An additional methylene group driving the conformation and assembly of two arylsulfonamide para-alkoxychalcone hybrids

Article abstract of DOI:10.1107/S0108270113002291

The structures of two arylsulfonamide para-alkoxychalcones, namely, N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C ₂₂H₁₉NO₄S, (I), and N-{4-[(E)-3-(4- ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide, C₂₃H ₂₁NO₄S, (II), reveal the effect of the inclusion of one -CH₂- group between the CH₃ branch and the alkoxy O atom on the conformation and crystal structure. Although the molecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent molecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C - H?π and π-π interactions, while only C - H?π contacts occur in the structure of (II). The role of the additional methylene group in the crystal packing can also be seen in the fact that the alkoxy O atom is an acceptor in nonclassical hydrogen bonds only in the para-ethoxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N - H?O hydrogen-bonded ribbons, a synthon commonly found in related compounds. Copyright

Full text of DOI:10.1107/S0108270113002291

organic compounds
Acta Crystallographica Section C
Crystal Structure
al., 2010). Chalcones containing an arylsulfonamide group are
emerging compounds for which antimalarial properties have
Communications
´
already been demonstrated (Domınguez et al., 2005).
ISSN 0108-2701
As part of our ongoing studies of sulfonamides in terms of
their structural features (Martins et al., 2009; Fernandes et al.,
2011), in this study the arylsulfonamide para-alkoxychalcones,
N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}benzene-
sulfonamide, (I), and N-{4-[(E)-3-(4-ethoxyphenyl)prop-2-en-
oyl]phenyl}benzenesulfonamide, (II), differing only in one
methylene group in the para-alkoxy fragment on the chalcone
skeleton, were synthesized and their crystal structures deter-
mined using single-crystal X-ray diffraction. This molecular
difference of only one –CH2– group is enough to change the
crystal assembly and symmetry. Likewise, the absence of
methylene in the para-alkoxy group of (I) is also related to the
conformational variability observed in this compound.
An additional methylene group driving
the conformation and assembly of two
arylsulfonamide para-alkoxychalcone
hybrids
Mirian R. C. de Castro,a Angelo Q. Arag˜ao,b Hamilton B.
Napolitano,b Caridad Noda-Pereza and Felipe T. Martinsa*
a
´
ˆ
Institute of Chemistry, Federal University of Goias, Goiania, GO 74001-970, Brazil,
b
´
´
and Science and Technology Center, State University of Goias, Anapolis, GO
75132-903, Brazil
Correspondence e-mail: felipetmartins@yahoo.com.br
Received 6 December 2012
Accepted 23 January 2013
Online 5 February 2013
The structures of two arylsulfonamide para-alkoxychalcones,
namely, N-{4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl}-
benzenesulfonamide, C22H19NO4S, (I), and N-{4-[(E)-3-
(4-ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide,
C23H21NO4S, (II), reveal the effect of the inclusion of one
–CH2– group between the CH3 branch and the alkoxy O atom
on the conformation and crystal structure. Although the
molecular conformations and one-dimensional chain motifs
are the same in both structures, their crystallographic
symmetry, number of independent molecules and crystal
packing are different. The crystal packing of (I) is stabilized by
weak C—Hꢀ ꢀ ꢀꢀ and ꢀ–ꢀ interactions, while only C—Hꢀ ꢀ ꢀꢀ
contacts occur in the structure of (II). The role of the
additional methylene group in the crystal packing can also be
seen in the fact that the alkoxy O atom is an acceptor in
nonclassical hydrogen bonds only in the para-ethoxy
analogue, (II). The remarkable similarity between the crystal
packing features of (I) and (II) lies in the formation of N—
Hꢀ ꢀ ꢀO hydrogen-bonded ribbons, a synthon commonly found
in related compounds.
Because of the slight molecular structure differences
between (I) and (II), they crystallize in different crystal
systems and space groups. While the crystal structure of (I)
was solved in the centrosymmetric triclinic space group P1,
with two independent molecules in the asymmetric unit, (II)
crystallizes in the monoclinic space group P21/c with only one
molecule in the asymmetric unit (Fig. 1).
Compound (I) has two conformers in its crystal structure,
labelled A and B. The chalcone molecular backbones of both
conformers are almost completely planar [r.m.s. deviations =
˚
0.0537 and 0.0440 A, respectively, for conformers A and B,
˚
with the greatest deviations being ꢁ0.2053 A for atom C18A
˚
and 0.2076 A for atom C8B, where the chalcone plane is
defined by atoms C13–C15/O3 and the C atoms of rings B
(central) and C (alkoxy-substituted) in Fig. 1] and therefore
similar, even though there are slight rotations about the
sulfamyl S1—N1 and sulfonyl S1—C1 bridging bond axes
(Fig. 2). More specifically, the chalcone group of conformer A
is more planar than that of conformer B. In the latter, there
are three slight rotations on the bond axes of: (i) C10B—
C13B, which displaces central ring B from the neighbouring
carbonyl group [e.g. the C9B—C10B—C13B—O3B torsion
angle is 8.3 (4)ꢂ, cf. 5.6 (5)ꢂ for the corresponding torsion
angle in conformer A]; (ii) C15B—C16B, twisting the para-
alkoxy-substituted ring C from the C14 C15 group [e.g. the
C14B—C15B—C16B—C21B torsion angle is ꢁ7.8 (4)ꢂ, cf.
ꢁ0.6 (6)ꢂ for the corresponding torsion angle in conformer A];
(iii) C19B—O4B, setting the methyl group of the methoxy in
the para position out of the ring C plane [e.g. the C18B—
C19B—O4B—C22B torsion angle is 7.8 (4)ꢂ, cf. 6.9 (5)ꢂ for
the corresponding torsion angle in conformer A]. The rotation
on this last bond axis is also appreciable in conformer A of (I)
Comment
Compounds containing a sulfonamide group are well known
to possess strong antibacterial effects, and they are widely
used against common bacterial diseases due to their low cost,
low toxicity and excellent pharmacological profiles (Ozbek et
al., 2007). The sulfonamide group is also present in many
biologically active compounds, such as antimicrobial, anti-
thyroid, antitumour and antimalarial drugs (Ozdemir et al.,
´
2009; Seo et al., 2010; Domınguez et al., 2005; Connor, 1998;
Hanson et al., 1999). In addition, many substituted aromatic
and heterocyclic sulfonamides have been synthesized and
their activity against glaucoma has been evaluated (Remko et
Acta Cryst. (2013). C69, 267–272
doi:10.1107/S0108270113002291
# 2013 International Union of Crystallography 267

organic compounds
Figure 1
A view of the molecular structures of (a) (I) and (b) (II), showing the atom- and ring-labelling schemes. Displacement ellipsoids are drawn at the 30%
probability level.
and in (II), which also shows a remarkable planarity of its
˚
chalcone skeleton (r.m.s. deviation = 0.0371 A, with the
˚
greatest deviation being 0.1563 A for atom C8), except that
the ethyl group is slightly out of the ring C plane, as mentioned
above.
a further intermolecular classical O—Hꢀ ꢀ ꢀO hydrogen bond
involving the para-hydroxy and sulfamyl groups of TSAHC,
which is not present in (I) and (II). However, the N—Hꢀ ꢀ ꢀO
hydrogen bonding between the amino and carbonyl groups is
It is interesting to note that in the crystal structure of the
only other example of an arylsulfonamide chalcone hybrid
found in the Cambridge Structural Database (CSD, Version
5.33, August 2012 update; Allen, 2002), namely, 40-(p-tolu-
enesulfonylamino)-4-hydroxychalcone (TSAHC; CSD ref-
code NARZIR; Seo et al., 2010), the chalcone skeleton is
strongly twisted, wherein the least-squares planes through the
corresponding rings B and C form an angle of 33.9 (8)ꢂ. We
observe values of 10.8 (1), 10.02 (8) and 5.2 (8)ꢂ in molecules
A and B of (I) and in (II), respectively. In the structure of
TSAHC, the observed twist may be related to the presence of
Figure 2
A superposition of the conformers A (grey) and B (black) of (I). H atoms
have been omitted for clarity.
ꢃ
268 Castro et al. C22H19NO4S and C23H21NO4S
Acta Cryst. (2013). C69, 267–272

