6-Methyl-2-phenyl-4,5-dihydro­pyridazin-3(2H)-one

Sekkak, H.; Rakib, E.M.; Zouihri, H.

doi:10.1107/S1600536811021970

organic compounds

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Volume 67| Part 7| July 2011| Page o1709

doi:10.1107/S1600536811021970

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6-Methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one

Hanan Sekkak,^a El Mostapha Rakib ^a ^* and Hafid Zouihri ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoires de Diffraction des Rayons X, Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: elmostapha1@ymail.com

(Received 14 May 2011; accepted 7 June 2011; online 18 June 2011)

In the title molecule, C₁₁H₁₂N₂O, the pyridazine ring has a skew-boat conformation. The dihedral angle between the phenyl ring [r.m.s deviation = 0.0039 (15) Å] and the best mean-plane of the pyridazine ring [r.m.s deviations = 0.2629 (15) Å] is 53.27 (10)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions involving the methyl group and the phenyl ring of a symmetry-related molecule.

Related literature

For the similar structure, 2-(4-methoxyphenyl)-6-(trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one, see: Wan et al. (2009 ). For conformation analysis of six-membered rings, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₁H₁₂N₂O
M_r = 188.23
Monoclinic, P 2₁
a = 6.4151 (2) Å
b = 7.9010 (2) Å
c = 10.1888 (3) Å
β = 106.607 (1)°
V = 494.89 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.24 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD detector diffractometer
7678 measured reflections
1220 independent reflections
1154 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.094
S = 1.06
1220 reflections
129 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.54	3.371 (3)	149
C5—H5⋯O1ⁱⁱ	0.93	2.50	3.346 (2)	152
C8—H8B⋯O1ⁱⁱⁱ	0.97	2.55	3.474 (3)	159
C11—H11B⋯Cg1^iv	0.96	2.89	3.812 (3)	161
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (ii) x-1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536811021970/su2275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021970/su2275Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021970/su2275Isup3.cml

checkCIF report

Comment top

The molecular structure of the title molecule is illustrated in Fig. 1. The bond distances and angles are simliar to those reported for 2-(4-Methoxyphenyl)-6-(trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one (Wan et al., 2009). The pyridazine ring has a skew-boat conformation; Puckering Amplitude (Q) = 0.428 (2) Å, θ = 69.9 (2)°, ϕ = 207.6 (3) ° (Cremer and Pople, 1975). The dihedral angle between the phenyl ring and the best mean-plane of the pyridazine ring (r.m.s deviations: 0.2629 (15) Å) is 53.27 (10)°.

In the crystal molecules are linked via non-classical C—H···O hydrogen bonds (Table 1), forming a two-dimensional network (Fig. 2). Molecules are also linked by C—H···π interactions involving a methyl H-atom and the phenyl ring of a symmetry related molecule (Table 1).

Related literature top

For the similar structure, 2-(4-methoxyphenyl)-6-(trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one, see: Wan et al. (2009). For conformation analysis of six-membered rings, see: Cremer & Pople (1975).

Experimental top

A mixture of phenylhydrazine (2.7 ml, 27 mmol) and levulinic acid (2.6 ml, 25 mmol) in 60 ml of ethanol were refluxed for 4 h. After cooling the reaction mixture was poured onto ice. The solid obtained was filtered off and recrystallized from methanol to give the title compound as colourless crystals: Yield 3.9 g (85%); Mp: 367–369 K. Spectroscopic data for the title compound is given in the archived CIF.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound, showing the chain formed by C—H···O interactions (dashed lines; see Table 1 for details). H-atoms not involved in hydrogen bonding have been omitted for clarity.

6-Methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one top

Crystal data top

C₁₁H₁₂N₂O	F(000) = 200
M_r = 188.23	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁	Melting point: 397 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.4151 (2) Å	Cell parameters from 256 reflections
b = 7.9010 (2) Å	θ = 2.4–26.5°
c = 10.1888 (3) Å	µ = 0.08 mm⁻¹
β = 106.607 (1)°	T = 296 K
V = 494.89 (2) Å³	Prism, colourless
Z = 2	0.24 × 0.15 × 0.12 mm

Data collection top

Bruker APEXII CCD detector diffractometer	1154 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.5°, θ_min = 2.1°
ω and ϕ scans	h = −8→7
7678 measured reflections	k = −8→10
1220 independent reflections	l = −12→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0443P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1220 reflections	Δρ_max = 0.15 e Å⁻³
129 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.21 (2)

