organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-{3-(4-Methyl­phen­yl)-5-[5-(2-nitro­phen­yl)furan-2-yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: dr@physics.uni-mysore.ac.in

(Received 2 September 2013; accepted 4 September 2013; online 12 September 2013)

In the title compound, C22H19N3O4, the dihedral angle between the furan and pyrazole rings is 82.73 (19)° while the dihedral angles between the furan and pyrazole rings and their attached benzene rings are 31.93 (18) and 1.88 (18)°, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R22(16) loops. In addition, weak C—H⋯π and aromatic ππ stacking [minimum centroid–centroid distance = 3.5374 (17) Å] inter­actions are observed.

Related literature

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008[Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918-922.]); Husain et al. (2008[Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393-403.]).

[Scheme 1]

Experimental

Crystal data
  • C22H19N3O4

  • Mr = 389.40

  • Triclinic, [P \overline 1]

  • a = 7.6235 (3) Å

  • b = 10.5652 (4) Å

  • c = 13.1177 (4) Å

  • α = 103.344 (2)°

  • β = 95.025 (2)°

  • γ = 108.221 (2)°

  • V = 961.78 (6) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.78 mm−1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.842, Tmax = 0.854

  • 10640 measured reflections

  • 3083 independent reflections

  • 2186 reflections with I > 2σ(I)

  • Rint = 0.138

Refinement
  • R[F2 > 2σ(F2)] = 0.084

  • wR(F2) = 0.242

  • S = 1.06

  • 3083 reflections

  • 265 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C23–C28 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O19i 0.93 2.56 3.462 (4) 162
C18—H18CCg4ii 0.96 2.69 3.595 (4) 158
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The ongoing work in our lab for synthesizing pyrozoline derivatives resulted the title molecule. Similar compounds are used for the preparation of drugs in the pharmacological industries (Amir et al., 2008; Husain et al., 2008).

In the title compound (Fig. 1), the pyrazole ring makes a dihedral angle of 82.73 (19) °, 88.84 (18) ° and 1.88 (18) ° with furan, nitrophenyl and terminal methylphenyl rings, respectively. The furan ring makes a dihedral angle of 82.35 (18) ° and 31.93 (18) ° with methyl phenyl and nitrophenyl rings, respectively. The dihedral angle between terminal nitrophenyl and methylphenyl ring is 88.23 (17) °.

The title molecules are linked to one another with C14—H14···O19 intermolecular hydrogen bonds with R22(16) ring motif (Fig. 2 and Table 1). In addition, short contacts C—H···π (Cg4) with distance 3.595 (4) Å (angle 158 °) [-x, -y, z - 1]. And π···π between Cg2 and Cg1 with distance 3.5374 (17) ° [x,y,z] and between Cg2 and Cg4 with a distance 3.641 (2) ° [x - 1, -y, z - 1] were observed, where Cg1:O11/C10/C14/C13/C12, Cg2:N16/N20/C21/C22/C15 and Cg4:C23/C24/C25/C26/C27/C28.

Related literature top

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008); Husain et al. (2008).

Experimental top

A mixture of 4-methylphenyl-3-[5-(2-nitrophenyl)furan-2-yl]prop-2-en-1-one (10 mmol), hydrazine hydrate (50 mmol) and glacial acetic acid (40 ml) were refluxed for 24 h. The resulting mixture was poured into water (100 ml) and allowed to stand. The precipitate that formed was separated by filtration, washed with cold water and then recrystallized from mixed DMF-ethanol solvents to yield brown blocks.

