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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o222.
Published online 2007 December 6. doi:  10.1107/S1600536807064598
PMCID: PMC2915283

2-(1H-Imidazol-1-yl)-3-isopropyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one

Abstract

In the title compound, C16H14N4OS, the three fused rings of the benzothieno[3,2-d]pyrimidinone unit are essentially coplanar, the maximum deviation from the mean plane being 0.067 (3) Å. The dihedral angle between the mean plane of the fused rings and the imidazole ring is 72.00 (3)°. Offset π–π stacking inter­actions involving the fused rings are effective in the stabilization of the crystal structure. The centroid–centroid distances between the thienophene and benzene rings, and between the pyrimidine and benzene rings are 3.67 (1) and 3.93 (1) Å, respectively. There are two intramolecular C—H(...)O interactions.

Related literature

For related literature, see: Chambhare et al. (2003 [triangle]); Ding et al. (2004 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Cao (2007 [triangle]); Xu et al. (2005 [triangle], 2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o222-scheme1.jpg

Experimental

Crystal data

  • C16H14N4OS
  • M r = 310.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o222-efi1.jpg
  • a = 15.2759 (16) Å
  • b = 12.1387 (12) Å
  • c = 8.0172 (8) Å
  • β = 97.439 (2)°
  • V = 1474.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 (2) K
  • 0.36 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: none
  • 8864 measured reflections
  • 3216 independent reflections
  • 2657 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.132
  • S = 1.08
  • 3216 reflections
  • 201 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Bruker, 2001 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064598/is2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064598/is2265Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author acknowledges the National Basic Research Program of China (grant No. 2004CCA00100) and the National Natural Science Foundation of China (project No. 20102001).

supplementary crystallographic information

Comment

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 present here the structure of one such thienopyrimidine derivative, the title compound (I), (Fig. 1). Crystal structures of similar compounds have been reported (Cao, 2007; Xu et al., 2005, 2006).

In the molecule of (I), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). The three fused rings of (I) are essentially coplanar, the maximum deviation from the benzo[4,5]thieno[3,2-e]pyrimidinone mean plane being 0.067 (3) Å for atom N2. The dihedral angle between the three fused rings (S1/N1–2/C1–10) and imidazole ring B (N3–4/C11–13) is 72.00 (3)°.

Offset π-π stacking interactions, involving the rings; A (S1/C1/C6—C8), B (C1—C6) and C (N1—N2/C7—C10) are effective in the stabilization of the crystal structure. The adjacent thienophene ring A (S1/C1/C6—C8) and the benzene ring B (C1—C6) at (-x, 1 - y, 2 - z) have a centroid-centroid distance of 3.67 (1) Å The adjacent pyrimidine ring C (N2—N3/C10—C13) and the benzene ring B (C1—C6) at (-x, 1 - y, 2 - z) have a centroid-centroid distance of 3.93 (1) Å

Experimental

The title compound was synthesized according to the literature method (Ding et al., 2004). The product was recrystallized from ethanol/dichloromethane (1:2 v/v) at room temperature to give crystals suitable for single-crystal X-ray diffraction.

Refinement

All H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C), allowing for free rotation of the methyl groups.

Figures

Fig. 1.
View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C16H14N4OSF000 = 648
Mr = 310.37Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3860 reflections
a = 15.2759 (16) Åθ = 2.7–28.0º
b = 12.1387 (12) ŵ = 0.23 mm1
c = 8.0172 (8) ÅT = 298 (2) K
β = 97.439 (2)ºBlock, colorless
V = 1474.1 (3) Å30.36 × 0.23 × 0.20 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer2657 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Monochromator: graphiteθmax = 27.0º
T = 298(2) Kθmin = 2.2º
[var phi] and ω scansh = −19→16
Absorption correction: nonek = −14→15
8864 measured reflectionsl = −7→10
3216 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0813P)2 + 0.01P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.017
3216 reflectionsΔρmax = 0.31 e Å3
201 parametersΔρmin = −0.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.01352 (10)0.41878 (12)0.82291 (18)0.0377 (3)
C2−0.04456 (11)0.48730 (14)0.7227 (2)0.0477 (4)
H2−0.02320.54380.66080.057*
C3−0.13345 (12)0.47032 (16)0.7166 (3)0.0591 (5)
H3−0.17280.51580.65040.071*
C4−0.16574 (12)0.38522 (16)0.8090 (3)0.0641 (5)
H4−0.22640.37500.80290.077*
C5−0.10994 (12)0.31650 (15)0.9083 (3)0.0567 (5)
H5−0.13200.26010.96950.068*
C6−0.01944 (11)0.33330 (12)0.9151 (2)0.0435 (4)
C70.10839 (10)0.41943 (11)0.84835 (18)0.0357 (3)
C80.14306 (10)0.33777 (12)0.95497 (19)0.0404 (4)
C90.23580 (11)0.32519 (13)1.0012 (2)0.0455 (4)
C100.24368 (10)0.47907 (11)0.81241 (18)0.0368 (3)
C110.30832 (14)0.65924 (14)0.7549 (3)0.0616 (5)
H110.28320.69830.83650.074*
C120.34470 (12)0.52387 (15)0.5998 (2)0.0520 (4)
H120.35050.45480.55210.062*
C130.37967 (12)0.61901 (15)0.5549 (2)0.0544 (4)
H130.41490.62610.46920.065*
C140.38228 (10)0.41578 (14)0.9892 (2)0.0459 (4)
H140.40430.47660.92590.055*
C150.39582 (13)0.44994 (16)1.1717 (3)0.0630 (5)
H15A0.36720.39801.23700.095*
H15B0.37100.52181.18270.095*
H15C0.45790.45181.21140.095*
C160.43350 (13)0.31491 (17)0.9501 (3)0.0676 (6)
H16A0.41570.25331.01280.101*
H16B0.49550.32810.98050.101*
H16C0.42200.29910.83190.101*
N10.16018 (8)0.48993 (10)0.77008 (16)0.0375 (3)
N20.28561 (8)0.40583 (10)0.92822 (16)0.0402 (3)
N30.29862 (8)0.54942 (10)0.73057 (16)0.0397 (3)
N40.35659 (12)0.70387 (13)0.6517 (2)0.0699 (5)
O10.27164 (10)0.25478 (10)1.09671 (19)0.0662 (4)
S10.06414 (3)0.25652 (3)1.02987 (6)0.05010 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0434 (8)0.0343 (7)0.0358 (8)−0.0020 (6)0.0073 (6)−0.0069 (6)
C20.0488 (9)0.0438 (8)0.0502 (10)0.0038 (7)0.0054 (7)−0.0002 (7)
C30.0465 (10)0.0589 (11)0.0709 (13)0.0070 (8)0.0035 (9)−0.0047 (9)
C40.0433 (10)0.0640 (11)0.0865 (15)−0.0031 (9)0.0140 (10)−0.0157 (11)
C50.0538 (11)0.0523 (10)0.0672 (12)−0.0111 (8)0.0201 (9)−0.0072 (9)
C60.0501 (9)0.0383 (7)0.0433 (9)−0.0063 (7)0.0112 (7)−0.0071 (7)
C70.0438 (8)0.0309 (7)0.0317 (7)−0.0031 (6)0.0024 (6)−0.0017 (6)
C80.0501 (9)0.0343 (7)0.0359 (8)−0.0054 (6)0.0022 (6)0.0029 (6)
C90.0505 (9)0.0401 (8)0.0435 (9)−0.0035 (7)−0.0021 (7)0.0067 (7)
C100.0447 (8)0.0313 (7)0.0337 (8)−0.0021 (6)0.0025 (6)0.0000 (6)
C110.0814 (14)0.0351 (8)0.0741 (13)−0.0054 (8)0.0322 (11)−0.0024 (8)
C120.0597 (11)0.0528 (10)0.0457 (10)−0.0058 (8)0.0147 (8)−0.0054 (8)
C130.0521 (10)0.0655 (11)0.0472 (10)−0.0090 (9)0.0123 (8)0.0030 (8)
C140.0402 (8)0.0494 (9)0.0459 (9)0.0004 (7)−0.0033 (7)0.0003 (7)
C150.0559 (10)0.0709 (12)0.0573 (12)0.0044 (9)−0.0118 (9)−0.0140 (9)
C160.0576 (11)0.0676 (13)0.0756 (14)0.0157 (9)0.0014 (10)−0.0118 (10)
N10.0406 (7)0.0349 (6)0.0363 (7)−0.0002 (5)0.0029 (5)0.0040 (5)
N20.0423 (7)0.0381 (6)0.0381 (7)−0.0013 (5)−0.0030 (5)0.0029 (5)
N30.0409 (7)0.0369 (6)0.0411 (7)−0.0022 (5)0.0044 (5)0.0016 (5)
N40.0847 (13)0.0507 (9)0.0801 (12)−0.0141 (8)0.0333 (10)0.0046 (8)
O10.0630 (9)0.0585 (8)0.0717 (10)−0.0013 (6)−0.0118 (7)0.0320 (6)
S10.0584 (3)0.0417 (3)0.0497 (3)−0.01108 (17)0.0051 (2)0.01099 (17)

Geometric parameters (Å, °)

C1—C21.393 (2)C10—N31.4166 (18)
C1—C61.405 (2)C11—N41.296 (2)
C1—C71.437 (2)C11—N31.353 (2)
C2—C31.368 (3)C11—H110.9300
C2—H20.9300C12—C131.341 (2)
C3—C41.397 (3)C12—N31.372 (2)
C3—H30.9300C12—H120.9300
C4—C51.371 (3)C13—N41.363 (2)
C4—H40.9300C13—H130.9300
C5—C61.392 (2)C14—N21.499 (2)
C5—H50.9300C14—C161.508 (2)
C6—S11.7437 (18)C14—C151.509 (3)
C7—C81.370 (2)C14—H140.9800
C7—N11.3713 (18)C15—H15A0.9600
C8—C91.425 (2)C15—H15B0.9600
C8—S11.7247 (15)C15—H15C0.9600
C9—O11.2279 (19)C16—H16A0.9600
C9—N21.4126 (19)C16—H16B0.9600
C10—N11.2835 (19)C16—H16C0.9600
C10—N21.3816 (18)
C2—C1—C6119.98 (14)C13—C12—N3105.79 (15)
C2—C1—C7129.35 (14)C13—C12—H12127.1
C6—C1—C7110.66 (13)N3—C12—H12127.1
C3—C2—C1119.07 (16)C12—C13—N4110.89 (16)
C3—C2—H2120.5C12—C13—H13124.6
C1—C2—H2120.5N4—C13—H13124.6
C2—C3—C4120.61 (18)N2—C14—C16112.49 (14)
C2—C3—H3119.7N2—C14—C15110.11 (14)
C4—C3—H3119.7C16—C14—C15114.53 (15)
C5—C4—C3121.45 (17)N2—C14—H14106.4
C5—C4—H4119.3C16—C14—H14106.4
C3—C4—H4119.3C15—C14—H14106.4
C4—C5—C6118.25 (17)C14—C15—H15A109.5
C4—C5—H5120.9C14—C15—H15B109.5
C6—C5—H5120.9H15A—C15—H15B109.5
C5—C6—C1120.63 (16)C14—C15—H15C109.5
C5—C6—S1126.75 (14)H15A—C15—H15C109.5
C1—C6—S1112.62 (12)H15B—C15—H15C109.5
C8—C7—N1122.53 (14)C14—C16—H16A109.5
C8—C7—C1112.70 (13)C14—C16—H16B109.5
N1—C7—C1124.70 (13)H16A—C16—H16B109.5
C7—C8—C9122.07 (14)C14—C16—H16C109.5
C7—C8—S1113.57 (12)H16A—C16—H16C109.5
C9—C8—S1124.34 (11)H16B—C16—H16C109.5
O1—C9—N2121.34 (15)C10—N1—C7115.30 (12)
O1—C9—C8125.79 (15)C10—N2—C9119.78 (12)
N2—C9—C8112.86 (12)C10—N2—C14121.25 (12)
N1—C10—N2127.02 (13)C9—N2—C14118.78 (12)
N1—C10—N3116.35 (12)C11—N3—C12106.00 (14)
N2—C10—N3116.63 (12)C11—N3—C10125.99 (14)
N4—C11—N3112.37 (17)C12—N3—C10127.67 (13)
N4—C11—H11123.8C11—N4—C13104.96 (15)
N3—C11—H11123.8C8—S1—C690.44 (8)
C6—C1—C2—C30.4 (2)C1—C7—N1—C10178.52 (13)
C7—C1—C2—C3179.29 (16)N1—C10—N2—C96.4 (2)
C1—C2—C3—C4−0.3 (3)N3—C10—N2—C9−173.15 (12)
C2—C3—C4—C50.1 (3)N1—C10—N2—C14−168.50 (14)
C3—C4—C5—C6−0.1 (3)N3—C10—N2—C1411.9 (2)
C4—C5—C6—C10.2 (2)O1—C9—N2—C10175.54 (16)
C4—C5—C6—S1−179.33 (14)C8—C9—N2—C10−5.9 (2)
C2—C1—C6—C5−0.3 (2)O1—C9—N2—C14−9.4 (2)
C7—C1—C6—C5−179.46 (14)C8—C9—N2—C14169.11 (13)
C2—C1—C6—S1179.26 (12)C16—C14—N2—C10−119.77 (17)
C7—C1—C6—S10.14 (15)C15—C14—N2—C10111.16 (16)
C2—C1—C7—C8−179.09 (15)C16—C14—N2—C965.26 (19)
C6—C1—C7—C8−0.07 (17)C15—C14—N2—C9−63.80 (18)
C2—C1—C7—N1−1.9 (2)N4—C11—N3—C12−0.4 (2)
C6—C1—C7—N1177.12 (13)N4—C11—N3—C10−174.04 (16)
N1—C7—C8—C94.5 (2)C13—C12—N3—C110.6 (2)
C1—C7—C8—C9−178.29 (13)C13—C12—N3—C10174.10 (15)
N1—C7—C8—S1−177.29 (11)N1—C10—N3—C1170.9 (2)
C1—C7—C8—S1−0.03 (17)N2—C10—N3—C11−109.48 (18)
C7—C8—C9—O1179.45 (17)N1—C10—N3—C12−101.43 (18)
S1—C8—C9—O11.4 (3)N2—C10—N3—C1278.2 (2)
C7—C8—C9—N21.0 (2)N3—C11—N4—C130.0 (2)
S1—C8—C9—N2−177.07 (11)C12—C13—N4—C110.4 (2)
N3—C12—C13—N4−0.6 (2)C7—C8—S1—C60.09 (12)
N2—C10—N1—C7−0.9 (2)C9—C8—S1—C6178.31 (14)
N3—C10—N1—C7178.70 (12)C5—C6—S1—C8179.44 (16)
C8—C7—N1—C10−4.6 (2)C1—C6—S1—C8−0.14 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O10.962.382.963 (3)119
C15—H15A···O10.962.453.046 (2)120

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2265).

References

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  • Bruker (2001). SMART (Version 5.628), SAINT (Version 6.45) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cao, M.-H. (2007). Acta Cryst. E63, o2660.
  • Chambhare, R. V., Khadse, B. G., Bobde, A. S. & Bahekar, R. H. (2003). Eur. J. Med. Chem.38, 89–100. [PubMed]
  • Ding, M.-W., Xu, S.-Z. & Zhao, J.-F. (2004). J. Org. Chem.69, 8366–8371. [PubMed]
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Xu, S.-Z., Cao, M.-H., Hu, Y.-G., Ding, M.-W. & Xiao, W.-J. (2005). Acta Cryst. E61, o2789–o2790.
  • Xu, S.-Z., Hu, Y.-G., Liu, M.-G. & Ding, M.-W. (2006). Acta Cryst. E62, o3428–o3429.

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