organic compounds
ꢀ
Ê
Re®nement
and N-tert-butyldithiophthalimide (CÁ Á ÁO 3.53 A and 153 ;
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.061
wR(F2) = 0.157
S = 1.100
2552 re¯ections
w = 1/[ꢇ2(Fo2) + (0.0533P)2
+ 1.2199P]
Mazhar-ul-Haque & Behforouz, 1979).
There is one short intermolecular interaction of 3.350 (3) A
between neighboring Cl atoms which is less than the van der
Ê
where P = (Fo2 + 2Fc2)/3
(Á/ꢇ)max < 0.001
Ê
Waals distance (Cl radius = 1.75 A; Bondi, 1964)). Addition-
3
Ê
Áꢈmax = 0.40 e A
3
Ê
0.52 e A
Extinction correction: SHELXTL
146 parameters
H-atom parameters constrained
Áꢈmin
=
ally, one borderline ClÁ Á ÁCl interaction is observed with a
Ê
distance of 3.529 (2) A, which is slightly longer than the van
der Waals distance. The corresponding closest contact distance
Extinction coef®cient: 0.022 (2)
Ê
between Cl atoms in Captan is 3.556 A (Moss & Jacobson,
1981). In Folpet, the nearest-neighbor contact between Cl and
Ê
S atoms is Cl3Á Á ÁS of 3.675 (2) A.
Data collection: P3±P4/PC (Siemens, 1989); cell re®nement: P3±
P4/PC; data reduction: XDISK (Siemens, 1989); program(s) used to
solve structure: SHELXTL (Sheldrick, 1994); program(s) used to
re®ne structure: SHELXTL; molecular graphics: SHELXTL; soft-
ware used to prepare material for publication: SHELXTL.
Experimental
A heptane solution of trichloromethanesulfenyl chloride was added
dropwise to a stirred dimethylformamide solution of phthalimide and
triethylamine producing (I) (Wunderly, 1972). Crystals of (I) were
obtained by slow evaporation from CH2Cl2 at 298 K and was fully
characterized by spectroscopic techniques. 1H NMR (250 MHz,
CDCl3): ꢁ 7.88±7.93 (m, 2H), 8.02±8.07 (m, 2H) p.p.m.; 13C NMR
(63 MHz, CDCl3): ꢁ 99.11, 124.65, 131.30, 135.44, 165.77 p.p.m.; IR
(CH2Cl2): 3948 (m), 3692±3750 (w), 3054 (vs), 2987 (s), 2681 (m), 2410
(m), 2306 (s), 1798 (w), 1752 (s), 1721 (w), 1422 (s), 1259 (vs), 1150
(m), 1026 (w), 896 (s), 763 (vs), 711 (vs) cm 1; UV/vis (CH2Cl2): ꢂ
239, 296 nm; HRMS (EI): m/z 295 (M+), 260, 241, 150, 130, 114, 104,
79, 70; exact mass for C9H4Cl3NO2S calculated 294.903, found
294.898; m.p. 448±449 K.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SX1096). Services for accessing these data are
described at the back of the journal.
References
Crystal data
3
Bondi, A. (1964). J. Phys. Chem. 68, 441±451.
C9H4Cl3NO2S
Mr = 296.54
Monoclinic, P21=c
a = 9.7666 (19) A
b = 5.7576 (12) A
Dx = 1.780 Mg m
Mo Kꢄ radiation
Cell parameters from 25
re¯ections
Carle, A. B. (1997). Masters thesis, University of Cincinnati, USA.
Hargreaves, M. K., Pritchard, J. G. & Dave, H. R. (1970). Chem. Rev. 70, 439±
469.
Iwasaki, F. & Masuko, Y. (1986). Acta Cryst. C42, 124±127.
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, pp. 85±97. New
York: Oxford University Press.
Ê
Ê
ꢅ = 7.5±15.0ꢀ
ꢆ = 0.996 mm
T = 298 (2) K
1
Ê
c = 19.754 (3) A
ꢃ = 94.905 (14)ꢀ
3
Mazhar-ul-Haque & Behforouz, M. (1979). Acta Cryst. B35, 845±848.
Moss, L. E.
1545±1548.
Ê
V = 1106.8 (4) A
Z = 4
Rod, colorless
0.45 Â 0.30 Â 0.25 mm
& Jacobson, R. A. (1981). Cryst. Struct. Commun. 10,
Sheldrick, G. M. (1994). SHELXTL. Program for Structure Determination.
Version 5.03. Siemens Analytical X-ray Instruments Inc., Madison,
Wisconsin, USA.
Siemens (1989). P3±P4/PC (Version 4.27) and XDISK (Version 4.27).
Programs for Data Collection and Reduction. Siemens Analytical X-ray
Instruments Inc., Madison, Wisconsin, USA.
Steiner, T. (1996). Crystallogr. Rev. 6, 1±57.
Taylor, R. & Kennard, O. (1982). J. Am. Chem. Soc. 104, 5063±5070.
Wunderly, S. (1972). Unpublished results.
Data collection
Siemens P3 diffractometer
ꢅ±2ꢅ scans
h = 0 ! 12
k = 0 ! 7
2702 measured re¯ections
2554 independent re¯ections
1281 re¯ections with I > 2ꢇ(I)
Rint = 0.035
l = 25 ! 25
3 standard re¯ections
every 250 re¯ections
intensity decay: negligible
ꢅmax = 27.55ꢀ
ꢁ
98 Carle, Krause Bauer and Wilson C9H4Cl3NO2S
Acta Cryst. (2000). C56, 97±98