Ζ. Kristallogr. NCS 214 (1999) 265-266
© by R. Oldenbourg Verlag, München
2 6 5
C r y s t a l s t r u c t u r e o f rac-(6R,l7£)-6-(r,2'-diacetoxyethyl)-2-phenyl-5,6-
d i h y d r o - 4 i / - l , 3 - o x a z i n e , ( C 6 H 5 ) C 4 H 5 N O [ C 2 H 3 ( O C O C H 3 ) 2 ]
K. Peters*·
1, E.-M. Peters
1, R. Kugler" and V. Jäger
111 Max-Planck-Institut für Festkörperforschung, Heisenbergstraße 1, D-70506 Stuttgart, Germany
" Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany Received November 24, 1998, CCD-No. 1267/73
C 4
0 1 5
Table 1. Data collection and handling.
Crystal: colorless plate, size 0.7 χ 0.5 χ 0.2 mm Wavelength: Mo Ka radiation (0.71073 Ä)
μ: 1.00 cm"1
Diffractometer, scan mode: Siemens P4, ω
20max: 55°
N(hkl)measured, /V(M/)unique: 4217, 3555 Criterion for Fobs, N(hkl)gc. Fobs > 3 o(Fobs), 2472 N(param) refined: 200
Program: SHELXTL-plus [3]
Table 2. Atomic coordinates and displacement parameters (in A2).
Atom Site χ y ζ Uho
Abstract
C16H19NO5, triclinic, PI (No. 2), a = 9.211(1) Ä, b = 9.259(2) Ä, c = 9.796(2) Ä, cc = 84.36(1)°, β = 85.26(1)°, γ = 69.21(1)°, V = 116.2 Ä
3, Ζ = 2, RoJF) = 0.069, RJF) = 0.069, Τ = 293 Κ.
Source of material
The title compound was prepared by polar [4-
+,+2]-cycloaddition f r o m /V-chloromethylbenzamide and 1,2-diacetoxy-3-butene with tin(IV)chloride as Lewis acid. The isomers (d:r = 65:35) were separated by MPLC and the minor (threo) isomer was recrystallized from pentane/diethyl ether (mp 367 Κ) [1, 2],
Discussion
The phenyl and the oxazine ring systems are stacked along [101].
H(4A) 2i 0.2500(4) 0.4158(4) 0.7864(3) 0.08 H(4B) 2i 0.3437(4) 0.2502(4) 0.8511(3) 0.08 H(5A) 2 i 0.3821(4) 0.2312(3) 0.6189(3) 0.08 H(5B) 2i 0.2038(4) 0.3145(3) 0.5979(3) 0.08 H(6) 2i 0.3331(3) 0.0266(3) 0.7344(3) 0.08 H(7) 2 i 0.3768(3) -0.0144(3) 0.5107(2) 0.08 H(11A) 2 i 0.1681(4) 0.3409(4) 0.1783(3) 0.08 H(11B) 2 i 0.0512(4) 0.3765(4) 0.3068(3) 0.08 H(11C) 2 i 0.0584(4) 0.2447(4) 0.2147(3) 0.08 H(12A) 2 i 0.1189(3) -0.1046(3) 0.5643(3) 0.08 H(12B) 2 i 0.2672(3) -0.1867(3) 0.6490(3) 0.08 H(16A) 2 i 0.3644(4) -0.5460(4) 0.3356(3) 0.08 H(16B) 2 i 0.4882(4) -0.4669(4) 0.3423(3) 0.08 H(16C) 2i 0.3472(4) -0.3902(4) 0.2481(3) 0.08 H(18) 2 i -0.1053(4) 0.0227(3) 0.8214(3) 0.08 H(19) 2 i -0.3442(4) 0.0273(4) 0.9263(3) 0.08 H(20) 2 i -0.4777(4) 0.2169(4) 1.0795(3) 0.08 H(21) 2 i -0.3767(4) 0.4062(4) 1.1178(3) 0.08 H(22) 2i -0.1374(3) 0.4022(4) 1.0146(3) 0.08
Table 3. Atomic coordinates and displacement parameters (in Ä2).
