Two androst-5-ene derivatives: 16-[4-(3-chloropropoxy)-3-methoxybenzylidene]-17-oxoandrost-5-en-3 beta-ol and 16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3 beta-pyrrolidinoandrost-5-en-17 beta-ol monohydrate.

Article abstract of DOI:10.1107/S0108270103025605

In the steroidal nucleus of 16-[4-(3-chloropropoxy)-3-methoxybenzylidene]-17-oxoandrost-5-en-3 beta-ol, C(30)H(29)ClO(4), (I), the outer two six-membered rings are in chair conformations, while the five-membered ring and the central six-membered ring of the steroidal nucleus adopt half-chair and envelope conformations, respectively. In 16-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)benzylidene]-3 beta-pyrrolidinoandrost-5-en-17 beta-ol monohydrate, C(37)H(54)N(2)O(3).H(2)O, (II), one C atom of one of the outer six-membered rings of the steroid nucleus and the four C atoms of the ethoxypyrrolidine ring are disordered over two sites. The five-membered ring, and the central and one of the outer six-membered rings of the steroidal nucleus exhibit distorted half-chair, chair and envelope conformations, respectively. In (I), intermolecular O-H...O hydrogen bonds link the molecules into chains via a co-operative O-H...O-H...O-H pattern. In (II), intermolecular O-H...O and O-H...N hydrogen bonds link the steroid and water molecules alternately into extended chains.

Full text of DOI:10.1107/S0108270103025605

organic compounds
Acta Crystallographica Section C
Crystal Structure
rolidin-1-ylethoxy)benzylidene]-3ꢀ-pyrrolidinoandrost-5-en-
1
7ꢀ-ol monohydrate, (II), have been carried out to study the
Communications
in¯uence of different functionalities on the steroid skeleton, in
particular substituents at the C3, C16 and C17 positions. This
study extends ongoing investigations into a series of similar
synthetic androstene derivatives (Thamotharan et al., 2002,
and references therein; Hema et al., 2003).
ISSN 0108-2701
Two androst-5-ene derivatives:
1
6-[4-(3-chloropropoxy)-3-methoxy-
benzylidene]-17-oxoandrost-5-en-
b-ol and 16-[3-methoxy-4-(2-pyr-
rolidin-1-ylethoxy)benzylidene]-
b-pyrrolidinoandrost-5-en-17b-ol
3
3
monohydrate
a
a
b
S. Thamotharan, V. Parthasarathi, * Ranju Gupta,
b
b
c
Sheetal Guleria, D. P. Jindal ² and Anthony Linden
Compounds (I) and (II) are androstene steroid derivatives
in which rings A, B and C are essentially rigid, whereas ring D
has a ¯exible conformation with respect to the side chain.
Both compounds have the normal 8ꢀ,9ꢁ,10ꢀ,13ꢀ,14ꢁ con®g-
uration, and the B/C and C/D ring junctions have trans
con®gurations (Figs. 1 and 2). The crystals of (I) are enan-
tiomerically pure and the absolute con®guration of the mol-
ecule has been con®rmed independently by the X-ray
diffraction experiment. In (II), the absence of any signi®cant
anomalous scatterers in the compound prevented the deter-
mination of the absolute con®guration and the enantiomer
used in the re®nement was assigned to correspond with the
known chiral centres in a precursor molecule, which remained
unchanged during the synthesis of (II).
a
Department of Physics, Bharathidasan University, Tiruchirappalli 620 024, India,
b
University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh
c
1
60 014, India, and Institute of Organic Chemistry, University of Z uÈ rich,
Winterthurerstrasse 190, CH-8057 Z uÈ rich, Switzerland
Correspondence e-mail: vpsarati@yahoo.com
Received 3 November 2003
Accepted 5 November 2003
Online 13 December 2003
In the steroidal nucleus of 16-[4-(3-chloropropoxy)-3-
methoxybenzylidene]-17-oxoandrost-5-en-3ꢀ-ol, C H ClO ,
(
tions, while the ®ve-membered ring and the central six-
membered ring of the steroidal nucleus adopt half-chair and
envelope conformations, respectively. In 16-[3-methoxy-4-(2-
pyrrolidin-1-ylethoxy)benzylidene]-3ꢀ-pyrrolidinoandrost-5-
en-17ꢀ-ol monohydrate, C H N O ÁH O, (II), one C atom of
3
0
29
4
I), the outer two six-membered rings are in chair conforma-
In compound (I) (Fig. 1), rings A and C are in chair
conformations, as shown by the Cremer & Pople (1975)
Ê
puckering parameters [ring A: Q = 0.550 (3) A, q2
ꢀ
=
Ê
Ê
ꢀ
3
7
54
2
3
2
0.078 (3) A, q = 0.545 (3) A, ꢂ = 7.9 (3) and ' = 107 (2) for
3
2
Ê
the atom sequence C1±C5/C10; ring C: Q = 0.577 (3) A, q =
2
one of the outer six-membered rings of the steroid nucleus and
the four C atoms of the ethoxypyrrolidine ring are disordered
over two sites. The ®ve-membered ring, and the central and
one of the outer six-membered rings of the steroidal nucleus
exhibit distorted half-chair, chair and envelope conformations,
respectively. In (I), intermolecular OÐHÁ Á ÁO hydrogen bonds
link the molecules into chains via a co-operative OÐHÁ Á ÁOÐ
HÁ Á ÁOÐH pattern. In (II), intermolecular OÐHÁ Á ÁO and OÐ
HÁ Á ÁN hydrogen bonds link the steroid and water molecules
alternately into extended chains.
Ê
Ê
ꢀ
ꢀ
0.053 (3) A, q = 0.575 (3) A, ꢂ = 5.2 (3) and ' = 269 (3) for
3
2
the atom sequence C8/C9/C11±C14]. Thus, the presence of a
hydroxy group at C3 has not disturbed the usual chair
conformation of ring A of the steroid nucleus. The C3ÐO3
bond is oriented equatorially and (� )synclinal to the C3ÐC4
bond. In contrast, it lies (+)antiperiplanar to the C3ÐC4 bond
in a related structure reported from our laboratory (Hema et
2
2
al., 2003). In ring B, the C5 C6 (Csp ÐCsp ) distance of
Ê
1.324 (3) A con®rms the localization of a double bond at this
position. This double bond imposes an 8ꢀ,9ꢁ-half-chair
conformation on ring B, with puckering parameters of Q =
Ê
Ê
Ê
ꢀ
Comment
0.468 (3) A, q = 0.365 (3) A, q = 0.292 (3) A, ꢂ = 51.5 (3)
2
3
ꢀ
and ' = 211.4 (4) for the atom sequence C5±C10. Similar
observations on the conformation of ring B in related struc-
tures have been reported by Caira et al. (1995), Hema et al.
2002), Vasuki et al. (2002) and Thamotharan et al. (2002).
Ring D has a 14ꢁ-envelope conformation, with a pseudo-
2
It is well known that minor changes in the basic composition of
steroids signi®cantly alter their chemical and biological
activities (Duax & Norton, 1975). The present crystallographic
analyses of 16-[4-(3-chloropropoxy)-3-methoxybenzylidene]-
(
1
7-oxoandrost-5-en-3ꢀ-ol, (I), and 16-[3-methoxy-4-(2-pyr-
ꢀ
rotation angle of 12.4 (2) and a maximum torsion angle of
ꢀ
²
Deceased.
42.5 (1) (Rao et al., 1981) for the atom sequence C13±C17.
Acta Cryst. (2004). C60, o75±o78
DOI: 10.1107/S0108270103025605
# 2004 International Union of Crystallography o75

organic compounds
Ê
ꢀ ꢀ
.574 (3) A, ꢂ = 8.7 (3) and ' = 268.4 (18) for the atom
2
0
sequence C8/C9/C11±C14]. Ring D of the steroid exhibits an
envelope conformation, as is evident from the pseudorotation
ꢀ
ꢀ
angle of 345.0 (2) and maximum torsion angle of 45.4 (1) for
the atom sequence C13±C17.
