3-(1,3-Di­phenyl­propan-2-yl)-4-methyl-6-phenyl­isoxazolo[3,4-d]pyridazin-7(6H)-one

Campana, C.F.; Mirzaei, J.; Koerner, C.; Gates, C.; Natale, N.R.

doi:10.1107/S160053681302802X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1680-o1681

doi:10.1107/S160053681302802X

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3-(1,3-Diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one

Charles F. Campana,^a Joseph Mirzaei,^b Chris Koerner,^b Christina Gates ^b and Nicholas R. Natale ^b ^*

^aBruker AXS Inc., 5465 East Cheryl Parkway, Madison, WI 53711, USA, and ^bThe University of Montana-Missoula, The Department of Biomedical & Pharmaceutical Sciences, Missoula, MT 59812-1552, USA
^*Correspondence e-mail: nicholas.natale@umontana.edu

(Received 27 August 2013; accepted 11 October 2013; online 23 October 2013)

In the title compound, C₂₇H₂₃N₃O₂, the geminal benzyl groups branching out from the methine adjacent to the isoxazole group are both syn-oriented to the methyl group of the pyridazinone moiety, as reflected by C—C distances of 3.812 (2) and 4.369 (2) Å between the methyl carbon and the nearest ring carbon of each benzyl group. This kind of conformation is retained in CDCl₃ solution, as evidenced by distinct phenyl-shielding effects on the ¹H NMR signals of the methyl H atoms. The isoxazolo[3,4-d]pyridazin ring system is virtually planar (r.m.s. deviation from planarity = 0.031 Å), but the N-bonded phenyl group is inclined to the former by an ring–ring angle of 55.05 (3)°. In the crystal, the T-shaped molecules are arranged in an interlocked fashion, forming rod-like assemblies along [10-1]. The molecules are held together by unremarkable weak C—H⋯N, C—H⋯O and C—H⋯π interactions (C—O,N,C > 3.4 A), while significant π–π-stacking interactions are absent.

CCDC reference: 966122

Related literature

For chemistry of isoxazolo[3,4-d]pyridazinone preparation, see: Renzi & Dal Piaz (1965 ). For deprotonation with sodium alkoxides, see: Dal Piaz et al. (1975 ); Chimichi et al. (1986 ). For the rearrangement of the isoxazolo[3,4-d]pyridazinone ring system to pyrazole, see: Dal Piaz et al. (1985 ). For isoxazole lateral metalation, see: Natale & Niou (1984 ); Natale et al. (1985 ); Niou & Natale (1986 ); Schlicksupp & Natale (1987 ). For recent applications of lateral metalation and electrophilic quenching of isoxazoles to targets of biological interest, see: Nakamura et al. (2010 ); Hulubei et al. (2012 ). For a review of the lateral metalation and electrophilic quenching of isoxazoles, see: Natale & Mirzaei (1993 ).

Experimental

Crystal data

C₂₇H₂₃N₃O₂
M_r = 421.48
Triclinic, $[P \overline 1]$
a = 7.5163 (4) Å
b = 9.6774 (5) Å
c = 15.9053 (8) Å
α = 86.798 (1)°
β = 83.512 (1)°
γ = 69.385 (1)°
V = 1075.75 (10) Å³
Z = 2
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 100 K
0.40 × 0.22 × 0.19 mm

Data collection

Bruker D8 Venture PHOTON 100 CMOS diffractometer
Absorption correction: numerical (SADABS; Bruker, 2012 ) T_min = 0.80, T_max = 0.89
12012 measured reflections
3714 independent reflections
3597 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.078
S = 1.03
3714 reflections
313 parameters
86 restraints
Only H-atom displacement parameters refined
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O1ⁱ	0.95	2.61	3.4159 (13)	143
C24—H24⋯N1ⁱⁱ	0.95	2.73	3.5407 (15)	143
C11—H11⋯C18ⁱⁱⁱ	0.95	2.78	3.6182 (15)	148
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 966122

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681302802X/qk2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302802X/qk2060Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302802X/qk2060Isup3.cml

checkCIF report

Comment top

The title compound (Fig. 1) was prepared by lateral metalation with lithium hexamethyldisilazide and electrophilic quenching with benzyl bromide (Natale & Mirzaei, 1993), under thermodynamic conditions (Niou & Natale, 1986; Schlicksupp & Natale, 1987), during which a facile second deprotonation and quenching leads to double incorporation (Natale et al., 1985, Natale & Niou, 1984). Mono-alkylation and recovered starting material account for sufficient material balance to rule out substantial rearrangement under these conditions. The present study unambiguously establishes the regiochemistry of double alkylation. Previous reports on analogous deprotonation with sodium alkoxides (Dal Piaz, et al., 1975; Chimichi, et al., 1986), reported rearrangement to pyrazoles with longer reaction times (Dal Piaz et al., 1985). The lateral metalation and electrophilic quenching of isoxazoles continues to lead to candidates with promising biological activity (Nakamura, et al., 2010; Hulubei et al., 2012) and is the subject of active investigation, to be reported in due course. The conformation observed in the solid state (Fig. 1) would be expected to result in magnetic anisotropy if maintained in solution, and this is indeed observed, as the ¹H NMR resonance of the C(4) methyl is observed at δ 2.55 in the starting material, δ 2.21 in the monoalkylated product, and δ 1.86 in the title compound. Further chemistry and pharmacology studies based upon this reaction are underway and will be reported in due course.

Related literature top

For chemistry of isoxazolo[3,4-d]pyridazinone preparation, see: Renzi & Dal Piaz (1965). For deprotonation with sodium alkoxides, see: Dal Piaz et al. (1975); Chimichi et al. (1986). For the rearrangement of the isoxazolo[3,4-d]pyridazinone ring system to pyrazole, see: Dal Piaz et al. (1985). For isoxazole lateral metalation, see: Natale & Niou (1984); Natale et al. (1985); Niou & Natale (1986); Schlicksupp & Natale (1987). For recent applications of lateral metalation and electrophilic quenching of isoxazoles to targets of biological interest, see: Nakamura et al. (2010); Hulubei et al. (2012). For a review of the lateral metalation and electrophilic quenching of isoxazoles, see: Natale & Mirzaei (1993).

Experimental top

Starting material, 3-methyl-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one (Fig. 2) was prepared according to Renzi and Dal Piaz (1965). To starting material (88 mg, 0.36 mmol) was added freshly distilled tetrahydrofuran (THF, 25 ml), under an argon atmosphere. The temperature was lowered to 195 K, and a solution of lithium hexamethyldisilazide (1 ml, 1.0M in THF, Aldrich, 28% excess) was added dropwise over five minutes. After stirring for 1 h, benzyl bromide was added via syringe (0.1 ml, 0.84 mmol, 14% excess). The reaction was allowed to come to room temperature with stirring overnight, after which time the solvent was removed in vacuo by rotary evaporator, and the residue chromatographed on an 80 x 35 cm silica gel column. Gradient chromatogrpahy was performed beginning with chloroform-hexane (1:1), and the gradient slowly increased in polarity to ethyl acetate (EtOAc)-hexane-chloroform (1:2:1). The product 3-(1,3-diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one was obtained from the column fraction with R_f 0.6 (SiO2, EtOAc-hexane-chloroform 2:1:1) as a solid (57.1 mg, 38% yield), and was recrystallized by slow evaporation from EtOAc/hexanes to which a small amount of heptane had been added. The resulting crystals were used in the single crystal X-ray study. A clear light yellow prism-like specimen was selected for the X-ray data collection with a Bruker D8 Venture PHOTON 100 CMOS system equipped with a Cu K_α INCOATEC micro-focus source (λ = 1.54178 Å).

Computing details top

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, with H atoms represented by small spheres of arbitrary radius and displacement ellipsoids at the 50% probability level.
	Fig. 2. Benzylation of 3-methyl-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one as precursor to give the title compound.
	Fig. 3. The unit cell of the title compound.

3-(1,3-Diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one top

Crystal data top

C₂₇H₂₃N₃O₂	Z = 2
M_r = 421.48	F(000) = 444
Triclinic, P1	calculated from global refinement
Hall symbol: -P 1	D_x = 1.301 Mg m⁻³
a = 7.5163 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.6774 (5) Å	Cell parameters from 9923 reflections
c = 15.9053 (8) Å	θ = 2.8–68.4°
α = 86.798 (1)°	µ = 0.66 mm⁻¹
β = 83.512 (1)°	T = 100 K
γ = 69.385 (1)°	Prism, clear light yellow
V = 1075.75 (10) Å³	0.40 × 0.22 × 0.19 mm

Data collection top

Bruker D8 Venture PHOTON 100 CMOS diffractometer	3714 independent reflections
Radiation source: Cu Kα	3597 reflections with I > 2σ(I)
Mirrors monochromator	R_int = 0.017
Detector resolution: 10.4167 pixels mm^-1	θ_max = 66.6°, θ_min = 2.8°
ω and phi scans	h = −8→3
Absorption correction: numerical (SADABS; Bruker, 2012)	k = −11→11
T_min = 0.80, T_max = 0.89	l = −18→18
12012 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	Only H-atom displacement parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0352P)² + 0.337P] where P = (F_o² + 2F_c²)/3
3714 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.22 e Å⁻³
86 restraints	Δρ_min = −0.14 e Å⁻³
0 constraints

Crystal data top

C₂₇H₂₃N₃O₂	γ = 69.385 (1)°
M_r = 421.48	V = 1075.75 (10) Å³
Triclinic, P1	Z = 2
a = 7.5163 (4) Å	Cu Kα radiation
b = 9.6774 (5) Å	µ = 0.66 mm⁻¹
c = 15.9053 (8) Å	T = 100 K
α = 86.798 (1)°	0.40 × 0.22 × 0.19 mm
β = 83.512 (1)°

Data collection top

Bruker D8 Venture PHOTON 100 CMOS diffractometer	3714 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2012)	3597 reflections with I > 2σ(I)
T_min = 0.80, T_max = 0.89	R_int = 0.017
12012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	86 restraints
wR(F²) = 0.078	Only H-atom displacement parameters refined
S = 1.03	Δρ_max = 0.22 e Å⁻³
3714 reflections	Δρ_min = −0.14 e Å⁻³
313 parameters

Special details top

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
O1	0.00502 (11)	0.47448 (8)	0.64153 (5)	0.02756 (18)
N1	0.15001 (13)	0.33590 (10)	0.65000 (6)	0.0270 (2)
C1	0.25346 (14)	0.36020 (11)	0.70485 (6)	0.0222 (2)
C2	0.42780 (15)	0.24940 (11)	0.73381 (6)	0.0226 (2)
O2	0.49243 (11)	0.11970 (8)	0.71482 (5)	0.02828 (18)
N2	0.51293 (12)	0.31237 (9)	0.78613 (5)	0.02217 (19)
N3	0.44085 (12)	0.45480 (9)	0.81882 (5)	0.0235 (2)
C3	0.28457 (14)	0.54911 (11)	0.79389 (6)	0.0224 (2)
C4	0.18507 (14)	0.50724 (11)	0.73305 (6)	0.0217 (2)
C5	0.02762 (15)	0.57547 (12)	0.69057 (6)	0.0232 (2)
C6	0.69832 (14)	0.22965 (11)	0.81342 (7)	0.0224 (2)
C7	0.85159 (15)	0.16976 (11)	0.75336 (7)	0.0260 (2)
H7	0.8334	0.1771	0.6949	0.030 (3)*
C8	1.03243 (15)	0.09880 (12)	0.77969 (7)	0.0278 (2)
H8	1.1385	0.0572	0.739	0.034 (3)*
C9	1.05866 (16)	0.08840 (12)	0.86484 (7)	0.0284 (2)
H9	1.1823	0.0391	0.8826	0.033 (3)*
C10	0.90441 (16)	0.15001 (12)	0.92425 (7)	0.0273 (2)
H10	0.9229	0.1434	0.9827	0.032 (3)*
C11	0.72289 (15)	0.22140 (11)	0.89891 (7)	0.0248 (2)
H11	0.6171	0.264	0.9396	0.025 (3)*
C12	0.21729 (16)	0.69938 (12)	0.83066 (8)	0.0295 (2)
H12A	0.3036	0.7028	0.8717	0.039 (4)*
H12B	0.0879	0.7216	0.8591	0.039 (4)*
H12C	0.2161	0.7725	0.7854	0.043 (4)*
C13	−0.11611 (15)	0.72853 (12)	0.68583 (7)	0.0255 (2)
H13	−0.0688	0.7945	0.7162	0.019 (3)*
C14	−0.31156 (15)	0.73629 (12)	0.73267 (7)	0.0279 (2)
H14A	−0.4109	0.831	0.7186	0.032 (3)*
H14B	−0.3481	0.6549	0.7141	0.029 (3)*
C15	−0.29925 (14)	0.72404 (12)	0.82684 (7)	0.0256 (2)
C16	−0.24282 (15)	0.58718 (12)	0.86891 (7)	0.0280 (2)
H16	−0.222	0.5	0.8387	0.028 (3)*
C17	−0.21682 (16)	0.57717 (13)	0.95421 (7)	0.0306 (3)
H17	−0.1802	0.4835	0.9822	0.038 (4)*
C18	−0.24399 (15)	0.70303 (13)	0.99886 (7)	0.0302 (3)
H18	−0.2237	0.6958	1.0571	0.034 (3)*
C19	−0.30114 (15)	0.83994 (13)	0.95784 (7)	0.0296 (2)
H19	−0.3209	0.9268	0.9882	0.032 (3)*
C20	−0.32932 (15)	0.85002 (12)	0.87290 (7)	0.0278 (2)
H20	−0.3697	0.9442	0.8456	0.034 (3)*
C21	−0.12730 (16)	0.78383 (13)	0.59301 (7)	0.0302 (3)
H21A	−0.1683	0.7183	0.5602	0.029 (3)*
H21B	−0.2235	0.8846	0.5907	0.038 (4)*
C22	0.13242 (17)	0.89367 (13)	0.57720 (7)	0.0308 (3)
H22	0.0532	0.9691	0.6146	0.037 (4)*
C23	0.31273 (18)	0.89326 (13)	0.54685 (7)	0.0336 (3)
H23	0.357	0.9668	0.5641	0.039 (4)*
C24	0.42832 (17)	0.78538 (14)	0.49126 (7)	0.0343 (3)
H24	0.5519	0.7848	0.47	0.039 (4)*
C25	0.36233 (18)	0.67858 (14)	0.46702 (7)	0.0355 (3)
H25	0.4407	0.6048	0.4285	0.046 (4)*
C26	0.18236 (18)	0.67824 (13)	0.49847 (7)	0.0322 (3)
H26	0.1394	0.6036	0.4817	0.036 (3)*
C27	0.06465 (16)	0.78583 (12)	0.55409 (7)	0.0271 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0275 (4)	0.0247 (4)	0.0302 (4)	−0.0066 (3)	−0.0104 (3)	0.0004 (3)
N1	0.0273 (5)	0.0231 (5)	0.0295 (5)	−0.0062 (4)	−0.0071 (4)	0.0001 (4)
C1	0.0238 (5)	0.0218 (5)	0.0219 (5)	−0.0093 (4)	−0.0024 (4)	0.0019 (4)
C2	0.0245 (5)	0.0203 (5)	0.0230 (5)	−0.0085 (4)	−0.0019 (4)	0.0013 (4)
O2	0.0309 (4)	0.0197 (4)	0.0334 (4)	−0.0068 (3)	−0.0064 (3)	−0.0008 (3)
N2	0.0219 (4)	0.0175 (4)	0.0257 (4)	−0.0045 (3)	−0.0044 (3)	0.0001 (3)
N3	0.0227 (4)	0.0194 (4)	0.0273 (5)	−0.0057 (3)	−0.0033 (3)	−0.0016 (3)
C3	0.0203 (5)	0.0218 (5)	0.0249 (5)	−0.0074 (4)	−0.0030 (4)	0.0017 (4)
C4	0.0218 (5)	0.0200 (5)	0.0229 (5)	−0.0075 (4)	−0.0013 (4)	0.0021 (4)
C5	0.0232 (5)	0.0241 (5)	0.0236 (5)	−0.0094 (4)	−0.0042 (4)	0.0017 (4)
C6	0.0216 (5)	0.0163 (5)	0.0296 (5)	−0.0063 (4)	−0.0059 (4)	0.0031 (4)
C7	0.0282 (6)	0.0219 (5)	0.0261 (5)	−0.0065 (4)	−0.0039 (4)	0.0013 (4)
C8	0.0244 (5)	0.0222 (5)	0.0336 (6)	−0.0045 (4)	−0.0011 (4)	−0.0012 (4)
C9	0.0241 (5)	0.0215 (5)	0.0383 (6)	−0.0049 (4)	−0.0097 (4)	0.0030 (4)
C10	0.0300 (6)	0.0238 (5)	0.0283 (6)	−0.0083 (4)	−0.0089 (4)	0.0037 (4)
C11	0.0249 (5)	0.0219 (5)	0.0273 (5)	−0.0081 (4)	−0.0027 (4)	0.0013 (4)
C12	0.0243 (5)	0.0244 (6)	0.0389 (6)	−0.0051 (4)	−0.0086 (5)	−0.0052 (5)
C13	0.0237 (5)	0.0230 (5)	0.0295 (6)	−0.0065 (4)	−0.0082 (4)	0.0033 (4)
C14	0.0224 (5)	0.0244 (6)	0.0363 (6)	−0.0064 (4)	−0.0080 (4)	0.0026 (4)
C15	0.0171 (5)	0.0251 (5)	0.0349 (6)	−0.0078 (4)	−0.0035 (4)	0.0023 (4)
C16	0.0235 (5)	0.0232 (5)	0.0387 (6)	−0.0097 (4)	−0.0046 (4)	0.0010 (5)
C17	0.0270 (6)	0.0267 (6)	0.0391 (6)	−0.0116 (4)	−0.0044 (5)	0.0081 (5)
C18	0.0246 (5)	0.0354 (6)	0.0303 (6)	−0.0111 (5)	−0.0002 (4)	0.0022 (5)
C19	0.0230 (5)	0.0274 (6)	0.0365 (6)	−0.0072 (4)	0.0013 (4)	−0.0040 (5)
C20	0.0210 (5)	0.0214 (5)	0.0384 (6)	−0.0050 (4)	−0.0018 (4)	0.0033 (4)
C21	0.0293 (6)	0.0295 (6)	0.0318 (6)	−0.0084 (5)	−0.0124 (5)	0.0076 (5)
C22	0.0362 (6)	0.0266 (6)	0.0277 (6)	−0.0081 (5)	−0.0059 (5)	0.0013 (4)
C23	0.0416 (7)	0.0345 (6)	0.0302 (6)	−0.0188 (5)	−0.0100 (5)	0.0050 (5)
C24	0.0332 (6)	0.0421 (7)	0.0279 (6)	−0.0138 (5)	−0.0056 (5)	0.0075 (5)
C25	0.0425 (7)	0.0348 (7)	0.0256 (6)	−0.0099 (5)	−0.0003 (5)	−0.0002 (5)
C26	0.0437 (7)	0.0307 (6)	0.0251 (5)	−0.0153 (5)	−0.0088 (5)	0.0018 (4)
C27	0.0304 (6)	0.0271 (6)	0.0235 (5)	−0.0081 (4)	−0.0116 (4)	0.0078 (4)

Geometric parameters (Å, º) top

O1—C5	1.3506 (13)	C13—H13	1.0
O1—N1	1.4100 (11)	C14—C15	1.5067 (16)
N1—C1	1.3138 (14)	C14—H14A	0.99
C1—C4	1.4122 (14)	C14—H14B	0.99
C1—C2	1.4734 (14)	C15—C20	1.3937 (16)
C2—O2	1.2176 (13)	C15—C16	1.3968 (15)
C2—N2	1.3873 (13)	C16—C17	1.3857 (17)
N2—N3	1.3979 (12)	C16—H16	0.95
N2—C6	1.4434 (13)	C17—C18	1.3851 (17)
N3—C3	1.2961 (13)	C17—H17	0.95
C3—C4	1.4425 (15)	C18—C19	1.3898 (16)
C3—C12	1.4909 (15)	C18—H18	0.95
C4—C5	1.3688 (15)	C19—C20	1.3839 (17)
C5—C13	1.4986 (14)	C19—H19	0.95
C6—C7	1.3851 (15)	C20—H20	0.95
C6—C11	1.3869 (15)	C21—C27	1.5105 (16)
C7—C8	1.3906 (16)	C21—H21A	0.99
C7—H7	0.95	C21—H21B	0.99
C8—C9	1.3835 (16)	C22—C23	1.3850 (17)
C8—H8	0.95	C22—C27	1.3940 (16)
C9—C10	1.3861 (16)	C22—H22	0.95
C9—H9	0.95	C23—C24	1.3847 (18)
C10—C11	1.3895 (15)	C23—H23	0.95
C10—H10	0.95	C24—C25	1.3825 (18)
C11—H11	0.95	C24—H24	0.95
C12—H12A	0.98	C25—C26	1.3893 (18)
C12—H12B	0.98	C25—H25	0.95
C12—H12C	0.98	C26—C27	1.3881 (16)
C13—C21	1.5431 (15)	C26—H26	0.95
C13—C14	1.5492 (15)

C5—O1—N1	110.86 (8)	C14—C13—H13	107.2
C1—N1—O1	103.37 (8)	C15—C14—C13	109.92 (8)
N1—C1—C4	113.41 (9)	C15—C14—H14A	109.7
N1—C1—C2	124.88 (9)	C13—C14—H14A	109.7
C4—C1—C2	121.68 (9)	C15—C14—H14B	109.7
O2—C2—N2	123.36 (9)	C13—C14—H14B	109.7
O2—C2—C1	125.71 (10)	H14A—C14—H14B	108.2
N2—C2—C1	110.93 (9)	C20—C15—C16	118.33 (10)
C2—N2—N3	127.80 (8)	C20—C15—C14	119.92 (10)
C2—N2—C6	120.74 (8)	C16—C15—C14	121.55 (10)
N3—N2—C6	111.46 (8)	C17—C16—C15	120.73 (10)
C3—N3—N2	119.61 (9)	C17—C16—H16	119.6
N3—C3—C4	120.23 (9)	C15—C16—H16	119.6
N3—C3—C12	116.70 (9)	C18—C17—C16	120.33 (10)
C4—C3—C12	123.07 (9)	C18—C17—H17	119.8
C5—C4—C1	104.21 (9)	C16—C17—H17	119.8
C5—C4—C3	136.51 (10)	C17—C18—C19	119.48 (11)
C1—C4—C3	119.28 (9)	C17—C18—H18	120.3
O1—C5—C4	108.15 (9)	C19—C18—H18	120.3
O1—C5—C13	115.96 (9)	C20—C19—C18	120.14 (11)
C4—C5—C13	135.89 (10)	C20—C19—H19	119.9
C7—C6—C11	121.11 (10)	C18—C19—H19	119.9
C7—C6—N2	119.36 (9)	C19—C20—C15	120.97 (10)
C11—C6—N2	119.33 (9)	C19—C20—H20	119.5
C6—C7—C8	119.17 (10)	C15—C20—H20	119.5
C6—C7—H7	120.4	C27—C21—C13	110.58 (9)
C8—C7—H7	120.4	C27—C21—H21A	109.5
C9—C8—C7	120.33 (10)	C13—C21—H21A	109.5
C9—C8—H8	119.8	C27—C21—H21B	109.5
C7—C8—H8	119.8	C13—C21—H21B	109.5
C8—C9—C10	119.94 (10)	H21A—C21—H21B	108.1
C8—C9—H9	120.0	C23—C22—C27	121.42 (11)
C10—C9—H9	120.0	C23—C22—H22	119.3
C9—C10—C11	120.40 (10)	C27—C22—H22	119.3
C9—C10—H10	119.8	C24—C23—C22	119.85 (11)
C11—C10—H10	119.8	C24—C23—H23	120.1
C6—C11—C10	119.05 (10)	C22—C23—H23	120.1
C6—C11—H11	120.5	C25—C24—C23	119.42 (11)
C10—C11—H11	120.5	C25—C24—H24	120.3
C3—C12—H12A	109.5	C23—C24—H24	120.3
C3—C12—H12B	109.5	C24—C25—C26	120.56 (11)
H12A—C12—H12B	109.5	C24—C25—H25	119.7
C3—C12—H12C	109.5	C26—C25—H25	119.7
H12A—C12—H12C	109.5	C27—C26—C25	120.70 (11)
H12B—C12—H12C	109.5	C27—C26—H26	119.6
C5—C13—C21	110.34 (9)	C25—C26—H26	119.6
C5—C13—C14	110.96 (9)	C26—C27—C22	118.05 (11)
C21—C13—C14	113.70 (9)	C26—C27—C21	121.96 (10)
C5—C13—H13	107.2	C22—C27—C21	119.91 (10)
C21—C13—H13	107.2

