(IUCr) 7-Benzenesulfonamido-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate

Volume 65
Part 8
Page o1737
August 2009

Received 8 June 2009
Accepted 26 June 2009
Online 1 July 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.008 Å
R = 0.051
wR = 0.120
Data-to-parameter ratio = 16.2
Details

7-Benzenesulfonamido-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate

Irfana Mariam,^a Mehmet Akkurt,^b ^* Shahzad Sharif,^a Syed Kamran Haider ^a and Islam Ullah Khan ^a ⁺

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₁₅H₁₄N₂O₅S₂·CH₄O, the six-membered ring fused to the [beta] -lactam unit adopts a twisted conformation. In the crystal structure, the component molecules are linked into a three-dimensional framework through intermolecular N-HS, N-HO and O-HO hydrogen bonds and C-HO contacts.

Related literature

For background to the use of the title compound in organic synthesis, see: Yamanaka et al. (1985). For ring puckering analysis, see: Cremer & Pople (1975). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₄N₂O₅S₂·CH₄O
M_r = 398.46
Monoclinic, P 2₁
a = 12.0000 (2) Å
b = 6.0964 (8) Å
c = 13.602 (2) Å
= 109.412 (7)°
V = 938.51 (19) Å³
Z = 2
Mo K radiation
= 0.32 mm^-1
T = 296 K
0.31 × 0.28 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: none
9995 measured reflections
3862 independent reflections
2296 reflections with I > 2(I)
R_int = 0.125

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.120
S = 0.96
3862 reflections
238 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 1498 Freidel pairs
Flack parameter: 0.01 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S2	0.86	2.76	3.111 (4)	106
N1-H1O5ⁱ	0.86	2.30	2.888 (5)	126
O4-H4AO6ⁱⁱ	0.82	1.76	2.575 (5)	171
O6-H6AO3	0.82	2.00	2.799 (5)	166
C2-H2O1	0.93	2.53	2.888 (7)	103
C7-H7O1ⁱⁱⁱ	0.98	2.34	3.037 (6)	127
C7-H7O2	0.98	2.45	2.906 (6)	108
C12-H12AO2^iv	0.97	2.46	3.327 (6)	148
C13-H13O4	0.93	2.44	2.982 (6)	117
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5002 ).

References

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.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yamanaka, H., Chiba, T., Takasugi, H., Masugi, T. & Takaya, T. (1985). J. Antibiot. pp. 1738-1751.

organic compounds