Literature DB >> 22606091

(Z)-3-p-Tolyl-2-(p-tolyl-imino)-1,3-thia-zolidin-4-one.

Hatem A Abdel-Aziz, Hazem A Ghabbour, Tze Shyang Chia, Hoong-Kun Fun.   

Abstract

In the title compound, C(17)H(16)N(2)OS, the central thia-zolidin-4-one ring forms dihedral angles of 66.49 (9) and 79.45 (6)° with the two methyl-substituted benzene rings. In the crystal, mol-ecules are stacked in columns along the b axis through C-H⋯π inter-actions. The H atoms of one of the methyl groups are disordered over two orientations with equal site occupancies.

Entities:  

Year:  2012        PMID： 22606091      PMCID： PMC3344088          DOI： 10.1107/S160053681201149X

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


Related literature

For the chemistry of thia­zolidin-4-one and its experimental preparation, see: Abdel-Aziz et al. (2010 ▶). For a related structure, see: Zeller et al. (2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16N2OS M = 296.38 Monoclinic, a = 14.1321 (4) Å b = 5.8524 (2) Å c = 19.0076 (6) Å β = 100.307 (2)° V = 1546.69 (8) Å3 Z = 4 Cu Kα radiation μ = 1.85 mm−1 T = 296 K 0.98 × 0.21 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.264, T max = 0.897 10830 measured reflections 2849 independent reflections 2293 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.135 S = 1.07 2849 reflections 194 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.35 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681201149X/is5090sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201149X/is5090Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681201149X/is5090Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H16N2OSF(000) = 624
Mr = 296.38Dx = 1.273 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 1135 reflections
a = 14.1321 (4) Åθ = 4.7–69.2°
b = 5.8524 (2) ŵ = 1.85 mm−1
c = 19.0076 (6) ÅT = 296 K
β = 100.307 (2)°Needle, colourless
V = 1546.69 (8) Å30.98 × 0.21 × 0.06 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer2849 independent reflections
Radiation source: fine-focus sealed tube2293 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 69.8°, θmin = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→17
Tmin = 0.264, Tmax = 0.897k = −5→6
10830 measured reflectionsl = −23→22
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.135w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2896P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2849 reflectionsΔρmax = 0.35 e Å−3
194 parametersΔρmin = −0.35 e Å−3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0124 (10)
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.
xyzUiso*/UeqOcc. (<1)
S10.86258 (4)−0.00010 (12)0.47164 (3)0.0765 (3)
N10.84789 (10)−0.0771 (3)0.32906 (8)0.0522 (4)
N20.73053 (10)0.1441 (3)0.36745 (8)0.0523 (4)
O10.63384 (14)0.3619 (4)0.42357 (10)0.1118 (8)
C10.7698 (2)0.1807 (7)0.49367 (13)0.1031 (11)
H1A0.73490.10190.52600.124*
H1B0.79770.31850.51710.124*
