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

In the title compound, C(15)H(18)ClNO(4)S, the thia-zolidine ring adopts a twisted conformation about the S-C(methyl-ene) bond. The dihedral angle between the five- and six-membered rings is 77.2 (3)°. In the crystal, the mol-ecules are linked by O-H⋯O hydrogen bonds, generating C(7) chains propagating in [100].

Related literature

For background to the biological properties of the title compound, see: Lu et al. (2010 ▶); Song et al. (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H18ClNO4S

M = 343.81

Monoclinic,

a = 6.4600 (13) Å

b = 10.641 (2) Å

c = 12.411 (3) Å

β = 94.52 (3)°

V = 850.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.899, T max = 0.965

1638 measured reflections

1638 independent reflections

1363 reflections with I > 2σ(I)

200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.159

S = 1.08

1638 reflections

185 parameters

89 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: −0.09 (19)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037396/hb5637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037396/hb5637Isup2.hkl

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

C15H18ClNO4S	F(000) = 360
Mr = 343.81	Dx = 1.343 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.4600 (13) Å	θ = 9–12°
b = 10.641 (2) Å	µ = 0.36 mm−1
c = 12.411 (3) Å	T = 293 K
β = 94.52 (3)°	Block, colorless
V = 850.5 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	1363 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 1.7°
ω/2θ scan	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.899, Tmax = 0.965	l = 0→14
1638 measured reflections	200 standard reflections every 3 reflections
1638 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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0649P)2 + 1.2912P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1638 reflections	Δρmax = 0.43 e Å−3
185 parameters	Δρmin = −0.37 e Å−3
89 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (19)

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
C1	0.3575 (11)	0.4607 (7)	0.7980 (6)	0.0457 (16)
H1	0.4776	0.4984	0.7768	0.055*
C2	0.3229 (12)	0.3336 (8)	0.7816 (6)	0.0519 (17)
H2	0.4183	0.2863	0.7465	0.062*
C3	0.1505 (12)	0.2766 (8)	0.8162 (7)	0.0555 (18)
C4	0.0021 (13)	0.3440 (8)	0.8654 (6)	0.0585 (18)
H4	−0.1163	0.3054	0.8879	0.070*
C5	0.0368 (11)	0.4720 (7)	0.8800 (6)	0.0492 (16)
H5	−0.0604	0.5195	0.9136	0.059*
C6	0.2109 (9)	0.5308 (6)	0.8464 (5)	0.0349 (13)
C7	0.2361 (9)	0.6677 (6)	0.8692 (4)	0.0358 (13)
H7	0.1036	0.7023	0.8887	0.043*
C8	0.4770 (9)	0.8351 (7)	0.8161 (5)	0.0409 (14)
H8	0.4364	0.9165	0.7842	0.049*
O1	0.8408 (8)	0.8639 (5)	0.8109 (4)	0.060
C9	0.4827 (11)	0.8471 (7)	0.9375 (5)	0.0494 (16)
H9A	0.3760	0.9043	0.9583	0.059*
H9B	0.6170	0.8774	0.9671	0.059*
C10	0.6910 (9)	0.8031 (8)	0.7835 (5)	0.0459 (17)
C11	0.2163 (9)	0.7473 (7)	0.6838 (5)	0.0373 (14)
C12	0.2095 (11)	0.8500 (8)	0.5098 (5)	0.0520 (18)
C13	0.2564 (14)	0.7386 (9)	0.4443 (8)	0.070
H13A	0.3999	0.7161	0.4586	0.106*
H13B	0.2293	0.7579	0.3690	0.106*
H13C	0.1705	0.6695	0.4629	0.106*
C14	−0.0195 (13)	0.8803 (9)	0.4998 (8)	0.069
H14A	−0.0975	0.8056	0.5123	0.104*
H14B	−0.0583	0.9117	0.4286	0.104*
H14C	−0.0483	0.9429	0.5523	0.104*
C15	0.3316 (15)	0.9649 (10)	0.4750 (7)	0.078 (3)
H15A	0.2943	1.0371	0.5156	0.116*
H15B	0.2992	0.9802	0.3993	0.116*
H15C	0.4777	0.9492	0.4883	0.116*
Cl1	0.1156 (5)	0.1156 (2)	0.7961 (2)	0.0908 (9)
N1	0.3167 (7)	0.7456 (5)	0.7848 (4)	0.0336 (11)
O2	0.6980 (6)	0.7001 (6)	0.7256 (4)	0.0534 (12)
H2A	0.8185	0.6858	0.7131	0.080*
O3	0.0721 (6)	0.6749 (5)	0.6573 (3)	0.0398 (10)
O4	0.2916 (7)	0.8324 (5)	0.6216 (3)	0.0448 (11)
S1	0.4357 (3)	0.68989 (18)	0.98363 (12)	0.0481 (5)

