organic compounds
distance of 3.345 (2) A [symmetry code: (i) 1 x, 12 + y, 23 z]
Ê
Table 2
Hydrogen-bonding geometry (A, ).
ꢁ
Ê
is signi®cantly shorter than the same distance in S-methyl N,N-
Ê
dimethyldithiocarbazate [3.480 (4) A; Lanfredi et al., 1977]
Ê
and is comparable with the values of 3.389 (6) A in S-methyl
ꢀ-N-[4-(dimethylamino)benzylidene]dithiocarbazate (Zhao et
Ê
al., 1997), 3.343 (2) and 3.490 (3) A in dimethylammonium
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N2ÐH2AÁ Á ÁS1
0.86
0.86
2.35
2.58
2.772 (2)
3.345 (2)
110
149
N1ÐH1AÁ Á ÁS2i
Symmetry code: (i) 1 x; 12 y; 23 z.
Ê
dithiocarbazate (Wahlberg, 1978a), and 3.348 (3) A in diiso-
propylammonium diisopropyldithiocarbamate (Wahlberg,
1978b). This value is at the upper end of the range described
by Srinivasan & Chackko (1967). Moreover, atom H2B of the
amino group is involved in two slightly longer NÐHÁ Á ÁS
Re®nement
Re®nement on F2
R[F2 > 2ꢄ(F2)] = 0.060
wR(F2) = 0.113
S = 0.976
2398 re¯ections
w = 1/[ꢄ2(Fo2) + (0.1096P)2
+ 0.5240P]
i
i
Ê
where P = (Fo2 + 2Fc2)/3
(Á/ꢄ)max < 0.001
interactions [H2BÁ Á ÁS2 3.413 (1) and N2Á Á ÁS2 3.780 (2) A;
H2BÁ Á ÁS2ii 3.295 (1) and N2Á Á ÁS2ii 3.456 (2) A; symmetry
Ê
3
Ê
Áꢅmax = 0.52 e A
3
2
1
code: (ii) x,
atoms of two different molecules.
y, + z], since it points towards the thione-S
2
3
Ê
0.52 e A
109 parameters
H-atom parameters constrained
Áꢅmin
=
After checking their presence in the difference map, all H atoms
were ®xed geometrically and allowed to ride on their attached atoms
Experimental
Ê
(NÐH = 0.86 A, CÐH = 0.93 and 0.97 A)
Ê
Hydrazine hydrate (10 g) was mixed with potassium hydroxide
(11.4 g) in 90% ethanol (70 ml) and cooled to 273 K in an ice bath.
The addition of carbon disul®de (15.2 g) with constant stirring over a
period of 1 h formed two layers. The light-brown layer was separated,
dissolved in cold 40% ethanol (60 ml) and kept in an ice bath. Benzyl
chloride (25 g) was added dropwise with vigorous stirring of the
mixture. A white product was formed after complete addition of the
benzyl chloride. This product, (I), was ®ltered off and washed with
water. After drying, it was recrystallized from benzene. An equimolar
mixture of (I) and dimethyltin dichloride in ethanol, after a few days
of evaporation, gave good crystals of (I), as identi®ed by IR spec-
troscopy and elemental analysis.
Data collection: SMART (Siemens, 1996); cell re®nement: SAINT
(Siemens, 1996); data reduction: SAINT; program(s) used to solve
structure: SHELXTL (Sheldrick, 1997); program(s) used to re®ne
structure: SHELXTL; molecular graphics: SHELXTL; software used
to prepare material for publication: SHELXTL and PARST
(Nardelli, 1995).
The authors would like to thank the Malaysian Govern-
ment, Universiti Kebangsaan Malaysia and Universiti Sains
Malaysia for research grant R & D Nos. 03-02-02-005 and 305/
p®zik/610942. SSSR thanks the Universiti Sains Malaysia for a
Visiting Postdoctoral Fellowship.
Crystal data
3
C8H10N2S2
Mr = 198.30
Dx = 1.348 Mg m
Mo Kꢁ radiation
Cell parameters from 4301
re¯ections
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: NA1480). Services for accessing these data are
described at the back of the journal.
Monoclinic, P21=c
Ê
a = 19.7221 (9) A
ꢂ = 3.12±28.42ꢁ
ꢃ = 0.492 mm
T = 293 (2) K
Ê
b = 4.8605 (2) A
1
Ê
c = 10.2699 (5) A
ꢀ = 97.121 (1)ꢁ
V = 976.87 (8) A
Z = 4
References
3
Ê
Parallelepiped, yellow
0.48 Â 0.36 Â 0.32 mm
Andreocci, M. V., Bossa, M., Ramunni, G., Scazzocchio, M., Gattegno, D. &
Giuliani, A. M. (1974). J. Chem. Soc. Dalton Trans. pp. 41±43.
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Data collection
Siemens SMART CCD area-
detector diffractometer
! scans
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
Tmin = 0.798, Tmax = 0.859
6578 measured re¯ections
2398 independent re¯ections
1760 re¯ections with I > 2ꢄ(I)
Rint = 0.061
ꢂ
max = 28.28ꢁ
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Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
h = 24 ! 26
k = 6 ! 6
l = 13 ! 8
È
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Inc., Madison, Wisconsin, USA.
Table 1
Selected geometric parameters (A, ).
ꢁ
Ê
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edited by E. D. Bergmann & B. Pullman, p. 607. New York: Academic Press.
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S1ÐC8
S1ÐC7
1.753 (2)
1.816 (3)
N1ÐN2
1.406 (3)
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C8ÐS1ÐC7
103.4 (1)
169.7 (2)
C8ÐN1ÐN2
121.0 (2)
179.5 (2)
È
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N2ÐN1ÐC8ÐS2
ꢀ
Acta Cryst. (2000). C56, 1236±1237
S. Shanmuga Sundara Raj et al. C8H10N2S2 1237