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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o756.
Published online 2008 March 29. doi:  10.1107/S1600536808007691
PMCID: PMC2960892

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

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0o756-scheme1.jpg

Experimental

Crystal data

  • C10H10N2O2
  • M r = 190.20
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o756-efi10.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.40 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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%).

Refinement

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of (I), showing the formation of R44(22) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) 3/2 - x, y, z - 1/2; (ii) x - 1/2, 1 - y, z; (iii) 3/2 - x, y, 1/2 + z]. H atoms not involved in hydrogen bondings ...
Fig. 3.
A partial packing diagram of (I), showing the formation of C(7) chain [symmetry code: (i) x, y - 1, z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
Fig. 4.
A partial packing diagram of (I), showing the formation of R44(24) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, y + 1, z; (ii) 3/2 - x, y + 1, z - 1/2; (iii) 3/2 - x, y, z - 1/2]. H atoms not involved in hydrogen bondings ...
Fig. 5.
A packing diagram of (I), showing the π···π interactions [symmetry code: (i) x, y - 1, z]. Cg1 and Cg2 denote the centroids of the rings. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen ...

Crystal data

C10H10N2O2F000 = 400
Mr = 190.20Dx = 1.367 Mg m3
Orthorhombic, Pca21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4205 reflections
a = 7.3278 (6) Åθ = 2.5–27.8º
b = 8.1823 (8) ŵ = 0.10 mm1
c = 15.4108 (19) ÅT = 296 K
V = 924.00 (16) Å3Prism, colorless
Z = 40.76 × 0.45 × 0.21 mm

Data collection

Stoe IPDS II diffractometer944 independent reflections
Monochromator: plane graphite720 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.067
T = 296 Kθmax = 26.0º
w–scan rotation methodθmin = 2.5º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −8→8
Tmin = 0.964, Tmax = 0.982k = −10→9
4205 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.089H-atom parameters constrained
wR(F2) = 0.240  w = 1/[σ2(Fo2) + (0.074P)2 + 0.0928P] where P = (Fo2 + 2Fc2)/3
S = 1.90(Δ/σ)max < 0.001
944 reflectionsΔρmax = 0.43 e Å3
98 parametersΔρmin = −0.40 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) 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)

xyzUiso*/Ueq
O10.5413 (10)0.4049 (8)0.4806 (3)0.095 (2)
O20.7978 (10)0.7890 (10)0.3983 (4)0.110 (2)
H20.87540.74730.42960.166*
N10.5944 (8)0.6385 (7)0.5551 (4)0.0586 (15)
C10.5917 (10)0.4717 (9)0.5492 (4)0.0575 (17)
C20.6416 (14)0.3841 (8)0.6254 (6)0.0726 (10)
C30.6338 (13)0.2106 (9)0.6331 (6)0.0726 (10)
H30.59120.14910.58660.087*
C40.6862 (12)0.1342 (10)0.7055 (5)0.0726 (10)
H40.68270.02060.70750.087*
C50.7455 (13)0.2200 (9)0.7774 (6)0.0726 (10)
H50.78160.16400.82700.087*
C60.7513 (13)0.3874 (9)0.7757 (6)0.0726 (10)
H60.79070.44550.82400.087*
C70.6975 (14)0.4696 (9)0.7008 (5)0.0726 (10)
C80.6945 (12)0.6446 (8)0.6931 (5)0.0624 (19)
H80.73270.70410.74120.075*
N20.6454 (10)0.7246 (6)0.6280 (4)0.0609 (15)
C90.5268 (12)0.7439 (14)0.4850 (6)0.090 (3)
H9A0.47740.67530.43930.108*
H9B0.42770.81030.50730.108*
C100.6667 (14)0.8531 (12)0.4469 (6)0.092 (3)
H10A0.60360.93400.41200.110*
H10B0.72480.91120.49430.110*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.106 (5)0.124 (5)0.056 (3)−0.042 (4)0.003 (3)−0.022 (3)
O20.098 (5)0.156 (6)0.077 (4)0.036 (5)0.017 (4)0.032 (4)
N10.048 (3)0.066 (4)0.061 (3)−0.004 (3)0.003 (3)0.002 (3)
C10.050 (4)0.073 (4)0.050 (3)−0.017 (4)0.016 (3)−0.002 (4)
C20.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C30.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C40.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C50.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C60.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C70.079 (2)0.0575 (16)0.081 (2)0.0007 (18)0.0200 (16)0.0076 (17)
C80.085 (5)0.051 (4)0.052 (4)−0.008 (4)0.003 (3)−0.004 (3)
N20.073 (4)0.048 (3)0.062 (3)−0.002 (3)0.006 (3)0.011 (3)
C90.063 (5)0.124 (7)0.082 (6)0.013 (5)−0.007 (5)0.040 (6)
C100.107 (8)0.084 (5)0.084 (5)0.039 (6)0.027 (5)0.032 (5)

Geometric parameters (Å, °)

O2—H20.8200C6—H60.9300
C1—O11.246 (9)C7—C81.436 (10)
C1—N11.368 (9)C8—N21.251 (9)
C1—C21.423 (11)C8—H80.9300
C2—C71.417 (12)N2—N11.377 (9)
C2—C31.426 (10)C9—C101.481 (14)
C3—C41.335 (11)C9—N11.469 (10)
C3—H30.9300C9—H9A0.9700
C4—C51.382 (13)C9—H9B0.9700
C4—H40.9300C10—O21.327 (10)
C5—C61.371 (11)C10—H10A0.9700
C5—H50.9300C10—H10B0.9700
C6—C71.392 (12)
C10—O2—H2109.5C7—C6—H6120.3
C1—N1—N2124.7 (6)C6—C7—C2121.5 (7)
C1—N1—C9122.1 (7)C6—C7—C8123.7 (8)
N2—N1—C9113.0 (7)C2—C7—C8114.8 (7)
O1—C1—N1119.9 (7)N2—C8—C7126.4 (7)
O1—C1—C2123.7 (7)N2—C8—H8116.8
N1—C1—C2116.4 (7)C7—C8—H8116.8
C7—C2—C3115.8 (8)C8—N2—N1117.6 (5)
C7—C2—C1120.1 (6)C10—C9—N1114.3 (7)
C3—C2—C1124.0 (9)C10—C9—H9A108.7
C4—C3—C2121.6 (9)N1—C9—H9A108.7
C4—C3—H3119.2C10—C9—H9B108.7
C2—C3—H3119.2N1—C9—H9B108.7
C5—C4—C3121.5 (8)H9A—C9—H9B107.6
C5—C4—H4119.2O2—C10—C9119.1 (9)
C3—C4—H4119.2O2—C10—H10A107.5
C6—C5—C4120.1 (8)C9—C10—H10A107.5
C6—C5—H5119.9O2—C10—H10B107.5
C4—C5—H5119.9C9—C10—H10B107.5
C5—C6—C7119.3 (8)H10A—C10—H10B107.0
C5—C6—H6120.3
C8—N2—N1—C10.7 (11)C4—C5—C6—C7−0.2 (14)
C8—N2—N1—C9175.8 (7)C5—C6—C7—C2−1.8 (15)
O1—C1—N1—N2179.2 (6)C5—C6—C7—C8178.5 (8)
C2—C1—N1—N21.6 (10)C3—C2—C7—C63.6 (14)
O1—C1—N1—C94.6 (10)C1—C2—C7—C6−178.5 (8)
C2—C1—N1—C9−173.0 (7)C3—C2—C7—C8−176.7 (8)
O1—C1—C2—C7180.0 (8)C1—C2—C7—C81.3 (13)
N1—C1—C2—C7−2.5 (12)C6—C7—C8—N2−179.1 (9)
O1—C1—C2—C3−2.2 (13)C2—C7—C8—N21.2 (13)
N1—C1—C2—C3175.3 (8)C7—C8—N2—N1−2.2 (13)
C7—C2—C3—C4−3.7 (13)C10—C9—N1—C1−118.4 (9)
C1—C2—C3—C4178.4 (8)C10—C9—N1—N266.5 (11)
C2—C3—C4—C51.9 (14)N1—C9—C10—O270.9 (12)
C3—C4—C5—C60.1 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.912.704 (9)163
C4—H4···N2ii0.932.733.570 (10)151
C8—H8···O2iii0.932.533.376 (11)152

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2435).

References

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  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Cheng, Y., Ma, B. & Wuld, F. (1999). J. Mater. Chem.9, 2183–88.
  • Dantzer, F., Schreiber, V., Niedergang, C., Trucco, C., Flatter, E., De la Rubia, G., Oliver, J., Rolli, V., Menissier-de Murcia, J. & de Murcia, G. (1999). Biochimie, 81, 69–75. [PubMed]
  • Etter, M. C. (1990). Acc. Chem. Res.23, 120–126.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
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  • Büyükgüngör, O., Odabaşoğlu, M., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3198.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Smith, S. (2001). Trends Biochem. Sci.26, 174-179. [PubMed]
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