3-(4-Methoxy­phenoxy)-2-phenyl-3H-1-benzofuro[3,2-d]pyrimidin-1-one

In the title compound, C₂₃H₁₆N₂O₄, the mol­ecules form a supramolecular structure via inter­molecular C—H...O hydrogen bonds and inter­molecular π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.051
• wR factor = 0.115
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

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S1. Comment

Pyrimidine derivatives are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, antibiotics and drugs (Ding et al., 2004). In recent years, we have been engaged in the preparation of derivatives of heterocycles using the aza-Wittig reaction. In this paper, we present the X-ray crystallographic analysis of the title compound, (I).

The structure of (I) is shown schematically in Fig. 1, and selected bond lengths and angles are listed in Table 1. A l l ring atoms in the benzofuro[3,2-d]pyrimidine system are essentially coplanar in the molecule.

The asymmetric unit is shown in Fig. 2. A number of weak intermolecular C—H···O hydrogen-bonding interactions are present. Atom O3 and atom H23C on atom C23 of the neighbouring OCH₃ group form a weak C—H···O interaction (Table 2). The symmetry-imposed dihedral angle between two aromatic rings (atoms C17–C22) of adjacent molecules is 0° and the distance between ring centroids is 3.852 (1) Å, showing that π–π stacking interactions exist (Janiak, 2000).

S2. Experimental

The title compound, (I), was obtained in excellent yield via the aza-Wittig reaction. [Please give brief details of quantities and reagents.] Suitable crystals were obtained by vapour diffusion of ethanol and dichloromethane at room temperature. Elemental analysis, calculated for C₂₀H₁₉N₃O₄: C 71.87, H 4.21, N 7.29%; found: C 71.80, H 4.26, N 7.35%.

S3. Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.91–1.00 Å and with U_iso(H) = 1.2U_eq(C). [Please clarify, as all data relating to H atoms in the CIF tables have s.u.s.]

Computing details

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: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A stereoview of the crystal structure of (I), showing the formation of the C—H···O hydrogen bonds and the π–π stacking interactions [symmetry code: (a) −x + 1, −y + 1, −z + 2].

2-(4-methoxyphenoxy)-3-phenyl-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one