C5—O1—N1—C1	0.42 (11)	C6—C7—C8—C9	−0.07 (16)
O1—N1—C1—C4	−0.08 (11)	C7—C8—C9—C10	−0.54 (16)
O1—N1—C1—C2	−178.31 (9)	C8—C9—C10—C11	0.47 (16)
N1—C1—C2—O2	−4.53 (17)	C7—C6—C11—C10	−0.83 (16)
C4—C1—C2—O2	177.38 (10)	N2—C6—C11—C10	−175.73 (9)
N1—C1—C2—N2	174.91 (10)	C9—C10—C11—C6	0.20 (16)
C4—C1—C2—N2	−3.18 (13)	O1—C5—C13—C21	−53.31 (12)
O2—C2—N2—N3	−172.66 (9)	C4—C5—C13—C21	125.98 (13)
C1—C2—N2—N3	7.88 (14)	O1—C5—C13—C14	73.63 (11)
O2—C2—N2—C6	7.42 (15)	C4—C5—C13—C14	−107.07 (14)
C1—C2—N2—C6	−172.03 (8)	C5—C13—C14—C15	71.49 (11)
C2—N2—N3—C3	−6.84 (15)	C21—C13—C14—C15	−163.44 (9)
C6—N2—N3—C3	173.09 (9)	C13—C14—C15—C20	86.05 (12)
N2—N3—C3—C4	0.28 (14)	C13—C14—C15—C16	−88.63 (12)
N2—N3—C3—C12	−179.32 (9)	C20—C15—C16—C17	−0.22 (15)
N1—C1—C4—C5	−0.26 (12)	C14—C15—C16—C17	174.54 (10)
C2—C1—C4—C5	178.03 (9)	C15—C16—C17—C18	−0.90 (16)
N1—C1—C4—C3	179.63 (9)	C16—C17—C18—C19	1.23 (16)
C2—C1—C4—C3	−2.08 (15)	C17—C18—C19—C20	−0.44 (16)
N3—C3—C4—C5	−176.42 (11)	C18—C19—C20—C15	−0.69 (16)
C12—C3—C4—C5	3.15 (19)	C16—C15—C20—C19	1.01 (15)
N3—C3—C4—C1	3.73 (15)	C14—C15—C20—C19	−173.84 (10)
C12—C3—C4—C1	−176.70 (10)	C5—C13—C21—C27	−59.69 (12)
N1—O1—C5—C4	−0.60 (11)	C14—C13—C21—C27	174.90 (9)
N1—O1—C5—C13	178.88 (8)	C27—C22—C23—C24	1.06 (17)
C1—C4—C5—O1	0.51 (11)	C22—C23—C24—C25	−0.34 (17)
C3—C4—C5—O1	−179.35 (11)	C23—C24—C25—C26	−0.50 (17)
C1—C4—C5—C13	−178.82 (11)	C24—C25—C26—C27	0.65 (17)
C3—C4—C5—C13	1.3 (2)	C25—C26—C27—C22	0.05 (16)
C2—N2—C6—C7	56.43 (13)	C25—C26—C27—C21	−176.67 (10)
N3—N2—C6—C7	−123.50 (10)	C23—C22—C27—C26	−0.90 (16)
C2—N2—C6—C11	−128.58 (10)	C23—C22—C27—C21	175.88 (10)
N3—N2—C6—C11	51.49 (12)	C13—C21—C27—C26	103.38 (12)
C11—C6—C7—C8	0.76 (16)	C13—C21—C27—C22	−73.27 (12)
N2—C6—C7—C8	175.67 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1ⁱ	0.95	2.61	3.4159 (13)	143
C24—H24···N1ⁱⁱ	0.95	2.73	3.5407 (15)	143
C11—H11···C18ⁱⁱⁱ	0.95	2.78	3.6182 (15)	148

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1ⁱ	0.95	2.61	3.4159 (13)	142.8
C24—H24···N1ⁱⁱ	0.95	2.73	3.5407 (15)	143.4
C11—H11···C18ⁱⁱⁱ	0.95	2.78	3.6182 (15)	148.1

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

Acknowledgements

NRN, JM, CG and CK thank the National Institutes of Health for grants NINDS P20RR015583 Center for Structural and Functional Neuroscience (CSFN) and P20 RR017670 Center for Environmental Health Sciences (CEHS), We also thank NINDS P30 (NN and JM), and the University of Montana Grant Program (NN).

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Volume 69| Part 11| November 2013| Pages o1680-o1681

doi:10.1107/S160053681302802X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(1,3-Di­phenyl­propan-2-yl)-4-methyl-6-phenyl­isoxazolo[3,4-d]pyridazin-7(6H)-one

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organic compounds

3-(1,3-Diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one