organic compounds
(yield: 1.10 g, 83.66%; m.p. 481±483 K). Spectrosopic analysis: 1H
NMR (DMSO-d6, 400 MHz, ꢂ, p.p.m.): 7.10 (s, 1H, 3-H), 7.52 (ddd,
1H, 6-H), 7.76±7.85 (m, 3H, 7-H, 40-H, 60-H), 7.98 (d, 1H, 8-H), 8.05
(dd, 1H, 50-H), 8.28 (d, 1H, 5-H), 8.48 (s, 1H, 20-H); mass spectroscopy
(70 eV), m/e: 301 (M+), 302 (M + 1), 303 (M + 2), 221, 193, 121, 120,
101, 92 (%100), 64, 63; IR (cm 1): 1614 (ꢀ-pyrone C O).
Table 2
Hydrogen-bond and short-contact geometry (A, ).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C7ÐH7Á Á ÁO3i
0.95
0.95
0.95
0.95
0.95
0.95
0.94
2.67
2.78
2.61
2.71
2.89
1.99
2.05
3.442 (3)
3.526 (4)
3.417 (3)
3.643 (3)
3.391 (2)
2.928 (3)
2.976 (3)
139
137
144
168
115
172
169
C6ÐH6Á Á ÁN1i
C8ÐH8Á Á ÁO4ii
C12ÐH12Á Á ÁO4ii
C12ÐH12Á Á ÁO4iii
N1ÐH1NÁ Á ÁO2iv
N1ÐH2NÁ Á ÁO2v
Crystal data
C15H11NO4S
Mr = 301.32
Triclinic, P1
a = 8.6654 (5) A
Ê
b = 8.7898 (6) A
c = 10.0105 (6) A
ꢃ = 98.183 (7)ꢀ
ꢄ = 112.991 (6)ꢀ
ꢀ = 104.673 (6)ꢀ
Z = 2
Dx = 1.531 Mg m
Mo Kꢃ radiation
3
Ê
Symmetry codes: (i) x 1; 1 y; z; (ii) x; 1 y; z; (iii) 1 x; 1 y; 1 z; (iv) 1 x; y; z;
(v) 1 x; 1 y; 2 z.
Cell parameters from 25
re¯ections
ꢅ = 9.4±18.2ꢀ
ꢆ = 0.263 mm
T = 295 K
Ê
1
Prismatic, colourless
0.56 Â 0.40 Â 0.20 mm
1995); program(s) used to re®ne structure: MolEN; molecular
graphics: ORTEPII (Johnson, 1976); software used to prepare
material for publication: MolEN.
3
Ê
V = 653.6 (2) A
Data collection
Enraf±Nonius CAD-4 diffract-
ometer
!/2ꢅ scans
Absorption correction: empirical
via scans (North et al., 1968)
Tmin = 0.869, Tmax = 0.951
2834 measured re¯ections
2649 independent re¯ections
2057 re¯ections with I > 2ꢇ(I)
Rint = 0.010
max = 26.3ꢀ
The authors acknowledge the purchase of the CAD-4
diffractometer under Grant DPT/TBAG1 of the Scienti®c and
Technical Research Council of Turkey.
ꢅ
h = 10 ! 0
k = 10 ! 10
l = 11 ! 12
3 standard re¯ections
frequency: 120 min
intensity decay: 1.5%
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: FR1229). Services for accessing these data are
described at the back of the journal.
Re®nement
Re®nement on F
R = 0.037
wR = 0.044
S = 0.90
2057 re¯ections
192 parameters
H atoms constrained
w = 1/(ꢇF2)
References
(Á/ꢇ)max < 0.001
Â
AFECT (Association FrancËaise des Enseignants de chimie Therapeutique)
(1995). Traite de chimie Therapeutique, Vol. 4, Medicament en Relation Avec
3
Ê
Áꢈmax = 0.23 e A
Â
Â
Â
3
Ê
0.09 e A
Áꢈmin
=
Á
des systemes Hormonaux, edited by Y. Adam et al., Tec. Doc. Lavoisier
Paris.
Aida, K., Tawata, M., Shindo, S., Onaya, T., Sasaki, H., Yamaguchi, T., Chin, M.
& Mitsuhasi, H. (1990). Planta Med. 56, 254±258.
Basnet, P., Kadota, S., Shimizu, M., Xu, H. X. & Namba, T. (1993). Chem.
Pharm. Bull. 41, 1790±1795.
Table 1
Selected geometric parameters (A, ).
ꢀ
Ê
S1ÐO3
S1ÐO4
S1ÐN1
S1ÐC15
O1ÐC2
1.431 (2)
1.423 (2)
1.613 (2)
1.776 (2)
1.348 (3)
O1ÐC9
O2ÐC4
C2ÐC3
C2ÐC11
1.373 (3)
1.247 (3)
1.346 (3)
1.478 (3)
Enraf±Nonius (1993). CAD-4 EXPRESS. Version 1.1. Enraf±Nonius, Delft,
The Netherlands.
Fair, C. K. (1990). MolEN. Enraf±Nonius, Delft, The Netherlands.
Hii, C. S. T. & Howell, S. L. (1985). J. Endocrinol. 107, 1±8.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National
Laboratory, Tennessee, USA.
O3ÐS1ÐO4
O3ÐS1ÐN1
O3ÐS1ÐC15
120.1 (1)
107.3 (9)
107.2 (1)
C3ÐC4ÐC10
O1ÐC9ÐC10
115.2 (2)
121.6 (2)
È
Kendi, E., Ozbey, S., TuncËbilek, M. & Ertan, R. (1996). Cryst. Res. Technol. 31,
611±615.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351±
359.
Okuda, J., Miwa, I., Inagaki, K., Horie, T. & Nakayama, M. (1984). Chem.
Pharm. Bull. 32, 767±772.
O3ÐS1ÐC15ÐC16
O4ÐS1ÐC15ÐC14
N1ÐS1ÐC15ÐC14
176.82 (15)
135.03 (16)
110.72 (16)
O1ÐC2ÐC11ÐC16
C13ÐC14ÐC15ÐS1
173.58 (16)
179.03 (15)
È
È
Ozbey, S., Kendi, E., Goker, H. & Ertan, R. (1997). Acta Cryst. C53, 1981±
1983.
Ragunathan, V. & Sulochana, N. (1994). J. Indian Chem. Soc. 71, 705±706.
Rossi, M., Cantrell, J. S., Farber, A. J., Dyott, T., Carrell, H. L. & Glusker, J. P.
(1980). Cancer Res. 40, 2774±2778.
Shoja, M. (1990). Acta Cryst. C46, 517±519.
Varma, S. D. & Kinoshita, J. H. (1976). Biochem. Pharmacol. 25, 2502±2513.
Data collection: CAD-4 EXPRESS (Enraf±Nonius, 1993); cell
re®nement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990);
program(s) used to solve structure: MolEN and PARST (Nardelli,
ꢁ
458 Engin Kendi et al. C15H11NO4S
Acta Cryst. (2000). C56, 457±458