Ethyl 4-(5-bromo-1H-indol-3-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

Gündüz, M.G.; Butcher, R.J.; Öztürk Yildirim, S.; El-Khouly, A.; Şafak, C.; Şimşek, R.

doi:10.1107/S1600536812046909

Volume 68
Part 12
Pages o3404-o3405
December 2012

Received 5 November 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.159
Data-to-parameter ratio = 16.2
Details

Ethyl 4-(5-bromo-1H-indol-3-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Miyase Gözde Gündüz,^a Ray J. Butcher,^b ^* Sema Öztürk Yildirim,^b,^c Ahmed El-Khouly,^a Cihat Safak ^a and Rahime Simsek ^a

^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: rbutcher99@yahoo.com

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 [110]. A C-HO contact occurs between the independent molecules.

Related literature

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).

Experimental

Crystal data

C₂₃H₂₅BrN₂O₃
M_r = 457.36
Monoclinic, P 2₁ /c
a = 14.0044 (6) Å
b = 16.8802 (5) Å
c = 18.8341 (7) Å
= 105.582 (4)°
V = 4288.7 (3) Å³
Z = 8
Cu K radiation
= 2.83 mm^-1
T = 123 K
0.83 × 0.69 × 0.48 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical [(Clark & Reid, 1995) in CrysAlis RED (Agilent (2011)] T_min = 0.270, T_max = 0.514
17300 measured reflections
8621 independent reflections
7227 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.159
S = 1.02
8621 reflections
531 parameters
H-atom parameters constrained
_max = 1.31 e Å^-3
_min = -1.01 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2A-H2ABO1B	0.99	2.51	3.296 (4)	136
N1A-H1AAO1B	0.88	2.01	2.870 (3)	165
N2A-H2ACO2Bⁱ	0.88	1.94	2.807 (3)	167
N1B-H1BAO1Aⁱⁱ	0.88	1.97	2.845 (3)	173
N2B-H2BCO2Aⁱⁱⁱ	0.88	2.05	2.889 (3)	159
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Gordeev, M. F., Patel, D. V., England, B. P., Jonnalagadda, S., Combs, J. D. & Gordon, E. M. (1998). Bioorg. Med. Chem. 6, 883-889.
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.
Safak, C. & Simsek, R. (2006). Mini Rev. Med. Chem. 6, 747-755.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Triggle, D. J. (2003). Mini Rev. Med. Chem. 3, 215-223.

organic compounds