Three novel benzothia­zine-fused triazoles as potential centrally acting muscle relaxants

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 [beta]-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 examples of benzothia­zine-fused triazoles in the crystallographic literature. The heterocyclic thia­zine rings in all three structures adopt a distorted half-chair conformation. Com­pound (III) exists in the trans-[beta]-diketo form. Other than N-H...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-H...O/N and [pi]-[pi] stacking inter­actions.

S1. 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), antimalarial (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 the substituents on the triazole ring can be varied but 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., 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).

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 N···S axis is considered to be one of the structural features to impart 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). In 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 triazoles, IDPH-791, (I), and its N-substituted derivatives, (II) and (III).

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 propanoate 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), and the r.m.s. deviation for the mutual fit of the two molecules is 0.047 Å. 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 ring 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 not equal, owing to different environments. The C2—S1—C3 angles of 99.3 (1) and 97.9 (1)° in (I), 97.4 (1)° in (II) and 98.1 (2)° in (III) suggest that atom S1 uses only its p-orbitals to form bonds with C2 and 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 conformationally similar (Fig. 4). The thiazine ring is in a distorted half-chair conformation, with atoms S1 and C2 displaced by 1.057 (1) and -1.122 (1) and 0.473 (2) and -0.488 (2) Å, respectively, in (I), 1.177 (1) and 0.547 (2) Å, respectively, in (II), and 1.076 (1) and 0.428 (2) Å, respectively, in (III), from the plane defined by atoms C3/C4/N3/C5 (Nardelli, 1983). The dihedral angles between the triazole and benzene rings are 22.1 (1) and 21.8 (1)° in (I), 25.2 (1)° in (II) and 18.4 (1)° in (III), reflecting the twist created by the central thiazine ring in the tricyclic ring system. Another feature common to all three structures is an intramolecular interaction in the tricyclic ring system, observed between carbonyl atom O1 and atom C6 of the benzene ring, generating an S(6) graph-set motif.

The presence of bulky benzylol [in (II)] and phenylpropanoate [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 = 165.4 (2)°, 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 [-81.1 (4)°], perhaps due to the propanoate substitution at C10. Compound (III) exists in the trans β-diketo form. As suggested by Bertolasi et al. (2008) on keto–enol tautomerization of β-diketones from X-ray structure data and density functional theory calculations, the steric hindrance of bulky group substituents plays a role in shifting the more common β-keto–enol tautomer to the β-diketo form. Furthermore, they also reported that the occurrence of the trans β-diketo form in crystal structures can be interpreted in terms of the existence of a high activation energy in the mechanism to attain the β-keto–enol form. The O atoms of 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 (3)°. The 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)].

The packing diagrams for (I)–(III) are given in Figs. 5–7. In the absence of conventional hydrogen bonds, other than N—H···O hydrogen bonds in (I) as mentioned earlier, the crystal packing of (I)–(III) is essentially governed by C—H···O/N and π–π 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—H···O interactions (C3A—H···O1Bⁱ; details and symmetry code in Table 2), forming an R₂⁴(14) ring motif. These dimers are further linked by C—H···N and C—H···O interactions (C3B—H3D···N1Bⁱⁱ and C3B—H3C···O1Aⁱⁱ; details and symmetry code in Table 2), generating an R₃²(7) ring motif and forming a two-dimensional network in the [011] direction. A π–π stacking interaction is observed between the triazole and benzene ring systems [ring-centroid separation = 3.673 (2) Å; symmetry code: x, y - 1, z].

The molecules of (II) are linked together by paired C10—H···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 two benzene rings, centrosymmetrically related, results in a π–π stacking interaction [ring-centroid separation = 3.651 (1) Å; symmetry code: ? Please complete] and links the dimers.

In (III) there are more intermolecular C—H···O interactions than in (II), due to the presence of the additional propanoate group. The molecules are linked by paired C3—H···O3ⁱ, C8—H···O3ⁱⁱ and C13—H···O1ⁱⁱⁱ interactions (details and symmetry codes Table 4), forming centrosymmetric R₂²(16), R₂²(22) and R₂²(16) dimers, which are interconnected. As also seen in (II), there is a π–π stacking interaction between centrosymmetrically related benzene rings [ring-centroid separation = 3.987 (2) Å; symmetry code: ? Please complete].

In conclusion, this is the first report presenting the crystal structures of benzothiazine-fused triazoles. The tricyclic ring system generates an S(6) graph-set motif in all three title crystal structures. Crystallographic study shows that the N2 substitution has no significant effect on the conformation of the tricyclic ring system. The validity of the postulate that C—H···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 interactions and their role in supramolecular networks, molecular recognition and crystal engineering.

Related literature

For related literature, see: Aravindan et al. (2003); Bernstein et al. (1995); Bertolasi et al. (2008); Dalvie et al. (2002); Desiraju (2005); Duran et al. (2002); Etter (1990); Etter, MacDonald & Bernstein (1990); Fringuelli et al. (1998); Girmenia (2009); Guan et al. (2007); Gujjar et al. (2009); Gupta & Ojha (1988); Hafez et al. (2008); Holla et al. (2001, 2002); Horne et al. (2004); Johns et al. (2009); Junnarkar et al. (1992); Kobayashi et al. (1997); Liu et al. (2008); Matsumoto et al. (2000); Meester et al. (1986); Nardelli (1983); Pilati & Simonetta (1986); Ravikumar & Sridhar (2010); Ravikumar et al. (2011, 2012); Reddy Sastry, Narayan, Krishnan, Vemana, Shridhar, Singh & Junnarkar (1991); Sheldrick (2008); Silverman (2004).

S2. Experimental

The synthesis of (I) and (II) (SMS Pharma Research Centre, Hyderabad) was reported previously (Reddy Sastry et al., 1991). They were recrystallized from solutions in methanol (30 ml) for (I) and ethylacetate (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-phenyl propanoate (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 reaction 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 of a solution in methanol (30 ml).

S3. Refinement

In (III), the atoms O4, C19 and C20 are disordered over two sites and the site-occupancy 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 be 1.55 (2) Å and the C18—O4 and O4—C19 distances to be 1.33 (2) and 1.45 (2) Å. The N-bound H atoms of (I) were located in a difference Fourier map and their positions and isotropic displacement 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 Å (methylene), and with U_iso(H) = 1.5U_eq(C) for the methyl groups or 1.2U_eq(C) otherwise. The methyl groups were allowed to rotate but not to tip.

Computing details

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures

	Fig. 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.
	Fig. 2. A view of the molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 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 atoms O41, C191 and C201 have been omitted for clarity.
	Fig. 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 (Å) and labels are as follows: 0.005, molecule B of (I) (IB); 0.008, (II); and 0.012, (III).
	Fig. 5. A partial packing diagram for (I), showing the two-dimensional network formed by the intermolecular N—H···O and C—H···O interactions across the centres of symmetry, and by the C—H···N interactions. All these interactions are shown as dashed lines and non-associated H atoms have been omitted for clarity. Only atoms involved in the interactions are labelled. [Symmetry codes: (i) 2 - x, 1 - y, 1 - z; (ii) 2 - x, 1/2 + y, 3/2 - z.]
	Fig. 6. A partial packing diagram for (II), showing the formation of the C—H···O centrosymmetric dimer [R2^2(10)] and the intermolecular π–π 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) 2 - x, -y, 2 - z.]
	Fig. 7. A partial packing diagram for (III), showing the formation of the centrosymmetric rings [R2^2(22) and R2^2(16)], along with another R2^2(16) ring built from C—H···O interactions (dashed lines). The minor components of the 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) 1/2 - x, 1/2 - y, 1 - z; (ii) -x, 1 - y, 1 - z; (iii) -x, y, 1/2 - z.]