Crystal data

C23H16N2O4	F(000) = 800
Mr = 384.38	Dx = 1.361 Mg m^−3
Monoclinic, P21/c	Melting point: 504 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3415 (12) Å	Cell parameters from 1839 reflections
b = 10.0584 (12) Å	θ = 2.2–21.6°
c = 19.976 (3) Å	µ = 0.10 mm^−1
β = 92.262 (2)°	T = 292 K
V = 1875.5 (4) Å^3	Needle, colourless
Z = 4	0.55 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 27.0°, θmin = 2.0°
ϕ and ω scans	h = −11→11
10770 measured reflections	k = −12→10
4082 independent reflections	l = −25→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.0501P] where P = (Fo^2 + 2Fc^2)/3
4082 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.3281 (2)	0.92190 (18)	0.92301 (10)	0.0488 (5)
C2	−0.4394 (2)	0.9694 (2)	0.88229 (12)	0.0574 (6)
C3	−0.4309 (2)	0.9425 (2)	0.81543 (12)	0.0627 (6)
C4	−0.3175 (2)	0.8703 (2)	0.79014 (12)	0.0607 (6)
C5	−0.2080 (2)	0.8238 (2)	0.83143 (10)	0.0529 (5)
C6	−0.21220 (19)	0.85171 (17)	0.89949 (9)	0.0446 (5)
C7	−0.12260 (19)	0.82395 (18)	0.95778 (9)	0.0438 (4)
C8	−0.18955 (19)	0.87587 (18)	1.01080 (10)	0.0472 (5)
C9	−0.14243 (19)	0.85635 (19)	1.07855 (10)	0.0487 (5)
C10	0.05363 (19)	0.74293 (18)	1.02393 (9)	0.0457 (5)
C11	0.04642 (19)	0.74160 (19)	1.14638 (9)	0.0431 (4)
C12	0.0477 (2)	0.6089 (2)	1.16387 (11)	0.0590 (6)
C13	0.1079 (3)	0.5720 (3)	1.22527 (12)	0.0649 (6)
C14	0.1608 (2)	0.6659 (3)	1.26917 (12)	0.0624 (6)
C15	0.1568 (2)	0.7973 (3)	1.25171 (11)	0.0598 (6)
C16	0.1008 (2)	0.8359 (2)	1.18976 (10)	0.0508 (5)
C17	0.25735 (18)	0.6253 (2)	0.98775 (9)	0.0452 (5)
C18	0.2719 (2)	0.4900 (2)	0.99041 (11)	0.0549 (5)
C19	0.3580 (2)	0.4261 (2)	0.94572 (10)	0.0533 (5)
C20	0.42756 (18)	0.49888 (19)	0.89880 (9)	0.0458 (5)
C21	0.4119 (2)	0.6356 (2)	0.89692 (10)	0.0534 (5)
C22	0.3271 (2)	0.6996 (2)	0.94145 (10)	0.0536 (5)
C23	0.5381 (3)	0.3050 (2)	0.85497 (15)	0.0659 (7)
N1	0.00604 (15)	0.75732 (16)	0.96303 (8)	0.0476 (4)
N2	−0.01209 (15)	0.78231 (15)	1.08121 (7)	0.0451 (4)
O1	−0.31652 (13)	0.93815 (13)	0.99220 (7)	0.0555 (4)
O2	−0.20163 (14)	0.88970 (15)	1.12925 (7)	0.0655 (4)
O3	0.18059 (13)	0.68573 (14)	1.03888 (6)	0.0579 (4)
O4	0.51598 (14)	0.44561 (14)	0.85298 (7)	0.0616 (4)
H18	0.2215 (19)	0.4460 (18)	1.0246 (9)	0.053 (5)*
H5	−0.131 (2)	0.7786 (18)	0.8140 (9)	0.052 (6)*
H3	−0.507 (2)	0.9748 (19)	0.7854 (10)	0.070 (6)*
H15	0.194 (2)	0.8634 (19)	1.2828 (9)	0.062 (6)*
H23A	0.448 (3)	0.254 (2)	0.8465 (10)	0.078 (7)*
H12	0.0112 (19)	0.5466 (19)	1.1315 (9)	0.058 (6)*
H14	0.200 (2)	0.6408 (18)	1.3122 (10)	0.060 (6)*
H13	0.113 (2)	0.482 (2)	1.2366 (10)	0.074 (7)*
H21	0.463 (2)	0.6837 (19)	0.8652 (10)	0.065 (6)*
H19	0.372 (2)	0.332 (2)	0.9490 (9)	0.067 (6)*
H16	0.097 (2)	0.929 (2)	1.1774 (9)	0.069 (6)*
H23C	0.584 (2)	0.279 (2)	0.9012 (12)	0.086 (7)*
H22	0.316 (2)	0.794 (2)	0.9419 (10)	0.070 (7)*
H4	−0.312 (2)	0.8552 (18)	0.7409 (10)	0.065 (6)*
H2	−0.512 (2)	1.0156 (19)	0.9009 (10)	0.061 (6)*
H23B	0.603 (3)	0.290 (2)	0.8195 (12)	0.094 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0455 (11)	0.0449 (12)	0.0559 (13)	0.0007 (9)	0.0001 (9)	0.0034 (9)
C2	0.0499 (12)	0.0499 (13)	0.0724 (16)	0.0083 (11)	0.0007 (12)	0.0085 (11)
C3	0.0509 (13)	0.0642 (15)	0.0719 (17)	−0.0013 (11)	−0.0136 (12)	0.0158 (12)
C4	0.0561 (13)	0.0699 (16)	0.0556 (15)	−0.0061 (12)	−0.0057 (11)	0.0037 (11)
C5	0.0471 (12)	0.0573 (13)	0.0542 (13)	−0.0026 (11)	0.0009 (10)	0.0010 (10)
C6	0.0414 (10)	0.0407 (11)	0.0515 (12)	−0.0030 (9)	0.0017 (9)	0.0032 (9)
C7	0.0389 (10)	0.0424 (11)	0.0502 (12)	0.0005 (8)	0.0031 (9)	−0.0006 (9)
C8	0.0405 (10)	0.0471 (12)	0.0540 (12)	0.0082 (9)	0.0013 (9)	−0.0027 (9)
C9	0.0435 (11)	0.0485 (12)	0.0543 (13)	0.0024 (9)	0.0044 (10)	−0.0096 (9)
C10	0.0388 (10)	0.0509 (12)	0.0476 (12)	0.0040 (9)	0.0022 (9)	−0.0044 (9)
C11	0.0413 (10)	0.0474 (12)	0.0411 (11)	0.0009 (9)	0.0070 (8)	0.0000 (9)
C12	0.0682 (14)	0.0511 (14)	0.0581 (15)	−0.0079 (11)	0.0080 (11)	−0.0035 (11)
C13	0.0734 (15)	0.0567 (16)	0.0654 (16)	0.0010 (13)	0.0115 (12)	0.0157 (13)
C14	0.0593 (14)	0.0805 (19)	0.0477 (14)	0.0071 (12)	0.0050 (11)	0.0135 (13)
C15	0.0573 (13)	0.0733 (17)	0.0484 (13)	0.0010 (12)	−0.0017 (10)	−0.0084 (12)
C16	0.0540 (12)	0.0475 (13)	0.0509 (13)	0.0005 (10)	−0.0013 (10)	−0.0024 (10)
C17	0.0352 (10)	0.0583 (13)	0.0423 (11)	0.0086 (9)	0.0016 (8)	−0.0032 (9)
C18	0.0492 (12)	0.0609 (15)	0.0552 (13)	−0.0033 (11)	0.0116 (10)	0.0065 (11)
C19	0.0518 (12)	0.0451 (13)	0.0634 (14)	0.0006 (10)	0.0068 (10)	−0.0008 (10)
C20	0.0378 (10)	0.0545 (13)	0.0451 (11)	0.0029 (9)	0.0005 (8)	−0.0058 (9)
C21	0.0584 (13)	0.0519 (13)	0.0507 (13)	0.0050 (11)	0.0118 (10)	0.0064 (10)
C22	0.0585 (13)	0.0464 (13)	0.0562 (13)	0.0102 (11)	0.0050 (10)	0.0035 (10)
C23	0.0609 (16)	0.0629 (17)	0.0740 (18)	0.0164 (13)	0.0010 (14)	−0.0135 (13)
N1	0.0399 (9)	0.0564 (10)	0.0463 (10)	0.0062 (8)	−0.0009 (7)	−0.0037 (7)
N2	0.0422 (9)	0.0507 (10)	0.0426 (9)	0.0044 (7)	0.0034 (7)	−0.0033 (7)
O1	0.0499 (8)	0.0561 (9)	0.0606 (9)	0.0154 (7)	0.0027 (6)	−0.0026 (7)
O2	0.0578 (9)	0.0823 (11)	0.0567 (9)	0.0157 (8)	0.0068 (7)	−0.0180 (7)
O3	0.0452 (8)	0.0837 (11)	0.0448 (8)	0.0206 (7)	0.0003 (6)	−0.0064 (7)
O4	0.0636 (9)	0.0595 (10)	0.0629 (9)	0.0079 (8)	0.0170 (7)	−0.0080 (7)

