N-[3a-(4-Bromo­phen­yl)-8b-hy­droxy-6,8-dimeth­oxy-3-phenyl-2,3,3a,8b-tetra­hydro-1H-cyclo­penta­[b]benzofuran-1-yl]formamide monohydrate

Emmanuel Aubert; Frédéric Thuaud; Nigel Ribeiro; Laurent Désaubry; Enrique Espinosa

doi:10.1107/S1600536812049641

. 2012 Dec 8;69(Pt 1):o52–o53. doi: 10.1107/S1600536812049641

N-[3a-(4-Bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl]formamide monohydrate

Emmanuel Aubert ^a,^*, Frédéric Thuaud ^b, Nigel Ribeiro ^b, Laurent Désaubry ^b, Enrique Espinosa ^a

PMCID: PMC3588239 PMID: 23476436

Abstract

In the title compound, C₂₆H₂₄BrNO₅·H₂O, a synthetic analogue of natural flavagline, the cyclopentane ring adopts an envelope conformation (the flap atom bearing the phenyl group) and the vicinal phenyl and bromophenyl groups are slightly shifted relative to each other [C_Ph—C—C—C_PhBr = 36.3 (2)°]. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds form S(5) motifs. In the crystal, the organic and the water molecules are linked by an O—H⋯O hydrogen bond. Pairs of organic and water molecules, located about inversion centers, interact through O—H⋯O hydrogen bonds, forming R ₄ ⁴(20) and R ₄ ⁴(26) motifs, which together lead to C ₂ ²(9) motifs. The crystal packing is also characterized by N—H⋯O and C—H⋯O hydrogen bonds between neighbouring organic molecules, forming R ₂ ²(10) and R ₂ ²(18) motifs, respectively.

Related literature

For flavaglines and their anticancer, neuro- and cardioprotective activities, see: Ribeiro et al. (2012a ▶,b ▶); Bernard et al. (2011 ▶); Thuaud et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₄BrNO₅·H₂O
M _r = 528.39
Triclinic,
a = 8.5941 (2) Å
b = 12.1107 (4) Å
c = 12.6642 (3) Å
α = 70.537 (2)°
β = 73.495 (2)°
γ = 73.898 (2)°
V = 1166.98 (5) Å³
Z = 2
Cu Kα radiation
μ = 2.77 mm⁻¹
T = 110 K
0.34 × 0.26 × 0.07 mm

Data collection

Agilent SuperNova diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T _min = 0.551, T _max = 0.868
24473 measured reflections
4860 independent reflections
4814 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.074
S = 1.05
4860 reflections
322 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ▶; molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012) ▶.

Supplementary Material

Click here for additional data file.^{(34.3KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049641/bx2432sup1.cif

e-69-00o52-sup1.cif^{(34.3KB, cif)}

Click here for additional data file.^{(233.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049641/bx2432Isup2.hkl

e-69-00o52-Isup2.hkl^{(233.2KB, hkl)}

Click here for additional data file.^{(9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812049641/bx2432Isup3.cml

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
N18—H18⋯O17	0.83	2.31	2.652 (2)	106
C32—H32⋯O1	0.95	2.28	2.661 (2)	103
O17—H17⋯O33	0.84	1.90	2.686 (2)	156
N18—H18⋯O17ⁱ	0.83	2.38	3.185 (2)	163
C28—H28⋯O33ⁱ	0.95	2.53	3.328 (2)	142
C29—H29⋯O15ⁱ	0.95	2.62	3.516 (2)	157
O33—H33A⋯O13ⁱⁱ	0.81	2.21	3.015 (2)	179
O33—H33B⋯O20ⁱⁱⁱ	0.81	1.90	2.699 (2)	170

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

Acknowledgments

The Service Commun de Diffraction X of the Université de Lorraine is thanked for providing access to crystallographic facilities. Generous financial support for this work was provided to LD by the Association pour la Recherche sur le Cancer (ARC, grant Nos. 3940 and SFI20111204054) and the Fondation pour la Recherche Médicale. We also thank the ARC (NR) and MNESR (FT) for fellowships.

supplementary crystallographic information

Experimental

Suitable crystals of the title compound were obtained by slow evaporation from acetone at room temperature.