3-(4-Fluoro­phen­yl)-2-(4-methoxy­phen­oxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

Guo-Ping Zeng; Shi-Rong Yan

doi:10.1107/S1600536808024410

. 2008 Aug 6;64(Pt 9):o1680. doi: 10.1107/S1600536808024410

3-(4-Fluorophenyl)-2-(4-methoxyphenoxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

Guo-Ping Zeng ^a,^b, Shi-Rong Yan ^a,^*

PMCID: PMC2960589 PMID: 21201670

Abstract

There are two crystallographically independent molecules in the asymmetric unit of the title compound, C₂₆H₁₇FN₄O₃, which differ in the dihedral angles between the aromatic rings (fluorophenyl, phenyl) and the pyrrolopyrimidine rings [0.6 (3)/76.3° and 73.7 (3)/64.6°, respectively]. The crystal structure is mainly stabilized by C—H⋯O and C—H⋯F interactions.

Related literature

For related preparation and biological activity, see: Shih et al. (2002 ▶); Niwas et al. (1994 ▶). For related literature, see: Ding et al. (2004 ▶).

Experimental

Crystal data

C₂₆H₁₇FN₄O₃
M _r = 452.44
Tetragonal,
a = 17.7893 (14) Å
c = 14.332 (12) Å
V = 4536 (1) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.36 × 0.23 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.967, T _max = 0.981
29534 measured reflections
4649 independent reflections
2383 reflections with I > 2σ(I)
R _int = 0.136

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.087
S = 0.89
4649 reflections
615 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024410/bt2753sup1.cif

e-64-o1680-sup1.cif^{(34.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024410/bt2753Isup2.hkl

e-64-o1680-Isup2.hkl^{(227.7KB, 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
C19—H19⋯O6	0.93	2.57	3.421 (8)	152
C38—H38⋯O2ⁱ	0.93	2.61	3.405 (8)	144
C50—H50B⋯F1ⁱⁱ	0.96	2.51	3.407 (7)	155
C15—H15⋯O1ⁱⁱⁱ	0.93	2.41	3.201 (9)	143

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

Acknowledgments

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D200724002).

supplementary crystallographic information

Comment

Heterocyclic compounds containing a fused pyrimidinone system have various applications in agriculture and exhibit remarkable biological activity (Ding et al., 2004). Pyrrolopyrimidine derivatives are of great importance because of their remarkable biological properties (Shih, et al., 2002; Niwas, et al., 1994). We present here the crystal structure of the title compound, (Fig. 1), which can be used as a precursor for obtaining bioactive molecules. Within the molecule of the title compound, the bond lengths and angles present no unusual features. In the crystal stucture, two crystallographically independent molecules are found in the asymmetric unit. The mean planes of the pyrrolo[3,2-d]pyrimidine ring system [maximum deviation of 0.028 (4)Å and -0.044 Å for atom C31 and C28, respectively] (A), and the fluorophenyl (B) and phenyl (C12–17 and C35–40) rings (C) form dihedral angles of A/B=80.6 (3)/76.3° and A/C=73.7 (3)/64.6°, respectively. The crystal packing is mainly stabilized by C—H···O and C—H···F interactions (Table 1, Fig.2).

Experimental

The title compound was obtained in excellent yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:2 v/v) at room temperature.