4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-yl]-2H-1,4-benzo-thia-zin-3(4H)-one.

In the title compound, C18H16N4OS, the six-membered heterocycle of the benzo-thia-zine fragment exhibits a screw-boat conformation. The dihedral angles between the plane through the triazole ring and those through the fused and terminal benzene rings are 76.68 (11) and 71.0 (1)°, respectively; the benzene rings are nearly perpendicular [dihedral angle = 79.6 (1)°]. In the crystal, mol-ecules are linked by C-H⋯N and C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For the biological activity of 1,4-benzo­thia­zin-3-one derivatives, see: Rathore & Kumar (2006 ▶); Baraza­rte et al. (2008 ▶); Chia et al. (2008 ▶). For related structures, see: Ouzidan et al. (2011 ▶); Sebbar et al. (2014 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H16N4OS

M = 336.41

Monoclinic,

a = 13.283 (2) Å

b = 5.3661 (10) Å

c = 23.281 (4) Å

β = 96.633 (10)°

V = 1648.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.39 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.649, T max = 0.747

15366 measured reflections

3526 independent reflections

2540 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.149

S = 1.03

3526 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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/S1600536814000786/tk5287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000786/tk5287Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000786/tk5287Isup3.cml

CCDC reference:

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

C18H16N4OS	F(000) = 704
Mr = 336.41	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3526 reflections
a = 13.283 (2) Å	θ = 1.8–27.1°
b = 5.3661 (10) Å	µ = 0.21 mm−1
c = 23.281 (4) Å	T = 296 K
β = 96.633 (10)°	Block, colourless
V = 1648.3 (5) Å3	0.39 × 0.35 × 0.28 mm
Z = 4

Bruker X8 APEX diffractometer	3526 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→17
Tmin = 0.649, Tmax = 0.747	k = −6→5
15366 measured reflections	l = −29→29

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.087P)2 + 0.1602P] where P = (Fo2 + 2Fc2)/3
3526 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

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 > σ(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	0.22144 (17)	1.2104 (4)	0.32721 (9)	0.0608 (6)
H1	0.2703	1.3328	0.3361	0.073*
C2	0.13131 (19)	1.2201 (4)	0.35176 (10)	0.0663 (6)
H2	0.1207	1.3471	0.3776	0.080*
C3	0.05772 (18)	1.0436 (4)	0.33828 (10)	0.0620 (6)
H3	−0.0028	1.0501	0.3547	0.074*
C4	0.07467 (19)	0.8572 (5)	0.30010 (9)	0.0675 (7)
H4	0.0246	0.7387	0.2901	0.081*
C5	0.16506 (19)	0.8438 (4)	0.27650 (8)	0.0577 (6)
H5	0.1759	0.7140	0.2515	0.069*
C6	0.23928 (15)	1.0199 (4)	0.28950 (7)	0.0457 (4)
C7	0.33713 (17)	1.0077 (4)	0.26263 (8)	0.0597 (6)
H7A	0.3309	0.8829	0.2323	0.072*
H7B	0.3490	1.1673	0.2450	0.072*
C8	0.48825 (17)	1.0970 (4)	0.33613 (9)	0.0545 (5)
H8	0.4885	1.2703	0.3354	0.065*
C9	0.55342 (15)	0.9457 (3)	0.36961 (7)	0.0424 (4)
C10	0.64140 (18)	1.0099 (4)	0.41219 (9)	0.0555 (5)
H10A	0.6711	1.1646	0.4006	0.067*
H10B	0.6181	1.0363	0.4497	0.067*
C11	0.72308 (14)	0.6346 (4)	0.46251 (7)	0.0438 (4)
C12	0.64100 (17)	0.6069 (5)	0.49446 (8)	0.0581 (6)
H12	0.5823	0.6994	0.4847	0.070*
C13	0.6465 (2)	0.4417 (5)	0.54082 (8)	0.0727 (8)
H13	0.5923	0.4296	0.5627	0.087*
C14	0.7301 (2)	0.2979 (6)	0.55454 (8)	0.0780 (8)
H14	0.7327	0.1873	0.5854	0.094*
C15	0.81136 (19)	0.3164 (5)	0.52239 (8)	0.0683 (7)
H15	0.8680	0.2154	0.5311	0.082*
C16	0.80820 (15)	0.4867 (4)	0.47686 (7)	0.0499 (5)
C17	0.84430 (15)	0.5783 (4)	0.36944 (7)	0.0526 (5)
H17A	0.8910	0.6067	0.3410	0.063*
H17B	0.8032	0.4341	0.3572	0.063*
C18	0.77735 (15)	0.8007 (4)	0.37190 (7)	0.0480 (5)
N1	0.42420 (12)	0.9464 (3)	0.30471 (6)	0.0442 (4)
N2	0.44742 (13)	0.7078 (3)	0.31697 (6)	0.0482 (4)
N3	0.52629 (12)	0.7072 (3)	0.35664 (6)	0.0461 (4)
N4	0.71926 (12)	0.8149 (3)	0.41721 (6)	0.0451 (4)
O1	0.77092 (14)	0.9600 (3)	0.33403 (6)	0.0689 (5)
S1	0.91484 (4)	0.51598 (14)	0.43858 (2)	0.0692 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0529 (13)	0.0505 (13)	0.0794 (14)	−0.0036 (10)	0.0088 (11)	−0.0073 (10)
C2	0.0640 (15)	0.0553 (13)	0.0817 (14)	0.0067 (11)	0.0168 (12)	−0.0186 (11)
C3	0.0530 (13)	0.0659 (14)	0.0694 (13)	0.0021 (11)	0.0169 (11)	0.0023 (11)
C4	0.0738 (16)	0.0651 (15)	0.0658 (12)	−0.0245 (12)	0.0177 (12)	−0.0075 (11)
C5	0.0784 (16)	0.0501 (12)	0.0461 (9)	−0.0030 (11)	0.0137 (10)	−0.0047 (9)
C6	0.0480 (11)	0.0503 (11)	0.0385 (8)	0.0108 (9)	0.0041 (7)	0.0125 (8)
C7	0.0553 (13)	0.0785 (16)	0.0465 (10)	0.0182 (11)	0.0108 (9)	0.0225 (10)
C8	0.0598 (13)	0.0292 (9)	0.0759 (13)	0.0004 (9)	0.0141 (11)	0.0046 (9)
C9	0.0480 (11)	0.0325 (9)	0.0483 (9)	−0.0044 (8)	0.0125 (8)	−0.0029 (7)
C10	0.0621 (13)	0.0426 (11)	0.0615 (11)	−0.0112 (10)	0.0064 (10)	−0.0110 (9)
C11	0.0433 (10)	0.0563 (11)	0.0312 (7)	−0.0180 (9)	0.0015 (7)	−0.0067 (7)
C12	0.0483 (12)	0.0824 (15)	0.0449 (10)	−0.0193 (11)	0.0101 (9)	−0.0094 (10)
C13	0.0673 (16)	0.114 (2)	0.0379 (9)	−0.0397 (15)	0.0129 (10)	−0.0035 (11)
C14	0.0828 (19)	0.110 (2)	0.0378 (9)	−0.0344 (16)	−0.0084 (10)	0.0178 (11)
C15	0.0655 (15)	0.0909 (18)	0.0437 (10)	−0.0127 (13)	−0.0145 (9)	0.0138 (11)
C16	0.0410 (10)	0.0736 (14)	0.0332 (8)	−0.0165 (10)	−0.0039 (7)	−0.0012 (8)
C17	0.0461 (11)	0.0736 (14)	0.0391 (8)	−0.0139 (10)	0.0094 (8)	−0.0017 (9)
C18	0.0469 (11)	0.0581 (12)	0.0387 (8)	−0.0221 (9)	0.0036 (7)	−0.0004 (8)
N1	0.0450 (9)	0.0419 (9)	0.0469 (8)	0.0054 (7)	0.0102 (7)	0.0093 (6)
N2	0.0531 (10)	0.0375 (9)	0.0513 (8)	0.0015 (7)	−0.0049 (7)	0.0012 (7)
N3	0.0538 (10)	0.0318 (8)	0.0503 (8)	−0.0042 (7)	−0.0035 (7)	−0.0009 (6)
N4	0.0435 (9)	0.0497 (9)	0.0419 (7)	−0.0123 (7)	0.0044 (6)	−0.0033 (7)
O1	0.0803 (12)	0.0684 (10)	0.0588 (8)	−0.0190 (8)	0.0122 (8)	0.0172 (7)
S1	0.0364 (3)	0.1170 (6)	0.0528 (3)	−0.0050 (3)	−0.0005 (2)	0.0036 (3)

C1—C6	1.385 (3)	C10—H10B	0.9700
C1—C2	1.386 (3)	C11—C16	1.390 (3)
C1—H1	0.9300	C11—C12	1.397 (3)
C2—C3	1.371 (3)	C11—N4	1.428 (2)
C2—H2	0.9300	C12—C13	1.392 (3)
C3—C4	1.374 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.360 (4)
C4—C5	1.379 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.387 (4)
C5—C6	1.374 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.396 (3)
C6—C7	1.508 (3)	C15—H15	0.9300
C7—N1	1.464 (3)	C16—S1	1.766 (2)
C7—H7A	0.9700	C17—C18	1.493 (3)
C7—H7B	0.9700	C17—S1	1.798 (2)
C8—N1	1.330 (3)	C17—H17A	0.9700
C8—C9	1.364 (3)	C17—H17B	0.9700
C8—H8	0.9300	C18—O1	1.224 (2)
C9—N3	1.354 (2)	C18—N4	1.379 (2)
C9—C10	1.483 (3)	N1—N2	1.340 (2)
C10—N4	1.466 (3)	N2—N3	1.314 (2)
C10—H10A	0.9700
C6—C1—C2	120.5 (2)	C16—C11—C12	118.32 (18)
C6—C1—H1	119.7	C16—C11—N4	121.53 (16)
C2—C1—H1	119.7	C12—C11—N4	120.14 (19)
C3—C2—C1	120.5 (2)	C13—C12—C11	120.4 (2)
C3—C2—H2	119.8	C13—C12—H12	119.8
C1—C2—H2	119.8	C11—C12—H12	119.8
C2—C3—C4	119.0 (2)	C14—C13—C12	120.8 (2)
C2—C3—H3	120.5	C14—C13—H13	119.6
C4—C3—H3	120.5	C12—C13—H13	119.6
C3—C4—C5	120.7 (2)	C13—C14—C15	119.9 (2)
C3—C4—H4	119.6	C13—C14—H14	120.1
C5—C4—H4	119.6	C15—C14—H14	120.1
C6—C5—C4	120.80 (19)	C14—C15—C16	120.0 (2)
C6—C5—H5	119.6	C14—C15—H15	120.0
C4—C5—H5	119.6	C16—C15—H15	120.0
C5—C6—C1	118.43 (18)	C11—C16—C15	120.55 (19)
C5—C6—C7	120.64 (18)	C11—C16—S1	120.37 (14)
C1—C6—C7	120.92 (19)	C15—C16—S1	119.07 (18)
N1—C7—C6	112.60 (14)	C18—C17—S1	111.42 (13)
N1—C7—H7A	109.1	C18—C17—H17A	109.3
C6—C7—H7A	109.1	S1—C17—H17A	109.3
N1—C7—H7B	109.1	C18—C17—H17B	109.3
C6—C7—H7B	109.1	S1—C17—H17B	109.3
H7A—C7—H7B	107.8	H17A—C17—H17B	108.0
N1—C8—C9	106.02 (17)	O1—C18—N4	120.9 (2)
N1—C8—H8	127.0	O1—C18—C17	121.52 (17)
C9—C8—H8	127.0	N4—C18—C17	117.51 (16)
N3—C9—C8	107.47 (18)	C8—N1—N2	110.29 (16)
N3—C9—C10	122.51 (17)	C8—N1—C7	129.57 (18)
C8—C9—C10	130.00 (18)	N2—N1—C7	120.13 (17)
N4—C10—C9	112.43 (15)	N3—N2—N1	107.31 (15)
N4—C10—H10A	109.1	N2—N3—C9	108.92 (15)
C9—C10—H10A	109.1	C18—N4—C11	123.52 (17)
N4—C10—H10B	109.1	C18—N4—C10	115.48 (16)
C9—C10—H10B	109.1	C11—N4—C10	120.46 (15)
H10A—C10—H10B	107.8	C16—S1—C17	95.91 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2i	0.93	2.44	3.344 (3)	165
C8—H8···N3i	0.93	2.44	3.339 (3)	164
C5—H5···O1ii	0.93	2.58	3.477 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N2i	0.93	2.44	3.344 (3)	165
C8—H8⋯N3i	0.93	2.44	3.339 (3)	164
C5—H5⋯O1ii	0.93	2.58	3.477 (2)	163

Symmetry codes: (i) ; (ii) .