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

In the title compound, C(22)H(17)N(3)O(5), synthesized via the aza-Wittig reaction of ethyl 3-(phenyl-imino-methyl-ene-amino)-benzofuran-2-carboxyl-ate, benzene isocyanate and diethyl 2-amino-succinate, the imidazo[1,2-a]benzo[4,5]furo[2,3-d]pyrim-idine 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 inter-molecular C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C22H17N3O5

M = 403.39

Triclinic,

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 ▶) 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 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 ▶).

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

C22H17N3O5	Z = 2
Mr = 403.39	F(000) = 420
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5418 (12) Å	Cell parameters from 2477 reflections
b = 8.6553 (12) Å	θ = 6.0–25.0°
c = 14.519 (2) Å	µ = 0.10 mm−1
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

Bruker SMART 4K CCD area-detector diffractometer	3663 independent reflections
Radiation source: fine-focus sealed tube	2844 reflections with I > 2σ(I)
graphite	Rint = 0.084
φ and ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.970, Tmax = 0.990	k = −5→10
5574 measured reflections	l = −17→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.002P] where P = (Fo2 + 2Fc2)/3
3663 reflections	(Δ/σ)max = 0.003
272 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	0.8363 (2)	0.04672 (19)	0.37332 (10)	0.0385 (4)
C2	0.9489 (2)	0.0189 (2)	0.29234 (11)	0.0477 (4)
H2	0.9210	0.0987	0.2437	0.057*
C3	1.1056 (2)	−0.1346 (2)	0.28769 (11)	0.0492 (4)
H3	1.1857	−0.1587	0.2345	0.059*
C4	1.1467 (2)	−0.2539 (2)	0.36064 (11)	0.0461 (4)
H4	1.2535	−0.3556	0.3551	0.055*
C5	1.0323 (2)	−0.2243 (2)	0.44088 (11)	0.0414 (4)
H5	1.0602	−0.3045	0.4893	0.050*
C6	0.8732 (2)	−0.07023 (19)	0.44725 (10)	0.0361 (3)
C7	0.72423 (19)	0.00914 (18)	0.51685 (10)	0.0352 (3)
C8	0.6108 (2)	0.16444 (19)	0.48043 (10)	0.0382 (4)
C9	0.4462 (2)	0.2830 (2)	0.52864 (11)	0.0422 (4)
C10	0.5479 (2)	0.05584 (19)	0.64773 (10)	0.0366 (4)
C11	0.5896 (2)	−0.1152 (2)	0.79340 (10)	0.0411 (4)
C12	0.6649 (2)	−0.2842 (2)	0.76226 (12)	0.0493 (4)
H12	0.6413	−0.3092	0.7056	0.059*
C13	0.7760 (2)	−0.4161 (2)	0.81653 (13)	0.0547 (5)
H13	0.8279	−0.5307	0.7962	0.066*
C14	0.8108 (2)	−0.3794 (3)	0.90068 (13)	0.0580 (5)
H14	0.8876	−0.4687	0.9362	0.070*
C15	0.7316 (2)	−0.2107 (3)	0.93184 (13)	0.0609 (5)
H15	0.7522	−0.1864	0.9894	0.073*
C16	0.6215 (2)	−0.0769 (2)	0.87790 (11)	0.0530 (4)
H16	0.5696	0.0376	0.8984	0.064*
C17	0.3210 (2)	0.1644 (2)	0.76449 (11)	0.0430 (4)
C18	0.2735 (2)	0.2986 (2)	0.68624 (10)	0.0422 (4)
H18	0.1697	0.3053	0.6606	0.051*
C19	0.2319 (2)	0.4798 (2)	0.71761 (11)	0.0473 (4)
H19A	0.2548	0.5430	0.6646	0.057*
H19B	0.1068	0.5419	0.7397	0.057*
C20	0.3383 (2)	0.4779 (2)	0.79307 (11)	0.0424 (4)
C21	0.3358 (2)	0.6322 (2)	0.92299 (12)	0.0550 (5)
H21A	0.4454	0.6372	0.9012	0.066*
H21B	0.3634	0.5308	0.9626	0.066*
C22	0.2109 (3)	0.7929 (3)	0.97571 (15)	0.0814 (7)
H22A	0.1900	0.8929	0.9371	0.122*
H22B	0.2614	0.8000	1.0298	0.122*
H22C	0.1007	0.7893	0.9943	0.122*
N1	0.69428 (17)	−0.05275 (16)	0.60320 (8)	0.0381 (3)
N2	0.42881 (16)	0.21602 (16)	0.61779 (8)	0.0392 (3)
N3	0.48245 (17)	0.02592 (16)	0.73590 (8)	0.0413 (3)
O1	0.67400 (14)	0.19234 (13)	0.39205 (7)	0.0442 (3)
O2	0.33196 (16)	0.42088 (15)	0.50277 (8)	0.0599 (4)
O3	0.23141 (16)	0.17923 (16)	0.83798 (8)	0.0561 (3)
O4	0.48112 (15)	0.36241 (16)	0.80601 (10)	0.0646 (4)
O5	0.25135 (14)	0.62047 (14)	0.84498 (8)	0.0501 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0384 (8)	0.0302 (8)	0.0392 (8)	−0.0076 (7)	−0.0086 (6)	−0.0031 (6)
C2	0.0559 (10)	0.0411 (9)	0.0391 (9)	−0.0164 (8)	−0.0047 (7)	0.0019 (7)
C3	0.0470 (10)	0.0478 (10)	0.0451 (9)	−0.0156 (8)	0.0005 (8)	−0.0065 (8)
C4	0.0367 (8)	0.0387 (9)	0.0510 (10)	−0.0056 (7)	−0.0073 (7)	−0.0087 (8)
C5	0.0429 (9)	0.0336 (8)	0.0421 (9)	−0.0105 (7)	−0.0132 (7)	−0.0004 (7)
C6	0.0400 (8)	0.0310 (8)	0.0349 (8)	−0.0122 (7)	−0.0112 (6)	−0.0021 (6)
C7	0.0397 (8)	0.0298 (8)	0.0336 (8)	−0.0118 (7)	−0.0115 (6)	−0.0002 (6)
C8	0.0434 (9)	0.0325 (8)	0.0328 (8)	−0.0113 (7)	−0.0088 (6)	0.0006 (6)
C9	0.0455 (9)	0.0336 (8)	0.0394 (9)	−0.0096 (7)	−0.0123 (7)	0.0011 (7)
C10	0.0425 (8)	0.0290 (8)	0.0364 (8)	−0.0131 (7)	−0.0097 (6)	−0.0016 (6)
C11	0.0463 (9)	0.0405 (9)	0.0369 (8)	−0.0206 (8)	−0.0052 (7)	0.0044 (7)
C12	0.0645 (11)	0.0440 (10)	0.0416 (9)	−0.0260 (9)	−0.0097 (8)	0.0034 (7)
C13	0.0581 (11)	0.0401 (10)	0.0590 (11)	−0.0171 (9)	−0.0069 (9)	0.0066 (8)
C14	0.0498 (10)	0.0613 (12)	0.0549 (11)	−0.0191 (9)	−0.0122 (8)	0.0176 (9)
C15	0.0632 (12)	0.0756 (14)	0.0420 (10)	−0.0287 (11)	−0.0136 (8)	0.0033 (9)
C16	0.0632 (11)	0.0542 (11)	0.0425 (9)	−0.0266 (9)	−0.0082 (8)	−0.0031 (8)
C17	0.0439 (9)	0.0425 (9)	0.0425 (9)	−0.0188 (8)	−0.0050 (7)	−0.0072 (7)
C18	0.0379 (8)	0.0406 (9)	0.0421 (9)	−0.0119 (7)	−0.0051 (7)	−0.0076 (7)
C19	0.0458 (9)	0.0385 (9)	0.0464 (9)	−0.0088 (8)	−0.0058 (7)	−0.0060 (7)
C20	0.0364 (9)	0.0330 (8)	0.0502 (9)	−0.0098 (7)	−0.0004 (7)	−0.0049 (7)
C21	0.0577 (11)	0.0603 (12)	0.0495 (10)	−0.0277 (10)	−0.0094 (8)	−0.0048 (9)
C22	0.0964 (17)	0.0683 (14)	0.0747 (15)	−0.0303 (13)	−0.0108 (12)	−0.0264 (12)
N1	0.0424 (7)	0.0304 (7)	0.0353 (7)	−0.0105 (6)	−0.0085 (6)	0.0006 (5)
N2	0.0403 (7)	0.0319 (7)	0.0368 (7)	−0.0083 (6)	−0.0064 (6)	−0.0020 (5)
N3	0.0468 (8)	0.0347 (7)	0.0371 (7)	−0.0143 (6)	−0.0036 (6)	−0.0006 (5)
O1	0.0457 (6)	0.0329 (6)	0.0374 (6)	−0.0038 (5)	−0.0062 (5)	0.0032 (5)
O2	0.0555 (7)	0.0413 (7)	0.0512 (7)	0.0054 (6)	−0.0110 (6)	0.0065 (6)
O3	0.0540 (7)	0.0614 (8)	0.0462 (7)	−0.0224 (6)	0.0045 (6)	−0.0055 (6)
O4	0.0422 (7)	0.0484 (8)	0.0882 (10)	−0.0036 (6)	−0.0173 (6)	−0.0173 (7)
O5	0.0492 (7)	0.0386 (7)	0.0494 (7)	−0.0065 (5)	−0.0104 (5)	−0.0098 (5)

