1-Ethyl-4-{2-[1-(4-methyl-phen-yl)ethyl-idene]hydrazinyl-idene}-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(19)H(21)N(3)O(2)S, the dihedral angle between the aromatic rings is 6.7 (2)° and the C=N-N=C torsion angle is 178.0 (2)°. The conformation of the thia-zine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). In the crystal, mol-ecules are linked by C-H⋯O inter-actions, generating C(5) chains propagating in [010]. A weak C-H⋯π inter-action is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a ▶). For further synthetic details, see: Shafiq et al. (2011b ▶). For a related structure, see: Shafiq et al. (2013 ▶).

Experimental

Crystal data

C19H21N3O2S

M = 355.45

Monoclinic,

a = 15.9018 (10) Å

b = 7.3716 (4) Å

c = 16.8376 (10) Å

β = 111.644 (3)°

V = 1834.57 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.34 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.937, T max = 0.955

14168 measured reflections

3597 independent reflections

2598 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.02

3597 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000202/ld2091sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000202/ld2091Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000202/ld2091Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H21N3O2S	F(000) = 752
Mr = 355.45	Dx = 1.287 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 335 reflections
a = 15.9018 (10) Å	θ = 3.1–23.5°
b = 7.3716 (4) Å	µ = 0.19 mm−1
c = 16.8376 (10) Å	T = 296 K
β = 111.644 (3)°	Prism, yellow
V = 1834.57 (19) Å3	0.34 × 0.26 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	3597 independent reflections
Radiation source: fine-focus sealed tube	2598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −19→18
Tmin = 0.937, Tmax = 0.955	k = −9→8
14168 measured reflections	l = −18→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.6783P] where P = (Fo2 + 2Fc2)/3
3597 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.40 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	0.53653 (13)	0.1072 (3)	0.23121 (12)	0.0401 (5)
C2	0.62165 (14)	0.1299 (3)	0.22572 (14)	0.0504 (6)
H2	0.6306	0.2260	0.1940	0.060*
C3	0.69200 (16)	0.0146 (4)	0.26570 (16)	0.0610 (7)
H3	0.7478	0.0324	0.2609	0.073*
C4	0.67962 (16)	−0.1279 (4)	0.31306 (17)	0.0629 (7)
H4	0.7274	−0.2057	0.3411	0.076*
C5	0.59694 (17)	−0.1552 (3)	0.31882 (16)	0.0609 (7)
H5	0.5891	−0.2528	0.3504	0.073*
C6	0.52430 (14)	−0.0399 (3)	0.27836 (14)	0.0460 (5)
C7	0.4152 (2)	−0.2572 (4)	0.3072 (2)	0.0795 (9)
H7A	0.3511	−0.2787	0.2768	0.095*
H7B	0.4483	−0.3488	0.2894	0.095*
C8	0.4360 (3)	−0.2746 (6)	0.3986 (3)	0.1315 (16)
H8A	0.4972	−0.2366	0.4293	0.197*
H8B	0.4290	−0.3989	0.4121	0.197*
H8C	0.3954	−0.1999	0.4147	0.197*
C9	0.37033 (14)	0.2050 (3)	0.18892 (14)	0.0478 (5)
H9A	0.3372	0.1275	0.1410	0.057*
H9B	0.3380	0.3191	0.1820	0.057*
C10	0.46398 (13)	0.2394 (3)	0.18915 (12)	0.0411 (5)
C11	0.43384 (14)	0.6397 (3)	0.08403 (13)	0.0451 (5)
C12	0.52607 (16)	0.6781 (3)	0.08357 (17)	0.0603 (6)
H12A	0.5486	0.7891	0.1138	0.090*
H12B	0.5226	0.6896	0.0257	0.090*
H12C	0.5661	0.5804	0.1110	0.090*
C13	0.36016 (14)	0.7729 (3)	0.04561 (13)	0.0443 (5)
C14	0.36872 (17)	0.9137 (3)	−0.00555 (15)	0.0558 (6)
H14	0.4221	0.9255	−0.0157	0.067*
C15	0.30017 (17)	1.0357 (4)	−0.04138 (15)	0.0620 (7)
H15	0.3081	1.1287	−0.0753	0.074*
C16	0.21992 (17)	1.0238 (3)	−0.02836 (14)	0.0553 (6)
C17	0.21100 (16)	0.8847 (3)	0.02377 (14)	0.0532 (6)
H17	0.1578	0.8748	0.0344	0.064*
C18	0.27955 (15)	0.7613 (3)	0.05990 (13)	0.0497 (5)
H18	0.2719	0.6691	0.0943	0.060*
C19	0.1445 (2)	1.1567 (5)	−0.0695 (2)	0.0903 (10)
H19A	0.1632	1.2757	−0.0467	0.135*
H19B	0.0920	1.1212	−0.0580	0.135*
H19C	0.1301	1.1580	−0.1302	0.135*
S1	0.37561 (4)	0.10183 (9)	0.28376 (4)	0.0544 (2)
O1	0.42132 (12)	0.2209 (3)	0.35183 (11)	0.0773 (6)
O2	0.28939 (11)	0.0333 (3)	0.27645 (13)	0.0771 (6)
N1	0.43901 (13)	−0.0742 (3)	0.28385 (14)	0.0600 (6)
N2	0.48467 (12)	0.3786 (3)	0.15443 (12)	0.0536 (5)
N3	0.41244 (13)	0.4972 (3)	0.11660 (12)	0.0546 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0382 (11)	0.0417 (12)	0.0417 (10)	0.0006 (9)	0.0160 (8)	−0.0016 (9)
C2	0.0434 (12)	0.0530 (14)	0.0597 (13)	0.0020 (10)	0.0248 (10)	0.0066 (11)
C3	0.0432 (13)	0.0687 (17)	0.0777 (16)	0.0086 (11)	0.0300 (12)	0.0084 (14)
C4	0.0482 (14)	0.0678 (17)	0.0753 (16)	0.0203 (12)	0.0257 (12)	0.0186 (13)
C5	0.0576 (15)	0.0597 (16)	0.0716 (15)	0.0152 (12)	0.0311 (12)	0.0236 (13)
C6	0.0406 (12)	0.0484 (13)	0.0526 (12)	0.0046 (9)	0.0214 (9)	0.0069 (10)
C7	0.0672 (18)	0.071 (2)	0.109 (2)	−0.0089 (14)	0.0431 (17)	0.0118 (17)
C8	0.167 (4)	0.132 (4)	0.138 (3)	0.049 (3)	0.105 (3)	0.063 (3)
C9	0.0376 (11)	0.0468 (13)	0.0555 (12)	0.0009 (9)	0.0132 (9)	0.0071 (10)
C10	0.0383 (11)	0.0425 (12)	0.0425 (10)	0.0002 (9)	0.0146 (9)	0.0005 (9)
C11	0.0472 (12)	0.0440 (13)	0.0459 (11)	−0.0017 (9)	0.0194 (9)	0.0027 (10)
C12	0.0517 (14)	0.0525 (15)	0.0792 (16)	−0.0029 (11)	0.0272 (12)	0.0070 (13)
C13	0.0477 (12)	0.0415 (12)	0.0425 (10)	−0.0024 (9)	0.0150 (9)	0.0020 (9)
C14	0.0538 (14)	0.0563 (15)	0.0589 (13)	−0.0025 (11)	0.0227 (11)	0.0149 (11)
C15	0.0665 (16)	0.0588 (16)	0.0601 (14)	0.0018 (12)	0.0226 (12)	0.0227 (12)
C16	0.0605 (15)	0.0522 (14)	0.0467 (12)	0.0083 (11)	0.0122 (11)	0.0093 (11)
C17	0.0489 (13)	0.0597 (15)	0.0511 (12)	0.0041 (11)	0.0186 (10)	0.0026 (11)
C18	0.0528 (13)	0.0472 (13)	0.0492 (12)	−0.0005 (10)	0.0191 (10)	0.0074 (10)
C19	0.083 (2)	0.099 (2)	0.089 (2)	0.0348 (18)	0.0322 (17)	0.0373 (19)
S1	0.0401 (3)	0.0653 (4)	0.0638 (4)	0.0066 (3)	0.0262 (3)	0.0137 (3)
O1	0.0671 (12)	0.1064 (16)	0.0636 (10)	0.0069 (10)	0.0302 (9)	−0.0119 (10)
O2	0.0449 (10)	0.0878 (13)	0.1101 (15)	0.0094 (9)	0.0422 (10)	0.0334 (11)
N1	0.0461 (11)	0.0570 (13)	0.0836 (14)	0.0062 (9)	0.0316 (10)	0.0266 (11)
N2	0.0456 (11)	0.0509 (12)	0.0679 (12)	0.0070 (8)	0.0251 (9)	0.0179 (10)
N3	0.0481 (11)	0.0499 (12)	0.0687 (12)	0.0076 (9)	0.0249 (9)	0.0193 (10)

