Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057923/zl2088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057923/zl2088Isup2.hkl |
CCDC reference: 673000
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.107
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for S2 - C2 .. 5.16 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The starting material was prepared in a manner similar to that described by Ziegler et al. (1967). Biological activities of pyrimidines and pyrimidinethiones are described by Brown (1984, 1985), Cannito et al. (1990), Chakaravorty et al. (1992), De Clerq & Walker (1985), Kleemann & Engel (1982), Lomis et al. (1988), Perrissin et al. (1988), Shishoo & Jain (1992), Smith & Kan (1964), Tetsuo et al. (1987) and Vega et al. (1990).
An equimolar mixture of 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-dihydro-2,3-furandione (0.50 g, 1.63 mmol), easily obtained from oxalyl chloride and 1,3-bis(4-methylphenyl)propane-1,3-dione, in a similar way as described by Ziegler et al. (1967), and N-methylthiourea (0.15 g, 1.63 mmol) were refluxed in 30 ml boiling benzene for 3 h. After the evaporation of the solvent, the oily residue was treated with dry diethylether to give a yellow precipitate, which was filtered off and recrystallized from acetic acid (yield: 0.35 g, 64%; m.p. 483 K). IR (KBr, ν, cm-1): 3040–2840 (w, aromatic and aliphatic C—H), 1650 (s, C═O), 1603 s, 1567 w, 1514 s, 1492 m (C≐C, C≐N, phenyl and aromatic rings), 1185 (m, C═S); 1H NMR (300 MHz, CDCl3, p.p.m.): δ 8.16 (s, 1H at C-6), 7.56–6.99 (m, 8H, Ar—H), 3.97 (s, 3H, N—CH3), 2.31, 2.24 (two s, 6H, Ar—CH3). Analysis calculated for C20H18N2OS: C 71.83, H 5.42, N 8.38, S 9.59%; found: C 71.80, H 5.47, N 8.18, S 9.60%.
H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.96 and 0.93 Å for CH3 and CH(aromatic), respectively. The displacement parameters of the H atoms were constrained as Uiso(H)= 1.2Ueq(1.5Ueq for methyl groups). Riding methyl H atoms were allowed to rotate freely during refinement using the AFIX 137 command of SHELXL97 (Sheldrick, 1997).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
C20H18N2OS | F(000) = 704 |
Mr = 334.42 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20480 reflections |
a = 5.8203 (5) Å | θ = 1.7–27.9° |
b = 15.6178 (10) Å | µ = 0.20 mm−1 |
c = 19.4161 (16) Å | T = 296 K |
β = 104.466 (6)° | Prismatic rod, colorless |
V = 1709.0 (2) Å3 | 0.61 × 0.35 × 0.20 mm |
Z = 4 |
Stoe IPDSII diffractometer | 3294 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2225 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.043 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
w scans | h = −7→6 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.923, Tmax = 0.978 | l = −23→23 |
14819 measured reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3 |
3294 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C20H18N2OS | V = 1709.0 (2) Å3 |
Mr = 334.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.8203 (5) Å | µ = 0.20 mm−1 |
b = 15.6178 (10) Å | T = 296 K |
c = 19.4161 (16) Å | 0.61 × 0.35 × 0.20 mm |
β = 104.466 (6)° |
Stoe IPDSII diffractometer | 3294 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2225 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.978 | Rint = 0.043 |
14819 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3294 reflections | Δρmin = −0.27 e Å−3 |
220 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S2 | 0.46693 (13) | 0.34236 (4) | 0.50064 (3) | 0.0795 (2) | |
O5 | 0.6981 (3) | 0.54459 (8) | 0.24409 (7) | 0.0582 (3) | |
N1 | 0.2814 (3) | 0.44445 (10) | 0.39131 (7) | 0.0513 (4) | |
N3 | 0.5736 (3) | 0.34751 (9) | 0.37627 (8) | 0.0522 (4) | |
C1 | 0.1086 (4) | 0.47291 (14) | 0.43011 (11) | 0.0665 (6) | |
H1A | 0.1881 | 0.5061 | 0.4707 | 0.100* | |
H1B | 0.0355 | 0.4239 | 0.4456 | 0.100* | |
H1C | −0.0108 | 0.5074 | 0.3994 | 0.100* | |
C2 | 0.4422 (3) | 0.37950 (12) | 0.41885 (9) | 0.0518 (4) | |
C4 | 0.5771 (3) | 0.38456 (11) | 0.31569 (9) | 0.0450 (4) | |
C5 | 0.4461 (3) | 0.46083 (11) | 0.29287 (8) | 0.0447 (4) | |
C6 | 0.2926 (3) | 0.48546 (12) | 0.33108 (9) | 0.0502 (4) | |
H6 | 0.1924 | 0.5317 | 0.3155 | 0.060* | |
C41 | 0.7127 (3) | 0.34048 (10) | 0.27081 (9) | 0.0464 (4) | |
C42 | 0.6388 (4) | 0.34305 (11) | 0.19719 (9) | 0.0525 (5) | |
H42 | 0.5051 | 0.3747 | 0.1754 | 0.063* | |
C43 | 0.7608 (4) | 0.29933 (12) | 0.15594 (10) | 0.0555 (5) | |
H43 | 0.7066 | 0.3014 | 0.1067 | 0.067* | |
C44 | 0.9619 (4) | 0.25246 (11) | 0.18617 (10) | 0.0531 (4) | |
C45 | 1.0344 (4) | 0.24938 (12) | 0.25993 (10) | 0.0598 (5) | |
H45 | 1.1682 | 0.2176 | 0.2815 | 0.072* | |
C46 | 0.9127 (3) | 0.29225 (12) | 0.30189 (10) | 0.0539 (5) | |
H46 | 0.9646 | 0.2889 | 0.3512 | 0.065* | |
C47 | 1.0966 (4) | 0.20643 (14) | 0.14034 (12) | 0.0702 (6) | |
H47A | 0.9894 | 0.1908 | 0.0960 | 0.105* | |
H47B | 1.1683 | 0.1558 | 0.1644 | 0.105* | |
H47C | 1.2177 | 0.2434 | 0.1314 | 0.105* | |
C51 | 0.4959 (3) | 0.51927 (10) | 0.23664 (9) | 0.0450 (4) | |
C52 | 0.2996 (3) | 0.54438 (10) | 0.17599 (8) | 0.0447 (4) | |
C53 | 0.0838 (4) | 0.50202 (11) | 0.16035 (9) | 0.0514 (4) | |
H53 | 0.0575 | 0.4584 | 0.1901 | 0.062* | |
C54 | −0.0921 (4) | 0.52392 (13) | 0.10124 (10) | 0.0581 (5) | |
H54 | −0.2355 | 0.4945 | 0.0914 | 0.070* | |
C55 | −0.0594 (4) | 0.58882 (13) | 0.05625 (9) | 0.0566 (5) | |
C56 | 0.1566 (4) | 0.63170 (13) | 0.07211 (10) | 0.0624 (5) | |
H56 | 0.1813 | 0.6759 | 0.0427 | 0.075* | |
C57 | 0.3338 (4) | 0.60988 (12) | 0.13040 (10) | 0.0559 (5) | |
H57 | 0.4780 | 0.6388 | 0.1397 | 0.067* | |
C58 | −0.2554 (5) | 0.61164 (16) | −0.00808 (11) | 0.0796 (7) | |
H58A | −0.3507 | 0.6566 | 0.0041 | 0.119* | |
H58B | −0.3525 | 0.5622 | −0.0235 | 0.119* | |
H58C | −0.1875 | 0.6307 | −0.0457 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0944 (5) | 0.0918 (4) | 0.0535 (3) | −0.0007 (3) | 0.0208 (3) | 0.0217 (3) |
O5 | 0.0490 (9) | 0.0646 (8) | 0.0613 (8) | −0.0083 (7) | 0.0141 (6) | 0.0010 (6) |
