organic compounds
1,3-Diethyl-2-sulfanylidene-5-(2,4,5-trimethoxybenzylidene)-1,3-diazinane-4,6-dione
aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
*Correspondence e-mail: aasiri2@kau.edu.sa, rehman_pcsir@yahoo.com
The title compound, C18H22N2O5S, is largely planar, with an r.m.s. deviation of 0.0546 (1) Å of atoms from the mean plane through all non-H atoms except for the methyl groups. The benzene and pyrimidinedione rings are inclined to one another at a dihedral angle of 1.41 (7)°. In the crystal, weak C—H⋯O interactions connect the molecules into chains propagating along the b-axis direction.
Related literature
For the synthesis of the title compound, see: Asiri et al. (2004). For a related structure, see: Asiri et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).
Supporting information
https://doi.org/10.1107/S1600536812049707/sj5286sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049707/sj5286Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049707/sj5286Isup3.cml
1,3-Diethyl-2-thiobarbituric acid (0.005 mol) and 2,4,5-trimethoxybenzaldehyde (0.005 mol) were heated in ethanol (15 ml) for 3 h; several drops of diethylamine were added. The progress of reaction was monitored by TLC. The mixture was cooled and the resulting solid was recrystallized from methanol (Asiri et al. 2004) by slow evaporation at room temperature.
All the H-atoms bound to C were positioned with idealized geometry with C—H = 0.93 Å for aromatic, C—H = 0.97 Å for methylene & C—H = 0.96 Å for methyl groups. H-atoms were refined as riding with Uiso(H) = kUeq(C), where k = 1.5 for methyl H-atoms & k = 1.2 for other H-atoms .
The title compound is related to the arylidene 5-[3-(2,5-dimethoxyphenyl)prop- 2-enylidene]-1,3-diethyl-2-thioxohexahydropyrimidine-4,6-dione (II) already reported by our group (Asiri et al., 2009). The molecule is largely planar with a dihedral angle between the benzene and pyrimidine dione rings of 1.41 (7)°. The r. m. s. deviation of atoms from the best fit plane through the non-hydrogen atoms C1/N1/C2/C3/C4/N2/S1/O1/O2/C5/C6/C7/C8/C9/C10/C11/C12/ C14/O3/O4/O5) is 0.0546 (1) Å. Atoms S1 and O1 are displaced from this plane by -0.1187 (1) Å and 0.1131 (2) Å respectively. Non-classical C13–H13C···O2 hydrogen bonds connect the molecule into chains along the b axis (Table. 1, Fig. 2).
For the synthesis of the title compound, see: Asiri et al. (2004). For a related structure, see: Asiri et al. (2009).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).Fig. 1. The structure of (I) with 50% probability ellipsoids. | |
Fig. 2. Unit cell diagram showing C—H···O hydrogen bonds, drawn as dashed lines. |
C18H22N2O5S | F(000) = 800 |
Mr = 378.44 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 6212 reflections |
a = 7.9711 (1) Å | θ = 3.3–75.4° |
b = 17.4106 (3) Å | µ = 1.83 mm−1 |
c = 13.5265 (2) Å | T = 296 K |
β = 99.237 (2)° | Needle like, red |
V = 1852.89 (5) Å3 | 0.29 × 0.10 × 0.09 mm |
Z = 4 |
Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer | 3777 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3083 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.027 |
ω scans | θmax = 75.6°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −9→7 |
Tmin = 0.875, Tmax = 1.000 | k = −21→21 |
14850 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.385P] where P = (Fo2 + 2Fc2)/3 |
3777 reflections | (Δ/σ)max = 0.001 |
240 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C18H22N2O5S | V = 1852.89 (5) Å3 |
Mr = 378.44 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.9711 (1) Å | µ = 1.83 mm−1 |
b = 17.4106 (3) Å | T = 296 K |
c = 13.5265 (2) Å | 0.29 × 0.10 × 0.09 mm |
β = 99.237 (2)° |
Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer | 3777 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3083 reflections with I > 2σ(I) |
Tmin = 0.875, Tmax = 1.000 | Rint = 0.027 |
14850 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.25 e Å−3 |
3777 reflections | Δρmin = −0.20 e Å−3 |
240 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.22340 (6) | 0.56530 (3) | 0.08605 (3) | 0.05970 (16) | |
O1 | 0.0851 (2) | 0.69234 (8) | 0.38430 (11) | 0.0875 (5) | |
O2 | 0.10560 (19) | 0.42242 (7) | 0.36247 (9) | 0.0651 (4) | |
O3 | 0.40703 (17) | 0.63202 (7) | 0.63548 (9) | 0.0591 (3) | |
O4 | 0.58803 (17) | 0.38883 (7) | 0.78593 (9) | 0.0595 (3) | |
O5 | 0.42004 (19) | 0.31584 (7) | 0.63615 (9) | 0.0646 (4) | |
N1 | −0.05338 (18) | 0.62856 (8) | 0.25049 (10) | 0.0472 (3) | |
N2 | −0.05463 (17) | 0.49412 (7) | 0.24558 (10) | 0.0435 (3) | |
C1 | −0.1055 (2) | 0.56302 (9) | 0.19924 (12) | 0.0431 (4) | |
C2 | 0.0503 (2) | 0.63052 (10) | 0.34507 (13) | 0.0527 (4) | |
C3 | 0.1117 (2) | 0.55692 (9) | 0.38958 (11) | 0.0415 (3) | |
C4 | 0.0594 (2) | 0.48671 (9) | 0.33594 (11) | 0.0428 (3) | |
C5 | 0.2186 (2) | 0.56421 (8) | 0.47980 (11) | 0.0411 (3) | |
H5 | 0.2339 | 0.6157 | 0.4973 | 0.049* | |
C6 | 0.31256 (19) | 0.51620 (9) | 0.55427 (11) | 0.0388 (3) | |
C7 | 0.4108 (2) | 0.55426 (9) | 0.63690 (11) | 0.0420 (3) | |
C8 | 0.5034 (2) | 0.51281 (10) | 0.71486 (11) | 0.0456 (4) | |
H8 | 0.5662 | 0.5387 | 0.7686 | 0.055* | |
