2-Benzyl-6-benz-yloxypyridazin-3(2H)-one.

In the title compound, C(18)H(16)N(2)O(2), 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 intra-molecular C-H⋯N hydrogen bond and an intra-molecular C-H⋯π inter-action occur. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π and π-π stacking inter-actions [centroid-centroid distance = 3.6867 (10) Å].

Related literature

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

Crystal data

C18H16N2O2

M = 292.33

Monoclinic,

a = 32.741 (4) Å

b = 10.9198 (14) Å

c = 8.1228 (10) Å

β = 95.92 (2)°

V = 2888.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.982, T max = 0.989

18031 measured reflections

3448 independent reflections

2142 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 0.95

3448 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011597/fj2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011597/fj2404Isup2.hkl

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

C18H16N2O2	F(000) = 1232
Mr = 292.33	Dx = 1.344 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4881 reflections
a = 32.741 (4) Å	θ = 1.3–28.0°
b = 10.9198 (14) Å	µ = 0.09 mm−1
c = 8.1228 (10) Å	T = 113 K
β = 95.92 (2)°	Prism, colorless
V = 2888.6 (6) Å3	0.20 × 0.18 × 0.12 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	3448 independent reflections
Radiation source: rotating anode	2142 reflections with I > 2σ(I)
multilayer	Rint = 0.063
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.3°
ω and φ scans	h = −43→41
Absorption correction: multi-scan CrystalClear	k = −14→14
Tmin = 0.982, Tmax = 0.989	l = −10→10
18031 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-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 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.20711 (3)	0.14159 (10)	0.06099 (12)	0.0315 (3)
O2	0.20245 (3)	0.38939 (9)	0.62925 (12)	0.0282 (3)
N1	0.18498 (4)	0.16470 (11)	0.31678 (14)	0.0221 (3)
N2	0.18241 (4)	0.22441 (11)	0.46481 (14)	0.0229 (3)
C1	0.20713 (5)	0.20250 (14)	0.19094 (18)	0.0241 (3)
C2	0.22975 (5)	0.31536 (14)	0.22369 (18)	0.0257 (4)
H2	0.2460	0.3470	0.1432	0.031*
C3	0.22792 (5)	0.37578 (14)	0.36727 (18)	0.0253 (4)
H3	0.2427	0.4499	0.3894	0.030*
C4	0.20319 (5)	0.32523 (14)	0.48542 (17)	0.0231 (3)
C5	0.15786 (4)	0.05874 (13)	0.29089 (17)	0.0232 (3)
H5A	0.1559	0.0173	0.3982	0.028*
H5B	0.1698	0.0000	0.2164	0.028*
C6	0.11536 (5)	0.09390 (13)	0.21683 (17)	0.0222 (3)
C7	0.09415 (5)	0.01638 (14)	0.10195 (17)	0.0257 (4)
H7	0.1068	−0.0570	0.0701	0.031*
C8	0.05468 (5)	0.04490 (15)	0.03337 (18)	0.0298 (4)
