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Acta Cryst. (2011). E67, o1042    [ doi:10.1107/S1600536811011597 ]

2-Benzyl-6-benzyloxypyridazin-3(2H)-one

Z.-Y. Ju, W.-X. Jiang and F.-L. Yang

Abstract top

In the title compound, C18H16N2O2, the central pyridazine ring forms dihedral angles of 77.08 (5)° and 84.62 (5)° with the two benzene rings. The dihedral angle between the two benzene rings is 68.18 (4)°. A very weak intramolecular C-H...N hydrogen bond and an intramolecular C-H...[pi] interaction occur. The crystal structure is stabilized by weak intermolecular C-H...O hydrogen bonds and weak C-H...[pi] and [pi]-[pi] stacking interactions [centroid-centroid distance = 3.6867 (10) Å].

Comment top

Pyridazinone analogues have been reported to have a variety of biological activities, such as highly-selective anti-HIV agents (Loksha et al., 2007), pesticide(Li et al., 2005), highly herbicidal activity (Xu et al., 2006). In order to discover further biologically active Pyridazinone analogues, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

In a continuation of our studies on the crystal structures of Pyridazinone analogues (Liu et al., 2005), we report here the synthesis and crystal structure of the title molecule, the central pyridazine ring forms dihedral angles of 77.08 (5)° and 84.62 (5)° with the two benzene rings, The dihedral angle between two benzene rings is 68.18 (4)°. The Crystal structure is stabilized by a weak intramolecular C—H···N hydrogen bond (Table 1), a weak intermolecular C—H···O hydrogen bond (Table 1), C—H···Cg π—ring (Table 1) and π-π stacking interactions where Cg(1)—Cg(1) (1/2 - x, 1/2 - y, 1 - z) is 3.6867 (10) Å [Cg(1) is the centroid of the N1,N2, C1—C4 ring] (Table 2).

Related literature top

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007). For applications as pesticide agents, see: Li et al. (2005); Selby et al. (2002). For applications as herbicides, see: Xu et al. (2006). For related structures, see: Liu et al. (2005).

