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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2173–o2174.
Published online 2010 July 31. doi:  10.1107/S1600536810029521
PMCID: PMC3007370

Ethyl (2,5-dioxo-1-phenyl-2,3-dihydro-1H,5H-1-benzofuro[3,2-d]imidazo[1,2-a]pyrimidin-3-yl)acetate

Abstract

In the title compound, C22H17N3O5, synthesized via the aza-Wittig reaction of ethyl 3-(phenyl­imino­methyl­ene­amino)­benzofuran-2-carboxyl­ate, benzene isocyanate and diethyl 2-amino­succinate, the imidazo[1,2-a]benzo[4,5]furo[2,3-d]pyrim­idine ring system is essentially planar (r.m.s. deviation for all 16 non-H atoms = 0.020 Å). The phenyl ring is twisted with respect to this ring system, making a dihedral angle of 54.23 (4)°. The crystal packing is stabilized by weak inter­molecular C—H(...)O inter­actions.

Related literature

The title compound may be used as a precursor for obtaining bioactive mol­ecules, see: Bellarosa et al. (1996 [triangle]). For the biological activity of benzofuropyrimidine derivatives, see: Moneam et al. (2004 [triangle]); Bodke et al. (2003 [triangle]); Palacios et al. (2007 [triangle]); Duval et al. (2005 [triangle]); Teimouria et al. (2006 [triangle]). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 [triangle], 2006 [triangle], 2007 [triangle], 2008 [triangle]).

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Object name is e-66-o2173-scheme1.jpg

Experimental

Crystal data

  • C22H17N3O5
  • M r = 403.39
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2173-efi1.jpg
  • a = 8.5418 (12) Å
  • b = 8.6553 (12) Å
  • c = 14.519 (2) Å
  • α = 86.642 (2)°
  • β = 82.873 (2)°
  • γ = 62.619 (2)°
  • V = 945.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 292 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.970, T max = 0.990
  • 5574 measured reflections
  • 3663 independent reflections
  • 2844 reflections with I > 2σ(I)
  • R int = 0.084

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.129
  • S = 1.06
  • 3663 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029521/bt5306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029521/bt5306Isup2.hkl

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

Acknowledgments

The authors are grateful to Dr Y. G. Hu (Institute of Medicinal Chemistry, Hubei Medical University, Shiyan, China) and Dr X. G. Meng (Key Laboratory of Pesticides & Chemical Biology of the Ministry of Education, Central China Normal University, Wuhan, Hubei, China) for the synthesis, data collection and analysis. This work were supported by the Education Commission of Hubei Province of China (grant No. B200624004), Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant No. 2008QDJ1).

supplementary crystallographic information

Comment

The derivatives of benzofuropyrimidine are of great importance because of their remarkable biological properties. Some of them have shown good analgesic, anti-inflammatory and antimicrobial activities (Moneam et al., 2004 and Bodke et al., 2003). On the other hand, heterocycles containing an imidazolone nucleus also exhibit various biological activities. Several of them have shown good antibacterial, antifungal activities or are used as leukotriene B4 receptor antagonist and potassium channel openers (Palacios et al., 2007 and Duval et al., 2005, Teimouria et al., 2006). The introduction of an imidazolone ring to the benzofuro[3,2-d]pyrimidin-4(3H)-one system is expected to influence the biological activities significantly. As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Hu et al., 2005, 2006, 2007, 2008), we have synthesized and structurally characterized the title compound, and here we report its crystal structure (Fig. 1).

In the crystal structure of the title compound, all ring atoms of imidazo[1,2-a]benzo[4,5]furo [2,3-d]pyrimidine system are essentially coplanar, with maximum deviations -0.039 (3)Å and 0.057 (1)Å for O3 and N2, respectively. The phenyl (C11—C16) ring is twisted with respect to it, making dihedral angles of 54.23 (4)°. The structure is mainly stabilized by weak C—H···O interactions.

Experimental

The title compound was obtained in excellent yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:2 v/v) at room temperature.

Refinement

All H-atoms were found in a difference map but positioned with idealized geometry and refined with Uiso(H)= 1.5Ueq(C) for methyl H atoms and Uiso(H) =1.2Ueq(C) for all other H atoms using a riding model with C—H ranging from 0.93Å to 0.97Å.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are at the 50% probability level.

