2-Chlorophenyl 3-nitrobenzene-sulfonate and 2,4-dichlorophenyl 3-nitrobenzenesulfonate: Supramolecular aggregation through C-H...O, π-π and van der Waals interactions

Article abstract of DOI:10.1107/S0108270103027380

The molecular and crystal structures of 2-chlorophenyl 3-nitrobenzene-sulfonate and 2,4-dichlorophenyl 3-nitrobenzenesulfonate were analyzed. It was found that weak C-H···O interactions generated S(5), S(6) and R₂²(7) rings in the compounds. The supramolecular aggregation was also found to be completed by the presence of π-π interactions and intermolecular van der Walls short contacts. The analysis showed that the antiperiplanar/anticlinical orientation relieved the molecule from the steric strain, thereby facilitating the adoption of a coplanar orientation.

Full text of DOI:10.1107/S0108270103027380

organic compounds
Ê
Acta Crystallographica Section C
Crystal Structure
Communications
0.043 (3) A, respectively, from the mean plane formed by
atoms C7±C12. The dihedral angle between the planes of the
two aromatic rings is 53.03 (4)ꢀ in (I) and 50.0 (6)ꢀ in (II).
ISSN 0108-2701
2-Chlorophenyl 3-nitrobenzene-
sulfonate and 2,4-dichlorophenyl
3-nitrobenzenesulfonate: supramole-
cular aggregation through C±HÁ Á ÁO,
p±p and van der Waals interactions
Nagarajan Vembu,a Maruthai Nallu,a* Semih Durmus,b
Mathew Pazner,b Jered Garrisonb and Wiley J. Youngsb
aDepartment of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India,
and bDepartment of Chemistry, University of Akron, 190 East Buchtel Commons,
Akron, Ohio 44325-3601, USA
These rings thus have a non-coplanar orientation, similar to
that reported for other aromatic sulfonates (Vembu, Nallu,
Garrison & Youngs, 2003b,c,d,e; Vembu, Nallu, Spencer &
Howard, 2003a,b,d,e,g,h) and in contrast to the near coplanar
orientation found in 2,4-dinitrophenyl 4-toluenesulfonate
(Vembu, Nallu, Garrison & Youngs, 2003a), 4-methoxyphenyl
4-toluenesulfonate (Vembu, Nallu, Garrison, Hindi & Youngs,
2003) and 8-quinolyl 3-nitrobenzenesulfonate (Vembu, Nallu,
Spencer & Howard, 2003f). In these compounds, the anti-
periplanar/anticlinal (Ar)CÐSÐOÐC(OÐAr) conformation
Correspondence e-mail: mnalv2003@yahoo.com
Received 18 November 2003
Accepted 28 November 2003
Online 13 December 2003
In 2-chlorophenyl 3-nitrobenzenesulfonate, C12H8ClNO5S,
and 2,4-dichlorophenyl 3-nitrobenzenesulfonate, C12H7Cl2N-
O5S, weak CÐHÁ Á ÁO interactions generate S(5), S(6) and
R22(7) rings. The supramolecular aggregation is completed by
the presence of ꢀ±ꢀ interactions and intermolecular van der
Waals short contacts.
Comment
Aromatic sulfonates are used in monitoring the merging of
lipids (Yachi et al., 1989) and in many other ®elds (Narayanan
& Krakow, 1983; Jiang et al., 1990; Alford et al., 1991; Spungin
et al., 1992; Tharakan et al., 1992). The molecular and crystal
structures of 3-nitrobenzenesulfonyl chloride (Vembu, Nallu,
Spencer & Howard, 2003c) and a few of its derivatives
(Vembu, Nallu, Spencer & Howard, 2003d,e,f,g,h) have been
reported recently. An X-ray study of the title compounds, (I)
and (II), was undertaken in order to determine their crystal
and molecular structures. This study may serve as a forerunner
both for an assessment of the biological signi®cance of these
compounds and for studies of the quantitative structure±
activity relationships of aromatic sulfonates.
Figure 1
The molecular structure of (I), showing 50% probability displacement
ellipsoids.
The molecular structure of (I) is shown in Fig. 1 and
selected geometric parameters are given in Table 1. Atoms N,
O1 and O2 deviate from the mean plane formed by atoms C1±
Ê
C6 by 0.087 (2), 0.360 (3) and 0.125 (2) A, respectively. The
Ê
Cl atom deviates by 0.009 (2) A from the C7±C12 plane. The
molecular structure of (II) is shown in Fig. 2 and selected
geometric parameters are given in Table 3. Atoms N1, O1 and
O2 lie on the same side of the mean plane formed by atoms
Figure 2
The molecular structure of (II), showing 50% probability displacement
ellipsoids.
Ê
C1±C6, deviating by 0.075 (3), 0.043 (4) and 0.152 (4) A,
respectively. Atoms Cl1 and Cl2 deviate by 0.018 (3) and
Acta Cryst. (2004). C60, o65±o68
DOI: 10.1107/S0108270103027380
# 2004 International Union of Crystallography o65

organic compounds
leads to the two aromatic rings adopting a free coplanar
orientation; the CÐSÐOÐC torsion angle is 162.5 (2)ꢀ in
4-methoxyphenyl 4-toluenesulfonate, for example. The anti-
periplanar/anticlinal orientation relieves the molecule from
steric strain, thereby facilitating the adoption of a coplanar
orientation. In (I) and (II), the CÐSÐOÐC torsion angles
(Tables 1 and 3) are synclinal and therefore the two aromatic
rings are non-coplanar.
C2ÐH2Á Á ÁO1, C4ÐH4Á Á ÁO4, C6ÐH6Á Á ÁO2 and C6Ð
H6Á Á ÁO3 interactions generates an S(5) graph-set motif (Etter,
1990; Bernstein et al., 1995). The C6ÐH6Á Á ÁO2 and C6Ð
H6Á Á ÁO3 interactions constitute a pair of bifurcated donor
bonds. The S(5) rings generated by the C2ÐH2Á Á ÁO1, C4Ð
H4Á Á ÁO4, C6ÐH6Á Á ÁO2 and C6ÐH6Á Á ÁO3 interactions in (I)
are non-planar, with atoms O1, O4, O2 and O3 deviating by
Ê
0.27 (1), 0.548 (8), 0.22 (1) and 0.49 (2) A, respectively, from
The crystal structures of (I) and (II) are stabilized by weak
CÐHÁ Á ÁO interactions (Tables 2 and 4). The HÁ Á ÁO distances
found in (I) and (II) agree with those found for weak CÐ
HÁ Á ÁO bonds (Desiraju & Steiner, 1999). In (I), each of the
the corresponding mean planes formed by the other four
atoms in the ring. The non-planar orientation of these rings
can best be described as an envelope conformation, similar to
that observed in cyclopentane derivatives. The C8ÐH8Á Á ÁO4
interaction generates an S(6) motif. The C4ÐH4Á Á ÁO2ii and
C3ÐH3Á Á ÁO1ii interactions [symmetry code: (ii) x 1, y, z]
generate a nitro-fork R22(7) motif. Several other weak CÐ
HÁ Á ÁO interactions contribute to the supramolecular aggre-
gation of (I). In the crystal structure of (I) (Fig. 3), the mol-
ecules are stacked in layers held together by a ꢀ±ꢀ interaction,
Ê
with a centroid±centroid separation of 3.746 A between the
inversion-related chlorophenyl rings (symmetry code: 2 x,
y, z) (PLATON; Spek, 2003). There is an intermolecular
Ê
short contact, C1Á Á ÁO3(1 x, 2 y, 1 z), of 3.212 (2) A.
In (II), each of the C1ÐH1Á Á ÁO4, C3ÐH3Á Á ÁO2, C3Ð
H3Á Á ÁO3 and C5ÐH5Á Á ÁO1 interactions generates an S(5)
graph-set motif. The C3ÐH3Á Á ÁO2 and C3ÐH3Á Á ÁO3 inter-
actions constitute a pair of bifurcated donor bonds. The S(5)
rings generated by the C3ÐH3Á Á ÁO2 and C5ÐH5Á Á ÁO1
interactions in (II) are planar, whereas the S(5) rings formed
by the C1ÐH1Á Á ÁO4 and C3ÐH3Á Á ÁO3 interactions are non-
planar, with atoms O4 and O3 deviating by 0.53 (2) and
Ê
0.52 (2) A from the corresponding mean planes formed by the
other four atoms in the ring. The non-planar orientation of
these rings can best be described as an envelope conformation.
The C8ÐH8Á Á ÁO3 interaction generates an S(6) motif. The
C3ÐH3Á Á ÁO3 and C8ÐH8Á Á ÁO3 interactions together
constitute a pair of bifurcated acceptor bonds. The C6Ð
H6Á Á ÁO5vi and C1ÐH1Á Á ÁO4vi interactions [symmetry code:
Figure 3
The packing of (I) in the unit cell, viewed along the b axis.
1
2
1
2
(vi) x
,
y, 2 z] generate a fork R22(7) motif. Several
other weak CÐHÁ Á ÁO interactions contribute to the supra-
molecular aggregation of (II). In the crystal structure of (II)
(Fig. 4), the molecules are stacked in layers held together by a
pair of ꢀ±ꢀ interactions, with a centroid±centroid separation
Ê
of 3.873 A between the symmetry-related aromatic rings
[Cg1Á Á ÁCg2(12 x, y, 21 + z) and Cg2Á Á ÁCg1(21 x, y, z 12 ),
where Cg1 and Cg2 are the centroids of the C1±C6 and C7±
C12 rings, respectively] (PLATON; Spek, 2003). Other short
1
2
3
2
intermolecular contacts are Cl1Á Á ÁO2(x
,
y, 2 z) of
Ê
Ê
3.143 (2) A, N1Á Á ÁO3(x 1, y, z) of 3.022 (3) A, O1Á Á Á
O3(x 1, y, z) of 3.016 (3) A, O1Á Á ÁO5(2 x, 1 y, z 12 ) of
3
Ê
Ê
Ê
2.930 (3) A and C5Á Á ÁO4(x 1, y, z) of 3.119 (3) A.
Experimental
For the preparation of (I), 3-nitrobenzenesulfonyl chloride (5 mmol)
dissolved in acetone (5 ml) was added to 2-chlorophenol (5 mmol)
dissolved in NaOH (4 ml, 5%) and the mixture was shaken well. The
precipitated solid product, (I) (2 mmol, yield 40%), was recrystallized
from a 1:1 mixture of petroleum ether and acetone. For the
Figure 4
The packing of (II) in the unit cell, viewed along the b axis.
ꢁ
o66 Nagarajan Vembu et al.
C12H8ClNO5S and C12H7Cl2NO5S
Acta Cryst. (2004). C60, o65±o68

organic compounds
preparation of (II), 3-nitrobenzenesulfonyl chloride (5 mmol)
dissolved in acetone (5 ml) was added to 2,4-dichlorophenol
(5.5 mmol) dissolved in NaOH (4 ml, 5%) and the mixture was
shaken well. The precipitated solid product, (II) (2.9 mmol, yield
58%), was recrystallized from a 1:1 mixture of petroleum ether and
acetone.
