(2Z)-2-Benzyl-idene-4-n-butyl-3,4-di-hydro-2H-1,4-benzo-thia-zin-3-one.

In the title compound, C19H19NOS, the six-membered hetero-cyclic ring of the benzo-thia-zine fragment exhibits a screw boat conformation. The plane of the fused benzene ring makes a dihedral angle of 72.38 (12)° with that of the terminal phenyl ring, and is nearly perpendicular to the mean plane formed by the atoms through the n-butyl chain, as indicated by the dihedral angle of 88.1 (2)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions to form supra-molecular chains along [110].

Related literature

For the pharmaceutical and biochemical properties of benzo­thia­zine and their derivatives, see: Malagu et al. (1998 ▶); Wammack et al. (2002 ▶); Rathore & Kumar (2006 ▶); Zia-ur-Rehman et al. (2009 ▶). For related structures, see: Sebbar et al. (2014 ▶); Saeed et al. (2010 ▶). For puckering calculations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H19NOS

M = 309.41

Triclinic,

a = 8.7717 (13) Å

b = 8.8631 (13) Å

c = 12.3184 (16) Å

α = 88.283 (9)°

β = 82.302 (9)°

γ = 60.895 (8)°

V = 828.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.20 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 = 0.641, T max = 0.746

17374 measured reflections

3923 independent reflections

2912 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.04

3923 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 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/S160053681401054X/tk5313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401054X/tk5313Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401054X/tk5313Isup3.cml

CCDC reference: 1001815

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

C19H19NOS	Z = 2
Mr = 309.41	F(000) = 328
Triclinic, P1	Dx = 1.240 Mg m−3
Hall symbol: -P 1	Melting point: 363 K
a = 8.7717 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8631 (13) Å	Cell parameters from 3923 reflections
c = 12.3184 (16) Å	θ = 2.6–27.9°
α = 88.283 (9)°	µ = 0.20 mm−1
β = 82.302 (9)°	T = 296 K
γ = 60.895 (8)°	Block, yellow
V = 828.5 (2) Å3	0.37 × 0.34 × 0.28 mm

Bruker X8 APEX diffractometer	3923 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 27.9°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.641, Tmax = 0.746	k = −11→11
17374 measured reflections	l = −16→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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.061P)2 + 0.1635P] where P = (Fo2 + 2Fc2)/3
3923 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 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	0.9210 (2)	0.3479 (2)	0.82655 (15)	0.0483 (4)
C2	1.0667 (3)	0.2113 (2)	0.76691 (19)	0.0648 (5)
H2	1.0839	0.2136	0.6909	0.078*
C3	1.1845 (3)	0.0746 (3)	0.8185 (2)	0.0758 (7)
H3	1.2794	−0.0181	0.7779	0.091*
C4	1.1622 (3)	0.0746 (3)	0.9299 (2)	0.0761 (7)
H4	1.2449	−0.0169	0.9653	0.091*
C5	1.0181 (3)	0.2089 (2)	0.99169 (18)	0.0622 (5)
H5	1.0048	0.2067	1.0678	0.075*
C6	0.8931 (2)	0.3472 (2)	0.93992 (14)	0.0447 (4)
C7	0.6448 (2)	0.6452 (2)	0.96790 (12)	0.0416 (3)
C8	0.69106 (19)	0.6857 (2)	0.85347 (12)	0.0408 (3)
C9	0.6528 (2)	0.8484 (2)	0.83178 (12)	0.0449 (4)
H9	0.5991	0.9273	0.8912	0.054*
C10	0.6840 (2)	0.9191 (2)	0.72724 (13)	0.0466 (4)
C11	0.6707 (3)	0.8635 (3)	0.62735 (15)	0.0647 (5)
H11	0.6374	0.7790	0.6247	0.078*
C12	0.7061 (3)	0.9318 (3)	0.53127 (16)	0.0779 (7)
H12	0.6960	0.8930	0.4646	0.093*
C13	0.7560 (3)	1.0563 (3)	0.53309 (18)	0.0795 (7)
H13	0.7860	1.0976	0.4680	0.095*
C14	0.7610 (4)	1.1182 (3)	0.6313 (2)	0.0900 (8)
H14	0.7893	1.2064	0.6335	0.108*
C15	0.7245 (3)	1.0520 (3)	0.72774 (17)	0.0720 (6)
H15	0.7271	1.0971	0.7942	0.086*
C16	0.6813 (2)	0.4450 (2)	1.11277 (13)	0.0498 (4)
H16A	0.7185	0.3226	1.1158	0.060*
H16B	0.5536	0.5075	1.1257	0.060*
C17	0.7506 (3)	0.4944 (3)	1.20408 (14)	0.0575 (5)
H17A	0.7010	0.6189	1.2084	0.069*
H17B	0.8776	0.4429	1.1879	0.069*
C18	0.7032 (4)	0.4335 (4)	1.31329 (17)	0.0835 (7)
H18A	0.5767	0.4786	1.3261	0.100*
H18B	0.7586	0.3084	1.3093	0.100*
C19	0.7580 (5)	0.4878 (5)	1.4086 (2)	0.1144 (11)
H19A	0.7221	0.4471	1.4750	0.172*
H19B	0.7032	0.6116	1.4136	0.172*
H19C	0.8837	0.4394	1.3983	0.172*
N1	0.73979 (17)	0.48044 (16)	1.00182 (10)	0.0425 (3)
O1	0.52331 (16)	0.75693 (15)	1.02912 (9)	0.0587 (3)
S1	0.77675 (6)	0.51831 (6)	0.75323 (3)	0.05429 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (8)	0.0423 (8)	0.0613 (10)	−0.0214 (7)	0.0011 (7)	−0.0073 (7)
C2	0.0519 (11)	0.0527 (10)	0.0814 (13)	−0.0224 (9)	0.0096 (10)	−0.0181 (10)
C3	0.0487 (11)	0.0488 (11)	0.114 (2)	−0.0139 (9)	0.0033 (12)	−0.0223 (12)
C4	0.0515 (11)	0.0422 (10)	0.127 (2)	−0.0129 (9)	−0.0271 (13)	0.0001 (11)
C5	0.0576 (11)	0.0471 (10)	0.0800 (13)	−0.0209 (9)	−0.0224 (10)	0.0038 (9)
C6	0.0390 (8)	0.0371 (8)	0.0612 (10)	−0.0204 (7)	−0.0090 (7)	−0.0005 (7)
C7	0.0403 (8)	0.0431 (8)	0.0394 (8)	−0.0188 (7)	−0.0045 (6)	−0.0009 (6)
C8	0.0358 (7)	0.0442 (8)	0.0376 (7)	−0.0160 (6)	−0.0026 (6)	−0.0032 (6)
C9	0.0464 (9)	0.0444 (8)	0.0371 (7)	−0.0174 (7)	−0.0028 (6)	−0.0013 (6)
C10	0.0470 (9)	0.0444 (8)	0.0422 (8)	−0.0184 (7)	−0.0021 (7)	0.0014 (7)
C11	0.0884 (14)	0.0673 (12)	0.0484 (10)	−0.0453 (11)	−0.0118 (10)	0.0071 (9)
C12	0.1082 (18)	0.0814 (15)	0.0432 (10)	−0.0467 (14)	−0.0055 (11)	0.0038 (10)
C13	0.1030 (18)	0.0853 (16)	0.0524 (12)	−0.0518 (14)	0.0037 (11)	0.0152 (11)
C14	0.139 (2)	0.0867 (16)	0.0709 (15)	−0.0779 (17)	−0.0069 (15)	0.0133 (12)
C15	0.1083 (17)	0.0646 (12)	0.0529 (11)	−0.0508 (12)	−0.0056 (11)	0.0009 (9)
C16	0.0588 (10)	0.0537 (10)	0.0468 (9)	−0.0350 (9)	−0.0085 (8)	0.0085 (7)
C17	0.0750 (13)	0.0627 (11)	0.0488 (9)	−0.0431 (10)	−0.0157 (9)	0.0101 (8)
C18	0.128 (2)	0.1015 (18)	0.0516 (11)	−0.0780 (17)	−0.0226 (12)	0.0191 (11)
C19	0.181 (3)	0.155 (3)	0.0538 (13)	−0.114 (3)	−0.0322 (17)	0.0187 (16)
N1	0.0422 (7)	0.0427 (7)	0.0425 (7)	−0.0207 (6)	−0.0057 (5)	0.0029 (5)
O1	0.0574 (7)	0.0498 (7)	0.0433 (6)	−0.0096 (6)	0.0075 (5)	−0.0014 (5)
S1	0.0622 (3)	0.0504 (3)	0.0421 (2)	−0.0221 (2)	−0.00101 (19)	−0.00837 (17)

C1—C6	1.386 (2)	C11—H11	0.9300
C1—C2	1.391 (2)	C12—C13	1.373 (4)
C1—S1	1.7505 (19)	C12—H12	0.9300
C2—C3	1.361 (3)	C13—C14	1.358 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.360 (4)	C14—C15	1.377 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.388 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—N1	1.474 (2)
C5—C6	1.394 (2)	C16—C17	1.516 (2)
C5—H5	0.9300	C16—H16A	0.9700
C6—N1	1.421 (2)	C16—H16B	0.9700
C7—O1	1.2199 (18)	C17—C18	1.516 (3)
C7—N1	1.369 (2)	C17—H17A	0.9700
C7—C8	1.496 (2)	C17—H17B	0.9700
C8—C9	1.339 (2)	C18—C19	1.500 (3)
C8—S1	1.7514 (16)	C18—H18A	0.9700
C9—C10	1.466 (2)	C18—H18B	0.9700
C9—H9	0.9300	C19—H19A	0.9600
C10—C11	1.379 (3)	C19—H19B	0.9600
C10—C15	1.386 (3)	C19—H19C	0.9600
C11—C12	1.380 (3)
C6—C1—C2	120.52 (18)	C14—C13—H13	120.5
C6—C1—S1	121.86 (12)	C12—C13—H13	120.5
C2—C1—S1	117.62 (16)	C13—C14—C15	120.8 (2)
C3—C2—C1	120.8 (2)	C13—C14—H14	119.6
C3—C2—H2	119.6	C15—C14—H14	119.6
C1—C2—H2	119.6	C14—C15—C10	121.0 (2)
C4—C3—C2	119.40 (19)	C14—C15—H15	119.5
C4—C3—H3	120.3	C10—C15—H15	119.5
C2—C3—H3	120.3	N1—C16—C17	114.51 (14)
C3—C4—C5	121.1 (2)	N1—C16—H16A	108.6
C3—C4—H4	119.5	C17—C16—H16A	108.6
C5—C4—H4	119.5	N1—C16—H16B	108.6
C4—C5—C6	120.2 (2)	C17—C16—H16B	108.6
C4—C5—H5	119.9	H16A—C16—H16B	107.6
C6—C5—H5	119.9	C16—C17—C18	110.99 (16)
C1—C6—C5	117.94 (16)	C16—C17—H17A	109.4
C1—C6—N1	121.31 (14)	C18—C17—H17A	109.4
C5—C6—N1	120.73 (16)	C16—C17—H17B	109.4
O1—C7—N1	120.87 (14)	C18—C17—H17B	109.4
O1—C7—C8	120.34 (14)	H17A—C17—H17B	108.0
N1—C7—C8	118.79 (13)	C19—C18—C17	113.8 (2)
C9—C8—C7	118.94 (14)	C19—C18—H18A	108.8
C9—C8—S1	123.81 (12)	C17—C18—H18A	108.8
C7—C8—S1	117.05 (12)	C19—C18—H18B	108.8
C8—C9—C10	128.90 (15)	C17—C18—H18B	108.8
C8—C9—H9	115.5	H18A—C18—H18B	107.7
C10—C9—H9	115.5	C18—C19—H19A	109.5
C11—C10—C15	117.53 (17)	C18—C19—H19B	109.5
C11—C10—C9	123.43 (17)	H19A—C19—H19B	109.5
C15—C10—C9	119.02 (16)	C18—C19—H19C	109.5
C10—C11—C12	120.8 (2)	H19A—C19—H19C	109.5
C10—C11—H11	119.6	H19B—C19—H19C	109.5
C12—C11—H11	119.6	C7—N1—C6	124.49 (13)
C13—C12—C11	120.6 (2)	C7—N1—C16	116.46 (13)
C13—C12—H12	119.7	C6—N1—C16	118.97 (13)
C11—C12—H12	119.7	C1—S1—C8	99.56 (8)
C14—C13—C12	119.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.93	2.50	3.407 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.50	3.407 (2)	165

Symmetry code: (i) .