Acta Cryst. (2011). E67, o261 [ doi:10.1107/S1600536810053559 ]
The asymmetric unit of the title compound, C23H23N5OS, contains two independent molecules. In one molecule, the thiazole and pyrimidine rings are almost co-planar, making a dihedral angle of 2.48 (8)°. In the other molecule, the corresponding dihedral angle is 12.82 (8)°. The crystal structure is stabilized by weak intermolecular N-H
N and C-HO interactions that extend along the b axis.
A mixture of
3-Dimethylamino-1-[2-(methyl-p-tolyl-amino)-4-methyl-thiazol-5-yl]-propenone (1.575 g, 5 mmol) and NaOH (0.2 g, 5 mmol) in 2-methoxylethanol (35 ml) was treated with N-(3-Methoxy-phenyl)-guanidine carbonate (1.476 g, 6.5 mmol). The reaction mixture was heated at 383 K under N2 for 11 h. After concentration, the residue was filtered and washed liberally with ethanol and water. Recrystallization from THF affored the title compound as brown-yellow crystals, 0.97 g, m.p.453–456 K, yield 46.7%.Since the crystal product was not found to be suitable for X-ray diffraction studies,a few crystals were dissolved in 2-butanone, which was allowed to evaporate slowly to give yellow crystals of (I) suitable for X-ray diffraction studies. 1H NMR(CDCl3, TMS, 400 MHz, δp.p.m.): 8.27 (s, 1H, J = 4.8 Hz, py—H), 7.53 (s, 1H, Ar—H), 7.29–7.07 (m, 5H, Ar—H), 6.87 (d, 1H,J = 8.0 Hz, Ar—H), 6.83 (d, 1H, J = 5.2 Hz, py—H), 6.54 (d, 1H, J = 8.0 Hz, Ar—H), 3.64 (s, 3H, OCH3), 3.54 (s, 3H, CH3), 2.60 (s, 3H, CH3), 2.41 (s, 3H, CH3). EIMS m/z (%): 417 (M+,100), 402 (7), 311 (12), 105 (9), 91 (10), 73 (12), 57 (17).
All H atoms were placed in calculated positions (C—H 0.95–0.98 Å, N—H 0.87–0.89 Å) and refined as riding with Uiso(H) = 1.2–1.22Ueq of the parent atom.
Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
![[Figure 1]](./ng5080fig1thm.gif)
| Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids. |
![[Figure 2]](./ng5080fig2thm.gif)
| Fig. 2. Packing of the molecules down b axis. Dashed lines denote intermolecular N—H···N and C—H···O hydrogen bonds. |
| C23H23N5OS | Z = 4 |
| Mr = 417.52 | F(000) = 880 |
| Triclinic, P1 | Dx = 1.379 Mg m−3 |
| Hall symbol: -P 1 | Melting point = 456–453 K |
| a = 10.280 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 12.413 (2) Å | Cell parameters from 5913 reflections |
| c = 17.671 (4) Å | θ = 3.0–27.5° |
| α = 74.290 (9)° | µ = 0.19 mm−1 |
| β = 87.96 (1)° | T = 153 K |
| γ = 68.281 (7)° | Block, yellow |
| V = 2011.3 (8) Å3 | 0.40 × 0.40 × 0.23 mm |
| Rigaku AFC10/Saturn724+ diffractometer | 9061 independent reflections |
| Radiation source: fine-focus sealed tube | 6741 reflections with I > 2σ(I) |
| graphite | Rint = 0.028 |
| Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
| phi and ω scans | h = −13→13 |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008) | k = −16→12 |
| Tmin = 0.929, Tmax = 0.958 | l = −22→21 |
| 19475 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3 |
| 9061 reflections | (Δ/σ)max = 0.002 |
| 551 parameters | Δρmax = 0.34 e Å−3 |
| 0 restraints | Δρmin = −0.25 e Å−3 |
| C23H23N5OS | γ = 68.281 (7)° |
| Mr = 417.52 | V = 2011.3 (8) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 10.280 (3) Å | Mo Kα radiation |
| b = 12.413 (2) Å | µ = 0.19 mm−1 |
| c = 17.671 (4) Å | T = 153 K |
| α = 74.290 (9)° | 0.40 × 0.40 × 0.23 mm |
| β = 87.96 (1)° |
| Rigaku AFC10/Saturn724+ diffractometer | 9061 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008) | 6741 reflections with I > 2σ(I) |
| Tmin = 0.929, Tmax = 0.958 | Rint = 0.028 |
| 19475 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.115 | Δρmax = 0.34 e Å−3 |
| S = 1.03 | Δρmin = −0.25 e Å−3 |
| 9061 reflections | Absolute structure: ? |
| 551 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.50315 (4) | 0.38212 (4) | 0.11927 (2) | 0.02004 (11) | |
| O1 | 0.31361 (12) | 0.76460 (10) | 0.16457 (7) | 0.0297 (3) | |
| N1 | 0.74892 (14) | 0.22921 (12) | 0.20606 (8) | 0.0237 (3) | |
| N2 | 0.66177 (14) | 0.16781 (12) | 0.11226 (8) | 0.0215 (3) | |
| N3 | 0.07766 (14) | 0.54098 (12) | −0.08838 (8) | 0.0226 (3) | |
| N4 | 0.25101 (14) | 0.50344 (11) | 0.01314 (7) | 0.0183 (3) | |
| C1 | 0.61409 (18) | 0.34713 (15) | 0.29291 (9) | 0.0233 (4) | |
| H1 | 0.5369 | 0.3255 | 0.2855 | 0.028* | |
| C2 | 0.60597 (19) | 0.41897 (16) | 0.34179 (10) | 0.0287 (4) | |
| H2 | 0.5222 | 0.4465 | 0.3674 | 0.034* | |
| C3 | 0.7163 (2) | 0.45221 (16) | 0.35466 (10) | 0.0301 (4) | |
| C4 | 0.8380 (2) | 0.40956 (16) | 0.31677 (10) | 0.0307 (4) | |
| H4 | 0.9158 | 0.4298 | 0.3252 | 0.037* | |
| C5 | 0.84791 (18) | 0.33830 (16) | 0.26710 (10) | 0.0264 (4) | |
| H5 | 0.9317 | 0.3108 | 0.2414 | 0.032* | |
| C6 | 0.73559 (17) | 0.30653 (14) | 0.25448 (9) | 0.0202 (3) | |
| C7 | 0.64954 (17) | 0.24899 (14) | 0.14957 (9) | 0.0204 (3) | |
| C8 | 0.55242 (17) | 0.20873 (14) | 0.05698 (9) | 0.0203 (3) | |
| C9 | 0.45492 (16) | 0.32321 (14) | 0.05084 (9) | 0.0186 (3) | |
| C10 | 0.32638 (16) | 0.39460 (14) | 0.00112 (9) | 0.0186 (3) | |
| C11 | 0.27980 (18) | 0.35759 (15) | −0.05700 (10) | 0.0257 (4) | |
| H11 | 0.3320 | 0.2823 | −0.0668 | 0.031* | |
| C12 | 0.15554 (18) | 0.43451 (15) | −0.09934 (10) | 0.0266 (4) | |
| H12 | 0.1230 | 0.4102 | −0.1391 | 0.032* | |
| C13 | 0.13195 (16) | 0.57067 (14) | −0.03208 (9) | 0.0191 (3) | |
| C14 | 0.06599 (17) | 0.74316 (14) | 0.02929 (9) | 0.0202 (3) | |
| C15 | −0.05486 (18) | 0.83747 (15) | 0.03962 (10) | 0.0272 (4) | |
| H15 | −0.1416 | 0.8547 | 0.0126 | 0.033* | |
| C16 | −0.04857 (19) | 0.90526 (16) | 0.08867 (10) | 0.0316 (4) | |
| H16 | −0.1305 | 0.9703 | 0.0941 | 0.038* | |
| C17 | 0.07593 (19) | 0.87930 (15) | 0.12995 (10) | 0.0278 (4) | |
| H17 | 0.0801 | 0.9256 | 0.1641 | 0.033* | |
| C18 | 0.19478 (17) | 0.78470 (14) | 0.12089 (10) | 0.0225 (4) | |
| C19 | 0.19246 (17) | 0.71745 (14) | 0.07009 (9) | 0.0213 (4) | |
| H19 | 0.2757 | 0.6549 | 0.0632 | 0.026* | |
| C20 | 0.7059 (3) | 0.52907 (19) | 0.40976 (12) | 0.0483 (6) | |
| H20A | 0.7917 | 0.5462 | 0.4096 | 0.058* | |
| H20B | 0.6946 | 0.4857 | 0.4633 | 0.058* | |
| H20C | 0.6248 | 0.6051 | 0.3921 | 0.058* | |
| C21 | 0.87705 (18) | 0.12023 (16) | 0.21626 (11) | 0.0303 (4) | |
| H21A | 0.8514 | 0.0509 | 0.2184 | 0.036* | |
| H21B | 0.9303 | 0.1054 | 0.2654 | 0.036* | |
| H21C | 0.9348 | 0.1318 | 0.1717 | 0.036* | |
| C22 | 0.55248 (19) | 0.12289 (15) | 0.01110 (10) | 0.0276 (4) | |
| H22A | 0.6287 | 0.0447 | 0.0330 | 0.033* | |
| H22B | 0.5664 | 0.1557 | −0.0442 | 0.033* | |
| H22C | 0.4624 | 0.1123 | 0.0147 | 0.033* | |
| C23 | 0.42224 (18) | 0.64788 (16) | 0.17922 (11) | 0.0312 (4) | |
| H23A | 0.3823 | 0.5860 | 0.1995 | 0.037* | |
| H23B | 0.4933 | 0.6396 | 0.2182 | 0.037* | |
| H23C | 0.4658 | 0.6378 | 0.1301 | 0.037* | |
| S1' | 0.62905 (4) | 0.02186 (4) | 0.35481 (2) | 0.02269 (11) | |
| O1' | 0.32556 (14) | 0.34116 (11) | 0.45343 (7) | 0.0364 (3) | |
| N1' | 0.86877 (15) | −0.12792 (13) | 0.44911 (8) | 0.0268 (3) | |
| N2' | 0.81090 (15) | −0.18076 (13) | 0.34154 (9) | 0.0273 (3) | |
| N3' | 0.21894 (15) | 0.16941 (12) | 0.14055 (8) | 0.0236 (3) | |
| N4' | 0.39489 (14) | 0.14313 (11) | 0.23753 (8) | 0.0188 (3) | |
| C1' | 0.80415 (18) | 0.07463 (16) | 0.46503 (10) | 0.0269 (4) | |
| H1' | 0.8030 | 0.1065 | 0.4096 | 0.032* | |
| C2' | 0.7700 (2) | 0.15134 (17) | 0.51301 (11) | 0.0312 (4) | |
| H2' | 0.7424 | 0.2357 | 0.4895 | 0.037* | |
| C3' | 0.7748 (2) | 0.10854 (18) | 0.59446 (11) | 0.0336 (4) | |
| C4' | 0.8157 (2) | −0.01508 (18) | 0.62604 (11) | 0.0324 (4) | |
| H4' | 0.8218 | −0.0473 | 0.6816 | 0.039* | |
| C5' | 0.84775 (19) | −0.09272 (17) | 0.57929 (10) | 0.0279 (4) | |
| H5' | 0.8753 | −0.1770 | 0.6030 | 0.033* | |
| C6' | 0.84012 (17) | −0.04864 (16) | 0.49739 (10) | 0.0250 (4) | |
| C7' | 0.78435 (17) | −0.10428 (15) | 0.38390 (10) | 0.0237 (4) | |
| C8' | 0.70529 (18) | −0.14324 (15) | 0.28392 (10) | 0.0259 (4) | |
| C9' | 0.59585 (17) | −0.03712 (14) | 0.28235 (9) | 0.0212 (4) | |
| C10' | 0.46677 (17) | 0.02952 (14) | 0.23224 (9) | 0.0204 (3) | |
| C11' | 0.41421 (19) | −0.01837 (16) | 0.18333 (10) | 0.0269 (4) | |
| H11' | 0.4618 | −0.0989 | 0.1807 | 0.032* | |
| C12' | 0.29073 (19) | 0.05571 (15) | 0.13900 (10) | 0.0270 (4) | |
| H12' | 0.2542 | 0.0242 | 0.1052 | 0.032* | |
| C13' | 0.27571 (17) | 0.20653 (14) | 0.19190 (9) | 0.0195 (3) | |
| C14' | 0.20829 (16) | 0.38181 (14) | 0.24965 (9) | 0.0194 (3) | |
| C15' | 0.13941 (18) | 0.50655 (15) | 0.22759 (10) | 0.0260 (4) | |
| H15' | 0.0979 | 0.5474 | 0.1755 | 0.031* | |
| C16' | 0.1311 (2) | 0.57126 (16) | 0.28114 (12) | 0.0328 (4) | |
| H16' | 0.0825 | 0.6563 | 0.2658 | 0.039* | |
| C17' | 0.1926 (2) | 0.51390 (16) | 0.35649 (11) | 0.0327 (4) | |
| H17' | 0.1850 | 0.5586 | 0.3935 | 0.039* | |
| C18' | 0.26553 (18) | 0.39037 (16) | 0.37766 (10) | 0.0251 (4) | |
| C19' | 0.27451 (17) | 0.32300 (15) | 0.32526 (9) | 0.0210 (3) | |
| H19' | 0.3249 | 0.2382 | 0.3405 | 0.025* | |
| C20' | 0.7379 (3) | 0.1922 (2) | 0.64597 (13) | 0.0567 (7) | |
| H20D | 0.6760 | 0.1704 | 0.6856 | 0.068* | |
| H20E | 0.6897 | 0.2754 | 0.6136 | 0.068* | |
| H20F | 0.8238 | 0.1856 | 0.6724 | 0.068* | |
| C21' | 0.96868 (19) | −0.25356 (16) | 0.47869 (12) | 0.0358 (5) | |
| H21D | 0.9171 | −0.3061 | 0.5006 | 0.043* | |
| H21E | 1.0339 | −0.2588 | 0.5199 | 0.043* | |
| H21F | 1.0214 | −0.2794 | 0.4353 | 0.043* | |
| C22' | 0.7241 (2) | −0.22037 (18) | 0.22881 (12) | 0.0422 (5) | |
| H22D | 0.8231 | −0.2735 | 0.2320 | 0.051* | |
| H22E | 0.6952 | −0.1686 | 0.1747 | 0.051* | |
| H22F | 0.6664 | −0.2693 | 0.2438 | 0.051* | |
| C23' | 0.4145 (2) | 0.21765 (16) | 0.47661 (10) | 0.0311 (4) | |
| H23D | 0.3615 | 0.1684 | 0.4712 | 0.037* | |
| H23E | 0.4501 | 0.1951 | 0.5317 | 0.037* | |
| H23F | 0.4936 | 0.2039 | 0.4430 | 0.037* | |
| N5 | 0.05080 (14) | 0.68186 (12) | −0.02343 (8) | 0.0225 (3) | |
| H0 | −0.0238 | 0.7215 | −0.0569 | 0.036 (6)* | |
| N5' | 0.19792 (14) | 0.32157 (12) | 0.19486 (8) | 0.0212 (3) | |
| H0' | 0.1314 | 0.3641 | 0.1567 | 0.029 (5)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.01671 (19) | 0.0193 (2) | 0.0227 (2) | −0.00196 (15) | −0.00337 (16) | −0.00978 (17) |
| O1 | 0.0243 (6) | 0.0262 (7) | 0.0397 (7) | −0.0040 (5) | −0.0083 (6) | −0.0170 (6) |
| N1 | 0.0176 (7) | 0.0247 (8) | 0.0249 (7) | 0.0006 (6) | −0.0038 (6) | −0.0121 (6) |
| N2 | 0.0193 (7) | 0.0222 (7) | 0.0209 (7) | −0.0032 (5) | −0.0003 (6) | −0.0090 (6) |
| N3 | 0.0186 (7) | 0.0256 (8) | 0.0212 (7) | −0.0033 (6) | −0.0033 (6) | −0.0094 (6) |
| N4 | 0.0169 (6) | 0.0182 (7) | 0.0180 (7) | −0.0034 (5) | 0.0000 (5) | −0.0067 (5) |
| C1 | 0.0204 (8) | 0.0272 (9) | 0.0201 (8) | −0.0070 (7) | −0.0018 (7) | −0.0053 (7) |
| C2 | 0.0279 (9) | 0.0303 (10) | 0.0222 (9) | −0.0042 (7) | 0.0002 (7) | −0.0076 (8) |
| C3 | 0.0407 (11) | 0.0258 (9) | 0.0211 (9) | −0.0085 (8) | −0.0074 (8) | −0.0065 (7) |
| C4 | 0.0348 (10) | 0.0340 (10) | 0.0270 (9) | −0.0183 (8) | −0.0060 (8) | −0.0056 (8) |
| C5 | 0.0233 (9) | 0.0352 (10) | 0.0213 (9) | −0.0132 (7) | 0.0009 (7) | −0.0059 (8) |
| C6 | 0.0199 (8) | 0.0206 (8) | 0.0163 (8) | −0.0041 (6) | −0.0031 (6) | −0.0036 (7) |
| C7 | 0.0177 (8) | 0.0201 (8) | 0.0207 (8) | −0.0041 (6) | 0.0008 (6) | −0.0052 (7) |
| C8 | 0.0205 (8) | 0.0204 (8) | 0.0196 (8) | −0.0053 (6) | 0.0023 (6) | −0.0084 (7) |
| C9 | 0.0179 (8) | 0.0200 (8) | 0.0185 (8) | −0.0054 (6) | 0.0003 (6) | −0.0084 (7) |
| C10 | 0.0165 (7) | 0.0203 (8) | 0.0186 (8) | −0.0055 (6) | 0.0018 (6) | −0.0071 (7) |
| C11 | 0.0212 (8) | 0.0255 (9) | 0.0292 (9) | −0.0010 (7) | −0.0036 (7) | −0.0160 (8) |
| C12 | 0.0244 (9) | 0.0309 (10) | 0.0253 (9) | −0.0064 (7) | −0.0042 (7) | −0.0141 (8) |
| C13 | 0.0181 (8) | 0.0217 (8) | 0.0162 (8) | −0.0061 (6) | 0.0017 (6) | −0.0054 (6) |
| C14 | 0.0224 (8) | 0.0186 (8) | 0.0178 (8) | −0.0044 (6) | −0.0012 (7) | −0.0064 (7) |
| C15 | 0.0222 (9) | 0.0257 (9) | 0.0271 (9) | 0.0008 (7) | −0.0066 (7) | −0.0099 (8) |
| C16 | 0.0251 (9) | 0.0278 (10) | 0.0356 (10) | 0.0027 (7) | −0.0046 (8) | −0.0160 (8) |
| C17 | 0.0290 (9) | 0.0237 (9) | 0.0311 (10) | −0.0038 (7) | −0.0019 (8) | −0.0162 (8) |
| C18 | 0.0218 (8) | 0.0205 (8) | 0.0252 (9) | −0.0073 (7) | −0.0023 (7) | −0.0064 (7) |
| C19 | 0.0190 (8) | 0.0201 (8) | 0.0233 (8) | −0.0041 (6) | 0.0005 (7) | −0.0081 (7) |
| C20 | 0.0673 (16) | 0.0416 (12) | 0.0410 (12) | −0.0169 (11) | −0.0073 (11) | −0.0226 (10) |
| C21 | 0.0207 (9) | 0.0302 (10) | 0.0326 (10) | 0.0022 (7) | −0.0060 (8) | −0.0126 (8) |
| C22 | 0.0285 (9) | 0.0221 (9) | 0.0294 (9) | −0.0019 (7) | −0.0033 (8) | −0.0130 (7) |
| C23 | 0.0217 (9) | 0.0282 (10) | 0.0412 (11) | −0.0024 (7) | −0.0087 (8) | −0.0139 (8) |
| S1' | 0.0201 (2) | 0.0222 (2) | 0.0229 (2) | −0.00219 (16) | −0.00535 (17) | −0.00906 (17) |
| O1' | 0.0433 (8) | 0.0365 (8) | 0.0248 (7) | −0.0039 (6) | −0.0043 (6) | −0.0159 (6) |
| N1' | 0.0207 (7) | 0.0268 (8) | 0.0279 (8) | −0.0031 (6) | −0.0071 (6) | −0.0064 (6) |
| N2' | 0.0223 (7) | 0.0244 (8) | 0.0308 (8) | −0.0016 (6) | −0.0017 (6) | −0.0104 (7) |
| N3' | 0.0215 (7) | 0.0252 (8) | 0.0238 (7) | −0.0068 (6) | −0.0044 (6) | −0.0081 (6) |
| N4' | 0.0176 (7) | 0.0187 (7) | 0.0187 (7) | −0.0053 (5) | −0.0003 (5) | −0.0049 (5) |
| C1' | 0.0254 (9) | 0.0333 (10) | 0.0225 (9) | −0.0136 (7) | −0.0051 (7) | −0.0040 (8) |
| C2' | 0.0342 (10) | 0.0330 (10) | 0.0298 (10) | −0.0180 (8) | −0.0047 (8) | −0.0057 (8) |
| C3' | 0.0375 (11) | 0.0421 (12) | 0.0317 (10) | −0.0235 (9) | 0.0017 (8) | −0.0145 (9) |
| C4' | 0.0332 (10) | 0.0455 (12) | 0.0233 (9) | −0.0225 (9) | −0.0010 (8) | −0.0057 (8) |
| C5' | 0.0252 (9) | 0.0315 (10) | 0.0254 (9) | −0.0137 (7) | −0.0068 (7) | −0.0001 (8) |
| C6' | 0.0160 (8) | 0.0310 (10) | 0.0280 (9) | −0.0091 (7) | −0.0041 (7) | −0.0071 (8) |
| C7' | 0.0194 (8) | 0.0235 (9) | 0.0250 (9) | −0.0052 (7) | −0.0009 (7) | −0.0052 (7) |
| C8' | 0.0240 (9) | 0.0236 (9) | 0.0286 (9) | −0.0041 (7) | 0.0000 (7) | −0.0112 (7) |
| C9' | 0.0229 (8) | 0.0195 (8) | 0.0200 (8) | −0.0057 (7) | −0.0022 (7) | −0.0062 (7) |
| C10' | 0.0221 (8) | 0.0208 (8) | 0.0175 (8) | −0.0072 (6) | 0.0006 (7) | −0.0050 (7) |
| C11' | 0.0287 (9) | 0.0236 (9) | 0.0281 (9) | −0.0069 (7) | −0.0039 (8) | −0.0101 (7) |
| C12' | 0.0310 (10) | 0.0288 (10) | 0.0245 (9) | −0.0114 (8) | −0.0038 (8) | −0.0114 (8) |
| C13' | 0.0190 (8) | 0.0224 (8) | 0.0165 (8) | −0.0081 (6) | 0.0017 (6) | −0.0043 (7) |
| C14' | 0.0133 (7) | 0.0231 (8) | 0.0230 (8) | −0.0077 (6) | 0.0025 (6) | −0.0070 (7) |
| C15' | 0.0223 (9) | 0.0244 (9) | 0.0295 (9) | −0.0076 (7) | −0.0030 (7) | −0.0057 (7) |
| C16' | 0.0289 (10) | 0.0208 (9) | 0.0463 (12) | −0.0051 (7) | −0.0039 (9) | −0.0105 (8) |
| C17' | 0.0318 (10) | 0.0302 (10) | 0.0396 (11) | −0.0071 (8) | 0.0013 (9) | −0.0213 (9) |
| C18' | 0.0223 (8) | 0.0304 (9) | 0.0239 (9) | −0.0086 (7) | 0.0015 (7) | −0.0114 (7) |
| C19' | 0.0178 (8) | 0.0220 (8) | 0.0233 (8) | −0.0063 (6) | 0.0033 (7) | −0.0082 (7) |
| C20' | 0.091 (2) | 0.0563 (15) | 0.0408 (13) | −0.0408 (14) | 0.0134 (13) | −0.0252 (11) |
| C21' | 0.0256 (10) | 0.0303 (10) | 0.0405 (11) | 0.0005 (8) | −0.0110 (9) | −0.0064 (9) |
| C22' | 0.0319 (11) | 0.0401 (12) | 0.0520 (13) | 0.0012 (9) | −0.0059 (10) | −0.0285 (10) |
| C23' | 0.0325 (10) | 0.0335 (10) | 0.0235 (9) | −0.0081 (8) | −0.0051 (8) | −0.0073 (8) |
| N5 | 0.0193 (7) | 0.0212 (7) | 0.0225 (7) | −0.0002 (6) | −0.0070 (6) | −0.0083 (6) |
| N5' | 0.0179 (7) | 0.0220 (7) | 0.0209 (7) | −0.0035 (5) | −0.0043 (6) | −0.0064 (6) |
| S1—C7 | 1.7377 (16) | S1'—C7' | 1.7427 (17) |
| S1—C9 | 1.7414 (16) | O1'—C18' | 1.372 (2) |
| O1—C18 | 1.3739 (19) | O1'—C23' | 1.416 (2) |
| O1—C23 | 1.4259 (19) | N1'—C7' | 1.366 (2) |
| N1—C7 | 1.362 (2) | N1'—C6' | 1.416 (2) |
| N1—C6 | 1.418 (2) | N1'—C21' | 1.474 (2) |
| N1—C21 | 1.4709 (19) | N2'—C7' | 1.309 (2) |
| N2—C7 | 1.314 (2) | N2'—C8' | 1.371 (2) |
| N2—C8 | 1.365 (2) | N3'—C12' | 1.336 (2) |
| N3—C12 | 1.330 (2) | N3'—C13' | 1.356 (2) |
| N3—C13 | 1.352 (2) | N4'—C13' | 1.336 (2) |
| N4—C13 | 1.3362 (19) | N4'—C10' | 1.356 (2) |
| N4—C10 | 1.3563 (19) | C1'—C2' | 1.385 (2) |
| C1—C2 | 1.380 (2) | C1'—C6' | 1.388 (2) |
| C1—C6 | 1.391 (2) | C1'—H1' | 0.9500 |
| C1—H1 | 0.9500 | C2'—C3' | 1.389 (3) |
| C2—C3 | 1.387 (3) | C2'—H2' | 0.9500 |
| C2—H2 | 0.9500 | C3'—C4' | 1.385 (3) |
| C3—C4 | 1.391 (3) | C3'—C20' | 1.499 (3) |
| C3—C20 | 1.513 (2) | C4'—C5' | 1.377 (3) |
| C4—C5 | 1.382 (2) | C4'—H4' | 0.9500 |
| C4—H4 | 0.9500 | C5'—C6' | 1.395 (2) |
| C5—C6 | 1.393 (2) | C5'—H5' | 0.9500 |
| C5—H5 | 0.9500 | C8'—C9' | 1.374 (2) |
| C8—C9 | 1.381 (2) | C8'—C22' | 1.502 (2) |
| C8—C22 | 1.503 (2) | C9'—C10' | 1.450 (2) |
| C9—C10 | 1.448 (2) | C10'—C11' | 1.393 (2) |
| C10—C11 | 1.396 (2) | C11'—C12' | 1.374 (2) |
| C11—C12 | 1.372 (2) | C11'—H11' | 0.9500 |
| C11—H11 | 0.9500 | C12'—H12' | 0.9500 |
| C12—H12 | 0.9500 | C13'—N5' | 1.369 (2) |
| C13—N5 | 1.370 (2) | C14'—C15' | 1.390 (2) |
| C14—C19 | 1.395 (2) | C14'—C19' | 1.396 (2) |
| C14—N5 | 1.398 (2) | C14'—N5' | 1.402 (2) |
| C14—C15 | 1.404 (2) | C15'—C16' | 1.380 (2) |
| C15—C16 | 1.379 (2) | C15'—H15' | 0.9500 |
| C15—H15 | 0.9500 | C16'—C17' | 1.376 (3) |
| C16—C17 | 1.381 (2) | C16'—H16' | 0.9500 |
| C16—H16 | 0.9500 | C17'—C18' | 1.383 (2) |
| C17—C18 | 1.387 (2) | C17'—H17' | 0.9500 |
| C17—H17 | 0.9500 | C18'—C19' | 1.386 (2) |
| C18—C19 | 1.388 (2) | C19'—H19' | 0.9500 |
| C19—H19 | 0.9500 | C20'—H20D | 0.9800 |
| C20—H20A | 0.9800 | C20'—H20E | 0.9800 |
| C20—H20B | 0.9800 | C20'—H20F | 0.9800 |
| C20—H20C | 0.9800 | C21'—H21D | 0.9800 |
| C21—H21A | 0.9800 | C21'—H21E | 0.9800 |
| C21—H21B | 0.9800 | C21'—H21F | 0.9800 |
| C21—H21C | 0.9800 | C22'—H22D | 0.9800 |
| C22—H22A | 0.9800 | C22'—H22E | 0.9800 |
| C22—H22B | 0.9800 | C22'—H22F | 0.9800 |
| C22—H22C | 0.9800 | C23'—H23D | 0.9800 |
| C23—H23A | 0.9800 | C23'—H23E | 0.9800 |
| C23—H23B | 0.9800 | C23'—H23F | 0.9800 |
| C23—H23C | 0.9800 | N5—H0 | 0.8800 |
| S1'—C9' | 1.7367 (16) | N5'—H0' | 0.8800 |
| C7—S1—C9 | 88.64 (8) | C7'—N1'—C21' | 115.57 (15) |
| C18—O1—C23 | 116.99 (13) | C6'—N1'—C21' | 119.97 (14) |
| C7—N1—C6 | 124.09 (13) | C7'—N2'—C8' | 110.83 (14) |
| C7—N1—C21 | 116.77 (14) | C12'—N3'—C13' | 114.45 (14) |
| C6—N1—C21 | 119.14 (13) | C13'—N4'—C10' | 116.72 (14) |
| C7—N2—C8 | 110.62 (13) | C2'—C1'—C6' | 120.40 (16) |
| C12—N3—C13 | 114.57 (13) | C2'—C1'—H1' | 119.8 |
| C13—N4—C10 | 117.02 (14) | C6'—C1'—H1' | 119.8 |
| C2—C1—C6 | 119.79 (17) | C1'—C2'—C3' | 121.91 (18) |
| C2—C1—H1 | 120.1 | C1'—C2'—H2' | 119.0 |
| C6—C1—H1 | 120.1 | C3'—C2'—H2' | 119.0 |
| C1—C2—C3 | 122.08 (17) | C4'—C3'—C2' | 116.98 (18) |
| C1—C2—H2 | 119.0 | C4'—C3'—C20' | 121.47 (18) |
| C3—C2—H2 | 119.0 | C2'—C3'—C20' | 121.55 (18) |
| C2—C3—C4 | 117.55 (17) | C5'—C4'—C3' | 122.02 (17) |
| C2—C3—C20 | 121.09 (19) | C5'—C4'—H4' | 119.0 |
| C4—C3—C20 | 121.34 (19) | C3'—C4'—H4' | 119.0 |
| C5—C4—C3 | 121.29 (17) | C4'—C5'—C6' | 120.58 (17) |
| C5—C4—H4 | 119.4 | C4'—C5'—H5' | 119.7 |
| C3—C4—H4 | 119.4 | C6'—C5'—H5' | 119.7 |
| C4—C5—C6 | 120.32 (17) | C1'—C6'—C5' | 118.04 (16) |
| C4—C5—H5 | 119.8 | C1'—C6'—N1' | 121.29 (15) |
| C6—C5—H5 | 119.8 | C5'—C6'—N1' | 120.66 (16) |
| C1—C6—C5 | 118.96 (16) | N2'—C7'—N1' | 121.33 (15) |
| C1—C6—N1 | 121.09 (15) | N2'—C7'—S1' | 115.06 (12) |
| C5—C6—N1 | 119.88 (15) | N1'—C7'—S1' | 123.46 (13) |
| N2—C7—N1 | 121.04 (14) | N2'—C8'—C9' | 115.64 (15) |
| N2—C7—S1 | 115.41 (12) | N2'—C8'—C22' | 116.69 (15) |
| N1—C7—S1 | 123.51 (13) | C9'—C8'—C22' | 127.65 (16) |
| N2—C8—C9 | 115.91 (14) | C8'—C9'—C10' | 131.90 (15) |
| N2—C8—C22 | 115.90 (14) | C8'—C9'—S1' | 109.75 (12) |
| C9—C8—C22 | 128.19 (15) | C10'—C9'—S1' | 118.34 (12) |
| C8—C9—C10 | 131.61 (15) | N4'—C10'—C11' | 120.66 (14) |
| C8—C9—S1 | 109.42 (12) | N4'—C10'—C9' | 115.53 (14) |
| C10—C9—S1 | 118.95 (12) | C11'—C10'—C9' | 123.78 (15) |
| N4—C10—C11 | 120.22 (14) | C12'—C11'—C10' | 117.26 (16) |
| N4—C10—C9 | 116.07 (14) | C12'—C11'—H11' | 121.4 |
| C11—C10—C9 | 123.70 (14) | C10'—C11'—H11' | 121.4 |
| C12—C11—C10 | 117.24 (15) | N3'—C12'—C11' | 123.97 (16) |
| C12—C11—H11 | 121.4 | N3'—C12'—H12' | 118.0 |
| C10—C11—H11 | 121.4 | C11'—C12'—H12' | 118.0 |
| N3—C12—C11 | 124.25 (15) | N4'—C13'—N3' | 126.86 (15) |
| N3—C12—H12 | 117.9 | N4'—C13'—N5' | 119.53 (14) |
| C11—C12—H12 | 117.9 | N3'—C13'—N5' | 113.61 (14) |
| N4—C13—N3 | 126.68 (14) | C15'—C14'—C19' | 119.57 (15) |
| N4—C13—N5 | 120.21 (14) | C15'—C14'—N5' | 116.54 (14) |
| N3—C13—N5 | 113.11 (13) | C19'—C14'—N5' | 123.74 (14) |
| C19—C14—N5 | 124.14 (14) | C16'—C15'—C14' | 120.21 (16) |
| C19—C14—C15 | 119.27 (15) | C16'—C15'—H15' | 119.9 |
| N5—C14—C15 | 116.57 (14) | C14'—C15'—H15' | 119.9 |
| C16—C15—C14 | 120.50 (16) | C17'—C16'—C15' | 120.70 (17) |
| C16—C15—H15 | 119.7 | C17'—C16'—H16' | 119.6 |
| C14—C15—H15 | 119.7 | C15'—C16'—H16' | 119.6 |
| C15—C16—C17 | 120.48 (16) | C16'—C17'—C18' | 119.15 (17) |
| C15—C16—H16 | 119.8 | C16'—C17'—H17' | 120.4 |
| C17—C16—H16 | 119.8 | C18'—C17'—H17' | 120.4 |
| C16—C17—C18 | 119.04 (16) | O1'—C18'—C17' | 115.16 (15) |
| C16—C17—H17 | 120.5 | O1'—C18'—C19' | 123.49 (15) |
| C18—C17—H17 | 120.5 | C17'—C18'—C19' | 121.34 (16) |
| O1—C18—C17 | 115.16 (15) | C18'—C19'—C14' | 118.95 (15) |
| O1—C18—C19 | 123.15 (14) | C18'—C19'—H19' | 120.5 |
| C17—C18—C19 | 121.68 (15) | C14'—C19'—H19' | 120.5 |
| C18—C19—C14 | 118.98 (15) | C3'—C20'—H20D | 109.5 |
| C18—C19—H19 | 120.5 | C3'—C20'—H20E | 109.5 |
| C14—C19—H19 | 120.5 | H20D—C20'—H20E | 109.5 |
| C3—C20—H20A | 109.5 | C3'—C20'—H20F | 109.5 |
| C3—C20—H20B | 109.5 | H20D—C20'—H20F | 109.5 |
| H20A—C20—H20B | 109.5 | H20E—C20'—H20F | 109.5 |
| C3—C20—H20C | 109.5 | N1'—C21'—H21D | 109.5 |
| H20A—C20—H20C | 109.5 | N1'—C21'—H21E | 109.5 |
| H20B—C20—H20C | 109.5 | H21D—C21'—H21E | 109.5 |
| N1—C21—H21A | 109.5 | N1'—C21'—H21F | 109.5 |
| N1—C21—H21B | 109.5 | H21D—C21'—H21F | 109.5 |
| H21A—C21—H21B | 109.5 | H21E—C21'—H21F | 109.5 |
| N1—C21—H21C | 109.5 | C8'—C22'—H22D | 109.5 |
| H21A—C21—H21C | 109.5 | C8'—C22'—H22E | 109.5 |
| H21B—C21—H21C | 109.5 | H22D—C22'—H22E | 109.5 |
| C8—C22—H22A | 109.5 | C8'—C22'—H22F | 109.5 |
| C8—C22—H22B | 109.5 | H22D—C22'—H22F | 109.5 |
| H22A—C22—H22B | 109.5 | H22E—C22'—H22F | 109.5 |
| C8—C22—H22C | 109.5 | O1'—C23'—H23D | 109.5 |
| H22A—C22—H22C | 109.5 | O1'—C23'—H23E | 109.5 |
| H22B—C22—H22C | 109.5 | H23D—C23'—H23E | 109.5 |
| O1—C23—H23A | 109.5 | O1'—C23'—H23F | 109.5 |
| O1—C23—H23B | 109.5 | H23D—C23'—H23F | 109.5 |
| H23A—C23—H23B | 109.5 | H23E—C23'—H23F | 109.5 |
| O1—C23—H23C | 109.5 | C13—N5—C14 | 131.15 (13) |
| H23A—C23—H23C | 109.5 | C13—N5—H0 | 114.4 |
| H23B—C23—H23C | 109.5 | C14—N5—H0 | 114.4 |
| C9'—S1'—C7' | 88.66 (8) | C13'—N5'—C14' | 129.69 (13) |
| C18'—O1'—C23' | 118.32 (13) | C13'—N5'—H0' | 115.2 |
| C7'—N1'—C6' | 122.53 (14) | C14'—N5'—H0' | 115.2 |
| C6—C1—C2—C3 | −0.4 (3) | C20'—C3'—C4'—C5' | 178.9 (2) |
| C1—C2—C3—C4 | −0.5 (3) | C3'—C4'—C5'—C6' | 0.1 (3) |
| C1—C2—C3—C20 | −178.81 (17) | C2'—C1'—C6'—C5' | −3.3 (3) |
| C2—C3—C4—C5 | 1.0 (3) | C2'—C1'—C6'—N1' | 176.88 (16) |
| C20—C3—C4—C5 | 179.31 (17) | C4'—C5'—C6'—C1' | 2.2 (3) |
| C3—C4—C5—C6 | −0.6 (3) | C4'—C5'—C6'—N1' | −178.01 (16) |
| C2—C1—C6—C5 | 0.8 (2) | C7'—N1'—C6'—C1' | −46.7 (3) |
| C2—C1—C6—N1 | 177.79 (14) | C21'—N1'—C6'—C1' | 149.80 (17) |
| C4—C5—C6—C1 | −0.3 (2) | C7'—N1'—C6'—C5' | 133.47 (18) |
| C4—C5—C6—N1 | −177.33 (15) | C21'—N1'—C6'—C5' | −30.0 (2) |
| C7—N1—C6—C1 | 48.2 (2) | C8'—N2'—C7'—N1' | 174.26 (16) |
| C21—N1—C6—C1 | −131.79 (17) | C8'—N2'—C7'—S1' | −1.4 (2) |
| C7—N1—C6—C5 | −134.82 (18) | C6'—N1'—C7'—N2' | −177.96 (16) |
| C21—N1—C6—C5 | 45.2 (2) | C21'—N1'—C7'—N2' | −13.8 (3) |
| C8—N2—C7—N1 | −178.21 (15) | C6'—N1'—C7'—S1' | −2.7 (3) |
| C8—N2—C7—S1 | −0.28 (19) | C21'—N1'—C7'—S1' | 161.47 (14) |
| C6—N1—C7—N2 | −172.95 (15) | C9'—S1'—C7'—N2' | 2.15 (15) |
| C21—N1—C7—N2 | 7.1 (2) | C9'—S1'—C7'—N1' | −173.40 (17) |
| C6—N1—C7—S1 | 9.3 (2) | C7'—N2'—C8'—C9' | −0.5 (2) |
| C21—N1—C7—S1 | −170.69 (13) | C7'—N2'—C8'—C22' | 177.95 (17) |
| C9—S1—C7—N2 | 0.00 (14) | N2'—C8'—C9'—C10' | −178.95 (18) |
| C9—S1—C7—N1 | 177.87 (16) | C22'—C8'—C9'—C10' | 2.9 (3) |
| C7—N2—C8—C9 | 0.5 (2) | N2'—C8'—C9'—S1' | 2.0 (2) |
| C7—N2—C8—C22 | −178.81 (15) | C22'—C8'—C9'—S1' | −176.16 (17) |
| N2—C8—C9—C10 | −178.73 (17) | C7'—S1'—C9'—C8' | −2.23 (14) |
| C22—C8—C9—C10 | 0.5 (3) | C7'—S1'—C9'—C10' | 178.60 (15) |
| N2—C8—C9—S1 | −0.52 (19) | C13'—N4'—C10'—C11' | −2.3 (2) |
| C22—C8—C9—S1 | 178.71 (15) | C13'—N4'—C10'—C9' | 179.90 (15) |
| C7—S1—C9—C8 | 0.28 (13) | C8'—C9'—C10'—N4' | −167.75 (18) |
| C7—S1—C9—C10 | 178.75 (14) | S1'—C9'—C10'—N4' | 11.2 (2) |
| C13—N4—C10—C11 | 0.7 (2) | C8'—C9'—C10'—C11' | 14.5 (3) |
| C13—N4—C10—C9 | −179.93 (15) | S1'—C9'—C10'—C11' | −166.56 (14) |
| C8—C9—C10—N4 | 177.00 (17) | N4'—C10'—C11'—C12' | 2.5 (3) |
| S1—C9—C10—N4 | −1.1 (2) | C9'—C10'—C11'—C12' | −179.83 (17) |
| C8—C9—C10—C11 | −3.7 (3) | C13'—N3'—C12'—C11' | −1.8 (3) |
| S1—C9—C10—C11 | 178.22 (14) | C10'—C11'—C12'—N3' | −0.4 (3) |
| N4—C10—C11—C12 | −1.0 (3) | C10'—N4'—C13'—N3' | −0.2 (3) |
| C9—C10—C11—C12 | 179.69 (17) | C10'—N4'—C13'—N5' | 179.63 (15) |
| C13—N3—C12—C11 | 1.3 (3) | C12'—N3'—C13'—N4' | 2.2 (3) |
| C10—C11—C12—N3 | −0.1 (3) | C12'—N3'—C13'—N5' | −177.63 (15) |
| C10—N4—C13—N3 | 0.7 (3) | C19'—C14'—C15'—C16' | −2.9 (3) |
| C10—N4—C13—N5 | −179.70 (15) | N5'—C14'—C15'—C16' | 172.79 (16) |
| C12—N3—C13—N4 | −1.7 (3) | C14'—C15'—C16'—C17' | 1.1 (3) |
| C12—N3—C13—N5 | 178.67 (15) | C15'—C16'—C17'—C18' | 1.3 (3) |
| C19—C14—C15—C16 | 0.9 (3) | C23'—O1'—C18'—C17' | −173.22 (17) |
| N5—C14—C15—C16 | −178.00 (16) | C23'—O1'—C18'—C19' | 7.4 (3) |
| C14—C15—C16—C17 | −1.7 (3) | C16'—C17'—C18'—O1' | 178.81 (18) |
| C15—C16—C17—C18 | 0.5 (3) | C16'—C17'—C18'—C19' | −1.8 (3) |
| C23—O1—C18—C17 | 158.88 (17) | O1'—C18'—C19'—C14' | 179.33 (16) |
| C23—O1—C18—C19 | −22.2 (2) | C17'—C18'—C19'—C14' | 0.0 (3) |
| C16—C17—C18—O1 | −179.50 (16) | C15'—C14'—C19'—C18' | 2.3 (2) |
| C16—C17—C18—C19 | 1.5 (3) | N5'—C14'—C19'—C18' | −173.03 (15) |
| O1—C18—C19—C14 | 178.81 (15) | N4—C13—N5—C14 | −2.6 (3) |
| C17—C18—C19—C14 | −2.3 (3) | N3—C13—N5—C14 | 177.09 (16) |
| N5—C14—C19—C18 | 179.88 (15) | C19—C14—N5—C13 | 20.4 (3) |
| C15—C14—C19—C18 | 1.1 (3) | C15—C14—N5—C13 | −160.71 (17) |
| C6'—C1'—C2'—C3' | 2.3 (3) | N4'—C13'—N5'—C14' | −12.8 (3) |
| C1'—C2'—C3'—C4' | 0.0 (3) | N3'—C13'—N5'—C14' | 167.01 (16) |
| C1'—C2'—C3'—C20' | 179.9 (2) | C15'—C14'—N5'—C13' | 164.55 (17) |
| C2'—C3'—C4'—C5' | −1.2 (3) | C19'—C14'—N5'—C13' | −20.0 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H0···N3'i | 0.88 | 2.27 | 3.151 (2) | 177 |
| N5'—H0'···N3i | 0.88 | 2.24 | 3.089 (2) | 164 |
| C22—H22B···O1ii | 0.98 | 2.57 | 3.500 (2) | 159 |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H0···N3'i | 0.88 | 2.27 | 3.151 (2) | 177 |
| N5'—H0'···N3i | 0.88 | 2.24 | 3.089 (2) | 164 |
| C22—H22B···O1ii | 0.98 | 2.57 | 3.500 (2) | 159 |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
We are very thankful to the Natural Science Foundation of Ningbo City (grant No. 2009 A610185) for financial support. We are also grateful to the Beijing Institute of Technology for the X-ray diffraction measurements.
Bredereck, H., Effenberger, F. & Botsch, H. (1964). Chem. Ber. 97, 3397–3406.
Narayana, B., Raj, K. K. V., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2004). Eur. J. Med. Chem. 39, 867–872.
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Thiazole derivatives are found to be associated with various biological activities (Narayana et al., 2004). In order to further study the structure-activity relationship (SAR) of the thiazolyl-pyrimidine derivatives, we introduced arylamino group into 2-position of thiazole ring of thiazolyl-pyrimidine according to the general pyrimidine condensation method of Bredereck (Bredereck et al., 1964). But, it was found that the obtained compound was not desired compound that confirmed by 1H NMR, MS. So, the structure of (I) was further determined using single-crystal X-ray diffraction.
The molecular structure of (I) is illustrated in Fig. 1. The benzene ring makes opposite angles with thiazole-pyrimidine ring. The thiazole ring (S1/C7/N2/C8/C9) and the pyrimidine ring (C10/C11/C12/N3/C13/N4) are almost planar, with a dihedral angle of 2.48 (8)°. The aniline rings (C1/C2/C3/C4/C5/C6/N1) and (C14/C15/C16/C17/C18/C19/N5) make dihedral angles of 53.06 (8) Å and 19.21 (8) Å with the thiazole ring, respectively. In contrast, in the other independent molecule, the thiazole ring (S1'/C7'/N2'/C8'/C9') and the pyrimidine ring (C10'/C11'/C12'/N3'/C13'/N4') make a dihedral angle of 12.82 (8)°. The aniline rings (C1'/C2'/C3'/C4'/C5'/C6'/N1') and (C14'/C15'/C16'/C17'/C18'/C19'/N5') make dihedral angles of 51.09 (9) Å and 29.07 (9) Å with the thiazole ring, respectively. Moreover, there exist different bond lengths in the two independent molecules due to different intermolecular hydrogen bonding interactions (Table 1). The crystal structure is stabilized by intermolecular weak N—H···N and C—H···O interactions, which extending down b axis.