1-Benzoyl-4-(4-methyl­phen­yl)phthal­azine

Karuppusamy Sakthivel; Kannupal Srinivasan; Sampath Natarajan

doi:10.1107/S1600536811050641

. 2011 Nov 30;67(Pt 12):o3497. doi: 10.1107/S1600536811050641

1-Benzoyl-4-(4-methylphenyl)phthalazine

Karuppusamy Sakthivel ^a, Kannupal Srinivasan ^a, Sampath Natarajan ^b,^*

PMCID: PMC3239121 PMID: 22199969

Abstract

In the title molecule, C₂₂H₁₆N₂O, the tolyl and benzoyl rings make dihedral angles 50.2 (5) and 56.4 (5)°, respectively, with the phthalazine ring system while the dihedral angle between the tolyl and benzoyl rings is 0.70 (4)°. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯N hydrogen bonds, as well as weak C—H⋯π interactions.

Related literature

For the biological activity of phthalazine derivatives, see: Grasso et al. (2000 ▶). For related structures, see: Dilek et al. (2004 ▶); Rajnikant et al. (2006 ▶).

Experimental

Crystal data

C₂₂H₁₆N₂O
M _r = 324.37
Monoclinic,
a = 12.4873 (2) Å
b = 8.8011 (1) Å
c = 15.4425 (2) Å
β = 92.458 (1)°
V = 1695.60 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.10 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
30411 measured reflections
3519 independent reflections
2606 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.130
S = 1.07
3519 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050641/pv2486sup1.cif

e-67-o3497-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050641/pv2486Isup2.hkl

e-67-o3497-Isup2.hkl^{(169.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050641/pv2486Isup3.cml

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

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

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.71	3.400 (3)	132
C13—H13⋯N2ⁱⁱ	0.93	2.73	3.654 (3)	170
C20—H20⋯N2ⁱⁱⁱ	0.93	2.61	3.522 (2)	166
C6—H6⋯Cg1^iv	0.93	2.76	3.549 (2)	143

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

Acknowledgments

KS thanks the Department of Science and Technology (DST) and the Council of Scientific and Industrial Research (CSIR), India, for financial support.

supplementary crystallographic information

Comment

Phthalazine (2,3 benzodiazine) is a well known heterocyclic system which is widely used in synthetic organic chemistry as an intermediate. Its derivatives possess remarkable biological activity, such as anticonvulsant antimicrobial, anti-inflammatory, antifungal, antibacterial, vasorelaxant and cardiotonic activity (Grasso et al., 2000).

In the title molecule (Fig. 1), the phthalazine moiety consists of a benzene and a pyridazine rings fused together and shows a planar conformation; the dihedral angle between these rings is 0.70 (4)°. A tolyl and a benzoyl rings are substituted on the pyridazine ring and dihedral angle of these rings with the pyridazine ring are 50.2 (5) and 56.4 (5)°, respectively. Though the molecules do not show any classical hydrogen bonds, these molecules are connected by C–H···O and C—H···N types of intermolecular hydrogen bonds. In addition to these, a C—H···π weak interaction also helps to consolidate the molecules in the unit cell crystal packing (Fig. 2 and Tab. 1). The molecular dimensions in the title compound are in excellent agreement with the corresponding molecular dimensions reported in closely related compounds (Dilek et al., 2004; Rajnikant et al., 2006).

Experimental

The title compound was synthesized in 70% yield by heating the compounds 1-[2-(4-methylbenzoyl)phenyl]-2-phenylethane-1,2-dione (50 mg, 0.15 mmol) with hydrazine hydrate (11 mg, 0.23 mmol) under reflux in acetonitrile (5 ml) for 6 hr. The crystals suitable for crystallographic study were grown from dichloromethane by slow evaporation at room temperature.