organic papers
o690
Manivannanet al. C13H12O3S doi:10.1107/S1600536805001029 Acta Cryst.(2005). E61, o690–o692 Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Phenyl 4-toluenesulfonate: supramolecular
aggregation through weak C—H
O and
C—H
p
interactions
Vadivelu Manivannan,a
Nagarajan Vembu,b*‡ Maruthai Nallu,bKandasamy Sivakumarc and Anthony Lindend
aDepartment of Physics, Presidency College,
Chennai 600 005, India,bDepartment of
Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India,cDepartment of
Physics, Anna University, Chennai 600 025, India, anddInstitute of Organic Chemistry,
University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland
‡ Correspondence address: Department of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, Tamil Nadu, India.
Correspondence e-mail: vembu57@yahoo.com
Key indicators
Single-crystal X-ray study T= 173 K
Mean(C–C) = 0.005 A˚ Rfactor = 0.067 wRfactor = 0.177
Data-to-parameter ratio = 20.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the crystal structure of the title compound, C13H12O3S, the
dihedral angle between the mean planes of the 4-tolyl and
phenyl rings is 52.6 (1). There are weak C—H O hydrogen
bonds, which generate rings of graph-set motifs R1
2
(4) and
R2 1
(9). The supramolecular aggregation is completed by the
presence of van der Waals short contacts and C—H
interactions.
Comment
Aromatic sulfonates are used in monitoring the merging of
lipids (Yachiet al., 1989) and in many other fields (Spunginet
al., 1992; Tharakanet al., 1992; Alfordet al., 1991; Jianget al., 1990; Narayanan & Krakow, 1983). The crystal structure of the title compound was determined because of the biological importance of its analogues. A search of Version 5.23 (July 2002 updates) of the Cambridge Structural Database (Allen,
2002) revealed 16 structures [refcodes KAWDAN (Niestrojet
al., 1998), FIXCAQ (Chinnakali et al., 1999), NEDXUP,
NEDYAW and NEDYIE (Gallucci et al., 1998), NUNCII
(Goswamiet al., 1998), RASSOT (Is¸iket al., 1997), RELVUZ
(Bott et al., 1996), SIMVUF (Bindalet al., 1990), TCPTOS
(Wieczorek & Galdecki, 1978), TEBFOV (Princeet al., 1991),
TMPDTS (Wieczoreket al., 1975), TSMIPH (Sarkar & Gupta,
1980), WOHCUR (Meents et al., 2000), ZZZBDA10
(Wiec-zorek, 1980) and MIWHIJ (Lee et al., 2001)] that are closely
related to the title compound in having benzene rings attached
to the sulfonate group. The S—C, S—O and S O bond
lengths (Table 1) are comparable to those found in related structures (Vembu, Nallu, Garrison & Youngs, 2003a,b,c,d,e,f; Vembu, Nallu, Spencer & Howard, 2003a,b,c,d,e,f,g; Vembuet al., 2003; Vembu, Nallu, Durmuset al., 2004a,b,c). The mole-cular structure of (I) is shown in Fig. 1 and selected geometric parameters are given in Table 1. The dihedral angle between
[image:1.610.272.390.587.646.2]the mean planes of the C1–C6 and C8–C13 rings is 52.6 (1).
Fig. 2 shows a Newman projection along the S1—O3 bond, with atom C8 at the top for reference. Helical nomenclature is
followed in assigning + or synclinal and +antiperiplanar
conformations. Since the C1—S1—O3—C8 torsion angle is
72.1 (2), which corresponds to asynclinal conformation,
the dihedral angle between the two aromatic planes is, as
expected, large [52.6 (1)].
The crystal structure of (I) is stabilized by weak C—H O
interactions (Table 2). The H O distances found in (I) agree
with those found for weak C—H O bonds (Desiraju &
Steiner, 1999). The C2—H2 O1i and C13—H13 O1i
interactions (see Table 2 for symmetry codes) together constitute a pair of bifurcated acceptor bonds generating a
ring of graph set R1
2(9). The C5—H5 O3
iii
and C5—
H5 O2iii interactions together form a pair of bifurcated
donor bonds generating a ring of graph setR2
1(4). This motif
can be considered as a symmetrical three-center
hydrogen-bonded chelate, as the difference in H Adistances andD—
H Aangles are 0.02 A˚ and 19.7, respectively, and the sum
of the angles around the chelating H atom is 341. There are a
few other C—H O, C—H and van der Waals
interac-tions, which contribute to the supramolecular aggregation (Fig. 3) of the title compound.
