M. MILLAN, C. F. CONDE, A.
CONDE AND
R.
M,~RQUEZ 277
CRIADO, A., CONDE,
A. &
M.h.RQUEZ,
R. (1983).
Ac a C ys .
C39,
122-125.
CRIADO, A., CONDE, A. & MARQUEZ, R.
(1984).
Ac a C ys .
C40,
188-190.
GALBIS PI~REZ, J.
A.,
AVALOS GONZALEZ,
M.,
JIMIgNEZ REQUEJO,
J. L. & PALACIOS ALBARRAN, J. C.
(1983).
Ca bohyd . Res.
124,
C15-C17.
HAMILTON,
W. C. (1959).
Ac a C ys .
12, 609-610.
In e na ional Tables o X- ay C ys allog aphy
(1974). Vol. IV.
Bi mingham: Kynoch P ess. (P esen dis ibu o D. Reidel,
Do d ech .)
LONGCHAMBON, F., OHANESSIAN, J., AVENEL, D. (~ NEWMAN, A.
(1975).
Ac a C ys .
B31, 2623-2627.
LONGCHAMBON, F., OHANESSIAN, J. (~ GILLIER-PANDRAUD, H.
(1981).
Ac a C ys .
B37, 601-607.
MAIN, P., FISKE, S. J., HULL, S. E., LESSINGER, L., GERMAIN, P.,
DECLERCQ,
J.-P. &
WOOLFSON,
M. M. (1980).
MULTANSO. A
Sys em o Compu e P og ams o he Au oma ic Solu ion o
C ys al S uc u es om X- ay Di ac ion Da a.
Uni s. o Yo k,
England, and Lou ain, Belgium.
NARDELLI,
M. (1983).
Ac a C ys .
C39, 1141-1142.
OHANESSIAN, J.,
LONGCHAMBON,
F. & ARENE, C. (1978).
Ac a
C ys .
B34, 3666-3671.
SHIMIZU, N., NISHIGAKI, S., NAKAI, Y. & OSAKI, K. (1982).
Ac a
C ys .
B38, 2309-231 I.
STEWART, J. M., KUNDELL, F. A. (~ BALDWIN, J. C. (1970). The
XRA
Y70 sys em. Compu e Science Cen e , Uni . o Ma yland,
College Pa k, Ma yland.
TAYLOR,
R. (~
KENNARD,
O. (1982).
J. Am. Chem. Soc.
104,
5063-5070.
Ac a C ys .
(1985). C41, 277-280
S uc u e and Absolu e Con igu a ion o l'-(p-B omophenyl)-3'-e hyl-l',Y,4',5'-
e ahyd o- 1,2-dideoxy-u-L-gluco u anoso[2,l-d]imidazole-2'- hione Monohyd a e,*
C15H19B N204S.H20
By
C. F. CONDE, M. MILLAN, A.
CONDE AND
R.
M.~,RQUEZ
Depa amen o de Op ica y Secci6n de F[sica del Cen o Coo dinado del CSIC, Uni e sidad de Se illa, Spain
(Recei ed
27
June
1984;
accep ed 15 Oc obe
1984)
Abs ac .
M
=
421-30, monoclinic, P2~, a = 7.531 (1),
b=8.148(4), c= 14. 625 (2) ,~, l=97.14(1) °, V=
890.5 (5) ,~3, Z= 2,
Din=
1.58 (1),
Dx=
1.571 Mg m -3, Mo Kc , 2 = 0.7107 ,~,/~ = 2.42 mm -1,
F(000)=432, T= 300 K, R =0.065 o 1672 ob-
se ed independen e lexions. The suga ing adop s a
4T 3 con o ma ion and he dihed al angle in he bicyclic
sys em is 72.3 (4) °. A h ee-dimensional ne wo k o
hyd ogen bonds links he molecules o build up he
c ys al s uc u e.
In oduc ion.
