Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027535/is2172sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027535/is2172Isup2.hkl |
CCDC reference: 654941
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.158
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 150.00 A 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added 4-fluorophenyl isocyanate (3 mmol) under dry nitrogen at room temperature. The reaction mixture was left unstirred for 8 h at room temperature and then the solvent was removed under reduced pressure and ether-petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solution of carbodiimide was added to a solution of diethyl-amine in anhydrous dichloromethane. After stirring the reaction mixture for 8 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, (I), in a yield of 90% (m.p. 394–396 K). Single crystals suitable for X-ray diffraction were obtained by recrystallization from a mixed solvent of hexane and dichloromethane (1:3 v/v) at room temperature.
H atoms were placed at calculated positions (C—H = 0.97 or 0.93 Å) and were refined using a riding model, with Uiso(H) = 1.2Ueq(C).
Quinazolinones are important heterocyclic compounds which exhibit good biological and pharmaceutical activities, including anti-inflammotory, antifunga, anticancer and AMPA-receptor antagonistic properties (Shiba et al., 1997). As part of our work on the preparation of potentially active heterocycles (Ding et al., 2000), we have obtained the title compound, (I).
Within the molecule of (I), the bond lengths and angles present no unusual features. In (I), the quinazolinone ring system is approximately planar, with a maximum deviation of 0.060 (1) and 0.028 (1) Å for atoms N1 and N2, respectively; the C13—C18 benzene ring is twisted with respect to it, with a dihedral angle of 67.09 (8)°. The morpholine ring shows a distorted chair conformation [φ = 341.64 (1)° and θ = 176.25 (1)°, Puckering Amplitude = 0.586 (1) Å] (Cremer & Pople, 1975). The structure is stabilized by a weak C—H···O hydrogen bond and C—H···π interactions (Table 1); Cg1, Cg2 and Cg3 are the centroids of C1—C6, N1/C7/C5/C6/N2/C8 and C13—C18 rings, respectively..
Biological and pharmaceutical activities have been described by Shiba et al. (1997) and the preparation of potentially active heterocycles has been described by Ding et al. (2000). For ring-puckering analysis, see Cremer & Pople (1975).
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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
C18H16FN3O2 | Dx = 1.289 Mg m−3 |
Mr = 325.34 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 8691 reflections |
Hall symbol: -I 4ad | θ = 2.5–24.9° |
a = 22.9526 (7) Å | µ = 0.09 mm−1 |
c = 12.7318 (7) Å | T = 291 K |
V = 6707.4 (5) Å3 | Plate, colourless |
Z = 16 | 0.30 × 0.20 × 0.20 mm |
F(000) = 2720 |
