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

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

aChemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 4 July 2009; accepted 5 July 2009; online 11 July 2009)

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[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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O4S

  • Mr = 374.45

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.932, Tmax = 0.970

  • 12384 measured reflections

  • 4124 independent reflections

  • 3351 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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).

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C19H22N2O4S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
5-[3-(2,5-Dimethoxyphenyl)prop-2-enylidene]-1,3-diethyl-2- thioxohexahydropyrimidine-4,6-dione top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
4124 independent reflections
Radiation source: fine-focus sealed tube3351 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.932, Tmax = 0.970k = 2019
12384 measured reflectionsl = 1515
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.02 w = 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
Crystal data top
C19H22N2O4SV = 1816.88 (6) Å3
Mr = 374.45Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0519 (2) ŵ = 0.21 mm1
b = 15.5942 (3) ÅT = 140 K
c = 11.5920 (2) Å0.35 × 0.25 × 0.15 mm
β = 90.813 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4124 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3351 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.970Rint = 0.021
12384 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.02Δρmax = 0.38 e Å3
4124 reflectionsΔρmin = 0.31 e Å3
239 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H8A0.74660.01210.54580.062*
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) top
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, º) top
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—O1172.42 (15)C4—N2—C7—C888.82 (18)
C5—N1—C1—O16.6 (2)C3—N2—C7—C886.77 (18)
C4—N1—C1—C28.2 (2)C1—C2—C9—C102.7 (3)
C5—N1—C1—C2172.73 (13)C3—C2—C9—C10176.85 (15)
O1—C1—C2—C911.3 (3)C2—C9—C10—C11179.44 (16)
N1—C1—C2—C9167.98 (14)C9—C10—C11—C12179.07 (15)
O1—C1—C2—C3169.12 (15)C10—C11—C12—C170.0 (3)
N1—C1—C2—C311.6 (2)C10—C11—C12—C13179.19 (15)
C4—N2—C3—O2173.69 (15)C18—O3—C13—C140.2 (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—C2177.84 (13)C11—C12—C13—O30.1 (2)
C9—C2—C3—O25.6 (2)C17—C12—C13—C140.8 (2)
C1—C2—C3—O2174.83 (15)C11—C12—C13—C14179.99 (14)
C9—C2—C3—N2174.93 (14)O3—C13—C14—C15179.33 (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—N2176.56 (13)C19—O4—C16—C173.6 (3)
C1—N1—C4—S1177.59 (12)C19—O4—C16—C15176.54 (16)
C5—N1—C4—S13.42 (19)C14—C15—C16—O4178.46 (15)
C3—N2—C4—N110.5 (2)C14—C15—C16—C171.4 (2)
C7—N2—C4—N1174.31 (13)O4—C16—C17—C12178.52 (15)
C3—N2—C4—S1169.52 (12)C15—C16—C17—C121.3 (2)
C7—N2—C4—S15.67 (19)C13—C12—C17—C160.2 (2)
C4—N1—C5—C682.80 (17)C11—C12—C17—C16178.91 (15)
C1—N1—C5—C696.28 (16)

Experimental details

Crystal data
Chemical formulaC19H22N2O4S
Mr374.45
Crystal system, space groupMonoclinic, P21/n
Temperature (K)140
a, b, c (Å)10.0519 (2), 15.5942 (3), 11.5920 (2)
β (°) 90.813 (1)
V3)1816.88 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.932, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
12384, 4124, 3351
Rint0.021
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.119, 1.02
No. of reflections4124
No. of parameters239
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.31

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationAdamson, 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.  Web of Science CSD CrossRef Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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