C1—C2	1.380 (2)	C13—C14	1.380 (2)
C1—O1	1.3871 (17)	C13—H13	0.9300
C1—C6	1.393 (2)	C14—C15	1.374 (3)
C2—C3	1.384 (2)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.383 (2)
C3—C4	1.394 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.378 (2)	C17—O3	1.2096 (18)
C4—H4	0.9300	C17—N3	1.381 (2)
C5—C6	1.396 (2)	C17—C18	1.527 (2)
C5—H5	0.9300	C18—N2	1.4638 (18)
C6—C7	1.439 (2)	C18—C19	1.524 (2)
C7—C8	1.368 (2)	C18—H18	0.9800
C7—N1	1.3756 (18)	C19—C20	1.502 (2)
C8—O1	1.3811 (18)	C19—H19A	0.9700
C8—C9	1.426 (2)	C19—H19B	0.9700
C9—O2	1.2183 (18)	C20—O4	1.1984 (18)
C9—N2	1.406 (2)	C20—O5	1.3303 (18)
C10—N1	1.2863 (19)	C21—O5	1.4482 (19)
C10—N2	1.3738 (19)	C21—C22	1.488 (2)
C10—N3	1.3910 (19)	C21—H21A	0.9700
C11—C12	1.378 (2)	C21—H21B	0.9700
C11—C16	1.380 (2)	C22—H22A	0.9600
C11—N3	1.438 (2)	C22—H22B	0.9600
C12—C13	1.381 (2)	C22—H22C	0.9600
C12—H12	0.9300
C2—C1—O1	125.12 (14)	C16—C15—H15	119.9
C2—C1—C6	123.52 (15)	C11—C16—C15	119.29 (17)
O1—C1—C6	111.37 (13)	C11—C16—H16	120.4
C1—C2—C3	116.09 (16)	C15—C16—H16	120.4
C1—C2—H2	122.0	O3—C17—N3	127.00 (16)
C3—C2—H2	122.0	O3—C17—C18	125.28 (15)
C2—C3—C4	121.75 (15)	N3—C17—C18	107.72 (13)
C2—C3—H3	119.1	N2—C18—C19	115.56 (13)
C4—C3—H3	119.1	N2—C18—C17	101.49 (12)
C5—C4—C3	121.36 (15)	C19—C18—C17	113.30 (12)
C5—C4—H4	119.3	N2—C18—H18	108.7
C3—C4—H4	119.3	C19—C18—H18	108.7
C4—C5—C6	117.96 (15)	C17—C18—H18	108.7
C4—C5—H5	121.0	C20—C19—C18	113.46 (13)
C6—C5—H5	121.0	C20—C19—H19A	108.9
C1—C6—C5	119.32 (14)	C18—C19—H19A	108.9
C1—C6—C7	105.44 (13)	C20—C19—H19B	108.9
C5—C6—C7	135.23 (14)	C18—C19—H19B	108.9
C8—C7—N1	124.78 (14)	H19A—C19—H19B	107.7
C8—C7—C6	106.21 (13)	O4—C20—O5	124.28 (15)
N1—C7—C6	129.01 (13)	O4—C20—C19	124.77 (14)
C7—C8—O1	112.30 (13)	O5—C20—C19	110.94 (13)
C7—C8—C9	123.50 (14)	O5—C21—C22	107.98 (15)
O1—C8—C9	124.20 (13)	O5—C21—H21A	110.1
O2—C9—N2	121.73 (15)	C22—C21—H21A	110.1
O2—C9—C8	129.66 (16)	O5—C21—H21B	110.1
N2—C9—C8	108.61 (13)	C22—C21—H21B	110.1
N1—C10—N2	127.32 (14)	H21A—C21—H21B	108.4
N1—C10—N3	124.27 (14)	C21—C22—H22A	109.5
N2—C10—N3	108.40 (13)	C21—C22—H22B	109.5
C12—C11—C16	121.05 (16)	H22A—C22—H22B	109.5
C12—C11—N3	120.22 (13)	C21—C22—H22C	109.5
C16—C11—N3	118.67 (15)	H22A—C22—H22C	109.5
C11—C12—C13	118.91 (15)	H22B—C22—H22C	109.5
C11—C12—H12	120.5	C10—N1—C7	111.84 (13)
C13—C12—H12	120.5	C10—N2—C9	123.79 (13)
C14—C13—C12	120.62 (17)	C10—N2—C18	111.50 (12)
C14—C13—H13	119.7	C9—N2—C18	124.39 (13)