Experimental
4-Toluenesulfonyl chloride (4.7 mmol), dissolved in acetone (4 ml), was added dropwise to phenol (4.3 mmol) in aqueous NaOH (2.5 ml, 10%) with constant shaking. The precipitated compound (2.9 mmol, yield 67%) was filtered off and recrystallized from aqueous ethanol.
Crystal data
C13H12O3S
Mr= 248.29 Orthorhombic,Pca21
a= 25.149 (4) A˚
b= 7.976 (5) A˚
c= 5.916 (4) A˚
V= 1186.7 (10) A˚3
Z= 4
Dx= 1.390 Mg m
3
MoKradiation
Cell parameters from 25 reflections
= 15–19 = 0.27 mm1
T= 173 (2) K Thick plate, colorless 0.500.330.15 mm
Data collection
Rigaku AFC-5Rdiffractometer
!scans
Absorption correction: scan (Northet al., 1968)
Tmin= 0.946,Tmax= 0.963
3909 measured reflections 3277 independent reflections 2819 reflections withI> 2(I)
Rint= 0.052 max= 30.0
h=35!35
k=11!10
l=8!8 3 standard reflections
every 150 reflections intensity decay: none
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.067
wR(F2) = 0.177
S= 1.09 3277 reflections 157 parameters
H-atom parameters constrained
w= 1/[2(F2
o) + (0.1163P)2 + 0.1087P]
whereP= (F2
o+ 2F2c)/3 (/)max= 0.001 max= 0.60 e A˚
3 min=1.40 e A˚ 3
Absolute structure: (Flack, 1983), 1386 Friedel pairs
Flack parameter:0.07 (12)
organic papers
Acta Cryst.(2005). E61, o690–o692 Manivannanet al. C
[image:2.610.45.294.70.247.2]13H12O3S
o691
Figure 3
[image:2.610.312.564.70.306.2]Packing of the title molecule, viewed down thec axis. Dashed lines indicate hydrogen bonds.
Figure 1
The molecular structure of the title molecule, showing 50% probability displacement ellipsoids. H atoms have been omitted.
Figure 2
[image:2.610.56.235.319.502.2]Table 1
Selected geometric parameters (A˚ ,).
S1—O2 1.427 (2)
S1—O1 1.431 (3)
S1—O3 1.611 (2)
S1—C1 1.754 (3)
O3—C8 1.410 (3)
O2—S1—O1 120.98 (17)
O2—S1—O3 103.05 (13)
O1—S1—O3 108.36 (14)
O2—S1—C1 110.40 (14)
O1—S1—C1 108.99 (14)
O3—S1—C1 103.50 (13)
C8—O3—S1 117.68 (18)
O2—S1—O3—C8 172.8 (2)
O1—S1—O3—C8 43.5 (3)
[image:3.610.43.296.266.380.2]C1—S1—O3—C8 72.1 (2)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
C13—H13 O1i
0.93 2.76 3.643 (4) 158
C2—H2 O2ii
0.93 2.99 3.761 (4) 141
C5—H5 O3iii
0.93 2.78 3.649 (4) 155
C5—H5 O2iii 0.93 2.76 3.484 (4) 135
C7—H7B O2iv
0.96 2.98 3.543 (5) 119
C7—H7C O2v
0.96 2.53 3.406 (4) 152
C10—H10 O3vi 0.93 2.89 3.644 (4) 140
C3—H3 Cg1ii
0.93 2.83 3.58 138
C9—H9 Cg2vii
0.93 2.92 3.64 135
C11—H11 Cg1viii
0.93 3.33 4.09 141
C12—H12 Cg2ix 0.93 3.08 3.84 141
Symmetry codes: (i)x;y;zþ1; (ii)xþ1 2;y;zþ
1
2; (iii)x;yþ1;z; (iv)x;yþ1;zþ1;
(v) xþ1 2;yþ1;zþ
1
2; (vi) xþ1;yþ1;z 1
2; (vii) x;yþ1;z 1 2; (viii)
x;yþ2;z1
2; (ix)x;yþ2;zþ 1
2. Notes:Cg1 andCg2 are the ceentroids of
the C1–C6 and C8–C13 rings, respectively.
