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In the title compound, C
23H
16N
2O
4, the molecules form a supramolecular structure
via intermolecular C—H
O hydrogen bonds and intermolecular π–π interactions.
Supporting information
CCDC reference: 287441
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C)= 0.003 Å
- R factor = 0.051
- wR factor = 0.115
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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%.
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 Uiso(H) = 1.2Ueq(C). [Please clarify, as all data relating to H atoms in the CIF tables have s.u.s.]
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.
2-(4-methoxyphenoxy)-3-phenyl-3
H-benzo[4,5]furo[3,2-
d]pyrimidin-4-one
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.55 × 0.20 × 0.20 mm |
Data collection top
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 top
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0435P)2 + 0.0501P] where P = (Fo2 + 2Fc2)/3 |
4082 reflections | (Δ/σ)max = 0.001 |
326 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C23H16N2O4 | V = 1875.5 (4) Å3 |
Mr = 384.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3415 (12) Å | µ = 0.10 mm−1 |
b = 10.0584 (12) Å | T = 292 K |
c = 19.976 (3) Å | 0.55 × 0.20 × 0.20 mm |
β = 92.262 (2)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2620 reflections with I > 2σ(I) |
10770 measured reflections | Rint = 0.042 |
4082 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.115 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.13 e Å−3 |
4082 reflections | Δρmin = −0.18 e Å−3 |
326 parameters | |
Special details top
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) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23C···O3i | 1.04 (2) | 2.48 (2) | 3.312 (3) | 136.4 (16) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data |
Chemical formula | C23H16N2O4 |
Mr | 384.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 9.3415 (12), 10.0584 (12), 19.976 (3) |
β (°) | 92.262 (2) |
V (Å3) | 1875.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.55 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10770, 4082, 2620 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.639 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.115, 1.02 |
No. of reflections | 4082 |
No. of parameters | 326 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.13, −0.18 |
Selected geometric parameters (Å, º) topC1—C2 | 1.380 (3) | C9—N2 | 1.426 (2) |
C1—C6 | 1.389 (2) | C10—N1 | 1.287 (2) |
C1—O1 | 1.392 (2) | C10—O3 | 1.341 (2) |
C4—C5 | 1.370 (3) | C11—N2 | 1.451 (2) |
C6—C7 | 1.434 (2) | C17—O3 | 1.409 (2) |
C7—N1 | 1.376 (2) | C20—O4 | 1.366 (2) |
C8—O1 | 1.379 (2) | C23—O4 | 1.430 (3) |
C9—O2 | 1.220 (2) | | |
| | | |
C2—C1—C6 | 123.7 (2) | C12—C11—N2 | 119.96 (17) |
C6—C1—O1 | 111.39 (16) | C18—C17—O3 | 116.99 (17) |
C5—C6—C7 | 135.76 (18) | C22—C17—O3 | 121.44 (18) |
C8—C7—N1 | 123.80 (17) | O4—C20—C19 | 124.30 (18) |
C7—C8—O1 | 112.51 (16) | C10—N2—C9 | 121.79 (15) |
O1—C8—C9 | 123.39 (16) | C8—O1—C1 | 104.26 (14) |
O2—C9—N2 | 121.79 (18) | C10—O3—C17 | 119.65 (14) |
N1—C10—O3 | 121.88 (16) | C20—O4—C23 | 117.37 (18) |
N1—C10—N2 | 127.16 (17) | | |
| | | |
C6—C1—C2—C3 | 0.5 (3) | C17—C18—C19—C20 | −0.3 (3) |
O1—C1—C2—C3 | −179.80 (17) | O4—C20—C21—C22 | −179.04 (18) |
C3—C4—C5—C6 | −0.6 (3) | C6—C7—N1—C10 | −175.86 (18) |
C1—C6—C7—N1 | −179.80 (18) | O3—C10—N2—C11 | −9.5 (2) |
N1—C7—C8—O1 | 179.74 (16) | O2—C9—N2—C10 | 179.01 (17) |
C7—C8—C9—O2 | −173.48 (19) | C6—C1—O1—C8 | 0.1 (2) |
O1—C8—C9—N2 | 176.54 (16) | C19—C20—O4—C23 | −0.8 (3) |
N2—C11—C16—C15 | −179.87 (17) | C21—C20—O4—C23 | 178.07 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23C···O3i | 1.04 (2) | 2.48 (2) | 3.312 (3) | 136.4 (16) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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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).