Synthesis and crystal structure analysis of 2-(fluorobenzyl)-6-(4- nitrophenyl) imidazo[2,1-b][1,3,4]thiadiazole

Article abstract of DOI:10.1080/15421406.2010.526558

Preparation of 2-(4-fluorobexzyl)-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4] thiadiazole is described and its crystal structure is discussed. The compound crystallizes in the monoclinic space group C2/c with a=39.941(6) A, b=5.698(2) A, c=13.272(5) A=90.880°,

Full text of DOI:10.1080/15421406.2010.526558

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Synthesis and Crystal Structure Analysis
of 2-(Fluorobenzyl)-6-(4-Nitrophenyl)
Imidazo[2,1-b][,,]Thiadiazole
Afshan Banu a , Ravi S. Lamani b , I. M. Khazi b & Noor Shahina
Begum a
a Department of Chemistry, Bangalore University, Bangalore, India
b Department of Chemistry, Karnatak University, Dharwad, India
Published online: 14 Dec 2010.
To cite this article: Afshan Banu , Ravi S. Lamani , I. M. Khazi & Noor Shahina Begum (2010) Synthesis
and Crystal Structure Analysis of 2-(Fluorobenzyl)-6-(4-Nitrophenyl) Imidazo[2,1-b][,,]Thiadiazole,
Molecular Crystals and Liquid Crystals, 533:1, 162-171, DOI: 10.1080/15421406.2010.526558
To link to this article: http://dx.doi.org/10.1080/15421406.2010.526558
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Mol. Cryst. Liq. Cryst., Vol. 533: pp. 162–171, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 1542-1406 print=1563-5287 online
DOI: 10.1080/15421406.2010.526558
Synthesis and Crystal Structure Analysis
of 2-(Fluorobenzyl)-6-(4-Nitrophenyl)
Imidazo[2,1-b][1,3,4]Thiadiazole
AFSHAN BANU,1 RAVI S. LAMANI,2 I. M. KHAZI,2
AND NOOR SHAHINA BEGUM1
1Department of Chemistry, Bangalore University, Bangalore, India
2Department of Chemistry, Karnatak University, Dharwad, India
Preparation of 2-(4-fluorobexzyl)-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole
is described and its crystal structure is discussed. The compound crystallizes in the
˚
˚
˚
monoclinic space group C2=c with a ¼ 39.941(6) A, b ¼ 5.698(2) A, c ¼ 13.272(5) A
3
ꢀ
˚
b ¼ 90.880 , V ¼ 3020(2) A , z ¼ 8. The crystal structure is stabilized by weak
intermolecular C-H . . . N,C-H . . . O,C-H . . . S, and C-H . . . F interactions.
Keywords C-H . . . N, C-H . . . O, C-H . . . S, and C-H . . . F; crystal structure;
imidazo[2,1-b] 1,3,4-thiadiazoles derivative; weak interactions
Introduction
1,3,4-Thiadiazoles are known for their promising biological and pharmacological
activities, possibly due to the presence of a pharmacophoric isothioamide
=
(SꢁC Nꢁ) unit [1,2] in the thiadiazole nucleus. Secondly, the thiadiazole ring
is bioisosteric with the thiazole moiety of the novel broad-spectrum anthelmintic
tetramisole [3,4]. Some thiadiazole derivatives are reported to possess anticancer
properties [5] and hence they have potential pharmaceutical prospects.
Many imidazothiadiazole derivatives have been reported to possess diverse med-
icinal properties such as anthelmintic [6], antimicrobial [7], and anti-inflammatory,
antipyretic, analgesic [8], and many other activities of therapeutic significance
[9,10]. Moreover, the presence of fluoro substituent in the molecule provides com-
pounds with enhanced biological activity. Accumulation of fluorine [11] on carbon
leads to increased oxidative and thermal stability. Further, it leads to increased lipid
solubility, thereby enchancing the rate of absorption and transport of drug in vivo.
These findings prompted us to synthesize the title compound so that it could be
screened for its pharmacological activities and to carry out its crystallographic struc-
ture elucidation. The title compound will be a good intermediate to synthesize vari-
ous candidate compounds for pharmacological testing.
Address correspondence to Dr. Noor Shahina Begum, Department of Chemistry,
Central College Campus, Dr. B.R. Ambedkar Street, Bangalore University, Bangalore
560001, Karnataka, India. E-mail: noorsb@rediffmail.com
162

Synthesis and Crystal Structure Analysis
Synthesis and Characterization
163
The title compound was prepared as shown in Scheme 1. The reaction of 2-amino-
(4-fluorobenzyl)-1,3,4-thiadiazole [12] 1) and nitro phenacyl bromide (2) in boiling
ethanol afforded the 2-amino-(4-fluorobenzyl)-6-(4-nitrophenyl)-imidazo[2,1-b]
[1,3,4]thiadiazole (3) as hydrobromide salt, which was neutralized by sodium carbon-
ate solution to get the free base. It is well established that this reaction proceeds via
the intermediate iminothiadiazole, which under reflux temperature spontaneously
undergoes dehydrocyclization to form the desired fused heterocycle [13].
Experimental
2-(4-Fluorobenzyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazole
A mixture of 2-amino-(4-fluorobenzyl)-1,3,4-thiadiazole (1) (2.69, 0.013 mol) and
nitro phenacyl bromide (2) (0.01 mol) of equimolar quantities was refluxed in dry
ethanol for 18 h. The excess of solvent was distilled off and by filtration the solid
hydrobromide salt that separated was collected, suspended in water, and neutralized
by aqueous sodium carbonate solution to get free base (3). It was filtered,washed
with water, dried, and recrystallized from ethanol.
Physical Measurements
Melting points were determined in open capillaries. Infrared (IR) spectra were
recorded on a Nicolet Fourier transform infrared spectrophotometer (University
1
Science Instrument Centre, Karnatak University Dharwad, Karnataka), H nuclear
magnetic resonance (NMR) spectra were recorded on Varian RX-300 MHz spec-
trometer using trimethyl siloxane (TMS) as internal standard.
The structure of imidazothiadiazole derivative 3 was established by the absence
of a nN-H band in the IR spectra and the appearance of imidazole proton (C5ꢁH)
around d 8 in the 1H NMR spectra. The 13C NMR and mass spectra of this
compound further confirmed the assigned structure.
2-(4-Fluorobenzyl)-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole (3)ꢁ. 1Yellow
crystalline solid (ethanolþdiaxon), yield 64% m.p. 212–214ꢀC; UV-Vis
(nm):
1
316. IR (KBr) vcm: 3,107, 2,924, 2,854, 1,603, 1,524, 1,501; H NMR (300 MHz,
CDCl3) d: 4.31 (s, 2H, CH2), 7.07–7.39 (m, 4H, Ar-H), 7.83 (d, J ¼ 8.4 Hz, 2H,
Ar-H), 7.91 (d, J ¼ 8.4 Hz, 2H, Ar–H), 8.12 (s, 1H, C-H, imidazole). 13C NMR
(75 MHz, CDCl3) d : 37.8, 109.6, 116.3, 121.7, 127.0, 30.9, 131.0, 132.2, 145.4,
146.2, 161.1, 164.1. Anal. calcd. for C17H11FN4O2S: C, 57.62: H, 3.10; N, 15.81;
Found: C,57.48; H, 3.08; N, 15.78% MS (m=z): 354.
X-Ray Analysis
The X-ray diffraction data for compound 3 were collected on a Bruker Smart
˚
CCD Area Detector System (I.I.Sc, Bangalore), using MoKa (0.71073 A) radiation
for the crystal. Intensity data were collected up to a maximum of 28.58ꢀ in the
x–U scan mode. The data were reduced using SAINTPLUS [14]. The structure
was solved by direct methods using SHELXS97 [15] and difference Fourier
syntheis using SHELXL97 [16]. The positions and anisotropic displacement para-
meters of all nonhydrogen atoms were included in the full-matrix least-squares

164
A. Banu et al.
Figure 1. ORTEP diagram of compound 3 showing 50% probability displacement ellipsoids
and the atom-numbering scheme.Dotted line indicates intramolcular C7-H7 . . . N3 interaction.
Figure 2. Packing of the molecules in crystal of 3 viewed along the b axis. Dotted line indicates C-
H . . . S (a-a), and C-H . . . N (a1-a1), and C-H . . . O (a2-a21, a22, a23) intermolecular interactions.
Figure 3. Packing of the molecules of 3 with dotted lines indicating C-H . . . F intermolecular
interactions generating zig-zag tapes along the b axis.