	U11	U22	U33	U12	U13	U23
C1	0.047 (4)	0.049 (3)	0.041 (4)	0.001 (3)	0.003 (3)	0.001 (3)
C2	0.059 (4)	0.055 (4)	0.041 (4)	0.010 (3)	0.001 (3)	−0.006 (3)
C3	0.064 (4)	0.047 (4)	0.053 (4)	−0.006 (3)	−0.014 (3)	0.007 (3)
C4	0.060 (4)	0.057 (4)	0.058 (4)	−0.014 (3)	0.004 (3)	0.004 (4)
C5	0.046 (3)	0.056 (4)	0.045 (4)	−0.004 (3)	0.003 (3)	0.011 (3)
C6	0.039 (3)	0.035 (3)	0.031 (3)	0.000 (2)	0.002 (2)	0.008 (3)
C7	0.035 (3)	0.043 (4)	0.030 (3)	0.005 (3)	0.003 (2)	0.006 (3)
C8	0.042 (3)	0.038 (3)	0.042 (3)	0.001 (3)	−0.004 (3)	0.001 (3)
O1	0.060	0.060	0.060	0.000	0.005	0.000
C9	0.052 (4)	0.052 (4)	0.043 (3)	0.008 (3)	−0.006 (3)	−0.009 (3)
C10	0.026 (3)	0.074 (5)	0.037 (3)	−0.015 (3)	−0.006 (2)	−0.002 (3)
C11	0.028 (3)	0.053 (4)	0.031 (3)	0.009 (3)	−0.002 (2)	−0.002 (3)
C12	0.050 (4)	0.070 (5)	0.035 (3)	−0.008 (4)	−0.003 (3)	0.019 (4)
C13	0.070	0.070	0.070	0.000	0.006	0.000
C14	0.070	0.070	0.070	0.000	0.006	0.000
C15	0.086 (6)	0.085 (7)	0.061 (5)	−0.007 (5)	0.006 (4)	0.036 (5)
Cl1	0.115 (2)	0.0475 (12)	0.1032 (19)	−0.0122 (13)	−0.0338 (16)	0.0021 (13)
N1	0.030 (2)	0.038 (3)	0.033 (2)	0.004 (2)	0.0010 (19)	0.001 (2)
O2	0.032 (2)	0.066 (3)	0.064 (3)	−0.010 (2)	0.012 (2)	−0.018 (3)
O3	0.029 (2)	0.058 (3)	0.0317 (19)	−0.007 (2)	−0.0026 (15)	−0.005 (2)
O4	0.044 (2)	0.055 (3)	0.035 (2)	−0.015 (2)	0.0001 (18)	0.016 (2)
S1	0.0578 (10)	0.0564 (10)	0.0285 (7)	−0.0005 (9)	−0.0071 (6)	−0.0025 (9)

