1-(4-Bromo­benzo­yl)-2-phenyl­pyrrolidine-2-carboxamide

Rafael Tamazyan; Armen Ayvazyan; Ashot Martirosyan; Gohar Harutunyan; Vahan Martirosyan

doi:10.1107/S1600536808003954

. 2008 Feb 13;64(Pt 3):o580. doi: 10.1107/S1600536808003954

1-(4-Bromobenzoyl)-2-phenylpyrrolidine-2-carboxamide

Rafael Tamazyan ^a,^*, Armen Ayvazyan ^a, Ashot Martirosyan ^b, Gohar Harutunyan ^b, Vahan Martirosyan ^b

PMCID: PMC2960799 PMID: 21201919

Abstract

In the title compound, C₁₈H₁₇BrN₂O₂, which is a potential human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor, the pyrrolidine ring exhibits an envelope conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds [N⋯O = 2.861 (3) Å] link the molecules into centrosymmetric dimers.

Related literature

For related crystal structures, see: Karapetyan et al. (2002 ▶); Tamazyan et al. (2002 ▶, 2007 ▶). For details of the synthesis, see: Martirosyan et al. (2000 ▶, 2004 ▶). For potential pharmacological applications, see: De Clercq (1996 ▶).

Experimental

Crystal data

C₁₈H₁₇BrN₂O₂
M _r = 373.25
Monoclinic,
a = 9.5707 (19) Å
b = 13.738 (3) Å
c = 13.302 (3) Å
β = 96.99 (2)°
V = 1736.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 260 (2) K
0.14 mm (radius)

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: for a sphere (SHELXTL; Sheldrick, 2008 ▶) T _min = 0.612, T _max = 0.617
8356 measured reflections
4180 independent reflections
2941 reflections with I > 2σ(I)
R _int = 0.050
3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.118
S = 1.02
4180 reflections
216 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Data collection: DATACOL in CAD-4 (Enraf–Nonius, 1988 ▶); cell refinement: LS in CAD-4; data reduction: HELENA (Spek, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003954/cv2386sup1.cif

e-64-0o580-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003954/cv2386Isup2.hkl

e-64-0o580-Isup2.hkl^{(204.9KB, 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
N7—H7b⋯O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a⋯O8ⁱ	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Armenian Science and Education Foundation (ANSEF) (grant No. PS-chemorg-907).

supplementary crystallographic information

Comment

The title compound, (I), belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs), which exhibit potential HIV-1 RT inhibition properties (De Clercq, 1996).

In (I) (Fig. 1), all bond lengths and angles are in good agreement with those observed in the related compounds (Karapetyan et al., 2002; Tamazyan et al., 2002, 2007). Both H atoms of amide group, H7b and H7a, respectively, are involved in intra- and intermolecular N—H···O hydrogen bonds (Table 1). The latter one links the molecules into centrosymmetric dimers (Fig. 2).

Experimental

The title compound was synthesized by cycloalkylation of N1-(3-chloropropyl)-N1-cyano(phenyl)methyl-4-bromobenzamide in phase transfer catalyses condition to 1-(4-bromobenzoyl)-2-phenyl-2-pyrrolidinecarbonitrile and then by hydrolizes with concentric sulfuric acid (Martirosyan et al., 2000, 2004). The compound as synthesized is a racemic mixture of optical isomers (R and S) of 1-(4-bromobenzoyl)-2-phenyl-2-pyrrolidinecarboxamide molecule. The crystals were grown from methanol solution. The suitable sample with spherical shape of the size ~0.28 mm was prepared and selected for X-ray diffraction experiment.