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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1820.
Published online 2009 July 11. doi:  10.1107/S1600536809026099
PMCID: PMC2977468

5-[3-(2,5-Dimethoxy­phen­yl)prop-2-enyl­idene]-1,3-diethyl-2-thioxohexa­hydro­pyrimidine-4,6-dione

Abstract

1,3-Diethyl-2-thio­barbituric acid reacts with 2,5-dimethoxy­benzaldehyde to form the title Knoevenagel product, C19H22N2O4S. In the compound, the two six-membered rings at either end of the three-membered –CHCHCH– chain are nearly coplanar with this fragment (r.m.s. deviation of the two six-membered rings and the three chain atoms = 0.08 Å).

Related literature

For the reaction of 1,3-diethyl-2-thio­barbituric acid with aromatic aldehydes to form the Knoevenagel and Michael products, see: Adamson et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1820-scheme1.jpg

Experimental

Crystal data

  • C19H22N2O4S
  • M r = 374.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1820-efi1.jpg
  • a = 10.0519 (2) Å
  • b = 15.5942 (3) Å
  • c = 11.5920 (2) Å
  • β = 90.813 (1)°
  • V = 1816.88 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 140 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.932, T max = 0.970
  • 12384 measured reflections
  • 4124 independent reflections
  • 3351 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.119
  • S = 1.02
  • 4124 reflections
  • 239 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026099/xu2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026099/xu2548Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