Refinement top

All the H atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELX:97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram of molecule, viewed along the crystallographic a axis. Dotted lines represent hydrogen bonds.
1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone top
Crystal data top
C22H19N3O4Z = 2
Mr = 389.40F(000) = 408
Triclinic, P1Dx = 1.345 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 7.6235 (3) ÅCell parameters from 3083 reflections
b = 10.5652 (4) Åθ = 3.5–64.8°
c = 13.1177 (4) ŵ = 0.78 mm1
α = 103.344 (2)°T = 296 K
β = 95.025 (2)°Block, brown
γ = 108.221 (2)°0.23 × 0.22 × 0.21 mm
V = 961.78 (6) Å3
Data collection top
Bruker X8 Proteum CCD
diffractometer
3083 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode2186 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.138
Detector resolution: 10.7 pixels mm-1θmax = 64.8°, θmin = 3.5°
ϕ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1212
Tmin = 0.842, Tmax = 0.854l = 1415
10640 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084H-atom parameters constrained
wR(F2) = 0.242 w = 1/[σ2(Fo2) + (0.1607P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3083 reflectionsΔρmax = 0.40 e Å3
265 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (3)
Crystal data top
C22H19N3O4γ = 108.221 (2)°
Mr = 389.40V = 961.78 (6) Å3
Triclinic, P1Z = 2
a = 7.6235 (3) ÅCu Kα radiation
b = 10.5652 (4) ŵ = 0.78 mm1
c = 13.1177 (4) ÅT = 296 K
α = 103.344 (2)°0.23 × 0.22 × 0.21 mm
β = 95.025 (2)°
Data collection top
Bruker X8 Proteum CCD
diffractometer
3083 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
2186 reflections with I > 2σ(I)
Tmin = 0.842, Tmax = 0.854Rint = 0.138
10640 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0840 restraints
wR(F2) = 0.242H-atom parameters constrained
S = 1.06Δρmax = 0.40 e Å3
3083 reflectionsΔρmin = 0.38 e Å3
265 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O80.2462 (4)0.4170 (3)0.8072 (2)0.0736 (10)
O90.0362 (6)0.3831 (5)0.6738 (2)0.1186 (18)
O110.1066 (3)0.1532 (2)0.82063 (14)0.0429 (7)
O190.0746 (4)0.2396 (2)0.77708 (19)0.0647 (9)
N70.0831 (5)0.3916 (3)0.7666 (2)0.0603 (11)
N160.1731 (4)0.0929 (2)0.67816 (18)0.0445 (8)
N200.1833 (4)0.0661 (2)0.57957 (19)0.0423 (8)
C10.2096 (5)0.2889 (3)0.9665 (3)0.0561 (11)
C20.3242 (5)0.3645 (4)0.9620 (3)0.0652 (14)
C30.3090 (5)0.4456 (4)0.8924 (3)0.0649 (14)
C40.1778 (5)0.4506 (3)0.8273 (3)0.0587 (11)
C50.0621 (4)0.3744 (3)0.8330 (2)0.0469 (10)
C60.0729 (4)0.2910 (3)0.9021 (2)0.0418 (9)
C100.0452 (4)0.2079 (3)0.9105 (2)0.0425 (9)