Geometric parameters (Å, º)

C1—C2	1.380 (3)	C12—H12	0.954 (19)
C1—C6	1.389 (2)	C13—C14	1.368 (3)
C1—O1	1.392 (2)	C13—H13	0.93 (2)
C2—C3	1.368 (3)	C14—C15	1.367 (3)
C2—H2	0.916 (19)	C14—H14	0.957 (19)
C3—C4	1.395 (3)	C15—C16	1.380 (3)
C3—H3	0.97 (2)	C15—H15	0.966 (19)
C4—C5	1.370 (3)	C16—H16	0.96 (2)
C4—H4	1.00 (2)	C17—C18	1.368 (3)
C5—C6	1.390 (3)	C17—C22	1.374 (3)
C5—H5	0.933 (18)	C17—O3	1.409 (2)
C6—C7	1.434 (2)	C18—C19	1.383 (3)
C7—C8	1.356 (2)	C18—H18	0.954 (18)
C7—N1	1.376 (2)	C19—C20	1.373 (3)
C8—O1	1.379 (2)	C19—H19	0.95 (2)
C8—C9	1.420 (3)	C20—O4	1.366 (2)
C9—O2	1.220 (2)	C20—C21	1.383 (3)
C9—N2	1.426 (2)	C21—C22	1.375 (3)
C10—N1	1.287 (2)	C21—H21	0.94 (2)
C10—O3	1.341 (2)	C22—H22	0.96 (2)
C10—N2	1.378 (2)	C23—O4	1.430 (3)
C11—C16	1.369 (3)	C23—H23A	1.00 (2)
C11—C12	1.380 (3)	C23—H23C	1.04 (2)
C11—N2	1.451 (2)	C23—H23B	0.96 (3)
C12—C13	1.380 (3)
C2—C1—C6	123.7 (2)	C15—C14—H14	119.4 (12)
C2—C1—O1	124.87 (18)	C13—C14—H14	120.7 (11)
C6—C1—O1	111.39 (16)	C14—C15—C16	120.4 (2)
C3—C2—C1	115.8 (2)	C14—C15—H15	119.7 (11)
C3—C2—H2	124.7 (13)	C16—C15—H15	119.9 (12)
C1—C2—H2	119.5 (13)	C11—C16—C15	119.4 (2)
C2—C3—C4	122.0 (2)	C11—C16—H16	119.8 (11)
C2—C3—H3	117.9 (12)	C15—C16—H16	120.7 (12)
C4—C3—H3	120.1 (12)	C18—C17—C22	121.23 (18)
C5—C4—C3	121.2 (2)	C18—C17—O3	116.99 (17)
C5—C4—H4	118.2 (12)	C22—C17—O3	121.44 (18)
C3—C4—H4	120.4 (12)	C17—C18—C19	119.8 (2)
C4—C5—C6	118.1 (2)	C17—C18—H18	116.0 (11)
C4—C5—H5	120.8 (11)	C19—C18—H18	124.2 (11)
C6—C5—H5	121.1 (11)	C20—C19—C18	119.8 (2)
C1—C6—C5	119.06 (18)	C20—C19—H19	120.4 (12)
C1—C6—C7	105.18 (16)	C18—C19—H19	119.8 (12)
C5—C6—C7	135.76 (18)	O4—C20—C19	124.30 (18)
C8—C7—N1	123.80 (17)	O4—C20—C21	115.96 (17)
C8—C7—C6	106.67 (16)	C19—C20—C21	119.73 (18)
N1—C7—C6	129.53 (17)	C22—C21—C20	120.8 (2)
C7—C8—O1	112.51 (16)	C22—C21—H21	121.0 (12)
C7—C8—C9	123.78 (17)	C20—C21—H21	118.3 (12)
O1—C8—C9	123.39 (16)	C17—C22—C21	118.8 (2)
O2—C9—C8	128.28 (18)	C17—C22—H22	118.7 (12)
O2—C9—N2	121.79 (18)	C21—C22—H22	122.5 (12)
C8—C9—N2	109.86 (16)	O4—C23—H23A	112.4 (13)
N1—C10—O3	121.88 (16)	O4—C23—H23C	109.0 (12)
N1—C10—N2	127.16 (17)	H23A—C23—H23C	110.2 (17)
O3—C10—N2	110.95 (15)	O4—C23—H23B	103.0 (14)
