Zeitschrift für Kristallographie - New Crystal Structures 212, 211-212
© by R. Oldenbourg Verlag, München 1997
211
Crystal structure of (3Ä,45,l'Ä,l
,/S,2
,'Ä)-3-acetoxy-4-(2
/,-acetoxyacetoxy- l
/',3"-ethylidenedioxy-propyl)-l-(l
/-phenylethyl)-azetidin-2-one,
C 2 2 H 2 7 N O 9
S. Henkel, Β. Krämer and V. Jäger
Universität Stuttgart, Institut für Organische Chemie, Pfaffenwaldring 55, D-70569 Stuttgart, Germany Received August 16, 1996, CSD-No. 402603
C22H27NO9, orthorhombic, P2i2i2i (No. 19), a =8.269(1) Â,
¿>=11.383(2) Â, c=24.568(3) Â, V=2312.5Â3, Z=4, R(F)=0.057, R^F1) =0.140.
Table 1. Parameters used for the X-ray data collection
Crystal: colorless block, size 0.5 χ 0.5 χ 0.6 mm Wavelength: Mo Ka radiation (0.71073 Â)
μ: 1.01 cm"1
Diffractometer: Nicolet P3
Scan mode: Wyckoff Τ measurement'· 293 Κ
29max: 54°
NCWrOimii«: 2670 Criterion for /0: /o > 2 σ(Λ>) Ν (param)refined: 290
Programs: SHELXS-86, SHELXL-93
Source of material: The title compound (alternative name: (17?)- 2-0-acetyl-5-acetoxyacetoxy-3-amino-3-deoxy-4,6-0-ethylidene- /V-phenylethyl-D-glucono-1,3-lactam; see ref. 1 ) was prepared by [2+2]-cycloaddition of (2S,3/?,17?)-2,4-0-ethylidene-erythrose /V-(l'-phenylethyl)imine (see refs. 2, 3) with acetoxyacetyl chloride in CH2Ch/Et3N at 243 Κ (see ref. 1). The reaction gave a 77 : 23 mixture of cis diastereomers, which were separated by chromatography on silica with petroleum ether/ethyl acetate (60 : 40). The structure represents the minor diastereomer.
Table 2. Final atomic coordinates and displacement parameters (in Â2)
Atom Site X y ζ ÍAso
H(3) 4a -0.1121 -0.1013 0.8651 0.051 H(4) 4a 0.1033 -0.0612 0.9252 0.046 H(5) 4a 0.0293(4) 0.1537(3) 0.9150(1) 0.043 H(7) 4a 0.1054{5) 0.3314(3) 0.8787(2) 0.053 H(71A) 4a 0.1772(6) 0.3405(4) 0.7863(2) 0.094 H(71B) 4a 0.3588(6) 0.3175(4) 0.8012(2) 0.094 H(71C) 4a 0.2755(6) 0.4355(4) 0.8186(2) 0.094 H(9A) 4a 0.1855(6) 0.3080(4) 0.9700(2) 0.062 H(9B) 4a 0.3681(6) 0.2831(4) 0.9838(2) 0.062 H(10) 4a 0.3551(5) 0.0961(3) 0.9438(2) 0.047 H(13A) 4a 0.0580(6) 0.0480(5) 1.0881(2) 0.073 H(13B) 4a 0.1350(6) -0.0736(5) 1.0729(2) 0.073 H(16A) 4a 0.355(1) -0.0152(5) 1.2215(2) 0.131 H(16B) 4a 0.492(1) -0.1026(5) 1.2038(2) 0.131 H(16C) 4a 0.330(1) -0.1510(5) 1.2281(2) 0.131 H(17) 4a 0.4379(5) -0.0516(4) 0.8818(2) 0.055 H(17A) 4a 