C9 | 0.5032 (2) | 0.43358 (10) | 0.71329 (11) | 0.0449 (4) | |
C10 | 0.4101 (2) | 0.39422 (9) | 0.63098 (11) | 0.0454 (4) | |
C11 | 0.3173 (2) | 0.43493 (9) | 0.55483 (11) | 0.0421 (3) | |
H11 | 0.2552 | 0.4083 | 0.5015 | 0.050* | |
C12 | −0.1014 (3) | 0.70471 (10) | 0.20484 (14) | 0.0615 (5) | |
H12A | −0.1120 | 0.7414 | 0.2574 | 0.074* | |
H12B | −0.2111 | 0.7007 | 0.1621 | 0.074* | |
C13 | 0.0275 (3) | 0.73339 (11) | 0.14422 (17) | 0.0764 (6) | |
H13A | 0.0335 | 0.6987 | 0.0897 | 0.115* | |
H13B | 0.1367 | 0.7364 | 0.1859 | 0.115* | |
H13C | −0.0052 | 0.7834 | 0.1182 | 0.115* | |
C14 | −0.1166 (2) | 0.42108 (10) | 0.19685 (13) | 0.0537 (4) | |
H14A | −0.2290 | 0.4291 | 0.1586 | 0.064* | |
H14B | −0.1263 | 0.3830 | 0.2480 | 0.064* | |
C15 | −0.0014 (3) | 0.39104 (12) | 0.12873 (15) | 0.0670 (5) | |
H15A | 0.1113 | 0.3852 | 0.1656 | 0.101* | |
H15B | 0.0009 | 0.4265 | 0.0746 | 0.101* | |
H15C | −0.0425 | 0.3422 | 0.1023 | 0.101* | |
C16 | 0.5046 (3) | 0.67409 (11) | 0.71491 (15) | 0.0659 (5) | |
H16A | 0.6227 | 0.6615 | 0.7185 | 0.099* | |
H16B | 0.4682 | 0.6610 | 0.7771 | 0.099* | |
H16C | 0.4887 | 0.7281 | 0.7027 | 0.099* | |
C17 | 0.6693 (3) | 0.42503 (13) | 0.87605 (14) | 0.0652 (5) | |
H17A | 0.5884 | 0.4565 | 0.9028 | 0.098* | |
H17B | 0.7613 | 0.4564 | 0.8616 | 0.098* | |
H17C | 0.7126 | 0.3865 | 0.9241 | 0.098* | |
C18 | 0.3502 (4) | 0.27476 (12) | 0.54961 (16) | 0.0889 (8) | |
H18A | 0.3996 | 0.2927 | 0.4936 | 0.133* | |
H18B | 0.2294 | 0.2826 | 0.5364 | 0.133* | |
H18C | 0.3739 | 0.2210 | 0.5598 | 0.133* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0627 (3) | 0.0666 (3) | 0.0436 (2) | 0.0013 (2) | −0.01048 (19) | 0.00529 (18) |
O1 | 0.1387 (15) | 0.0401 (7) | 0.0671 (9) | 0.0214 (8) | −0.0336 (9) | −0.0107 (6) |
O2 | 0.0932 (10) | 0.0372 (6) | 0.0533 (7) | −0.0014 (6) | −0.0234 (7) | 0.0007 (5) |
O3 | 0.0709 (8) | 0.0411 (6) | 0.0572 (7) | −0.0051 (6) | −0.0145 (6) | −0.0083 (5) |
O4 | 0.0676 (8) | 0.0606 (7) | 0.0434 (6) | 0.0106 (6) | −0.0122 (5) | 0.0023 (5) |
O5 | 0.0981 (10) | 0.0408 (6) | 0.0467 (7) | 0.0036 (6) | −0.0128 (6) | 0.0039 (5) |
N1 | 0.0545 (8) | 0.0427 (7) | 0.0412 (7) | 0.0128 (6) | −0.0015 (6) | −0.0003 (5) |
N2 | 0.0476 (7) | 0.0419 (7) | 0.0382 (6) | −0.0027 (6) | −0.0019 (5) | −0.0003 (5) |
C1 | 0.0397 (8) | 0.0492 (9) | 0.0399 (8) | 0.0026 (6) | 0.0047 (6) | 0.0014 (6) |
C2 | 0.0670 (11) | 0.0424 (9) | 0.0441 (8) | 0.0112 (8) | −0.0048 (8) | −0.0045 (7) |
C3 | 0.0467 (8) | 0.0389 (8) | 0.0374 (7) | 0.0037 (6) | 0.0023 (6) | −0.0004 (6) |