organic compounds
Figure 3
(a) The infinite one-dimensional chains of (I), propagating along the [001] direction, (b) the stacking of the chains of (I), (c) the infinite one-dimensional
chains of (II), propagating along the [001] direction, and (d) the stacking of the chains of (II). Classical N—Hꢀ ꢀ ꢀO and nonclassical C—Hꢀ ꢀ ꢀO hydrogen-
1
bond interactions are shown as dashed lines. [Symmetry codes, (a): (i) ꢁx + 1, ꢁy + 1, ꢁz; (ii) ꢁx + 1, ꢁy + 1, ꢁz + 1; (c): (i) x, ꢁy + 12, z ꢁ ; (ii) x, ꢁy + 21,
2
z + 12.]
conserved in the structures of TSAHC, (I) and (II). In all three
sulfonamide chalcone derivatives, these N—Hꢀ ꢀ ꢀO inter-
actions give rise to infinite one-dimensional ribbons running
along the [001] (or [010] in TSAHC) direction (Fig. 3). In the
structures of both (I) and (II), each chain has all phenyl rings
A oriented towards the same side of the sulfonamide–chal-
cone plane (Fig. 3). These ribbons are made up of alternating
molecules A and B in (I), while c-glide-related units assemble
these supramolecular motifs in (II). The linear ribbons are
stacked face-to-face, along the [120] direction in (I) and along
the a axis in (II). In contrast, a zigzag chain is formed with 21-
screw axis symmetry-related molecules in TSAHC.
(Tables 1 and 2). The pairwise interactions co-exist with a
degree of coplanarity between sulfonamide–chalcone frag-
ments of the hydrogen-bonded molecules. Between successive
molecules along the chain, these fragments, defined as the
chalcone plane plus atoms N1 and S1, form dihedral angles of
15.0 and 6.4ꢂ in (I) and (II).
The supramolecular assemblies of (I) and (II) are thus
similar in the formation of linear ribbons, but the structural
similarities between them end there. While the crystal packing
of (I) is stabilized by weak C—Hꢀ ꢀ ꢀꢀ and ꢀ–ꢀ interactions,
only the former interactions occur in (II). In (I), inversion-
related molecules A interact through their CH3 groups and
phenyl A rings in very weak but co-operative C—Hꢀ ꢀ ꢀꢀ
interactions involving two methyl H atoms (CgAꢀ ꢀ ꢀH22Div =
In addition to the classical hydrogen bonds, the ribbons in
(I) and (II) are supported by C9—H9ꢀ ꢀ ꢀO1 hydrogen bonds
ꢃ
Acta Cryst. (2013). C69, 267–272
Castro et al.
C22H19NO4S and C23H21NO4S 269

organic compounds
Figure 4
The C—Hꢀ ꢀ ꢀO, C—Hꢀ ꢀ ꢀꢀ and ꢀ–ꢀ interactions (dashed lines) in the structure of (I). [Symmetry codes: (iii) ꢁx, ꢁy + 1, ꢁz; (iv) x, y ꢁ 1, z + 1; (v) ꢁx,
ꢁy + 1, ꢁz + 2.]
iv
˚
˚
3.28 A and CgAꢀ ꢀ ꢀH22E = 3.33 A, where CgA is the centroid
calculated through the ring A C atoms of molecule A; see
Table 1 for symmetry code) (Fig. 4). The rings of both mol-
ecules A and B are further connected by weak ꢀ–ꢀ inter-
actions in (I), with a CgAꢀ ꢀ ꢀCgA0 distance between translation
O4 atom by a CH2 moiety of the ethoxy group in (II) leads
to the formation of
a
C23—H23Aꢀ ꢀ ꢀCgA interaction
(CgAꢀ ꢀ ꢀH23Aiii = 3.04 A; see Table 2 for symmetry code),
assembling dimers made up of inversion-related molecules
(Fig. 5a). In this figure, it is possible to see the occurrence of a
ꢀ–ꢀ interaction between the ꢀ-electrons of the double bond
between atoms C14 and C15 and the C atoms of ring B
˚
˚
symmetry-related molecules at (x, y + 1, z ꢁ 1) of 3.72 (5) A
(Fig. 4). However, the ethoxy CH3 group in (II) is involved in
C—Hꢀ ꢀ ꢀꢀ contacts in this structure and ꢀ–ꢀ interactions do
not occur. The intercalation between the CH3 group and the
v
˚
[CgDꢀ ꢀ ꢀCgB = 3.56 A, where CgD is the centroid calculated
through atoms C14 and C15, and CgB is the centroid calcu-
Figure 5
(a) The C—Hꢀ ꢀ ꢀꢀ interaction and (b) the bifurcated C—Hꢀ ꢀ ꢀO hydrogen-bond contacts in the structure of (II). These interactions are shown as dashed
1
lines. [Symmetry codes: (iii) ꢁx + 1, ꢁy, ꢁz + 2; (iv) ꢁx + 1, y + , ꢁz + 32.]
2
ꢃ
270 Castro et al. C22H19NO4S and C23H21NO4S
Acta Cryst. (2013). C69, 267–272

organic compounds
Table 1
Hydrogen-bond geometry (A, ) for (I).
lated through the C atoms of ring B; symmetry code: (v) ꢁx + 1,
ꢁy, ꢁz + 2]. In this structure, the role of the additional
methylene group in the crystal packing and symmetry can also
be seen in the fact that alkoxy atom O4 is involved as an
acceptor in weak acceptor-bifurcated nonclassical hydrogen
bonds, having as donors the neighbouring C2—H2 and C3—
H3 groups of phenyl ring A. Both C2—H2ꢀ ꢀ ꢀO4iv and C3—
H3ꢀ ꢀ ꢀO4iv contacts occur between 21-screw axis symmetry-
related molecules assembled into zigzag chains along the [010]
direction (see Fig. 5b for symmetry code). These contacts and
chains are not observed in (I). In the structure of (I), the
methoxy group is involved in nonclassical C—Hꢀ ꢀ ꢀO
hydrogen bonding, viz. C22B—H22Aꢀ ꢀ ꢀO2Biii, as a donor to
an O atom of SO2 in an inversion-related molecule B (Fig. 4)
(see Table 1 for symmetry code).
ꢂ
˚
CgA is the centroid calculated through the C atoms of benzenesulfonamide
ring A of molecule A.
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1A—H1Aꢀ ꢀ ꢀO3Bi
N1B—H1Bꢀ ꢀ ꢀO3Aii
C9A—H9Aꢀ ꢀ ꢀO1Bii
C9B—H9Bꢀ ꢀ ꢀO1Ai
C22B—H22Aꢀ ꢀ ꢀO2Biii
C22A—H22Dꢀ ꢀ ꢀCgAiv
C22A—H22Eꢀ ꢀ ꢀCgAiv
0.81 (5)
0.81 (5)
0.93
0.93
0.96
2.16 (5)
2.11 (5)
2.43
2.49
2.40
2.950 (3)
2.892 (3)
3.320 (4)
3.366 (3)
3.317 (4)
3.580 (4)
3.580 (4)
166 (5)
163 (5)
160
157
160
0.96
0.96
3.28
3.33
101
97
Symmetry codes: (i) ꢁx þ 1; ꢁy þ 1; ꢁz; (ii) ꢁx þ 1; ꢁy þ 1; ꢁz þ 1; (iii) ꢁx; ꢁy þ 1,
ꢁz; (iv) ꢁx; ꢁy þ 2; ꢁz þ 1.
Refinement
R[F2 > 2ꢅ(F2)] = 0.054
wR(F2) = 0.152
S = 1.02
8378 reflections
512 parameters
H atoms treated by a mixture of
independent and constrained
refinement
In conclusion, this study presents an interesting example in
which a molecular difference of only one CH2 group in the
terminal alkoxy group has altered the crystal packing and
symmetry in two otherwise identical compounds. While clas-
sical hydrogen-bonding patterns are conserved in both struc-
tures investigated here, the combination of weak C—Hꢀ ꢀ ꢀO,
C—Hꢀ ꢀ ꢀꢀ and ꢀ–ꢀ contacts involving the phenyl heads and
alkoxy tails differs, and this is responsible for the differences
observed in the conformations and intermolecular archi-
tectures of these two chalcone–sulfonamide analogues. From a
crystallographic point of view, not only are the crystal systems
and space groups different for (I) and (II), but the Z0 values
also differ. This reveals that their crystal structures must
depend on the intermolecular contact patterns involving the
methylene group of the alkoxy substituent.
ꢁ3
˚
Áꢆmax = 0.24 e A
ꢁ3
˚
Áꢆmin = ꢁ0.27 e A
Compound (II)
Crystal data
3
˚
V = 2115.49 (9) A
Z = 4
C23H21NO4S
Mr = 407.47
Monoclinic, P21=c
Mo Kꢁ radiation
ꢄ = 0.18 mmꢁ1
T = 298 K
0.25 ꢄ 0.20 ꢄ 0.15 mm
˚
a = 8.4506 (2) A
b = 20.1587 (6) A
˚
˚
c = 14.2120 (3) A
ꢂ = 119.098 (2)ꢂ
Data collection
Nonius KappaCCD area-detector
diffractometer
7397 measured reflections
4185 independent reflections
3072 reflections with I > 2ꢅ(I)
Rint = 0.036
Experimental
Compounds (I) and (II) were synthesized by Claisen–Schmidt
condensation from N-(4-acetylphenyl)benzenesulfonamide with
either p-methoxybenzene [for (I)] or p-ethoxybenzaldehyde [for (II)],
using sodium hydroxide in ethanol (50% w/w) as catalyst. The reac-
tions were performed at 343 K for about either 22 h [for (I)] or 24 h
[for (II)]. In each case, the precipitate was recrystallized from
dichloromethane to obtain single crystals. The reaction yields were 57
and 65% for (I) and (II), respectively, and the melting-point ranges
were 446–448 K and 425–427 K, respectively.
Refinement
R[F2 > 2ꢅ(F2)] = 0.049
wR(F2) = 0.143
S = 1.05
4185 reflections
265 parameters
H atoms treated by a mixture of
independent and constrained
refinement
ꢁ3
˚
Áꢆmax = 0.17 e A
ꢁ3
˚
Áꢆmin = ꢁ0.27 e A
All C-bound H atoms were placed geometrically and refined using
˚
a riding model, with C—H = 0.97 (CH2), 0.96 (CH3) or 0.93 A
(aromatic groups), and with Uiso(H) = 1.2Ueq(C). The N-bound H
atoms were found in difference Fourier maps and their positional
parameters were refined freely; Uiso(H) values were set at 1.2Ueq(N).
Compound (I)
Crystal data
Table 2
Hydrogen-bond geometry (A, ) for (II).
C22H19NO4S
Mr = 393.44
Triclinic, P1
ꢃ = 80.437 (1)ꢂ
V = 1948.99 (8) A
Z = 4
Mo Kꢁ radiation
ꢄ = 0.19 mmꢁ1
T = 298 K
0.28 ꢄ 0.15 ꢄ 0.08 mm
ꢂ
˚
3
˚
CgA is the centroid calculated through the C atoms of benzenesulfonamide
ring A.
˚
˚
a = 11.8650 (3) A
b = 12.2420 (3) A
˚
c = 14.7287 (3) A
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
ꢁ = 68.075 (1)ꢂ
ꢂ = 81.665 (1)ꢂ
N1—H1ꢀ ꢀ ꢀO3i
0.91 (3)
0.93
0.96
0.93
0.93
2.08 (3)
2.34
3.04
2.65
2.68
2.987 (2)
3.228 (2)
3.816 (3)
3.269 (2)
3.285 (2)
175 (3)
160
138
125
124
C9—H9ꢀ ꢀ ꢀO1ii
C23—H23Aꢀ ꢀ ꢀCgAiii
C2—H2ꢀ ꢀ ꢀO4iv
C3—H3ꢀ ꢀ ꢀO4iv
Data collection
Nonius KappaCCD area-detector
diffractometer
22723 measured reflections
8378 independent reflections
5268 reflections with I > 2ꢅ(I)
Rint = 0.039
1
1
1
2
1
2
Symmetry codes: (i) x; ꢁy þ ; z ꢁ ; (ii) x; ꢁy þ ; z þ ; (iii) ꢁx þ 1; ꢁy; ꢁz þ 2; (iv)
2
2
1
2
3
2
ꢁx þ 1; y þ ; ꢁz þ .
ꢃ
Acta Cryst. (2013). C69, 267–272
Castro et al.
C22H19NO4S and C23H21NO4S 271

organic compounds
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272 Castro et al. C22H19NO4S and C23H21NO4S
Acta Cryst. (2013). C69, 267–272

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 267-272 [doi:10.1107/S0108270113002291]
An additional methylene group driving the conformation and assembly of two
arylsulfonamide para-alkoxychalcone hybrids
Mirian R. C. de Castro, Angelo Q. Aragão, Hamilton B. Napolitano, Caridad Noda-Perez and
Felipe T. Martins
(I) N-{4-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide
Crystal data
C22H19NO4S
Z = 4
Mr = 393.44
Triclinic, P1
F(000) = 824
Dx = 1.341 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 6621 reflections
θ = 2.4–22.8°
Hall symbol: -P1
a = 11.8650 (3) Å
b = 12.2420 (3) Å
c = 14.7287 (3) Å
α = 68.075 (1)°
β = 81.665 (1)°
γ = 80.437 (1)°
V = 1948.99 (8) Å3
µ = 0.19 mm−1
T = 298 K
Prism, yellow
0.28 × 0.15 × 0.08 mm
Data collection
Nonius KappaCCD area-detector
diffractometer
5268 reflections with I > 2σ(I)
Rint = 0.039
Graphite monochromator
Detector resolution: 9 pixels mm-1
CCD scans
22723 measured reflections
8378 independent reflections
θmax = 26.9°, θmin = 1.5°
h = −15→14
k = −14→15
l = −18→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.054
wR(F2) = 0.152
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.01
8378 reflections
512 parameters
0 restraints
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0555P)2 + 0.7349P]
where P = (Fo2 + 2Fc2)/3
Primary atom site location: structure-invariant
direct methods
(Δ/σ)max < 0.001
Δρmax = 0.24 e Å−3
Δρmin = −0.26 e Å−3
Acta Cryst. (2013). C69, 267-272
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supplementary materials
Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles;
correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1A
0.17904 (5)
0.36203 (6)
0.52135 (14)
0.25459 (15)
0.41481 (16)
0.24599 (18)
0.21279 (16)
0.05999 (14)
−0.05735 (17)
0.31611 (18)
0.4446 (2)
0.2188 (2)
0.2373 (2)
0.3123
0.79421 (6)
0.34197 (7)
0.35404 (17)
0.40900 (18)
0.3584 (2)
0.70776 (19)
0.73965 (17)
0.81540 (18)
0.4984 (2)
0.7139 (2)
0.3629 (2)
0.4344 (2)
0.4527 (2)
0.4498
−0.03767 (5)
0.55077 (5)
0.02461 (12)
0.52211 (13)
0.62501 (13)
0.05831 (16)
−0.10896 (14)
−0.00745 (14)
−0.28263 (16)
0.47768 (16)
0.36402 (17)
−0.11850 (18)
−0.21827 (18)
−0.2471
0.0646 (2)
0.0694 (2)
0.0722 (5)
0.0816 (6)
0.0854 (6)
0.0661 (6)
0.0795 (5)
0.0799 (5)
0.0947 (6)
0.1072 (8)
0.0602 (6)
0.0582 (6)
0.0635 (6)
0.076*
S1B
O3B
O2B
O1B
N1A
O1A
O2A
O4B
O3A
C7B
C16B
C17B
H17B
N1B
0.45667 (19)
0.3353 (2)
0.2642
0.3690 (2)
0.3661 (3)
0.3687
0.45617 (16)
0.23888 (19)
0.218
0.0751 (7)
0.0766 (8)
0.092*
C11B
H11B
C7A
0.2392 (2)
0.1051 (2)
0.0897
0.7274 (2)
0.4378 (2)
0.425
0.14772 (18)
−0.0777 (2)
−0.011
0.0602 (6)
0.0706 (7)
0.085*
C21B
H21B
C12B
H12B
C15B
H15B
C18B
H18B
C8B
0.3402 (2)
0.2734
0.3639 (3)
0.3631
0.3323 (2)
0.0850 (9)
0.102*
0.3741
0.3171 (2)
0.3879
0.4082 (2)
0.3988
−0.06264 (18)
−0.0971
0.0601 (6)
0.072*
0.1485 (2)
0.1635
0.4750 (2)
0.4873
−0.27569 (19)
−0.3423
0.0689 (7)
0.083*
0.5424 (2)
0.6135
0.3574 (2)
0.3533
0.30272 (18)
0.3242
0.0647 (6)
0.078*
H8B
C13B
C9B
0.4309 (2)
0.5370 (2)
0.6046
0.3695 (2)
0.3578 (2)
0.3535
0.07319 (17)
0.21029 (18)
0.1703
0.0565 (6)
0.0630 (6)
0.076*
H9B
C1A
0.2357 (2)
0.43259 (19)
−0.2762 (2)
0.3211 (2)
0.253
0.9295 (2)
0.3645 (2)
0.9286 (3)
0.3955 (2)
0.4032
−0.07958 (17)
0.17527 (17)
0.78912 (19)
0.03014 (18)
0.0687
0.0630 (6)
0.0546 (5)
0.1242 (9)
0.0618 (6)
0.074*
C10B
O4A
C14B
H14B
C13A
0.2292 (3)
0.7493 (3)
0.4336 (2)
0.0765 (8)
Acta Cryst. (2013). C69, 267-272
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supplementary materials
C10A
C16A
C6A
0.2314 (2)
0.0107 (3)
0.1643 (3)
0.0865
0.7464 (2)
0.8190 (2)
1.0319 (3)
1.0294
0.3332 (2)
0.62976 (19)
−0.0857 (2)
−0.0652
0.0689 (7)
0.0719 (7)
0.0810 (8)
0.097*
H6A
C11A
H11A
C21A
H21A
C15A
H15A
C1B
0.1398 (2)
0.0735
0.7892 (3)
0.826
0.2768 (2)
0.3007
0.0840 (9)
0.101*
−0.0923 (3)
−0.0983
0.1104 (3)
0.1746
0.8748 (3)
0.889
0.5895 (2)
0.5237
0.0926 (9)
0.111*
0.7821 (3)
0.7466
0.5737 (2)
0.6083
0.0760 (8)
0.091*
0.3442 (3)
0.2092 (3)
0.1613
0.1908 (3)
1.1388 (3)
1.2089
0.58692 (18)
−0.1228 (3)
−0.1283
0.0731 (7)
0.0997 (10)
0.12*
C5A
H5A
C19B
C12A
H12A
C8A
0.0369 (2)
0.1428 (2)
0.0786
0.4788 (2)
0.7795 (3)
0.8086
−0.2336 (2)
0.1863 (2)
0.1509
0.0690 (7)
0.0888 (9)
0.107*
0.3326 (2)
0.3995
0.6855 (3)
0.6507
0.2022 (2)
0.1773
0.0859 (9)
0.103*
H8A
C17A
H17A
C18A
H18A
C19A
C2A
0.0138 (3)
0.0808
0.8004 (3)
0.7627
0.7279 (2)
0.7575
0.0867 (9)
0.104*
−0.0784 (3)
−0.0728
−0.1785 (3)
0.3500 (3)
0.398
0.8354 (3)
0.8222
0.7838 (2)
0.8495
0.0889 (9)
0.107*
0.8901 (3)
0.9334 (3)
0.864
0.7413 (2)
−0.1101 (3)
−0.1067
0.0907 (9)
0.0908 (9)
0.109*
H2A
C14A
H14A
C22B
H22A
H22B
H22C
C20B
H20B
C4A
0.1232 (3)
0.0615
0.7920 (3)
0.8277
0.4799 (2)
0.4421
0.0790 (8)
0.095*
−0.0381 (3)
−0.1104
0.0024
0.5009 (3)
0.5143
−0.3814 (3)
−0.408
0.1051 (11)
0.158*
0.4265
−0.382
0.158*
0.0067
0.5638
−0.4203
0.158*
0.0157 (2)
−0.0594
0.3235 (4)
0.3538
0.4595 (3)
0.4612
−0.1338 (2)
−0.1051
0.0755 (8)
0.091*
1.1419 (3)
1.2138
−0.1512 (2)
−0.1744
0.0980 (10)
0.118*
H4A
C4B
0.3128 (6)
0.302
−0.0426 (4)
−0.1222
1.0399 (3)
1.0425
0.6518 (3)
0.6734
0.1318 (15)
0.158*
H4B
C3A
0.3934 (3)
0.4712
−0.1455 (3)
−0.1659
0.1055 (11)
0.127*
H3A
C9A
0.3279 (3)
0.3919
0.6945 (3)
0.6646
0.2930 (2)
0.3286
0.0925 (10)
0.111*
H9A
C20A
H20A
C6B
−0.1851 (3)
−0.2528
0.2361 (3)
0.1729
0.9093 (3)
0.9459
0.6440 (3)
0.6151
0.1008 (10)
0.121*
0.1570 (4)
0.2142
0.6157 (2)
0.6121
0.0991 (10)
0.119*
H6B
C5B
0.2204 (4)
0.1474
0.0392 (5)
0.0161
0.6498 (3)
0.6711
0.1245 (15)
0.149*
H5B
C3B
0.4211 (5)
0.4834
−0.0121 (4)
−0.0698
0.6233 (4)
0.6251
0.1494 (19)
0.179*
H3B
Acta Cryst. (2013). C69, 267-272
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supplementary materials
