)	−0.0057 (4)	0.0010 (5)
O2	0.0157 (5)	0.0147 (5)	0.0221 (5)	0.0011 (4)	−0.0050 (4)	−0.0010 (4)
O4	0.0204 (6)	0.0186 (6)	0.0275 (6)	0.0026 (5)	−0.0058 (5)	0.0039 (5)
C5	0.0156 (7)	0.0200 (8)	0.0158 (7)	0.0006 (6)	−0.0014 (6)	0.0012 (6)
C10	0.0137 (7)	0.0187 (7)	0.0151 (7)	−0.0017 (6)	−0.0013 (6)	−0.0015 (6)
C9	0.0165 (7)	0.0159 (7)	0.0144 (7)	0.0012 (6)	0.0019 (6)	0.0003 (6)
O3	0.0172 (5)	0.0184 (5)	0.0235 (6)	0.0000 (4)	−0.0059 (4)	−0.0012 (4)
N1	0.0163 (6)	0.0135 (6)	0.0184 (6)	−0.0009 (5)	−0.0024 (5)	0.0009 (5)
C6	0.0156 (7)	0.0166 (7)	0.0144 (7)	0.0008 (6)	0.0014 (5)	0.0008 (6)
C1	0.0161 (7)	0.0176 (8)	0.0145 (7)	−0.0017 (6)	−0.0003 (6)	−0.0019 (6)
C4	0.0176 (8)	0.0193 (8)	0.0203 (7)	−0.0037 (6)	−0.0022 (6)	−0.0004 (6)
C12	0.0168 (7)	0.0171 (8)	0.0145 (7)	0.0010 (6)	0.0015 (6)	0.0004 (6)
C2	0.0180 (8)	0.0174 (8)	0.0198 (7)	0.0036 (6)	−0.0012 (6)	0.0012 (6)
C3	0.0232 (8)	0.0145 (7)	0.0227 (8)	−0.0006 (6)	−0.0003 (6)	0.0008 (6)
C11	0.0142 (7)	0.0169 (7)	0.0147 (7)	−0.0008 (6)	−0.0005 (5)	0.0001 (6)
C7	0.0155 (7)	0.0186 (8)	0.0138 (7)	0.0012 (6)	0.0016 (6)	0.0010 (6)
C13	0.0169 (7)	0.0182 (7)	0.0156 (7)	−0.0002 (6)	−0.0002 (6)	0.0000 (6)
C8	0.0174 (7)	0.0156 (7)	0.0176 (7)	−0.0015 (6)	−0.0003 (6)	−0.0019 (6)
C14	0.0228 (8)	0.0127 (7)	0.0273 (9)	−0.0002 (6)	−0.0042 (7)	0.0009 (6)

Geometric parameters (Å, º)

S1—C11	1.7528 (15)	N1—C13	1.3821 (19)
S1—C13	1.7754 (15)	N1—C14	1.4559 (19)
O1—C7	1.2289 (18)	C6—C1	1.390 (2)
O2—C8	1.3367 (18)	C6—C7	1.470 (2)
O2—C1	1.3784 (17)	C1—C2	1.389 (2)
O4—C13	1.2102 (18)	C4—C3	1.401 (2)
C5—C4	1.376 (2)	C4—H4	0.93
C5—C6	1.396 (2)	C12—C11	1.490 (2)
C5—H5	0.93	C2—C3	1.380 (2)
C10—C11	1.345 (2)	C2—H2	0.93
C10—C9	1.453 (2)	C3—H3	0.93
C10—H10	0.937 (19)	C8—H8	0.93
C9—C8	1.355 (2)	C14—H14A	0.97 (2)
C9—C7	1.466 (2)	C14—H14C	0.987 (19)
O3—C12	1.2122 (18)	C14—H14B	0.995 (19)
N1—C12	1.3790 (19)
C11—S1—C13	91.81 (7)	N1—C12—C11	110.78 (12)
C8—O2—C1	118.30 (11)	C3—C2—C1	118.11 (13)
C4—C5—C6	120.64 (14)	C3—C2—H2	120.9
C4—C5—H5	119.7	C1—C2—H2	120.9
C6—C5—H5	119.7	C2—C3—C4	120.57 (14)