C120.2155 (4)0.0806 (3)0.8501 (2)0.0415 (9)
C130.2212 (5)0.0893 (3)0.9544 (2)0.0497 (11)
C140.1110 (5)0.1697 (3)0.9934 (2)0.0505 (11)
C150.3075 (4)0.0204 (3)0.7665 (2)0.0447 (10)
C170.0708 (5)0.2192 (3)0.6880 (2)0.0472 (11)
C180.0432 (5)0.3260 (3)0.5893 (3)0.0592 (11)
C210.3124 (4)0.0530 (3)0.5932 (2)0.0414 (9)
C220.4090 (4)0.1216 (3)0.7063 (2)0.0502 (10)
C230.3564 (4)0.1109 (3)0.5040 (2)0.0440 (10)
C240.2619 (4)0.0440 (3)0.4011 (3)0.0487 (10)
C250.3054 (5)0.1030 (3)0.3190 (3)0.0539 (12)
C260.4428 (5)0.2314 (4)0.3360 (3)0.0556 (12)
C270.5380 (5)0.2980 (4)0.4389 (3)0.0628 (12)
C280.4980 (5)0.2405 (3)0.5222 (3)0.0565 (11)
C290.4863 (6)0.2965 (5)0.2462 (4)0.0812 (17)
H10.222700.234501.013800.0670*
H20.413500.361401.006200.0780*
H30.387800.496900.889800.0780*
H40.167000.504700.779800.0700*
H130.285600.049700.993700.0600*
H140.088300.191901.062700.0610*
H150.396800.014900.798600.0540*
H18A0.083500.415100.603000.0890*
H18B0.031400.327800.534000.0890*
H18C0.150800.303800.567200.0890*
H22A0.395300.211300.731800.0600*
H22B0.541400.133600.713700.0600*
H240.167900.042000.387100.0580*
H250.240600.055400.250400.0650*
H270.631700.384000.452300.0750*
H280.564800.287600.590500.0680*
H29A0.371700.280300.200400.1220*
H29B0.564600.256200.206300.1220*
H29C0.550400.394400.274700.1220*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O80.0562 (17)0.0598 (16)0.093 (2)0.0000 (13)0.0194 (14)0.0235 (14)
O90.146 (3)0.173 (4)0.052 (2)0.063 (3)0.025 (2)0.045 (2)
O110.0469 (13)0.0401 (11)0.0322 (11)0.0069 (9)0.0038 (9)0.0041 (9)
O190.0872 (19)0.0492 (14)0.0484 (15)0.0091 (12)0.0117 (12)0.0156 (11)
N70.074 (2)0.0525 (17)0.0494 (18)0.0117 (15)0.0152 (15)0.0165 (13)
N160.0507 (16)0.0337 (13)0.0352 (14)0.0011 (11)0.0061 (11)0.0024 (10)
N200.0471 (15)0.0354 (13)0.0372 (14)0.0060 (11)0.0074 (11)0.0073 (10)
C10.053 (2)0.0454 (18)0.058 (2)0.0071 (16)0.0147 (16)0.0032 (15)
C20.046 (2)0.055 (2)0.076 (3)0.0071 (17)0.0142 (17)0.0045 (18)
C30.049 (2)0.052 (2)0.077 (3)0.0146 (17)0.0064 (19)0.0037 (18)
C40.054 (2)0.0459 (19)0.062 (2)0.0099 (16)0.0063 (17)0.0042 (16)
C50.0431 (18)0.0403 (16)0.0397 (17)0.0005 (14)0.0028 (13)0.0006 (13)
C60.0390 (17)0.0326 (15)0.0387 (16)0.0003 (12)0.0022 (12)0.0003 (12)
C100.0443 (17)0.0364 (15)0.0343 (16)0.0024 (13)0.0076 (12)0.0017 (12)
C120.0425 (17)0.0342 (15)0.0372 (16)0.0050 (13)0.0002 (12)0.0034 (12)
C130.061 (2)0.0467 (18)0.0371 (18)0.0125 (16)0.0043 (14)0.0129 (14)
C140.065 (2)0.0474 (18)0.0332 (17)0.0101 (16)0.0105 (14)0.0116 (13)
C150.0438 (18)0.0418 (16)0.0360 (17)0.0050 (13)0.0009 (13)0.0035 (13)
C170.056 (2)0.0347 (16)0.0447 (19)0.0083 (14)0.0122 (14)0.0079 (13)
C180.067 (2)0.0382 (17)0.052 (2)0.0020 (16)0.0078 (17)0.0026 (15)
C210.0368 (16)0.0359 (15)0.0432 (17)0.0043 (12)0.0065 (12)0.0066 (12)
C220.0432 (18)0.0457 (17)0.0453 (19)0.0002 (14)0.0049 (13)0.0037 (14)
C230.0371 (17)0.0373 (15)0.0501 (19)0.0035 (13)0.0059 (13)0.0111 (13)
C240.0404 (17)0.0403 (16)0.052 (2)0.0003 (13)0.0050 (14)0.0070 (14)
C250.050 (2)0.054 (2)0.048 (2)0.0048 (16)0.0060 (15)0.0147 (15)
C260.045 (2)0.057 (2)0.064 (2)0.0092 (16)0.0070 (15)0.0276 (17)
C270.048 (2)0.052 (2)0.072 (2)0.0072 (16)0.0014 (17)0.0230 (18)
C280.0463 (19)0.0471 (18)0.056 (2)0.0073 (15)0.0026 (15)0.0128 (15)
C290.076 (3)0.082 (3)0.083 (3)0.006 (2)0.011 (2)0.048 (2)
Geometric parameters (Å, º) top
O8—N71.229 (5)C23—C281.406 (5)
O9—N71.213 (4)C24—C251.379 (5)
O11—C101.376 (3)C25—C261.385 (5)
O11—C121.381 (4)C26—C271.384 (5)
O19—C171.236 (4)C26—C291.507 (6)
N7—C51.461 (5)C27—C281.380 (5)
N16—N201.390 (3)C1—H10.9300
N16—C151.487 (4)C2—H20.9300
N16—C171.361 (4)C3—H30.9300
N20—C211.294 (4)C4—H40.9300
C1—C21.362 (6)C13—H130.9300
C1—C61.396 (5)C14—H140.9300
C2—C31.378 (6)C15—H150.9800
C3—C41.367 (6)C18—H18A0.9600
C4—C51.376 (5)C18—H18B0.9600
C5—C61.393 (4)C18—H18C0.9600
C6—C101.454 (4)C22—H22A0.9700
C10—C141.353 (4)C22—H22B0.9700
C12—C131.346 (4)C24—H240.9300
C12—C151.480 (4)C25—H250.9300
C13—C141.418 (5)C27—H270.9300
C15—C221.531 (4)C28—H280.9300
C17—C181.490 (5)C29—H29A0.9600
C21—C221.499 (4)C29—H29B0.9600
C21—C231.458 (4)C29—H29C0.9600
C23—C241.383 (5)
C10—O11—C12106.9 (2)C27—C26—C29121.3 (4)
O8—N7—O9123.2 (4)C26—C27—C28121.9 (4)
O8—N7—C5119.1 (3)C23—C28—C27120.1 (3)
O9—N7—C5117.7 (4)C2—C1—H1119.00
N20—N16—C15113.1 (2)C6—C1—H1119.00
N20—N16—C17121.9 (2)C1—C2—H2120.00
C15—N16—C17124.3 (2)C3—C2—H2120.00
N16—N20—C21108.1 (2)C2—C3—H3120.00
C2—C1—C6121.8 (3)C4—C3—H3120.00
C1—C2—C3120.5 (4)C3—C4—H4120.00
C2—C3—C4119.9 (4)C5—C4—H4120.00
C3—C4—C5119.0 (3)C12—C13—H13126.00
N7—C5—C4116.3 (3)C14—C13—H13126.00
N7—C5—C6120.8 (3)C10—C14—H14127.00
C4—C5—C6122.9 (3)C13—C14—H14127.00
C1—C6—C5115.9 (3)N16—C15—H15109.00
C1—C6—C10119.2 (3)C12—C15—H15109.00
C5—C6—C10124.9 (3)C22—C15—H15109.00
O11—C10—C6118.5 (2)C17—C18—H18A109.00
O11—C10—C14109.5 (3)C17—C18—H18B109.00
C6—C10—C14132.0 (3)C17—C18—H18C109.00
O11—C12—C13109.3 (3)H18A—C18—H18B109.00
O11—C12—C15116.1 (2)H18A—C18—H18C110.00
C13—C12—C15134.5 (3)H18B—C18—H18C109.00
C12—C13—C14107.5 (3)C15—C22—H22A111.00
C10—C14—C13106.8 (2)C15—C22—H22B111.00
N16—C15—C12113.3 (3)C21—C22—H22A111.00
N16—C15—C22101.4 (2)C21—C22—H22B111.00
C12—C15—C22114.1 (3)H22A—C22—H22B109.00
O19—C17—N16119.2 (3)C23—C24—H24120.00
O19—C17—C18123.3 (3)C25—C24—H24120.00
N16—C17—C18117.5 (2)C24—C25—H25119.00
N20—C21—C22114.0 (2)C26—C25—H25119.00
N20—C21—C23121.3 (2)C26—C27—H27119.00
C22—C21—C23124.7 (3)C28—C27—H27119.00
C15—C22—C21103.4 (2)C23—C28—H28120.00
C21—C23—C24122.5 (3)C27—C28—H28120.00
C21—C23—C28119.5 (3)C26—C29—H29A109.00
C24—C23—C28118.0 (3)C26—C29—H29B109.00
C23—C24—C25120.9 (3)C26—C29—H29C109.00
C24—C25—C26121.8 (3)H29A—C29—H29B109.00
C25—C26—C27117.4 (4)H29A—C29—H29C109.00
C25—C26—C29121.4 (4)H29B—C29—H29C110.00
C12—O11—C10—C6179.6 (3)C1—C6—C10—O11147.6 (3)
C12—O11—C10—C140.8 (3)C1—C6—C10—C1431.9 (5)
C10—O11—C12—C130.2 (3)C5—C6—C10—O1132.0 (4)
C10—O11—C12—C15176.0 (3)C5—C6—C10—C14148.5 (4)
O8—N7—C5—C4129.4 (3)O11—C10—C14—C131.0 (4)
O8—N7—C5—C647.1 (4)C6—C10—C14—C13179.5 (3)
O9—N7—C5—C448.9 (5)O11—C12—C13—C140.4 (4)
O9—N7—C5—C6134.6 (4)C15—C12—C13—C14175.6 (3)
C15—N16—N20—C210.7 (4)O11—C12—C15—N1667.3 (3)
C17—N16—N20—C21169.8 (3)O11—C12—C15—C2248.1 (4)
N20—N16—C15—C12121.0 (3)C13—C12—C15—N16117.7 (4)
N20—N16—C15—C221.7 (3)C13—C12—C15—C22126.9 (4)
C17—N16—C15—C1268.8 (4)C12—C13—C14—C100.8 (4)
C17—N16—C15—C22168.5 (3)N16—C15—C22—C211.9 (3)
N20—N16—C17—O19176.2 (3)C12—C15—C22—C21120.3 (3)
N20—N16—C17—C184.7 (5)N20—C21—C22—C151.8 (4)
C15—N16—C17—O196.8 (5)C23—C21—C22—C15178.7 (3)
C15—N16—C17—C18174.0 (3)N20—C21—C23—C241.1 (5)
N16—N20—C21—C220.8 (4)N20—C21—C23—C28179.9 (3)
N16—N20—C21—C23179.7 (3)C22—C21—C23—C24179.4 (3)
C6—C1—C2—C30.4 (6)C22—C21—C23—C280.4 (5)
C2—C1—C6—C50.3 (5)C21—C23—C24—C25179.0 (3)
C2—C1—C6—C10180.0 (3)C28—C23—C24—C250.1 (5)
C1—C2—C3—C40.1 (6)C21—C23—C28—C27178.5 (3)
C2—C3—C4—C50.3 (6)C24—C23—C28—C270.6 (5)
C3—C4—C5—N7176.0 (3)C23—C24—C25—C260.8 (6)
C3—C4—C5—C60.4 (5)C24—C25—C26—C271.1 (6)
N7—C5—C6—C1176.1 (3)C24—C25—C26—C29178.6 (4)
N7—C5—C6—C104.2 (4)C25—C26—C27—C280.5 (6)
C4—C5—C6—C10.1 (4)C29—C26—C27—C28179.1 (4)
C4—C5—C6—C10179.6 (3)C26—C27—C28—C230.3 (6)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C23–C28 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···O19i0.932.563.462 (4)162
C18—H18C···Cg4ii0.962.693.595 (4)158
Symmetry codes: (i) x, y, z+2; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C23–C28 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···O19i0.932.563.462 (4)162
C18—H18C···Cg4ii0.962.693.595 (4)158
Symmetry codes: (i) x, y, z+2; (ii) x, y, z+1.
 

Acknowledgements

The authors thank the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC, New Delhi, for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

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