organic compounds
4-Methyl-3-(2-phenoxyacetyl)-5-phenyl-1,3,4-oxadiazinan-2-one
aUniversidade Federal de São Carlos, Laboratório de Cristalografia, Estereodinâmica e, Modelagem Molecular, Departamento de Química, 13565-905 São Carlos, SP, Brazil, and bUniversidade de São Paulo, Conformational Analysis and Electronic Interactions, Laboratory, Instituto de Química, São Paulo, SP, Brazil
*Correspondence e-mail: julio@power.ufscar.br
The 1,3,4-oxadiazinane ring in the title compound, C18H18N2O4, is in a twisted boat conformation. The two carbonyl groups are orientated towards the same side of the molecule. The dihedral angle between the planes of the benzene rings is 76.6 (3)°. Molecules are sustained in the three-dimensional structure by a combination of C—H⋯O, C—H⋯π and π–π [shortest centroid–centroid distance = 3.672 (6) Å] interactions.
Related literature
For synthetic and structural studies of substituted heterocyclic rings, see: Rodrigues et al. (2006). For puckering parameters, see: Cremer & Pople (1975); Iulek & Zukerman-Schpector (1997). For the synthesis, see: Rodrigues et al. (2005).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and MarvinSketch (ChemAxon, 2008).
Supporting information
10.1107/S1600536809020285/tk2466sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020285/tk2466Isup2.hkl
The starting (R)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one was synthesized by using a previously reported procedure (Rodrigues et al. 2005). The phenoxyacetyl-1,3,4-oxadiazinan-2-one derivative was prepared by an acylation reaction of 1,3,4-oxadiazinan-2-one (Rodrigues et al. 2005). To a mixture of 1,3,4-oxadiazinan-2-one (500 mg, 2.60 mmol), 4-dimethylaminopyridine (16 mg, 0.13 mmol) and 2-phenoxyacetic acid (435 mg, 2.86 mmol) in CH2Cl2 (4 ml) at 273 K, under a nitrogen atmosphere, N,N-Dicyclohexylcarbodiimide was added in one portion (590 mg, 2.86 mmol). The temperature of the resulting suspension was allowed to reach room temperature. Stirring was continued until no starting material was left, as confirmed by TLC (20 h). The dicyclohexylurea formed was filtered and the precipitate washed with CH2Cl2 (20 ml). The filtrate was washed with a saturated aqueous solution of NaHCO3 (15 ml) and dried over Na2SO4. Filtration and evaporation yielded the crude solid, which was purified by flash
on silica gel (hexane-EtOAc, 6:4). Colourless crystals of (I) were obtained by vapour diffusion from hexane/chloroform at 298 K.The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.98 Å, and with Uiso set to 1.2 times (1.5 for methyl) Ueq(parent atom).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and MarvinSketch (ChemAxon, 2008).Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms). |
C18H18N2O4 | F(000) = 688 |