C12—C13—H13	119.7	C17—N3—C10	110.86 (13)
C15—C14—C13	119.84 (17)	C17—N3—C11	125.99 (13)
C15—C14—H14	120.1	C10—N3—C11	122.06 (13)
C13—C14—H14	120.1	C8—O1—C1	104.69 (11)
C14—C15—C16	120.26 (17)	C20—O5—C21	116.76 (13)
C14—C15—H15	119.9
O1—C1—C2—C3	179.50 (14)	C18—C19—C20—O4	26.2 (2)
C6—C1—C2—C3	−0.4 (2)	C18—C19—C20—O5	−152.67 (14)
C1—C2—C3—C4	0.1 (2)	N2—C10—N1—C7	0.0 (2)
C2—C3—C4—C5	0.1 (3)	N3—C10—N1—C7	178.67 (13)
C3—C4—C5—C6	−0.2 (2)	C8—C7—N1—C10	−2.0 (2)
C2—C1—C6—C5	0.4 (2)	C6—C7—N1—C10	178.43 (14)
O1—C1—C6—C5	−179.53 (13)	N1—C10—N2—C9	3.6 (2)
C2—C1—C6—C7	179.39 (14)	N3—C10—N2—C9	−175.22 (13)
O1—C1—C6—C7	−0.51 (16)	N1—C10—N2—C18	177.39 (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—C10	175.24 (15)
C1—C6—C7—C8	0.13 (16)	C8—C9—N2—C10	−4.5 (2)
C5—C6—C7—C8	178.92 (17)	O2—C9—N2—C18	2.2 (2)
C1—C6—C7—N1	179.78 (14)	C8—C9—N2—C18	−177.54 (13)
C5—C6—C7—N1	−1.4 (3)	C19—C18—N2—C10	124.87 (14)
N1—C7—C8—O1	−179.38 (12)	C17—C18—N2—C10	1.87 (15)
C6—C7—C8—O1	0.29 (17)	C19—C18—N2—C9	−61.38 (19)
N1—C7—C8—C9	0.5 (2)	C17—C18—N2—C9	175.62 (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—C10	0.95 (16)
O1—C8—C9—O2	2.8 (3)	O3—C17—N3—C11	−10.7 (3)
C7—C8—C9—N2	2.7 (2)	C18—C17—N3—C11	169.13 (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—C17	0.25 (17)
N3—C11—C12—C13	176.04 (15)	N1—C10—N3—C11	12.7 (2)
C11—C12—C13—C14	0.2 (3)	N2—C10—N3—C11	−168.47 (13)
C12—C13—C14—C15	1.3 (3)	C12—C11—N3—C17	134.92 (17)
C13—C14—C15—C16	−2.0 (3)	C16—C11—N3—C17	−48.0 (2)
C12—C11—C16—C15	0.3 (3)	C12—C11—N3—C10	−58.1 (2)
N3—C11—C16—C15	−176.76 (15)	C16—C11—N3—C10	118.95 (17)
C14—C15—C16—C11	1.2 (3)	C7—C8—O1—C1	−0.59 (16)
O3—C17—C18—N2	178.21 (15)	C9—C8—O1—C1	179.56 (14)
N3—C17—C18—N2	−1.66 (15)	C2—C1—O1—C8	−179.22 (14)
O3—C17—C18—C19	53.7 (2)	C6—C1—O1—C8	0.68 (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—C21	177.50 (14)
C17—C18—C19—C20	33.47 (19)	C22—C21—O5—C20	−175.36 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5i	0.93	2.56	3.442 (2)	159
C3—H3···O4ii	0.93	2.58	3.305 (2)	135
C5—H5···O2iii	0.93	2.46	3.132 (2)	129
C15—H15···O3iv	0.93	2.53	3.434 (2)	163
C19—H19A···O2	0.97	2.52	3.137 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5i	0.93	2.56	3.442 (2)	159
C3—H3⋯O4ii	0.93	2.58	3.305 (2)	135
C5—H5⋯O2iii	0.93	2.46	3.132 (2)	129
C15—H15⋯O3iv	0.93	2.53	3.434 (2)	163
C19—H19A⋯O2	0.97	2.52	3.137 (2)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .