3-(2H-1,3-Benzodioxol-5-ylmeth­yl)-2-(2-meth­oxy­phen­yl)-1,3-thia­zolidin-4-one

Facchinetti, V.; Gomes, C.R.B.; Cunico, W.; Wardell, S.M.S.V.; Wardell, J.L.; Tiekink, E.R.T.

doi:10.1107/S1600536811041262

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2970-o2971

doi:10.1107/S1600536811041262

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3-(2H-1,3-Benzodioxol-5-ylmethyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one

Victor Facchinetti,^a Claudia R. B. Gomes,^a Wilson Cunico,^b Solange M. S. V. Wardell,^c James L. Wardell ^d ‡ and Edward R. T. Tiekink ^e ^*

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos–Farmanguinhos, R. Sizenando Nabuco 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^bDepartamento de Química Orgânica, Universidade Federal de Pelotas (UFPel), Campus Universitário, s/n, Caixa Postal 354, 96010-900 Pelotas, RS, Brazil, ^cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 October 2011; accepted 7 October 2011; online 22 October 2011)

The title molecule, C₁₈H₁₇NO₄S, features a 1,3-thiazolidine ring that is twisted about the S—C(methylene) bond. With reference to this ring, the 1,3-benzodioxole and benzene rings lie to either side and form dihedral angles of 69.72 (16) and 83.60 (14)°, respectively, with the central ring. Significant twisting in the molecule is confirmed by the dihedral angle of 79.91 (13)° formed between the outer rings. Linear supramolecular chains along the a-axis direction mediated by C—H⋯O interactions feature in the crystal packing.

Related literature

For background to the biological activity of thiazolidinones, see: Cunico et al. (2008a ); Solomon et al. (2007 ); Kavitha et al. (2006 ); Sharma et al. (2006 ); Ravichandran et al. (2009 ); Rao et al. (2004 ). For background to the synthesis, see: Cunico et al. (2008b ); Rawal et al. (2008 ), Gomes et al. (2010 ), Neuenfeldt et al. (2011 ). For related studies on the synthesis and biological evaluation of thiazolidinones, see: Cunico et al. (2006 , 2007 ). For a thiazolidinone structure, see: Neuenfeldt et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₇NO₄S
M_r = 343.39
Monoclinic, P 2₁ /n
a = 6.8137 (3) Å
b = 12.5753 (7) Å
c = 18.5071 (9) Å
β = 91.825 (3)°
V = 1584.96 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 120 K
0.16 × 0.06 × 0.05 mm

Data collection

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.553, T_max = 0.746
21683 measured reflections
3625 independent reflections
1935 reflections with I > 2σ(I)
R_int = 0.159

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.180
S = 1.02
3625 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.95	2.36	3.302 (4)	170
C13—H13⋯O1ⁱⁱ	0.95	2.43	3.352 (4)	163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041262/hb6438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041262/hb6438Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041262/hb6438Isup3.cml

checkCIF report

Comment top

Thiazolidinones constitute an important group of heterocyclic compounds (Cunico et al., 2008a), having valuable biological uses, for example, as anti-malarial (Solomon et al., 2007), anti-microbial (Kavitha et al., 2006), anti-inflammatory (Sharma et al., 2006), and anti-viral agents, especially as anti-HIV agents (Ravichandran et al., 2009; Rao et al., 2004). The main synthetic routes to 1,3-thiazolidin-4-ones involve three components (an aldehyde, an amine and mercaptoacetic acid), either in a one- or two-step process (Cunico et al., 2008a; Rawal et al., 2008), and also under ultrasound irradiation (Neuenfeldt et al., 2011). The structure of 1-thia-4-azaspiro[4.5]decan-3-one has been reported recently (Neuenfeldt et al., 2009). In continuation of our research on thiazolidinones, (Cunico et al., 2006; Cunico et al., 2007; Cunico et al., 2008b; Gomes et al., 2010; Neuenfeldt et al., 2011), we now wish to report the structure of 2-(2-methoxybenzaldehyde)-3-piperonyl-1,3-thiazolidin-4-one, (I), synthesized, as reported from piperonylamine, 2-methoxybenzaldehyde and mercaptoacetic acid under ultrasound irradiation (Neuenfeldt et al., 2011). The sample used in the structure determination was grown from its EtOH solution.

