Three novel benzothia-zine-fused triazoles as potential centrally acting muscle relaxants

Article abstract of DOI:10.1107/S0108270112040759

The structures of the novel triazolobenzothia-zines 2,4-di-hydro-1H- benzo[b][1,2,4]triazolo[4,3-d][1,4]thia-zin-1-one (IDPH-791), C9H7N3OS, (I), a potential muscle relaxant, its benzoyl derivative, 2-(2-oxo-2-phenyl-ethyl)-2,4- dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thia-zin-1-one, C20H17N3O4S, (II), and the Β-keto ester derivative, ethyl 3-oxo-2-(1-oxo-2,4-dihydro-1H- benzo[b][1,2,4]triazolo[4,3-d][1,4]thia-zin-2-yl)-3-phenylpropano-ate, C17H13N3O2S, (III), are the first examples of benzothia-zine-fused triazoles in the crystallographic literature. The heterocyclic thia-zine rings in all three structures adopt a distorted half-chair conformation. Com-pound (III) exists in the trans-Β-diketo form. Other than N - H...O hydrogen bonds in (I) forming dimers, no formal inter-molecular hydrogen bonds are involved in the crystal packing of any of the three structures, which is dominated by C - H...O/N and π-π stacking inter-actions.

Full text of DOI:10.1107/S0108270112040759

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
2002; Horne et al., 2004). The synthesis of triazoles fused to
another heterocyclic ring has attracted widespread attention
due to possible diverse applications in therapeutics and as
pesticides, herbicides, dyes, lubricants and analytical reagents
(Holla et al., 2001, 2002).
ISSN 0108-2701
Three novel benzothiazine-fused
triazoles as potential centrally acting
muscle relaxants
Krishnan Ravikumar,a* Balasubramanian Sridhar,a
Venkatasubramanian Hariharakrishnanb and
Awadesh Narain Singhb
aLaboratory of X-ray Crystallography, CSIR Indian Institute of Chemical Technology,
Hyderabad 500 007, India, and bSMS Pharma Research Centre, Hyderabad 500 038,
India
Correspondence e-mail: sshiya@yahoo.com
Received 3 August 2012
Accepted 27 September 2012
Online 27 October 2012
The structures of the novel triazolobenzothiazines 2,4-
dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-one
(IDPH-791), C9H7N3OS, (I), a potential muscle relaxant, its
benzoyl derivative, 2-(2-oxo-2-phenylethyl)-2,4-dihydro-1H-
benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-one, C20H17N3O4S,
(II), and the ꢀ-keto ester derivative, ethyl 3-oxo-2-(1-oxo-
2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-2-yl)-
3-phenylpropanoate, C17H13N3O2S, (III), are the first exam-
ples of benzothiazine-fused triazoles in the crystallographic
literature. The heterocyclic thiazine rings in all three
structures adopt a distorted half-chair conformation. Com-
pound (III) exists in the trans-ꢀ-diketo form. Other than N—
Hꢀ ꢀ ꢀO hydrogen bonds in (I) forming dimers, no formal
intermolecular hydrogen bonds are involved in the crystal
packing of any of the three structures, which is dominated by
C—Hꢀ ꢀ ꢀO/N and ꢁ–ꢁ stacking interactions.
1,4-Benzothiazines, structural analogues of phenothiazines,
possess a wide range of pharmacological activities (Fringuelli
et al., 1998; Matsumoto et al., 2000; Kobayashi et al., 1997), and
the presence of a fold along the Nꢀ ꢀ ꢀS axis is considered to be
one of the structural features responsible for these activities
(Silverman, 2004; Gupta & Ojha, 1988). A novel series of
triazolobenzothiazines was synthesized by Reddy Sastry et al.
(1991) and they were reported to be potential centrally acting
muscle relaxant agents. Among these, the compound IDPH-
791, (I), was stated as exhibiting significant muscle relaxant
activity, being twice as potent and with a longer duration of
action than mephenesin (Junnarkar et al., 1992). Recently, we
have reported the crystal structures of triazolobenzoxazines
(Ravikumar et al., 2012). As a continuation of our work on the
structural elucidation of bioactive molecules (Ravikumar &
Sridhar, 2010; Ravikumar et al., 2011), we report here the
crystal structures of three novel 1,4-benzothiazine-fused tri-
azoles, IDPH-791, (I), and its 2-substituted 2-oxo-2-phenyl-
Comment
The triazole scaffold, one of the most important and well
known heterocycles, is a common and integral feature of a
variety of natural products and medicinal agents. It is present
as an important structural component in an array of drug
categories, such as antimicrobial (Girmenia, 2009), analgesic
(Hafez et al., 2008), anticonvulsant (Guan et al., 2007), anti-
malarial (Gujjar et al., 2009), antiviral (Johns et al., 2009) and
anticancer agents (Duran et al., 2002). In the last few decades,
the structure–activity relationships of triazole derivatives have
revealed that, while the substituents on the triazole ring can be
varied, the greatest difference, both structurally and in terms
of properties, is exerted by the groups attached to the N atom
(Liu et al., 2008). The triazole ring is an attractive connecting
unit, since it is stable to metabolic degradation and capable of
hydrogen bonding, which can be favourable in the binding of
biomolecular targets and in improving solubility (Dalvie et al.,
Figure 1
A view of the asymmetric unit of (I), showing the two crystallographically
independent molecules related by pseudo-inversion, and the atom-
labelling scheme. Displacement ellipsoids are drawn at the 30%
probability level. Dashed lines indicate intermolecular hydrogen bonds.
Acta Cryst. (2012). C68, o475–o480
doi:10.1107/S0108270112040759
# 2012 International Union of Crystallography o475

organic compounds
C3 (Aravindan et al., 2003). Thiazine atom N3 shows planarity,
as the sums of the C—N3—C bond angles are 359.4 (1) and
359.9 (1)ꢁ in (I), 359.7 (2)ꢁ in (II) and 360.0 (2)ꢁ in (III).
In all three structures, the tricyclic ring system is confor-
mationally similar (Fig. 4). The thiazine ring is in a distorted
half-chair conformation, with atoms S1 and C2 displaced by
˚
1.057 (1) and ꢂ1.122 (1), and 0.473 (2) and ꢂ0.488 (2) A,
respectively, in the two molecules of (I), 1.177 (1) and
˚
˚
0.547 (2) A, respectively, in (II), and 1.076 (1) and 0.428 (2) A,
respectively, in (III), from the plane defined by atoms C3/C4/
N3/C5. The dihedral angles between the triazole and benzene
ring planes are 22.05 (8) and 21.72 (8)ꢁ in (I), 25.26 (11)ꢁ in
(II) and 18.08 (17)ꢁ in (III), reflecting the twist created by the
central thiazine ring in the tricyclic ring system.
Figure 2
A view of the molecule of (II), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
The presence of bulky 2-oxo-2-phenylethyl [in (II)] and
1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl [in (III)] substituents
on N2 of the triazole ring is the cause of asymmetry in the
angles around N2 (Table 1). In (II), the orientation of the
phenyl ring with respect to the tricylic ring system is defined by
the torsion angle N2—C10—C11—C12 of 165.41 (18)ꢁ, which
also reflects the overall conformation of the molecule in
extended form. On the other hand, in (III), the phenyl ring is
in an almost perpendicular orientation [ꢂ81.1 (4)ꢁ], perhaps
due to the more bulky 1-ethoxy-1,3-dioxo-3-phenylpropan-2-
yl substituent at N2. Compound (III) exists in the trans-
ꢀ-diketo form. As suggested by Bertolasi et al. (2008), on
keto–enol tautomerization of ꢀ-diketones from X-ray struc-
ture data and density functional theory calculations, the steric
hindrance of bulky group substituents plays a role in shifting
the more common ꢀ-keto–enol tautomer to the ꢀ-diketo form.
Furthermore, they also reported that the occurrence of the
trans ꢀ-diketo form in crystal structures can be interpreted in
terms of the existence of a high activation energy in the
mechanism to attain the ꢀ-keto–enol form. The O atoms of
Figure 3
A view of the molecule of (III), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level. The
minor components of the disordered ethoxy group (atoms O41, C191 and
C201) have been omitted for clarity.
ethyl, (II), and 1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl, (III),
derivatives.
The structures of (I)–(III) (Figs. 1–3) consist of a tricyclic
core, with triazole and benzene rings sharing the thiazine ring.
The interatomic distances and angles are unexceptional and
are comparable with those reported for related structures (de
Meester et al., 1986; Pilati & Simonetta, 1986). In (III), atoms
O4, C19 and C20 of the ethoxy group of the 1-ethoxy-1,3-
dioxo-3-phenylpropan-2-yl side chain are disordered over two
sites, with occupancies of 0.596 (15) and 0.404 (15).
The two crystallographically independent molecules in the
asymmetric unit of (I), labelled with the suffixes A and B, are
related by a pseudo-inversion centre which lies at
(0.0, 0.62, 0.63); the r.m.s. deviation for the mutual fit of the
˚
two molecules is 0.047 A. Dimers with pseudo-inversion
centres are formed by hydrogen bonds between the triazole
NH group of one molecule in the asymmetric unit and the
carbonyl O atom of the other, generating an R22(8) graph-set
motif (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995).
Significant structural similarities are seen in (I)–(III). In the
thiazine ring, the two S—C and N—C bond lengths (Table 1)
are unequal, owing to different environments. The C2—S1—
C3 angles of 99.26 (7) and 97.88 (7)ꢁ for molecules A and B,
respectively, in (I), 97.36 (10)ꢁ in (II) and 98.09 (15)ꢁ in (III)
suggest that atom S1 is involved solely in ꢂ bonds with C2 and
Figure 4
A superposition of the molecular conformations of (I)–(III), showing the
conformational similarity in their tricyclic ring systems, and also
highlighting the fact that the N2 substitution has no significant effect
on the conformation of the tricyclic ring systems. The overlay was made
by making a least-squares fit through the benzene ring (C1/C2/C5–C8) of
˚
molecule A of (I) [labelled (IA)]. The r.m.s. deviations (A) and labels are
as follows: 0.005, molecule B of (I), (IB); 0.008, (II); and 0.012, (III).
ꢃ
o476 Ravikumar et al.
C9H7N3OS, C17H13N3O2S and C20H17N3O4S Acta Cryst. (2012). C68, o475–o480

