rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyri­din-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Hu, S.; Liang, G.; Fang, D.; Gan, Y.; Hu, X.

doi:10.1107/S1600536811012177

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1075

doi:10.1107/S1600536811012177

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rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Sixing Hu,^a Guojuan Liang,^a Dashu Fang,^a Yongjun Gan ^a and Xiangnan Hu ^a ^*

^aCollege of Pharmaceutical Sciences, Chongqing Medical University, Chongqing 400016, People's Republic of China
^*Correspondence e-mail: huxiangnan62@163.com

(Received 8 March 2011; accepted 1 April 2011; online 7 April 2011)

The title compound, C₂₄H₂₉N₃O₅S, is a chiral molecule which crystallizes in a centrosymmetric space group as a racemate. The thiazolidine ring forms the dihedral angles of 29.22 (12) and 67.79 (10)° with the benzene and pyridine rings, respectively. The benzene and pyridine rings are tilted by dihedral angle of 67.18 (9)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a two-dimensional network.

Related literature

For the related structure of 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, see: Lei et al. (2003 ); Balint & Nagy (2006 ).

Experimental

Crystal data

C₂₄H₂₉N₃O₅S
M_r = 471.56
Monoclinic, P 2₁ /c
a = 25.621 (5) Å
b = 9.886 (2) Å
c = 9.874 (2) Å
β = 97.32 (3)°
V = 2480.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 291 K
0.40 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.936, T_max = 0.980
23230 measured reflections
5574 independent reflections
2632 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.162
S = 1.01
5574 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6C⋯O1ⁱ	0.96	2.59	3.501 (3)	159
C19—H19B⋯O2ⁱⁱ	0.97	2.59	3.302 (4)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012177/kp2314sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012177/kp2314Isup2.hkl

checkCIF report

Comment top

The title compound is a type of thiazolidinedione material, which was synthesised from rosiglitazone and tert-butyl chloroacetate. In this paper, we report the synthesis and crystal structure of the title compound.

The title compound is chiral with a stereogenic centre C16 of the thiazolidine ring. However, it crystallises in the centrosymmetric space group as a racemate. The thiazolidine ring forms the dihedral angles of 29.22 (12) ° and 67.79 (10) ° with the benzene ring and pyridine ring, respectively. The benzene ring and the pyridine ring are tilted by 67.18 (9) ° (Fig. 1). In the crystal, intermolecular C—H···O hydrogen bonds link the molecules into a two-dimensional network (Table 1 and Fig. 2).

Related literature top

For the related structure of 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, see: Lei et al. (2003); Balint & Nagy (2006).

Experimental top

A solution of C₂H₅ONa (1.00 g) in anhydrous ethanol (50 mL) was added slowly to a solution of rosiglitazone (5 g) in anhydrous ethanol (125 mL) at room temperature and the mixture was stirred for 12 h. After completion of the reaction, the mixture was filtered and the white powder was dried at 323 K to afford sodium rosiglitazone (5.15 g). tert-Butyl chloroacetate (0.80 g) was added to a suspension of sodium rosiglitazone (1.51 g) in acetonitrile (70 mL) and the mixture was refluxed for 11 h. After completion of the reaction, the warm suspension was filtered and the filtrates were concentrated under vacuum. Single crystals were obtained by recrystallisation from EtOH : EtOAc (1 : 2) at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku 1998); cell refinement: RAPID-AUTO (Rigaku 1998 ); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing the two-dimensional network. Dashed lines indicate the hydrogen bonds, H atoms not involved in hydrogen bonds have been omitted for clarity.

rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo- 1,3-thiazolidin-3-yl}acetate top