Mr = 326.34 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Melting point = 385–387 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6024 (9) Å | Cell parameters from 24 reflections |
b = 9.4203 (10) Å | θ = 10.5–15.1° |
c = 19.275 (3) Å | µ = 0.10 mm−1 |
β = 114.206 (9)° | T = 290 K |
V = 1590.3 (4) Å3 | Irregular, colourless |
Z = 4 | 0.15 × 0.10 × 0.08 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −11→0 |
ω–2θ scans | k = 0→11 |
2971 measured reflections | l = −20→20 |
2793 independent reflections | 3 standard reflections every 60 min |
1355 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.246 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0852P)2 + 2.8996P] where P = (Fo2 + 2Fc2)/3 |
2793 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C18H18N2O4 | V = 1590.3 (4) Å3 |
Mr = 326.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.6024 (9) Å | µ = 0.10 mm−1 |
b = 9.4203 (10) Å | T = 290 K |
c = 19.275 (3) Å | 0.15 × 0.10 × 0.08 mm |
β = 114.206 (9)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.030 |
2971 measured reflections | 3 standard reflections every 60 min |
2793 independent reflections | intensity decay: <1% |
1355 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.246 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.19 e Å−3 |
2793 reflections | Δρmin = −0.23 e Å−3 |
218 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | 0.6770 (6) | 0.3140 (6) | −0.0050 (3) | 0.0504 (14) | |
H1 | 0.6177 | 0.3840 | −0.0433 | 0.060* | |
C2 | 0.5715 (6) | 0.1861 (6) | −0.0126 (4) | 0.0676 (18) | |
H2A | 0.5123 | 0.2040 | 0.0169 | 0.081* | |
H2B | 0.5008 | 0.1758 | −0.0655 | 0.081* | |
C3 | 0.8059 (6) | 0.0406 (6) | 0.0376 (3) | 0.0530 (14) | |
C4 | 1.0422 (5) | 0.1778 (6) | 0.0667 (3) | 0.0411 (12) | |
C5 | 1.0994 (5) | 0.3123 (6) | 0.0478 (3) | 0.0492 (13) | |
H5A | 1.0756 | 0.3145 | −0.0062 | 0.059* | |
H5B | 1.0487 | 0.3921 | 0.0593 | 0.059* | |
C6 | 0.7359 (5) | 0.3870 (6) | 0.0714 (3) | 0.0419 (12) | |
C7 | 0.7468 (6) | 0.5357 (6) | 0.0737 (3) | 0.0550 (14) | |
H7 | 0.7155 | 0.5862 | 0.0284 | 0.066* | |
C8 | 0.8025 (8) | 0.6080 (7) | 0.1415 (4) | 0.0690 (18) | |
H8 | 0.8055 | 0.7067 | 0.1416 | 0.083* | |
C9 | 0.8541 (7) | 0.5350 (9) | 0.2091 (4) | 0.0735 (19) | |
H9 | 0.8956 | 0.5837 | 0.2551 | 0.088* | |
C10 | 0.8439 (7) | 0.3903 (8) | 0.2083 (3) | 0.0643 (17) | |
H10 | 0.8769 | 0.3407 | 0.2539 | 0.077* | |
C11 | 0.7850 (6) | 0.3167 (7) | 0.1400 (3) | 0.0596 (16) | |
H11 | 0.7784 | 0.2182 | 0.1405 | 0.071* | |
C12 | 1.3081 (6) | 0.3918 (6) | 0.1593 (3) | 0.0452 (12) | |
C13 | 1.4569 (5) | 0.4434 (6) | 0.1878 (3) | 0.0498 (14) | |
H13 | 1.5174 | 0.4293 | 0.1612 | 0.060* | |
C18 | 0.7580 (7) | 0.2267 (6) | −0.1031 (3) | 0.0593 (16) | |
H18A | 0.8470 | 0.2022 | −0.1114 | 0.089* | |
H18B | 0.7058 | 0.3041 | −0.1358 | 0.089* | |
H18C | 0.6912 | 0.1461 | −0.1141 | 0.089* | |
