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

Büyükgüngör, O.; Odabaşoğlu, M.

doi:10.1107/S1600536808007691

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o756

doi:10.1107/S1600536808007691

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

Orhan Büyükgüngör ^a ^* and Mustafa Odabaşoğlu ^b

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 19 March 2008; accepted 20 March 2008; online 29 March 2008)

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 R₄⁴(22) and R₄⁴(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, P c a 2₁
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[F² > 2σ(F²)] = 0.089
wR(F²) = 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

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
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+1, z]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	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 have been omitted for clarity.
	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 have been omitted for clarity.
	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 bondings have been omitted for clarity.

2-(2-hydroxyethyl)phthalazin-1(2H)-one top

Crystal data top

C₁₀H₁₀N₂O₂	F(000) = 400
M_r = 190.20	D_x = 1.367 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4205 reflections
a = 7.3278 (6) Å	θ = 2.5–27.8°
b = 8.1823 (8) Å	µ = 0.10 mm⁻¹
c = 15.4108 (19) Å	T = 296 K
V = 924.00 (16) Å³	Prism, colorless
Z = 4	0.76 × 0.45 × 0.21 mm

Data collection top

Stoe IPDS II diffractometer	944 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	720 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.067
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
w–scan rotation method	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→9
T_min = 0.964, T_max = 0.982	l = −18→18
4205 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.240	H-atom parameters constrained
S = 1.90	w = 1/[σ²(F_o²) + (0.074P)² + 0.0928P] where P = (F_o² + 2F_c²)/3
944 reflections	(Δ/σ)_max < 0.001
98 parameters	Δρ_max = 0.43 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O₂	V = 924.00 (16) Å³
M_r = 190.20	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 7.3278 (6) Å	µ = 0.10 mm⁻¹
b = 8.1823 (8) Å	T = 296 K
c = 15.4108 (19) Å	0.76 × 0.45 × 0.21 mm

Data collection top

Stoe IPDS II diffractometer	944 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	720 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.982	R_int = 0.067
4205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	1 restraint
wR(F²) = 0.240	H-atom parameters constrained
S = 1.90	Δρ_max = 0.43 e Å⁻³
944 reflections	Δρ_min = −0.40 e Å⁻³
98 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	0.5413 (10)	0.4049 (8)	0.4806 (3)	0.095 (2)
O2	0.7978 (10)	0.7890 (10)	0.3983 (4)	0.110 (2)
H2	0.8754	0.7473	0.4296	0.166*
N1	0.5944 (8)	0.6385 (7)	0.5551 (4)	0.0586 (15)
C1	0.5917 (10)	0.4717 (9)	0.5492 (4)	0.0575 (17)
C2	0.6416 (14)	0.3841 (8)	0.6254 (6)	0.0726 (10)
C3	0.6338 (13)	0.2106 (9)	0.6331 (6)	0.0726 (10)
H3	0.5912	0.1491	0.5866	0.087*
C4	0.6862 (12)	0.1342 (10)	0.7055 (5)	0.0726 (10)
H4	0.6827	0.0206	0.7075	0.087*
C5	0.7455 (13)	0.2200 (9)	0.7774 (6)	0.0726 (10)
H5	0.7816	0.1640	0.8270	0.087*
C6	0.7513 (13)	0.3874 (9)	0.7757 (6)	0.0726 (10)
H6	0.7907	0.4455	0.8240	0.087*
C7	0.6975 (14)	0.4696 (9)	0.7008 (5)	0.0726 (10)
C8	0.6945 (12)	0.6446 (8)	0.6931 (5)	0.0624 (19)
H8	0.7327	0.7041	0.7412	0.075*
N2	0.6454 (10)	0.7246 (6)	0.6280 (4)	0.0609 (15)
C9	0.5268 (12)	0.7439 (14)	0.4850 (6)	0.090 (3)
H9A	0.4774	0.6753	0.4393	0.108*
H9B	0.4277	0.8103	0.5073	0.108*
C10	0.6667 (14)	0.8531 (12)	0.4469 (6)	0.092 (3)
H10A	0.6036	0.9340	0.4120	0.110*
H10B	0.7248	0.9112	0.4943	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.106 (5)	0.124 (5)	0.056 (3)	−0.042 (4)	0.003 (3)	−0.022 (3)
O2	0.098 (5)	0.156 (6)	0.077 (4)	0.036 (5)	0.017 (4)	0.032 (4)
N1	0.048 (3)	0.066 (4)	0.061 (3)	−0.004 (3)	0.003 (3)	0.002 (3)
C1	0.050 (4)	0.073 (4)	0.050 (3)	−0.017 (4)	0.016 (3)	−0.002 (4)
C2	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C3	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C4	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C5	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C6	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C7	0.079 (2)	0.0575 (16)	0.081 (2)	0.0007 (18)	0.0200 (16)	0.0076 (17)
C8	0.085 (5)	0.051 (4)	0.052 (4)	−0.008 (4)	0.003 (3)	−0.004 (3)
N2	0.073 (4)	0.048 (3)	0.062 (3)	−0.002 (3)	0.006 (3)	0.011 (3)
C9	0.063 (5)	0.124 (7)	0.082 (6)	0.013 (5)	−0.007 (5)	0.040 (6)
C10	0.107 (8)	0.084 (5)	0.084 (5)	0.039 (6)	0.027 (5)	0.032 (5)

Geometric parameters (Å, º) top

O2—H2	0.8200	C6—H6	0.9300
C1—O1	1.246 (9)	C7—C8	1.436 (10)
C1—N1	1.368 (9)	C8—N2	1.251 (9)
C1—C2	1.423 (11)	C8—H8	0.9300
C2—C7	1.417 (12)	N2—N1	1.377 (9)
C2—C3	1.426 (10)	C9—C10	1.481 (14)
C3—C4	1.335 (11)	C9—N1	1.469 (10)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.382 (13)	C9—H9B	0.9700
C4—H4	0.9300	C10—O2	1.327 (10)
C5—C6	1.371 (11)	C10—H10A	0.9700
C5—H5	0.9300	C10—H10B	0.9700
C6—C7	1.392 (12)

C10—O2—H2	109.5	C7—C6—H6	120.3
C1—N1—N2	124.7 (6)	C6—C7—C2	121.5 (7)
C1—N1—C9	122.1 (7)	C6—C7—C8	123.7 (8)
N2—N1—C9	113.0 (7)	C2—C7—C8	114.8 (7)
O1—C1—N1	119.9 (7)	N2—C8—C7	126.4 (7)
O1—C1—C2	123.7 (7)	N2—C8—H8	116.8
N1—C1—C2	116.4 (7)	C7—C8—H8	116.8
C7—C2—C3	115.8 (8)	C8—N2—N1	117.6 (5)
C7—C2—C1	120.1 (6)	C10—C9—N1	114.3 (7)
C3—C2—C1	124.0 (9)	C10—C9—H9A	108.7
C4—C3—C2	121.6 (9)	N1—C9—H9A	108.7
C4—C3—H3	119.2	C10—C9—H9B	108.7
C2—C3—H3	119.2	N1—C9—H9B	108.7
C5—C4—C3	121.5 (8)	H9A—C9—H9B	107.6
C5—C4—H4	119.2	O2—C10—C9	119.1 (9)
C3—C4—H4	119.2	O2—C10—H10A	107.5
C6—C5—C4	120.1 (8)	C9—C10—H10A	107.5
C6—C5—H5	119.9	O2—C10—H10B	107.5
C4—C5—H5	119.9	C9—C10—H10B	107.5
C5—C6—C7	119.3 (8)	H10A—C10—H10B	107.0
C5—C6—H6	120.3

C8—N2—N1—C1	0.7 (11)	C4—C5—C6—C7	−0.2 (14)
C8—N2—N1—C9	175.8 (7)	C5—C6—C7—C2	−1.8 (15)
O1—C1—N1—N2	179.2 (6)	C5—C6—C7—C8	178.5 (8)
C2—C1—N1—N2	1.6 (10)	C3—C2—C7—C6	3.6 (14)
O1—C1—N1—C9	4.6 (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—C7	180.0 (8)	C1—C2—C7—C8	1.3 (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—N2	1.2 (13)
N1—C1—C2—C3	175.3 (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—C4	178.4 (8)	C10—C9—N1—N2	66.5 (11)
C2—C3—C4—C5	1.9 (14)	N1—C9—C10—O2	70.9 (12)
C3—C4—C5—C6	0.1 (14)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O₂
M_r	190.20
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	7.3278 (6), 8.1823 (8), 15.4108 (19)
V (Å³)	924.00 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.76 × 0.45 × 0.21

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4205, 944, 720
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.240, 1.90
No. of reflections	944
No. of parameters	98
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.40

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.91	2.704 (9)	162.7
C4—H4···N2ⁱⁱ	0.93	2.73	3.570 (10)	151.0
C8—H8···O2ⁱⁱⁱ	0.93	2.53	3.376 (11)	151.7

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

Acknowledgements

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).

References

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