(I) 4H-1,2,4-Triazolo[3,4-c][1,4]benzothiazin-1(2H)-one

Crystal data

C9H7N3OS	F(000) = 1696
Mr = 205.24	Dx = 1.548 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7940 reflections
a = 14.6307 (11) Å	θ = 2.8–27.9°
b = 8.5718 (7) Å	µ = 0.33 mm^−1
c = 28.083 (2) Å	T = 294 K
V = 3521.9 (5) Å^3	Block, colourless
Z = 16	0.18 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2895 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −17→17
23641 measured reflections	k = −10→10
3092 independent reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 1.2353P] where P = (Fo^2 + 2Fc^2)/3
3092 reflections	(Δ/σ)max = 0.002
261 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.18 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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.84019 (11)	−0.11143 (18)	0.61793 (6)	0.0445 (4)
H1A	0.8313	−0.2029	0.6007	0.053*
C2A	0.85524 (10)	0.02781 (17)	0.59376 (5)	0.0357 (3)
C3A	0.82292 (12)	0.2168 (2)	0.51776 (6)	0.0469 (4)
H3A	0.8329	0.2402	0.4844	0.056*
H3B	0.7578	0.2214	0.5240	0.056*
C4A	0.87140 (10)	0.33258 (18)	0.54789 (5)	0.0395 (3)
C5A	0.86734 (9)	0.16437 (16)	0.62042 (5)	0.0323 (3)
C6A	0.86333 (10)	0.15985 (18)	0.66991 (5)	0.0391 (3)
H6A	0.8697	0.2512	0.6875	0.047*
C7A	0.84988 (11)	0.0189 (2)	0.69286 (6)	0.0456 (4)
H7A	0.8487	0.0153	0.7260	0.055*
C8A	0.83823 (11)	−0.1162 (2)	0.66694 (6)	0.0483 (4)
H8A	0.8291	−0.2106	0.6825	0.058*
C9A	0.93332 (10)	0.43507 (17)	0.61350 (5)	0.0390 (3)
N1A	0.90420 (10)	0.46461 (16)	0.53405 (5)	0.0499 (4)
N2A	0.94070 (10)	0.52891 (16)	0.57515 (5)	0.0473 (3)
N3A	0.88573 (8)	0.30624 (13)	0.59590 (4)	0.0342 (3)
H1N	0.9754 (13)	0.608 (2)	0.5746 (6)	0.057 (5)*
O1A	0.96071 (9)	0.45606 (13)	0.65440 (4)	0.0504 (3)
S1A	0.86581 (3)	0.02384 (5)	0.531275 (14)	0.04670 (14)
C1B	1.18683 (11)	1.36233 (19)	0.63302 (6)	0.0453 (4)
H1B	1.2178	1.4384	0.6502	0.054*
C2B	1.16244 (10)	1.22315 (17)	0.65508 (5)	0.0352 (3)
C3B	1.09811 (12)	1.07916 (19)	0.73374 (5)	0.0444 (4)
H3C	1.1078	1.0400	0.7657	0.053*
H3D	1.0444	1.1454	0.7340	0.053*
C4B	1.08442 (10)	0.94730 (17)	0.70038 (5)	0.0352 (3)
C5B	1.11430 (9)	1.11109 (16)	0.62890 (5)	0.0312 (3)
C6B	1.09161 (10)	1.13879 (18)	0.58181 (5)	0.0374 (3)
H6B	1.0589	1.0648	0.5646	0.045*
C7B	1.11793 (11)	1.2773 (2)	0.56047 (6)	0.0457 (4)
H7B	1.1034	1.2954	0.5287	0.055*
C8B	1.16549 (12)	1.38856 (19)	0.58584 (6)	0.0505 (4)
H8B	1.1831	1.4811	0.5712	0.061*
C9B	1.06956 (10)	0.82465 (16)	0.63058 (5)	0.0359 (3)
N1B	1.06615 (9)	0.80492 (15)	0.71179 (4)	0.0421 (3)
N2B	1.05896 (9)	0.72947 (15)	0.66834 (5)	0.0426 (3)
N3B	1.08893 (8)	0.96891 (13)	0.65165 (4)	0.0320 (3)
H2N	1.0370 (12)	0.634 (2)	0.6670 (6)	0.054 (5)*
O1B	1.06371 (8)	0.79255 (12)	0.58797 (4)	0.0466 (3)
S1B	1.19697 (3)	1.19015 (5)	0.714522 (14)	0.04555 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0450 (8)	0.0329 (8)	0.0556 (10)	−0.0063 (7)	−0.0041 (7)	−0.0022 (7)
C2A	0.0336 (7)	0.0351 (8)	0.0384 (8)	−0.0025 (6)	−0.0004 (6)	−0.0035 (6)
C3A	0.0514 (9)	0.0545 (10)	0.0347 (8)	−0.0057 (8)	−0.0059 (7)	0.0021 (7)
C4A	0.0423 (8)	0.0397 (8)	0.0365 (8)	−0.0004 (7)	−0.0011 (6)	0.0042 (6)
C5A	0.0310 (7)	0.0306 (7)	0.0353 (7)	−0.0015 (6)	0.0020 (5)	−0.0001 (6)
C6A	0.0441 (8)	0.0382 (8)	0.0349 (8)	−0.0009 (7)	0.0029 (6)	−0.0027 (6)
C7A	0.0473 (9)	0.0521 (10)	0.0375 (8)	−0.0018 (7)	0.0035 (7)	0.0085 (7)
C8A	0.0483 (9)	0.0408 (9)	0.0559 (10)	−0.0058 (7)	−0.0006 (8)	0.0150 (7)
C9A	0.0447 (8)	0.0306 (7)	0.0417 (8)	−0.0034 (6)	0.0047 (6)	−0.0026 (6)
N1A	0.0581 (9)	0.0465 (8)	0.0450 (8)	−0.0050 (7)	−0.0045 (6)	0.0118 (6)
N2A	0.0581 (9)	0.0331 (7)	0.0507 (8)	−0.0098 (6)	−0.0014 (6)	0.0052 (6)
N3A	0.0396 (6)	0.0298 (6)	0.0333 (6)	−0.0023 (5)	0.0015 (5)	0.0004 (5)
O1A	0.0686 (8)	0.0412 (6)	0.0414 (6)	−0.0170 (5)	0.0016 (5)	−0.0068 (5)
S1A	0.0572 (3)	0.0463 (2)	0.0366 (2)	−0.00550 (18)	0.00072 (17)	−0.01162 (17)
C1B	0.0451 (9)	0.0338 (8)	0.0571 (10)	−0.0073 (7)	0.0042 (7)	−0.0038 (7)
C2B	0.0348 (7)	0.0323 (7)	0.0385 (7)	0.0002 (6)	0.0024 (6)	−0.0042 (6)
C3B	0.0562 (9)	0.0444 (9)	0.0327 (8)	−0.0037 (7)	0.0056 (7)	−0.0050 (7)
C4B	0.0383 (7)	0.0368 (7)	0.0304 (7)	−0.0021 (6)	0.0025 (6)	−0.0007 (6)
C5B	0.0304 (7)	0.0280 (7)	0.0351 (7)	0.0001 (5)	0.0049 (5)	−0.0010 (6)
C6B	0.0386 (7)	0.0380 (8)	0.0354 (7)	−0.0017 (6)	0.0024 (6)	−0.0004 (6)
C7B	0.0508 (9)	0.0462 (9)	0.0401 (8)	0.0036 (7)	0.0064 (7)	0.0090 (7)
C8B	0.0561 (10)	0.0353 (8)	0.0600 (10)	−0.0036 (7)	0.0112 (8)	0.0103 (7)
C9B	0.0394 (8)	0.0305 (7)	0.0378 (8)	−0.0042 (6)	0.0016 (6)	−0.0032 (6)
N1B	0.0526 (8)	0.0394 (7)	0.0343 (7)	−0.0066 (6)	0.0001 (5)	0.0024 (5)
N2B	0.0578 (8)	0.0307 (7)	0.0394 (7)	−0.0096 (6)	−0.0013 (6)	0.0001 (5)
N3B	0.0376 (6)	0.0283 (6)	0.0301 (6)	−0.0039 (5)	0.0020 (5)	−0.0022 (5)
O1B	0.0658 (7)	0.0385 (6)	0.0355 (6)	−0.0128 (5)	0.0034 (5)	−0.0075 (4)
S1B	0.0524 (3)	0.0455 (2)	0.0388 (2)	−0.00944 (17)	−0.00671 (16)	−0.00798 (16)

Geometric parameters (Å, º)

C1A—C8A	1.377 (2)	C1B—C8B	1.380 (2)
C1A—C2A	1.391 (2)	C1B—C2B	1.391 (2)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C5A	1.401 (2)	C2B—C5B	1.400 (2)
C2A—S1A	1.7619 (15)	C2B—S1B	1.7668 (15)
C3A—C4A	1.485 (2)	C3B—C4B	1.482 (2)
C3A—S1A	1.8092 (18)	C3B—S1B	1.8133 (17)
C3A—H3A	0.9700	C3B—H3C	0.9700
C3A—H3B	0.9700	C3B—H3D	0.9700
C4A—N1A	1.289 (2)	C4B—N1B	1.2898 (19)
C4A—N3A	1.3831 (18)	C4B—N3B	1.3826 (18)
C5A—C6A	1.392 (2)	C5B—C6B	1.384 (2)
C5A—N3A	1.4231 (18)	C5B—N3B	1.4252 (17)
C6A—C7A	1.383 (2)	C6B—C7B	1.384 (2)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.379 (2)	C7B—C8B	1.379 (2)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—O1A	1.2299 (18)	C9B—O1B	1.2310 (18)
C9A—N2A	1.348 (2)	C9B—N2B	1.347 (2)
C9A—N3A	1.3959 (19)	C9B—N3B	1.3998 (18)
N1A—N2A	1.386 (2)	N1B—N2B	1.3849 (18)
N2A—H1N	0.85 (2)	N2B—H2N	0.88 (2)
C8A—C1A—C2A	121.10 (15)	C8B—C1B—C2B	120.63 (15)
C8A—C1A—H1A	119.4	C8B—C1B—H1B	119.7
C2A—C1A—H1A	119.4	C2B—C1B—H1B	119.7
C1A—C2A—C5A	118.45 (14)	C1B—C2B—C5B	118.93 (14)
C1A—C2A—S1A	118.90 (11)	C1B—C2B—S1B	119.00 (12)
C5A—C2A—S1A	122.51 (11)	C5B—C2B—S1B	122.02 (11)
C4A—C3A—S1A	109.02 (11)	C4B—C3B—S1B	108.66 (10)
C4A—C3A—H3A	109.9	C4B—C3B—H3C	110.0
S1A—C3A—H3A	109.9	S1B—C3B—H3C	110.0
C4A—C3A—H3B	109.9	C4B—C3B—H3D	110.0
S1A—C3A—H3B	109.9	S1B—C3B—H3D	110.0
H3A—C3A—H3B	108.3	H3C—C3B—H3D	108.3
N1A—C4A—N3A	112.38 (14)	N1B—C4B—N3B	112.49 (12)
N1A—C4A—C3A	126.36 (14)	N1B—C4B—C3B	126.36 (13)
N3A—C4A—C3A	121.25 (13)	N3B—C4B—C3B	121.14 (13)
C6A—C5A—C2A	120.35 (13)	C6B—C5B—C2B	120.32 (13)
C6A—C5A—N3A	120.99 (13)	C6B—C5B—N3B	120.84 (13)
C2A—C5A—N3A	118.64 (12)	C2B—C5B—N3B	118.84 (12)
C7A—C6A—C5A	119.71 (14)	C5B—C6B—C7B	119.61 (14)
C7A—C6A—H6A	120.1	C5B—C6B—H6B	120.2
C5A—C6A—H6A	120.1	C7B—C6B—H6B	120.2
C8A—C7A—C6A	120.35 (14)	C8B—C7B—C6B	120.65 (15)
C8A—C7A—H7A	119.8	C8B—C7B—H7B	119.7
C6A—C7A—H7A	119.8	C6B—C7B—H7B	119.7
C1A—C8A—C7A	120.00 (15)	C7B—C8B—C1B	119.84 (15)
C1A—C8A—H8A	120.0	C7B—C8B—H8B	120.1
C7A—C8A—H8A	120.0	C1B—C8B—H8B	120.1
O1A—C9A—N2A	129.24 (14)	O1B—C9B—N2B	128.46 (13)
O1A—C9A—N3A	127.51 (14)	O1B—C9B—N3B	128.49 (13)
N2A—C9A—N3A	103.25 (13)	N2B—C9B—N3B	103.04 (12)
C4A—N1A—N2A	103.97 (13)	C4B—N1B—N2B	103.81 (12)
C9A—N2A—N1A	113.39 (13)	C9B—N2B—N1B	113.71 (12)
C9A—N2A—H1N	122.6 (13)	C9B—N2B—H2N	124.8 (12)
N1A—N2A—H1N	122.3 (12)	N1B—N2B—H2N	120.1 (12)