Bruker SMART 4K CCD area-detector diffractometer | 3033 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.081 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
φ and ω scans | h = −29→29 |
37145 measured reflections | k = −29→29 |
3665 independent reflections | l = −16→16 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0883P)2 + 2.6139P] where P = (Fo2 + 2Fc2)/3 |
3665 reflections | (Δ/σ)max = 0.009 |
217 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C18H16FN3O2 | Z = 16 |
Mr = 325.34 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.09 mm−1 |
a = 22.9526 (7) Å | T = 291 K |
c = 12.7318 (7) Å | 0.30 × 0.20 × 0.20 mm |
V = 6707.4 (5) Å3 |
Bruker SMART 4K CCD area-detector diffractometer | 3033 reflections with I > 2σ(I) |
37145 measured reflections | Rint = 0.081 |
3665 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.29 e Å−3 |
3665 reflections | Δρmin = −0.34 e Å−3 |
217 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 | 0.59565 (8) | 0.62432 (8) | −0.12006 (15) | 0.0401 (4) | |
H1 | 0.5653 | 0.6505 | −0.1093 | 0.048* | |
C2 | 0.63280 (9) | 0.63192 (9) | −0.20375 (15) | 0.0430 (5) | |
H2 | 0.6271 | 0.6630 | −0.2495 | 0.052* | |
C3 | 0.67875 (9) | 0.59369 (9) | −0.22054 (15) | 0.0427 (5) | |
H3 | 0.7034 | 0.5990 | −0.2777 | 0.051* | |
C4 | 0.68773 (8) | 0.54821 (8) | −0.15293 (15) | 0.0375 (4) | |
H4 | 0.7189 | 0.5230 | −0.1637 | 0.045* | |
C5 | 0.65010 (7) | 0.53949 (7) | −0.06747 (13) | 0.0305 (4) | |
C6 | 0.60337 (7) | 0.57732 (7) | −0.05088 (13) | 0.0310 (4) | |
C7 | 0.65773 (7) | 0.48957 (8) | 0.00124 (13) | 0.0319 (4) | |
C8 | 0.57321 (7) | 0.52771 (7) | 0.09563 (13) | 0.0281 (4) | |
C9 | 0.56338 (8) | 0.52223 (9) | 0.28622 (13) | 0.0356 (4) | |
H9A | 0.5693 | 0.5627 | 0.3058 | 0.043* | |
H9B | 0.6009 | 0.5028 | 0.2863 | 0.043* | |
C10 | 0.52302 (8) | 0.49319 (10) | 0.36305 (15) | 0.0429 (5) | |
H10A | 0.5182 | 0.4526 | 0.3439 | 0.051* | |
H10B | 0.5399 | 0.4947 | 0.4328 | 0.051* | |
C11 | 0.48082 (8) | 0.54901 (9) | 0.18113 (14) | 0.0383 (4) | |
H11A | 0.4629 | 0.5465 | 0.1122 | 0.046* | |
H11B | 0.4863 | 0.5898 | 0.1984 | 0.046* | |
C12 | 0.44237 (8) | 0.52015 (10) | 0.26214 (14) | 0.0434 (5) | |
H12A | 0.4051 | 0.5400 | 0.2642 | 0.052* | |
H12B | 0.4354 | 0.4801 | 0.2416 | 0.052* | |
C13 | 0.61453 (7) | 0.43071 (7) | 0.14019 (13) | 0.0311 (4) | |
C14 | 0.65930 (8) | 0.41819 (8) | 0.20947 (14) | 0.0363 (4) | |
H14 | 0.6903 | 0.4440 | 0.2172 | 0.044* | |
C15 | 0.65774 (9) | 0.36692 (9) | 0.26745 (15) | 0.0445 (5) | |
H15 | 0.6876 | 0.3577 | 0.3140 | 0.053* | |
C16 | 0.61141 (10) | 0.33061 (9) | 0.25439 (18) | 0.0522 (6) | |
C17 | 0.56688 (10) | 0.34217 (10) | 0.1861 (2) | 0.0601 (6) | |
H17 | 0.5358 | 0.3164 | 0.1796 | 0.072* | |
C18 | 0.56866 (9) | 0.39266 (9) | 0.12670 (17) | 0.0449 (5) | |
H18 | 0.5394 | 0.4008 | 0.0784 | 0.054* | |
F1 | 0.60879 (7) | 0.28091 (7) | 0.31230 (15) | 0.0853 (5) | |
N1 | 0.61561 (6) | 0.48459 (6) | 0.08071 (10) | 0.0288 (3) | |