Crystal data top

C₂₄H₂₉N₃O₅S	F(000) = 1000
M_r = 471.56	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10831 reflections
a = 25.621 (5) Å	θ = 3.1–27.5°
b = 9.886 (2) Å	µ = 0.17 mm⁻¹
c = 9.874 (2) Å	T = 291 K
β = 97.32 (3)°	Rod, colorless
V = 2480.6 (9) Å³	0.40 × 0.13 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5574 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −33→33
T_min = 0.936, T_max = 0.980	k = −12→12
23230 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0701P)²] where P = (F_o² + 2F_c²)/3
5574 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₄H₂₉N₃O₅S	V = 2480.6 (9) Å³
M_r = 471.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 25.621 (5) Å	µ = 0.17 mm⁻¹
b = 9.886 (2) Å	T = 291 K
c = 9.874 (2) Å	0.40 × 0.13 × 0.12 mm
β = 97.32 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5574 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2632 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.980	R_int = 0.084
23230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	Δρ_max = 0.31 e Å⁻³
5574 reflections	Δρ_min = −0.37 e Å⁻³
301 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.48020 (14)	0.6375 (3)	0.8137 (3)	0.0804 (9)
H1	0.5087	0.6933	0.8041	0.097*
C2	0.45977 (18)	0.6428 (4)	0.9329 (4)	0.0888 (11)
H2	0.4740	0.6990	1.0037	0.107*
C3	0.41744 (19)	0.5625 (4)	0.9454 (3)	0.0924 (12)
H3	0.4020	0.5643	1.0257	0.111*
C4	0.39732 (14)	0.4788 (3)	0.8404 (3)	0.0754 (9)
H4	0.3681	0.4248	0.8481	0.090*
C5	0.42170 (11)	0.4768 (3)	0.7222 (3)	0.0564 (7)
C6	0.35989 (14)	0.3066 (3)	0.6164 (3)	0.0863 (10)
H6A	0.3548	0.2545	0.5337	0.129*
H6B	0.3294	0.3618	0.6225	0.129*
H6C	0.3651	0.2466	0.6934	0.129*
C7	0.42961 (11)	0.4002 (3)	0.4911 (3)	0.0596 (7)
H7A	0.4261	0.3132	0.4455	0.072*
H7B	0.4669	0.4185	0.5142	0.072*
C8	0.40612 (10)	0.5069 (3)	0.3943 (3)	0.0553 (7)
H8A	0.4049	0.5928	0.4413	0.066*
H8B	0.4271	0.5180	0.3201	0.066*
C9	0.32627 (10)	0.5409 (2)	0.2430 (2)	0.0485 (6)
C10	0.34080 (11)	0.6687 (2)	0.2067 (3)	0.0528 (7)
H10	0.3712	0.7089	0.2507	0.063*
C11	0.30955 (11)	0.7364 (3)	0.1040 (3)	0.0586 (7)
H11	0.3195	0.8226	0.0794	0.070*
C12	0.26421 (11)	0.6808 (3)	0.0368 (3)	0.0543 (7)
C13	0.25053 (11)	0.5518 (3)	0.0757 (3)	0.0592 (7)
H13	0.2201	0.5116	0.0322	0.071*
C14	0.28120 (11)	0.4822 (3)	0.1775 (3)	0.0570 (7)
H14	0.2715	0.3958	0.2019	0.068*
C15	0.23076 (12)	0.7571 (3)	−0.0749 (3)	0.0651 (8)
H15A	0.2124	0.6925	−0.1378	0.078*
H15B	0.2536	0.8104	−0.1253	0.078*
C16	0.19073 (11)	0.8502 (3)	−0.0224 (3)	0.0579 (7)
H16	0.1655	0.7957	0.0207	0.070*
C17	0.16154 (12)	0.9282 (3)	−0.1407 (3)	0.0644 (8)
C18	0.19831 (12)	1.1093 (3)	−0.0082 (3)	0.0621 (8)
C19	0.14767 (14)	1.1623 (3)	−0.2281 (3)	0.0773 (10)
H19A	0.1337	1.1146	−0.3106	0.093*
H19B	0.1758	1.2207	−0.2502	0.093*
C20	0.10508 (13)	1.2475 (3)	−0.1812 (3)	0.0659 (8)
C21	0.05990 (12)	1.4630 (3)	−0.2386 (3)	0.0626 (8)
C22	0.00677 (15)	1.4008 (4)	−0.2715 (5)	0.1199 (15)
H22A	0.0054	1.3502	−0.3548	0.180*
H22B	−0.0194	1.4708	−0.2823	0.180*
H22C	0.0001	1.3416	−0.1987	0.180*
C23	0.06953 (16)	1.5643 (3)	−0.3460 (3)	0.0941 (11)
H23A	0.1036	1.6043	−0.3229	0.141*
H23B	0.0431	1.6335	−0.3510	0.141*