C20.70278 (16)0.2406 (5)0.42561 (12)0.0757 (7)
C30.81438 (12)0.0103 (3)0.37930 (10)0.0496 (4)
C40.93412 (12)−0.2091 (3)0.34399 (9)0.0479 (4)
C50.93843 (14)−0.4167 (3)0.37968 (12)0.0584 (5)
H5A0.8857−0.46780.39830.070*
C61.02137 (14)−0.5478 (3)0.38750 (12)0.0591 (5)
H6A1.0236−0.68640.41170.071*
C71.10064 (13)−0.4772 (3)0.36010 (11)0.0515 (5)
C81.09587 (13)−0.2684 (3)0.32587 (10)0.0530 (4)
H8A1.1492−0.21550.30830.064*
C91.01362 (13)−0.1362 (3)0.31707 (10)0.0514 (4)
H9A1.01170.00250.29290.062*
C100.67884 (12)0.1860 (3)0.29574 (10)0.0475 (4)
C110.61531 (13)0.0238 (3)0.26253 (11)0.0535 (5)
H11A0.6064−0.11240.28570.064*
C120.56500 (14)0.0659 (4)0.19452 (11)0.0584 (5)
H12A0.5222−0.04340.17210.070*
C130.57711 (13)0.2673 (4)0.15916 (10)0.0561 (5)
C140.64077 (14)0.4275 (4)0.19421 (11)0.0592 (5)
H14A0.64950.56440.17140.071*
C150.69157 (13)0.3888 (3)0.26226 (11)0.0563 (5)
H15A0.73380.49860.28510.068*
C160.52221 (18)0.3121 (5)0.08465 (13)0.0838 (8)
H16A0.45670.26390.08160.126*
H16B0.55120.22840.05060.126*
H16C0.52390.47250.07440.126*
C171.18878 (15)−0.6264 (4)0.36447 (13)0.0688 (6)
H17A1.2442−0.54490.38850.103*0.50
H17B1.1977−0.66590.31710.103*0.50
H17C1.1804−0.76310.39060.103*0.50
H17D1.2256−0.62030.41200.103*0.50
H17E1.2273−0.57240.33110.103*0.50
H17F1.1694−0.78110.35300.103*0.50
U11U22U33U12U13U23
S10.0617 (4)0.1143 (5)0.0480 (4)0.0285 (3)−0.0047 (2)0.0048 (3)
N10.0461 (8)0.0559 (9)0.0516 (9)0.0101 (7)0.0007 (6)0.0030 (7)
N20.0441 (8)0.0635 (10)0.0461 (8)0.0110 (7)−0.0010 (6)−0.0011 (7)
O10.0957 (13)0.165 (2)0.0691 (11)0.0751 (14)−0.0007 (9)−0.0207 (12)
C10.0900 (18)0.159 (3)0.0529 (13)0.0537 (19)−0.0063 (12)−0.0151 (16)
C20.0616 (12)0.1040 (18)0.0575 (12)0.0279 (13)−0.0003 (10)−0.0105 (12)
C30.0412 (9)0.0541 (10)0.0502 (10)0.0044 (7)−0.0009 (8)0.0044 (8)
C40.0464 (9)0.0470 (9)0.0472 (9)0.0061 (7)0.0003 (7)−0.0010 (7)
C50.0487 (10)0.0565 (11)0.0701 (13)0.0018 (8)0.0110 (9)0.0098 (9)
C60.0561 (11)0.0474 (11)0.0718 (13)0.0066 (8)0.0062 (9)0.0119 (9)
C70.0491 (10)0.0494 (10)0.0530 (10)0.0064 (7)0.0013 (8)−0.0053 (8)
C80.0492 (9)0.0546 (11)0.0550 (10)0.0001 (8)0.0092 (8)−0.0027 (8)
C90.0559 (10)0.0455 (10)0.0516 (10)0.0038 (8)0.0061 (8)0.0039 (7)
C100.0377 (8)0.0539 (10)0.0477 (9)0.0077 (7)−0.0010 (7)−0.0008 (7)
C110.0495 (10)0.0507 (10)0.0573 (11)−0.0010 (7)0.0017 (8)0.0047 (8)
C120.0487 (10)0.0642 (12)0.0575 (11)−0.0066 (8)−0.0030 (8)−0.0023 (9)
C130.0456 (9)0.0677 (12)0.0524 (11)0.0038 (8)0.0017 (8)0.0036 (9)
C140.0572 (11)0.0557 (11)0.0625 (12)0.0008 (9)0.0053 (9)0.0117 (9)
C150.0492 (10)0.0516 (11)0.0639 (12)−0.0032 (8)−0.0011 (8)−0.0037 (9)
C160.0790 (15)0.108 (2)0.0574 (13)−0.0013 (14)−0.0077 (11)0.0135 (13)
C170.0595 (11)0.0652 (13)0.0810 (15)0.0165 (10)0.0111 (10)0.0006 (11)
S1—C31.7664 (19)C9—H9A0.9300
S1—C11.792 (3)C10—C151.374 (3)
N1—C31.249 (2)C10—C111.379 (3)
N1—C41.428 (2)C11—C121.381 (3)
N2—C21.360 (3)C11—H11A0.9300
N2—C31.405 (2)C12—C131.383 (3)
N2—C101.448 (2)C12—H12A0.9300