The s uc u e de e mina ion o he i le
compound (I) was unde aken as pa o a con inuing
esea ch p ojec in his labo a o y in ol ing
glucimidazoles and imidazole C-nucleosides. Du ing
he pas ew yea s amino-suga s ha e been used
in he p epa a ion o hese compounds (Ga cia
Gonz~lez, Fe n/mdez-Bola ios & Lopez-Apa icio,
1976; Fe n/mdez-Bola ios, Galbis P6 ez & Zamo a
Ma a, 1984; Galbis P6 ez, Palacios Alba ~n, Jim~nez
Requejo & A aloN Gonzhlez, 1984)
ia
1-a yl-
gluco u anosoimidazolidine-2- hiones. Some o hese
compounds, p epa ed in he O ganic Chemis y
Depa men o he Uni e si y o Ex emadu a, ha e
* IUPAC name: 6-(p-b omophenyl)-2-(l,2-dihyd oxye hyl)-4-
e hyl-3 -hyd oxy-2,3,3 a,5,6,6a-hexahyd o u ol 2,3-dlimidazole-
5(4H)- hione monohyd a e.
0108-2701/85/020277-04501.50
been s udied in o de o es ablish he con o ma ional
de ails o he molecule in he solid s a e ( o example,
Es ada, Conde & M~ quez, 1983, 1984). Galbis P6 ez
e al.
(1984) ha e epo ed he applica ion o
aminoni ile syn hesis o he p epa a ion o he
new 2-deoxy-2-(e hylamino)-c -L-glucopy anose hyd o-
chlo ide and i s eac ion wi h 4-b omophenyl iso hio-
cyana e, o a o d he i le compound. I s chemical
na u e was es ablished om elemen al analysis and
spec oscopic IR and NMR da a and he X- ay
analysis was ca ied ou o de ine he s uc u al de ails.
.OCH~ /0 ~ ~N /C,.,B,
"
OH OH
C2H5
(I)
•
H20
Expe imen al.
Single c ys als in he o m o colou less
needles elonga ed along [100] p epa ed in he O ganic
Chemis y Depa men o he Uni e si y o Ex-
emadu a and kindly supplied by P o esso J. A.
Galbis.
D m
by lo a ion me hod. C ys al 0.09 × 0.14 x
0.30 mm. Uni -cell pa ame e s by leas squa es om 25
e lexions, 5 < 0 < 18 °. En a -Nonius CAD-4 di ac-
ome e , g aphi e monoch oma o , 20 < 60 °
(-10 _< h _<10, 0<_k_<ll, 0</<20), o--20 scan
© 1985 In e na ional Union o C ys allog aphy
278 C 15H x9B N204S.H20
mode. Two s anda d e lexions (103, 004): a ia ion in
in ensi y less han 2.5% o he mean alue. 2745
independen e lexions measu ed, 1073 conside ed
unobse ed [I < 2a(/)]. Lo en z and pola iza ion co -
ec ion; no co ec ion o abso p ion (/zR ~0.15) o
ex inc ion. Pa e son unc ion and hea y-a om me hod
wi h he ini ial se o phases based on B -a om posi ion.
Full-ma ix leas -squa es e inemen on F, aniso opic;
di e ence Fou ie syn hesis e ealed he 21 H-a om
posi ions; iso opic empe a u e ac o o each H a om
equal o ha o he a om bonded o i ; u he
leas -squa es e inemen including he posi ional
pa ame e s o he H a oms and anomalous-dispe sion
co ec ions o B and S a omic sca e ing ac o s
(In e na ional Tables o X- ay C ys allog aphy,
1974)
educed
R w
o 0.071 (R = 0.065); weigh ing scheme
based on a s a is ical coun c i e ion (w=
1/a2).
B
(A/O)max
= 0.04. S = 2.05 o 217 e ined pa ame e s, s
Final di e ence syn hesis showed 0.40 >
Ap
> c(I)
--0.30 e A -3.
c(2)
C(3)
The enan iomo phic o m o he molecule was e ined c(4)
sepa a ely and con e ged o a inal
R w
alue o 0.076 c(5)
(R 0.071). The applica ion o he ~' es (Hamil on, c(6)
= C(7)
1965) indica es ha he i s enan iomo ph is co ec a c(8)
a signi icance le el much lowe han 0.005 [Rw(2)/ c(9) c(10)
Rw(1 ) = 1.092; ~'L1455,0.005 ~- 1.003] and, he e o e, can c(11)
be e ained as he absolu e con igu a ion. Mo eo e , c(12)
his absolu e con igu a ion is consis en wi h ha c(13)
C(14)
de ined by e e ence o he suga moie y. C ys al- c(15)
log aphic p og ams o he
XRAY70
sys em (S ewa , o(1) 0(2)
Kundell & Baldwin, 1970) we e used h oughou .