1,3-Diethyl-2-thiobarbituric acid (1 g, 0.005 mol) and 2,5-dimethoxybenzaldehyde (0.83 g, 0.005 mol) were heated in ethanol (15 ml) for 3 h; several drops of pyridine were added. The progress of reaction was monitored by TLC. The solid that seperated from the cool mixture was collected and recrystallized from a methanol-chloroform mixture in 50% yield; m.p. 454 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) fixed at 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C19H22N2O4S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C19H22N2O4SF(000) = 792
Mr = 374.45Dx = 1.369 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4985 reflections
a = 10.0519 (2) Åθ = 2.2–28.3°
b = 15.5942 (3) ŵ = 0.21 mm1
c = 11.5920 (2) ÅT = 140 K
β = 90.813 (1)°Irregular, gold–green
V = 1816.88 (6) Å30.35 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4124 independent reflections
Radiation source: fine-focus sealed tube3351 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→13
Tmin = 0.932, Tmax = 0.970k = −20→19
12384 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0635P)2 + 0.8319P] where P = (Fo2 + 2Fc2)/3
4124 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.31 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.45514 (5)0.17006 (3)0.48043 (5)0.04028 (15)
O10.65557 (12)0.44794 (7)0.58487 (12)0.0369 (3)
O20.88016 (13)0.19441 (7)0.68934 (12)0.0368 (3)
O31.30863 (11)0.51465 (7)0.76778 (11)0.0323 (3)
O41.02427 (13)0.79694 (8)0.61792 (13)0.0412 (3)
N10.57177 (12)0.31723 (8)0.53660 (11)0.0229 (3)
N20.67570 (13)0.19089 (8)0.60462 (11)0.0238 (3)
C10.67099 (15)0.37060 (9)0.58438 (13)0.0242 (3)
C20.78972 (15)0.32772 (9)0.63022 (13)0.0229 (3)
C30.78870 (16)0.23434 (9)0.64445 (13)0.0250 (3)
C40.57229 (15)0.22878 (10)0.54306 (14)0.0248 (3)
C50.45950 (15)0.36105 (10)0.47751 (14)0.0265 (3)
H5A0.43190.32740.40880.032*
H5B0.48900.41820.45080.032*
C60.34165 (17)0.37168 (11)0.55619 (16)0.0341 (4)
H6A0.27050.40260.51520.051*
H6B0.36900.40420.62490.051*
H6C0.30920.31510.57940.051*
C70.67507 (17)0.09673 (10)0.62395 (15)0.0303 (4)
H7A0.58200.07660.63010.036*
H7B0.72160.08370.69770.036*
C80.7422 (2)0.04915 (11)0.52713 (19)0.0415 (4)
H8A0.7466−0.01210.54580.062*
H8B0.83250.07150.51750.062*
H8C0.69110.05720.45530.062*
C90.90368 (16)0.36954 (10)0.66047 (13)0.0250 (3)
H90.97180.33420.69230.030*
C100.93689 (16)0.45823 (10)0.65184 (13)0.0254 (3)
H100.87410.49810.62160.031*
C111.05873 (16)0.48485 (10)0.68724 (14)0.0258 (3)
