Crystal structure of 3-(4-methyl­phen­yl)-1-phenyl-5-[(E)-2-phenyl­ethen­yl]-1H-pyrazole

Adam, F.; Charishma, S.P.; Prabhu, B.R.; Samshuddin, S.; Ameram, N.

doi:10.1107/S2056989015022811

organic compounds

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Volume 71| Part 12| December 2015| Page o1020

https://doi.org/10.1107/S2056989015022811

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Crystal structure of 3-(4-methylphenyl)-1-phenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole

Farook Adam,^a ^* Sharath Poojary Charishma,^b Basrur Ramya Prabhu,^b Seranthimata Samshuddin ^b and Nadiah Ameram ^a

^aSchool of Chemical Sciences,Universiti Sains Malaysia, 18000, Pulau Pinang, Malaysia, and ^bDepartment of P.G. Studies in Chemistry, Alvas College, Moodbidri, Karnataka, 574 227, India
^*Correspondence e-mail: farook@usm.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 November 2015; accepted 28 November 2015; online 6 December 2015)

In the title compound, C₂₄H₂₀N₂, the dihedral angles between the pyrazole ring and the pendant phenyl, toluoyl and phenylethenyl rings are 41.50 (8), 4.41 (8) and 31.07 (8)°, respectively. In the crystal, inversion dimers linked by a π–π stacking interactions between the phenylethenyl rings are observed [centroid–centroid separation = 3.5857 (9) Å].

Keywords: crystal structure; pyrazole; π–π stacking interactions.

CCDC reference: 1439397

1. Related literature

For background to pyrazoles, see: Samshuddin et al. (2012 ); Sarojini et al. (2010 ); For related crystal structures, see: Jasinski et al. (2012 ); Baktır et al. (2011 ).

2. Experimental

2.1. Crystal data

C₂₄H₂₀N₂
M_r = 336.42
Monoclinic, P 2₁ /c
a = 9.6470 (8) Å
b = 14.1077 (12) Å
c = 14.0062 (12) Å
β = 104.891 (1)°
V = 1842.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.38 × 0.24 × 0.14 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.915, T_max = 0.963
32138 measured reflections
5495 independent reflections
4226 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.167
S = 1.04
5495 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1439397

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015022811/hb7552sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022811/hb7552Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015022811/hb7552Isup3.cml

checkCIF report

Comment top

Pyrazoles are well known as important structural units in a wide variety of biologically active natural products as well as useful synthetic intermediates (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines were utilized in industries as scintillation solutes and as fluorescent agents. The crystal structures of some pyrazolines viz., 3,5-bis(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, 3,5-bis(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (Baktir et al., 2011) have been reported. In view of the importance of pyrazolines, the title compound (I) is prepared and its crystal structure is reported.

Related literature top

For background to pyrazoles, see: Samshuddin et al. (2012); Sarojini et al. (2010); For related crystal structures, see: Jasinski et al. (2012); Baktir et al. (2011).

Experimental top

A mixture of (2E,4E)-1-(4-methylphenyl)-5-phenylpenta-2,4-dien-1-one (2.48 g, 0.01 mol) and phenylhydrazine (1.08 g,0.01 mol) in 30 ml acetic acid was refluxed for 10 hours. The reaction mixture was cooled and poured into 500 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Colourless blocks were grown from acetone solution by slow evaporation; m. p. 471-474 K. Yield: 63%.

Structure description top

For background to pyrazoles, see: Samshuddin et al. (2012); Sarojini et al. (2010); For related crystal structures, see: Jasinski et al. (2012); Baktir et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound.

3-(4-Methylphenyl)-1-phenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole top

Crystal data top

C₂₄H₂₀N₂	D_x = 1.213 Mg m⁻³
M_r = 336.42	Melting point = 471–474 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6470 (8) Å	Cell parameters from 9097 reflections
b = 14.1077 (12) Å	θ = 2.2–30.1°
c = 14.0062 (12) Å	µ = 0.07 mm⁻¹
β = 104.891 (1)°	T = 100 K
V = 1842.2 (3) Å³	Block, colourless
Z = 4	0.38 × 0.24 × 0.14 mm
F(000) = 712

Data collection top

Bruker APEXII CCD diffractometer	4226 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 30.3°, θ_min = 2.1°
T_min = 0.915, T_max = 0.963	h = −13→13
32138 measured reflections	k = −19→20
5495 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0767P)² + 0.886P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5495 reflections	Δρ_max = 0.57 e Å⁻³
236 parameters	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₄H₂₀N₂	V = 1842.2 (3) Å³
M_r = 336.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6470 (8) Å	µ = 0.07 mm⁻¹
b = 14.1077 (12) Å	T = 100 K
c = 14.0062 (12) Å	0.38 × 0.24 × 0.14 mm
β = 104.891 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5495 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	4226 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.963	R_int = 0.033
32138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.04	Δρ_max = 0.57 e Å⁻³
5495 reflections	Δρ_min = −0.24 e Å⁻³
236 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.64167 (12)	0.60320 (9)	0.42861 (8)	0.0265 (3)
N2	0.69140 (12)	0.59884 (9)	0.52903 (8)	0.0269 (3)
C1	0.10080 (17)	0.75054 (12)	0.13886 (13)	0.0383 (4)
H1A	0.0740	0.7816	0.1916	0.046*
C2	0.02522 (18)	0.76888 (14)	0.04221 (14)	0.0437 (4)
H2A	−0.0527	0.8122	0.0295	0.052*
C3	0.06214 (17)	0.72491 (14)	−0.03526 (13)	0.0423 (4)
H3A	0.0112	0.7387	−0.1013	0.051*
C4	0.17484 (18)	0.65993 (15)	−0.01636 (13)	0.0417 (4)
H4A	0.1995	0.6282	−0.0695	0.050*
C5	0.25128 (16)	0.64156 (12)	0.08087 (12)	0.0355 (4)
H5A	0.3284	0.5976	0.0934	0.043*
C6	0.21586 (14)	0.68694 (11)	0.15970 (11)	0.0296 (3)
C7	0.29464 (15)	0.67433 (11)	0.26385 (11)	0.0298 (3)
H7A	0.2541	0.7019	0.3124	0.036*
C8	0.41821 (15)	0.62750 (11)	0.29599 (11)	0.0275 (3)
H8A	0.4572	0.5962	0.2488	0.033*
C9	0.49623 (14)	0.62204 (10)	0.39980 (10)	0.0254 (3)
C10	0.45197 (14)	0.63017 (10)	0.48572 (10)	0.0261 (3)
H10A	0.3578	0.6433	0.4913	0.031*
C11	0.57660 (14)	0.61475 (10)	0.56396 (10)	0.0242 (3)
C12	0.59023 (15)	0.61272 (10)	0.67117 (10)	0.0249 (3)
C13	0.72390 (16)	0.60008 (11)	0.73861 (11)	0.0302 (3)
H13A	0.8072	0.5928	0.7150	0.036*
C14	0.73624 (18)	0.59809 (12)	0.83953 (11)	0.0359 (4)
H14A	0.8279	0.5893	0.8840	0.043*
C15	0.61633 (19)	0.60878 (12)	0.87664 (12)	0.0370 (4)