0.4638(7) -0.0889(5) 0.7885(2) 0.106 H(17B) 4a 0.4011(7) -0.2175(5) 0.7971(2) 0.106 H(17C) 4a 0.5676(7) -0.1789(5) 0.8218(2) 0.106 H(19) 4a 0.4917(6) -0.1319(4) 0.9659(2) 0.068 H(20) 4a 0.4646(7) -0.2718(5) 1.0320(2) 0.085 H(21) 4a 0.3099(7) -0.4364(5) 1.0158(2) 0.083 H(22) 4a 0.1846(6) -0.4601(4) 0.9318(2) 0.083 H(23) 4a 0.2199(6) -0.3197(4) 0.8648(2) 0.066 H(26A) 4a -0.2756(8) 0.1969(6) 0.7879(2) 0.140 H(26B) 4a -0.3243(8) 0.2602(6) 0.8421(2) 0.140 H(26C) 4a -0.4394(8) 0.1657(6) 0.8166(2) 0.140
Table 3. Final atomic coordinates and displacement parameters (in Â2)
Atom Site X y ζ Un t/22 I/33 Un Un t/23
N(l) 4a 0.2123(4) -0.0691(3) 0.8543(1) 0.044(2) 0.038(2) 0.040(2) 0.003(2) -0.005(2) 0.002(1) C(2) 4a 0.0959(5) -0.1001(4) 0.8180(2) 0.058(2) 0.042(2) 0.039(2) -0.004(2) -0.006(2) 0.005(2) 0(2) 4a 0.0979(5) -0.1565(3) 0.7760(1) 0.089(2) 0.064(2) 0.046(2) 0.003(2) -0.016(2) -0.015(2) C(3) 4a -0.0359(5) -0.0449(4) 0.8530(2) 0.043(2) 0.041(2) 0.044(2) -0.008(2) -0.010(2) 0.010(2)
212 C 2 2 H 2 7 N O 9
Table 3. (Continued)
Atom Site X y ζ l/ii Un ί/33 ί/12 1/13 t/23
C(4) 4a 0.1008(5) -0.0121(3) 0.8930(2) 0.039(2) 0.038(2) 0.037(2) -0.002(2) -0.006(2) 0.006(2) C(5) 4a 0.1321(4) 0.1174(3) 0.9046(1) 0.032(2) 0.040(2) 0.035(2) 0.002(2) -0.002(2) 0.004(2) CK6) 4a 0.1885(3) 0.1743(2) 0.8571(1) 0.048(1) 0.037(1) 0.035(1) -0.001(1) -0.001(1) 0.004(1) C(7) 4a 0.2076(5) 0.2970(3) 0.8663(2) 0.044(2) 0.038(2) 0.049(2) -0.001(2) -0.003(2) 0.003(2) C(71) 4a 0.2595(6) 0.3527(4) 0.8132(2) 0.069(3) 0.052(2) 0.066(3) -0.001(2) 0.001(3) 0.014(2) 0(8) 4a 0.3298(4) 0.3159(3) 0.9053(1) 0.049(2) 0.047(2) 0.059(2) -0.010(1) -0.005(2) 0.003(1) C(9) 4a 0.2832(6) 0.2695(4) 0.9573(2) 0.050(2) 0.053(2) 0.052(2) -0.005(2) -0.010(2) -0.002(2) C(10) 4a 0.2536(5) 0.1378(3) 0.9508(2) 0.035(2) 0.044(2) 0.040(2) -0.001(2) -0.003(2) 0.002(2) 0(11) 4a 0.1734(3) 0.0915(3) 0.9991(1) 0.041(1) 0.062(2) 0.034(1) -0.002(1) -0.005(1) 0.006(1) C(12) 4a 0.2640(5) 0.0653(4) 1.0425(2) 0.048(2) 0.044(2) 0.045(2) 0.002(2) -0.010(2) -0.002(2) 0(12) 4a 0.4046(4) 0.0848(4) 1.0459(1) 0.053(2) 0.094(3) 0.067(2) -0.012(2) -0.023(2) 0.018(2) C(13) 4a 0.1593(6) 0.0057(5) 1.0847(2) 0.067(3) 0.071(3) 0.044(2) 0.011(3) -0.006(2) 0.012(2) 0(14) 4a 0.2371(6) 0.0020(3) 1.1358(1) 0.104(3) 0.060(2) 0.052(2) 0.010(2) -0.019(2) 0.007(2) 0(15) 4a 