Experimental top

Maleic hydrazide(0.56 g, 5 mmol), Benzyl chloride(1.52 g, 12 mmol) and K2CO3 (1.66 g, 12 mmol) were added to absolute ethanol(30 ml). The mixture was stirred in the room temperature for 6 h. The suspension was filtered and the residue was washed with absolute ethanol. The title compound was recrystallized from the mother solution and single crystals of (I) were obtained by slow evaporation.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.95 Å and C—H = 0.99 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2009); cell refinement: CrystalClear (Rigaku/MSC, 2009); data reduction: CrystalClear (Rigaku/MSC, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku/MSC, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.
2-Benzyl-6-benzyloxypyridazin-3(2H)-one top
Crystal data top
C18H16N2O2F(000) = 1232
Mr = 292.33Dx = 1.344 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4881 reflections
a = 32.741 (4) Åθ = 1.3–28.0°
b = 10.9198 (14) ŵ = 0.09 mm−1
c = 8.1228 (10) ÅT = 113 K
β = 95.92 (2)°Prism, colorless
V = 2888.6 (6) Å30.20 × 0.18 × 0.12 mm
Z = 8
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3448 independent reflections
Radiation source: rotating anode2142 reflections with I > 2σ(I)
multilayerRint = 0.063
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.3°
ω and φ scansh = −43→41
Absorption correction: multi-scan
CrystalClear		k = −14→14
Tmin = 0.982, Tmax = 0.989l = −10→10
18031 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0548P)2]
where P = (Fo2 + 2Fc2)/3
3448 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C18H16N2O2V = 2888.6 (6) Å3
Mr = 292.33Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.741 (4) ŵ = 0.09 mm−1
b = 10.9198 (14) ÅT = 113 K
c = 8.1228 (10) Å0.20 × 0.18 × 0.12 mm
β = 95.92 (2)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3448 independent reflections
Absorption correction: multi-scan
CrystalClear		2142 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.989Rint = 0.063
18031 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.116Δρmax = 0.23 e Å−3
S = 0.95Δρmin = −0.23 e Å−3
3448 reflectionsAbsolute structure: ?
199 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 > σ(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
xyzUiso*/Ueq
O10.20711 (3)0.14159 (10)0.06099 (12)0.0315 (3)
O20.20245 (3)0.38939 (9)0.62925 (12)0.0282 (3)
N10.18498 (4)0.16470 (11)0.31678 (14)0.0221 (3)
N20.18241 (4)0.22441 (11)0.46481 (14)0.0229 (3)
C10.20713 (5)0.20250 (14)0.19094 (18)0.0241 (3)
C20.22975 (5)0.31536 (14)0.22369 (18)0.0257 (4)
H20.24600.34700.14320.031*
C30.22792 (5)0.37578 (14)0.36727 (18)0.0253 (4)
H30.24270.44990.38940.030*
C40.20319 (5)0.32523 (14)0.48542 (17)0.0231 (3)
C50.15786 (4)0.05874 (13)0.29089 (17)0.0232 (3)
H5A0.15590.01730.39820.028*
H5B0.16980.00000.21640.028*
C60.11536 (5)0.09390 (13)0.21683 (17)0.0222 (3)
C70.09415 (5)0.01638 (14)0.10195 (17)0.0257 (4)
H70.1068−0.05700.07010.031*
C80.05468 (5)0.04490 (15)0.03337 (18)0.0298 (4)
H80.0406−0.0082−0.04610.036*
C90.03585 (5)0.15088 (15)0.08102 (19)0.0304 (4)
