(2Z)-2-Benzyl-idene-4-(prop-2-yn-1-yl)-2H-1,4-benzo-thia-zin-3(4H)-one.

The mol-ecule of the title compound, C18H13NOS, is build up from two fused six-membered rings, with the heterocyclic component linked to a benzyl-idene group and to a prop-2-yn-1-yl chain. The six-membered heterocycle adopts a distorted screw-boat conformation. The prop-2-yn-1-yl chain is almost perpendicular to the mean plane through benzo-thia-zine as indicated by the C-N-C-C torsion angle of 86.5 (2)°. The dihedral angle between the benzene rings is 47.53 (12)°. There are no specific inter-molecular inter-actions in the crystal packing.

Related literature

For the pharmacological activity of benzo­thia­zine derivatives, see: Aotsuka et al. (1994 ▶); Fujimura et al. (1996 ▶); Rathore & Kumar (2006 ▶); Fringuelli et al. (1998 ▶). For related structures, see: Sebbar et al. (2014a ▶,; Zerzouf et al. (2001 ▶). For conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H13NOS

M = 291.35

Orthorhombic,

a = 9.0254 (13) Å

b = 7.7388 (12) Å

c = 42.488 (7) Å

V = 2967.6 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.42 × 0.36 × 0.31 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.579, T max = 0.746

14350 measured reflections

3248 independent reflections

2227 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.02

3248 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 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/S1600536814009179/tk5310sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009179/tk5310Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009179/tk5310Isup3.cml

CCDC reference: 999032

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

C18H13NOS	Dx = 1.304 Mg m−3
Mr = 291.35	Melting point: 404 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3248 reflections
a = 9.0254 (13) Å	θ = 2.5–27.1°
b = 7.7388 (12) Å	µ = 0.22 mm−1
c = 42.488 (7) Å	T = 296 K
V = 2967.6 (8) Å3	Block, yellow
Z = 8	0.42 × 0.36 × 0.31 mm
F(000) = 1216

Bruker X8 APEX diffractometer	3248 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.579, Tmax = 0.746	k = −5→9
14350 measured reflections	l = −54→42

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) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.8991P] where P = (Fo2 + 2Fc2)/3
3248 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 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	0.2609 (2)	0.8787 (2)	0.10840 (5)	0.0479 (5)
C2	0.1083 (2)	0.8810 (3)	0.10322 (6)	0.0565 (6)
H2	0.0443	0.8448	0.1191	0.068*
C3	0.0518 (2)	0.9359 (3)	0.07502 (6)	0.0615 (6)
H3	−0.0501	0.9412	0.0720	0.074*
C4	0.1463 (2)	0.9829 (3)	0.05121 (6)	0.0606 (6)
H4	0.1081	1.0198	0.0320	0.073*
C5	0.2986 (2)	0.9758 (3)	0.05563 (5)	0.0531 (5)
H5	0.3618	1.0037	0.0391	0.064*
C6	0.35728 (19)	0.9276 (2)	0.08436 (5)	0.0438 (5)
C7	0.5877 (2)	0.8372 (3)	0.11202 (5)	0.0476 (5)
C8	0.5034 (2)	0.7547 (3)	0.13808 (5)	0.0479 (5)
C9	0.5746 (2)	0.6372 (3)	0.15553 (5)	0.0552 (5)
H9	0.6729	0.6203	0.1498	0.066*
C10	0.5260 (2)	0.5307 (3)	0.18189 (5)	0.0570 (5)
C11	0.6072 (3)	0.3823 (4)	0.18816 (7)	0.0896 (9)
H11	0.6905	0.3577	0.1761	0.107*
C12	0.5674 (4)	0.2717 (5)	0.21174 (8)	0.1084 (11)
H12	0.6237	0.1730	0.2154	0.130*
C13	0.4463 (3)	0.3036 (4)	0.23001 (7)	0.0863 (8)
H13	0.4196	0.2274	0.2460	0.104*
C14	0.3653 (3)	0.4485 (4)	0.22456 (6)	0.0762 (7)
H14	0.2826	0.4716	0.2369	0.091*
C15	0.4043 (3)	0.5618 (3)	0.20089 (5)	0.0671 (6)
H15	0.3478	0.6608	0.1977	0.081*
C16	0.6078 (2)	1.0153 (3)	0.06611 (5)	0.0508 (5)
H16A	0.5557	1.1143	0.0575	0.061*
H16B	0.6966	1.0574	0.0764	0.061*
C17	0.6504 (2)	0.9004 (3)	0.04036 (5)	0.0532 (5)
C18	0.6844 (3)	0.8080 (4)	0.01999 (6)	0.0761 (7)
H18	0.7116	0.7341	0.0037	0.091*
N1	0.51305 (15)	0.9304 (2)	0.08949 (4)	0.0455 (4)
O1	0.72273 (14)	0.8256 (2)	0.11070 (4)	0.0649 (4)
S1	0.32280 (6)	0.82420 (9)	0.145920 (14)	0.0667 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0428 (9)	0.0399 (10)	0.0610 (13)	0.0036 (8)	0.0089 (9)	−0.0108 (9)
C2	0.0426 (10)	0.0505 (12)	0.0763 (16)	0.0000 (9)	0.0150 (11)	−0.0098 (11)
C3	0.0394 (10)	0.0539 (12)	0.0912 (18)	0.0034 (9)	−0.0007 (11)	−0.0134 (13)
C4	0.0519 (11)	0.0600 (13)	0.0698 (15)	0.0084 (10)	−0.0087 (11)	−0.0048 (12)
C5	0.0457 (10)	0.0527 (12)	0.0610 (14)	−0.0002 (9)	0.0028 (10)	−0.0015 (10)
C6	0.0371 (9)	0.0355 (9)	0.0586 (13)	0.0003 (7)	0.0039 (8)	−0.0079 (9)
C7	0.0424 (10)	0.0479 (11)	0.0525 (12)	−0.0026 (8)	0.0020 (8)	−0.0078 (10)
C8	0.0468 (10)	0.0494 (11)	0.0476 (11)	−0.0006 (9)	0.0022 (9)	−0.0093 (10)
C9	0.0527 (11)	0.0587 (13)	0.0543 (13)	−0.0017 (10)	−0.0018 (10)	−0.0070 (11)
C10	0.0606 (12)	0.0624 (14)	0.0481 (12)	−0.0023 (10)	−0.0088 (10)	−0.0051 (11)
C11	0.0892 (18)	0.100 (2)	0.0790 (19)	0.0273 (16)	0.0084 (15)	0.0242 (17)
C12	0.117 (3)	0.110 (2)	0.098 (2)	0.032 (2)	0.006 (2)	0.045 (2)
C13	0.099 (2)	0.094 (2)	0.0654 (18)	−0.0107 (17)	−0.0083 (16)	0.0213 (16)
C14	0.0838 (16)	0.094 (2)	0.0507 (14)	−0.0108 (15)	0.0001 (13)	−0.0006 (14)
C15	0.0807 (15)	0.0700 (15)	0.0506 (14)	0.0014 (13)	0.0015 (12)	−0.0025 (12)
C16	0.0395 (9)	0.0467 (11)	0.0662 (14)	−0.0037 (8)	0.0062 (9)	0.0011 (10)
C17	0.0492 (11)	0.0534 (12)	0.0569 (14)	0.0037 (9)	0.0078 (10)	0.0095 (11)
C18	0.0952 (18)	0.0717 (17)	0.0614 (16)	0.0160 (14)	0.0134 (14)	0.0044 (14)
N1	0.0373 (7)	0.0437 (9)	0.0555 (10)	−0.0022 (6)	0.0045 (7)	−0.0020 (8)
O1	0.0399 (7)	0.0831 (11)	0.0718 (10)	−0.0003 (7)	0.0004 (7)	0.0077 (9)
S1	0.0603 (3)	0.0835 (4)	0.0565 (4)	0.0174 (3)	0.0176 (3)	0.0016 (3)

C1—C6	1.394 (3)	C9—H9	0.9300
C1—C2	1.394 (3)	C10—C15	1.384 (3)
C1—S1	1.741 (2)	C10—C11	1.388 (3)
C2—C3	1.369 (3)	C11—C12	1.366 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.372 (3)	C12—C13	1.363 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.389 (3)	C13—C14	1.358 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.382 (3)	C14—C15	1.380 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—N1	1.423 (2)	C15—H15	0.9300
C7—O1	1.224 (2)	C16—C17	1.461 (3)
C7—N1	1.375 (2)	C16—N1	1.466 (2)
C7—C8	1.488 (3)	C16—H16A	0.9700
C8—C9	1.338 (3)	C16—H16B	0.9700
C8—S1	1.7482 (19)	C17—C18	1.164 (3)
C9—C10	1.458 (3)	C18—H18	0.9300
C6—C1—C2	119.8 (2)	C11—C10—C9	117.1 (2)
C6—C1—S1	122.42 (15)	C12—C11—C10	121.3 (3)
C2—C1—S1	117.68 (16)	C12—C11—H11	119.3
C3—C2—C1	120.6 (2)	C10—C11—H11	119.3
C3—C2—H2	119.7	C13—C12—C11	121.0 (3)
C1—C2—H2	119.7	C13—C12—H12	119.5
C2—C3—C4	119.73 (19)	C11—C12—H12	119.5
C2—C3—H3	120.1	C14—C13—C12	118.9 (3)
C4—C3—H3	120.1	C14—C13—H13	120.5
C3—C4—C5	120.3 (2)	C12—C13—H13	120.5
C3—C4—H4	119.8	C13—C14—C15	120.8 (3)
C5—C4—H4	119.8	C13—C14—H14	119.6
C6—C5—C4	120.6 (2)	C15—C14—H14	119.6
C6—C5—H5	119.7	C14—C15—C10	121.1 (2)
C4—C5—H5	119.7	C14—C15—H15	119.4
C5—C6—C1	118.78 (17)	C10—C15—H15	119.4
C5—C6—N1	120.64 (17)	C17—C16—N1	112.83 (16)
C1—C6—N1	120.57 (18)	C17—C16—H16A	109.0
O1—C7—N1	119.64 (18)	N1—C16—H16A	109.0
O1—C7—C8	120.80 (19)	C17—C16—H16B	109.0
N1—C7—C8	119.54 (16)	N1—C16—H16B	109.0
C9—C8—C7	117.30 (18)	H16A—C16—H16B	107.8
C9—C8—S1	123.48 (16)	C18—C17—C16	179.5 (2)
C7—C8—S1	119.10 (15)	C17—C18—H18	180.0
C8—C9—C10	131.7 (2)	C7—N1—C6	125.65 (16)
C8—C9—H9	114.1	C7—N1—C16	114.90 (15)
C10—C9—H9	114.1	C6—N1—C16	118.65 (16)
C15—C10—C11	116.8 (2)	C1—S1—C8	101.50 (9)
C15—C10—C9	126.0 (2)