H23C	0.0680	1.5198	−0.4329	0.141*
C24	0.06951 (18)	1.5227 (4)	−0.0975 (4)	0.1122 (14)
H24A	0.0647	1.4541	−0.0313	0.168*
H24B	0.0451	1.5951	−0.0899	0.168*
H24C	0.1048	1.5569	−0.0811	0.168*
N1	0.46247 (10)	0.5579 (3)	0.7084 (2)	0.0678 (7)
N2	0.40565 (10)	0.3921 (2)	0.6158 (2)	0.0644 (6)
N3	0.16884 (9)	1.0652 (2)	−0.1261 (2)	0.0588 (6)
O1	0.35434 (7)	0.46396 (17)	0.34286 (17)	0.0591 (5)
O2	0.20758 (10)	1.2268 (2)	0.0164 (2)	0.0896 (7)
O3	0.13683 (10)	0.8764 (2)	−0.2388 (2)	0.0971 (8)
O4	0.07940 (10)	1.2150 (2)	−0.0940 (3)	0.1076 (9)
O5	0.10097 (8)	1.36116 (17)	−0.25172 (18)	0.0631 (5)
S1	0.21978 (3)	0.97432 (8)	0.09819 (7)	0.0724 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.079 (3)	0.076 (2)	0.083 (2)	−0.0036 (18)	−0.0055 (19)	−0.0139 (18)
C2	0.108 (3)	0.082 (2)	0.071 (2)	0.023 (2)	−0.006 (2)	−0.0150 (19)
C3	0.119 (3)	0.103 (3)	0.059 (2)	0.039 (3)	0.027 (2)	0.004 (2)
C4	0.081 (2)	0.080 (2)	0.0676 (19)	0.0148 (18)	0.0219 (18)	0.0188 (17)
C5	0.0554 (18)	0.0565 (16)	0.0555 (16)	0.0087 (14)	0.0001 (13)	0.0145 (13)
C6	0.080 (2)	0.083 (2)	0.093 (2)	−0.027 (2)	−0.0012 (18)	0.0209 (18)
C7	0.0552 (18)	0.0625 (17)	0.0587 (16)	0.0017 (14)	−0.0017 (14)	−0.0014 (13)
C8	0.0478 (17)	0.0593 (16)	0.0578 (15)	−0.0049 (13)	0.0025 (13)	−0.0015 (13)
C9	0.0478 (16)	0.0450 (14)	0.0531 (14)	0.0036 (12)	0.0084 (12)	−0.0045 (12)
C10	0.0476 (17)	0.0481 (15)	0.0627 (16)	−0.0029 (13)	0.0069 (13)	−0.0044 (13)
C11	0.063 (2)	0.0463 (15)	0.0677 (17)	0.0011 (14)	0.0115 (15)	0.0017 (13)
C12	0.0566 (18)	0.0488 (15)	0.0574 (16)	0.0090 (14)	0.0064 (14)	−0.0015 (12)
C13	0.0552 (18)	0.0460 (15)	0.0729 (17)	0.0014 (13)	−0.0052 (14)	−0.0078 (13)
C14	0.0558 (18)	0.0393 (13)	0.0738 (17)	−0.0004 (13)	0.0001 (14)	−0.0012 (13)
C15	0.070 (2)	0.0600 (17)	0.0648 (16)	0.0129 (15)	0.0057 (15)	0.0017 (14)
C16	0.0604 (19)	0.0500 (15)	0.0625 (16)	0.0020 (13)	0.0047 (14)	0.0025 (13)
C17	0.065 (2)	0.0519 (16)	0.0727 (19)	0.0055 (15)	−0.0069 (16)	0.0018 (15)
C18	0.069 (2)	0.0494 (17)	0.0690 (18)	0.0050 (15)	0.0149 (16)	−0.0065 (13)
C19	0.105 (3)	0.0603 (18)	0.0681 (18)	0.0257 (18)	0.0189 (18)	0.0154 (15)
C20	0.072 (2)	0.0533 (17)	0.0719 (18)	0.0089 (15)	0.0084 (17)	0.0161 (15)
C21	0.062 (2)	0.0532 (16)	0.0734 (18)	0.0148 (15)	0.0103 (15)	0.0081 (14)
C22	0.063 (3)	0.107 (3)	0.181 (4)	−0.002 (2)	−0.015 (3)	0.037 (3)
C23	0.109 (3)	0.065 (2)	0.111 (3)	0.026 (2)	0.025 (2)	0.0304 (19)
C24	0.143 (4)	0.104 (3)	0.088 (2)	0.043 (3)	0.011 (2)	−0.012 (2)
N1	0.0619 (17)	0.0731 (16)	0.0675 (15)	−0.0104 (14)	0.0039 (12)	−0.0074 (13)
N2	0.0641 (16)	0.0662 (15)	0.0616 (14)	−0.0177 (13)	0.0031 (12)	0.0030 (12)
N3	0.0716 (17)	0.0434 (12)	0.0600 (13)	0.0119 (11)	0.0029 (12)	0.0051 (11)
O1	0.0539 (12)	0.0533 (10)	0.0666 (11)	−0.0021 (9)	−0.0060 (9)	0.0092 (9)
O2	0.1121 (19)	0.0509 (12)	0.1059 (16)	−0.0064 (12)	0.0145 (14)	−0.0160 (12)
O3	0.103 (2)	0.0739 (15)	0.0992 (16)	0.0017 (13)	−0.0450 (14)	−0.0055 (13)
O4	0.106 (2)	0.0959 (17)	0.131 (2)	0.0322 (15)	0.0555 (17)	0.0592 (16)
O5	0.0707 (14)	0.0510 (10)	0.0696 (11)	0.0146 (10)	0.0165 (10)	0.0144 (9)
S1	0.0846 (6)	0.0628 (5)	0.0646 (5)	0.0150 (4)	−0.0102 (4)	−0.0077 (4)

