organic compounds
3-Isopropyl-2-p-tolyloxy-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one
aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, bCenter of Oncology, People's Hospital Affiliated with YunYang Medical College, Shi Yan 442000, People's Republic of China, and cDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
*Correspondence e-mail: dengshouheng@yahoo.cn
In the title compound, C20H22N2O2S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.023 (2) Å. The attached cyclohexene ring is disordered over two possible conformations, with an occupancy ratio of 0.776 (12):0.224 (12). Neither intermolecular hydrogen-bonding interactions nor π–π stacking interactions are present in the The molecular conformation and crystal packing are stabilized by three intramolecular C—H⋯O hydrogen bonds and two C—H⋯π interactions.
Related literature
For the biological activity of thienopyrimidin-4(3H)-one derivatives, see: De Laszlo et al. (1992a,b); Taguchi et al. (1993a,b); Walter (1999a,b,c,d); Walter & Zeun (2004); Ding et al. (2004); Santagati et al. (2003); Abbott GmbH Co KG (2004a, 2004b); Waehaelae et al. (2004a,b); Ford et al. (2004a,b); Duval et al. (2005). For a description of the Cambridge Structural Database, see: Allen (2002). For related structures, see: Xie et al. (2008); Xu et al. (2005); Zeng et al. (2005, 2006, 2007, 2008); Wang et al. (2006, 2007, 2008); Zheng et al. (2007).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536809014962/at2765sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809014962/at2765Isup2.hkl
To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added iso-propyl isocyanate (3 mmol) under dry nitrogen at room temperature. After the reaction mixture was left unstirred for 48 h at room temperature, the solvent was removed off under reduced pressure and ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed, and the residue was dissolved in CH3CN (15 ml). After adding 4-CH3—PhOH (3.1 mmol) and excess K2CO3 to the solution of carbodiimide, the mixture was stirred for 15 h at room temperature. The solution was condensed and the residue was recrystallized by EtOH to give the title compound, (I), in yield of 65% (m.p. 436 K). Elemental analysis calculated for C20H22N2O2S: C 67.77, H 6.26, N 7.90%. Found: C 67.54, H 6.32, N 7.83%. Crystals suitable for single crystal X-ray diffraction were obtained by vapor diffusion of hexane and dichloromethane (1:3 v/v) at room temperature.