Crystal data

C22H17N3O5Z = 2
Mr = 403.39F(000) = 420
Triclinic, P1Dx = 1.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5418 (12) ÅCell parameters from 2477 reflections
b = 8.6553 (12) Åθ = 6.0–25.0°
c = 14.519 (2) ŵ = 0.10 mm1
α = 86.642 (2)°T = 292 K
β = 82.873 (2)°Block, colourless
γ = 62.619 (2)°0.30 × 0.20 × 0.10 mm
V = 945.8 (2) Å3

Data collection

Bruker SMART 4K CCD area-detector diffractometer3663 independent reflections
Radiation source: fine-focus sealed tube2844 reflections with I > 2σ(I)
graphiteRint = 0.084
[var phi] and ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −10→10
Tmin = 0.970, Tmax = 0.990k = −5→10
5574 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0729P)2 + 0.002P] where P = (Fo2 + 2Fc2)/3
3663 reflections(Δ/σ)max = 0.003
272 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.35 e Å3

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
C10.8363 (2)0.04672 (19)0.37332 (10)0.0385 (4)
C20.9489 (2)0.0189 (2)0.29234 (11)0.0477 (4)
H20.92100.09870.24370.057*
C31.1056 (2)−0.1346 (2)0.28769 (11)0.0492 (4)
H31.1857−0.15870.23450.059*
C41.1467 (2)−0.2539 (2)0.36064 (11)0.0461 (4)
H41.2535−0.35560.35510.055*
C51.0323 (2)−0.2243 (2)0.44088 (11)0.0414 (4)
H51.0602−0.30450.48930.050*
C60.8732 (2)−0.07023 (19)0.44725 (10)0.0361 (3)
C70.72423 (19)0.00914 (18)0.51685 (10)0.0352 (3)
C80.6108 (2)0.16444 (19)0.48043 (10)0.0382 (4)
C90.4462 (2)0.2830 (2)0.52864 (11)0.0422 (4)
C100.5479 (2)0.05584 (19)0.64773 (10)0.0366 (4)
C110.5896 (2)−0.1152 (2)0.79340 (10)0.0411 (4)
C120.6649 (2)−0.2842 (2)0.76226 (12)0.0493 (4)
H120.6413−0.30920.70560.059*
C130.7760 (2)−0.4161 (2)0.81653 (13)0.0547 (5)
H130.8279−0.53070.79620.066*
C140.8108 (2)−0.3794 (3)0.90068 (13)0.0580 (5)
H140.8876−0.46870.93620.070*
C150.7316 (2)−0.2107 (3)0.93184 (13)0.0609 (5)
H150.7522−0.18640.98940.073*
C160.6215 (2)−0.0769 (2)0.87790 (11)0.0530 (4)
H160.56960.03760.89840.064*
C170.3210 (2)0.1644 (2)0.76449 (11)0.0430 (4)
C180.2735 (2)0.2986 (2)0.68624 (10)0.0422 (4)
H180.16970.30530.66060.051*
C190.2319 (2)0.4798 (2)0.71761 (11)0.0473 (4)
H19A0.25480.54300.66460.057*
H19B0.10680.54190.73970.057*
C200.3383 (2)0.4779 (2)0.79307 (11)0.0424 (4)
C210.3358 (2)0.6322 (2)0.92299 (12)0.0550 (5)
H21A0.44540.63720.90120.066*
H21B0.36340.53080.96260.066*
C220.2109 (3)0.7929 (3)0.97571 (15)0.0814 (7)
H22A0.19000.89290.93710.122*
H22B0.26140.80001.02980.122*
H22C0.10070.78930.99430.122*