Table 2
Hydrogen-bonding and short-contact geometry (A, ) for (I).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C2ÐH2Á Á ÁO1
C4ÐH4Á Á ÁO4
C6ÐH6Á Á ÁO2
C6ÐH6Á Á ÁO3
C8ÐH8Á Á ÁO4
C2ÐH2Á Á ÁO3i
C4ÐH4Á Á ÁO2ii
C3ÐH3Á Á ÁO1ii
C9ÐH9Á Á ÁO3ii
C4ÐH4Á Á ÁO4iii
C8ÐH8Á Á ÁO1iv
C11ÐH11Á Á ÁO2v
0.931 (19)
0.93 (2)
0.909 (19)
0.909 (19)
0.95 (2)
0.931 (19)
0.93 (2)
0.90 (2)
0.90 (2)
0.93 (2)
2.472 (18)
2.626 (19)
2.404 (18)
2.615 (18)
2.67 (2)
2.531 (19)
2.511 (19)
2.99 (2)
2.86 (2)
2.59 (2)
2.40 (2)
2.532 (19)
2.740 (2)
2.973 (2)
2.6968 (19)
2.9396 (19)
3.0772 (19)
3.324 (2)
3.033 (2)
3.733 (2)
3.539 (2)
3.335 (2)
3.316 (2)
3.3726 (19)
96.6 (13)
102.8 (13)
98.8 (13)
101.9 (13)
106.4 (14)
143.2 (15)
115.7 (14)
141.9 (16)
132.8 (15)
137.6 (15)
162.5 (16)
153.8 (15)
Compound (I)
Crystal data
C12H8ClNO5S
Mr = 313.70
Triclinic, P1
a = 7.4315 (18) A
Ê
b = 8.474 (2) A
Z = 2
Dx = 1.643 Mg m
Mo Kꢁ radiation
3
0.95 (2)
0.910 (19)
Ê
Cell parameters from 3667
re¯ections
ꢄ = 2.6±28.3ꢀ
ꢅ = 0.48 mm
T = 100 (2) K
Ê
Symmetry codes: (i) x; y 1; z; (ii) x 1; y; z; (iii) x; 2 y; 1 z; (iv) x 1; 1 ‡ y; z;
(v) 1 x; 1 y; 2 z.
c = 10.991 (3) A
1
ꢁ = 67.889 (4)ꢀ
ꢂ = 85.220 (4)ꢀ
ꢃ = 81.617 (4)ꢀ
Block, colorless
0.40 Â 0.20 Â 0.10 mm
3
Ê
V = 634.1 (3) A
Table 3
Selected geometric parameters (A, ) for (II).
Data collection
ꢀ
Ê
Bruker SMART CCD area-detector
diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.830, Tmax = 0.953
5585 measured re¯ections
2918 independent re¯ections
2723 re¯ections with I > 2ꢆ(I)
Rint = 0.017
Cl1ÐC10
Cl2ÐC12
S1ÐO3
S1ÐO4
S1ÐO5
1.739 (2)
1.722 (2)
1.4229 (17)
1.4240 (16)
1.6006 (18)
S1ÐC2
N1ÐO1
N1ÐO2
N1ÐC4
O5ÐC7
1.757 (2)
1.219 (3)
1.232 (3)
1.467 (3)
1.406 (2)
ꢄ
max = 28.3ꢀ
h = 9 ! 9
k = 11 ! 11
l = 14 ! 14
Re®nement
O3ÐS1ÐO4
O3ÐS1ÐO5
O4ÐS1ÐO5
O3ÐS1ÐC2
O4ÐS1ÐC2
120.90 (10)
108.26 (9)
103.06 (9)
109.18 (10)
110.45 (10)
O5ÐS1ÐC2
O1ÐN1ÐO2
O1ÐN1ÐC4
O2ÐN1ÐC4
C7ÐO5ÐS1
103.41 (9)
124.1 (2)
117.7 (2)
118.16 (19)
118.30 (12)
Re®nement on F2
R[F2 > 2ꢆ(F2)] = 0.031
wR(F2) = 0.083
S = 1.06
2918 re¯ections
w = 1/[ꢆ2(F2o) + (0.045P)2
+ 0.2748P]
where P = (F2o + 2Fc2)/3
(Á/ꢆ)max = 0.001
3
Ê
Áꢇmax = 0.46 e A
3
Ê
0.29 e A
213 parameters
All H-atom parameters re®ned
Áꢇmin
=
C2ÐS1ÐO5ÐC7
55.15 (16)
Table 1
Selected geometric parameters (A, ) for (I).
