3-(tert-But­oxy­carbon­yl)-2-(4-chloro­phen­yl)-1,3-thia­zolidine-4-carb­oxy­lic acid

Ding, S.-M.

doi:10.1107/S1600536810037396

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2633

doi:10.1107/S1600536810037396

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ADDENDA AND ERRATA

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3-(tert-Butoxycarbonyl)-2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid

Shu-Min Ding ^a ^*

^aSchool of Chemical Engineering, Changzhou University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: dsm@cczu.edu.cn

(Received 11 September 2010; accepted 18 September 2010; online 25 September 2010)

In the title compound, C₁₅H₁₈ClNO₄S, the thiazolidine ring adopts a twisted conformation about the S—C(methylene) bond. The dihedral angle between the five- and six-membered rings is 77.2 (3)°. In the crystal, the molecules 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_r = 343.81
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.159
S = 1.08
1638 reflections
185 parameters
89 restraints
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 )
Flack parameter: −0.09 (19)

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) x+1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Recently, 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives have been reported to possess antimicrobial and antitumor activities (Song et al., 2009; Lu et al., 2010). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). There are intermolecular O—H···O hydrogen bonds in (I).

Related literature top

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). PLATON indicates 0 Frie

Experimental top

A mixture of L-cysteine (1.41 g, 10 mmol) and 4-chlorobenzaldehyde (1.4 g, 10 mmol) in methanol (100 ml) was stirred at room temperature for 10 h, and the separated solid was collected, washed with diethyl ether, and dried to obtain 2-(4-chlorophenyl)thiazolidine-4-carboxylic with yield of 90%. In ice water, 2-(4-chlorophenyl)thiazolidine-4-carboxylic (1 mmol) was dissolved in 1 N NaOH (1 ml) and 1,4-dioxane (10 ml); then di-tert-butyldicarbonate (1 mmol) was added slowly and stirred at room temperature for 6 h. The reaction mixture was concentrated in a vacuum and washed with ethyl acetate (10 ml). The aqueous phase was adjusted to pH 4 by adding 1 N HCl, then extracted with ethyl acetate, dried with magnesium sulfate, filtered, After keeping the filtrate in air for 5 d, colorless block-shaped crystals of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.

3-(tert-Butoxycarbonyl)-2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid top

Crystal data top

C₁₅H₁₈ClNO₄S	F(000) = 360
M_r = 343.81	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1363 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scan	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.899, T_max = 0.965	l = 0→14
1638 measured reflections	200 standard reflections every 3 reflections
1638 independent reflections	intensity decay: 1%

Refinement top

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(F_o²) + (0.0649P)² + 1.2912P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1638 reflections	Δρ_max = 0.43 e Å⁻³
185 parameters	Δρ_min = −0.37 e Å⁻³
89 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (19)

Crystal data top

C₁₅H₁₈ClNO₄S	V = 850.5 (3) Å³
M_r = 343.81	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.4600 (13) Å	µ = 0.36 mm⁻¹
b = 10.641 (2) Å	T = 293 K
c = 12.411 (3) Å	0.30 × 0.20 × 0.10 mm
β = 94.52 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1363 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.899, T_max = 0.965	200 standard reflections every 3 reflections
1638 measured reflections	intensity decay: 1%
1638 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	H-atom parameters constrained
wR(F²) = 0.159	Δρ_max = 0.43 e Å⁻³
S = 1.08	Δρ_min = −0.37 e Å⁻³
1638 reflections	Absolute structure: Flack (1983)
185 parameters	Absolute structure parameter: −0.09 (19)
89 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈ClNO₄S
M_r	343.81
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.4600 (13), 10.641 (2), 12.411 (3)
β (°)	94.52 (3)
V (Å³)	850.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.899, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	1638, 1638, 1363
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.159, 1.08
No. of reflections	1638
No. of parameters	185
No. of restraints	89
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.37
Absolute structure	Flack (1983)
Absolute structure parameter	−0.09 (19)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Acknowledgements

The work was supported by youthfund project (project JQ201006) of Changzhou University.

References

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Volume 66| Part 10| October 2010| Page o2633

doi:10.1107/S1600536810037396

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(tert-But­­oxy­carbon­yl)-2-(4-chloro­phen­yl)-1,3-thia­zolidine-4-carb­­oxy­lic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(tert-Butoxycarbonyl)-2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid