(2R,4R)-3-(tert-But-oxy-carbon-yl)-2-(3-chloro-phen-yl)-1,3-thia-zolidine-4-carb-oxy-lic acid monohydrate.

In the title compound, C(15)H(18)ClNO(4)S·H(2)O, the thia-zolidine ring displays a half-chair conformation. In the crystal, the water mol-ecules are linked to the organic acid mol-ecules via inter-molecular O-H⋯O hydrogen bonds.

Related literature

For applications of thia­zolidine derivatives, see: Kallen (1971 ▶); Seki et al. (2004 ▶); Song et al. (2009 ▶).

Experimental

Crystal data

C15H18ClNO4S·H2O

M = 361.83

Monoclinic,

a = 8.2460 (16) Å

b = 5.9660 (12) Å

c = 18.132 (4) Å

β = 99.81 (3)°

V = 879.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 293 K

0.20 × 0.17 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (ABSCOR; Higashi, 1995 ▶) T min = 0.932, T max = 0.948

3417 measured reflections

3182 independent reflections

2169 reflections with I > 2σ(I)

R int = 0.080

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.167

S = 1.03

3182 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1451 Friedel pairs

Flack parameter: −0.11 (16)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042133/xu5054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042133/xu5054Isup2.hkl

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

C15H18ClNO4S·H2O	F(000) = 380
Mr = 361.83	Dx = 1.367 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.2460 (16) Å	θ = 9–12°
b = 5.9660 (12) Å	µ = 0.36 mm−1
c = 18.132 (4) Å	T = 293 K
β = 99.81 (3)°	Block, colorless
V = 879.0 (3) Å3	0.20 × 0.17 × 0.15 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	2169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
graphite	θmax = 25.3°, θmin = 1.1°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (ABSCOR; Higashi, 1995)	k = −7→7
Tmin = 0.932, Tmax = 0.948	l = −21→21
3417 measured reflections	3 standard reflections every 200 reflections
3182 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.2379P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3182 reflections	Δρmax = 0.19 e Å−3
208 parameters	Δρmin = −0.28 e Å−3
1 restraint	Absolute structure: Flack (1983), 1451 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (16)

