6-Benz-yloxy-2-phenyl-pyridazin-3(2H)-one.

In the title compound, C(17)H(14)N(2)O(2), the central pyridazine ring forms dihedral angles of 47.29 (5) and 88.54 (5)° with the benzene rings, while the dihedral angle between the benzene rings is 62.68 (6)°. In the crystal, molecules are linked by two weak C-H⋯O hydrogen bonds and three weak C-H⋯π inter-actions.

Related literature

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007 ▶), as pesticides, see: Li et al. (2005 ▶) and as herbicides, see: Xu et al. (2006 ▶). For a related structure, see: Ju et al. (2011 ▶).

Experimental

Crystal data

C17H14N2O2

M = 278.30

Triclinic,

a = 7.390 (4) Å

b = 9.385 (5) Å

c = 10.587 (6) Å

α = 106.618 (7)°

β = 97.489 (6)°

γ = 101.098 (9)°

V = 676.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.982, T max = 0.987

7083 measured reflections

3167 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.070

S = 1.02

3167 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018776/bg2457sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018776/bg2457Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018776/bg2457Isup3.cml

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

C17H14N2O2	Z = 2
Mr = 278.30	F(000) = 292
Triclinic, P1	Dx = 1.365 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.390 (4) Å	Cell parameters from 2420 reflections
b = 9.385 (5) Å	θ = 2.0–27.9°
c = 10.587 (6) Å	µ = 0.09 mm−1
α = 106.618 (7)°	T = 113 K
β = 97.489 (6)°	Prism, colorless
γ = 101.098 (9)°	0.20 × 0.18 × 0.14 mm
V = 676.9 (6) Å3

Rigaku Saturn CCD area-detector diffractometer	3167 independent reflections
Radiation source: rotating anode	2103 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.037
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
Tmin = 0.982, Tmax = 0.987	l = −13→13
7083 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.014P)2] where P = (Fo2 + 2Fc2)/3
3167 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 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	0.42844 (11)	0.94745 (8)	0.63170 (7)	0.0233 (2)
O2	0.77932 (11)	0.49972 (8)	0.63235 (8)	0.0216 (2)
N1	0.48299 (13)	0.75278 (10)	0.71052 (9)	0.0164 (2)
N2	0.57426 (13)	0.63946 (10)	0.71641 (9)	0.0175 (2)
C1	0.36869 (16)	0.78488 (12)	0.81087 (11)	0.0167 (3)
C2	0.18835 (17)	0.79994 (12)	0.77449 (12)	0.0201 (3)
H2	0.1387	0.7879	0.6836	0.024*
C3	0.08053 (17)	0.83289 (12)	0.87255 (12)	0.0220 (3)
H3	−0.0429	0.8447	0.8488	0.026*
C4	0.15216 (17)	0.84853 (12)	1.00468 (12)	0.0226 (3)
H4	0.0780	0.8708	1.0713	0.027*
C5	0.33193 (17)	0.83158 (12)	1.03932 (12)	0.0216 (3)
H5	0.3805	0.8414	1.1298	0.026*
C6	0.44193 (17)	0.80031 (12)	0.94267 (11)	0.0194 (3)
H6	0.5658	0.7896	0.9667	0.023*
C7	0.50525 (16)	0.84005 (12)	0.62487 (11)	0.0175 (3)
C8	0.62325 (15)	0.79457 (12)	0.52976 (11)	0.0187 (3)
H8	0.6404	0.8461	0.4653	0.022*
C9	0.70914 (16)	0.68125 (12)	0.53036 (11)	0.0190 (3)
H9	0.7855	0.6509	0.4669	0.023*
C10	0.68183 (16)	0.60737 (12)	0.63011 (11)	0.0172 (3)
C11	0.76814 (17)	0.43746 (13)	0.74356 (11)	0.0219 (3)
H11A	0.6432	0.3673	0.7289	0.026*
H11B	0.7866	0.5214	0.8293	0.026*
C12	0.91981 (16)	0.35233 (12)	0.74890 (11)	0.0178 (3)
C13	1.09241 (17)	0.42585 (13)	0.83407 (11)	0.0218 (3)
H13	1.1142	0.5302	0.8874	0.026*
C14	1.23333 (17)	0.34891 (13)	0.84226 (11)	0.0230 (3)
H14	1.3512	0.4006	0.9008	0.028*
C15	1.20271 (17)	0.19639 (13)	0.76516 (11)	0.0217 (3)
H15	1.2986	0.1428	0.7712	0.026*
C16	1.03045 (17)	0.12308 (13)	0.67916 (11)	0.0217 (3)
H16	1.0090	0.0189	0.6255	0.026*
C17	0.89004 (17)	0.19985 (12)	0.67083 (11)	0.0206 (3)
H17	0.7727	0.1484	0.6116	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0327 (5)	0.0207 (5)	0.0235 (5)	0.0139 (4)	0.0090 (4)	0.0113 (4)
O2	0.0276 (5)	0.0237 (5)	0.0227 (5)	0.0151 (4)	0.0099 (4)	0.0134 (4)
N1	0.0187 (6)	0.0172 (5)	0.0177 (5)	0.0093 (4)	0.0052 (5)	0.0083 (4)
N2	0.0189 (6)	0.0168 (5)	0.0198 (5)	0.0085 (4)	0.0041 (5)	0.0074 (4)
C1	0.0200 (7)	0.0130 (6)	0.0188 (7)	0.0044 (5)	0.0066 (5)	0.0062 (5)
C2	0.0241 (7)	0.0176 (6)	0.0199 (7)	0.0065 (5)	0.0040 (6)	0.0075 (5)
C3	0.0196 (7)	0.0181 (6)	0.0314 (8)	0.0078 (5)	0.0071 (6)	0.0096 (5)
C4	0.0290 (8)	0.0176 (7)	0.0243 (7)	0.0080 (6)	0.0129 (6)	0.0067 (5)
C5	0.0271 (8)	0.0199 (7)	0.0169 (7)	0.0034 (6)	0.0043 (6)	0.0061 (5)
C6	0.0202 (7)	0.0180 (6)	0.0209 (7)	0.0050 (5)	0.0038 (6)	0.0077 (5)
C7	0.0201 (7)	0.0170 (6)	0.0158 (6)	0.0044 (5)	0.0016 (5)	0.0067 (5)
C8	0.0224 (7)	0.0195 (6)	0.0165 (6)	0.0056 (5)	0.0052 (6)	0.0081 (5)
C9	0.0201 (7)	0.0215 (7)	0.0163 (7)	0.0053 (5)	0.0056 (5)	0.0062 (5)
C10	0.0185 (7)	0.0164 (6)	0.0170 (6)	0.0067 (5)	0.0012 (5)	0.0051 (5)
C11	0.0255 (8)	0.0243 (7)	0.0223 (7)	0.0104 (6)	0.0078 (6)	0.0132 (5)
C12	0.0210 (7)	0.0199 (6)	0.0185 (7)	0.0098 (5)	0.0081 (6)	0.0102 (5)
C13	0.0270 (8)	0.0166 (6)	0.0238 (7)	0.0074 (6)	0.0066 (6)	0.0074 (5)
C14	0.0194 (7)	0.0240 (7)	0.0257 (7)	0.0058 (6)	0.0014 (6)	0.0090 (6)
C15	0.0249 (7)	0.0259 (7)	0.0229 (7)	0.0151 (6)	0.0095 (6)	0.0128 (6)
C16	0.0322 (8)	0.0167 (6)	0.0186 (7)	0.0101 (6)	0.0071 (6)	0.0056 (5)
C17	0.0219 (7)	0.0216 (7)	0.0187 (7)	0.0052 (5)	0.0020 (5)	0.0080 (5)

O1—C7	1.2379 (14)	C8—C9	1.3405 (15)
O2—C10	1.3526 (14)	C8—H8	0.9500
O2—C11	1.4611 (14)	C9—C10	1.4343 (16)
N1—N2	1.3758 (13)	C9—H9	0.9500
N1—C7	1.3899 (14)	C11—C12	1.5006 (16)
N1—C1	1.4429 (14)	C11—H11A	0.9900
N2—C10	1.2967 (14)	C11—H11B	0.9900
C1—C2	1.3836 (17)	C12—C13	1.3862 (16)
C1—C6	1.3850 (17)	C12—C17	1.3907 (16)
C2—C3	1.3911 (16)	C13—C14	1.3839 (16)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.3851 (17)	C14—C15	1.3875 (17)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.3829 (17)	C15—C16	1.3875 (16)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.3896 (16)	C16—C17	1.3799 (16)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.4432 (16)
C10—O2—C11	115.71 (9)	C8—C9—H9	121.1
N2—N1—C7	125.17 (10)	C10—C9—H9	121.1
N2—N1—C1	113.91 (9)	N2—C10—O2	119.85 (10)
C7—N1—C1	120.75 (10)	N2—C10—C9	124.22 (12)
C10—N2—N1	116.73 (10)	O2—C10—C9	115.93 (11)
C2—C1—C6	120.99 (11)	O2—C11—C12	107.55 (9)
C2—C1—N1	119.79 (11)	O2—C11—H11A	110.2
C6—C1—N1	119.22 (11)	C12—C11—H11A	110.2
C1—C2—C3	119.21 (11)	O2—C11—H11B	110.2
C1—C2—H2	120.4	C12—C11—H11B	110.2
C3—C2—H2	120.4	H11A—C11—H11B	108.5
C4—C3—C2	120.34 (12)	C13—C12—C17	119.09 (12)
C4—C3—H3	119.8	C13—C12—C11	119.69 (11)
C2—C3—H3	119.8	C17—C12—C11	121.21 (11)
C5—C4—C3	119.82 (11)	C14—C13—C12	120.71 (11)
C5—C4—H4	120.1	C14—C13—H13	119.6
C3—C4—H4	120.1	C12—C13—H13	119.6
C4—C5—C6	120.45 (12)	C13—C14—C15	120.09 (12)
C4—C5—H5	119.8	C13—C14—H14	120.0
C6—C5—H5	119.8	C15—C14—H14	120.0
C1—C6—C5	119.19 (12)	C14—C15—C16	119.22 (12)
C1—C6—H6	120.4	C14—C15—H15	120.4
C5—C6—H6	120.4	C16—C15—H15	120.4
O1—C7—N1	121.54 (11)	C17—C16—C15	120.69 (12)
O1—C7—C8	123.94 (10)	C17—C16—H16	119.7
N1—C7—C8	114.53 (11)	C15—C16—H16	119.7
C9—C8—C7	121.43 (11)	C16—C17—C12	120.20 (12)
C9—C8—H8	119.3	C16—C17—H17	119.9
C7—C8—H8	119.3	C12—C17—H17	119.9
C8—C9—C10	117.73 (11)
C7—N1—N2—C10	−3.67 (15)	N1—C7—C8—C9	−2.77 (16)
C1—N1—N2—C10	−178.83 (9)	C7—C8—C9—C10	−0.74 (16)
N2—N1—C1—C2	−134.36 (10)	N1—N2—C10—O2	178.41 (9)
C7—N1—C1—C2	50.24 (14)	N1—N2—C10—C9	−0.47 (16)
N2—N1—C1—C6	45.70 (13)	C11—O2—C10—N2	−5.75 (15)
C7—N1—C1—C6	−129.70 (12)	C11—O2—C10—C9	173.22 (9)
C6—C1—C2—C3	0.78 (16)	C8—C9—C10—N2	2.57 (17)
N1—C1—C2—C3	−179.16 (9)	C8—C9—C10—O2	−176.35 (9)
C1—C2—C3—C4	−0.80 (16)	C10—O2—C11—C12	−166.04 (9)
C2—C3—C4—C5	0.13 (16)	O2—C11—C12—C13	94.70 (12)
C3—C4—C5—C6	0.58 (16)	O2—C11—C12—C17	−86.01 (13)
C2—C1—C6—C5	−0.09 (16)	C17—C12—C13—C14	−0.35 (17)
N1—C1—C6—C5	179.85 (9)	C11—C12—C13—C14	178.96 (10)
C4—C5—C6—C1	−0.60 (16)	C12—C13—C14—C15	−0.22 (18)
N2—N1—C7—O1	−174.84 (10)	C13—C14—C15—C16	0.68 (17)
C1—N1—C7—O1	0.01 (17)	C14—C15—C16—C17	−0.59 (17)
N2—N1—C7—C8	5.19 (16)	C15—C16—C17—C12	0.02 (17)
C1—N1—C7—C8	−179.96 (9)	C13—C12—C17—C16	0.44 (17)
O1—C7—C8—C9	177.26 (11)	C11—C12—C17—C16	−178.85 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.95	2.54	3.389 (2)	149
C15—H15···O1ii	0.95	2.44	3.235 (2)	141
C4—H4···Cg2iii	0.95	2.76	3.494 (2)	135
C9—H9···Cg2iv	0.95	2.95	3.752 (2)	143
C13—H13···Cg1v	0.95	2.63	3.456 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.95	2.54	3.389 (2)	149
C15—H15⋯O1ii	0.95	2.44	3.235 (2)	141
C4—H4⋯Cg2iii	0.95	2.76	3.494 (2)	135
C9—H9⋯Cg2iv	0.95	2.95	3.752 (2)	143
C13—H13⋯Cg1v	0.95	2.63	3.456 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .