Received 5 November 2012
aHacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 06100 Sihhiye-Ankara, Turkey,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: firstname.lastname@example.org
The title compound, C23H25BrN2O3, crystallizes with two independent molecules in the asymmetric unit (Z' = 2) which differ in the twist of the 5-bromo-1H-indole ring with respect to the plane of the 4-methyl-1,4,5,6,7,8-hexahydroquinoline ring [dihedral angles of 78.55 (9) and 89.70 (8)° in molecules A and B, respectively]. The indole ring is planar in both molecules [maximum deviations = 0.021 (3) and -0.020 (3) Å for the N atom] while the cyclohexene ring has adopts a sofa conformation. In the crystal, molecules are linked by pairs of N-HO hydrogen bonds, forming dimers with R12(6) ring motifs. These dimers are connected by N-HO hydrogen bonds, generating chains along . A C-HO contact occurs between the independent molecules.
For biological properties of 1,4-dihydropyridines, see: Triggle, (2003); Safak & Simsek (2006). For the introduction of nifedipine into clinical use, see: Gordeev et al. (1998). For a description of the Cambridge Structural Database, see: Allen, (2002). For geometric analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990). For similar structures, see: El-Khouly et al. (2012); Öztürk Yildirim et al. (2012).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5269 ).
RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.
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