N1 | 0.0519 (10) | 0.0569 (9) | 0.0478 (8) | −0.0017 (7) | 0.0174 (7) | −0.0001 (6) |
N3 | 0.0521 (10) | 0.0539 (9) | 0.0485 (8) | 0.0008 (7) | 0.0087 (7) | 0.0058 (6) |
C1 | 0.0691 (16) | 0.0777 (14) | 0.0615 (11) | 0.0007 (11) | 0.0330 (10) | −0.0042 (10) |
C2 | 0.0502 (12) | 0.0544 (10) | 0.0494 (9) | −0.0073 (9) | 0.0100 (8) | 0.0030 (8) |
C4 | 0.0392 (11) | 0.0486 (9) | 0.0444 (8) | −0.0035 (7) | 0.0048 (7) | 0.0002 (7) |
C5 | 0.0430 (11) | 0.0472 (9) | 0.0428 (8) | 0.0001 (8) | 0.0088 (7) | 0.0012 (7) |
C6 | 0.0512 (12) | 0.0528 (10) | 0.0468 (9) | 0.0026 (8) | 0.0124 (8) | 0.0034 (7) |
C41 | 0.0449 (11) | 0.0437 (9) | 0.0494 (9) | −0.0019 (8) | 0.0095 (7) | 0.0007 (7) |
C42 | 0.0497 (12) | 0.0505 (10) | 0.0518 (9) | 0.0060 (8) | 0.0020 (8) | −0.0040 (8) |
C43 | 0.0617 (14) | 0.0518 (10) | 0.0500 (9) | 0.0036 (9) | 0.0084 (9) | −0.0049 (8) |
C44 | 0.0531 (12) | 0.0418 (9) | 0.0668 (11) | −0.0025 (8) | 0.0193 (9) | −0.0019 (8) |
C45 | 0.0528 (13) | 0.0585 (11) | 0.0672 (12) | 0.0133 (9) | 0.0135 (9) | 0.0079 (9) |
C46 | 0.0517 (12) | 0.0552 (11) | 0.0521 (10) | 0.0057 (9) | 0.0078 (8) | 0.0062 (8) |
C47 | 0.0744 (17) | 0.0586 (13) | 0.0851 (14) | 0.0067 (11) | 0.0342 (12) | −0.0048 (10) |
C51 | 0.0461 (12) | 0.0441 (9) | 0.0466 (9) | −0.0016 (8) | 0.0151 (7) | −0.0043 (7) |
C52 | 0.0495 (12) | 0.0422 (9) | 0.0442 (9) | 0.0031 (8) | 0.0151 (7) | 0.0009 (7) |
C53 | 0.0505 (13) | 0.0534 (10) | 0.0508 (9) | −0.0005 (8) | 0.0138 (8) | 0.0097 (8) |
C54 | 0.0477 (13) | 0.0680 (12) | 0.0568 (10) | 0.0016 (9) | 0.0094 (8) | 0.0054 (9) |
C55 | 0.0635 (14) | 0.0570 (11) | 0.0481 (9) | 0.0169 (10) | 0.0118 (9) | 0.0028 (8) |
C56 | 0.0816 (17) | 0.0527 (11) | 0.0536 (11) | 0.0070 (11) | 0.0181 (10) | 0.0144 (8) |
C57 | 0.0636 (14) | 0.0494 (10) | 0.0560 (10) | −0.0073 (9) | 0.0174 (9) | 0.0033 (8) |
C58 | 0.0835 (18) | 0.0877 (16) | 0.0610 (12) | 0.0265 (13) | 0.0054 (11) | 0.0140 (11) |
S2—C2 | 1.6628 (18) | C44—C47 | 1.507 (3) |
O5—C51 | 1.215 (2) | C45—C46 | 1.379 (3) |
N1—C6 | 1.349 (2) | C45—H45 | 0.9300 |
N1—C2 | 1.393 (2) | C46—H46 | 0.9300 |
N1—C1 | 1.468 (2) | C47—H47A | 0.9600 |
N3—C4 | 1.316 (2) | C47—H47B | 0.9600 |
N3—C2 | 1.354 (2) | C47—H47C | 0.9600 |
C1—H1A | 0.9600 | C51—C52 | 1.474 (2) |
C1—H1B | 0.9600 | C52—C53 | 1.384 (3) |
C1—H1C | 0.9600 | C52—C57 | 1.399 (2) |
C4—C5 | 1.424 (2) | C53—C54 | 1.377 (3) |
C4—C41 | 1.483 (2) | C53—H53 | 0.9300 |
C5—C6 | 1.352 (2) | C54—C55 | 1.382 (3) |
C5—C51 | 1.506 (2) | C54—H54 | 0.9300 |
C6—H6 | 0.9300 | C55—C56 | 1.390 (3) |
C41—C42 | 1.387 (2) | C55—C58 | 1.509 (3) |
C41—C46 | 1.391 (3) | C56—C57 | 1.370 (3) |
C42—C43 | 1.377 (3) | C56—H56 | 0.9300 |
C42—H42 | 0.9300 | C57—H57 | 0.9300 |
C43—C44 | 1.381 (3) | C58—H58A | 0.9600 |
C43—H43 | 0.9300 | C58—H58B | 0.9600 |
C44—C45 | 1.389 (3) | C58—H58C | 0.9600 |
C6—N1—C2 | 120.33 (16) | C45—C46—C41 | 120.27 (17) |
C6—N1—C1 | 119.26 (16) | C45—C46—H46 | 119.9 |
C2—N1—C1 | 120.28 (15) | C41—C46—H46 | 119.9 |
