3,3'-(1-Oxopropane-1,3-di-yl)bis-(1,3-thia-zolidine-2-thione) chloro-benzene hemisolvate.

The title compound, C9H12N2OS4·0.5C6H5Cl, which contains two 1,3-thia-zolidine-2-thione rings, is a by-product of the synthesis of 3-acryloyl-1,3-thia-zolidine-2-thione. The dihedral angle between these rings is 79.95 (9)°, with both rings displaying a twisted conformation. The twist angle of the amide group is 5.6 (1)°. In the crystal, the molecules are linked into [001] chains by C-H⋯O interactions. The chloro-benzene solvent mol-ecule was found to show unresolvable disorder about a centre of inversion and its contribution to the scattering was removed with the SQUEEZE option in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155].

Related literature

For N-substituted 1,3-thia­zolidine-2-thione and for further synthetic details, see: Evans & Thomson (2005 ▶). For the defin­ition of amide twist angles, see: Yamada et al. (1993 ▶). For details of the use of SQUEEZE, see: van der Sluis & Spek (1990 ▶).

Experimental

Crystal data

C9H12N2OS4·0.5C6H5Cl

M = 348.72

Monoclinic,

a = 8.59506 (18) Å

b = 9.4435 (2) Å

c = 18.2640 (4) Å

β = 92.614 (2)°

V = 1480.90 (6) Å3

Z = 4

Cu Kα radiation

μ = 6.68 mm−1

T = 123 K

0.45 × 0.25 × 0.14 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2012 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.757, T max = 1.000

5329 measured reflections

2971 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.05

2971 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003292/hb7002sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003292/hb7002Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003292/hb7002Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003292/hb7002Isup4.cml

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

C9H12N2OS4·0.5C6H5Cl	F(000) = 724
Mr = 348.72	Dx = 1.564 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.59506 (18) Å	Cell parameters from 2930 reflections
b = 9.4435 (2) Å	θ = 4.7–75.6°
c = 18.2640 (4) Å	µ = 6.68 mm−1
β = 92.614 (2)°	T = 123 K
V = 1480.90 (6) Å3	Prism, colorless
Z = 4	0.45 × 0.25 × 0.14 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	2971 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2486 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.5081 pixels mm-1	θmax = 75.8°, θmin = 4.9°
ω scans	h = −9→10
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)]	k = −11→10
Tmin = 0.757, Tmax = 1.000	l = −22→20
5329 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0574P)2 + 1.0183P] where P = (Fo2 + 2Fc2)/3
2971 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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
S1	0.38391 (7)	0.58687 (8)	0.30163 (4)	0.02748 (18)
S2	0.16697 (8)	0.60275 (8)	0.17409 (4)	0.02960 (19)
S3	0.75412 (7)	0.06152 (7)	0.39778 (4)	0.02613 (18)
S4	1.01178 (8)	0.25235 (8)	0.44956 (4)	0.02741 (18)
O1	0.5444 (2)	0.2367 (2)	0.15272 (10)	0.0247 (4)
N1	0.3858 (2)	0.4161 (2)	0.17961 (11)	0.0194 (4)
N2	0.8680 (3)	0.2837 (2)	0.32473 (12)	0.0232 (5)
C1	0.3274 (3)	0.5256 (3)	0.22011 (14)	0.0210 (5)
C2	0.1553 (4)	0.4708 (4)	0.10302 (18)	0.0398 (8)
H2A	0.0692	0.4039	0.1114	0.048*
H2B	0.1363	0.5160	0.0545	0.048*
C3	0.3092 (3)	0.3939 (3)	0.10594 (14)	0.0235 (5)
H3A	0.2922	0.2915	0.0971	0.028*
H3B	0.3762	0.4309	0.0676	0.028*
C4	0.5170 (3)	0.3302 (3)	0.19528 (14)	0.0193 (5)
C5	0.6201 (3)	0.3555 (3)	0.26305 (13)	0.0180 (5)
H5A	0.5621	0.3338	0.3073	0.022*
H5B	0.6522	0.4561	0.2653	0.022*
C6	0.7637 (3)	0.2609 (3)	0.26076 (14)	0.0254 (5)
H6A	0.7308	0.1604	0.2590	0.030*
H6B	0.8196	0.2815	0.2158	0.030*
C7	0.8692 (3)	0.2009 (3)	0.38392 (13)	0.0195 (5)
C8	1.0683 (4)	0.4060 (4)	0.39771 (18)	0.0404 (8)
H8A	1.0306	0.4937	0.4206	0.048*
H8B	1.1831	0.4111	0.3959	0.048*
C9	0.9945 (4)	0.3887 (3)	0.32101 (18)	0.0355 (7)
H9A	0.9523	0.4804	0.3030	0.043*
H9B	1.0732	0.3558	0.2869	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0230 (3)	0.0325 (4)	0.0272 (3)	0.0043 (3)	0.0034 (2)	−0.0095 (3)
S2	0.0241 (3)	0.0368 (4)	0.0281 (3)	0.0123 (3)	0.0033 (2)	−0.0017 (3)
S3	0.0224 (3)	0.0275 (3)	0.0290 (3)	−0.0045 (2)	0.0071 (2)	−0.0041 (3)
S4	0.0287 (3)	0.0288 (4)	0.0242 (3)	−0.0057 (3)	−0.0048 (2)	0.0034 (3)
O1	0.0292 (9)	0.0204 (9)	0.0244 (9)	0.0041 (8)	0.0012 (7)	−0.0059 (7)
N1	0.0190 (9)	0.0212 (10)	0.0180 (9)	−0.0019 (8)	0.0027 (7)	0.0001 (8)
N2	0.0277 (11)	0.0201 (11)	0.0216 (10)	0.0042 (9)	−0.0003 (8)	−0.0007 (8)
C1	0.0167 (11)	0.0217 (12)	0.0252 (12)	−0.0014 (9)	0.0066 (9)	0.0029 (10)
C2	0.0347 (16)	0.0485 (19)	0.0350 (16)	0.0171 (15)	−0.0120 (13)	−0.0150 (14)
C3	0.0253 (12)	0.0265 (13)	0.0189 (12)	0.0016 (11)	0.0019 (9)	−0.0003 (10)
C4	0.0189 (11)	0.0175 (11)	0.0218 (12)	−0.0024 (9)	0.0053 (9)	0.0025 (9)
C5	0.0201 (11)	0.0170 (11)	0.0170 (11)	0.0000 (9)	0.0024 (9)	0.0004 (9)
C6	0.0257 (12)	0.0271 (14)	0.0228 (12)	0.0075 (11)	−0.0038 (10)	−0.0027 (11)
C7	0.0157 (10)	0.0224 (12)	0.0205 (11)	0.0063 (9)	0.0019 (9)	−0.0045 (9)
C8	0.0521 (19)	0.0308 (16)	0.0373 (17)	−0.0188 (14)	−0.0080 (14)	0.0101 (13)
C9	0.0443 (17)	0.0287 (15)	0.0327 (15)	−0.0086 (13)	−0.0064 (13)	0.0085 (12)

S1—C1	1.650 (3)	C2—H2B	0.9900
S2—C1	1.741 (3)	C3—H3A	0.9900
S2—C2	1.799 (3)	C3—H3B	0.9900
S3—C7	1.673 (3)	C4—C5	1.508 (3)
S4—C7	1.744 (3)	C5—C6	1.526 (3)
S4—C8	1.811 (3)	C5—H5A	0.9900
O1—C4	1.206 (3)	C5—H5B	0.9900
N1—C1	1.379 (3)	C6—H6A	0.9900
N1—C4	1.408 (3)	C6—H6B	0.9900
N1—C3	1.486 (3)	C8—C9	1.520 (4)
N2—C7	1.334 (4)	C8—H8A	0.9900
N2—C6	1.456 (3)	C8—H8B	0.9900
N2—C9	1.475 (4)	C9—H9A	0.9900
C2—C3	1.508 (4)	C9—H9B	0.9900
C2—H2A	0.9900
C1—S2—C2	94.31 (13)	C4—C5—H5A	109.8
C7—S4—C8	93.47 (14)	C6—C5—H5A	109.8
C1—N1—C4	129.1 (2)	C4—C5—H5B	109.8
C1—N1—C3	115.8 (2)	C6—C5—H5B	109.8
C4—N1—C3	114.9 (2)	H5A—C5—H5B	108.3
C7—N2—C6	123.1 (2)	N2—C6—C5	111.2 (2)
C7—N2—C9	116.9 (2)	N2—C6—H6A	109.4
C6—N2—C9	119.4 (2)	C5—C6—H6A	109.4
N1—C1—S1	130.4 (2)	N2—C6—H6B	109.4
N1—C1—S2	110.76 (19)	C5—C6—H6B	109.4
S1—C1—S2	118.87 (15)	H6A—C6—H6B	108.0
C3—C2—S2	106.8 (2)	N2—C7—S3	127.0 (2)
C3—C2—H2A	110.4	N2—C7—S4	111.9 (2)
S2—C2—H2A	110.4	S3—C7—S4	121.13 (15)
C3—C2—H2B	110.4	C9—C8—S4	106.6 (2)
S2—C2—H2B	110.4	C9—C8—H8A	110.4
H2A—C2—H2B	108.6	S4—C8—H8A	110.4
N1—C3—C2	108.4 (2)	C9—C8—H8B	110.4
N1—C3—H3A	110.0	S4—C8—H8B	110.4
C2—C3—H3A	110.0	H8A—C8—H8B	108.6
N1—C3—H3B	110.0	N2—C9—C8	107.9 (2)
C2—C3—H3B	110.0	N2—C9—H9A	110.1
H3A—C3—H3B	108.4	C8—C9—H9A	110.1
O1—C4—N1	117.9 (2)	N2—C9—H9B	110.1
O1—C4—C5	121.4 (2)	C8—C9—H9B	110.1
N1—C4—C5	120.7 (2)	H9A—C9—H9B	108.4
C4—C5—C6	109.3 (2)
C4—N1—C1—S1	−3.8 (4)	N1—C4—C5—C6	−172.5 (2)
C3—N1—C1—S1	−177.4 (2)	C7—N2—C6—C5	97.3 (3)
C4—N1—C1—S2	177.3 (2)	C9—N2—C6—C5	−92.1 (3)
C3—N1—C1—S2	3.7 (3)	C4—C5—C6—N2	179.0 (2)
C2—S2—C1—N1	8.0 (2)	C6—N2—C7—S3	−1.3 (4)
C2—S2—C1—S1	−170.96 (19)	C9—N2—C7—S3	−172.1 (2)
C1—S2—C2—C3	−16.8 (3)	C6—N2—C7—S4	177.92 (19)
C1—N1—C3—C2	−16.4 (3)	C9—N2—C7—S4	7.1 (3)
C4—N1—C3—C2	169.0 (2)	C8—S4—C7—N2	4.2 (2)
S2—C2—C3—N1	20.6 (3)	C8—S4—C7—S3	−176.58 (19)
C1—N1—C4—O1	177.7 (2)	C7—S4—C8—C9	−13.2 (3)
C3—N1—C4—O1	−8.6 (3)	C7—N2—C9—C8	−17.1 (4)
C1—N1—C4—C5	−2.6 (4)	C6—N2—C9—C8	171.7 (3)
C3—N1—C4—C5	171.0 (2)	S4—C8—C9—N2	18.3 (3)
O1—C4—C5—C6	7.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.99	2.55	3.340 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.99	2.55	3.340 (4)	137

Symmetry code: (i) .