Ethyl 2-{5-[(3-oxo-3,4-di-hydro-2H-1,4-benzo-thia-zin-4-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

In the title compound, C15H16N4O3S, the six-membered heterocycle of the benzo-thia-zine fragment exhibits a screw boat conformation. The dihedral angle between the planes through the triazole ring and the benzene ring fused to the 1,4-thia-zine ring is 62.98 (11)°. The mean plane formed by the atoms belonging to the acetate group is nearly perpendicular to the triazole ring [dihedral angle = 74.65 (12)°]. In the crystal, mol-ecules are linked by pairs of C-H⋯O inter-actions, forming dimeric aggregates.

Related literature

For the pharmacological activity of benzo­thia­zine derivatives, see: Fringuelli et al. (1998 ▶); Lopatina et al. (1982 ▶); Rathore & Kumar (2006 ▶). For related structures, see: Keita et al. (2000 ▶); Zerzouf et al. (2001 ▶); Barryala et al. (2011 ▶). For puckering calculation see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H16N4O3S

M = 332.38

Triclinic,

a = 5.6414 (2) Å

b = 11.1604 (4) Å

c = 13.3724 (5) Å

α = 73.823 (2)°

β = 87.226 (2)°

γ = 88.566 (2)°

V = 807.59 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.37 × 0.34 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.692, T max = 0.747

16305 measured reflections

3560 independent reflections

2963 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.05

3560 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034697/tk5283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034697/tk5283Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034697/tk5283Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H16N4O3S	Z = 2
Mr = 332.38	F(000) = 348
Triclinic, P1	Dx = 1.367 Mg m−3
a = 5.6414 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1604 (4) Å	Cell parameters from 3560 reflections
c = 13.3724 (5) Å	θ = 2.8–27.1°
α = 73.823 (2)°	µ = 0.22 mm−1
β = 87.226 (2)°	T = 296 K
γ = 88.566 (2)°	Block, yellow
V = 807.59 (5) Å3	0.37 × 0.34 × 0.28 mm

Bruker X8 APEX diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.692, Tmax = 0.747	k = −14→14
16305 measured reflections	l = −17→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.3602P] where P = (Fo2 + 2Fc2)/3
3560 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.0414 (3)	0.32734 (16)	0.35494 (13)	0.0404 (4)
C2	−0.1005 (4)	0.43140 (19)	0.35277 (16)	0.0584 (5)
H2	−0.1086	0.4960	0.2916	0.070*
C3	−0.2296 (5)	0.4392 (3)	0.4410 (2)	0.0816 (8)
H3	−0.3226	0.5097	0.4391	0.098*
C4	−0.2224 (5)	0.3437 (3)	0.5320 (2)	0.0848 (8)
H4	−0.3130	0.3488	0.5907	0.102*
C5	−0.0814 (4)	0.2415 (3)	0.53555 (16)	0.0681 (6)
H5	−0.0755	0.1775	0.5972	0.082*
C6	0.0537 (3)	0.23176 (18)	0.44807 (14)	0.0469 (4)
C7	0.4681 (3)	0.1852 (2)	0.36729 (17)	0.0589 (5)
H7A	0.5360	0.2444	0.3986	0.071*
H7B	0.5927	0.1272	0.3581	0.071*
C8	0.3767 (3)	0.25404 (16)	0.26244 (15)	0.0435 (4)
C9	0.0720 (3)	0.38039 (16)	0.16053 (13)	0.0386 (4)
H9A	−0.0999	0.3767	0.1659	0.046*
H9B	0.1268	0.3362	0.1106	0.046*
C10	0.1439 (3)	0.51384 (15)	0.12016 (12)	0.0351 (3)
C11	0.3619 (3)	0.56739 (15)	0.10351 (14)	0.0399 (4)
H11	0.5090	0.5274	0.1139	0.048*
C12	0.4837 (3)	0.79233 (16)	0.04712 (13)	0.0422 (4)
H12A	0.4078	0.8677	0.0059	0.051*
H12B	0.6199	0.7737	0.0066	0.051*
C13	0.5656 (4)	0.81404 (19)	0.14565 (15)	0.0498 (4)
C14	0.8094 (7)	0.9430 (4)	0.2083 (2)	0.1208 (14)
H14A	0.6953	0.9796	0.2482	0.145*
H14B	0.8669	0.8653	0.2541	0.145*
C15	0.9975 (6)	1.0233 (3)	0.1746 (3)	0.1089 (12)
H15A	1.0693	1.0380	0.2337	0.163*
H15B	0.9412	1.1010	0.1303	0.163*
H15C	1.1128	0.9867	0.1364	0.163*
N1	0.1656 (2)	0.31606 (12)	0.26288 (10)	0.0359 (3)
N2	−0.0215 (3)	0.60571 (14)	0.09455 (13)	0.0471 (4)
N3	0.0854 (3)	0.71393 (14)	0.06368 (13)	0.0486 (4)
N4	0.3184 (2)	0.69022 (13)	0.06899 (11)	0.0380 (3)
O1	0.4877 (3)	0.25525 (15)	0.18177 (12)	0.0619 (4)
O2	0.5302 (4)	0.7457 (2)	0.23075 (13)	0.1013 (8)
O3	0.6924 (3)	0.91691 (13)	0.12300 (11)	0.0560 (4)
S1	0.23551 (10)	0.10089 (5)	0.45316 (4)	0.06117 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0407 (9)	0.0437 (9)	0.0341 (8)	−0.0073 (7)	0.0014 (7)	−0.0060 (7)
C2	0.0686 (13)	0.0517 (11)	0.0476 (11)	0.0061 (10)	0.0149 (10)	−0.0052 (9)
C3	0.097 (2)	0.0739 (16)	0.0688 (16)	0.0123 (14)	0.0299 (14)	−0.0176 (13)
C4	0.098 (2)	0.104 (2)	0.0478 (13)	0.0025 (17)	0.0262 (13)	−0.0187 (13)
C5	0.0732 (15)	0.0872 (17)	0.0330 (10)	−0.0082 (13)	0.0021 (10)	0.0015 (10)
C6	0.0438 (9)	0.0539 (10)	0.0369 (9)	−0.0068 (8)	−0.0049 (7)	−0.0015 (8)
C7	0.0386 (10)	0.0640 (13)	0.0608 (13)	0.0032 (9)	−0.0069 (9)	0.0052 (10)
C8	0.0369 (9)	0.0409 (9)	0.0481 (10)	−0.0043 (7)	−0.0002 (7)	−0.0046 (7)
C9	0.0370 (8)	0.0419 (9)	0.0338 (8)	−0.0049 (7)	−0.0042 (6)	−0.0049 (7)
C10	0.0326 (8)	0.0403 (8)	0.0291 (8)	0.0007 (6)	−0.0027 (6)	−0.0039 (6)
C11	0.0327 (8)	0.0367 (8)	0.0453 (9)	0.0027 (6)	−0.0022 (7)	−0.0031 (7)
C12	0.0479 (10)	0.0376 (8)	0.0360 (9)	−0.0069 (7)	−0.0020 (7)	−0.0014 (7)
C13	0.0559 (11)	0.0526 (11)	0.0380 (10)	−0.0085 (9)	−0.0009 (8)	−0.0073 (8)
C14	0.153 (3)	0.155 (3)	0.0655 (18)	−0.077 (3)	−0.0210 (19)	−0.039 (2)
C15	0.117 (3)	0.116 (3)	0.096 (2)	−0.047 (2)	−0.038 (2)	−0.0240 (19)
N1	0.0348 (7)	0.0363 (7)	0.0326 (7)	−0.0022 (5)	−0.0014 (5)	−0.0028 (5)
N2	0.0332 (7)	0.0468 (8)	0.0536 (9)	0.0020 (6)	−0.0060 (6)	−0.0009 (7)
N3	0.0394 (8)	0.0432 (8)	0.0555 (10)	0.0059 (6)	−0.0070 (7)	−0.0008 (7)
N4	0.0358 (7)	0.0362 (7)	0.0368 (7)	−0.0004 (5)	−0.0022 (5)	−0.0018 (6)
O1	0.0508 (8)	0.0707 (10)	0.0586 (9)	0.0096 (7)	0.0109 (7)	−0.0119 (7)
O2	0.1505 (19)	0.1102 (15)	0.0355 (9)	−0.0617 (14)	−0.0002 (10)	−0.0028 (9)
O3	0.0673 (9)	0.0560 (8)	0.0456 (8)	−0.0148 (7)	−0.0102 (6)	−0.0131 (6)
S1	0.0544 (3)	0.0533 (3)	0.0578 (3)	−0.0006 (2)	−0.0062 (2)	0.0150 (2)

C1—C2	1.388 (3)	C9—H9B	0.9700
C1—C6	1.399 (2)	C10—N2	1.351 (2)
C1—N1	1.421 (2)	C10—C11	1.362 (2)
C2—C3	1.379 (3)	C11—N4	1.339 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.378 (4)	C12—N4	1.448 (2)
C3—H3	0.9300	C12—C13	1.500 (3)
C4—C5	1.365 (4)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.394 (3)	C13—O2	1.191 (2)
C5—H5	0.9300	C13—O3	1.322 (2)
C6—S1	1.751 (2)	C14—C15	1.381 (4)
C7—C8	1.507 (3)	C14—O3	1.446 (3)
C7—S1	1.800 (2)	C14—H14A	0.9700
C7—H7A	0.9700	C14—H14B	0.9700
C7—H7B	0.9700	C15—H15A	0.9600
C8—O1	1.217 (2)	C15—H15B	0.9600
C8—N1	1.363 (2)	C15—H15C	0.9600
C9—N1	1.473 (2)	N2—N3	1.314 (2)
C9—C10	1.495 (2)	N3—N4	1.335 (2)
C9—H9A	0.9700
C2—C1—C6	119.07 (17)	C11—C10—C9	131.21 (15)
C2—C1—N1	120.41 (15)	N4—C11—C10	104.97 (14)
C6—C1—N1	120.48 (17)	N4—C11—H11	127.5
C3—C2—C1	120.2 (2)	C10—C11—H11	127.5
C3—C2—H2	119.9	N4—C12—C13	111.39 (14)
C1—C2—H2	119.9	N4—C12—H12A	109.4
C4—C3—C2	120.8 (2)	C13—C12—H12A	109.4
C4—C3—H3	119.6	N4—C12—H12B	109.4
C2—C3—H3	119.6	C13—C12—H12B	109.4
C5—C4—C3	119.6 (2)	H12A—C12—H12B	108.0
C5—C4—H4	120.2	O2—C13—O3	125.37 (19)
C3—C4—H4	120.2	O2—C13—C12	124.90 (19)
C4—C5—C6	120.9 (2)	O3—C13—C12	109.65 (15)
C4—C5—H5	119.5	C15—C14—O3	112.4 (3)
C6—C5—H5	119.5	C15—C14—H14A	109.1
C5—C6—C1	119.4 (2)	O3—C14—H14A	109.1
C5—C6—S1	120.78 (16)	C15—C14—H14B	109.1
C1—C6—S1	119.84 (15)	O3—C14—H14B	109.1
C8—C7—S1	111.53 (13)	H14A—C14—H14B	107.8
C8—C7—H7A	109.3	C14—C15—H15A	109.5
S1—C7—H7A	109.3	C14—C15—H15B	109.5
C8—C7—H7B	109.3	H15A—C15—H15B	109.5
S1—C7—H7B	109.3	C14—C15—H15C	109.5
H7A—C7—H7B	108.0	H15A—C15—H15C	109.5
O1—C8—N1	121.92 (17)	H15B—C15—H15C	109.5
O1—C8—C7	121.56 (17)	C8—N1—C1	123.85 (14)
N1—C8—C7	116.51 (16)	C8—N1—C9	116.72 (14)
N1—C9—C10	113.91 (13)	C1—N1—C9	119.33 (14)
N1—C9—H9A	108.8	N3—N2—C10	109.05 (14)
C10—C9—H9A	108.8	N2—N3—N4	106.88 (14)
N1—C9—H9B	108.8	N3—N4—C11	111.00 (14)
C10—C9—H9B	108.8	N3—N4—C12	119.89 (14)
H9A—C9—H9B	107.7	C11—N4—C12	128.89 (14)
N2—C10—C11	108.10 (14)	C13—O3—C14	116.59 (19)
N2—C10—C9	120.68 (14)	C6—S1—C7	95.49 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.59	3.445 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.59	3.445 (3)	154

Symmetry code: (i) .