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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o919-o920
https://doi.org/10.1107/S2056989015020654

Crystal structure of (5Z)-5-(5-bromo-2-hy­dr­oxy­benzyl­­idene)-1,3-thia­zolidine-2,4-dione

Joel T. Mague,a Shaaban K. Mohamed,b,c Mehmet Akkurt,d Sabry H. H. Younese and Mustafa R. Albayatif*

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 30 October 2015; accepted 31 October 2015; online 7 November 2015)

In the title compound, C10H6BrNO3S, the dihedral angle between the thia­zolidine ring (r.m.s. deviation = 0.014 Å) and the benzene ring is 5.78 (14)°. The S atom of the heterocyclic ring is syn to the OH group attached to the benzene ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops. The dimers are linked into [001] ribbons by pairwise O—H⋯O hydrogen bonds with R22(18) motifs. There are no short contacts involving the Br atom.

CCDC reference: 1434469

Similar articles

1. Related literature

For the biological activities of chalcones, see: Nowakowska (2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]); Singh et al. (2011[Singh, S., Sharma, P. K., Kumar, N. & Dudhe, R. (2011). Asian J. Pharm. Biol. Res. 1, 412-418.]). For the various biological activities of thia­zolidinones, see: Cunico et al. (2008[Cunico, W., Gomes, C. R. B. & Vellasco, W. Jr (2008). Mini-Rev. Org. Chem. 5, 336-344.]); Verma & Saraf, (2008[Verma, A. & Saraf, S. K. (2008). Eur. J. Med. Chem. 43, 897-905.]); Hamama et al. (2008[Hamama, W. S., Ismail, M. A., Shaaban, S. & Zoorob, H. H. (2008). J. Heterocycl. Chem. 45, 939-956.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C10H6BrNO3S

  • Mr = 300.13

  • Triclinic, [P \overline 1]

  • a = 7.0680 (7) Å

  • b = 7.6770 (8) Å

  • c = 9.9977 (10) Å

  • α = 68.119 (2)°

  • β = 86.049 (1)°

  • γ = 83.658 (1)°

  • V = 500.10 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 4.31 mm−1

  • T = 150 K

  • 0.25 × 0.15 × 0.04 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 2015[Sheldrick, G. M. (2015). CELL NOW and TWINABS. University of Göttingen, Germany.]) Tmin = 0.41, Tmax = 0.85

  • 25727 measured reflections

  • 2629 independent reflections

  • 2220 reflections with I > 2σ(I)

  • Rint = 0.060

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.01

  • 2629 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.77 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O3i 0.84 1.91 2.740 (3) 168
N1—H2⋯O3ii 0.91 2.08 2.941 (3) 157
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2015[Bruker (2015). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2015[Bruker (2015). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and CELL_NOW (Sheldrick, 2015[Sheldrick, G. M. (2015). CELL NOW and TWINABS. University of Göttingen, Germany.]); program(s) used to solve structure: SHELXT (Sheldrick, 2015[Sheldrick, G. M. (2015). CELL NOW and TWINABS. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). CELL NOW and TWINABS. University of Göttingen, Germany.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1434469

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015020654/hb7533sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020654/hb7533Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020654/hb7533Isup3.cml

checkCIF report


Comment top

Chalcones exhibit a wide spectrum of biological activities including antimicrobial, anticancer, anti-protozoal, antiulcer, and antiinflammatory ones (Nowakowska, 2007; Singh et al., 2011). The tiazolidinone ring system has attracted the attention of many researchers to explore this skeleton to its multiple potential against several activities (Cunico et al., 2008; Verma & Saraf, 2008; Hamama et al., 2008). In this context we report here the synthesis and crystal structure of the title compound.

In the title molecule, the dihedral angle between the 6- and 5-membered rings is 5.8 (1)°. The molecules associate into dimers across centers of symmetry via pairwise N1—H2···O3 hydrogen bonds and these dimers associate with neighboring dimers through pairwise O1—H1···O3 hydrogen bonds across additional centers of symmetry to form ribbons (Fig. 2 and Table 1). Stacking of these ribbons generates the three-dimensional structure (Fig. 3).

