organic compounds
The N1ÐC9ÐC11ÐO3 torsion angle [164.6 (2)ꢀ], char-
acterizes the antiperiplanar conformation for the N1 and O3
atoms. The conformation observed across the S1ÐN1ÐC9Ð
C11 linkage is ( )-anticlinal [torsion angle 136.3 (2)ꢀ]. The
two phenyl ring planes are at a dihedral angle of 59.3 (1)ꢀ (see
Fig. 1).
Acta Crystallographica Section C
Crystal Structure
Communications
ISSN 0108-2701
In the solid state, the molecules translated in the c direction
are linked through O3ÐH3BÁ Á ÁO2i intermolecular hydrogen
bonds (Table 2) to form in®nite one-dimensional chains.
Along the chain, the phenyl rings are stacked without any ꢀ ±ꢀ
interactions.
(1R,2S)-2-[N-Methyl-N-(4-toluene-
sulfonyl)amino]-1-phenylpropan-1-ol
Kandasamy Chinnakali,a² S. Shanmuga Sundara Raj,b
Hoong-Kun Fun,b* Kamaraj Sriraghavanc and
Vayalakkavoor T. Ramakrishnanc
aDepartment of Physics, Anna University, Chennai 600 025, India, bX-ray Crystal-
lography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang,
Malaysia, and cDepartment of Organic Chemistry, University of Madras, Guindy
Campus, Chennai 600 025, India
Correspondence e-mail: hkfun@usm.my
Received 19 November 1998
Accepted 5 November 1999
In the title compound, C17H21NO3S, the S atom is in a
distorted tetrahedral geometry and the N atom exhibits sp2
character. The antiperiplanar conformation is observed for the
N and hydroxyl-O atoms and the torsion angle around the NÐ
C linkage is 136.3 (2)ꢀ. The molecules are linked by OÐ
HÁ Á ÁO intermolecular hydrogen bonds to form an in®nite one-
dimensional chains along the c axis.
Figure 1
The structure of title compound showing 50% probability displacement
ellipsoids and the atom-numbering scheme.
Experimental
Ephedrine (1 g, 6.05 mmol), p-toluenesulfonyl chloride (1.73 g,
9.07 mmol) and tetra-n-butylammonium hydrogen sulfate (0.410 g,
1.21 mmol) in 50 ml of dry benzene were stirred with 10 ml of 50%
NaOH at room temperature for 1 h. After completion of the reaction,
the organic layer was separated, washed with water and dried over
MgSO4. After removal of the solvent, it gave a solid which was
recrystallized from methyl alcohol (yield 80%, m.p. 397±399 K).
Comment
The title compound is an N-tosyl derivative of ( )-ephedrine.
Generally ephedrine and its derivatives are used as sympa-
thomimetic agents for allergic disorders, central nervous
system stimulation, prophylaxis and treatment of hypotension
and hypersensitive carotid sinus. The structure determination
of the title compound, (I), was carried out in order to elucidate
the molecular conformation and packing arrangements.
Crystal data
C17H21NO3S
Mr = 319.41
Monoclinic, P21
Dm not measured
Mo Kꢂ radiation
ꢃ = 0.71073 A
Ê
Ê
a = 6.0272 (2) A
b = 18.6624 (8) A
Cell parameters from 4453
re¯ections
Ê
ꢄ = 2.79±33.14ꢀ
ꢅ = 0.209 mm
T = 293 (2) K
Ê
c = 7.3642 (3) A
1
ꢁ = 98.148 (1)ꢀ
V = 819.98 (6) A
3
Ê
Z = 2
Dx = 1.294 Mg m
Parallelepiped, colourless
0.50 Â 0.34 Â 0.26 mm
3
Data collection
Siemens SMART CCD area-
detector diffractometer
! scans
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
Tmin = 0.903, Tmax = 0.948
5485 measured re¯ections
3379 independent re¯ections
3038 re¯ections with I > 2ꢆ(I)
Rint = 0.027
The S atom is in a distorted tetrahedral geometry with the
maximum and minimum bond angles around this atom being
119.8 (1) and 106.4 (1)ꢀ, respectively. The sum of the bond
angles around the N1 atom [354.6 (2)ꢀ] indicates the sp2
character of this atom; the deviation of N1 from the S1±C8±C9
ꢄmax = 27.50ꢀ
h = 7 ! 7
k = 24 ! 24
l = 0 ! 9
Re®nement
Re®nement on F2
R[F2> 2ꢆ(F2)] = 0.041
wR(F2) = 0.104
w = 1/[ꢆ2(Fo2) + (0.0586P)2 +
Ê
plane is 0.206 (2) A. The SÐN, SÐO and CÐS distances
agree with those values reported for the toluenesulfonylamino
derivatives (Urtiaga et al., 1994; Arriortua et al., 1995).
0.0071P] where P = (Fo2 + 2Fc2)/3
(Á/ꢆ)max < 0.001
3
Ê
S = 1.060
3379 re¯ections
Áꢇmax = 0.40 e A
3
Ê
0.34 e A
Áꢇmin
=
199 parameters
H-atom parameters constrained
Absolute structure: Flack (1983)
Flack parameter = 0.13 (7)
² Visiting Postdoctoral Fellow, School of Physics, Universiti Sains Malaysia,
11800 USM, Penang, Malaysia.
ꢁ
Acta Cryst. (2000). C56, 227±228
Kandasamy Chinnakali et al. C17H21NO3S 227
Chinnakali, Kandasamy
