organic papers
Acta Cryst.(2006). E62, o49–o51 doi:10.1107/S1600536805039589 Palaniet al. C
22H18O2S
o49
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
1,3-Bis(4-methoxyphenyl)-2-benzothiophene
K. Palani,aP. Amaladass,b A. K. Mohanakrishnanband M. N. Ponnuswamya*
aDepartment of Crystallography and Biophysics,
University of Madras, Guindy Campus, Chennai 600 025, India, andbDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 293 K
Mean(C–C) = 0.004 A˚ Rfactor = 0.058 wRfactor = 0.235
Data-to-parameter ratio = 22.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2006 International Union of Crystallography
Printed in Great Britain – all rights reserved
In the title compound, C22H18O2S, the two benzene rings are
twisted away from the thiophene ring by 34.99 (9) and
41.57 (9). C—H O and C—H hydrogen bonds are
observed in the crystal structure.
Comment
Most Schiff bases and their thiophene derivatives possess pharmacological activities such as antibacterial, anticancer,
anti-inflammatory and antitoxic properties (Gewald et al.,
1966). The diaryl-substituted heterocyclic molecules act as
selective COX-2 inhibitors (Portevin et al., 2000) and
anti-tumor agents (Szczepankiewicz et al., 2001). In view of this
importance, the crystal structure of the title compound, (I), has been determined and the results are presented here.
AZORTEP(Zsolnai, 1997) plot of the molecule is shown in Fig.1. The bond lengths and bond angles (Table 1) in the thiophene ring are comparable with those reported for 4-
{5-[3,4-dimethyl-5-(3,4,5-trimethoxyphenyl)thiophen-2-yl]-2-methoxyphenyl}morpholine (Shiet al., 2004). The C9–C14 and
C16–C21 benzene rings are oriented at angles of 34.99 (9) and 41.57 (9), respectively, with respect to the thiophene ring.
The dihedral angle between the C9–C14 and C16–C21
benzene rings is 71.2 (1). Both the methoxy groups are
coplanar with the attached rings. The crystal packing is
stabilized by C—H O and C—H type hydrogen bonds
(Table 2 and Fig. 2).
Experimental
4-Methoxymagnesium bromide was prepared from 4-bromoanisole (23 mmol) and Mg (25 mmol). 4-Methoxymagnesium bromide was added to a solution of 3-(4-methoxyphenyl)isobenzofuran-1(3H)-one (20.8 mmol) at 273 K. The reaction mixture was stirred at room temperature for 5 h and then poured into an ice-cooled aqueous NH4Cl solution, extracted with CH2Cl2 (50 ml) and dried over
Na2SO4. The reaction mixture was treated with Lawesson’s reagent
(10.4 mmol) and stirred at room temperature for 5 h. The solvent was removed and the residue was gently heated on a steam bath with ethanol. The product was purified by column chromatography (neutral alumina, hexane) to afford compound (I) as a yellow
powder. Single crystals of (I) were obtained by recrystallization from boiling hexane.
Crystal data
C22H18O2S Mr= 346.42 Orthorhombic,Pcab a= 7.508 (6) A˚
b= 16.493 (9) A˚
c= 27.952 (9) A˚
V= 3461 (4) A˚3 Z= 8
Dx= 1.330 Mg m
3
MoKradiation Cell parameters from 25
reflections = 1.5–30.0
= 0.20 mm1 T= 293 (2) K Block, yellow 0.240.220.19 mm
Data collection
Enraf–Nonius CAD-4 diffractometer !scans
Absorption correction: none 5044 measured reflections 5044 independent reflections 3579 reflections withI> 2(I)
max= 30.0 h= 0!10
k= 0!23
l= 0!39
3 standard reflections frequency: 60 min intensity decay: none
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.058 wR(F2) = 0.235 S= 1.04 5044 reflections 228 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.1453P)2
+ 1.73P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.65 e A˚
3
min=0.49 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
S1—C1 1.710 (3) S1—C8 1.712 (3) O1—C12 1.378 (3)
O1—C15 1.422 (4) O2—C19 1.367 (3) O2—C22 1.420 (4)
C1—S1—C8 94.5 (2) C12—O1—C15 117.3 (2) C19—O2—C22 116.7 (2)
[image:2.610.343.533.235.497.2]C14—C9—C10 116.9 (2) C21—C16—C17 117.7 (2)
Table 2
Hydrogen-bond geometry (A˚ ,).