Related literature top

For the biological activities of chalcones, see: Nowakowska (2007); Singh et al. (2011). For the various biological activities of thiazolidinones, see: Cunico et al. (2008); Verma & Saraf, (2008); Hamama et al. (2008).

Experimental top

The title compound was obtained as a major product from a three component reaction of 5-bromo-2-hydroxy-benzaldehyde (1 mmol, 201 mg), thiazolidine-2,4-dione (1 mmol, 117 mg) and 1-aminopropan-2-ol (1 mmol, 75 mg) under reflux in 30 ml e thanol. The reaction was monitored by TLC till completion. On cooling the solid product was collected by filteration, dried under vacuum and recrystallized from ethanol to afford colourless plates. M.p. 503 K.

Refinement top

Analysis of 1039 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2015) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about c*. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen and to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å and O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. In the final stages of the refinement, runs using the full set of twinned data gave poorer results (in particular large residual peaks in the vicinity of Br1) than did the single-component data extracted with TWINABS. Consequently the refinement was completed with the single-component data.

Structure description top

Chalcones exhibit a wide spectrum of biological activities including antimicrobial, anticancer, anti-protozoal, antiulcer, and antiinflammatory ones (Nowakowska, 2007; Singh et al., 2011). The tiazolidinone ring system has attracted the attention of many researchers to explore this skeleton to its multiple potential against several activities (Cunico et al., 2008; Verma & Saraf, 2008; Hamama et al., 2008). In this context we report here the synthesis and crystal structure of the title compound.

In the title molecule, the dihedral angle between the 6- and 5-membered rings is 5.8 (1)°. The molecules associate into dimers across centers of symmetry via pairwise N1—H2···O3 hydrogen bonds and these dimers associate with neighboring dimers through pairwise O1—H1···O3 hydrogen bonds across additional centers of symmetry to form ribbons (Fig. 2 and Table 1). Stacking of these ribbons generates the three-dimensional structure (Fig. 3).

For the biological activities of chalcones, see: Nowakowska (2007); Singh et al. (2011). For the various biological activities of thiazolidinones, see: Cunico et al. (2008); Verma & Saraf, (2008); Hamama et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015) and CELL_NOW (Sheldrick, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title molecule with 50% displacement ellipsoids.
[Figure 2] Fig. 2. A portion of one layer generated by N—H···O and O—H···O hydrogen bonds (blue and red dotted lines respectively.
[Figure 3] Fig. 3. Elevation view of the layer structure with hydrogen bonds shown as in Fig. 2.
(5Z)-5-(5-Bromo-2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione top
Crystal data top
C10H6BrNO3SZ = 2
Mr = 300.13F(000) = 296
Triclinic, P1Dx = 1.993 Mg m−3
a = 7.0680 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.6770 (8) ÅCell parameters from 6176 reflections
c = 9.9977 (10) Åθ = 2.9–29.0°
α = 68.119 (2)°µ = 4.31 mm−1
β = 86.049 (1)°T = 150 K
γ = 83.658 (1)°Plate, colourless
V = 500.10 (9) Å30.25 × 0.15 × 0.04 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		2629 independent reflections
Radiation source: fine-focus sealed tube2220 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 8.3333 pixels mm-1θmax = 29.1°, θmin = 2.2°
φ and ω scansh = −9→9
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2015)		k = −10→10
Tmin = 0.41, Tmax = 0.85l = −12→12
25727 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: mixed
wR(F2) = 0.085H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0497P)2]
where P = (Fo2 + 2Fc2)/3
2629 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.82 e Å−3
0 restraintsΔρmin = −0.77 e Å−3
Crystal data top
C10H6BrNO3Sγ = 83.658 (1)°
Mr = 300.13V = 500.10 (9) Å3
Triclinic, P1Z = 2
a = 7.0680 (7) ÅMo Kα radiation
b = 7.6770 (8) ŵ = 4.31 mm−1
c = 9.9977 (10) ÅT = 150 K
α = 68.119 (2)°0.25 × 0.15 × 0.04 mm
β = 86.049 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2629 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2015)		2220 reflections with I > 2σ(I)
Tmin = 0.41, Tmax = 0.85Rint = 0.060
25727 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.01Δρmax = 0.82 e Å−3
2629 reflectionsΔρmin = −0.77 e Å−3
145 parameters
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 20 sec/frame.