organic compounds
Figure 5
A partial packing diagram for (I), showing the two-dimensional network formed by intermolecular N—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀO interactions across the
centres of symmetry, and by C—Hꢀ ꢀ ꢀN interactions. All these interactions are shown as dashed lines and non-associated H atoms have been omitted for
1
3
clarity. Only atoms involved in the interactions are labelled. [Symmetry codes: (i) ꢂx + 2, ꢂy + 1, ꢂz + 1; (ii) ꢂx + 2, y + , ꢂz + .]
2
2
both the ketone (O2) and the ester (O3) carbonyl groups do
not point in the same direction. The dihedral angle between
the planes defined by atoms O2/C11/C10 and O3/C18/C10 is
81.2 (6)ꢁ. Carbonyl atom O2 of the ketone group and the
benzene ring are coplanar [O2—C11—C12—C17 = 0.9 (3)ꢁ in
(II) and 3.0 (5)ꢁ in (III)].
N—Hꢀ ꢀ ꢀO hydrogen bonds in (I) as mentioned earlier, the
crystal packing of (I)–(III) is essentially governed by C—
Hꢀ ꢀ ꢀO/N and ꢁ–ꢁ stacking interactions (Tables 2–4).
In (I), dimers related to each other by an inversion centre
are linked alternately in a head-to-tail manner via C—Hꢀ ꢀ ꢀO
Partial packing diagrams for (I)–(III) are given in Figs. 5–7.
In the absence of conventional hydrogen bonds, other than
Figure 7
Figure 6
A partial packing diagram for (III), showing the formation of the
centrosymmetric rings [R22(22) and R22(16)], along with another R22(16)
ring built from C—Hꢀ ꢀ ꢀO interactions (dashed lines). The minor
components of disordered atoms O41/C191/C201 and non-associated H
atoms have been omitted for clarity. Only atoms involved in the
interactions are labelled. [Symmetry codes: (i) ꢂx + 12, ꢂy + 21, ꢂz + 1; (ii)
A partial packing diagram for (II), showing the formation of the C—
Hꢀ ꢀ ꢀO centrosymmetric dimer [R22(10)] and the intermolecular ꢁ–ꢁ
interaction (dashed lines). Cg1 is the centroid of the six-membered C1/
C2/C5–C8 benzene ring. Non-associated H atoms have been omitted for
clarity. Only atoms involved in the interactions are labelled. [Symmetry
code: (i) ꢂx + 2, ꢂy, ꢂz + 2; (ii) x, ꢂy + 12, z ꢂ ; (iii) ꢂx + 1, y + 21, ꢂz + 23.]
ꢂx, ꢂy + 1, ꢂz + 1; (iii) ꢂx, y, ꢂz + .]
1
2
1
2
ꢃ
Acta Cryst. (2012). C68, o475–o480
Ravikumar et al.
C9H7N3OS, C17H13N3O2S and C20H17N3O4S o477

organic compounds
interactions (C3A—Hꢀ ꢀ ꢀO1Bi; details and symmetry code in
Table 2), forming an R42(14) ring motif. These dimers are
further linked by C—Hꢀ ꢀ ꢀN and C—Hꢀ ꢀ ꢀO interactions
(C3B—H3Dꢀ ꢀ ꢀN1Bii and C3B—H3Cꢀ ꢀ ꢀO1Aii), generating an
R23(7) ring motif and forming a two-dimensional network that
extends parallel to the (100) plane. ꢁ–ꢁ stacking interactions
are observed between the triazole ring of molecule A and the
benzene ring of a neighbouring molecule B at (x, y ꢂ 1, z), and
between the triazole ring of molecule B and the benzene ring
of molecule A in the same pair of molecules [ring-centroid
Table 1
Selected geometric parameters (A, ) for (I), (II) and (III).
ꢁ
˚
Parameter
(IA)
(IB)
(II)
(III)
C2—S1
C3—S1
C4—N3
C5—N3
C9—N2
1.7619 (15)
1.8092 (18)
1.3831 (18)
1.4231 (18)
1.348 (2)
1.7668 (15)
1.8133 (17)
1.3826 (18)
1.4252 (17)
1.347 (2)
1.772 (2)
1.809 (2)
1.379 (3)
1.421 (2)
1.358 (3)
1.769 (3)
1.800 (3)
1.382 (3)
1.429 (4)
1.367 (4)
C4—N3—C9
C4—N3—C5
C9—N3—C5
106.95 (12)
125.63 (12)
126.80 (12)
106.88 (11)
124.80 (11)
128.22 (11)
107.32 (16)
124.48 (17)
127.94 (17)
107.6 (2)
124.8 (2)
127.6 (2)
˚
separations = 3.6373 (9) and 3.8044 (9) A, respectively].
The molecules of (II) are linked together by paired C10—
Hꢀ ꢀ ꢀO1i (details and symmetry code in Table 3) interactions,
forming a centrosymmetric R22(10) dimer. We believe this
could be facilitated by the extended conformation of the
molecule mentioned earlier. The face-to-face orientation of
the fused benzene rings from two centrosymmetrically related
molecules results in a ꢁ–ꢁ stacking interaction [ring-centroid
Compound (I)
Crystal data
3
˚
V = 3521.9 (5) A
Z = 16
C9H7N3OS
Mr = 205.24
Orthorhombic, Pbca
Mo Kꢃ radiation
ꢄ = 0.33 mmꢂ1
T = 294 K
0.18 ꢄ 0.16 ꢄ 0.07 mm
˚
a = 14.6307 (11) A
˚
separation = 3.6514 (14) A] and links the dimers into chains
which run parallel to the [100] direction.
˚
b = 8.5718 (7) A
˚
c = 28.083 (2) A
In (III), there are more intermolecular C—Hꢀ ꢀ ꢀO inter-
actions than in (II), due to the presence of the additional
1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl group. The molecules
are linked by paired C3—Hꢀ ꢀ ꢀO3i, C8—Hꢀ ꢀ ꢀO3ii and C13—
Hꢀ ꢀ ꢀO1iii interactions (details and symmetry codes Table 4),
forming centrosymmetric R22(16), R22(22) and R22(16) dimers,
respectively, which are interconnected. As also seen in (II),
there is a ꢁ–ꢁ stacking interaction between the fused benzene
rings of two centrosymmetrically related molecules [ring-
Data collection
Bruker SMART APEX CCD area-
detector diffractometer
23641 measured reflections
3092 independent reflections
2895 reflections with I > 2ꢂ(I)
Rint = 0.020
Refinement
R[F2 > 2ꢂ(F2)] = 0.030
wR(F2) = 0.083
S = 1.03
3092 reflections
261 parameters
H atoms treated by a mixture of
independent and constrained
refinement
ꢂ3
˚
˚
Áꢅmax = 0.24 e A
Áꢅmin = ꢂ0.18 e A
centroid separation = 3.987 (2) A], forming a two-dimensional
network parallel to (110).
ꢂ3
˚
In conclusion, this is the first report presenting the crystal
structures of benzothiazine-fused triazoles. The crystal-
lographic study shows that the N2 substitution has no signifi-
cant effect on the conformation of the tricyclic ring system.
The validity of the postulate that C—Hꢀ ꢀ ꢀO/N interactions
play a significant role in molecular assembly and crystal
packing (Desiraju, 2005) has been illustrated. These structures
are a useful addition to current knowledge of weak inter-
actions and their role in supramolecular networks, molecular
recognition and crystal engineering.
Compound (II)
Crystal data
3
˚
V = 1454.3 (4) A
Z = 4
C17H13N3O2S
Mr = 323.36
Monoclinic, P21=c
Mo Kꢃ radiation
ꢄ = 0.24 mmꢂ1
T = 294 K
0.21 ꢄ 0.12 ꢄ 0.08 mm
˚
a = 11.6248 (18) A
˚
b = 14.920 (2) A
˚
c = 8.5909 (13) A
ꢀ = 102.564 (3)ꢁ
Data collection
Bruker SMART APEX CCD area-
detector diffractometer
13803 measured reflections
2562 independent reflections
2175 reflections with I > 2ꢂ(I)
Rint = 0.035
Experimental
The syntheses of (I) and (II) (SMS Pharma Research Centre,
Hyderabad) were reported previously (Reddy Sastry et al., 1991).
They were recrystallized from solutions in methanol (30 ml) for (I)
and ethyl acetate (30 ml) for (II) by slow evaporation. Compound
(III) (SMS Pharma Research Centre, Hyderabad) was prepared by
heating a mixture of (I) (100 mmol) and ethyl 2-bromo-3-oxo-3-
phenylpropanoate (105 mmol) in acetonitrile (20 ml) containing
anhydrous K2CO3 (200 mmol) and tetrabutylammonium bromide
(10 mmol) for 3 h under stirring and refluxing conditions. The reac-
tion mixture was then cooled to room temperature, filtered,
concentrated, triturated with ether (10 ml) and again filtered to yield
(III). Suitable single crystals of (III) were grown by slow evaporation
from a solution in methanol (30 ml).
Table 2
Hydrogen-bond geometry (A, ) for (I).
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N2B—H2Nꢀ ꢀ ꢀO1A
N2A—H1Nꢀ ꢀ ꢀO1B
C3A—H3Aꢀ ꢀ ꢀO1Bi
C3B—H3Cꢀ ꢀ ꢀO1Aii
C3B—H3Dꢀ ꢀ ꢀN1Bii
0.88 (2)
0.85 (2)
0.97
0.97
0.97
1.93 (2)
2.08 (2)
2.55
2.7771 (17)
2.9112 (18)
3.402 (2)
163.4 (17)
168.4 (17)
147
2.56
2.61
3.4238 (19)
3.444 (2)
149
144
1
3
Symmetry codes: (i) ꢂx þ 2; ꢂy þ 1; ꢂz þ 1; (ii) ꢂx þ 2; y þ ; ꢂz þ .
2
2
ꢃ
o478 Ravikumar et al.
C9H7N3OS, C17H13N3O2S and C20H17N3O4S
Acta Cryst. (2012). C68, o475–o480

organic compounds
Table 3
Hydrogen-bond geometry (A, ) for (II).
For all compounds, data collection: SMART (Bruker, 2001); cell
refinement: SAINT (Bruker, 2001); data reduction: SAINT;
program(s) used to solve structure: SHELXS97 (Sheldrick, 2008);
program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);
molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and
Mercury (Macrae et al., 2008); software used to prepare material for
publication: SHELXL97.
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
C10—H10Aꢀ ꢀ ꢀO1i
0.97
2.50
3.377 (3)
150
Symmetry code: (i) ꢂx þ 2; ꢂy; ꢂz þ 2.
Table 4
Hydrogen-bond geometry (A, ) for (III).
The authors thank Dr J. S. Yadav, Director, IICT, Hyder-
abad, for his kind encouragement.
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SF3180). Services for accessing these data are
described at the back of the journal.
C3—H3Aꢀ ꢀ ꢀO3i
C8—H8ꢀ ꢀ ꢀO3ii
C13—H13ꢀ ꢀ ꢀO1iii
0.97
0.93
0.93
2.47
2.46
2.58
3.153 (4)
3.265 (4)
3.330 (4)
127
145
138
1
2
1
2
Symmetry codes: (i) ꢂx þ ; ꢂy þ ; ꢂz þ 1; (ii) ꢂx; ꢂy þ 1; ꢂz þ 1; (iii) ꢂx; y,
1
ꢂz þ .
2
References
Aravindan, P. G., Rajakannan, V., Yogavel, M., Velmurugan, D., Senthilvelan,
A. & Suh, I.-H. (2003). Acta Cryst. E59, o622–o624.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555–1573.
Bertolasi, V., Ferretti, V., Gilli, P., Yao, X. & Li, C.-J. (2008). New J. Chem. 32,
694–704.
Refinement
R[F2 > 2ꢂ(F2)] = 0.046
wR(F2) = 0.110
S = 1.09
208 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢅmax = 0.29 e A
ꢂ3
˚
2562 reflections
Áꢅmin = ꢂ0.15 e A
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn,
Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin,
USA.
Compound (III)
Dalvie, D. K., Kalgutkar, A. S., Khojasteh-Bakht, S. C., Obach, R. S. &
O’Donnell, J. P. (2002). Chem. Res. Toxicol. 15, 269–299.
Desiraju, G. R. (2005). Chem. Commun. pp. 2995–3001.
Duran, A., Dogan, H. N. & Rollas, H. (2002). Il Farmaco, 57, 559–564.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.
Fringuelli, R., Schiaffella, F., Bistoni, F., Pitzurra, L. & Vecchiarelli, A. (1998).
Bioorg. Med. Chem. 6, 103–108.
Girmenia, C. (2009). Expert Opin. Investig. Drugs, 18, 1279–1295.
Guan, L. P., Jin, Q. H., Tian, G. R., Ghai, K. Y. & Quan, Z. S. (2007). J. Pharm.
Sci. 10, 254–262.
Gujjar, R., Marwaha, A., White, J., White, L., Creason, S., Shackleford, D. M.,
Baldwin, J., Charman, W. N., Buckner, F. S., Charman, S., Rathod, P. K. &
Philips, M. A. (2009). J. Med. Chem. 52, 1864–1872.
Gupta, R. R. & Ojha, K. G. (1988). Phenothiazines and 1,4-Benzothiazines:
Chemical and Biomedical Aspects, edited by R. R. Gupta, pp. 163–260.
Amsterdam: Elsevier.
Crystal data
3
˚
V = 3807.9 (6) A
Z = 8
C20H17N3O4S
Mr = 395.43
Monoclinic, C2=c
a = 13.6533 (14) A
Mo Kꢃ radiation
ꢄ = 0.20 mmꢂ1
T = 294 K
0.16 ꢄ 0.14 ꢄ 0.05 mm
˚
˚
b = 12.7279 (13) A
˚
c = 22.2927 (19) A
ꢀ = 100.601 (3)ꢁ
Data collection
Bruker SMART APEX CCD area-
detector diffractometer
17579 measured reflections
3355 independent reflections
2804 reflections with I > 2ꢂ(I)
Rint = 0.048
Refinement
Hafez, H. N., Abbas, H. A. & El-Gazzar, A. R. (2008). Acta Pharm. 58, 359–
378.
Holla, B. S., Akberali, P. M. & Shivananda, M. K. (2001). Il Farmaco, 56, 919–
927.
Holla, B. S., Poorjary, N. K., Rao, S. B. & Shivananda, M. K. (2002). Eur. J.
Med. Chem. 37, 511–517.
R[F2 > 2ꢂ(F2)] = 0.064
wR(F2) = 0.166
S = 1.19
3355 reflections
283 parameters
52 restraints
H-atom parameteꢂrs3 constrained
˚
Áꢅmax = 0.46 e A
ꢂ3
˚
Áꢅmin = ꢂ0.28 e A
Horne, W. S., Yadav, M. K., Stout, C. D. & Ghadiri, M. R. (2004). J. Am. Chem.
Soc. 126, 15366–15367.
Johns, B. A., Weatherhead, J. G., Allen, S. H., Thompson, J. B., Garvey, E. P. &
Foster, S. A. (2009). Bioorg. Med. Chem. Lett. 19, 1802–1806.
Junnarkar, A. Y., Singh, P. P., Patnaik, G. K. & Shrotri, D. S. (1992). Pharmacol.
Res. 26, 131–141.
Kobayashi, T., Strobek, M., Shwartz, A. & Mori, Y. (1997). Eur. J. Pharmacol.
332, 313–320.
Liu, P., Zhu, S. & Xie, W. (2008). Bioorg. Med. Chem. Lett. 18, 3261–3265.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,
Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood,
P. A. (2008). J. Appl. Cryst. 41, 466–470.
Matsumoto, Y., Tsuzuki, R., Matsuhisa, A., Yamagiwa, Y., Yanagisawa, I.,
Shibanuma, T. & Nohira, H. (2000). Bioorg. Med. Chem. 8, 393–404.
Meester, P. de, Chu, S. S. C. & Biehl, E. R. (1986). Acta Cryst. C42, 877–879.
Pilati, T. & Simonetta, M. (1986). Acta Cryst. C42, 1425–1428.
Ravikumar, K. & Sridhar, B. (2010). Acta Cryst. C66, o317–o320.
Ravikumar, K., Sridhar, B., Bhujanga Rao, A. K. S. & Pulla Reddy, M. (2011).
Acta Cryst. C67, o29–o32.
In (III), atoms O4, C19 and C20 are disordered over two sites and
the site-occupation factors refined to 0.596 (15) and 0.404 (15). The
anisotropic displacement parameters of the disordered atoms were
restrained to be similar [SIMU instruction in SHELXL97 (Sheldrick,
2008)] and the direction of motion along the axis between these
atoms was also restrained (DELU instruction in SHELXL97). The
C—C distances of the disordered groups were restrained to
˚
1.55 (1) A and the C18—O4 and O4—C19 distances to 1.33 (1) and
˚
1.45 (1) A, respectively. The N-bound H atoms of (I) were located in
a difference Fourier map and their positions and isotropic displace-
ment parameters were refined. The C-bound H atoms of (I), (II) and
(III) were located in difference density maps, but were positioned
geometrically and included as riding atoms, with C—H = 0.93
˚
(aromatic), 0.96 (methyl) or 0.97 A (methylene), and with Uiso(H) =
1.5Ueq(C) for the methyl groups or 1.2Ueq(C) otherwise. The methyl
groups were allowed to rotate but not to tip.
Ravikumar, K., Sridhar, B., Nanubolu, J. B., Hariharakrishnan, V. & Singh,
A. N. (2012). Acta Cryst. C68, o302–o307.
ꢃ
Acta Cryst. (2012). C68, o475–o480
Ravikumar et al.
C9H7N3OS, C17H13N3O2S and C20H17N3O4S o479

organic compounds
Reddy Sastry, C. V., Narayan, G. K. A. S. S., Krishnan, V. S. H., Vemana, K.,
Shridhar, D. R., Singh, P. P. & Junnarkar, A. Y. (1991). Indian J. Chem. Sect.
B, 30, 953–961.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Silverman, R. B. (2004). Editor. The Organic Chemistry of Drug Design and
Drug Action, 2nd ed. New York: Academic Press.
ꢃ
o480 Ravikumar et al.
C9H7N3OS, C17H13N3O2S and C20H17N3O4S
Acta Cryst. (2012). C68, o475–o480

supplementary materials
supplementary materials
Acta Cryst. (2012). C68, o475–o480 [doi:10.1107/S0108270112040759]
Three novel benzothiazine-fused triazoles as potential centrally acting muscle
relaxants
Krishnan Ravikumar, Balasubramanian Sridhar, Venkatasubramanian Hariharakrishnan and
Awadesh Narain Singh
(I) 4H-1,2,4-Triazolo[3,4-c][1,4]benzothiazin-1(2H)-one
Crystal data
C9H7N3OS
Mr = 205.24
F(000) = 1696
Dx = 1.548 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 7940 reflections
θ = 2.8–27.9°
Orthorhombic, Pbca
Hall symbol: -P 2ac 2ab
a = 14.6307 (11) Å
b = 8.5718 (7) Å
c = 28.083 (2) Å
V = 3521.9 (5) Å3
Z = 16
µ = 0.33 mm−1
T = 294 K
Block, colourless
0.18 × 0.16 × 0.07 mm
Data collection
Bruker SMART APEX CCD area-detector
diffractometer
2895 reflections with I > 2σ(I)
Rint = 0.020
Radiation source: fine-focus sealed tube
Graphite monochromator
ω scans
23641 measured reflections
3092 independent reflections
θmax = 25.0°, θmin = 2.0°
h = −17→17
k = −10→10
l = −33→33
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.030
wR(F2) = 0.083
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.03
3092 reflections
261 parameters
0 restraints
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0472P)2 + 1.2353P]
where P = (Fo2 + 2Fc2)/3
Primary atom site location: structure-invariant
direct methods
(Δ/σ)max = 0.002
Δρmax = 0.24 e Å−3
Δρmin = −0.18 e Å−3
Acta Cryst. (2012). C68, o475–o480
sup-1