Cg1 andCg2 are the centroids of the C16–C21 and C9–C14 benzene rings, respectively.
D—H A D—H H A D A D—H A
C15—H15A O2i
0.96 2.52 3.385 (5) 149 C11—H11 Cg1ii 0.93 2.73 3.595 (4) 155 C14—H14 Cg2iii
0.93 2.78 3.550 (4) 141 C18—H18 Cg2iv
0.93 2.88 3.662 (4) 143
Symmetry codes: (i)xþ3 2;yþ
1
2;zþ1; (ii)xþ2;y;zþ1; (iii)x 1 2;yþ
1 2;z;
(iv)xþ1;y;zþ1.
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93 or 0.96 A˚ andUiso(H) = 1.2–
1.5Ueq(C).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction:XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication:PLATON(Spek, 2003).
KP thanks the University Grants Commission (UCG) Herbal Science programme for financial support under the ‘University with Potential for Excellence’ scheme. The UGC and the Department of Science & Technology (DST) are gratefully acknowledged for financial support to the Depart-ment of Crystallography and Biophysics under the UGC-SAP and DST-FIST programmes.
References
Enraf–Nonius (1994).CAD-4 EXPRESS. Enraf-Nonius, Delft, The Nether-lands.
Gewald, K., Schinke., E. & Botcher, H. (1966).Chem. Ber.99, 99–100. Harms, K. & Wocadlo, S. (1995).XCAD4. University of Marburg, Germany. Portevin, B., Tordjman, C., Pastoureau, P., Bonnet, J. & De Nanteuil, G. (2000).
J. Med. Chem.43, 4582–4593.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
organic papers
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Palaniet al. C22H18O2S Acta Cryst.(2006). E62, o49–o51
Figure 1
The molecular structure of (I), showing 30% probability displacement ellipsoids.
Figure 2
[image:2.610.45.295.551.607.2]Shi, J.-X., Hu, Q.-P., Lei, Y.-J. & Reiner, J. (2004).Acta Cryst.E60, o1810– o1811.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
Szczepankiewicz, B. G., Liu, G., Jac, H.-S., Tasker, A. & Gunawardana, I. W. (2001).J. Med. Chem.44, 4416–1492.
Zsolnai, L. (1997).ZORTEP. Univeristy of Heidelberg, Germany.
organic papers
Acta Cryst.(2006). E62, o49–o51 Palaniet al. C
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Acta Cryst. (2006). E62, o49–o51
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Acta Cryst. (2006). E62, o49–o51 [doi:10.1107/S1600536805039589]
1,3-Bis(4-methoxyphenyl)-2-benzothiophene
K. Palani, P. Amaladass, A. K. Mohanakrishnan and M. N. Ponnuswamy
S1. Comment
Most Schiff bases and their thiophene derivatives possess pharmacological activities such as antibacterial, anticancer,
anti-inflammatory and antitoxic properties (Gewald et al., 1996 or 1966). The diaryl-substituted heterocyclic molecules
act as selective COX-2 inhibitors (Portevin et al., 2000) and antitumor agents (Szczepankiewicz et al., 2001 or 2000). In
view of this importance, the crystal structure of the title compound, (I), has been determined and the results are presented
here.
A ZORTEP (Zsolnai, 1997) plot of the molecule is shown in Fig.1. The bond lengths and bond angles (Table 1) in the
thiophene moiety are comparable to those reported for
4-{5-[3,4-dimethyl-5-(3,4,5-trimethoxyphenyl)thiophen-2-yl]-2-methoxyphenyl}morpholine (Shi et al., 2004). The C9–C14 and C16–C21 benzene rings are oriented at angles of
34.99 (9) and 41.57 (9)°, respectively, with respect to the thiophene ring. The dihedral angle between the C9–C14 and
C16–C21 benzene rings is 71.2 (1)°. Both the methoxy groups are coplanar with the attached rings. The crystal packing is
stabilized by C—H···O and C—H···π type hydrogen bonds (Table 2 and Fig. 2). In Table 2, Cg1 and Cg2 denote the
centroids of the C16—C21 and C9—C14 benzene rings, respectively.