N2 | 0.56556 (6) | 0.57138 (6) | 0.03353 (11) | 0.0338 (3) | |
N3 | 0.53697 (6) | 0.51878 (6) | 0.18116 (11) | 0.0309 (3) | |
O1 | 0.69568 (6) | 0.45289 (6) | −0.00868 (12) | 0.0501 (4) | |
O2 | 0.46772 (6) | 0.52110 (7) | 0.36408 (10) | 0.0459 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0392 (10) | 0.0398 (10) | 0.0414 (10) | 0.0016 (8) | −0.0009 (8) | 0.0097 (8) |
C2 | 0.0477 (11) | 0.0422 (11) | 0.0390 (10) | −0.0081 (9) | −0.0020 (8) | 0.0140 (8) |
C3 | 0.0434 (11) | 0.0512 (12) | 0.0334 (9) | −0.0132 (9) | 0.0089 (8) | 0.0047 (8) |
C4 | 0.0345 (9) | 0.0406 (10) | 0.0374 (10) | −0.0032 (8) | 0.0064 (7) | −0.0011 (8) |
C5 | 0.0290 (8) | 0.0332 (9) | 0.0292 (8) | −0.0039 (7) | 0.0013 (6) | −0.0014 (7) |
C6 | 0.0326 (9) | 0.0315 (9) | 0.0288 (8) | −0.0027 (7) | −0.0014 (7) | 0.0021 (7) |
C7 | 0.0278 (8) | 0.0340 (9) | 0.0340 (9) | 0.0004 (7) | 0.0030 (7) | −0.0003 (7) |
C8 | 0.0251 (8) | 0.0326 (8) | 0.0266 (8) | −0.0002 (6) | −0.0007 (6) | −0.0003 (6) |
C9 | 0.0293 (9) | 0.0485 (11) | 0.0291 (9) | 0.0012 (8) | 0.0000 (7) | −0.0041 (8) |
C10 | 0.0418 (11) | 0.0580 (12) | 0.0289 (9) | 0.0035 (9) | 0.0033 (8) | 0.0037 (8) |
C11 | 0.0318 (9) | 0.0481 (11) | 0.0351 (9) | 0.0099 (8) | 0.0036 (7) | 0.0015 (8) |
C12 | 0.0317 (9) | 0.0631 (13) | 0.0354 (10) | 0.0017 (9) | 0.0043 (7) | −0.0038 (9) |
C13 | 0.0328 (9) | 0.0308 (9) | 0.0298 (8) | 0.0035 (7) | 0.0020 (7) | 0.0045 (7) |
C14 | 0.0363 (9) | 0.0380 (10) | 0.0346 (9) | 0.0050 (8) | −0.0031 (7) | 0.0001 (7) |
C15 | 0.0479 (11) | 0.0508 (12) | 0.0347 (10) | 0.0151 (9) | −0.0043 (8) | 0.0071 (8) |
C16 | 0.0576 (13) | 0.0409 (11) | 0.0581 (13) | 0.0072 (10) | 0.0063 (11) | 0.0215 (10) |
C17 | 0.0500 (13) | 0.0445 (12) | 0.0859 (17) | −0.0114 (10) | −0.0091 (12) | 0.0211 (12) |
C18 | 0.0391 (10) | 0.0405 (11) | 0.0552 (12) | −0.0031 (8) | −0.0098 (9) | 0.0106 (9) |
F1 | 0.0905 (11) | 0.0613 (9) | 0.1042 (13) | 0.0037 (8) | 0.0010 (9) | 0.0498 (9) |
N1 | 0.0270 (7) | 0.0314 (7) | 0.0282 (7) | 0.0016 (6) | 0.0006 (5) | 0.0029 (6) |
N2 | 0.0335 (8) | 0.0345 (8) | 0.0333 (8) | 0.0040 (6) | 0.0053 (6) | 0.0041 (6) |
N3 | 0.0268 (7) | 0.0390 (8) | 0.0270 (7) | 0.0042 (6) | 0.0028 (5) | 0.0029 (6) |
O1 | 0.0454 (8) | 0.0460 (8) | 0.0591 (9) | 0.0174 (6) | 0.0204 (7) | 0.0123 (7) |
O2 | 0.0357 (7) | 0.0717 (10) | 0.0304 (7) | 0.0037 (7) | 0.0073 (5) | −0.0033 (6) |
C1—C2 | 1.376 (3) | C10—H10A | 0.9700 |
C1—C6 | 1.404 (2) | C10—H10B | 0.9700 |
C1—H1 | 0.9300 | C11—N3 | 1.464 (2) |
C2—C3 | 1.388 (3) | C11—C12 | 1.510 (3) |
C2—H2 | 0.9300 | C11—H11A | 0.9700 |
C3—C4 | 1.369 (3) | C11—H11B | 0.9700 |
C3—H3 | 0.9300 | C12—O2 | 1.423 (2) |
C4—C5 | 1.404 (2) | C12—H12A | 0.9700 |
C4—H4 | 0.9300 | C12—H12B | 0.9700 |
C5—C6 | 1.396 (2) | C13—C18 | 1.379 (3) |
C5—C7 | 1.452 (2) | C13—C14 | 1.384 (2) |
C6—N2 | 1.388 (2) | C13—N1 | 1.450 (2) |
C7—O1 | 1.218 (2) | C14—C15 | 1.390 (3) |
C7—N1 | 1.404 (2) | C14—H14 | 0.9300 |
