Synthesis, growth, and characterization of 3-(4-Methoxyphenyl)-1-(pyridin- 2-yl) prop-2-en-1-one single crystal: A potential NLO material

Article abstract of DOI:10.1016/j.molstruc.2013.08.026

New nonlinear optical chalcone material, 3-(4-Methoxyphenyl)-1-(pyridin-2- yl) prop-2-en-1-one (MPP) has been synthesized and grown as a high quality single crystal by the slow evaporation solution growth technique using acetone as solvent. The grown crys

Full text of DOI:10.1016/j.molstruc.2013.08.026

Accepted Manuscript
Synthesis, growth, and characterization of 3-(4-Methoxyphenyl)-1-(pyridin-2-
yl) prop-2-en-1-one single crystal: A potential NLO material
A. Jayarama, H.J. Ravindra, Anthoni Praveen Menezes, S.M. Dharmaprakash,
Seik Weng Ng
PII:
S0022-2860(13)00702-3
DOI:
http://dx.doi.org/10.1016/j.molstruc.2013.08.026
MOLSTR 19961
Reference:
To appear in:
Journal of Molecular Structure
Received Date:
Revised Date:
Accepted Date:
28 May 2013
12 August 2013
14 August 2013
Please cite this article as: A. Jayarama, H.J. Ravindra, A.P. Menezes, S.M. Dharmaprakash, S.W. Ng, Synthesis,
growth, and characterization of 3-(4-Methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-1-one single crystal: A potential
NLO material, Journal of Molecular Structure (2013), doi: http://dx.doi.org/10.1016/j.molstruc.2013.08.026
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Synthesis, growth, and characterization of 3-(4-
Methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-1-one single
crystal: A potential NLO material
A. Jayaramaa,*, H.J Ravindrab, Anthoni Praveen Menezesa, S.M. Dharmaprakashc, Seik Weng
Ngd,e
aDepartment of Physics, Mangalore Institute of Technology & Engineering (MITE), Moodabidri, 574 225 India.
bDepartment of Physics, Shri Madhwa Vadiraja Institute of Technology and Management, Bantakal, Udupi
574115, India
cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199, India.
dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
eChemistry department, Faculty of Science King Abdulaziz University, PO Box 80203, Jeddah.
*E-mail: jrmarasalike@yahoo.co.in; Ph : +91 9611945201
Abstract
New nonlinear optical chalcone material, 3-(4-Methoxyphenyl)-1-(pyridin-2-yl) prop-
2-en-1-one (MPP) has been synthesized and grown as a high quality single crystal by the slow
evaporation solution growth technique using acetone as solvent. The grown crystals were
characterized by Fourier transform infrared (FTIR) spectroscopy, Laser Raman spectroscopy,
FT-NMR spectroscopy, single crystal X-ray diffraction (XRD), thermal analysis and UV–
VIS–NIR spectroscopy. The presence of functional groups was confirmed by FTIR and Laser
Raman spectroscopic analysis and the structural elucidation was done using FT- NMR
spectral analysis. Thermo gravimetric analysis shows that initial weight loss of the material is
found at around 1600C. MPP crystallizes with non-centrosymmetric Pna21 space group with
cell parameters a = 25.6311(3) Å, b = 11.6419(2) Å, c = 3.9742(1) Å and volume =
1185.88(4) Å3. The powder Second Harmonic Generation (SHG) conversion efficiency is
found by Kurtz powder technique and is 4.7 times more than that of urea. The UV-VIS-NIR
absorption spectral analysis revealed that the crystal can be used for down conversion of the
laser wavelength up to 410 nm. The observed SHG efficiency of the MPP crystal is attributed
to zig-zag head-to-tail alignment of molecular dipoles in crystallographic c-direction which
results in establishing net polarization in the bulk crystal.

Keywords:
A. Optical material
B. Crystal growth
C. X-ray diffraction
C. Thermo gravimetric analysis
D. Crystal structure
1. Introduction
Organic crystals have been the subject of interest in nonlinear optics due to their large
optical nonlinearities combined with advantages over other materials in terms of easy
fabrication, flexibility for structural modifications and their applications in optoelectronics
such as optical data storage, optical limiters, modulators and optical switches [1, 2]. Well
designed organic nonlinear optical crystals generally show high and faster nonlinear response
compared to their inorganic counterparts. Among the organic nonlinear optical materials the
chalcone derivatives are interesting materials because of their large NLO coefficients, high
laser damage threshold, good crystallizability and excellent blue light transmittance [3-5].
Moreover, the optical nonlinearity in this class of materials is electronic in origin and hence
exhibits an ultra fast response [5]. The substitution of electron acceptors/donors on either end
of the phenyl rings of chalcones greatly influences the noncentrosymmetric crystal packing
required for second harmonic generation (SHG) [6]. The second order molecular nonlinearity
can be enhanced by large delocalized π-electron systems with strong donor and acceptor
groups at the ends of the highly polarizable conjugated bridge [7, 8]. Wu et al [9] suggested
from their theoretical hyperpolarizability studies that the carbonyl group present at the middle
in these molecules splits the conjugated system into relatively two independent parts.
Therefore, chalcones can be regarded as cross-conjugated molecules that possess two
independent hyperpolarizable parts to have a two-dimensional β character. It was also
suggested by Zhao et al [10] and Wu et al [9] that electron donors such as -OCH3, -CH3, -Cl
and -Br are the best donor groups for enhancing SHG in chalcones. Based on the design
criterion proposed by Zhao et al [10] and Ravindra et al [5] we designed a pyridine based
moiety by replacing phenyl moiety at the benzoyl group arm. The current molecular design
resulted in enhanced molecular first hyperpolarizability of the chalcone derivative. A chalcone
molecule with methoxy groups substituted at meta- and ortho-position was reported in the
literature which shows SHG efficiency equal to that of KDP [11]. In this paper we present our

experimental results on the crystal growth, characterization and structure-NLO property
relationship in a new nonlinear optical crystal 3-(4-Methoxyphenyl)-1-(pyridin-2-yl) prop-2-
en-1-one (MPP).
2. Experimental procedure
2.1. Synthesis, Solubility and Crystal growth
MPP was synthesized by Claisen–Schimidt condensation reaction [13]. To synthesize
3-(4-Methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, commercially available Analytical
Reagent (AR) grade chemicals were used without further purification. The starting
compounds, 2-Acetyl pyridine (0.01mol) and 4-methoxy benzaldehyde (0.01mol) were
dissolved in methanol (60 ml). Sodium hydroxide (5 ml, 20%) was then added to this solution,
and stirred for 2 hours. The content of the flask were poured into ice-cold water and the
resulting crude solid was collected by filtration and dried. The light yellow colour compound
obtained was re-crystallized twice from acetone solution. During the recrystallization the
mother solution was treated with activated charcoal and filtered solution was subjected to
rapid crystallization. The synthetic scheme for the title compound is shown in Fig. 1.
Fig.1. Synthetic scheme of MPP crystal
The solubility of the compound in a particular solvent is determined by adding a
known amount of compound to the known volume of solvent until the dissolution ceases.
Using this simple procedure it is found that the title compound is insoluble in water, sparingly
soluble in methanol and ethanol, and moderately soluble in acetone, benzene, and N,N-
dimethylformamide (DMF).
The acetone was selected as solvent to grow single crystals of MPP due to its moderate
solubility and gives better control over the growth rate by means of controlling the
evaporation rate. Single crystals of MPP were grown by adopting slow evaporation solution

growth technique [14] at room temperature. A saturated solution of MPP was prepared in a
beaker and was then covered with a perforated sheet to control the evaporation rate. The
growth solution was kept in a dust free atmosphere. The tiny crystals of MPP were appeared
in two days and were allowed to grow further. The crystal reached a maximum dimension of
6×1×1mm3 in five days. The harvested pale yellowish transparent crystals of MPP are shown
in Fig.2a. The morphology of the single crystal of MPP was simulated using WinXMorph
software [19] and is shown in Fig.2b. The crystal was found to be elongated along the
crystallographic c-axis due to larger growth rate in comparison with the other two axes. The
simulated morphology of the crystal resembles closely with the actual morphology of the
crystal. One should note here that the solvent play a major role on the morphology of the
crystals and it may vary if the MPP is crystallized from other solvents.
(a)
(b)
Fig.2. a) Photograph of MPP single crystals b) Simulated morphology of MPP
3. Results and Discussion
3.1. CHN analysis
To confirm the chemical composition of MPP, CHN analysis was carried out on the
re-crystallized sample using the Elementar Vario EL III CHNS analyzer. The results of the

analysis are presented in Table 1. The experimental and calculated values of C, H and N are in
good agreement with each other which confirms the molecular formula MPP as C15H13NO2.
Table 1
CHN Analysis of MPP
Element
Carbon
Experimental (%)
Computed (%)
75.30
73.51
4.61
6.02
Hydrogen
Nitrogen
5.48
5.85
3.2. FT-IR & Laser Raman spectral analysis
To investigate the presence of functional groups and their vibrational modes, FT-IR
and Laser Raman spectral analysis of MPP was carried out. The MPP sample used for FTIR
study was in pallet form in KBr phase. The FT-IR spectrum was recorded between 400 cm-1
and 4000 cm-1 using a BRUKER 66V FT-IR spectrometer. Laser Raman spectrum of MPP
crystal was obtained using Dilor Z 24 Laser Raman spectrometer using an excitation
wavelength of 647.1 nm. The Laser Raman and FT-IR spectra of MPP are shown in Fig. 3 and
Fig. 4 respectively. The characteristic frequencies and the corresponding assignments are
recorded in Table.2. The FT-IR and Raman spectrum confirms the functional groups present
in the MPP.

Fig.3. FTIR spectrum of MPP Crystal

Table 2
Assignment of vibrational frequencies
Wave number (cm-1)
______________________________________
Assignment
Infrared lines
3049.65
Raman lines
3057.2
-
Aromatic C-H stretching
Asymmetric and symmetric
C-H Stretching of CH3
C=O stretching vibration
conjugated C=C stretching
vibrations
2969.8, 2840.9
1691.3
-
-
1665.67
1598.4
1566.1
1509.0
1596.3
1572.9
-
Aromatic ring vibrations
C=C aromatic stretching
C=C bending modes of α, β
– unsaturated Carbons
Alkyl C-H bending of CH3-O
C – N stretching vibration
C-H in plane deformation of
methyl group
1443.0, 1418.5
1343
1418.5
-
1308.15
1310
1257.88
1258.58
Asymmetric C-O-C
stretching vibrations
1170.7
1170.7
1032
C – C stretching vibrations
1029.87
Symmetric C-O-C stretching
Vibration
985.35
-
-
CH=CH stretching vibration
Out of plane C – H aromatic
bending vibrations
826.43 to 674.63

Fig.4. Laser Raman Spectrum of MPP Crystal
3.3. NMR spectral study
The structure of MPP was confirmed with the help of 1H NMR and 13C NMR spectral
study. The sample was dissolved in CDCl3 and NMR spectrum was recorded using a Bruker
Advance III FT-NMR spectrometer and TMS as the internal standard. The 1H NMR and 13C
NMR spectra are shown in Fig. 5 and Fig.6 respectively. The characteristic peaks observed in
the spectra are assigned as given below.
1H NMR spectrum (CDCl3, ppm), δ: 8.74-8.75 (1H, s, C1-H), 8.16-8.20 (2H, d, C2-H,
C3-H), 7.91-7.95 (1H, d, C7-H, J=16Hz), 7.85-7.89 (1H, m, C4-H), 7.69-7.71 (2H, m, C11-H,
C13-H, J=8.4Hz), 7.45-7.49 (1H, d, C8-H, J=12Hz), 6.93-6.95 (2H, d, C10-H, C14-H,
J=8.8Hz), 3.83-3.91 (3H, s, -OCH3).
13C NMR spectrum (CDCl3, ppm), δ: 189.4(C6), 161.6 (C12), 154.5 (C7), 148.8 (C8),
144.7 (C1), 136.99 (C2), 130.7 (C11, C13), 127.99 (C3), 126.7 (C4), 122.9 (C5), 118.54 (C9),
114.34 (C10, C14), 55.4 (C15).

Fig. 5. 1H NMR spectrum of MPP
Fig.6. 13C NMR spectrum of MPP

3.4. Crystal structure determination
MPP was subjected to single crystal X-ray diffraction (XRD) using a Bruker SMART
APEX2 CCD area detector diffractometer. The X-ray generator was operated at 50kV and
1mA using enhanced Mo Kα radiation. Data were collected with a scan width of 1 . From
single crystal XRD studies, it has been found that the compound crystallizes in the
orthorhombic system with a non-centrosymmetric space group Pna21, thus satisfying one of
the basic requirement for the crystal to exhibit SHG activity. The molecular structure of MPP
with displacement ellipsoids were drawn at the 50% probability is shown in Fig. 7.
The molecule of the title chalcone derivative exists in E-configuration with respect to
the C7=C8 double bond [1.341(5) Å]. The C6-C7-C8-C9 torsion angle is -179.7(3)o. The
molecule is almost planar with dihedral angle between the pyridine and 4- methoxyphenyl
rings of 2.04o. Atoms of the propenone bridge (C6, C7, C8 and O1) lie on the same plane and
the O1-C6-C7-C8 torsion angle is 3.8(6)o. The mean plane through this bridge makes dihedral
angles of 3.32o and 3.58o with the planes of pyridine and benzene rings respectively. The
Benzene ring and substituted methoxy group of the 4-menthoxy phenyl unit are co-planar as
indicated by the torsion angle C15-O2-C12-C13=-2.5(2)o. The C-H…O interactions helps in
consolidating the structure of MPP in non-centrosymmetric structure and also responsible for
the control of molecular orientation in the crystal structure. The C-H…O interactions are
shown as dashed lines in Fig.8 and the corresponding geometric parameters are listed in
Table.4.
Moreover, the molecules packed in zig-zag head-to tail parallel fashion along the c-
axis contribute to the increased second order hyper-polarizability of the crystal [15-17, 21].
The details of the crystal data and refinement are given in Table 3. Further details such as
bond lengths, angles and torsion angles are shown in Table 5 and 6, respectively.

Fig.7. The molecular structure of MPP with atom-labelling scheme. Displacement ellipsoids
are drawn at the 50% probability level
Table 3
Crystallographic details of MPP
Formula
C15H13NO2
0.3X0.20X0.15
Acetone
Crystal Size (mm)
Solvent
Formula weight/gm mol-1
Temperature/K
Radiation
239.26
100 (2)
Mo K radiation
0.71073
Radiation Wavelength/Å
Crystal System
Space group
a/Å
Orthorhombic
Pna21
25.6311(3)
11.6419(2)
3.9742(1)
90
b/Å
c/Å
o
/
o
/
90

o
/
90
Volume/Å3
1185.88(4)
4
Z
Density/gcm-1
/mm-1
1.34
0.089
F(000)
504
range for data collection
hmin,max, kmin,max, lmin,max
No. of reflections
Measured No. of unique reflections
No. of parameters
No. of restraints
1.6- 27.50
(-30 33), (-15 15), (-5 5)
9579
1552
164
1
R_all, R_obs.
0.056, 0.054
0.160 , 0.156
1.11
wR2_all, wR2_obs.
Goodness of Fit on F2
min, max/e Å-3
-0.296 , 0.288
Table 4
Geometries of Intermolecular Interactions obtained from structural analysis of MPP
__________________________________________________________________________
Interactions
X-H [Å]
H-D [Å]
X-D [Å]
X-H-D[deg]
symmetry
___________________________________________________________________________
C4-H4…O2
C15-H15A…O1
C15-H15C…O1
0.95
0.98
0.979
2.521
2.583
2.677
3.429
3.504
3.572
59.9
x,-1+y, 1+z
x, 1+y,-1+z
156.63
152.18
-x, 2-y,-1/2+z
___________________________________________________________________________

Fig.8. A packing diagram of MPP displaying C H O intermolecular interactions as dashed
lines in the crystal lattice. (For clarity, hydrogen atoms except those involved in
intermolecular interactions are omitted).
3.5. Thermal studies
Thermo gravimetric (TG) and differential thermal analysis (DTA) was carried out for
MPP crystal in the temperature range of 270C to 5450C in nitrogen atmosphere using Perkin-
Elmer thermal analyzer. The TG/DTA curves are presented in Fig.9. The sharp endothermic
peak observed in DT curve at 810C corresponds to the melting point of MPP and at this
temperature no weight loss was observed in the TG curve. In the TG curve, the weight loss
occurs at around 1600C, which is due to the volatilization of the sample without being
decomposed. A major weight loss (about 41%) was observed over a large temperature range
from 1800C to 3550C which may be due to the decomposition of MPP. Though MPP is
chemically stable up to 1600C, it has lesser melting temperature compared to standard NLO
urea crystal which is 1300C [17].

Fig.9. TGA/DTA curves of MPP crystal
3.6. UV–VIS–NIR spectrum
Optical transparency is one of important parameter that a NLO material must possess.
Wider transparency is needed for most of the practical applications. UV–VIS–NIR absorption
spectrum of the crystal was recorded using a Varian, cary 5000 UV–VIS spectrophotometer in
the wavelength range of 200–1000 nm. A solution of MPP in DMF was placed in a 1 cm
cuvette for measurement. The recorded spectrum is shown in Fig. 10. The crystal has a wider
transparency range extending into the entire visible and IR region (cut off 410nm). The MPP
has a strong absorption band in the UV region at 345nm which is due to n-π* transition and is
attributed to the excitation of aromatic ring and C=O group. The MPP can be used for down
conversion of wavelength by SHG in the blue-green region of the electromagnetic spectrum.

Fig. 10. Optical absorption spectrum MPP crystal
3.7. Non linear optical property
The SHG efficiency of MPP was measured using the powder method developed by
Kurtz and Perry [18]. A Q-switched Nd: YAG laser beam of wavelength 1064 nm with 8ns
pulse width and beam energy of 1.3mJ/pulse is used as a source for powder SHG
measurement of the compound. The MPP crystal was powdered and packed in a micro-
capillary of uniform bore size and exposed to fundamental laser radiations. The output from
the sample was monochromated to collect the intensity of 532nm component and to eliminate
the fundamental wavelength. Second harmonic radiation generated by the randomly oriented
micro crystals was focused by a lens and detected by a photo multiplier tube. Two reference
standard samples viz urea and KDP were used for comparison purpose. The crystals of urea
and KDP are powdered to the same particle size as that of MPP sample was used as a
reference material for the present measurement. The SHG conversion efficiency of MPP
crystal was found to be 4.7 U (1U= SHG efficiency of urea) and 31 times greater than that of
KDP.

3.8. Structure-NLO property relationship
The molecular structure of MPP is shown in Fig.7. The MPP molecule contains an electron
donor methoxy group attached to the para-position of phenylene moiety and the carbonyl
group (-C=O-) along with the pyridine moiety at the other end acts as an electron acceptor.
The charge transfer takes place through the -conjugation path way formed by carbon-carbon
double bond connecting the electron donor and acceptor groups. Thus MPP molecule
possesses a D-π-A type push-pull structure where charge transfer is from end to end of the
molecule. This ensures the electronic delocalization within the molecule which helps to
possess optical nonlinearity. Ganapayya et al [11] reported that a pyridine based chalcone 3-
(2,3-Dimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one (DMPP) exhibits SHG efficiency
comparable to that of KDP. In the present case a single electron donating methoxy group is
attached at the para position of the phenylene moiety. It is observed that SHG efficiency of
MPP is greater than that of efficiency of DMPP. Also the SHG efficiency of MPP is 4.7U and
31 times larger than KDP. The substitution of an electron donor group at the para position of
the phenylene group increases the charge on the carbonyl group and results in an effective
transfer of charge from one end of the molecule to the other [5]. Wu et al[9] reported that the
substitution of a single electron donor group at the para position of the phenylene group is
more effective in enhancing the NLO response of the materials than two electron donating
methoxy groups at ortho and para position.
Further, it was observed in some organic crystals that the molecular dipoles are
aligned in parallel and zig-zag head-to-tail fashion resulted in enhanced SHG conversion
efficiency due to adding up of the individual molecular dipole contribution to create a net
polarization in the bulk crystal [5]. Such a head-to-tail parallel molecular dipole alignment
was observed in crystals like MMONS [20] and PDBA [21] which resulted in very high SHG
efficiency. In these crystals the hydrogen bond interactions are also expected to play a
combined role in enhancing the nonlinear optical effect during the excitation. Also, a chalcone
co-crystal (APTP/APBDP) reported by Ravindra et.al., [5] possess zig-zag head-to-tail
molecular dipoles alignment along crystallographic c-direction which resulted in SHG
efficiency of 7 times larger than that of Urea.
In order to understand the structure-NLO property relationship in MPP, the molecular
dipole was computed using MOPAC2012 [22] semi-empirical package and is shown in the
Fig.11 as inset. The packing diagram of MPP as viewed down the b-axis is shown in Fig.11.
The red arrows in Fig.11 represent molecular dipoles of MPP molecules in the crystal

structure. From the Fig.11, it is clear that the molecular dipoles of MPP are arranged in a zig-
zag head-to-tail fashion in which individual dipoles adds to establish a net polarization in the
crystal resulted in high SHG efficiency of 4.7U. The molecular dipoles of MPP make an angle
of 76.99o with respect to crystallographic c-axis. The observed high SHG efficiency of MPP is
attributed to the zig-zag head-to-tail alignment of molecular dipoles along c-axis in crystal
structure which helps in establishing the net polarization in the bulk crystal. Further, the
intermolecular interactions observed in crystal lattice of MPP are expected to play a promising
role in the excited state by extending the molecular charge transfer into supramolecular realm.
The MPP has good thermal and chemical stability, optical transparency and SHG efficiency
which make this material attractive for SHG applications.
Fig. 11. Packing diagram of MPP exhibiting zig-zag head-to-tail molecular diple alignement
along the crystallogrphic c-direction in the crystal structure (the hydrogen atoms are igonred
for clarity). The red arrows in the packing diagram represents the molecular dipoles of MPP.
The inset figure shows the molecular dipole of MPP computed using semiemperical package
MOPAC2012.

4. Conclusions
The new NLO chalcone derivative, MPP, was synthesized and single crystals of this
compound were successfully grown by the solution growth technique at room temperature
using acetone as a solvent. FT-IR and Laser Raman spectroscopy were used to confirm the
1
13
functional groups of the grown crystal. The structure was reconfirmed by H NMR and C
NMR spectral analysis. Single-crystal XRD studies shows that MPP crystallizes in
orthorhombic crystal system with noncentrosymmetric Pna21 space group. This crystal has a
powder SHG conversion efficiency of 4.7 times greater than that of urea. The high conversion
efficiency of MPP is attributed to zig-zag head-to-tail alignment of the dipoles along the c-
axis. The UV–VIS–NIR spectrum reveals that the crystal is transparent in the entire visible
region with cut off wavelength of 410 nm. The substitution of a single electron donor group at
the para position of the phenylene group was found to be more effective for enhancing NLO
response of the chalcone derivatives than two electron donating methoxy groups at ortho and
para position. Due to the presence of a wide transparency range and higher second harmonic
efficiency, the crystal may be used for frequency doubling and other NLO applications.
Acknowledgements
Authors are thankful to the University of Malaya for the structure determination of MPP
crystal. HJR thank DAE-BRNS for the project funding (Sanction no: 2012/34/18/BRNS). The
authors also acknowledge SAIF, IIT Madras and STIC, Cochin for providing experimental
facility.
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Table 5
Bond Lengths [Å] & Bond angles [deg]
Atoms
O1-C6
O2-C12
O2-C15
N1-C1
N1-C5
C1-H1
C1-C2
C2-H2
C2-C3
C3-H3
C3-C4
C4-H4
C4-C5
C5-C6
C6-C7
C7-H7
Length
1.220(4)
1.365(4)
1.433(4)
1.338(4)
1.343(4)
0.950(4)
1.393(5)
0.949(4)
1.382(5)
0.950(4)
1.385(5)
0.950(4)
1.391(5)
1.509(5)
1.480(5)
0.950(4)
1.341(5)
0.950(3)
1.467(5)
1.400(5)
1.393(5)
0.949(3)
1.395(5)
0.951(3)
1.386(5)
1.396(5)
0.950(3)
1.380(5)
0.951(3)
0.980(4)
0.980(4)
0.979(3)
Atoms
C12-O2-C15
C1-N1-C5
N1-C1-H1
N1-C1-C2
C1-C2-H2
C1-C2-C3
C2-C3-H3
C2-C3-C4
H3-C3-C4
C3-C4-C5
H4-C4-C5
N1-C5-C4
N1-C5-C6
C4-C5-C6
O1-C6-C5
O1-C6-C7
Angle
117.0(3)
117.3(3)
118.4(4)
123.3(3)
120.7(4)
118.5(4)
120.4(4)
119.2(4)
120.4(4)
118.3(3)
120.8(3)
123.4(3)
117.3(3)
119.3(3)
120.2(3)
122.9(3)
116.9(3)
117.2(3)
125.6(3)
119.0(3)
123.0(3)
118.0(3)
119.2(3)
121.5(3)
119.3(3)
120.5(3)
119.0(3)
124.4(3)
115.4(3)
120.2(3)
119.4(3)
109.5(3)
C7-C8
C8-H8
C8-C9
C5-C6-C7
C7-C8-H8
C7-C8-C9
C9-C10
C9-C14
C10-H10
C10-C11
C11-H11
C11-C12
C12-C13
C13-H13
C13-C14
C14-H14
C15-H15A
C15-H15B
C15-H15C
C8-C9-C10
C8-C9-C14
C10-C9-C14
C9-C10-H10
C9-C10-C11
H10-C10-C11
C10-C11-H11
C10-C11-C12
O2-C12-C11
O2-C12-C13
C11-C12-C13
C9-C14-H14
O2-C15-H15A

Table 6
Torsion angles [deg]
Atoms
C15‐O2‐C12‐C11
C15‐O2‐C12‐C13
C12‐O2‐C15‐H15A
C12‐O2‐C15‐H15B
C12‐O2‐C15‐H15C
C5‐N1‐C1‐H1
C5‐N1‐C1‐C2
C1‐N1‐C5‐C4
C1‐N1‐C5‐C6
N1‐C1‐C2‐H2
N1‐C1‐C2‐C3
H1‐C1‐C2‐H2
H1‐C1‐C2‐C3
C1‐C2‐C3‐H3
C1‐C2‐C3‐C4
H2‐C2‐C3‐H3
H2‐C2‐C3‐C4
C2‐C3‐C4‐H4
C2‐C3‐C4‐C5
H3‐C3‐C4‐H4
H3‐C3‐C4‐C5
C3‐C4‐C5‐N1
C3‐C4‐C5‐C6
H4‐C4‐C5‐N1
H4‐C4‐C5‐C6
N1‐C5‐C6‐O1
N1‐C5‐C6‐C7
C4‐C5‐C6‐O1
C4‐C5‐C6‐C7
O1‐C6‐C7‐H7
O1‐C6‐C7‐C8
Torsion
5.4(5)
Atoms
C5‐C6‐C7‐C8
C6‐C7‐C8‐H8
C‐C7‐C8‐C9
H7‐C7‐C8‐H8
H7‐C7‐C8‐C9
C7‐C8‐C9‐C10
C7‐C8‐C9‐C14
Torsion
‐176.0(3)
0.4(5)
‐179.7(3)
‐179.7(3)
0.3(6)
176.2(3)
‐6.6(6)
‐3.8(5)
173.4(3)
0.7(5)
‐179.4(3)
‐176.7(3)
3.2(5)
‐179.1(3)
0.9(6)
‐1.8(5)
‐174.3(3)
178.0(3)
57.9(4)
‐62.1(4)
179.1(3)
‐0.9(5)
1.1(5)
H8‐C8‐C9‐C10
H8‐C8‐C9‐C14
‐179.0(3)
‐179.9(4)
0.2(6)
C8‐C9‐C10‐H10
C8‐C9‐C10‐C11
C14‐C9‐C10‐H10
C14‐C9‐C10‐C11
C8‐C9‐C14‐C13
C8‐C9‐C14‐H14
C10‐C9‐C14‐C13
C10‐C9‐C14‐H14
C9‐C10‐C11‐H11
C9‐C10‐C11‐C12
H10‐C10‐C11‐H11
H10‐C10‐C11‐C12
C10‐C11‐C12‐O2
C10‐C11‐C12‐C13
H11‐C11‐C12‐O2
H11‐C11‐C12‐C13
O2‐C12‐C13‐H13
O2‐C12‐C13‐C14
C11‐C12‐C13‐H13
C11‐C12‐C13‐C14
C12‐C13‐C14‐H14
H13‐C13‐C14‐C9
0.1(6)
‐179.8(4)
‐179.5(4)
0.5(6)
0.6(7)
‐179.4(4)
179.5(4)
‐0.4(6)
‐0.4(6)
179.6(4)
‐0.4(5)
179.7(3)
179.7(3)
‐0.3(5)
‐177.0(3)
2.8(5)
178.2(3)
177.9(3)
‐2.1(5)
‐2.2(6)
177.9(3)
179.8(3)
‐0.5(5)
‐0.2(6)
179.5(3)
1.6(5)
‐178.4(3)
‐178.0(3)
2.0(5)
179.3(3)
179.2(3)
3.0(5)
‐177.3(3)
‐176.2(4)
3.8(6)

Highlights (for review)
A new high efficient NLO Material 3-(4-Methoxyphenyl)-1-(pyridin-2-yl) prop-2-
en-1-one is synthesized and grown using slow evaporation technique
The replacement of phenyl group by pyridine group significantly alters the NLO
response.
The substitution of a single electron donor at the para position of the phenylene
moiety increases the SHG efficiency.