N-(2,4-Dioxo-1,3-thia-zolidin-3-yl)-2-(4-isobutyl-phen-yl)propanamide.

In the title compound, C(16)H(20)N(2)O(3)S, the thia-zolidine ring is approximately planar [maximum deviation = 0.020 (2) Å] and forms a dihedral angle of 86.20 (11)° with the benzene ring. The mean plane through the propanamide unit forms dihedral angles of 88.54 (12) and 76.36 (12)°, respectively, with the thia-zolidine and benzene rings. In the crystal structure, mol-ecules are linked into chains along the a axis by N-H⋯O inter-actions. These chains are inter-connected into two-dimensional arrays parallel to the ab plane by three different C-H⋯O inter-actions. The crystal structure is further stabilized by weak inter-molecular C-H⋯π and N⋯O [2.713 (2) Å] inter-actions.

Related literature

For general background to the synthesis, pharmacological properties and applications of compounds incorporating ibuprofen, see: Aktay et al. (2005 ▶); Palaska et al. (2002 ▶); Verma & Saraf (2008 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H20N2O3S

M = 320.40

Orthorhombic,

a = 9.7305 (1) Å

b = 11.3991 (2) Å

c = 29.6323 (4) Å

V = 3286.78 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.24 × 0.21 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.951, T max = 0.981

33569 measured reflections

3783 independent reflections

2927 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.143

S = 1.20

3783 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903027X/tk2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903027X/tk2517Isup2.hkl

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

C16H20N2O3S	F(000) = 1360
Mr = 320.40	Dx = 1.295 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5195 reflections
a = 9.7305 (1) Å	θ = 2.5–30.0°
b = 11.3991 (2) Å	µ = 0.21 mm−1
c = 29.6323 (4) Å	T = 100 K
V = 3286.78 (8) Å3	Plate, colourless
Z = 8	0.24 × 0.21 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
graphite	Rint = 0.079
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.951, Tmax = 0.981	k = −14→13
33569 measured reflections	l = −38→36

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.7928P] where P = (Fo2 + 2Fc2)/3
3783 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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.

