(Z)-5-[(5-Methyl-1H-imidazol-4-yl)methyl-idene]-2-sulfanyl-idene-1, 3-thia-zolidin-4-one monohydrate: A three-dimensional hydrogen-bonded framework structure

Article abstract of DOI:10.1107/S0108270112043260

The non-H atoms in the organic component of the title compound, C8H7N3OS2·H2O, are almost coplanar, as the dihedral angle between the two ring planes is only 1.8 (2)°; there is a wide C - C - C angle of 127.8 (3)° at the methine C atom linking the two rin

Full text of DOI:10.1107/S0108270112043260

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
the S1—C5—C57—C54 and C5—C57—C54—N53 torsion
angles; the dihedral angle between the mean planes through
the two independent rings is 1.8 (2) . At the same time, there
is a wide C—C—C angle at methine atom C57 which links the
ꢁ
ISSN 0108-2701
(
Z)-5-[(5-Methyl-1H-imidazol-4-yl)-
methylidene]-2-sulfanylidene-1,3-thia-
zolidin-4-one monohydrate: a three-
dimensional hydrogen-bonded frame-
work structure
a
a
b
Alberto Insuasty, Braulio Insuasty, Justo Cobo and
c
Christopher Glidewell *
a
Departamento de Qu ´ı mica, Universidad de Valle, AA 25360 Cali, Colombia,
b
Departamento de Qu ´ı mica Inorg a´ nica y Org a´ nica, Universidad de Ja e´ n, 23071
c
Ja e´ n, Spain, and School of Chemistry, University of St Andrews, Fife KY16 9ST,
Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 10 September 2012
Accepted 17 October 2012
Online 23 October 2012
two rings (Table 1), while of the exocyclic angles at C5 the
ꢁ
value of S1—C5—C57 exceeds that of C4—C5—C57 by ca 5 .
Although the values of the N53—C54—C57 and C55—C54—
The non-H atoms in the organic component of the title
compound, C H N OS ꢀH O, are almost coplanar, as the
ꢁ
C57 angles differ by only ca 2 , in the simple analogue
8
7
3
2
2
ꢁ
1-methylimidazole-4-carboxaldehyde monohydrate, (IX)
[Cambridge Structural Database (CSD; Allen, 2002) refcode
BEHBIA; Cheruzel et al., 2003], the corresponding N—C—C
dihedral angle between the two ring planes is only 1.8 (2) ;
ꢁ
there is a wide C—C—C angle of 127.8 (3) at the methine C
atom linking the two rings. The molecular components are
linked into a three-dimensional framework structure by two-
centre hydrogen bonds of N—Hꢀ ꢀ ꢀO and O—Hꢀ ꢀ ꢀN types,
together with a three-centre O—Hꢀ ꢀ ꢀ(N,S) system. Compar-
isons are made with some (Z)-5-arylmethylidene-2-sulfanyl-
idene-1,3-thiazolidin-4-ones.
ꢁ
and C—C—C angles are 121.0 (2) and 129.2 (2) , respectively.
These observations taken together suggest that the short
intramolecular nonbonded S1ꢀ ꢀ ꢀN53 contact, with an Sꢀ ꢀ ꢀN
˚
distance of 3.048 (3) A, somewhat shorter than the sum of the
˚
van der Waals radii (3.35 A; Bondi, 1964), is strongly repulsive.
This behaviour in compound (I) closely resembles that in
compounds (II)–(VIII), each of which has an almost planar
ꢁ
Comment
molecular skeleton and a wide angle, ca 130 , at the linking
methine C atom. Compounds (II)–(VIII) differ from com-
pound (I) in that the short repulsive intramolecular contact is
We report here the molecular and supramolecular structure of
(
Z)-5-[(5-methyl-1H-imidazol-4-yl)methylidene]-2-sulfanyli-
dene-1,3-thiazolidin-4-one monohydrate, (I) (Fig. 1), which we
briefly compare with those of the related (Z)-5-aryl-
methylidene-2-sulfanylidene-1,3-thiazolidin-4-ones (II)–(VIII)
(Delgado et al., 2005, 2006) (see Scheme). Compound (I) was
prepared using a base-catalysed condensation reaction
between rhodanine (2-sulfanylidene-1,3-thiazolidin-4-one)
and 4-methylimidazole-5-carbaldehyde in refluxing ethanol,
whereas compounds (II)–(VIII) were all prepared by
condensation reactions between rhodanine and the appro-
priately substituted aryl aldehydes using microwave radiation
in solvent-free systems. Compounds (II)–(VIII) were obtained
in solvent-free form by crystallization from solutions in
dimethylformamide, whereas crystallization of compound (I)
from a solution in ethanol provided a stoichiometric mono-
hydrate.