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	−0.27417 (18)	0.2513 (3)	0.65551 (8)	0.0556 (4)
Cl	0.2514 (3)	0.2819 (5)	0.47181 (11)	0.1051 (8)
N1	−0.0494 (5)	0.1770 (7)	0.7725 (2)	0.0353 (10)
O1	−0.0704 (5)	−0.2937 (7)	0.8136 (2)	0.0621 (12)
C1	−0.1971 (6)	0.0662 (9)	0.7899 (3)	0.0379 (13)
H1A	−0.2563	0.1677	0.8185	0.045*
O2	−0.2241 (5)	−0.1623 (7)	0.8928 (2)	0.0531 (11)
H2C	−0.1984	−0.2805	0.9148	0.080*
C2	−0.3015 (7)	0.0154 (11)	0.7147 (3)	0.0519 (16)
H2A	−0.4163	−0.0005	0.7195	0.062*
H2B	−0.2653	−0.1222	0.6940	0.062*
O3	0.0636 (4)	0.1875 (6)	0.89459 (18)	0.0422 (9)
C3	−0.0548 (6)	0.2640 (10)	0.6970 (3)	0.0415 (12)
H3A	−0.0212	0.4217	0.7007	0.050*
O4	0.1931 (4)	0.3384 (6)	0.80485 (18)	0.0407 (9)
C4	0.0541 (7)	0.1417 (9)	0.6516 (3)	0.0395 (13)
C5	0.0950 (7)	0.2482 (12)	0.5896 (3)	0.0505 (14)
H5C	0.0531	0.3897	0.5759	0.061*
C6	0.1987 (8)	0.1427 (12)	0.5482 (3)	0.0592 (17)
C7	0.2659 (8)	−0.0660 (13)	0.5677 (4)	0.0651 (19)
H7A	0.3366	−0.1334	0.5394	0.078*
C8	0.2260 (8)	−0.1720 (11)	0.6297 (3)	0.0590 (17)
H8A	0.2689	−0.3131	0.6433	0.071*
C9	0.1218 (7)	−0.0688 (10)	0.6721 (3)	0.0487 (15)
H9A	0.0970	−0.1402	0.7144	0.058*
C10	−0.1541 (6)	−0.1503 (10)	0.8333 (3)	0.0390 (13)
C11	0.0700 (6)	0.2343 (9)	0.8296 (3)	0.0366 (11)
C12	0.3466 (7)	0.4010 (9)	0.8560 (3)	0.0424 (14)
C13	0.4314 (7)	0.1879 (12)	0.8896 (4)	0.0663 (19)
H13A	0.3687	0.1236	0.9243	0.099*
H13B	0.5400	0.2238	0.9152	0.099*
H13C	0.4388	0.0823	0.8504	0.099*
C14	0.4440 (8)	0.5092 (12)	0.8017 (4)	0.0635 (19)
H14A	0.3894	0.6438	0.7819	0.095*
H14B	0.4516	0.4071	0.7615	0.095*
H14C	0.5525	0.5451	0.8274	0.095*
C15	0.3093 (9)	0.5670 (12)	0.9141 (4)	0.073 (2)
H15A	0.2574	0.6973	0.8894	0.110*
H15B	0.4099	0.6100	0.9457	0.110*
H15C	0.2369	0.4989	0.9438	0.110*
O5	0.8493 (5)	0.4638 (7)	0.9669 (2)	0.0585 (12)
H5B	0.7943	0.4847	1.0019	0.070*
H5A	0.9053	0.3446	0.9659	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.0481 (8)	0.0689 (11)	0.0474 (8)	0.0106 (9)	0.0013 (6)	0.0065 (8)
Cl	0.1239 (18)	0.130 (2)	0.0752 (12)	0.0239 (16)	0.0570 (12)	0.0417 (14)
N1	0.041 (2)	0.034 (2)	0.030 (2)	−0.003 (2)	0.0042 (19)	−0.0031 (19)
O1	0.076 (3)	0.049 (3)	0.069 (3)	0.013 (2)	0.031 (2)	0.005 (2)
C1	0.037 (3)	0.038 (3)	0.040 (3)	−0.002 (2)	0.011 (2)	−0.004 (2)
O2	0.061 (3)	0.048 (3)	0.055 (2)	0.005 (2)	0.021 (2)	0.012 (2)
C2	0.042 (3)	0.061 (4)	0.052 (4)	−0.007 (3)	0.005 (3)	−0.006 (3)
O3	0.047 (2)	0.046 (2)	0.034 (2)	−0.0027 (18)	0.0101 (16)	0.0039 (17)
C3	0.046 (3)	0.035 (3)	0.041 (3)	−0.001 (3)	0.001 (2)	−0.001 (3)
O4	0.042 (2)	0.041 (2)	0.0399 (19)	−0.0063 (18)	0.0093 (16)	−0.0023 (18)
C4	0.042 (3)	0.040 (3)	0.035 (3)	−0.001 (3)	0.002 (2)	−0.002 (3)
C5	0.061 (4)	0.046 (3)	0.047 (3)	0.001 (3)	0.017 (3)	0.003 (3)
C6	0.064 (4)	0.070 (5)	0.045 (4)	0.000 (4)	0.014 (3)	0.006 (3)
C7	0.063 (4)	0.082 (5)	0.054 (4)	0.011 (4)	0.023 (3)	−0.008 (4)
C8	0.077 (4)	0.049 (4)	0.055 (4)	0.015 (3)	0.023 (3)	0.000 (3)
C9	0.059 (4)	0.051 (4)	0.039 (3)	0.003 (3)	0.016 (3)	0.006 (3)
C10	0.035 (3)	0.041 (3)	0.042 (3)	−0.003 (3)	0.006 (2)	−0.002 (3)
C11	0.044 (3)	0.027 (3)	0.041 (3)	0.006 (3)	0.012 (2)	0.000 (2)
C12	0.037 (3)	0.039 (3)	0.051 (3)	−0.010 (3)	0.004 (3)	−0.001 (3)
C13	0.044 (3)	0.066 (5)	0.086 (5)	0.003 (3)	0.004 (3)	0.023 (4)
C14	0.052 (4)	0.059 (4)	0.080 (5)	−0.014 (3)	0.009 (4)	0.017 (4)
C15	0.079 (5)	0.067 (5)	0.071 (5)	−0.021 (4)	0.004 (4)	−0.021 (4)
O5	0.079 (3)	0.047 (3)	0.054 (3)	0.008 (2)	0.024 (2)	0.006 (2)

S1—C2	1.807 (6)	C5—H5C	0.9300
S1—C3	1.838 (5)	C6—C7	1.384 (10)
Cl—C6	1.733 (6)	C7—C8	1.379 (9)
N1—C11	1.346 (6)	C7—H7A	0.9300
N1—C3	1.457 (6)	C8—C9	1.390 (8)
N1—C1	1.466 (6)	C8—H8A	0.9300
O1—C10	1.192 (6)	C9—H9A	0.9300
C1—C2	1.513 (7)	C12—C15	1.515 (8)
C1—C10	1.524 (7)	C12—C14	1.516 (8)
C1—H1A	0.9800	C12—C13	1.527 (8)
O2—C10	1.309 (6)	C13—H13A	0.9600
O2—H2C	0.8200	C13—H13B	0.9600
C2—H2A	0.9700	C13—H13C	0.9600
C2—H2B	0.9700	C14—H14A	0.9600
O3—C11	1.221 (6)	C14—H14B	0.9600
C3—C4	1.505 (7)	C14—H14C	0.9600
C3—H3A	0.9800	C15—H15A	0.9600
O4—C11	1.332 (6)	C15—H15B	0.9600
O4—C12	1.483 (6)	C15—H15C	0.9600
C4—C5	1.383 (8)	O5—H5B	0.8499
C4—C9	1.398 (8)	O5—H5A	0.8500
C5—C6	1.382 (8)
C2—S1—C3	90.2 (3)	C7—C8—H8A	119.9
C11—N1—C3	122.2 (4)	C9—C8—H8A	119.9
C11—N1—C1	118.3 (4)	C8—C9—C4	120.5 (5)
C3—N1—C1	118.0 (4)	C8—C9—H9A	119.7
N1—C1—C2	105.2 (4)	C4—C9—H9A	119.7
N1—C1—C10	111.4 (4)	O1—C10—O2	124.6 (5)
C2—C1—C10	110.0 (5)	O1—C10—C1	123.3 (5)
N1—C1—H1A	110.0	O2—C10—C1	112.1 (5)
C2—C1—H1A	110.0	O3—C11—O4	126.3 (5)
C10—C1—H1A	110.0	O3—C11—N1	122.6 (5)
C10—O2—H2C	109.5	O4—C11—N1	111.1 (4)
C1—C2—S1	105.6 (4)	O4—C12—C15	110.3 (5)
C1—C2—H2A	110.6	O4—C12—C14	101.0 (4)
S1—C2—H2A	110.6	C15—C12—C14	111.5 (5)
C1—C2—H2B	110.6	O4—C12—C13	108.9 (4)
S1—C2—H2B	110.6	C15—C12—C13	113.6 (5)
H2A—C2—H2B	108.7	C14—C12—C13	110.9 (5)
N1—C3—C4	114.5 (4)	C12—C13—H13A	109.5
N1—C3—S1	103.9 (3)	C12—C13—H13B	109.5
C4—C3—S1	113.2 (4)	H13A—C13—H13B	109.5
N1—C3—H3A	108.3	C12—C13—H13C	109.5
C4—C3—H3A	108.3	H13A—C13—H13C	109.5
S1—C3—H3A	108.3	H13B—C13—H13C	109.5
C11—O4—C12	121.7 (4)	C12—C14—H14A	109.5
C5—C4—C9	119.1 (5)	C12—C14—H14B	109.5
C5—C4—C3	118.2 (5)	H14A—C14—H14B	109.5
C9—C4—C3	122.6 (5)	C12—C14—H14C	109.5
C6—C5—C4	119.5 (6)	H14A—C14—H14C	109.5
C6—C5—H5C	120.3	H14B—C14—H14C	109.5
C4—C5—H5C	120.3	C12—C15—H15A	109.5
C5—C6—C7	121.9 (6)	C12—C15—H15B	109.5
C5—C6—Cl	118.6 (5)	H15A—C15—H15B	109.5
C7—C6—Cl	119.4 (5)	C12—C15—H15C	109.5
C8—C7—C6	118.6 (6)	H15A—C15—H15C	109.5
C8—C7—H7A	120.7	H15B—C15—H15C	109.5
C6—C7—H7A	120.7	H5B—O5—H5A	120.0
C7—C8—C9	120.3 (6)
C11—N1—C1—C2	−177.5 (5)	C4—C5—C6—Cl	−178.7 (5)
C3—N1—C1—C2	16.0 (6)	C5—C6—C7—C8	0.9 (11)
C11—N1—C1—C10	−58.3 (6)	Cl—C6—C7—C8	178.4 (5)
C3—N1—C1—C10	135.3 (5)	C6—C7—C8—C9	−0.8 (10)
N1—C1—C2—S1	−37.1 (5)	C7—C8—C9—C4	1.1 (10)
C10—C1—C2—S1	−157.2 (4)	C5—C4—C9—C8	−1.5 (9)
C3—S1—C2—C1	39.2 (4)	C3—C4—C9—C8	−177.9 (5)
C11—N1—C3—C4	82.2 (6)	N1—C1—C10—O1	−51.4 (7)
C1—N1—C3—C4	−111.8 (5)	C2—C1—C10—O1	64.9 (7)
C11—N1—C3—S1	−153.8 (4)	N1—C1—C10—O2	130.8 (5)
C1—N1—C3—S1	12.1 (5)	C2—C1—C10—O2	−112.9 (5)
C2—S1—C3—N1	−29.0 (4)	C12—O4—C11—O3	3.2 (8)
C2—S1—C3—C4	95.7 (4)	C12—O4—C11—N1	−174.5 (4)
N1—C3—C4—C5	−161.1 (5)	C3—N1—C11—O3	169.7 (5)
S1—C3—C4—C5	80.0 (6)	C1—N1—C11—O3	3.9 (7)
N1—C3—C4—C9	15.4 (8)	C3—N1—C11—O4	−12.4 (6)
S1—C3—C4—C9	−103.5 (6)	C1—N1—C11—O4	−178.3 (4)
C9—C4—C5—C6	1.5 (9)	C11—O4—C12—C15	−62.5 (6)
C3—C4—C5—C6	178.1 (5)	C11—O4—C12—C14	179.5 (5)
C4—C5—C6—C7	−1.2 (10)	C11—O4—C12—C13	62.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O5i	0.82	1.80	2.620 (6)	177
O5—H5A···O3ii	0.85	2.20	2.890 (5)	139
O5—H5B···O3iii	0.85	2.37	2.827 (5)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2C⋯O5i	0.82	1.80	2.620 (6)	177
O5—H5A⋯O3ii	0.85	2.20	2.890 (5)	139
O5—H5B⋯O3iii	0.85	2.37	2.827 (5)	114

Symmetry codes: (i) ; (ii) ; (iii) .