J Chem Crystallogr (2014) 44:360–367
361
Lorentz and polarization effects were performed with
Bruker SAINT [16]. A symmetry-related (multi-scan)
absorption correction had been applied. Structure solution,
followed by full-matrix least squares refinement was per-
formed using the WINGX-1.70 suite [17] of programs
throughout. All non-hydrogen atoms were refined aniso-
tropically; hydrogen atoms were located at calculated
positions and refined using a riding model with isotropic
thermal parameters fixed at 1.2 times the Ueq value of the
appropriate carrier atom. Figure was prepared using OR-
TEP [18]. Crystal data for the title compound: C H O ,
[24, 25]. For a given crystal structure and a set of spherical
atomic densities, the Hirshfeld surface is unique [26]. The
normalized contact distance (dnorm) based on both d and di
e
(where d is distance from a point on the surface to the
e
nearest nucleus outside the surface and d is distance from a
i
point on the surface to the nearest nucleus inside the sur-
face) and the vdW radii of the atom, as given by Eq. 1
enables identification of the regions of particular impor-
tance to intermolecular interactions [22]. The combination
of d and d in the form of two-dimensional (2D) fingerprint
e
i
plot [27, 28] provides a summary of intermolecular con-
tacts in the crystal [22]. The Hirshfeld surfaces mapped
with dnorm and 2D fingerprint plots were generated using
the Crystal-Explorer 2.1 [29]. Graphical plots of the
molecular Hirshfeld surfaces mapped with dnorm used a
red-white-blue colour scheme, where red highlight shorter
contacts, white represents the contact around vdW sepa-
ration, and blue is for longer contact. Additionally, two
further coloured plots representing shape index and curv-
edness based on local curvatures are also presented in this
paper [30].
1
4 12 2
formula mass 212.24, orthorhombic space group Pbca,
˚
a = 12.012(3), b = 8.5385(19), c = 20.189(5) A, V =
3
,070.6(8) A , Z = 8, dcalcd = 1.362 mg m
-3
˚
2
,
linear
-
1
absorption coefficient 0.090 mm , F(000) = 896, crystal
size 0.35 9 0.20 9 0.15 mm, reflections collected 12596,
independent reflections 2540 [Rint = 0.0737], Final indices
[
I [ 2r(I)] R = 0.0553 wR = 0.1337, R indices (all
1
2
data) R = 0.0812, wR = 0.1562, gof 1.068, Largest
3
1
2
-
˚
difference peak and hole 0.268 and -0.312 e A
.
Computational Details
vdW
i
vdW
vdW
e
vdW
di ꢁ r
de ꢁ r
dnorm ¼
þ
ð1Þ
Quantum mechanical calculations were performed in order to
achieve deeper understanding regarding the nature and
behavior of various non-covalent interactions. All the calcu-
lations were performed using the Gaussian03 package [19].
Initial geometries of the C–HꢀꢀꢀO and C–Hꢀꢀꢀp bonded dimers
and trimers were taken from the X-ray structure. Starting from
these initial geometries all dimeric and trimeric motifs were
optimized by keeping the interaction distances frozen. All
calculations were performed at the density functional theory
r
r
e
i
Synthesis
The a-naphthol (1.44 g, 10 mmol) and dihydro-furan-2-
one (0.86 g, 10 mmol) were dissolved in 50 mL ethanol
and to it was added sodium ethoxide (0.80 g 11.7 mmol) in
portions. The whole mixture was stirred with reflux for 4 h
and finally the mixture was poured on the crushed ice and
then neutralized with dil. HCl to obtain the solid product
2-(Naphthalen-1-yloxy)-butyric acid. The product was then
dissolved in Eaton’s reagent [31] and heated up to 50 °C
for 2 h to obtain the crude final title compound. The
solution was transferred to separating funnel and to this
was added 200 mL of distilled water in dropwise manner
and shaken with precaution to ensure hydrolysis of me-
thanesulfonic anhydride. After complete hydrolysis of
methanesulfonic anhydride the product was extracted with
dichloromethane (2 9 100 mL). The extract was washed
once with dilute aqueous sodium bicarbonate (100 mL)
and twice with water, dried over sodium sulphate and
concentrated. The concentrated solution was allowed to
evaporate slowly to obtain the crystalline pure form of the
(
DFT) level using B3LYP [20, 21] functional and 6-31G**
basis set for all the atoms. The energies (DEdimer and DEtrimer
)
for dimeric and trimeric motifs involving the 2 and 3 mole-
cules, respectively were calculated using the formula
DEdimer ¼ Edimer ꢁ ð2 ꢂ EmonomerÞ and DEtrimer ¼ Etrimerꢁ
ð3 ꢂ E
Þ, where E
, E
, E
are the ener-
monomer
monomer
dimer
trimer-
gies of the monomer, dimer and trimer motifs, respectively.
Emonomer wascalculatedbyoptimizinga singlemoleculeatthe
same level of theory. The intermolecular interaction strengths
are significantly weaker than either ionic or covalent bonding,
therefore it was essential to do basis set superposition error
(
BSSE) corrections. The BSSE corrections in the interaction
energies were done using Boys–Bernardi scheme. In this
paper all the interaction energies have been reported after
BSSE correction [22].
title compound (yield 1.49 g, 70 %).
1
H NMR (300.40 MHz, CDCl ) d 8.37 (d, 1H, Ph), d
3
Hirshfeld Surface Analysis
7.80–7.83 (d, 1H, Ph), d 7.50–7.62 (m, 4H, Ph), d
4
.45–4.49 (t, 2H, CH –CO), d 2.99–3.04 (t, 2H, –CH –O),
2
2
-
1
Molecular Hirshfeld surfaces [23] in the crystal structure
were constructed on the basis of the electron distribution
calculated as the sum of spherical atom electron densities
d 2.30–2.39 (q, 2H, –CH –). mmax(KBr)/cm 1,700 (C=O).
2
Anal. Calc. for C14
H O : C, 79.23; H, 5.70 %. Found: C,
12 2
?
79.85; H, 5.93 %. ESI–MS (m/z): 213.31 (M ).
123
Aditya