H atoms were placed at calculated positions and treated as riding atoms, with C—H = 0.93–0.98 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. View of the molecule of showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size. Only the major component of the disordered cyclohexene ring is shown. |
C20H22N2O2S | F(000) = 376 |
Mr = 354.47 | Dx = 1.280 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2048 reflections |
a = 13.2367 (7) Å | θ = 2.9–24.5° |
b = 5.7493 (3) Å | µ = 0.19 mm−1 |
c = 13.4306 (7) Å | T = 298 K |
β = 115.858 (4)° | Block, colourless |
V = 919.76 (8) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3920 independent reflections |
Radiation source: fine-focus sealed tube | 3370 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.963, Tmax = 0.981 | k = −7→7 |
6373 measured reflections | l = −17→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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0798P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3920 reflections | Δρmax = 0.20 e Å−3 |
248 parameters | Δρmin = −0.32 e Å−3 |
16 restraints | Absolute structure: Flack (1983), 1702 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.16 (10) |
C20H22N2O2S | V = 919.76 (8) Å3 |
Mr = 354.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 13.2367 (7) Å | µ = 0.19 mm−1 |
b = 5.7493 (3) Å | T = 298 K |
c = 13.4306 (7) Å | 0.20 × 0.10 × 0.10 mm |
β = 115.858 (4)° |
Bruker SMART CCD area-detector diffractometer | 3920 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3370 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.981 | Rint = 0.079 |
6373 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.141 | Δρmax = 0.20 e Å−3 |
S = 1.01 | Δρmin = −0.32 e Å−3 |
3920 reflections | Absolute structure: Flack (1983), 1702 Freidel pairs |
248 parameters | Absolute structure parameter: 0.16 (10) |
16 restraints |
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 | Occ. (<1) | |
C1 | 0.20878 (19) | 0.6656 (5) | 0.88050 (19) | 0.0448 (6) | |
C2 | 0.0948 (2) | 0.6877 (6) | 0.8794 (2) | 0.0563 (7) | |
H2A | 0.0446 | 0.7700 | 0.8132 | 0.068* | 0.776 (12) |
H2B | 0.0639 | 0.5339 | 0.8776 | 0.068* | 0.776 (12) |
H2C | 0.0817 | 0.5593 | 0.9191 | 0.068* | 0.224 (12) |
H2D | 0.0370 | 0.6849 | 0.8037 | 0.068* | 0.224 (12) |
C3 | 0.1018 (4) | 0.8162 (11) | 0.9796 (5) | 0.0662 (16) | 0.776 (12) |
H3A | 0.1348 | 0.7157 | 1.0439 | 0.079* | 0.776 (12) |
H3B | 0.0268 | 0.8576 | 0.9693 | 0.079* | 0.776 (12) |
C4 | 0.1717 (4) | 1.0336 (10) | 0.9996 (6) | 0.0690 (17) | 0.776 (12) |