C1—C6	1.379 (9)	C9—H9A	0.9700
C1—C2	1.384 (11)	C9—H9B	0.9700
C1—H1	0.9300	C10—O2	1.313 (9)
C2—C3	1.367 (11)	C11—O3	1.234 (8)
C2—H2	0.9300	C11—O4	1.308 (8)
C3—C4	1.378 (12)	C11—N1	1.365 (8)
C3—Cl1	1.744 (8)	C12—O4	1.457 (8)
C4—C5	1.390 (11)	C12—C13	1.483 (12)
C4—H4	0.9300	C12—C14	1.510 (11)
C5—C6	1.380 (9)	C12—C15	1.535 (11)
C5—H5	0.9300	C13—H13A	0.9600
C6—C7	1.490 (9)	C13—H13B	0.9600
C7—N1	1.464 (8)	C13—H13C	0.9600
C7—S1	1.857 (6)	C14—H14A	0.9600
C7—H7	0.9800	C14—H14B	0.9600
C8—N1	1.437 (8)	C14—H14C	0.9600
C8—C10	1.510 (9)	C15—H15A	0.9600
C8—C9	1.510 (9)	C15—H15B	0.9600
C8—H8	0.9800	C15—H15C	0.9600
O1—C10	1.191 (8)	O2—H2A	0.8200
C9—S1	1.801 (8)
C6—C1—C2	119.0 (7)	O1—C10—O2	123.2 (6)
C6—C1—H1	120.5	O1—C10—C8	122.8 (7)
C2—C1—H1	120.5	O2—C10—C8	114.0 (5)
C3—C2—C1	120.9 (7)	O3—C11—O4	125.6 (5)
C3—C2—H2	119.6	O3—C11—N1	122.1 (6)
C1—C2—H2	119.6	O4—C11—N1	112.3 (5)
C2—C3—C4	121.4 (8)	O4—C12—C13	110.1 (7)
C2—C3—Cl1	119.4 (7)	O4—C12—C14	112.7 (6)
C4—C3—Cl1	119.2 (7)	C13—C12—C14	111.5 (7)
C3—C4—C5	117.2 (8)	O4—C12—C15	102.4 (6)
C3—C4—H4	121.4	C13—C12—C15	110.5 (6)
C5—C4—H4	121.4	C14—C12—C15	109.2 (7)
C6—C5—C4	122.2 (8)	C12—C13—H13A	109.5
C6—C5—H5	118.9	C12—C13—H13B	109.5
C4—C5—H5	118.9	H13A—C13—H13B	109.5
C1—C6—C5	119.3 (6)	C12—C13—H13C	109.5
C1—C6—C7	122.9 (6)	H13A—C13—H13C	109.5
C5—C6—C7	117.8 (6)	H13B—C13—H13C	109.5
N1—C7—C6	117.2 (5)	C12—C14—H14A	109.5
N1—C7—S1	102.2 (4)	C12—C14—H14B	109.5
C6—C7—S1	109.2 (4)	H14A—C14—H14B	109.5
N1—C7—H7	109.3	C12—C14—H14C	109.5
C6—C7—H7	109.3	H14A—C14—H14C	109.5
S1—C7—H7	109.3	H14B—C14—H14C	109.5
N1—C8—C10	115.7 (6)	C12—C15—H15A	109.5
N1—C8—C9	106.7 (5)	C12—C15—H15B	109.5
C10—C8—C9	109.6 (5)	H15A—C15—H15B	109.5
N1—C8—H8	108.2	C12—C15—H15C	109.5
C10—C8—H8	108.2	H15A—C15—H15C	109.5
C9—C8—H8	108.2	H15B—C15—H15C	109.5
C8—C9—S1	104.3 (5)	C11—N1—C8	121.3 (5)
C8—C9—H9A	110.9	C11—N1—C7	119.6 (5)
S1—C9—H9A	110.9	C8—N1—C7	118.1 (5)
C8—C9—H9B	110.9	C10—O2—H2A	109.5
S1—C9—H9B	110.9	C11—O4—C12	121.8 (5)
H9A—C9—H9B	108.9	C9—S1—C7	90.0 (3)
C6—C1—C2—C3	−2.5 (11)	O3—C11—N1—C8	−176.7 (6)
C1—C2—C3—C4	2.1 (12)	O4—C11—N1—C8	3.6 (8)
C1—C2—C3—Cl1	−178.8 (6)	O3—C11—N1—C7	−8.1 (9)
C2—C3—C4—C5	−1.1 (11)	O4—C11—N1—C7	172.2 (5)
Cl1—C3—C4—C5	179.8 (6)	C10—C8—N1—C11	−83.3 (7)
C3—C4—C5—C6	0.5 (11)	C9—C8—N1—C11	154.5 (5)
C2—C1—C6—C5	1.9 (10)	C10—C8—N1—C7	107.9 (6)
C2—C1—C6—C7	178.9 (6)	C9—C8—N1—C7	−14.2 (7)
C4—C5—C6—C1	−0.9 (10)	C6—C7—N1—C11	56.7 (7)
C4—C5—C6—C7	−178.1 (6)	S1—C7—N1—C11	176.0 (4)
C1—C6—C7—N1	42.7 (8)	C6—C7—N1—C8	−134.4 (6)
C5—C6—C7—N1	−140.2 (6)	S1—C7—N1—C8	−15.1 (6)
C1—C6—C7—S1	−72.7 (7)	O3—C11—O4—C12	−0.4 (10)
C5—C6—C7—S1	104.3 (6)	N1—C11—O4—C12	179.3 (6)
N1—C8—C9—S1	37.6 (6)	C13—C12—O4—C11	−67.2 (8)
C10—C8—C9—S1	−88.4 (6)	C14—C12—O4—C11	58.1 (10)
N1—C8—C10—O1	−174.4 (6)	C15—C12—O4—C11	175.3 (6)
C9—C8—C10—O1	−53.8 (9)	C8—C9—S1—C7	−40.6 (5)
N1—C8—C10—O2	3.4 (8)	N1—C7—S1—C9	31.7 (4)
C9—C8—C10—O2	124.0 (6)	C6—C7—S1—C9	156.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3i	0.82	1.83	2.638 (6)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.82	1.83	2.638 (6)	167

Symmetry code: (i) .