C16—C11—C12	120.73 (19)	H23A—C23—H23B	110.5 (18)
C16—C11—N2	119.32 (17)	H23C—C23—H23B	111.6 (19)
C12—C11—N2	119.96 (17)	C10—N1—C7	113.26 (15)
C11—C12—C13	119.0 (2)	C10—N2—C9	121.79 (15)
C11—C12—H12	117.7 (11)	C10—N2—C11	119.97 (15)
C13—C12—H12	123.3 (11)	C9—N2—C11	118.13 (14)
C14—C13—C12	120.6 (2)	C8—O1—C1	104.26 (14)
C14—C13—H13	120.0 (13)	C10—O3—C17	119.65 (14)
C12—C13—H13	119.5 (13)	C20—O4—C23	117.37 (18)
C15—C14—C13	119.9 (2)
C6—C1—C2—C3	0.5 (3)	C18—C19—C20—O4	179.26 (17)
O1—C1—C2—C3	−179.80 (17)	C18—C19—C20—C21	0.5 (3)
C1—C2—C3—C4	0.7 (3)	O4—C20—C21—C22	−179.04 (18)
C2—C3—C4—C5	−0.6 (3)	C19—C20—C21—C22	−0.1 (3)
C3—C4—C5—C6	−0.6 (3)	C18—C17—C22—C21	0.5 (3)
C2—C1—C6—C5	−1.7 (3)	O3—C17—C22—C21	173.58 (17)
O1—C1—C6—C5	178.57 (16)	C20—C21—C22—C17	−0.3 (3)
C2—C1—C6—C7	179.13 (18)	O3—C10—N1—C7	−176.98 (16)
O1—C1—C6—C7	−0.6 (2)	N2—C10—N1—C7	2.3 (3)
C4—C5—C6—C1	1.7 (3)	C8—C7—N1—C10	3.4 (3)
C4—C5—C6—C7	−179.5 (2)	C6—C7—N1—C10	−175.86 (18)
C1—C6—C7—C8	0.9 (2)	N1—C10—N2—C9	−5.1 (3)
C5—C6—C7—C8	−178.1 (2)	O3—C10—N2—C9	174.31 (16)
C1—C6—C7—N1	−179.80 (18)	N1—C10—N2—C11	171.13 (18)
C5—C6—C7—N1	1.2 (4)	O3—C10—N2—C11	−9.5 (2)
N1—C7—C8—O1	179.74 (16)	O2—C9—N2—C10	179.01 (17)
C6—C7—C8—O1	−0.9 (2)	C8—C9—N2—C10	1.8 (2)
N1—C7—C8—C9	−6.5 (3)	O2—C9—N2—C11	2.7 (3)
C6—C7—C8—C9	172.83 (17)	C8—C9—N2—C11	−174.46 (16)
C7—C8—C9—O2	−173.48 (19)	C16—C11—N2—C10	114.5 (2)
O1—C8—C9—O2	−0.4 (3)	C12—C11—N2—C10	−65.0 (2)
C7—C8—C9—N2	3.5 (3)	C16—C11—N2—C9	−69.1 (2)
O1—C8—C9—N2	176.54 (16)	C12—C11—N2—C9	111.3 (2)
C16—C11—C12—C13	−1.6 (3)	C7—C8—O1—C1	0.5 (2)
N2—C11—C12—C13	177.99 (18)	C9—C8—O1—C1	−173.24 (18)
C11—C12—C13—C14	2.4 (3)	C2—C1—O1—C8	−179.64 (18)
C12—C13—C14—C15	−1.3 (3)	C6—C1—O1—C8	0.1 (2)
C13—C14—C15—C16	−0.6 (3)	N1—C10—O3—C17	−7.7 (3)
C12—C11—C16—C15	−0.3 (3)	N2—C10—O3—C17	172.92 (15)
N2—C11—C16—C15	−179.87 (17)	C18—C17—O3—C10	−112.5 (2)
C14—C15—C16—C11	1.4 (3)	C22—C17—O3—C10	74.1 (2)
C22—C17—C18—C19	−0.2 (3)	C19—C20—O4—C23	−0.8 (3)
O3—C17—C18—C19	−173.56 (17)	C21—C20—O4—C23	178.07 (19)
C17—C18—C19—C20	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23C···O3^i	1.04 (2)	2.48 (2)	3.312 (3)	136.4 (16)

Symmetry code: (i) −x+1, −y+1, −z+2.