Literature DB >> 21587914

N-[(2S)-2-(4-Bromo-phen-yl)-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide.

Mehmet Akkurt, Ismail Celik, Hale Demir, Sumru Ozkırımlı, Orhan Büyükgüngör.   

Abstract

In the title compound, C(15)H(12)BrN(3)O(2)S, the dihedral angle between the pyridine and benzene rings is 73.17 (19)°. The five-membered 1,3-thia-zolidine ring has an envelope conformation, with the S atom displaced by 0.196 (1) Å from the mean plane of the four other ring atoms. An intra-molecular C-H⋯N inter-action occurs. The crystal structure is stabil-ized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions. In addition, a weak π-π stacking inter-action is also observed between the 1,3-thia-zolidine and pyridine rings [centroid-centroid distance = 3.805 (2) Å].

Entities:  

Year:  2010        PMID： 21587914      PMCID： PMC3006680          DOI： 10.1107/S1600536810022506

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the cytoprotective and anti­viral properties of nicotinamide, see: Gaudineau & Auclair (2004 ▶); Moell et al. (2009 ▶). For 3-pyridine­carboxamide derivatives with anti­tumor activity, see: Elbaum et al. (2003 ▶). For the various biological activities of thia­zolidinones, see: Capan et al. (1999 ▶) and Ozkırımlı et al. (2009 ▶) (anti­fungal); Guzel et al. (2006 ▶) (anti­tuberculosis); Rawal et al. (2007 ▶) (RT Inhibitor); Vanderlinden et al. (2010 ▶) (anti­viral). For standard bond-length data, see: Allen et al. (1987 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H12BrN3O2S M = 378.25 Trigonal, a = 24.9588 (9) Å c = 12.8013 (5) Å V = 6906.1 (4) Å3 Z = 18 Mo Kα radiation μ = 2.82 mm−1 T = 296 K 0.28 × 0.23 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.505, T max = 0.616 13554 measured reflections 3174 independent reflections 1963 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.085 S = 0.95 3174 reflections 202 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.35 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022506/lh5067sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022506/lh5067Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H12BrN3O2SDx = 1.637 Mg m−3
Mr = 378.25Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 10912 reflections
Hall symbol: -R 3θ = 1.6–28.0°
a = 24.9588 (9) ŵ = 2.82 mm−1
c = 12.8013 (5) ÅT = 296 K
V = 6906.1 (4) Å3Block, colourless
Z = 180.28 × 0.23 × 0.19 mm
F(000) = 3420
Stoe IPDS 2 diffractometer3174 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1963 reflections with I > 2σ(I)
plane graphiteRint = 0.050
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.6°
ω scansh = −30→27
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −31→31
Tmin = 0.505, Tmax = 0.616l = −15→16
13554 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 0.95w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
3174 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.22 e Å−3
1 restraintΔρmin = −0.35 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
Br10.04324 (2)0.93003 (2)0.13333 (3)0.0833 (2)
S10.18291 (4)0.97254 (4)0.63617 (6)0.0594 (3)
O10.35556 (11)1.03443 (11)0.58153 (16)0.0609 (9)
O20.33205 (10)1.15286 (10)0.51669 (15)0.0561 (8)
N10.27161 (11)1.03012 (11)0.50268 (17)0.0459 (8)
N20.30533 (11)1.06767 (12)0.41953 (17)0.0456 (8)
N30.41259 (16)1.17793 (16)0.1703 (2)0.0802 (13)
C10.16764 (13)0.99737 (13)0.4306 (2)0.0403 (9)
C20.16483 (14)0.95013 (14)0.3696 (2)0.0496 (11)
C30.12676 (15)0.92888 (15)0.2825 (2)0.0533 (11)
C40.09162 (14)0.95549 (15)0.2568 (2)0.0522 (11)
C50.09214 (14)1.00079 (15)0.3177 (2)0.0534 (11)
C60.13042 (14)1.02166 (14)0.4045 (2)0.0474 (10)
C70.21047 (13)1.02331 (14)0.5225 (2)0.0444 (10)
C80.30194 (16)1.02317 (14)0.5850 (2)0.0488 (11)
C90.26115 (15)1.00121 (17)0.6800 (2)0.0610 (11)
C100.33513 (13)1.13027 (15)0.4341 (2)0.0443 (10)
C110.37035 (14)1.16854 (14)0.3424 (2)0.0451 (10)
C120.39270 (18)1.23136 (16)0.3450 (3)0.0687 (14)
C130.4255 (2)1.26670 (18)0.2588 (3)0.0816 (16)
C140.43328 (19)1.2376 (2)0.1757 (3)0.0802 (17)
C150.38243 (17)1.14490 (17)0.2539 (3)0.0653 (14)
H20.188700.932500.387400.0600*
H2A0.3055 (19)1.0477 (17)0.366 (2)0.1000*
H30.125000.897100.241900.0640*
H50.067101.017400.301100.0640*
H60.131001.052600.445900.0570*
H70.215501.063700.541100.0530*
H9A0.273101.035000.728800.0730*
H9B0.264800.968600.714700.0730*
H120.386101.249800.402900.0820*
H130.441601.309300.258300.0980*
H140.454901.261700.118500.0960*
H150.368401.102700.252500.0780*
U11U22U33U12U13U23
Br10.0755 (3)0.1114 (4)0.0638 (2)0.0473 (3)−0.0204 (2)−0.0167 (2)
S10.0544 (5)0.0724 (6)0.0463 (4)0.0279 (5)0.0077 (4)0.0159 (4)
O10.0534 (15)0.0774 (17)0.0589 (13)0.0380 (13)−0.0050 (11)0.0014 (11)
O20.0534 (14)0.0621 (14)0.0462 (12)0.0240 (12)0.0031 (9)−0.0101 (10)
N10.0430 (14)0.0531 (16)0.0386 (12)0.0218 (13)0.0041 (11)0.0096 (11)
N20.0462 (15)0.0478 (16)0.0370 (13)0.0192 (13)0.0057 (11)0.0030 (11)
N30.095 (3)0.068 (2)0.0646 (18)0.031 (2)0.0335 (17)0.0100 (16)
C10.0415 (17)0.0418 (17)0.0388 (14)0.0217 (14)0.0059 (12)0.0077 (12)
C20.0474 (19)0.052 (2)0.0564 (17)0.0300 (16)0.0032 (14)0.0058 (14)
C30.053 (2)0.052 (2)0.0570 (18)0.0278 (17)0.0042 (15)−0.0056 (15)
C40.0463 (19)0.058 (2)0.0486 (16)0.0233 (17)0.0024 (14)0.0021 (15)
C50.0477 (19)0.056 (2)0.0630 (19)0.0309 (17)−0.0008 (15)0.0061 (16)
C60.0514 (19)0.0434 (18)0.0514 (16)0.0268 (16)0.0050 (14)0.0040 (13)
C70.0421 (18)0.0465 (18)0.0456 (15)0.0229 (15)0.0027 (13)0.0031 (13)
C80.058 (2)0.0515 (19)0.0404 (16)0.0299 (17)−0.0024 (14)−0.0005 (13)
C90.064 (2)0.076 (2)0.0430 (17)0.035 (2)−0.0016 (15)0.0114 (16)
C100.0359 (16)0.053 (2)0.0425 (16)0.0212 (15)−0.0028 (12)−0.0033 (14)
C110.0401 (17)0.0482 (19)0.0452 (16)0.0207 (15)−0.0005 (13)0.0004 (13)
C120.080 (3)0.056 (2)0.058 (2)0.025 (2)0.0008 (18)−0.0047 (17)
C130.098 (3)0.044 (2)0.078 (3)0.017 (2)0.006 (2)0.0110 (19)
C140.078 (3)0.071 (3)0.070 (3)0.021 (2)0.021 (2)0.011 (2)
C150.076 (3)0.057 (2)0.0571 (19)0.029 (2)0.0231 (17)0.0053 (17)
Br1—C41.896 (3)C5—C61.386 (4)
S1—C71.823 (3)C8—C91.503 (4)
S1—C91.801 (4)C10—C111.491 (4)
O1—C81.223 (5)C11—C121.377 (5)
O2—C101.219 (3)C11—C151.379 (5)
N1—N21.390 (3)C12—C131.394 (6)
N1—C71.471 (5)C13—C141.356 (6)
N1—C81.358 (4)C2—H20.9300
N2—C101.366 (4)C3—H30.9300
N3—C141.312 (6)C5—H50.9300
N3—C151.331 (5)C6—H60.9300
N2—H2A0.85 (3)C7—H70.9800
C1—C61.380 (5)C9—H9A0.9700
C1—C71.501 (4)C9—H9B0.9700
C1—C21.386 (4)C12—H120.9300
C2—C31.387 (4)C13—H130.9300
C3—C41.379 (5)C14—H140.9300
C4—C51.368 (4)C15—H150.9300
Br1···H5i3.1900C15···O1vi3.399 (5)
S1···C6ii3.524 (4)C1···H6ii2.9800
S1···N3iii3.003 (3)C2···H7ii2.7800
S1···C14iii3.644 (5)C3···H7ii2.9100
S1···H6ii3.0300C4···H14viii3.0000
O1···N22.757 (4)C5···H5i3.0700
O1···C103.281 (4)C5···H14viii2.9100
O1···N2iv2.914 (4)C6···H14viii3.0100
O1···C2iv3.369 (4)C6···H6ii2.9700
O1···C15iv3.399 (6)C8···H2Aiv3.00 (6)
O2···C2v3.415 (6)C10···H3iv2.9500
O2···C83.062 (4)C10···H72.9300
O2···N12.659 (3)C12···H9Bv3.0200
O2···C73.140 (4)C15···H2A2.64 (4)
O2···C3iv3.237 (6)H2···N12.7100
O1···H15iv2.5000H2···O2ii2.7500
O1···H2Aiv2.07 (5)H2A···C152.64 (4)
O2···H72.6500H2A···H152.0700
O2···H2v2.7500H2A···O1vi2.07 (3)
O2···H122.5600H2A···C8vi3.00 (4)
O2···H3iv2.4300H3···O2vi2.4300
N1···O22.659 (3)H3···C10vi2.9500
N2···O12.757 (4)H5···Br1ix3.1900
N2···C23.320 (4)H5···C5ix3.0700
N2···O1vi2.914 (4)H6···H72.3300
N3···C9vii3.262 (5)H6···S1v3.0300
N3···S1vii3.003 (3)H6···C1v2.9800
N1···H22.7100H6···C6v2.9700
N2···H152.5400H7···O22.6500
N3···H9Bvii2.8500H7···C102.9300
C2···N23.320 (4)H7···H62.3300
C2···O2ii3.415 (4)H7···C2v2.7800
C2···O1vi3.369 (5)H7···C3v2.9100
C3···O2vi3.237 (5)H9B···C12ii3.0200
C6···S1v3.524 (3)H9B···N3iii2.8500
C7···O23.140 (4)H12···O22.5600
C8···O23.062 (4)H14···C4viii3.0000
C9···N3iii3.262 (5)H14···C5viii2.9100
C10···O13.281 (4)H14···C6viii3.0100
C14···S1vii3.644 (4)H15···N22.5400
C14···C15viii3.507 (7)H15···H2A2.0700
C15···C14viii3.507 (7)H15···O1vi2.5000
C7—S1—C990.87 (15)C10—C11—C15123.9 (3)
N2—N1—C7117.0 (2)C11—C12—C13118.5 (3)
N2—N1—C8119.5 (3)C12—C13—C14118.6 (4)
C7—N1—C8117.6 (2)N3—C14—C13124.7 (4)
N1—N2—C10117.8 (2)N3—C15—C11124.9 (3)
C14—N3—C15116.1 (3)C1—C2—H2120.00
C10—N2—H2A129 (2)C3—C2—H2120.00
N1—N2—H2A114 (2)C2—C3—H3120.00
C2—C1—C7122.0 (3)C4—C3—H3120.00
C2—C1—C6118.6 (3)C4—C5—H5120.00
C6—C1—C7119.4 (3)C6—C5—H5120.00
C1—C2—C3120.8 (3)C1—C6—H6119.00
C2—C3—C4119.1 (3)C5—C6—H6119.00
C3—C4—C5121.1 (3)S1—C7—H7109.00
Br1—C4—C3119.3 (2)N1—C7—H7109.00
Br1—C4—C5119.6 (3)C1—C7—H7109.00
C4—C5—C6119.2 (3)S1—C9—H9A110.00
C1—C6—C5121.2 (3)S1—C9—H9B110.00
S1—C7—C1112.7 (2)C8—C9—H9A110.00
S1—C7—N1103.1 (2)C8—C9—H9B110.00
N1—C7—C1112.9 (2)H9A—C9—H9B109.00
N1—C8—C9110.8 (3)C11—C12—H12121.00
O1—C8—C9125.3 (3)C13—C12—H12121.00
O1—C8—N1123.9 (3)C12—C13—H13121.00
S1—C9—C8107.2 (2)C14—C13—H13121.00
N2—C10—C11115.8 (2)N3—C14—H14118.00
O2—C10—N2121.6 (3)C13—C14—H14118.00
O2—C10—C11122.7 (3)N3—C15—H15118.00
C12—C11—C15117.2 (3)C11—C15—H15118.00
C10—C11—C12118.9 (3)
C7—S1—C9—C8−26.5 (3)C7—C1—C2—C3−177.2 (3)
C9—S1—C7—N129.0 (2)C6—C1—C7—S1104.9 (3)
C9—S1—C7—C1151.0 (3)C6—C1—C7—N1−138.8 (3)
C7—N1—N2—C1078.1 (4)C1—C2—C3—C40.2 (5)
C8—N1—C7—S1−26.4 (3)C2—C3—C4—C5−2.3 (5)
N2—N1—C7—C158.8 (3)C2—C3—C4—Br1176.3 (2)
N2—N1—C7—S1−179.29 (19)Br1—C4—C5—C6−176.3 (2)
N2—N1—C8—O1−19.3 (4)C3—C4—C5—C62.4 (5)
C7—N1—C8—O1−171.5 (3)C4—C5—C6—C1−0.3 (5)
N2—N1—C8—C9159.6 (3)O1—C8—C9—S1−165.2 (3)
C7—N1—C8—C97.4 (4)N1—C8—C9—S116.0 (3)
C8—N1—C7—C1−148.3 (3)N2—C10—C11—C12169.1 (4)
C8—N1—N2—C10−74.3 (4)O2—C10—C11—C12−9.9 (6)
N1—N2—C10—O2−0.7 (5)O2—C10—C11—C15169.9 (4)
N1—N2—C10—C11−179.7 (3)N2—C10—C11—C15−11.1 (6)
C14—N3—C15—C111.9 (7)C15—C11—C12—C130.3 (6)
C15—N3—C14—C13−0.6 (8)C10—C11—C15—N3178.5 (4)
C6—C1—C2—C31.8 (5)C10—C11—C12—C13−179.9 (4)
C2—C1—C6—C5−1.7 (5)C12—C11—C15—N3−1.8 (7)
C2—C1—C7—N140.2 (4)C11—C12—C13—C140.8 (7)
C7—C1—C6—C5177.3 (3)C12—C13—C14—N3−0.7 (8)
C2—C1—C7—S1−76.2 (3)
Cg3 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1vi0.85 (3)2.07 (3)2.914 (4)172 (4)
C3—H3···O2vi0.932.433.237 (5)146
C15—H15···N20.932.542.864 (5)101
C15—H15···O1vi0.932.503.399 (5)162
C14—H14···Cg3i0.932.793.692 (4)164
Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O1i0.85 (3)2.07 (3)2.914 (4)172 (4)
C3—H3⋯O2i0.932.433.237 (5)146
C15—H15⋯N20.932.542.864 (5)101
C15—H15⋯O1i0.932.503.399 (5)162
C14—H14⋯Cg3ii0.932.793.692 (4)164

Symmetry codes: (i) ; (ii) .

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5.  Antiviral effect of nicotinamide on enterovirus-infected human islets in vitro: effect on virus replication and chemokine secretion.

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1.  2-(4-Bromo-phen-yl)-3-(4-hy-droxy-phen-yl)-1,3-thia-zolidin-4-one.

Authors:  Jasmine P Vennila; D John Thiruvadigal; Helen P Kavitha; G Chakkaravarthi; V Manivannan
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2.  5-Chloro-N-{4-oxo-2-[4-(trifluoro-meth-yl)phen-yl]-1,3-thia-zolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide.

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  2 in total

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