In (II), the four ring C atoms of the ethoxypyrrolidine ring
are disordered over two almost equally occupied conforma-
tions. Both disordered components exhibit envelope confor-
mations, as can be seen from the pseudorotation angles of
ꢀ
3
44.8 (8) and 346.8 (8) and maximum torsion angles of
ꢀ
4
C32A/C33A/C34A and N30/C31B/C32B/C33B/C34B, respec-
4.2 (6) and 44.3 (5) for the atom sequences N30/C31A/
tively. The pyrrolidine-ring substituent at C3 has an envelope
ꢀ
conformation, with a pseudorotation angle of 348.0 (3) and a
ꢀ
maximum torsion angle of 42.7 (2) for the atom sequence
N37/C38±C41.
ꢀ
The C17ÐC16ÐC20ÐC21 torsion angles of � 173.5 (2) in
Figure 1
ꢀ
A view of the molecule of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level and H
atoms are shown as small circles of arbitrary radii.
(I) and 179.2 (2) in (II) indicate that the benzylidene moiety
has an E con®guration with respect to the carbonyl or hydroxy
substituted atom, C17. The chloropropoxy group in (I)
projects in a planar zigzag fashion slightly away from the plane
of the methoxybenzylidene ring [C25ÐC24ÐO28ÐC29 =
Ê
Atom C14 is 0.142 (2) A from the plane containing the four
remaining atoms.
ꢀ
6.9 (4) ].
In compound (II) (Fig. 2), atom C4 in ring A of the steroid
nucleus is disordered over two sites, so that ring A adopts two
alternate conformations, with the major conformation existing
in 78.8 (7)% of the molecules. As seen from the puckering
parameters, the major disordered component has a chair
The C19ÐC10Á Á ÁC13ÐC18 pseudo-torsion angle, which
gives a quantitative measure of the molecular twist, is
ꢀ
ꢀ
13.84 (18) in (I) and 11.34 (19) in (II). These values are
comparable with those of related structures with bulky
substitutions at C3 and C16 (Hema et al., 2002; Thamotharan
et al., 2002). The C16ÐC20ÐC21ÐC22 torsion angle of
Ê
Ê
conformation [Q = 0.558 (3) A, q = 0.087 (3) A, q
2
=
3
Ê
ꢀ
ꢀ
ꢀ
ꢀ
0
sequence C1±C4A/C5/C10], while the minor disordered
.551 (3) A, ꢂ = 9.0 (3) and ' = 113 (2) for the atom
160.8 (3) in (I) and 5.7 (4) in (II) indicate that the benzyl-
ꢀ
2
idene moiety has been ¯ipped by almost 180 about the C20Ð
component has a boat conformation distorted towards that of
Ê
C21 bond in (II) with respect to its orientation in (I), thus
bringing the methoxy group to the other side of the molecule.
The A/B/C/D ring systems of both (I) and (II) can be super-
imposed on each other, with a small r.m.s. deviation of the
Ê
a screw-boat [Q = 0.569 (5) A, q2 = 0.556 (6) A, q
=
3
Ê
ꢀ ꢀ
.120 (5) A, ꢂ = 77.8 (5) and ' = 8.8 (3) for the atom
2
0
sequence C1±C4B/C5/C10]. Ring B exhibits a slightly ¯at-
=
Ê
tened half-chair conformation [Q = 0.454 (3) A, q
Ê
2
atoms of 0.084 A.
Ê
Ê
ꢀ
ꢀ
0
for the atom sequence C5±C10], while ring C adopts a chair
.281 (3) A, q = 0.356 (3) A, ꢂ = 38.3 (4) and ' = 208.7 (6)
In (I), the hydroxy substituent on atom C3 forms an inter-
molecular hydrogen bond with hydroxy atom O3 of a
symmetry-related molecule (Table 1). This interaction leads
3
2
Ê
conformation [Q = 0.581 (3) A, q = 0.084 (3) A, q
Ê
=
2
3
Figure 2
A view of the molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. For clarity, all H
atoms of the disordered rings have been omitted. The other H atoms are shown as small circles of arbitrary radii.