C4 | 0.0481 (9) | 0.0403 (8) | 0.0377 (7) | −0.0016 (6) | −0.0005 (6) | 0.0020 (6) |
C5 | 0.0459 (8) | 0.0370 (7) | 0.0394 (8) | 0.0006 (6) | 0.0037 (6) | −0.0036 (6) |
C6 | 0.0391 (7) | 0.0413 (8) | 0.0352 (7) | −0.0016 (6) | 0.0033 (6) | −0.0020 (6) |
C7 | 0.0412 (8) | 0.0420 (8) | 0.0417 (8) | −0.0030 (6) | 0.0033 (6) | −0.0041 (6) |
C8 | 0.0417 (8) | 0.0520 (9) | 0.0401 (8) | −0.0026 (7) | −0.0027 (6) | −0.0073 (6) |
C9 | 0.0427 (8) | 0.0536 (9) | 0.0363 (8) | 0.0034 (7) | −0.0002 (6) | 0.0023 (6) |
C10 | 0.0538 (9) | 0.0413 (8) | 0.0390 (8) | 0.0000 (7) | 0.0009 (7) | 0.0013 (6) |
C11 | 0.0485 (9) | 0.0412 (8) | 0.0343 (7) | −0.0030 (6) | −0.0001 (6) | −0.0009 (6) |
C12 | 0.0780 (13) | 0.0455 (9) | 0.0548 (10) | 0.0238 (9) | −0.0076 (9) | −0.0010 (8) |
C13 | 0.1027 (17) | 0.0430 (10) | 0.0783 (14) | 0.0035 (11) | −0.0015 (12) | 0.0120 (9) |
C14 | 0.0613 (11) | 0.0513 (9) | 0.0444 (9) | −0.0132 (8) | −0.0039 (8) | 0.0005 (7) |
C15 | 0.0834 (15) | 0.0549 (11) | 0.0608 (11) | −0.0030 (10) | 0.0053 (10) | −0.0092 (9) |
C16 | 0.0708 (12) | 0.0523 (11) | 0.0663 (12) | −0.0143 (9) | −0.0142 (10) | −0.0139 (9) |
C17 | 0.0611 (11) | 0.0810 (14) | 0.0456 (10) | 0.0059 (10) | −0.0158 (8) | −0.0016 (9) |
C18 | 0.157 (2) | 0.0432 (10) | 0.0560 (11) | 0.0000 (13) | −0.0162 (13) | −0.0037 (9) |
S1—C1 | 1.6634 (16) | C9—C10 | 1.412 (2) |
O1—C2 | 1.212 (2) | C10—C11 | 1.366 (2) |
O2—C4 | 1.2145 (19) | C11—H11 | 0.9300 |
O3—C7 | 1.3542 (19) | C12—C13 | 1.499 (3) |
O3—C16 | 1.424 (2) | C12—H12A | 0.9700 |
O4—C9 | 1.3478 (19) | C12—H12B | 0.9700 |
O4—C17 | 1.431 (2) | C13—H13A | 0.9600 |
O5—C10 | 1.368 (2) | C13—H13B | 0.9600 |
O5—C18 | 1.408 (2) | C13—H13C | 0.9600 |
N1—C1 | 1.365 (2) | C14—C15 | 1.496 (3) |
N1—C2 | 1.407 (2) | C14—H14A | 0.9700 |
N1—C12 | 1.487 (2) | C14—H14B | 0.9700 |
N2—C1 | 1.384 (2) | C15—H15A | 0.9600 |
N2—C4 | 1.407 (2) | C15—H15B | 0.9600 |
N2—C14 | 1.480 (2) | C15—H15C | 0.9600 |
C2—C3 | 1.466 (2) | C16—H16A | 0.9600 |
C3—C5 | 1.377 (2) | C16—H16B | 0.9600 |
C3—C4 | 1.448 (2) | C16—H16C | 0.9600 |
C5—C6 | 1.426 (2) | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C6—C11 | 1.415 (2) | C17—H17C | 0.9600 |
C6—C7 | 1.421 (2) | C18—H18A | 0.9600 |
C7—C8 | 1.389 (2) | C18—H18B | 0.9600 |
C8—C9 | 1.380 (2) | C18—H18C | 0.9600 |
C8—H8 | 0.9300 | ||
C7—O3—C16 | 119.70 (14) | N1—C12—C13 | 111.77 (15) |
C9—O4—C17 | 118.14 (15) | N1—C12—H12A | 109.3 |
C10—O5—C18 | 116.88 (14) | C13—C12—H12A | 109.3 |
C1—N1—C2 | 124.63 (13) | N1—C12—H12B | 109.3 |
C1—N1—C12 | 119.84 (14) | C13—C12—H12B | 109.3 |
C2—N1—C12 | 115.49 (14) | H12A—C12—H12B | 107.9 |