All H atoms were included in calculated positions, with aromatic C—H distances of 0.93 A˚ and methyl C—H distances of 0.96 A˚, and refined with a riding model. Their displacement parameters were tied to common free varibles which were refined.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement:MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Mole-cular Structure Corporation, 1999); program(s) used to solve struc-ture: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication:SHELXL97.
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organic papers
o692
Manivannanet al. Csupporting information
sup-1
Acta Cryst. (2005). E61, o690–o692
supporting information
Acta Cryst. (2005). E61, o690–o692 [https://doi.org/10.1107/S1600536805001029]
Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C
—
H
···
O
and C
—
H
···
π
interactions
Vadivelu Manivannan, Nagarajan Vembu, Maruthai Nallu, Kandasamy Sivakumar and Anthony
Linden
Phenyl 4-toluenesulfonate
Crystal data
C13H12O3S Mr = 248.29
Orthorhombic, Pca21
Hall symbol: P 2c -2ac
a = 25.149 (4) Å
b = 7.976 (5) Å
c = 5.916 (4) Å
V = 1186.7 (10) Å3 Z = 4
F(000) = 520
Dx = 1.390 Mg m−3
Melting point = 367–368 K Mo Kα radiation, λ = 0.71069 Å Cell parameters from 25 reflections
θ = 15–19°
µ = 0.27 mm−1 T = 173 K Plate, colorless 0.50 × 0.33 × 0.15 mm
Data collection
Rigaku AFC-5R diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: ψ scan (North et al., 1968)
Tmin = 0.946, Tmax = 0.963
3909 measured reflections
3277 independent reflections 2819 reflections with I > 2σ(I)
Rint = 0.052
θmax = 30.0°, θmin = 2.6° h = −35→35
k = −11→10
l = −8→8
3 standard reflections every 150 reflections intensity decay: none
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.067 wR(F2) = 0.177 S = 1.09 3277 reflections 157 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.1163P)2 + 0.1087P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.60 e Å−3
Δρmin = −1.40 e Å−3
Absolute structure: (Flack, 1983), 1386 Friedel pairs?
supporting information
sup-2
Acta Cryst. (2005). E61, o690–o692 Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
S1 0.34695 (2) 0.69543 (8) 0.44852 (13) 0.02728 (19) O1 0.36778 (11) 0.7369 (3) 0.2305 (4) 0.0381 (5) O2 0.30335 (9) 0.5822 (3) 0.4718 (5) 0.0418 (6) O3 0.39332 (8) 0.6063 (2) 0.5929 (4) 0.0287 (4) C1 0.33453 (10) 0.8811 (4) 0.5984 (5) 0.0237 (5) C2 0.30789 (11) 0.8722 (4) 0.8058 (5) 0.0268 (5) H2 0.2964 0.7699 0.8632 0.055 (4)* C3 0.29905 (11) 1.0202 (4) 0.9237 (5) 0.0293 (6) H3 0.2813 1.0159 1.0614 0.055 (4)* C4 0.31605 (12) 1.1749 (4) 0.8415 (5) 0.0285 (6) C5 0.34174 (12) 1.1797 (4) 0.6319 (6) 0.0308 (6) H5 0.3526 1.2821 0.5725 0.055 (4)* C6 0.35127 (12) 1.0336 (4) 0.5115 (5) 0.0290 (6) H6 0.3688 1.0379 0.3732 0.055 (4)* C7 0.30695 (14) 1.3344 (5) 0.9751 (7) 0.0412 (8) H7A 0.3371 1.4071 0.9581 0.083 (11)* H7B 0.3023 1.3072 1.1319 0.083 (11)* H7C 0.2757 1.3898 0.9199 0.083 (11)* C8 0.44463 (11) 0.6773 (4) 0.5835 (5) 0.0268 (5) C9 0.47793 (12) 0.6383 (4) 0.4047 (5) 0.0318 (6) H9 0.4662 0.5698 0.2876 0.055 (4)* C10 0.52921 (13) 0.7034 (4) 0.4036 (5) 0.0371 (7) H10 0.5521 0.6782 0.2850 0.055 (4)* C11 0.54647 (13) 0.8061 (5) 0.5794 (7) 0.0400 (8) H11 0.5807 0.8503 0.5770 0.055 (4)* C12 0.51273 (13) 0.8425 (5) 0.7578 (6) 0.0394 (7) H12 0.5244 0.9110 0.8749 0.055 (4)* C13 0.46117 (13) 0.7769 (4) 0.7629 (5) 0.0335 (7) H13 0.4385 0.7994 0.8833 0.055 (4)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
supporting information
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Acta Cryst. (2005). E61, o690–o692
O3 0.0305 (9) 0.0282 (10) 0.0272 (9) 0.0022 (7) −0.0014 (8) 0.0034 (8) C1 0.0238 (10) 0.0289 (13) 0.0183 (10) 0.0032 (9) −0.0010 (9) 0.0002 (10) C2 0.0309 (12) 0.0304 (14) 0.0190 (11) 0.0002 (10) −0.0005 (10) 0.0065 (11) C3 0.0307 (11) 0.0389 (15) 0.0183 (11) 0.0019 (10) 0.0012 (10) 0.0019 (12) C4 0.0289 (12) 0.0326 (14) 0.0240 (12) 0.0031 (11) −0.0027 (10) −0.0017 (11) C5 0.0362 (14) 0.0294 (14) 0.0267 (15) −0.0051 (11) 0.0024 (11) 0.0013 (12) C6 0.0332 (12) 0.0319 (15) 0.0219 (11) −0.0022 (11) 0.0031 (9) −0.0004 (10) C7 0.0463 (16) 0.0402 (17) 0.0372 (18) 0.0077 (13) −0.0025 (15) −0.0108 (16) C8 0.0294 (12) 0.0282 (13) 0.0227 (11) 0.0014 (9) −0.0016 (10) 0.0019 (11) C9 0.0350 (14) 0.0367 (15) 0.0238 (13) 0.0034 (12) −0.0020 (11) −0.0077 (12) C10 0.0353 (14) 0.0484 (18) 0.0276 (16) 0.0036 (12) 0.0051 (12) −0.0081 (14) C11 0.0321 (14) 0.055 (2) 0.0330 (15) −0.0025 (13) −0.0011 (14) −0.0089 (15) C12 0.0363 (15) 0.052 (2) 0.0298 (15) −0.0009 (14) −0.0044 (13) −0.0141 (15) C13 0.0364 (14) 0.0451 (18) 0.0189 (12) 0.0045 (13) −0.0014 (10) −0.0048 (12)
Geometric parameters (Å, º)
S1—O2 1.427 (2) C6—H6 0.9300
S1—O1 1.431 (3) C7—H7A 0.9600
S1—O3 1.611 (2) C7—H7B 0.9600
S1—C1 1.754 (3) C7—H7C 0.9600
O3—C8 1.410 (3) C8—C9 1.384 (4)
C1—C6 1.386 (4) C8—C13 1.390 (4)
C1—C2 1.400 (4) C9—C10 1.390 (4)
C2—C3 1.388 (4) C9—H9 0.9300
C2—H2 0.9300 C10—C11 1.394 (5)
C3—C4 1.394 (4) C10—H10 0.9300
C3—H3 0.9300 C11—C12 1.385 (5)
C4—C5 1.399 (4) C11—H11 0.9300
C4—C7 1.515 (4) C12—C13 1.398 (5)
C5—C6 1.387 (4) C12—H12 0.9300
C5—H5 0.9300 C13—H13 0.9300
O2—S1—O1 120.98 (17) C4—C7—H7A 109.5 O2—S1—O3 103.05 (13) C4—C7—H7B 109.5 O1—S1—O3 108.36 (14) H7A—C7—H7B 109.5 O2—S1—C1 110.40 (14) C4—C7—H7C 109.5 O1—S1—C1 108.99 (14) H7A—C7—H7C 109.5 O3—S1—C1 103.50 (13) H7B—C7—H7C 109.5 C8—O3—S1 117.68 (18) C9—C8—C13 122.1 (3) C6—C1—C2 121.0 (3) C9—C8—O3 119.6 (3) C6—C1—S1 120.0 (2) C13—C8—O3 118.2 (3) C2—C1—S1 119.1 (2) C8—C9—C10 118.7 (3)
C3—C2—C1 118.3 (3) C8—C9—H9 120.6
C3—C2—H2 120.9 C10—C9—H9 120.6
C1—C2—H2 120.9 C9—C10—C11 120.3 (3) C2—C3—C4 121.9 (3) C9—C10—H10 119.8
supporting information
sup-4
Acta Cryst. (2005). E61, o690–o692
C4—C3—H3 119.1 C12—C11—C10 120.1 (3) C3—C4—C5 118.3 (3) C12—C11—H11 120.0 C3—C4—C7 121.0 (3) C10—C11—H11 120.0 C5—C4—C7 120.6 (3) C11—C12—C13 120.4 (3) C6—C5—C4 120.8 (3) C11—C12—H12 119.8
C6—C5—H5 119.6 C13—C12—H12 119.8
C4—C5—H5 119.6 C8—C13—C12 118.4 (3) C1—C6—C5 119.6 (3) C8—C13—H13 120.8
C1—C6—H6 120.2 C12—C13—H13 120.8
C5—C6—H6 120.2
O2—S1—O3—C8 172.8 (2) C7—C4—C5—C6 178.5 (3) O1—S1—O3—C8 43.5 (3) C2—C1—C6—C5 0.3 (4) C1—S1—O3—C8 −72.1 (2) S1—C1—C6—C5 −179.4 (2) O2—S1—C1—C6 −143.2 (2) C4—C5—C6—C1 0.9 (4) O1—S1—C1—C6 −8.1 (3) S1—O3—C8—C9 −82.7 (3) O3—S1—C1—C6 107.1 (2) S1—O3—C8—C13 101.1 (3) O2—S1—C1—C2 37.1 (3) C13—C8—C9—C10 −1.1 (5) O1—S1—C1—C2 172.2 (2) O3—C8—C9—C10 −177.1 (3) O3—S1—C1—C2 −72.6 (2) C8—C9—C10—C11 −0.1 (5) C6—C1—C2—C3 −0.6 (4) C9—C10—C11—C12 0.7 (6) S1—C1—C2—C3 179.1 (2) C10—C11—C12—C13 −0.1 (6) C1—C2—C3—C4 −0.2 (4) C9—C8—C13—C12 1.6 (5) C2—C3—C4—C5 1.3 (4) O3—C8—C13—C12 177.7 (3) C2—C3—C4—C7 −178.8 (3) C11—C12—C13—C8 −1.0 (5) C3—C4—C5—C6 −1.6 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C2—H2···O2 0.93 2.76 3.044 (4) 99
C6—H6···O1 0.93 2.54 2.921 (4) 105
C9—H9···O1 0.93 2.83 3.058 (4) 95
C2—H2···O1i 0.93 2.83 3.122 (4) 100
C13—H13···O1i 0.93 2.76 3.643 (4) 158
C2—H2···O2ii 0.93 2.99 3.761 (4) 141
C5—H5···O3iii 0.93 2.78 3.649 (4) 155
C5—H5···O2iii 0.93 2.76 3.484 (4) 135
C7—H7B···O2iv 0.96 2.98 3.543 (5) 119
C7—H7C···O2v 0.96 2.53 3.406 (4) 152
C10—H10···O3vi 0.93 2.89 3.644 (4) 140
C3—H3···Cg1ii 0.93 2.83 3.577 138
C9—H9···Cg2vii 0.93 2.92 3.638 135
C11—H11···Cg1viii 0.93 3.33 4.094 141
C12—H12···Cg2ix 0.93 3.08 3.843 141