organic compounds
Table 1
Selected geometric parameters (A, ).
Ê
ꢀ
i
SÐC1
NÐC1
NÐC2
1.660 (1)
1.316 (2)
1.455 (2)
C1ÐC1
C2ÐC3
C3ÐC8
1.533 (2)
1.513 (2)
1.379 (2)
i
C1ÐNÐC2
NÐC1ÐC1
NÐC1ÐS
126.1 (1)
113.4 (1)
125.3 (1)
C1 ÐC1ÐS
NÐC2ÐC3
121.3 (1)
113.4 (1)
i
Figure 1
A perspective molecular view of (IV), showing the atomic numbering
scheme for the asymmetric unit. Displacement ellipsoids are drawn at the
5
i
C2ÐNÐC1ÐC1
179.2 (1)
C1ÐNÐC2ÐC3
� 99.6 (1)
0% probability level and H atoms are shown as small spheres of
arbitrary radii. Open atoms and bonds represent the equivalent part of
the molecule obtained by the symmetry operation (� x, � y, � z). Dotted
lines represent intramolecular hydrogen-bond interactions.
Symmetry code: (i) � x; � y; � z.
Table 2
Ê
ꢀ
Intramolecular contact geometry (A, ).
ꢀ
the corresponding value of 99.6 (1) in (IV). On the other
hand, the 4-pyridyl isomer reported by Liu et al. (1999) shows
the planar conformation, with the amide H atom interacting
with both the adjacent O and pyridine N atoms.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
i
NÐHÁ Á ÁS
0.80 (2)
0.96 (2)
2.42 (2)
2.51 (2)
2.926 (1)
2.855 (2)
122 (1)
101 (1)
C8ÐH8Á Á ÁN
Symmetry code: (i) � x; � y; � z.
Experimental
Dibenzyldithiooxamide was synthesized by a slight modi®cation of
the method of Hurd et al. (1961). Benzylamine (two equivalents,
All H atoms were located in difference Fourier syntheses and were
included in the re®nement as free isotropic atoms.
2.14 g) was mixed with dithiooxamide (0.002 mol). The mixture was
Data collection: P3/V (Siemens, 1989); cell re®nement: P3/V; data
reduction: SHELXTL-Plus (Siemens, 1990); program(s) used to
solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to
re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
XPW (Siemens, 1996); software used to prepare material for publi-
cation: PARST97 (Nardelli, 1995) and SHELXL97.
homogenized in a mortar and, after a few minutes, the crude di-
benzyldithiooxamidate solidi®ed. The pure compound was crystal-
lized from ethanol. For the diffraction study, suitable crystals of (IV)
were grown by slow evaporation of an ethanol solution at room
temperature. The compound was initially identi®ed from the NMR
1
spectra. Spectroscopic analysis, H NMR (300.13 MHz, CDCl
p.p.m): 10.55 (bs, 1H, NH), 7.2±7.4 (mm, 5H, phenyl H), 4.93 (d,
3
, ꢁ,
3
13
1
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GG1132). Services for accessing these data are
described at the back of the journal.
J
HH = 6.10 Hz, 2H, NÐCH
p.p.m.): C 184.5, C 131.01, C
four aromatic C), 51.5 (NÐCH
2
); C{ H} NMR (75.47 MHz, CDCl
±C 129.00, C ±C 128.09, C 128.20
).
3
, ꢁ,
S
1
2
6
3
5
4
(
2
Crystal data
References
�
3
C
16
H
16
N S
2 2
D
x
= 1.349 Mg m
Bermejo, E., Carballo, R., Casti nÄ eiras, A. & Maichle-M oÈ ssmer, C. (1998). Acta
Cryst. C54, 1130±1131.
Bruno, G., Lanza, S., Nicol o , F., Tresoldi, G. & Rosace, G. (2002). Acta Cryst.
C58, m316±m318.
Emsley, J. (1980). Chem. Soc. Rev. 9, 91±124.
Hurd, R. N., De La Mater, J., McEleheny, G. C., Turner, R. J. & Wallingford,
V. H. (1961). J. Org. Chem. 26, 3980±3987.
Lanza, S., Bruno, G., Nicol o , F., Rotondo, A., Scopelliti, R. & Rotondo, E.
r
M = 300.43
Mo Kꢃ radiation
Monoclinic, P2 =c
Cell parameters from 34
re¯ections
1
Ê
a = 7.665 (2) A
Ê
b = 10.533 (2) A
ꢀ
ꢄ = 6.8±12.9
Ê
c = 9.263 (2) A
� 1
ꢅ = 0.35 mm
T = 293 (2) K
ꢀ
ꢂ = 98.57 (2)
V = 739.5 (3) A
Z = 2
Ê
3
Irregular, orange
0.68 Â 0.40 Â 0.12 mm
(
2000). Organometallics, 19, 2462±2469.
Lanza, S., Bruno, G., Nicol o , F., Rotondo, A. & Tresoldi, G. (2002). Eur. J.
Inorg. Chem. 1, 65±72.
Lanza, S., Bruno, G., Nicol o , F. & Scopelliti, R. (1996). Tetrahedron Asymetry,
Data collection
Siemens P4 diffractometer
/2ꢄ scans
h = 0 ! 10
!
k = 0 ! 14
7
, 3347±3350.
2
1
1
167 measured re¯ections
986 independent re¯ections
568 re¯ections with I > 2ꢆ(I)
l = � 12 ! 12
Liu, B., Wang, H.-M., Yan, S.-P., Liao, D.-Z., Jiang, Z.-H., Huang, X.-Y. &
Wang, G.-L. (1999). J. Chem. Crystollgr. 29, 62±69.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659±671.
Nguyen, T. L., Scott, A., Dinkelmeyer, B., Fowler, F. W. & Lauher, J. W. (1998).
New J. Chem. (Nouv. J. Chim.), 22, 129±135.
3 standard re¯ections
every 197 re¯ections
intensity decay: 2%
R
int = 0.014
ꢀ
ꢄ
max = 29.1
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
G oÈ ttingen, Germany.
Siemens (1989). P3/V. Release 4.21/V. Siemens Analytical X-ray Instruments
Inc., Madison, Wisconsin, USA.
Siemens (1990). SHELXTL-Plus. Release 4.21/V for VMS. Siemens
Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Siemens (1996). XPW in SHELXTL. Version 5.0.5. Siemens Analytical X-ray
Instruments Inc., Madison, Wisconsin, USA.
Re®nement
2
Re®nement on F
2
All H-atom parameters re®ned
2
2
2
2
R[F > 2ꢆ(F )] = 0.034
wR(F ) = 0.096
S = 1.03
w = 1/[ꢆ (F
where P = (F
(Á/ꢆ)max < 0.001
Áꢇmax = 0.29 e A
Áꢇmin = � 0.27 e AÊ
o
) + (0.0642P) ]
2
2 2
+ 2F
c
o
)/3
Ê
� 3
1
1
986 re¯ections
24 parameters
� 3
ꢁ
Acta Cryst. (2002). C58, o608±o609
Giuseppe Bruno et al.
16 16 2
C H N S
2
o609