0(3)
0(4)
0(5)
N(I)
N(2)
Discussion. F ac ional a omic coo dina es and equi -
alen iso opic empe a u e ac o s (Hamil on, 1959)
o non-hyd ogen a oms a e gi en in Table 1.* Bond
leng hs and angles in ol ing non-hyd ogen a oms a e
lis ed in Fig. 1.
Bond dis ances and angles in he imidazolidine ing
ag ee wi h he mean alues epo ed o analogous
gluco u anoimidazolidine-2- hione compounds (Conde,
Be nie & M~quez, 1980; Es ada, Conde & M~quez,
1983, 1984).
The obse ed asymme y o he N(1)-C(I) and
N(2)-C(1) leng hs
(A/a
= 3.5 1) indica es he in luence
o he subs i uen s a N(1) and N(2) on he esonance:
-S-C
//N +- N-
-s-c /
N-
~N +-
/
* Lis s o s uc u e ac o s, aniso opic he mal pa ame e s and
H-a om pa ame e s ha e been deposi ed wi h he B i ish Lib a y
Lending Di ision as Supplemen a y Publica ion No. SUP 39834
(14 pp.). Copies may be ob ained h ough The Execu i e Sec e a y,
In e na ional Union o C ys allog aphy, 5 Abbey Squa e, Ches e
CH 1 2HU, England.
The imidazolidine ing is no plana ; he ing a oms
de ia e signi ican ly
[~.(A/a)2=
156.5] om he leas -
squa es plane [ he alue o he o al pucke ing
ampli ude (C eme & Pople, 1975) is Q=
0.122 (10)A] and his ea u e, no ound o mono-
subs i u ed [only a N(1)] gluco u anoimidazolidine
compounds, has been obse ed also in a ecen ly
epo ed analogous s uc u e (Es ada, Conde &
M& quez, 1983).
Table 1.
A omic ac ional coo dina es
equi alen iso opic empe a u e ac o s
Ue q 1%" N- * *
= ~,_.i=jUuai a i aiajcos(a aj).
(x 10
4)
and
(A 2
x
103)
x y z UeQ
9014 (2) 10000 -21 (1) 607 (5)
5891 (4) 3728 (5) 2514 (2) 389 (9)
3943 (12) 4787 (15) 2400 (7) 260 (29)
2069 (14) 7112 (15) 2276 (7) 308 (34)
1012 (13) 5565 (12) 2538 (7) 235 (27)
366 (12) 6051 (15) 3449 (7) 294 (32)
1849 (13) 7221 (15) 3835 (6) 261 (30)
1455 (13) 8395 (15) 4592 (6) 292 (33)
3007 (14) 9499 (15) 4901 (8) 345 (37)
4983 (13) 7236 (12) 1589 (6) 208 (27)
5718 (15) 6453 (16) 884 (8) 372 (37)
6911 (15) 7311 (18) 406(8) 420(41)
7359 (15) 8912 (15) 636 (8) 337 (35)
6594 (16) 9698 (16) 1313 (8) 396 (39)
5425 (16) 8869 (17) 1809 (8) 378 (38)
2042 (16) 2651 (15) 2994 (9) 353 (39)
585 (22) 1816 (17) 2390 (14) 789 (69)
2274 (10) 8127 (10) 3054 (5) 308 (25)
-1270 (9) 6957 (10) 3255 (6) 367 (26)
895 (1 I) 7503 (12) 5327 (5) 413 (28)
4545 (9) 8597 (13) 5279 (5) 417 (27)
2948 (11) 4691 (12) 5852 (7) 574 (36)
3781 (12) 6407 (12) 2089 (6) 309 (29)
2399 (12) 4279 (12) 2644 (6) 292 (28)
~ .&.,~c(15)
C(14~l l l
,.; ,, o
'2&6,~, q'c° - /
,_ ~ b-"~e.o~ 8 b,q-2/"~ "-2.20 o .,7-
.,~ $ c(ioi
B b~
Fig. 1. Bond leng hs (A) and angles (o) in he molecule. (S anda d
de ia ions a e in he anges O.010-O.020A and 0-7-1.1 °,
espec i ely.)
C. F. CONDE, M. MILLAN, A. CONDE AND R. M/~RQUEZ 279
Bond leng hs and angles in he u anosyl ing a e
close o he mean alues obse ed o analogous
compounds. The ypical asymme y o he endocyclic
bonds O(1)-C(2) and O(1)-C(5) in hese compounds
due o anome ic e ec s seems o be p esen ; howe e ,
he ea u e is di icul o es ablish in his case because o
he high e.s.d.'s
(A/ --
1.58). The gluco u anose ing is
no plana as expec ed. In e ms o he ing-pucke ing
coo dina es (C eme & Pople, 1975) he ampli ude and
phase magni udes a e 0.373 (11) A and 125.5 (15) ° o
he sequence O(1)-C(2)-C(3)-C(4)-C(5) and he
esul ing con o ma ion co esponds o a pucke ing
mode (4T3) simila o ha ound in a ecen ly epo ed
analogous compound (Es ada, Conde & M~ quez,
1983). The asymme y pa ame e o Na delli (1983a)is
AC2[C(2)]=0.0052(46). The small alue o he
o sion angle O(1)-C(2)-C(3)-C(4)= 11.4 (10) ° is
ano he ea u e o hese compounds and may be
a ibu ed o dis o ion o he u anosyl ing due o he
ing usion.
The wo ings show a
eis
o m o junc ion, as is
ound in analogous compounds, wi h he bonds a C(2)
and C(3) nea ly eclipsed. The dihed al angle be ween
he leas -squa es planes h ough he imidazolidine and
u anosyl ings is 72.9 (4) °.
The phenyl ing, plana as expec ed [Z(A/a) 2 = 3.8;
Z2= 7.8 a 95%], o ms a dihed al angle o 47.2 (4) °
wi h he imidazolidine ing. Values o his dihed al angle
in he ange 45-80 ° we e ound in analogous com-
pounds, excep o he alue o 15.1 (6) ° in he case o
l'-phenyl- l',3',4',5'- e ahyd o-l,2-dideoxygluco u an-
oso[ 1,2-d]imidazol-2-one (Conde, Be nie & M/u'quez,
1980).
The e hyl g oup is also wis ed wi h espec o he
imidazolidine ing as indica ed by he o sion angle
C(1)-N(2)-C(14)-C(15) =-120.1 (13) °.
o
Fig. 2. A iew along [ 100] o he uni -cell con en s. Hyd ogen bonds
a e indica ed by dashed lines.
Table 2.
Geome y o he possible hyd ogen bonds
X-H... Y X... Y (A) X-H (A) H... Y (A) X-H... Y (°)
C(13)-H(13)...O(l) 3.223 (15) 0.94 (15) 2.53 (15) 130 (ll)
C(6)-H(6)...O(2) 2.900(12) 0.80 (13) 2.39(15) 122 (14)
C(15)-H(153)...O(1 ~) 3.359 (13) 1.04 (21) 2.53 (20) 136 (14)
C(6)-H(6)...O(5 H) 3.463(13) 0.80(13) 2.78(14) 144(12)
C(7)-H(71)...O(5 "~) 3.369(14) 0.85(15) 2.80(15) 126(13)
O(5)-H(O51)...O(2 ~ ) 2.945 (13) 1.08 (19) 2. l0 (18) 134 (14)
O(5)-H(O52)...O(4 ) 2.806 (13) 1.06 (18) 1-89 (18) 143 (14)
O(4)-H(O4)...S u~ 3.287 (9) 0-87 (15) 2.47 (15) 156 (13)
Symme y code: none x, y, z; (i) x, y - 1, z; (ii) -x, y + ½, -z + 1 ;
(iii)-x+ l,y+½,-z+ l;(i )-x,y-½,-z+ l;( )-x+ 1,Y-½,
--z+ I.
C ys al paeking
Fig. 2 shows he con en s o he uni cell iewed
down [100]. The c ys al s uc u e is s abilized by a
h ee-dimensional hyd ogen-bonding ne wo k; he e a e
also wo in amolecula in e ac ions [C (13)-H (13)...
O(1) and C(6)-H(6)...O(2)] ha could also be
hyd ogen bonds (Je ey & Maluszynska, 1982;
Be ko i ch-Yellin & Leise owi z, 1984). Molecules
a e linked o o m chains pa allel o [010] by
C(15)-H(153)..-O(1)(x, y - 1, z) hyd ogen bonds. On
he o he hand molecules a e linked along [100],
h ough he hyd a ion wa e molecule, by wo hyd ogen
bonds: O(5)-H(O51)...O(2)(-x, y- ½, -z + 1) and
O(5)-H(O52)...O(4)(-x + 1, y-½, -z + 1). Finally,
each molecule is linked o he neighbou ela ed by a
wo old sc ew axis by O(4)-H(O4)...S(-x + 1, y + ½,
-z + 1). De ails o he geome y o hese hyd ogen
bonds a e gi en in Table 2.
Fo he wo O-H...O con ac s lis ed in Table 2
in ol ing he hyd a ion wa e molecule, he alues o
he d pa ame e , de ined as he di e ence be ween he
sum o he an de Waals adii and he in e a omic
dis ance (Taylo & Kenna d, 1982), a e 0.60 and
0.81 A espec i ely, bo h sa is ying he ule d > 0.3 A.
Fo he sho C-H...O in e ac ions only he
in amolecula con ac C(6)-H(6)...O(2) has a alue
d_~ 0.3 and he angles C--H...O a e, in all cases, a
om he ideal linea con igu a ion. Howe e , a high
dispe sion in expe imen al alues o C-H...O angle is
ound o in e ac ions wi h d > 0-3 (Taylo & Kenna d,
1982). Finally, he exis ence o sho O--H...S con ac s
has been ound in o he imidazolidine-2- hione com-
pounds and, pe haps, i could be associa ed wi h he
nega i e cha ge a S in he esonance o ms o he
hiou ea sys em. No o he in e molecula con ac
signi ican ly sho e han he sum o he an de Waals
adii has been de ec ed. The molecula geome y and
c ys al packing we e compu ed by
PARST
(Na delli,
1983b).
The au ho s hank P o esso J. Galbis o supplying
he c ys als and o help ul discussions on chemical
aspec s and P o esso A. L6pez-Cas o o collec ing
he di ac ome ic da a. The p esen wo k is pa o a
esea ch p ojec suppo ed by a g an om he
CAICYT o he Go e nmen .
280 C 15H
19B N 2045.H20
Re e ences
BERKOVITCH-YELLIN, C. & LEISEROWITZ, L. (1984).
Ac a C ys .
B40, 159-165.
CONDE, A., BERNIER, F. & MARQUEZ, R. (1980).
Ac a C ys .
B36,
3048-3052.
CREMER, D. & POPLE, J. A. (1975).
J. Am. Chem. Soc.
97,
1354-1358.
ESTRADA, M. D.,
CONDE,
A. &
MARQUEZ,
R. (1983). Ac a C ys .
C39, 1418-1421.
ESTRADA, M. D., CONDE, A. & MARQUEZ, R. (1984).
Ac a C ys .
C40, 898-901.
FERNANDEZ BOLAI~IOS, J., GALBIS P~REZ, J. A. & ZAMORA MATA,
F. (1984). An. Quim. 80C. In he p ess.
GALBIS P~REZ, J. A., PALACIOS ALBARRAN, J. C., JIMI~NEZ
REQUEJO, J. L. & AVALOS GONZALEZ, M. (1984).
Ca bohyd .
Res. 129. In he p ess.
GARC1A GONZALEZ, F., FERNANDEZ BOLAI~IOS, J. & LOPEZ
APARICIO, F. J. (1976).
Am. Chem. Soc. Sy up. Se .
39,
207-226.
HAMILTON, W. C. (1959).
Ac a C ys .
12, 609-610.
HAMILTON, W. C. (1965).
Ac a C ys .
18, 502-510.
In e na ional Tables o X- ay C ys allog aphy
(1974). Vol. IV.
Bi mingham: Kynoch P ess.
JEFFREY, G. A. & MALUSZYNSKA, n. (1982).
In . J. Biol.
Mac omol.
4, 173-185.
NARDELLI, M. (1983a).
Ac a C ys .
C39, 1141-1142.
NARDELLI, M. (1983b).
Compu . Chem.
7, 95-98.
STEWART, J. M., KUNDELL, F. A. & BALDWIN, J. C. (1970). The
XRA Y70
sys em. Compu e Science Cen e , Uni . o Ma yland,
College Pa k, Ma yland.
TAYLOR, R. & KENNARD, O. (1982).
J. Am. Chem. Soc.
104,
5063-5070.
Ac a C ys . (1985). C41,280-282
S uc u e o Nap oxen,*
C14H1403
BY K. RAVIKUMAR,~ S. S. RAJAN~ AND VASANTHA PATTABHI
Depa men o C ys allog aphy and Biophysics, Uni e si y o Mad as, Guindy Campus, Mad as-600025, India
AND
E. J.
GABE§
Depa men o Chemis y, Na ional R esea ch Council o Canada, O awa, Canada K 1A OR 9
(Recei ed 27 Decembe 1983; accep ed 17 Oc obe 1984)
Abs ac . An e ec i e inhibi o o cyclo-oxygenase.
M =230.25 , monoclinic, P21, a= 13.3150(10), b
= 5.7765 (4), c= 7.8732 (4)A, l= 93.88 (1) °, V=
604.2 (1)A 3, Z= 2, Din= 1.25 (2) ( lo a ion), D~=
1.265 Mg m -3, 2(Mo Ka 1) = 0.70926/~, #(Mo Ka) =
0.095 mm -1, F(000) = 244, T= 296 K, inal R(F)
= 0.061 o 1037 obse ed e lec ions. The o a ion o
he ca boxyl g oup wi h espec o he benezene ing,
which seems o be connec ed wi h an i-in lamma o y
po en ial, is simila o he o he wo subs i u ed
p opionic acids al eady epo ed. The benzene ings in
he naph hyl g oup a e inclined a an angle o 5.2 (2) °.
In oduc ion.
The i le compound, an e ec i e inhibi o
o he cyclo-oxygenase esponsible o biosyn hesis o
p os aglandins, was ob ained om D Na a ajan,
Ins i u e o Basic Medical Sciences, Mad as. I exhibi s
an i-in lamma o y, analgesic and an ipy e ic ac i i y in
man (Goodman & Gilman, 1980). The analysis o i s
s uc u e was unde aken o help o es ablish he
s uc u e-ac i i y ela ionship in p opionic acid
de i a i es.
* IUPAC name: (+)-2-(6-me hoxy-2-naph hyl)p opionic acid.
5" Con ibu ion No. 654 om he Depa men o C ys allog aphy
and Biophysics, Uni e si y o Mad as, Mad as-600 025, India.
$ To whom co espondence should be add essed.
§ NRC No. 24032.
Expe imen al. Single c ys als we e g own by slow
e apo a ion o a sa u a ed solu ion in benzene a oom
empe a u e. C ys al 0.3 × 0.3 x 0.3 mm, moun ed
pa allel o i s long axis (b) and aligned o place his
along he ins umen (0 axis. Picke PDP8E ou -ci cle
di ac ome e a he Na ional Resea ch Council,
Canada. G aphi e-monoch oma ized Mo Kc adia ion,
0/20 scan echnique, line p o ile analysis (G an &
Gabe, 1978), 20 < 60 °, 1167 unique e lec ions wi h
-15 < h < 15, 0 < k < 6, 0 < l < 9; 1037 wi h /ne >
2.5 (Ine ) based on coun ing s a is ics. In ensi ies o
measu ed di ec -beam pola iza ion (Le Page, Gabe &
Cal e , 1979) and Lo en z e ec s. Abso p ion co ec-
ions no applied. Uni -cell pa ame e s om he
leas -squa es e inemen o he se ing angles o 40
e lec ions wi h 20 > 40 °. S uc u e sol ed by di ec
me hods wi h MULTAN (Ge main, Main & Wool son,
1971). E alues la ge han 1.5 used o phase
gene a ion; solu ion om he se ha ing he highes
combined igu e o me i . The E map e ealed he 17
non-hyd ogen a oms. All 14 H a oms loca ed om he
AF map. Full-ma ix e inemen was comple ed wi h
aniso opic empe a u e ac o s o non-hyd ogen
a oms and iso opic o H a oms. Final R(F)= 0.061
and Rw(F) = 0.053 o obse ed e lec ions; R = 0.074
and R w = 0.053 o all e lec ions; w = 1/a2(Fo) based
on coun ing s a is ics; goodness o i 2.6. The inal
di e ence syn hesis showed no peaks abo e 0.3 e A-3;
0108-2701/85/020280-03501.50 © 1985 In e na ional Union o C ys allog aphy