Atom Site
X y
ζυ
π U22 t/33 U12 U13 t/23O(l) 2
i
0.0984(2) 0.1153(2) 0.7346(2) 0.044(1) 0.050(1) 0.045(1) -0.0198(8) 0.0131(8) -0.0189(8) C(2) 2 i 0.0493(3) 0.2149(3) 0.8380(2) 0.042(1) 0.046(1) 0.035(1) -0.008(1) 0.003(1) -0.010(1) N(3) 2 i 0.1159(3) 0.3023(3) 0.8738(2) 0.055(1) 0.065(2) 0.047(1) -0.024(1) 0.006(1) -0.022(1) C(4) 2 i 0.2559(4) 0.3098(4) 0.7984(3) 0.059(2) 0.074(2) 0.062(2) -0.034(2) 0.011(2) -0.030(2) C(5) 2 i 0.2794(4) 0.2447(3) 0.6580(3) 0.052(2) 0.058(2) 0.054(2) -0.028(1) 0.013(1) -0.018(1) C(6) 2 i 0.2538(3) 0.0920(3) 0.6753(3) 0.035(1) 0.045(1) 0.041(1) -0.010(1) 0.003(1) -0.011(1) C(7) 2/ 0.2699(3) 0.0133(3) 0.5433(2) 0.033(1) 0.042(1) 0.038(1) -0.011(1) 0.006(1) -0.007(1)* Correspondence author
(e-mail: karpet@vsibml.mpi-stuttgart.mpg.de)
266
(C6H5)C4H5NO[C2H3(OCOCH3)2]Table 3. Continued.
Atom Site X y ζ Un U22 i/33 Un Un U2 3
0(8) 2i 0.1715(2) 0.1172(2) 0.4422(2) 0.038(1) 0.047(1) 0.0402(9) -0.0160(8) 0.0033(8) -0.0018(7) C(9) 2 i 0.2367(3) 0.1831(3) 0.3384(3) 0.051(2) 0.047(1) 0.039(1) -0.018(1) 0.003(1) -0.006(1) O(10) 2 i 0.3744(3) 0.1535(3) 0.3221(2) 0.050(1) 0.087(2) 0.064(1) -0.023(1) 0.014(1) 0.012(1) C(ll) 2 i 0.1185(4) 0.2962(4) 0.2519(3) 0.071(2) 0.070(2) 0.055(2) -0.023(2) -0.005(2) 0.009(2) C(12) 2 i 0.2296(3) -0.1307(3) 0.5638(3) 0.052(2) 0.043(1) 0.042(1) -0.017(1) 0.013(1) -rO.OlO(l) 0(13) 2 i 0.3054(2) -0.2234(2) 0.4511(2) 0.070(1) 0.048(1) 0.046(1) -0.029(1) 0.013(1) -0.0161(8) C(14) 2 i 0.2870(4) -0.3590(3) 0.4491(3) 0.054(2) 0.039(1) 0.063(2) -0.016(1) 0.003(1) -0.002(1) 0(15) 2 i 0.2102(4) -0.4018(3) 0.5333(3) 0.155(3) 0.056(1) 0.149(3) -0.054(2) 0.084(2) -0.031(2) C(16) 2 i 0.3800(4) -0.4486(4) 0.3336(3) 0.082(2) 0.053(2) 0.060(2) -0.019(2) -0.004(2) -0.019(1) C(17) 2 i -0.0992(3) 0.2122(3) 0.9054(2) 0.042(1) 0.048(1) 0.034(1) -0.008(1) 0.001(1) -0.005(1) C(18) 2 i -0.1612(4) 0.1018(3) 0.8821(3) 0.052(2) 0.055(2) 0.054(2) -0.015(1) 0.013(1) -0.009(1) C(19) 2i -0.3012(4) 0.1032(4) 0.9453(3) 0.062(2) 0.071(2) 0.062(2) -0.029(2) 0.011(2) -0.005(2) C(20) 2 i -0.3815(4) 0.2165(4) 1.0335(3) 0.049(2) 0.089(2) 0.047(2) -0.013(2) 0.012(1) 0.001(2) C(2I) 2 i -0.3204(4) 0.3268(4) 1.0576(3) 0.053(2) 0.086(2) 0.042(1) -0.013(2) 0.011(1) -0.020(2) C(22) 2 i -0.1797(3) 0.3257(4) 0.9957(3) 0.052(2) 0.065(2) 0.039(1) -0.011(1) 0.005(1) -0.017(1)
Acknowledgments. We are grateful to the Fonds der Chemischen Industrie for financial support and to Dr. Wolfgang Frey for helpful discussions.
References
1. Kugler, R.: Unpublished results.
2. Kugler, R.: Dissertation, Stuttgart (planned).
3. Sheldrick, G. M.: Program Package SHELXTL-plus. Release 4.1. Sie- mens Analytical X-Ray Instruments Inc., Madison (WI 53719), USA 1990.
