Acta Cryst. (2009). E65, o235 [ doi:10.1107/S1600536808041019 ]
In the title compound, C27H28N2O7S, the dihedral angles between the thiazole ring and the mono- and trisubstituted benzene rings are 87.8 (2) and 17.9 (3)°, respectively. The dihydropyrimidine ring adopts a flattened boat conformation. In the crystal structure, ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking occurs [centroid-centroid separation = 3.6611 (11) Å].
A mixture of ethyl 6-methyl-4-(4-methoxyphenyl)-2-thioxo-1,2,3,4- tetrahydropyrimidine-5-carboxylate (0.01 mol), chloroacetic acid (0.01 mol), fused sodium acetate (6 g) in glacial acetic acid (25 ml), acetic anhydride (10 ml) and 3,4,5-trimethoxybenzaldehyde (0.01 mol) was refluxed for 3 h. The reaction mixture was cooled and poured into cold water. The resulting solid was collected and crystallized from methanol to obtain the final product (80% yield, mp 448–449 K). ^1Ĥ NMR (CDCl~3~, p.p.m.): 1.23 (3H, m), 2.60 (3H, s), 3.78(3H,s),3.92(9H,m),4.13(2H,m),6.21 (1H, s), 6.73(2H,s), 6.85 (2H, d),7.36 (2H, d), 7.74 (1H,s). The compound was recrystallized by slow evaporation of an ethanol solution, yielding yellow blocks of (I).
The H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined as riding with Uiso (H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hb2872fig1thm.gif)
| Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms). |
| C27H28N2O7S | Z = 2 |
| Mr = 524.57 | F(000) = 552 |
| Triclinic, P1 | Dx = 1.394 Mg m−3 |
| Hall symbol: -P 1 | Melting point = 448–449 K |
| a = 10.485 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 10.854 (2) Å | Cell parameters from 3693 reflections |
| c = 11.318 (2) Å | θ = 1.9–27.5° |
| α = 83.42 (3)° | µ = 0.18 mm−1 |
| β = 77.65 (3)° | T = 113 K |
| γ = 89.00 (3)° | Block, yellow |
| V = 1250.0 (4) Å3 | 0.24 × 0.18 × 0.16 mm |
| Rigaku Saturn CCD diffractometer | 5632 independent reflections |
| Radiation source: rotating anode | 4018 reflections with I > 2σ(I) |
| confocal | Rint = 0.042 |
| Detector resolution: 7.31 pixels mm-1 | θmax = 27.5°, θmin = 1.9° |
| ω and φ scans | h = −13→13 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −12→14 |
| Tmin = 0.958, Tmax = 0.972 | l = −13→14 |
| 11123 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.107 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.057P)2] where P = (Fo2 + 2Fc2)/3 |
| 5632 reflections | (Δ/σ)max = 0.002 |
| 340 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.25 e Å−3 |
| C27H28N2O7S | γ = 89.00 (3)° |
| Mr = 524.57 | V = 1250.0 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.485 (2) Å | Mo Kα radiation |
| b = 10.854 (2) Å | µ = 0.18 mm−1 |
| c = 11.318 (2) Å | T = 113 K |
| α = 83.42 (3)° | 0.24 × 0.18 × 0.16 mm |
| β = 77.65 (3)° |
| Rigaku Saturn CCD diffractometer | 5632 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 4018 reflections with I > 2σ(I) |
| Tmin = 0.958, Tmax = 0.972 | Rint = 0.042 |
| 11123 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.107 | Δρmax = 0.33 e Å−3 |
| S = 1.01 | Δρmin = −0.25 e Å−3 |
| 5632 reflections | Absolute structure: ? |
| 340 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 | 1.07890 (3) | 0.91459 (4) | 0.32208 (3) | 0.01833 (11) | |
| N1 | 0.86811 (11) | 1.04443 (13) | 0.32885 (11) | 0.0150 (3) | |
| N2 | 1.04753 (12) | 1.11583 (13) | 0.17148 (12) | 0.0199 (3) | |
| O1 | 0.72626 (10) | 0.95600 (11) | 0.49886 (9) | 0.0221 (3) | |
| O2 | 0.79838 (11) | 1.43070 (12) | 0.09675 (10) | 0.0278 (3) | |
| O3 | 0.64354 (10) | 1.32735 (11) | 0.23970 (10) | 0.0205 (3) | |
| O4 | 0.42971 (11) | 0.82312 (12) | 0.11235 (10) | 0.0255 (3) | |
| O5 | 1.35655 (9) | 0.56820 (11) | 0.49941 (10) | 0.0214 (3) | |
| O6 | 1.24509 (10) | 0.37222 (11) | 0.62307 (10) | 0.0225 (3) | |
| O7 | 0.98144 (10) | 0.37091 (11) | 0.73924 (10) | 0.0225 (3) | |
| C1 | 0.94447 (13) | 0.87479 (16) | 0.44286 (13) | 0.0166 (3) | |
| C2 | 0.83361 (14) | 0.95891 (15) | 0.43168 (13) | 0.0154 (3) | |
| C3 | 0.99406 (13) | 1.03930 (15) | 0.26268 (13) | 0.0161 (3) | |
| C4 | 0.97211 (14) | 1.22004 (16) | 0.14268 (13) | 0.0177 (3) | |
| C5 | 0.84306 (14) | 1.23011 (15) | 0.19470 (13) | 0.0156 (3) | |
| C6 | 0.77098 (13) | 1.12589 (15) | 0.28340 (13) | 0.0148 (3) | |
| H6 | 0.7168 | 1.1634 | 0.3541 | 0.018* | |
| C7 | 0.92965 (14) | 0.78128 (15) | 0.53324 (13) | 0.0174 (3) | |
| H7 | 0.8471 | 0.7793 | 0.5881 | 0.021* | |
| C8 | 1.01696 (14) | 0.68271 (15) | 0.56224 (13) | 0.0161 (3) | |
| C9 | 1.15188 (13) | 0.68154 (15) | 0.51196 (13) | 0.0156 (3) | |
| H9 | 1.1927 | 0.7507 | 0.4592 | 0.019* | |
| C10 | 1.22455 (13) | 0.57908 (15) | 0.53991 (13) | 0.0163 (3) | |
| C11 | 1.16642 (14) | 0.47343 (15) | 0.61507 (13) | 0.0158 (3) | |
| C12 | 1.03251 (14) | 0.47620 (16) | 0.66753 (13) | 0.0165 (3) | |
| C13 | 0.96062 (14) | 0.58019 (15) | 0.64275 (13) | 0.0166 (3) | |
| H13 | 0.8708 | 0.5825 | 0.6811 | 0.020* | |
| C14 | 1.42504 (14) | 0.67531 (16) | 0.43143 (15) | 0.0223 (4) | |
| H14A | 1.3988 | 0.6921 | 0.3531 | 0.033* | |
| H14B | 1.5192 | 0.6603 | 0.4172 | 0.033* | |
| H14C | 1.4040 | 0.7469 | 0.4774 | 0.033* | |
| C15 | 1.23394 (15) | 0.29536 (17) | 0.73613 (15) | 0.0261 (4) | |
| H15A | 1.2244 | 0.3476 | 0.8026 | 0.039* | |
| H15B | 1.3125 | 0.2447 | 0.7339 | 0.039* | |
| H15C | 1.1572 | 0.2411 | 0.7495 | 0.039* | |
| C16 | 0.84708 (14) | 0.37320 (17) | 0.80105 (15) | 0.0232 (4) | |
| H16A | 0.8338 | 0.4411 | 0.8525 | 0.035* | |
| H16B | 0.8239 | 0.2942 | 0.8519 | 0.035* | |
| H16C | 0.7918 | 0.3859 | 0.7411 | 0.035* | |
| C17 | 1.05115 (15) | 1.31680 (18) | 0.05259 (15) | 0.0262 (4) | |
| H17A | 1.0379 | 1.3080 | −0.0292 | 0.039* | |
| H17B | 1.1439 | 1.3061 | 0.0539 | 0.039* | |
| H17C | 1.0233 | 1.3995 | 0.0742 | 0.039* | |
| C18 | 0.76540 (14) | 1.34015 (16) | 0.16950 (13) | 0.0182 (3) | |
| C19 | 0.55395 (15) | 1.42883 (17) | 0.22755 (17) | 0.0269 (4) | |
| H19A | 0.5610 | 1.4598 | 0.1406 | 0.032* | |
| H19B | 0.5742 | 1.4980 | 0.2706 | 0.032* | |
| C20 | 0.41855 (16) | 1.37926 (19) | 0.28279 (17) | 0.0324 (5) | |
| H20A | 0.3995 | 1.3115 | 0.2389 | 0.049* | |
| H20B | 0.3550 | 1.4457 | 0.2769 | 0.049* | |
| H20C | 0.4131 | 1.3483 | 0.3686 | 0.049* | |
| C21 | 0.68099 (14) | 1.05058 (15) | 0.23002 (13) | 0.0150 (3) | |
| C22 | 0.72323 (14) | 1.00178 (15) | 0.12062 (13) | 0.0168 (3) | |
| H22 | 0.8091 | 1.0202 | 0.0749 | 0.020* | |
| C23 | 0.64275 (15) | 0.92636 (16) | 0.07619 (13) | 0.0187 (3) | |
| H23 | 0.6736 | 0.8927 | 0.0015 | 0.022* | |
| C24 | 0.51625 (15) | 0.90098 (16) | 0.14285 (14) | 0.0188 (3) | |
| C25 | 0.47053 (14) | 0.95390 (16) | 0.25009 (14) | 0.0193 (4) | |
| H25 | 0.3829 | 0.9397 | 0.2933 | 0.023* | |
| C26 | 0.55228 (14) | 1.02701 (15) | 0.29392 (13) | 0.0174 (3) | |
| H26 | 0.5210 | 1.0616 | 0.3680 | 0.021* | |
| C27 | 0.47355 (17) | 0.76215 (18) | 0.00619 (15) | 0.0294 (4) | |
| H27A | 0.4963 | 0.8241 | −0.0652 | 0.044* | |
| H27B | 0.4039 | 0.7080 | −0.0042 | 0.044* | |
| H27C | 0.5506 | 0.7124 | 0.0149 | 0.044* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.01300 (17) | 0.0183 (2) | 0.0222 (2) | 0.00274 (15) | −0.00159 (14) | −0.00044 (16) |
| N1 | 0.0122 (5) | 0.0157 (7) | 0.0170 (6) | 0.0011 (5) | −0.0034 (5) | −0.0009 (5) |
| N2 | 0.0158 (6) | 0.0206 (8) | 0.0208 (7) | 0.0009 (6) | −0.0002 (5) | 0.0008 (6) |
| O1 | 0.0149 (5) | 0.0287 (7) | 0.0198 (5) | 0.0038 (5) | −0.0003 (4) | 0.0025 (5) |
| O2 | 0.0297 (6) | 0.0207 (7) | 0.0289 (6) | 0.0022 (5) | −0.0024 (5) | 0.0063 (5) |
| O3 | 0.0165 (5) | 0.0171 (6) | 0.0270 (6) | 0.0034 (5) | −0.0043 (4) | 0.0000 (5) |
| O4 | 0.0257 (6) | 0.0267 (7) | 0.0262 (6) | −0.0093 (5) | −0.0089 (5) | −0.0039 (5) |
| O5 | 0.0133 (5) | 0.0206 (7) | 0.0264 (6) | 0.0021 (5) | 0.0009 (4) | 0.0030 (5) |
| O6 | 0.0215 (5) | 0.0194 (7) | 0.0229 (6) | 0.0066 (5) | −0.0012 (4) | 0.0050 (5) |
| O7 | 0.0157 (5) | 0.0193 (7) | 0.0285 (6) | −0.0007 (5) | 0.0001 (4) | 0.0053 (5) |
| C1 | 0.0141 (6) | 0.0186 (9) | 0.0176 (7) | 0.0004 (6) | −0.0033 (6) | −0.0041 (6) |
| C2 | 0.0151 (6) | 0.0155 (8) | 0.0167 (7) | 0.0015 (6) | −0.0060 (6) | −0.0019 (6) |
| C3 | 0.0121 (6) | 0.0164 (9) | 0.0197 (8) | 0.0020 (6) | −0.0025 (6) | −0.0034 (6) |
| C4 | 0.0173 (7) | 0.0192 (9) | 0.0162 (7) | −0.0004 (7) | −0.0040 (6) | 0.0003 (6) |
| C5 | 0.0175 (7) | 0.0148 (8) | 0.0148 (7) | −0.0012 (6) | −0.0042 (6) | −0.0014 (6) |
| C6 | 0.0134 (6) | 0.0143 (8) | 0.0163 (7) | 0.0017 (6) | −0.0023 (5) | −0.0018 (6) |
| C7 | 0.0143 (6) | 0.0188 (9) | 0.0193 (8) | 0.0023 (6) | −0.0035 (6) | −0.0030 (7) |
| C8 | 0.0175 (7) | 0.0175 (9) | 0.0146 (7) | 0.0019 (6) | −0.0061 (6) | −0.0028 (6) |
| C9 | 0.0153 (6) | 0.0173 (9) | 0.0146 (7) | −0.0013 (6) | −0.0047 (6) | 0.0002 (6) |
| C10 | 0.0144 (6) | 0.0188 (9) | 0.0157 (7) | 0.0019 (6) | −0.0028 (5) | −0.0032 (6) |
| C11 | 0.0170 (7) | 0.0151 (9) | 0.0157 (7) | 0.0036 (6) | −0.0053 (6) | −0.0008 (6) |
| C12 | 0.0170 (7) | 0.0165 (9) | 0.0154 (7) | −0.0017 (6) | −0.0034 (6) | 0.0013 (6) |
| C13 | 0.0137 (6) | 0.0197 (9) | 0.0165 (7) | 0.0020 (6) | −0.0037 (5) | −0.0017 (6) |
| C14 | 0.0159 (7) | 0.0235 (10) | 0.0244 (8) | −0.0023 (7) | 0.0011 (6) | 0.0006 (7) |
| C15 | 0.0203 (7) | 0.0244 (10) | 0.0296 (9) | 0.0017 (7) | −0.0034 (7) | 0.0098 (8) |
| C16 | 0.0170 (7) | 0.0243 (10) | 0.0247 (8) | −0.0025 (7) | 0.0024 (6) | −0.0001 (7) |
| C17 | 0.0196 (7) | 0.0283 (11) | 0.0267 (9) | −0.0032 (7) | −0.0004 (7) | 0.0056 (8) |
| C18 | 0.0206 (7) | 0.0186 (9) | 0.0166 (7) | −0.0002 (7) | −0.0057 (6) | −0.0035 (7) |
| C19 | 0.0229 (8) | 0.0212 (10) | 0.0385 (10) | 0.0092 (7) | −0.0102 (7) | −0.0057 (8) |
| C20 | 0.0203 (8) | 0.0355 (12) | 0.0430 (11) | 0.0075 (8) | −0.0080 (7) | −0.0092 (9) |
| C21 | 0.0152 (6) | 0.0131 (8) | 0.0169 (7) | 0.0005 (6) | −0.0064 (6) | 0.0027 (6) |
| C22 | 0.0164 (6) | 0.0158 (9) | 0.0176 (7) | 0.0004 (6) | −0.0043 (6) | 0.0011 (6) |
| C23 | 0.0231 (7) | 0.0183 (9) | 0.0155 (7) | 0.0022 (7) | −0.0060 (6) | −0.0017 (6) |
| C24 | 0.0203 (7) | 0.0159 (9) | 0.0219 (8) | −0.0018 (7) | −0.0109 (6) | 0.0034 (7) |
| C25 | 0.0158 (7) | 0.0199 (9) | 0.0218 (8) | −0.0022 (7) | −0.0047 (6) | 0.0012 (7) |
| C26 | 0.0169 (7) | 0.0181 (9) | 0.0169 (7) | 0.0012 (6) | −0.0034 (6) | −0.0010 (6) |
| C27 | 0.0357 (9) | 0.0259 (11) | 0.0307 (10) | −0.0048 (8) | −0.0135 (8) | −0.0076 (8) |
| S1—C3 | 1.7552 (18) | C11—C12 | 1.4039 (19) |
| S1—C1 | 1.7616 (15) | C12—C13 | 1.382 (2) |
| N1—C3 | 1.3754 (17) | C13—H13 | 0.9500 |
| N1—C2 | 1.390 (2) | C14—H14A | 0.9800 |
| N1—C6 | 1.474 (2) | C14—H14B | 0.9800 |
| N2—C3 | 1.281 (2) | C14—H14C | 0.9800 |
| N2—C4 | 1.416 (2) | C15—H15A | 0.9800 |
| O1—C2 | 1.2147 (17) | C15—H15B | 0.9800 |
| O2—C18 | 1.212 (2) | C15—H15C | 0.9800 |
| O3—C18 | 1.3526 (17) | C16—H16A | 0.9800 |
| O3—C19 | 1.449 (2) | C16—H16B | 0.9800 |
| O4—C24 | 1.3727 (19) | C16—H16C | 0.9800 |
| O4—C27 | 1.424 (2) | C17—H17A | 0.9800 |
| O5—C10 | 1.3693 (17) | C17—H17B | 0.9800 |
| O5—C14 | 1.431 (2) | C17—H17C | 0.9800 |
| O6—C11 | 1.3686 (19) | C19—C20 | 1.505 (2) |
| O6—C15 | 1.429 (2) | C19—H19A | 0.9900 |
| O7—C12 | 1.369 (2) | C19—H19B | 0.9900 |
| O7—C16 | 1.4338 (16) | C20—H20A | 0.9800 |
| C1—C7 | 1.342 (2) | C20—H20B | 0.9800 |
| C1—C2 | 1.483 (2) | C20—H20C | 0.9800 |
| C4—C5 | 1.3632 (19) | C21—C22 | 1.385 (2) |
| C4—C17 | 1.501 (2) | C21—C26 | 1.4006 (19) |
| C5—C18 | 1.469 (2) | C22—C23 | 1.391 (2) |
| C5—C6 | 1.518 (2) | C22—H22 | 0.9500 |
| C6—C21 | 1.519 (2) | C23—C24 | 1.393 (2) |
| C6—H6 | 1.0000 | C23—H23 | 0.9500 |
| C7—C8 | 1.451 (2) | C24—C25 | 1.391 (2) |
| C7—H7 | 0.9500 | C25—C26 | 1.381 (2) |
| C8—C13 | 1.406 (2) | C25—H25 | 0.9500 |
| C8—C9 | 1.4078 (19) | C26—H26 | 0.9500 |
| C9—C10 | 1.382 (2) | C27—H27A | 0.9800 |
| C9—H9 | 0.9500 | C27—H27B | 0.9800 |
| C10—C11 | 1.410 (2) | C27—H27C | 0.9800 |
| C3—S1—C1 | 91.65 (8) | O6—C15—H15A | 109.5 |
| C3—N1—C2 | 116.73 (14) | O6—C15—H15B | 109.5 |
| C3—N1—C6 | 120.95 (12) | H15A—C15—H15B | 109.5 |
| C2—N1—C6 | 121.87 (11) | O6—C15—H15C | 109.5 |
| C3—N2—C4 | 116.26 (12) | H15A—C15—H15C | 109.5 |
| C18—O3—C19 | 117.21 (13) | H15B—C15—H15C | 109.5 |
| C24—O4—C27 | 117.49 (12) | O7—C16—H16A | 109.5 |
| C10—O5—C14 | 116.92 (13) | O7—C16—H16B | 109.5 |
| C11—O6—C15 | 120.08 (12) | H16A—C16—H16B | 109.5 |
| C12—O7—C16 | 117.54 (13) | O7—C16—H16C | 109.5 |
| C7—C1—C2 | 119.69 (13) | H16A—C16—H16C | 109.5 |
| C7—C1—S1 | 129.97 (13) | H16B—C16—H16C | 109.5 |
| C2—C1—S1 | 110.26 (11) | C4—C17—H17A | 109.5 |
| O1—C2—N1 | 122.85 (15) | C4—C17—H17B | 109.5 |
| O1—C2—C1 | 127.13 (15) | H17A—C17—H17B | 109.5 |
| N1—C2—C1 | 110.02 (12) | C4—C17—H17C | 109.5 |
| N2—C3—N1 | 126.15 (15) | H17A—C17—H17C | 109.5 |
| N2—C3—S1 | 122.60 (11) | H17B—C17—H17C | 109.5 |
| N1—C3—S1 | 111.22 (11) | O2—C18—O3 | 122.02 (15) |
| C5—C4—N2 | 122.62 (14) | O2—C18—C5 | 128.08 (14) |
| C5—C4—C17 | 124.96 (16) | O3—C18—C5 | 109.89 (13) |
| N2—C4—C17 | 112.40 (13) | O3—C19—C20 | 107.07 (15) |
| C4—C5—C18 | 123.03 (14) | O3—C19—H19A | 110.3 |
| C4—C5—C6 | 121.00 (15) | C20—C19—H19A | 110.3 |
| C18—C5—C6 | 115.96 (12) | O3—C19—H19B | 110.3 |
| N1—C6—C5 | 108.39 (12) | C20—C19—H19B | 110.3 |
| N1—C6—C21 | 110.15 (13) | H19A—C19—H19B | 108.6 |
| C5—C6—C21 | 114.06 (12) | C19—C20—H20A | 109.5 |
| N1—C6—H6 | 108.0 | C19—C20—H20B | 109.5 |
| C5—C6—H6 | 108.0 | H20A—C20—H20B | 109.5 |
| C21—C6—H6 | 108.0 | C19—C20—H20C | 109.5 |
| C1—C7—C8 | 131.59 (13) | H20A—C20—H20C | 109.5 |
| C1—C7—H7 | 114.2 | H20B—C20—H20C | 109.5 |
| C8—C7—H7 | 114.2 | C22—C21—C26 | 118.61 (14) |
| C13—C8—C9 | 118.62 (15) | C22—C21—C6 | 121.88 (12) |
| C13—C8—C7 | 116.98 (13) | C26—C21—C6 | 119.49 (13) |
| C9—C8—C7 | 124.36 (14) | C21—C22—C23 | 121.50 (13) |
| C10—C9—C8 | 119.55 (14) | C21—C22—H22 | 119.2 |
| C10—C9—H9 | 120.2 | C23—C22—H22 | 119.2 |
| C8—C9—H9 | 120.2 | C22—C23—C24 | 119.01 (14) |
| O5—C10—C9 | 125.01 (14) | C22—C23—H23 | 120.5 |
| O5—C10—C11 | 113.31 (14) | C24—C23—H23 | 120.5 |
| C9—C10—C11 | 121.69 (13) | O4—C24—C25 | 115.17 (13) |
| O6—C11—C12 | 125.18 (14) | O4—C24—C23 | 124.71 (14) |
| O6—C11—C10 | 116.08 (12) | C25—C24—C23 | 120.10 (15) |
| C12—C11—C10 | 118.54 (15) | C26—C25—C24 | 120.12 (13) |
| O7—C12—C13 | 124.32 (13) | C26—C25—H25 | 119.9 |
| O7—C12—C11 | 115.93 (15) | C24—C25—H25 | 119.9 |
| C13—C12—C11 | 119.73 (14) | C25—C26—C21 | 120.55 (14) |
| C12—C13—C8 | 121.71 (13) | C25—C26—H26 | 119.7 |
| C12—C13—H13 | 119.1 | C21—C26—H26 | 119.7 |
| C8—C13—H13 | 119.1 | O4—C27—H27A | 109.5 |
| O5—C14—H14A | 109.5 | O4—C27—H27B | 109.5 |
| O5—C14—H14B | 109.5 | H27A—C27—H27B | 109.5 |
| H14A—C14—H14B | 109.5 | O4—C27—H27C | 109.5 |
| O5—C14—H14C | 109.5 | H27A—C27—H27C | 109.5 |
| H14A—C14—H14C | 109.5 | H27B—C27—H27C | 109.5 |
| H14B—C14—H14C | 109.5 | ||
| C3—S1—C1—C7 | 178.36 (16) | C8—C9—C10—C11 | 1.9 (2) |
| C3—S1—C1—C2 | 1.65 (12) | C15—O6—C11—C12 | −42.5 (2) |
| C3—N1—C2—O1 | 178.34 (15) | C15—O6—C11—C10 | 142.70 (15) |
| C6—N1—C2—O1 | −9.4 (2) | O5—C10—C11—O6 | −8.2 (2) |
| C3—N1—C2—C1 | −2.69 (19) | C9—C10—C11—O6 | 171.73 (14) |
| C6—N1—C2—C1 | 169.60 (13) | O5—C10—C11—C12 | 176.62 (13) |
| C7—C1—C2—O1 | 2.0 (3) | C9—C10—C11—C12 | −3.5 (2) |
| S1—C1—C2—O1 | 179.09 (14) | C16—O7—C12—C13 | −5.8 (2) |
| C7—C1—C2—N1 | −176.92 (14) | C16—O7—C12—C11 | 175.85 (13) |
| S1—C1—C2—N1 | 0.18 (16) | O6—C11—C12—O7 | 5.1 (2) |
| C4—N2—C3—N1 | 5.0 (2) | C10—C11—C12—O7 | 179.79 (13) |
| C4—N2—C3—S1 | −172.73 (11) | O6—C11—C12—C13 | −173.40 (14) |
| C2—N1—C3—N2 | −173.96 (15) | C10—C11—C12—C13 | 1.3 (2) |
| C6—N1—C3—N2 | 13.7 (2) | O7—C12—C13—C8 | −175.95 (14) |
| C2—N1—C3—S1 | 3.99 (17) | C11—C12—C13—C8 | 2.4 (2) |
| C6—N1—C3—S1 | −168.38 (11) | C9—C8—C13—C12 | −4.0 (2) |
| C1—S1—C3—N2 | 174.90 (14) | C7—C8—C13—C12 | 173.80 (14) |
| C1—S1—C3—N1 | −3.13 (12) | C19—O3—C18—O2 | −2.0 (2) |
| C3—N2—C4—C5 | −10.3 (2) | C19—O3—C18—C5 | 179.21 (13) |
| C3—N2—C4—C17 | 168.19 (14) | C4—C5—C18—O2 | 5.3 (3) |
| N2—C4—C5—C18 | 177.23 (14) | C6—C5—C18—O2 | −174.66 (16) |
| C17—C4—C5—C18 | −1.1 (3) | C4—C5—C18—O3 | −175.97 (14) |
| N2—C4—C5—C6 | −2.8 (2) | C6—C5—C18—O3 | 4.04 (19) |
| C17—C4—C5—C6 | 178.91 (14) | C18—O3—C19—C20 | 163.14 (14) |
| C3—N1—C6—C5 | −23.72 (19) | N1—C6—C21—C22 | −71.70 (18) |
| C2—N1—C6—C5 | 164.31 (13) | C5—C6—C21—C22 | 50.4 (2) |
| C3—N1—C6—C21 | 101.71 (16) | N1—C6—C21—C26 | 106.86 (16) |
| C2—N1—C6—C21 | −70.26 (17) | C5—C6—C21—C26 | −131.01 (15) |
| C4—C5—C6—N1 | 18.5 (2) | C26—C21—C22—C23 | −2.7 (2) |
| C18—C5—C6—N1 | −161.48 (13) | C6—C21—C22—C23 | 175.85 (15) |
| C4—C5—C6—C21 | −104.57 (17) | C21—C22—C23—C24 | 0.9 (2) |
| C18—C5—C6—C21 | 75.42 (17) | C27—O4—C24—C25 | −177.30 (15) |
| C2—C1—C7—C8 | 176.39 (16) | C27—O4—C24—C23 | 1.3 (2) |
| S1—C1—C7—C8 | −0.1 (3) | C22—C23—C24—O4 | −176.48 (15) |
| C1—C7—C8—C13 | −162.98 (17) | C22—C23—C24—C25 | 2.1 (2) |
| C1—C7—C8—C9 | 14.6 (3) | O4—C24—C25—C26 | 175.59 (15) |
| C13—C8—C9—C10 | 1.8 (2) | C23—C24—C25—C26 | −3.1 (3) |
| C7—C8—C9—C10 | −175.79 (15) | C24—C25—C26—C21 | 1.2 (3) |
| C14—O5—C10—C9 | 5.4 (2) | C22—C21—C26—C25 | 1.7 (2) |
| C14—O5—C10—C11 | −174.66 (13) | C6—C21—C26—C25 | −176.93 (15) |
| C8—C9—C10—O5 | −178.22 (14) |
Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380–385.
Liu, X.-G., Feng, Y.-Q., Li, X.-F. & Gao, B. (2004a). Acta Cryst. E60, o464–o465.
Liu, X.-G., Feng, Y.-Q., Li, X.-F. & Liang, Z.-P. (2004b). Acta Cryst. E60, o344–o345.
Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Langley, J., Cronise, P., Vaigro-Wolff, A., Gray-Goodrich, M., Campbell, H., Mayo, J. & Boyd, M. (1991). J. Natl Cancer Inst. 83, 757–766.
Rigaku (2005). CrystalClear. Rigaku Inc., Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sridhar, B., Ravikumar, K. & Sadanandam, Y. S. (2006). Acta Cryst. C62, o687–o690.
Fused pyrimidine derivatives represent important target molecules due to their highly pronounced biological properties (Ashok et al., 2007; Monks et al., 1991). In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1.
The fused thiazole ring C1—C2—N1—C3—S1 has usual geometry as observed in other fused thiazolopyrimidine compounds (Liu et al., 2004a,b; Sridhar et al., 2006). The thiazole ring makes dihedral angles of 87.8 (2) and 17.9 (3)° with the benzene rings C21–C26 and C8–C13, respectively. The pyrimidine ring adopts a flattened boat conformation. The crystal packing of (I) is stabilized by π-π stacking interactions.