Figure 1
The molecular components of compound (I), showing the atom-labelling
scheme and the N—Hꢀ ꢀ ꢀO hydrogen bond within the selected
asymmetric unit. Displacement ellipsoids are drawn at the 30%
probability level.
Within the organic component of compound (I), the non-H
atoms are almost coplanar, as shown by the values (Table 1) of
o468 # 2012 International Union of Crystallography
doi:10.1107/S0108270112043260
Acta Cryst. (2012). C68, o468–o471

organic compounds
Figure 2
A stereoview of part of the crystal structure of compound (I), showing the
2
2
formation of a C (9) chain parallel to [100]. For the sake of clarity, H
atoms other than atoms H3, H11 and H12 have been omitted.
of the Sꢀ ꢀ ꢀH—C type, rather than of the Sꢀ ꢀ ꢀN type, as in (I).
In every case, it appears that a distortion of the central C—
C—C angles is energetically more economical in minimizing
the effects of the repulsive contact than a rotation about the
formal single bridge bond, viz. C54—C57 in (I) and the
corresponding bonds in (II)–(VIII). However, in none of
compounds (I)–(VIII) do the bond lengths provide any
evidence for the type of electronic polarization which could
lead to the development of canonical forms having restricted
rotation about the bond in question.
Figure 3
A stereoview of part of the crystal structure of compound (I), showing the
formation of a C(8) chain parallel to [001]. For the sake of clarity, the
water molecule and H atoms other than atom H51 have been omitted.
two-coordinate S atoms as the acceptors found that for O—
˚
Hꢀ ꢀ ꢀS interactions, the mean Hꢀ ꢀ ꢀS distance was 2.63 (4) A
˚
and the mean Oꢀ ꢀ ꢀS distance was 3.37 (5) A. In general, the
distances in three-centre interactions are expected to be
longer than those in similar two-centre interactions, and this is
well illustrated by the two O—Hꢀ ꢀ ꢀN hydrogen bonds, one
two-centre and one three-centre, present in compound (I)
The molecular components of compound (I) are linked into
a three-dimensional framework structure, which contains two-
centre hydrogen bonds of N—Hꢀ ꢀ ꢀO and O—Hꢀ ꢀ ꢀN types,
along with an almost planar three-centre O—Hꢀ ꢀ ꢀ(N,S)
(
Table 2). By way of comparison, the intermolecular compo-
system in compound (V)
system (Table 2); the sum of the bond angles at atom H11 is
ꢁ
nent of a three-centre C—Hꢀ ꢀ ꢀ(S)
2
357 . However, the formation of the framework structure is
readily analysed in terms of three independent one-dimen-
˚
has Hꢀ ꢀ ꢀS and Cꢀ ꢀ ꢀS distances of 2.86 and 3.588 (2) A,
respectively (Delgado et al., 2005), fully consistent with the
sional substructures (Ferguson et al., 1998a,b; Gregson et al.,
2000) and their combinations.
Within the selected asymmetric unit (Fig. 1), thiazolidine
ring atom N3 acts as hydrogen-bond donor to water atom O1.
In the first one-dimensional substructure, atom O1 at (x, y, z)
acts as hydrogen-bond donor, via atom H12, to imidazole ring
1
2
3
2
2
atom N53 at (x + , y, ꢂz + ), so generating a C (9) (Bernstein
2
et al., 1995) chain running parallel to the [100] direction and
built from bimolecular units related to one another by the
a-glide plane at z = 0.75 (Fig. 2).
Two further substructures take the form of chains running
parallel to the [001] direction and comprising building blocks
related, respectively, by a 2 screw axis and a c-glide plane. The
1
simpler of these two substructures involves the organic
component only, with no participation by the water molecule.
Atom N51 at (x, y, z) acts as hydrogen-bond donor to carbonyl
1
1
atom O4 at (ꢂx + , ꢂy + 1, z ꢂ ), so forming a simple C(8)
2
2
chain running parallel to the [001] direction and containing
organic molecules which are related to one another by the 2
1
1
1
screw axis along ( , , z) (Fig. 3).
In the final substructure, atom O1 at (x, y, z) acts as
hydrogen-bond donor, via atom H11, in a three-centre system
4
2
Figure 4
A stereoview of part of the crystal structure of compound (I), showing the
2
2
2
formation of a C (6)C (9)[R (6)] chain of rings parallel to [001]. For the
sake of clarity, H atoms other than atoms H3, H11 and H12 have been
omitted.
3
1
2
2
1
to atoms N53 and S1, both at (x, ꢂy + , z + ). A database
2
2
study (Allen et al., 1997) of two-centre hydrogen bonds having
ꢃ
Acta Cryst. (2012). C68, o468–o471
Insuasty et al.
C H N OS
8 7 3 2
ꢀH O
2
o469

organic compounds
Experimental
To a mixture of 4-methylimidazole-5-carbaldehyde (1.1 mmol) and
2-sulfanylidene-1,3-thiazolidin-4-one (1.0 mmol) in dry ethanol
(10 ml) was added one drop of piperidine, and the mixture was then
heated under reflux for 6 h. The resulting solid precipitate was
collected by filtration and recrystallized from ethanol (yield 91%;
+
m.p. 307–309 K). MS (EI, 70 eV) m/z (%): 225 (M , 38), 139 (1),
138 (70), 137 (100), 69 (25), 42 (13). Crystals suitable for single-
crystal X-ray diffraction were obtained by slow evaporation, at
ambient temperature and in air, of a solution in ethanol.
Crystal data
˚
V = 2074.5 (4) A
3
C
8
H
7
N
3
OS
2
ꢀH
2
O
M
r
= 243.32
Orthorhombic, Pbca
Z = 8
Mo Kꢁ radiation
˚
a = 7.4110 (6) A
ꢂ1
ꢂ = 0.50 mm
T = 120 K
˚
b = 16.2739 (18) A
Figure 5
A stereoview of part of the crystal structure of compound (I), showing the
˚
c = 17.201 (2) A
0.40 ꢄ 0.28 ꢄ 0.10 mm
2
1
6
6
formation of a sheet of R (6) and R (24) rings parallel to (100). For the
sake of clarity, H atoms bonded to C atoms have been omitted.
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
23037 measured reflections
2384 independent reflections
1449 reflections with I > 2ꢃ(I)
values for the O—Hꢀ ꢀ ꢀS interaction in (I). This three-
centre hydrogen bond in compound (I) gives rise to a
2
2
2
1
Rint = 0.119
C (6)C (9)[R (6)] chain of rings running parallel to the [001]
2
2
T
min = 0.826, Tmax = 0.952
direction and containing bimolecular units related to one
another by the c-glide plane at y = 0.75 (Fig. 4).
The combination of the two independent chains parallel to
Refinement
2
2
R[F > 2ꢃ(F )] = 0.056
wR(F ) = 0.164
137 parameters
H-atom parameters constrained
[001] generates a sheet lying parallel to (100), which contains
equal numbers of R (6) and R (24) rings and which lies in the
2
2
1
6
6
Áꢄmax = 0.47 e A˚
ꢂ3
S = 1.08
2384 reflections
Áꢄmin = ꢂ0.39 e A˚
ꢂ3
domain 0.0 < x < 0.5 (Fig. 5). A second such sheet, related to
the first by inversion, lies in the domain 0.5 < x < 1.0, and the
successive (100) sheets are linked by the chains parallel to
[100] (Fig. 2) to form a continuous three-dimensional frame-
work structure.
