1-Benzoyl-5-phenyl-2-(propan-2-yl)-1,2,3,4-tetra­hydro­pyrimidin-4-one

Caracelli, I.; Zukerman-Schpector, J.; Amaral, M.F.Z.J.; Stefani, H.A.; Tiekink, E.R.T.

doi:10.1107/S1600536809036356

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2466

doi:10.1107/S1600536809036356

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1-Benzoyl-5-phenyl-2-(propan-2-yl)-1,2,3,4-tetrahydropyrimidin-4-one

Ignez Caracelli,^a ^* Julio Zukerman-Schpector,^b Mônica F. Z. J. Amaral,^c Hélio A. Stefani ^c and Edward R. T. Tiekink ^b

^aBioMat-Physics Department, Universidade Estadual Paulista Júlio de Mesquita Filho, UNESP, 17033-360 Bauru, SP, Brazil, ^bDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and ^cDepartamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil
^*Correspondence e-mail: ignez@fc.unesp.br

(Received 7 September 2009; accepted 8 September 2009; online 16 September 2009)

The tetrahydropyrimidinone ring in the title compound, C₂₀H₂₀N₂O₂, is in a half-boat conformation with the N—C—N C atom 0.580 (2) Å out of the plane defined by the remaining five atoms. In the crystal structure, molecules are connected into centrosymmetric dimers via N—H⋯O interactions. The dimeric aggregates are linked into supramolecular chains along the a axis via C—H⋯π interactions.

Related literature

For background to the use of potassium organotrifluoroborate salts in organic synthesis, see: Caracelli et al. (2007 ); Stefani et al. (2007 ); Vieira et al. (2008 ). For a related structure, see: Vega-Teijido et al. (2007 ). For conformational analysis, see: Cremer & Pople (1975 ); Iulek & Zukerman-Schpector (1997 ).

Experimental

Crystal data

C₂₀H₂₀N₂O₂
M_r = 320.38
Monoclinic, P 2₁ /n
a = 9.346 (4) Å
b = 8.001 (3) Å
c = 22.528 (9) Å
β = 96.843 (9)°
V = 1672.6 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 98 K
0.35 × 0.22 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan ABSCOR (Higashi, 1995 ) T_min = 0.811, T_max = 1
5658 measured reflections
3094 independent reflections
2636 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.126
S = 1.09
3094 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.22 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
N3—H1N3⋯O1ⁱ	0.93	1.90	2.827 (2)	174
C9—H9⋯Cgⁱⁱ	0.93	2.82	3.632 (2)	147
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z. Cg is the centroid of the C14–C19 ring.

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036356/ng2639sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036356/ng2639Isup2.hkl

checkCIF report

Comment top

As part of our on-going research interest efforts exploring the chemistry of potassium organotrifluoroborate salts, including their potential use as intermediates in organic synthesis (Caracelli et al., 2007; Stefani et al., 2007; Vieira et al. 2008), we have started to use the Suzuki–Miyaura cross-coupling reaction as a new tool to synthesize β-amino acids. Herein, the crystal structure of (I) is described.

The molecular structure of (I), Fig. 1, shows the tetrahydropyrimidinone ring to adopt a half-boat conformation with the C2 atom being displaced 0.580 (2) Å out of the plane defined by the remaining five atoms. The ring-puckering parameters are q₂ = 0.374 (2) Å, q₃ = 0.187 (1) Å, Q = 0.418 (2) Å, and ϕ₂ = 54.0 (2)° (Cremer & Pople, 1975; Iulek & Zukerman-Schpector, 1997). The dihedral angle between the aryl rings is 55.55 (8)°. The deviation of the torsion angle C4—C5—C14—C15 from the ideal value of 60°, which would indicate bisection of the dihydripyrimidinone ring by the plane of the phenyl ring, is of 15.7°.

In the crystal packing, centrosymmetric dimers are formed being consolidated by eight-membered {O═C—N—H···}₂ synthons, Table 1. The carbonyl-O2 atom is involved in an intramolecular C—H···O contact with the C—H2 atom (2.34 Å) and does not particiate in a significant intermolecular contact. The aggregates thus formed are linked into supramolecular chains, Fig. 2, aligned along the a axis via C—H···π interactions: C9—H9···Cg(C14–C19)ⁱ = 2.82 Å, C9···Cg(C14–C19)ⁱ = 3.632 (2) Å with an angle of 147° at H9; symmetry operation i: 1 - x, -y, -z.

Related literature top

For background to the use of potassium organotrifluoroborate salts in organic synthesis, see: Caracelli et al. (2007); Stefani et al. (2007); Vieira et al. (2008). For a related structure, see: Vega-Teijido et al. (2007). For conformational analysis, see: Cremer & Pople (1975); Iulek & Zukerman-Schpector (1997). Cg is the centroid of the C14–C19 ring.

Experimental top

A 50 ml flask under N₂ atmosphere was charged with potassium phenyltrifluoroborate (1.2 mmol), (S)-5-iodopyrimidinone 3 (1.0 mmol, 370 mg), Pd(OAc)₂ (9 mol%, 20.02 mg), K₂CO₃ (2 mmol, 276 mg), and 16 ml of degassed dioxane/H₂O (3/1). The reaction mixture was refluxed at 383 K and the reaction followed by TLC and GC. After completion, the reaction mixture was cooled and then extracted with ethyl acetate (3 × 50 ml). The organic layers were combined, dried (MgSO₄), and the solvent removed under vacuum to give a viscous oil. The oil was purified via column chromatography using a mixture of ethyl acetate/hexane (1:1) as the eluent. Single crystals of (I) were obtained by slow evaporation from ethyl acetate.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. Supramolecular chain in (I) comprising centrosymmetric dimers mediated by {O═C—N—H···}₂ synthons (hydrogen bonds shown as orange dashed lines) linked by C—H···π interactions (shown as purple dashed lines).

1-Benzoyl-5-phenyl-2-(propan-2-yl)-1,2,3,4-tetrahydropyrimidin-4-one top

Crystal data top

C₂₀H₂₀N₂O₂	F(000) = 680
M_r = 320.38	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6484 reflections
a = 9.346 (4) Å	θ = 2.5–40.2°
b = 8.001 (3) Å	µ = 0.08 mm⁻¹
c = 22.528 (9) Å	T = 98 K
β = 96.843 (9)°	Prism, colourless
V = 1672.6 (12) Å³	0.35 × 0.22 × 0.10 mm
Z = 4

Data collection top

Rigaku AFC12/SATURN724 diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2636 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	h = −11→8
T_min = 0.811, T_max = 1	k = −6→9
5658 measured reflections	l = −26→27

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0541P)² + 0.6346P] where P = (F_o² + 2F_c²)/3
3094 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₀N₂O₂	V = 1672.6 (12) Å³
M_r = 320.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.346 (4) Å	µ = 0.08 mm⁻¹
b = 8.001 (3) Å	T = 98 K
c = 22.528 (9) Å	0.35 × 0.22 × 0.10 mm
β = 96.843 (9)°

Data collection top

Rigaku AFC12/SATURN724 diffractometer	3094 independent reflections
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	2636 reflections with I > 2σ(I)
T_min = 0.811, T_max = 1	R_int = 0.035
5658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	Δρ_max = 0.22 e Å⁻³
3094 reflections	Δρ_min = −0.20 e Å⁻³
213 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C2	0.91894 (17)	0.2343 (2)	0.10191 (7)	0.0228 (4)
H2	0.9791	0.1868	0.1364	0.027*
C4	0.81099 (17)	0.1247 (2)	0.00497 (7)	0.0227 (4)
C5	0.68065 (16)	0.2234 (2)	0.01348 (7)	0.0215 (4)
C6	0.66388 (17)	0.2745 (2)	0.06922 (7)	0.0225 (4)
H6	0.5782	0.3264	0.0759	0.027*
C7	0.74672 (18)	0.2425 (2)	0.17669 (7)	0.0250 (4)
C8	0.59340 (18)	0.2378 (2)	0.19000 (7)	0.0249 (4)
C9	0.49283 (19)	0.1281 (2)	0.16115 (8)	0.0289 (4)
H9	0.5177	0.0606	0.1304	0.035*
C10	0.3547 (2)	0.1194 (3)	0.17838 (8)	0.0346 (4)
H10	0.2877	0.0448	0.1596	0.041*
C11	0.3174 (2)	0.2217 (3)	0.22339 (9)	0.0362 (5)
H11	0.2248	0.2171	0.2345	0.043*
C12	0.4177 (2)	0.3315 (2)	0.25215 (8)	0.0346 (4)
H12	0.3917	0.4005	0.2823	0.041*
C13	0.5563 (2)	0.3389 (2)	0.23625 (8)	0.0296 (4)
H13	0.6239	0.4107	0.2562	0.036*
C14	0.56628 (17)	0.2461 (2)	−0.03774 (7)	0.0219 (4)
C15	0.60156 (17)	0.2860 (2)	−0.09467 (7)	0.0235 (4)
H15	0.6977	0.2993	−0.1005	0.028*
C16	0.49504 (18)	0.3061 (2)	−0.14248 (7)	0.0264 (4)
H16	0.5201	0.3327	−0.1801	0.032*
C17	0.35113 (18)	0.2865 (2)	−0.13443 (8)	0.0279 (4)
H17	0.2796	0.3000	−0.1665	0.033*
C18	0.31473 (18)	0.2469 (2)	−0.07842 (8)	0.0285 (4)
H18	0.2184	0.2339	−0.0729	0.034*
C19	0.42147 (17)	0.2262 (2)	−0.03020 (7)	0.0245 (4)
H19	0.3958	0.1990	0.0073	0.029*
C20	0.98292 (17)	0.4034 (2)	0.08670 (7)	0.0260 (4)
H20	0.9135	0.4597	0.0573	0.031*
C21	1.12258 (19)	0.3783 (2)	0.05890 (8)	0.0323 (4)
H21A	1.1605	0.4851	0.0492	0.048*
H21B	1.1035	0.3125	0.0232	0.048*
H21C	1.1916	0.3215	0.0868	0.048*
C22	1.01001 (18)	0.5154 (2)	0.14175 (8)	0.0318 (4)
H22A	0.9239	0.5223	0.1610	0.048*
H22B	1.0367	0.6252	0.1298	0.048*
H22C	1.0865	0.4692	0.1691	0.048*
N1	0.77103 (14)	0.25198 (17)	0.11728 (6)	0.0226 (3)
N3	0.91274 (14)	0.11564 (18)	0.05278 (6)	0.0232 (3)
H1N3	0.9978	0.0622	0.0463	0.028*
O1	0.82249 (12)	0.04539 (16)	−0.04171 (5)	0.0292 (3)
O2	0.84733 (13)	0.23635 (17)	0.21657 (5)	0.0335 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0202 (8)	0.0296 (9)	0.0179 (8)	0.0028 (7)	0.0000 (6)	−0.0023 (7)
C4	0.0207 (8)	0.0246 (8)	0.0227 (8)	−0.0016 (7)	0.0022 (6)	−0.0002 (7)
C5	0.0201 (8)	0.0254 (8)	0.0191 (8)	−0.0008 (7)	0.0022 (6)	0.0008 (7)
C6	0.0198 (7)	0.0273 (8)	0.0203 (8)	0.0023 (7)	0.0018 (6)	0.0029 (7)
C7	0.0308 (9)	0.0247 (9)	0.0192 (8)	0.0059 (7)	0.0015 (7)	0.0028 (7)
C8	0.0307 (9)	0.0265 (9)	0.0180 (8)	0.0051 (7)	0.0047 (6)	0.0049 (7)
C9	0.0337 (9)	0.0316 (9)	0.0220 (8)	0.0023 (8)	0.0061 (7)	0.0021 (7)
C10	0.0345 (10)	0.0382 (11)	0.0318 (10)	−0.0026 (8)	0.0072 (7)	0.0062 (8)
C11	0.0342 (10)	0.0420 (11)	0.0346 (10)	0.0079 (9)	0.0129 (8)	0.0104 (9)
C12	0.0454 (11)	0.0349 (10)	0.0257 (9)	0.0146 (9)	0.0137 (8)	0.0055 (8)
C13	0.0383 (10)	0.0281 (9)	0.0226 (8)	0.0056 (8)	0.0041 (7)	0.0020 (7)
C14	0.0223 (8)	0.0227 (8)	0.0206 (8)	0.0007 (7)	0.0026 (6)	−0.0009 (6)
C15	0.0220 (8)	0.0266 (8)	0.0220 (8)	−0.0008 (7)	0.0030 (6)	−0.0003 (7)
C16	0.0306 (9)	0.0292 (9)	0.0191 (8)	−0.0001 (7)	0.0024 (7)	0.0012 (7)
C17	0.0272 (8)	0.0317 (9)	0.0228 (8)	0.0052 (8)	−0.0049 (6)	−0.0012 (7)
C18	0.0199 (8)	0.0370 (10)	0.0283 (9)	0.0023 (7)	0.0012 (7)	−0.0021 (8)
C19	0.0232 (8)	0.0311 (9)	0.0194 (8)	0.0012 (7)	0.0037 (6)	0.0007 (7)
C20	0.0243 (8)	0.0282 (9)	0.0242 (8)	0.0011 (7)	−0.0026 (6)	−0.0001 (7)
C21	0.0334 (9)	0.0343 (10)	0.0297 (9)	−0.0054 (8)	0.0060 (7)	−0.0005 (8)
C22	0.0281 (9)	0.0325 (10)	0.0338 (10)	0.0004 (8)	−0.0006 (7)	−0.0090 (8)
N1	0.0212 (7)	0.0292 (8)	0.0169 (7)	0.0030 (6)	0.0008 (5)	0.0012 (6)
N3	0.0196 (6)	0.0270 (7)	0.0223 (7)	0.0034 (6)	0.0003 (5)	−0.0030 (6)
O1	0.0247 (6)	0.0379 (7)	0.0243 (6)	0.0044 (5)	0.0001 (4)	−0.0091 (5)
O2	0.0325 (7)	0.0468 (8)	0.0197 (6)	0.0053 (6)	−0.0031 (5)	0.0007 (6)