C2B
0.4373 (4)
0.5106
0.1087 (4)
0.1316
0.5910 (3)
0.5727
0.1212 (13)
0.145*
H2B
C22A
H22D
H22E
H22F
H1B
−0.2706 (4)
−0.344
0.9231 (4)
0.953
0.8865 (3)
0.9108
0.1404 (16)
0.211*
−0.2136
−0.2505
0.521 (4)
0.308 (4)
0.9704
0.8865
0.211*
0.8423
0.928
0.211*
0.361 (4)
0.679 (4)
0.471 (3)
0.040 (3)
0.169*
H1A
0.169*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
S1A
0.0553 (4)
0.0604 (4)
0.0583 (10)
0.0657 (11)
0.0745 (12)
0.0606 (13)
0.0751 (12)
0.0517 (10)
0.0730 (13)
0.0757 (14)
0.0583 (14)
0.0558 (14)
0.0593 (15)
0.0599 (13)
0.0513 (14)
0.0553 (14)
0.0653 (16)
0.0521 (15)
0.0570 (14)
0.0739 (17)
0.0514 (14)
0.0575 (14)
0.0479 (13)
0.0626 (15)
0.0537 (13)
0.126 (2)
0.0775 (4)
0.1005 (5)
0.0951 (13)
0.1114 (15)
0.1324 (17)
0.0687 (13)
0.0964 (14)
0.1042 (15)
0.1227 (17)
0.164 (2)
0.0618 (4)
0.0065 (3)
−0.0138 (3)
−0.0090 (3)
−0.0088 (8)
−0.0165 (9)
−0.0132 (9)
−0.0115 (10)
−0.0203 (10)
−0.0121 (9)
−0.0369 (11)
−0.0336 (12)
−0.0085 (11)
−0.0119 (11)
−0.0062 (12)
−0.0065 (10)
−0.0116 (12)
−0.0114 (12)
−0.0069 (13)
−0.0034 (12)
−0.0082 (11)
−0.0158 (13)
−0.0112 (11)
−0.0095 (11)
−0.0055 (11)
−0.0095 (11)
−0.0097 (10)
−0.0049 (16)
−0.0090 (11)
−0.0217 (15)
−0.0155 (13)
−0.0189 (14)
−0.0063 (15)
−0.0137 (14)
−0.0263 (17)
−0.0256 (15)
−0.0095 (13)
−0.004 (2)
−0.0289 (3)
−0.0352 (4)
−0.0392 (10)
−0.0414 (11)
−0.0524 (12)
−0.0211 (11)
−0.0484 (11)
−0.0340 (11)
−0.0536 (14)
−0.0555 (15)
−0.0204 (12)
−0.0290 (12)
−0.0305 (13)
−0.0374 (13)
−0.0412 (16)
−0.0159 (12)
−0.0411 (15)
−0.0483 (18)
−0.0294 (12)
−0.0292 (13)
−0.0246 (13)
−0.0230 (11)
−0.0268 (13)
−0.0226 (12)
−0.0201 (11)
−0.0699 (17)
−0.0327 (13)
−0.0258 (15)
−0.0251 (14)
−0.0223 (14)
−0.0275 (16)
−0.0364 (17)
−0.0391 (18)
−0.0221 (15)
−0.0269 (14)
−0.0243 (18)
−0.0371 (14)
−0.0364 (18)
S1B
0.0534 (4)
−0.0051 (4)
0.0153 (9)
O3B
0.0643 (11)
0.0710 (12)
0.0662 (11)
0.0635 (13)
0.0790 (12)
0.0810 (12)
0.1015 (16)
0.0926 (15)
0.0510 (13)
0.0597 (14)
0.0599 (15)
0.0549 (12)
0.0639 (16)
0.0621 (15)
0.0630 (16)
0.0620 (16)
0.0591 (14)
0.0601 (15)
0.0603 (15)
0.0564 (14)
0.0600 (15)
0.0516 (13)
0.0531 (13)
0.1018 (18)
0.0590 (15)
0.0734 (18)
0.0700 (17)
0.0593 (15)
0.0747 (19)
0.0673 (17)
0.0650 (18)
0.0682 (17)
0.0503 (14)
0.092 (2)
O2B
0.0104 (10)
−0.0121 (11)
0.0062 (11)
0.0091 (10)
0.0051 (10)
0.0099 (12)
0.0032 (14)
−0.0083 (12)
0.0014 (11)
−0.0029 (12)
−0.0170 (13)
−0.0070 (15)
−0.0011 (11)
0.0027 (14)
−0.0130 (16)
0.0024 (12)
−0.0018 (14)
−0.0081 (12)
0.0043 (11)
−0.0009 (12)
0.0099 (13)
0.0010 (11)
−0.0054 (18)
0.0043 (12)
−0.0095 (15)
−0.0040 (13)
−0.0168 (15)
0.0129 (16)
0.0186 (16)
−0.002 (2)
O1B
N1A
O1A
O2A
O4B
O3A
C7B
0.0712 (16)
0.0639 (15)
0.0751 (17)
0.1186 (19)
0.122 (2)
C16B
C17B
N1B
C11B
C7A
0.0580 (14)
0.0911 (19)
0.150 (3)
C21B
C12B
C15B
C18B
C8B
0.0673 (15)
0.0772 (17)
0.0833 (18)
0.0554 (13)
0.0803 (17)
0.0704 (16)
0.0562 (13)
0.159 (2)
C13B
C9B
C1A
C10B
O4A
C14B
C13A
C10A
C16A
C6A
0.0543 (14)
0.0696 (18)
0.0612 (16)
0.0840 (19)
0.0802 (19)
0.0661 (17)
0.100 (2)
0.0764 (16)
0.089 (2)
0.0761 (17)
0.0770 (18)
0.079 (2)
C11A
C21A
C15A
C1B
0.114 (2)
0.120 (3)
0.0801 (19)
0.0768 (18)
0.118 (3)
0.0826 (19)
0.093 (2)
−0.0127 (15)
−0.0054 (16)
0.012 (2)
C5A
0.074 (2)
C19B
C12A
0.0652 (16)
0.0637 (17)
0.0740 (17)
0.127 (3)
0.0773 (18)
0.0692 (18)
0.0078 (13)
0.0210 (17)
−0.0270 (14)
−0.0213 (14)
Acta Cryst. (2013). C69, 267-272
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supplementary materials
C8A
0.0595 (16)
0.097 (2)
0.108 (3)
0.103 (3)
0.0691 (19)
0.0752 (19)
0.099 (2)
0.0546 (15)
0.121 (3)
0.179 (5)
0.084 (2)
0.0646 (18)
0.089 (2)
0.089 (2)
0.132 (4)
0.167 (5)
0.111 (3)
0.186 (5)
0.114 (2)
0.102 (2)
0.108 (2)
0.102 (2)
0.074 (2)
0.098 (2)
0.136 (3)
0.101 (2)
0.078 (2)
0.113 (3)
0.092 (2)
0.129 (3)
0.133 (3)
0.116 (3)
0.127 (4)
0.107 (4)
0.110 (3)
0.159 (4)
0.092 (2)
0.0659 (18)
0.0611 (17)
0.078 (2)
0.116 (3)
0.0655 (17)
0.099 (2)
0.0814 (19)
0.085 (2)
0.105 (3)
0.124 (3)
0.094 (2)
0.087 (2)
0.090 (2)
0.109 (3)
0.137 (4)
0.117 (3)
0.090 (3)
0.0184 (16)
−0.0175 (18)
−0.028 (2)
−0.021 (2)
0.0040 (16)
−0.0035 (16)
0.002 (2)
−0.0214 (15)
−0.0259 (17)
−0.0124 (18)
−0.0070 (19)
−0.0033 (17)
−0.0215 (14)
−0.050 (2)
−0.0536 (19)
−0.0260 (17)
−0.0346 (17)
−0.0424 (19)
−0.0263 (18)
−0.0293 (16)
−0.055 (2)
C17A
C18A
C19A
C2A
C14A
C22B
C20B
C4A
0.0029 (14)
−0.014 (2)
−0.033 (4)
−0.010 (2)
0.0162 (18)
0.006 (2)
−0.0103 (13)
−0.002 (2)
−0.0483 (17)
−0.0197 (17)
−0.032 (3)
C4B
−0.019 (3)
C3A
0.003 (2)
−0.025 (2)
C9A
−0.0349 (16)
−0.0235 (18)
−0.0312 (18)
−0.045 (3)
0.030 (3)
−0.053 (2)
C20A
C6B
−0.050 (2)
−0.019 (2)
−0.046 (3)
0.012 (3)
−0.024 (2)
C5B
−0.011 (3)
C3B
−0.029 (3)
C2B
0.000 (2)
0.026 (2)
−0.030 (2)
C22A
−0.029 (3)
0.015 (3)
−0.067 (3)
Geometric parameters (Å, º)
S1A—O1A
S1A—O2A
S1A—N1A
S1A—C1A
S1B—O2B
1.4220 (18)
C10A—C9A
1.381 (4)
1.4293 (17)
1.637 (2)
1.749 (3)
1.4235 (19)
1.4258 (18)
1.624 (2)
1.764 (3)
1.229 (3)
1.414 (3)
0.82 (4)
C16A—C17A
C16A—C21A
C16A—C15A
C6A—C5A
1.381 (4)
1.393 (4)
1.451 (4)
1.382 (4)
0.93
S1B—O1B
C6A—H6A
S1B—N1B
C11A—C12A
C11A—H11A
C21A—C20A
C21A—H21A
C15A—C14A
C15A—H15A
C1B—C2B
1.377 (4)
0.93
S1B—C1B
O3B—C13B
N1A—C7A
N1A—H1A
O4B—C19B
O4B—C22B
O3A—C13A
C7B—C8B
C7B—C12B
C7B—N1B
C16B—C17B
C16B—C21B
C16B—C15B
C17B—C18B
C17B—H17B
N1B—H1B
C11B—C12B
C11B—C10B
C11B—H11B
C7A—C12A
C7A—C8A
C21B—C20B
1.371 (4)
0.93
1.330 (4)
0.93
1.359 (3)
1.428 (4)
1.228 (3)
1.372 (3)
1.382 (3)
1.416 (3)
1.391 (3)
1.396 (3)
1.447 (3)
1.375 (3)
0.93
1.356 (4)
1.373 (4)
1.362 (5)
0.93
C1B—C6B
C5A—C4A
C5A—H5A
C19B—C20B
C12A—H12A
C8A—C9A
1.389 (4)
0.93
1.375 (4)
0.93
C8A—H8A
C17A—C18A
C17A—H17A
C18A—C19A
C18A—H18A
C19A—C20A
C2A—C3A
1.381 (4)
0.93
0.80 (4)
1.374 (4)
0.93
1.376 (4)
1.380 (3)
0.93
1.374 (4)
1.369 (4)
0.93
1.371 (4)
1.377 (3)
1.370 (4)
C2A—H2A
C14A—H14A
C22B—H22A
0.93
0.96
Acta Cryst. (2013). C69, 267-272
sup-5

supplementary materials
C21B—H21B
C12B—H12B
C15B—C14B
C15B—H15B
C18B—C19B
C18B—H18B
C8B—C9B
0.93
C22B—H22B
C22B—H22C
C20B—H20B
C4A—C3A
C4A—H4A
C4B—C5B
C4B—C3B
C4B—H4B
C3A—H3A
C9A—H9A
C20A—H20A
C6B—C5B
C6B—H6B
C5B—H5B
C3B—C2B
C3B—H3B
C2B—H2B
C22A—H22D
C22A—H22E
C22A—H22F
0.96
0.93
0.96
1.323 (3)
0.93
0.93
1.361 (5)
0.93
1.379 (4)
0.93
1.351 (6)
1.362 (6)
0.93
1.370 (3)
0.93
C8B—H8B
C13B—C14B
C13B—C10B
C9B—C10B
C9B—H9B
1.467 (3)
1.485 (3)
1.389 (3)
0.93
0.93
0.93
0.93
1.374 (5)
0.93
C1A—C2A
1.368 (4)
1.372 (4)
1.375 (4)
1.421 (4)
0.93
C1A—C6A
0.93
O4A—C19A
O4A—C22A
C14B—H14B
C13A—C14A
C13A—C10A
C10A—C11A
1.411 (6)
0.93
0.93
1.456 (4)
1.489 (4)
1.376 (4)
0.96
0.96
0.96
O1A—S1A—O2A
O1A—S1A—N1A
O2A—S1A—N1A
O1A—S1A—C1A
O2A—S1A—C1A
N1A—S1A—C1A
O2B—S1B—O1B
O2B—S1B—N1B
O1B—S1B—N1B
O2B—S1B—C1B
O1B—S1B—C1B
N1B—S1B—C1B
C7A—N1A—S1A
C7A—N1A—H1A
S1A—N1A—H1A
C19B—O4B—C22B
C8B—C7B—C12B
C8B—C7B—N1B
C12B—C7B—N1B
C17B—C16B—C21B
C17B—C16B—C15B
C21B—C16B—C15B
C18B—C17B—C16B
C18B—C17B—H17B
C16B—C17B—H17B
C7B—N1B—S1B
C7B—N1B—H1B
S1B—N1B—H1B
119.61 (12)
104.80 (11)
109.01 (11)
108.43 (12)
107.90 (12)
106.36 (12)
119.17 (12)
109.69 (12)
105.01 (12)
107.17 (13)
109.08 (13)
106.03 (13)
125.13 (17)
116 (3)
C12A—C11A—H11A
C20A—C21A—C16A
C20A—C21A—H21A
C16A—C21A—H21A
C14A—C15A—C16A
C14A—C15A—H15A
C16A—C15A—H15A
C2B—C1B—C6B
118.8
121.9 (3)
119
119
129.1 (3)
115.4
115.4
120.6 (3)
120.0 (3)
119.3 (3)
120.2 (3)
119.9
C2B—C1B—S1B
C6B—C1B—S1B
C4A—C5A—C6A
C4A—C5A—H5A
C6A—C5A—H5A
119.9
O4B—C19B—C18B
O4B—C19B—C20B
C18B—C19B—C20B
C7A—C12A—C11A
C7A—C12A—H12A
C11A—C12A—H12A
C9A—C8A—C7A
124.5 (3)
115.7 (3)
119.7 (2)
120.8 (3)
119.6
110 (3)
116.9 (2)
118.7 (2)
117.6 (2)
123.7 (2)
117.1 (2)
118.8 (2)
124.0 (2)
122.3 (2)
118.9
119.6
120.6 (3)
119.7
C9A—C8A—H8A
C7A—C8A—H8A
119.7
C18A—C17A—C16A
C18A—C17A—H17A
C16A—C17A—H17A
C19A—C18A—C17A
C19A—C18A—H18A
C17A—C18A—H18A
122.8 (3)
118.6
118.9
118.6
126.34 (18)
117 (3)
119.2 (3)
120.4
112 (3)
120.4
Acta Cryst. (2013). C69, 267-272
sup-6

