CH(CH3)SCH3

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H(13C) 4e. 0.2864(5) 0.3563(4). 0.4957(4) 0.08. Table 3. Atomic coordinates and displacement parameters (in k2). Atom. Site. X. У г. U и. Uzi ί/33 υπ ί/.з. 1/23. S.
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Ζ. Kristallogr. NCS 215 (2000) 3 7 - 3 8 © by Oldenbourg Wissenschaftsverlag, München

Crystal structure of

3-hydroxy-3-(l-methylthioethyl)-2-methyl-

2,3-dihydroisoindol-1 -one,

C8H4ONCH3(OH)[CH(CH3)SCH3]

K. Peters*·1, E.-M. Peters', M. Oelgemöller", J.-M. Cho11 and A. Griesbeck11 1

Max-Planck-Institut für Festkörperforschung, Heisenbergstraße 1, D-70506 Stuttgart, Germany " Universität zu Köln, Institut für Organische Chemie, Greinstraße 4, D-50939 Köln, Germany

Received June 17, 1999, CCDC-No. 1267/210

tion is initiated by electron transfer from the thioether f o l l o w e d by rapid extrusion o f carbon dioxide. In the crystal t w o m o l e c u l e s build a pair around a symmetry center via the hydrogen bridge 0 3 - - H l a ( 1 7 6 pm).

Table 1. Data collection and handling. Crystal: Wavelength: μ: Diffractometer, scan mode: 20max*. N(hkl)measured, N(/lW)unique: Criterion for F0bs, N(hkl)gt: N(param) refined: Program:

colourless prism, size 0.35 χ 0 7 5 χ 0.4 mm Mo Ka radiation (0.71073 Ä) 2.50 cm"1 Bruker AXS P4, ω 55° 3093, 2755 Fobs > 3 a(Fobs), 2336 150 SHELXTL-plus [4]

Abstract

Table 2. Atomic coordinates and displacement parameters (in A").

C12H15NO2S, monoclinic, P\2\!n\ ( N 0 . 14), a = 8 . 0 3 9 ( 1 ) Ä, b= 1 1 . 7 3 7 ( l ) Ä , c = 1 2 . 7 3 1 ( l ) Ä , ß = 9 1 . 0 9 ( 1 ) ° , V = 1 2 0 1 . 0 Ä 3 , Ζ = 4, Rgt(F) = 0 . 0 8 3 , wR(F) = 0 . 0 8 8 , Τ = 2 9 3 К.

Atom

Site

H(l) H(5) H(6) H(7) H(8) H(10) H(11A) H(11B) H(11C) H(12A) H(12B) H(12C) H(13A) H(13B) H(13C)

4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e

Source of material The title c o m p o u n d was prepared from /V-methyl phthalimide and potassium 2-methylsulfanyl propionate by irradiation ( 3 0 0 nm, 2 4 h) in an acetone/water mixture (4:1). Extraction and recrystallization from ethyl acetate/n-hexane yielded 3 4 % of colorless crystals [1].

Discussion This reaction w a s studied in context with mechanistic problems in intermolecular photoreactions b e t w e e n phthalimides and c a r b o x y l a t e s [2]. In contrast to the intramolecular p h o t o decarboxylation of ω-phthalimido alkylcarboxylates [3] the reac-

X -0.074(6) 0.0065(6) -0.1793(7) -0.2252(7) -0.0988(6) 0.3216(5) 0.0356(7) 0.1651(7) -0.0015(7) 0.4737(6) 0.3385(6) 0.4513(6) 0.3439(5) 0.4380(5) 0.2864(5)

У

ζ

l/i«.

0.400(5) 0.7830(4) 0.8599(4) 0.7693(5) 0.5970(5) 0.4004(3) 0.3288(4) 0.2755(4) 0.3271(4) 0.5591(4) 0.6397(4) 0.5655(4) 0.3358(4) 0.4243(4) 0.3563(4)

0.660(4) 0.5053(4) 0.6262(5) 0.7840(5) 0.8254(4) 0.7712(3) 0.9968(4) 0.9204(4) 0.8755(4) 0.8383(4) 0.7881(4) 0.7158(4) 0.6125(4) 0.5431(4) 0.4957(4)

