(Z)-5-(3-Nitro­benzyl­idene)-1,3-thia­zolidine-2,4-dione

In the title compound, C₁₀H₆N₂O₄S, the benzene and thia­zolidine rings are oriented at a dihedral angle of 8.8 (5)° to one another. In the crystal structure, intra­molecular C—H...O and C—H...S hydrogen bonds are present; inter­molecular N—H...O and C—H...O hydrogen bonds link the mol­ecules into rows down the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.077
• wR factor = 0.194
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.03
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 142
              The title compound, C~10~H~6~N~2~O~4~S~, is a thiazolidine derivative. The
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Comment

Thiazolidines are an important class of heteroaromatic compounds and have widespread applications from pharmaceuticals (Barreca & Balzarini, 2002) to materials (Botti et al., 1996). As part of our studies in this area (Guo et al., 2006), we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C1—C6) and B (C8/C10/N/C9/S) are planar and oriented at a dihedral angle of 8.8 (5)° to one another.

In the crystal structure, intramolecular C—H···O and C—H···S hydrogen bonds affect the conformation of the molecule while intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into rows down the a axis (Fig. 2).

Related literature

For background to thiazolidine compounds, see: Barreca & Balzarini (2002); Botti et al. (1996). For a related structure, see: Guo et al. (2006). For reference structural data, see: Allen et al. (1987).

S2. Experimental

Thiazolidine-2,4-dione(10 mmol) and 3-nitrobenzaldehyde(10 mmol) were dissolved in ethanol (10 ml) in a 50 mL round-bottomed flask and 5 drops of piperidine were added. The flask was heated in a modified domestic microwave oven at 300 W for 5 minutes. After cooling, the mixture was poured into water, the crude compound (I) filtered out, and recrystallized from ethanol. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

S3. Refinement

H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93, 0.98 and 0.96 Å for aromatic, methine and methyl H, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens,1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and intramolecular hydrogen bonds are drawn as dashed lines.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(Z)-5-(3-Nitrobenzylidene)-1,3-thiazolidine-2,4-dione

Crystal data

C10H6N2O4S	Z = 2
Mr = 250.23	F(000) = 256
Triclinic, P1	Dx = 1.637 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7270 (9) Å	Cell parameters from 25 reflections
b = 10.936 (2) Å	θ = 9–13°
c = 11.276 (2) Å	µ = 0.32 mm^−1
α = 117.41 (3)°	T = 293 K
β = 97.93 (3)°	Block, colorless
γ = 93.36 (3)°	0.30 × 0.10 × 0.10 mm
V = 507.6 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1409 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 26.0°, θmin = 2.1°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = −13→11
Tmin = 0.909, Tmax = 0.968	l = 0→13
2246 measured reflections	3 standard reflections every 200 reflections
1992 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 1.7P] where P = (Fo^2 + 2Fc^2)/3
1992 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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
S	0.3581 (3)	0.59718 (13)	0.63995 (13)	0.0598 (4)
C1	−0.3675 (11)	0.2519 (5)	0.7606 (5)	0.0531 (12)
N1	−0.5780 (11)	0.2091 (4)	0.8249 (5)	0.0633 (12)
O1	−0.6747 (10)	0.0859 (4)	0.7697 (4)	0.0766 (12)
O2	−0.6415 (10)	0.2990 (4)	0.9278 (4)	0.0765 (12)
N2	0.5030 (10)	0.8520 (4)	0.8274 (4)	0.0593 (11)
H2A	0.5898	0.9360	0.8731	0.071*
C2	−0.2926 (12)	0.1520 (5)	0.6454 (5)	0.0568 (13)
H2B	−0.3610	0.0583	0.6112	0.068*
O3	0.7236 (10)	0.7914 (4)	0.6431 (4)	0.0825 (13)
C3	−0.1128 (12)	0.1953 (5)	0.5825 (5)	0.0611 (14)
H3A	−0.0614	0.1303	0.5028	0.073*
O4	0.2315 (9)	0.8721 (3)	0.9849 (4)	0.0656 (11)
C4	−0.0071 (12)	0.3341 (5)	0.6359 (5)	0.0567 (13)
H4A	0.1131	0.3610	0.5908	0.068*
C5	−0.0757 (11)	0.4342 (5)	0.7550 (5)	0.0501 (12)
C6	−0.2752 (11)	0.3898 (5)	0.8169 (5)	0.0533 (12)
H6A	−0.3393	0.4536	0.8934	0.064*
C7	0.0334 (12)	0.5816 (5)	0.8209 (5)	0.0548 (13)
H7A	−0.0274	0.6345	0.9024	0.066*
C8	0.2062 (11)	0.6537 (5)	0.7841 (5)	0.0502 (11)
C9	0.5580 (12)	0.7639 (5)	0.7014 (5)	0.0586 (13)
C10	0.3069 (12)	0.8021 (5)	0.8776 (5)	0.0549 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0842 (10)	0.0441 (7)	0.0461 (7)	0.0083 (6)	0.0215 (6)	0.0146 (6)
C1	0.069 (3)	0.037 (2)	0.044 (3)	0.008 (2)	0.005 (2)	0.012 (2)
N1	0.091 (3)	0.044 (2)	0.058 (3)	0.010 (2)	0.010 (2)	0.027 (2)
O1	0.101 (3)	0.044 (2)	0.080 (3)	−0.002 (2)	0.017 (2)	0.027 (2)
O2	0.112 (3)	0.049 (2)	0.073 (3)	0.017 (2)	0.043 (2)	0.026 (2)
N2	0.084 (3)	0.035 (2)	0.055 (2)	0.017 (2)	0.024 (2)	0.0147 (19)
C2	0.074 (4)	0.035 (2)	0.055 (3)	0.008 (2)	0.010 (3)	0.017 (2)
O3	0.113 (3)	0.062 (2)	0.078 (3)	0.007 (2)	0.052 (3)	0.029 (2)
C3	0.083 (4)	0.038 (3)	0.049 (3)	0.005 (2)	0.020 (3)	0.008 (2)
O4	0.096 (3)	0.0364 (18)	0.056 (2)	0.0065 (17)	0.032 (2)	0.0109 (16)
C4	0.076 (4)	0.043 (3)	0.046 (3)	0.013 (2)	0.019 (2)	0.015 (2)
C5	0.068 (3)	0.033 (2)	0.041 (2)	0.012 (2)	0.011 (2)	0.0099 (19)
C6	0.067 (3)	0.040 (3)	0.047 (3)	0.017 (2)	0.010 (2)	0.015 (2)
C7	0.077 (4)	0.042 (3)	0.040 (3)	0.018 (2)	0.014 (2)	0.014 (2)
C8	0.067 (3)	0.036 (2)	0.046 (3)	0.013 (2)	0.017 (2)	0.015 (2)
C9	0.070 (3)	0.044 (3)	0.057 (3)	0.004 (2)	0.013 (3)	0.020 (2)
C10	0.069 (3)	0.045 (3)	0.051 (3)	0.015 (2)	0.012 (2)	0.022 (2)