The thiazolidinyl ring in (I), Fig. 1, is twisted about the S1—C3 bond but, the deviations from co-planarity for the five atoms are not great, i.e. the maximum and minimum deviations are 0.109 (1) Å for atom S1 and -0.117 (4) Å for atom C3; the ketone-O1 atom lies 0.244 (2) Å out of the least-squares plane through the five-membered ring. The dioxole ring has an envelope conformation with the C15 atom being the flap atom. The r.m.s. deviation for the 13 non-hydrogen atoms comprising the 1,3-benzodioxole ring is 0.110 Å. With reference to the thiazolidinyl ring, the 1,3-benzodioxole and benzene rings lie to either side and form dihedral angles with this ring of 69.72 (16) and 83.60 (14)°, respectively. The outer rings form a dihedral angle of 79.91 (13)° with each other, indicating that the molecule is highly twisted.

The most prominent feature of the crystal packing is the formation of C—H···O interactions involving the bifurcated carbonyl-O1 atom, Table 1. These lead to linear supramolecular chains along the a axis, Fig. 2.

Related literature top

For background to the biological activity of thiazolidinones, see: Cunico et al. (2008a); Solomon et al. (2007); Kavitha et al. (2006); Sharma et al. (2006); Ravichandran et al. (2009); Rao et al. (2004). For background to the synthesis, see: Cunico et al. (2008b); Rawal et al. (2008), Gomes et al. (2010), Neuenfeldt et al. (2011). For related studies on the synthesis and biological evaluation of thiazolidinones, see: Cunico et al. (2006, 2007). For a thiazolidinone structure, see: Neuenfeldt et al. (2009).

Experimental top

The title compound was synthesized as described in the literature (Neuenfeldt et al., 2011) and crystals were obtained from its EtOH solution.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the linear supramolecular chain propogated down the a axis via C—H···O interactions (orange dashed lines) in the crystal structure of (I).

3-(2H-1,3-Benzodioxol-5-ylmethyl)-2-(2-methoxyphenyl)- 1,3-thiazolidin-4-one top

Crystal data top

C₁₈H₁₇NO₄S	F(000) = 720
M_r = 343.39	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7149 reflections
a = 6.8137 (3) Å	θ = 2.9–27.5°
b = 12.5753 (7) Å	µ = 0.23 mm⁻¹
c = 18.5071 (9) Å	T = 120 K
β = 91.825 (3)°	Block, colourless
V = 1584.96 (14) Å³	0.16 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer	3625 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1935 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	R_int = 0.159
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −15→16
T_min = 0.553, T_max = 0.746	l = −23→24
21683 measured reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0754P)²] where P = (F_o² + 2F_c²)/3
3625 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₈H₁₇NO₄S	V = 1584.96 (14) Å³
M_r = 343.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.8137 (3) Å	µ = 0.23 mm⁻¹
b = 12.5753 (7) Å	T = 120 K
c = 18.5071 (9) Å	0.16 × 0.06 × 0.05 mm
β = 91.825 (3)°