H90.00880.17060.03470.036*
C100.05657 (5)0.22800 (14)0.19643 (19)0.0289 (4)
H100.04360.30040.22990.035*
C110.09614 (5)0.20016 (14)0.26341 (18)0.0261 (4)
H110.11020.25400.34170.031*
C120.17631 (5)0.34314 (15)0.74918 (18)0.0281 (4)
H12A0.18350.38520.85620.034*
H12B0.18180.25460.76650.034*
C130.13136 (5)0.36113 (13)0.69709 (17)0.0246 (4)
C140.10296 (5)0.28071 (14)0.75401 (18)0.0274 (4)
H140.11220.21560.82600.033*
C150.06137 (5)0.29469 (14)0.70671 (19)0.0301 (4)
H150.04220.23890.74540.036*
C160.04764 (5)0.39007 (14)0.60290 (19)0.0317 (4)
H160.01910.39960.56980.038*
C170.07560 (5)0.47139 (15)0.54761 (19)0.0317 (4)
H170.06630.53710.47680.038*
C180.11706 (5)0.45739 (14)0.59503 (18)0.0293 (4)
H180.13600.51420.55750.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0356 (7)0.0367 (7)0.0229 (6)−0.0022 (5)0.0066 (5)−0.0036 (5)
O20.0292 (6)0.0304 (6)0.0252 (6)−0.0038 (5)0.0037 (5)−0.0070 (5)
N10.0246 (7)0.0239 (7)0.0177 (6)−0.0016 (5)0.0020 (5)−0.0007 (5)
N20.0239 (7)0.0255 (7)0.0191 (6)0.0017 (5)0.0009 (5)−0.0020 (5)
C10.0244 (8)0.0282 (9)0.0194 (7)0.0034 (6)0.0016 (6)0.0022 (6)
C20.0243 (8)0.0280 (9)0.0247 (8)−0.0005 (7)0.0026 (6)0.0038 (7)
C30.0223 (8)0.0243 (8)0.0288 (8)−0.0007 (6)0.0003 (7)0.0015 (7)
C40.0221 (8)0.0253 (8)0.0213 (8)0.0022 (6)−0.0008 (6)−0.0018 (6)
C50.0266 (8)0.0211 (8)0.0220 (7)−0.0021 (6)0.0029 (6)−0.0001 (6)
C60.0248 (8)0.0228 (8)0.0193 (7)−0.0019 (6)0.0032 (6)0.0028 (6)
C70.0300 (9)0.0251 (8)0.0225 (8)−0.0044 (7)0.0059 (7)−0.0006 (6)
C80.0301 (9)0.0333 (9)0.0256 (8)−0.0082 (7)0.0006 (7)−0.0015 (7)
C90.0274 (9)0.0332 (9)0.0298 (9)−0.0029 (7)−0.0008 (7)0.0063 (7)
C100.0304 (9)0.0259 (9)0.0304 (9)0.0019 (7)0.0028 (7)0.0021 (7)
C110.0283 (8)0.0245 (8)0.0247 (8)−0.0005 (7)−0.0011 (6)−0.0018 (7)
C120.0322 (9)0.0329 (9)0.0194 (8)−0.0013 (7)0.0034 (7)−0.0020 (7)
C130.0336 (9)0.0216 (8)0.0190 (7)0.0002 (7)0.0047 (6)−0.0041 (6)
C140.0357 (9)0.0240 (8)0.0222 (8)0.0001 (7)0.0023 (7)0.0001 (6)
C150.0327 (9)0.0292 (9)0.0289 (8)−0.0041 (7)0.0057 (7)−0.0016 (7)
C160.0314 (9)0.0340 (10)0.0294 (9)0.0024 (7)0.0020 (7)−0.0030 (7)
C170.0385 (10)0.0275 (9)0.0293 (9)0.0056 (7)0.0036 (7)0.0030 (7)
C180.0345 (9)0.0259 (9)0.0283 (8)−0.0012 (7)0.0071 (7)0.0034 (7)
Geometric parameters (Å, °) top
O1—C11.2476 (17)C8—H80.9500
O2—C41.3647 (17)C9—C101.385 (2)
O2—C121.4522 (18)C9—H90.9500
N1—C11.3763 (19)C10—C111.386 (2)
N1—N21.3780 (15)C10—H100.9500
N1—C51.4605 (18)C11—H110.9500
N2—C41.2959 (18)C12—C131.502 (2)
C1—C21.448 (2)C12—H12A0.9900
C2—C31.347 (2)C12—H12B0.9900
C2—H20.9500C13—C181.390 (2)
C3—C41.429 (2)C13—C141.392 (2)
C3—H30.9500C14—C151.385 (2)
C5—C61.507 (2)C14—H140.9500
C5—H5A0.9900C15—C161.385 (2)
C5—H5B0.9900C15—H150.9500
C6—C111.391 (2)C16—C171.383 (2)
C6—C71.392 (2)C16—H160.9500
C7—C81.389 (2)C17—C181.381 (2)
C7—H70.9500C17—H170.9500
C8—C91.385 (2)C18—H180.9500
C4—O2—C12117.36 (12)C10—C9—H9120.1
C1—N1—N2126.19 (12)C8—C9—H9120.1
C1—N1—C5119.33 (12)C9—C10—C11120.34 (15)
N2—N1—C5114.18 (11)C9—C10—H10119.8
C4—N2—N1115.86 (12)C11—C10—H10119.8
O1—C1—N1120.95 (14)C10—C11—C6120.47 (15)
O1—C1—C2124.38 (14)C10—C11—H11119.8
N1—C1—C2114.67 (13)C6—C11—H11119.8
C3—C2—C1120.56 (14)O2—C12—C13113.20 (12)
C3—C2—H2119.7O2—C12—H12A108.9
C1—C2—H2119.7C13—C12—H12A108.9
C2—C3—C4118.12 (14)O2—C12—H12B108.9
C2—C3—H3120.9C13—C12—H12B108.9
C4—C3—H3120.9H12A—C12—H12B107.8
N2—C4—O2119.42 (13)C18—C13—C14118.68 (15)
N2—C4—C3124.59 (13)C18—C13—C12121.80 (14)
O2—C4—C3115.98 (13)C14—C13—C12119.51 (14)
N1—C5—C6112.22 (12)C15—C14—C13120.64 (15)
N1—C5—H5A109.2C15—C14—H14119.7
C6—C5—H5A109.2C13—C14—H14119.7
N1—C5—H5B109.2C14—C15—C16119.97 (16)
C6—C5—H5B109.2C14—C15—H15120.0
H5A—C5—H5B107.9C16—C15—H15120.0
C11—C6—C7118.77 (14)C17—C16—C15119.76 (16)
C11—C6—C5121.93 (14)C17—C16—H16120.1
C7—C6—C5119.28 (14)C15—C16—H16120.1
C8—C7—C6120.80 (15)C18—C17—C16120.19 (15)
C8—C7—H7119.6C18—C17—H17119.9
C6—C7—H7119.6C16—C17—H17119.9
C9—C8—C7119.86 (15)C17—C18—C13120.74 (15)
C9—C8—H8120.1C17—C18—H18119.6
C7—C8—H8120.1C13—C18—H18119.6
C10—C9—C8119.75 (15)
C1—N1—N2—C4−0.3 (2)C11—C6—C7—C80.7 (2)
C5—N1—N2—C4−173.91 (12)C5—C6—C7—C8178.90 (13)
N2—N1—C1—O1−179.53 (13)C6—C7—C8—C9−0.9 (2)
C5—N1—C1—O1−6.3 (2)C7—C8—C9—C100.2 (2)
N2—N1—C1—C20.8 (2)C8—C9—C10—C110.5 (2)
C5—N1—C1—C2174.04 (12)C9—C10—C11—C6−0.6 (2)
O1—C1—C2—C3179.70 (14)C7—C6—C11—C100.0 (2)
N1—C1—C2—C3−0.6 (2)C5—C6—C11—C10−178.11 (14)
C1—C2—C3—C40.1 (2)C4—O2—C12—C13−72.05 (17)
N1—N2—C4—O2−179.59 (11)O2—C12—C13—C18−28.7 (2)
N1—N2—C4—C3−0.3 (2)O2—C12—C13—C14152.30 (13)
C12—O2—C4—N2−3.1 (2)C18—C13—C14—C151.5 (2)
C12—O2—C4—C3177.58 (12)C12—C13—C14—C15−179.46 (14)
C2—C3—C4—N20.4 (2)C13—C14—C15—C16−0.6 (2)
C2—C3—C4—O2179.72 (13)C14—C15—C16—C17−0.3 (2)
C1—N1—C5—C6−88.39 (16)C15—C16—C17—C180.3 (2)
N2—N1—C5—C685.65 (14)C16—C17—C18—C130.7 (2)
N1—C5—C6—C11−38.55 (18)C14—C13—C18—C17−1.6 (2)
N1—C5—C6—C7143.33 (13)C12—C13—C18—C17179.41 (14)
Hydrogen-bond geometry (Å, °) top
Cg3 is the centroid of the C13–C18 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.383.2906 (19)161 (19)
C11—H11···N20.952.493.126 (2)124
C11—H11···Cg30.952.983.7103 (17)135
C17—H17···Cg3ii0.952.983.6991 (17)133
Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, −y+1, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg3 is the centroid of the C13–C18 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.383.2906 (19)161 (19)
C11—H11···N20.952.493.126 (2)124
C11—H11···Cg30.952.983.7103 (17)135
C17—H17···Cg3ii0.952.983.6991 (17)133
Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, −y+1, z−1/2.
Table 2
Comparative geometrical parameters (Å) for selected Cg—Cg Π stacking interaction, Cg1 is the centroid of the N1,N2,C1-C4 ring (Symmetry codes: 1/2-X,1/2-Y,1-Z). top
CgI—CgJCg—Cg(Å)CgIPerp(Å)CgjPerp(Å)Slippage(Å)
Cg1—Cg13.6867 (10)3.2243.2241.789
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20972143), the Natural Science Foundation of Henan Province Educational Committee, China (grant Nos. 2010 A150021 and 2007150036) and the High-level Talents Foundation of Xuchang University (grant No. 2010 GC033).

references
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