4-Benzyl-6-p-tolyl-pyridazin-3(2H)-one.

The title compound, C(18)H(16)N(2)O, is a new dihydro-pyridazin-3(2H)-one derivative synthesized in one step by condensation of α-benzyl-idene-γ-tolyl-butenolide with hydrazine. The mol-ecule is not planar; the tolyl and pyridazine rings are twisted with respect to each other making a dihedral angle of 27.35 (9)° and the benzyl ring is nearly perpendicular to the pyridazine ring with a dihedral angle of 85.24 (5)°. In the crystal structure, inversion dimers arise, being linked by pairs of N-H⋯O hydrogen bonds. Weak C-H⋯O hydrogen bonds and weak offset π-π stacking stabilize the packing. The π-π stacking occurs between the pyridazine rings of symmetry-related mol-ecules, with a centroid-centroid distance of 3.748 Å, an inter-planar distance of 3.605 Å and a slippage of 1.024 Å.

Related literature

For related compounds displaying biological activities, see: Sayed et al. (2002 ▶); Frolov et al. (2004 ▶); Piaz et al. (1994 ▶); Coelho et al. (2004 ▶); Malinka et al. (2004 ▶); Ogretir et al. (2002 ▶); Okcelik et al. (2003 ▶); Sotelo et al. (2003 ▶); Youssef et al. (2005 ▶). For related structures, see: Cao et al. (2003 ▶); Daran et al. (2006 ▶); Fihi et al. (1995 ▶); Filler & Piasek (1973 ▶); Roussel et al. (2000 ▶, 2003 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H16N2O

M = 276.33

Monoclinic,

a = 7.2487 (4) Å

b = 10.4469 (5) Å

c = 19.1869 (9) Å

β = 99.598 (5)°

V = 1432.62 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 180 K

0.50 × 0.48 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.965, T max = 0.993

10925 measured reflections

2914 independent reflections

1622 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 0.94

2914 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018376/bg2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018376/bg2256Isup2.hkl

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

C18H16N2O	F(000) = 584
Mr = 276.33	Dx = 1.281 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3436 reflections
a = 7.2487 (4) Å	θ = 2.8–32.0°
b = 10.4469 (5) Å	µ = 0.08 mm−1
c = 19.1869 (9) Å	T = 180 K
β = 99.598 (5)°	Fragment, colourless
V = 1432.62 (12) Å3	0.50 × 0.48 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	2914 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω and φ scans	h = −7→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −12→13
Tmin = 0.965, Tmax = 0.993	l = −23→23
10925 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0125P] where P = (Fo2 + 2Fc2)/3
2914 reflections	(Δ/σ)max = 0.008
190 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.97 Å (methylene), 0.98Å (methyl) and N—H = 0.86 Å with Uiso(H) = xUeq(C or N) where x=1.2 or 1.5(methyl).Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlis RED (Oxford Diffraction, 2006)

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	Occ. (<1)
O1	0.58992 (17)	−0.03563 (12)	0.42289 (6)	0.0387 (4)
N1	0.8190 (2)	0.19591 (14)	0.54067 (8)	0.0336 (4)
N2	0.7005 (2)	0.10629 (14)	0.50803 (7)	0.0335 (4)
H2	0.6067	0.0848	0.5294	0.040*
C1	0.9570 (3)	0.22886 (16)	0.50837 (9)	0.0296 (4)
C2	0.7092 (3)	0.04582 (17)	0.44647 (9)	0.0297 (4)
C3	0.8621 (2)	0.08373 (17)	0.41181 (9)	0.0296 (4)
C4	0.9807 (2)	0.17325 (17)	0.44281 (9)	0.0309 (4)
H4	1.0821	0.1999	0.4206	0.037*
C11	1.0846 (3)	0.32907 (17)	0.54285 (9)	0.0314 (5)
C12	1.0234 (3)	0.41994 (17)	0.58693 (9)	0.0360 (5)
H12	0.8983	0.4168	0.5956	0.043*
C13	1.1423 (3)	0.51460 (18)	0.61821 (10)	0.0398 (5)
H13	1.0974	0.5757	0.6480	0.048*
C14	1.3252 (3)	0.52198 (18)	0.60691 (10)	0.0392 (5)
C15	1.3863 (3)	0.43020 (19)	0.56396 (10)	0.0414 (5)
H15	1.5122	0.4326	0.5561	0.050*
C16	1.2684 (3)	0.33473 (18)	0.53210 (9)	0.0372 (5)
H16	1.3141	0.2731	0.5028	0.045*
C17	1.4555 (3)	0.6246 (2)	0.64031 (11)	0.0547 (6)
H17A	1.5780	0.6138	0.6259	0.082*	0.50
H17B	1.4691	0.6182	0.6919	0.082*	0.50
H17C	1.4044	0.7087	0.6250	0.082*	0.50
H17D	1.3897	0.6800	0.6693	0.082*	0.50
H17E	1.4986	0.6756	0.6033	0.082*	0.50
H17F	1.5633	0.5851	0.6702	0.082*	0.50
C31	0.8735 (3)	0.02039 (18)	0.34214 (9)	0.0359 (5)
H31A	0.9169	−0.0688	0.3513	0.043*
H31B	0.7463	0.0170	0.3138	0.043*
C32	1.0013 (3)	0.08604 (17)	0.29952 (9)	0.0292 (4)
C33	0.9342 (3)	0.18115 (18)	0.25246 (9)	0.0376 (5)
H33	0.8063	0.2054	0.2473	0.045*
C34	1.0500 (3)	0.2416 (2)	0.21276 (10)	0.0438 (5)
H34	1.0024	0.3074	0.1806	0.053*
C35	1.2341 (3)	0.20623 (19)	0.21994 (11)	0.0467 (6)
H35	1.3142	0.2470	0.1923	0.056*
C36	1.3030 (3)	0.11236 (19)	0.26684 (11)	0.0454 (6)
H36	1.4309	0.0881	0.2719	0.054*
C37	1.1874 (3)	0.05337 (18)	0.30651 (10)	0.0358 (5)
H37	1.2363	−0.0111	0.3394	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0398 (8)	0.0418 (8)	0.0372 (8)	−0.0120 (7)	0.0141 (6)	−0.0062 (7)
N1	0.0369 (10)	0.0355 (9)	0.0299 (8)	−0.0082 (7)	0.0094 (7)	−0.0015 (7)
N2	0.0344 (9)	0.0379 (9)	0.0311 (8)	−0.0100 (8)	0.0139 (7)	−0.0040 (8)
C1	0.0326 (11)	0.0290 (10)	0.0281 (10)	−0.0032 (8)	0.0076 (8)	0.0052 (8)
C2	0.0331 (11)	0.0289 (11)	0.0278 (10)	−0.0029 (9)	0.0071 (8)	0.0012 (9)
C3	0.0306 (11)	0.0313 (11)	0.0285 (10)	0.0012 (8)	0.0093 (8)	0.0027 (8)
C4	0.0315 (11)	0.0336 (11)	0.0293 (10)	−0.0036 (9)	0.0100 (8)	0.0014 (9)
C11	0.0364 (12)	0.0327 (11)	0.0254 (9)	−0.0034 (9)	0.0064 (8)	0.0064 (9)
C12	0.0373 (12)	0.0382 (12)	0.0336 (11)	−0.0028 (9)	0.0088 (9)	0.0027 (10)
C13	0.0497 (14)	0.0344 (12)	0.0340 (11)	−0.0034 (10)	0.0034 (10)	0.0020 (9)
C14	0.0464 (13)	0.0354 (12)	0.0326 (11)	−0.0070 (10)	−0.0028 (9)	0.0077 (9)
C15	0.0336 (12)	0.0472 (13)	0.0420 (12)	−0.0084 (10)	0.0019 (9)	0.0116 (11)
C16	0.0395 (13)	0.0390 (12)	0.0341 (11)	−0.0023 (10)	0.0087 (9)	0.0041 (9)
C17	0.0584 (16)	0.0471 (14)	0.0534 (14)	−0.0177 (11)	−0.0058 (11)	0.0017 (11)
C31	0.0388 (12)	0.0403 (12)	0.0307 (10)	−0.0067 (9)	0.0119 (9)	−0.0046 (9)
C32	0.0354 (12)	0.0307 (11)	0.0227 (9)	−0.0041 (8)	0.0085 (8)	−0.0046 (8)
C33	0.0390 (12)	0.0408 (12)	0.0328 (11)	0.0043 (9)	0.0056 (9)	−0.0016 (9)
C34	0.0649 (16)	0.0374 (12)	0.0303 (11)	−0.0026 (11)	0.0111 (10)	0.0051 (9)
C35	0.0588 (16)	0.0452 (13)	0.0422 (12)	−0.0158 (11)	0.0257 (11)	−0.0073 (11)
C36	0.0353 (13)	0.0461 (13)	0.0575 (14)	−0.0009 (10)	0.0162 (11)	−0.0041 (12)
C37	0.0368 (12)	0.0366 (12)	0.0349 (11)	0.0014 (9)	0.0087 (9)	0.0002 (9)

O1—C2	1.243 (2)	C16—H16	0.9500
N1—C1	1.308 (2)	C17—H17A	0.9800
N1—N2	1.3515 (19)	C17—H17B	0.9800
N2—C2	1.350 (2)	C17—H17C	0.9800
N2—H2	0.8800	C17—H17D	0.9800
C1—C4	1.422 (2)	C17—H17E	0.9800
C1—C11	1.478 (2)	C17—H17F	0.9800
C2—C3	1.440 (2)	C31—C32	1.500 (2)
C3—C4	1.341 (2)	C31—H31A	0.9900
C3—C31	1.506 (2)	C31—H31B	0.9900
C4—H4	0.9500	C32—C37	1.376 (3)
C11—C16	1.383 (3)	C32—C33	1.376 (2)
C11—C12	1.392 (2)	C33—C34	1.377 (3)
C12—C13	1.381 (2)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.369 (3)
C13—C14	1.381 (3)	C34—H34	0.9500
C13—H13	0.9500	C35—C36	1.368 (3)
C14—C15	1.384 (3)	C35—H35	0.9500
C14—C17	1.500 (3)	C36—C37	1.369 (3)
C15—C16	1.387 (2)	C36—H36	0.9500
C15—H15	0.9500	C37—H37	0.9500
C1—N1—N2	116.10 (15)	C14—C17—H17D	109.5
C2—N2—N1	127.66 (15)	H17A—C17—H17D	141.1
C2—N2—H2	116.2	H17B—C17—H17D	56.3
N1—N2—H2	116.2	H17C—C17—H17D	56.3
N1—C1—C4	121.77 (17)	C14—C17—H17E	109.5
N1—C1—C11	116.46 (16)	H17A—C17—H17E	56.3
C4—C1—C11	121.76 (16)	H17B—C17—H17E	141.1
O1—C2—N2	120.52 (16)	H17C—C17—H17E	56.3
O1—C2—C3	124.21 (16)	H17D—C17—H17E	109.5
N2—C2—C3	115.27 (16)	C14—C17—H17F	109.5
C4—C3—C2	118.24 (16)	H17A—C17—H17F	56.3
C4—C3—C31	125.03 (17)	H17B—C17—H17F	56.3
C2—C3—C31	116.72 (16)	H17C—C17—H17F	141.1
C3—C4—C1	120.96 (17)	H17D—C17—H17F	109.5
C3—C4—H4	119.5	H17E—C17—H17F	109.5
C1—C4—H4	119.5	C32—C31—C3	114.42 (15)
C16—C11—C12	118.29 (17)	C32—C31—H31A	108.7
C16—C11—C1	120.67 (17)	C3—C31—H31A	108.7
C12—C11—C1	121.03 (17)	C32—C31—H31B	108.7
C13—C12—C11	120.87 (18)	C3—C31—H31B	108.7
C13—C12—H12	119.6	H31A—C31—H31B	107.6
C11—C12—H12	119.6	C37—C32—C33	118.48 (17)
C14—C13—C12	121.16 (19)	C37—C32—C31	121.19 (17)
C14—C13—H13	119.4	C33—C32—C31	120.33 (17)
C12—C13—H13	119.4	C32—C33—C34	120.83 (18)
C13—C14—C15	117.75 (18)	C32—C33—H33	119.6
C13—C14—C17	121.70 (19)	C34—C33—H33	119.6
C15—C14—C17	120.6 (2)	C35—C34—C33	119.65 (19)
C14—C15—C16	121.71 (19)	C35—C34—H34	120.2
C14—C15—H15	119.1	C33—C34—H34	120.2
C16—C15—H15	119.1	C36—C35—C34	120.14 (19)
C11—C16—C15	120.20 (18)	C36—C35—H35	119.9
C11—C16—H16	119.9	C34—C35—H35	119.9
C15—C16—H16	119.9	C35—C36—C37	119.89 (19)
C14—C17—H17A	109.5	C35—C36—H36	120.1
C14—C17—H17B	109.5	C37—C36—H36	120.1
H17A—C17—H17B	109.5	C36—C37—C32	121.01 (19)
C14—C17—H17C	109.5	C36—C37—H37	119.5
H17A—C17—H17C	109.5	C32—C37—H37	119.5
H17B—C17—H17C	109.5
C1—N1—N2—C2	0.8 (3)	C12—C13—C14—C15	−0.9 (3)
N2—N1—C1—C4	−0.1 (2)	C12—C13—C14—C17	179.75 (17)
N2—N1—C1—C11	178.59 (14)	C13—C14—C15—C16	1.0 (3)
N1—N2—C2—O1	179.62 (16)	C17—C14—C15—C16	−179.62 (17)
N1—N2—C2—C3	−0.9 (3)	C12—C11—C16—C15	−0.9 (3)
O1—C2—C3—C4	179.72 (16)	C1—C11—C16—C15	179.14 (16)
N2—C2—C3—C4	0.3 (2)	C14—C15—C16—C11	−0.1 (3)
O1—C2—C3—C31	0.8 (3)	C4—C3—C31—C32	−14.1 (3)
N2—C2—C3—C31	−178.64 (15)	C2—C3—C31—C32	164.73 (16)
C2—C3—C4—C1	0.3 (3)	C3—C31—C32—C37	90.5 (2)
C31—C3—C4—C1	179.16 (17)	C3—C31—C32—C33	−89.3 (2)
N1—C1—C4—C3	−0.5 (3)	C37—C32—C33—C34	0.6 (3)
C11—C1—C4—C3	−179.06 (16)	C31—C32—C33—C34	−179.63 (17)
N1—C1—C11—C16	153.12 (17)	C32—C33—C34—C35	0.3 (3)
C4—C1—C11—C16	−28.2 (3)	C33—C34—C35—C36	−0.7 (3)
N1—C1—C11—C12	−26.8 (2)	C34—C35—C36—C37	0.2 (3)
C4—C1—C11—C12	151.86 (17)	C35—C36—C37—C32	0.7 (3)
C16—C11—C12—C13	1.0 (2)	C33—C32—C37—C36	−1.1 (3)
C1—C11—C12—C13	−179.02 (16)	C31—C32—C37—C36	179.14 (17)
C11—C12—C13—C14	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88	1.89	2.7686 (19)	178
C34—H34···O1ii	0.95	2.57	3.512 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88	1.89	2.7686 (19)	178
C34—H34⋯O1ii	0.95	2.57	3.512 (2)	169

Symmetry codes: (i) ; (ii) .