Crystal data top

C₁₁H₁₂N₂O	V = 494.89 (2) Å³
M_r = 188.23	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.4151 (2) Å	µ = 0.08 mm⁻¹
b = 7.9010 (2) Å	T = 296 K
c = 10.1888 (3) Å	0.24 × 0.15 × 0.12 mm
β = 106.607 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	1154 reflections with I > 2σ(I)
7678 measured reflections	R_int = 0.031
1220 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
1220 reflections	Δρ_min = −0.13 e Å⁻³
129 parameters

Special details top

Experimental. Spectroscopic data for the title compound: ¹H-NMR (CDCl₃): δ 2.14 (s, 3H, CH3), 2.54–2.65 (m, 4H, –CH2—CH2-), 7.20–7.31 (m, 2H, H—Ar), 7.36–7–40 (m, 1H, H—Ar), 7.48–7.51 (m, 2H, H—Ar); ¹³C-NMR (CDCl₃): δ 23.2 (CH3), 26.3 (CH2), 27.7 (CH2), 125 (2CH-Ar), 126.5 (CH—Ar), 128.6 (2CH-Ar), 141.1, 154 (2 C), 165 (C═O).

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

	x	y	z	U_iso*/U_eq
C1	0.4300 (3)	0.0477 (3)	0.83092 (17)	0.0488 (5)
C10	0.4122 (2)	0.2873 (2)	0.59455 (17)	0.0413 (4)
C11	−0.1543 (3)	0.1310 (3)	0.2779 (2)	0.0598 (6)
C2	0.4258 (4)	−0.0098 (3)	0.95947 (18)	0.0608 (6)
C3	0.2448 (4)	0.0173 (4)	1.00372 (19)	0.0673 (7)
C4	0.0679 (4)	0.1005 (4)	0.92101 (19)	0.0652 (6)
C5	0.0682 (3)	0.1580 (3)	0.79218 (17)	0.0488 (4)
C6	0.2502 (3)	0.1303 (2)	0.74779 (15)	0.0389 (4)
C7	0.0504 (3)	0.1740 (2)	0.38723 (16)	0.0416 (4)
C8	0.2420 (3)	0.2321 (3)	0.34560 (17)	0.0513 (4)
C9	0.3773 (3)	0.3520 (3)	0.45107 (18)	0.0527 (5)
H1	0.5527	0.0307	0.8012	0.059*
H11A	−0.1265	0.0394	0.2233	0.090*
H11B	−0.2028	0.2282	0.2207	0.090*
H11C	−0.2646	0.0979	0.3195	0.090*
H2	0.5454	−0.0666	1.0154	0.073*
H3	0.2425	−0.0207	1.0897	0.081*
H4	−0.0537	0.1187	0.9516	0.078*
H5	−0.0522	0.2143	0.7365	0.059*
H8A	0.1937	0.2887	0.2576	0.062*
H8B	0.3295	0.1353	0.3359	0.062*
H9A	0.5173	0.3679	0.4341	0.063*
H9B	0.3053	0.4611	0.4420	0.063*
N1	0.25017 (19)	0.18561 (19)	0.61361 (12)	0.0389 (3)
N2	0.0518 (2)	0.1529 (2)	0.51137 (14)	0.0434 (4)
O1	0.5696 (2)	0.3270 (2)	0.68880 (14)	0.0560 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0539 (9)	0.0478 (11)	0.0389 (8)	0.0057 (8)	0.0038 (7)	−0.0021 (8)
C10	0.0413 (7)	0.0409 (9)	0.0420 (8)	−0.0027 (7)	0.0125 (6)	−0.0036 (7)
C11	0.0667 (12)	0.0614 (14)	0.0393 (9)	−0.0110 (11)	−0.0044 (8)	0.0058 (9)
C2	0.0803 (13)	0.0507 (11)	0.0362 (8)	0.0005 (11)	−0.0081 (8)	0.0020 (9)
C3	0.0981 (17)	0.0708 (15)	0.0300 (7)	−0.0190 (14)	0.0136 (9)	0.0020 (9)
C4	0.0708 (12)	0.0870 (17)	0.0420 (9)	−0.0164 (12)	0.0230 (9)	−0.0045 (11)
C5	0.0465 (8)	0.0620 (11)	0.0374 (8)	−0.0036 (9)	0.0112 (6)	0.0008 (8)
C6	0.0448 (8)	0.0387 (8)	0.0301 (7)	−0.0042 (7)	0.0056 (6)	−0.0015 (6)
C7	0.0499 (8)	0.0360 (8)	0.0346 (7)	−0.0007 (7)	0.0048 (6)	0.0022 (7)
C8	0.0625 (10)	0.0570 (11)	0.0352 (7)	−0.0039 (9)	0.0151 (7)	0.0019 (8)
C9	0.0579 (10)	0.0550 (11)	0.0474 (9)	−0.0115 (9)	0.0189 (8)	0.0028 (9)
N1	0.0390 (6)	0.0451 (8)	0.0306 (6)	−0.0027 (6)	0.0067 (5)	0.0004 (6)
N2	0.0416 (7)	0.0494 (9)	0.0342 (6)	−0.0062 (7)	0.0027 (5)	0.0034 (6)
O1	0.0454 (6)	0.0631 (9)	0.0533 (7)	−0.0136 (7)	0.0044 (5)	−0.0029 (7)

