4-Benzyl-6-p-tolyl­pyridazin-3(2H)-one

Oubair, A.; Daran, J.-C.; Fihi, R.; Majidi, L.; Azrour, M.

doi:10.1107/S1600536809018376

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1350-o1351

doi:10.1107/S1600536809018376

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4-Benzyl-6-p-tolylpyridazin-3(2H)-one

Ahmad Oubair,^a Jean-Claude Daran,^b Rachid Fihi,^a Lhou Majidi ^a and Mohamed Azrour ^c ^*

^aLaboratoire des Substances Naturelles et Synthèse et Dynamique Moléculaire, Faculté des Sciences et Techniques, BP 509, Errachidia, Morocco, ^bLaboratoire de Chimie de Coordination, UPR–CNRS 8241, 205 Route de Narbonne, 31077 Toulouse Cedex, France, and ^cLaboratoire de Physico-Chimie des Matériaux, Faculté des Sciences et Techniques, BP 509, Errachidia, Morocco
^*Correspondence e-mail: mohamedazrour@yahoo.fr

(Received 28 April 2009; accepted 14 May 2009; online 20 May 2009)

The title compound, C₁₈H₁₆N₂O, is a new dihydropyridazin-3(2H)-one derivative synthesized in one step by condensation of α-benzylidene-γ-tolylbutenolide with hydrazine. The molecule 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 molecules, with a centroid–centroid distance of 3.748 Å, an interplanar 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_r = 276.33
Monoclinic, P 2₁ /n
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) 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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 0.94
2914 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) -x+1, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

In recent years a number of 6-arylpyridazin-3(2H)-ones have been reported to possess antimicrobial (Sayed et al., 2002), anti-inflammatory (Frolov et al., 2004), herbicidal (Piaz et al.,1994), antiplatelet activities (Coelho et al., 2004), anticancer effects (Malinka et al., 2004), antifeedant (Cao et al., 2003), antihypertensive (Ogretir et al.,2002), potent analgesic (Okcelik et al., 2003) and other anticipated biological(Youssef et al., 2005) and pharmacological properties (Sotelo et al., 2003).

In previous papers treating the reactivity of lactones bearing an exocyclic carbon-carbon double bond with 1,3-dipoles (Fihi et al., 1995; Roussel et al., 2000, 2003; Daran et al., 2006), we reported that cycloaddition reactions lead to spiroheterocyclic compounds or evolutive products. In this paper, we describe the synthesis of a new dihydro-2 H– pyridazin-3-onederivative. The condensation ofα-benzylidene-γ-tolylbutenolide(1) and hydrazine (2) in reflux in toluene leads in one step to pyridazin-3-one(3). (Scheme).

Since the ¹H and ¹³CNMR studies did not provide unambiguous information, a single-crystal of (3) was subjected to X-ray diffraction analysis to determine the structure of the product.

The molecule is not planar, the tolyl and the pyridazin rings are twisted to each other making a dihedral angle of 27.35 (9)° and the phenyl ring is nearly perpendicular to the pyridazin ring with a dihedral angle of 85.24 (5)° (Fig. 1).

The molecules are connected two by two through N—H···O hydrogen bonds with a R₂²(8) graph set motif (Bernstein et al., 1995) then building a pseudo dimer arranged around the inversion center (Fig. 1, Table 1). Weak C—H···O hydrogen bonds and weak offset π-π stacking stabilize the packing. The π-π stacking occurs between the pyridazin rings of symmetry related molecules with centroid-to-centroid distance of 3.748 Å and interplanar distance of 3.605Å and a slippage of 1.024 Å.

Related literature top

For general backgound, 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 structural discussion, see: Bernstein et al. (1995).

Experimental top

α-benzylidene-γ-tolylbutenolide (1) was synthesized according to the literature procedure (Filler & Piasek, 1973). (0.036 g, 1.125 mmol) of hydrazine was added to a solution of (1) (0.2 g, 0.76 mmol) in toluene (25 ml) and the mixture was stirred at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was recrystallized from ethanol, and purified by chromatography on silica gel (eluant: ethyl acetate / hexane: 20 / 80). The pyridazinone was recrystallized from ethanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii and hydrogen bonds are shown as dashed lines.[symmetry codes: (i) -x + 1, -y, -z + 1].
	Fig. 2. The formation of the title compound.

4-Benzyl-6-p-tolylpyridazin-3(2H)-one top

Crystal data top

C₁₈H₁₆N₂O	F(000) = 584
M_r = 276.33	D_x = 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

Data collection top

Oxford Diffraction Xcalibur diffractometer	2914 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω and ϕ scans	h = −7→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −12→13
T_min = 0.965, T_max = 0.993	l = −23→23
10925 measured reflections

Refinement top

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(F_o²) + (0.0651P)² + 0.0125P] where P = (F_o² + 2F_c²)/3
2914 reflections	(Δ/σ)_max = 0.008
190 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O	V = 1432.62 (12) Å³
M_r = 276.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2487 (4) Å	µ = 0.08 mm⁻¹
b = 10.4469 (5) Å	T = 180 K
c = 19.1869 (9) Å	0.50 × 0.48 × 0.08 mm
β = 99.598 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2914 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1622 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.993	R_int = 0.044
10925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 0.94	Δρ_max = 0.20 e Å⁻³
2914 reflections	Δρ_min = −0.20 e Å⁻³
190 parameters

Special details top

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 U_iso(H) = xU_eq(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O
M_r	276.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	180
a, b, c (Å)	7.2487 (4), 10.4469 (5), 19.1869 (9)
β (°)	99.598 (5)
V (Å³)	1432.62 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.48 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.965, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10925, 2914, 1622
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 0.94
No. of reflections	2914
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.88	1.89	2.7686 (19)	178.3
C34—H34···O1ⁱⁱ	0.95	2.57	3.512 (2)	169

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2.

References

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Volume 65| Part 6| June 2009| Pages o1350-o1351

doi:10.1107/S1600536809018376

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