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Volume 69 
Part 6 
Page o980  
June 2013  

Received 21 May 2013
Accepted 22 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.122
Data-to-parameter ratio = 15.7
Details
Open access

Rupatadine

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cCR & D, Cadila Pharmaceuticals Ltd, 1389, Trasad Road, Dholka, Ahmedabad 387 810, Gujarat, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound (systematic name: 8-chloro-11-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine), C26H26ClN3, the dihedral angle between the mean planes of the chlorophenyl and cyclohepta[1,2-b]pyridinyl rings fused to the cycloheptane ring is 56.6 (1)°. The mean planes of the cyclohepta[1,2-b]pyridinyl and 5-methylpyridin-3-yl rings are twisted by 64.9 (4)°. The central piperizene group is in a slightly distorted chair configuration. A weak intramolecular C-H...N interaction is observed between the cyclohepta[1,2-b]pyridinyl and piperidin-4-ylidene moieties.

Related literature

For the pharmacological importance of rupatadine, see: Kean & Plosker (2007[Kean, S. J. & Plosker, G. L. (2007). Drugs, 67, 457-474.]); Merlos et al. (1997[Merlos, M., Giral, M., Balsa, D., Ferrando, R., Queralt, M., Puigdemont, A., Garcia-Rafanell, J. & Forn, J. (1997). J. Pharmacol. Exp. Ther. 280, 114-121.]); Mullol et al. (2008[Mullol, J., Bousquet, J., Bachert, C., Canonica, W. G., Gimenez-Arnau, A., Kowalski, M. L., Martí-Guadaño, E., Maurer, M., Picado, C., Scadding, G. & Van Cauwenberge, P. (2008). Allergy, 63, 5-28.]); Picado (2006[Picado, C. (2006). Expert Opin. Pharmacother. 7, 1989-2001.]). For the reported synthesis methodology of rupatadine, see: Agarwal et al. (2008[Agarwal, R., Bhirud, S. B., Bijukumar, G. & Khude, G. D. (2008). Synth. Commun. 38, 122-127.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H26ClN3

  • Mr = 415.95

  • Monoclinic, P 21 /n

  • a = 10.2655 (3) Å

  • b = 11.3341 (4) Å

  • c = 18.8111 (6) Å

  • [beta] = 90.874 (3)°

  • V = 2188.43 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.67 mm-1

  • T = 173 K

  • 0.42 × 0.38 × 0.22 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.673, Tmax = 1.000

  • 13849 measured reflections

  • 4281 independent reflections

  • 3565 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.122

  • S = 1.05

  • 4281 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C19-H19B...N1 0.99 2.60 3.229 (2) 121

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5317 ).


Acknowledgements

HSY thanks the UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agarwal, R., Bhirud, S. B., Bijukumar, G. & Khude, G. D. (2008). Synth. Commun. 38, 122-127.  [CrossRef] [ChemPort]
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Kean, S. J. & Plosker, G. L. (2007). Drugs, 67, 457-474.  [PubMed]
Merlos, M., Giral, M., Balsa, D., Ferrando, R., Queralt, M., Puigdemont, A., Garcia-Rafanell, J. & Forn, J. (1997). J. Pharmacol. Exp. Ther. 280, 114-121.  [ChemPort] [PubMed]
Mullol, J., Bousquet, J., Bachert, C., Canonica, W. G., Gimenez-Arnau, A., Kowalski, M. L., Martí-Guadaño, E., Maurer, M., Picado, C., Scadding, G. & Van Cauwenberge, P. (2008). Allergy, 63, 5-28.  [CrossRef] [PubMed]
Picado, C. (2006). Expert Opin. Pharmacother. 7, 1989-2001.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o980  [ doi:10.1107/S1600536813014256 ]

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