C8—N2 | 1.289 (2) | C15—C16 | 1.361 (3) |
C8—N3 | 1.386 (2) | C15—H15 | 0.9300 |
C8—N1 | 1.401 (2) | C16—F1 | 1.360 (2) |
C9—N3 | 1.471 (2) | C16—C17 | 1.368 (3) |
C9—C10 | 1.503 (3) | C17—C18 | 1.384 (3) |
C9—H9A | 0.9700 | C17—H17 | 0.9300 |
C9—H9B | 0.9700 | C18—H18 | 0.9300 |
C10—O2 | 1.422 (2) | ||
C2—C1—C6 | 120.34 (18) | N3—C11—H11A | 110.1 |
C2—C1—H1 | 119.8 | C12—C11—H11A | 110.1 |
C6—C1—H1 | 119.8 | N3—C11—H11B | 110.1 |
C1—C2—C3 | 120.66 (17) | C12—C11—H11B | 110.1 |
C1—C2—H2 | 119.7 | H11A—C11—H11B | 108.5 |
C3—C2—H2 | 119.7 | O2—C12—C11 | 112.17 (16) |
C4—C3—C2 | 119.97 (17) | O2—C12—H12A | 109.2 |
C4—C3—H3 | 120.0 | C11—C12—H12A | 109.2 |
C2—C3—H3 | 120.0 | O2—C12—H12B | 109.2 |
C3—C4—C5 | 120.24 (17) | C11—C12—H12B | 109.2 |
C3—C4—H4 | 119.9 | H12A—C12—H12B | 107.9 |
C5—C4—H4 | 119.9 | C18—C13—C14 | 120.98 (16) |
C6—C5—C4 | 120.09 (16) | C18—C13—N1 | 119.23 (15) |
C6—C5—C7 | 119.49 (15) | C14—C13—N1 | 119.79 (15) |
C4—C5—C7 | 120.35 (16) | C13—C14—C15 | 119.68 (18) |
N2—C6—C5 | 122.43 (15) | C13—C14—H14 | 120.2 |
N2—C6—C1 | 118.84 (16) | C15—C14—H14 | 120.2 |
C5—C6—C1 | 118.68 (16) | C16—C15—C14 | 118.28 (18) |
O1—C7—N1 | 120.72 (16) | C16—C15—H15 | 120.9 |
O1—C7—C5 | 124.69 (16) | C14—C15—H15 | 120.9 |
N1—C7—C5 | 114.54 (14) | F1—C16—C15 | 118.8 (2) |
N2—C8—N3 | 121.03 (15) | F1—C16—C17 | 118.3 (2) |
N2—C8—N1 | 124.13 (14) | C15—C16—C17 | 122.85 (18) |
N3—C8—N1 | 114.77 (14) | C16—C17—C18 | 119.2 (2) |
N3—C9—C10 | 108.30 (14) | C16—C17—H17 | 120.4 |
N3—C9—H9A | 110.0 | C18—C17—H17 | 120.4 |
C10—C9—H9A | 110.0 | C13—C18—C17 | 119.01 (19) |
N3—C9—H9B | 110.0 | C13—C18—H18 | 120.5 |
C10—C9—H9B | 110.0 | C17—C18—H18 | 120.5 |
H9A—C9—H9B | 108.4 | C8—N1—C7 | 121.23 (14) |
O2—C10—C9 | 110.88 (16) | C8—N1—C13 | 121.31 (13) |
O2—C10—H10A | 109.5 | C7—N1—C13 | 117.23 (13) |
C9—C10—H10A | 109.5 | C8—N2—C6 | 117.79 (15) |
O2—C10—H10B | 109.5 | C8—N3—C11 | 117.28 (14) |
C9—C10—H10B | 109.5 | C8—N3—C9 | 117.35 (13) |
H10A—C10—H10B | 108.1 | C11—N3—C9 | 109.72 (13) |
N3—C11—C12 | 107.85 (15) | C10—O2—C12 | 110.48 (14) |
C6—C1—C2—C3 | −0.7 (3) | N2—C8—N1—C7 | 7.1 (2) |
C1—C2—C3—C4 | −0.6 (3) | N3—C8—N1—C7 | −176.00 (14) |
C2—C3—C4—C5 | 1.0 (3) | N2—C8—N1—C13 | −167.20 (16) |
C3—C4—C5—C6 | −0.2 (3) | N3—C8—N1—C13 | 9.7 (2) |
C3—C4—C5—C7 | 176.81 (17) | O1—C7—N1—C8 | 177.33 (17) |
C4—C5—C6—N2 | −178.68 (16) | C5—C7—N1—C8 | −5.0 (2) |
C7—C5—C6—N2 | 4.3 (3) | O1—C7—N1—C13 | −8.2 (2) |
C4—C5—C6—C1 | −1.0 (3) | C5—C7—N1—C13 | 169.47 (14) |
C7—C5—C6—C1 | −178.05 (16) | C18—C13—N1—C8 | 64.6 (2) |
C2—C1—C6—N2 | 179.18 (17) | C14—C13—N1—C8 | −115.37 (18) |
C2—C1—C6—C5 | 1.4 (3) | C18—C13—N1—C7 | −109.90 (19) |
C6—C5—C7—O1 | 177.26 (18) | C14—C13—N1—C7 | 70.1 (2) |
C4—C5—C7—O1 | 0.3 (3) | N3—C8—N2—C6 | −179.62 (15) |
C6—C5—C7—N1 | −0.3 (2) | N1—C8—N2—C6 | −2.9 (2) |
C4—C5—C7—N1 | −177.26 (15) | C5—C6—N2—C8 | −2.8 (2) |
N3—C9—C10—O2 | −59.7 (2) | C1—C6—N2—C8 | 179.56 (16) |