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. Analysis of 1039 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about c*. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen and to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91%A and O—H = 0.84%A. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. In the final stages of the refinement, runs using the full set of twinned data gave poorer results (in particular large residual peaks in the vicinity of Br1) than did the single-component data extracted with TWINABS (Sheldrick, 2015). Consequently the refinement was completed with the single-component data.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.07477 (3)0.44030 (4)0.79200 (3)0.02259 (10)
S10.14496 (8)0.91252 (9)0.38107 (7)0.01849 (15)
O10.2982 (2)0.8558 (3)0.6342 (2)0.0209 (4)
H10.24460.87450.70590.025*
O20.5262 (2)0.7995 (3)0.1222 (2)0.0241 (4)
O3−0.0849 (2)1.0476 (3)0.1603 (2)0.0228 (4)
N10.2180 (3)0.9316 (3)0.1180 (2)0.0194 (5)
H20.20250.95970.02240.023*
C10.5808 (3)0.7087 (4)0.5672 (3)0.0161 (5)
C20.4680 (3)0.7553 (4)0.6732 (3)0.0169 (5)
C30.5335 (3)0.7033 (4)0.8128 (3)0.0206 (5)
H30.45450.73370.88330.025*
C40.7120 (4)0.6080 (4)0.8501 (3)0.0202 (5)
H40.75570.57300.94520.024*
C50.8263 (3)0.5644 (4)0.7449 (3)0.0180 (5)
C60.7631 (3)0.6130 (3)0.6081 (3)0.0165 (5)
H60.84370.58170.53870.020*
C70.5313 (3)0.7529 (4)0.4200 (3)0.0172 (5)
H70.63470.71950.36560.021*
C80.3763 (3)0.8294 (3)0.3389 (3)0.0165 (5)
C90.3887 (3)0.8481 (4)0.1850 (3)0.0184 (5)
C100.0738 (3)0.9734 (4)0.2026 (3)0.0178 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01631 (13)0.02877 (16)0.02252 (17)0.00492 (10)−0.00595 (10)−0.01027 (12)
S10.0135 (3)0.0290 (3)0.0140 (3)0.0040 (2)−0.0010 (2)−0.0106 (3)
O10.0166 (8)0.0310 (10)0.0165 (10)0.0072 (7)−0.0018 (7)−0.0126 (8)
O20.0184 (8)0.0378 (11)0.0164 (10)0.0069 (8)0.0002 (7)−0.0132 (9)
O30.0162 (8)0.0351 (11)0.0194 (10)0.0064 (8)−0.0033 (7)−0.0145 (9)
N10.0155 (9)0.0303 (12)0.0137 (11)0.0044 (9)−0.0017 (8)−0.0113 (10)
C10.0134 (10)0.0203 (12)0.0152 (13)0.0007 (9)−0.0011 (9)−0.0077 (10)
C20.0146 (10)0.0215 (12)0.0154 (13)−0.0005 (9)−0.0007 (9)−0.0081 (10)
C30.0197 (12)0.0248 (13)0.0187 (14)0.0003 (10)0.0000 (10)−0.0102 (11)
C40.0216 (11)0.0240 (13)0.0140 (13)0.0009 (10)−0.0043 (9)−0.0059 (11)
C50.0144 (10)0.0195 (12)0.0203 (14)0.0021 (9)−0.0017 (9)−0.0084 (11)
C60.0136 (10)0.0201 (12)0.0161 (13)0.0013 (9)−0.0003 (9)−0.0080 (10)
C70.0160 (10)0.0205 (12)0.0164 (13)0.0019 (9)0.0010 (9)−0.0094 (10)
C80.0150 (10)0.0207 (12)0.0142 (13)0.0008 (9)0.0009 (9)−0.0076 (10)
C90.0159 (11)0.0224 (13)0.0169 (13)0.0017 (9)−0.0023 (9)−0.0078 (11)
C100.0170 (11)0.0231 (13)0.0139 (13)0.0018 (9)−0.0012 (9)−0.0084 (11)
Geometric parameters (Å, º) top
Br1—C51.903 (2)C1—C71.441 (4)
S1—C101.762 (3)C2—C31.398 (4)
S1—C81.770 (2)C3—C41.387 (3)
O1—C21.350 (3)C3—H30.9500
O1—H10.8399C4—C51.399 (3)
O2—C91.220 (3)C4—H40.9500
O3—C101.227 (3)C5—C61.370 (4)
N1—C101.367 (3)C6—H60.9500
N1—C91.391 (3)C7—C81.352 (3)
N1—H20.9099C7—H70.9500
C1—C21.411 (3)C8—C91.489 (4)
C1—C61.416 (3)
C10—S1—C891.56 (12)C6—C5—Br1119.73 (18)
C2—O1—H1109.1C4—C5—Br1119.4 (2)
C10—N1—C9116.6 (2)C5—C6—C1121.8 (2)
C10—N1—H2121.1C5—C6—H6119.1
C9—N1—H2122.3C1—C6—H6119.1
C2—C1—C6117.0 (2)C8—C7—C1136.7 (2)
C2—C1—C7126.5 (2)C8—C7—H7111.7
C6—C1—C7116.5 (2)C1—C7—H7111.7
O1—C2—C3121.5 (2)C7—C8—C9118.3 (2)
O1—C2—C1117.9 (2)C7—C8—S1132.0 (2)
C3—C2—C1120.6 (2)C9—C8—S1109.68 (17)
C4—C3—C2121.1 (2)O2—C9—N1122.9 (2)
C4—C3—H3119.5O2—C9—C8126.6 (2)
C2—C3—H3119.5N1—C9—C8110.5 (2)
C3—C4—C5118.6 (2)O3—C10—N1124.8 (2)
C3—C4—H4120.7O3—C10—S1123.58 (19)
C5—C4—H4120.7N1—C10—S1111.62 (18)
C6—C5—C4120.9 (2)
C6—C1—C2—O1176.4 (2)C1—C7—C8—C9−179.6 (3)
C7—C1—C2—O1−1.9 (4)C1—C7—C8—S1−1.4 (5)
C6—C1—C2—C3−1.8 (4)C10—S1—C8—C7−179.7 (3)
C7—C1—C2—C3179.9 (2)C10—S1—C8—C9−1.38 (19)
O1—C2—C3—C4−176.9 (2)C10—N1—C9—O2178.0 (3)
C1—C2—C3—C41.3 (4)C10—N1—C9—C8−2.2 (3)
C2—C3—C4—C50.0 (4)C7—C8—C9—O20.7 (4)
C3—C4—C5—C6−0.6 (4)S1—C8—C9—O2−177.9 (2)
C3—C4—C5—Br1178.16 (19)C7—C8—C9—N1−179.2 (2)
C4—C5—C6—C10.0 (4)S1—C8—C9—N12.2 (3)
Br1—C5—C6—C1−178.79 (18)C9—N1—C10—O3179.7 (2)
C2—C1—C6—C51.2 (4)C9—N1—C10—S11.1 (3)
C7—C1—C6—C5179.7 (2)C8—S1—C10—O3−178.4 (2)
C2—C1—C7—C8−6.4 (5)C8—S1—C10—N10.2 (2)
C6—C1—C7—C8175.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.841.912.740 (3)168
N1—H2···O3ii0.912.082.941 (3)157
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.841.912.740 (3)168
N1—H2···O3ii0.912.082.941 (3)157
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+2, −z.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2015). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCunico, W., Gomes, C. R. B. & Vellasco, W. Jr (2008). Mini-Rev. Org. Chem. 5, 336–344.  Web of Science CrossRef CAS Google Scholar
 First citationHamama, W. S., Ismail, M. A., Shaaban, S. & Zoorob, H. H. (2008). J. Heterocycl. Chem. 45, 939–956.  CrossRef CAS Google Scholar
 First citationNowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125–137.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). CELL NOW and TWINABS. University of Göttingen, Germany.  Google Scholar
 First citationSingh, S., Sharma, P. K., Kumar, N. & Dudhe, R. (2011). Asian J. Pharm. Biol. Res. 1, 412–418.  Google Scholar
 First citationVerma, A. & Saraf, S. K. (2008). Eur. J. Med. Chem. 43, 897–905.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o919-o920
https://doi.org/10.1107/S2056989015020654
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