supplementary materials
C12B—C11B—C10B
C12B—C11B—H11B
C10B—C11B—H11B
C12A—C7A—C8A
C12A—C7A—N1A
C8A—C7A—N1A
121.9 (2)
119
C20A—C19A—C18A
119.6 (3)
115.6 (3)
124.8 (3)
119.7 (3)
120.1
C20A—C19A—O4A
C18A—C19A—O4A
C1A—C2A—C3A
C1A—C2A—H2A
C3A—C2A—H2A
C15A—C14A—C13A
C15A—C14A—H14A
C13A—C14A—H14A
O4B—C22B—H22A
O4B—C22B—H22B
H22A—C22B—H22B
O4B—C22B—H22C
H22A—C22B—H22C
H22B—C22B—H22C
C21B—C20B—C19B
C21B—C20B—H20B
C19B—C20B—H20B
C3A—C4A—C5A
C3A—C4A—H4A
C5A—C4A—H4A
C5B—C4B—C3B
C5B—C4B—H4B
C3B—C4B—H4B
C4A—C3A—C2A
C4A—C3A—H3A
C2A—C3A—H3A
C8A—C9A—C10A
C8A—C9A—H9A
C10A—C9A—H9A
C21A—C20A—C19A
C21A—C20A—H20A
C19A—C20A—H20A
C1B—C6B—C5B
C1B—C6B—H6B
C5B—C6B—H6B
C4B—C5B—C6B
C4B—C5B—H5B
C6B—C5B—H5B
C4B—C3B—C2B
C4B—C3B—H3B
C2B—C3B—H3B
C1B—C2B—C3B
C1B—C2B—H2B
C3B—C2B—H2B
O4A—C22A—H22D
O4A—C22A—H22E
H22D—C22A—H22E
O4A—C22A—H22F
119
117.9 (3)
123.8 (2)
118.1 (2)
121.3 (2)
119.3
120.1
C20B—C21B—C16B
C20B—C21B—H21B
C16B—C21B—H21B
C11B—C12B—C7B
C11B—C12B—H12B
C7B—C12B—H12B
C14B—C15B—C16B
C14B—C15B—H15B
C16B—C15B—H15B
C17B—C18B—C19B
C17B—C18B—H18B
C19B—C18B—H18B
C9B—C8B—C7B
122.9 (3)
118.5
119.3
118.5
120.0 (2)
120
109.5
109.5
120
109.5
129.6 (2)
115.2
109.5
109.5
115.2
109.5
119.4 (2)
120.3
120.2 (2)
119.9
120.3
119.9
121.0 (2)
119.5
120.1 (3)
120
C9B—C8B—H8B
C7B—C8B—H8B
119.5
120
O3B—C13B—C14B
O3B—C13B—C10B
C14B—C13B—C10B
C8B—C9B—C10B
C8B—C9B—H9B
120.4 (2)
120.0 (2)
119.7 (2)
121.2 (2)
119.4
122.0 (5)
119
119
120.4 (3)
119.8
C10B—C9B—H9B
C2A—C1A—C6A
119.4
119.8
120.3 (3)
119.9 (2)
119.8 (2)
117.1 (2)
123.7 (2)
119.2 (2)
118.1 (3)
121.2 (2)
119.4
122.3 (3)
118.9
C2A—C1A—S1A
C6A—C1A—S1A
118.9
C11B—C10B—C9B
C11B—C10B—C13B
C9B—C10B—C13B
C19A—O4A—C22A
C15B—C14B—C13B
C15B—C14B—H14B
C13B—C14B—H14B
O3A—C13A—C14A
O3A—C13A—C10A
C14A—C13A—C10A
C11A—C10A—C9A
C11A—C10A—C13A
C9A—C10A—C13A
C17A—C16A—C21A
C17A—C16A—C15A
C21A—C16A—C15A
C1A—C6A—C5A
120.3 (3)
119.9
119.9
120.5 (4)
119.7
119.7
119.4
119.0 (4)
120.5
120.3 (3)
119.9 (3)
119.7 (2)
116.1 (3)
123.9 (3)
120.0 (3)
116.1 (3)
120.7 (3)
123.2 (3)
119.2 (3)
120.4
120.5
118.9 (4)
120.6
120.6
119.0 (4)
120.5
120.5
109.5
109.5
C1A—C6A—H6A
109.5
C5A—C6A—H6A
120.4
109.5
Acta Cryst. (2013). C69, 267-272
sup-7

supplementary materials
C10A—C11A—C12A
C10A—C11A—H11A
122.3 (3)
118.8
H22D—C22A—H22F
109.5
109.5
H22E—C22A—H22F
O1A—S1A—N1A—C7A
O2A—S1A—N1A—C7A
C1A—S1A—N1A—C7A
C21B—C16B—C17B—C18B
C15B—C16B—C17B—C18B
C8B—C7B—N1B—S1B
179.4 (2)
−51.5 (2)
64.6 (2)
C17A—C16A—C15A—C14A
C21A—C16A—C15A—C14A
O2B—S1B—C1B—C2B
179.6 (3)
−0.7 (5)
161.1 (3)
−68.6 (3)
44.0 (3)
−22.3 (3)
108.0 (2)
−139.4 (2)
−1.1 (5)
7.7 (4)
0.9 (4)
O1B—S1B—C1B—C2B
178.3 (2)
−162.9 (2)
18.1 (4)
N1B—S1B—C1B—C2B
O2B—S1B—C1B—C6B
C12B—C7B—N1B—S1B
O2B—S1B—N1B—C7B
O1B—S1B—N1B—C7B
C1B—S1B—N1B—C7B
O1B—S1B—C1B—C6B
−51.6 (3)
179.2 (2)
63.8 (3)
N1B—S1B—C1B—C6B
C1A—C6A—C5A—C4A
C22B—O4B—C19B—C18B
C22B—O4B—C19B—C20B
C17B—C18B—C19B—O4B
C17B—C18B—C19B—C20B
C8A—C7A—C12A—C11A
N1A—C7A—C12A—C11A
C10A—C11A—C12A—C7A
C12A—C7A—C8A—C9A
N1A—C7A—C8A—C9A
C21A—C16A—C17A—C18A
C15A—C16A—C17A—C18A
C16A—C17A—C18A—C19A
C17A—C18A—C19A—C20A
C17A—C18A—C19A—O4A
C22A—O4A—C19A—C20A
C22A—O4A—C19A—C18A
C6A—C1A—C2A—C3A
S1A—C1A—C2A—C3A
C16A—C15A—C14A—C13A
O3A—C13A—C14A—C15A
C10A—C13A—C14A—C15A
C16B—C21B—C20B—C19B
O4B—C19B—C20B—C21B
C18B—C19B—C20B—C21B
C6A—C5A—C4A—C3A
C5A—C4A—C3A—C2A
C1A—C2A—C3A—C4A
C7A—C8A—C9A—C10A
C11A—C10A—C9A—C8A
C13A—C10A—C9A—C8A
C16A—C21A—C20A—C19A
C18A—C19A—C20A—C21A
O4A—C19A—C20A—C21A
C2B—C1B—C6B—C5B
S1A—N1A—C7A—C12A
S1A—N1A—C7A—C8A
C17B—C16B—C21B—C20B
C15B—C16B—C21B—C20B
C10B—C11B—C12B—C7B
C8B—C7B—C12B—C11B
N1B—C7B—C12B—C11B
C17B—C16B—C15B—C14B
C21B—C16B—C15B—C14B
C16B—C17B—C18B—C19B
C12B—C7B—C8B—C9B
N1B—C7B—C8B—C9B
C7B—C8B—C9B—C10B
O1A—S1A—C1A—C2A
O2A—S1A—C1A—C2A
N1A—S1A—C1A—C2A
O1A—S1A—C1A—C6A
O2A—S1A—C1A—C6A
N1A—S1A—C1A—C6A
C12B—C11B—C10B—C9B
C12B—C11B—C10B—C13B
C8B—C9B—C10B—C11B
C8B—C9B—C10B—C13B
O3B—C13B—C10B—C11B
C14B—C13B—C10B—C11B
O3B—C13B—C10B—C9B
C14B—C13B—C10B—C9B
C16B—C15B—C14B—C13B
O3B—C13B—C14B—C15B
C10B—C13B—C14B—C15B
O3A—C13A—C10A—C11A
C14A—C13A—C10A—C11A
O3A—C13A—C10A—C9A
C14A—C13A—C10A—C9A
C2A—C1A—C6A—C5A
S1A—C1A—C6A—C5A
33.5 (4)
−150.6 (2)
−0.7 (4)
−177.9 (3)
1.5 (5)
−170.9 (3)
−179.0 (3)
−0.4 (4)
−0.1 (5)
175.9 (3)
−0.9 (5)
0.8 (5)
−3.6 (5)
175.4 (3)
175.0 (3)
−7.9 (4)
−0.4 (4)
2.7 (4)
−175.3 (3)
−0.7 (5)
179.1 (3)
0.7 (5)
−176.4 (2)
0.4 (4)
−0.2 (5)
179.7 (3)
−173.2 (3)
6.9 (5)
−51.2 (3)
177.8 (2)
61.0 (3)
0.9 (5)
125.9 (2)
−5.0 (2)
−121.8 (2)
1.5 (4)
178.1 (3)
−179.4 (3)
−8.1 (5)
170.6 (3)
−0.1 (4)
179.4 (3)
0.7 (4)
−178.6 (3)
−2.5 (4)
177.6 (2)
−171.6 (2)
9.8 (4)
1.7 (5)
−0.9 (6)
−0.4 (6)
−0.7 (5)
−0.2 (5)
177.4 (3)
0.4 (6)
8.3 (3)
−170.3 (2)
−179.5 (2)
−3.1 (4)
175.5 (2)
−177.0 (3)
4.3 (4)
−0.3 (5)
179.7 (3)
0.5 (5)
5.6 (5)
−173.1 (3)
−0.2 (4)
−177.4 (2)
S1B—C1B—C6B—C5B
−176.1 (3)
1.6 (7)
C3B—C4B—C5B—C6B
C1B—C6B—C5B—C4B
−1.9 (6)
Acta Cryst. (2013). C69, 267-272
sup-8