C1—C6	1.399 (3)	C11—N3	1.287 (3)
C1—C2	1.400 (3)	C11—C13	1.482 (3)
C1—C10	1.477 (3)	C11—C12	1.497 (3)
C2—C3	1.368 (3)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.376 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—C14	1.387 (3)
C4—C5	1.368 (3)	C13—C18	1.391 (3)
C4—H4	0.9300	C14—C15	1.370 (3)
C5—C6	1.393 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.375 (3)
C6—N1	1.416 (3)	C15—H15	0.9300
C7—C8	1.456 (5)	C16—C17	1.391 (3)
C7—N1	1.493 (3)	C16—C19	1.505 (3)
C7—H7A	0.9700	C17—C18	1.377 (3)
C7—H7B	0.9700	C17—H17	0.9300
C8—H8A	0.9600	C18—H18	0.9300
C8—H8B	0.9600	C19—H19A	0.9600
C8—H8C	0.9600	C19—H19B	0.9600
C9—C10	1.509 (3)	C19—H19C	0.9600
C9—S1	1.742 (2)	S1—O1	1.4135 (19)
C9—H9A	0.9700	S1—O2	1.4233 (17)
C9—H9B	0.9700	S1—N1	1.643 (2)
C10—N2	1.282 (3)	N2—N3	1.397 (2)
C6—C1—C2	118.04 (19)	C11—C12—H12A	109.5
C6—C1—C10	122.43 (18)	C11—C12—H12B	109.5
C2—C1—C10	119.52 (19)	H12A—C12—H12B	109.5
C3—C2—C1	121.9 (2)	C11—C12—H12C	109.5
C3—C2—H2	119.1	H12A—C12—H12C	109.5
C1—C2—H2	119.1	H12B—C12—H12C	109.5
C2—C3—C4	119.6 (2)	C14—C13—C18	117.4 (2)
C2—C3—H3	120.2	C14—C13—C11	121.6 (2)
C4—C3—H3	120.2	C18—C13—C11	120.97 (19)
C5—C4—C3	120.0 (2)	C15—C14—C13	121.4 (2)
C5—C4—H4	120.0	C15—C14—H14	119.3
C3—C4—H4	120.0	C13—C14—H14	119.3
C4—C5—C6	121.4 (2)	C14—C15—C16	121.5 (2)
C4—C5—H5	119.3	C14—C15—H15	119.3
C6—C5—H5	119.3	C16—C15—H15	119.3
C5—C6—C1	119.1 (2)	C15—C16—C17	117.7 (2)
C5—C6—N1	120.1 (2)	C15—C16—C19	120.9 (2)
C1—C6—N1	120.82 (18)	C17—C16—C19	121.4 (2)
C8—C7—N1	112.2 (3)	C18—C17—C16	121.2 (2)
C8—C7—H7A	109.2	C18—C17—H17	119.4
N1—C7—H7A	109.2	C16—C17—H17	119.4
C8—C7—H7B	109.2	C17—C18—C13	120.9 (2)
N1—C7—H7B	109.2	C17—C18—H18	119.6
H7A—C7—H7B	107.9	C13—C18—H18	119.6
C7—C8—H8A	109.5	C16—C19—H19A	109.5
C7—C8—H8B	109.5	C16—C19—H19B	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
C7—C8—H8C	109.5	C16—C19—H19C	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
C10—C9—S1	110.92 (14)	O1—S1—O2	118.78 (12)
C10—C9—H9A	109.5	O1—S1—N1	110.96 (11)
S1—C9—H9A	109.5	O2—S1—N1	106.91 (11)
C10—C9—H9B	109.5	O1—S1—C9	107.98 (12)
S1—C9—H9B	109.5	O2—S1—C9	110.88 (10)
H9A—C9—H9B	108.0	N1—S1—C9	99.65 (11)
N2—C10—C1	117.42 (19)	C6—N1—C7	121.4 (2)
N2—C10—C9	123.51 (19)	C6—N1—S1	117.47 (16)
C1—C10—C9	119.07 (18)	C7—N1—S1	119.90 (17)
N3—C11—C13	115.83 (19)	C10—N2—N3	113.76 (18)
N3—C11—C12	124.8 (2)	C11—N3—N2	113.78 (19)
C13—C11—C12	119.40 (19)
C6—C1—C2—C3	−0.8 (3)	C15—C16—C17—C18	−1.1 (3)
C10—C1—C2—C3	177.9 (2)	C19—C16—C17—C18	178.7 (2)
C1—C2—C3—C4	−0.2 (4)	C16—C17—C18—C13	0.3 (3)
C2—C3—C4—C5	1.0 (4)	C14—C13—C18—C17	0.5 (3)
C3—C4—C5—C6	−0.8 (4)	C11—C13—C18—C17	−179.7 (2)
C4—C5—C6—C1	−0.3 (4)	C10—C9—S1—O1	61.17 (18)
C4—C5—C6—N1	178.5 (2)	C10—C9—S1—O2	−167.11 (16)
C2—C1—C6—C5	1.1 (3)	C10—C9—S1—N1	−54.73 (18)
C10—C1—C6—C5	−177.7 (2)	C5—C6—N1—C7	−19.6 (4)
C2—C1—C6—N1	−177.7 (2)	C1—C6—N1—C7	159.1 (2)
C10—C1—C6—N1	3.6 (3)	C5—C6—N1—S1	147.7 (2)
C6—C1—C10—N2	173.5 (2)	C1—C6—N1—S1	−33.5 (3)
C2—C1—C10—N2	−5.2 (3)	C8—C7—N1—C6	92.8 (3)
C6—C1—C10—C9	−6.5 (3)	C8—C7—N1—S1	−74.3 (3)
C2—C1—C10—C9	174.75 (19)	O1—S1—N1—C6	−57.8 (2)
S1—C9—C10—N2	−144.76 (19)	O2—S1—N1—C6	171.25 (17)
S1—C9—C10—C1	35.3 (2)	C9—S1—N1—C6	55.80 (19)
N3—C11—C13—C14	−167.5 (2)	O1—S1—N1—C7	109.8 (2)
C12—C11—C13—C14	13.1 (3)	O2—S1—N1—C7	−21.2 (2)
N3—C11—C13—C18	12.7 (3)	C9—S1—N1—C7	−136.6 (2)
C12—C11—C13—C18	−166.7 (2)	C1—C10—N2—N3	−179.62 (17)
C18—C13—C14—C15	−0.7 (3)	C9—C10—N2—N3	0.4 (3)
C11—C13—C14—C15	179.6 (2)	C13—C11—N3—N2	−178.06 (18)
C13—C14—C15—C16	−0.1 (4)	C12—C11—N3—N2	1.3 (3)
C14—C15—C16—C17	1.0 (4)	C10—N2—N3—C11	177.98 (19)
C14—C15—C16—C19	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.97	2.50	3.402 (4)	155
C9—H9A···Cg3ii	0.97	2.67	3.613 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.97	2.50	3.402 (4)	155
C9—H9A⋯Cg3ii	0.97	2.67	3.613 (2)	165

Symmetry codes: (i) ; (ii) .