Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040377/sj6175sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040377/sj6175Isup2.hkl |
CCDC reference: 296663
To a solution of iminophosphorane (1.40 g, 3 mmol) in dry dichloromethane (15 ml) was added phenyl isocyanate (3 mmol) under nitrogen at room temperature. After standing for 10 h at 273–278 K, the solvent was removed under reduced pressure and ether/petroleum ether (1:2, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration the solvent was removed to give the carbodiimide, (II), which was used directly without further purification. To the solution of (II) prepared above in dichloromethane (15 ml) was added diethylamine (3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) and several drops of EtONa in EtOH were added. The mixture was stirred for 3 h at room temperature, concentrated under reduced pressure and the residue recrystallized from ethanol to give the title compound (I) (yield 0.81 g, 78%, m.p. 420 K). Suitable crystals were obtained by vapor diffusion of ethanol and dichloromethane at room temperature. Spectroscopic analysis:1H NMR (CDCl3, 400 MHz): 0.84–0.88(t, 6H, CH3, J=7.2 Hz), 2.42 (s, 3H, CH3), 3.12–3.17 (q, 4H, CH2, J = 6.8 Hz), 7.14–8.03 (m, 8H, Ar—H). MS (EI 70 eV) m/z(%): 347 (M+, 62), 318 (86), 275 (65), 130 (84), 91 (100). Elemental analysis: calculated for C21H21N3O2: C 72.60, H 6.09, N 12.10%; found: C 72.52, H 6.16, N 12.07%.
The H atoms were positioned geometrically [0.93 (CH), 0.97 (CH2) and 0.96 Å (CH3)] and constrained to ride on their parent atoms with Uiso(H) = 1.2 (1.5 for methyl) Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C21H21N3O2 | F(000) = 736 |
Mr = 347.41 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/n | Melting point: 420 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 16.164 (2) Å | Cell parameters from 1397 reflections |
b = 7.0063 (9) Å | θ = 2.5–21.6° |
c = 17.627 (2) Å | µ = 0.08 mm−1 |
β = 113.685 (2)° | T = 292 K |
V = 1828.1 (4) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.16 mm |
Bruker CCD area-detector diffractometer | 1941 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 26.0°, θmin = 2.5° |
ϕ and ω scans | h = −19→19 |
11487 measured reflections | k = −8→8 |
3590 independent reflections | l = −19→21 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3 |
3590 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C21H21N3O2 | V = 1828.1 (4) Å3 |
Mr = 347.41 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.164 (2) Å | µ = 0.08 mm−1 |
b = 7.0063 (9) Å | T = 292 K |
c = 17.627 (2) Å | 0.30 × 0.20 × 0.16 mm |
β = 113.685 (2)° |
Bruker CCD area-detector diffractometer | 1941 reflections with I > 2σ(I) |
11487 measured reflections | Rint = 0.069 |
3590 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.20 e Å−3 |
3590 reflections | Δρmin = −0.16 e Å−3 |
238 parameters |
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 | 0.95360 (17) | 0.7410 (3) | 0.98052 (16) | 0.0438 (6) | |
C2 | 0.87591 (18) | 0.7069 (4) | 0.99426 (19) | 0.0570 (8) | |
H2 | 0.8197 | 0.6966 | 0.9504 | 0.068* | |
C3 | 0.8853 (2) | 0.6889 (4) | 1.0754 (2) | 0.0694 (9) | |
H3 | 0.8346 | 0.6654 | 1.0865 | 0.083* | |
C4 | 0.9698 (3) | 0.7056 (4) | 1.1407 (2) | 0.0711 (9) | |
H4 | 0.9738 | 0.6945 | 1.1946 | 0.085* | |
C5 | 1.0471 (2) | 0.7376 (4) | 1.12877 (18) | 0.0586 (8) | |
H5 | 1.1032 | 0.7485 | 1.1728 | 0.070* | |
C6 | 1.03678 (18) | 0.7524 (3) | 1.04780 (16) | 0.0457 (6) | |
C7 | 0.97333 (15) | 0.7684 (3) | 0.90768 (16) | 0.0408 (6) | |
C8 | 1.06472 (15) | 0.7894 (3) | 0.93737 (16) | 0.0429 (6) | |
C9 | 1.11201 (17) | 0.8024 (4) | 0.88575 (17) | 0.0494 (7) | |
C10 | 0.95607 (15) | 0.8036 (3) | 0.77603 (16) | 0.0418 (6) | |
C11 | 0.81104 (16) | 0.7555 (4) | 0.66205 (18) | 0.0625 (8) | |
H11A | 0.7780 | 0.7999 | 0.6057 | 0.075* | |
H11B | 0.7832 | 0.8114 | 0.6964 | 0.075* | |
C12 | 0.8040 (2) | 0.5421 (5) | 0.6641 (2) | 0.0952 (12) | |
H12A | 0.8283 | 0.4864 | 0.6277 | 0.143* | |
H12B | 0.7417 | 0.5062 | 0.6464 | 0.143* | |
H12C | 0.8374 | 0.4973 | 0.7195 | 0.143* | |
C13 | 0.91523 (18) | 0.9989 (4) | 0.65194 (16) | 0.0583 (8) | |
H13A | 0.9735 | 1.0553 | 0.6850 | 0.070* | |
H13B | 0.8688 | 1.0882 | 0.6507 | 0.070* | |
C14 | 0.9083 (2) | 0.9687 (5) | 0.56471 (18) | 0.0911 (11) | |
H14A | 0.9580 | 0.8917 | 0.5661 | 0.137* | |
H14B | 0.9100 | 1.0900 | 0.5400 | 0.137* | |
H14C | 0.8525 | 0.9053 | 0.5326 | 0.137* | |
C15 | 1.09034 (16) | 0.7812 (4) | 0.74123 (16) | 0.0457 (6) | |
C16 | 1.14573 (17) | 0.9188 (4) | 0.73121 (17) | 0.0579 (8) | |
H16 | 1.1564 | 1.0317 | 0.7614 | 0.069* | |
C17 | 1.18547 (18) | 0.8880 (5) | 0.67595 (19) | 0.0664 (9) | |
H17 | 1.2226 | 0.9808 | 0.6685 | 0.080* | |
C18 | 1.17019 (19) | 0.7215 (5) | 0.63244 (19) | 0.0667 (9) | |
H18 | 1.1977 | 0.7027 | 0.5958 | 0.080* | |
C19 | 1.11495 (17) | 0.5793 (4) | 0.64104 (17) | 0.0544 (7) | |
C20 | 1.07530 (16) | 0.6136 (4) | 0.69651 (16) | 0.0499 (7) | |
H20 | 1.0377 | 0.5213 | 0.7037 | 0.060* | |
C21 | 1.0999 (2) | 0.3947 (5) | 0.5943 (2) | 0.0851 (10) | |
H21A | 1.0808 | 0.4207 | 0.5363 | 0.128* | |
H21B | 1.0540 | 0.3223 | 0.6031 | 0.128* | |
H21C | 1.1551 | 0.3229 | 0.6137 | 0.128* | |
N1 | 0.91649 (13) | 0.7793 (3) | 0.82638 (13) | 0.0443 (5) | |
N2 | 1.04982 (12) | 0.8066 (3) | 0.80046 (12) | 0.0436 (5) | |
