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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 [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.159
Data-to-parameter ratio = 16.2
Details
Open access

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

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-H...O hydrogen bonds, forming dimers with R12(6) ring motifs. These dimers are connected by N-H...O hydrogen bonds, generating chains along [110]. A C-H...O contact occurs between the independent molecules.

Related literature

For biological properties of 1,4-dihydropyridines, see: Triggle, (2003[Triggle, D. J. (2003). Mini Rev. Med. Chem. 3, 215-223.]); Safak & Simsek (2006[Safak, C. & Simsek, R. (2006). Mini Rev. Med. Chem. 6, 747-755.]). For the introduction of nifedipine into clinical use, see: Gordeev et al. (1998[Gordeev, M. F., Patel, D. V., England, B. P., Jonnalagadda, S., Combs, J. D. & Gordon, E. M. (1998). Bioorg. Med. Chem. 6, 883-889.]). For a description of the Cambridge Structural Database, see: Allen, (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For geometric analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For similar structures, see: El-Khouly et al. (2012[El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.]); Öztürk Yildirim et al. (2012[Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.]).

[Scheme 1]

Experimental

Crystal data
  • C23H25BrN2O3

  • Mr = 457.36

  • Monoclinic, P 21 /c

  • a = 14.0044 (6) Å

  • b = 16.8802 (5) Å

  • c = 18.8341 (7) Å

  • [beta] = 105.582 (4)°

  • V = 4288.7 (3) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 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[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.]) in CrysAlis RED (Agilent (2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.])] Tmin = 0.270, Tmax = 0.514

  • 17300 measured reflections

  • 8621 independent reflections

  • 7227 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.159

  • S = 1.02

  • 8621 reflections

  • 531 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.31 e Å-3

  • [Delta][rho]min = -1.01 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2A-H2AB...O1B 0.99 2.51 3.296 (4) 136
N1A-H1AA...O1B 0.88 2.01 2.870 (3) 165
N2A-H2AC...O2Bi 0.88 1.94 2.807 (3) 167
N1B-H1BA...O1Aii 0.88 1.97 2.845 (3) 173
N2B-H2BC...O2Aiii 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Gordeev, M. F., Patel, D. V., England, B. P., Jonnalagadda, S., Combs, J. D. & Gordon, E. M. (1998). Bioorg. Med. Chem. 6, 883-889.  [CrossRef] [ChemPort] [PubMed]
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.  [CrossRef] [details]
Safak, C. & Simsek, R. (2006). Mini Rev. Med. Chem. 6, 747-755.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Triggle, D. J. (2003). Mini Rev. Med. Chem. 3, 215-223.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3404-o3405   [ doi:10.1107/S1600536812046909 ]

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