Data collection top

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer	3625 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1935 reflections with I > 2σ(I)
T_min = 0.553, T_max = 0.746	R_int = 0.159
21683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.02	Δρ_max = 0.33 e Å⁻³
3625 reflections	Δρ_min = −0.43 e Å⁻³
218 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.48794 (13)	0.72256 (9)	0.17227 (5)	0.0365 (3)
O1	0.3856 (3)	0.60647 (19)	−0.01787 (12)	0.0321 (6)
O2	0.9136 (3)	0.76552 (19)	0.24212 (12)	0.0291 (6)
O3	1.2380 (3)	0.9163 (2)	−0.11437 (14)	0.0358 (6)
O4	1.0102 (3)	1.05303 (19)	−0.11655 (13)	0.0328 (6)
N1	0.6500 (4)	0.6556 (2)	0.05355 (13)	0.0231 (6)
C1	0.7138 (4)	0.6948 (3)	0.12420 (17)	0.0246 (8)
H1	0.7849	0.7635	0.1174	0.029*
C2	0.4558 (5)	0.6343 (3)	0.04091 (18)	0.0260 (8)
C3	0.3391 (5)	0.6492 (3)	0.10759 (19)	0.0358 (9)
H3A	0.3034	0.5792	0.1279	0.043*
H3B	0.2167	0.6888	0.0957	0.043*
C4	0.8488 (4)	0.6199 (3)	0.16581 (17)	0.0239 (8)
C5	0.9521 (4)	0.6609 (3)	0.22695 (17)	0.0236 (8)
C6	1.0804 (5)	0.5969 (3)	0.26668 (18)	0.0278 (8)
H6	1.1525	0.6253	0.3070	0.033*
C7	1.1036 (5)	0.4905 (3)	0.24740 (18)	0.0300 (9)
H7	1.1917	0.4465	0.2747	0.036*
C8	0.9991 (5)	0.4487 (3)	0.18869 (18)	0.0289 (8)
H8	1.0127	0.3757	0.1765	0.035*
C9	0.8740 (5)	0.5139 (3)	0.14744 (17)	0.0260 (8)
H9	0.8053	0.4856	0.1063	0.031*
C10	0.9967 (5)	0.8064 (3)	0.30861 (18)	0.0321 (9)
H10A	0.9499	0.7642	0.3491	0.048*
H10B	0.9568	0.8807	0.3145	0.048*
H10C	1.1402	0.8022	0.3077	0.048*
C11	0.7881 (5)	0.6555 (3)	−0.00479 (17)	0.0281 (8)
H11A	0.7309	0.6146	−0.0460	0.034*
H11B	0.9099	0.6188	0.0119	0.034*
C12	0.8399 (5)	0.7660 (3)	−0.03050 (16)	0.0254 (8)
C13	1.0282 (5)	0.7820 (3)	−0.05777 (17)	0.0245 (8)
H13	1.1244	0.7273	−0.0570	0.029*
C14	1.0652 (4)	0.8808 (3)	−0.08553 (18)	0.0264 (8)
C15	1.1839 (5)	1.0137 (3)	−0.1505 (2)	0.0372 (9)
H15A	1.1562	1.0004	−0.2026	0.045*
H15B	1.2917	1.0662	−0.1456	0.045*
C16	0.9303 (5)	0.9626 (3)	−0.08612 (18)	0.0285 (8)
C17	0.7480 (5)	0.9499 (3)	−0.05749 (17)	0.0280 (8)
H17	0.6563	1.0068	−0.0562	0.034*
C18	0.7038 (5)	0.8489 (3)	−0.03018 (17)	0.0260 (8)
H18	0.5781	0.8366	−0.0110	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0270 (5)	0.0496 (7)	0.0329 (5)	0.0028 (4)	0.0009 (4)	−0.0113 (5)
O1	0.0314 (13)	0.0343 (16)	0.0300 (14)	0.0017 (11)	−0.0083 (11)	−0.0041 (12)
O2	0.0332 (13)	0.0292 (15)	0.0245 (13)	0.0021 (11)	−0.0070 (10)	−0.0028 (11)
O3	0.0291 (13)	0.0316 (16)	0.0472 (16)	0.0008 (11)	0.0082 (11)	0.0041 (12)
O4	0.0329 (14)	0.0290 (15)	0.0367 (14)	−0.0010 (11)	0.0049 (11)	0.0016 (12)
N1	0.0231 (14)	0.0276 (17)	0.0183 (13)	−0.0027 (12)	−0.0017 (11)	−0.0009 (12)
C1	0.0246 (17)	0.026 (2)	0.0232 (17)	−0.0041 (14)	−0.0026 (14)	−0.0039 (15)
C2	0.0269 (17)	0.023 (2)	0.0279 (19)	−0.0020 (14)	−0.0041 (15)	0.0032 (16)
C3	0.0270 (18)	0.050 (3)	0.0305 (19)	−0.0054 (17)	0.0024 (15)	−0.0001 (18)
C4	0.0199 (16)	0.030 (2)	0.0223 (17)	−0.0005 (14)	0.0019 (13)	0.0035 (15)
C5	0.0213 (16)	0.028 (2)	0.0218 (17)	−0.0039 (14)	0.0000 (13)	−0.0007 (15)
C6	0.0255 (17)	0.035 (2)	0.0225 (18)	−0.0062 (16)	−0.0016 (14)	0.0015 (16)
C7	0.0307 (19)	0.029 (2)	0.030 (2)	0.0074 (16)	0.0020 (16)	0.0040 (17)
C8	0.0306 (19)	0.027 (2)	0.0294 (19)	−0.0010 (15)	0.0006 (15)	−0.0041 (16)
C9	0.0280 (18)	0.029 (2)	0.0207 (17)	−0.0037 (15)	−0.0012 (14)	0.0010 (15)
C10	0.037 (2)	0.031 (2)	0.0284 (19)	−0.0037 (17)	−0.0062 (15)	−0.0091 (17)
C11	0.0308 (18)	0.031 (2)	0.0220 (17)	0.0019 (16)	0.0018 (14)	−0.0015 (16)
C12	0.0283 (18)	0.031 (2)	0.0164 (17)	−0.0006 (15)	−0.0049 (14)	−0.0026 (15)
C13	0.0251 (17)	0.024 (2)	0.0239 (17)	0.0047 (14)	−0.0016 (14)	0.0000 (15)
C14	0.0231 (17)	0.031 (2)	0.0250 (18)	−0.0010 (15)	−0.0005 (14)	−0.0027 (16)
C15	0.036 (2)	0.032 (2)	0.044 (2)	0.0046 (17)	0.0117 (18)	0.0017 (18)
C16	0.0322 (19)	0.029 (2)	0.0240 (18)	−0.0043 (16)	−0.0032 (15)	0.0000 (16)
C17	0.0296 (19)	0.030 (2)	0.0239 (18)	0.0047 (15)	−0.0020 (15)	−0.0021 (16)
C18	0.0225 (16)	0.030 (2)	0.0256 (17)	−0.0013 (15)	−0.0020 (14)	0.0000 (16)

