Synthesis and structure determination of 3β-hydroxyandrost-5-en-17-one (C19H28O2·CH3OH)

Article abstract of DOI:10.1023/B:JOCC.0000042020.64194.55

3β-Hydroxyandrost-5-en-17-one (C₁₉H₂₈O ₂.CH₃OH) has been prepared for undertaking its crystallographic analysis and to investigate the role of intra- and intermolecular interactions in steroids. The title compound crystallizes in the orthorhombic space group C222₁ with unit cell parameters a = 6.7892(17), b = 12.624(2), and c = 41.136(5) A; V = 3525.7(12) A³ and Z = 8. The three-dimensional structure has been solved by direct methods. The final reliability index for the computed structure is 0.050 for 1088 observed reflections. Ring A exist in chair conformation, Ring B in half-chair conformation, and the Ring C assumes a distorted chair conformation. The five-membered Ring D adopts half-chair conformation. The A/B ring junction is quasi-trans while as B/C and C/D are trans-fused. The oxygen atom of the solvent molecule (CH₃OH) is involved in O-H···O intermolecular interaction.

Full text of DOI:10.1023/B:JOCC.0000042020.64194.55

Journal of Chemical Crystallography, Vol. 34, No. 8, August 2004 (ꢀC 2004)
Synthesis and structure determination
of 3β-hydroxyandrost-5-en-17-one (C19H28O2·CH3OH)
Rajnikant Verma,(1),∗ Dinesh Jasrotia,(1) Anshu Sawhney,(1) Mousmi Bhat,(1)
and B.D. Gupta(2)
Received May 3, 2004
3β-Hydroxyandrost-5-en-17-one(C19H28O2.CH3OH)hasbeenpreparedforundertakingits
crystallographic analysis and to investigate the role of intra- and intermolecular interactions
in steroids. The title compound crystallizes in the orthorhombic space group C2221 with unit
3
˚
˚
cell parameters a = 6.7892(17), b = 12.624(2), and c = 41.136(5) A; V = 3525.7(12) A
and Z = 8. The three-dimensional structure has been solved by direct methods. The final
reliability index for the computed structure is 0.050 for 1088 observed reflections. Ring A
exist in chair conformation, Ring B in half-chair conformation, and the Ring C assumes a
distorted chair conformation. The five-membered Ring D adopts half-chair conformation.
The A/B ring junction is quasi-trans while as B/C and C/D are trans-fused. The oxygen
atom of the solvent molecule (CH3OH) is involved in O H· · ·O intermolecular interaction.
KEY WORDS: Crystal structure; direct methods; conformation; quasi-trans; trans-fused.
Introduction
and may also be a blood thinner and help protect
against heart diseases.10
Steroids are known to have multifaceted
As a part of our ongoing work on the prepara-
tion of X-ray diffraction quality single crystals of
some steroids and their three-dimensional struc-
ture analyses,11−17 the title compound has been
prepared for its crystallographic analysis and also
to understand the role of intra- and intermolecular
interactions in molecules of this kind.
biological activities.1−4 3β-Hydroxyandrost-5-
en-17-one, commonly known as the dehy-
droepiandrosterone, is a natural steroid produced
in the adrenal glands, testes, and brain. After be-
ing secreted in the adrenal glands, it circulates in
the blood stream and is converted as needed into
other hormones. It is considered as a possible an-
tiaging hormone5,6 and is found to lower fat mass
without reducing total body weight.7,8 Some re-
ports suggest that it might reduce the risk of heart
disease, perhaps by lowering cholesterol levels,9
Experimental
16-Dehydropregnenolone acetate (I) is dis-
solved in ethanol and anhydrous pyridine and hy-
droxylamine hydrochloride is added to it. The
mixture is refluxed on a water bath for 30 min,
cooled, filtered, and dried to yield its oxime. Treat-
ment of the oxime with a Lewis acid (phospho-
rous oxychloride in anhydrous pyridine at −5◦C)
induces a Beckmann rearrangement providing
(1) Condensed Matter Physics Group, Post Graduate Department of
Physics, University of Jammu, Jammu Tawi 180 006, India.