H8	0.0406	−0.0082	−0.0461	0.036*
C9	0.03585 (5)	0.15088 (15)	0.08102 (19)	0.0304 (4)
H9	0.0088	0.1706	0.0347	0.036*
C10	0.05657 (5)	0.22800 (14)	0.19643 (19)	0.0289 (4)
H10	0.0436	0.3004	0.2299	0.035*
C11	0.09614 (5)	0.20016 (14)	0.26341 (18)	0.0261 (4)
H11	0.1102	0.2540	0.3417	0.031*
C12	0.17631 (5)	0.34314 (15)	0.74918 (18)	0.0281 (4)
H12A	0.1835	0.3852	0.8562	0.034*
H12B	0.1818	0.2546	0.7665	0.034*
C13	0.13136 (5)	0.36113 (13)	0.69709 (17)	0.0246 (4)
C14	0.10296 (5)	0.28071 (14)	0.75401 (18)	0.0274 (4)
H14	0.1122	0.2156	0.8260	0.033*
C15	0.06137 (5)	0.29469 (14)	0.70671 (19)	0.0301 (4)
H15	0.0422	0.2389	0.7454	0.036*
C16	0.04764 (5)	0.39007 (14)	0.60290 (19)	0.0317 (4)
H16	0.0191	0.3996	0.5698	0.038*
C17	0.07560 (5)	0.47139 (15)	0.54761 (19)	0.0317 (4)
H17	0.0663	0.5371	0.4768	0.038*
C18	0.11706 (5)	0.45739 (14)	0.59503 (18)	0.0293 (4)
H18	0.1360	0.5142	0.5575	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0356 (7)	0.0367 (7)	0.0229 (6)	−0.0022 (5)	0.0066 (5)	−0.0036 (5)
O2	0.0292 (6)	0.0304 (6)	0.0252 (6)	−0.0038 (5)	0.0037 (5)	−0.0070 (5)
N1	0.0246 (7)	0.0239 (7)	0.0177 (6)	−0.0016 (5)	0.0020 (5)	−0.0007 (5)
N2	0.0239 (7)	0.0255 (7)	0.0191 (6)	0.0017 (5)	0.0009 (5)	−0.0020 (5)
C1	0.0244 (8)	0.0282 (9)	0.0194 (7)	0.0034 (6)	0.0016 (6)	0.0022 (6)
C2	0.0243 (8)	0.0280 (9)	0.0247 (8)	−0.0005 (7)	0.0026 (6)	0.0038 (7)
C3	0.0223 (8)	0.0243 (8)	0.0288 (8)	−0.0007 (6)	0.0003 (7)	0.0015 (7)
C4	0.0221 (8)	0.0253 (8)	0.0213 (8)	0.0022 (6)	−0.0008 (6)	−0.0018 (6)
C5	0.0266 (8)	0.0211 (8)	0.0220 (7)	−0.0021 (6)	0.0029 (6)	−0.0001 (6)
C6	0.0248 (8)	0.0228 (8)	0.0193 (7)	−0.0019 (6)	0.0032 (6)	0.0028 (6)
C7	0.0300 (9)	0.0251 (8)	0.0225 (8)	−0.0044 (7)	0.0059 (7)	−0.0006 (6)
C8	0.0301 (9)	0.0333 (9)	0.0256 (8)	−0.0082 (7)	0.0006 (7)	−0.0015 (7)
C9	0.0274 (9)	0.0332 (9)	0.0298 (9)	−0.0029 (7)	−0.0008 (7)	0.0063 (7)
C10	0.0304 (9)	0.0259 (9)	0.0304 (9)	0.0019 (7)	0.0028 (7)	0.0021 (7)
C11	0.0283 (8)	0.0245 (8)	0.0247 (8)	−0.0005 (7)	−0.0011 (6)	−0.0018 (7)
C12	0.0322 (9)	0.0329 (9)	0.0194 (8)	−0.0013 (7)	0.0034 (7)	−0.0020 (7)
C13	0.0336 (9)	0.0216 (8)	0.0190 (7)	0.0002 (7)	0.0047 (6)	−0.0041 (6)
C14	0.0357 (9)	0.0240 (8)	0.0222 (8)	0.0001 (7)	0.0023 (7)	0.0001 (6)
C15	0.0327 (9)	0.0292 (9)	0.0289 (8)	−0.0041 (7)	0.0057 (7)	−0.0016 (7)
C16	0.0314 (9)	0.0340 (10)	0.0294 (9)	0.0024 (7)	0.0020 (7)	−0.0030 (7)
C17	0.0385 (10)	0.0275 (9)	0.0293 (9)	0.0056 (7)	0.0036 (7)	0.0030 (7)
C18	0.0345 (9)	0.0259 (9)	0.0283 (8)	−0.0012 (7)	0.0071 (7)	0.0034 (7)

O1—C1	1.2476 (17)	C8—H8	0.9500
O2—C4	1.3647 (17)	C9—C10	1.385 (2)
O2—C12	1.4522 (18)	C9—H9	0.9500
N1—C1	1.3763 (19)	C10—C11	1.386 (2)
N1—N2	1.3780 (15)	C10—H10	0.9500
N1—C5	1.4605 (18)	C11—H11	0.9500
N2—C4	1.2959 (18)	C12—C13	1.502 (2)
C1—C2	1.448 (2)	C12—H12A	0.9900
C2—C3	1.347 (2)	C12—H12B	0.9900
C2—H2	0.9500	C13—C18	1.390 (2)
C3—C4	1.429 (2)	C13—C14	1.392 (2)
C3—H3	0.9500	C14—C15	1.385 (2)
C5—C6	1.507 (2)	C14—H14	0.9500
C5—H5A	0.9900	C15—C16	1.385 (2)
C5—H5B	0.9900	C15—H15	0.9500
C6—C11	1.391 (2)	C16—C17	1.383 (2)
C6—C7	1.392 (2)	C16—H16	0.9500
C7—C8	1.389 (2)	C17—C18	1.381 (2)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.385 (2)	C18—H18	0.9500
C4—O2—C12	117.36 (12)	C10—C9—H9	120.1
C1—N1—N2	126.19 (12)	C8—C9—H9	120.1
C1—N1—C5	119.33 (12)	C9—C10—C11	120.34 (15)
N2—N1—C5	114.18 (11)	C9—C10—H10	119.8
C4—N2—N1	115.86 (12)	C11—C10—H10	119.8
O1—C1—N1	120.95 (14)	C10—C11—C6	120.47 (15)
O1—C1—C2	124.38 (14)	C10—C11—H11	119.8
N1—C1—C2	114.67 (13)	C6—C11—H11	119.8
C3—C2—C1	120.56 (14)	O2—C12—C13	113.20 (12)
C3—C2—H2	119.7	O2—C12—H12A	108.9
C1—C2—H2	119.7	C13—C12—H12A	108.9
C2—C3—C4	118.12 (14)	O2—C12—H12B	108.9
C2—C3—H3	120.9	C13—C12—H12B	108.9
C4—C3—H3	120.9	H12A—C12—H12B	107.8
N2—C4—O2	119.42 (13)	C18—C13—C14	118.68 (15)
N2—C4—C3	124.59 (13)	C18—C13—C12	121.80 (14)
O2—C4—C3	115.98 (13)	C14—C13—C12	119.51 (14)
N1—C5—C6	112.22 (12)	C15—C14—C13	120.64 (15)
N1—C5—H5A	109.2	C15—C14—H14	119.7
C6—C5—H5A	109.2	C13—C14—H14	119.7
N1—C5—H5B	109.2	C14—C15—C16	119.97 (16)
C6—C5—H5B	109.2	C14—C15—H15	120.0
H5A—C5—H5B	107.9	C16—C15—H15	120.0
C11—C6—C7	118.77 (14)	C17—C16—C15	119.76 (16)
C11—C6—C5	121.93 (14)	C17—C16—H16	120.1
C7—C6—C5	119.28 (14)	C15—C16—H16	120.1
C8—C7—C6	120.80 (15)	C18—C17—C16	120.19 (15)
C8—C7—H7	119.6	C18—C17—H17	119.9
C6—C7—H7	119.6	C16—C17—H17	119.9
C9—C8—C7	119.86 (15)	C17—C18—C13	120.74 (15)
C9—C8—H8	120.1	C17—C18—H18	119.6
C7—C8—H8	120.1	C13—C18—H18	119.6
C10—C9—C8	119.75 (15)
C1—N1—N2—C4	−0.3 (2)	C11—C6—C7—C8	0.7 (2)
C5—N1—N2—C4	−173.91 (12)	C5—C6—C7—C8	178.90 (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—C10	0.2 (2)
N2—N1—C1—C2	0.8 (2)	C8—C9—C10—C11	0.5 (2)
C5—N1—C1—C2	174.04 (12)	C9—C10—C11—C6	−0.6 (2)
O1—C1—C2—C3	179.70 (14)	C7—C6—C11—C10	0.0 (2)
N1—C1—C2—C3	−0.6 (2)	C5—C6—C11—C10	−178.11 (14)
C1—C2—C3—C4	0.1 (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—C14	152.30 (13)
C12—O2—C4—N2	−3.1 (2)	C18—C13—C14—C15	1.5 (2)
C12—O2—C4—C3	177.58 (12)	C12—C13—C14—C15	−179.46 (14)
C2—C3—C4—N2	0.4 (2)	C13—C14—C15—C16	−0.6 (2)
C2—C3—C4—O2	179.72 (13)	C14—C15—C16—C17	−0.3 (2)
C1—N1—C5—C6	−88.39 (16)	C15—C16—C17—C18	0.3 (2)
N2—N1—C5—C6	85.65 (14)	C16—C17—C18—C13	0.7 (2)
N1—C5—C6—C11	−38.55 (18)	C14—C13—C18—C17	−1.6 (2)
N1—C5—C6—C7	143.33 (13)	C12—C13—C18—C17	179.41 (14)

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.38	3.2906 (19)	161 (19)
C11—H11···N2	0.95	2.49	3.126 (2)	124
C11—H11···Cg3	0.95	2.98	3.7103 (17)	135
C17—H17···Cg3ii	0.95	2.98	3.6991 (17)	133

CgI—CgJ	Cg—Cg(Å)	CgIPerp(Å)	CgjPerp(Å)	Slippage(Å)
Cg1—Cg1	3.6867 (10)	3.224	3.224	1.789

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.38	3.2906 (19)	161 (19)
C11—H11⋯N2	0.95	2.49	3.126 (2)	124
C11—H11⋯Cg3	0.95	2.98	3.7103 (17)	135
C17—H17⋯Cg3ii	0.95	2.98	3.6991 (17)	133

Symmetry codes: (i) ; (ii) .