Synthesis and Crystal Structure Analysis
165
Figure 4. View of the molecular packing in 3 showing p-p stacking interactions between
imidazothiadiazole and nitro benzene rings.
refinement using SHELXL97 [16] and the procedure was carried out for a few
cycles until convergence was reached. A total of 9,096 reflections was collected,
resulting in 3,701 [R(int) ¼ 0.0847] independent reflections, of which the number
of reflections satisfying I > 2r(I) criteria was 2,733.
Table 1. Crystal data and structure refinement
CCDC deposite no.
Empirical formula
Formula weight
763068
C17 H11 F N4 O2 S
354.36
Temperature
Wavelength
293(2) K
˚
0.71073 A
Monoclinic, C2=c
Crystal system, space group
Unit cell dimensions
˚
a (A)
39.941(6)
5.698(2)
13.272(5)
90.880
3,020(2)
˚
b (A)
˚
c (A)
b (ꢀ)
Volume (A )
3
˚
Z
8
1.559
0.246
1,456
Calculated density (Mg=m3)
Absorption coefficient (mmꢁ1
F(000)
)
Crystal size
Theta range for data collection
Limiting indices
Reflection collected = unique
Completeness of theta
Refinement method
0.4 mm ꢂ 0.35 mm ꢂ 0.3 mm
2.04–28.58ꢀ.
ꢁ52 ꢃ h ꢃ 45, 7 ꢃ k ꢃ 6, 17 ꢃ I ꢃ 17
9,096=3,701 [R (int) ¼ 0.0847]
28.58 95.8%
Full-matrix least-squares on F2
3,701=0=230
1.108
Data=restraints=parameters
Goodness-of-fit on F2
Final R indices [I > 2 sigma(I)]
R indices (all data)
R1 ¼ 0.0742, wR2 ¼ 0.1817
R1 ¼ 0.1053, wR2 ¼ 0.2283
0.874 and ꢁ0.854
ꢁ3
˚
Largest diff. peak and hole (e A
)

166
A. Banu et al.
These were treated as observed. The H atoms were placed at calculated positions
˚
in the riding model approximation (C—H 0.93 A); their temperature factors were set
to 1.2 times those of the equivalent isotropic temperature factors of the parent
atoms. All other non-H atoms were refined anisotropically. The R factor for
observed data finally converged to R ¼ 0.0742 with wR2 ¼ 0.1990 in the compound.
The maximum and minimum values of residual electron density were 0.874 and
ꢁ0.854 eAꢁ3. Molecular diagrams were generated using ORTEP [17]. The mean
˚
plane calculation was done using the program PARST [18].
Results and Discussion
Figure 1 shows the ORTEP diagram of the molecule with thermal ellipsoids drawn
at 50% probability of the title compound. Figures 2, 3, and 4 show hydrogen-bond
interactions and crystal packing of the compound. The details of crystal data and
refinements are given in Table 1. Table 2 gives the list of atomic coordinates and
equivalent isotropic displacement parameters of the nonhydrogen atoms. Table 3
gives the list of anisotropic displacement parameters of the nonhydrogen atoms.
Table 2. Atomic coordinate (ꢂ 104) and equivalent isotropic displacement parameter
(ꢂ 103) nonhydrogen atoms
Atoms
x
Y
z
U(eq)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
O(1)
O(2)
N(1)
N(2)
N(3)
N(4)
S(1)
929(1)
1,291(1)
1,818(1)
2,148(1)
2,685(1)
2,325(1)
2,830(1)
3,165(1)
3,363(1)
3,232(1)
2,893(1)
696(1)
575(1)
369(1)
282(1)
399(1)
604(1)
3,824(1)
3,901(1)
1,528(1)
1,825(1)
2,115(1)
3,720(1)
1,406(1)
77(1)
8,704(6)
7,996(6)
5,890(6)
8,836(6)
6,405(6)
6,796(6)
4,249(6)
3,849(6)
5,627(6)
7,779(6)
8,154(6)
6,639(6)
5,541(7)
3,612(7)
2,771(7)
3,791(8)
5,714(7)
3,180(5)
6,846(5)
9,466(5)
8,245(5)
4,936(5)
5,183(5)
5,057(2)
901(5)
810(2)
887(2)
882(2)
25(1)
21(1)
20(1)
19(1)
18(1)
20(1)
21(1)
22(1)
22(1)
23(1)
23(1)
26(1)
29(1)
33(1)
31(1)
33(1)
32(1)
35(1)
33(1)
23(1)
20(1)
19(1)
24(1)
24(1)
43(1)
1,284(2)
1,286(2)
1,172(2)
1,013(2)
1,132(2)
1,529(2)
1,800(2)
1,685(2)
885(2)
16(3)
79(3)
1020(3)
1894(3)
1814(3)
1541(2)
1875(2)
1094(2)
1094(2)
916(2)
1662(2)
691(1)
1096(2)
F(1)

Synthesis and Crystal Structure Analysis
167
Table 3. Anisotropic displacement parameters (ꢂ 104) of non hydrogen atoms
Atom
U11
U22
U33
U23
U13
U12
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
O(1)
O(2)
N(1)
N(2)
N(3)
N(4)
S(1)
28(2)
30(2)
28(2)
28(2)
29(2)
27(2)
27(2)
33(2)
25(2)
31(2)
33(2)
25(2)
30(2)
35(2)
22(2)
31(2)
29(2)
35(1)
28(1)
28(1)
29(1)
24(1)
31(1)
25(1)
41(1)
28(2)
22(2)
20(2)
19(2)
21(2)
23(2)
21(2)
22(2)
28(2)
23(2)
20(2)
33(2)
39(2)
38(2)
34(2)
47(2)
46(2)
36(1)
39(2)
26(2)
16(1)
18(1)
30(2)
22(1)
40(2)
20(2)
11(1)
13(1)
10(1)
4(1)
ꢁ2(1)
0(1)
1(1)
0(1)
1(1)
0(1)
0(1)
0(1)
4(1)
ꢁ1(1)
ꢁ1(1)
2(1)
0(1)
0(1)
ꢁ2(1)
ꢁ3(1)
1(1)
9(1)
1(1)
ꢁ1(1)
ꢁ3(1)
2(1)
9(1)
1(1)
ꢁ2(1)
16(1)
11(1)
14(1)
14(1)
15(1)
18(2)
18(2)
25(2)
36(2)
20(2)
20(2)
33(1)
31(1)
15(1)
14(1)
16(1)
12(1)
25(1)
47(1)
5(1)
1(1)
ꢁ3(1)
ꢁ1(1)
ꢁ7(1)
0(1)
7(1)
1(2)
2(1)
ꢁ1(1)
0(1)
0(1)
0(1)
ꢁ3(1)
ꢁ9(2)
ꢁ2(2)
4(2)
ꢁ4(2)
ꢁ6(1)
1(1)
1(1)
1(1)
1(1)
1(1)
ꢁ4(1)
ꢁ8(2)
ꢁ2(1)
1(1)
ꢁ5(1)
ꢁ7(1)
ꢁ5(1)
2(1)
6(2)
3(1)
ꢁ1(2)
ꢁ2(2)
10(1)
ꢁ5(1)
3(1)
0(1)
4(1)
ꢁ1(1)
ꢁ1(1)
ꢁ2(1)
ꢁ2(1)
ꢁ2(1)
1(1)
1(1)
ꢁ3(1)
F(1)
ꢁ3(1)
ꢁ9(1)
The selected bond lengths and bond angles of all the nonhydrogen atoms are given in
Tables 4 and 5. Table 6 gives selected torsion angles. Table 7 shows the respective
hydrogen bond interactions for compound 3. In the molecule, the dihedral angle
between fluorobenzyl and imidazothiadaizole is 89.26(5)ꢀ, which is Almost orthog-
onal. The nitrophenyl and imidazothiadiazole are planar with only 10.02(7)ꢀ between
them and the NO2 group is cis to imidazothiadiazole and aryl ring. Specifically, in
nitrobenzene, the nitro group is essentially coplanar with the adjacent aryl ring
because the molecule is highly polar, having significant negative charge on the O
atoms, with minimum energy conformation [20]. The mesomeric interaction between
the nitro group and the aryl ring in nitrobenzene is rather small,so that the C-N bond
is effectively a single bond with a correspondingly small barrier to roation. Hence,
the intermolecular interaction could be quite modest in solid state,if the Nitro-aryl
˚
moiety perturbs its planar conformation. The C-N bond distance is 1.461(5) A in
nitrobenzene. This value is typical of C(aryl)–NO2 distances [19], where the mean
˚
value is 1.468 A. Within the nitrated aryl rings,the C-C-C angle shows significant
deviations from 120ꢀ.The O-N-O angle is 123.6ꢀ, which is greater than the ideal
trigonal value. This can be attributed to the substantial negative charges on the
paired O atoms in this unit.

168
A. Banu et al.
˚
Table 4. Bond lengths (A)
Atom
Length
C(2)-N(1)
C(2)-S(1)
C(3)-N(4)
C(3)-N(2)
C(3)-S(1)
1.289(4)
1.755(3)
1.311(4)
1.373(4)
1.720(3)
1.355(4)
1.374(4)
1.392(4)
1409(4)
1.460(4)
1.388(4)
1.361(4)
1.378(5)
1.382(5)
1.457(4)
1.379(4)
1.387(5)
1.397(5)
1.381(5)
1.384(5)
1.352(4)
1.364(5)
1.379(5)
1.376(4)
1.220(4)
1.227(4)
C(4)-N(2)
C(4)-C(6)
C(5)-C(11)
C(5)-C(7)
C(5)-C(6)
C(6)-N(4)
C(7)-C(8)
C(8)-C(9)
C(9)-C(10)
C(9)-N(3)
C(10)-C(11)
C(12)-C(13)
C(12)-C(17)
C(13)-C(14)
C(14)-C(15)
C(15)-F(1)
C(15)-C(16)
C(16)-C(17)
N(1)-N(2)
N(3)-O(2)
N(3)-O(1)
The molecular structure is primarily stabilized by weak intramolecular
˚
˚
C7-H7 . . . N3 hydrogen bond (C7-H7 ¼ 0.930(3) A, H7 . . . N3 ¼ 2.557(3) A, C7 . . .
ꢀ
˚
N3 ¼ 2.881(4) A, and the angle C7-H7 . . . N3 ¼ 100.87(1) ), leading to the
formation of a pseudo-five-membered hydrogen-bonded pattern with Etter’s graph
set analysis S(5) [21], thus locking the molecular conformation and eliminating
conformational flexibility.
Further, the crystal structure is stabilized by intermolecular interactions into a
three-dimensional framework structure by the combination of C-H . . . N, C-H . . . O,
C-H . . . S, and C-H . . . F. In C-H . . . N interaction, the molecules are linked by paired
C-H . . . N hydrogen bonds into centrosymmetric dimers corresponding to Etter’s
graph set notation R22(10) [21], the C-H . . . S interaction sets a bonded dimers
corresponding to graph set R22(16) that is formed between C21 and S1 of another
molecule, and the C-H . . . O interaction generates trifurcated bonds from three
donors C1 and C17 of one molecule and C1 of another molecule to the same
acceptor O1 linking the molecule into a zig-zag ribbon structure along b axis
(Fig. 2). The C-H . . . F interaction generates bifurcated bonds from two donors,
C14 and the C16, to the same acceptor, F1, linking the dimers so formed into zig-zag

Synthesis and Crystal Structure Analysis
Table 5. Bond angles(ꢀ)
169
Atoms
Angle
C(2)-C(1)-C(12)
N(1)-C(2)-C(1)
N(1)-C(2)-S(1)
C(1)-C(2)-S(1)
112.3(3)
122.6(3)
117.4(2)
120.1(2)
112.3(3)
139.0(3)
108.6(2)
118.3(3)
120.5(3)
121.1(3)
111.7)3)
128.6(3)
119.7(3)
121.5(3)
118.6(3)
122.0(3)
118.3(3)
119.7(3)
119.0(3)
118.1(3)
120.1(3)
121.8(3)
120.4(3)
119.3(3)
117.7(3)
120.0(3)
122.2(3)
117.7(3)
122.3(3)
107.5(3)
107.5(3)
133.8(3)
118.4(3)
123.6(3)
117.8(3)
118.5(3)
103.6(3)
88.11(15)
N(4)-C(3)-N(2)
N(4)-C(3)-S(1)
N(2)-C(3)-S(1)
C(11)-C(5)-C(7)
C(11)-C(5)-C(6)
C(7)-C(5)-C(6)
C(4)-C(6)-N(4)
C(4)-C(6)-C(5)
N(4)-C(6)-C(5)
C(8)-C(7)-C(5)
C(7)-C(8)-C(9)
C(8)-C(9)-C(10)
C(8)-C(9)-N(3)
C(10)-C(9)-N(3)
C(11)-C(10)-C(9)
C(13)-C(12)-C(17)
C(13)-C(12)-C(1)
C(17)-C(12)-C(1)
C(14)-C(13)-C(12)
C(13)-C(14)-C(15)
F(1)-C(15)-C(16)
F(1)-C(15)-C(14)
C(16)-C(15)-C(14)
C(15)-C(16)-C(17)
C(16)-C(17)-C(12)
C(2)-N(1)-N(2)
C(4)-N(2)-C(3)
C(4)-N(2)-N(1)
C(3)-N(2)-N(1)
O(2)-N(3)-O(1)
O(2)-N(3)-O(9)
O(1)-N(3)-C(9)
C(3)-N(4)-C(6)
C(3)-S(1)-C(2)
tapes leading to a two-dimensional network and resulting in centrosymmetric
dimmers corresponding to graph set R22 (8) along ‘b’ axis (Fig. 3). The molecular
packing is further stabilized by p-p stacking interactions between the nitro benzene
and imidazothiadiazole ring systems with C4-C7 atoms of two molecules being sepa-
1
2
˚
rated by a distance of 3.238(4) A (Fig. 4) (symmetry code. ꢁx,y,ꢁz).

170
A. Banu et al.
Table 6. Selected torsion angles (ꢀ)
C(12-C(1)-C(2)-N(1)
C(12)-C(1)-C(2)-S(1)
N(2)-C(4)-C(6)-N(3)
N(2)-C(4)-C(6)-C(5)
C(7)-C(8)-C(9)-N(4)
N(4)-C(9)-C(10)-C(11)
C(13)-C(14)-C(15)-F(1)
F(1)-C(15)-C(16)-C(17)
C(1)-C(2)-N(1)-N(2)
S(1)-C(2)-N(1)-N(2)
C(6)-C(4)-N(2)-C(3)
C(6)-C(4)-N(2)-N(1)
N(3)-C(3)-N(2)-C(4)
S(1)-C(3)-N(2)-C(4)
N(3)-C(3)-N(2)-N(1)
S(1)-C(3)-N(2)-C(1)
C(2)-N(1)-N(2)-C(4)
C(2)-N(1)-N(2)-C(3)
N(2)-C(3)-N(3)-C(6)
S(1)-C(3)-N(3)-C(6)
C(4)-C(6)-N(3)-C(3)
C(5)-C(6)-N(3)-C(3)
C(10)-C(9)-N(4)-O(2)
C(8)-C(9)-N(4)-O(2)
C(10)-C(9)-N(4)-O(1)
C(8)-C(9)-N(4)-O(1)
N(3)-C(3)-S(1)-C(2)
N(2)-C(3)-S(1)-C(2)
N(1)-C(2)-S(1)-C(2)
C(1)-C(2)-S(1)-C(3)
ꢁ162.1(3)
17.9(4)
ꢁ0.1(3)
179.9(3)
179.5(3)
178.9(3)
179.1(3)
ꢁ179.1(3)
ꢁ179.3(3)
0.7(3)
0.3(3)
179.0(3)
ꢁ0.5(3)
177.43(19)
179.4(2)
1.4(3)
178.0(3)
0.5(4)
0.4(3)
ꢁ176.6(3)
ꢁ0.2(3)
179.8(3)
ꢁ10.4(4)
169.8(3)
170.8(3)
ꢁ9.1(4)
178.5(4)
1.4(2)
ꢁ1.2(2)
ꢁ178.8(3)
ꢀ
˚
Table 7. Non-bonded interaction and possible hytrogen bonds(A, ) for compound 3
D—H . . . A
D—H
H . . . A
D . . . A
D—H . . . A
C7–H7 . . . N3
C7–H7 . . . N3i
C8-h8 . . . s1i
C1–H1A . . . O2ii
C1–H1B . . . O2ii
C13–H13 . . . O2iii
C14–H14 . . . F1iv
C16–H16 . . . F1v
0.930(3)
0.930(3)
0.930(3)
0.970(3)
0.970(3)
0.930(4)
0.930(4)
0.930(4)
2.557(3)
2.904(3)
2.936(1)
2.955(3)
2.764(3)
2.776(3)
2.713(3)
2.822(3)
2.881(4)
3.509(4)
3.724(3)
3. 651(4)
3.613(4)
3.614(4)
3.438(5)
3.687(5)
100
123
143(9)
129(9)
146(2)
150
140(4)
155(3)
1
1
1
1
1
Symmetry code: (0) x, y, z; (i)–x þ 2, ꢁy þ 2, ꢁz; (ii)–x þ 2, ꢁ1=2, ꢁy þ 2 þ 1, ꢁz; (iii) ꢁx þ 2,
1
1
þy þ 2, ꢁz þ 2; (iv) –x, ꢁy, ꢁz; (v)–x, þy, ꢁz þ 1=2.

Synthesis and Crystal Structure Analysis
171
Acknowledgment
N.S.B. is thankful to the University Grants Commission (UGC), India, for financial
assistance and the Department of Science and Technology (DST), India, for collec-
tion on the CCD facility set up under the IRHPA-DST program.
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