It is of interest briefly to compare the three-dimensional
supramolecular aggregation in compound (I) with that in
compounds (II)–(VIII), where the dimensionality is always
less than three (Delgado et al., 2005, 2006). Compounds (II)–
All H atoms were located in difference maps. H atoms bonded to C
atoms were subsequently treated as riding atoms in geometrically
idealized positions, with C—H distances of 0.95 (imidazole and
˚
methine) or 0.98 A (methyl), and with Uiso(H) = kUeq(C), where k =
1.5 for the methyl group, which was permitted to rotate but not to tilt,
and k = 1.2 otherwise. H atoms bonded to N atoms were permitted to
ride at the positions located in the difference maps, with Uiso(H) =
(VIII) all crystallize in solvent-free forms and the dominant
mode of aggregation is the formation of cyclic R (8) dimers
2
2
built from pairs of N—Hꢀ ꢀ ꢀO hydrogen bonds; the sole
Table 1
Selected bond and torsion angles ( ).
exception to this pattern occurs in compound (IV), where an
2
ꢁ
R (8) dimer is formed from paired N—Hꢀ ꢀ ꢀS hydrogen bonds.
2
C5—C57—C54
S1—C5—C57
C4—C5—C57
127.8 (3)
127.8 (3)
122.6 (3)
N53—C54—C57
C55—C54—C57
124.0 (3)
126.0 (3)
There are no direction-specific interactions between the
dimers in compounds (III) and (VIII), so that the aggregation
here can be regarded as zero-dimensional. The aggregation in
compounds (VI) and (VII) is one-dimensional; there are no
further hydrogen bonds in the structures of compounds (VI)
and (VII), but instead the dimers are linked into chains by,
respectively, an aromatic ꢀ–ꢀ stacking interaction and a
dipolar carbonyl–carbonyl interaction. By contrast, the
dimeric units in compound (IV) are linked into a chain of rings
by a C—Hꢀ ꢀ ꢀO hydrogen bond, while those in compound (V)
are linked into a chain of rings by a C—Hꢀ ꢀ ꢀS hydrogen bond.
S1—C5—C57—C54
0.8 (6)
C5—C57—C54—N53
ꢂ3.3 (6)
Table 2
Hydrogen-bond geometry (A, ).
˚
ꢁ
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N3—H3ꢀ ꢀ ꢀO1
1.06
0.90
0.88
0.88
0.86
1.69
1.96
2.07
2.80
2.29
2.736 (4)
2.848 (4)
2.857 (4)
3.456 (3)
3.122 (4)
169
171
149
132
164
i
0
N51—H51ꢀ ꢀ ꢀO4
O1—H11ꢀ ꢀ ꢀN53
Finally, in compound (II), where Z = 2 and which forms the
ii
ii
only two-dimensional aggregation so far observed in this
series, three independent C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds
link the dimeric units into complex sheets.
O1—H11ꢀ ꢀ ꢀS1
iii
O1—H12ꢀ ꢀ ꢀN53
1
2
1
2
3
1
1
2
3
2
Symmetry codes: (i) ꢂx þ ; ꢂy þ 1; z ꢂ ; (ii) x; ꢂy þ ; z þ ; (iii) x þ ; y; ꢂz þ .
2
2
ꢃ
o470 Insuasty et al.
C
8
H N
7
3
OS
2
2
ꢀH O
Acta Cryst. (2012). C68, o468–o471

organic compounds
˚
.2Ueq(N), giving N—H distances of 0.90 and 1.06 A (see Table 2). H
1
atoms bonded to O atoms were permitted to ride at the positions
located in the difference maps, with Uiso(H) = 1.5Ueq(O), giving
References
Allen, F. H., Bird, C. M., Rowland, R. S. & Raithby, P. R. (1997). Acta Cryst.
B53, 696–701.
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Int. Ed. Engl. 34, 1555–1573.
Bondi, A. (1964). J. Phys. Chem. 68, 441–451.
˚
O—H distances of 0.86 and 0.88 A (see Table 2), and an H—O—H
ꢁ
angle of 103.9 .
Data collection: COLLECT (Hooft, 1999); cell refinement:
DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De
Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38,
(
(
(
Duisenberg et al., 2003); program(s) used to solve structure: SIR2004
Burla et al., 2005); program(s) used to refine structure: SHELXL97
Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); soft-
3
81–388.
Cheruzel, L. E., Pometun, M. S., Cecil, M. R., Mashuta, M. S., Wittebort, R. J.
Buchanan, R. M. (2003). Angew. Chem. Int. Ed. 42, 5452–5455.
&
ware used to prepare material for publication: SHELXL97 and
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C61, o477–o482.
Delgado, P., Quiroga, J., de la Torre, J. M., Cobo, J., Low, J. N. & Glidewell, C.
(
2006). Acta Cryst. C62, o382–o385.
The authors thank ‘Centro de Instrumentaci o´ n Cient ı´ fico-
T e´ cnica of Universidad de Ja e´ n’ and the staff for data collec-
tion. AI and BI thank UNIVALLE and COLCIENCIAS for
financial support. JC thanks the Consejer ı´ a de Innovaci o´ n,
Ciencia y Empresa (Junta de Andaluc ı´ a, Spain), the Univer-
sidad de Ja e´ n and Ministerio de Ciencia e Innovaci o´ n for
financial support.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000).
J. Appl. Cryst. 33, 893–898.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220–229.
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Cryst. B54, 129–138.
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Cryst. B54, 139–150.
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B56, 39–57.
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Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SF3183). Services for accessing these data are
described at the back of the journal.
ꢃ
Acta Cryst. (2012). C68, o468–o471
Insuasty et al.
C H N OS
8 7 3 2
ꢀH O
2
o471

supplementary materials
supplementary materials
Acta Cryst. (2012). C68, o468–o471 [doi:10.1107/S0108270112043260]
(
Z)-5-[(5-Methyl-1H-imidazol-4-yl)methylidene]-2-sulfanylidene-1,3-thia-
zolidin-4-one monohydrate: a three-dimensional hydrogen-bonded framework
structure
Alberto Insuasty, Braulio Insuasty, Justo Cobo and Christopher Glidewell
(Z)-5-[(5-Methyl-1H-imidazol-4-yl)methylidene]-2-sulfanylidene- 1,3-thiazolidin-4-one monohydrate
Crystal data
OS ·H
= 243.32
C
M
8
H
7
N
3
2
2
O
F(000) = 1008
= 1.558 Mg m
−3
r
D
x
Orthorhombic, Pbca
Hall symbol: -P 2ac 2ab
a = 7.4110 (6) Å
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2384 reflections
θ = 2.8–27.5°
µ = 0.50 mm
T = 120 K
−1
b = 16.2739 (18) Å
c = 17.201 (2) Å
3
V = 2074.5 (4) Å
Plate, colourless
Z = 8
0.40 × 0.28 × 0.10 mm
Data collection
Bruker–Nonius KappaCCD
diffractometer
Radiation source: Bruker–Nonius FR591
rotating anode
Tmin = 0.826, Tmax = 0.952
23037 measured reflections
2384 independent reflections
1449 reflections with I > 2σ(I)
Graphite monochromator
Detector resolution: 9.091 pixels mm
φ and ω scans
R
int = 0.119
-1
θmax = 27.5°, θmin = 2.8°