C4—N3—C2 | 121.39 (16) | C44—C47—H47A | 109.5 |
N1—C1—H1A | 109.5 | C44—C47—H47B | 109.5 |
N1—C1—H1B | 109.5 | H47A—C47—H47B | 109.5 |
H1A—C1—H1B | 109.5 | C44—C47—H47C | 109.5 |
N1—C1—H1C | 109.5 | H47A—C47—H47C | 109.5 |
H1A—C1—H1C | 109.5 | H47B—C47—H47C | 109.5 |
H1B—C1—H1C | 109.5 | O5—C51—C52 | 122.87 (16) |
N3—C2—N1 | 117.52 (15) | O5—C51—C5 | 117.83 (16) |
N3—C2—S2 | 121.80 (15) | C52—C51—C5 | 119.29 (16) |
N1—C2—S2 | 120.67 (14) | C53—C52—C57 | 118.39 (16) |
N3—C4—C5 | 121.29 (16) | C53—C52—C51 | 121.85 (15) |
N3—C4—C41 | 116.78 (15) | C57—C52—C51 | 119.68 (17) |
C5—C4—C41 | 121.84 (15) | C54—C53—C52 | 120.61 (17) |
C6—C5—C4 | 116.30 (15) | C54—C53—H53 | 119.7 |
C6—C5—C51 | 119.91 (15) | C52—C53—H53 | 119.7 |
C4—C5—C51 | 123.21 (16) | C53—C54—C55 | 121.2 (2) |
N1—C6—C5 | 121.48 (17) | C53—C54—H54 | 119.4 |
N1—C6—H6 | 119.3 | C55—C54—H54 | 119.4 |
C5—C6—H6 | 119.3 | C54—C55—C56 | 118.24 (17) |
C42—C41—C46 | 118.24 (17) | C54—C55—C58 | 120.1 (2) |
C42—C41—C4 | 121.24 (16) | C56—C55—C58 | 121.65 (19) |
C46—C41—C4 | 120.46 (16) | C57—C56—C55 | 121.07 (18) |
C43—C42—C41 | 120.87 (18) | C57—C56—H56 | 119.5 |
C43—C42—H42 | 119.6 | C55—C56—H56 | 119.5 |
C41—C42—H42 | 119.6 | C56—C57—C52 | 120.49 (19) |
C42—C43—C44 | 121.41 (17) | C56—C57—H57 | 119.8 |
C42—C43—H43 | 119.3 | C52—C57—H57 | 119.8 |
C44—C43—H43 | 119.3 | C55—C58—H58A | 109.5 |
C43—C44—C45 | 117.60 (18) | C55—C58—H58B | 109.5 |
C43—C44—C47 | 120.84 (18) | H58A—C58—H58B | 109.5 |
C45—C44—C47 | 121.56 (19) | C55—C58—H58C | 109.5 |
C46—C45—C44 | 121.58 (18) | H58A—C58—H58C | 109.5 |
C46—C45—H45 | 119.2 | H58B—C58—H58C | 109.5 |
C44—C45—H45 | 119.2 | ||
C4—N3—C2—N1 | 10.2 (3) | C42—C43—C44—C47 | −178.71 (19) |
C4—N3—C2—S2 | −170.65 (14) | C43—C44—C45—C46 | −0.8 (3) |
C6—N1—C2—N3 | −13.5 (3) | C47—C44—C45—C46 | 179.28 (19) |
C1—N1—C2—N3 | 170.69 (17) | C44—C45—C46—C41 | −0.3 (3) |
C6—N1—C2—S2 | 167.39 (14) | C42—C41—C46—C45 | 0.8 (3) |
C1—N1—C2—S2 | −8.4 (2) | C4—C41—C46—C45 | 178.15 (17) |
C2—N3—C4—C5 | 1.1 (3) | C6—C5—C51—O5 | 118.22 (19) |
C2—N3—C4—C41 | −175.58 (16) | C4—C5—C51—O5 | −52.7 (2) |
N3—C4—C5—C6 | −9.4 (3) | C6—C5—C51—C52 | −60.9 (2) |
C41—C4—C5—C6 | 167.09 (16) | C4—C5—C51—C52 | 128.16 (18) |
N3—C4—C5—C51 | 161.81 (16) | O5—C51—C52—C53 | 166.43 (17) |
C41—C4—C5—C51 | −21.7 (3) | C5—C51—C52—C53 | −14.5 (2) |
C2—N1—C6—C5 | 5.2 (3) | O5—C51—C52—C57 | −10.3 (2) |
C1—N1—C6—C5 | −178.97 (18) | C5—C51—C52—C57 | 168.79 (15) |
C4—C5—C6—N1 | 6.1 (3) | C57—C52—C53—C54 | 0.1 (3) |
C51—C5—C6—N1 | −165.48 (16) | C51—C52—C53—C54 | −176.60 (17) |
N3—C4—C41—C42 | 145.70 (18) | C52—C53—C54—C55 | −0.4 (3) |
C5—C4—C41—C42 | −31.0 (3) | C53—C54—C55—C56 | 0.1 (3) |
N3—C4—C41—C46 | −31.5 (2) | C53—C54—C55—C58 | −179.87 (19) |
C5—C4—C41—C46 | 151.79 (18) | C54—C55—C56—C57 | 0.6 (3) |
C46—C41—C42—C43 | −0.3 (3) | C58—C55—C56—C57 | −179.47 (19) |
C4—C41—C42—C43 | −177.57 (17) | C55—C56—C57—C52 | −0.9 (3) |
C41—C42—C43—C44 | −0.8 (3) | C53—C52—C57—C56 | 0.5 (3) |