ꢁ
o76 S. Thamotharan et al.
C
30
H39ClO
4
and C37
H
54
N
2
O
3
ÁH
2
O
Acta Cryst. (2004). C60, o75±o78

organic compounds
co-operatively to an OÐHÁ Á ÁOÐHÁ Á ÁOÐH pattern, produ-
cing a chain which runs parallel to the [001] direction and has a
graph-set motif of C(2) (Bernstein et al., 1995). As can be seen
from Table 2, the hydroxy substituent on atom C17 in (II)
forms an intermolecular OÐHÁ Á ÁO hydrogen bond with the O
atom of the water molecule. In turn, the water molecule forms
two intermolecular OÐHÁ Á ÁO and one intermolecular OÐ
HÁ Á ÁN hydrogen bonds with the methoxy, ethoxy and
ethoxypyrrolidine O and N atoms, respectively, of a single
adjacent steroid molecule. These three acceptor atoms form a
pocket into which the water molecule is bound. The combi-
nation of all these interactions links the steroid and water
molecules alternately into extended chains which run in the
Re®nement
2
Re®nement on F
2
(Á/ꢅ)max < 0.001
2
Ê
� 3
Áꢆmax = 0.60 e A
R[F > 2ꢅ(F )] = 0.049
wR(F ) = 0.127
2
Ê
� 3
Áꢆmin = � 0.34 e A
S = 1.02
5987 re¯ections
Extinction correction: SHELXL97
(Sheldrick, 1997)
324 parameters
Extinction coef®cient: 0.00078 (19)
Absolute structure: Flack &
Bernardinelli (2000)
Flack parameter = � 0.21 (7)
H atoms treated by a mixture of
independent and constrained
re®nement
2
2
2
w = 1/[ꢅ (F
o
) + (0.0672P)
+ 7.0766P]
where P = (F
2
2
c
o
+ 2F
)/3
Table 1
Hydrogen-bonding geometry ( AÊ , ) for (I).
ꢀ
[101] direction. Binary graph-set motifs (Bernstein et al., 1995)
of C (11), C (12) and C (15) are present for the chain routes
2
2
2
2
2
2
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
through acceptor atoms O37, O25 and N30, respectively. Ring
2
2
2
2
2
i
motifs of R (5), R (7) and R (10) are also formed by the
1
O3ÐH3AÁ Á ÁO3
Symmetry code: (i) � y; x � y � ; z �
0.76 (3)
1.95 (3)
2.710 (2)
177 (3)
various combinations of donor±acceptor interactions between
the water molecule and the single acceptor steroid molecule.
1
3
1
3
1
.
3
Experimental
Compound (II)
To a solution of dehydroepiandrosterone (0.75 g, 2.60 mmol) in
methanol (10 ml), sodium hydroxide pellets (1.5 g) were added
and dissolved. 4-(3-Chloropropoxy)-3-methoxybenzaldehyde (1 g,
Crystal data
�
3
C
37
H
54
N
2
O
3
ÁH
2
O
D
x
= 1.185 Mg m
4.373 mmol) was added dropwise and stirred for 2 h. The completion
M = 592.86
r
Monoclinic, P21
Ê
a = 6.4219 (1) A
Ê
b = 32.4115 (5) A
Mo Kꢁ radiation
Cell parameters from 3313
re¯ections
of the reaction was monitored using thin-layer chromatography. Ice-
cold water was added to the reaction mixture and the precipitate
obtained was ®ltered off, washed, dried and crystallized from acetone
to afford (I) (institution code: DPJ-RG-1150; yield: 1.5 g, 86.7%; m.p.
ꢀ
ꢂ = 2.0±26.0
ꢃ = 0.08 mm
T = 160 (2) K
Ê
ꢀ
� 1
c = 8.0981 (1) A
= 99.6510 (7)
ꢀ
4
1
0
83±485 K). To a stirred suspension of 16-[3-methoxy-4-(2-pyrrolidin-
-ylethoxy)benzylidene]-3-pyrrolidino-3,5-androstadien-17-one (0.5 g,
.871 mmol) in methanol (75 ml), sodium borohydride (1.0 g) was
Ê
3
V = 1661.71 (4) A
Z = 2
Prism, colourless
0.28 Â 0.18 Â 0.15 mm
added in small amounts over a period of 2 h at room temperature.
Stirring was continued for a further 4 h. Excess solvent was removed
under vacuum and the reaction mixture was poured into ice-cold
water (100 ml). The precipitate obtained was ®ltered off, washed with
water, dried and crystallized from methanol±acetone (9:1) to afford
Data collection
Nonius KappaCCD area-detector
diffractometer
' and ! scans with ꢄ offsets
Rint = 0.052
ꢂmax = 26.0
h = � 7 ! 7
k = � 39 ! 39
l = � 9 ! 9
ꢀ
3
3
2
6 139 measured re¯ections
302 independent re¯ections
865 re¯ections with I > 2ꢅ(I)
(II) (institution code: DPJ-RG-1122; yield: 0.38 g, 75.54%; m.p. 469±
472 K).
Re®nement
Compound (I)
2
2
2
2
Re®nement on F
2
o
w = 1/[ꢅ (F ) + (0.0500P)
2
R[F > 2ꢅ(F )] = 0.037
wR(F ) = 0.092
+ 0.1844P]
where P = (F
Crystal data
2
2
2
c
o
+ 2F
)/3
C
M
30
H
39ClO
= 499.09
Trigonal, R3
4
Mo Kꢁ radiation
Cell parameters from 19 304
re¯ections
S = 1.04
3299 re¯ections
451 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
(Á/ꢅ)max < 0.001
Áꢆmax = 0.23 e A
Ê
� 3
r
Ê
� 3
Áꢆmin = � 0.22 e A
Ê
ꢀ
Extinction correction: SHELXL97
(Sheldrick, 1997)
Extinction coef®cient: 0.017 (5)
a = 34.3749 (8) A
Ê
b = 34.3749 (8) A
c = 5.7585 (1) A
Ê
V = 5892.8 (2) A
Z = 9
�
D = 1.266 Mg m
x
ꢂ = 2.0±27.5
ꢃ = 0.18 mm
T = 160 (2) K
� 1
Ê
3
Prism, colourless
0.30 Â 0.12 Â 0.10 mm
3
Table 2
Hydrogen-bonding geometry (A, ) for (II).
Ê
ꢀ
Data collection
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Nonius KappaCCD area-detector
diffractometer
5990 independent re¯ections
5077 re¯ections with I > 2ꢅ(I)
O17ÐH17AÁ Á ÁO1W
0.85 (4)
0.87 (2)
0.88 (2)
0.88 (2)
1.90 (4)
1.95 (2)
1.96 (2)
2.47 (4)
2.748 (3)
2.813 (3)
2.835 (3)
2.987 (3)
172 (3)
169 (4)
170 (4)
118 (3)
'
and ! scans with ꢄ offsets
Absorption correction: multi-scan
SORTAV; Blessing, 1995)
min = 0.909, Tmax = 0.984
9 761 measured re¯ections
R
int = 0.062
i
O1WÐH1WÁ Á ÁN30
ꢀ
ꢂ
max = 27.5
i
O1WÐH2WÁ Á ÁO35
(
T
h = � 44 ! 41
k = � 44 ! 44
l = � 7 ! 7
i
O1WÐH2WÁ Á ÁO27
2
Symmetry code: (i) x � 1; y; 1 ‡ z.
ꢁ
Acta Cryst. (2004). C60, o75±o78
S. Thamotharan et al.
C
30
H
39ClO
4
and C37H
54
N O
2
3
2
ÁH O
o77

organic compounds
For compound (II), atom C4 on ring A of the steroid nucleus is
disordered over two sites. The four ring C atoms of the ethoxy-
pyrrolidine moiety are also disordered over two conformations and
two sets of positions were de®ned for pyrrolidine ring atoms C31±
C34. Constrained re®nement of the site-occupation factors for the
two disordered regions led to values of 0.788 (7) and 0.510 (13),
respectively, for the major conformations. Chemically equivalent
bonds involving the disordered C atoms were constrained to have
similar lengths and the 1,3-distances within each conformation of the
pyrrolidine ring were also restrained to be similar. Neighbouring
disordered atoms within and between each conformation of the
disordered region were also restrained to have similar atomic
displacement parameters. The position of the hydroxy H atom in (I)
was determined from a difference Fourier map and re®ned freely
along with its isotropic displacement parameters. The positions of the
water H atoms in (II) were also determined from a difference Fourier
map and were re®ned along with their isotropic displacement para-
1994); program(s) used to re®ne structure: SHELXL97 (Sheldrick,
1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used
to prepare material for publication: SHELXL97 and PLATON
(Spek, 2003).
RG and SG wish to acknowledge Cipla Ltd, Mumbai, India,
for the generous supply of steroid, and SG thanks the CSIR,
India, for ®nancial assistance.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK1678). Services for accessing these data are
described at the back of the journal.
References
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
Blessing, R. H. (1995). Acta Cryst. A51, 33±38.
Caira, M. R., Guillory, K. J. & Chang, L. (1995). J. Chem. Crystallogr. 25, 393±
400.
Ê
meters, while restraining the OÐH bond length to 0.82 A. The methyl
H atoms in both compounds were constrained to an ideal geometry
Ê
(CÐH = 0.98 A), with Uiso(H) = 1.5Ueq(C), but were allowed to
rotate freely about the CÐC bonds. All remaining H atoms were
Ê
placed in geometrically idealized positions (CÐH = 0.95±1.00 A) and
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354±1358.
Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures, Vol. 1. New
York: Plenum.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837±838.
Flack, H. D. (1983). Acta Cryst. A39, 876±881.
were constrained to ride on their parent atoms. The presence of Cl in
compound (I) permitted the determination of the absolute con®g-
uration of the molecule by re®ning the Flack parameter [� 0.21 (7),
2
982 Friedel pairs; Flack, 1983; Flack & Bernardinelli, 2000]. Due to
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143±1148.
Hema, R., Parthasarathi, V., Thamotharan, S., Dubey, S. & Jindal, D. P. (2002).
Acta Cryst. C58, o421±o422.
Hema, R., Parthasarathi, V., Thamotharan, S., Dubey, S. & Jindal, D. P. (2003).
Acta Cryst. C59, o213±o215.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307±326. New York: Academic Press.
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421±425.
Sheldrick, G. M. (1997). SHELXL97. University of G oÈ ttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
the absence of any signi®cant anomalous scatterers in (II), attempts
to con®rm the absolute structure by re®nement of the Flack para-
meter in the presence of 3177 sets of Friedel equivalents led to an
inconclusive value of 0.0 (8). Therefore, the Friedel pairs were
merged before the ®nal re®nement and the absolute con®guration
was assigned to correspond with the known chiral centres in a
precursor molecule, which remained unchanged during the synthesis
of (II). Re¯ections 112, 012 and 111 in (I), and 021, 011 and 040 in (II)
were partially obscured by the beam stop and were omitted.
For both compounds, data collection: COLLECT (Nonius, 2000);
cell re®nement: DENZO±SMN (Otwinowski & Minor, 1997); data
reduction: DENZO±SMN and SCALEPACK (Otwinowski & Minor,
Thamotharan, S., Parthasarathi, V., Gupta, R., Guleria, S., Jindal, D. P. &
Linden, A. (2002). Acta Cryst. C58, o727±o729.
Vasuki, G., Thamotharan, S., Parthasarathi, V., Ramamurthi, K., Dubey, S. &
Jindal, D. P. (2002). Acta Cryst. C58, o598±o599.
1997); program(s) used to solve structure: SIR92 (Altomare et al.,
ꢁ
o78 S. Thamotharan et al.
C
30
H39ClO
4
and C37
H
54
N
2
O
3
ÁH
2
O
Acta Cryst. (2004). C60, o75±o78