C1—N2—C4 | 125.06 (13) | C12—C13—H13A | 109.5 |
C1—N2—C14 | 119.37 (13) | C12—C13—H13B | 109.5 |
C4—N2—C14 | 115.52 (13) | H13A—C13—H13B | 109.5 |
N1—C1—N2 | 116.84 (14) | C12—C13—H13C | 109.5 |
N1—C1—S1 | 121.91 (12) | H13A—C13—H13C | 109.5 |
N2—C1—S1 | 121.25 (12) | H13B—C13—H13C | 109.5 |
O1—C2—N1 | 118.63 (15) | N2—C14—C15 | 112.36 (15) |
O1—C2—C3 | 123.93 (16) | N2—C14—H14A | 109.1 |
N1—C2—C3 | 117.44 (14) | C15—C14—H14A | 109.1 |
C5—C3—C4 | 127.53 (14) | N2—C14—H14B | 109.1 |
C5—C3—C2 | 113.68 (14) | C15—C14—H14B | 109.1 |
C4—C3—C2 | 118.78 (14) | H14A—C14—H14B | 107.9 |
O2—C4—N2 | 117.66 (14) | C14—C15—H15A | 109.5 |
O2—C4—C3 | 125.48 (15) | C14—C15—H15B | 109.5 |
N2—C4—C3 | 116.85 (13) | H15A—C15—H15B | 109.5 |
C3—C5—C6 | 138.77 (14) | C14—C15—H15C | 109.5 |
C3—C5—H5 | 110.6 | H15A—C15—H15C | 109.5 |
C6—C5—H5 | 110.6 | H15B—C15—H15C | 109.5 |
C11—C6—C7 | 116.80 (14) | O3—C16—H16A | 109.5 |
C11—C6—C5 | 126.91 (14) | O3—C16—H16B | 109.5 |
C7—C6—C5 | 116.29 (14) | H16A—C16—H16B | 109.5 |
O3—C7—C8 | 122.56 (14) | O3—C16—H16C | 109.5 |
O3—C7—C6 | 116.54 (14) | H16A—C16—H16C | 109.5 |
C8—C7—C6 | 120.90 (15) | H16B—C16—H16C | 109.5 |
C9—C8—C7 | 120.58 (14) | O4—C17—H17A | 109.5 |
C9—C8—H8 | 119.7 | O4—C17—H17B | 109.5 |
C7—C8—H8 | 119.7 | H17A—C17—H17B | 109.5 |
O4—C9—C8 | 124.58 (15) | O4—C17—H17C | 109.5 |
O4—C9—C10 | 115.65 (15) | H17A—C17—H17C | 109.5 |
C8—C9—C10 | 119.77 (14) | H17B—C17—H17C | 109.5 |
C11—C10—O5 | 125.18 (15) | O5—C18—H18A | 109.5 |
C11—C10—C9 | 119.67 (15) | O5—C18—H18B | 109.5 |
O5—C10—C9 | 115.14 (14) | H18A—C18—H18B | 109.5 |
C10—C11—C6 | 122.25 (14) | O5—C18—H18C | 109.5 |
C10—C11—H11 | 118.9 | H18A—C18—H18C | 109.5 |
C6—C11—H11 | 118.9 | H18B—C18—H18C | 109.5 |
C2—N1—C1—N2 | 1.4 (2) | C3—C5—C6—C7 | 178.82 (18) |
C12—N1—C1—N2 | 179.25 (15) | C16—O3—C7—C8 | 1.8 (3) |
C2—N1—C1—S1 | −178.14 (14) | C16—O3—C7—C6 | −178.93 (16) |
C12—N1—C1—S1 | −0.3 (2) | C11—C6—C7—O3 | 179.37 (14) |
C4—N2—C1—N1 | −6.7 (2) | C5—C6—C7—O3 | −1.0 (2) |
C14—N2—C1—N1 | 175.91 (14) | C11—C6—C7—C8 | −1.3 (2) |
C4—N2—C1—S1 | 172.90 (12) | C5—C6—C7—C8 | 178.27 (14) |
C14—N2—C1—S1 | −4.5 (2) | O3—C7—C8—C9 | 179.83 (15) |
C1—N1—C2—O1 | −178.32 (19) | C6—C7—C8—C9 | 0.6 (2) |
C12—N1—C2—O1 | 3.8 (3) | C17—O4—C9—C8 | 7.1 (3) |
C1—N1—C2—C3 | 2.5 (3) | C17—O4—C9—C10 | −173.28 (16) |
C12—N1—C2—C3 | −175.38 (16) | C7—C8—C9—O4 | −179.43 (15) |
O1—C2—C3—C5 | −2.0 (3) | C7—C8—C9—C10 | 1.0 (2) |
N1—C2—C3—C5 | 177.12 (15) | C18—O5—C10—C11 | 10.0 (3) |
O1—C2—C3—C4 | 179.2 (2) | C18—O5—C10—C9 | −171.0 (2) |