C11—C10—C9	134.22 (14)	C2—C3—H3	119.7
C11—C10—H10	111.2 (11)	C4—C3—H3	119.7
C9—C10—H10	114.6 (11)	C10—C11—C12	117.38 (13)
C8—C9—C10	115.42 (13)	C10—C11—S1	132.67 (12)
C8—C9—C7	119.09 (13)	C12—C11—S1	109.95 (10)
C10—C9—C7	125.50 (13)	O1—C7—C9	123.44 (13)
C12—N1—C13	116.54 (12)	O1—C7—C6	122.11 (13)
C12—N1—C14	120.96 (12)	C9—C7—C6	114.45 (12)
C13—N1—C14	122.47 (12)	O4—C13—N1	124.91 (14)
C1—C6—C5	117.82 (13)	O4—C13—S1	124.47 (12)
C1—C6—C7	120.69 (13)	N1—C13—S1	110.62 (10)
C5—C6—C7	121.48 (13)	O2—C8—C9	126.03 (14)
O2—C1—C2	115.83 (13)	O2—C8—H8	117
O2—C1—C6	121.43 (13)	C9—C8—H8	117
C2—C1—C6	122.74 (13)	N1—C14—H14A	109.0 (11)
C5—C4—C3	120.11 (14)	N1—C14—H14C	110.0 (11)
C5—C4—H4	119.9	H14A—C14—H14C	109.0 (15)
C3—C4—H4	119.9	N1—C14—H14B	108.2 (11)
O3—C12—N1	122.95 (13)	H14A—C14—H14B	109.6 (15)
O3—C12—C11	126.27 (13)	H14C—C14—H14B	111.0 (15)
C11—C10—C9—C8	178.10 (16)	N1—C12—C11—C10	−174.39 (13)
C11—C10—C9—C7	−2.3 (3)	O3—C12—C11—S1	−175.34 (13)
C4—C5—C6—C1	−0.5 (2)	N1—C12—C11—S1	5.22 (15)
C4—C5—C6—C7	178.55 (14)	C13—S1—C11—C10	176.88 (16)
C8—O2—C1—C2	179.55 (13)	C13—S1—C11—C12	−2.65 (11)
C8—O2—C1—C6	0.5 (2)	C8—C9—C7—O1	−179.13 (15)
C5—C6—C1—O2	179.84 (13)	C10—C9—C7—O1	1.3 (2)
C7—C6—C1—O2	0.8 (2)	C8—C9—C7—C6	0.77 (19)
C5—C6—C1—C2	0.8 (2)	C10—C9—C7—C6	−178.84 (14)
C7—C6—C1—C2	−178.25 (14)	C1—C6—C7—O1	178.57 (14)
C6—C5—C4—C3	−0.2 (2)	C5—C6—C7—O1	−0.5 (2)
C13—N1—C12—O3	174.59 (14)	C1—C6—C7—C9	−1.33 (19)
C14—N1—C12—O3	−3.6 (2)	C5—C6—C7—C9	179.62 (13)
C13—N1—C12—C11	−5.94 (18)	C12—N1—C13—O4	−176.28 (15)
C14—N1—C12—C11	175.85 (13)	C14—N1—C13—O4	1.9 (2)
O2—C1—C2—C3	−179.45 (13)	C12—N1—C13—S1	3.91 (16)
C6—C1—C2—C3	−0.4 (2)	C14—N1—C13—S1	−177.91 (12)
C1—C2—C3—C4	−0.4 (2)	C11—S1—C13—O4	179.71 (14)
C5—C4—C3—C2	0.7 (2)	C11—S1—C13—N1	−0.48 (11)
C9—C10—C11—C12	179.47 (16)	C1—O2—C8—C9	−1.1 (2)
C9—C10—C11—S1	0.0 (3)	C10—C9—C8—O2	−179.91 (13)
O3—C12—C11—C10	5.0 (2)	C7—C9—C8—O2	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.936 (17)	2.393 (19)	2.836 (2)	108.7 (13)
C14—H14A···O4	0.970 (17)	2.474 (18)	2.866 (2)	103.9 (13)