supplementary materials
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
C1A
H1A
C2A
C3A
H3A
H3B
C4A
C5A
C6A
H6A
C7A
H7A
C8A
H8A
C9A
N1A
N2A
N3A
H1N
O1A
S1A
C1B
H1B
C2B
C3B
H3C
H3D
C4B
C5B
C6B
H6B
C7B
H7B
C8B
H8B
C9B
N1B
N2B
N3B
H2N
0.84019 (11)
0.8313
−0.11143 (18)
−0.2029
0.61793 (6)
0.6007
0.0445 (4)
0.053*
0.85524 (10)
0.82292 (12)
0.8329
0.02781 (17)
0.2168 (2)
0.2402
0.59376 (5)
0.51776 (6)
0.4844
0.0357 (3)
0.0469 (4)
0.056*
0.7578
0.2214
0.5240
0.056*
0.87140 (10)
0.86734 (9)
0.86333 (10)
0.8697
0.33258 (18)
0.16437 (16)
0.15985 (18)
0.2512
0.54789 (5)
0.62042 (5)
0.66991 (5)
0.6875
0.0395 (3)
0.0323 (3)
0.0391 (3)
0.047*
0.84988 (11)
0.8487
0.0189 (2)
0.0153
0.69286 (6)
0.7260
0.0456 (4)
0.055*
0.83823 (11)
0.8291
−0.1162 (2)
−0.2106
0.66694 (6)
0.6825
0.0483 (4)
0.058*
0.93332 (10)
0.90420 (10)
0.94070 (10)
0.88573 (8)
0.9754 (13)
0.96071 (9)
0.86581 (3)
1.18683 (11)
1.2178
0.43507 (17)
0.46461 (16)
0.52891 (16)
0.30624 (13)
0.608 (2)
0.61350 (5)
0.53405 (5)
0.57515 (5)
0.59590 (4)
0.5746 (6)
0.65440 (4)
0.531275 (14)
0.63302 (6)
0.6502
0.0390 (3)
0.0499 (4)
0.0473 (3)
0.0342 (3)
0.057 (5)*
0.0504 (3)
0.04670 (14)
0.0453 (4)
0.054*
0.45606 (13)
0.02384 (5)
1.36233 (19)
1.4384
1.16244 (10)
1.09811 (12)
1.1078
1.22315 (17)
1.07916 (19)
1.0400
0.65508 (5)
0.73374 (5)
0.7657
0.0352 (3)
0.0444 (4)
0.053*
1.0444
1.1454
0.7340
0.053*
1.08442 (10)
1.11430 (9)
1.09161 (10)
1.0589
0.94730 (17)
1.11109 (16)
1.13879 (18)
1.0648
0.70038 (5)
0.62890 (5)
0.58181 (5)
0.5646
0.0352 (3)
0.0312 (3)
0.0374 (3)
0.045*
1.11793 (11)
1.1034
1.2773 (2)
1.2954
0.56047 (6)
0.5287
0.0457 (4)
0.055*
1.16549 (12)
1.1831
1.38856 (19)
1.4811
0.58584 (6)
0.5712
0.0505 (4)
0.061*
1.06956 (10)
1.06615 (9)
1.05896 (9)
1.08893 (8)
1.0370 (12)
0.82465 (16)
0.80492 (15)
0.72947 (15)
0.96891 (13)
0.634 (2)
0.63058 (5)
0.71179 (4)
0.66834 (5)
0.65165 (4)
0.6670 (6)
0.0359 (3)
0.0421 (3)
0.0426 (3)
0.0320 (3)
0.054 (5)*
Acta Cryst. (2012). C68, o475–o480
sup-2

supplementary materials
O1B
S1B
1.06371 (8)
1.19697 (3)
0.79255 (12)
1.19015 (5)
0.58797 (4)
0.0466 (3)
0.714522 (14)
0.04555 (14)
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1A
C2A
C3A
C4A
C5A
C6A
C7A
C8A
C9A
N1A
N2A
N3A
O1A
S1A
C1B
C2B
C3B
C4B
C5B
C6B
C7B
C8B
C9B
N1B
N2B
N3B
O1B
S1B
0.0450 (8)
0.0336 (7)
0.0514 (9)
0.0423 (8)
0.0310 (7)
0.0441 (8)
0.0473 (9)
0.0483 (9)
0.0447 (8)
0.0581 (9)
0.0581 (9)
0.0396 (6)
0.0686 (8)
0.0572 (3)
0.0451 (9)
0.0348 (7)
0.0562 (9)
0.0383 (7)
0.0304 (7)
0.0386 (7)
0.0508 (9)
0.0561 (10)
0.0394 (8)
0.0526 (8)
0.0578 (8)
0.0376 (6)
0.0658 (7)
0.0524 (3)
0.0329 (8)
0.0351 (8)
0.0545 (10)
0.0397 (8)
0.0306 (7)
0.0382 (8)
0.0521 (10)
0.0408 (9)
0.0306 (7)
0.0465 (8)
0.0331 (7)
0.0298 (6)
0.0412 (6)
0.0463 (2)
0.0338 (8)
0.0323 (7)
0.0444 (9)
0.0368 (7)
0.0280 (7)
0.0380 (8)
0.0462 (9)
0.0353 (8)
0.0305 (7)
0.0394 (7)
0.0307 (7)
0.0283 (6)
0.0385 (6)
0.0455 (2)
0.0556 (10)
−0.0063 (7)
−0.0025 (6)
−0.0057 (8)
−0.0004 (7)
−0.0015 (6)
−0.0009 (7)
−0.0018 (7)
−0.0058 (7)
−0.0034 (6)
−0.0050 (7)
−0.0098 (6)
−0.0023 (5)
−0.0170 (5)
−0.00550 (18)
−0.0073 (7)
0.0002 (6)
−0.0041 (7)
−0.0004 (6)
−0.0059 (7)
−0.0011 (6)
0.0020 (5)
0.0029 (6)
0.0035 (7)
−0.0006 (8)
0.0047 (6)
−0.0045 (6)
−0.0014 (6)
0.0015 (5)
0.0016 (5)
0.00072 (17)
0.0042 (7)
0.0024 (6)
0.0056 (7)
0.0025 (6)
0.0049 (5)
0.0024 (6)
0.0064 (7)
0.0112 (8)
0.0016 (6)
0.0001 (5)
−0.0013 (6)
0.0020 (5)
0.0034 (5)
−0.00671 (16)
−0.0022 (7)
−0.0035 (6)
0.0021 (7)
0.0042 (6)
−0.0001 (6)
−0.0027 (6)
0.0085 (7)
0.0150 (7)
−0.0026 (6)
0.0118 (6)
0.0384 (8)
0.0347 (8)
0.0365 (8)
0.0353 (7)
0.0349 (8)
0.0375 (8)
0.0559 (10)
0.0417 (8)
0.0450 (8)
0.0507 (8)
0.0333 (6)
0.0414 (6)
0.0366 (2)
0.0571 (10)
0.0385 (7)
0.0327 (8)
0.0304 (7)
0.0351 (7)
0.0354 (7)
0.0401 (8)
0.0600 (10)
0.0378 (8)
0.0343 (7)
0.0394 (7)
0.0301 (6)
0.0355 (6)
0.0388 (2)
0.0052 (6)
0.0004 (5)
−0.0068 (5)
−0.01162 (17)
−0.0038 (7)
−0.0042 (6)
−0.0050 (7)
−0.0007 (6)
−0.0010 (6)
−0.0004 (6)
0.0090 (7)
−0.0037 (7)
−0.0021 (6)
0.0001 (5)
−0.0017 (6)
0.0036 (7)
−0.0036 (7)
−0.0042 (6)
−0.0066 (6)
−0.0096 (6)
−0.0039 (5)
−0.0128 (5)
−0.00944 (17)
0.0103 (7)
−0.0032 (6)
0.0024 (5)
0.0001 (5)
−0.0022 (5)
−0.0075 (4)
−0.00798 (16)
Geometric parameters (Å, º)
C1A—C8A
C1A—C2A
C1A—H1A
C2A—C5A
C2A—S1A
C3A—C4A
C3A—S1A
C3A—H3A
C3A—H3B
C4A—N1A
C4A—N3A
C5A—C6A
C5A—N3A
1.377 (2)
C1B—C8B
C1B—C2B
C1B—H1B
C2B—C5B
C2B—S1B
C3B—C4B
C3B—S1B
C3B—H3C
C3B—H3D
C4B—N1B
C4B—N3B
C5B—C6B
C5B—N3B
1.380 (2)
1.391 (2)
0.9300
1.391 (2)
0.9300
1.401 (2)
1.7619 (15)
1.485 (2)
1.8092 (18)
0.9700
1.400 (2)
1.7668 (15)
1.482 (2)
1.8133 (17)
0.9700
0.9700
0.9700
1.289 (2)
1.3831 (18)
1.392 (2)
1.4231 (18)
1.2898 (19)
1.3826 (18)
1.384 (2)
1.4252 (17)
Acta Cryst. (2012). C68, o475–o480
sup-3