H4A | 0.1703 | 1.1175 | 1.0616 | 0.083* | 0.776 (12) |
H4B | 0.1383 | 1.1329 | 0.9349 | 0.083* | 0.776 (12) |
C3' | 0.0904 (12) | 0.916 (2) | 0.9334 (14) | 0.061 (5) | 0.224 (12) |
H3'1 | 0.0829 | 1.0405 | 0.8817 | 0.073* | 0.224 (12) |
H3'2 | 0.0230 | 0.9169 | 0.9448 | 0.073* | 0.224 (12) |
C4' | 0.1882 (9) | 0.974 (5) | 1.0420 (11) | 0.068 (6) | 0.224 (12) |
H4'1 | 0.1965 | 0.8556 | 1.0964 | 0.081* | 0.224 (12) |
H4'2 | 0.1758 | 1.1224 | 1.0692 | 0.081* | 0.224 (12) |
C5 | 0.2932 (2) | 0.9853 (6) | 1.0236 (3) | 0.0615 (8) | |
H5A | 0.3283 | 1.1265 | 1.0144 | 0.074* | 0.776 (12) |
H5B | 0.3346 | 0.9322 | 1.0993 | 0.074* | 0.776 (12) |
H5C | 0.2996 | 1.1376 | 0.9958 | 0.074* | 0.224 (12) |
H5D | 0.3578 | 0.9636 | 1.0943 | 0.074* | 0.224 (12) |
C6 | 0.2953 (2) | 0.8022 (5) | 0.9451 (2) | 0.0489 (6) | |
C7 | 0.3471 (2) | 0.5369 (5) | 0.8298 (2) | 0.0457 (6) | |
C8 | 0.23832 (18) | 0.5102 (5) | 0.81357 (19) | 0.0419 (5) | |
C9 | 0.1665 (2) | 0.3547 (5) | 0.7278 (2) | 0.0440 (5) | |
C10 | 0.33155 (19) | 0.2882 (5) | 0.6970 (2) | 0.0472 (6) | |
C11 | 0.1476 (2) | 0.1089 (5) | 0.5680 (2) | 0.0476 (6) | |
H11 | 0.0727 | 0.1104 | 0.5658 | 0.057* | |
C12 | 0.1818 (3) | −0.1432 (6) | 0.5773 (3) | 0.0763 (10) | |
H12A | 0.2536 | −0.1556 | 0.5760 | 0.114* | |
H12B | 0.1269 | −0.2287 | 0.5163 | 0.114* | |
H12C | 0.1867 | −0.2060 | 0.6455 | 0.114* | |
C13 | 0.1348 (3) | 0.2214 (6) | 0.4619 (2) | 0.0640 (8) | |
H13A | 0.1085 | 0.3781 | 0.4587 | 0.096* | |
H13B | 0.0817 | 0.1349 | 0.4001 | 0.096* | |
H13C | 0.2061 | 0.2229 | 0.4591 | 0.096* | |
C14 | 0.4833 (2) | 0.1798 (5) | 0.6585 (2) | 0.0515 (7) | |
C15 | 0.5521 (3) | 0.0051 (7) | 0.7178 (3) | 0.0704 (9) | |
H15 | 0.5252 | −0.1141 | 0.7466 | 0.084* | |
C16 | 0.6628 (3) | 0.0076 (7) | 0.7348 (3) | 0.0743 (9) | |
H16 | 0.7098 | −0.1137 | 0.7741 | 0.089* | |
C17 | 0.7055 (2) | 0.1829 (6) | 0.6956 (2) | 0.0592 (8) | |
C18 | 0.6321 (3) | 0.3536 (7) | 0.6344 (3) | 0.0721 (9) | |
H18 | 0.6583 | 0.4727 | 0.6050 | 0.086* | |
C19 | 0.5207 (3) | 0.3543 (6) | 0.6149 (3) | 0.0710 (9) | |
H19 | 0.4724 | 0.4715 | 0.5730 | 0.085* | |
C20 | 0.8275 (2) | 0.1872 (10) | 0.7183 (3) | 0.0936 (15) | |
H20A | 0.8639 | 0.3178 | 0.7646 | 0.140* | |
H20B | 0.8332 | 0.2006 | 0.6496 | 0.140* | |
H20C | 0.8632 | 0.0460 | 0.7549 | 0.140* | |
N1 | 0.22102 (15) | 0.2496 (4) | 0.66777 (15) | 0.0435 (4) | |
N2 | 0.39874 (17) | 0.4226 (4) | 0.77485 (19) | 0.0524 (6) | |
O2 | 0.36853 (15) | 0.1676 (4) | 0.63340 (17) | 0.0689 (7) | |
O1 | 0.06852 (14) | 0.3137 (4) | 0.70296 (16) | 0.0607 (6) | |
S1 | 0.41623 (5) | 0.74703 (15) | 0.92707 (6) | 0.0585 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0409 (13) | 0.0542 (15) | 0.0392 (12) | 0.0072 (10) | 0.0172 (10) | 0.0072 (11) |
C2 | 0.0453 (14) | 0.068 (2) | 0.0600 (16) | 0.0029 (12) | 0.0267 (12) | −0.0012 (14) |
C3 | 0.062 (3) | 0.086 (4) | 0.062 (3) | −0.003 (2) | 0.038 (2) | −0.010 (3) |
C4 | 0.075 (3) | 0.074 (4) | 0.070 (4) | 0.005 (2) | 0.042 (3) | −0.014 (3) |
C3' | 0.053 (7) | 0.072 (8) | 0.060 (8) | 0.002 (6) | 0.026 (6) | 0.000 (6) |
C4' | 0.075 (9) | 0.081 (10) | 0.056 (9) | 0.012 (6) | 0.036 (7) | 0.012 (7) |
C5 | 0.0554 (16) | 0.071 (2) | 0.0553 (16) | 0.0041 (14) | 0.0213 (13) | −0.0128 (15) |
C6 | 0.0409 (12) | 0.0616 (17) | 0.0410 (12) | 0.0051 (11) | 0.0149 (10) | −0.0014 (12) |
C7 | 0.0371 (13) | 0.0556 (15) | 0.0383 (12) | 0.0036 (11) | 0.0107 (10) | −0.0022 (11) |
C8 | 0.0347 (11) | 0.0508 (13) | 0.0373 (12) | 0.0014 (10) | 0.0130 (10) | 0.0026 (10) |
C9 | 0.0369 (12) | 0.0502 (14) | 0.0449 (13) | 0.0016 (10) | 0.0179 (10) | 0.0058 (11) |
C10 | 0.0360 (11) | 0.0563 (16) | 0.0490 (13) | 0.0013 (11) | 0.0182 (10) | −0.0032 (12) |
C11 | 0.0381 (13) | 0.0495 (15) | 0.0485 (14) | −0.0052 (11) | 0.0127 (11) | −0.0059 (12) |
C12 | 0.095 (3) | 0.0463 (17) | 0.072 (2) | −0.0096 (16) | 0.0220 (19) | 0.0016 (16) |
C13 | 0.0728 (18) | 0.0565 (18) | 0.0483 (15) | 0.0039 (15) | 0.0130 (13) | −0.0016 (14) |
C14 | 0.0381 (13) | 0.0631 (18) | 0.0561 (15) | −0.0044 (11) | 0.0232 (12) | −0.0184 (13) |
C15 | 0.0602 (18) | 0.075 (2) | 0.082 (2) | −0.0034 (17) | 0.0366 (17) | 0.0130 (19) |
C16 | 0.0570 (18) | 0.083 (2) | 0.077 (2) | 0.0165 (17) | 0.0243 (16) | 0.0157 (19) |
C17 | 0.0473 (14) | 0.085 (2) | 0.0514 (15) | −0.0026 (14) | 0.0276 (12) | −0.0128 (15) |
C18 | 0.0622 (19) | 0.085 (2) | 0.076 (2) | −0.0121 (18) | 0.0372 (17) | 0.0070 (18) |
C19 | 0.0608 (18) | 0.067 (2) | 0.083 (2) | 0.0070 (16) | 0.0292 (17) | 0.0075 (18) |
C20 | 0.0496 (17) | 0.166 (5) | 0.073 (2) | 0.002 (2) | 0.0332 (16) | −0.020 (3) |
N1 | 0.0338 (9) | 0.0498 (11) | 0.0439 (10) | −0.0019 (10) | 0.0143 (8) | −0.0033 (10) |
N2 | 0.0319 (10) | 0.0662 (15) | 0.0566 (13) | −0.0020 (10) | 0.0169 (9) | −0.0152 (11) |
O2 | 0.0398 (10) | 0.0937 (17) | 0.0744 (13) | −0.0097 (10) | 0.0261 (9) | −0.0374 (12) |
O1 | 0.0361 (9) | 0.0808 (15) | 0.0670 (11) | −0.0103 (9) | 0.0242 (8) | −0.0142 (11) |
S1 | 0.0359 (3) | 0.0722 (5) | 0.0603 (4) | −0.0040 (3) | 0.0144 (3) | −0.0216 (4) |
C1—C6 | 1.347 (4) | C9—O1 | 1.213 (3) |
C1—C8 | 1.437 (4) | C9—N1 | 1.429 (3) |
C1—C2 | 1.508 (3) | C10—N2 | 1.292 (3) |
C2—C3 | 1.502 (5) | C10—O2 | 1.348 (3) |
C2—C3' | 1.515 (10) | C10—N1 | 1.358 (3) |
C2—H2A | 0.9700 | C11—N1 | 1.503 (3) |
C2—H2B | 0.9700 | C11—C13 | 1.506 (4) |
C2—H2C | 0.9700 | C11—C12 | 1.508 (5) |
C2—H2D | 0.9700 | C11—H11 | 0.9800 |
C3—C4 | 1.508 (7) | C12—H12A | 0.9600 |
C3—H3A | 0.9700 | C12—H12B | 0.9600 |
C3—H3B | 0.9700 | C12—H12C | 0.9600 |
C4—C5 | 1.521 (5) | C13—H13A | 0.9600 |
C4—H4A | 0.9700 | C13—H13B | 0.9600 |
C4—H4B | 0.9700 | C13—H13C | 0.9600 |
C3'—C4' | 1.505 (10) | C14—C15 | 1.356 (5) |
C3'—H3'1 | 0.9700 | C14—C19 | 1.359 (4) |
C3'—H3'2 | 0.9700 | C14—O2 | 1.407 (3) |
C4'—C5 | 1.515 (9) | C15—C16 | 1.382 (4) |
C4'—H4'1 | 0.9700 | C15—H15 | 0.9300 |
C4'—H4'2 | 0.9700 | C16—C17 | 1.368 (5) |
C5—C6 | 1.499 (4) | C16—H16 | 0.9300 |
C5—H5A | 0.9700 | C17—C18 | 1.373 (5) |
C5—H5B | 0.9700 | C17—C20 | 1.508 (4) |
C5—H5C | 0.9700 | C18—C19 | 1.381 (4) |
C5—H5D | 0.9700 | C18—H18 | 0.9300 |
C6—S1 | 1.749 (3) | C19—H19 | 0.9300 |
C7—C8 | 1.368 (3) | C20—H20A | 0.9600 |
C7—N2 | 1.372 (3) | C20—H20B | 0.9600 |
C7—S1 | 1.721 (3) | C20—H20C | 0.9600 |
C8—C9 | 1.440 (4) | ||
C6—C1—C8 | 112.2 (2) | H5A—C5—H5D | 88.0 |
C6—C1—C2 | 121.6 (2) | H5B—C5—H5D | 23.0 |
C8—C1—C2 | 126.2 (2) | H5C—C5—H5D | 107.8 |
C3—C2—C1 | 111.2 (3) | C1—C6—C5 | 126.2 (2) |
C3—C2—C3' | 31.2 (6) | C1—C6—S1 | 112.19 (19) |
C1—C2—C3' | 108.4 (7) | C5—C6—S1 | 121.6 (2) |
C3—C2—H2A | 109.4 | C8—C7—N2 | 126.7 (2) |
C1—C2—H2A | 109.4 | C8—C7—S1 | 111.93 (19) |
C3'—C2—H2A | 82.1 | N2—C7—S1 | 121.34 (18) |
C3—C2—H2B | 109.4 | C7—C8—C1 | 112.7 (2) |
C1—C2—H2B | 109.4 | C7—C8—C9 | 118.6 (2) |
C3'—C2—H2B | 134.4 | C1—C8—C9 | 128.4 (2) |
H2A—C2—H2B | 108.0 | O1—C9—N1 | 120.3 (2) |
C3—C2—H2C | 80.7 | O1—C9—C8 | 126.4 (2) |
C1—C2—H2C | 110.4 | N1—C9—C8 | 113.2 (2) |
C3'—C2—H2C | 110.1 | N2—C10—O2 | 120.6 (2) |
H2A—C2—H2C | 131.4 | N2—C10—N1 | 127.4 (2) |
H2B—C2—H2C | 31.3 | O2—C10—N1 | 112.1 (2) |
C3—C2—H2D | 131.3 | N1—C11—C13 | 112.0 (2) |
C1—C2—H2D | 109.7 | N1—C11—C12 | 112.9 (2) |
C3'—C2—H2D | 109.9 | C13—C11—C12 | 113.4 (3) |
H2A—C2—H2D | 30.2 | N1—C11—H11 | 105.9 |
H2B—C2—H2D | 80.0 | C13—C11—H11 | 105.9 |
H2C—C2—H2D | 108.4 | C12—C11—H11 | 105.9 |
C2—C3—C4 | 111.1 (5) | C11—C12—H12A | 109.5 |
C2—C3—H3A | 109.4 | C11—C12—H12B | 109.5 |
C4—C3—H3A | 109.4 | H12A—C12—H12B | 109.5 |
C2—C3—H3B | 109.4 | C11—C12—H12C | 109.5 |
C4—C3—H3B | 109.4 | H12A—C12—H12C | 109.5 |
H3A—C3—H3B | 108.0 | H12B—C12—H12C | 109.5 |
C3—C4—C5 | 113.3 (4) | C11—C13—H13A | 109.5 |
C3—C4—H4A | 108.9 | C11—C13—H13B | 109.5 |
C5—C4—H4A | 108.9 | H13A—C13—H13B | 109.5 |
C3—C4—H4B | 108.9 | C11—C13—H13C | 109.5 |
C5—C4—H4B | 108.9 | H13A—C13—H13C | 109.5 |
H4A—C4—H4B | 107.7 | H13B—C13—H13C | 109.5 |
C4'—C3'—C2 | 117.3 (15) | C15—C14—C19 | 121.5 (3) |
C4'—C3'—H3'1 | 108.0 | C15—C14—O2 | 118.8 (3) |
C2—C3'—H3'1 | 108.0 | C19—C14—O2 | 119.4 (3) |
C4'—C3'—H3'2 | 108.0 | C14—C15—C16 | 118.8 (3) |
C2—C3'—H3'2 | 108.0 | C14—C15—H15 | 120.6 |
H3'1—C3'—H3'2 | 107.2 | C16—C15—H15 | 120.6 |
C3'—C4'—C5 | 108.3 (10) | C17—C16—C15 | 122.0 (3) |
C3'—C4'—H4'1 | 110.0 | C17—C16—H16 | 119.0 |
C5—C4'—H4'1 | 110.0 | C15—C16—H16 | 119.0 |
C3'—C4'—H4'2 | 110.0 | C16—C17—C18 | 117.0 (3) |
C5—C4'—H4'2 | 110.0 | C16—C17—C20 | 121.3 (3) |
H4'1—C4'—H4'2 | 108.4 | C18—C17—C20 | 121.6 (3) |
C6—C5—C4' | 112.6 (9) | C17—C18—C19 | 122.2 (3) |
C6—C5—C4 | 108.8 (3) | C17—C18—H18 | 118.9 |
C4'—C5—C4 | 23.5 (6) | C19—C18—H18 | 118.9 |
C6—C5—H5A | 109.9 | C14—C19—C18 | 118.4 (3) |
C4'—C5—H5A | 125.5 | C14—C19—H19 | 120.8 |
C4—C5—H5A | 109.9 | C18—C19—H19 | 120.8 |
C6—C5—H5B | 109.9 | C17—C20—H20A | 109.5 |
C4'—C5—H5B | 87.4 | C17—C20—H20B | 109.5 |
C4—C5—H5B | 109.9 | H20A—C20—H20B | 109.5 |
H5A—C5—H5B | 108.3 | C17—C20—H20C | 109.5 |
C6—C5—H5C | 109.4 | H20A—C20—H20C | 109.5 |
C4'—C5—H5C | 110.0 | H20B—C20—H20C | 109.5 |
C4—C5—H5C | 90.9 | C10—N1—C9 | 120.8 (2) |
H5A—C5—H5C | 21.3 | C10—N1—C11 | 122.9 (2) |
H5B—C5—H5C | 125.7 | C9—N1—C11 | 116.21 (18) |
C6—C5—H5D | 108.6 | C10—N2—C7 | 113.1 (2) |
C4'—C5—H5D | 108.3 | C10—O2—C14 | 118.4 (2) |
C4—C5—H5D | 129.0 | C7—S1—C6 | 90.97 (12) |
C6—C1—C2—C3 | −17.9 (5) | C19—C14—C15—C16 | 0.6 (5) |
C8—C1—C2—C3 | 164.4 (4) | O2—C14—C15—C16 | 174.8 (3) |
C6—C1—C2—C3' | 15.2 (8) | C14—C15—C16—C17 | 1.4 (5) |
C8—C1—C2—C3' | −162.5 (8) | C15—C16—C17—C18 | −2.5 (5) |
C1—C2—C3—C4 | 46.7 (6) | C15—C16—C17—C20 | 177.8 (3) |
C3'—C2—C3—C4 | −44.0 (11) | C16—C17—C18—C19 | 1.7 (5) |
C2—C3—C4—C5 | −62.5 (8) | C20—C17—C18—C19 | −178.6 (3) |
C3—C2—C3'—C4' | 53.3 (13) | C15—C14—C19—C18 | −1.4 (5) |
C1—C2—C3'—C4' | −47.5 (19) | O2—C14—C19—C18 | −175.5 (3) |
C2—C3'—C4'—C5 | 61 (3) | C17—C18—C19—C14 | 0.2 (5) |
C3'—C4'—C5—C6 | −39 (2) | N2—C10—N1—C9 | −2.7 (4) |
C3'—C4'—C5—C4 | 46.5 (12) | O2—C10—N1—C9 | 177.7 (2) |
C3—C4—C5—C6 | 43.0 (7) | N2—C10—N1—C11 | 173.4 (3) |
C3—C4—C5—C4' | −61 (2) | O2—C10—N1—C11 | −6.3 (4) |
C8—C1—C6—C5 | 179.2 (3) | O1—C9—N1—C10 | −177.9 (3) |
C2—C1—C6—C5 | 1.2 (4) | C8—C9—N1—C10 | 3.8 (3) |
C8—C1—C6—S1 | 0.0 (3) | O1—C9—N1—C11 | 5.8 (4) |
C2—C1—C6—S1 | −178.0 (2) | C8—C9—N1—C11 | −172.6 (2) |
C4'—C5—C6—C1 | 11.4 (9) | C13—C11—N1—C10 | −64.3 (3) |
C4—C5—C6—C1 | −13.4 (5) | C12—C11—N1—C10 | 65.2 (3) |
C4'—C5—C6—S1 | −169.5 (9) | C13—C11—N1—C9 | 112.0 (3) |
C4—C5—C6—S1 | 165.8 (3) | C12—C11—N1—C9 | −118.6 (3) |
N2—C7—C8—C1 | −176.8 (3) | O2—C10—N2—C7 | 178.4 (3) |
S1—C7—C8—C1 | 0.7 (3) | N1—C10—N2—C7 | −1.2 (4) |
N2—C7—C8—C9 | −2.7 (4) | C8—C7—N2—C10 | 4.0 (4) |
S1—C7—C8—C9 | 174.81 (19) | S1—C7—N2—C10 | −173.3 (2) |
C6—C1—C8—C7 | −0.4 (3) | N2—C10—O2—C14 | 4.1 (4) |
C2—C1—C8—C7 | 177.4 (2) | N1—C10—O2—C14 | −176.3 (2) |
C6—C1—C8—C9 | −173.8 (2) | C15—C14—O2—C10 | 98.6 (3) |
C2—C1—C8—C9 | 4.1 (4) | C19—C14—O2—C10 | −87.0 (3) |
C7—C8—C9—O1 | −179.5 (3) | C8—C7—S1—C6 | −0.6 (2) |
C1—C8—C9—O1 | −6.5 (4) | N2—C7—S1—C6 | 177.0 (2) |
C7—C8—C9—N1 | −1.3 (3) | C1—C6—S1—C7 | 0.4 (2) |
C1—C8—C9—N1 | 171.7 (2) | C5—C6—S1—C7 | −178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···O2 | 0.96 | 2.41 | 2.959 (4) | 116 |
C12—H12A···O2 | 0.96 | 2.31 | 2.871 (4) | 117 |
C11—H11···O1 | 0.98 | 2.20 | 2.725 (3) | 112 |
C12—H12C···Cg1i | 0.96 | 2.94 | 3.838 (4) | 156 |
C12—H12C···Cg2i | 0.96 | 2.72 | 3.413 (4) | 130 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C20H22N2O2S |
Mr | 354.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 13.2367 (7), 5.7493 (3), 13.4306 (7) |
β (°) | 115.858 (4) |
V (Å3) | 919.76 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.963, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6373, 3920, 3370 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.638 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.141, 1.01 |
No. of reflections | 3920 |
No. of parameters | 248 |
No. of restraints | 16 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.32 |
Absolute structure | Flack (1983), 1702 Freidel pairs |
Absolute structure parameter | 0.16 (10) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···O2 | 0.96 | 2.41 | 2.959 (4) | 115.9 |
C12—H12A···O2 | 0.96 | 2.31 | 2.871 (4) | 116.6 |
C11—H11···O1 | 0.98 | 2.20 | 2.725 (3) | 112.0 |
C12—H12C···Cg1i | 0.96 | 2.94 | 3.838 (4) | 156 |
C12—H12C···Cg2i | 0.96 | 2.72 | 3.413 (4) | 130 |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
We gratefully acknowledge financial support of this work by the Education Commission of Hubei Province of China (grant Nos. B200624004, B20092412), Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).
References
Abbott GmbH & Co. KG (2004a). Chem. Abstr. 141, 89095. Google Scholar
Abbott GmbH & Co. KG (2004b). German Patent 10259382. Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De Laszlo, S. E., Patchett, A. A., Allen, E. E. & Greenlee, W. J. (1992a). Chem. Abstr. 118, 22249v. Google Scholar
De Laszlo, S. E., Patchett, A. A., Allen, E. E. & Greenlee, W. J. (1992b). European Patent 502 725. Google Scholar
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366–8371. Web of Science CrossRef PubMed CAS Google Scholar
Duval, E., Case, A., Stein, R. L. & Cuny, G. D. (2005). Bioorg. Med. Chem. Lett. 15, 1885–1889. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ford, J., Palmer, N. J., Atherall, J. F., Madge, D. J., Sherborne, B., Bushfield, M. & Stevens, E. B. (2004a). Chem. Abstr. 142, 74599. Google Scholar
Ford, J., Palmer, N. J., Atherall, J. F., Madge, D. J., Sherborne, B., Bushfield, M. & Stevens, E. B. (2004b). World Patent 2004111057. Google Scholar
Santagati, A., Marrazzo, A. & Granata, G. (2003). J. Heterocycl. Chem. 40, 869–873. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taguchi, M., Ota, T. & Hatayama, K. (1993a). Chem. Abstr. 119, 160309m. Google Scholar
Taguchi, M., Ota, T. & Hatayama, K. (1993b). World Patent 9303040. Google Scholar
Waehaelae, K., Lilienkampf, A., Alho, S., Huhtinen, K., Johansson, N., Koskimies, P. & Vihko, K. (2004a). Chem. Abstr. 142, 74590. Google Scholar
Waehaelae, K., Lilienkampf, A., Alho, S., Huhtinen, K., Johansson, N., Koskimies, P. & Vihko, K. (2004b). World Patent 2004110 459. Google Scholar
Walter, H. (1999a). Chem. Abstr. 130, 237580e. Google Scholar
Walter, H. (1999b). World Patent 9911631. Google Scholar
Walter, H. (1999c). Chem. Abstr. 130, 252368k. Google Scholar
Walter, H. (1999d). World Patent 9914202. Google Scholar
Walter, H. & Zeun, R. (2004). Chimia, 57, 692–696. Web of Science CrossRef Google Scholar
Wang, H.-M., Chen, L.-L., Hu, T. & Zeng, X.-H. (2008). Acta Cryst. E64, o2404. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, H.-M., Zeng, X.-H., Hu, Z.-Q., Li, G.-H. & Tian, J.-H. (2006). Acta Cryst. E62, o5038–o5040. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, H.-M., Zeng, X.-H., Zheng, A.-H., Tian, J.-H. & He, T.-Y. (2007). Acta Cryst. E63, o4365. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, H., Meng, S.-M., Fan, Y.-Q. & Guo, Y. (2008). Acta Cryst. E64, o2434. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, S.-Z., Cao, M.-H., Hu, Y.-G., Ding, M.-W. & Xiao, W.-J. (2005). Acta Cryst. E61, o2789–o2790. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, X.-H., Ding, M.-W. & He, H.-W. (2006). Acta Cryst. E62, o731–o732. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, G., Li, Q. & Hu, Y. (2008). Acta Cryst. E64, o535. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, X.-H., Wang, H.-M., Luo, Z.-G., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o4160–o4161. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, X.-H., Zhao, L.-H., Luo, H. & Long, J.-Y. (2007). Acta Cryst. E63, o3004. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, A.-H., Long, J.-Y., Zeng, X.-H. & Wang, H.-M. (2007). Acta Cryst. E63, o1142–o1144. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The derivatives of heterocycles containing thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (De Laszlo et al., 1992a,b; Walter, 1999a,b,c,d); Ding et al., 2004; Walter et al., 2004), significant 5-HT1A and 5-HT1B receptor activities (Taguchi et al., 1993a,b; Abbott GmbH & Co. KG., 2004a,b), potential selective COX-2 enzyme inhibitor activity (Santagati et al., 2003), 17beta-hydroxysteroid dehydrogenase inhibitor activity (Waehaelae et al., 2004a,b), potassium channel inhibitor activity (Ford et al., 2004a,b), and tissue transglutaminase inhibitor activity (Duval et al., 2005).
In recent years, we have been engaged in the preparation of the derivatives of heterocycles via aza-Wittig reaction. The title compound, (I), was synthesized and structurally characterized in this context.
The molecular structure indicates that the thieno[2,3-d]pyrimidine moiety is a conjugated system (Fig.1). All ring atoms in thieno[2,3-d]pyrimidine are essentially coplanar (Xu et al., 2005; Zeng et al., 2005, 2006, 2007, 2008; Wang et al., 2006, 2007, 2008; Zheng et al., 2007; Xie et al., 2008). The bond lengths and angles are within experimental error, in the ranges of values in previously reported structures in the Cambridge Structural Database (Version 5.26; Allen, 2002).
The attached cyclohexene ring is disordered. There are two possible conformations, C2—C5 and C2/C3'/C4'/C5, with an occupancy ratio of 0.77:0.23. There exists no intermolecular hydrogen bonding interaction and no π-π stacking. The molecular conformation and crystal packing are stabilized by three intramolecular C—H···O hydrogen bonds and two C—H···π interactions.