N10.69428 (17)−0.05275 (16)0.60320 (8)0.0381 (3)
N20.42881 (16)0.21602 (16)0.61779 (8)0.0392 (3)
N30.48245 (17)0.02592 (16)0.73590 (8)0.0413 (3)
O10.67400 (14)0.19234 (13)0.39205 (7)0.0442 (3)
O20.33196 (16)0.42088 (15)0.50277 (8)0.0599 (4)
O30.23141 (16)0.17923 (16)0.83798 (8)0.0561 (3)
O40.48112 (15)0.36241 (16)0.80601 (10)0.0646 (4)
O50.25135 (14)0.62047 (14)0.84498 (8)0.0501 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0384 (8)0.0302 (8)0.0392 (8)−0.0076 (7)−0.0086 (6)−0.0031 (6)
C20.0559 (10)0.0411 (9)0.0391 (9)−0.0164 (8)−0.0047 (7)0.0019 (7)
C30.0470 (10)0.0478 (10)0.0451 (9)−0.0156 (8)0.0005 (8)−0.0065 (8)
C40.0367 (8)0.0387 (9)0.0510 (10)−0.0056 (7)−0.0073 (7)−0.0087 (8)
C50.0429 (9)0.0336 (8)0.0421 (9)−0.0105 (7)−0.0132 (7)−0.0004 (7)
C60.0400 (8)0.0310 (8)0.0349 (8)−0.0122 (7)−0.0112 (6)−0.0021 (6)
C70.0397 (8)0.0298 (8)0.0336 (8)−0.0118 (7)−0.0115 (6)−0.0002 (6)
C80.0434 (9)0.0325 (8)0.0328 (8)−0.0113 (7)−0.0088 (6)0.0006 (6)
C90.0455 (9)0.0336 (8)0.0394 (9)−0.0096 (7)−0.0123 (7)0.0011 (7)
C100.0425 (8)0.0290 (8)0.0364 (8)−0.0131 (7)−0.0097 (6)−0.0016 (6)
C110.0463 (9)0.0405 (9)0.0369 (8)−0.0206 (8)−0.0052 (7)0.0044 (7)
C120.0645 (11)0.0440 (10)0.0416 (9)−0.0260 (9)−0.0097 (8)0.0034 (7)
C130.0581 (11)0.0401 (10)0.0590 (11)−0.0171 (9)−0.0069 (9)0.0066 (8)
C140.0498 (10)0.0613 (12)0.0549 (11)−0.0191 (9)−0.0122 (8)0.0176 (9)
C150.0632 (12)0.0756 (14)0.0420 (10)−0.0287 (11)−0.0136 (8)0.0033 (9)
C160.0632 (11)0.0542 (11)0.0425 (9)−0.0266 (9)−0.0082 (8)−0.0031 (8)
C170.0439 (9)0.0425 (9)0.0425 (9)−0.0188 (8)−0.0050 (7)−0.0072 (7)
C180.0379 (8)0.0406 (9)0.0421 (9)−0.0119 (7)−0.0051 (7)−0.0076 (7)
C190.0458 (9)0.0385 (9)0.0464 (9)−0.0088 (8)−0.0058 (7)−0.0060 (7)
C200.0364 (9)0.0330 (8)0.0502 (9)−0.0098 (7)−0.0004 (7)−0.0049 (7)
C210.0577 (11)0.0603 (12)0.0495 (10)−0.0277 (10)−0.0094 (8)−0.0048 (9)
C220.0964 (17)0.0683 (14)0.0747 (15)−0.0303 (13)−0.0108 (12)−0.0264 (12)
N10.0424 (7)0.0304 (7)0.0353 (7)−0.0105 (6)−0.0085 (6)0.0006 (5)
N20.0403 (7)0.0319 (7)0.0368 (7)−0.0083 (6)−0.0064 (6)−0.0020 (5)
N30.0468 (8)0.0347 (7)0.0371 (7)−0.0143 (6)−0.0036 (6)−0.0006 (5)
O10.0457 (6)0.0329 (6)0.0374 (6)−0.0038 (5)−0.0062 (5)0.0032 (5)
O20.0555 (7)0.0413 (7)0.0512 (7)0.0054 (6)−0.0110 (6)0.0065 (6)
O30.0540 (7)0.0614 (8)0.0462 (7)−0.0224 (6)0.0045 (6)−0.0055 (6)
O40.0422 (7)0.0484 (8)0.0882 (10)−0.0036 (6)−0.0173 (6)−0.0173 (7)
O50.0492 (7)0.0386 (7)0.0494 (7)−0.0065 (5)−0.0104 (5)−0.0098 (5)

Geometric parameters (Å, °)

C1—C21.380 (2)C13—C141.380 (2)
C1—O11.3871 (17)C13—H130.9300
C1—C61.393 (2)C14—C151.374 (3)
C2—C31.384 (2)C14—H140.9300
C2—H20.9300C15—C161.383 (2)
C3—C41.394 (2)C15—H150.9300
C3—H30.9300C16—H160.9300
C4—C51.378 (2)C17—O31.2096 (18)
C4—H40.9300C17—N31.381 (2)
C5—C61.396 (2)C17—C181.527 (2)
C5—H50.9300C18—N21.4638 (18)
C6—C71.439 (2)C18—C191.524 (2)
C7—C81.368 (2)C18—H180.9800
C7—N11.3756 (18)C19—C201.502 (2)
C8—O11.3811 (18)C19—H19A0.9700
C8—C91.426 (2)C19—H19B0.9700
C9—O21.2183 (18)C20—O41.1984 (18)
C9—N21.406 (2)C20—O51.3303 (18)
C10—N11.2863 (19)C21—O51.4482 (19)
C10—N21.3738 (19)C21—C221.488 (2)
C10—N31.3910 (19)C21—H21A0.9700
C11—C121.378 (2)C21—H21B0.9700
C11—C161.380 (2)C22—H22A0.9600
C11—N31.438 (2)C22—H22B0.9600
C12—C131.381 (2)C22—H22C0.9600
C12—H120.9300
C2—C1—O1125.12 (14)C16—C15—H15119.9
C2—C1—C6123.52 (15)C11—C16—C15119.29 (17)
O1—C1—C6111.37 (13)C11—C16—H16120.4
C1—C2—C3116.09 (16)C15—C16—H16120.4
C1—C2—H2122.0O3—C17—N3127.00 (16)
C3—C2—H2122.0O3—C17—C18125.28 (15)
C2—C3—C4121.75 (15)N3—C17—C18107.72 (13)
C2—C3—H3119.1N2—C18—C19115.56 (13)
C4—C3—H3119.1N2—C18—C17101.49 (12)
C5—C4—C3121.36 (15)C19—C18—C17113.30 (12)
C5—C4—H4119.3N2—C18—H18108.7
C3—C4—H4119.3C19—C18—H18108.7
C4—C5—C6117.96 (15)C17—C18—H18108.7
C4—C5—H5121.0C20—C19—C18113.46 (13)
C6—C5—H5121.0C20—C19—H19A108.9
C1—C6—C5119.32 (14)C18—C19—H19A108.9
C1—C6—C7105.44 (13)C20—C19—H19B108.9
C5—C6—C7135.23 (14)C18—C19—H19B108.9
C8—C7—N1124.78 (14)H19A—C19—H19B107.7
C8—C7—C6106.21 (13)O4—C20—O5124.28 (15)
N1—C7—C6129.01 (13)O4—C20—C19124.77 (14)
C7—C8—O1112.30 (13)O5—C20—C19110.94 (13)
C7—C8—C9123.50 (14)O5—C21—C22107.98 (15)
O1—C8—C9124.20 (13)O5—C21—H21A110.1
O2—C9—N2121.73 (15)C22—C21—H21A110.1
O2—C9—C8129.66 (16)O5—C21—H21B110.1
N2—C9—C8108.61 (13)C22—C21—H21B110.1
N1—C10—N2127.32 (14)H21A—C21—H21B108.4
N1—C10—N3124.27 (14)C21—C22—H22A109.5
N2—C10—N3108.40 (13)C21—C22—H22B109.5
C12—C11—C16121.05 (16)H22A—C22—H22B109.5
C12—C11—N3120.22 (13)C21—C22—H22C109.5
C16—C11—N3118.67 (15)H22A—C22—H22C109.5
C11—C12—C13118.91 (15)H22B—C22—H22C109.5
C11—C12—H12120.5C10—N1—C7111.84 (13)
C13—C12—H12120.5C10—N2—C9123.79 (13)
C14—C13—C12120.62 (17)C10—N2—C18111.50 (12)
C14—C13—H13119.7C9—N2—C18124.39 (13)
C12—C13—H13119.7C17—N3—C10110.86 (13)
