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Volume 69 
Part 1 
Pages o40-o41  
January 2013  

Received 14 November 2012
Accepted 21 November 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 15.7
Details
Open access

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

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and cHacettepe University, Faculty of Pharmacy, Dept. of Pharmaceutical Chemistry, 06100 Sihhiye-Ankara, Turkey
Correspondence e-mail: rbutcher99@yahoo.com

In the title molecule, C24H28N2O3, the cyclohexene ring is in a sofa conformation and the 1,4-dihydropyridine ring is in a slight boat conformation. In the indole ring system, the pyrrole and benzene rings form a dihedral angle of 2.63 (7)°. In the crystal, N-H...O hydrogen bonds connect the molecules into C(6) chains parallel to the b axis and pairs of weak C-H...O hydrogen bonds link inversion-related chains into a ladder motif through R22(18) rings. A weak intramolecular C-H...O hydrogen bond is also observed.

Related literature

For the biological functions of calcium ions, see: Triggle & Swamy (1980[Triggle, D. J. & Swamy, V. C. (1980). Chest, 78, 174-179.]) and for the biological functions and physiological roles of calcium channels, see: Zamponi (1997[Zamponi, G. W. (1997). Drug Dev. Res. 42, 131-143.]); Dolphin (2006[Dolphin, A. C. (2006). Br. J. Pharmacol. 147, 56-62.]). For the biological properties of 1,4-dihydro pyridines (DHP), see: Vaghy et al. (1987[Vaghy, P. L., Williams, J. S. & Schwartz, A. (1987). Am. J. Cardiol. 23, 9A-17A.]); 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.]); Zhou et al., (2011[Zhou, K., Wang, X.-M., Zhao, Y.-Z., Cao, Y.-X., Fu, Q. & Zhang, S. (2011). Med. Chem. Res. 20, 1325-1330.]). For nifedipine (the prototypical DHP) in 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 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.]). 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.]); Gündüz, et al. (2012[Gündüz, M. G., Butcher, R. J., Öztürk Yildirim, S., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3404-o3405.]).

[Scheme 1]

Experimental

Crystal data
  • C24H28N2O3

  • Mr = 392.48

  • Monoclinic, P 21 /c

  • a = 17.4656 (4) Å

  • b = 10.1883 (2) Å

  • c = 12.3465 (3) Å

  • [beta] = 106.806 (2)°

  • V = 2103.16 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.65 mm-1

  • T = 123 K

  • 0.55 × 0.40 × 0.35 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]), based on expressions derived from Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.715, Tmax = 0.804

  • 8035 measured reflections

  • 4246 independent reflections

  • 3533 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.03

  • 4246 reflections

  • 271 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21A...O2 0.98 2.28 2.8073 (19) 113
N1-H1N...O1i 0.86 (2) 1.98 (2) 2.8161 (15) 163.9 (19)
C24-H24C...O2ii 0.98 2.60 3.1693 (19) 118
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5560 ).


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, Oxfordshire, England.
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]
Dolphin, A. C. (2006). Br. J. Pharmacol. 147, 56-62.  [ISI] [CrossRef]
El-Khouly, A., Öztürk Yildirim, S., Butcher, R. J., Simsek, R. & Safak, C. (2012). Acta Cryst. E68, o3337.  [CSD] [CrossRef] [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]
Gündüz, M. G., Butcher, R. J., Öztürk Yildirim, S., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3404-o3405.  [CSD] [CrossRef] [details]
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.  [CSD] [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]
Triggle, D. J. & Swamy, V. C. (1980). Chest, 78, 174-179.  [ChemPort] [PubMed] [ISI]
Vaghy, P. L., Williams, J. S. & Schwartz, A. (1987). Am. J. Cardiol. 23, 9A-17A.  [CrossRef]
Zamponi, G. W. (1997). Drug Dev. Res. 42, 131-143.  [CrossRef] [ChemPort]
Zhou, K., Wang, X.-M., Zhao, Y.-Z., Cao, Y.-X., Fu, Q. & Zhang, S. (2011). Med. Chem. Res. 20, 1325-1330.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o40-o41   [ doi:10.1107/S1600536812047976 ]

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