Geometric parameters (Å, º)

S—C8	1.729 (5)	O3—C9	1.197 (6)
S—C9	1.775 (5)	C3—C4	1.379 (7)
C1—C6	1.353 (7)	C3—H3A	0.9300
C1—C2	1.368 (7)	O4—C10	1.215 (6)
C1—N1	1.482 (7)	C4—C5	1.384 (6)
N1—O2	1.218 (6)	C4—H4A	0.9300
N1—O1	1.220 (5)	C5—C6	1.433 (7)
N2—C10	1.359 (7)	C5—C7	1.453 (6)
N2—C9	1.374 (6)	C6—H6A	0.9300
N2—H2A	0.8600	C7—C8	1.334 (7)
C2—C3	1.371 (7)	C7—H7A	0.9300
C2—H2B	0.9300	C8—C10	1.472 (7)
C8—S—C9	91.7 (2)	C4—C5—C6	117.6 (4)
C6—C1—C2	124.7 (5)	C4—C5—C7	125.2 (5)
C6—C1—N1	116.8 (4)	C6—C5—C7	117.2 (4)
C2—C1—N1	118.4 (4)	C1—C6—C5	117.9 (5)
O2—N1—O1	125.4 (5)	C1—C6—H6A	121.1
O2—N1—C1	117.7 (4)	C5—C6—H6A	121.1
O1—N1—C1	116.9 (4)	C8—C7—C5	130.8 (5)
C10—N2—C9	117.8 (4)	C8—C7—H7A	114.6
C10—N2—H2A	121.1	C5—C7—H7A	114.6
C9—N2—H2A	121.1	C7—C8—C10	119.5 (4)
C1—C2—C3	117.3 (5)	C7—C8—S	129.5 (4)
C1—C2—H2B	121.3	C10—C8—S	110.9 (4)
C3—C2—H2B	121.3	O3—C9—N2	126.1 (5)
C2—C3—C4	120.9 (5)	O3—C9—S	124.4 (4)
C2—C3—H3A	119.6	N2—C9—S	109.4 (4)
C4—C3—H3A	119.6	O4—C10—N2	123.6 (5)
C3—C4—C5	121.5 (5)	O4—C10—C8	126.3 (5)
C3—C4—H4A	119.3	N2—C10—C8	110.1 (4)
C5—C4—H4A	119.3
C6—C1—N1—O2	−3.9 (7)	C6—C5—C7—C8	−176.0 (5)
C2—C1—N1—O2	179.6 (5)	C5—C7—C8—C10	−174.0 (5)
C6—C1—N1—O1	175.7 (5)	C5—C7—C8—S	1.8 (9)
C2—C1—N1—O1	−0.7 (7)	C9—S—C8—C7	−175.0 (5)
C6—C1—C2—C3	−0.5 (8)	C9—S—C8—C10	1.2 (4)
N1—C1—C2—C3	175.6 (5)	C10—N2—C9—O3	−180.0 (6)
C1—C2—C3—C4	1.6 (9)	C10—N2—C9—S	−3.0 (6)
C2—C3—C4—C5	0.6 (9)	C8—S—C9—O3	177.9 (6)
C3—C4—C5—C6	−3.7 (8)	C8—S—C9—N2	0.9 (4)
C3—C4—C5—C7	177.8 (5)	C9—N2—C10—O4	−176.6 (5)
C2—C1—C6—C5	−2.6 (8)	C9—N2—C10—C8	3.9 (7)
N1—C1—C6—C5	−178.8 (4)	C7—C8—C10—O4	−5.8 (9)
C4—C5—C6—C1	4.6 (7)	S—C8—C10—O4	177.6 (5)
C7—C5—C6—C1	−176.7 (5)	C7—C8—C10—N2	173.6 (5)
C4—C5—C7—C8	2.5 (9)	S—C8—C10—N2	−3.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4^i	0.86	2.00	2.846 (6)	167
C4—H4A···S	0.93	2.54	3.246 (6)	132
C6—H6A···O2^ii	0.93	2.54	3.387 (7)	152
C7—H7A···O4	0.93	2.49	2.856 (7)	104
C7—H7A···O2^ii	0.93	2.51	3.390 (7)	157

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