Geometric parameters (Å, º) top

C2—N3	1.454 (2)	C12—H12	0.9300
C2—N1	1.471 (2)	C13—H13	0.9300
C2—C20	1.534 (2)	C14—C19	1.393 (2)
C2—H2	0.9800	C14—C15	1.399 (2)
C4—O1	1.244 (2)	C15—C16	1.386 (2)
C4—N3	1.351 (2)	C15—H15	0.9300
C4—C5	1.483 (2)	C16—C17	1.387 (2)
C5—C6	1.347 (2)	C16—H16	0.9300
C5—C14	1.488 (2)	C17—C18	1.382 (3)
C6—N1	1.396 (2)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.394 (2)
C7—O2	1.222 (2)	C18—H18	0.9300
C7—N1	1.386 (2)	C19—H19	0.9300
C7—C8	1.499 (2)	C20—C22	1.526 (2)
C8—C9	1.389 (3)	C20—C21	1.527 (2)
C8—C13	1.395 (2)	C20—H20	0.9800
C9—C10	1.394 (2)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.380 (3)	C21—H21C	0.9600
C10—H10	0.9300	C22—H22A	0.9600
C11—C12	1.387 (3)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—C13	1.386 (3)	N3—H1N3	0.9300

N3—C2—N1	106.75 (12)	C16—C15—C14	120.86 (15)
N3—C2—C20	112.78 (14)	C16—C15—H15	119.6
N1—C2—C20	111.71 (13)	C14—C15—H15	119.6
N3—C2—H2	108.5	C15—C16—C17	120.20 (15)
N1—C2—H2	108.5	C15—C16—H16	119.9
C20—C2—H2	108.5	C17—C16—H16	119.9
O1—C4—N3	121.55 (15)	C18—C17—C16	119.55 (15)
O1—C4—C5	122.39 (14)	C18—C17—H17	120.2
N3—C4—C5	115.88 (14)	C16—C17—H17	120.2
C6—C5—C4	118.07 (15)	C17—C18—C19	120.48 (16)
C6—C5—C14	122.20 (15)	C17—C18—H18	119.8
C4—C5—C14	119.36 (14)	C19—C18—H18	119.8
C5—C6—N1	122.08 (15)	C14—C19—C18	120.44 (16)
C5—C6—H6	119.0	C14—C19—H19	119.8
N1—C6—H6	119.0	C18—C19—H19	119.8
O2—C7—N1	120.79 (16)	C22—C20—C21	110.07 (14)
O2—C7—C8	121.49 (15)	C22—C20—C2	111.56 (15)
N1—C7—C8	117.71 (14)	C21—C20—C2	110.53 (14)
C9—C8—C13	120.04 (16)	C22—C20—H20	108.2
C9—C8—C7	122.16 (15)	C21—C20—H20	108.2
C13—C8—C7	117.61 (16)	C2—C20—H20	108.2
C8—C9—C10	119.94 (17)	C20—C21—H21A	109.5
C8—C9—H9	120.0	C20—C21—H21B	109.5
C10—C9—H9	120.0	H21A—C21—H21B	109.5
C11—C10—C9	119.90 (18)	C20—C21—H21C	109.5
C11—C10—H10	120.0	H21A—C21—H21C	109.5
C9—C10—H10	120.0	H21B—C21—H21C	109.5
C10—C11—C12	120.21 (17)	C20—C22—H22A	109.5
C10—C11—H11	119.9	C20—C22—H22B	109.5
C12—C11—H11	119.9	H22A—C22—H22B	109.5
C13—C12—C11	120.43 (17)	C20—C22—H22C	109.5
C13—C12—H12	119.8	H22A—C22—H22C	109.5
C11—C12—H12	119.8	H22B—C22—H22C	109.5
C12—C13—C8	119.46 (18)	C7—N1—C6	124.81 (14)
C12—C13—H13	120.3	C7—N1—C2	119.25 (13)
C8—C13—H13	120.3	C6—N1—C2	115.93 (13)
C19—C14—C15	118.46 (15)	C4—N3—C2	122.15 (14)
C19—C14—C5	120.67 (15)	C4—N3—H1N3	115.7
C15—C14—C5	120.87 (14)	C2—N3—H1N3	117.6

