1-[(4S)-4-Benzyl-2-thioxo-1,3-thia-zol-idin-3-yl]propan-1-one.

The analysis of the title chiral auxiliary compound, C(13)H(15)NOS(2), has enabled the determination of the absolute configuration at the benzyl-bearing ring C atom as S. In the crystal structure, mol-ecules aggregate into helical chains along the b axis via C-H⋯O contacts.

Related literature

For background to the use of N-acyl thia­zolidinethio­nes as versatile chiral auxiliaries for asymmetric aldol reactions, see: Crimmins & Chaudhary (2000 ▶); Crimmins et al. (2005 ▶); Crimmins & Haley (2006 ▶); Crimmins & Dechert (2009 ▶). For the synthesis, see: McKennon & Meyer (1993 ▶); Delaunay et al. (1995 ▶); Lu et al. (2009 ▶).

Experimental

Crystal data

C13H15NOS2

M = 265.39

Monoclinic,

a = 8.850 (6) Å

b = 7.189 (5) Å

c = 10.595 (7) Å

β = 95.537 (6)°

V = 670.9 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.831, T max = 0.925

7301 measured reflections

2734 independent reflections

2361 reflections with F 2 > 2σ(F 2)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.048

S = 0.86

2734 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1138 Friedel pairs

Flack parameter: −0.05 (6)

Data collection: CrystalClear (Pflugrath, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: X-SEED (Barbour et al., 2001 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030104/tk2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030104/tk2514Isup2.hkl

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

C13H15NOS2	F(000) = 280
Mr = 265.39	Dx = 1.314 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 3674 reflections
a = 8.850 (6) Å	θ = 2.3–27.4°
b = 7.189 (5) Å	µ = 0.38 mm−1
c = 10.595 (7) Å	T = 298 K
β = 95.537 (6)°	Prism, yellow
V = 670.9 (8) Å3	0.50 × 0.40 × 0.20 mm
Z = 2

Rigaku Mercury diffractometer	2361 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1	Rint = 0.038
ω scans	θmax = 27.4°
Absorption correction: multi-scan (Jacobson, 1998)	h = −11→11
Tmin = 0.831, Tmax = 0.925	k = −6→9
7301 measured reflections	l = −13→13
2734 independent reflections

Refinement on F2	Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 10359.0000 14093.9000 3595.6900
R[F2 > 2σ(F2)] = 0.041	(Δ/σ)max < 0.001
wR(F2) = 0.048	Δρmax = 0.32 e Å−3
S = 0.86	Δρmin = −0.35 e Å−3
2734 reflections	Absolute structure: Flack (1983), 1138 Friedel pairs
170 parameters	Flack parameter: −0.05 (6)
H-atom parameters constrained

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	0.55104 (6)	1.08609 (10)	0.94969 (5)	0.0574 (2)
S2	0.80540 (7)	1.31770 (10)	1.04864 (6)	0.0630 (2)
O1	0.96079 (17)	1.0605 (2)	0.69074 (15)	0.0720 (6)
N1	0.79082 (15)	1.1039 (2)	0.83154 (13)	0.0410 (4)
C1	0.6994 (2)	0.9543 (2)	0.76431 (19)	0.0436 (6)
C2	0.5366 (2)	0.9806 (2)	0.79429 (19)	0.0498 (7)
C3	0.7324 (2)	1.1748 (2)	0.93706 (19)	0.0462 (6)
C4	0.7616 (2)	0.7610 (2)	0.80159 (19)	0.0469 (6)
C5	0.7183 (2)	0.6180 (2)	0.70140 (17)	0.0441 (6)
C6	0.5872 (2)	0.5119 (2)	0.7014 (2)	0.0561 (7)
C7	0.5469 (3)	0.3871 (3)	0.6051 (2)	0.0673 (9)
C8	0.6379 (3)	0.3610 (3)	0.5087 (2)	0.0704 (9)
C9	0.7667 (3)	0.4651 (3)	0.5063 (2)	0.0719 (9)
C10	0.8074 (2)	0.5935 (3)	0.60097 (19)	0.0569 (7)
C11	0.9289 (2)	1.1496 (2)	0.7801 (2)	0.0501 (7)
C12	1.0320 (2)	1.3001 (3)	0.8384 (2)	0.0545 (7)
C13	1.1629 (2)	1.3369 (4)	0.7610 (2)	0.0861 (10)
H1	0.70330	0.96970	0.67560	0.0520*
H6	0.52430	0.52600	0.76860	0.0670*
H7	0.45570	0.31750	0.60530	0.0790*
H8	0.61000	0.27260	0.44400	0.0830*
H9	0.83030	0.44600	0.44020	0.0870*
H10	0.89540	0.66810	0.59680	0.0690*
H21	0.48380	1.06070	0.73390	0.0600*
H22	0.48550	0.86440	0.79480	0.0590*
H41	0.72130	0.72350	0.87750	0.0550*
H42	0.86910	0.76750	0.81570	0.0560*
H121	1.07080	1.26210	0.92110	0.0650*
H122	0.97480	1.41110	0.84380	0.0650*
H131	1.19300	1.46340	0.77050	0.1050*
H132	1.24580	1.25860	0.78930	0.1050*
H133	1.13230	1.31200	0.67430	0.1050*