h = −9→9
Absorption correction: multi-scan
k = −21→17
l = −22→22
(
SADABS; Sheldrick, 2003)
Refinement
2
Refinement on F
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
Least-squares matrix: full
R[F > 2σ(F )] = 0.056
2
2
2
wR(F ) = 0.164
S = 1.08
H-atom parameters constrained
2
2
2
2
1
0
384 reflections
37 parameters
restraints
w = 1/[σ (F
where P = (F
o
) + (0.0867P) + 0.5619P]
2
2
o
+ 2F )/3
c
(Δ/σ)max = 0.001
Δρmax = 0.47 e Å
Δρmin = −0.39 e Å
−
3
Primary atom site location: structure-invariant
direct methods
−
3
Acta Cryst. (2012). C68, o468–o471
sup-1

supplementary materials
2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å )
x
y
z
Uiso*/Ueq
S1
0.47426 (13)
0.5126 (5)
0.58807 (13)
0.4701 (4)
0.4801
0.72683 (5)
0.7666 (2)
0.85987 (6)
0.70945 (19)
0.7237
0.63974 (5)
0.7330 (2)
0.74867 (5)
0.78858 (16)
0.8483
0.0228 (3)
0.0224 (8)
0.0256 (3)
0.0235 (7)
0.028*
C2
S2
N3
H3
C4
0.4014 (5)
0.3547 (4)
0.3927 (5)
0.3266 (5)
0.2872
0.6349 (2)
0.57928 (16)
0.6334 (2)
0.5694 (2)
0.5239
0.7630 (2)
0.80648 (14)
0.6771 (2)
0.6375 (2)
0.6678
0.0234 (8)
0.0307 (7)
0.0210 (8)
0.0216 (8)
0.026*
O4
C5
C57
H57
N51
H51
C52
H52
N53
C54
C55
C56
H56A
H56B
H56C
O1
0.2541 (4)
0.2324
0.51311 (19)
0.4824
0.43903 (17)
0.3967
0.0248 (7)
0.030*
0.3172 (5)
0.3352
0.5909 (2)
0.6188
0.4338 (2)
0.3860
0.0253 (8)
0.030*
0.3509 (4)
0.3082 (5)
0.2464 (5)
0.1835 (5)
0.2791
0.62340 (18)
0.5612 (2)
0.4923 (2)
0.4106 (2)
0.3852
0.50189 (17)
0.55531 (19)
0.5162 (2)
0.5454 (2)
0.5766
0.0225 (7)
0.0213 (8)
0.0241 (8)
0.0319 (9)
0.048*
0.1546
0.3750
0.5012
0.048*
0.0755
0.4181
0.5776
0.048*
0.5304 (4)
0.5010
0.73387 (15)
0.7729
0.94381 (14)
0.9771
0.0267 (6)
0.040*
H11
H12
0.6091
0.7053
0.9682
0.040*
2
Atomic displacement parameters (Å )
11
22
33
12
13
23
U
U
U
U
U
U
S1
0.0305 (5)
0.0203 (19)
0.0299 (5)
0.0288 (17)
0.0211 (18)
0.0497 (18)
0.0222 (19)
0.0224 (19)
0.0220 (17)
0.027 (2)
0.0221 (5)
0.027 (2)
0.0158 (4)
0.0199 (18)
0.0219 (5)
0.0174 (15)
0.021 (2)
−0.0029 (4)
0.0004 (16)
−0.0050 (4)
−0.0010 (14)
0.0032 (16)
−0.0059 (13)
−0.0005 (15)
−0.0004 (15)
0.0040 (14)
−0.0004 (17)
−0.0006 (12)
0.0001 (15)
0.0039 (16)
−0.0013 (17)
0.0046 (12)
−0.0005 (4)
−0.0005 (14)
0.0019 (4)
0.0000 (3)
C2
−0.0012 (15)
−0.0042 (4)
−0.0020 (12)
−0.0014 (16)
0.0061 (11)
0.0038 (14)
0.0027 (15)
−0.0076 (13)
0.0017 (16)
0.0002 (12)
0.0018 (15)
−0.0023 (16)
−0.0019 (18)
−0.0036 (10)
S2
0.0250 (5)
0.0243 (16)
0.028 (2)
N3
0.0003 (13)
0.0002 (15)
0.0012 (12)
−0.0001 (14)
0.0003 (15)
−0.0015 (13)
−0.0002 (16)
0.0001 (12)
−0.0009 (14)
−0.0008 (16)
−0.0032 (19)
0.0011 (11)
C4
O4
0.0258 (15)
0.024 (2)
0.0167 (12)
0.0172 (17)
0.0222 (18)
0.0226 (17)
0.0194 (18)
0.0174 (15)
0.0217 (17)
0.025 (2)
C5
C57
N51
C52
N53
C54
C55
C56
O1
0.0202 (18)
0.0298 (18)
0.030 (2)
0.0260 (17)
0.0220 (18)
0.0214 (19)
0.032 (2)
0.0242 (16)
0.0202 (19)
0.026 (2)
0.022 (2)
0.042 (2)
0.0378 (15)
0.0252 (14)
0.0170 (12)
Acta Cryst. (2012). C68, o468–o471
sup-2

supplementary materials
Geometric parameters (Å, º)
S1—C2
1.754 (4)
1.759 (4)
1.371 (5)
1.639 (4)
1.387 (5)
1.0563
N51—C55
N51—H51
C52—N53
C52—H52
N53—C54
C54—C55
C55—C56
C56—H56A
C56—H56B
C56—H56C
O1—H11
1.372 (4)
0.8973
S1—C5
C2—N3
C2—S2
1.309 (5)
0.9500
N3—C4
N3—H3
C4—O4
C4—C5
C5—C57
C57—C54
C57—H57
N51—C52
1.404 (4)
1.385 (5)
1.495 (5)
0.9800
1.225 (4)
1.478 (5)
1.337 (5)
1.427 (5)
0.9500
0.9800
0.9800
0.8826
1.352 (5)
O1—H12
0.8564
C2—S1—C5
N3—C2—S2
N3—C2—S1
S2—C2—S1
92.32 (17)
126.3 (3)
110.5 (3)
123.2 (2)
117.2 (3)
120.9
C55—N51—H51
N53—C52—N51
N53—C52—H52
N51—C52—H52
C52—N53—C54
C55—C54—N53
N53—C54—C57
C55—C54—C57
N51—C55—C54
N51—C55—C56
C54—C55—C56
C55—C56—H56A
C55—C56—H56B
129.8
112.7 (3)
123.7
123.7
C2—N3—C4
C2—N3—H3
C4—N3—H3
O4—C4—N3
O4—C4—C5
N3—C4—C5
C5—C57—C54
S1—C5—C57
C4—C5—C57
C4—C5—S1
C5—C57—H57
C54—C57—H57
C52—N51—C55
C52—N51—H51
104.5 (3)
109.9 (3)
124.0 (3)
126.0 (3)
104.8 (3)
123.9 (3)
131.3 (3)
109.5
121.8
123.8 (3)
125.8 (3)
110.4 (3)
127.8 (3)
127.8 (3)
122.6 (3)
109.6 (3)
116.1
109.5
H56A—C56—H56B
C55—C56—H56C
H56A—C56—H56C
H56B—C56—H56C
H11—O1—H12
109.5
109.5
109.5
109.5
103.9
116.1
108.0 (3)
122.0
C5—S1—C2—N3
C5—S1—C2—S2
S2—C2—N3—C4
S1—C2—N3—C4
C2—N3—C4—O4
C2—N3—C4—C5
O4—C4—C5—C57
N3—C4—C5—C57
O4—C4—C5—S1
N3—C4—C5—S1
C2—S1—C5—C57
C2—S1—C5—C4
C4—C5—C57—C54
1.9 (3)
S1—C5—C57—C54
0.8 (6)
−177.8 (3)
177.5 (3)
−2.2 (4)
−178.5 (4)
1.2 (4)
C55—N51—C52—N53
N51—C52—N53—C54
C52—N53—C54—C55
C52—N53—C54—C57
C5—C57—C54—C55
C5—C57—C54—N53
C52—N51—C55—C54
C52—N51—C55—C56
N53—C54—C55—N51
C57—C54—C55—N51
N53—C54—C55—C56
C57—C54—C55—C56
−0.4 (4)
0.8 (4)
−0.9 (4)
179.3 (3)
176.9 (4)
−3.3 (6)
−0.2 (4)
−179.8 (3)
0.7 (4)
1.7 (6)
−178.0 (3)
−180.0 (3)
0.3 (4)
177.0 (4)
−1.3 (3)
178.8 (3)
−179.5 (3)
−179.7 (4)
0.1 (6)
Acta Cryst. (2012). C68, o468–o471
sup-3

supplementary materials
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N3—H3···O1
1.06
0.90
0.88
0.88
0.86
1.69
1.96
2.07
2.80
2.29
2.736 (4)
2.848 (4)
2.857 (4)
3.456 (3)
3.122 (4)
169
171
149
132
164
i
N51—H51···O4
ii
O1—H11···N53
ii
O1—H11···S1
iii
O1—H12···N53
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1/2, y, −z+3/2.
Acta Cryst. (2012). C68, o468–o471
sup-4