


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014027455/su5040sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989014027455/su5040Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014027455/su5040Isup3.cml |
CCDC reference: 1039815
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.060
- wR factor = 0.105
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0060 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 10.584 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.252 Check PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 9 Report
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.03000 Degree PLAT343_ALERT_2_G Unusual sp3 Angle Range in Main Residue for C7 Che PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The title compound was synthesized by adding m-chloroperbenzoic acid (4.5 g, 20 mmol) to a solution containing 1,3-dimethyl-5-bis-(thiomethyl)methylenebarbituric acid (1.3 g, 5 mmol; Sweidan et al., 2009), in dichloromethane (20 ml) at 213 K. After stirring overnight, the solvent was removed in vacuo. Diethylether (20 ml) was added and the precipitated solid was collected and recrystallized from CH2Cl2/Et2O to give colourless crystals (yield: 1.0 g, 51%).
The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.98–1.00 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.
Compounds containing pyrimidine play a vital role in biological activity (Habibi & Tarameshloo, 2011; Holtkamp & Meierkord, 2007). This activity differs from molecule to molecule depending on the tautomery and the nature of the substituents (Demeunynck et al., 2004). In view of the pharmaceutical significance of pyrimidines we became interested in obtaining new barbituric acid derivatives. C5-substituted barbituric and 2-thiobarbituric acids have been used for sedative, hypnotics and anticonvulsant drug applications (Getova & Georgiev 1989; Kratt et al., 1990; Kotha et al., 2005). 1,3-dimethyl barbituric acid has a tendency to accept negative charges by delocalization of π electrons and can exhibit zwitterionic nature. The title compound, which was synthesized via the reaction of 1,3-dimethyl-5-bis-(thiomethyl)methylenebarbituric acid and m-chloroperbenzoic acid, may find applications in bio-organic chemistry.
Several noteworthy features are evident in the crystal structure of the title compound, Fig. 1. The three central sulfonyl groups utilize one methyl group which have almost identical S—C bond lengths [S1—C9 1.752 (4) Å, S2—C8 1.744 (4) Å, S3—C10 1.762 (4) Å] and they are slightly shorter than those reported for (PhSO2)2CH2 (1.786 Å; Glidewell et al. 1995) and for bis(methylsulfonyl)methane (1.781 Å; Awad et al. 2014). Interestingly, significant elongation of the (C4—C7) bond length [1.547 (5) Å] may be attributed to interactions between the sulfonyl groups located at position C7.
As a result of crystal packing the geometry of one of the sulfonyl groups is as expected; having one sulfur-oxygen bond slightly shorter than the other [S2—O1 = 1.415 (3) Å, and S1—O3 = 1.434 (3) Å]. The carbonyl groups that are located on the barbituric acid ring have approximately the same bond lengths, varying from 1.200 (4) to 1.211 (4) Å. The pyrimidine ring in barbituric acid moiety is significantly distorted from planarity and has an envelope conformation with atom C as the flap.
In the crystal, molecules are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2)
For examples of the biological activity of pyrimidines, see: Habibi & Tarameshloo (2011); Holtkamp & Meierkord (2007). For aspects of nucleic acid binding, see: Demeunynck et al. (2004). For drug applications of C5-substituted barbituric and 2-thiobarbituric acids, see: Getova & Georgiev (1989); Kratt et al. (1990); Kotha et al. (2005). For the structures of similar compounds, see: Huang & Chen (1986); Ye et al. (1989); Al-Sheikh et al. (2009); Awad et al. (2014); Glidewell et al. (1995). For the synthesis of the starting material, see: Sweidan et al. (2009).
Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008; molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
C10H16N2O9S3 | Z = 2 |
Mr = 404.43 | F(000) = 420 |
Triclinic, P1 | Dx = 1.722 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9415 (16) Å | Cell parameters from 30 reflections |
b = 8.5796 (17) Å | θ = 10.3–20.1° |
c = 12.756 (3) Å | µ = 0.53 mm−1 |
α = 77.08 (3)° | T = 173 K |
β = 79.50 (3)° | Plate, colourless |
γ = 67.83 (3)° | 0.15 × 0.10 × 0.05 mm |
V = 779.9 (3) Å3 |
Stoe IPDS diffractometer | 2582 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 26.4°, θmin = 3.1° |
phi scans | h = −9→9 |
11105 measured reflections | k = −10→10 |
3175 independent reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.P)2 + 1.8882P] where P = (Fo2 + 2Fc2)/3 |
S = 1.24 | (Δ/σ)max < 0.001 |
3175 reflections | Δρmax = 0.39 e Å−3 |
223 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (11) |
C10H16N2O9S3 | γ = 67.83 (3)° |
Mr = 404.43 | V = 779.9 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9415 (16) Å | Mo Kα radiation |
b = 8.5796 (17) Å | µ = 0.53 mm−1 |
c = 12.756 (3) Å | T = 173 K |
α = 77.08 (3)° | 0.15 × 0.10 × 0.05 mm |
β = 79.50 (3)° |
Stoe IPDS diffractometer | 2582 reflections with I > 2σ(I) |
11105 measured reflections | Rint = 0.069 |
3175 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.24 | Δρmax = 0.39 e Å−3 |
3175 reflections | Δρmin = −0.44 e Å−3 |
223 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 | ||
S1 | 0.26932 (13) | 0.98015 (13) | 0.40183 (7) | 0.0206 (2) | |
S2 | 0.04979 (12) | 1.12489 (12) | 0.20775 (7) | 0.0203 (2) | |
S3 | 0.36913 (12) | 0.56897 (12) | 0.32733 (8) | 0.0203 (2) | |
N1 | 0.0632 (4) | 0.6845 (4) | 0.1414 (3) | 0.0199 (7) | |
N2 | 0.3363 (4) | 0.7382 (4) | 0.0629 (2) | 0.0194 (7) | |
O1 | 0.1593 (4) | 1.2283 (4) | 0.1838 (3) | 0.0357 (7) | |
O2 | 0.1389 (4) | 1.1372 (4) | 0.4315 (2) | 0.0322 (7) | |
O3 | 0.3197 (4) | 0.8360 (4) | 0.4871 (2) | 0.0312 (7) | |
O4 | 0.0233 (4) | 1.0569 (4) | 0.1216 (2) | 0.0308 (7) | |
O5 | 0.5284 (4) | 0.5940 (4) | 0.3464 (2) | 0.0289 (7) | |
O6 | 0.3920 (4) | 0.4469 (4) | 0.2607 (2) | 0.0287 (6) | |
O7 | −0.0780 (4) | 0.7631 (4) | 0.3019 (2) | 0.0267 (6) | |
O8 | 0.2123 (4) | 0.6024 (4) | −0.0170 (2) | 0.0255 (6) | |
O9 | 0.4500 (3) | 0.8776 (3) | 0.1470 (2) | 0.0222 (6) | |
C1 | 0.0528 (5) | 0.7430 (5) | 0.2337 (3) | 0.0186 (7) | |
C2 | 0.2063 (5) | 0.6684 (5) | 0.0579 (3) | 0.0177 (7) | |
C3 | 0.3452 (5) | 0.8054 (5) | 0.1483 (3) | 0.0164 (7) | |
C4 | 0.2215 (5) | 0.7758 (5) | 0.2529 (3) | 0.0171 (7) | |
C5 | −0.0927 (5) | 0.6445 (6) | 0.1232 (3) | 0.0275 (9) | |
H5A | −0.1683 | 0.6306 | 0.1920 | 0.041* | |
H5B | −0.0473 | 0.5383 | 0.0935 | 0.041* | |
H5C | −0.1662 | 0.7378 | 0.0721 | 0.041* | |
C6 | 0.4587 (5) | 0.7625 (5) | −0.0362 (3) | 0.0257 (9) | |
H6A | 0.4152 | 0.8825 | −0.0712 | 0.039* | |
H6B | 0.4591 | 0.6901 | −0.0859 | 0.039* | |
H6C | 0.5830 | 0.7309 | −0.0175 | 0.039* | |
C7 | 0.1493 (5) | 0.9322 (5) | 0.3113 (3) | 0.0169 (7) | |
H7 | 0.0390 | 0.9184 | 0.3587 | 0.020* | |
C8 | −0.1646 (5) | 1.2318 (5) | 0.2710 (3) | 0.0272 (9) | |
H8A | −0.1492 | 1.2715 | 0.3338 | 0.041* | |
H8B | −0.2333 | 1.1540 | 0.2949 | 0.041* | |
H8C | −0.2316 | 1.3301 | 0.2199 | 0.041* | |
C9 | 0.4678 (5) | 1.0156 (5) | 0.3342 (3) | 0.0241 (8) | |
H9A | 0.5235 | 1.0504 | 0.3833 | 0.036* | |
H9B | 0.4363 | 1.1060 | 0.2711 | 0.036* | |
H9C | 0.5546 | 0.9102 | 0.3105 | 0.036* | |
C10 | 0.2393 (6) | 0.5223 (5) | 0.4497 (3) | 0.0280 (9) | |
H10A | 0.3164 | 0.4225 | 0.4954 | 0.042* | |
H10B | 0.1361 | 0.4979 | 0.4342 | 0.042* | |
H10C | 0.1930 | 0.6206 | 0.4874 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0214 (5) | 0.0306 (5) | 0.0163 (4) | −0.0142 (4) | 0.0000 (3) | −0.0093 (4) |
S2 | 0.0178 (4) | 0.0206 (5) | 0.0194 (5) | −0.0040 (4) | 0.0005 (3) | −0.0038 (4) |
S3 | 0.0173 (4) | 0.0210 (5) | 0.0207 (5) | −0.0057 (4) | −0.0023 (4) | −0.0016 (4) |
N1 | 0.0153 (15) | 0.0221 (17) | 0.0245 (17) | −0.0071 (13) | −0.0042 (12) | −0.0058 (13) |
N2 | 0.0209 (16) | 0.0235 (17) | 0.0146 (15) | −0.0078 (13) | 0.0004 (12) | −0.0070 (13) |
O1 | 0.0328 (17) | 0.0331 (18) | 0.0394 (18) | −0.0133 (14) | −0.0022 (14) | −0.0010 (14) |
O2 | 0.0262 (15) | 0.0404 (18) | 0.0368 (17) | −0.0127 (13) | 0.0034 (12) | −0.0236 (14) |
O3 | 0.0381 (17) | 0.0426 (18) | 0.0188 (14) | −0.0216 (14) | −0.0056 (12) | −0.0014 (12) |
O4 | 0.0357 (16) | 0.0259 (16) | 0.0254 (15) | −0.0020 (13) | −0.0083 (12) | −0.0056 (12) |
O5 | 0.0196 (14) | 0.0361 (17) | 0.0314 (16) | −0.0106 (12) | −0.0068 (12) | −0.0019 (13) |
O6 | 0.0330 (16) | 0.0234 (15) | 0.0272 (15) | −0.0053 (12) | −0.0050 (12) | −0.0059 (12) |
O7 | 0.0186 (13) | 0.0409 (18) | 0.0274 (15) | −0.0162 (12) | 0.0049 (11) | −0.0151 (13) |
O8 | 0.0302 (15) | 0.0265 (15) | 0.0230 (14) | −0.0091 (12) | −0.0045 (12) | −0.0105 (12) |
O9 | 0.0220 (13) | 0.0283 (15) | 0.0216 (14) | −0.0147 (12) | 0.0020 (11) | −0.0083 (11) |
C1 | 0.0161 (17) | 0.0206 (19) | 0.0201 (18) | −0.0068 (15) | −0.0023 (14) | −0.0043 (15) |
C2 | 0.0185 (17) | 0.0152 (18) | 0.0179 (18) | −0.0024 (14) | −0.0067 (14) | −0.0025 (14) |
C3 | 0.0127 (16) | 0.0166 (18) | 0.0185 (18) | −0.0033 (14) | −0.0016 (13) | −0.0035 (14) |
C4 | 0.0150 (16) | 0.0226 (19) | 0.0150 (17) | −0.0081 (14) | −0.0004 (13) | −0.0040 (14) |
C5 | 0.025 (2) | 0.033 (2) | 0.033 (2) | −0.0163 (18) | −0.0071 (17) | −0.0088 (18) |
C6 | 0.029 (2) | 0.032 (2) | 0.0184 (19) | −0.0129 (18) | 0.0041 (16) | −0.0089 (17) |
C7 | 0.0159 (17) | 0.023 (2) | 0.0136 (17) | −0.0085 (15) | 0.0010 (13) | −0.0051 (14) |
C8 | 0.0178 (18) | 0.031 (2) | 0.026 (2) | −0.0027 (17) | 0.0022 (16) | −0.0050 (17) |
C9 | 0.0219 (19) | 0.035 (2) | 0.023 (2) | −0.0167 (17) | −0.0028 (15) | −0.0069 (17) |
C10 | 0.032 (2) | 0.031 (2) | 0.022 (2) | −0.0180 (19) | 0.0004 (17) | 0.0011 (17) |
S1—O3 | 1.434 (3) | O9—C3 | 1.207 (4) |
S1—O2 | 1.436 (3) | C1—C4 | 1.539 (5) |
S1—C9 | 1.752 (4) | C3—C4 | 1.539 (5) |
S1—C7 | 1.823 (4) | C4—C7 | 1.547 (5) |
S2—O1 | 1.415 (3) | C5—H5A | 0.9800 |
S2—O4 | 1.434 (3) | C5—H5B | 0.9800 |
S2—C8 | 1.744 (4) | C5—H5C | 0.9800 |
S2—C7 | 1.876 (4) | C6—H6A | 0.9800 |
S3—O5 | 1.430 (3) | C6—H6B | 0.9800 |
S3—O6 | 1.432 (3) | C6—H6C | 0.9800 |
S3—C10 | 1.762 (4) | C7—H7 | 1.0000 |
S3—C4 | 1.873 (4) | C8—H8A | 0.9800 |
N1—C1 | 1.358 (5) | C8—H8B | 0.9800 |
N1—C2 | 1.396 (5) | C8—H8C | 0.9800 |
N1—C5 | 1.471 (5) | C9—H9A | 0.9800 |
N2—C3 | 1.365 (5) | C9—H9B | 0.9800 |
N2—C2 | 1.392 (5) | C9—H9C | 0.9800 |
N2—C6 | 1.474 (5) | C10—H10A | 0.9800 |
O7—C1 | 1.211 (4) | C10—H10B | 0.9800 |
O8—C2 | 1.200 (4) | C10—H10C | 0.9800 |
O3—S1—O2 | 117.09 (19) | C7—C4—S3 | 117.1 (2) |
O3—S1—C9 | 108.84 (19) | N1—C5—H5A | 109.5 |
O2—S1—C9 | 109.23 (19) | N1—C5—H5B | 109.5 |
O3—S1—C7 | 107.80 (17) | H5A—C5—H5B | 109.5 |
O2—S1—C7 | 102.30 (17) | N1—C5—H5C | 109.5 |
C9—S1—C7 | 111.45 (17) | H5A—C5—H5C | 109.5 |
O1—S2—O4 | 118.50 (19) | H5B—C5—H5C | 109.5 |
O1—S2—C8 | 110.4 (2) | N2—C6—H6A | 109.5 |
O4—S2—C8 | 108.3 (2) | N2—C6—H6B | 109.5 |
O1—S2—C7 | 110.32 (17) | H6A—C6—H6B | 109.5 |
O4—S2—C7 | 104.43 (17) | N2—C6—H6C | 109.5 |
C8—S2—C7 | 103.80 (18) | H6A—C6—H6C | 109.5 |
O5—S3—O6 | 118.38 (18) | H6B—C6—H6C | 109.5 |
O5—S3—C10 | 111.37 (19) | C4—C7—S1 | 126.6 (3) |
O6—S3—C10 | 108.29 (19) | C4—C7—S2 | 106.8 (2) |
O5—S3—C4 | 107.38 (17) | S1—C7—S2 | 110.83 (19) |
O6—S3—C4 | 103.90 (17) | C4—C7—H7 | 103.3 |
C10—S3—C4 | 106.69 (18) | S1—C7—H7 | 103.3 |
C1—N1—C2 | 125.2 (3) | S2—C7—H7 | 103.3 |
C1—N1—C5 | 118.2 (3) | S2—C8—H8A | 109.5 |
C2—N1—C5 | 116.4 (3) | S2—C8—H8B | 109.5 |
C3—N2—C2 | 124.9 (3) | H8A—C8—H8B | 109.5 |
C3—N2—C6 | 116.8 (3) | S2—C8—H8C | 109.5 |
C2—N2—C6 | 117.7 (3) | H8A—C8—H8C | 109.5 |
O7—C1—N1 | 123.2 (3) | H8B—C8—H8C | 109.5 |
O7—C1—C4 | 119.7 (3) | S1—C9—H9A | 109.5 |
N1—C1—C4 | 117.0 (3) | S1—C9—H9B | 109.5 |
O8—C2—N2 | 121.6 (3) | H9A—C9—H9B | 109.5 |
O8—C2—N1 | 120.9 (3) | S1—C9—H9C | 109.5 |
N2—C2—N1 | 117.4 (3) | H9A—C9—H9C | 109.5 |
O9—C3—N2 | 123.5 (3) | H9B—C9—H9C | 109.5 |
O9—C3—C4 | 119.5 (3) | S3—C10—H10A | 109.5 |
N2—C3—C4 | 116.9 (3) | S3—C10—H10B | 109.5 |
C1—C4—C3 | 113.4 (3) | H10A—C10—H10B | 109.5 |
C1—C4—C7 | 106.7 (3) | S3—C10—H10C | 109.5 |
C3—C4—C7 | 111.2 (3) | H10A—C10—H10C | 109.5 |
C1—C4—S3 | 105.6 (2) | H10B—C10—H10C | 109.5 |
C3—C4—S3 | 102.9 (2) | ||
C2—N1—C1—O7 | 176.2 (4) | O5—S3—C4—C1 | 179.8 (2) |
C5—N1—C1—O7 | 0.3 (6) | O6—S3—C4—C1 | 53.6 (3) |
C2—N1—C1—C4 | −6.8 (5) | C10—S3—C4—C1 | −60.7 (3) |
C5—N1—C1—C4 | 177.2 (3) | O5—S3—C4—C3 | 60.6 (3) |
C3—N2—C2—O8 | −175.6 (4) | O6—S3—C4—C3 | −65.6 (3) |
C6—N2—C2—O8 | 12.9 (5) | C10—S3—C4—C3 | −179.9 (2) |
C3—N2—C2—N1 | 7.1 (5) | O5—S3—C4—C7 | −61.6 (3) |
C6—N2—C2—N1 | −164.4 (3) | O6—S3—C4—C7 | 172.2 (3) |
C1—N1—C2—O8 | 173.7 (4) | C10—S3—C4—C7 | 57.9 (3) |
C5—N1—C2—O8 | −10.2 (5) | C1—C4—C7—S1 | 153.1 (3) |
C1—N1—C2—N2 | −8.9 (5) | C3—C4—C7—S1 | −82.7 (4) |
C5—N1—C2—N2 | 167.1 (3) | S3—C4—C7—S1 | 35.1 (4) |
C2—N2—C3—O9 | −173.7 (3) | C1—C4—C7—S2 | −73.5 (3) |
C6—N2—C3—O9 | −2.2 (5) | C3—C4—C7—S2 | 50.7 (3) |
C2—N2—C3—C4 | 10.1 (5) | S3—C4—C7—S2 | 168.54 (17) |
C6—N2—C3—C4 | −178.3 (3) | O3—S1—C7—C4 | −55.8 (3) |
O7—C1—C4—C3 | −160.3 (3) | O2—S1—C7—C4 | −179.8 (3) |
N1—C1—C4—C3 | 22.6 (5) | C9—S1—C7—C4 | 63.5 (4) |
O7—C1—C4—C7 | −37.5 (5) | O3—S1—C7—S2 | 172.24 (18) |
N1—C1—C4—C7 | 145.4 (3) | O2—S1—C7—S2 | 48.2 (2) |
O7—C1—C4—S3 | 87.7 (4) | C9—S1—C7—S2 | −68.4 (2) |
N1—C1—C4—S3 | −89.3 (3) | O1—S2—C7—C4 | −110.8 (3) |
O9—C3—C4—C1 | 159.5 (3) | O4—S2—C7—C4 | 17.5 (3) |
N2—C3—C4—C1 | −24.2 (5) | C8—S2—C7—C4 | 130.9 (3) |
O9—C3—C4—C7 | 39.3 (4) | O1—S2—C7—S1 | 30.6 (2) |
N2—C3—C4—C7 | −144.4 (3) | O4—S2—C7—S1 | 158.95 (19) |
O9—C3—C4—S3 | −86.9 (4) | C8—S2—C7—S1 | −87.7 (2) |
N2—C3—C4—S3 | 89.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O8i | 0.98 | 2.51 | 3.240 (6) | 131 |
C6—H6A···O9ii | 0.98 | 2.59 | 3.380 (5) | 138 |
C8—H8C···O8iii | 0.98 | 2.51 | 3.263 (5) | 133 |
C10—H10A···O5iv | 0.98 | 2.50 | 3.219 (5) | 130 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z; (iv) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O8i | 0.98 | 2.51 | 3.240 (6) | 131 |
C6—H6A···O9ii | 0.98 | 2.59 | 3.380 (5) | 138 |
C8—H8C···O8iii | 0.98 | 2.51 | 3.263 (5) | 133 |
C10—H10A···O5iv | 0.98 | 2.50 | 3.219 (5) | 130 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z; (iv) −x+1, −y+1, −z+1. |
Compounds containing pyrimidine play a vital role in biological activity (Habibi & Tarameshloo, 2011; Holtkamp & Meierkord, 2007). This activity differs from molecule to molecule depending on the tautomery and the nature of the substituents (Demeunynck et al., 2004). In view of the pharmaceutical significance of pyrimidines we became interested in obtaining new barbituric acid derivatives. C5-substituted barbituric and 2-thiobarbituric acids have been used for sedative, hypnotics and anticonvulsant drug applications (Getova & Georgiev 1989; Kratt et al., 1990; Kotha et al., 2005). 1,3-dimethyl barbituric acid has a tendency to accept negative charges by delocalization of π electrons and can exhibit zwitterionic nature. The title compound, which was synthesized via the reaction of 1,3-dimethyl-5-bis-(thiomethyl)methylenebarbituric acid and m-chloroperbenzoic acid, may find applications in bio-organic chemistry.
Several noteworthy features are evident in the crystal structure of the title compound, Fig. 1. The three central sulfonyl groups utilize one methyl group which have almost identical S—C bond lengths [S1—C9 1.752 (4) Å, S2—C8 1.744 (4) Å, S3—C10 1.762 (4) Å] and they are slightly shorter than those reported for (PhSO2)2CH2 (1.786 Å; Glidewell et al. 1995) and for bis(methylsulfonyl)methane (1.781 Å; Awad et al. 2014). Interestingly, significant elongation of the (C4—C7) bond length [1.547 (5) Å] may be attributed to interactions between the sulfonyl groups located at position C7.
As a result of crystal packing the geometry of one of the sulfonyl groups is as expected; having one sulfur-oxygen bond slightly shorter than the other [S2—O1 = 1.415 (3) Å, and S1—O3 = 1.434 (3) Å]. The carbonyl groups that are located on the barbituric acid ring have approximately the same bond lengths, varying from 1.200 (4) to 1.211 (4) Å. The pyrimidine ring in barbituric acid moiety is significantly distorted from planarity and has an envelope conformation with atom C as the flap.
In the crystal, molecules are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2)