	x	y	z	Uiso*/Ueq
S1	0.07397 (7)	0.09512 (5)	0.38158 (2)	0.02357 (19)
O1	0.15979 (17)	0.01544 (15)	0.50523 (6)	0.0235 (4)
O2	0.13357 (18)	0.31521 (14)	0.40290 (6)	0.0234 (4)
O3	−0.03571 (16)	0.26390 (15)	0.51261 (6)	0.0209 (4)
N1	0.15610 (19)	0.17543 (16)	0.45864 (6)	0.0154 (4)
N2	0.1867 (2)	0.25414 (17)	0.49260 (6)	0.0164 (4)
C1	0.1250 (2)	0.2144 (2)	0.41525 (8)	0.0169 (5)
C2	0.0969 (3)	−0.0098 (2)	0.42684 (8)	0.0193 (5)
C3	0.1398 (2)	0.0567 (2)	0.46830 (8)	0.0171 (5)
C4	0.0839 (2)	0.28924 (18)	0.52017 (8)	0.0134 (5)
C5	0.1292 (2)	0.35908 (19)	0.56150 (8)	0.0154 (5)
C6	0.1110 (2)	0.27896 (19)	0.60228 (8)	0.0161 (5)
C7	0.2173 (3)	0.2042 (2)	0.61513 (8)	0.0214 (5)
C8	0.2021 (3)	0.1278 (2)	0.65112 (9)	0.0231 (6)
C9	0.0800 (3)	0.1236 (2)	0.67589 (8)	0.0186 (5)
C10	−0.0259 (3)	0.1977 (2)	0.66277 (8)	0.0199 (5)
C11	−0.0112 (3)	0.2746 (2)	0.62666 (8)	0.0191 (5)
C12	0.0669 (3)	0.0436 (2)	0.71635 (8)	0.0225 (5)
C13	0.1343 (3)	0.0931 (2)	0.75930 (8)	0.0241 (6)
C14	0.0692 (4)	0.2092 (3)	0.77362 (11)	0.0338 (7)
C15	0.1251 (4)	0.0031 (3)	0.79731 (10)	0.0343 (7)
C16	0.0467 (3)	0.4732 (2)	0.56402 (9)	0.0211 (5)
H2A	0.018 (3)	−0.046 (3)	0.4334 (10)	0.037 (8)*
H2B	0.166 (3)	−0.062 (2)	0.4197 (9)	0.029 (7)*
H5	0.231 (3)	0.381 (2)	0.5594 (8)	0.014 (6)*
H7	0.299 (3)	0.204 (2)	0.5973 (9)	0.027 (7)*
H8	0.277 (3)	0.074 (2)	0.6603 (9)	0.023 (7)*
H10	−0.111 (3)	0.198 (2)	0.6778 (8)	0.016 (6)*
H11	−0.083 (3)	0.326 (3)	0.6170 (9)	0.028 (7)*
H12A	0.107 (3)	−0.031 (2)	0.7094 (9)	0.023 (7)*
H12B	−0.031 (3)	0.031 (2)	0.7228 (8)	0.015 (6)*
H13	0.232 (3)	0.109 (2)	0.7529 (10)	0.034 (8)*
H14A	0.109 (3)	0.239 (3)	0.7992 (11)	0.037 (8)*
H14B	−0.031 (3)	0.197 (3)	0.7814 (10)	0.038 (8)*
H14C	0.075 (3)	0.270 (3)	0.7520 (11)	0.046 (9)*
H15A	0.167 (3)	0.035 (3)	0.8251 (11)	0.042 (9)*
H15B	0.029 (3)	−0.021 (3)	0.8030 (10)	0.039 (8)*
H15C	0.171 (3)	−0.073 (3)	0.7888 (10)	0.036 (8)*
H16A	−0.054 (3)	0.457 (2)	0.5618 (9)	0.030 (8)*
H16B	0.078 (3)	0.527 (2)	0.5401 (9)	0.024 (7)*
H16C	0.063 (3)	0.507 (3)	0.5937 (10)	0.032 (8)*
H1N2	0.271 (3)	0.270 (2)	0.4968 (9)	0.031 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0388 (4)	0.0173 (3)	0.0146 (3)	−0.0015 (3)	−0.0018 (3)	−0.0025 (2)
O1	0.0259 (10)	0.0239 (9)	0.0207 (9)	0.0021 (7)	−0.0022 (7)	0.0052 (7)
O2	0.0339 (10)	0.0151 (8)	0.0213 (9)	−0.0008 (7)	−0.0007 (8)	0.0013 (7)
O3	0.0120 (8)	0.0254 (9)	0.0254 (10)	−0.0013 (7)	−0.0005 (7)	−0.0031 (7)
N1	0.0155 (10)	0.0149 (9)	0.0157 (10)	−0.0010 (7)	−0.0002 (8)	−0.0018 (8)
N2	0.0140 (11)	0.0208 (10)	0.0144 (10)	−0.0025 (8)	−0.0004 (9)	−0.0047 (8)
C1	0.0174 (12)	0.0183 (12)	0.0150 (12)	0.0025 (9)	0.0029 (10)	−0.0019 (9)
C2	0.0265 (14)	0.0139 (11)	0.0174 (12)	0.0006 (10)	0.0028 (10)	0.0025 (9)
C3	0.0137 (11)	0.0194 (11)	0.0182 (12)	0.0041 (9)	0.0027 (10)	0.0002 (9)
C4	0.0152 (12)	0.0118 (10)	0.0132 (11)	0.0013 (9)	−0.0005 (9)	0.0044 (8)
C5	0.0152 (12)	0.0153 (11)	0.0158 (12)	−0.0012 (9)	0.0000 (10)	0.0026 (9)
C6	0.0212 (12)	0.0144 (11)	0.0128 (11)	−0.0016 (9)	−0.0006 (9)	−0.0016 (9)
C7	0.0200 (13)	0.0241 (12)	0.0200 (13)	0.0020 (10)	0.0044 (11)	0.0015 (10)
C8	0.0250 (14)	0.0236 (13)	0.0208 (13)	0.0063 (10)	−0.0005 (11)	0.0027 (10)
C9	0.0284 (13)	0.0162 (11)	0.0113 (11)	−0.0060 (10)	−0.0025 (10)	−0.0024 (9)
C10	0.0207 (13)	0.0214 (12)	0.0176 (12)	−0.0040 (10)	0.0033 (11)	−0.0030 (10)
C11	0.0204 (13)	0.0182 (11)	0.0186 (13)	0.0010 (10)	−0.0032 (10)	−0.0004 (9)
C12	0.0301 (15)	0.0202 (13)	0.0171 (13)	−0.0034 (11)	0.0014 (11)	0.0002 (10)
C13	0.0297 (15)	0.0264 (13)	0.0163 (13)	−0.0029 (11)	−0.0020 (11)	0.0050 (10)
C14	0.051 (2)	0.0285 (15)	0.0223 (15)	0.0008 (14)	−0.0058 (15)	−0.0052 (13)
C15	0.0472 (19)	0.0352 (16)	0.0205 (15)	−0.0025 (14)	−0.0038 (13)	0.0081 (12)
C16	0.0266 (14)	0.0158 (12)	0.0210 (14)	0.0009 (10)	0.0011 (11)	−0.0008 (10)

S1—C1	1.758 (2)	C8—H8	0.99 (3)
S1—C2	1.811 (2)	C9—C10	1.388 (3)
O1—C3	1.207 (3)	C9—C12	1.511 (3)
O2—C1	1.209 (3)	C10—C11	1.391 (3)
O3—C4	1.220 (3)	C10—H10	0.94 (3)
N1—N2	1.381 (3)	C11—H11	0.96 (3)
N1—C3	1.392 (3)	C12—C13	1.538 (4)
N1—C1	1.394 (3)	C12—H12A	0.96 (3)
N2—C4	1.352 (3)	C12—H12B	0.99 (2)
N2—H1N2	0.85 (3)	C13—C15	1.526 (4)
C2—C3	1.503 (3)	C13—C14	1.527 (4)
C2—H2A	0.90 (3)	C13—H13	0.99 (3)
C2—H2B	0.92 (3)	C14—H14A	0.92 (3)
C4—C5	1.526 (3)	C14—H14B	1.01 (3)
C5—C6	1.525 (3)	C14—H14C	0.95 (3)
C5—C16	1.530 (3)	C15—H15A	0.99 (3)
C5—H5	1.02 (2)	C15—H15B	0.98 (3)
C6—C11	1.392 (3)	C15—H15C	1.01 (3)
C6—C7	1.393 (3)	C16—H16A	1.00 (3)
C7—C8	1.385 (3)	C16—H16B	0.98 (3)
C7—H7	0.95 (3)	C16—H16C	0.97 (3)
C8—C9	1.398 (4)
C1—S1—C2	93.19 (11)	C10—C9—C12	121.8 (2)
N2—N1—C3	120.43 (19)	C8—C9—C12	120.6 (2)
N2—N1—C1	120.79 (18)	C9—C10—C11	121.5 (2)
C3—N1—C1	118.35 (19)	C9—C10—H10	121.4 (15)
C4—N2—N1	118.2 (2)	C11—C10—H10	117.1 (15)
C4—N2—H1N2	124.4 (19)	C10—C11—C6	120.6 (2)
N1—N2—H1N2	116.8 (19)	C10—C11—H11	122.8 (16)
O2—C1—N1	124.6 (2)	C6—C11—H11	116.6 (16)
O2—C1—S1	125.66 (19)	C9—C12—C13	113.6 (2)
N1—C1—S1	109.77 (16)	C9—C12—H12A	109.3 (16)
C3—C2—S1	107.87 (16)	C13—C12—H12A	109.3 (16)
C3—C2—H2A	107.0 (19)	C9—C12—H12B	109.0 (14)
S1—C2—H2A	110.9 (19)	C13—C12—H12B	108.0 (14)
C3—C2—H2B	108.1 (17)	H12A—C12—H12B	108 (2)
S1—C2—H2B	110.2 (18)	C15—C13—C14	110.7 (2)
H2A—C2—H2B	112 (3)	C15—C13—C12	109.9 (2)
O1—C3—N1	123.1 (2)	C14—C13—C12	111.8 (2)
O1—C3—C2	126.1 (2)	C15—C13—H13	108.6 (17)
N1—C3—C2	110.7 (2)	C14—C13—H13	107.3 (16)
O3—C4—N2	121.7 (2)	C12—C13—H13	108.5 (17)
O3—C4—C5	123.1 (2)	C13—C14—H14A	111.8 (19)
N2—C4—C5	115.2 (2)	C13—C14—H14B	109.8 (18)
C6—C5—C4	106.87 (17)	H14A—C14—H14B	106 (3)
C6—C5—C16	114.2 (2)	C13—C14—H14C	115 (2)
C4—C5—C16	109.36 (19)	H14A—C14—H14C	105 (3)
C6—C5—H5	107.9 (13)	H14B—C14—H14C	109 (3)
C4—C5—H5	110.9 (13)	C13—C15—H15A	109.8 (18)
C16—C5—H5	107.7 (13)	C13—C15—H15B	111.4 (18)
