2-Imino-3-(2-nitro-phen-yl)-1,3-thia-zolidin-4-one.

In the title compound, C(9)H(7)N(3)O(3)S, the nitro and thia-zolidinone moieties are inclined with respect to the aromatic ring at dihedral angles of 9.57 (16) and 78.42 (4)°, respectively. In the crystal, N-H⋯O hydrogen bonding connects the mol-ecules along the c and a axes to form a two-dimensional polymeric network. A weak S⋯O inter-action [3.2443 (11) Å] and phenyl ring to phenyl ring off-set π⋯π stacking [with centroid-centroid separation of 3.6890 (7) Å and ring slippage of 1.479 Å] link the polymeric chains along the b and a axes, respectively.

Related literature

For the biological activities of thia­zolidinones, see: Barreca et al. (2001 ▶); Shah & Desai (2007 ▶); Mehta et al. (2006 ▶); Vazzana et al. (2004 ▶); Wrobel et al. (2006 ▶). For related structures, see: Shahwar et al. (2009 ▶, 2011 ▶); Zhou et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the comparative C—C separation in graphite, see: Trucano & Chen (1975 ▶).

Experimental

Crystal data

C9H7N3O3S

M = 237.24

Monoclinic,

a = 7.3036 (5) Å

b = 16.4409 (10) Å

c = 8.2455 (5) Å

β = 102.1321 (9)°

V = 967.99 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 150 K

0.70 × 0.61 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.802, T max = 0.880

11000 measured reflections

2938 independent reflections

2675 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.03

2938 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033812/ez2256sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033812/ez2256Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033812/ez2256Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H7N3O3S	F(000) = 488
Mr = 237.24	Dx = 1.628 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6547 reflections
a = 7.3036 (5) Å	θ = 2.5–30.5°
b = 16.4409 (10) Å	µ = 0.33 mm−1
c = 8.2455 (5) Å	T = 150 K
β = 102.1321 (9)°	Block, light yellow
V = 967.99 (11) Å3	0.70 × 0.61 × 0.40 mm
Z = 4

Bruker APEXII CCD diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2675 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω rotation with narrow frames scans	θmax = 30.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.802, Tmax = 0.880	k = −23→23
11000 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.3974P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.43457 (15)	0.75201 (6)	0.52262 (14)	0.0182 (2)
N1	0.58325 (14)	0.79287 (6)	0.55992 (14)	0.0239 (2)
H1	0.686 (2)	0.7635 (10)	0.564 (2)	0.029*
S1	0.40353 (4)	0.646740 (16)	0.48418 (4)	0.02236 (9)
C2	0.15109 (16)	0.65317 (6)	0.44907 (16)	0.0213 (2)
H2A	0.0937	0.6319	0.3376	0.026*
H2B	0.1044	0.6207	0.5330	0.026*
C3	0.10139 (15)	0.74173 (6)	0.46228 (14)	0.0186 (2)
O1	−0.05729 (12)	0.76769 (5)	0.43725 (12)	0.02667 (19)
N2	0.25861 (12)	0.78966 (5)	0.50525 (12)	0.01726 (18)
C4	0.24651 (14)	0.87451 (6)	0.53960 (13)	0.01660 (19)
C5	0.26722 (14)	0.93712 (6)	0.42976 (13)	0.01709 (19)
C6	0.25532 (15)	1.01822 (7)	0.47384 (14)	0.0206 (2)
H6	0.2702	1.0601	0.3984	0.025*
C7	0.22162 (16)	1.03764 (7)	0.62847 (15)	0.0233 (2)
H7	0.2142	1.0930	0.6595	0.028*
C8	0.19873 (17)	0.97645 (7)	0.73760 (15)	0.0243 (2)
H8	0.1740	0.9899	0.8430	0.029*
C9	0.21179 (16)	0.89517 (7)	0.69338 (14)	0.0215 (2)
H9	0.1968	0.8535	0.7693	0.026*
N3	0.30099 (14)	0.92086 (6)	0.26329 (12)	0.02117 (19)
O2	0.33657 (15)	0.85158 (5)	0.22577 (12)	0.0294 (2)
O3	0.29218 (19)	0.97834 (6)	0.16775 (13)	0.0414 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0191 (5)	0.0140 (4)	0.0231 (5)	0.0032 (4)	0.0083 (4)	0.0021 (4)
N1	0.0180 (4)	0.0189 (4)	0.0361 (5)	0.0019 (3)	0.0085 (4)	0.0007 (4)
S1	0.02110 (15)	0.01369 (14)	0.03376 (17)	0.00281 (9)	0.00911 (11)	−0.00049 (10)
C2	0.0203 (5)	0.0130 (4)	0.0310 (6)	0.0007 (4)	0.0060 (4)	−0.0002 (4)
C3	0.0191 (5)	0.0148 (4)	0.0231 (5)	−0.0007 (4)	0.0072 (4)	0.0011 (4)
O1	0.0182 (4)	0.0202 (4)	0.0424 (5)	0.0015 (3)	0.0081 (3)	−0.0003 (4)
N2	0.0164 (4)	0.0119 (4)	0.0249 (4)	0.0013 (3)	0.0074 (3)	0.0004 (3)
C4	0.0153 (4)	0.0125 (4)	0.0224 (5)	0.0018 (3)	0.0049 (4)	0.0003 (4)
C5	0.0167 (4)	0.0150 (4)	0.0194 (4)	−0.0005 (3)	0.0035 (3)	0.0003 (4)
C6	0.0212 (5)	0.0138 (5)	0.0256 (5)	−0.0011 (4)	0.0020 (4)	0.0009 (4)
C7	0.0233 (5)	0.0157 (5)	0.0294 (6)	0.0019 (4)	0.0023 (4)	−0.0047 (4)
C8	0.0274 (5)	0.0219 (5)	0.0245 (5)	0.0043 (4)	0.0073 (4)	−0.0043 (4)
C9	0.0249 (5)	0.0181 (5)	0.0232 (5)	0.0032 (4)	0.0091 (4)	0.0018 (4)
N3	0.0243 (5)	0.0192 (4)	0.0201 (4)	−0.0040 (3)	0.0049 (3)	0.0003 (3)
O2	0.0430 (5)	0.0220 (4)	0.0257 (4)	0.0011 (4)	0.0125 (4)	−0.0036 (3)
O3	0.0751 (8)	0.0249 (5)	0.0263 (5)	−0.0035 (5)	0.0156 (5)	0.0074 (4)

C1—N1	1.2589 (15)	C4—C5	1.4002 (14)
C1—N2	1.4064 (13)	C5—C6	1.3895 (14)
C1—S1	1.7655 (11)	C5—N3	1.4693 (14)
N1—H1	0.886 (18)	C6—C7	1.3857 (17)
S1—C2	1.8083 (12)	C6—H6	0.9500
C2—C3	1.5100 (14)	C7—C8	1.3831 (17)
C2—H2A	0.9900	C7—H7	0.9500
C2—H2B	0.9900	C8—C9	1.3938 (15)
C3—O1	1.2113 (14)	C8—H8	0.9500
C3—N2	1.3762 (14)	C9—H9	0.9500
N2—C4	1.4299 (13)	N3—O2	1.2225 (13)
C4—C9	1.3866 (15)	N3—O3	1.2234 (13)
N1—C1—N2	120.86 (10)	C5—C4—N2	124.72 (9)
N1—C1—S1	129.69 (9)	C6—C5—C4	121.00 (10)
N2—C1—S1	109.45 (8)	C6—C5—N3	116.81 (9)
C1—N1—H1	113.5 (11)	C4—C5—N3	122.19 (9)
C1—S1—C2	93.42 (5)	C7—C6—C5	119.65 (10)
C3—C2—S1	107.29 (7)	C7—C6—H6	120.2
C3—C2—H2A	110.3	C5—C6—H6	120.2
S1—C2—H2A	110.3	C8—C7—C6	120.02 (10)
C3—C2—H2B	110.3	C8—C7—H7	120.0
S1—C2—H2B	110.3	C6—C7—H7	120.0
H2A—C2—H2B	108.5	C7—C8—C9	120.19 (11)
O1—C3—N2	123.96 (10)	C7—C8—H8	119.9
O1—C3—C2	124.29 (10)	C9—C8—H8	119.9
N2—C3—C2	111.75 (9)	C4—C9—C8	120.65 (11)
C3—N2—C1	117.99 (9)	C4—C9—H9	119.7
C3—N2—C4	121.79 (9)	C8—C9—H9	119.7
C1—N2—C4	120.16 (9)	O2—N3—O3	122.83 (11)
C9—C4—C5	118.48 (10)	O2—N3—C5	119.50 (9)
C9—C4—N2	116.80 (9)	O3—N3—C5	117.68 (10)
N1—C1—S1—C2	178.92 (12)	C1—N2—C4—C5	80.50 (14)
N2—C1—S1—C2	−1.26 (9)	C9—C4—C5—C6	0.66 (16)
C1—S1—C2—C3	2.58 (9)	N2—C4—C5—C6	−179.31 (10)
S1—C2—C3—O1	176.24 (10)	C9—C4—C5—N3	−178.92 (10)
S1—C2—C3—N2	−3.36 (12)	N2—C4—C5—N3	1.11 (16)
O1—C3—N2—C1	−176.90 (11)	C4—C5—C6—C7	−0.29 (16)
C2—C3—N2—C1	2.70 (14)	N3—C5—C6—C7	179.30 (10)
O1—C3—N2—C4	6.11 (17)	C5—C6—C7—C8	−0.45 (17)
C2—C3—N2—C4	−174.29 (9)	C6—C7—C8—C9	0.81 (18)
N1—C1—N2—C3	179.21 (11)	C5—C4—C9—C8	−0.29 (17)
S1—C1—N2—C3	−0.64 (12)	N2—C4—C9—C8	179.68 (10)
N1—C1—N2—C4	−3.75 (16)	C7—C8—C9—C4	−0.44 (18)
S1—C1—N2—C4	176.40 (8)	C6—C5—N3—O2	170.66 (11)
C3—N2—C4—C9	77.45 (13)	C4—C5—N3—O2	−9.75 (16)
C1—N2—C4—C9	−99.47 (12)	C6—C5—N3—O3	−9.25 (16)
C3—N2—C4—C5	−102.57 (13)	C4—C5—N3—O3	170.35 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.886 (18)	2.334 (18)	3.0337 (13)	135.9 (14)
N1—H1···O2ii	0.886 (18)	2.439 (17)	3.1416 (14)	136.5 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.886 (18)	2.334 (18)	3.0337 (13)	135.9 (14)
N1—H1⋯O2ii	0.886 (18)	2.439 (17)	3.1416 (14)	136.5 (14)

Symmetry codes: (i) ; (ii) .