Geometric parameters (Å, º) top

S1—C3	1.799 (4)	C7—C8	1.384 (5)
S1—C1	1.836 (3)	C7—H7	0.9500
O1—C2	1.225 (4)	C8—C9	1.393 (5)
O2—C5	1.372 (4)	C8—H8	0.9500
O2—C10	1.433 (4)	C9—H9	0.9500
O3—C14	1.382 (4)	C10—H10A	0.9800
O3—C15	1.437 (4)	C10—H10B	0.9800
O4—C16	1.388 (4)	C10—H10C	0.9800
O4—C15	1.445 (4)	C11—C12	1.514 (5)
N1—C2	1.363 (4)	C11—H11A	0.9900
N1—C1	1.451 (4)	C11—H11B	0.9900
N1—C11	1.455 (4)	C12—C18	1.395 (5)
C1—C4	1.510 (5)	C12—C13	1.408 (5)
C1—H1	1.0000	C13—C14	1.372 (5)
C2—C3	1.501 (5)	C13—H13	0.9500
C3—H3A	0.9900	C14—C16	1.379 (5)
C3—H3B	0.9900	C15—H15A	0.9900
C4—C9	1.387 (5)	C15—H15B	0.9900
C4—C5	1.411 (4)	C16—C17	1.375 (5)
C5—C6	1.382 (5)	C17—C18	1.404 (5)
C6—C7	1.395 (5)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500

C3—S1—C1	92.50 (15)	C4—C9—H9	119.7
C5—O2—C10	116.5 (3)	C8—C9—H9	119.7
C14—O3—C15	104.2 (2)	O2—C10—H10A	109.5
C16—O4—C15	103.5 (3)	O2—C10—H10B	109.5
C2—N1—C1	118.9 (3)	H10A—C10—H10B	109.5
C2—N1—C11	121.3 (3)	O2—C10—H10C	109.5
C1—N1—C11	119.1 (3)	H10A—C10—H10C	109.5
N1—C1—C4	114.1 (3)	H10B—C10—H10C	109.5
N1—C1—S1	105.6 (2)	N1—C11—C12	113.3 (3)
C4—C1—S1	112.2 (2)	N1—C11—H11A	108.9
N1—C1—H1	108.2	C12—C11—H11A	108.9
C4—C1—H1	108.2	N1—C11—H11B	108.9
S1—C1—H1	108.2	C12—C11—H11B	108.9
O1—C2—N1	123.9 (3)	H11A—C11—H11B	107.7
O1—C2—C3	124.3 (3)	C18—C12—C13	120.5 (3)
N1—C2—C3	111.8 (3)	C18—C12—C11	121.5 (3)
C2—C3—S1	108.0 (2)	C13—C12—C11	117.9 (3)
C2—C3—H3A	110.1	C14—C13—C12	116.4 (3)
S1—C3—H3A	110.1	C14—C13—H13	121.8
C2—C3—H3B	110.1	C12—C13—H13	121.8
S1—C3—H3B	110.1	C13—C14—C16	123.2 (3)
H3A—C3—H3B	108.4	C13—C14—O3	127.3 (3)
C9—C4—C5	119.0 (3)	C16—C14—O3	109.4 (3)
C9—C4—C1	123.5 (3)	O3—C15—O4	106.9 (3)
C5—C4—C1	117.5 (3)	O3—C15—H15A	110.3
O2—C5—C6	124.8 (3)	O4—C15—H15A	110.3
O2—C5—C4	114.9 (3)	O3—C15—H15B	110.3
C6—C5—C4	120.3 (3)	O4—C15—H15B	110.3
C5—C6—C7	119.8 (3)	H15A—C15—H15B	108.6
C5—C6—H6	120.1	C17—C16—C14	121.4 (3)
C7—C6—H6	120.1	C17—C16—O4	128.5 (3)
C8—C7—C6	120.4 (3)	C14—C16—O4	110.1 (3)
C8—C7—H7	119.8	C16—C17—C18	116.8 (3)
C6—C7—H7	119.8	C16—C17—H17	121.6
C7—C8—C9	119.8 (3)	C18—C17—H17	121.6
C7—C8—H8	120.1	C12—C18—C17	121.7 (3)
C9—C8—H8	120.1	C12—C18—H18	119.2
C4—C9—C8	120.7 (3)	C17—C18—H18	119.2