N1—C2—C3—C4 | −1.7 (3) | O4—C9—C10—C11 | 178.64 (15) |
C1—N2—C4—O2 | −172.69 (16) | C8—C9—C10—C11 | −1.7 (2) |
C14—N2—C4—O2 | 4.8 (2) | O4—C9—C10—O5 | −0.4 (2) |
C1—N2—C4—C3 | 7.3 (2) | C8—C9—C10—O5 | 179.17 (15) |
C14—N2—C4—C3 | −175.18 (14) | O5—C10—C11—C6 | 179.94 (16) |
C5—C3—C4—O2 | −1.4 (3) | C9—C10—C11—C6 | 1.0 (2) |
C2—C3—C4—O2 | 177.22 (18) | C7—C6—C11—C10 | 0.5 (2) |
C5—C3—C4—N2 | 178.57 (15) | C5—C6—C11—C10 | −178.98 (16) |
C2—C3—C4—N2 | −2.8 (2) | C1—N1—C12—C13 | −89.7 (2) |
C4—C3—C5—C6 | −1.4 (3) | C2—N1—C12—C13 | 88.3 (2) |
C2—C3—C5—C6 | 179.87 (18) | C1—N2—C14—C15 | 90.12 (19) |
C3—C5—C6—C11 | −1.6 (3) | C4—N2—C14—C15 | −87.55 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···O2i | 0.96 | 2.58 | 3.455 (2) | 152 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H22N2O5S |
Mr | 378.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.9711 (1), 17.4106 (3), 13.5265 (2) |
β (°) | 99.237 (2) |
V (Å3) | 1852.89 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.83 |
Crystal size (mm) | 0.29 × 0.10 × 0.09 |
Data collection | |
Diffractometer | Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.875, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14850, 3777, 3083 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.121, 1.05 |
No. of reflections | 3777 |
No. of parameters | 240 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···O2i | 0.96 | 2.58 | 3.455 (2) | 152.4 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Acknowledgements
The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via the Research Group Track (grant No. 3-102/428).
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Asiri, A. M., Alamry, K. A., Jalboutb, A. F. & Zhang, S. (2004). Molbank, 2004, m359. CrossRef Google Scholar
Asiri, A. M., Khan, S. A. & Ng, S. W. (2009). Acta Cryst. E65, o1820. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The title compound is related to the arylidene 5-[3-(2,5-dimethoxyphenyl)prop- 2-enylidene]-1,3-diethyl-2-thioxohexahydropyrimidine-4,6-dione (II) already reported by our group (Asiri et al., 2009). The molecule is largely planar with a dihedral angle between the benzene and pyrimidine dione rings of 1.41 (7)°. The r. m. s. deviation of atoms from the best fit plane through the non-hydrogen atoms C1/N1/C2/C3/C4/N2/S1/O1/O2/C5/C6/C7/C8/C9/C10/C11/C12/ C14/O3/O4/O5) is 0.0546 (1) Å. Atoms S1 and O1 are displaced from this plane by -0.1187 (1) Å and 0.1131 (2) Å respectively. Non-classical C13–H13C···O2 hydrogen bonds connect the molecule into chains along the b axis (Table. 1, Fig. 2).