O1—C4—C5—C6	165.73 (16)	C14—C15—C16—C17	−0.1 (3)
N3—C4—C5—C6	−9.5 (2)	C15—C16—C17—C18	0.0 (3)
O1—C4—C5—C14	−7.5 (2)	C16—C17—C18—C19	−0.1 (3)
N3—C4—C5—C14	177.25 (14)	C15—C14—C19—C18	−0.4 (3)
C4—C5—C6—N1	6.5 (2)	C5—C14—C19—C18	−179.68 (16)
C14—C5—C6—N1	179.57 (15)	C17—C18—C19—C14	0.3 (3)
O2—C7—C8—C9	−129.50 (19)	N3—C2—C20—C22	−171.05 (13)
N1—C7—C8—C9	49.6 (2)	N1—C2—C20—C22	68.70 (17)
O2—C7—C8—C13	45.5 (2)	N3—C2—C20—C21	−48.23 (18)
N1—C7—C8—C13	−135.33 (17)	N1—C2—C20—C21	−168.48 (13)
C13—C8—C9—C10	0.1 (3)	O2—C7—N1—C6	−173.99 (16)
C7—C8—C9—C10	175.01 (16)	C8—C7—N1—C6	6.9 (2)
C8—C9—C10—C11	1.1 (3)	O2—C7—N1—C2	7.3 (2)
C9—C10—C11—C12	−1.0 (3)	C8—C7—N1—C2	−171.89 (14)
C10—C11—C12—C13	−0.3 (3)	C5—C6—N1—C7	−155.06 (17)
C11—C12—C13—C8	1.5 (3)	C5—C6—N1—C2	23.7 (2)
C9—C8—C13—C12	−1.4 (3)	N3—C2—N1—C7	132.30 (15)
C7—C8—C13—C12	−176.52 (15)	C20—C2—N1—C7	−104.00 (17)
C6—C5—C14—C19	−38.0 (2)	N3—C2—N1—C6	−46.57 (18)
C4—C5—C14—C19	134.97 (17)	C20—C2—N1—C6	77.13 (17)
C6—C5—C14—C15	142.74 (18)	O1—C4—N3—C2	165.52 (15)
C4—C5—C14—C15	−44.3 (2)	C5—C4—N3—C2	−19.2 (2)
C19—C14—C15—C16	0.3 (3)	N1—C2—N3—C4	46.0 (2)
C5—C14—C15—C16	179.55 (15)	C20—C2—N3—C4	−77.04 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.93	1.90	2.827 (2)	174
C9—H9···Cgⁱⁱ	0.93	2.82	3.632 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₂
M_r	320.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	98
a, b, c (Å)	9.346 (4), 8.001 (3), 22.528 (9)
β (°)	96.843 (9)
V (Å³)	1672.6 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.22 × 0.10

Data collection
Diffractometer	Rigaku AFC12/SATURN724 diffractometer
Absorption correction	Multi-scan ABSCOR (Higashi, 1995)
T_min, T_max	0.811, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	5658, 3094, 2636
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.126, 1.09
No. of reflections	3094
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.93	1.90	2.827 (2)	174
C9—H9···Cgⁱⁱ	0.93	2.82	3.632 (2)	147

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

Acknowledgements

We thank FAPESP (grant Nos. 07/59404-2 to HAS and 08/02531-5 to JZS), CNPq (grant Nos. 472237/2008-0 to IC, 300613/2007 to HAS and 307121/2006-0 to JZS) and CAPES for financial support.

References

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