2-(2-Hydroxy­ethyl)phthalazin-1(2H)-one

Orhan Büyükgüngör; Mustafa Odabaşoğlu

doi:10.1107/S1600536808007691

. 2008 Mar 29;64(Pt 4):o756. doi: 10.1107/S1600536808007691

2-(2-Hydroxyethyl)phthalazin-1(2H)-one

Orhan Büyükgüngör ^a,^*, Mustafa Odabaşoğlu ^b

PMCID: PMC2960892 PMID: 21202145

Abstract

In the molecule of the title compound, C₁₀H₁₀N₂O₂, the rings are nearly coplanar, making a dihedral angle of 2.35 (5)°. In the crystal structure, intermolecular C—H⋯O, C—H⋯N and O—H⋯O hydrogen bonds link the molecules, generating R ₄ ⁴(22) and R ₄ ⁴(24) ring motifs to form a three-dimensional network. A weak π–π interaction between the pyridazinone and benzene rings further stabilizes the crystal structure, with a centroid–centroid distance of 3.709 (3) Å and an interplanar separation of 3.312 Å.

Related literature

For general background, see: Cheng et al. (1999 ▶); Smith (2001 ▶); Dantzer et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Büyükgüngör et al. (2007 ▶). For ring motif details, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₁₀N₂O₂
M _r = 190.20
Orthorhombic,
a = 7.3278 (6) Å
b = 8.1823 (8) Å
c = 15.4108 (19) Å
V = 924.00 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.76 × 0.45 × 0.21 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.964, T _max = 0.982
4205 measured reflections
944 independent reflections
720 reflections with I > 2σ(I)
R _int = 0.067

Refinement

R[F ² > 2σ(F ²)] = 0.089
wR(F ²) = 0.240
S = 1.90
944 reflections
98 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808007691/hk2435sup1.cif

e-64-0o756-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007691/hk2435Isup2.hkl

e-64-0o756-Isup2.hkl^{(45.9KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.91	2.704 (9)	163
C4—H4⋯N2ⁱⁱ	0.93	2.73	3.570 (10)	151
C8—H8⋯O2ⁱⁱⁱ	0.93	2.53	3.376 (11)	152

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Phthalazines, also called benzo-ortho-diazines or benzopyridazines, are a group of heterocyclic compounds, isomeric with the cinnolines. The practical interest upon phthalazine derivatives is based on their widespread applications. Benzopyridazines, like other members of the isomeric diazene series, have found wide applications such as therapeutic agents, ligands in transition metal catalysis, chemiluminescent and optical materials (Cheng et al., 1999). 2-Substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazine-1-one derivatives are used as herbicides and imide-substituted-4-Benzyl-(2H) -phthalazin-1-ones are used as potent inhibitors of poly (ADP-ribose) polymerase-1 (PARP-1) (Smith, 2001; Dantzer et al., 1999). In view of the importance of the phthalazines, we herein report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges (Büyükgüngör et al., 2007). The homoaromatic and heterocyclic rings are, of course, planar and they are also nearly coplanar with a dihedral angle of 2.35 (5)°.

In the crystal structure, intermolecular C-H···O, C-H···N and O-H···O hydrogen bonds (Table 1) link the molecules, generating R₄⁴(22) (Fig. 2) and R₄⁴(24) (Fig. 4) ring motifs by C(7) chains (Fig. 3) (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure. A weak π···π interaction between the pyridazinone and benzene rings, at x, y, z and x - 1/2, 1 - y, z, respectively, further stabilizes the structure, with a centroid-centroid distance of 3.709 (3) Å and plane-plane separation of 3.312 Å (Fig. 5).

Experimental

A solution of phthalaldehydic acid (1.50 g, 10 mmol) and 3-aminopropan-1-ol (1.52 g, 20 mmol) in DMF (500 ml) was refluxed for 3 h. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a reaction mixture at room temperature (yield; 90%).