C16	0.48304 (19)	0.61886 (13)	0.80913 (12)	0.0377 (4)
H16A	0.3994	0.6243	0.8327	0.045*
C17	0.46994 (16)	0.62111 (11)	0.70806 (11)	0.0317 (3)
H17A	0.3779	0.6284	0.6637	0.038*
C18	0.74029 (14)	0.59214 (10)	0.37003 (10)	0.0261 (3)
C19	0.73476 (15)	0.65173 (11)	0.28996 (10)	0.0296 (3)
H19A	0.6638	0.6999	0.2731	0.036*
C20	0.83463 (17)	0.63971 (12)	0.23509 (11)	0.0344 (3)
H20A	0.8307	0.6791	0.1795	0.041*
C21	0.94044 (17)	0.57045 (13)	0.26085 (12)	0.0361 (4)
H21A	1.0084	0.5627	0.2230	0.043*
C22	0.94626 (17)	0.51269 (12)	0.34226 (12)	0.0358 (3)
H22A	1.0196	0.4662	0.3607	0.043*
C23	0.84600 (15)	0.52252 (11)	0.39652 (11)	0.0302 (3)
H23A	0.8490	0.4822	0.4514	0.036*
C24	0.6314 (3)	0.61195 (17)	0.98668 (13)	0.0542 (5)
H24A	0.7114	0.5714	1.0205	0.081*
H24B	0.5426	0.5893	1.0006	0.081*
H24C	0.6500	0.6773	1.0103	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0212 (5)	0.0337 (6)	0.0215 (5)	−0.0003 (4)	0.0000 (4)	0.0022 (4)
N2	0.0236 (5)	0.0334 (7)	0.0207 (5)	−0.0019 (4)	0.0000 (4)	0.0029 (4)
C1	0.0330 (8)	0.0356 (9)	0.0409 (9)	0.0033 (6)	0.0000 (6)	0.0059 (7)
C2	0.0317 (8)	0.0431 (10)	0.0480 (10)	0.0059 (7)	−0.0049 (7)	0.0160 (8)
C3	0.0286 (7)	0.0552 (11)	0.0353 (8)	−0.0063 (7)	−0.0061 (6)	0.0203 (8)
C4	0.0344 (8)	0.0574 (11)	0.0316 (8)	−0.0025 (7)	0.0052 (6)	0.0101 (7)
C5	0.0247 (6)	0.0409 (9)	0.0377 (8)	0.0027 (6)	0.0024 (6)	0.0123 (7)
C6	0.0213 (6)	0.0294 (7)	0.0325 (7)	−0.0036 (5)	−0.0033 (5)	0.0090 (6)
C7	0.0256 (6)	0.0299 (7)	0.0306 (7)	0.0013 (5)	0.0014 (5)	0.0007 (6)
C8	0.0231 (6)	0.0298 (7)	0.0265 (7)	−0.0018 (5)	0.0007 (5)	0.0027 (5)
C9	0.0221 (6)	0.0241 (7)	0.0262 (6)	0.0012 (5)	−0.0005 (5)	0.0006 (5)
C10	0.0234 (6)	0.0241 (7)	0.0278 (7)	0.0015 (5)	0.0010 (5)	−0.0001 (5)
C11	0.0230 (6)	0.0218 (6)	0.0255 (6)	−0.0011 (5)	0.0018 (5)	0.0005 (5)
C12	0.0266 (6)	0.0217 (6)	0.0248 (6)	−0.0010 (5)	0.0040 (5)	−0.0015 (5)
C13	0.0265 (6)	0.0347 (8)	0.0276 (7)	−0.0018 (5)	0.0035 (5)	0.0007 (6)
C14	0.0371 (8)	0.0388 (9)	0.0271 (7)	−0.0030 (6)	−0.0004 (6)	−0.0002 (6)
C15	0.0484 (9)	0.0354 (8)	0.0265 (7)	0.0006 (7)	0.0086 (6)	−0.0029 (6)
C16	0.0405 (8)	0.0409 (9)	0.0346 (8)	0.0071 (7)	0.0150 (7)	−0.0015 (7)
C17	0.0305 (7)	0.0319 (8)	0.0317 (7)	0.0041 (6)	0.0065 (6)	−0.0027 (6)
C18	0.0206 (6)	0.0323 (7)	0.0227 (6)	−0.0040 (5)	0.0004 (5)	0.0003 (5)
C19	0.0268 (6)	0.0341 (8)	0.0240 (6)	−0.0040 (5)	−0.0004 (5)	0.0028 (5)
C20	0.0355 (8)	0.0434 (9)	0.0221 (6)	−0.0076 (6)	0.0032 (5)	0.0023 (6)
C21	0.0331 (7)	0.0455 (9)	0.0300 (7)	−0.0048 (7)	0.0086 (6)	−0.0030 (7)
C22	0.0291 (7)	0.0394 (9)	0.0376 (8)	0.0009 (6)	0.0061 (6)	−0.0003 (7)
C23	0.0250 (6)	0.0352 (8)	0.0280 (7)	−0.0013 (6)	0.0024 (5)	0.0042 (6)
C24	0.0701 (13)	0.0646 (13)	0.0279 (8)	0.0045 (11)	0.0123 (8)	−0.0029 (8)

Geometric parameters (Å, º) top

N1—N2	1.3657 (15)	C12—C13	1.4003 (19)
N1—C9	1.3824 (17)	C13—C14	1.388 (2)
N1—C18	1.4156 (18)	C13—H13A	0.9500
N2—C11	1.3397 (18)	C14—C15	1.393 (2)
C1—C2	1.387 (2)	C14—H14A	0.9500
C1—C6	1.398 (2)	C15—C16	1.394 (2)
C1—H1A	0.9500	C15—C24	1.511 (2)
C2—C3	1.374 (3)	C16—C17	1.389 (2)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.394 (3)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.392 (2)
C4—C5	1.396 (2)	C18—C23	1.396 (2)
C4—H4A	0.9500	C19—C20	1.389 (2)
C5—C6	1.393 (2)	C19—H19A	0.9500
C5—H5A	0.9500	C20—C21	1.392 (2)
C6—C7	1.472 (2)	C20—H20A	0.9500
C7—C8	1.336 (2)	C21—C22	1.391 (2)
C7—H7A	0.9500	C21—H21A	0.9500
C8—C9	1.4574 (19)	C22—C23	1.382 (2)
C8—H8A	0.9500	C22—H22A	0.9500
C9—C10	1.381 (2)	C23—H23A	0.9500
C10—C11	1.4201 (18)	C24—H24A	0.9800
C10—H10A	0.9500	C24—H24B	0.9800
C11—C12	1.4736 (19)	C24—H24C	0.9800
C12—C17	1.391 (2)

N2—N1—C9	111.77 (11)	C14—C13—C12	120.84 (14)
N2—N1—C18	118.78 (11)	C14—C13—H13A	119.6
C9—N1—C18	129.41 (12)	C12—C13—H13A	119.6
C11—N2—N1	105.30 (11)	C13—C14—C15	121.05 (15)
C2—C1—C6	120.89 (17)	C13—C14—H14A	119.5
C2—C1—H1A	119.6	C15—C14—H14A	119.5
C6—C1—H1A	119.6	C14—C15—C16	117.89 (14)
C3—C2—C1	120.57 (16)	C14—C15—C24	120.83 (16)
C3—C2—H2A	119.7	C16—C15—C24	121.27 (17)
C1—C2—H2A	119.7	C17—C16—C15	121.34 (15)
C2—C3—C4	119.65 (15)	C17—C16—H16A	119.3
C2—C3—H3A	120.2	C15—C16—H16A	119.3
C4—C3—H3A	120.2	C16—C17—C12	120.70 (14)
C3—C4—C5	119.85 (18)	C16—C17—H17A	119.7
C3—C4—H4A	120.1	C12—C17—H17A	119.7
C5—C4—H4A	120.1	C19—C18—C23	120.89 (14)
C6—C5—C4	120.81 (15)	C19—C18—N1	120.55 (13)
C6—C5—H5A	119.6	C23—C18—N1	118.52 (13)
C4—C5—H5A	119.6	C20—C19—C18	118.94 (14)
C5—C6—C1	118.21 (14)	C20—C19—H19A	120.5
C5—C6—C7	124.10 (13)	C18—C19—H19A	120.5
C1—C6—C7	117.67 (15)	C19—C20—C21	120.61 (14)
C8—C7—C6	125.62 (15)	C19—C20—H20A	119.7
C8—C7—H7A	117.2	C21—C20—H20A	119.7
C6—C7—H7A	117.2	C22—C21—C20	119.75 (15)
C7—C8—C9	123.35 (14)	C22—C21—H21A	120.1
C7—C8—H8A	118.3	C20—C21—H21A	120.1
C9—C8—H8A	118.3	C23—C22—C21	120.36 (15)
C10—C9—N1	106.23 (11)	C23—C22—H22A	119.8
C10—C9—C8	131.97 (13)	C21—C22—H22A	119.8
N1—C9—C8	121.78 (13)	C22—C23—C18	119.42 (14)
C9—C10—C11	105.64 (12)	C22—C23—H23A	120.3
C9—C10—H10A	127.2	C18—C23—H23A	120.3
C11—C10—H10A	127.2	C15—C24—H24A	109.5
N2—C11—C10	111.06 (12)	C15—C24—H24B	109.5
N2—C11—C12	120.22 (12)	H24A—C24—H24B	109.5
C10—C11—C12	128.72 (13)	C15—C24—H24C	109.5
C17—C12—C13	118.14 (13)	H24A—C24—H24C	109.5
C17—C12—C11	120.82 (13)	H24B—C24—H24C	109.5
C13—C12—C11	121.02 (13)

C9—N1—N2—C11	0.18 (16)	C10—C11—C12—C17	4.1 (2)
C18—N1—N2—C11	177.93 (12)	N2—C11—C12—C13	4.0 (2)
C6—C1—C2—C3	−0.1 (3)	C10—C11—C12—C13	−177.46 (14)
C1—C2—C3—C4	1.2 (3)	C17—C12—C13—C14	−1.4 (2)
C2—C3—C4—C5	−1.4 (3)	C11—C12—C13—C14	−179.92 (14)
C3—C4—C5—C6	0.4 (3)	C12—C13—C14—C15	−0.1 (3)
C4—C5—C6—C1	0.7 (2)	C13—C14—C15—C16	1.8 (3)
C4—C5—C6—C7	−177.47 (15)	C13—C14—C15—C24	−176.62 (17)
C2—C1—C6—C5	−0.8 (2)	C14—C15—C16—C17	−1.9 (3)
C2—C1—C6—C7	177.42 (15)	C24—C15—C16—C17	176.47 (17)
C5—C6—C7—C8	8.2 (2)	C15—C16—C17—C12	0.4 (3)
C1—C6—C7—C8	−169.96 (16)	C13—C12—C17—C16	1.3 (2)
C6—C7—C8—C9	176.13 (14)	C11—C12—C17—C16	179.79 (14)
N2—N1—C9—C10	0.13 (16)	N2—N1—C18—C19	−136.00 (14)
C18—N1—C9—C10	−177.32 (14)	C9—N1—C18—C19	41.3 (2)
N2—N1—C9—C8	−178.33 (13)	N2—N1—C18—C23	41.74 (19)
C18—N1—C9—C8	4.2 (2)	C9—N1—C18—C23	−140.95 (15)
C7—C8—C9—C10	24.7 (3)	C23—C18—C19—C20	1.3 (2)
C7—C8—C9—N1	−157.24 (15)	N1—C18—C19—C20	179.02 (13)
N1—C9—C10—C11	−0.37 (15)	C18—C19—C20—C21	−1.3 (2)
C8—C9—C10—C11	177.87 (15)	C19—C20—C21—C22	0.0 (2)
N1—N2—C11—C10	−0.42 (16)	C20—C21—C22—C23	1.2 (2)
N1—N2—C11—C12	178.39 (12)	C21—C22—C23—C18	−1.2 (2)
C9—C10—C11—N2	0.50 (16)	C19—C18—C23—C22	−0.1 (2)
C9—C10—C11—C12	−178.17 (13)	N1—C18—C23—C22	−177.85 (13)
N2—C11—C12—C17	−174.51 (14)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂
M_r	336.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.6470 (8), 14.1077 (12), 14.0062 (12)
β (°)	104.891 (1)
V (Å³)	1842.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.24 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014)
T_min, T_max	0.915, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	32138, 5495, 4226
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.167, 1.04
No. of reflections	5495
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.24

Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXS97 (Sheldrick 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008).

Acknowledgements

SS thanks Alva's Education Foundation, Moodbidri, for the research facilities. The authors are thankful for RU Research grant 1001/PKIMIA/811269.

References

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