C4A—N3A—C9A	106.95 (12)	C4B—N3B—C9B	106.88 (11)
C4A—N3A—C5A	125.63 (12)	C4B—N3B—C5B	124.80 (11)
C9A—N3A—C5A	126.80 (12)	C9B—N3B—C5B	128.22 (11)
C2A—S1A—C3A	99.26 (7)	C2B—S1B—C3B	97.88 (7)
C8A—C1A—C2A—C5A	−0.8 (2)	C8B—C1B—C2B—C5B	−1.2 (2)
C8A—C1A—C2A—S1A	175.12 (12)	C8B—C1B—C2B—S1B	176.39 (13)
S1A—C3A—C4A—N1A	135.55 (15)	S1B—C3B—C4B—N1B	135.70 (14)
S1A—C3A—C4A—N3A	−44.59 (18)	S1B—C3B—C4B—N3B	−45.50 (18)
C1A—C2A—C5A—C6A	−0.6 (2)	C1B—C2B—C5B—C6B	0.1 (2)
S1A—C2A—C5A—C6A	−176.39 (11)	S1B—C2B—C5B—C6B	−177.41 (11)
C1A—C2A—C5A—N3A	177.98 (13)	C1B—C2B—C5B—N3B	−179.66 (13)
S1A—C2A—C5A—N3A	2.23 (19)	S1B—C2B—C5B—N3B	2.84 (18)
C2A—C5A—C6A—C7A	1.8 (2)	C2B—C5B—C6B—C7B	0.9 (2)
N3A—C5A—C6A—C7A	−176.78 (14)	N3B—C5B—C6B—C7B	−179.36 (13)
C5A—C6A—C7A—C8A	−1.6 (2)	C5B—C6B—C7B—C8B	−0.8 (2)
C2A—C1A—C8A—C7A	1.0 (2)	C6B—C7B—C8B—C1B	−0.3 (3)
C6A—C7A—C8A—C1A	0.2 (3)	C2B—C1B—C8B—C7B	1.3 (3)
N3A—C4A—N1A—N2A	−0.83 (18)	N3B—C4B—N1B—N2B	0.40 (17)
C3A—C4A—N1A—N2A	179.04 (15)	C3B—C4B—N1B—N2B	179.30 (15)
O1A—C9A—N2A—N1A	177.94 (16)	O1B—C9B—N2B—N1B	−177.27 (15)
N3A—C9A—N2A—N1A	−2.56 (18)	N3B—C9B—N2B—N1B	2.78 (17)
C4A—N1A—N2A—C9A	2.19 (19)	C4B—N1B—N2B—C9B	−2.08 (18)
N1A—C4A—N3A—C9A	−0.68 (18)	N1B—C4B—N3B—C9B	1.26 (17)
C3A—C4A—N3A—C9A	179.44 (14)	C3B—C4B—N3B—C9B	−177.70 (14)
N1A—C4A—N3A—C5A	−172.14 (14)	N1B—C4B—N3B—C5B	−175.30 (13)
C3A—C4A—N3A—C5A	8.0 (2)	C3B—C4B—N3B—C5B	5.7 (2)
O1A—C9A—N3A—C4A	−178.59 (16)	O1B—C9B—N3B—C4B	177.70 (15)
N2A—C9A—N3A—C4A	1.90 (16)	N2B—C9B—N3B—C4B	−2.35 (15)
O1A—C9A—N3A—C5A	−7.3 (2)	O1B—C9B—N3B—C5B	−5.9 (3)
N2A—C9A—N3A—C5A	173.22 (13)	N2B—C9B—N3B—C5B	174.06 (13)
C6A—C5A—N3A—C4A	−164.62 (14)	C6B—C5B—N3B—C4B	−160.55 (13)
C2A—C5A—N3A—C4A	16.8 (2)	C2B—C5B—N3B—C4B	19.2 (2)
C6A—C5A—N3A—C9A	25.6 (2)	C6B—C5B—N3B—C9B	23.6 (2)
C2A—C5A—N3A—C9A	−153.01 (14)	C2B—C5B—N3B—C9B	−156.61 (14)
C1A—C2A—S1A—C3A	150.82 (13)	C1B—C2B—S1B—C3B	146.30 (13)
C5A—C2A—S1A—C3A	−33.45 (14)	C5B—C2B—S1B—C3B	−36.20 (13)
C4A—C3A—S1A—C2A	50.69 (12)	C4B—C3B—S1B—C2B	53.54 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H2N···O1A	0.88 (2)	1.93 (2)	2.7771 (17)	163.4 (17)
N2A—H1N···O1B	0.85 (2)	2.08 (2)	2.9112 (18)	168.4 (17)
C3A—H3A···O1B^i	0.97	2.55	3.402 (2)	147
C3B—H3C···O1A^ii	0.97	2.56	3.4238 (19)	149
C3B—H3D···N1B^ii	0.97	2.61	3.444 (2)	144
C6A—H6A···O1A	0.93	2.39	2.9438 (19)	118
C6B—H6B···O1B	0.93	2.43	3.0009 (19)	120

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.

(II) 2-(2-Oxo-2-phenylethyl)-4H-1,2,4-triazolo[3,4- c][1,4]benzothiazin-1(2H)-one

Crystal data

C17H13N3O2S	F(000) = 672
Mr = 323.36	Dx = 1.477 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3459 reflections
a = 11.6248 (18) Å	θ = 2.7–24.8°
b = 14.920 (2) Å	µ = 0.24 mm^−1
c = 8.5909 (13) Å	T = 294 K
β = 102.564 (3)°	Needle, colourless
V = 1454.3 (4) Å^3	0.21 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2175 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = −13→13
13803 measured reflections	k = −17→17
2562 independent reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.4963P] where P = (Fo^2 + 2Fc^2)/3
2562 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.29 e Å^−3
0 restraints	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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4068 (2)	0.09302 (16)	1.1514 (3)	0.0476 (6)
H1	0.3310	0.1167	1.1253	0.057*
C2	0.49454 (18)	0.12968 (14)	1.0841 (2)	0.0385 (5)
C3	0.59868 (19)	0.27745 (14)	0.9999 (3)	0.0430 (5)
H3A	0.5992	0.3281	0.9293	0.052*
H3B	0.6110	0.2996	1.1084	0.052*
C4	0.69294 (18)	0.21352 (14)	0.9852 (3)	0.0380 (5)
C5	0.60792 (17)	0.09307 (13)	1.1240 (2)	0.0347 (5)
C6	0.6323 (2)	0.02331 (14)	1.2319 (3)	0.0416 (5)
H6	0.7082	0.0000	1.2604	0.050*
C7	0.5428 (2)	−0.01189 (16)	1.2975 (3)	0.0482 (6)
H7	0.5591	−0.0589	1.3700	0.058*
C8	0.4305 (2)	0.02227 (17)	1.2560 (3)	0.0509 (6)
H8	0.3706	−0.0024	1.2986	0.061*
C9	0.79549 (18)	0.08501 (14)	1.0186 (2)	0.0378 (5)
C10	0.94467 (19)	0.13928 (16)	0.8692 (3)	0.0458 (6)
H10A	0.9951	0.0922	0.9245	0.055*
H10B	0.9892	0.1948	0.8831	0.055*
C11	0.91012 (19)	0.11681 (14)	0.6929 (3)	0.0408 (5)
C12	1.00213 (18)	0.12699 (14)	0.5969 (3)	0.0392 (5)
C13	1.11552 (19)	0.15584 (15)	0.6638 (3)	0.0454 (6)
H13	1.1364	0.1689	0.7722	0.055*
C14	1.1977 (2)	0.16532 (17)	0.5704 (3)	0.0532 (6)
H14	1.2733	0.1854	0.6157	0.064*
C15	1.1678 (2)	0.14515 (17)	0.4112 (3)	0.0552 (7)
H15	1.2233	0.1517	0.3486	0.066*
C16	1.0565 (2)	0.11529 (18)	0.3433 (3)	0.0586 (7)
H16	1.0371	0.1007	0.2355	0.070*
C17	0.9732 (2)	0.10688 (16)	0.4353 (3)	0.0500 (6)
H17	0.8974	0.0877	0.3887	0.060*
N1	0.77836 (17)	0.22750 (12)	0.9143 (2)	0.0466 (5)
N2	0.84323 (16)	0.14868 (12)	0.9388 (2)	0.0456 (5)
N3	0.69649 (14)	0.12901 (11)	1.05118 (19)	0.0349 (4)
O1	0.83143 (13)	0.00975 (10)	1.05492 (19)	0.0483 (4)
O2	0.81152 (14)	0.09055 (12)	0.6344 (2)	0.0599 (5)
S1	0.45916 (5)	0.21922 (4)	0.94660 (7)	0.0491 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0356 (12)	0.0601 (15)	0.0513 (14)	−0.0071 (11)	0.0185 (11)	−0.0126 (12)
C2	0.0360 (11)	0.0436 (12)	0.0382 (11)	−0.0042 (9)	0.0129 (9)	−0.0081 (9)
C3	0.0449 (13)	0.0395 (12)	0.0483 (13)	0.0035 (10)	0.0183 (10)	0.0024 (10)
C4	0.0393 (12)	0.0375 (11)	0.0400 (12)	0.0003 (9)	0.0149 (9)	0.0010 (9)
C5	0.0339 (11)	0.0393 (11)	0.0350 (11)	−0.0047 (9)	0.0161 (9)	−0.0056 (9)
C6	0.0423 (12)	0.0420 (12)	0.0437 (12)	−0.0004 (10)	0.0161 (10)	0.0000 (10)
C7	0.0581 (15)	0.0461 (13)	0.0470 (13)	−0.0074 (11)	0.0258 (11)	0.0011 (11)
C8	0.0516 (14)	0.0569 (15)	0.0529 (14)	−0.0192 (12)	0.0307 (12)	−0.0110 (12)
C9	0.0320 (11)	0.0429 (12)	0.0409 (12)	0.0009 (9)	0.0130 (9)	−0.0001 (10)
C10	0.0368 (12)	0.0519 (14)	0.0553 (14)	0.0019 (10)	0.0242 (10)	0.0048 (11)
C11	0.0348 (12)	0.0358 (11)	0.0551 (14)	0.0009 (9)	0.0171 (10)	0.0076 (10)
C12	0.0380 (12)	0.0352 (11)	0.0475 (13)	0.0018 (9)	0.0160 (10)	0.0044 (9)
C13	0.0402 (12)	0.0552 (14)	0.0442 (13)	−0.0009 (11)	0.0163 (10)	0.0015 (11)
C14	0.0384 (13)	0.0649 (16)	0.0613 (16)	−0.0015 (11)	0.0216 (11)	0.0047 (13)
C15	0.0531 (15)	0.0637 (16)	0.0582 (16)	0.0097 (12)	0.0326 (13)	0.0083 (13)
C16	0.0686 (18)	0.0667 (17)	0.0446 (14)	0.0063 (14)	0.0215 (13)	−0.0011 (12)
C17	0.0456 (13)	0.0531 (15)	0.0516 (14)	−0.0020 (11)	0.0111 (11)	−0.0027 (11)
N1	0.0469 (11)	0.0433 (11)	0.0566 (12)	0.0031 (9)	0.0266 (9)	0.0075 (9)
N2	0.0401 (10)	0.0443 (11)	0.0607 (12)	0.0060 (8)	0.0294 (9)	0.0082 (9)
N3	0.0324 (9)	0.0366 (9)	0.0392 (10)	0.0000 (7)	0.0157 (7)	0.0017 (7)
O1	0.0435 (9)	0.0432 (9)	0.0630 (10)	0.0098 (7)	0.0222 (8)	0.0093 (8)
O2	0.0381 (9)	0.0722 (12)	0.0709 (12)	−0.0120 (8)	0.0155 (8)	0.0020 (9)
S1	0.0369 (3)	0.0576 (4)	0.0528 (4)	0.0076 (3)	0.0098 (3)	0.0049 (3)

Geometric parameters (Å, º)

C1—C8	1.375 (3)	C9—N3	1.405 (3)
C1—C2	1.389 (3)	C10—N2	1.440 (3)
C1—H1	0.9300	C10—C11	1.518 (3)
C2—C5	1.399 (3)	C10—H10A	0.9700
C2—S1	1.772 (2)	C10—H10B	0.9700
C3—C4	1.479 (3)	C11—O2	1.212 (3)
C3—S1	1.809 (2)	C11—C12	1.494 (3)
C3—H3A	0.9700	C12—C13	1.387 (3)
C3—H3B	0.9700	C12—C17	1.388 (3)
C4—N1	1.290 (3)	C13—C14	1.382 (3)
C4—N3	1.379 (3)	C13—H13	0.9300
C5—C6	1.381 (3)	C14—C15	1.370 (4)
C5—N3	1.421 (2)	C14—H14	0.9300
C6—C7	1.389 (3)	C15—C16	1.373 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.374 (3)	C16—C17	1.382 (3)
C7—H7	0.9300	C16—H16	0.9300
C8—H8	0.9300	C17—H17	0.9300
C9—O1	1.215 (3)	N1—N2	1.388 (3)
C9—N2	1.358 (3)
C8—C1—C2	120.9 (2)	N2—C10—H10B	109.2
C8—C1—H1	119.6	C11—C10—H10B	109.2
C2—C1—H1	119.6	H10A—C10—H10B	107.9
C1—C2—C5	118.8 (2)	O2—C11—C12	122.0 (2)
C1—C2—S1	119.30 (17)	O2—C11—C10	120.42 (19)
C5—C2—S1	121.83 (16)	C12—C11—C10	117.57 (18)
C4—C3—S1	108.00 (15)	C13—C12—C17	118.9 (2)
C4—C3—H3A	110.1	C13—C12—C11	122.2 (2)
S1—C3—H3A	110.1	C17—C12—C11	118.9 (2)
C4—C3—H3B	110.1	C14—C13—C12	120.4 (2)
S1—C3—H3B	110.1	C14—C13—H13	119.8
H3A—C3—H3B	108.4	C12—C13—H13	119.8
N1—C4—N3	112.62 (18)	C15—C14—C13	120.0 (2)
N1—C4—C3	126.63 (19)	C15—C14—H14	120.0
N3—C4—C3	120.75 (18)	C13—C14—H14	120.0
C6—C5—C2	120.21 (19)	C14—C15—C16	120.4 (2)
C6—C5—N3	121.15 (18)	C14—C15—H15	119.8
C2—C5—N3	118.64 (18)	C16—C15—H15	119.8
C5—C6—C7	119.6 (2)	C15—C16—C17	120.0 (2)
C5—C6—H6	120.2	C15—C16—H16	120.0
C7—C6—H6	120.2	C17—C16—H16	120.0
C8—C7—C6	120.5 (2)	C16—C17—C12	120.3 (2)
C8—C7—H7	119.8	C16—C17—H17	119.8
C6—C7—H7	119.8	C12—C17—H17	119.8
C7—C8—C1	119.9 (2)	C4—N1—N2	103.88 (17)
C7—C8—H8	120.1	C9—N2—N1	113.63 (16)
C1—C8—H8	120.1	C9—N2—C10	127.04 (19)
O1—C9—N2	128.37 (19)	N1—N2—C10	119.11 (17)
O1—C9—N3	129.14 (19)	C4—N3—C9	107.32 (16)
N2—C9—N3	102.48 (18)	C4—N3—C5	124.48 (17)
N2—C10—C11	111.90 (19)	C9—N3—C5	127.94 (17)
N2—C10—H10A	109.2	C2—S1—C3	97.36 (10)
C11—C10—H10A	109.2
C8—C1—C2—C5	0.3 (3)	C11—C12—C17—C16	−179.8 (2)
C8—C1—C2—S1	178.64 (17)	N3—C4—N1—N2	−1.6 (2)
S1—C3—C4—N1	132.3 (2)	C3—C4—N1—N2	178.2 (2)
S1—C3—C4—N3	−47.9 (2)	O1—C9—N2—N1	179.0 (2)
C1—C2—C5—C6	−1.8 (3)	N3—C9—N2—N1	−2.4 (2)
S1—C2—C5—C6	179.94 (16)	O1—C9—N2—C10	4.4 (4)
C1—C2—C5—N3	178.11 (18)	N3—C9—N2—C10	−177.0 (2)
S1—C2—C5—N3	−0.2 (3)	C4—N1—N2—C9	2.6 (3)
C2—C5—C6—C7	1.7 (3)	C4—N1—N2—C10	177.6 (2)
N3—C5—C6—C7	−178.20 (19)	C11—C10—N2—C9	95.9 (3)
C5—C6—C7—C8	−0.1 (3)	C11—C10—N2—N1	−78.4 (3)
C6—C7—C8—C1	−1.4 (3)	N1—C4—N3—C9	0.2 (2)
C2—C1—C8—C7	1.3 (3)	C3—C4—N3—C9	−179.6 (2)
N2—C10—C11—O2	−15.5 (3)	N1—C4—N3—C5	−174.29 (19)
N2—C10—C11—C12	165.41 (18)	C3—C4—N3—C5	5.9 (3)
O2—C11—C12—C13	−179.1 (2)	O1—C9—N3—C4	179.9 (2)
C10—C11—C12—C13	0.0 (3)	N2—C9—N3—C4	1.3 (2)
O2—C11—C12—C17	0.9 (3)	O1—C9—N3—C5	−5.8 (4)
C10—C11—C12—C17	180.0 (2)	N2—C9—N3—C5	175.59 (19)
C17—C12—C13—C14	0.7 (3)	C6—C5—N3—C4	−158.2 (2)
C11—C12—C13—C14	−179.3 (2)	C2—C5—N3—C4	21.9 (3)
C12—C13—C14—C15	−0.8 (4)	C6—C5—N3—C9	28.4 (3)
C13—C14—C15—C16	−0.1 (4)	C2—C5—N3—C9	−151.4 (2)
C14—C15—C16—C17	1.1 (4)	C1—C2—S1—C3	146.39 (18)
C15—C16—C17—C12	−1.1 (4)	C5—C2—S1—C3	−35.34 (19)
C13—C12—C17—C16	0.2 (4)	C4—C3—S1—C2	55.21 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.51	3.040 (3)	117
C10—H10A···O1^i	0.97	2.50	3.377 (3)	150

Symmetry code: (i) −x+2, −y, −z+2.

(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	F(000) = 1648
Mr = 395.43	Dx = 1.380 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6533 (14) Å	Cell parameters from 8703 reflections
b = 12.7279 (13) Å	θ = 2.2–27.6°
c = 22.2927 (19) Å	µ = 0.20 mm^−1
β = 100.601 (3)°	T = 294 K
V = 3807.9 (6) Å^3	Plate, colourless
Z = 8	0.16 × 0.14 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2804 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −16→16
17579 measured reflections	k = −15→15
3355 independent reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 5.1188P] where P = (Fo^2 + 2Fc^2)/3
3355 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.46 e Å^−3
52 restraints	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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1257 (3)	0.6780 (3)	0.49936 (17)	0.0713 (9)
H1	0.1707	0.7171	0.5270	0.086*
C2	0.1566 (2)	0.5858 (2)	0.47527 (14)	0.0561 (8)
C3	0.2717 (2)	0.4125 (3)	0.49316 (17)	0.0663 (9)
H3A	0.3365	0.3798	0.4959	0.080*
H3B	0.2449	0.3923	0.5289	0.080*
C4	0.2046 (2)	0.3758 (2)	0.43767 (14)	0.0508 (7)
C5	0.0868 (2)	0.5255 (2)	0.43667 (13)	0.0479 (7)
C6	−0.0116 (2)	0.5580 (3)	0.42121 (15)	0.0583 (8)
H6	−0.0584	0.5167	0.3963	0.070*
C7	−0.0390 (3)	0.6533 (3)	0.44355 (19)	0.0731 (10)
H7	−0.1040	0.6774	0.4319	0.088*
C8	0.0284 (3)	0.7121 (3)	0.48249 (19)	0.0786 (11)
H8	0.0088	0.7753	0.4977	0.094*
C9	0.0701 (2)	0.3720 (2)	0.36308 (14)	0.0512 (7)
C10	0.1045 (2)	0.1956 (3)	0.32654 (15)	0.0570 (8)
H10	0.0648	0.2151	0.2869	0.068*
C11	0.1969 (2)	0.1345 (3)	0.31531 (15)	0.0588 (8)
C12	0.2457 (2)	0.1677 (3)	0.26426 (15)	0.0588 (8)
C13	0.2119 (3)	0.2520 (3)	0.22691 (17)	0.0736 (10)
H13	0.1581	0.2916	0.2342	0.088*
C14	0.2591 (4)	0.2773 (4)	0.1783 (2)	0.0971 (13)
H14	0.2368	0.3338	0.1530	0.117*
C15	0.3389 (4)	0.2178 (5)	0.1682 (2)	0.1049 (16)
H15	0.3703	0.2342	0.1357	0.126*
C16	0.3723 (3)	0.1355 (5)	0.2052 (2)	0.0965 (14)
H16	0.4269	0.0969	0.1981	0.116*
C17	0.3264 (3)	0.1085 (3)	0.25296 (17)	0.0759 (10)
H17	0.3489	0.0512	0.2776	0.091*
C18	0.0409 (3)	0.1266 (3)	0.35988 (17)	0.0711 (9)
C19	−0.0499 (11)	−0.0273 (12)	0.3580 (5)	0.108 (4)	0.596 (15)
H19A	−0.0983	0.0121	0.3757	0.129*	0.596 (15)
H19B	−0.0074	−0.0663	0.3900	0.129*	0.596 (15)
C20	−0.1003 (9)	−0.0990 (9)	0.3092 (5)	0.125 (5)	0.596 (15)
H20A	−0.1326	−0.0583	0.2750	0.188*	0.596 (15)
H20B	−0.1489	−0.1405	0.3246	0.188*	0.596 (15)
H20C	−0.0517	−0.1445	0.2966	0.188*	0.596 (15)
C191	−0.0936 (11)	−0.0043 (9)	0.3354 (8)	0.086 (3)	0.404 (15)
H19C	−0.1499	−0.0133	0.3023	0.103*	0.404 (15)
H19D	−0.1177	0.0216	0.3710	0.103*	0.404 (15)
C201	−0.0385 (14)	−0.1068 (13)	0.3497 (11)	0.129 (7)	0.404 (15)
H20D	−0.0022	−0.1229	0.3178	0.194*	0.404 (15)
H20E	−0.0854	−0.1620	0.3525	0.194*	0.404 (15)
H20F	0.0071	−0.1007	0.3878	0.194*	0.404 (15)
N1	0.21558 (17)	0.2914 (2)	0.40800 (13)	0.0592 (7)
N2	0.13419 (17)	0.2904 (2)	0.36024 (12)	0.0578 (7)
N3	0.11885 (16)	0.42965 (18)	0.41295 (11)	0.0474 (6)
O1	−0.00803 (16)	0.3894 (2)	0.32908 (10)	0.0698 (7)
O2	0.2266 (2)	0.0622 (2)	0.34810 (13)	0.0842 (8)
O3	0.03282 (19)	0.1373 (3)	0.41169 (12)	0.0878 (8)
O4	0.0093 (8)	0.0430 (8)	0.3264 (5)	0.091 (3)	0.596 (15)
O41	−0.0202 (9)	0.0687 (9)	0.3178 (6)	0.073 (3)	0.404 (15)
S1	0.28467 (6)	0.55313 (7)	0.49131 (5)	0.0726 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.090 (3)	0.055 (2)	0.073 (2)	−0.0011 (18)	0.0260 (19)	−0.0096 (17)
C2	0.0635 (18)	0.0490 (17)	0.0590 (18)	0.0027 (14)	0.0198 (15)	0.0010 (14)
C3	0.0559 (19)	0.0572 (19)	0.079 (2)	0.0015 (15)	−0.0043 (16)	−0.0038 (17)
C4	0.0424 (15)	0.0464 (16)	0.0624 (18)	0.0051 (12)	0.0067 (13)	0.0011 (14)
C5	0.0512 (16)	0.0467 (15)	0.0503 (16)	0.0045 (12)	0.0212 (13)	0.0035 (13)
C6	0.0512 (17)	0.0616 (19)	0.0671 (19)	0.0080 (14)	0.0239 (14)	0.0053 (16)
C7	0.066 (2)	0.070 (2)	0.093 (3)	0.0186 (18)	0.041 (2)	0.006 (2)
C8	0.097 (3)	0.056 (2)	0.096 (3)	0.014 (2)	0.051 (2)	−0.009 (2)
C9	0.0418 (15)	0.0578 (18)	0.0547 (17)	0.0035 (13)	0.0110 (13)	−0.0003 (14)
C10	0.0527 (16)	0.0626 (19)	0.0563 (18)	0.0011 (14)	0.0115 (14)	−0.0158 (15)
C11	0.0608 (19)	0.0549 (19)	0.0608 (19)	0.0033 (15)	0.0114 (15)	−0.0112 (16)
C12	0.0554 (17)	0.063 (2)	0.0593 (19)	0.0015 (15)	0.0144 (14)	−0.0100 (16)
C13	0.078 (2)	0.077 (2)	0.069 (2)	0.0050 (19)	0.0207 (18)	0.0039 (19)
C14	0.119 (4)	0.098 (3)	0.079 (3)	−0.006 (3)	0.028 (3)	0.010 (2)
C15	0.105 (3)	0.141 (5)	0.079 (3)	−0.025 (3)	0.043 (3)	−0.015 (3)
C16	0.076 (3)	0.142 (4)	0.078 (3)	0.009 (3)	0.032 (2)	−0.024 (3)
C17	0.065 (2)	0.093 (3)	0.072 (2)	0.0142 (19)	0.0188 (18)	−0.019 (2)
C18	0.065 (2)	0.085 (2)	0.068 (2)	−0.0078 (17)	0.0224 (17)	−0.0222 (18)
C19	0.109 (9)	0.122 (8)	0.096 (7)	−0.053 (7)	0.030 (6)	−0.012 (6)
C20	0.125 (9)	0.110 (7)	0.132 (8)	−0.061 (6)	0.000 (7)	−0.001 (6)
C191	0.084 (8)	0.086 (7)	0.087 (9)	−0.014 (4)	0.011 (6)	0.006 (6)
C201	0.124 (13)	0.100 (8)	0.161 (17)	0.002 (8)	0.018 (12)	0.044 (11)
N1	0.0419 (13)	0.0564 (15)	0.0753 (17)	0.0074 (11)	−0.0001 (12)	−0.0112 (13)
N2	0.0450 (13)	0.0596 (15)	0.0659 (16)	0.0069 (11)	0.0031 (11)	−0.0143 (13)
N3	0.0415 (12)	0.0463 (13)	0.0546 (14)	0.0039 (10)	0.0099 (10)	−0.0015 (11)
O1	0.0531 (13)	0.0799 (16)	0.0703 (15)	0.0147 (11)	−0.0047 (11)	−0.0089 (12)
O2	0.101 (2)	0.0672 (16)	0.0906 (18)	0.0221 (14)	0.0334 (15)	0.0120 (14)
O3	0.0776 (17)	0.124 (2)	0.0666 (16)	−0.0106 (15)	0.0268 (13)	−0.0198 (15)
O4	0.099 (6)	0.100 (6)	0.085 (5)	−0.042 (5)	0.040 (4)	−0.030 (4)
O41	0.075 (6)	0.065 (4)	0.082 (5)	−0.010 (4)	0.027 (4)	−0.019 (4)
S1	0.0596 (5)	0.0562 (5)	0.0978 (7)	−0.0064 (4)	0.0033 (5)	−0.0099 (5)

Geometric parameters (Å, º)

C1—C8	1.382 (5)	C12—C17	1.396 (5)
C1—C2	1.388 (5)	C13—C14	1.396 (6)
C1—H1	0.9300	C13—H13	0.9300
C2—C5	1.392 (4)	C14—C15	1.380 (7)
C2—S1	1.769 (3)	C14—H14	0.9300
C3—C4	1.473 (4)	C15—C16	1.359 (7)
C3—S1	1.800 (3)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.375 (6)
C3—H3B	0.9700	C16—H16	0.9300
C4—N1	1.284 (4)	C17—H17	0.9300
C4—N3	1.382 (3)	C18—O3	1.188 (4)
C5—C6	1.387 (4)	C18—O4	1.325 (7)
C5—N3	1.429 (4)	C18—O41	1.354 (9)
C6—C7	1.388 (5)	C19—O4	1.469 (8)
C6—H6	0.9300	C19—C20	1.488 (9)
C7—C8	1.367 (5)	C19—H19A	0.9700
C7—H7	0.9300	C19—H19B	0.9700
C8—H8	0.9300	C20—H20A	0.9600
C9—O1	1.210 (3)	C20—H20B	0.9600
C9—N2	1.367 (4)	C20—H20C	0.9600
C9—N3	1.394 (4)	C191—O41	1.473 (9)
C10—N2	1.439 (4)	C191—C201	1.510 (9)
C10—C18	1.522 (5)	C191—H19C	0.9700
C10—C11	1.541 (4)	C191—H19D	0.9700
C10—H10	0.9800	C201—H20D	0.9600
C11—O2	1.198 (4)	C201—H20E	0.9600
C11—C12	1.482 (5)	C201—H20F	0.9600
C12—C13	1.384 (5)	N1—N2	1.390 (3)
C8—C1—C2	120.4 (4)	C15—C14—C13	119.4 (5)
C8—C1—H1	119.8	C15—C14—H14	120.3
C2—C1—H1	119.8	C13—C14—H14	120.3
C1—C2—C5	119.0 (3)	C16—C15—C14	120.7 (4)
C1—C2—S1	118.7 (3)	C16—C15—H15	119.6
C5—C2—S1	122.2 (2)	C14—C15—H15	119.6
C4—C3—S1	110.2 (2)	C15—C16—C17	120.9 (4)
C4—C3—H3A	109.6	C15—C16—H16	119.6
S1—C3—H3A	109.6	C17—C16—H16	119.6
C4—C3—H3B	109.6	C16—C17—C12	119.5 (4)
S1—C3—H3B	109.6	C16—C17—H17	120.3
H3A—C3—H3B	108.1	C12—C17—H17	120.3
N1—C4—N3	112.3 (3)	O3—C18—O4	124.1 (6)
N1—C4—C3	125.8 (3)	O3—C18—O41	125.5 (8)
N3—C4—C3	121.8 (3)	O3—C18—C10	124.9 (3)
C6—C5—C2	120.6 (3)	O4—C18—C10	110.2 (5)
C6—C5—N3	120.7 (3)	O41—C18—C10	108.0 (7)
C2—C5—N3	118.6 (3)	O4—C19—C20	104.2 (7)
C5—C6—C7	119.0 (3)	O4—C19—H19A	110.9
C5—C6—H6	120.5	C20—C19—H19A	110.9
C7—C6—H6	120.5	O4—C19—H19B	110.9
C8—C7—C6	120.8 (3)	C20—C19—H19B	110.9
C8—C7—H7	119.6	H19A—C19—H19B	108.9
C6—C7—H7	119.6	O41—C191—C201	105.3 (12)
C7—C8—C1	120.1 (3)	O41—C191—H19C	110.7
C7—C8—H8	119.9	C201—C191—H19C	110.7
C1—C8—H8	119.9	O41—C191—H19D	110.7
O1—C9—N2	127.4 (3)	C201—C191—H19D	110.7
O1—C9—N3	129.7 (3)	H19C—C191—H19D	108.8
N2—C9—N3	102.8 (2)	C191—C201—H20D	109.5
N2—C10—C18	111.1 (3)	C191—C201—H20E	109.5
N2—C10—C11	110.3 (2)	H20D—C201—H20E	109.5
C18—C10—C11	110.2 (3)	C191—C201—H20F	109.5
N2—C10—H10	108.4	H20D—C201—H20F	109.5
C18—C10—H10	108.4	H20E—C201—H20F	109.5
C11—C10—H10	108.4	C4—N1—N2	104.5 (2)
O2—C11—C12	122.6 (3)	C9—N2—N1	112.7 (2)
O2—C11—C10	118.9 (3)	C9—N2—C10	122.7 (2)
C12—C11—C10	118.5 (3)	N1—N2—C10	121.1 (2)
C13—C12—C17	119.8 (3)	C4—N3—C9	107.6 (2)
C13—C12—C11	122.5 (3)	C4—N3—C5	124.8 (2)
C17—C12—C11	117.7 (3)	C9—N3—C5	127.6 (2)
C12—C13—C14	119.8 (4)	C18—O4—C19	111.8 (8)
C12—C13—H13	120.1	C18—O41—C191	121.4 (13)
C14—C13—H13	120.1	C2—S1—C3	98.09 (15)
C8—C1—C2—C5	−3.6 (5)	N3—C4—N1—N2	1.5 (3)
C8—C1—C2—S1	172.9 (3)	C3—C4—N1—N2	179.4 (3)
S1—C3—C4—N1	141.6 (3)	O1—C9—N2—N1	−177.5 (3)
S1—C3—C4—N3	−40.6 (4)	N3—C9—N2—N1	4.1 (3)
C1—C2—C5—C6	1.6 (4)	O1—C9—N2—C10	−18.7 (5)
S1—C2—C5—C6	−174.7 (2)	N3—C9—N2—C10	162.9 (3)
C1—C2—C5—N3	−178.9 (3)	C4—N1—N2—C9	−3.6 (4)
S1—C2—C5—N3	4.8 (4)	C4—N1—N2—C10	−162.8 (3)
C2—C5—C6—C7	1.7 (5)	C18—C10—N2—C9	−74.8 (4)
N3—C5—C6—C7	−177.8 (3)	C11—C10—N2—C9	162.6 (3)
C5—C6—C7—C8	−3.1 (5)	C18—C10—N2—N1	82.3 (3)
C6—C7—C8—C1	1.1 (6)	C11—C10—N2—N1	−40.3 (4)
C2—C1—C8—C7	2.3 (6)	N1—C4—N3—C9	1.0 (3)
N2—C10—C11—O2	98.8 (4)	C3—C4—N3—C9	−177.0 (3)
C18—C10—C11—O2	−24.3 (4)	N1—C4—N3—C5	179.3 (3)
N2—C10—C11—C12	−81.1 (4)	C3—C4—N3—C5	1.3 (4)
C18—C10—C11—C12	155.8 (3)	O1—C9—N3—C4	178.6 (3)
O2—C11—C12—C13	−179.2 (3)	N2—C9—N3—C4	−3.0 (3)
C10—C11—C12—C13	0.7 (5)	O1—C9—N3—C5	0.4 (5)
O2—C11—C12—C17	3.0 (5)	N2—C9—N3—C5	178.7 (3)
C10—C11—C12—C17	−177.1 (3)	C6—C5—N3—C4	−160.9 (3)
C17—C12—C13—C14	−0.2 (6)	C2—C5—N3—C4	19.6 (4)
C11—C12—C13—C14	−177.9 (4)	C6—C5—N3—C9	17.1 (4)
C12—C13—C14—C15	0.0 (7)	C2—C5—N3—C9	−162.4 (3)
C13—C14—C15—C16	−0.4 (7)	O3—C18—O4—C19	8.5 (12)
C14—C15—C16—C17	1.0 (8)	O41—C18—O4—C19	−93 (3)
C15—C16—C17—C12	−1.2 (7)	C10—C18—O4—C19	178.2 (8)
C13—C12—C17—C16	0.8 (6)	C20—C19—O4—C18	165.6 (16)
C11—C12—C17—C16	178.6 (3)	O3—C18—O41—C191	−11.8 (15)
N2—C10—C18—O3	−14.2 (5)	O4—C18—O41—C191	83 (3)
C11—C10—C18—O3	108.4 (4)	C10—C18—O41—C191	−178.2 (9)
N2—C10—C18—O4	176.1 (7)	C201—C191—O41—C18	−88 (2)
C11—C10—C18—O4	−61.2 (7)	C1—C2—S1—C3	146.7 (3)
N2—C10—C18—O41	152.3 (7)	C5—C2—S1—C3	−37.0 (3)
C11—C10—C18—O41	−85.1 (7)	C4—C3—S1—C2	51.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3^i	0.97	2.47	3.153 (4)	127
C6—H6···O1	0.93	2.39	2.977 (4)	121
C8—H8···O3^ii	0.93	2.46	3.265 (4)	145
C13—H13···O1^iii	0.93	2.58	3.330 (4)	138

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, y, −z+1/2.