(2) Natural Products Chemistry Division, Regional Research
Laboratory (CSIR), Jammu Tawi, India.
∗ To whom correspondence should be addressed; e-mail:
rkantverma@rediffmail.com.
523
ꢀ
C
1074-1542/04/0800-0523/0 2004 Springer Science+Business Media, Inc.

524
Verma, Jasrotia, Sawhney, Bhat, and Gupta
Table 1. Crystal Data and Structure Refinement Details
an enamide, which on hydrolysis yields 3β-
hydroxyandrost-5-en-17-one (III). Solvent loss
technique was then employed for the growth
of transparent plate-shaped crystals of 3β-
hydroxyandrost-5-en-17-one using methanol as
the solvent system. The chemical structure of the
title compound was established on the basis of IR,
UV, NMR, and mass spectral studies.18
Crystal description
CCDC reference no.
Empirical formula
Transparent rectangular plates
CCDC 216629
C19H28O2·CH3OH
Molecular weight
320.46
Crystal system, space group
Unit cell dimensions
Orthorhombic, C2221
a = 6.7892(17), b = 12.624(2),
˚
c = 41.136(5)A
3
˚
Volume
3525.7(12) A
Z, calculated density
Radiation wavelength (λ)
F(000)
8, 1.207 Mg/m3
˚
MoKα, 0.71073 A
1408
Crystal size
θ range for data collection
Limiting indices
0.30 × 0.30 × 0.20 mm
3.23–24.97◦
0 ≤ h ≤ 8, −4 ≤ k ≤ 14,
−12 ≤ l ≤ 48
Reflections collected/unique
Data/restraints/parameters
Goodness-of-fit on F2
Final R factor
1801/1753
1753/0/208
0.968
R1 = 0.050, wR2 = 0.152
Largest diff. peak and hole
−0.20 < ꢀρ < 0.27 e A−3
of the molecule, thermal ellipsoids drawn at 50%
probability level, with atomic numbering scheme
is shown in Fig. 1.22
Three-dimensional intensity data of a plate-
shaped crystal (0.30 × 0.30 × 0.20 mm) of 3β-
hydroxyandrost-5-en-17-one were collected on an
Enraf-Nonius CAD4 diffractometer (MoKα radi-
The observed bond distances and angles
are in good agreement with the correspond-
ing values obtained in case of 5-ene-steroidal
structures.23−30 In ring A the bond distance
˚
ation, λ = 0.71073 A, ω/2θ scan mode). A total of
1753reflectionswerefoundtobeunique(0 ≤ h ≤
8, −4 ≤ k ≤ 14, −12 ≤ l ≤ 48) and 1088 reflec-
tions were considered as observed [Fo > 4σ(Fo)].
The reflection data were corrected for Lorentz and
Polarization effects.
˚
C2 C3 (1.509(8) A) is smaller than the standard
˚
value (1.533 A).
Ring A has a chair conformation (asymme-
try parameters ꢀCs (C2) = 4.06, ꢀC2 (C2 C3) =
2.05).3 Ring B adopts a half-chair conformation
(asymmetry parameter ꢀC2 (C5 C6) = 2.26).
Ring C exists in distorted chair conformation
(asymmetry parameter ꢀCs (C9) = 1.58 and
ꢀC2 (C8 C9) = 7.85). Ring D occurs in half-
chair conformation (asymmetry parameter ꢀC2
(C13 C14) = 3.30).
The structure has been determined by direct
methods using SHELXS86.19 Isotropic refine-
ment of the structure by least-squares methods us-
ing SHELXL9320 was followed by anisotropic re-
finement of all the non-hydrogen atoms. The final
refinement cycle converged R to 0.050. The resid-
ual electron density in the final diffe−re3nce Fourier
˚
In case of Rings A and B, the atomic devia-
tions in the individual atoms make the methyl car-
bon C19 to deviate significantly above the mean
plane of Rings A and B (deviation being 1.665(5)
map ranges from 0.27 to −0.20 e A . Structural
calculations were obtained from the PC-version
of PARST.21 The crystallographic data are listed
in Table 1.
˚
˚
A), while maximum deviation of 1.750(6) A has
been observed for C18 from the mean plane of
Rings C and D. Ring junction A/B is quasi-trans
while B/C and C/D are trans-fused.
Results and discussion
Bond distances and angles for non-hydrogen
atoms are listed in Table 2. Precise supplementary
data is presented in Tables 1S–5S. A general view
Figure 2 illustrates unit cell molecular pack-
ing (thermal ellipsoids drawn at 10% probability

3β-hydroxyandrost-5-en-17-one
525
◦
˚
Table2. BondDistances(A)andBondAngles( )forNon-Hydrogen
Atoms (e.s.d.s are Given in Parentheses)
C1 C10
C2 C3
C3 C4
C5 C6
C6 C7
C8 C14
C9 C11
C10 C19
C12 C13
C13 C14
C14 C15
C16 C17
1.537(7)
1.508(7)
1.524(7)
1.304(7)
1.509(7)
1.516(6)
1.537(6)
1.544(7)
1.519(7)
1.527(7)
1.523(6)
1.497(8)
1.484(13)
115.5(4)
109.7(4)
110.0(4)
121.4(4)
115.8(4)
113.4(4)
110.6(3)
113.0(4)
112.1(3)
109.7(4)
108.9(4)
111.6(4)
109.3(3)
108.5(4)
112.2(4)
114.1(4)
119.1(4)
102.6(4)
125.7(5)
108.1(4)
C1 C2
C3 O1
C4 C5
C5 C10
C7 C8
1.539(7)
1.444(5)
1.517(6)
1.530(7)
1.522(6)
1.552(6)
1.544(6)
1.542(6)
1.525(6)
1.542(7)
1.546(7)
1.218(5)
C8 C9
C9 C10
C11 C12
C13 C17
C13 C18
C15 C16
C17 O2
O3 C20
C10 C1 C2
O1 C3 C2
C2 C3 C4
C6 C5 C4
C4 C5 C10
C6 C7 C8
C14 C8 C9
C11 C9 C8
C8 C9 C10
C1 C10 C19
C1 C10 C9
C19 C10 C9
C13 C12 C11
C12 C13 C14
C12 C13 C18
C14 C13 C18
C8 C14 C15
C14 C15 C16
O2 C17 C16
C16 C17 C13
C3 C2 C1
O1 C3 C4
C5 C4 C3
C6 C5 C10
C5 C6 C7
C14 C8 C7
C7 C8 C9
C11 C9 C10
C1 C10 C5
C5 C10 C19
C5 C10 C9
C9 C11 C12
C12 C13 C17 116.4(4)
C17 C13 C14 99.2(4)
C17 C13 C18 106.0(4)
C8 C14 C13 113.3(4)
C13 C14 C15 104.8(4)
C17 C16 C15 106.0(4)
119.7(4)
110.8(4)
113.0(4)
122.8(4)
125.0(5)
112.0(4)
108.6(4)
113.4(3)
108.3(4)
108.1(4)
110.1(4)
114.1(4)
Fig. 2. Unit cell molecular packing (thermal ellipsoids drawn
at 10% probability level).
Molecules are held head-to-head forming a he-
lix along the bc plane. The oxygen atom O3 of the
solvent molecule (methanol) is partly responsible
for providing stability to the structure by making
an intermolecular O H· · ·O contact with O1 of
the steroid nucleus (Fig. 3), while the atom O2
acts as a bifurcated acceptor forming intermolec-
ular hydrogen bonds with C14 and C16.31 The
values of three intermolecular contacts, with av-
O2 C17 C13
126.2(5)
˚
erage H· · ·A distance of 2.47 A, are in agreement
level) with extracellular molecules included to
show two hydrogen-bonded chains. Whenever
hydrogen-bonding network of this kind occurs,
their component molecules are often screw re-
lated, with the helices forming a cell axis.
with the theory and predictions made for weak
hydrogen bonds32 and these bonds have a greater
contribution to packing forces than van der Waals
attractions. Thegeometryofintra-andintermolec-
ular O H· · ·O and C H· · ·O hydrogen bonds are
presented below.
d[H· · ·A
D[ X· · ·A θ[D H· · ·A
(◦)]
˚
˚
X
H· · ·A
(A)]
(A)]
O1 H1. . . O3
1.99(1)
2.65(5)
2.70(5)
2.06(1)
2.76(1)
3.27(9)
3.51(8)
2.76(1)
157.4(2)
122.3(5)
140.4(4)
143.2(1)
C16 H16B. . . O2a
C14 H14. . . O2a
O3 H3A. . . O1b
Fig. 1. General view of the molecule, thermal ellipsoids
drawn at 50% probability level, indicating atomic numbering
scheme.
aSymmetry code: x − 1/2, −y + 1/2, −z + 1.
bSymmetry code: −x − 1, y, −z + 1/2.

526
Verma, Jasrotia, Sawhney, Bhat, and Gupta
Supplementary data
˚
Table 1S.Atomic Coordinates (A) and equivalent isotropic thermal
parameters for Hydrogen Atoms (e.s.d.’s are Given in Parentheses)
Atom
X
Y
Z
OH1
OH3
H1A
H1B
H2A
H2B
H3
H4A
H4B
H6
H7A
H7B
H8
H9
−0.2737(1)
−0.6111(1)
−0.0517(1)
0.1518(1)
0.1343(1)
−0.0550(1)
−0.2347(1)
0.1087(1)
−0.0933(1)
−0.0480(9)
−0.0308(1)
0.1346(1)
0.3655(1)
0.0476(1)
0.4383(1)
0.2492(1)
0.2018(1)
0.4186(1)
0.1331(1)
0.2129(1)
0.4318(1)
0.5047(1)
0.2810(1)
0.6643(1)
0.6658(1)
0.7047(1)
0.4580(1)
0.4461(1)
0.3718(1)
−0.5764(1)
−0.3672(1)
−0.5564(1)
−0.0170(1)
0.0455(1)
−0.0368(1)
−0.0943(1)
−0.0912(1)
−0.1468(1)
0.0096(1)
0.1018(1)
0.1604(1)
0.2900(4)
0.2937(1)
0.3580(1)
0.2324(1)
0.0968(1)
0.0235(1)
−0.0402(1)
0.0667(1)
0.0231(1)
0.2402(1)
0.4134(1)
0.3881(1)
0.3925(1)
0.3847(1)
0.2602(1)
0.1617(1)
0.1457(1)
0.0062(1)
0.1238(1)
0.0316(1)
0.2101(1)
0.2101(1)
0.2101(1)
0.2659(1)
0.2541(1)
0.3664(1)
0.3638(1)
0.3068(1)
0.3207(1)
0.3150(1)
0.2879(1)
0.2921(1)
0.3311(13)
0.3914(1)
0.3736(1)
0.3833(1)
0.3994(1)
0.4034(1)
0.4131(1)
0.4590(1)
0.4600(1)
0.4399(1)
0.4355(1)
0.4250(1)
0.4784(1)
0.4883(1)
0.4360(1)
0.4137(1)
0.4491(1)
0.3530(1)
0.3409(1)
0.3185(1)
0.2320(1)
0.2481(1)
0.2699(1)
H11A
H11B
H12A
H12B
H14
H15A
H15B
H16A
H16B
H18A
H18B
H18C
H19A
H19B
H19C
H20A
H20B
H20C
Table2S.AnisotropicThermalParametersofNon-HydrogenAtoms
(e.s.d.’s are Given in Parentheses)
Atom
U11
U22
U33
U23
U13
U12
O1
O2
O3
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
0.061(2) 0.098(3) 0.045(2) −0.013(2) −0.015(2) −0.007(2)
0.074(2) 0.078(3) 0.040(2) −0.006(2) −0.003(2) −0.001(2)
0.082(5) 0.128(6) 0.088(5) 0.001(1) −0.017(5) 0.001(2)
0.070(4) 0.049(3) 0.037(2) 0.002(2) −0.002(3) −0.004(3)
0.074(4) 0.060(3) 0.033(2) −0.002(2) 0.003(3) −0.006(3)
0.043(3) 0.081(4) 0.041(3) −0.010(3) 0.003(2) −0.002(3)
0.061(3) 0.065(3) 0.033(2) 0.002(2) −0.008(2) 0.018(3)
0.044(3) 0.057(3) 0.031(2) 0.003(2) 0.001(2) 0.007(3)
0.065(3) 0.048(3) 0.050(3) 0.005(2) −0.015(3) 0.022(3)
0.056(3) 0.051(3) 0.043(3) −0.001(2) −0.014(2) 0.013(3)
0.036(2) 0.044(3) 0.033(2) 0.001(2) −0.001(2) 0.006(2)
0.032(2) 0.035(2) 0.041(2) 0.001(2) −0.001(2) 0.002(2)
0.044(3) 0.042(3) 0.034(2) −0.001(2) 0.007(2) 0.011(2)
0.054(3) 0.041(3) 0.031(2) 0.006(2) −0.002(2) −0.002(2)
0.066(3) 0.047(3) 0.033(2) 0.008(2) −0.005(3) 0.003(3)
0.043(3) 0.048(3) 0.032(2) −0.001(2) −0.002(2) 0.001(2)
0.041(3) 0.040(2) 0.036(2) −0.004(2) 0.001(2) −0.003(2)
0.058(3) 0.048(3) 0.048(3) −0.008(2) 0.002(3) 0.001(3)
0.060(3) 0.061(3) 0.055(3) −0.014(3) 0.001(3) −0.014(3)
0.049(3) 0.060(3) 0.034(3) −0.006(2) −0.006(2) −0.010(3)
0.043(3) 0.075(4) 0.053(3) −0.011(3) −0.005(2) 0.004(3)
0.050(4) 0.062(3) 0.044(3) −0.004(2) 0.006(3) 0.010(3)
0.082(7) 0.162(12) 0.091(8) 0.001(2) −0.015(2) 0.001(1)
Fig. 3. Hydrogen bonding network between O3 of the alcohol
and O1 attached to the steroid nucleus.
Acknowledgments
The corresponding author (Rajnikant) is
thankful to the Council of Scientific & Industrial
Research, New Delhi, for the financial support un-
der Project No. 03 (0927)/ 01/EMR-II.

3β-hydroxyandrost-5-en-17-one
527
Table 3S.Torsion Angles (◦) for Non-Hydrogen Atoms (e.s.d.’s are
Table 5S.Dihedral Angles (◦)
Given in Parentheses)
Between Planes
C10 C1 C2 C3
C2 C1 C10 C5
C2 C1 C10 C9
C2 C1 C10 C19
C1 C2 C3 C4
C1 C2 C3 O1
C2 C3 C4 C5
O1 C3 C4 C5
C3 C4 C5 C6
C3 C4 C5 C10
C4 C5 C6 C7
C10 C5 C6 C7
C4 C5 C10 C1
C4 C5 C10 C9
C4 C5 C10 C19
C6 C5 C10 C1
C6 C5 C10 C9
−57.3(6)
49.9(6)
169.7(5)
−67.9(5)
57.0(6)
179.2(4)
−55.2(5)
−176.7(4)
−130.1(6)
51.2(6)
C8 C9 C10 C1
C8 C9 C10 C5
C8 C9 C10 C19
C11 C9 C10 C1
−165.8(4)
−47.2(5)
73.0(5)
Plane–plane
Angle (e.s.d.)
1–2
1–3
1–4
2–3
2–4
3–4
20.1(2)
10.9(1)
18.9(2)
10.2(2)
5.5(2)
64.8(5)
C11 C9 C10 C5 −176.6(4)
C11 C9 C10 C19 −56.4(5)
C8 C9 C11 C12
47.3(5)
C10 C9 C11 C12 176.3(4)
C9 C11 C12 C13 −54.5(6)
C11 C12 C13 C14 60.0(5)
C11 C12 C13 C17 170.6(4)
C11 C12 C13 C18 −67.0(5)
C12 C13 C14 C8 −62.7(5)
C12 C13 C14 C15 165.9(4)
C17 C13 C14 C8 175.4(4)
C17 C13 C14 C15 44.0(5)
7.9(2)
−177.3(5)
1.4(9)
−46.3(5)
−165.3(4)
72.5(5)
135.0(5)
16.0(7)
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C18 C13 C14 C8
63.2(5)
C6 C5 C10 C19 −106.2(6)
C18 C13 C14 C15 −68.2(5)
C5 C6 C7 C8
C6 C7 C8 C9
C6 C7 C8 C14
C7 C8 C9 C10
C7 C8 C9 C11
12.8(8)
−42.3(5)
−164.7(4)
61.3(5)
C12 C13 C17 C16 −150.3(5)
203.
C12 C13 C17 O2
29.9(8)
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C14 C13 C17 C16 −34.3(5)
C14 C13 C17 O2 145.9(6)
C18 C13 C17 C16 84.2(5)
C18 C13 C17 O2 −95.6(7)
C8 C14 C15 C16 −165.4(4)
C13 C14 C15 C16 −37.4(5)
C14 C15 C16 C17 15.2(6)
C15 C16 C17 C13 12.2(6)
C15 C16 C17 O2 −168.0(6)
−169.1(4)
C14 C8 C9 C10 −175.5(4)
C14 C8 C9 C11
C7 C8 C14 C13
C7 C8 C14 C15
C9 C8 C14 C13
C9 C8 C14 C15
−45.9(5)
175.9(4)
−60.1(6)
54.7(5)
178.6(4)
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Table 4S.Least-Squares Planes and Dihedral Angles (◦) Between
Various Planes (e.s.d.’s are Given in Parentheses)
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necol. 1993, 169, 1536.
˚
˚
Deviation (A)
Atom
Deviation (A)
Atom
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11. Rajnikant; Gupta, V.K.; Goswami, K.N.; Magotra, D.K.;
Bhutani, K.K.; Mol. Mater. 2000, 12, 101.
12. Rajnikant; Gupta, V.K.; Firoz, J.; Shafiullah; Gupta, R. Crystal-
logr. Rep. 2000, 5, 857.
Plane 1 equation of the plane: 0.8375(1)X − 0.1132(2) Y − 0.5345(2)
Z − 7.085(3) = 0
C1
C2
C3
C4
C5
−0.243(7)
C10
O1a
C6a
C9a
C19a
0.169(6)
0.283(5)
0.268(7)
−0.209(6)
0.261(6)
−0.163(5)
−0.749(7)
−0.624(5)
1.692(6)
13. Rajnikant; Gupta, V.K.; Firoz, J.; Shafiullah; Gupta, R. Cryst.
Res. Technol. 2001, 36, 215.
Plane 2 equation of the plane: 0.8775(1)X − 0.2172(3) Y − 0.4275(2)
Z − 5.198(3) = 0
14. Rajnikant; Gupta, V.K.; Firoz, J.; Shafiullah; Gupta, R. Cryst.
Res. Technol. 2001, 36, 471.
15. Rajnikant; Gupta, V.K.; Khan, E.H.; Safi, S.; Hashmi, S.;
Shafiullah; Varghese, B.; Dinesh, Crystallogr. Rep. 2001, 46,
963.
16. Rajnikant; Gupta, V.K.; Khan, E.H.; Shafi, S.; Hashmi, S.;
Shafiullah; Varghese, B.; Dinesh Cryst. Res. Technol. 2001, 36,
1281.
C5
C6
C7
C8
C9
C10
0.049(5)
−0.106(7)
−0.156(6)
0.294(5)
C1a
−0.728(7)
0.150(6)
C4a
C11a
C14a
C19a
−0.148(6)
−0.109(6)
1.640(6)
−0.313(5)
0.168(6)
Plane 3 equation of the plane: 0.8964(1)X − 0.0407(2) Y − 0.4414(2)
17. Rajnikant; Dinesh; Anshu; Mousmi. Cryst. Res. Technol. 2004,
Z − 5.787(4) = 0
39(4), 353.
C8
0.197(5)
−0.151(5)
0.179(6)
C7a
−0.410(6)
0.431(6)
−0.019(6)
−0.345(6)
1.752(6)
18. Gupta, B.D. Private communication, Regional Research Labo-
ratory, Jammu Tawi, India, 2003.
19. Sheldrick, G.M. SHELXS86, Program for Crystal Structure
Determination; University of Gottingen: Fedral Republic of
Germany, 1986.
20. Sheldrick, G.M. SHELXL93, Program for Refinement of Crystal
Structures; University of Gottingen: Germany, 1993.
21. Nardelli, M. Comput. Chem. 1983, 7, 95.
22. Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659.
23. Griffin, J.F.; Duax, W.L.; Weeks, G.M. Atlas of Steroid Struc-
ture; Plenum: New York, 1984; Vol. 2, p. 21.
24. Kennedy, A.R.; Pitt, A.R.; Suckling, C.J.; Suckling, K.E.;
Thomas, M. Acta Cryst. 1999, C55, 1570.
C9
C10a
C15a
C17a
C18a
C11
C12
C13
C14
−0.313(7)
0.221(5)
−0.292(6)
Plane 4 equation of the plane: 0.9180(1)X − 0.1553(3) Y − 0.3649(3)
Z − 4.051(6) = 0
C13
C14
C15
C16
C17
0.216(5)
−0.274(6)
0.197(6)
0.011(7)
−0.164(6)
C8a
0.056(5)
−0.492(7)
1.749(6)
−0.539(5)
C12a
C18a
O2a
aAtoms not included in plane calculation.

528
Verma, Jasrotia, Sawhney, Bhat, and Gupta
25. Gupta, V.K.; Rajnikant; Goswami, K.N.; Bhutani, K.K. Cryst.
Res. Technol. 1994, 29, 77.
26. Gupta, V.K.; Goswami, K.N.; Bhutani, K.K.; Vaid, R.M. Mol.
Mater. 1994, 4, 303.
29. Rajnikant; Gupta, V.K.; Firoz, J.; Shafiullah; Gupta, R. Cryst.
Res. Technol. 2001, 2, 215.
30. Rajnikant; Gupta, V.K.; Firoz, J.; Shafiullah; Gupta, R. Cryst.
Res. Technol. 2001, 36, 471.
27. Gupta, V.K., Rajnikant; Goswami, K.N.; Mazumdar, S.K.;
Bhutani, K.K. Acta Cryst. 1994, C50, 798.
28. Singh, A.;Gupta, V.K.;Goswami, K.N.;Rajnikant;Gupta, B.D.;
Banerjee, S.K. Mol. Mater. 1996, 6, 53.
31. Steiner, T. Cryst. Rev. 1995, 6, 1.
32. Desiraju, G.R.; Steiner, T. The Weak Hydrogen Bond in Struc-
tural Chemistry and Biology, IUCr; Oxford Press, U.K., 1999,
P. 48.