Crystal structure of (2S,4S)-5,5-dimethyl-2-(pyridin-2-yl)-1,3-thia-zolidine-4-carb-oxy-lic acid.

In the title compound, C11H14N2O2S, the thia-zolidine ring has an envelope conformation with the C atom bonded to the carb-oxy-lic acid group at the flap. Two C atoms of the thia-zolidine ring adopt S conformations. In the crystal, O-H⋯N hydrogen bonds between the amine and carb-oxy-lic acid groups construct a helical chain structure along the a-axis direction. The chains are further connected via weak C-H⋯π contacts, forming a layer parallel to the ac plane.

Related literature

For background to compounds containing thia­zoline or thia­zolidine rings, see: Bolos et al. (2002 ▶); Pontiki et al. (2006 ▶); Shih & Ke (2004 ▶). For related structures, see: Brunner et al. (1984 ▶, 2001 ▶). For the preparation of d-penicillamine-coordinated metal complexes, see: Igashira-Kamiyama & Konno (2011 ▶).

Experimental

Crystal data

C11H14N2O2S

M = 238.30

Orthorhombic,

a = 7.906 (4) Å

b = 11.306 (5) Å

c = 13.504 (7) Å

V = 1207.1 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 200 K

0.25 × 0.25 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.785, T max = 0.938

9629 measured reflections

2767 independent reflections

2711 reflections with F 2 > 2σ(F 2)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.10

2767 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack x determined using 1118 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.01 (9)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2014 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) New_Global_Publ_Block, I. DOI: 10.1107/S1600536814024854/is5377sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024854/is5377Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024854/is5377Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814024854/is5377fig1.tif

Mol­ecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are at the 70% probability level. H atoms are drawn as spheres of arbitrary radii.

Click here for additional data file.

a . DOI: 10.1107/S1600536814024854/is5377fig2.tif

Crystal packing diagram of the title compound, viewed along with the a axis. Orange and blue dotted lines indicate the weak C—H⋯π contact and the O—H⋯N hydrogen bond, respectively.

CCDC reference: 1033831

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H14N2O2S	Dx = 1.311 Mg m−3
Mr = 238.30	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, P212121	Cell parameters from 606 reflections
a = 7.906 (4) Å	θ = 3.0–21.8°
b = 11.306 (5) Å	µ = 0.26 mm−1
c = 13.504 (7) Å	T = 200 K
V = 1207.1 (10) Å3	Block, colorless
Z = 4	0.25 × 0.25 × 0.25 mm
F(000) = 504.00

Rigaku R-AXIS RAPID diffractometer	2711 reflections with F2 > 2σ(F2)
ω scans	Rint = 0.020
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.785, Tmax = 0.938	h = −10→10
9629 measured reflections	k = −14→13
2767 independent reflections	l = −17→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.045P)2 + 0.1433P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2767 reflections	Δρmax = 0.23 e Å−3
152 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (9)
Secondary atom site location: difference Fourier map

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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	0.73917 (6)	0.55168 (4)	0.77596 (3)	0.03414 (14)
O1	0.8795 (2)	0.83178 (13)	0.53057 (12)	0.0499 (4)
O2	0.9289 (2)	0.65820 (14)	0.45666 (11)	0.0409 (4)
N1	0.63325 (18)	0.85167 (14)	0.83052 (11)	0.0277 (3)
N2	0.65342 (19)	0.73327 (14)	0.65780 (10)	0.0261 (3)
C1	0.5500 (2)	0.74879 (16)	0.82907 (12)	0.0256 (3)
C2	0.4421 (3)	0.71255 (17)	0.90457 (14)	0.0334 (4)
C3	0.4220 (3)	0.78569 (19)	0.98617 (14)	0.0363 (4)
C4	0.5073 (3)	0.89258 (17)	0.98869 (14)	0.0335 (4)
C5	0.6099 (2)	0.92190 (16)	0.90928 (14)	0.0308 (4)
C6	0.5841 (2)	0.66856 (16)	0.74195 (12)	0.0263 (3)
C7	0.7626 (2)	0.65411 (15)	0.60028 (11)	0.0242 (3)
C8	0.8809 (2)	0.58482 (16)	0.67186 (13)	0.0265 (3)
C9	0.8626 (2)	0.72556 (17)	0.52484 (12)	0.0295 (4)
C10	0.9418 (3)	0.46896 (18)	0.62677 (16)	0.0390 (4)
C11	1.0304 (3)	0.6594 (2)	0.70700 (16)	0.0407 (5)
H2	0.38344	0.63938	0.90033	0.0401*
H3	0.35091	0.76278	1.03953	0.0436*
H4	0.49563	0.94457	1.04353	0.0402*
H5	0.66695	0.99584	0.91074	0.0369*
H6	0.47579	0.63008	0.72142	0.0315*
H7	0.68972	0.59616	0.56409	0.0290*
H10A	0.84418	0.42248	0.60474	0.0468*
H10B	1.01526	0.48577	0.57003	0.0468*
H10C	1.00522	0.42406	0.67652	0.0468*
H11A	0.98853	0.73348	0.73572	0.0488*
H11B	1.09424	0.61552	0.75716	0.0488*
H11C	1.10427	0.67722	0.65067	0.0488*
H12	0.711 (3)	0.790 (2)	0.6820 (17)	0.0392*
H13	0.992 (4)	0.696 (3)	0.424 (2)	0.0614*

