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

Aubert, E.; Thuaud, F.; Ribeiro, N.; Désaubry, L.; Espinosa, E.

doi:10.1107/S1600536812049641

Volume 69
Part 1
Pages o52-o53
January 2013

Received 22 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.074
Data-to-parameter ratio = 15.1
Details

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 and Enrique Espinosa ^a

^aCristallographie, Résonance Magnétique et Modélisations (CRM2), UMR CNRS-UHP 7036, Institut Jean Barriol, Université de Lorraine, BP 70239, Bd des Aiguillettes, 54506 Vandoeuvre-les-Nancy, France, and ^bTherapeutic Innovation Laboratory (UMR7200), Department of Medicinal Chemistry, Faculté de Pharmacie, CNRS Université de Strasbourg, 74 Route du Rhin, BP 60024, 67401 Illkirch, France
Correspondence e-mail: emmanuel.aubert@crm2.uhp-nancy.fr

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-HO and C-HO hydrogen bonds form S(5) motifs. In the crystal, the organic and the water molecules are linked by an O-HO hydrogen bond. Pairs of organic and water molecules, located about inversion centers, interact through O-HO hydrogen bonds, forming R₄⁴(20) and R₄⁴(26) motifs, which together lead to C₂²(9) motifs. The crystal packing is also characterized by N-HO and C-HO hydrogen bonds between neighbouring organic molecules, forming R₂²(10) and R₂²(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, $[P \overline 1]$
a = 8.5941 (2) Å
b = 12.1107 (4) Å
c = 12.6642 (3) Å
= 70.537 (2)°
= 73.495 (2)°
= 73.898 (2)°
V = 1166.98 (5) Å³
Z = 2
Cu K radiation
= 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 > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.074
S = 1.05
4860 reflections
322 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.38 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N18-H18O17	0.83	2.31	2.652 (2)	106
C32-H32O1	0.95	2.28	2.661 (2)	103
O17-H17O33	0.84	1.90	2.686 (2)	156
N18-H18O17ⁱ	0.83	2.38	3.185 (2)	163
C28-H28O33ⁱ	0.95	2.53	3.328 (2)	142
C29-H29O15ⁱ	0.95	2.62	3.516 (2)	157
O33-H33AO13ⁱⁱ	0.81	2.21	3.015 (2)	179
O33-H33BO20ⁱⁱⁱ	0.81	1.90	2.699 (2)	170
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) x-1, y, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: BX2432 ).

Acknowledgements

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.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Bernard, Y., Ribeiro, N., Thuaud, F., Türkeri, G., Dirr, R., Boulberdaa, M., Nebigil, C. G. & Désaubry, L. (2011). PLoS ONE, 6, e25302.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
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Ribeiro, N., Thuaud, F., Nebigil, C. G. & Désaubry, L. (2012b). Bioorg. Med. Chem. 20, 1857-1864.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Thuaud, F., Ribeiro, N., Gaiddon, C., Cresteil, T. & Désaubry, L. (2011). J. Med. Chem. 54, 411-415.

organic compounds