H111.11700.44150.71550.031*
C121.11166 (16)0.57152 (10)0.68749 (13)0.0246 (3)
C131.24183 (16)0.58518 (10)0.72991 (13)0.0252 (3)
C141.29543 (16)0.66804 (10)0.73119 (14)0.0275 (3)
H141.38360.67740.75890.033*
C151.21964 (17)0.73610 (10)0.69203 (15)0.0294 (4)
H151.25660.79220.69260.035*
C161.08972 (17)0.72399 (10)0.65159 (14)0.0288 (3)
C171.03685 (16)0.64216 (10)0.64830 (14)0.0262 (3)
H170.94900.63360.61920.031*
C181.44150 (17)0.52479 (11)0.81125 (16)0.0328 (4)
H18A1.47630.46900.83610.049*
H18B1.44150.56430.87700.049*
H18C1.49780.54810.75040.049*
C190.89413 (19)0.78713 (12)0.56997 (19)0.0415 (4)
H19A0.85760.84360.55030.062*
H19B0.83680.75920.62640.062*
H19C0.89830.75180.50020.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0323 (2)0.0271 (2)0.0610 (3)−0.00414 (17)−0.0128 (2)−0.0060 (2)
O10.0306 (6)0.0158 (5)0.0640 (8)0.0014 (5)−0.0106 (6)0.0012 (5)
O20.0364 (7)0.0202 (5)0.0534 (8)0.0041 (5)−0.0167 (6)0.0012 (5)
O30.0260 (6)0.0242 (6)0.0465 (7)−0.0029 (5)−0.0060 (5)−0.0024 (5)
O40.0380 (7)0.0223 (6)0.0629 (9)−0.0045 (5)−0.0123 (6)0.0066 (6)
N10.0214 (6)0.0185 (6)0.0287 (6)−0.0005 (5)−0.0028 (5)0.0002 (5)
N20.0250 (7)0.0158 (6)0.0307 (7)−0.0010 (5)−0.0004 (5)0.0005 (5)
C10.0230 (8)0.0185 (7)0.0312 (8)−0.0009 (6)−0.0002 (6)0.0016 (6)
C20.0249 (8)0.0167 (7)0.0270 (7)0.0005 (6)−0.0025 (6)−0.0014 (5)
C30.0274 (8)0.0186 (7)0.0288 (8)0.0006 (6)−0.0017 (6)−0.0006 (6)
C40.0244 (8)0.0200 (7)0.0300 (8)−0.0015 (6)0.0008 (6)−0.0011 (6)
C50.0242 (8)0.0241 (7)0.0309 (8)0.0020 (6)−0.0053 (6)0.0034 (6)
C60.0285 (9)0.0318 (9)0.0419 (10)0.0039 (7)−0.0002 (7)−0.0008 (7)
C70.0322 (9)0.0160 (7)0.0427 (9)−0.0018 (6)0.0037 (7)0.0029 (6)
C80.0402 (10)0.0252 (8)0.0594 (12)0.0003 (7)0.0068 (9)−0.0097 (8)
C90.0255 (8)0.0202 (7)0.0293 (8)0.0011 (6)−0.0020 (6)−0.0024 (6)
C100.0262 (8)0.0202 (7)0.0299 (8)−0.0005 (6)−0.0010 (6)−0.0021 (6)
C110.0270 (8)0.0207 (7)0.0298 (8)−0.0001 (6)0.0009 (6)−0.0033 (6)
C120.0260 (8)0.0220 (7)0.0260 (7)−0.0039 (6)0.0029 (6)−0.0045 (6)
C130.0254 (8)0.0228 (7)0.0275 (8)−0.0009 (6)0.0030 (6)−0.0036 (6)
C140.0254 (8)0.0271 (8)0.0300 (8)−0.0066 (6)0.0018 (6)−0.0054 (6)
C150.0313 (9)0.0226 (7)0.0345 (8)−0.0091 (6)0.0034 (7)−0.0039 (6)
C160.0328 (9)0.0224 (7)0.0314 (8)−0.0021 (6)0.0013 (7)0.0000 (6)
C170.0251 (8)0.0230 (7)0.0305 (8)−0.0038 (6)−0.0003 (6)−0.0008 (6)
C180.0264 (8)0.0320 (9)0.0398 (9)−0.0031 (7)−0.0051 (7)0.0009 (7)
C190.0365 (10)0.0292 (9)0.0587 (12)−0.0017 (7)−0.0097 (9)0.0094 (8)

Geometric parameters (Å, °)

S1—C41.6516 (16)C8—H8A0.9800
O1—C11.2160 (19)C8—H8B0.9800
O2—C31.2207 (19)C8—H8C0.9800
O3—C131.3582 (19)C9—C101.427 (2)
O3—C181.430 (2)C9—H90.9500
O4—C161.368 (2)C10—C111.351 (2)
O4—C191.422 (2)C10—H100.9500
N1—C41.3815 (19)C11—C121.453 (2)
N1—C11.4065 (19)C11—H110.9500
N1—C51.4791 (19)C12—C171.405 (2)
N2—C41.385 (2)C12—C131.407 (2)
N2—C31.396 (2)C13—C141.400 (2)
N2—C71.4852 (19)C14—C151.379 (2)
C1—C21.461 (2)C14—H140.9500
C2—C91.360 (2)C15—C161.394 (2)
C2—C31.465 (2)C15—H150.9500
C5—C61.514 (2)C16—C171.383 (2)
C5—H5A0.9900C17—H170.9500
C5—H5B0.9900C18—H18A0.9800
C6—H6A0.9800C18—H18B0.9800
C6—H6B0.9800C18—H18C0.9800
C6—H6C0.9800C19—H19A0.9800
C7—C81.512 (2)C19—H19B0.9800
C7—H7A0.9900C19—H19C0.9800
C7—H7B0.9900
C13—O3—C18118.65 (12)H8A—C8—H8C109.5
C16—O4—C19117.25 (14)H8B—C8—H8C109.5
C4—N1—C1124.56 (13)C2—C9—C10130.09 (15)
C4—N1—C5119.26 (13)C2—C9—H9115.0
C1—N1—C5116.18 (12)C10—C9—H9115.0
C4—N2—C3124.38 (13)C11—C10—C9119.24 (15)
C4—N2—C7119.65 (13)C11—C10—H10120.4
C3—N2—C7115.81 (13)C9—C10—H10120.4
O1—C1—N1119.92 (14)C10—C11—C12128.08 (15)
O1—C1—C2123.75 (14)C10—C11—H11116.0
N1—C1—C2116.32 (13)C12—C11—H11116.0
C9—C2—C1123.71 (14)C17—C12—C13119.00 (14)
C9—C2—C3117.04 (14)C17—C12—C11122.30 (15)
C1—C2—C3119.24 (13)C13—C12—C11118.70 (14)
O2—C3—N2119.86 (14)O3—C13—C14123.75 (15)
O2—C3—C2123.26 (14)O3—C13—C12116.31 (13)
N2—C3—C2116.89 (13)C14—C13—C12119.94 (15)
N1—C4—N2117.14 (13)C15—C14—C13119.73 (15)
N1—C4—S1121.84 (12)C15—C14—H14120.1
N2—C4—S1121.01 (11)C13—C14—H14120.1
N1—C5—C6111.71 (13)C14—C15—C16121.12 (14)
N1—C5—H5A109.3C14—C15—H15119.4
C6—C5—H5A109.3C16—C15—H15119.4
N1—C5—H5B109.3O4—C16—C17125.20 (16)
C6—C5—H5B109.3O4—C16—C15115.32 (14)
H5A—C5—H5B107.9C17—C16—C15119.48 (15)
C5—C6—H6A109.5C16—C17—C12120.71 (15)
C5—C6—H6B109.5C16—C17—H17119.6
H6A—C6—H6B109.5C12—C17—H17119.6
C5—C6—H6C109.5O3—C18—H18A109.5
H6A—C6—H6C109.5O3—C18—H18B109.5
H6B—C6—H6C109.5H18A—C18—H18B109.5
N2—C7—C8111.72 (14)O3—C18—H18C109.5
N2—C7—H7A109.3H18A—C18—H18C109.5
C8—C7—H7A109.3H18B—C18—H18C109.5
N2—C7—H7B109.3O4—C19—H19A109.5
C8—C7—H7B109.3O4—C19—H19B109.5
H7A—C7—H7B107.9H19A—C19—H19B109.5
C7—C8—H8A109.5O4—C19—H19C109.5
C7—C8—H8B109.5H19A—C19—H19C109.5
H8A—C8—H8B109.5H19B—C19—H19C109.5
C7—C8—H8C109.5
C4—N1—C1—O1−172.42 (15)C4—N2—C7—C888.82 (18)
C5—N1—C1—O16.6 (2)C3—N2—C7—C8−86.77 (18)
C4—N1—C1—C28.2 (2)C1—C2—C9—C10−2.7 (3)
C5—N1—C1—C2−172.73 (13)C3—C2—C9—C10176.85 (15)
O1—C1—C2—C9−11.3 (3)C2—C9—C10—C11−179.44 (16)
N1—C1—C2—C9167.98 (14)C9—C10—C11—C12−179.07 (15)
O1—C1—C2—C3169.12 (15)C10—C11—C12—C170.0 (3)
N1—C1—C2—C3−11.6 (2)C10—C11—C12—C13179.19 (15)
C4—N2—C3—O2−173.69 (15)C18—O3—C13—C14−0.2 (2)
C7—N2—C3—O21.7 (2)C18—O3—C13—C12179.70 (14)
C4—N2—C3—C26.8 (2)C17—C12—C13—O3179.26 (13)
C7—N2—C3—C2−177.84 (13)C11—C12—C13—O30.1 (2)
C9—C2—C3—O25.6 (2)C17—C12—C13—C14−0.8 (2)
C1—C2—C3—O2−174.83 (15)C11—C12—C13—C14−179.99 (14)
C9—C2—C3—N2−174.93 (14)O3—C13—C14—C15−179.33 (14)
C1—C2—C3—N24.7 (2)C12—C13—C14—C150.7 (2)
C1—N1—C4—N22.4 (2)C13—C14—C15—C160.4 (2)
C5—N1—C4—N2−176.56 (13)C19—O4—C16—C17−3.6 (3)
C1—N1—C4—S1−177.59 (12)C19—O4—C16—C15176.54 (16)
C5—N1—C4—S13.42 (19)C14—C15—C16—O4178.46 (15)
C3—N2—C4—N1−10.5 (2)C14—C15—C16—C17−1.4 (2)
C7—N2—C4—N1174.31 (13)O4—C16—C17—C12−178.52 (15)
C3—N2—C4—S1169.52 (12)C15—C16—C17—C121.3 (2)
C7—N2—C4—S1−5.67 (19)C13—C12—C17—C16−0.2 (2)
C4—N1—C5—C682.80 (17)C11—C12—C17—C16178.91 (15)
C1—N1—C5—C6−96.28 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2548).

References

  • Adamson, J., Coe, B. J., Grassam, H. L., Jeffery, J. C., Coles, S. J. & Hursthouse, M. B. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2483–2488.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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