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Volume 68 
Part 1 
Pages o54-o55  
January 2012  

Received 16 November 2011
Accepted 30 November 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.075
wR = 0.213
Data-to-parameter ratio = 17.4
Details
Open access

The desoxazoline asidiacyclamide analogue cyclo(Gly-Thr-D-Val-Thz-Ile-Thr-D-Val-Thz) acetonitrile monosolvate

aOsaka University of Pharmaceutical Sciences, Nasahara, Osaka 569-1094, Japan
Correspondence e-mail: doit@gly.oups.ac.jp

The title peptide [systematic name: 4-(butan-2-yl)-7,20-bis(1-hydroxyethyl)-10,23-bis(propan-2-yl)-12,25-dithia-3,6,9,16,19,22,27,28-octaazatricyclo[22.2.1.111,14]octacosa-1(26),11(28),13,24(27)-tetraene-2,5,8,15,18,21-hexone acetonitrile monosolvate], C32H48N8O8S2·CH3CN, an analogue of ascidiacyclamide (ASC) [cyclo(-Ile-Oxz-D-Val-Thz-)2], lies about a twofold rotation axis, so that the glycine (Gly) and isoleucine (Ile) residues are each disordered over two sites with equal occupancies. The acetonitrile molecule is also located on a twofold axis passing through the C and N atoms. In the peptide, the thiazole rings are faced to each other with a dihedral angle of 9.63 (15)° and intramolecular N-H...O and O-H...O hydrogen bonds are observed. A bifurcated N-H...(O,O) hydrogen bond links the peptide molecules into a layer parallel to the ab plane.

Related literature

For general background to ascidiacyclamide, see: Hamamoto et al. (1983[Hamamoto, Y., Endo, M., Nakagawa, M., Nakanishi, T. & Mizukawa, K. (1983). Chem. Commun. pp. 323-324.]); Shioiri et al. (1987[Shioiri, T., Hamada, Y., Kato, S., Shibata, M., Kondo, Y., Nakagawa, H. & Kohda, K. (1987). Biochem. Pharmacol. 36, 4181-4185.]); Ishida et al. (1988[Ishida, T., Tanaka, M., Nabae, M., Inoue, M., Kato, S., Hamada, Y. & Shioiri, T. (1988). J. Org. Chem. 53, 107-112.]); Degnan et al. (1989[Degnan, B. M., Hawkins, C. J., Lavin, M. F., McCaffrey, E. J., Parry, D. L., Van den Brenk, A. L. & Watters, D. J. (1989). J. Med. Chem. 32, 1349-1354.]); Doi et al. (1999[Doi, M., Shinozaki, F., In, Y., Ishida, T., Yamamoto, D., Kamigauchi, M., Sugiura, M., Hamada, Y., Kohda, K. & Shioiri, T. (1999). Biopolymers, 49, 459-469.]); Haberhauer & Rominger (2003[Haberhauer, G. & Rominger, F. (2003). Eur. J. Org. Chem. pp. 3209-3218.]). For related structures, see: Schmitz et al. (1989[Schmitz, F. J., Ksebati, M. B., Chang, J. S., Wang, J. L., Hossain, M. B., Van der Helm, D., Engel, M. H., Serban, A. & Silfer, J. A. (1989). J. Org. Chem. 54, 3463-3472.]); Asano, Doi et al. (2001[Asano, A., Doi, M., Kobayashi, K., Arimoto, M., Ishida, T., Katsuya, Y., Mezaki, Y., Hasegawa, H., Nakai, M., Sasaki, M., Taniguchi, T. & Terashima, A. (2001). Biopolymers, 58, 295-304.]); Asano, Taniguchi et al. (2001[Asano, A., Taniguchi, T., Sasaki, M., Hasegawa, H., Katsuya, Y. & Doi, M. (2001). Acta Cryst. E57, o834-o838.]); Asano et al. (2002[Asano, A., Yamada, T., Numata, A., Katsuya, Y., Sasaki, M., Taniguchi, T. & Doi, M. (2002). Biochem. Biophys. Res. Commun. 297, 143-147.], 2003[Asano, A., Yamada, T., Numata, A. & Doi, M. (2003). Acta Cryst. C59, o488-o490.], 2005[Asano, A., Yamada, T., Katsuya, Y., Taniguchi, T., Sasaki, M. & Doi, M. (2005). J. Pept. Res. 66 (Suppl. 1), 90-98.]).

[Scheme 1]

Experimental

Crystal data
  • C32H48N8O8S2·C2H3N

  • Mr = 777.96

  • Orthorhombic, P 21 21 2

  • a = 18.2019 (9) Å

  • b = 10.4667 (5) Å

  • c = 11.0695 (6) Å

  • V = 2108.89 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 200 K

  • 0.40 × 0.40 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.909, Tmax = 0.982

  • 24275 measured reflections

  • 4669 independent reflections

  • 4359 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.213

  • S = 1.09

  • 4669 reflections

  • 269 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.92 e Å-3

  • [Delta][rho]min = -1.42 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2016 Friedel pairs

  • Flack parameter: 0.11 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O22-H22...O16 0.84 1.87 2.674 (4) 160
N11-H11...O16i 0.88 2.12 2.984 (3) 166
N21-H21...O22ii 0.88 2.29 2.953 (4) 132
N21-H21...O24ii 0.88 2.25 3.013 (4) 145
N31-H31...O44i 0.88 2.27 3.074 (3) 152
Symmetry codes: (i) -x+1, -y+2, z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5015 ).


References

Asano, A., Doi, M., Kobayashi, K., Arimoto, M., Ishida, T., Katsuya, Y., Mezaki, Y., Hasegawa, H., Nakai, M., Sasaki, M., Taniguchi, T. & Terashima, A. (2001). Biopolymers, 58, 295-304.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Asano, A., Taniguchi, T., Sasaki, M., Hasegawa, H., Katsuya, Y. & Doi, M. (2001). Acta Cryst. E57, o834-o838.  [CSD] [CrossRef] [details]
Asano, A., Yamada, T., Katsuya, Y., Taniguchi, T., Sasaki, M. & Doi, M. (2005). J. Pept. Res. 66 (Suppl. 1), 90-98.
Asano, A., Yamada, T., Numata, A. & Doi, M. (2003). Acta Cryst. C59, o488-o490.  [CSD] [CrossRef] [details]
Asano, A., Yamada, T., Numata, A., Katsuya, Y., Sasaki, M., Taniguchi, T. & Doi, M. (2002). Biochem. Biophys. Res. Commun. 297, 143-147.  [CSD] [CrossRef] [PubMed] [ChemPort]
Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Degnan, B. M., Hawkins, C. J., Lavin, M. F., McCaffrey, E. J., Parry, D. L., Van den Brenk, A. L. & Watters, D. J. (1989). J. Med. Chem. 32, 1349-1354.  [CrossRef] [ChemPort] [PubMed] [ISI]
Doi, M., Shinozaki, F., In, Y., Ishida, T., Yamamoto, D., Kamigauchi, M., Sugiura, M., Hamada, Y., Kohda, K. & Shioiri, T. (1999). Biopolymers, 49, 459-469.  [ISI] [CrossRef] [PubMed] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Haberhauer, G. & Rominger, F. (2003). Eur. J. Org. Chem. pp. 3209-3218.  [CSD] [CrossRef]
Hamamoto, Y., Endo, M., Nakagawa, M., Nakanishi, T. & Mizukawa, K. (1983). Chem. Commun. pp. 323-324.
Ishida, T., Tanaka, M., Nabae, M., Inoue, M., Kato, S., Hamada, Y. & Shioiri, T. (1988). J. Org. Chem. 53, 107-112.  [CrossRef] [ChemPort]
Schmitz, F. J., Ksebati, M. B., Chang, J. S., Wang, J. L., Hossain, M. B., Van der Helm, D., Engel, M. H., Serban, A. & Silfer, J. A. (1989). J. Org. Chem. 54, 3463-3472.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shioiri, T., Hamada, Y., Kato, S., Shibata, M., Kondo, Y., Nakagawa, H. & Kohda, K. (1987). Biochem. Pharmacol. 36, 4181-4185.  [ChemPort] [PubMed] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o54-o55   [ doi:10.1107/S1600536811051543 ]

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