0.10(2) 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08

Table 3. Atomic coordinates and displacement parameters (in k 2 ). Atom

Site

X

У

г



Uzi

ί/33

S C(l) O(l) N(2) C(3)

4e 4e 4e 4e 4e

0.1832(2) 0.1336(5) 0.0348(4) 0.2183(4) 0.1765(5)

0.4723(1) 0.4782(3) 0.3803(3) 0.4819(3) 0.5721(3)

0.9157(1) 0.6953(3) 0.7014(2) 0.5923(3) 0.5329(3)

0.112(1) 0.053(2) 0.066(2) 0.052(2) 0.046(2)

0.0744(9) 0.049(2) 0.059(2) 0.047(2) 0.051(2)

0.0491(7) 0.043(2) 0.052(2) 0.048(2) 0.052(2)

υπ 0.0106(7) 0.001(2) -0.005(1) 0.001(1) -0.009(2)

ί/.з -0.0020(7) 0.004(2) 0.003(1) 0.004(1) -0.005(2)

1/23 -0.0066(6) -0.002(2) 0.008(1) -0.002(1) 0.004(2)

* Correspondence author (e-mail: [email protected])

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38

C8H 4 ONCH3(OH)[CH(CH3)SCH 3 ]

Table 3. Continued. Atom

Site

0(3) C(4) C(5) C(6) C(7)

4e

C(8)

4e

C(9) C(10) C(ll) C(12) C(13)

4e

4e 4e 4e 4e

4e 4e 4e 4e

X

0.2243(4) 0.0621(5) -0.0148(6) -0.1230(7) -0.1506(7) -0.0753(6) 0.0351(5) 0.2683(5) 0.0840(7) 0.3945(6) 0.3314(5)

У

ζ

ί/ιι

Uli

ί/эз

0.5904(3) 0.6424(3) 0.7449(4) 0.7896(4) 0.7354(5) 0.6345(5) 0.5874(4) 0.4720(3) 0.3348(4) 0.5679(4) 0.3918(4)

0.4425(2) 0.5954(3) 0.5704(4) 0.6418(5) 0.7350(5) 0.7604(4) 0.6905(3) 0.7846(3) 0.9287(4) 0.7814(4) 0.5579(4)

0.061(2) 0.051(2) 0.066(3) 0.075(3) 0.083(4) 0.073(3) 0.054(2) 0.068(3) 0.084(3) 0.089(4) 0.058(2)

0.079(2) 0.044(2) 0.044(2) 0.053(3) 0.091(4) 0.099(4) 0.057(2) 0.052(2) 0.082(3) 0.067(3) 0.060(3)

0.058(2) 0.068(3) 0.104(4) 0.125(5) 0.102(4) 0.069(3) 0.051(2) 0.049(2) 0.063(3) 0.082(4) 0.063(3)

References 1. Oelgemöller, M.: Photochemistry of phthalimides: decarboxylative addition of carboxylates and PET-induced macrocyclizations. Doctoral thesis, University of Cologne, Germany 1999. 2. Griesbeck, A. G.; Oelgemöller, Μ.: Photodecarboxylative Addition of Carboxylates and α-keto carboxylates. Synlett (1999) 492-494.

Ul2

-0.011(2) -0.003(2) -0.004(2) 0.017(2) 0.036(3) 0.028(3) 0.006(2) 0.009(2) 0.014(3) -0.010(3) 0.005(2)

Uii

0.004(1) -0.011(2) -0.030(3) -0.032(3) -υ.οΐ4(3) 0.001(3) -0.004(2) -0.005(2) 0.010(3) -0.037(3) 0.006(2)

t/23 0.014(2) -0.001(2) 0.002(2) -0.023(3) -0.042(4) -0.023(3) -0.008(2) -0.002(2) 0.010(3) 0.001(3) -0.008(2)

3. Griesbeck, A. G.; Henz, Α.; Kramer, W.; Nerowski, F.; Oelgemöller, Μ.; Peters, К.; Peters, E.-M.: Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of ω-phthalimido alkylcarboxylates. Helv. Chim. Acta 80 (1997) 912-933 4. Sheldrick, G. M.: Program Package SHELXTL-plus. Release 4.1. Siemens Analytical X-Ray Instruments Inc., Madison (WI 53719), USA 1990.

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