ꢀ
Ê
Table 4
Hydrogen-bonding and short-contact geometry (A, ) for (II).
ꢀ
ClÐC12
SÐO3
SÐO4
SÐO5
SÐC5
1.7334 (15)
1.4259 (12)
1.4263 (11)
1.5972 (11)
1.7560 (15)
O1ÐN
O2ÐN
O5ÐC7
NÐC1
1.2279 (17)
1.2285 (17)
1.4099 (17)
1.471 (2)
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C1ÐH1Á Á ÁO4
C3ÐH3Á Á ÁO2
C3ÐH3Á Á ÁO3
C5ÐH5Á Á ÁO1
C8ÐH8Á Á ÁO3
C6ÐH6Á Á ÁO5vi
C1ÐH1Á Á ÁO4vi
C9ÐH9Á Á ÁO2vii
C9ÐH9Á Á ÁO3viii
C11ÐH11Á Á ÁO1ix
0.94 (3)
0.98 (2)
0.98 (2)
0.81 (3)
0.84 (3)
0.93 (3)
0.94 (3)
0.85 (2)
0.85 (2)
0.85 (3)
2.63 (3)
2.41 (2)
2.60 (3)
2.37 (3)
2.65 (2)
2.95 (3)
2.83 (2)
2.72 (2)
2.56 (3)
2.48 (3)
2.982 (3)
2.708 (3)
2.935 (3)
2.716 (3)
3.055 (3)
3.805 (3)
3.349 (3)
3.294 (3)
3.362 (3)
3.301 (3)
102.8 (17)
96.7 (17)
100.2 (17)
106 (2)
111.3 (18)
153 (2)
116.1 (19)
126 (2)
158 (2)
O3ÐSÐO4
O3ÐSÐO5
O4ÐSÐO5
O3ÐSÐC5
O4ÐSÐC5
120.68 (7)
102.60 (6)
109.87 (6)
109.71 (7)
109.31 (7)
O5ÐSÐC5
C7ÐO5ÐS
O1ÐNÐO2
O1ÐNÐC1
O2ÐNÐC1
103.13 (6)
121.60 (9)
124.34 (14)
118.10 (13)
117.55 (13)
163 (2)
C5ÐSÐO5ÐC7
71.82 (11)
1
2
1
2
1
2
1
2
3
2
Symmetry codes: (vi) x
1
;
y; 2 z; (vii) ‡ x; 32 y; 2 z; (viii) x
;
y; 2 z;
(ix)
x; 1 y; 12 ‡ z.
2
Compound (II)
Crystal data
Data collection
C12H7Cl2NO5S
Mr = 348.15
Orthorhombic, P212121
Ê
a = 6.878 (5) A
b = 13.330 (10) A
c = 14.990 (11) A
Ê
V = 1374.3 (17) A
Mo Kꢁ radiation
Bruker SMART CCD area-detector
diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.739, Tmax = 0.830
11 316 measured re¯ections
3268 independent re¯ections
3158 re¯ections with I > 2ꢆ(I)
Rint = 0.037
ꢄmax = 28.4ꢀ
Cell parameters from 7544
re¯ections
ꢄ = 2.7±28.3ꢀ
ꢅ = 0.64 mm
T = 100 (2) K
1
Ê
Ê
h = 9 ! 9
k = 17 ! 17
l = 19 ! 19
3
Block, colorless
0.50 Â 0.30 Â 0.30 mm
Z = 4
Dx = 1.683 Mg m
3
ꢁ
Acta Cryst. (2004). C60, o65±o68
Nagarajan Vembu et al.
C12H8ClNO5S and C12H7Cl2NO5S o67

organic compounds
Bruker (1998). SMART-NT and SAINT-NT. Versions 5.0. Bruker AXS Inc.,
Madison, Wisconsin, USA.
Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural
Chemistry and Biology. New York: Oxford University Press.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120±126.
Re®nement
Re®nement on F2
R[F2 > 2ꢆ(F2)] = 0.032
wR(F2) = 0.081
S = 1.08
3268 re¯ections
218 parameters
All H-atom parameters re®ned
w = 1/[ꢆ2(F2o) + (0.0471P)2
+ 0.1269P]
where P = (F2o + 2Fc2)/3
(Á/ꢆ)max = 0.001
3
Ê
Áꢇmax = 0.38 e A
3
Ê
0.28 e A
Áꢇmin
=
Absolute structure: Flack (1983),
1283 Friedel pairs
Flack parameter = 0.02 (6)
Flack, H. D. (1983). Acta Cryst. A39, 876±881.
Jiang, F. N., Jiang, S., Liu, D., Richter, A. & Levy, J. G. (1990). J. Immunol.
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È
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (1998). SHELXTL. University of Gottingen, Germany.
È
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
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311, 155±160.
Tharakan, J., Highsmith, F., Clark, D. & Drohsn, W. (1992). J. Chromatogr. 595,
103±111.
All H atoms were located from difference Fourier maps and their
positional coordinates and isotropic displacement parameters were
re®ned. The CÐH bond lengths in (I) and (II) are in the ranges
Vembu, N., Nallu, M., Garrison, J., Hindi, K. & Youngs, W. J. (2003). Acta
Cryst. E59, o830±o832.
Ê
0.90 (2)±0.95 (2) and 0.81 (3)±0.98 (2) A, respectively.
For both compounds, data collection: SMART (Bruker, 1998); cell
re®nement: SMART; data reduction: SAINT (Bruker, 1998);
program(s) used to solve structure: SHELXTL (Sheldrick, 1998);
program(s) used to re®ne structure: SHELXTL; molecular graphics:
SHELXTL; software used to prepare material for publication:
SHELXTL.
Vembu, N., Nallu, M., Garrison, J. & Youngs, W. J. (2003a). Acta Cryst. E59,
o378±o380.
Vembu, N., Nallu, M., Garrison, J. & Youngs, W. J. (2003b). Acta Cryst. E59,
o503±o505.
Vembu, N., Nallu, M., Garrison, J. & Youngs, W. J. (2003c). Acta Cryst. E59,
o776±o779.
Vembu, N., Nallu, M., Garrison, J. & Youngs, W. J. (2003d). Acta Cryst. E59,
o936±o938.
NV thanks the University Grants Commission±SERO,
Government of India, for the award of a Faculty Improve-
ment Programme Grant (No. TFTNBD097 dt., 07.07.99).
This research was supported in part by grants to WJY from
the US National Science Foundation and the Ohio Board of
Regents.
Vembu, N., Nallu, M., Garrison, J. & Youngs, W. J. (2003e). Acta Cryst. E59,
o939±o941.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003a). Acta Cryst.
E59, o1009±o1011.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003b). Acta Cryst.
E59, o1033±o1035.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003c). Acta Cryst.
E59, o1036±o1038.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003d). Acta Cryst.
E59, o1213±o1215.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003e). Acta Cryst.
E59, o1216±o1219.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003f). Acta Cryst.
E59, o1379±o1382.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: OB1154). Services for accessing these data are
described at the back of the journal.
Vembu, N., Nallu, M., Spencer, E. C. & Howard, J. A. K. (2003g). Acta Cryst.
E59, o1387±o1389.
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ꢁ
o68 Nagarajan Vembu et al.
C12H8ClNO5S and C12H7Cl2NO5S
Acta Cryst. (2004). C60, o65±o68