	U11	U22	U33	U12	U13	U23
S1	0.0512 (2)	0.0621 (3)	0.0611 (3)	−0.0066 (3)	0.0167 (2)	−0.0116 (3)
S2	0.0587 (3)	0.0640 (4)	0.0664 (3)	−0.0025 (3)	0.0059 (2)	−0.0247 (3)
O1	0.0664 (9)	0.0751 (11)	0.0796 (10)	−0.0150 (9)	0.0330 (8)	−0.0265 (10)
N1	0.0401 (7)	0.0364 (8)	0.0470 (8)	−0.0001 (7)	0.0062 (6)	−0.0019 (7)
C1	0.0419 (10)	0.0430 (11)	0.0458 (10)	−0.0008 (8)	0.0035 (8)	0.0002 (8)
C2	0.0417 (10)	0.0508 (13)	0.0561 (12)	−0.0027 (9)	0.0011 (8)	−0.0019 (9)
C3	0.0427 (10)	0.0438 (11)	0.0513 (11)	0.0037 (8)	0.0008 (8)	−0.0042 (9)
C4	0.0510 (11)	0.0393 (11)	0.0487 (11)	0.0028 (8)	−0.0031 (8)	−0.0011 (8)
C5	0.0453 (10)	0.0389 (12)	0.0467 (10)	0.0008 (8)	−0.0027 (8)	0.0025 (8)
C6	0.0647 (13)	0.0460 (13)	0.0569 (12)	−0.0083 (10)	0.0017 (10)	0.0087 (9)
C7	0.0828 (17)	0.0465 (14)	0.0678 (15)	−0.0207 (11)	−0.0179 (13)	0.0093 (11)
C8	0.104 (2)	0.0511 (15)	0.0517 (13)	−0.0052 (13)	−0.0146 (13)	−0.0034 (11)
C9	0.0992 (19)	0.0603 (15)	0.0580 (14)	0.0079 (15)	0.0176 (13)	−0.0055 (12)
C10	0.0579 (11)	0.0527 (12)	0.0617 (12)	0.0015 (12)	0.0134 (9)	−0.0026 (12)
C11	0.0415 (11)	0.0480 (13)	0.0617 (12)	0.0026 (8)	0.0095 (9)	−0.0011 (9)
C12	0.0430 (10)	0.0488 (12)	0.0711 (13)	−0.0016 (10)	0.0032 (9)	−0.0073 (11)
C13	0.0543 (13)	0.086 (2)	0.121 (2)	−0.0223 (15)	0.0242 (13)	−0.0216 (19)

S1—C2	1.806 (2)	C12—C13	1.506 (3)
S1—C3	1.744 (2)	C1—H1	0.9500
S2—C3	1.650 (2)	C2—H21	0.9500
O1—C11	1.199 (3)	C2—H22	0.9500
N1—C1	1.486 (2)	C4—H41	0.9500
N1—C3	1.374 (3)	C4—H42	0.9500
N1—C11	1.424 (2)	C6—H6	0.9500
C1—C2	1.517 (3)	C7—H7	0.9500
C1—C4	1.532 (2)	C8—H8	0.9500
C4—C5	1.501 (3)	C9—H9	0.9500
C5—C6	1.389 (3)	C10—H10	0.9500
C5—C10	1.395 (3)	C12—H121	0.9500
C6—C7	1.380 (3)	C12—H122	0.9500
C7—C8	1.373 (3)	C13—H131	0.9500
C8—C9	1.366 (4)	C13—H132	0.9500
C9—C10	1.385 (3)	C13—H133	0.9500
C11—C12	1.509 (3)
C2—S1—C3	93.92 (9)	C1—C2—H21	110.00
C1—N1—C3	115.36 (14)	C1—C2—H22	111.00
C1—N1—C11	115.55 (14)	H21—C2—H22	109.00
C3—N1—C11	129.05 (14)	C1—C4—H41	109.00
N1—C1—C2	107.08 (13)	C1—C4—H42	109.00
N1—C1—C4	111.56 (15)	C5—C4—H41	108.00
C2—C1—C4	112.58 (14)	C5—C4—H42	109.00
S1—C2—C1	104.96 (13)	H41—C4—H42	109.00
S1—C3—S2	118.18 (11)	C5—C6—H6	119.00
S1—C3—N1	110.37 (12)	C7—C6—H6	120.00
S2—C3—N1	131.43 (14)	C6—C7—H7	120.00
C1—C4—C5	112.21 (15)	C8—C7—H7	119.00
C4—C5—C6	122.19 (16)	C7—C8—H8	120.00
C4—C5—C10	120.09 (16)	C9—C8—H8	121.00
C6—C5—C10	117.67 (16)	C8—C9—H9	119.00
C5—C6—C7	120.91 (19)	C10—C9—H9	120.00
C6—C7—C8	120.7 (2)	C5—C10—H10	119.00
C7—C8—C9	119.3 (2)	C9—C10—H10	120.00
C8—C9—C10	120.7 (2)	C11—C12—H121	109.00
C5—C10—C9	120.65 (18)	C11—C12—H122	109.00
O1—C11—N1	117.07 (15)	C13—C12—H121	109.00
O1—C11—C12	121.82 (17)	C13—C12—H122	109.00
N1—C11—C12	121.09 (16)	H121—C12—H122	109.00
C11—C12—C13	111.70 (18)	C12—C13—H131	109.00
N1—C1—H1	109.00	C12—C13—H132	110.00
C2—C1—H1	109.00	C12—C13—H133	109.00
C4—C1—H1	108.00	H131—C13—H132	109.00
S1—C2—H21	110.00	H131—C13—H133	110.00
S1—C2—H22	111.00	H132—C13—H133	109.00
C3—S1—C2—C1	22.91 (12)	C4—C1—C2—S1	93.51 (15)
C2—S1—C3—S2	171.92 (11)	N1—C1—C4—C5	−155.93 (15)
C2—S1—C3—N1	−9.64 (13)	C2—C1—C4—C5	83.7 (2)
C3—N1—C1—C2	25.15 (19)	C1—C4—C5—C6	−91.3 (2)
C3—N1—C1—C4	−98.44 (17)	C1—C4—C5—C10	86.0 (2)
C11—N1—C1—C2	−156.77 (15)	C4—C5—C6—C7	177.20 (17)
C11—N1—C1—C4	79.65 (19)	C10—C5—C6—C7	−0.1 (3)
C1—N1—C3—S1	−7.69 (18)	C4—C5—C10—C9	−178.46 (18)
C1—N1—C3—S2	170.47 (14)	C6—C5—C10—C9	−1.1 (3)
C11—N1—C3—S1	174.53 (14)	C5—C6—C7—C8	1.9 (3)
C11—N1—C3—S2	−7.3 (3)	C6—C7—C8—C9	−2.4 (3)
C1—N1—C11—O1	−2.2 (2)	C7—C8—C9—C10	1.2 (3)
C1—N1—C11—C12	179.47 (16)	C8—C9—C10—C5	0.6 (3)
C3—N1—C11—O1	175.56 (17)	O1—C11—C12—C13	7.3 (3)
C3—N1—C11—C12	−2.8 (3)	N1—C11—C12—C13	−174.42 (17)
N1—C1—C2—S1	−29.44 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.95	2.55	3.408 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.95	2.55	3.408 (4)	150

Symmetry code: (i) .