S2. Experimental
4-Methoxymagnesium bromide was prepared from 4-bromoanisole (23 mmol) and Mg (25 mmol). 4-Methoxymagnesium
bromide was added to a solution of pthalide (20.8 mmol) at 273 K. The reaction mixture was stirred at room temperature
for 5 h and then it was poured into an ice-cooled NH4 Cl solution and extracted with CH2Cl2 (50 ml) and dried over
Na2SO4. The reaction mixture was treated with Lawesson's reagent (10.4 mmol) and stirred at room temperature for 5 h.
The solvent was removed and the residue was gently heated on steam bath with ethanol. The product was purified by
column chromatography (neutral alumina, hexane) to afford compound (I) as a yellow powder. Single crystals of (I) were
obtained by recrystallization from boiling hexane.
S3. Refinement
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93 or 0.96 Å and
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Figure 1
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[image:6.610.145.466.70.520.2]Acta Cryst. (2006). E62, o49–o51
Figure 2
The crystal packing of (I), viewed approximately down the c axis. Dashed lines indicate C—H···π interactions.
1,3-Bis(4-methoxyphenyl)-2-benzothiophene
Crystal data
C22H18O2S
Mr = 346.42
Orthorhombic, Pcab Hall symbol: -P 2bc 2ac a = 7.508 (6) Å
b = 16.493 (9) Å c = 27.952 (9) Å V = 3461 (4) Å3
Z = 8
F(000) = 1456 Dx = 1.330 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 1.5–30.0°
µ = 0.20 mm−1
T = 293 K Block, yellow
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Acta Cryst. (2006). E62, o49–o51
Data collection
Enraf–Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
5044 measured reflections 5044 independent reflections 3579 reflections with I > 2σ(I)
Rint = 0.000
θmax = 30.0°, θmin = 1.5°
h = 0→10 k = 0→23 l = 0→39
3 standard reflections every 60 min intensity decay: none
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.058
wR(F2) = 0.235
S = 1.04 5044 reflections 228 parameters 0 restraints
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) + (0.1453P)2 + 1.73P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.65 e Å−3
Δρmin = −0.49 e Å−3
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 0.73445 (9) 0.07389 (4) 0.48152 (2) 0.0398 (2)
O1 0.9918 (3) 0.15231 (12) 0.70411 (7) 0.0496 (5)
O2 0.5670 (3) −0.08331 (12) 0.26912 (7) 0.0535 (5)
C1 0.7680 (3) 0.16315 (14) 0.51128 (9) 0.0355 (5)
C2 0.7421 (3) 0.22830 (14) 0.48059 (9) 0.0345 (5)
