Redetermination of rhodanine at 173 K

The crystal structure of the title compound, C₃H₃NOS₂, has been redetermined at 173 K. The geometric parameters show a significant improvement in precision from the orginal determination [Van der Helm, Lessor & Merritt (1962). Acta Cryst. 15, 1227–1232], where the data were measured using photographic film. In the crystal structure, mol­ecules form planar N—H...S hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.020
• wR factor = 0.058
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Computing details

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Rhodanine

Crystal data

C3H3NOS2	F(000) = 272
Mr = 133.18	Dx = 1.687 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5868 reflections
a = 7.1876 (1) Å	θ = 2.7–34.8°
b = 7.5574 (1) Å	µ = 0.88 mm^−1
c = 9.9110 (2) Å	T = 173 K
β = 103.031 (1)°	Plate, colorless
V = 524.50 (2) Å^3	0.75 × 0.38 × 0.10 mm
Z = 4

Data collection

Bruker APEX-II diffractometer	1202 independent reflections
Radiation source: medium-focus sealed tube	1143 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.678, Tmax = 0.916	k = −9→9
5865 measured reflections	l = −12→12

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0302P)^2 + 0.2928P] where P = (Fo^2 + 2Fc^2)/3
1202 reflections	(Δ/σ)max = 0.001
76 parameters	Δρmax = 0.39 e Å^−3
3 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. The diameter of the X-ray beam is 0.8 mm. A somewhat long platelet was used in the measurements.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.52483 (4)	0.03297 (4)	0.75315 (3)	0.01603 (11)
S2	0.82783 (4)	0.03632 (4)	0.59006 (3)	0.01717 (11)
O1	0.3128 (1)	0.4720 (1)	0.5899 (1)	0.01596 (19)
N1	0.5580 (1)	0.2808 (1)	0.5831 (1)	0.0132 (2)
C1	0.6416 (2)	0.1251 (2)	0.6347 (1)	0.0131 (2)
C2	0.3490 (2)	0.2075 (2)	0.7302 (1)	0.0142 (2)
C3	0.4004 (2)	0.3361 (2)	0.6284 (1)	0.0126 (2)
H1	0.602 (2)	0.344 (2)	0.525 (1)	0.023 (4)*
H2	0.221 (2)	0.159 (2)	0.693 (2)	0.023 (4)*
H3	0.352 (2)	0.268 (2)	0.818 (1)	0.023 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0164 (2)	0.0155 (2)	0.0170 (2)	0.0014 (1)	0.0054 (1)	0.0054 (1)
S2	0.0139 (2)	0.0191 (2)	0.0189 (2)	0.0044 (1)	0.0046 (1)	0.0007 (1)
O1	0.0180 (4)	0.0151 (4)	0.0166 (4)	0.0028 (3)	0.0077 (3)	0.0019 (3)
N1	0.0149 (4)	0.0129 (4)	0.0135 (4)	0.0005 (4)	0.0067 (4)	0.0018 (3)
C1	0.0128 (5)	0.0143 (5)	0.0119 (5)	−0.0011 (4)	0.0021 (4)	−0.0012 (4)
C2	0.0148 (5)	0.0140 (5)	0.0152 (5)	0.0000 (4)	0.0063 (4)	0.0017 (4)
C3	0.0133 (5)	0.0136 (5)	0.0112 (5)	−0.0015 (4)	0.0032 (4)	−0.0011 (4)

Geometric parameters (Å, º)

S1—C1	1.735 (1)	N1—C3	1.375 (1)
S1—C2	1.805 (1)	C2—C3	1.505 (2)
S2—C1	1.645 (1)	N1—H1	0.86 (1)
O1—C3	1.220 (1)	C2—H2	0.98 (1)
N1—C1	1.367 (1)	C2—H3	0.98 (1)
C1—S1—C2	93.1 (1)	N1—C3—C2	111.6 (1)
C1—N1—C3	117.7 (1)	C1—N1—H1	122 (1)
N1—C1—S2	124.5 (1)	C3—N1—H1	120 (1)
N1—C1—S1	111.1 (1)	C3—C2—H2	110 (1)
S2—C1—S1	124.4 (1)	S1—C2—H2	110 (1)
C3—C2—S1	106.6 (1)	C3—C2—H3	110 (1)
O1—C3—N1	124.0 (1)	S1—C2—H3	111 (1)
O1—C3—C2	124.5 (1)	H2—C2—H3	110 (1)
C3—N1—C1—S2	178.6 (1)	C1—N1—C3—O1	−179.8 (1)
C3—N1—C1—S1	−1.1 (1)	C1—N1—C3—C2	−0.2 (1)
C2—S1—C1—N1	1.63 (9)	S1—C2—C3—O1	−1791 (1)
C2—S1—C1—S2	−178.1 (1)	S1—C2—C3—N1	1.4 (1)
C1—S1—C2—C3	−1.7 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86 (1)	1.98 (1)	2.831 (1)	169 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.