Crystal and molecular structure analysis of 1-Acryloyl-3-methyl-2,6-bis(3, 4,5-trimethoxyphenyl)piperidine-4-one

Article abstract of DOI:10.1080/15421400903291426

The title compound C27H33NO8 crystallizes in the orthorhombic crystal class under the space group Pbca with cell parameters a=13.775(4)A , b=16.389(2)A, c=23.085(6)A, Z=8, and V=5212.6(3)A3. The piperidine ring in the structure adopts a twist boat conform

Full text of DOI:10.1080/15421400903291426

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Crystal and Molecular Structure
Analysis of 1-Acryloyl-3-
methyl-2,6-bis(3,4,5-
trimethoxyphenyl)piperidine-4-
one
C. R. Gnanendra a , B. N. Lakshminarayana b , G. B.
Thippeswamy b , M. A. Sridhar b , Nagaraja Naik a &
J. Shashidhara Prasad b
a Department of Studies in Physics , University of
Mysore , Mysore, India
b Department of Studies in Chemistry , University of
Mysore , Mysore, India
Published online: 17 Dec 2009.
To cite this article: C. R. Gnanendra , B. N. Lakshminarayana , G. B.
Thippeswamy , M. A. Sridhar , Nagaraja Naik & J. Shashidhara Prasad (2009)
Crystal and Molecular Structure Analysis of 1-Acryloyl-3-methyl-2,6-bis(3,4,5-
trimethoxyphenyl)piperidine-4-one, Molecular Crystals and Liquid Crystals, 515:1,
179-189, DOI: 10.1080/15421400903291426
To link to this article: http://dx.doi.org/10.1080/15421400903291426
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Mol. Cryst. Liq. Cryst., Vol. 515, pp. 179–189, 2009
Copyright # Taylor & Francis Group, LLC
ISSN: 1542-1406 print=1563-5287 online
DOI: 10.1080/15421400903291426
Crystal and Molecular Structure Analysis of 1-Acryloyl-
3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one
C. R. Gnanendra1, B. N. Lakshminarayana2,
G. B. Thippeswamy2, M. A. Sridhar2,
Nagaraja Naik1, and J. Shashidhara Prasad2
1Department of Studies in Physics, University of Mysore, Mysore, India
2Department of Studies in Chemistry, University of Mysore,
Mysore, India
The title compound C27H33NO8 crystallizes in the orthorhombic crystal class
˚
under the space group Pbca with cell parameters a ¼ 13.775(4) A, b ¼ 16.389(2)
3
˚
˚
˚
A, c ¼ 23.085(6) A, Z ¼ 8, and V ¼ 5212.6(3) A . The piperidine ring in the structure
adopts a twist boat conformation. The bond lengths and bond angles are in good
agreement with the standard values. The structure exhibits intermolecular hydro-
gen bond of the type C–H ꢀ ꢀ ꢀ O. The synthesized molecule was characterized
by FT-IR, 1H-NMR, MS, and elemental analysis.
Keywords: antifungal and tranquilizers; antimicrobial; piperidone
INTRODUCTION
Piperdines are an important group of compounds in the field of medic-
inal chemistry owing to the fact that these can frequently be recog-
nized in the structure of numerous naturally occurring alkaloid and
synthetic compounds with interesting biological and pharmacological
properties. This has been reviewed by Prostakov and Gaivoronskaya
[1]. A good number of reports are there to prove that the piperidine
derivatives have antimicrobial [2], analgesic [3], local anaesthetic
[4], and anti-fungal activities [5]. Further, the 2,6-substituted
piperdines are useful as tranquilizers and possess hypotensive
activity. In view of the above, 1-acryloyl-3-methyl-1-propionyl-2,6-bis
Address correspondence to Prof. J. Shashidhara Prasad, Department of Studies in
Physics, Manasagangotri, University of Mysore, Mysore 570 006, India. Fax: þ91-821-
2419333. E-mail: jsp@physics.uni-mysore.ac.in
179

180
C. R. Gnanendra et al.
(3,4,5-trimethoxy phenyl)piperidine-4-one was synthesized, and the
crystal structure is reported here.
EXPERIMENTAL
IR spectra were recorded in JASCO FT-IR 4100 spectrophotometer
with KBr only significant absorption levels (reciprocal centimeter)
1
are listed. H-NMR spectra were recorded on Bruker AMX-400 MHz
High Resolution Multinuclear FT-NMR Spectrometer in Dimethyl
Sulfoxide (DMSO) using tetramethyl silane (TMS) as internal stan-
dard. Mass spectra were recorded on a Waters-Q-TOF Ultimaspecto-
photometer. Elemental analysis (C, H, and N) of the synthesized
compound was carried out on Elementar Vario EL III CHN2 analyzer.
The crystallographic measurements were made on DIPLabo Imaging
plate system with graphite monochromated radiation (MoKa).
Synthesis of 1-Acryloyl-3-methyl-2,6-bis (3,4,5-Tri
methoxy Phenyl) Piperidine-4-one
To
a
well-stirred solution of 3-methyl-2,6-bis(3,4,5-trimethoxy
phenyl)piperidine-4-one (5 mmol) and triethylamine (5 mmol) in
30 ml of benzene, 3-chloropropanoyl chloride (5 mmol) in 20 ml
benzene was added dropwise through the addition funnel for about
an hour. The resulting mixture was stirred for about 4 hours under
room condition. After the completion of the reaction the mixture was
quenched in cold water, and the organic layer was extracted into ethyl
acetate, washed with 5% sodium bicarbonate solution and dried over
anhydrous sodium sulphate. This upon evaporation and recrystalliza-
tion in alcohol yields 2,6-bis(3,4,5-trimethoxy phenyl) piperidine-4-
one. Further, the sample was dissolved in ethanol (60 ml), refluxed
for half an hour and allowed to crystallize by slow evaporation to form
the title compound (Scheme 1). The schematic diagram of the molecule
is shown in Figure 1.
IR (KBr) (cmꢁ1): 3184.2, 3076.0, 2996.0, 2888.0, 28321.1 (C–H
=
=
stretching); 1724.9.6 (C O stretching); 1643.9 (N–C O stretching);
1586.4, 1508.8, 1454.5, 1426.6, 1323.4, 1122.2, 1036.1, 915.8, 840.2,
690.2.
1H NMR (d, ppm); 3.11 (t, CH, 2H, C5a, and C3); 2.75 (dd, CH, 1 H, C5b);
=
3.61 (d, CH2, CH, CH2); 2.556 (d, CH, H, CH–C O); 3.66 and 3.78 (2 S,
OCH3, 18H, 6 OCH3 in benzene ring); 5.19 (s, CH, 1H, C2); 5.79 (s, CH,
1H, C6) 6.53 (s Ar-H, 4 H, benzene ring); 1.15(d, CH3, 3H, CH3 at C3).
Mass (m=z): 500.00.
Elemental Analysis: C, 64.892; H, 6.61; N, 2.83; O, 25.53.

Crystal and Molecular Structure Analysis
181
SCHEME 1 The reaction scheme.
CRYSTAL STRUCTURE DETERMINATION
A single crystal of the title compound with dimensions 0.27 ꢂ
0.25 ꢂ 0.21 mm was chosen for X-ray diffraction study. The data were
collected on a DIPLabo Image Plate system equipped with a normal
focus, 3 kW sealed X-ray source (graphite monochromated MoKa).

182
C. R. Gnanendra et al.
The crystal to detector distance was fixed at 120 mm with a detector
area of 441 ꢂ 240 mm2. Thirty six frames of data were collected at room
temperature by the oscillation method. Each exposure of the image
plate was set to a period of 400 s. Successive frames were scanned in
steps of 5ꢃ per minute with an oscillation range of 5ꢃ. Image processing
and data reduction were done using Denzo [6]. The reflections were
merged with Scalepack [7]. All the frames could be indexed using a pri-
mitive orthorhombic lattice. Absorption correction was not applied.
The structure was solved by direct methods using SHELXS-97 [8].
All the non-hydrogen atoms were revealed in the first Fourier map
itself. Full matrix least squares refinement using SHELXL-97 [8] with
isotropic displacement factors for all the non-hydrogen atoms con-
verged the residual to 0.1865. Subsequent refinements were carried
TABLE 1 Crystal Data and Structure Refinement Table
CCDC Deposition Number
Empirical formula
Formula weight
Temperature
Wavelength
Crystal system
Space group
CCDC 725678
27H33NO8
499.54
C
293 (2) K
˚
0.71073 A
Orthorhombic
Pbca
˚
˚
Cell dimensions
a ¼ 13.775(4) A
b ¼ 16.389(2) A
˚
c ¼ 23.085(6) A
3
˚
Volume
5212(2) A
Z
4
Density (calculated)
Absorption coefficient
F000
1.273 Mg=m3
0.094 mmꢁ1
2128
Crystal Size
Theta range for data collection
Index ranges
0.27 ꢂ 0.25 ꢂ 0.21 mm
2.62ꢃ to 25.02ꢃ
ꢁ14 ꢄ h ꢄ 14
ꢁ18 ꢄk ꢄ 17
ꢁ27 ꢄl ꢄ 27
Reflections collected
6343
Independent reflections
Absorption correction
Refinement method
Data=restraints=parameters
Goodness-of-fit on F2
Final R indices [I > 2r(I)]
R indices (all data)
3711 [R(int) ¼ 0.0460]
None
Full-matrix least-squares on F2
3711=0=333
1.079
R1 ¼ 0.0694, wR2 ¼ 0.1704
R1 ¼ 0.1163, wR2 ¼ 0.1984
0.0088(1)
Extinction coefficient
Largest diff. peak and hole
ꢁ3
˚
0.249 and –0.210 eA

Crystal and Molecular Structure Analysis
183
out with anisotropic thermal parameters for non-hydrogen atoms and
isotropic displacement factors for the hydrogen atoms which were
placed at chemically acceptable positions. The residual finally con-
verged to 0.0694. The highest peak and the deepest hole in the final
difference map were 0.249 and ꢁ0.210 eꢁ3, respectively.
TABLE 2 Atomic Coordinates and Equivalent Thermal Parameters
of the Non-hydrogen Atoms
Atom
x
y
z
Ueq
N1
C2
C3
C4
C5
C6
O7
C8
1.3983(2)
1.3485(3)
1.3657(3)
1.4709(4)
1.5239(3)
1.4596(3)
1.5117(3)
1.3247(4)
1.3990(3)
1.4340(2)
1.3584(3)
1.3368(5)
1.2405(3)
1.1823(3)
1.0839(3)
1.0422(3)
1.0996(3)
1.1980(3)
1.02122(2)
1.0584(3)
0.9434(2)
0.9208(3)
1.0529(2)
1.4005(3)
1.1102(3)
1.3989(3)
1.3461(3)
1.2937(3)
1.2970(3)
1.3492(3)
1.3403(2)
1.3888(4)
1.2453(2)
1.1515(4)
1.2454(2)
1.2662(4)
0.2512(2)
0.2800(2)
0.3714(3)
0.3947(3)
0.3555(3)
0.3076(2)
0.4414(3)
0.3984(3)
0.1711(3)
0.14768(2)
0.1091(3)
0.0361(3)
0.2617(2)
0.2879(2)
0.2714(2)
0.2278(2)
0.2033(2)
0.2203(2)
0.29375(2)
0.3431(3)
0.21064(2)
0.1283(3)
0.16092(2)
0.3568(3)
0.1190(3)
0.4411(3)
0.4812(3)
0.4372(2)
0.3526(3)
0.3120(2)
0.56406(2)
0.6128(3)
0.47640(2)
0.5062(3)
0.31231(2)
0.2278(3)
0.36674(1)
0.31336(1)
0.30317(2)
0.31037(2)
0.35940(2)
0.40093(1)
0.27818(2)
0.2448(2)
0.38239(1)
0.42864(1)
0.34193(2)
0.3586(3)
0.31405(1)
0.35969(1)
0.35970(1)
0.31460(1)
0.26857(1)
0.26813(1)
0.40324(1)
0.44871(2)
0.31536(1)
0.33177(2)
0.22555(1)
0.44499(1)
0.18443(1)
0.44670(1)
0.48996(2)
0.53147(1)
0.52949(1)
0.48667(1)
0.49563(1)
0.4545(2)
0.0552(8)
0.0556(1)
0.0688(1)
0.0848(1)
0.0780(1)
0.0603(1)
0.1421(2)
0.1059(1)
0.0615(1)
0.0843(1)
0.0668(1)
0.125(2)
0.0537(1)
0.0554(1)
0.0594(1)
0.0588(1)
0.0591(1)
0.0581(1)
0.0711(9)
0.0794(1)
0.0704(8)
0.0896(1)
0.0753(9)
0.0591(1)
0.0766(1)
0.0673(1)
0.0675(1)
0.0623(1)
0.0620(1)
0.0591(1)
0.0889(1)
0.0996(1)
0.0772(9)
0.0913(16)
0.0731(9)
0.0807(1)
C9
O10
C11
C12
C13
C14
C15
C16
C17
C18
O19
C20
O21
C22
O23
C25
C24
C26
C27
C28
C29
C30
O31
C32
O33
C34
O35
C36
0.57552(1)
0.56022(2)
0.57164(1)
0.58071(2)
ꢀ
ꢁ
P P
Ueq ¼ ð1=3Þ
Uij aꢅi ajꢅ ðai ꢀ ajÞ:
i
j

184
C. R. Gnanendra et al.
RESULTS AND DISCUSSION
The details of crystal data and refinement are given in Table 1. Table 2
gives the list of atomic coordinates and equivalent thermal parameters
of the non-hydrogen atoms. Table 3 gives the list of anisotropic
thermal parameters of the non-hydrogen atoms. The bond lengths
and bond angles of all the non-hydrogen atoms are given in Table 4.
and are in good agreement with the standard values [9]. Figure 2
TABLE 3 Anisotropic Thermal Parameters of the Non-hydrogen Atoms
Atom
U11
U22
U33
U12
U13
U23
N1
C2
C3
C4
C5
C6
O7
C8
0.056(2)
0.060(3)
0.084(4)
0.101(4)
0.068(3)
0.048(3)
0.166(4)
0.148(5)
0.059(3)
0.107(3)
0.068(3)
0.176(6)
0.053(3)
0.056(3)
0.059(3)
0.050(3)
0.055(3)
0.062(3)
0.059(2)
0.083(4)
0.054(2)
0.068(3)
0.064(2)
0.056(3)
0.079(3)
0.078(3)
0.090(3)
0.074(3)
0.062(3)
0.067(3)
0.132(3)
0.148(5)
0.097(3)
0.094(4)
0.083(2)
0.089(4)
0.069(2)
0.069(3)
0.071(3)
0.086(4)
0.097(4)
0.079(3)
0.151(4)
0.097(4)
0.083(3)
0.086(2)
0.073(3)
0.089(4)
0.070(3)
0.072(3)
0.083(3)
0.086(3)
0.086(3)
0.078(3)
0.107(2)
0.097(3)
0.103(2)
0.123(4)
0.118(3)
0.078(3)
0.094(3)
0.077(3)
0.063(3)
0.067(3)
0.081(3)
0.061(3)
0.066(2)
0.069(3)
0.084(2)
0.101(4)
0.080(2)
0.078(3)
0.0405(2)
0.0378(2)
0.052(2)
0.067(3)
0.069(3)
0.054(2)
0.110(3)
0.073(3)
0.042(2)
0.0599(2)
0.060(2)
0.109(4)
0.0381(2)
0.0382(2)
0.037(2)
0.040(2)
0.037(2)
0.0336(2)
0.0471(1)
0.058(3)
0.0548(2)
0.077(3)
0.0436(1)
0.043(2)
0.058(2)
0.047(2)
0.050(2)
0.046(2)
0.043(2)
0.050(2)
0.0690(2)
0.081(3)
0.0505(1)
0.078(3)
0.0562(2)
0.074(3)
0.0030(2)
0.001(2)
0.003(2)
ꢁ0.023(3)
ꢁ0.011(2)
ꢁ0.003(2)
ꢁ0.075(3)
ꢁ0.002(3)
0.007(2)
0.0168(2)
0.004(2)
ꢁ0.020(4)
0.0056(2)
0.006(2)
0.014(2)
0.013(2)
0.006(2)
0.011(2)
0.0087(1)
0.006(3)
0.0101(2)
ꢁ0.004(3)
0.0070(2)
ꢁ0.002(2)
0.008(2)
ꢁ0.007(2)
ꢁ0.001(2)
0.005(2)
ꢁ0.001(2)
0.0016(2)
ꢁ0.0014(2)
ꢁ0.014(3)
0.0164(2)
0.027(3)
0.0051(1)
ꢁ0.001(3)
0.0037(1)
0.0080(2)
0.012(2)
0.024(3)
0.020(2)
0.0048(2)
0.020(3)
0.006(3)
ꢁ0.0029(1)
ꢁ0.0009(2)
0.0067(2)
ꢁ0.008(2)
ꢁ0.024(2)
ꢁ0.0134(2)
0.032(3)
0.028(3)
C9
ꢁ0.0002(2)
ꢁ0.0182(2)
ꢁ0.006(2)
ꢁ0.038(4)
0.0037(2)
0.0037(2)
0.0073(2)
0.0016(2)
ꢁ0.0046(2)
0.0052(2)
0.0103(1)
0.019(2)
ꢁ0.0015(1)
ꢁ0.007(2)
ꢁ0.0036(1)
0.0008(2)
ꢁ0.005(2)
0.0098(2)
0.004(2)
0.0061(2)
0.0023(2)
0.0021(2)
0.0303(2)
0.028(3)
0.0168(1)
0.027(3)
0.0165(1)
0.005(2)
ꢁ0.001(2)
ꢁ0.0010(1)
0.004(2)
O10
C11
C12
C13
C14
C15
C16
C17
C18
O19
C20
O21
C22
O23
C25
C24
C26
C27
C28
C29
C30
O31
C32
O33
C34
O35
C36
0.014(3)
0.0049(2)
0.0005(2)
0.0031(2)
0.0097(2)
0.0015(2)
ꢁ0.0007(2)
ꢁ0.0106(1)
ꢁ0.020(2)
0.0034(1)
0.023(3)
ꢁ0.0170(1)
ꢁ0.0103(2)
ꢁ0.017(2)
ꢁ0.0079(2)
ꢁ0.0065(2)
ꢁ0.0061(2)
ꢁ0.0003(2)
ꢁ0.0061(2)
ꢁ0.0039(1)
0.002(2)
ꢁ0.0083(1)
0.004(2)
0.0043(1)
0.008(2)

Crystal and Molecular Structure Analysis
185
o
˚
TABLE 4 Bond Lengths (A) and Bond Angles ( )
Atoms
Length
Atoms
Length
N1-C9
N1-C6
N1-C2
C2-C13
C2-C3
C3-C4
C3-C8
C4-O7
C4-C5
C5-C6
C6-C25
C9-O10
1.361(5)
1.481(5)
1.487(4)
1.518(5)
1.535(5)
1.508(6)
1.528(6)
1.206(5)
1.492(6)
1.523(5)
1.532(5)
1.233(4)
1.489(5)
1.292(6)
1.388(5)
1.391(5)
1.383(5)
1.374(4)
1.387(5)
117.2(3)
121.9(3)
120.4(3)
112.4(3)
111.4(3)
117.8(3)
120.9(5)
122.7(5)
112.3(3)
114.6(3)
118.5(4)
119.3(3)
116.1(3)
120.3(3)
C16-C17
C16-O21
C17-O23
C17-C18
O19-C20
O21-C22
O23-C24
C25-C26
C25-C30
C26-C27
C27-031
C27-C28
C28-033
C28-C29
C29-035
C29-C30
1.384(5)
1.390(5)
1.373(4)
1.383(5)
1.420(5)
1.435(5)
1.412(4)
1.382(6)
1.400(5)
1.399(5)
1.366(5)
1.400(5)
1.375(4)
1.388(5)
1.374(4)
1.391(5)
1.408(5)
1.426(5)
1.430(5)
115.2(4)
120.8(3)
120.0(3)
123.8(3)
115.7(4)
113.9(3)
118.1(3)
108.6(3)
124.5(3)
122.2(3)
120.5(3)
121.0(4)
122.8(4)
124.3(3)
C9-C11
C11-C12
C13-C18
C13-C14
C14-C15
C15-O19
C15-C16
C9-N1-C6
C9-N1-C2
C6-N1-C2
N1-C2-C13
N1-C2-C3
C15-O19-C20
O7-C4-C5
O7-C4-C3
N1-C6-C25
O31-C27-C28
O10-C9-C11
N1-C9-C11
O35-C29-C28
C15-C14-C13
O31-C32
O33-C34
O35-C36
O19-C15-C16
C17-C16-O21
C15-C16-O21
O23-C17-C18
O23-C17-C16
C16-O21-C22
C17-O23-C24
N1-C6-C5
O31-C27-C26
O10-C9-N1
O33-C28-C29
O33-C28-C27
O35-C29-C30
O19-C15-C14
represents the OR-TEP [10] diagram of the molecule with thermal
ellipsoids drawn at 50% probability. The piperidine ring is puckered.
The ring-puckering analysis [11] of six-membered ring in the molecule
indicates that the piperidine ring adopts twist boat conformation,
ꢃ
˚
with a puckering amplitude Q ¼ 0.650(4) A, h ¼ 91.6(4) , and / ¼
111.9(4)ꢃ. Atoms C2 and C6 deviate from the plane (Cremer and Pople,
˚
1975) defined by the atoms N1=C2=C3=C4=C5=C6 by ꢁ0.224(4) A and
˚
0.379(4) A, respectively. The piperdine ring in the molecule 1-
acryloyl-3-methyl-1-propionyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-
4-one has a weighted average torsion angle of 33.26ꢃ. The substituent at

186
C. R. Gnanendra et al.
FIGURE 1 Schematic diagram of the title compound.
FIGURE 2 ORTEP of the molecule plot at 50% probability.

Crystal and Molecular Structure Analysis
187
TABLE 5 Selected Torsion Angles (ꢃ)
Atoms
Angle
C2-N1-C9-O10
C6-N1-C9-O10
174.6(3)
12.9(5)
N1-C2-C9-C11
N1-C2-C3-C8
165.6(3)
173.3(3)
ꢁ164.2(3)
ꢁ178.2(4)
ꢁ166.1(3)
ꢁ176.0(4)
83.1(5)
C28-C29-O35-C36
C28-C27-O31-C32
C24-O23-C17-C16
C20-O19-C15-C16
C27-C28-O33-C34
C22-O21-C16-C17
78.8(4)
C6 exhibits equatorial conformation as indicated by the dihedral angle
of 84.2(2)ꢃ between piperidine ring 1 and the phenyl ring 3 and the
phenyl ring 2 and the piperidine ring 1 has dihedral angle of
71.68(2)ꢃ. The torsion angle value of 173.(3)ꢃ for N1-C6-C5-C8 indi-
cates that methyl group substituted at C5 is oriented in
anti-periplanar conformation. The methyl group substituted at the
C5 position have been reported to act as active anitbacterial activity
[12] against bacterial strains, i.e., Bacillus subtilis and Escherichia
coli. The literature survey [12,13] shows that the presence of an alkyl
group at the C5 position of the piperidone ring and also the attach-
ment of methoxy group to the phenyl ring at C2 and C6 positions have
reported to act as high antimicrobial activity [12]. The torsion angle
value of 174.6(3)ꢃ for C2-N1-C9-O10 indicates that O10 is oriented
in þanti-periplanar conformation. The acryloyl group substituted at
N1 is oriented in þsyn-periplanr conformation as indicated by the tor-
sion angle value of 12.9(5)ꢃ for C6-N1-C9-C10. The methoxy groups
substituted at C27, C29, C17, and C15 are nealry planar with the phe-
nyl ring whereas the methoxy groups substitued at C28 exhibits ortho-
gonal conformation as indicated by the torsion angles (Table 5). The
molecules are linked into a linear one dimensional complex chains
˚
TABLE 6 Hydrogen-bonding Geometry (A)
D–H ꢀꢀꢀ A
D–H
H–A
D–A
D–H ꢀꢀꢀ A
Symmetry codes
C2-H2 ꢀꢀꢀ O21
0.98
0.96
0.96
0.96
2.48
2.59
2.59
2.41
3.440(4)
3.432(6)
3.550(5)
3.313(5)
165
147
178
156
1=2 þ x,y, 1=2 ꢁ z
5=2 ꢁ x, ꢁ1=2 þ y, z
1=2 þ x, 1=2 ꢁ y, 1 ꢁ z
ꢁ1=2 þx, 1=2 ꢁ y, 1 ꢁ z
C22-H22A ꢀꢀꢀ O7
C36-H36C ꢀꢀꢀ O19
C20-H20B ꢀꢀꢀ O10
ꢅThe D–H and H–A distances are essentially standard values and are not derived from
the experiment.

188
C. R. Gnanendra et al.
FIGURE 3 Packing of the molecules down b axis.
by weak intermolecular hydrogen bond of the type C–H ꢀ ꢀ ꢀ O as shown
in Table 6.
ACKNOWLEDGMENTS
The authors are grateful to DST and Government of India project SP=
I2=FOO=93 and University of Mysore, Mysore for financial assistance.
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