0.3160(7) -0.1787(4) 1.1206(2) 0.146(4) 0.079(3) 0.083(3) 0.034(3) -0.023(3) -0.024(2) C(15) 4a 0.3077(7) -0.0964(4) 1.1506(2) 0.078(3) 0.048(2) 0.060(3) 0.004(3) -0.002(3) -0.002(2) C(16) 4a 0.377(1) -0.0908(5) 1.2058(2) 0.129(6) 0.076(4) 0.058(3) 0.018(4) -0.026(3) -0.004(3) C(17) 4a 0.3742(5) -0.1154(4) 0.8658(2) 0.042(2) 0.043(2) 0.053(2) 0.005(2) 0.001(2) -0.003(2) C(171) 4a 0.4596(7) -0.1537(5) 0.8134(2) 0.067(3) 0.080(3) 0.065(3) 0.016(3) 0.015(3) 0.006(3) C(18) 4a 0.3611(5) -0.2121(3) 0.9081(2) 0.040(2) 0.033(2) 0.046(2) 0.007(2) 0.000(2) -0.004(2) C(19) 4a 0.4312(6) -0.1990(4) 0.9587(2) 0.061(3) 0.053(3) 0.056(2) 0.011(2) -0.016(2) -0.003(2) C(20) 4a 0.4141(7) -0.2819(5) 0.9985(2) 0.085(4) 0.069(4) 0.059(3) 0.024(3) -0.008(3) 0.006(3) C(21) 4a 0.3224(7) -0.3798(5) 0.9888(2) 0.066(3) 0.068(3) 0.074(3) 0.020(3) 0.017(3) 0.029(3) C(22) 4a 0.2480(6) -0.3942(4) 0.9385(2) 0.049(2) 0.043(2) 0.114(4) 0.002(2) 0.006(3) 0.019(3) C(23) 4a 0.2690(6) -0.3098(4) 0.8986(2) 0.053(2) 0.043(2) 0.068(3) 0.002(2) -0.014(2) 0.000(2) 0(24) 4a -0.1206(3) 0.0473(3) 0.8262(1) 0.041(1) 0.054(2) 0.052(2) 0.001(1) -0.009(1) 0.015(1) C(25) 4a -0.2458(6) 0.0943(4) 0.8541(2) 0.042(2) 0.057(3) 0.069(3) -0.001(2) -0.012(2) 0.012(2) 0(25) 4a -0.2825(4) 0.0619(4) 0.8987(2) 0.060(2) 0.093(3) 0.072(2) 0.014(2) 0.011(2) 0.026(2) C(26) 4a -0.3286(8) 0.1875(6) 0.8224(2) 0.077(4) 0.104(5) 0.099(4) 0.036(4) 0.003(4) 0.037(4)
Acknowledgment. We thank the Fonds der Chemischen Industrie for financial support
References
1. Krämer, Β.: Diastereoselektive Darstellung von ß-Lactamen aus chiralen Iminen. Dissertation, University of Stuttgart, Germany, in preparation.
2. Ffengler-Veith, M.: Stereoselektive 1,3-dipolare Nitriloxid-Cycloadditionen unter Normal- und Hochdruck - Optisch aktive 4-Aminoisoxazoline durch Abbau bicyclischer Lactone. Dissertation, University of Stuttgart, Germany 19%.
3. Veith, U.; Leurs, S.; Jäger, V.: Auxiliary-controlled diastereoselection by N-(l-phenylethyl) in Grignard additions to 2-O-benzylglyceraldehyde imines. J. Chem. Soc. Chem. Commun. (19%) 329-330.
4. Sheldrick, G. M.: SHELXS-86. Program for the solution of crystal structures.
University of Göttingen, Germany 1986.
5. Sheldrick, G. M.: SHELXL-93, a program for refining crystal structures.
University of Göttingen, Germany 1993.