C14 | 1.5132 (6) | 0.5148 (6) | 0.2553 (3) | 0.0573 (15) | |
H14 | 1.6120 | 0.5508 | 0.2739 | 0.069* | |
C15 | 1.4279 (7) | 0.5343 (7) | 0.2958 (3) | 0.0640 (17) | |
H15 | 1.4668 | 0.5849 | 0.3412 | 0.077* | |
C16 | 1.2833 (7) | 0.4782 (7) | 0.2689 (3) | 0.0650 (16) | |
H16 | 1.2256 | 0.4878 | 0.2973 | 0.078* | |
C17 | 1.2231 (6) | 0.4082 (6) | 0.2007 (3) | 0.0544 (14) | |
H17 | 1.1244 | 0.3719 | 0.1826 | 0.065* | |
N1 | 0.8837 (4) | 0.1580 (4) | 0.0262 (2) | 0.0420 (10) | |
N2 | 0.8042 (4) | 0.2689 (4) | −0.0233 (2) | 0.0383 (10) | |
O1 | 0.6553 (4) | 0.0565 (4) | 0.0129 (3) | 0.0744 (13) | |
O2 | 0.8648 (5) | −0.0680 (4) | 0.0671 (3) | 0.0712 (12) | |
O3 | 1.1208 (4) | 0.0946 (4) | 0.1131 (2) | 0.0611 (11) | |
O4 | 1.2593 (4) | 0.3245 (4) | 0.0898 (2) | 0.0569 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.041 (3) | 0.043 (3) | 0.057 (3) | 0.004 (2) | 0.010 (2) | 0.003 (3) |
C2 | 0.041 (3) | 0.054 (4) | 0.098 (5) | −0.001 (3) | 0.019 (3) | 0.001 (3) |
C3 | 0.046 (3) | 0.046 (3) | 0.066 (4) | −0.001 (3) | 0.022 (3) | 0.003 (3) |
C4 | 0.041 (3) | 0.044 (3) | 0.035 (3) | 0.009 (2) | 0.012 (2) | 0.000 (2) |
C5 | 0.036 (3) | 0.063 (4) | 0.044 (3) | −0.001 (3) | 0.012 (2) | 0.000 (3) |
C6 | 0.037 (3) | 0.044 (3) | 0.049 (3) | 0.005 (2) | 0.022 (2) | 0.004 (3) |
C7 | 0.062 (4) | 0.051 (3) | 0.057 (3) | 0.001 (3) | 0.029 (3) | 0.003 (3) |
C8 | 0.089 (5) | 0.056 (4) | 0.073 (4) | −0.013 (4) | 0.045 (4) | −0.018 (4) |
C9 | 0.066 (4) | 0.100 (6) | 0.063 (4) | −0.003 (4) | 0.035 (3) | −0.020 (4) |
C10 | 0.067 (4) | 0.082 (5) | 0.053 (4) | 0.019 (4) | 0.034 (3) | 0.014 (4) |
C11 | 0.058 (4) | 0.058 (4) | 0.070 (4) | 0.005 (3) | 0.034 (3) | 0.011 (3) |
C12 | 0.040 (3) | 0.046 (3) | 0.047 (3) | 0.005 (2) | 0.016 (2) | 0.001 (3) |
C13 | 0.034 (3) | 0.057 (3) | 0.054 (3) | 0.003 (3) | 0.014 (2) | 0.004 (3) |
C18 | 0.059 (3) | 0.057 (4) | 0.046 (3) | 0.007 (3) | 0.005 (3) | −0.004 (3) |
C14 | 0.039 (3) | 0.062 (4) | 0.058 (3) | −0.003 (3) | 0.007 (3) | 0.005 (3) |
C15 | 0.063 (4) | 0.066 (4) | 0.053 (3) | 0.002 (3) | 0.014 (3) | −0.016 (3) |
C16 | 0.068 (4) | 0.066 (4) | 0.068 (4) | −0.001 (3) | 0.035 (3) | −0.015 (3) |
C17 | 0.046 (3) | 0.053 (3) | 0.065 (4) | −0.013 (3) | 0.024 (3) | −0.016 (3) |
N1 | 0.038 (2) | 0.038 (2) | 0.048 (2) | 0.0001 (19) | 0.0159 (19) | 0.006 (2) |
N2 | 0.036 (2) | 0.041 (2) | 0.035 (2) | 0.0063 (18) | 0.0121 (17) | 0.0054 (18) |
O1 | 0.047 (2) | 0.046 (2) | 0.125 (4) | −0.0046 (19) | 0.030 (2) | 0.012 (2) |
O2 | 0.078 (3) | 0.040 (2) | 0.099 (3) | 0.008 (2) | 0.040 (2) | 0.024 (2) |
O3 | 0.054 (2) | 0.056 (2) | 0.058 (2) | 0.009 (2) | 0.0075 (18) | 0.009 (2) |
O4 | 0.0379 (19) | 0.080 (3) | 0.050 (2) | −0.0048 (19) | 0.0159 (16) | −0.015 (2) |
C1—N2 | 1.466 (6) | C9—C10 | 1.366 (9) |
C1—C6 | 1.511 (7) | C9—H9 | 0.9300 |
C1—C2 | 1.542 (8) | C10—C11 | 1.386 (8) |
C1—H1 | 0.9800 | C10—H10 | 0.9300 |
C2—O1 | 1.433 (7) | C11—H11 | 0.9300 |
C2—H2A | 0.9700 | C12—C17 | 1.365 (7) |
C2—H2B | 0.9700 | C12—O4 | 1.378 (6) |
C3—O2 | 1.194 (6) | C12—C13 | 1.391 (7) |
C3—O1 | 1.332 (6) | C13—C14 | 1.364 (8) |
C3—N1 | 1.402 (7) | C13—H13 | 0.9300 |
C4—O3 | 1.195 (6) | C18—N2 | 1.469 (6) |
C4—N1 | 1.410 (6) | C18—H18A | 0.9600 |
C4—C5 | 1.484 (7) | C18—H18B | 0.9600 |
C5—O4 | 1.417 (6) | C18—H18C | 0.9600 |
C5—H5A | 0.9700 | C14—C15 | 1.355 (9) |
C5—H5B | 0.9700 | C14—H14 | 0.9300 |
C6—C11 | 1.378 (7) | C15—C16 | 1.373 (8) |
C6—C7 | 1.404 (8) | C15—H15 | 0.9300 |
C7—C8 | 1.372 (8) | C16—C17 | 1.369 (7) |
C7—H7 | 0.9300 | C16—H16 | 0.9300 |
C8—C9 | 1.374 (9) | C17—H17 | 0.9300 |
C8—H8 | 0.9300 | N1—N2 | 1.410 (5) |
N2—C1—C6 | 110.6 (4) | C9—C10—H10 | 119.7 |
N2—C1—C2 | 109.3 (4) | C11—C10—H10 | 119.7 |
C6—C1—C2 | 114.7 (5) | C6—C11—C10 | 121.1 (6) |
N2—C1—H1 | 107.3 | C6—C11—H11 | 119.5 |
C6—C1—H1 | 107.3 | C10—C11—H11 | 119.5 |
C2—C1—H1 | 107.3 | C17—C12—O4 | 125.0 (5) |
O1—C2—C1 | 112.2 (4) | C17—C12—C13 | 119.5 (5) |
O1—C2—H2A | 109.2 | O4—C12—C13 | 115.5 (5) |
C1—C2—H2A | 109.2 | C14—C13—C12 | 119.4 (5) |
O1—C2—H2B | 109.2 | C14—C13—H13 | 120.3 |
C1—C2—H2B | 109.2 | C12—C13—H13 | 120.3 |
H2A—C2—H2B | 107.9 | N2—C18—H18A | 109.5 |
O2—C3—O1 | 119.9 (5) | N2—C18—H18B | 109.5 |
O2—C3—N1 | 124.9 (5) | H18A—C18—H18B | 109.5 |
O1—C3—N1 | 115.2 (5) | N2—C18—H18C | 109.5 |
O3—C4—N1 | 122.3 (5) | H18A—C18—H18C | 109.5 |
O3—C4—C5 | 124.0 (5) | H18B—C18—H18C | 109.5 |
N1—C4—C5 | 113.6 (4) | C15—C14—C13 | 121.3 (5) |
O4—C5—C4 | 110.6 (4) | C15—C14—H14 | 119.4 |
O4—C5—H5A | 109.5 | C13—C14—H14 | 119.4 |
C4—C5—H5A | 109.5 | C14—C15—C16 | 119.1 (5) |
O4—C5—H5B | 109.5 | C14—C15—H15 | 120.5 |
C4—C5—H5B | 109.5 | C16—C15—H15 | 120.5 |
H5A—C5—H5B | 108.1 | C17—C16—C15 | 120.8 (6) |
C11—C6—C7 | 117.3 (5) | C17—C16—H16 | 119.6 |
C11—C6—C1 | 124.1 (5) | C15—C16—H16 | 119.6 |
C7—C6—C1 | 118.6 (5) | C12—C17—C16 | 119.8 (5) |
C8—C7—C6 | 121.4 (6) | C12—C17—H17 | 120.1 |
C8—C7—H7 | 119.3 | C16—C17—H17 | 120.1 |
C6—C7—H7 | 119.3 | C3—N1—N2 | 121.0 (4) |
C7—C8—C9 | 120.2 (6) | C3—N1—C4 | 122.8 (4) |
C7—C8—H8 | 119.9 | N2—N1—C4 | 116.0 (4) |
C9—C8—H8 | 119.9 | N1—N2—C1 | 109.0 (4) |
C10—C9—C8 | 119.5 (6) | N1—N2—C18 | 110.8 (4) |
C10—C9—H9 | 120.3 | C1—N2—C18 | 114.0 (4) |
C8—C9—H9 | 120.3 | C3—O1—C2 | 126.3 (4) |
C9—C10—C11 | 120.6 (6) | C12—O4—C5 | 116.7 (4) |
N2—C1—C2—O1 | 37.4 (7) | C15—C16—C17—C12 | 1.0 (10) |
C6—C1—C2—O1 | −87.4 (6) | O2—C3—N1—N2 | 165.9 (5) |
O3—C4—C5—O4 | 2.4 (7) | O1—C3—N1—N2 | −14.2 (7) |
N1—C4—C5—O4 | −179.3 (4) | O2—C3—N1—C4 | −18.8 (9) |
N2—C1—C6—C11 | −82.9 (6) | O1—C3—N1—C4 | 161.1 (5) |
C2—C1—C6—C11 | 41.2 (7) | O3—C4—N1—C3 | 0.8 (8) |
N2—C1—C6—C7 | 94.9 (6) | C5—C4—N1—C3 | −177.6 (5) |
C2—C1—C6—C7 | −141.0 (5) | O3—C4—N1—N2 | 176.3 (4) |
C11—C6—C7—C8 | −0.6 (8) | C5—C4—N1—N2 | −2.0 (6) |
C1—C6—C7—C8 | −178.5 (5) | C3—N1—N2—C1 | 49.4 (6) |
C6—C7—C8—C9 | 2.2 (9) | C4—N1—N2—C1 | −126.2 (4) |
C7—C8—C9—C10 | −2.5 (10) | C3—N1—N2—C18 | −76.8 (6) |
C8—C9—C10—C11 | 1.2 (10) | C4—N1—N2—C18 | 107.6 (5) |
C7—C6—C11—C10 | −0.6 (8) | C6—C1—N2—N1 | 68.9 (5) |
C1—C6—C11—C10 | 177.1 (5) | C2—C1—N2—N1 | −58.2 (5) |
C9—C10—C11—C6 | 0.3 (9) | C6—C1—N2—C18 | −166.8 (4) |
C17—C12—C13—C14 | −2.7 (8) | C2—C1—N2—C18 | 66.1 (6) |
O4—C12—C13—C14 | 178.3 (5) | O2—C3—O1—C2 | 169.7 (6) |
C12—C13—C14—C15 | 1.2 (9) | N1—C3—O1—C2 | −10.2 (9) |
C13—C14—C15—C16 | 1.4 (9) | C1—C2—O1—C3 | −3.0 (9) |
C14—C15—C16—C17 | −2.5 (10) | C17—C12—O4—C5 | 21.0 (8) |
O4—C12—C17—C16 | −179.5 (5) | C13—C12—O4—C5 | −160.0 (5) |
C13—C12—C17—C16 | 1.6 (9) | C4—C5—O4—C12 | −90.5 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O4i | 0.93 | 2.53 | 3.394 (7) | 154 |
C9—H9···O3ii | 0.93 | 2.61 | 3.383 (8) | 141 |
C13—H13···Cg2iii | 0.93 | 2.86 | 3.715 (6) | 153 |
C18—H18B···Cg3i | 0.96 | 2.74 | 3.672 (6) | 165 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H18N2O4 |
Mr | 326.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 290 |
a, b, c (Å) | 9.6024 (9), 9.4203 (10), 19.275 (3) |
β (°) | 114.206 (9) |
V (Å3) | 1590.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.15 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2971, 2793, 1355 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.246, 1.12 |
No. of reflections | 2793 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.23 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and MarvinSketch (ChemAxon, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O4i | 0.93 | 2.53 | 3.394 (7) | 154 |
C9—H9···O3ii | 0.93 | 2.61 | 3.383 (8) | 141 |
C13—H13···Cg2iii | 0.93 | 2.86 | 3.715 (6) | 153 |
C18—H18B···Cg3i | 0.96 | 2.74 | 3.672 (6) | 165 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2; (iii) x+1, y, z. |
Acknowledgements
We thank FAPESP (2008/02531–5 to JZ—S; 2003/05520–0 to AR), CNPq and CAPES for financial support.
References
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In continuation of synthetic and structural studies of substituted heterocyclic rings (Rodrigues et al., 2006), the title compound (I) was prepared. The 1,3,4-oxadiazinane ring in (I), Fig. 1, is in a distorted twist boat conformation with the distortion being towards a boat conformation. The ring-puckering parameters (Cremer & Pople, 1975; Iulek & Zukerman-Schpector, 1997) were calculated as q2 = 0.119 (6) Å, q3 = -0.496 (6) Å, Q = 0.510 (6) Å, and ϕ2 = -108 (3)°. The ring- and side-chain-bound carbonyl groups lie to the same side of the molecule. The dihedral angle between the phenyl rings is of 76.6 (3)°. Molecules are sustained in the 3-D structure by a combination of C-H···O and π–π interactions, Table 1.