C2—N1—C1—C4	115.2 (3)	C5—C4—C9—C8	0.1 (5)
C11—N1—C1—C4	−74.1 (4)	C1—C4—C9—C8	−179.2 (3)
C2—N1—C1—S1	−8.5 (4)	C7—C8—C9—C4	−1.8 (5)
C11—N1—C1—S1	162.2 (2)	C2—N1—C11—C12	101.4 (4)
C3—S1—C1—N1	14.3 (2)	C1—N1—C11—C12	−69.0 (4)
C3—S1—C1—C4	−110.5 (3)	N1—C11—C12—C18	−33.1 (4)
C1—N1—C2—O1	175.9 (3)	N1—C11—C12—C13	149.5 (3)
C11—N1—C2—O1	5.4 (5)	C18—C12—C13—C14	−2.1 (5)
C1—N1—C2—C3	−4.0 (4)	C11—C12—C13—C14	175.3 (3)
C11—N1—C2—C3	−174.5 (3)	C12—C13—C14—C16	1.4 (5)
O1—C2—C3—S1	−165.0 (3)	C12—C13—C14—O3	179.1 (3)
N1—C2—C3—S1	14.9 (4)	C15—O3—C14—C13	166.6 (3)
C1—S1—C3—C2	−16.7 (3)	C15—O3—C14—C16	−15.4 (4)
N1—C1—C4—C9	−14.6 (4)	C14—O3—C15—O4	23.8 (4)
S1—C1—C4—C9	105.4 (3)	C16—O4—C15—O3	−23.0 (3)
N1—C1—C4—C5	166.0 (3)	C13—C14—C16—C17	0.9 (5)
S1—C1—C4—C5	−73.9 (3)	O3—C14—C16—C17	−177.2 (3)
C10—O2—C5—C6	−7.3 (4)	C13—C14—C16—O4	179.2 (3)
C10—O2—C5—C4	172.6 (3)	O3—C14—C16—O4	1.1 (4)
C9—C4—C5—O2	−178.2 (3)	C15—O4—C16—C17	−168.2 (3)
C1—C4—C5—O2	1.2 (4)	C15—O4—C16—C14	13.7 (4)
C9—C4—C5—C6	1.7 (4)	C14—C16—C17—C18	−2.3 (5)
C1—C4—C5—C6	−179.0 (3)	O4—C16—C17—C18	179.8 (3)
O2—C5—C6—C7	178.1 (3)	C13—C12—C18—C17	0.8 (5)
C4—C5—C6—C7	−1.8 (5)	C11—C12—C18—C17	−176.6 (3)
C5—C6—C7—C8	0.0 (5)	C16—C17—C18—C12	1.5 (5)
C6—C7—C8—C9	1.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.95	2.36	3.302 (4)	170
C13—H13···O1ⁱⁱ	0.95	2.43	3.352 (4)	163

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇NO₄S
M_r	343.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	6.8137 (3), 12.5753 (7), 18.5071 (9)
β (°)	91.825 (3)
V (Å³)	1584.96 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.16 × 0.06 × 0.05

Data collection
Diffractometer	Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.553, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	21683, 3625, 1935
R_int	0.159
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.180, 1.02
No. of reflections	3625
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.43

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.95	2.36	3.302 (4)	170
C13—H13···O1ⁱⁱ	0.95	2.43	3.352 (4)	163

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

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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Volume 67| Part 11| November 2011| Pages o2970-o2971

doi:10.1107/S1600536811041262

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

3-(2H-1,3-Benzodioxol-5-ylmeth­yl)-2-(2-meth­­oxy­phen­yl)-1,3-thia­zolidin-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-(2H-1,3-Benzodioxol-5-ylmethyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one