4-(Prop-2-yn-yl)-2H-1,4-benzo-thia-zin-3(4H)-one.

In the title compound, C11H9NOS, the six-membered heterocycle of the benzo-thia-zine fragment exhibits a screw-boat conformation. The benzene ring makes a dihedral angle of 79.4 (1)° with the mean plane through the prop-2-ynyl chain and the ring N atom. In the crystal, mol-ecules are linked by C-H⋯O inter-actions of the acetyl-enic C-H group towards the carbonyl O atom of a neighbouring mol-ecule, forming zigzag chains running along the b-axis direction.

Related literature

For general background to the synthesis of 1,4-benzo­thia­zines derivatives, see: Sebbar et al. (2014 ▶); Zerzouf et al. (2001 ▶). For the pharmacological activity of 1,4-benzo­thia­zine derivatives, see: Trapani et al. (1985 ▶); Yaltirik et al. (2001 ▶); Wammack et al. (2002 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C11H9NOS

M = 203.25

Monoclinic,

a = 9.005 (2) Å

b = 10.889 (3) Å

c = 10.341 (3) Å

β = 104.565 (7)°

V = 981.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.39 × 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

9586 measured reflections

2532 independent reflections

2242 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.097

S = 1.05

2532 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 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/S160053681400943X/im2453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400943X/im2453Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400943X/im2453Isup3.cml

CCDC reference: 999603

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

C11H9NOS	F(000) = 424
Mr = 203.25	Dx = 1.376 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2532 reflections
a = 9.005 (2) Å	θ = 2.7–28.7°
b = 10.889 (3) Å	µ = 0.29 mm−1
c = 10.341 (3) Å	T = 296 K
β = 104.565 (7)°	Block, colourless
V = 981.3 (4) Å3	0.39 × 0.34 × 0.28 mm
Z = 4

Bruker X8 APEX diffractometer	2532 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 28.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.692, Tmax = 0.747	k = −14→14
9586 measured reflections	l = −13→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3
2532 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 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	0.72598 (13)	0.66267 (11)	0.41584 (11)	0.0349 (2)
C2	0.57459 (15)	0.63028 (14)	0.40891 (14)	0.0468 (3)
H2	0.5255	0.6635	0.4699	0.056*
C3	0.49680 (15)	0.54991 (15)	0.31310 (16)	0.0545 (4)
H3	0.3950	0.5302	0.3081	0.065*
C4	0.57071 (16)	0.49879 (14)	0.22443 (16)	0.0523 (3)
H4	0.5185	0.4439	0.1599	0.063*
C5	0.72189 (15)	0.52826 (12)	0.23035 (13)	0.0432 (3)
H5	0.7710	0.4922	0.1709	0.052*
C6	0.80051 (12)	0.61176 (10)	0.32501 (11)	0.0321 (2)
C7	1.05883 (13)	0.68706 (11)	0.43826 (12)	0.0365 (2)
C8	1.00619 (14)	0.69227 (13)	0.56496 (12)	0.0400 (3)
H8A	1.0811	0.7365	0.6327	0.048*
H8B	0.9981	0.6096	0.5974	0.048*
C9	1.00187 (16)	0.64258 (13)	0.20101 (12)	0.0430 (3)
H9A	0.9145	0.6591	0.1264	0.052*
H9B	1.0779	0.7059	0.2021	0.052*
C10	1.06719 (14)	0.52290 (14)	0.18089 (12)	0.0430 (3)
N1	0.95243 (11)	0.64883 (9)	0.32600 (9)	0.0343 (2)
C11	1.12110 (16)	0.42755 (16)	0.16435 (14)	0.0528 (3)
H11	1.1637	0.3522	0.1513	0.063*
O1	1.18902 (11)	0.71561 (11)	0.43539 (11)	0.0552 (3)
S1	0.82271 (4)	0.76777 (3)	0.53643 (3)	0.04266 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0342 (5)	0.0363 (6)	0.0354 (5)	0.0037 (4)	0.0114 (4)	0.0046 (4)
C2	0.0349 (6)	0.0579 (8)	0.0515 (7)	0.0039 (5)	0.0181 (5)	0.0071 (6)
C3	0.0322 (6)	0.0634 (9)	0.0667 (9)	−0.0064 (6)	0.0101 (6)	0.0087 (7)
C4	0.0433 (7)	0.0464 (7)	0.0602 (8)	−0.0078 (6)	−0.0002 (6)	−0.0034 (6)
C5	0.0411 (6)	0.0410 (6)	0.0456 (6)	0.0019 (5)	0.0074 (5)	−0.0055 (5)
C6	0.0299 (5)	0.0317 (5)	0.0350 (5)	0.0015 (4)	0.0086 (4)	0.0038 (4)
C7	0.0342 (5)	0.0343 (6)	0.0421 (6)	−0.0021 (4)	0.0115 (4)	0.0026 (5)
C8	0.0376 (6)	0.0451 (6)	0.0359 (6)	−0.0005 (5)	0.0067 (5)	−0.0010 (5)
C9	0.0458 (7)	0.0512 (7)	0.0373 (6)	0.0020 (5)	0.0202 (5)	0.0070 (5)
C10	0.0364 (6)	0.0614 (8)	0.0346 (6)	0.0008 (5)	0.0155 (5)	−0.0003 (5)
N1	0.0335 (5)	0.0389 (5)	0.0340 (5)	−0.0008 (4)	0.0147 (4)	0.0015 (4)
C11	0.0466 (7)	0.0656 (9)	0.0484 (7)	0.0069 (7)	0.0158 (6)	−0.0085 (7)
O1	0.0370 (5)	0.0686 (7)	0.0619 (6)	−0.0143 (4)	0.0160 (4)	0.0024 (5)
S1	0.0458 (2)	0.04378 (19)	0.04046 (19)	0.00495 (12)	0.01474 (14)	−0.00623 (12)

C1—C2	1.3924 (17)	C7—O1	1.2204 (15)
C1—C6	1.3990 (16)	C7—N1	1.3709 (16)
C1—S1	1.7542 (13)	C7—C8	1.5023 (16)
C2—C3	1.374 (2)	C8—S1	1.8021 (13)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.379 (2)	C8—H8B	0.9700
C3—H3	0.9300	C9—C10	1.4660 (19)
C4—C5	1.385 (2)	C9—N1	1.4707 (14)
C4—H4	0.9300	C9—H9A	0.9700
C5—C6	1.3919 (17)	C9—H9B	0.9700
C5—H5	0.9300	C10—C11	1.177 (2)
C6—N1	1.4239 (14)	C11—H11	0.9300
C2—C1—C6	119.60 (12)	N1—C7—C8	116.32 (10)
C2—C1—S1	120.43 (10)	C7—C8—S1	110.60 (9)
C6—C1—S1	119.97 (9)	C7—C8—H8A	109.5
C3—C2—C1	120.88 (13)	S1—C8—H8A	109.5
C3—C2—H2	119.6	C7—C8—H8B	109.5
C1—C2—H2	119.6	S1—C8—H8B	109.5
C2—C3—C4	119.52 (12)	H8A—C8—H8B	108.1
C2—C3—H3	120.2	C10—C9—N1	112.76 (10)
C4—C3—H3	120.2	C10—C9—H9A	109.0
C3—C4—C5	120.71 (13)	N1—C9—H9A	109.0
C3—C4—H4	119.6	C10—C9—H9B	109.0
C5—C4—H4	119.6	N1—C9—H9B	109.0
C4—C5—C6	120.20 (12)	H9A—C9—H9B	107.8
C4—C5—H5	119.9	C11—C10—C9	179.18 (14)
C6—C5—H5	119.9	C7—N1—C6	123.91 (9)
C5—C6—C1	119.07 (11)	C7—N1—C9	117.17 (10)
C5—C6—N1	120.54 (10)	C6—N1—C9	118.89 (10)
C1—C6—N1	120.34 (10)	C10—C11—H11	180.0
O1—C7—N1	121.86 (11)	C1—S1—C8	95.14 (6)
O1—C7—C8	121.83 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.32	3.1937 (19)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.32	3.1937 (19)	157

Symmetry code: (i) .