Geometric parameters (Å, º) top

C1—N1	1.337 (4)	C13—H13	0.9300
C1—C2	1.349 (5)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.517 (4)
C2—C3	1.363 (5)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.374 (5)	C16—C17	1.515 (4)
C3—H3	0.9300	C16—S1	1.803 (3)
C4—C5	1.392 (4)	C16—H16	0.9800
C4—H4	0.9300	C17—O3	1.202 (3)
C5—N1	1.337 (3)	C17—N3	1.373 (4)
C5—N2	1.365 (3)	C18—O2	1.204 (3)
C6—N2	1.446 (4)	C18—N3	1.375 (4)
C6—H6A	0.9600	C18—S1	1.744 (3)
C6—H6B	0.9600	C19—N3	1.446 (3)
C6—H6C	0.9600	C19—C20	1.498 (4)
C7—N2	1.446 (3)	C19—H19A	0.9700
C7—C8	1.497 (3)	C19—H19B	0.9700
C7—H7A	0.9700	C20—O4	1.193 (3)
C7—H7B	0.9700	C20—O5	1.319 (3)
C8—O1	1.424 (3)	C21—O5	1.474 (3)
C8—H8A	0.9700	C21—C22	1.491 (4)
C8—H8B	0.9700	C21—C23	1.501 (4)
C9—O1	1.374 (3)	C21—C24	1.505 (4)
C9—C14	1.377 (4)	C22—H22A	0.9600
C9—C10	1.378 (3)	C22—H22B	0.9600
C10—C11	1.382 (4)	C22—H22C	0.9600
C10—H10	0.9300	C23—H23A	0.9600
C11—C12	1.377 (4)	C23—H23B	0.9600
C11—H11	0.9300	C23—H23C	0.9600
C12—C13	1.390 (4)	C24—H24A	0.9600
C12—C15	1.509 (4)	C24—H24B	0.9600
C13—C14	1.378 (4)	C24—H24C	0.9600

N1—C1—C2	124.8 (4)	H15A—C15—H15B	107.7
N1—C1—H1	117.6	C17—C16—C15	109.5 (2)
C2—C1—H1	117.6	C17—C16—S1	106.53 (18)
C1—C2—C3	117.2 (3)	C15—C16—S1	113.5 (2)
C1—C2—H2	121.4	C17—C16—H16	109.1
C3—C2—H2	121.4	C15—C16—H16	109.1
C2—C3—C4	120.6 (3)	S1—C16—H16	109.1
C2—C3—H3	119.7	O3—C17—N3	123.8 (3)
C4—C3—H3	119.7	O3—C17—C16	124.2 (3)
C3—C4—C5	118.4 (3)	N3—C17—C16	111.9 (2)
C3—C4—H4	120.8	O2—C18—N3	123.4 (3)
C5—C4—H4	120.8	O2—C18—S1	125.3 (3)
N1—C5—N2	116.8 (2)	N3—C18—S1	111.37 (19)
N1—C5—C4	121.1 (3)	N3—C19—C20	112.4 (2)
N2—C5—C4	122.0 (3)	N3—C19—H19A	109.1
N2—C6—H6A	109.5	C20—C19—H19A	109.1
N2—C6—H6B	109.5	N3—C19—H19B	109.1
H6A—C6—H6B	109.5	C20—C19—H19B	109.1
N2—C6—H6C	109.5	H19A—C19—H19B	107.9
H6A—C6—H6C	109.5	O4—C20—O5	126.6 (3)
H6B—C6—H6C	109.5	O4—C20—C19	124.2 (3)
N2—C7—C8	113.8 (2)	O5—C20—C19	109.1 (3)
N2—C7—H7A	108.8	O5—C21—C22	110.0 (3)
C8—C7—H7A	108.8	O5—C21—C23	102.1 (2)
N2—C7—H7B	108.8	C22—C21—C23	110.4 (3)
C8—C7—H7B	108.8	O5—C21—C24	108.4 (3)
H7A—C7—H7B	107.7	C22—C21—C24	113.6 (3)
O1—C8—C7	107.4 (2)	C23—C21—C24	111.7 (3)
O1—C8—H8A	110.2	C21—C22—H22A	109.5
C7—C8—H8A	110.2	C21—C22—H22B	109.5
O1—C8—H8B	110.2	H22A—C22—H22B	109.5
C7—C8—H8B	110.2	C21—C22—H22C	109.5
H8A—C8—H8B	108.5	H22A—C22—H22C	109.5
O1—C9—C14	115.8 (2)	H22B—C22—H22C	109.5
O1—C9—C10	124.1 (2)	C21—C23—H23A	109.5
C14—C9—C10	120.1 (2)	C21—C23—H23B	109.5
C9—C10—C11	119.0 (3)	H23A—C23—H23B	109.5
C9—C10—H10	120.5	C21—C23—H23C	109.5
C11—C10—H10	120.5	H23A—C23—H23C	109.5
C12—C11—C10	122.3 (3)	H23B—C23—H23C	109.5
C12—C11—H11	118.8	C21—C24—H24A	109.5
C10—C11—H11	118.8	C21—C24—H24B	109.5
C11—C12—C13	117.4 (2)	H24A—C24—H24B	109.5
C11—C12—C15	121.2 (3)	C21—C24—H24C	109.5
C13—C12—C15	121.4 (3)	H24A—C24—H24C	109.5
C14—C13—C12	121.3 (3)	H24B—C24—H24C	109.5
C14—C13—H13	119.4	C1—N1—C5	117.8 (3)
C12—C13—H13	119.4	C5—N2—C7	120.2 (2)
C9—C14—C13	119.9 (2)	C5—N2—C6	121.4 (3)
C9—C14—H14	120.0	C7—N2—C6	117.9 (2)
C13—C14—H14	120.0	C17—N3—C18	117.1 (2)
C12—C15—C16	113.5 (2)	C17—N3—C19	123.2 (2)
C12—C15—H15A	108.9	C18—N3—C19	119.7 (2)
C16—C15—H15A	108.9	C9—O1—C8	118.04 (19)
C12—C15—H15B	108.9	C20—O5—C21	123.1 (2)
C16—C15—H15B	108.9	C18—S1—C16	92.91 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6C···O1ⁱ	0.96	2.59	3.501 (3)	159
C19—H19B···O2ⁱⁱ	0.97	2.59	3.302 (4)	130

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+5/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₉N₃O₅S
M_r	471.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	25.621 (5), 9.886 (2), 9.874 (2)
β (°)	97.32 (3)
V (Å³)	2480.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.40 × 0.13 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.936, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	23230, 5574, 2632
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.162, 1.01
No. of reflections	5574
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.37

Computer programs: RAPID-AUTO (Rigaku 1998), RAPID-AUTO (Rigaku 1998 ), CrystalStructure (Rigaku/MSC, 2002), 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
C6—H6C···O1ⁱ	0.96	2.59	3.501 (3)	159
C19—H19B···O2ⁱⁱ	0.97	2.59	3.302 (4)	130

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+5/2, z−1/2.

Acknowledgements

This work was supported by Natural Science Foundation of Chongqing. We also thank Chongqing Medical University for partial financial support of this work.

References

Balint, B. L. & Nagy, L. (2006). Endocr. Metab. Immune Disord. Drug. Targets, 6, 33–43. CrossRef PubMed CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Lei, Q., Guang, B., Wang, L. B., Wei, Y. Z. & Zhang, G. L. (2003). J. Sichuan Univ. 35, 107–109. CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1075

doi:10.1107/S1600536811012177

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

rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyri­din-2-yl)amino]eth­oxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-tert-Butyl 2-{5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate