Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017576/hk2230sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017576/hk2230Isup2.hkl |
CCDC reference: 647685
The title compound was synthesized according to the literature method (Cao, 2007). Crystals suitable for X-ray analysis were grown from acetone at 277 K.
H atoms were positioned geometrically, with C—H = 0.93, 0.98 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Thienopyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and antiinflammatory activities (Chambhare et al., 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing thienopyrimidine via aza-Wittig reactions at room temperature (Ding et al., 2004). We herein report the crystal structure of one such thienopyrimidine derivative, the title compound, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The ring C (N1/N2/C7—C10) is not planar having a total puckering amplitude, QT of 0.228 (2) Å and a flattened-boat conformation [φ = 54.10 (2)° and θ = 63.62 (3)°] (Cremer & Pople, 1975). Ring C has a pseudo mirror plane running through atoms N2 and C7, as can be deduced from the torsion angles (Table 1). Rings A (C1—C6), B (S1/C1/C6—C8), D (N2/N3/C10—C12) and E (C14—C19) are, of course, planar and the dihedral angles between them are A/B = 1.63 (3)°, A/D = 5.80 (2)°, B/D = 5.49 (3)° and D/E = 39.73 (3)°.
In the crystal structure, the weak intermolecular C—H···O hydrogen bonds (Table 2) cause to the formation of a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. Further stability is provided by offset π-π stacking interactions (Janiak, 2000), involving the rings; B, D and E. The adjacent B rings have a centroid-centroid distance of 3.79 (1) %A [symmetry code: 1 - x, 2 - y, 1 - z], while rings D and E have a centroid-centroid distance of 3.48 (1) %A [symmetry codes: 3/2 - x, y + 1/2, z; 3/2 - x, y - 1/2, z].
For related literature, see: Cao (2007); Chambhare et al. (2003); Ding et al. (2004); Janiak (2000).
For related literature, see: Allen et al. (1987); Cremer & Pople (1975).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C19H13N3O2S | F(000) = 1440 |
Mr = 347.38 | Dx = 1.431 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3753 reflections |
a = 12.6184 (18) Å | θ = 2.4–22.8° |
b = 11.0787 (16) Å | µ = 0.22 mm−1 |
c = 23.074 (3) Å | T = 292 K |
V = 3225.7 (8) Å3 | Block, colorless |
Z = 8 | 0.20 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 2529 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.109 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
φ and ω scans | h = −16→12 |
19405 measured reflections | k = −14→14 |
3847 independent reflections | l = −29→27 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0558P)2] where P = (Fo2 + 2Fc2)/3 |
3847 reflections | (Δ/σ)max = 0.002 |
227 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C19H13N3O2S | V = 3225.7 (8) Å3 |
Mr = 347.38 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.6184 (18) Å | µ = 0.22 mm−1 |
b = 11.0787 (16) Å | T = 292 K |
c = 23.074 (3) Å | 0.20 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 2529 reflections with I > 2σ(I) |
19405 measured reflections | Rint = 0.109 |
3847 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.30 e Å−3 |
3847 reflections | Δρmin = −0.21 e Å−3 |
227 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 | ||
C1 | 0.43864 (12) | 0.97800 (15) | 0.59301 (7) | 0.0371 (4) | |
C2 | 0.37664 (13) | 0.87999 (17) | 0.60996 (8) | 0.0438 (4) | |
H2 | 0.4039 | 0.8215 | 0.6347 | 0.053* | |
C3 | 0.27466 (14) | 0.87107 (18) | 0.58957 (8) | 0.0518 (5) | |
H3 | 0.2330 | 0.8055 | 0.6003 | 0.062* | |
C4 | 0.23303 (15) | 0.9589 (2) | 0.55310 (8) | 0.0549 (5) | |
H4 | 0.1637 | 0.9511 | 0.5400 | 0.066* | |
C5 | 0.29153 (15) | 1.0568 (2) | 0.53598 (8) | 0.0535 (5) | |
H5 | 0.2628 | 1.1151 | 0.5116 | 0.064* | |
C6 | 0.39535 (14) | 1.06644 (16) | 0.55618 (7) | 0.0422 (4) | |
C7 | 0.54732 (13) | 1.00455 (15) | 0.60685 (7) | 0.0362 (4) | |
C8 | 0.58174 (14) | 1.10884 (15) | 0.58091 (7) | 0.0409 (4) | |
C9 | 0.68825 (15) | 1.15173 (16) | 0.58730 (8) | 0.0441 (4) | |
C10 | 0.70455 (13) | 0.97290 (15) | 0.64790 (7) | 0.0371 (4) | |
C11 | 0.87532 (14) | 0.98872 (18) | 0.68008 (9) | 0.0472 (5) | |
C12 | 0.85911 (13) | 1.08834 (17) | 0.63630 (8) | 0.0470 (5) | |
H12 | 0.8682 | 1.1672 | 0.6549 | 0.056* | |
C13 | 0.93537 (16) | 1.0761 (2) | 0.58549 (10) | 0.0740 (7) | |
H13A | 0.9255 | 0.9990 | 0.5673 | 0.111* | |
H13B | 1.0069 | 1.0827 | 0.5992 | 0.111* | |
H13C | 0.9217 | 1.1390 | 0.5579 | 0.111* | |
C14 | 0.76691 (13) | 0.82173 (14) | 0.72199 (7) | 0.0378 (4) | |
C15 | 0.84826 (14) | 0.73933 (17) | 0.72829 (9) | 0.0472 (5) | |
H15 | 0.9104 | 0.7479 | 0.7070 | 0.057* | |
C16 | 0.83663 (16) | 0.64405 (18) | 0.76645 (10) | 0.0560 (5) | |
H16 | 0.8919 | 0.5895 | 0.7715 | 0.067* | |
C17 | 0.74425 (18) | 0.62940 (18) | 0.79685 (9) | 0.0576 (5) | |
H17 | 0.7363 | 0.5643 | 0.8219 | 0.069* | |
C18 | 0.66351 (16) | 0.71136 (19) | 0.79017 (9) | 0.0535 (5) | |
H18 | 0.6008 | 0.7013 | 0.8108 | 0.064* | |
C19 | 0.67441 (13) | 0.80874 (16) | 0.75303 (8) | 0.0432 (4) | |
H19 | 0.6199 | 0.8647 | 0.7491 | 0.052* | |
N1 | 0.60876 (10) | 0.93359 (12) | 0.64293 (6) | 0.0368 (3) | |
N2 | 0.74802 (10) | 1.07041 (12) | 0.62043 (6) | 0.0403 (4) | |
N3 | 0.78190 (10) | 0.92229 (12) | 0.68350 (6) | 0.0393 (4) | |
O1 | 0.72739 (11) | 1.24438 (12) | 0.56814 (6) | 0.0616 (4) | |
O2 | 0.95559 (11) | 0.96797 (14) | 0.70621 (7) | 0.0704 (5) | |
S1 | 0.48557 (4) | 1.18039 (5) | 0.53977 (2) | 0.05129 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0397 (10) | 0.0392 (10) | 0.0324 (9) | 0.0063 (8) | −0.0013 (7) | −0.0013 (7) |
C2 | 0.0434 (10) | 0.0456 (11) | 0.0423 (10) | 0.0043 (8) | −0.0025 (8) | 0.0016 (8) |
C3 | 0.0467 (11) | 0.0583 (13) | 0.0504 (12) | −0.0060 (10) | −0.0037 (9) | −0.0042 (10) |
C4 | 0.0433 (11) | 0.0738 (15) | 0.0477 (12) | 0.0029 (10) | −0.0129 (9) | −0.0055 (10) |
C5 | 0.0558 (13) | 0.0639 (14) | 0.0407 (11) | 0.0191 (11) | −0.0120 (9) | −0.0010 (9) |
C6 | 0.0481 (11) | 0.0449 (11) | 0.0337 (10) | 0.0081 (8) | −0.0039 (8) | −0.0015 (8) |
C7 | 0.0408 (10) | 0.0349 (10) | 0.0329 (9) | 0.0041 (7) | 0.0004 (7) | 0.0000 (7) |
C8 | 0.0478 (11) | 0.0387 (10) | 0.0363 (10) | 0.0037 (8) | 0.0004 (8) | 0.0038 (8) |
C9 | 0.0546 (11) | 0.0406 (11) | 0.0369 (10) | −0.0025 (9) | 0.0039 (9) | 0.0036 (8) |
C10 | 0.0380 (10) | 0.0369 (10) | 0.0365 (9) | 0.0027 (8) | 0.0029 (8) | −0.0006 (8) |
C11 | 0.0369 (10) | 0.0537 (12) | 0.0509 (12) | −0.0030 (9) | −0.0025 (9) | −0.0032 (9) |
C12 | 0.0411 (11) | 0.0496 (12) | 0.0502 (12) | −0.0097 (8) | 0.0000 (8) | −0.0008 (9) |
C13 | 0.0514 (13) | 0.1027 (19) | 0.0680 (15) | −0.0104 (12) | 0.0124 (11) | 0.0078 (14) |
C14 | 0.0374 (10) | 0.0348 (10) | 0.0414 (10) | 0.0019 (8) | −0.0076 (8) | −0.0007 (8) |
C15 | 0.0403 (10) | 0.0466 (12) | 0.0546 (12) | 0.0064 (8) | −0.0088 (9) | −0.0059 (9) |
C16 | 0.0588 (13) | 0.0429 (12) | 0.0662 (14) | 0.0134 (10) | −0.0237 (11) | −0.0006 (10) |
C17 | 0.0705 (14) | 0.0451 (12) | 0.0572 (13) | −0.0027 (11) | −0.0145 (11) | 0.0146 (10) |
C18 | 0.0548 (12) | 0.0558 (13) | 0.0501 (12) | −0.0011 (10) | −0.0009 (9) | 0.0097 (10) |
C19 | 0.0417 (11) | 0.0431 (11) | 0.0448 (11) | 0.0068 (8) | −0.0035 (8) | 0.0035 (8) |
N1 | 0.0325 (8) | 0.0378 (8) | 0.0402 (8) | 0.0024 (6) | −0.0016 (6) | 0.0051 (6) |
N2 | 0.0391 (8) | 0.0411 (9) | 0.0406 (8) | −0.0046 (6) | 0.0014 (6) | 0.0048 (7) |
N3 | 0.0326 (8) | 0.0422 (9) | 0.0432 (8) | 0.0002 (6) | −0.0050 (6) | 0.0043 (7) |
O1 | 0.0727 (10) | 0.0515 (9) | 0.0606 (9) | −0.0163 (7) | −0.0034 (7) | 0.0190 (7) |
O2 | 0.0430 (8) | 0.0753 (11) | 0.0928 (12) | −0.0110 (7) | −0.0214 (8) | 0.0140 (9) |
S1 | 0.0614 (3) | 0.0464 (3) | 0.0461 (3) | 0.0063 (2) | −0.0065 (2) | 0.0134 (2) |
C1—C2 | 1.394 (2) | C11—O2 | 1.201 (2) |
C1—C6 | 1.407 (2) | C11—N3 | 1.392 (2) |
C1—C7 | 1.439 (2) | C11—C12 | 1.510 (3) |
C2—C3 | 1.374 (2) | C12—N2 | 1.462 (2) |
C2—H2 | 0.9300 | C12—C13 | 1.523 (3) |
C3—C4 | 1.390 (3) | C12—H12 | 0.9800 |
C3—H3 | 0.9300 | C13—H13A | 0.9600 |
C4—C5 | 1.370 (3) | C13—H13B | 0.9600 |
C4—H4 | 0.9300 | C13—H13C | 0.9600 |
C5—C6 | 1.395 (2) | C14—C19 | 1.377 (2) |
C5—H5 | 0.9300 | C14—C15 | 1.381 (2) |
C6—S1 | 1.7416 (19) | C14—N3 | 1.437 (2) |
C7—C8 | 1.372 (2) | C15—C16 | 1.382 (3) |
C7—N1 | 1.383 (2) | C15—H15 | 0.9300 |
C8—C9 | 1.433 (3) | C16—C17 | 1.370 (3) |
C8—S1 | 1.7326 (17) | C16—H16 | 0.9300 |
C9—O1 | 1.222 (2) | C17—C18 | 1.373 (3) |
C9—N2 | 1.402 (2) | C17—H17 | 0.9300 |
C10—N1 | 1.2898 (19) | C18—C19 | 1.385 (3) |
C10—N2 | 1.367 (2) | C18—H18 | 0.9300 |
C10—N3 | 1.394 (2) | C19—H19 | 0.9300 |
C2—C1—C6 | 119.59 (15) | N2—C12—H12 | 110.0 |
C2—C1—C7 | 129.19 (16) | C11—C12—H12 | 110.0 |
C6—C1—C7 | 111.21 (15) | C13—C12—H12 | 110.0 |
C3—C2—C1 | 119.05 (17) | C12—C13—H13A | 109.5 |
C3—C2—H2 | 120.5 | C12—C13—H13B | 109.5 |
C1—C2—H2 | 120.5 | H13A—C13—H13B | 109.5 |
C2—C3—C4 | 120.73 (18) | C12—C13—H13C | 109.5 |
C2—C3—H3 | 119.6 | H13A—C13—H13C | 109.5 |
C4—C3—H3 | 119.6 | H13B—C13—H13C | 109.5 |
C5—C4—C3 | 121.69 (18) | C19—C14—C15 | 120.41 (17) |
C5—C4—H4 | 119.2 | C19—C14—N3 | 120.93 (15) |
C3—C4—H4 | 119.2 | C15—C14—N3 | 118.65 (16) |
C4—C5—C6 | 118.05 (18) | C14—C15—C16 | 119.52 (19) |
C4—C5—H5 | 121.0 | C14—C15—H15 | 120.2 |
C6—C5—H5 | 121.0 | C16—C15—H15 | 120.2 |
C5—C6—C1 | 120.88 (18) | C17—C16—C15 | 120.46 (18) |
C5—C6—S1 | 126.64 (15) | C17—C16—H16 | 119.8 |
C1—C6—S1 | 112.47 (13) | C15—C16—H16 | 119.8 |
C8—C7—N1 | 124.34 (16) | C16—C17—C18 | 119.70 (18) |
C8—C7—C1 | 112.15 (15) | C16—C17—H17 | 120.2 |
N1—C7—C1 | 123.50 (15) | C18—C17—H17 | 120.2 |
C7—C8—C9 | 122.08 (16) | C17—C18—C19 | 120.73 (19) |
C7—C8—S1 | 113.75 (14) | C17—C18—H18 | 119.6 |
C9—C8—S1 | 124.16 (13) | C19—C18—H18 | 119.6 |
O1—C9—N2 | 121.32 (18) | C14—C19—C18 | 119.18 (17) |
O1—C9—C8 | 128.33 (17) | C14—C19—H19 | 120.4 |
N2—C9—C8 | 110.34 (15) | C18—C19—H19 | 120.4 |
N1—C10—N2 | 126.98 (15) | C10—N1—C7 | 112.77 (14) |
N1—C10—N3 | 124.95 (15) | C10—N2—C9 | 123.00 (15) |
N2—C10—N3 | 108.07 (14) | C10—N2—C12 | 112.08 (14) |
O2—C11—N3 | 125.77 (18) | C9—N2—C12 | 124.40 (14) |
O2—C11—C12 | 126.16 (17) | C11—N3—C10 | 110.30 (14) |
N3—C11—C12 | 108.04 (15) | C11—N3—C14 | 123.81 (14) |
N2—C12—C11 | 101.42 (14) | C10—N3—C14 | 125.73 (14) |
N2—C12—C13 | 113.64 (16) | C8—S1—C6 | 90.41 (9) |
C11—C12—C13 | 111.38 (17) | ||
C6—C1—C2—C3 | 0.9 (3) | C17—C18—C19—C14 | 1.0 (3) |
C7—C1—C2—C3 | −177.67 (17) | N2—C10—N1—C7 | −2.4 (2) |
C1—C2—C3—C4 | −0.7 (3) | N3—C10—N1—C7 | 176.89 (15) |
C2—C3—C4—C5 | 0.3 (3) | C8—C7—N1—C10 | −2.8 (2) |
C3—C4—C5—C6 | 0.1 (3) | C1—C7—N1—C10 | 178.25 (15) |
C4—C5—C6—C1 | 0.1 (3) | N1—C10—N2—C9 | 8.1 (3) |
C4—C5—C6—S1 | 178.95 (15) | N3—C10—N2—C9 | −171.26 (15) |
C2—C1—C6—C5 | −0.6 (3) | N1—C10—N2—C12 | −179.83 (16) |
C7—C1—C6—C5 | 178.24 (15) | N3—C10—N2—C12 | 0.81 (19) |
C2—C1—C6—S1 | −179.58 (13) | O1—C9—N2—C10 | 172.59 (16) |
C7—C1—C6—S1 | −0.77 (18) | C8—C9—N2—C10 | −7.4 (2) |
C2—C1—C7—C8 | 178.66 (17) | O1—C9—N2—C12 | 1.5 (3) |
C6—C1—C7—C8 | 0.0 (2) | C8—C9—N2—C12 | −178.46 (15) |
C2—C1—C7—N1 | −2.3 (3) | C11—C12—N2—C10 | −2.32 (18) |
C6—C1—C7—N1 | 179.04 (15) | C13—C12—N2—C10 | 117.31 (18) |
N1—C7—C8—C9 | 2.6 (3) | C11—C12—N2—C9 | 169.62 (16) |
C1—C7—C8—C9 | −178.41 (15) | C13—C12—N2—C9 | −70.7 (2) |
N1—C7—C8—S1 | −178.25 (13) | O2—C11—N3—C10 | 179.24 (19) |
C1—C7—C8—S1 | 0.78 (19) | C12—C11—N3—C10 | −2.7 (2) |
C7—C8—C9—O1 | −177.43 (18) | O2—C11—N3—C14 | 3.6 (3) |
S1—C8—C9—O1 | 3.5 (3) | C12—C11—N3—C14 | −178.36 (15) |
C7—C8—C9—N2 | 2.5 (2) | N1—C10—N3—C11 | −178.10 (16) |
S1—C8—C9—N2 | −176.57 (13) | N2—C10—N3—C11 | 1.27 (19) |
O2—C11—C12—N2 | −179.01 (19) | N1—C10—N3—C14 | −2.6 (3) |
N3—C11—C12—N2 | 2.98 (18) | N2—C10—N3—C14 | 176.78 (14) |
O2—C11—C12—C13 | 59.8 (3) | C19—C14—N3—C11 | 136.45 (18) |
N3—C11—C12—C13 | −118.24 (18) | C15—C14—N3—C11 | −42.1 (2) |
C19—C14—C15—C16 | −0.6 (3) | C19—C14—N3—C10 | −38.5 (2) |
N3—C14—C15—C16 | 178.01 (16) | C15—C14—N3—C10 | 142.93 (17) |
C14—C15—C16—C17 | 1.6 (3) | C7—C8—S1—C6 | −1.03 (14) |
C15—C16—C17—C18 | −1.3 (3) | C9—C8—S1—C6 | 178.14 (16) |
C16—C17—C18—C19 | 0.0 (3) | C5—C6—S1—C8 | −177.92 (17) |
C15—C14—C19—C18 | −0.7 (3) | C1—C6—S1—C8 | 1.01 (14) |
N3—C14—C19—C18 | −179.25 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O2i | 0.93 | 2.58 | 3.409 (2) | 148 |
C16—H16···O2ii | 0.93 | 2.40 | 3.328 (2) | 172 |
C5—H5···O1iii | 0.93 | 2.45 | 3.358 (2) | 165 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x−1/2, −y+5/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H13N3O2S |
Mr | 347.38 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 292 |
a, b, c (Å) | 12.6184 (18), 11.0787 (16), 23.074 (3) |
V (Å3) | 3225.7 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19405, 3847, 2529 |
Rint | 0.109 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.115, 0.92 |
No. of reflections | 3847 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.21 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
N1—C7—C8—C9 | 2.6 (3) | C8—C7—N1—C10 | −2.8 (2) |
C7—C8—C9—N2 | 2.5 (2) | N1—C10—N2—C9 | 8.1 (3) |
N2—C10—N1—C7 | −2.4 (2) | C8—C9—N2—C10 | −7.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O2i | 0.93 | 2.58 | 3.409 (2) | 148.2 |
C16—H16···O2ii | 0.93 | 2.40 | 3.328 (2) | 172.2 |
C5—H5···O1iii | 0.93 | 2.45 | 3.358 (2) | 165.1 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x−1/2, −y+5/2, −z+1. |
Thienopyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and antiinflammatory activities (Chambhare et al., 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing thienopyrimidine via aza-Wittig reactions at room temperature (Ding et al., 2004). We herein report the crystal structure of one such thienopyrimidine derivative, the title compound, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The ring C (N1/N2/C7—C10) is not planar having a total puckering amplitude, QT of 0.228 (2) Å and a flattened-boat conformation [φ = 54.10 (2)° and θ = 63.62 (3)°] (Cremer & Pople, 1975). Ring C has a pseudo mirror plane running through atoms N2 and C7, as can be deduced from the torsion angles (Table 1). Rings A (C1—C6), B (S1/C1/C6—C8), D (N2/N3/C10—C12) and E (C14—C19) are, of course, planar and the dihedral angles between them are A/B = 1.63 (3)°, A/D = 5.80 (2)°, B/D = 5.49 (3)° and D/E = 39.73 (3)°.
In the crystal structure, the weak intermolecular C—H···O hydrogen bonds (Table 2) cause to the formation of a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. Further stability is provided by offset π-π stacking interactions (Janiak, 2000), involving the rings; B, D and E. The adjacent B rings have a centroid-centroid distance of 3.79 (1) %A [symmetry code: 1 - x, 2 - y, 1 - z], while rings D and E have a centroid-centroid distance of 3.48 (1) %A [symmetry codes: 3/2 - x, y + 1/2, z; 3/2 - x, y - 1/2, z].