C42—C43—C44—C45 | 1.4 (3) | C51—C52—C57—C56 | 177.33 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C47—H47B···O5i | 0.96 | 2.47 | 3.393 (3) | 162 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H18N2OS |
Mr | 334.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 5.8203 (5), 15.6178 (10), 19.4161 (16) |
β (°) | 104.466 (6) |
V (Å3) | 1709.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.61 × 0.35 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.923, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14819, 3294, 2225 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.107, 1.01 |
No. of reflections | 3294 |
No. of parameters | 220 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.27 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C47—H47B···O5i | 0.96 | 2.47 | 3.393 (3) | 162.0 |
Symmetry code: (i) −x+2, y−1/2, −z+1/2. |
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In general, pyrimidines have found much interest for their widespread potential biological activities (Kleemann & Engel, 1982) and medicinal applications, thus their chemistry has been investigated extensively (Brown, 1984, 1985; Lomis et al., 1988). In particular, various analogues of pyrimidine-thiones possess effective antibacterial, antifungal, antiviral, anti-AIDS, insecticidal and miticidal activities (De Clerq & Walker, 1985). Furthermore many condensed heterocyclic systems, especially when linked to a pyrimidine ring, play an important role as analgesic (Perrissin et al., 1988), antihypertensive (Cannito et al., 1990), antipyretic (Smith & Kan, 1964), and antiinflammatory drugs (Vega et al., 1990), also as pesticides (Tetsuo et al., 1987), herbicides (Chakaravorty et al., 1992), and plant growth regulators (Shishoo & Jain, 1992). In view of these important properties, we have undertaken the X-ray diffraction study of the title compound.
The structure of the title compound is shown in Fig. 1. The structure contains one central pyrimidine ring (N1/N3/C2/C4—C6) with a methyl substituent at N1, an S substituent at C2, a p-tolyl group (C41—C47) at C4 and a methylbenzoyl group (O5/C51—C58) at C5. The plane of the pyrimidine ring makes dihedral angles of 31.37 (8) and 68.84 (5)° with the (C41—C46) and (C52—C57) phenyl rings, respectively. The pyrimidine ring is planar with a maximum deviation of 0.0776 (12) Å for atom C2. The interatomic distances and angles show no anomalies.
The molecular structure of the title compound contains no significant intramolecular interactions. In the construction of the intermolecular connections, 21 screw symmetry-related molecules, which form pairs of neighbouring molecules translated linearly along the b axis of the unit cell, play an active bridging role. Atom C47 acts as a hydrogen-bond donor, via atom H47B, to atom O5 at (2 - x, -1/2 + y, 1/2 - z). Extension of this hydrogen-bonding interaction along b results in the formation of molecular chains along the [010] direction (Fig. 2).