N3 | 0.90515 (13) | 0.8210 (3) | 0.69147 (13) | 0.0476 (6) | |
O1 | 1.10616 (11) | 0.7816 (2) | 1.02253 (10) | 0.0494 (5) | |
O2 | 1.19323 (11) | 0.8035 (3) | 0.90580 (11) | 0.0702 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0516 (15) | 0.0299 (14) | 0.0528 (18) | 0.0072 (11) | 0.0241 (14) | 0.0018 (12) |
C2 | 0.0572 (17) | 0.0525 (18) | 0.068 (2) | 0.0084 (13) | 0.0316 (16) | 0.0056 (15) |
C3 | 0.089 (2) | 0.055 (2) | 0.089 (3) | 0.0060 (17) | 0.062 (2) | 0.0077 (18) |
C4 | 0.110 (3) | 0.051 (2) | 0.064 (2) | 0.0071 (18) | 0.048 (2) | 0.0059 (16) |
C5 | 0.083 (2) | 0.0458 (18) | 0.0457 (19) | 0.0045 (15) | 0.0242 (16) | 0.0022 (14) |
C6 | 0.0590 (17) | 0.0345 (15) | 0.0423 (17) | 0.0043 (12) | 0.0191 (14) | −0.0003 (12) |
C7 | 0.0405 (14) | 0.0335 (15) | 0.0453 (17) | 0.0036 (11) | 0.0140 (13) | −0.0007 (12) |
C8 | 0.0400 (14) | 0.0449 (16) | 0.0363 (16) | 0.0022 (11) | 0.0076 (12) | −0.0021 (12) |
C9 | 0.0379 (14) | 0.0582 (19) | 0.0455 (18) | 0.0008 (13) | 0.0097 (14) | 0.0025 (13) |
C10 | 0.0355 (13) | 0.0394 (15) | 0.0421 (17) | 0.0007 (11) | 0.0067 (13) | −0.0029 (12) |
C11 | 0.0404 (15) | 0.069 (2) | 0.056 (2) | −0.0023 (14) | −0.0035 (14) | 0.0012 (15) |
C12 | 0.071 (2) | 0.069 (2) | 0.105 (3) | −0.0172 (18) | −0.007 (2) | 0.007 (2) |
C13 | 0.0553 (17) | 0.0578 (19) | 0.0468 (18) | 0.0031 (14) | 0.0049 (14) | 0.0060 (14) |
C14 | 0.107 (3) | 0.104 (3) | 0.044 (2) | −0.006 (2) | 0.0106 (19) | 0.0175 (19) |
C15 | 0.0423 (14) | 0.0521 (18) | 0.0384 (16) | 0.0030 (12) | 0.0118 (12) | 0.0041 (13) |
C16 | 0.0499 (16) | 0.065 (2) | 0.056 (2) | −0.0104 (14) | 0.0187 (15) | 0.0002 (15) |
C17 | 0.0541 (18) | 0.080 (2) | 0.067 (2) | −0.0060 (16) | 0.0263 (16) | 0.0140 (18) |
C18 | 0.0565 (18) | 0.092 (3) | 0.057 (2) | 0.0103 (18) | 0.0284 (16) | 0.0110 (19) |
C19 | 0.0451 (15) | 0.067 (2) | 0.0501 (18) | 0.0096 (14) | 0.0176 (14) | 0.0012 (15) |
C20 | 0.0423 (15) | 0.0549 (19) | 0.0500 (18) | 0.0047 (13) | 0.0159 (14) | 0.0074 (14) |
C21 | 0.090 (2) | 0.086 (3) | 0.085 (3) | 0.013 (2) | 0.040 (2) | −0.012 (2) |
N1 | 0.0365 (11) | 0.0484 (14) | 0.0432 (14) | 0.0034 (9) | 0.0109 (11) | 0.0003 (10) |
N2 | 0.0345 (11) | 0.0543 (14) | 0.0382 (13) | 0.0006 (9) | 0.0105 (10) | −0.0002 (10) |
N3 | 0.0400 (12) | 0.0493 (14) | 0.0416 (14) | −0.0010 (10) | 0.0038 (11) | 0.0029 (11) |
O1 | 0.0493 (10) | 0.0553 (12) | 0.0365 (11) | 0.0003 (8) | 0.0098 (9) | −0.0008 (8) |
O2 | 0.0339 (10) | 0.1161 (18) | 0.0540 (13) | −0.0010 (10) | 0.0106 (9) | 0.0058 (11) |
C1—C2 | 1.392 (3) | C12—H12A | 0.9600 |
C1—C6 | 1.393 (3) | C12—H12B | 0.9600 |
C1—C7 | 1.455 (3) | C12—H12C | 0.9600 |
C2—C3 | 1.381 (4) | C13—N3 | 1.469 (3) |
C2—H2 | 0.9300 | C13—C14 | 1.511 (3) |
C3—C4 | 1.394 (4) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.365 (4) | C14—H14A | 0.9600 |
C4—H4 | 0.9300 | C14—H14B | 0.9600 |
C5—C6 | 1.373 (3) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | C15—C16 | 1.374 (3) |
C6—O1 | 1.378 (3) | C15—C20 | 1.380 (3) |
C7—N1 | 1.359 (3) | C15—N2 | 1.449 (3) |
C7—C8 | 1.363 (3) | C16—C17 | 1.382 (4) |
C8—O1 | 1.378 (3) | C16—H16 | 0.9300 |
C8—C9 | 1.407 (3) | C17—C18 | 1.363 (4) |
C9—O2 | 1.215 (3) | C17—H17 | 0.9300 |
C9—N2 | 1.434 (3) | C18—C19 | 1.386 (4) |
C10—N1 | 1.297 (3) | C18—H18 | 0.9300 |
C10—N3 | 1.389 (3) | C19—C20 | 1.388 (3) |
C10—N2 | 1.399 (3) | C19—C21 | 1.500 (4) |
C11—N3 | 1.470 (3) | C20—H20 | 0.9300 |
C11—C12 | 1.501 (4) | C21—H21A | 0.9600 |
C11—H11A | 0.9700 | C21—H21B | 0.9600 |
C11—H11B | 0.9700 | C21—H21C | 0.9600 |
C2—C1—C6 | 119.5 (2) | N3—C13—H13A | 109.0 |
C2—C1—C7 | 135.2 (3) | C14—C13—H13A | 109.0 |
C6—C1—C7 | 105.4 (2) | N3—C13—H13B | 109.0 |
C3—C2—C1 | 117.7 (3) | C14—C13—H13B | 109.0 |
C3—C2—H2 | 121.2 | H13A—C13—H13B | 107.8 |
C1—C2—H2 | 121.2 | C13—C14—H14A | 109.5 |
C2—C3—C4 | 120.7 (3) | C13—C14—H14B | 109.5 |
C2—C3—H3 | 119.6 | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 119.6 | C13—C14—H14C | 109.5 |
C5—C4—C3 | 122.7 (3) | H14A—C14—H14C | 109.5 |
C5—C4—H4 | 118.7 | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 118.7 | C16—C15—C20 | 119.8 (2) |
C4—C5—C6 | 115.9 (3) | C16—C15—N2 | 120.8 (2) |
C4—C5—H5 | 122.1 | C20—C15—N2 | 119.3 (2) |
C6—C5—H5 | 122.1 | C15—C16—C17 | 119.5 (3) |
C5—C6—O1 | 124.9 (3) | C15—C16—H16 | 120.3 |
C5—C6—C1 | 123.6 (3) | C17—C16—H16 | 120.3 |
O1—C6—C1 | 111.5 (2) | C18—C17—C16 | 120.0 (3) |
N1—C7—C8 | 124.6 (2) | C18—C17—H17 | 120.0 |
N1—C7—C1 | 130.0 (2) | C16—C17—H17 | 120.0 |
C8—C7—C1 | 105.3 (2) | C17—C18—C19 | 122.2 (3) |
C7—C8—O1 | 113.1 (2) | C17—C18—H18 | 118.9 |
C7—C8—C9 | 123.1 (2) | C19—C18—H18 | 118.9 |
O1—C8—C9 | 123.7 (2) | C18—C19—C20 | 116.9 (3) |
O2—C9—C8 | 128.1 (2) | C18—C19—C21 | 122.0 (3) |
O2—C9—N2 | 121.7 (2) | C20—C19—C21 | 121.1 (3) |
C8—C9—N2 | 110.2 (2) | C15—C20—C19 | 121.6 (3) |
N1—C10—N3 | 120.2 (2) | C15—C20—H20 | 119.2 |
N1—C10—N2 | 124.2 (2) | C19—C20—H20 | 119.2 |
N3—C10—N2 | 115.5 (2) | C19—C21—H21A | 109.5 |
N3—C11—C12 | 112.4 (2) | C19—C21—H21B | 109.5 |
N3—C11—H11A | 109.1 | H21A—C21—H21B | 109.5 |
C12—C11—H11A | 109.1 | C19—C21—H21C | 109.5 |
N3—C11—H11B | 109.1 | H21A—C21—H21C | 109.5 |
C12—C11—H11B | 109.1 | H21B—C21—H21C | 109.5 |
H11A—C11—H11B | 107.9 | C10—N1—C7 | 114.8 (2) |
C11—C12—H12A | 109.5 | C10—N2—C9 | 122.6 (2) |
C11—C12—H12B | 109.5 | C10—N2—C15 | 121.6 (2) |
H12A—C12—H12B | 109.5 | C9—N2—C15 | 115.05 (18) |
C11—C12—H12C | 109.5 | C10—N3—C13 | 116.9 (2) |
H12A—C12—H12C | 109.5 | C10—N3—C11 | 115.8 (2) |
H12B—C12—H12C | 109.5 | C13—N3—C11 | 113.2 (2) |
N3—C13—C14 | 112.8 (2) | C8—O1—C6 | 104.81 (19) |
C6—C1—C2—C3 | 1.0 (4) | C18—C19—C20—C15 | −0.2 (4) |
C7—C1—C2—C3 | −179.9 (3) | C21—C19—C20—C15 | 178.5 (3) |
C1—C2—C3—C4 | 0.3 (4) | N3—C10—N1—C7 | −178.6 (2) |
C2—C3—C4—C5 | −0.9 (5) | N2—C10—N1—C7 | 4.0 (3) |
C3—C4—C5—C6 | 0.0 (4) | C8—C7—N1—C10 | 3.0 (3) |
C4—C5—C6—O1 | −179.0 (2) | C1—C7—N1—C10 | −179.6 (2) |
C4—C5—C6—C1 | 1.5 (4) | N1—C10—N2—C9 | −6.6 (4) |
C2—C1—C6—C5 | −2.0 (4) | N3—C10—N2—C9 | 175.9 (2) |
C7—C1—C6—C5 | 178.7 (2) | N1—C10—N2—C15 | 162.6 (2) |
C2—C1—C6—O1 | 178.4 (2) | N3—C10—N2—C15 | −14.8 (3) |
C7—C1—C6—O1 | −1.0 (3) | O2—C9—N2—C10 | 179.4 (2) |
C2—C1—C7—N1 | 4.2 (5) | C8—C9—N2—C10 | 1.8 (3) |
C6—C1—C7—N1 | −176.6 (2) | O2—C9—N2—C15 | 9.5 (4) |
C2—C1—C7—C8 | −178.0 (3) | C8—C9—N2—C15 | −168.1 (2) |
C6—C1—C7—C8 | 1.2 (3) | C16—C15—N2—C10 | 121.6 (3) |
N1—C7—C8—O1 | 176.9 (2) | C20—C15—N2—C10 | −60.6 (3) |
C1—C7—C8—O1 | −1.0 (3) | C16—C15—N2—C9 | −68.4 (3) |
N1—C7—C8—C9 | −7.9 (4) | C20—C15—N2—C9 | 109.4 (3) |
C1—C7—C8—C9 | 174.2 (2) | N1—C10—N3—C13 | 120.2 (3) |
C7—C8—C9—O2 | −172.5 (3) | N2—C10—N3—C13 | −62.2 (3) |
O1—C8—C9—O2 | 2.2 (4) | N1—C10—N3—C11 | −17.2 (3) |
C7—C8—C9—N2 | 4.9 (3) | N2—C10—N3—C11 | 160.4 (2) |
O1—C8—C9—N2 | 179.6 (2) | C14—C13—N3—C10 | 145.1 (2) |
C20—C15—C16—C17 | 0.4 (4) | C14—C13—N3—C11 | −76.5 (3) |
N2—C15—C16—C17 | 178.1 (2) | C12—C11—N3—C10 | −71.8 (3) |
C15—C16—C17—C18 | −0.6 (4) | C12—C11—N3—C13 | 149.3 (3) |
C16—C17—C18—C19 | 0.4 (5) | C7—C8—O1—C6 | 0.5 (3) |
C17—C18—C19—C20 | 0.0 (4) | C9—C8—O1—C6 | −174.7 (2) |
C17—C18—C19—C21 | −178.7 (3) | C5—C6—O1—C8 | −179.2 (2) |
C16—C15—C20—C19 | 0.0 (4) | C1—C6—O1—C8 | 0.4 (3) |
N2—C15—C20—C19 | −177.8 (2) |
Experimental details
Crystal data | |
Chemical formula | C21H21N3O2 |
Mr | 347.41 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 292 |
a, b, c (Å) | 16.164 (2), 7.0063 (9), 17.627 (2) |
β (°) | 113.685 (2) |
V (Å3) | 1828.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11487, 3590, 1941 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.145, 0.94 |
No. of reflections | 3590 |
No. of parameters | 238 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.16 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
C1—C2 | 1.392 (3) | C10—N3 | 1.389 (3) |
C1—C6 | 1.393 (3) | C10—N2 | 1.399 (3) |
C1—C7 | 1.455 (3) | C11—N3 | 1.470 (3) |
C5—C6 | 1.373 (3) | C13—N3 | 1.469 (3) |
C6—O1 | 1.378 (3) | C15—C16 | 1.374 (3) |
C7—N1 | 1.359 (3) | C15—C20 | 1.380 (3) |
C7—C8 | 1.363 (3) | C15—N2 | 1.449 (3) |
C8—O1 | 1.378 (3) | C16—C17 | 1.382 (4) |
C8—C9 | 1.407 (3) | C17—C18 | 1.363 (4) |
C9—O2 | 1.215 (3) | C18—C19 | 1.386 (4) |
C9—N2 | 1.434 (3) | C19—C20 | 1.388 (3) |
C10—N1 | 1.297 (3) | C19—C21 | 1.500 (4) |
C2—C1—C6 | 119.5 (2) | C7—C8—C9 | 123.1 (2) |
C2—C1—C7 | 135.2 (3) | O1—C8—C9 | 123.7 (2) |
C6—C1—C7 | 105.4 (2) | O2—C9—C8 | 128.1 (2) |
C3—C2—C1 | 117.7 (3) | O2—C9—N2 | 121.7 (2) |
C2—C3—C4 | 120.7 (3) | C8—C9—N2 | 110.2 (2) |
C5—C4—C3 | 122.7 (3) | N1—C10—N3 | 120.2 (2) |
C5—C6—O1 | 124.9 (3) | N1—C10—N2 | 124.2 (2) |
C5—C6—C1 | 123.6 (3) | N3—C10—N2 | 115.5 (2) |
O1—C6—C1 | 111.5 (2) | C16—C15—N2 | 120.8 (2) |
N1—C7—C8 | 124.6 (2) | C20—C15—N2 | 119.3 (2) |
N1—C7—C1 | 130.0 (2) | C10—N3—C13 | 116.9 (2) |
C8—C7—C1 | 105.3 (2) | C10—N3—C11 | 115.8 (2) |
C7—C8—O1 | 113.1 (2) | C8—O1—C6 | 104.81 (19) |
C6—C1—C2—C3 | 1.0 (4) | C2—C1—C7—C8 | −178.0 (3) |
C7—C1—C2—C3 | −179.9 (3) | C6—C1—C7—C8 | 1.2 (3) |
C4—C5—C6—O1 | −179.0 (2) | C1—C7—C8—O1 | −1.0 (3) |
C4—C5—C6—C1 | 1.5 (4) | O1—C8—C9—O2 | 2.2 (4) |
C2—C1—C6—C5 | −2.0 (4) | O1—C8—C9—N2 | 179.6 (2) |
C7—C1—C6—C5 | 178.7 (2) | C1—C7—N1—C10 | −179.6 (2) |
C2—C1—C6—O1 | 178.4 (2) | O2—C9—N2—C10 | 179.4 (2) |
C7—C1—C6—O1 | −1.0 (3) | C8—C9—N2—C10 | 1.8 (3) |
C6—C1—C7—N1 | −176.6 (2) | C8—C9—N2—C15 | −168.1 (2) |
The derivatives of benzofuropyrimidines are of great importance because of their remarkable biological properties (Bodke & Sangapure, 2003). In recent years, we have been engaged in the preparation of the derivatives of heterocycles via an aza-Wittig reaction (Ding et al., 2004a,b). The heterocyclic title compound, (I), may be used as a new precursor for obtaining bioactive molecules and its structure is presented here (Fig. 1). The three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar, with a maximum deviation of −0.079 (2) Å for C9. This plane is at an angle of 63.79 (11)° to the substituted benzene ring. Bond lengths and angles (Table 1) are in agreement with reported literature values (Allen et al.,1987). [NB: the scheme is for a different compound; please replace]
The centroid-to-centroid distances are 3.5173 (2) for rings A (O1, C1 C6, C7, C8) and Bi (C1, C2, C3, C4, C5, C6) [symmetry code: (i) = 2 − x, 2 − y, 2 − z] and 3.6726 (3) Å for rings B and Aii [symmetry code: (ii) = 2 − x, 1 − y, 2 − z]. The corresponding dihedral angles are 0.03 (2) and 1.26 (2)°, respectively. The contribution of π–π stacking interactions to the stability of the crystal is further demonstrated by the angles between the ring-centroid vectors [7.84 (2) for A to Bi and 20.42 (3)° for B to Aii] and the angles between the ring normals [8.58 (3) and 20.87 (2)° (Janiak, 2000)].