N3—C11—C12—O2 | 57.9 (2) | N2—C8—N3—C11 | 17.8 (2) |
C18—C13—C14—C15 | −0.9 (3) | N1—C8—N3—C11 | −159.21 (15) |
N1—C13—C14—C15 | 179.11 (16) | N2—C8—N3—C9 | −116.15 (18) |
C13—C14—C15—C16 | −0.5 (3) | N1—C8—N3—C9 | 66.8 (2) |
C14—C15—C16—F1 | −178.64 (19) | C12—C11—N3—C8 | 163.67 (15) |
C14—C15—C16—C17 | 0.7 (4) | C12—C11—N3—C9 | −59.11 (19) |
F1—C16—C17—C18 | 179.8 (2) | C10—C9—N3—C8 | −162.18 (16) |
C15—C16—C17—C18 | 0.4 (4) | C10—C9—N3—C11 | 60.63 (19) |
C14—C13—C18—C17 | 2.0 (3) | C9—C10—O2—C12 | 58.3 (2) |
N1—C13—C18—C17 | −177.98 (19) | C11—C12—O2—C10 | −57.8 (2) |
C16—C17—C18—C13 | −1.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.93 | 2.57 | 3.306 (2) | 137 |
C9—H9A···Cg3i | 0.97 | 2.85 | 3.673 (2) | 143 |
C11—H11A···Cg2ii | 0.97 | 2.96 | 3.759 (2) | 141 |
C12—H12A···Cg1iii | 0.97 | 2.72 | 3.548 (2) | 143 |
C12—H12B···Cg1ii | 0.97 | 2.68 | 3.492 (2) | 141 |
Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −x+1, −y+1, −z; (iii) y−1/4, −x+5/4, −z+1/4. |
Experimental details
Crystal data | |
Chemical formula | C18H16FN3O2 |
Mr | 325.34 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 291 |
a, c (Å) | 22.9526 (7), 12.7318 (7) |
V (Å3) | 6707.4 (5) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37145, 3665, 3033 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.638 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.158, 1.06 |
No. of reflections | 3665 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.34 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.93 | 2.57 | 3.306 (2) | 137 |
C9—H9A···Cg3i | 0.97 | 2.85 | 3.673 (2) | 143 |
C11—H11A···Cg2ii | 0.97 | 2.96 | 3.759 (2) | 141 |
C12—H12A···Cg1iii | 0.97 | 2.72 | 3.548 (2) | 143 |
C12—H12B···Cg1ii | 0.97 | 2.68 | 3.492 (2) | 141 |
Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −x+1, −y+1, −z; (iii) y−1/4, −x+5/4, −z+1/4. |
Quinazolinones are important heterocyclic compounds which exhibit good biological and pharmaceutical activities, including anti-inflammotory, antifunga, anticancer and AMPA-receptor antagonistic properties (Shiba et al., 1997). As part of our work on the preparation of potentially active heterocycles (Ding et al., 2000), we have obtained the title compound, (I).
Within the molecule of (I), the bond lengths and angles present no unusual features. In (I), the quinazolinone ring system is approximately planar, with a maximum deviation of 0.060 (1) and 0.028 (1) Å for atoms N1 and N2, respectively; the C13—C18 benzene ring is twisted with respect to it, with a dihedral angle of 67.09 (8)°. The morpholine ring shows a distorted chair conformation [φ = 341.64 (1)° and θ = 176.25 (1)°, Puckering Amplitude = 0.586 (1) Å] (Cremer & Pople, 1975). The structure is stabilized by a weak C—H···O hydrogen bond and C—H···π interactions (Table 1); Cg1, Cg2 and Cg3 are the centroids of C1—C6, N1/C7/C5/C6/N2/C8 and C13—C18 rings, respectively..