C3 0.7623 (3) 0.31269 (14) 0.49035 (10) 0.0389 (5)
H3 0.7987 0.3302 0.5204 0.047*
C4 0.7274 (4) 0.36711 (15) 0.45499 (10) 0.0455 (6)
H4 0.7425 0.4221 0.4612 0.055*
C5 0.6690 (4) 0.34278 (16) 0.40919 (11) 0.0472 (6)
H5 0.6411 0.3819 0.3864 0.057*
C6 0.6530 (4) 0.26293 (15) 0.39783 (10) 0.0424 (6)
H6 0.6174 0.2475 0.3673 0.051*
C7 0.6912 (3) 0.20316 (13) 0.43306 (9) 0.0345 (5)
C8 0.6845 (3) 0.11937 (14) 0.42814 (9) 0.0353 (5)
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C10 0.9347 (3) 0.10018 (15) 0.57957 (9) 0.0388 (5)
H10 0.9746 0.0599 0.5589 0.047*
C11 0.9865 (3) 0.09821 (15) 0.62662 (10) 0.0411 (6)
H11 1.0596 0.0567 0.6376 0.049*
C12 0.9296 (3) 0.15848 (14) 0.65786 (9) 0.0368 (5)
C13 0.8177 (3) 0.22008 (15) 0.64162 (9) 0.0382 (5)
H13 0.7792 0.2604 0.6624 0.046*
C14 0.7646 (3) 0.22063 (15) 0.59424 (9) 0.0374 (5)
H14 0.6882 0.2613 0.5837 0.045*
C15 0.9334 (5) 0.21177 (19) 0.73747 (11) 0.0578 (8)
H15A 0.9667 0.2647 0.7263 0.087*
H15B 0.9877 0.2018 0.7680 0.087*
H15C 0.8062 0.2089 0.7406 0.087*
C16 0.6489 (3) 0.06917 (13) 0.38565 (9) 0.0355 (5)
C17 0.5482 (4) −0.00260 (16) 0.38883 (10) 0.0435 (6)
H17 0.4979 −0.0172 0.4180 0.052*
C18 0.5228 (4) −0.05154 (16) 0.34961 (11) 0.0451 (6)
H18 0.4551 −0.0985 0.3523 0.054*
C19 0.5986 (3) −0.03062 (15) 0.30588 (10) 0.0399 (5)
C20 0.6978 (4) 0.03999 (15) 0.30184 (10) 0.0405 (5)
H20 0.7477 0.0545 0.2726 0.049*
C21 0.7222 (3) 0.08870 (15) 0.34164 (9) 0.0393 (5)
H21 0.7895 0.1358 0.3388 0.047*
C22 0.6646 (5) −0.0704 (2) 0.22628 (12) 0.0594 (8)
H22A 0.6303 −0.0195 0.2124 0.089*
H22B 0.6400 −0.1134 0.2041 0.089*
H22C 0.7897 −0.0695 0.2334 0.089*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
S1 0.0468 (4) 0.0279 (3) 0.0448 (4) 0.0002 (2) −0.0019 (3) 0.0022 (2)
O1 0.0560 (12) 0.0498 (11) 0.0428 (10) 0.0087 (9) −0.0081 (9) 0.0046 (8)
O2 0.0609 (13) 0.0475 (11) 0.0520 (12) −0.0088 (9) −0.0044 (10) −0.0105 (9)
C1 0.0349 (11) 0.0303 (10) 0.0414 (12) 0.0013 (9) 0.0030 (9) 0.0003 (9)
C2 0.0292 (10) 0.0285 (10) 0.0458 (12) −0.0004 (8) 0.0022 (9) −0.0005 (9)
C3 0.0416 (13) 0.0310 (11) 0.0441 (13) −0.0015 (9) 0.0021 (10) −0.0035 (9)
C4 0.0554 (16) 0.0299 (11) 0.0512 (15) 0.0002 (11) 0.0066 (12) −0.0001 (10)
C5 0.0579 (16) 0.0357 (12) 0.0480 (15) 0.0047 (11) 0.0013 (13) 0.0063 (10)
C6 0.0467 (14) 0.0351 (12) 0.0454 (13) 0.0023 (10) −0.0036 (11) 0.0048 (10)
C7 0.0313 (10) 0.0292 (10) 0.0429 (12) 0.0001 (8) 0.0018 (9) 0.0009 (9)
C8 0.0352 (11) 0.0308 (10) 0.0399 (12) −0.0012 (9) 0.0010 (9) 0.0005 (9)
C9 0.0296 (10) 0.0315 (10) 0.0439 (12) −0.0006 (8) 0.0009 (9) 0.0027 (9)
C10 0.0373 (12) 0.0320 (11) 0.0470 (13) 0.0052 (9) 0.0002 (10) 0.0000 (9)
C11 0.0347 (12) 0.0341 (11) 0.0546 (15) 0.0055 (9) −0.0036 (10) 0.0066 (10)
C12 0.0327 (11) 0.0363 (11) 0.0415 (12) −0.0027 (9) −0.0011 (9) 0.0047 (9)
C13 0.0365 (12) 0.0354 (11) 0.0427 (13) 0.0033 (9) 0.0033 (10) 0.0007 (9)
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C15 0.075 (2) 0.0488 (16) 0.0499 (16) 0.0049 (15) −0.0012 (15) −0.0007 (13)
C16 0.0341 (11) 0.0300 (10) 0.0425 (12) 0.0004 (8) −0.0003 (9) −0.0014 (9)
C17 0.0430 (13) 0.0374 (12) 0.0502 (15) −0.0078 (10) 0.0079 (11) 0.0002 (10)
C18 0.0421 (13) 0.0375 (12) 0.0556 (15) −0.0112 (10) 0.0027 (12) −0.0043 (11)
C19 0.0361 (12) 0.0358 (11) 0.0478 (14) 0.0008 (9) −0.0073 (10) −0.0031 (10)
C20 0.0443 (13) 0.0372 (12) 0.0401 (12) −0.0012 (10) 0.0008 (10) 0.0028 (10)
C21 0.0404 (13) 0.0329 (11) 0.0445 (13) −0.0041 (9) 0.0010 (10) 0.0002 (9)
C22 0.066 (2) 0.0622 (19) 0.0507 (17) 0.0026 (15) −0.0043 (15) −0.0094 (14)
Geometric parameters (Å, º)
S1—C1 1.710 (3) C10—H10 0.93
S1—C8 1.712 (3) C11—C12 1.390 (4)
O1—C12 1.378 (3) C11—H11 0.93
O1—C15 1.422 (4) C12—C13 1.394 (3)
O2—C19 1.367 (3) C13—C14 1.383 (4)
O2—C22 1.420 (4) C13—H13 0.93
C1—C2 1.389 (3) C14—H14 0.93
C1—C9 1.466 (4) C15—H15A 0.96
C2—C3 1.427 (3) C15—H15B 0.96
C2—C7 1.443 (4) C15—H15C 0.96
C3—C4 1.361 (4) C16—C21 1.386 (4)
C3—H3 0.93 C16—C17 1.407 (3)
C4—C5 1.411 (4) C17—C18 1.375 (4)
C4—H4 0.93 C17—H17 0.93
C5—C6 1.360 (4) C18—C19 1.392 (4)
C5—H5 0.93 C18—H18 0.93
C6—C7 1.423 (3) C19—C20 1.387 (4)
C6—H6 0.93 C20—C21 1.384 (4)
C7—C8 1.390 (3) C20—H20 0.93
C8—C16 1.472 (3) C21—H21 0.93
C9—C14 1.400 (3) C22—H22A 0.96
C9—C10 1.413 (3) C22—H22B 0.96
C10—C11 1.372 (4) C22—H22C 0.96
C1—S1—C8 94.5 (2) C11—C12—C13 120.1 (2)
C12—O1—C15 117.3 (2) C14—C13—C12 119.4 (2)
C19—O2—C22 116.7 (2) C14—C13—H13 120.3
C2—C1—C9 130.1 (2) C12—C13—H13 120.3
C2—C1—S1 110.19 (19) C13—C14—C9 122.0 (2)
C9—C1—S1 119.68 (18) C13—C14—H14 119.0
C1—C2—C3 128.5 (2) C9—C14—H14 119.0
C1—C2—C7 112.5 (2) O1—C15—H15A 109.5
C3—C2—C7 119.0 (2) O1—C15—H15B 109.5
C4—C3—C2 119.0 (2) H15A—C15—H15B 109.5
C4—C3—H3 120.5 O1—C15—H15C 109.5
C2—C3—H3 120.5 H15A—C15—H15C 109.5
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C3—C4—H4 119.0 C21—C16—C17 117.7 (2)
C5—C4—H4 119.0 C21—C16—C8 120.9 (2)
C6—C5—C4 121.0 (3) C17—C16—C8 121.3 (2)
C6—C5—H5 119.5 C18—C17—C16 121.2 (2)
C4—C5—H5 119.5 C18—C17—H17 119.4
C5—C6—C7 119.4 (3) C16—C17—H17 119.4
C5—C6—H6 120.3 C17—C18—C19 119.9 (2)
C7—C6—H6 120.3 C17—C18—H18 120.1
C8—C7—C6 127.8 (2) C19—C18—H18 120.1
C8—C7—C2 112.7 (2) O2—C19—C20 124.5 (3)
C6—C7—C2 119.4 (2) O2—C19—C18 115.6 (2)
C7—C8—C16 130.2 (2) C20—C19—C18 120.0 (2)
C7—C8—S1 109.97 (18) C21—C20—C19 119.5 (2)
C16—C8—S1 119.77 (18) C21—C20—H20 120.2
C14—C9—C10 116.9 (2) C19—C20—H20 120.2
C14—C9—C1 121.9 (2) C20—C21—C16 121.8 (2)
C10—C9—C1 121.2 (2) C20—C21—H21 119.1
C11—C10—C9 121.7 (2) C16—C21—H21 119.1
C11—C10—H10 119.1 O2—C22—H22A 109.5
C9—C10—H10 119.1 O2—C22—H22B 109.5
C10—C11—C12 119.9 (2) H22A—C22—H22B 109.5
C10—C11—H11 120.1 O2—C22—H22C 109.5
C12—C11—H11 120.1 H22A—C22—H22C 109.5
O1—C12—C11 115.6 (2) H22B—C22—H22C 109.5
O1—C12—C13 124.3 (2)
C8—S1—C1—C2 −0.28 (19) C1—C9—C10—C11 180.0 (2)
C8—S1—C1—C9 −178.3 (2) C9—C10—C11—C12 −0.7 (4)
C9—C1—C2—C3 0.1 (4) C15—O1—C12—C11 −178.6 (3)
S1—C1—C2—C3 −177.7 (2) C15—O1—C12—C13 1.8 (4)
C9—C1—C2—C7 179.0 (2) C10—C11—C12—O1 −178.6 (2)
S1—C1—C2—C7 1.2 (3) C10—C11—C12—C13 1.0 (4)
C1—C2—C3—C4 −179.1 (3) O1—C12—C13—C14 179.5 (2)
C7—C2—C3—C4 2.1 (4) C11—C12—C13—C14 −0.1 (4)
C2—C3—C4—C5 1.1 (4) C12—C13—C14—C9 −1.2 (4)
C3—C4—C5—C6 −3.1 (5) C10—C9—C14—C13 1.5 (4)
C4—C5—C6—C7 1.7 (4) C1—C9—C14—C13 −179.1 (2)
C5—C6—C7—C8 −179.2 (3) C7—C8—C16—C21 41.7 (4)
C5—C6—C7—C2 1.5 (4) S1—C8—C16—C21 −135.8 (2)
C1—C2—C7—C8 −1.8 (3) C7—C8—C16—C17 −142.0 (3)
C3—C2—C7—C8 177.3 (2) S1—C8—C16—C17 40.5 (3)
C1—C2—C7—C6 177.6 (2) C21—C16—C17—C18 −0.2 (4)
C3—C2—C7—C6 −3.4 (3) C8—C16—C17—C18 −176.6 (2)
C6—C7—C8—C16 4.5 (4) C16—C17—C18—C19 0.5 (4)
C2—C7—C8—C16 −176.2 (2) C22—O2—C19—C20 9.7 (4)
C6—C7—C8—S1 −177.8 (2) C22—O2—C19—C18 −170.5 (3)
C2—C7—C8—S1 1.5 (3) C17—C18—C19—O2 179.5 (2)
supporting information
sup-8
Acta Cryst. (2006). E62, o49–o51
C1—S1—C8—C16 177.2 (2) O2—C19—C20—C21 −179.6 (2)
C2—C1—C9—C14 37.1 (4) C18—C19—C20—C21 0.7 (4)
S1—C1—C9—C14 −145.3 (2) C19—C20—C21—C16 −0.4 (4)
C2—C1—C9—C10 −143.5 (3) C17—C16—C21—C20 0.2 (4)
S1—C1—C9—C10 34.1 (3) C8—C16—C21—C20 176.6 (2)
C14—C9—C10—C11 −0.6 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C15—H15A···O2i 0.96 2.52 3.385 (5) 149
C11—H11···Cg1ii 0.93 2.73 3.595 (4) 155
C14—H14···Cg2iii 0.93 2.78 3.550 (4) 141
C18—H18···Cg2iv 0.93 2.88 3.662 (4) 143
