2-[4-(2-Methyl­prop­yl)phen­yl]-N′-[(E)-1-phenyl­ethyl­idene]propane­hydrazide

Hoong-Kun Fun; Samuel Robinson Jebas; K V Sujith; B Kalluraya

doi:10.1107/S1600536808036817

. 2008 Nov 20;64(Pt 12):o2377. doi: 10.1107/S1600536808036817

2-[4-(2-Methylpropyl)phenyl]-N′-[(E)-1-phenylethylidene]propanehydrazide

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, K V Sujith ^b, B Kalluraya ^b

PMCID: PMC2960058 PMID: 21581349

Abstract

In the title compound, C₂₁H₂₆N₂O, the dihedral angle between the two aromatic rings is 85.90 (19)°. The propenone–hydrazide unit forms dihedral angles of 21.62 (8) and 72.83 (9)°, respectively, with the terminal and central aromatic rings. The 2-methylpropyl group is disordered over two sites, with occupancies of 0.533 (13) and 0.467 (13). In crystal structure, molecules are linked into centrosymmetric dimers by paired N—H⋯O and C—H⋯O hydrogen bonds. In addition, C—H⋯π interactions are observed.

Related literature

For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002 ▶). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007 ▶). For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For a related structure, see: Fun et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₂₆N₂O
M _r = 322.44
Triclinic,
a = 5.4355 (2) Å
b = 10.2850 (4) Å
c = 17.3095 (6) Å
α = 80.821 (4)°
β = 84.312 (3)°
γ = 74.719 (3)°
V = 919.85 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100.0 (1) K
0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.984, T _max = 0.989
12794 measured reflections
4238 independent reflections
2556 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.194
S = 1.07
4238 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036817/ci2710sup1.cif

e-64-o2377-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036817/ci2710Isup2.hkl

e-64-o2377-Isup2.hkl^{(203.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.86 (2)	2.08 (2)	2.928 (3)	173 (2)
C20—H20A⋯O1ⁱ	0.96	2.31	3.247 (3)	165
C20—H20B⋯Cg1ⁱⁱ	0.96	2.75	3.609 (3)	150

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship.

supplementary crystallographic information

Comment

Ibuprofen belongs to the class of Non-Steroidal anti-Inflammatory Drugs (NSAIDs) with antipyretic, anti-inflammatory and analgesic properties (Palaska et al., 2002). Hydrazones containing an azometine -NHN═CH- moiety are synthesized by heating the appropriate substituted hydrazines/hydrazides with aldehydes and ketones in solvents like ethanol, methanol, tetrahydrofuran, butanol, glacial acetic acid, ethanol-glacial acetic acid. Another synthetic route for the synthesis of hydrazones is the coupling of aryldiazonium salts with active hydrogen compounds (Rollas & Kuckguzel, 2007). Hydrazide-hydrazones compounds are not only intermediates but they are also very effective organic compounds of their own. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gursoy, 2003). Prompted by these and in continuation of our work, (Fun et al., 2008) we are interested in the synthesis and crystal structure determination of ibuprofen derivatives. We report here the crystal structure of the title compound (I).

Bond lengths in the title molecule (Fig.1) have normal values (Allen et al., 1987). The two phenyl rings are essentially planar, with the maximum deviation from planarity being 0.003 (3)Å for atom C3 in the (C1-C6) ring and 0.012 (3)Å for atom C10 in the (C10-C15) ring. The two phenyl rings form a dihedral angle of 85.90 (11)°, indicating that they are almost orthogonal to each other. The propenone-hydrazide unit (O1/N1/N2/C8-C9) forms dihedral angles of 21.62 (8)° and 72.83 (9)° with (C1-C6) and (C10-C15) rings, respectively.

The crystal packing is consolidated by inter-molecular N—H···O and C—H···O hydrogen bonds together with C—H···π interactions (Table 1) involving the (C1-C6) ring (Centroid Cg1).

Experimental

The title compound was obtained by refluxing 2-[4-(2-methylpropyl)phenyl]propanehydrazide (0.01 mol) and acetophenone (0.01 mol) in ethanol (30 ml) with 3 drops of concentrated sulfuric acid for 1 h. The excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 87%; m.p.380–381 K).