C11—C6—C7	118.1 (2)	H15A—C15—H15B	111 (3)
C11—C6—C5	122.1 (2)	C13—C15—H15C	111.5 (17)
C7—C6—C5	119.8 (2)	H15A—C15—H15C	110 (2)
C8—C7—C6	121.1 (2)	H15B—C15—H15C	103 (2)
C8—C7—H7	121.0 (16)	C5—C16—H16A	110.8 (16)
C6—C7—H7	117.8 (16)	C5—C16—H16B	109.2 (15)
C7—C8—C9	121.1 (2)	H16A—C16—H16B	112 (2)
C7—C8—H8	121.5 (15)	C5—C16—H16C	107.1 (17)
C9—C8—H8	117.4 (15)	H16A—C16—H16C	107 (2)
C10—C9—C8	117.6 (2)	H16B—C16—H16C	111 (2)
C3—N1—N2—C4	−77.8 (3)	N2—C4—C5—C16	128.2 (2)
C1—N1—N2—C4	94.6 (2)	C4—C5—C6—C11	−89.8 (3)
N2—N1—C1—O2	6.7 (3)	C16—C5—C6—C11	31.2 (3)
C3—N1—C1—O2	179.2 (2)	C4—C5—C6—C7	87.9 (2)
N2—N1—C1—S1	−174.03 (16)	C16—C5—C6—C7	−151.0 (2)
C3—N1—C1—S1	−1.5 (2)	C11—C6—C7—C8	−0.1 (4)
C2—S1—C1—O2	178.7 (2)	C5—C6—C7—C8	−177.9 (2)
C2—S1—C1—N1	−0.56 (18)	C6—C7—C8—C9	−0.3 (4)
C1—S1—C2—C3	2.22 (19)	C7—C8—C9—C10	0.7 (4)
N2—N1—C3—O1	−4.9 (3)	C7—C8—C9—C12	−177.3 (2)
C1—N1—C3—O1	−177.5 (2)	C8—C9—C10—C11	−0.7 (3)
N2—N1—C3—C2	175.8 (2)	C12—C9—C10—C11	177.3 (2)
C1—N1—C3—C2	3.3 (3)	C9—C10—C11—C6	0.3 (4)
S1—C2—C3—O1	177.4 (2)	C7—C6—C11—C10	0.1 (3)
S1—C2—C3—N1	−3.3 (2)	C5—C6—C11—C10	177.8 (2)
N1—N2—C4—O3	−8.5 (3)	C10—C9—C12—C13	−98.4 (3)
N1—N2—C4—C5	169.96 (18)	C8—C9—C12—C13	79.5 (3)
O3—C4—C5—C6	70.7 (3)	C9—C12—C13—C15	−175.9 (2)
N2—C4—C5—C6	−107.7 (2)	C9—C12—C13—C14	60.8 (3)
O3—C4—C5—C16	−53.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3i	0.85 (3)	1.94 (3)	2.713 (2)	151 (2)
C2—H2A···O1ii	0.89 (3)	2.53 (3)	3.209 (3)	133 (3)
C2—H2B···O2iii	0.92 (3)	2.45 (3)	3.371 (3)	174 (2)
C5—H5···O1iv	1.02 (3)	2.46 (2)	3.190 (3)	127.6 (18)
C2—H2A···Cg2ii	0.90 (3)	2.99 (3)	3.474 (3)	116 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3i	0.85 (3)	1.94 (3)	2.713 (2)	151 (2)
C2—H2A⋯O1ii	0.89 (3)	2.53 (3)	3.209 (3)	133 (3)
C2—H2B⋯O2iii	0.92 (3)	2.45 (3)	3.371 (3)	174 (2)
C5—H5⋯O1iv	1.02 (3)	2.46 (2)	3.190 (3)	127.6 (18)
C2—H2A⋯Cg2ii	0.90 (3)	2.99 (3)	3.474 (3)	116 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C6–C11 ring ring.