1-Methyl-7-(4-nitro­phen­yl)-3-phenyl­pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

Jose R Sabino; Cecília M A Oliveira; Carlos A M Fraga; Eliezer J Barreiro; Valéria de Oliveira; Ricardo Menegatti

doi:10.1107/S1600536808037240

. 2008 Nov 13;64(Pt 12):o2356. doi: 10.1107/S1600536808037240

1-Methyl-7-(4-nitrophenyl)-3-phenylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

Jose R Sabino ^a,^*, Cecília M A Oliveira ^b, Carlos A M Fraga ^c, Eliezer J Barreiro ^c, Valéria de Oliveira ^d, Ricardo Menegatti ^d

PMCID: PMC2959918 PMID: 21581329

Abstract

In the title compound, C₂₁H₁₃N₅O₄, the dihedral angles formed between the planes of the phenyl and nitrophenyl rings and that of the heterotricyclic plane are 41.29 (7) and 61.35 (6)°, respectively. In the crystal, weak C—H⋯O interactions help to establish the packing.

Related literature

For background, see: Carneiro et al. (2005 ▶); Menegatti et al. (2006 ▶); Barreiro et al. (2006 ▶).

Experimental

Crystal data

C₂₁H₁₃N₅O₄
M _r = 399.36
Monoclinic,
a = 9.677 (2) Å
b = 12.141 (3) Å
c = 17.438 (4) Å
β = 119.451 (16)°
V = 1784.0 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.89 mm⁻¹
T = 297 (2) K
0.3 × 0.1 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3813 measured reflections
3259 independent reflections
2578 reflections with I > 2σ(I)
R _int = 0.023
2 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.198
S = 1.07
3259 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037240/tk2318sup1.cif

e-64-o2356-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037240/tk2318Isup2.hkl

e-64-o2356-Isup2.hkl^{(156.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O30ⁱ	0.93	2.55	3.216 (3)	129
C18—H18⋯O30ⁱⁱ	0.93	2.44	3.197 (3)	139

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors gratefully acknowledge the financial support of Conselho Nacional de Desenvolvimento Científico e Tecnológico - CNPq, Pró-Reitoria de Pesquisa e Pós Graduação-PRPPG/UFG.

supplementary crystallographic information

Comment

The title compound (I) (Carneiro et al., 2005; Menegatti et al., 2006; Barreiro et al., 2006) features a novel functionalized three-fused rings skeleton, Fig. 1. The bond distances within the pyridine ring are consistent with aromatic delocalization but the pyrazole ring presents a double bond, Table 1. The C8—C9 and C11—C12 bond lengths are elongated from the expected distances by 0.025 and 0.03 Å, respectively.

The pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine moiety is planar (plane α, with r.m.s. deviation of about 0.01 Å). Relative to plane α, the phenyl rings C21/C26 and C13/C18 form dihedral angles of 41.29 (7)° and 61.35 (6)°, respectively. The latter ring is slanted from the plane α so that the C21 and C24 atoms are shifted by 0.118 (3) and 0.436 (4) Å from the plane α, respectively. This might be in part due to the participation of the oxygen atom O30 in two C-H···O contacts, C7—H7···O30ⁱ and C18—H18···O30ⁱⁱ; see Table 2 for details. The former interaction connects molecules into a linear chain along the b-axis and the latter connects parallel chains to form sheets in the plane of approximate indices (-1 0 2). The molecules in the linear chains interact with centrosymmetrically related chains via π···π stacking [closest distance for C25···C25^iv: 3.380 (5) Å; (iv): 1 - x, 1 - y, 1 - z]. In addition, molecules participate in a C—H···π interaction: C25—H25···C15ⁱⁱⁱ [2.74 Å, 3.539 (4) Å, 144°; (iii) 1 -x, -y, 1 -z] to consolidate the crystal packing, Fig. 2.

Experimental

Compound (I) was synthesized as described previously (Menegatti et al., 2006). A colourless needle for crystallography was obtained by slow evaporation of a MeOH solution of (I) at room temperature.