C15—C14—C13119.84 (17)C17—N3—C11125.99 (13)
C15—C14—H14120.1C10—N3—C11122.06 (13)
C13—C14—H14120.1C8—O1—C1104.69 (11)
C14—C15—C16120.26 (17)C20—O5—C21116.76 (13)
C14—C15—H15119.9
O1—C1—C2—C3179.50 (14)C18—C19—C20—O426.2 (2)
C6—C1—C2—C3−0.4 (2)C18—C19—C20—O5−152.67 (14)
C1—C2—C3—C40.1 (2)N2—C10—N1—C70.0 (2)
C2—C3—C4—C50.1 (3)N3—C10—N1—C7178.67 (13)
C3—C4—C5—C6−0.2 (2)C8—C7—N1—C10−2.0 (2)
C2—C1—C6—C50.4 (2)C6—C7—N1—C10178.43 (14)
O1—C1—C6—C5−179.53 (13)N1—C10—N2—C93.6 (2)
C2—C1—C6—C7179.39 (14)N3—C10—N2—C9−175.22 (13)
O1—C1—C6—C7−0.51 (16)N1—C10—N2—C18177.39 (14)
C4—C5—C6—C1−0.1 (2)N3—C10—N2—C18−1.42 (16)
C4—C5—C6—C7−178.74 (15)O2—C9—N2—C10175.24 (15)
C1—C6—C7—C80.13 (16)C8—C9—N2—C10−4.5 (2)
C5—C6—C7—C8178.92 (17)O2—C9—N2—C182.2 (2)
C1—C6—C7—N1179.78 (14)C8—C9—N2—C18−177.54 (13)
C5—C6—C7—N1−1.4 (3)C19—C18—N2—C10124.87 (14)
N1—C7—C8—O1−179.38 (12)C17—C18—N2—C101.87 (15)
C6—C7—C8—O10.29 (17)C19—C18—N2—C9−61.38 (19)
N1—C7—C8—C90.5 (2)C17—C18—N2—C9175.62 (13)
C6—C7—C8—C9−179.86 (14)O3—C17—N3—C10−178.92 (15)
C7—C8—C9—O2−177.07 (16)C18—C17—N3—C100.95 (16)
O1—C8—C9—O22.8 (3)O3—C17—N3—C11−10.7 (3)
C7—C8—C9—N22.7 (2)C18—C17—N3—C11169.13 (13)
O1—C8—C9—N2−177.49 (13)N1—C10—N3—C17−178.61 (14)
C16—C11—C12—C13−1.0 (3)N2—C10—N3—C170.25 (17)
N3—C11—C12—C13176.04 (15)N1—C10—N3—C1112.7 (2)
C11—C12—C13—C140.2 (3)N2—C10—N3—C11−168.47 (13)
C12—C13—C14—C151.3 (3)C12—C11—N3—C17134.92 (17)
C13—C14—C15—C16−2.0 (3)C16—C11—N3—C17−48.0 (2)
C12—C11—C16—C150.3 (3)C12—C11—N3—C10−58.1 (2)
N3—C11—C16—C15−176.76 (15)C16—C11—N3—C10118.95 (17)
C14—C15—C16—C111.2 (3)C7—C8—O1—C1−0.59 (16)
O3—C17—C18—N2178.21 (15)C9—C8—O1—C1179.56 (14)
N3—C17—C18—N2−1.66 (15)C2—C1—O1—C8−179.22 (14)
O3—C17—C18—C1953.7 (2)C6—C1—O1—C80.68 (16)
N3—C17—C18—C19−126.20 (14)O4—C20—O5—C21−1.4 (2)
N2—C18—C19—C20−83.04 (17)C19—C20—O5—C21177.50 (14)
C17—C18—C19—C2033.47 (19)C22—C21—O5—C20−175.36 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O5i0.932.563.442 (2)159
C3—H3···O4ii0.932.583.305 (2)135
C5—H5···O2iii0.932.463.132 (2)129
C15—H15···O3iv0.932.533.434 (2)163
C19—H19A···O20.972.523.137 (2)122

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) x+1, y−1, z; (iv) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5306).

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