	U11	U22	U33	U12	U13	U23
S1	0.0440 (3)	0.0322 (2)	0.0262 (2)	0.0066 (2)	0.00704 (19)	0.00796 (16)
O1	0.0704 (11)	0.0304 (8)	0.0487 (9)	−0.0018 (7)	0.0192 (8)	0.0082 (7)
O2	0.0512 (9)	0.0432 (8)	0.0282 (7)	−0.0165 (7)	0.0152 (6)	−0.0046 (6)
N1	0.0281 (7)	0.0288 (8)	0.0263 (7)	−0.0001 (6)	0.0014 (6)	0.0008 (6)
N2	0.0305 (7)	0.0296 (8)	0.0183 (6)	0.0036 (6)	−0.0018 (6)	0.0012 (6)
C1	0.0241 (7)	0.0314 (9)	0.0214 (7)	0.0026 (6)	−0.0028 (6)	0.0014 (6)
C2	0.0336 (9)	0.0336 (10)	0.0331 (9)	−0.0037 (8)	0.0061 (8)	0.0012 (8)
C3	0.0391 (10)	0.0418 (11)	0.0281 (9)	0.0034 (9)	0.0105 (8)	0.0032 (8)
C4	0.0402 (10)	0.0344 (10)	0.0259 (8)	0.0106 (8)	0.0019 (7)	−0.0020 (7)
C5	0.0331 (9)	0.0274 (9)	0.0318 (9)	0.0026 (7)	−0.0001 (7)	−0.0002 (7)
C6	0.0262 (8)	0.0310 (8)	0.0216 (8)	−0.0017 (7)	−0.0010 (6)	0.0010 (7)
C7	0.0269 (7)	0.0273 (7)	0.0184 (6)	−0.0040 (7)	−0.0009 (6)	0.0005 (6)
C8	0.0289 (8)	0.0267 (8)	0.0238 (8)	−0.0004 (6)	0.0015 (7)	0.0013 (6)
C9	0.0331 (8)	0.0333 (9)	0.0222 (8)	−0.0035 (7)	−0.0001 (7)	0.0044 (7)
C10	0.0444 (11)	0.0324 (10)	0.0402 (11)	0.0066 (9)	0.0088 (9)	−0.0016 (8)
C11	0.0365 (10)	0.0435 (11)	0.0421 (11)	−0.0056 (9)	−0.0132 (9)	0.0019 (9)

S1—C6	1.8599 (19)	C8—C11	1.528 (3)
S1—C8	1.8362 (19)	O2—H13	0.79 (3)
O1—C9	1.211 (2)	N2—H12	0.85 (2)
O2—C9	1.305 (2)	C2—H2	0.950
N1—C1	1.337 (2)	C3—H3	0.950
N1—C5	1.340 (2)	C4—H4	0.950
N2—C6	1.458 (2)	C5—H5	0.950
N2—C7	1.466 (2)	C6—H6	1.000
C1—C2	1.391 (3)	C7—H7	1.000
C1—C6	1.510 (2)	C10—H10A	0.980
C2—C3	1.387 (3)	C10—H10B	0.980
C3—C4	1.384 (3)	C10—H10C	0.980
C4—C5	1.385 (3)	C11—H11A	0.980
C7—C8	1.556 (2)	C11—H11B	0.980
C7—C9	1.522 (2)	C11—H11C	0.980
C8—C10	1.523 (3)
C6—S1—C8	93.90 (8)	C7—N2—H12	110.5 (16)
C1—N1—C5	117.35 (15)	C1—C2—H2	120.764
C6—N2—C7	109.13 (14)	C3—C2—H2	120.760
N1—C1—C2	123.21 (16)	C2—C3—H3	120.513
N1—C1—C6	116.48 (15)	C4—C3—H3	120.502
C2—C1—C6	120.26 (16)	C3—C4—H4	120.818
C1—C2—C3	118.48 (18)	C5—C4—H4	120.808
C2—C3—C4	118.98 (18)	N1—C5—H5	118.207
C3—C4—C5	118.37 (18)	C4—C5—H5	118.203
N1—C5—C4	123.59 (17)	S1—C6—H6	108.899
S1—C6—N2	107.54 (12)	N2—C6—H6	108.902
S1—C6—C1	110.63 (12)	C1—C6—H6	108.903
N2—C6—C1	111.90 (15)	N2—C7—H7	108.652
N2—C7—C8	109.38 (13)	C8—C7—H7	108.655
N2—C7—C9	109.66 (14)	C9—C7—H7	108.656
C8—C7—C9	111.77 (14)	C8—C10—H10A	109.475
S1—C8—C7	102.22 (12)	C8—C10—H10B	109.471
S1—C8—C10	108.89 (13)	C8—C10—H10C	109.472
S1—C8—C11	110.30 (13)	H10A—C10—H10B	109.472
C7—C8—C10	112.01 (15)	H10A—C10—H10C	109.467
C7—C8—C11	112.32 (15)	H10B—C10—H10C	109.470
C10—C8—C11	110.76 (16)	C8—C11—H11A	109.470
O1—C9—O2	125.42 (18)	C8—C11—H11B	109.475
O1—C9—C7	122.76 (16)	C8—C11—H11C	109.473
O2—C9—C7	111.80 (16)	H11A—C11—H11B	109.465
C9—O2—H13	109 (2)	H11A—C11—H11C	109.474
C6—N2—H12	106.1 (15)	H11B—C11—H11C	109.470

D—H···A	D—H	H···A	D···A	D—H···A
O2—H13···N2i	0.79 (3)	1.87 (3)	2.654 (2)	173 (3)
C3—H3···Cgii	0.95	2.81	3.629 (2)	145

Table 1

Hydrogen-bond geometry (, )

Cg is the centroid of the N1/C1C5 ring.

DHA	DH	HA	D A	DHA
O2H13N2i	0.79(3)	1.87(3)	2.654(2)	173(3)
C3H3Cg ii	0.95	2.81	3.629(2)	145

Symmetry codes: (i) ; (ii) .