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Volume 67 
Part 6 
Page o1343  
June 2011  

Received 29 April 2011
Accepted 3 May 2011
Online 7 May 2011

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 14.2
Details
Open access

Gliquidone

Thomas Gelbrich,a* Mairi F. Haddowa+ and Ulrich J. Griessera

aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
Correspondence e-mail: thomas.gelbrich@uibk.ac.at

The title compound {systematic name: N-cyclohexylcarbamoyl-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide}, C27H33N3O6S, displays an intramolecular N-H...O=S interaction, as well as intermolecular N-H...O=C hydrogen bonds. The latter interactions lead to the formation of hydrogen-bonded chains parallel to the c axis. The conformation of the sulfonylurea fragment is in agreement with a recent theoretical study [Kasetti et al. (2010[Kasetti, Y., Patel, N. K., Sundriyal, S. & Bharatam, P. V. (2010). J. Phys. Chem. B, 114, 11603-11610.]). J. Phys. Chem. B, 114, 11603-11610].

Related literature

For theoretical studies of the molecular structure, see Lins et al. (1996[Lins, L., Brasseur, R. & Malaisse, W. J. (1996). Pharm. Res. 34, 9-10.]); Kasetti et al. (2010[Kasetti, Y., Patel, N. K., Sundriyal, S. & Bharatam, P. V. (2010). J. Phys. Chem. B, 114, 11603-11610.]). For thermomicroscopy, see Kuhnert-Brandstätter et al. (1982[Kuhnert-Brandstätter, M., Geiler, M. & Wurian, I. (1982). Sci. Pharm. 50, 324-331.]). For related crystal structures, see: Kobelt & Paulus (1972[Kobelt, D. & Paulus, E. F. (1972). Acta Cryst. B28, 3452-3457.]); Iwata et al. (1997[Iwata, M., Nagase, H., Endo, T. & Ueda, H. (1997). Acta Cryst. C53, 329-331.]); Grell et al. (1998[Grell, W., Hurnaus, R., Griss, G., Sauter, R., Rupprecht, E., Mark, M., Luger, P., Nar, H., Wittneben, H. & Müller, P. (1998). J. Med. Chem. 41, 5219-5246.]); Endo et al. (2003[Endo, T., Iwata, M., Nagase, H., Shiro, M. & Ueda, H. (2003). STP Pharma Sci. 13, 281-286.]).

[Scheme 1]

Experimental

Crystal data

  • C27H33N3O6S

  • Mr = 527.62

  • Monoclinic, P 21 /c

  • a = 19.1494 (4) Å

  • b = 10.7253 (3) Å

  • c = 13.8024 (2) Å

  • [beta] = 106.691 (1)°

  • V = 2715.34 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 120 K

  • 0.40 × 0.40 × 0.10 mm
Data collection

  • Bruker-Nonius Roper CCD camera on [kappa]-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.937, Tmax = 0.984

  • 28737 measured reflections

  • 5325 independent reflections

  • 4361 reflections with I > 2[sigma](I)

  • Rint = 0.044
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.101

  • S = 1.03

  • 5325 reflections

  • 376 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O5i 0.86 (1) 2.03 (2) 2.8702 (17) 167 (2)
N2-H2N...O1 0.87 (1) 2.15 (2) 2.8404 (17) 136 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: AcademicPress.]) and COLLECT; data reduction: DENZO and COLLECT; 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: XP in SHELXTL (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.] and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2285 ).

References

Endo, T., Iwata, M., Nagase, H., Shiro, M. & Ueda, H. (2003). STP Pharma Sci. 13, 281-286.  [ChemPort]
Grell, W., Hurnaus, R., Griss, G., Sauter, R., Rupprecht, E., Mark, M., Luger, P., Nar, H., Wittneben, H. & Müller, P. (1998). J. Med. Chem. 41, 5219-5246.  [ISI] [PubMed]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Iwata, M., Nagase, H., Endo, T. & Ueda, H. (1997). Acta Cryst. C53, 329-331.  [CrossRef] [details]
Kasetti, Y., Patel, N. K., Sundriyal, S. & Bharatam, P. V. (2010). J. Phys. Chem. B, 114, 11603-11610.  [ChemPort] [PubMed]
Kobelt, D. & Paulus, E. F. (1972). Acta Cryst. B28, 3452-3457.  [CrossRef] [ChemPort] [details]
Kuhnert-Brandstätter, M., Geiler, M. & Wurian, I. (1982). Sci. Pharm. 50, 324-331.
Lins, L., Brasseur, R. & Malaisse, W. J. (1996). Pharm. Res. 34, 9-10.  [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: AcademicPress.
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2011). E67, o1343  [ doi:10.1107/S1600536811016680 ]

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