O1—C21.200 (3)C13—C141.385 (3)
C1—C21.502 (3)C13—C161.511 (3)
C1—H1A0.9700C14—C151.381 (3)
C1—H1B0.9700C14—H14A0.9300
C4—C91.383 (3)C15—H15A0.9300
C4—C51.387 (3)C16—H16A0.9600
C5—C61.387 (3)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C6—C71.381 (3)C17—H17A0.9600
C6—H6A0.9300C17—H17B0.9600
C7—C81.380 (3)C17—H17C0.9600
C7—C171.511 (3)C17—H17D0.9600
C8—C91.381 (3)C17—H17E0.9600
C8—H8A0.9300C17—H17F0.9600
C3—S1—C192.50 (10)C4—C9—H9A119.9
C3—N1—C4119.78 (15)C15—C10—C11120.72 (17)
C2—N2—C3117.32 (15)C15—C10—N2119.79 (16)
C2—N2—C10121.64 (15)C11—C10—N2119.46 (17)
C3—N2—C10120.97 (15)C10—C11—C12119.31 (18)
C2—C1—S1108.16 (17)C10—C11—H11A120.3
C2—C1—H1A110.1C12—C11—H11A120.3
S1—C1—H1A110.1C11—C12—C13121.27 (18)
C2—C1—H1B110.1C11—C12—H12A119.4
S1—C1—H1B110.1C13—C12—H12A119.4
H1A—C1—H1B108.4C12—C13—C14118.00 (17)
O1—C2—N2124.7 (2)C12—C13—C16121.1 (2)
O1—C2—C1123.3 (2)C14—C13—C16120.9 (2)
N2—C2—C1111.96 (18)C15—C14—C13121.58 (19)
N1—C3—N2122.02 (16)C15—C14—H14A119.2
N1—C3—S1127.89 (14)C13—C14—H14A119.2
N2—C3—S1110.05 (13)C10—C15—C14119.10 (17)
C9—C4—C5118.94 (17)C10—C15—H15A120.4
C9—C4—N1118.71 (16)C14—C15—H15A120.4
C5—C4—N1122.16 (17)C13—C16—H16A109.5
C6—C5—C4119.96 (19)C13—C16—H16B109.5
C6—C5—H5A120.0H16A—C16—H16B109.5
C4—C5—H5A120.0C13—C16—H16C109.5
C7—C6—C5121.40 (18)H16A—C16—H16C109.5
C7—C6—H6A119.3H16B—C16—H16C109.5
C5—C6—H6A119.3C7—C17—H17A109.5
C8—C7—C6117.93 (17)C7—C17—H17B109.5
C8—C7—C17120.51 (19)C7—C17—H17C109.5
C6—C7—C17121.51 (19)C7—C17—H17D109.5
C7—C8—C9121.47 (18)C7—C17—H17E109.5
C7—C8—H8A119.3H17D—C17—H17E109.5
C9—C8—H8A119.3C7—C17—H17F109.5
C8—C9—C4120.27 (18)H17D—C17—H17F109.5
C8—C9—H9A119.9H17E—C17—H17F109.5
C3—S1—C1—C20.6 (3)C5—C6—C7—C17−176.1 (2)
C3—N2—C2—O1178.7 (3)C6—C7—C8—C9−2.0 (3)
C10—N2—C2—O11.7 (4)C17—C7—C8—C9175.62 (19)
C3—N2—C2—C1−0.4 (3)C7—C8—C9—C41.3 (3)
C10—N2—C2—C1−177.4 (2)C5—C4—C9—C8−0.1 (3)
S1—C1—C2—O1−179.3 (3)N1—C4—C9—C8−175.14 (17)
S1—C1—C2—N2−0.2 (4)C2—N2—C10—C1577.3 (3)
C4—N1—C3—N2179.14 (16)C3—N2—C10—C15−99.6 (2)
C4—N1—C3—S11.9 (3)C2—N2—C10—C11−101.0 (2)
C2—N2—C3—N1−176.8 (2)C3—N2—C10—C1182.1 (2)
C10—N2—C3—N10.2 (3)C15—C10—C11—C120.7 (3)
C2—N2—C3—S10.9 (2)N2—C10—C11—C12179.01 (17)
C10—N2—C3—S1177.91 (14)C10—C11—C12—C130.0 (3)
C1—S1—C3—N1176.7 (2)C11—C12—C13—C14−0.5 (3)
C1—S1—C3—N2−0.82 (19)C11—C12—C13—C16179.7 (2)
C3—N1—C4—C9−118.4 (2)C12—C13—C14—C150.4 (3)
C3—N1—C4—C566.7 (3)C16—C13—C14—C15−179.9 (2)
C9—C4—C5—C6−0.4 (3)C11—C10—C15—C14−0.9 (3)
N1—C4—C5—C6174.46 (19)N2—C10—C15—C14−179.14 (17)
C4—C5—C6—C7−0.3 (3)C13—C14—C15—C100.3 (3)
C5—C6—C7—C81.5 (3)
D—H···AD—HH···AD···AD—H···A
C5—H5A···Cg1i0.933.003.788 (2)144
C9—H9A···Cg2ii0.932.873.607 (2)138
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/N2/C1–C3 and C4–C9 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5—H5A⋯Cg1i0.933.003.788 (2)144
C9—H9A⋯Cg2ii0.932.873.607 (2)138

Symmetry codes: (i) ; (ii) .

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