supplementary materials
C6A—C7A
C6A—H6A
C7A—C8A
C7A—H7A
C8A—H8A
C9A—O1A
C9A—N2A
C9A—N3A
N1A—N2A
N2A—H1N
1.383 (2)
0.9300
C6B—C7B
C6B—H6B
C7B—C8B
C7B—H7B
C8B—H8B
C9B—O1B
C9B—N2B
C9B—N3B
N1B—N2B
N2B—H2N
1.384 (2)
0.9300
1.379 (2)
0.9300
1.379 (2)
0.9300
0.9300
0.9300
1.2299 (18)
1.348 (2)
1.3959 (19)
1.386 (2)
0.85 (2)
1.2310 (18)
1.347 (2)
1.3998 (18)
1.3849 (18)
0.88 (2)
C8A—C1A—C2A
C8A—C1A—H1A
C2A—C1A—H1A
C1A—C2A—C5A
C1A—C2A—S1A
C5A—C2A—S1A
C4A—C3A—S1A
C4A—C3A—H3A
S1A—C3A—H3A
C4A—C3A—H3B
S1A—C3A—H3B
H3A—C3A—H3B
N1A—C4A—N3A
N1A—C4A—C3A
N3A—C4A—C3A
C6A—C5A—C2A
C6A—C5A—N3A
C2A—C5A—N3A
C7A—C6A—C5A
C7A—C6A—H6A
C5A—C6A—H6A
C8A—C7A—C6A
C8A—C7A—H7A
C6A—C7A—H7A
C1A—C8A—C7A
C1A—C8A—H8A
C7A—C8A—H8A
O1A—C9A—N2A
O1A—C9A—N3A
N2A—C9A—N3A
C4A—N1A—N2A
C9A—N2A—N1A
C9A—N2A—H1N
N1A—N2A—H1N
C4A—N3A—C9A
C4A—N3A—C5A
C9A—N3A—C5A
C2A—S1A—C3A
121.10 (15)
119.4
C8B—C1B—C2B
C8B—C1B—H1B
C2B—C1B—H1B
C1B—C2B—C5B
C1B—C2B—S1B
C5B—C2B—S1B
C4B—C3B—S1B
C4B—C3B—H3C
S1B—C3B—H3C
C4B—C3B—H3D
S1B—C3B—H3D
H3C—C3B—H3D
N1B—C4B—N3B
N1B—C4B—C3B
N3B—C4B—C3B
C6B—C5B—C2B
C6B—C5B—N3B
C2B—C5B—N3B
C5B—C6B—C7B
C5B—C6B—H6B
C7B—C6B—H6B
C8B—C7B—C6B
C8B—C7B—H7B
C6B—C7B—H7B
C7B—C8B—C1B
C7B—C8B—H8B
C1B—C8B—H8B
O1B—C9B—N2B
O1B—C9B—N3B
N2B—C9B—N3B
C4B—N1B—N2B
C9B—N2B—N1B
C9B—N2B—H2N
N1B—N2B—H2N
C4B—N3B—C9B
C4B—N3B—C5B
C9B—N3B—C5B
C2B—S1B—C3B
120.63 (15)
119.7
119.4
119.7
118.45 (14)
118.90 (11)
122.51 (11)
109.02 (11)
109.9
118.93 (14)
119.00 (12)
122.02 (11)
108.66 (10)
110.0
109.9
110.0
109.9
110.0
109.9
110.0
108.3
108.3
112.38 (14)
126.36 (14)
121.25 (13)
120.35 (13)
120.99 (13)
118.64 (12)
119.71 (14)
120.1
112.49 (12)
126.36 (13)
121.14 (13)
120.32 (13)
120.84 (13)
118.84 (12)
119.61 (14)
120.2
120.1
120.2
120.35 (14)
119.8
120.65 (15)
119.7
119.8
119.7
120.00 (15)
120.0
119.84 (15)
120.1
120.0
120.1
129.24 (14)
127.51 (14)
103.25 (13)
103.97 (13)
113.39 (13)
122.6 (13)
122.3 (12)
106.95 (12)
125.63 (12)
126.80 (12)
99.26 (7)
128.46 (13)
128.49 (13)
103.04 (12)
103.81 (12)
113.71 (12)
124.8 (12)
120.1 (12)
106.88 (11)
124.80 (11)
128.22 (11)
97.88 (7)
Acta Cryst. (2012). C68, o475–o480
sup-4

supplementary materials
C8A—C1A—C2A—C5A
C8A—C1A—C2A—S1A
S1A—C3A—C4A—N1A
S1A—C3A—C4A—N3A
C1A—C2A—C5A—C6A
S1A—C2A—C5A—C6A
C1A—C2A—C5A—N3A
S1A—C2A—C5A—N3A
C2A—C5A—C6A—C7A
N3A—C5A—C6A—C7A
C5A—C6A—C7A—C8A
C2A—C1A—C8A—C7A
C6A—C7A—C8A—C1A
N3A—C4A—N1A—N2A
C3A—C4A—N1A—N2A
O1A—C9A—N2A—N1A
N3A—C9A—N2A—N1A
C4A—N1A—N2A—C9A
N1A—C4A—N3A—C9A
C3A—C4A—N3A—C9A
N1A—C4A—N3A—C5A
C3A—C4A—N3A—C5A
O1A—C9A—N3A—C4A
N2A—C9A—N3A—C4A
O1A—C9A—N3A—C5A
N2A—C9A—N3A—C5A
C6A—C5A—N3A—C4A
C2A—C5A—N3A—C4A
C6A—C5A—N3A—C9A
C2A—C5A—N3A—C9A
C1A—C2A—S1A—C3A
C5A—C2A—S1A—C3A
C4A—C3A—S1A—C2A
−0.8 (2)
C8B—C1B—C2B—C5B
−1.2 (2)
175.12 (12)
135.55 (15)
−44.59 (18)
−0.6 (2)
C8B—C1B—C2B—S1B
S1B—C3B—C4B—N1B
S1B—C3B—C4B—N3B
C1B—C2B—C5B—C6B
S1B—C2B—C5B—C6B
C1B—C2B—C5B—N3B
S1B—C2B—C5B—N3B
C2B—C5B—C6B—C7B
N3B—C5B—C6B—C7B
C5B—C6B—C7B—C8B
C6B—C7B—C8B—C1B
C2B—C1B—C8B—C7B
N3B—C4B—N1B—N2B
C3B—C4B—N1B—N2B
O1B—C9B—N2B—N1B
N3B—C9B—N2B—N1B
C4B—N1B—N2B—C9B
N1B—C4B—N3B—C9B
C3B—C4B—N3B—C9B
N1B—C4B—N3B—C5B
C3B—C4B—N3B—C5B
O1B—C9B—N3B—C4B
N2B—C9B—N3B—C4B
O1B—C9B—N3B—C5B
N2B—C9B—N3B—C5B
C6B—C5B—N3B—C4B
C2B—C5B—N3B—C4B
C6B—C5B—N3B—C9B
C2B—C5B—N3B—C9B
C1B—C2B—S1B—C3B
C5B—C2B—S1B—C3B
C4B—C3B—S1B—C2B
176.39 (13)
135.70 (14)
−45.50 (18)
0.1 (2)
−176.39 (11)
177.98 (13)
2.23 (19)
−177.41 (11)
−179.66 (13)
2.84 (18)
1.8 (2)
0.9 (2)
−176.78 (14)
−1.6 (2)
−179.36 (13)
−0.8 (2)
1.0 (2)
−0.3 (3)
0.2 (3)
1.3 (3)
−0.83 (18)
179.04 (15)
177.94 (16)
−2.56 (18)
2.19 (19)
0.40 (17)
179.30 (15)
−177.27 (15)
2.78 (17)
−2.08 (18)
1.26 (17)
−0.68 (18)
179.44 (14)
−172.14 (14)
8.0 (2)
−177.70 (14)
−175.30 (13)
5.7 (2)
−178.59 (16)
1.90 (16)
177.70 (15)
−2.35 (15)
−5.9 (3)
−7.3 (2)
173.22 (13)
−164.62 (14)
16.8 (2)
174.06 (13)
−160.55 (13)
19.2 (2)
25.6 (2)
23.6 (2)
−153.01 (14)
150.82 (13)
−33.45 (14)
50.69 (12)
−156.61 (14)
146.30 (13)
−36.20 (13)
53.54 (12)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N2B—H2N···O1A
N2A—H1N···O1B
C3A—H3A···O1Bi
C3B—H3C···O1Aii
C3B—H3D···N1Bii
C6A—H6A···O1A
C6B—H6B···O1B
0.88 (2)
0.85 (2)
0.97
1.93 (2)
2.08 (2)
2.55
2.7771 (17)
2.9112 (18)
3.402 (2)
163.4 (17)
168.4 (17)
147
0.97
2.56
3.4238 (19)
3.444 (2)
149
0.97
2.61
144
0.93
2.39
2.9438 (19)
3.0009 (19)
118
0.93
2.43
120
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.
Acta Cryst. (2012). C68, o475–o480
sup-5

supplementary materials
(II) 2-(2-Oxo-2-phenylethyl)-4H-1,2,4-triazolo[3,4- c][1,4]benzothiazin-1(2H)-one
Crystal data
C17H13N3O2S
Mr = 323.36
F(000) = 672
Dx = 1.477 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3459 reflections
θ = 2.7–24.8°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 11.6248 (18) Å
b = 14.920 (2) Å
c = 8.5909 (13) Å
β = 102.564 (3)°
V = 1454.3 (4) Å3
Z = 4
µ = 0.24 mm−1
T = 294 K
Needle, colourless
0.21 × 0.12 × 0.08 mm
Data collection
Bruker SMART APEX CCD area-detector
diffractometer
2175 reflections with I > 2σ(I)
Rint = 0.035
Radiation source: fine-focus sealed tube
Graphite monochromator
ω scans
13803 measured reflections
2562 independent reflections
θmax = 25.0°, θmin = 1.8°
h = −13→13
k = −17→17
l = −10→10
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.046
wR(F2) = 0.110
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.09
2562 reflections
208 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0521P)2 + 0.4963P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.29 e Å−3
Δρmin = −0.15 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
C1
0.4068 (2)
0.3310
0.09302 (16)
0.1167
1.1514 (3)
1.1253
0.0476 (6)
0.057*
H1
C2
0.49454 (18)
0.59868 (19)
0.5992
0.12968 (14)
0.27745 (14)
0.3281
1.0841 (2)
0.9999 (3)
0.9293
0.0385 (5)
0.0430 (5)
0.052*
C3
H3A
H3B
C4
0.6110
0.2996
1.1084
0.052*
0.69294 (18)
0.60792 (17)
0.6323 (2)
0.21352 (14)
0.09307 (13)
0.02331 (14)
0.9852 (3)
1.1240 (2)
1.2319 (3)
0.0380 (5)
0.0347 (5)
0.0416 (5)
C5
C6
Acta Cryst. (2012). C68, o475–o480
sup-6

supplementary materials
H6
0.7082
0.0000
1.2604
0.050*
C7
0.5428 (2)
0.5591
−0.01189 (16)
−0.0589
1.2975 (3)
1.3700
0.0482 (6)
0.058*
H7
C8
0.4305 (2)
0.3706
0.02227 (17)
−0.0024
1.2560 (3)
1.2986
0.0509 (6)
0.061*
H8
C9
0.79549 (18)
0.94467 (19)
0.9951
0.08501 (14)
0.13928 (16)
0.0922
1.0186 (2)
0.8692 (3)
0.9245
0.0378 (5)
0.0458 (6)
0.055*
C10
H10A
H10B
C11
C12
C13
H13
C14
H14
C15
H15
C16
H16
C17
H17
N1
0.9892
0.1948
0.8831
0.055*
0.91012 (19)
1.00213 (18)
1.11552 (19)
1.1364
0.11681 (14)
0.12699 (14)
0.15584 (15)
0.1689
0.6929 (3)
0.5969 (3)
0.6638 (3)
0.7722
0.0408 (5)
0.0392 (5)
0.0454 (6)
0.055*
1.1977 (2)
1.2733
0.16532 (17)
0.1854
0.5704 (3)
0.6157
0.0532 (6)
0.064*
1.1678 (2)
1.2233
0.14515 (17)
0.1517
0.4112 (3)
0.3486
0.0552 (7)
0.066*
1.0565 (2)
1.0371
0.11529 (18)
0.1007
0.3433 (3)
0.2355
0.0586 (7)
0.070*
0.9732 (2)
0.8974
0.10688 (16)
0.0877
0.4353 (3)
0.3887
0.0500 (6)
0.060*
0.77836 (17)
0.84323 (16)
0.69649 (14)
0.83143 (13)
0.81152 (14)
0.45916 (5)
0.22750 (12)
0.14868 (12)
0.12901 (11)
0.00975 (10)
0.09055 (12)
0.21922 (4)
0.9143 (2)
0.9388 (2)
1.05118 (19)
1.05492 (19)
0.6344 (2)
0.94660 (7)
0.0466 (5)
0.0456 (5)
0.0349 (4)
0.0483 (4)
0.0599 (5)
0.0491 (2)
N2
N3
O1
O2
S1
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.0356 (12)
0.0360 (11)
0.0449 (13)
0.0393 (12)
0.0339 (11)
0.0423 (12)
0.0581 (15)
0.0516 (14)
0.0320 (11)
0.0368 (12)
0.0348 (12)
0.0380 (12)
0.0402 (12)
0.0384 (13)
0.0531 (15)
0.0686 (18)
0.0456 (13)
0.0469 (11)
0.0401 (10)
0.0601 (15)
0.0436 (12)
0.0395 (12)
0.0375 (11)
0.0393 (11)
0.0420 (12)
0.0461 (13)
0.0569 (15)
0.0429 (12)
0.0519 (14)
0.0358 (11)
0.0352 (11)
0.0552 (14)
0.0649 (16)
0.0637 (16)
0.0667 (17)
0.0531 (15)
0.0433 (11)
0.0443 (11)
0.0513 (14)
−0.0071 (11)
−0.0042 (9)
0.0035 (10)
0.0003 (9)
0.0185 (11)
0.0129 (9)
0.0183 (10)
0.0149 (9)
0.0161 (9)
0.0161 (10)
0.0258 (11)
0.0307 (12)
0.0130 (9)
0.0242 (10)
0.0171 (10)
0.0160 (10)
0.0163 (10)
0.0216 (11)
0.0326 (13)
0.0215 (13)
0.0111 (11)
0.0266 (9)
0.0294 (9)
−0.0126 (12)
−0.0081 (9)
0.0024 (10)
0.0010 (9)
C2
0.0382 (11)
0.0483 (13)
0.0400 (12)
0.0350 (11)
0.0437 (12)
0.0470 (13)
0.0529 (14)
0.0409 (12)
0.0553 (14)
0.0551 (14)
0.0475 (13)
0.0442 (13)
0.0613 (16)
0.0582 (16)
0.0446 (14)
0.0516 (14)
0.0566 (12)
0.0607 (12)
C3
C4
C5
−0.0047 (9)
−0.0004 (10)
−0.0074 (11)
−0.0192 (12)
0.0009 (9)
−0.0056 (9)
0.0000 (10)
0.0011 (11)
−0.0110 (12)
−0.0001 (10)
0.0048 (11)
0.0076 (10)
0.0044 (9)
C6
C7
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
N1
0.0019 (10)
0.0009 (9)
0.0018 (9)
−0.0009 (11)
−0.0015 (11)
0.0097 (12)
0.0063 (14)
−0.0020 (11)
0.0031 (9)
0.0015 (11)
0.0047 (13)
0.0083 (13)
−0.0011 (12)
−0.0027 (11)
0.0075 (9)
N2
0.0060 (8)
0.0082 (9)
Acta Cryst. (2012). C68, o475–o480
sup-7

supplementary materials
N3
O1
O2
S1
0.0324 (9)
0.0435 (9)
0.0381 (9)
0.0369 (3)
0.0366 (9)
0.0432 (9)
0.0722 (12)
0.0576 (4)
0.0392 (10)
0.0630 (10)
0.0709 (12)
0.0528 (4)
0.0000 (7)
0.0098 (7)
−0.0120 (8)
0.0076 (3)
0.0157 (7)
0.0222 (8)
0.0155 (8)
0.0098 (3)
0.0017 (7)
0.0093 (8)
0.0020 (9)
0.0049 (3)
Geometric parameters (Å, º)
C1—C8
C1—C2
C1—H1
C2—C5
C2—S1
C3—C4
C3—S1
C3—H3A
C3—H3B
C4—N1
C4—N3
C5—C6
C5—N3
C6—C7
C6—H6
C7—C8
C7—H7
C8—H8
C9—O1
C9—N2
1.375 (3)
C9—N3
1.405 (3)
1.389 (3)
0.9300
C10—N2
1.440 (3)
1.518 (3)
0.9700
C10—C11
C10—H10A
C10—H10B
C11—O2
1.399 (3)
1.772 (2)
1.479 (3)
1.809 (2)
0.9700
0.9700
1.212 (3)
1.494 (3)
1.387 (3)
1.388 (3)
1.382 (3)
0.9300
C11—C12
C12—C13
C12—C17
C13—C14
C13—H13
C14—C15
C14—H14
C15—C16
C15—H15
C16—C17
C16—H16
C17—H17
N1—N2
0.9700
1.290 (3)
1.379 (3)
1.381 (3)
1.421 (2)
1.389 (3)
0.9300
1.370 (4)
0.9300
1.373 (4)
0.9300
1.374 (3)
0.9300
1.382 (3)
0.9300
0.9300
0.9300
1.215 (3)
1.358 (3)
1.388 (3)
C8—C1—C2
C8—C1—H1
C2—C1—H1
C1—C2—C5
C1—C2—S1
C5—C2—S1
C4—C3—S1
C4—C3—H3A
S1—C3—H3A
C4—C3—H3B
S1—C3—H3B
H3A—C3—H3B
N1—C4—N3
N1—C4—C3
N3—C4—C3
C6—C5—C2
C6—C5—N3
C2—C5—N3
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
120.9 (2)
119.6
N2—C10—H10B
C11—C10—H10B
H10A—C10—H10B
O2—C11—C12
O2—C11—C10
C12—C11—C10
C13—C12—C17
C13—C12—C11
C17—C12—C11
C14—C13—C12
C14—C13—H13
C12—C13—H13
C15—C14—C13
C15—C14—H14
C13—C14—H14
C14—C15—C16
C14—C15—H15
C16—C15—H15
C15—C16—C17
C15—C16—H16
C17—C16—H16
C16—C17—C12
109.2
109.2
119.6
107.9
118.8 (2)
122.0 (2)
120.42 (19)
117.57 (18)
118.9 (2)
122.2 (2)
118.9 (2)
120.4 (2)
119.8
119.30 (17)
121.83 (16)
108.00 (15)
110.1
110.1
110.1
110.1
108.4
119.8
112.62 (18)
126.63 (19)
120.75 (18)
120.21 (19)
121.15 (18)
118.64 (18)
119.6 (2)
120.2
120.0 (2)
120.0
120.0
120.4 (2)
119.8
119.8
120.0 (2)
120.0
120.2
120.0
120.5 (2)
120.3 (2)
Acta Cryst. (2012). C68, o475–o480
sup-8

supplementary materials
C8—C7—H7
C6—C7—H7
C7—C8—C1
C7—C8—H8
C1—C8—H8
O1—C9—N2
O1—C9—N3
N2—C9—N3
N2—C10—C11
N2—C10—H10A
C11—C10—H10A
119.8
C16—C17—H17
C12—C17—H17
C4—N1—N2
C9—N2—N1
C9—N2—C10
N1—N2—C10
C4—N3—C9
C4—N3—C5
C9—N3—C5
C2—S1—C3
119.8
119.8
119.8
119.9 (2)
120.1
103.88 (17)
113.63 (16)
127.04 (19)
119.11 (17)
107.32 (16)
124.48 (17)
127.94 (17)
97.36 (10)
120.1
128.37 (19)
129.14 (19)
102.48 (18)
111.90 (19)
109.2
109.2
C8—C1—C2—C5
0.3 (3)
C11—C12—C17—C16
N3—C4—N1—N2
C3—C4—N1—N2
O1—C9—N2—N1
N3—C9—N2—N1
O1—C9—N2—C10
N3—C9—N2—C10
C4—N1—N2—C9
C4—N1—N2—C10
C11—C10—N2—C9
C11—C10—N2—N1
N1—C4—N3—C9
C3—C4—N3—C9
N1—C4—N3—C5
C3—C4—N3—C5
O1—C9—N3—C4
N2—C9—N3—C4
O1—C9—N3—C5
N2—C9—N3—C5
C6—C5—N3—C4
C2—C5—N3—C4
C6—C5—N3—C9
C2—C5—N3—C9
C1—C2—S1—C3
C5—C2—S1—C3
C4—C3—S1—C2
−179.8 (2)
−1.6 (2)
C8—C1—C2—S1
178.64 (17)
132.3 (2)
−47.9 (2)
−1.8 (3)
179.94 (16)
178.11 (18)
−0.2 (3)
1.7 (3)
S1—C3—C4—N1
178.2 (2)
179.0 (2)
−2.4 (2)
S1—C3—C4—N3
C1—C2—C5—C6
S1—C2—C5—C6
4.4 (4)
C1—C2—C5—N3
−177.0 (2)
2.6 (3)
S1—C2—C5—N3
C2—C5—C6—C7
177.6 (2)
95.9 (3)
N3—C5—C6—C7
−178.20 (19)
−0.1 (3)
−1.4 (3)
1.3 (3)
C5—C6—C7—C8
−78.4 (3)
0.2 (2)
C6—C7—C8—C1
C2—C1—C8—C7
−179.6 (2)
−174.29 (19)
5.9 (3)
N2—C10—C11—O2
N2—C10—C11—C12
O2—C11—C12—C13
C10—C11—C12—C13
O2—C11—C12—C17
C10—C11—C12—C17
C17—C12—C13—C14
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C12
C13—C12—C17—C16
−15.5 (3)
165.41 (18)
−179.1 (2)
0.0 (3)
179.9 (2)
1.3 (2)
0.9 (3)
−5.8 (4)
180.0 (2)
0.7 (3)
175.59 (19)
−158.2 (2)
21.9 (3)
−179.3 (2)
−0.8 (4)
−0.1 (4)
1.1 (4)
28.4 (3)
−151.4 (2)
146.39 (18)
−35.34 (19)
55.21 (17)
−1.1 (4)
0.2 (4)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C6—H6···O1
C10—H10A···O1i
0.93
0.97
2.51
2.50
3.040 (3)
3.377 (3)
117
150
Symmetry code: (i) −x+2, −y, −z+2.
Acta Cryst. (2012). C68, o475–o480
sup-9

supplementary materials
(III) Ethyl 3-oxo-2-(1-oxo-1H,4H-1,2,4-triazolo[3,4- c][1,4]benzothiazin-2-yl)-3-phenylpropanoate
Crystal data
C20H17N3O4S
Mr = 395.43
F(000) = 1648
Dx = 1.380 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 8703 reflections
θ = 2.2–27.6°
Monoclinic, C2/c
a = 13.6533 (14) Å
b = 12.7279 (13) Å
c = 22.2927 (19) Å
β = 100.601 (3)°
V = 3807.9 (6) Å3
Z = 8
µ = 0.20 mm−1
T = 294 K
Plate, colourless
0.16 × 0.14 × 0.05 mm
Data collection
Bruker SMART APEX CCD area-detector
diffractometer
2804 reflections with I > 2σ(I)
Rint = 0.048
Radiation source: fine-focus sealed tube
Graphite monochromator
ω scans
17579 measured reflections
3355 independent reflections
θmax = 25.0°, θmin = 1.9°
h = −16→16
k = −15→15
l = −26→26
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.064
wR(F2) = 0.166
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.19
3355 reflections
283 parameters
52 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0585P)2 + 5.1188P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.46 e Å−3
Δρmin = −0.28 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
Occ. (<1)
C1
0.1257 (3)
0.1707
0.6780 (3)
0.7171
0.49936 (17)
0.5270
0.0713 (9)
0.086*
H1
C2
0.1566 (2)
0.2717 (2)
0.3365
0.5858 (2)
0.4125 (3)
0.3798
0.47527 (14)
0.49316 (17)
0.4959
0.0561 (8)
0.0663 (9)
0.080*
C3
H3A
H3B
C4
0.2449
0.3923
0.5289
0.080*
0.2046 (2)
0.0868 (2)
−0.0116 (2)
−0.0584
0.3758 (2)
0.5255 (2)
0.5580 (3)
0.5167
0.43767 (14)
0.43667 (13)
0.42121 (15)
0.3963
0.0508 (7)
0.0479 (7)
0.0583 (8)
0.070*
C5
C6
H6
Acta Cryst. (2012). C68, o475–o480
sup-10

supplementary materials
C7
−0.0390 (3)
−0.1040
0.6533 (3)
0.6774
0.44355 (19)
0.4319
0.0731 (10)
0.088*
H7
C8
0.0284 (3)
0.0088
0.7121 (3)
0.7753
0.48249 (19)
0.4977
0.0786 (11)
0.094*
H8
C9
0.0701 (2)
0.1045 (2)
0.0648
0.3720 (2)
0.1956 (3)
0.2151
0.36308 (14)
0.32654 (15)
0.2869
0.0512 (7)
0.0570 (8)
0.068*
C10
H10
C11
C12
C13
H13
C14
H14
C15
H15
C16
H16
C17
H17
C18
C19
H19A
H19B
C20
H20A
H20B
H20C
C191
H19C
H19D
C201
H20D
H20E
H20F
N1
0.1969 (2)
0.2457 (2)
0.2119 (3)
0.1581
0.1345 (3)
0.1677 (3)
0.2520 (3)
0.2916
0.31531 (15)
0.26426 (15)
0.22691 (17)
0.2342
0.0588 (8)
0.0588 (8)
0.0736 (10)
0.088*
0.2591 (4)
0.2368
0.2773 (4)
0.3338
0.1783 (2)
0.1530
0.0971 (13)
0.117*
0.3389 (4)
0.3703
0.2178 (5)
0.2342
0.1682 (2)
0.1357
0.1049 (16)
0.126*
0.3723 (3)
0.4269
0.1355 (5)
0.0969
0.2052 (2)
0.1981
0.0965 (14)
0.116*
0.3264 (3)
0.3489
0.1085 (3)
0.0512
0.25296 (17)
0.2776
0.0759 (10)
0.091*
0.0409 (3)
−0.0499 (11)
−0.0983
0.1266 (3)
−0.0273 (12)
0.0121
0.35988 (17)
0.3580 (5)
0.3757
0.0711 (9)
0.108 (4)
0.129*
0.596 (15)
0.596 (15)
0.596 (15)
0.596 (15)
0.596 (15)
0.596 (15)
0.596 (15)
0.404 (15)
0.404 (15)
0.404 (15)
0.404 (15)
0.404 (15)
0.404 (15)
0.404 (15)
−0.0074
−0.0663
0.3900
0.129*
−0.1003 (9)
−0.1326
−0.0990 (9)
−0.0583
0.3092 (5)
0.2750
0.125 (5)
0.188*
−0.1489
−0.1405
0.3246
0.188*
−0.0517
−0.1445
0.2966
0.188*
−0.0936 (11)
−0.1499
−0.0043 (9)
−0.0133
0.3354 (8)
0.3023
0.086 (3)
0.103*
−0.1177
0.0216
0.3710
0.103*
−0.0385 (14)
−0.0022
−0.1068 (13)
−0.1229
0.3497 (11)
0.3178
0.129 (7)
0.194*
−0.0854
−0.1620
0.3525
0.194*
0.0071
−0.1007
0.3878
0.194*
0.21558 (17)
0.13419 (17)
0.11885 (16)
−0.00803 (16)
0.2266 (2)
0.03282 (19)
0.0093 (8)
−0.0202 (9)
0.28467 (6)
0.2914 (2)
0.2904 (2)
0.42965 (18)
0.3894 (2)
0.0622 (2)
0.1373 (3)
0.0430 (8)
0.0687 (9)
0.55313 (7)
0.40800 (13)
0.36024 (12)
0.41295 (11)
0.32908 (10)
0.34810 (13)
0.41169 (12)
0.3264 (5)
0.3178 (6)
0.49131 (5)
0.0592 (7)
0.0578 (7)
0.0474 (6)
0.0698 (7)
0.0842 (8)
0.0878 (8)
0.091 (3)
0.073 (3)
0.0726 (3)
N2
N3
O1
O2
O3
O4
0.596 (15)
0.404 (15)
O41
S1
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
C2
C3
0.090 (3)
0.055 (2)
0.073 (2)
0.0590 (18)
0.079 (2)
−0.0011 (18)
0.0260 (19)
0.0198 (15)
−0.0043 (16)
−0.0096 (17)
0.0010 (14)
−0.0038 (17)
0.0635 (18)
0.0559 (19)
0.0490 (17)
0.0572 (19)
0.0027 (14)
0.0015 (15)
Acta Cryst. (2012). C68, o475–o480
sup-11

supplementary materials
C4
0.0424 (15)
0.0512 (16)
0.0512 (17)
0.066 (2)
0.0464 (16)
0.0467 (15)
0.0616 (19)
0.070 (2)
0.0624 (18)
0.0503 (16)
0.0671 (19)
0.093 (3)
0.0051 (12)
0.0045 (12)
0.0080 (14)
0.0186 (18)
0.014 (2)
0.0067 (13)
0.0212 (13)
0.0239 (14)
0.041 (2)
0.0011 (14)
0.0035 (13)
0.0053 (16)
0.006 (2)
C5
C6
C7
C8
0.097 (3)
0.056 (2)
0.096 (3)
0.051 (2)
−0.009 (2)
−0.0003 (14)
−0.0158 (15)
−0.0112 (16)
−0.0100 (16)
0.0039 (19)
0.010 (2)
C9
0.0418 (15)
0.0527 (16)
0.0608 (19)
0.0554 (17)
0.078 (2)
0.0578 (18)
0.0626 (19)
0.0549 (19)
0.063 (2)
0.0547 (17)
0.0563 (18)
0.0608 (19)
0.0593 (19)
0.069 (2)
0.0035 (13)
0.0011 (14)
0.0033 (15)
0.0015 (15)
0.0050 (19)
−0.006 (3)
−0.025 (3)
0.009 (3)
0.0110 (13)
0.0115 (14)
0.0114 (15)
0.0144 (14)
0.0207 (18)
0.028 (3)
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C191
C201
N1
0.077 (2)
0.119 (4)
0.098 (3)
0.079 (3)
0.105 (3)
0.141 (5)
0.079 (3)
0.043 (3)
−0.015 (3)
−0.024 (3)
−0.019 (2)
−0.0222 (18)
−0.012 (6)
−0.001 (6)
0.006 (6)
0.076 (3)
0.142 (4)
0.078 (3)
0.032 (2)
0.065 (2)
0.093 (3)
0.072 (2)
0.0142 (19)
−0.0078 (17)
−0.053 (7)
−0.061 (6)
−0.014 (4)
0.002 (8)
0.0188 (18)
0.0224 (17)
0.030 (6)
0.065 (2)
0.085 (2)
0.068 (2)
0.109 (9)
0.122 (8)
0.096 (7)
0.125 (9)
0.110 (7)
0.132 (8)
0.000 (7)
0.084 (8)
0.086 (7)
0.087 (9)
0.011 (6)
0.124 (13)
0.0419 (13)
0.0450 (13)
0.0415 (12)
0.0531 (13)
0.101 (2)
0.100 (8)
0.161 (17)
0.0753 (17)
0.0659 (16)
0.0546 (14)
0.0703 (15)
0.0906 (18)
0.0666 (16)
0.085 (5)
0.018 (12)
−0.0001 (12)
0.0031 (11)
0.0099 (10)
−0.0047 (11)
0.0334 (15)
0.0268 (13)
0.040 (4)
0.044 (11)
0.0564 (15)
0.0596 (15)
0.0463 (13)
0.0799 (16)
0.0672 (16)
0.124 (2)
0.0074 (11)
0.0069 (11)
0.0039 (10)
0.0147 (11)
0.0221 (14)
−0.0106 (15)
−0.042 (5)
−0.010 (4)
−0.0064 (4)
−0.0112 (13)
−0.0143 (13)
−0.0015 (11)
−0.0089 (12)
0.0120 (14)
−0.0198 (15)
−0.030 (4)
−0.019 (4)
−0.0099 (5)
N2
N3
O1
O2
O3
0.0776 (17)
0.099 (6)
O4
0.100 (6)
O41
S1
0.075 (6)
0.065 (4)
0.082 (5)
0.027 (4)
0.0596 (5)
0.0562 (5)
0.0978 (7)
0.0033 (5)
Geometric parameters (Å, º)
C1—C8
C1—C2
C1—H1
C2—C5
C2—S1
C3—C4
C3—S1
C3—H3A
C3—H3B
C4—N1
C4—N3
C5—C6
C5—N3
C6—C7
C6—H6
C7—C8
C7—H7
C8—H8
C9—O1
1.382 (5)
C12—C17
1.396 (5)
1.388 (5)
0.9300
C13—C14
C13—H13
C14—C15
C14—H14
C15—C16
C15—H15
C16—C17
C16—H16
C17—H17
C18—O3
1.396 (6)
0.9300
1.392 (4)
1.769 (3)
1.473 (4)
1.800 (3)
0.9700
1.380 (7)
0.9300
1.359 (7)
0.9300
1.375 (6)
0.9300
0.9700
1.284 (4)
1.382 (3)
1.387 (4)
1.429 (4)
1.388 (5)
0.9300
0.9300
1.188 (4)
1.325 (7)
1.354 (9)
1.469 (8)
1.488 (9)
0.9700
C18—O4
C18—O41
C19—O4
C19—C20
C19—H19A
C19—H19B
C20—H20A
C20—H20B
1.367 (5)
0.9300
0.9700
0.9300
0.9600
1.210 (3)
0.9600
Acta Cryst. (2012). C68, o475–o480
sup-12

supplementary materials
C9—N2
1.367 (4)
1.394 (4)
1.439 (4)
1.522 (5)
1.541 (4)
0.9800
C20—H20C
C191—O41
C191—C201
C191—H19C
C191—H19D
C201—H20D
C201—H20E
C201—H20F
N1—N2
0.9600
C9—N3
1.473 (9)
1.510 (9)
0.9700
C10—N2
C10—C18
C10—C11
C10—H10
C11—O2
C11—C12
C12—C13
0.9700
0.9600
1.198 (4)
1.482 (5)
1.384 (5)
0.9600
0.9600
1.390 (3)
C8—C1—C2
C8—C1—H1
C2—C1—H1
C1—C2—C5
C1—C2—S1
C5—C2—S1
C4—C3—S1
C4—C3—H3A
S1—C3—H3A
C4—C3—H3B
S1—C3—H3B
H3A—C3—H3B
N1—C4—N3
N1—C4—C3
N3—C4—C3
C6—C5—C2
C6—C5—N3
C2—C5—N3
C5—C6—C7
C5—C6—H6
C7—C6—H6
C8—C7—C6
C8—C7—H7
C6—C7—H7
C7—C8—C1
C7—C8—H8
C1—C8—H8
O1—C9—N2
O1—C9—N3
N2—C9—N3
N2—C10—C18
N2—C10—C11
C18—C10—C11
N2—C10—H10
C18—C10—H10
C11—C10—H10
O2—C11—C12
O2—C11—C10
C12—C11—C10
120.4 (4)
119.8
C15—C14—C13
C15—C14—H14
C13—C14—H14
C16—C15—C14
C16—C15—H15
C14—C15—H15
C15—C16—C17
C15—C16—H16
C17—C16—H16
C16—C17—C12
C16—C17—H17
C12—C17—H17
O3—C18—O4
119.4 (5)
120.3
119.8
120.3
119.0 (3)
118.7 (3)
122.2 (2)
110.2 (2)
109.6
120.7 (4)
119.6
119.6
120.9 (4)
119.6
109.6
119.6
109.6
119.5 (4)
120.3
109.6
108.1
120.3
112.3 (3)
125.8 (3)
121.8 (3)
120.6 (3)
120.7 (3)
118.6 (3)
119.0 (3)
120.5
124.1 (6)
125.5 (8)
124.9 (3)
110.2 (5)
108.0 (7)
104.2 (7)
110.9
O3—C18—O41
O3—C18—C10
O4—C18—C10
O41—C18—C10
O4—C19—C20
O4—C19—H19A
C20—C19—H19A
O4—C19—H19B
C20—C19—H19B
110.9
120.5
110.9
120.8 (3)
119.6
110.9
H19A—C19—H19B
O41—C191—C201
O41—C191—H19C
C201—C191—H19C
O41—C191—H19D
C201—C191—H19D
H19C—C191—H19D
C191—C201—H20D
C191—C201—H20E
H20D—C201—H20E
C191—C201—H20F
H20D—C201—H20F
H20E—C201—H20F
C4—N1—N2
108.9
119.6
105.3 (12)
110.7
120.1 (3)
119.9
110.7
119.9
110.7
127.4 (3)
129.7 (3)
102.8 (2)
111.1 (3)
110.3 (2)
110.2 (3)
108.4
110.7
108.8
109.5
109.5
109.5
109.5
109.5
108.4
109.5
108.4
104.5 (2)
112.7 (2)
122.7 (2)
121.1 (2)
122.6 (3)
118.9 (3)
118.5 (3)
C9—N2—N1
C9—N2—C10
N1—N2—C10
Acta Cryst. (2012). C68, o475–o480
sup-13

supplementary materials
C13—C12—C17
C13—C12—C11
C17—C12—C11
C12—C13—C14
C12—C13—H13
C14—C13—H13
119.8 (3)
122.5 (3)
117.7 (3)
119.8 (4)
120.1
C4—N3—C9
C4—N3—C5
C9—N3—C5
C18—O4—C19
C18—O41—C191
C2—S1—C3
107.6 (2)
124.8 (2)
127.6 (2)
111.8 (8)
121.4 (13)
98.09 (15)
120.1
C8—C1—C2—C5
−3.6 (5)
172.9 (3)
141.6 (3)
−40.6 (4)
1.6 (4)
N3—C4—N1—N2
C3—C4—N1—N2
O1—C9—N2—N1
N3—C9—N2—N1
1.5 (3)
C8—C1—C2—S1
179.4 (3)
−177.5 (3)
4.1 (3)
S1—C3—C4—N1
S1—C3—C4—N3
C1—C2—C5—C6
O1—C9—N2—C10
N3—C9—N2—C10
C4—N1—N2—C9
C4—N1—N2—C10
C18—C10—N2—C9
C11—C10—N2—C9
C18—C10—N2—N1
C11—C10—N2—N1
N1—C4—N3—C9
C3—C4—N3—C9
N1—C4—N3—C5
C3—C4—N3—C5
O1—C9—N3—C4
N2—C9—N3—C4
O1—C9—N3—C5
N2—C9—N3—C5
C6—C5—N3—C4
C2—C5—N3—C4
C6—C5—N3—C9
C2—C5—N3—C9
O3—C18—O4—C19
O41—C18—O4—C19
C10—C18—O4—C19
C20—C19—O4—C18
O3—C18—O41—C191
O4—C18—O41—C191
C10—C18—O41—C191
C201—C191—O41—C18
C1—C2—S1—C3
−18.7 (5)
162.9 (3)
−3.6 (4)
−162.8 (3)
−74.8 (4)
162.6 (3)
82.3 (3)
S1—C2—C5—C6
−174.7 (2)
−178.9 (3)
4.8 (4)
C1—C2—C5—N3
S1—C2—C5—N3
C2—C5—C6—C7
1.7 (5)
N3—C5—C6—C7
−177.8 (3)
−3.1 (5)
1.1 (6)
C5—C6—C7—C8
C6—C7—C8—C1
−40.3 (4)
1.0 (3)
C2—C1—C8—C7
2.3 (6)
N2—C10—C11—O2
C18—C10—C11—O2
N2—C10—C11—C12
C18—C10—C11—C12
O2—C11—C12—C13
C10—C11—C12—C13
O2—C11—C12—C17
C10—C11—C12—C17
C17—C12—C13—C14
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C12
C13—C12—C17—C16
C11—C12—C17—C16
N2—C10—C18—O3
C11—C10—C18—O3
N2—C10—C18—O4
C11—C10—C18—O4
N2—C10—C18—O41
C11—C10—C18—O41
98.8 (4)
−24.3 (4)
−81.1 (4)
155.8 (3)
−179.2 (3)
0.7 (5)
−177.0 (3)
179.3 (3)
1.3 (4)
178.6 (3)
−3.0 (3)
0.4 (5)
3.0 (5)
178.7 (3)
−160.9 (3)
19.6 (4)
−177.1 (3)
−0.2 (6)
−177.9 (4)
0.0 (7)
17.1 (4)
−162.4 (3)
8.5 (12)
−0.4 (7)
1.0 (8)
−93 (3)
−1.2 (7)
0.8 (6)
178.2 (8)
165.6 (16)
−11.8 (15)
83 (3)
178.6 (3)
−14.2 (5)
108.4 (4)
176.1 (7)
−61.2 (7)
152.3 (7)
−85.1 (7)
−178.2 (9)
−88 (2)
146.7 (3)
−37.0 (3)
51.2 (3)
C5—C2—S1—C3
C4—C3—S1—C2
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C3—H3A···O3i
C6—H6···O1
0.97
0.93
2.47
2.39
3.153 (4)
2.977 (4)
127
121
Acta Cryst. (2012). C68, o475–o480
sup-14

supplementary materials
C8—H8···O3ii
C13—H13···O1iii
0.93
0.93
2.46
2.58
3.265 (4)
3.330 (4)
145
138
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, y, −z+1/2.
Selected geometric parameters (Å ,° ) for (I), (II) and (III)
Parameter
C2-S1
(IA)
(IB)
(II)
(III)
1.762 (2)
1.809 (2)
1.383 (2)
1.423 (2)
1.348 (2)
106.95 (12)
125.63 (12)
126.80 (12)
1.767 (2)
1.813 (2)
1.383 (2)
1.425 (2)
1.347 (2)
106.88 (11)
124.80 (11)
128.22 (11)
1.772 (2)
1.809 (2)
1.379 (3)
1.421 (2)
1.358 (3)
107.32 (16)
124.48 (17)
127.94 (17)
1.769 (3)
1.800 (3)
1.382 (3)
1.429 (4)
1.367 (4)
107.6 (2)
124.8 (2)
127.6 (2)
C3-S1
C4-N3
C5-N3
C9-N2
C4-N3-C9
C4-N3-C5
C9-N3-C5
Acta Cryst. (2012). C68, o475–o480
sup-15