Geometric parameters (Å, º) top

C1—H1	0.9300	C5—C4	1.389 (3)
C1—C2	1.394 (3)	C6—N1	1.4351 (19)
C10—C9	1.504 (2)	C6—C5	1.385 (2)
C10—N1	1.371 (2)	C6—C1	1.384 (2)
C10—O1	1.219 (2)	C7—C11	1.498 (2)
C11—H11C	0.9600	C7—C8	1.483 (2)
C11—H11B	0.9600	C7—N2	1.273 (2)
C11—H11A	0.9600	C8—H8B	0.9700
C2—H2	0.9300	C8—H8A	0.9700
C2—C3	1.377 (4)	C9—H9B	0.9700
C3—H3	0.9300	C9—H9A	0.9700
C3—C4	1.373 (4)	C9—C8	1.507 (3)
C4—H4	0.9300	N2—N1	1.4191 (17)
C5—H5	0.9300

C2—C1—H1	120.2	C6—C5—C4	119.07 (19)
C6—C1—H1	120.2	C5—C6—N1	119.50 (15)
C6—C1—C2	119.50 (19)	C1—C6—N1	119.99 (15)
N1—C10—C9	115.39 (14)	C1—C6—C5	120.50 (15)
O1—C10—C9	122.55 (16)	C8—C7—C11	118.64 (15)
O1—C10—N1	122.02 (16)	N2—C7—C11	117.69 (17)
H11B—C11—H11C	109.5	N2—C7—C8	123.63 (14)
H11A—C11—H11C	109.5	H8A—C8—H8B	108.1
C7—C11—H11C	109.5	C9—C8—H8B	109.6
H11A—C11—H11B	109.5	C7—C8—H8B	109.6
C7—C11—H11B	109.5	C9—C8—H8A	109.6
C7—C11—H11A	109.5	C7—C8—H8A	109.6
C1—C2—H2	120.0	C7—C8—C9	110.26 (15)
C3—C2—H2	120.0	H9A—C9—H9B	107.9
C3—C2—C1	120.08 (19)	C8—C9—H9B	109.2
C2—C3—H3	120.0	C10—C9—H9B	109.2
C4—C3—H3	120.0	C8—C9—H9A	109.2
C4—C3—C2	120.02 (17)	C10—C9—H9A	109.2
C5—C4—H4	119.6	C10—C9—C8	112.02 (17)
C3—C4—H4	119.6	N2—N1—C6	113.57 (12)
C3—C4—C5	120.8 (2)	C10—N1—C6	121.30 (13)
C4—C5—H5	120.5	C10—N1—N2	124.06 (13)
C6—C5—H5	120.5	C7—N2—N1	117.09 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.54	3.371 (3)	149
C5—H5···O1ⁱⁱ	0.93	2.50	3.346 (2)	152
C8—H8B···O1ⁱⁱⁱ	0.97	2.55	3.474 (3)	159
C11—H11B···Cg1^iv	0.96	2.89	3.812 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O
M_r	188.23
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.4151 (2), 7.9010 (2), 10.1888 (3)
β (°)	106.607 (1)
V (Å³)	494.89 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7678, 1220, 1154
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.094, 1.06
No. of reflections	1220
No. of parameters	129
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.54	3.371 (3)	149
C5—H5···O1ⁱⁱ	0.93	2.50	3.346 (2)	152
C8—H8B···O1ⁱⁱⁱ	0.97	2.55	3.474 (3)	159
C11—H11B···Cg1^iv	0.96	2.89	3.812 (3)	161

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan, W., Hou, J., Jiang, H., Wang, Y., Zhu, S., Deng, H. & Hao, J. (2009). Tetrahedron, 65, 4212–4219. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1709

doi:10.1107/S1600536811021970

Open

access