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The title compound, C14H21NO5, possesses an isoxazolyl group in the axial position of the 1,3-dioxanyl ring. The two rings are rotated about the bond joining them such that the two C(methyl)-C(dioxanyl)-C-C torsion angles are 92.1 (2) and -84.1 (2)°. In this conformation, neither the methyl nor ethoxy­carbonyl substituents on the isoxazole are presented towards the dioxanyl chair.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008489/fr1265sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008489/fr1265Isup2.hkl
Contains datablock I

CCDC reference: 150855

Computing details top

Data collection: SMART (Bruker, 1997a); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C14H21NO5Z = 2
Mr = 283.32F(000) = 304
Triclinic, P1Dx = 1.279 Mg m3
a = 8.5710 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5382 (9) ÅCell parameters from 74 reflections
c = 10.3449 (9) Åθ = 2.1–27.0°
α = 105.7991 (10)°µ = 0.10 mm1
β = 94.1123 (11)°T = 193 K
γ = 112.6952 (13)°Block, colorless
V = 735.72 (12) Å30.40 × 0.20 × 0.20 mm
Data collection top
CCD area detector
diffractometer
2392 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 25.4°, θmin = 2.1°
phi and ω scansh = 109
3851 measured reflectionsk = 1012
2688 independent reflectionsl = 1210
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0451P)2 + 0.4327P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.005
2688 reflectionsΔρmax = 0.30 e Å3
182 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXTL (Bruker, 1997b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (4)
Special details top

Experimental. Data were acquired on a three-circle Bruker CCD diffractometer and detector with mounted LT-2 low temperature apparatus operating at 213 K. The crystal was mounted on the glass fiber of the goniometer head using silicone grease for adhesion. The cell constants were determined from 60 thirty-second frames. Data were measured using omega scans of 0.3° and 30 - s per frame until completion of the collection hemisphere. A complete hemisphere consisting of 1272 frames was collected in all with a maximum 0.83 Angstrom resolution. A fourth data collection iteration of 50 frames was collected in order to monitor for crystal decay (<1%). Cell parameters were retrieved using SMART (Bruker, 1997) software and refined using SAINT (Bruker, 1997) on all observed reflections. Data reduction was achieved through the use of the SAINT software, which corrects for Lp and decay. Absorption corrections were applied using SADABS supplied by George Sheldrick based on method of Blessing(1995). The structures are solved by the direct method using the SHELXS97 program (Sheldrick, 1990) and refined by least squares method on F2 SHELXL97 (Sheldrick, 1997), incorporated in SHELXTL-PC V 5.10 (Bruker, 1997). Non hydrogen atoms were refined anisotropically, whereas hydrogen atoms were located from difference map and subsequently refined isotropically.

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
xyzUiso*/Ueq
O10.68566 (16)0.50891 (15)0.94588 (13)0.0346 (3)
O20.4294 (2)0.01121 (17)0.73592 (14)0.0453 (4)
O30.31381 (18)0.05417 (15)0.91888 (13)0.0371 (3)
O40.21280 (15)0.15184 (14)0.61285 (12)0.0292 (3)
O50.34379 (15)0.40112 (14)0.57755 (12)0.0286 (3)
N10.6131 (2)0.35593 (19)0.96175 (15)0.0340 (4)
C10.6080 (2)0.5001 (2)0.82283 (17)0.0289 (4)
C20.4866 (2)0.3484 (2)0.75691 (17)0.0255 (4)
C30.4981 (2)0.2639 (2)0.84897 (17)0.0281 (4)
C40.4097 (2)0.0868 (2)0.82610 (17)0.0296 (4)
C50.2298 (3)0.1158 (2)0.9064 (2)0.0427 (5)
H5A0.31570.16170.90420.051*
H5B0.14130.17660.82080.051*
C60.1474 (3)0.1264 (3)1.0288 (2)0.0471 (5)
H6A0.08980.23921.02380.071*
H6B0.06230.08101.02970.071*
H6C0.23620.06581.11280.071*
C70.6729 (3)0.6518 (2)0.7889 (2)0.0383 (5)
H7A0.60930.63340.69890.057*
H7B0.79600.68700.78720.057*
H7C0.65600.73500.85850.057*
C80.3712 (2)0.2792 (2)0.61569 (17)0.0259 (4)
C90.1001 (2)0.2027 (2)0.68997 (19)0.0313 (4)
H9A0.15410.24880.78860.038*
H9B0.00990.10840.67770.038*
C100.0629 (2)0.3280 (2)0.64413 (19)0.0308 (4)
C110.2389 (2)0.4620 (2)0.65640 (18)0.0290 (4)
H11A0.22330.54500.62370.035*
H11B0.29810.51310.75390.035*
C120.4534 (3)0.2072 (2)0.50732 (19)0.0378 (5)
H12A0.37650.16360.41750.057*
H12B0.47320.12090.52900.057*
H12C0.56380.29070.50530.057*
C130.0370 (3)0.2545 (2)0.4957 (2)0.0411 (5)
H13A0.05980.33620.46780.062*
H13B0.14670.16440.48870.062*
H13C0.03150.21590.43570.062*
C140.0375 (3)0.3947 (3)0.7400 (2)0.0438 (5)
H14A0.02880.44110.83420.066*
H14B0.14880.30770.73500.066*
H14C0.05690.47800.71240.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0337 (7)0.0352 (7)0.0308 (7)0.0134 (6)0.0007 (5)0.0079 (5)
O20.0656 (10)0.0397 (8)0.0409 (8)0.0308 (7)0.0196 (7)0.0134 (6)
O30.0488 (8)0.0312 (7)0.0368 (7)0.0187 (6)0.0152 (6)0.0150 (6)
O40.0291 (6)0.0258 (6)0.0337 (7)0.0128 (5)0.0038 (5)0.0098 (5)
O50.0337 (7)0.0325 (7)0.0279 (6)0.0180 (5)0.0087 (5)0.0157 (5)
N10.0392 (9)0.0358 (9)0.0301 (8)0.0188 (7)0.0032 (7)0.0118 (7)
C10.0272 (9)0.0349 (9)0.0267 (9)0.0157 (7)0.0055 (7)0.0090 (7)
C20.0259 (8)0.0314 (9)0.0260 (8)0.0170 (7)0.0092 (7)0.0113 (7)
C30.0310 (9)0.0339 (9)0.0255 (8)0.0194 (8)0.0076 (7)0.0102 (7)
C40.0352 (9)0.0351 (10)0.0259 (9)0.0215 (8)0.0037 (7)0.0118 (7)
C50.0543 (12)0.0320 (10)0.0445 (11)0.0169 (9)0.0101 (10)0.0183 (9)
C60.0498 (13)0.0466 (12)0.0552 (13)0.0211 (10)0.0156 (10)0.0298 (10)
C70.0363 (10)0.0332 (10)0.0402 (11)0.0089 (8)0.0050 (8)0.0132 (8)
C80.0296 (9)0.0269 (8)0.0262 (8)0.0151 (7)0.0064 (7)0.0114 (7)
C90.0272 (9)0.0338 (10)0.0377 (10)0.0140 (7)0.0088 (7)0.0169 (8)
C100.0283 (9)0.0326 (9)0.0365 (10)0.0162 (8)0.0054 (7)0.0142 (8)
C110.0312 (9)0.0289 (9)0.0321 (9)0.0164 (7)0.0060 (7)0.0126 (7)
C120.0478 (11)0.0470 (12)0.0276 (9)0.0295 (10)0.0118 (8)0.0109 (8)
C130.0379 (10)0.0385 (11)0.0450 (11)0.0175 (9)0.0062 (9)0.0127 (9)
C140.0390 (11)0.0503 (12)0.0551 (13)0.0274 (10)0.0169 (10)0.0220 (10)
Geometric parameters (Å, º) top
O1—C11.359 (2)C7—H7A0.9800
O1—N11.410 (2)C7—H7B0.9800
O2—C41.201 (2)C7—H7C0.9800
O3—C41.331 (2)C8—C121.514 (2)
O3—C51.462 (2)C9—C101.528 (2)
O4—C81.422 (2)C9—H9A0.9900
O4—C91.438 (2)C9—H9B0.9900
O5—C81.418 (2)C10—C111.523 (2)
O5—C111.436 (2)C10—C141.526 (3)
N1—C31.309 (2)C10—C131.531 (3)
C1—C21.357 (2)C11—H11A0.9900
C1—C71.486 (3)C11—H11B0.9900
C2—C31.425 (2)C12—H12A0.9800
C2—C81.520 (2)C12—H12B0.9800
C3—C41.501 (2)C12—H12C0.9800
C5—C61.502 (3)C13—H13A0.9800
C5—H5A0.9900C13—H13B0.9800
C5—H5B0.9900C13—H13C0.9800
C6—H6A0.9800C14—H14A0.9800
C6—H6B0.9800C14—H14B0.9800
C6—H6C0.9800C14—H14C0.9800
C1—O1—N1108.82 (13)O4—C8—C2110.15 (13)
C4—O3—C5115.16 (14)C12—C8—C2111.17 (14)
C8—O4—C9114.37 (12)O4—C9—C10111.44 (14)
C8—O5—C11113.54 (12)O4—C9—H9A109.3
C3—N1—O1104.81 (14)C10—C9—H9A109.3
C2—C1—O1110.05 (15)O4—C9—H9B109.3
C2—C1—C7134.39 (16)C10—C9—H9B109.3
O1—C1—C7115.55 (15)H9A—C9—H9B108.0
C1—C2—C3103.36 (15)C11—C10—C14109.40 (15)
C1—C2—C8129.33 (15)C11—C10—C9105.59 (14)
C3—C2—C8127.23 (15)C14—C10—C9109.82 (16)
N1—C3—C2112.96 (16)C11—C10—C13110.58 (16)
N1—C3—C4118.36 (15)C14—C10—C13110.89 (16)
C2—C3—C4128.40 (15)C9—C10—C13110.41 (15)
O2—C4—O3125.16 (17)O5—C11—C10111.16 (14)
O2—C4—C3122.60 (17)O5—C11—H11A109.4
O3—C4—C3112.21 (14)C10—C11—H11A109.4
O3—C5—C6107.30 (16)O5—C11—H11B109.4
O3—C5—H5A110.3C10—C11—H11B109.4
C6—C5—H5A110.3H11A—C11—H11B108.0
O3—C5—H5B110.3C8—C12—H12A109.5
C6—C5—H5B110.3C8—C12—H12B109.5
H5A—C5—H5B108.5H12A—C12—H12B109.5
C5—C6—H6A109.5C8—C12—H12C109.5
C5—C6—H6B109.5H12A—C12—H12C109.5
H6A—C6—H6B109.5H12B—C12—H12C109.5
C5—C6—H6C109.5C10—C13—H13A109.5
H6A—C6—H6C109.5C10—C13—H13B109.5
H6B—C6—H6C109.5H13A—C13—H13B109.5
C1—C7—H7A109.5C10—C13—H13C109.5
C1—C7—H7B109.5H13A—C13—H13C109.5
H7A—C7—H7B109.5H13B—C13—H13C109.5
C1—C7—H7C109.5C10—C14—H14A109.5
H7A—C7—H7C109.5C10—C14—H14B109.5
H7B—C7—H7C109.5H14A—C14—H14B109.5
O5—C8—O4111.63 (13)C10—C14—H14C109.5
O5—C8—C12106.73 (14)H14A—C14—H14C109.5
O4—C8—C12106.27 (14)H14B—C14—H14C109.5
O5—C8—C2110.76 (13)
C1—O1—N1—C30.43 (18)C11—O5—C8—C12169.54 (14)
N1—O1—C1—C20.34 (18)C11—O5—C8—C269.31 (17)
N1—O1—C1—C7178.79 (15)C9—O4—C8—O552.55 (18)
O1—C1—C2—C30.89 (18)C9—O4—C8—C12168.54 (14)
C7—C1—C2—C3178.00 (19)C9—O4—C8—C270.94 (17)
O1—C1—C2—C8177.80 (15)C1—C2—C8—O526.4 (2)
C7—C1—C2—C81.1 (3)C3—C2—C8—O5157.39 (15)
O1—N1—C3—C21.03 (19)C1—C2—C8—O4150.38 (16)
O1—N1—C3—C4173.42 (14)C3—C2—C8—O433.4 (2)
C1—C2—C3—N11.23 (19)C1—C2—C8—C1292.1 (2)
C8—C2—C3—N1178.22 (16)C3—C2—C8—C1284.1 (2)
C1—C2—C3—C4172.54 (16)C8—O4—C9—C1055.23 (19)
C8—C2—C3—C44.5 (3)O4—C9—C10—C1154.89 (18)
C5—O3—C4—O20.5 (3)O4—C9—C10—C14172.74 (15)
C5—O3—C4—C3177.43 (15)O4—C9—C10—C1364.67 (19)
N1—C3—C4—O2113.8 (2)C8—O5—C11—C1058.18 (18)
C2—C3—C4—O259.7 (3)C14—C10—C11—O5174.55 (14)
N1—C3—C4—O364.2 (2)C9—C10—C11—O556.42 (18)
C2—C3—C4—O3122.30 (18)C13—C10—C11—O563.03 (18)
C4—O3—C5—C6172.98 (16)C2—C8—O4—C970.9 (2)
C11—O5—C8—O453.83 (17)C2—C8—O5—C1169.3 (2)
Comparison of the torsion angles for the isoxazolyl compounds (I)-(IV) top
CompoundC2-C3-C4-O3_angles(°)
(I)62.8 (1)
(II)175.8 (2)
(III)-1.6 (3)
(IV)108.2 (3)
 

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