supplementary materials
C9A—C10A—C11A—C12A
C13A—C10A—C11A—C12A
C17A—C16A—C21A—C20A
C15A—C16A—C21A—C20A
1.0 (5)
C5B—C4B—C3B—C2B
0.2 (8)
−176.5 (3)
0.1 (5)
C6B—C1B—C2B—C3B
S1B—C1B—C2B—C3B
C4B—C3B—C2B—C1B
1.3 (6)
177.9 (3)
−1.6 (7)
−179.6 (3)
Hydrogen-bond geometry (Å, º)
CgA is the centroid calculated through the ring A C atoms of molecule A.
D—H···A
D—H
H···A
D···A
D—H···A
N1A—H1A···O3Bi
N1B—H1B···O3Aii
C9A—H9A···O1Bii
C9B—H9B···O1Ai
C22B—H22A···O2Biii
C22A—H22D···CgAiv
C22A—H22E···CgAiv
0.81 (5)
0.81 (5)
0.93
2.16 (5)
2.11 (5)
2.43
2.950 (3)
2.892 (3)
3.320 (4)
3.366 (3)
3.317 (4)
3.580 (4)
3.580 (4)
166 (5)
163 (5)
160
0.93
2.49
157
0.96
2.40
160
0.96
3.28
101
0.96
3.33
97
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z+1.
(II) N-{4-[(E)-3-(4-Ethoxyphenyl)prop-2-enoyl]phenyl}benzenesulfonamide
Crystal data
C23H21NO4S
Mr = 407.47
F(000) = 856
Dx = 1.279 Mg m−3
Monoclinic, P21/c
Hall symbol: -P2ybc
a = 8.4506 (2) Å
b = 20.1587 (6) Å
c = 14.2120 (3) Å
β = 119.098 (2)°
V = 2115.49 (9) Å3
Z = 4
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4266 reflections
θ = 2.9–26.4°
µ = 0.18 mm−1
T = 298 K
Prism, yellow
0.25 × 0.20 × 0.15 mm
Data collection
Nonius KappaCCD area-detector
diffractometer
3072 reflections with I > 2σ(I)
Rint = 0.036
Graphite monochromator
Detector resolution: 9 pixels mm-1
CCD scans
7397 measured reflections
4185 independent reflections
θmax = 26.4°, θmin = 3.2°
h = −10→10
k = −23→25
l = −17→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.049
wR(F2) = 0.143
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.05
4185 reflections
265 parameters
0 restraints
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0875P)2 + 0.0704P]
where P = (Fo2 + 2Fc2)/3
Primary atom site location: structure-invariant
direct methods
(Δ/σ)max < 0.001
Δρmax = 0.17 e Å−3
Δρmin = −0.27 e Å−3
Acta Cryst. (2013). C69, 267-272
sup-9

supplementary materials
Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles;
correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
0.65679 (6)
0.76455 (19)
0.69037 (17)
0.70805 (17)
0.74263 (19)
0.4242 (2)
0.7578 (2)
0.3341 (2)
0.395
0.11848 (2)
0.16732 (8)
0.14641 (6)
0.05154 (6)
−0.16891 (7)
0.12732 (8)
0.15805 (8)
0.07890 (9)
0.0414
0.42888 (3)
0.53375 (12)
0.34799 (10)
0.46160 (10)
1.27909 (10)
0.38628 (13)
0.63097 (14)
0.41042 (16)
0.4491
0.05750 (19)
0.0606 (4)
0.0709 (4)
0.0678 (3)
0.0753 (4)
0.0546 (4)
0.0565 (4)
0.0677 (5)
0.081*
N1
O1
O2
O4
C1
C7
C6
H6
C13
C21
H21
C10
C19
O3
0.7446 (3)
0.7434 (3)
0.7525
0.13877 (10)
−0.05952 (10)
−0.0638
0.92840 (15)
1.07881 (15)
1.0165
0.0660 (5)
0.0723 (5)
0.087*
0.7513 (2)
0.7346 (2)
0.7338 (2)
0.7544 (3)
0.6452
0.14366 (9)
−0.11021 (9)
0.18963 (7)
−0.16605 (10)
−0.1466
0.82493 (14)
1.22857 (14)
0.97259 (11)
1.38310 (15)
1.3774
0.0601 (4)
0.0640 (5)
0.0833 (4)
0.0747 (5)
0.09*
C22
H22A
H22B
C15
H15
C9
0.8569
−0.139
1.4315
0.09*
0.7296 (3)
0.7149
0.06480 (10)
0.1035
1.06029 (15)
1.0908
0.0700 (5)
0.084*
0.7312 (3)
0.7166
0.20515 (9)
0.2424
0.77736 (16)
0.8109
0.0722 (5)
0.087*
H9
C18
H18
C17
H17
C8
0.7174 (3)
0.7081
−0.04923 (9)
−0.0455
1.26476 (15)
1.3271
0.0693 (5)
0.083*
0.7140 (3)
0.7017
0.00713 (10)
0.0484
1.20731 (15)
1.2322
0.0716 (5)
0.086*
0.7323 (3)
0.7157
0.21237 (9)
0.2541
0.68120 (15)
0.65
0.0684 (5)
0.082*
H8
C20
H20
C16
C2
0.7449 (3)
0.753
−0.11520 (10)
−0.1568
1.13412 (15)
1.1084
0.0722 (5)
0.087*
0.7284 (2)
0.3369 (3)
0.4002
0.00392 (9)
0.18415 (9)
0.2173
1.11405 (14)
0.33206 (16)
0.3189
0.0652 (5)
0.0700 (5)
0.084*
H2
C12
H12
C5
0.7835 (3)
0.8052
0.09649 (10)
0.0596
0.67957 (16)
0.6482
0.0743 (5)
0.089*
0.1508 (3)
0.0882
0.08715 (10)
0.055
0.37601 (17)
0.3918
0.0754 (5)
0.09*
H5
Acta Cryst. (2013). C69, 267-272
sup-10

supplementary materials
C14
H14
C4
0.7485 (3)
0.7649
0.07314 (10)
0.036
0.97391 (16)
0.9408
0.0720 (5)
0.086*
0.0624 (3)
−0.061
0.14239 (10)
0.1471
0.31898 (16)
0.2944
0.0741 (5)
0.089*
H4
C11
H11
C3
0.7769 (3)
0.7901
0.08960 (10)
0.0477
0.77449 (15)
0.8048
0.0728 (5)
0.087*
0.1549 (3)
0.0941
0.19133 (10)
0.2291
0.29755 (17)
0.2598
0.0783 (5)
0.094*
H3
C23
H23A
H23B
H23C
H1
0.7774 (4)
0.7856
−0.23565 (12)
−0.2351
1.42532 (19)
1.4951
0.0988 (7)
0.148*
0.8861
−0.2544
1.4309
0.148*
0.6752
−0.2619
1.377
0.148*
0.763 (3)
0.2108 (14)
0.516 (2)
0.119*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
S1
0.0687 (3)
0.0657 (8)
0.0923 (9)
0.0830 (8)
0.1070 (10)
0.0645 (9)
0.0548 (8)
0.0702 (11)
0.0730 (11)
0.0931 (13)
0.0624 (9)
0.0735 (11)
0.1218 (12)
0.0906 (13)
0.0829 (12)
0.0961 (14)
0.0853 (12)
0.0899 (13)
0.0866 (12)
0.0974 (14)
0.0715 (11)
0.0730 (11)
0.1028 (14)
0.0743 (12)
0.0874 (13)
0.0628 (10)
0.0958 (14)
0.0718 (12)
0.133 (2)
0.0501 (3)
0.0533 (8)
0.0643 (8)
0.0490 (7)
0.0633 (8)
0.0506 (9)
0.0524 (10)
0.0548 (10)
0.0624 (11)
0.0719 (13)
0.0547 (10)
0.0605 (11)
0.0609 (8)
0.0795 (13)
0.0629 (11)
0.0548 (11)
0.0675 (12)
0.0631 (12)
0.0506 (10)
0.0605 (11)
0.0628 (11)
0.0614 (11)
0.0555 (11)
0.0674 (13)
0.0615 (11)
0.0768 (13)
0.0563 (11)
0.0738 (13)
0.0928 (17)
0.0675 (3)
0.0708 (9)
0.0829 (8)
0.0819 (8)
0.0669 (7)
0.0551 (9)
0.0644 (10)
0.0800 (12)
0.0661 (10)
0.0617 (10)
0.0650 (10)
0.0616 (10)
0.0834 (9)
0.0630 (11)
0.0660 (11)
0.0798 (12)
0.0656 (11)
0.0714 (11)
0.0780 (12)
0.0687 (11)
0.0634 (10)
0.0834 (12)
0.0735 (12)
0.0917 (14)
0.0742 (12)
0.0832 (12)
0.0715 (11)
0.0887 (13)
0.0818 (14)
−0.00035 (18)
−0.0046 (6)
−0.0019 (6)
0.0063 (5)
0.0439 (2)
0.0394 (7)
0.0637 (8)
0.0485 (7)
0.0510 (7)
0.0340 (8)
0.0306 (8)
0.0382 (9)
0.0367 (9)
0.0453 (10)
0.0324 (8)
0.0356 (9)
0.0624 (9)
0.0443 (10)
0.0378 (10)
0.0539 (11)
0.0449 (10)
0.0466 (10)
0.0480 (10)
0.0483 (11)
0.0345 (9)
0.0442 (10)
0.0498 (11)
0.0462 (11)
0.0448 (11)
0.0360 (10)
0.0447 (11)
0.0385 (10)
0.0610 (15)
−0.00150 (18)
−0.0013 (7)
0.0005 (6)
N1
O1
O2
−0.0001 (6)
−0.0033 (6)
0.0008 (7)
O4
−0.0010 (7)
−0.0017 (7)
−0.0059 (7)
−0.0034 (8)
−0.0069 (8)
−0.0031 (10)
−0.0055 (8)
−0.0038 (8)
−0.0081 (7)
−0.0084 (10)
−0.0072 (9)
−0.0048 (9)
−0.0111 (9)
−0.0095 (9)
−0.0048 (8)
0.0015 (9)
C1
C7
−0.0057 (8)
0.0082 (9)
C6
C13
C21
C10
C19
O3
−0.0077 (9)
−0.0083 (9)
−0.0062 (8)
−0.0066 (8)
−0.0125 (7)
−0.0071 (10)
−0.0082 (9)
−0.0092 (9)
−0.0133 (9)
−0.0148 (9)
−0.0030 (9)
−0.0093 (9)
−0.0081 (9)
0.0143 (9)
C22
C15
C9
C18
C17
C8
C20
C16
C2
−0.0081 (8)
0.0005 (9)
C12
C5
0.0111 (10)
−0.0129 (9)
−0.0045 (9)
−0.0003 (9)
0.0035 (9)
0.0002 (9)
0.0025 (10)
−0.0070 (9)
−0.0007 (11)
0.0015 (9)
C14
C4
C11
C3
0.0083 (9)
0.0169 (11)
0.0078 (12)
C23
−0.0041 (14)
Acta Cryst. (2013). C69, 267-272
sup-11

supplementary materials
Geometric parameters (Å, º)
S1—O2
1.4245 (13)
1.4269 (12)
1.6432 (15)
1.7621 (17)
1.423 (2)
0.91 (3)
C22—H22B
C15—C14
C15—C16
C15—H15
C9—C8
0.97
S1—O1
1.324 (3)
1.448 (2)
0.93
S1—N1
S1—C1
N1—C7
1.379 (3)
0.93
N1—H1
C9—H9
O4—C19
O4—C22
C1—C2
1.369 (2)
1.434 (2)
1.378 (2)
1.380 (2)
1.380 (2)
1.385 (2)
1.388 (2)
0.93
C18—C17
C18—H18
C17—C16
C17—H17
C8—H8
1.391 (3)
0.93
1.390 (2)
0.93
C1—C6
C7—C8
0.93
C7—C12
C6—C5
C20—H20
C2—C3
0.93
1.376 (3)
0.93
C6—H6
C2—H2
C13—O3
C13—C14
C13—C10
C21—C20
C21—C16
C21—H21
C10—C11
C10—C9
C19—C18
C19—C20
C22—C23
C22—H22A
1.228 (2)
1.466 (3)
1.502 (2)
1.367 (3)
1.402 (2)
0.93
C12—C11
C12—H12
C5—C4
1.384 (3)
0.93
1.366 (3)
0.93
C5—H5
C14—H14
C4—C3
0.93
1.381 (3)
0.93
1.378 (2)
1.382 (3)
1.367 (3)
1.390 (2)
1.501 (3)
0.97
C4—H4
C11—H11
C3—H3
0.93
0.93
C23—H23A
C23—H23B
C23—H23C
0.96
0.96
0.96
O2—S1—O1
O2—S1—N1
O1—S1—N1
O2—S1—C1
O1—S1—C1
N1—S1—C1
C7—N1—S1
C7—N1—H1
S1—N1—H1
C19—O4—C22
C2—C1—C6
C2—C1—S1
C6—C1—S1
C8—C7—C12
C8—C7—N1
C12—C7—N1
C1—C6—C5
C1—C6—H6
C5—C6—H6
O3—C13—C14
O3—C13—C10
119.26 (7)
108.97 (8)
104.76 (8)
108.62 (7)
108.00 (8)
106.53 (7)
122.41 (11)
113.0 (16)
113.6 (17)
117.85 (14)
121.14 (16)
118.74 (12)
120.09 (13)
118.61 (16)
119.22 (15)
122.11 (15)
118.90 (17)
120.5
C19—C18—C17
C19—C18—H18
C17—C18—H18
C16—C17—C18
C16—C17—H17
C18—C17—H17
C9—C8—C7
119.28 (16)
120.4
120.4
122.35 (17)
118.8
118.8
120.45 (17)
119.8
C9—C8—H8
C7—C8—H8
119.8
C21—C20—C19
C21—C20—H20
C19—C20—H20
C17—C16—C21
C17—C16—C15
C21—C16—C15
C3—C2—C1
120.54 (17)
119.7
119.7
116.63 (17)
119.34 (17)
124.02 (17)
119.25 (17)
120.4
C3—C2—H2
C1—C2—H2
120.4
120.5
C11—C12—C7
C11—C12—H12
C7—C12—H12
120.35 (17)
119.8
121.27 (17)
119.55 (17)
119.8
Acta Cryst. (2013). C69, 267-272
sup-12

supplementary materials
C14—C13—C10
C20—C21—C16
C20—C21—H21
C16—C21—H21
C11—C10—C9
C11—C10—C13
C9—C10—C13
C18—C19—O4
C18—C19—C20
O4—C19—C20
O4—C22—C23
O4—C22—H22A
C23—C22—H22A
O4—C22—H22B
C23—C22—H22B
H22A—C22—H22B
C14—C15—C16
C14—C15—H15
C16—C15—H15
C8—C9—C10
119.18 (16)
121.40 (17)
119.3
C4—C5—C6
120.08 (17)
120
C4—C5—H5
C6—C5—H5
120
119.3
C15—C14—C13
C15—C14—H14
C13—C14—H14
C5—C4—C3
122.46 (18)
118.8
117.89 (16)
123.20 (17)
118.90 (16)
124.55 (16)
119.76 (18)
115.69 (16)
107.77 (16)
110.2
118.8
120.54 (18)
119.7
C5—C4—H4
C3—C4—H4
119.7
C10—C11—C12
C10—C11—H11
C12—C11—H11
C2—C3—C4
121.23 (18)
119.4
119.4
110.2
120.03 (18)
120
110.2
C2—C3—H3
110.2
C4—C3—H3
120
108.5
C22—C23—H23A
C22—C23—H23B
109.5
129.19 (18)
115.4
109.5
H23A—C23—H23B
C22—C23—H23C
H23A—C23—H23C
H23B—C23—H23C
109.5
109.5
109.5
109.5
115.4
121.40 (17)
119.3
C8—C9—H9
C10—C9—H9
119.3
O2—S1—N1—C7
O1—S1—N1—C7
C1—S1—N1—C7
−54.26 (15)
177.05 (13)
62.76 (15)
−167.78 (14)
−37.10 (16)
74.98 (15)
14.36 (17)
145.04 (14)
−102.89 (15)
−135.53 (15)
47.2 (2)
C12—C7—C8—C9
N1—C7—C8—C9
−0.5 (3)
−177.83 (16)
−1.1 (3)
C16—C21—C20—C19
C18—C19—C20—C21
O4—C19—C20—C21
C18—C17—C16—C21
C18—C17—C16—C15
C20—C21—C16—C17
C20—C21—C16—C15
C14—C15—C16—C17
C14—C15—C16—C21
C6—C1—C2—C3
O2—S1—C1—C2
1.9 (3)
O1—S1—C1—C2
−178.15 (18)
1.1 (3)
N1—S1—C1—C2
O2—S1—C1—C6
−178.05 (18)
−0.4 (3)
O1—S1—C1—C6
N1—S1—C1—C6
178.72 (19)
177.28 (19)
−1.8 (3)
S1—N1—C7—C8
S1—N1—C7—C12
C2—C1—C6—C5
S1—C1—C6—C5
2.1 (3)
−2.7 (3)
179.91 (14)
175.02 (19)
−5.8 (3)
S1—C1—C2—C3
179.41 (15)
2.3 (3)
O3—C13—C10—C11
C14—C13—C10—C11
O3—C13—C10—C9
C14—C13—C10—C9
C22—O4—C19—C18
C22—O4—C19—C20
C19—O4—C22—C23
C11—C10—C9—C8
C13—C10—C9—C8
O4—C19—C18—C17
C20—C19—C18—C17
C19—C18—C17—C16
C10—C9—C8—C7
C8—C7—C12—C11
N1—C7—C12—C11
C1—C6—C5—C4
179.61 (17)
0.2 (3)
−4.9 (3)
174.23 (18)
−7.4 (3)
C16—C15—C14—C13
O3—C13—C14—C15
C10—C13—C14—C15
C6—C5—C4—C3
179.29 (18)
4.3 (3)
172.68 (17)
−175.26 (17)
1.5 (3)
−174.90 (17)
−1.8 (3)
C9—C10—C11—C12
C13—C10—C11—C12
C7—C12—C11—C10
C1—C2—C3—C4
0.4 (3)
−178.55 (16)
178.87 (18)
−1.2 (3)
−179.56 (17)
−2.3 (3)
1.1 (3)
−0.3 (3)
C5—C4—C3—C2
1.2 (3)
−1.5 (3)
Acta Cryst. (2013). C69, 267-272
sup-13

supplementary materials
Hydrogen-bond geometry (Å, º)
CgA is the centroid calculated through the ring A C atoms.
D—H···A
D—H
H···A
D···A
D—H···A
N1—H1···O3i
0.91 (3)
0.93
2.08 (3)
2.34
2.987 (2)
3.228 (2)
3.816 (3)
3.269 (2)
3.285 (2)
175 (3)
160
C9—H9···O1ii
C23—H23A···CgAiii
C2—H2···O4iv
C3—H3···O4iv
0.96
3.04
138
0.93
2.65
125
0.93
2.68
124
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y+1/2, −z+3/2.
Acta Cryst. (2013). C69, 267-272
sup-14