1-Ethyl-4-[1-(1-phenyl-ethyl-idene)hydrazin-2-yl-idene]-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(18)H(19)N(3)O(2)S, the thia-zine ring adopts an envelope conformation, with the S atom displaced by 0.732 (1) Å from the other atoms of the ring. The phenyl ring is oriented at a dihedral angle of 79.33 (7)° with respect to the fused benzene ring. The conformations about the two double bonds in the R(2)C=N-N=C(CH(3))Ar grouping are Z and E, respectively. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R(2) (2)(8) and R(2) (2)(12) loops, as parts of infinite chains along the a-axis direction.

Related literature

For related structures and further synthetic details, see: Shafiq et al. (2011a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H19N3O2S

M = 341.42

Monoclinic,

a = 9.7278 (3) Å

b = 12.4327 (3) Å

c = 14.2607 (4) Å

β = 100.725 (1)°

V = 1694.60 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.41 × 0.08 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.920, T max = 0.988

16049 measured reflections

4129 independent reflections

2887 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.151

S = 1.00

4127 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.32 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022982/hb6798sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022982/hb6798Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022982/hb6798Isup3.cml

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

C18H19N3O2S	F(000) = 720
Mr = 341.42	Dx = 1.338 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4849 reflections
a = 9.7278 (3) Å	θ = 2.4–26.1°
b = 12.4327 (3) Å	µ = 0.21 mm−1
c = 14.2607 (4) Å	T = 296 K
β = 100.725 (1)°	Needle, colorless
V = 1694.60 (8) Å3	0.41 × 0.08 × 0.06 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4129 independent reflections
Radiation source: fine-focus sealed tube	2887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.920, Tmax = 0.988	k = −16→16
16049 measured reflections	l = −19→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0895P)2 + 0.2125P] where P = (Fo2 + 2Fc2)/3
4127 reflections	(Δ/σ)max = 0.002
219 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.78767 (5)	0.93644 (4)	1.05780 (3)	0.04426 (17)
O1	0.85670 (16)	1.03503 (13)	1.08838 (12)	0.0650 (4)
O2	0.71460 (14)	0.88277 (12)	1.12183 (10)	0.0557 (4)
N1	0.68626 (18)	0.95785 (12)	0.95522 (11)	0.0477 (4)
N2	0.89644 (17)	0.66151 (14)	0.96946 (13)	0.0556 (4)
N3	1.02548 (17)	0.65607 (14)	1.03083 (13)	0.0558 (5)
C1	0.62452 (18)	0.86638 (14)	0.90335 (12)	0.0367 (4)
C2	0.49509 (19)	0.87561 (16)	0.84347 (14)	0.0458 (5)
H2	0.4487	0.9414	0.8380	0.055*
C3	0.43489 (19)	0.78866 (17)	0.79221 (14)	0.0496 (5)
H3	0.3487	0.7963	0.7518	0.059*
C4	0.50112 (19)	0.69015 (17)	0.80018 (14)	0.0477 (5)
H4	0.4594	0.6311	0.7662	0.057*
C5	0.62979 (19)	0.68026 (15)	0.85904 (13)	0.0428 (4)
H5	0.6744	0.6138	0.8645	0.051*
C6	0.69472 (16)	0.76729 (14)	0.91056 (12)	0.0355 (4)
C7	0.83541 (17)	0.75244 (15)	0.96944 (13)	0.0401 (4)
C8	0.90722 (18)	0.84518 (16)	1.02506 (14)	0.0473 (5)
H8A	0.9653	0.8820	0.9869	0.057*
H8B	0.9677	0.8183	1.0821	0.057*
C9	1.1295 (2)	0.62777 (15)	0.99497 (15)	0.0497 (5)
C10	1.26558 (19)	0.62074 (14)	1.06248 (13)	0.0428 (4)
C11	1.3907 (2)	0.6245 (2)	1.03087 (17)	0.0634 (6)
H11	1.3910	0.6287	0.9658	0.076*
C12	1.5168 (2)	0.6219 (2)	1.09532 (19)	0.0724 (7)
H12	1.6007	0.6258	1.0731	0.087*
C13	1.5185 (2)	0.61366 (18)	1.19091 (17)	0.0589 (6)
H13	1.6030	0.6108	1.2338	0.071*
C14	1.3945 (2)	0.60965 (17)	1.22303 (15)	0.0534 (5)
H14	1.3951	0.6043	1.2882	0.064*
C15	1.2685 (2)	0.61348 (15)	1.15988 (14)	0.0471 (5)
H15	1.1851	0.6112	1.1828	0.057*
C16	0.6440 (2)	1.06836 (15)	0.92463 (15)	0.0509 (5)
H16A	0.6842	1.1183	0.9745	0.061*
H16B	0.5430	1.0742	0.9159	0.061*
C17	0.6891 (3)	1.0986 (2)	0.83489 (19)	0.0788 (8)
H17A	0.7893	1.0963	0.8440	0.118*
H17B	0.6572	1.1701	0.8170	0.118*
H17C	0.6500	1.0492	0.7854	0.118*
C18	1.1213 (3)	0.6043 (3)	0.89159 (19)	0.0970 (10)
H18A	1.0284	0.5811	0.8643	0.146*
H18B	1.1868	0.5485	0.8844	0.146*
H18C	1.1436	0.6681	0.8596	0.146*

	U11	U22	U33	U12	U13	U23
S1	0.0375 (3)	0.0554 (3)	0.0365 (3)	0.00157 (19)	−0.00216 (19)	−0.0074 (2)
O1	0.0602 (9)	0.0675 (10)	0.0606 (10)	−0.0076 (7)	−0.0063 (8)	−0.0235 (8)
O2	0.0478 (8)	0.0793 (10)	0.0402 (8)	0.0117 (7)	0.0085 (6)	0.0057 (7)
N1	0.0578 (10)	0.0388 (8)	0.0392 (9)	0.0005 (7)	−0.0099 (7)	0.0001 (7)
N2	0.0431 (9)	0.0559 (10)	0.0599 (11)	0.0109 (7)	−0.0106 (8)	0.0007 (9)
N3	0.0418 (9)	0.0636 (11)	0.0548 (11)	0.0136 (8)	−0.0097 (8)	0.0023 (9)
C1	0.0347 (9)	0.0442 (10)	0.0292 (8)	0.0000 (7)	0.0009 (7)	−0.0002 (7)
C2	0.0389 (10)	0.0519 (11)	0.0433 (10)	0.0099 (8)	−0.0009 (8)	0.0002 (9)
C3	0.0335 (9)	0.0670 (13)	0.0425 (11)	0.0018 (8)	−0.0077 (8)	−0.0021 (10)
C4	0.0447 (10)	0.0531 (11)	0.0416 (11)	−0.0072 (8)	−0.0021 (8)	−0.0084 (9)
C5	0.0426 (9)	0.0443 (10)	0.0396 (10)	0.0031 (7)	0.0023 (8)	−0.0025 (8)
C6	0.0307 (8)	0.0441 (10)	0.0300 (8)	0.0010 (7)	0.0014 (6)	0.0022 (7)
C7	0.0332 (9)	0.0498 (10)	0.0358 (9)	0.0016 (7)	0.0027 (7)	0.0014 (8)
C8	0.0306 (9)	0.0653 (12)	0.0437 (11)	0.0009 (8)	0.0010 (8)	−0.0070 (9)
C9	0.0460 (11)	0.0508 (11)	0.0484 (12)	0.0076 (8)	−0.0011 (9)	0.0052 (9)
C10	0.0396 (10)	0.0426 (10)	0.0435 (10)	0.0069 (7)	0.0009 (8)	0.0049 (8)
C11	0.0523 (13)	0.0906 (17)	0.0473 (12)	0.0097 (11)	0.0093 (10)	0.0146 (12)
C12	0.0398 (11)	0.1026 (19)	0.0750 (17)	0.0039 (11)	0.0114 (11)	0.0222 (14)
C13	0.0417 (11)	0.0669 (14)	0.0612 (14)	−0.0007 (9)	−0.0082 (10)	0.0135 (11)
C14	0.0525 (12)	0.0610 (12)	0.0429 (11)	0.0054 (9)	−0.0007 (9)	0.0061 (10)
C15	0.0419 (10)	0.0497 (11)	0.0487 (11)	0.0068 (8)	0.0057 (9)	0.0053 (9)
C16	0.0536 (12)	0.0411 (10)	0.0550 (12)	0.0094 (8)	0.0020 (10)	−0.0072 (9)
C17	0.111 (2)	0.0568 (14)	0.0637 (15)	−0.0098 (14)	0.0021 (15)	0.0094 (12)
C18	0.0702 (17)	0.163 (3)	0.0505 (15)	0.0186 (19)	−0.0083 (13)	−0.0103 (18)

S1—O2	1.4232 (15)	C9—C10	1.487 (3)
S1—O1	1.4264 (15)	C9—C18	1.490 (3)
S1—N1	1.6270 (16)	C10—C11	1.376 (3)
S1—C8	1.7493 (19)	C10—C15	1.387 (3)
N1—C1	1.427 (2)	C11—C12	1.390 (3)
N1—C16	1.477 (2)	C11—H11	0.9300
N2—C7	1.277 (2)	C12—C13	1.364 (3)
N2—N3	1.392 (2)	C12—H12	0.9300
N3—C9	1.266 (3)	C13—C14	1.368 (3)
C1—C2	1.388 (2)	C13—H13	0.9300
C1—C6	1.403 (2)	C14—C15	1.380 (3)
C2—C3	1.373 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.379 (3)	C16—C17	1.477 (3)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.377 (2)	C16—H16B	0.9700
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.392 (3)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.478 (2)	C18—H18A	0.9600
C7—C8	1.497 (3)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700
O2—S1—O1	118.02 (10)	N3—C9—C18	123.7 (2)
O2—S1—N1	111.22 (9)	C10—C9—C18	120.4 (2)
O1—S1—N1	107.84 (9)	C11—C10—C15	118.41 (18)
O2—S1—C8	107.66 (9)	C11—C10—C9	121.41 (19)
O1—S1—C8	109.90 (9)	C15—C10—C9	120.15 (18)
N1—S1—C8	100.84 (9)	C10—C11—C12	120.6 (2)
C1—N1—C16	121.41 (15)	C10—C11—H11	119.7
C1—N1—S1	117.52 (12)	C12—C11—H11	119.7
C16—N1—S1	120.46 (13)	C13—C12—C11	120.5 (2)
C7—N2—N3	114.08 (16)	C13—C12—H12	119.7
C9—N3—N2	117.05 (18)	C11—C12—H12	119.7
C2—C1—C6	119.40 (16)	C12—C13—C14	119.3 (2)
C2—C1—N1	119.94 (16)	C12—C13—H13	120.3
C6—C1—N1	120.64 (15)	C14—C13—H13	120.3
C3—C2—C1	120.69 (17)	C13—C14—C15	120.7 (2)
C3—C2—H2	119.7	C13—C14—H14	119.6
C1—C2—H2	119.7	C15—C14—H14	119.6
C2—C3—C4	120.59 (17)	C14—C15—C10	120.42 (19)
C2—C3—H3	119.7	C14—C15—H15	119.8
C4—C3—H3	119.7	C10—C15—H15	119.8
C5—C4—C3	119.17 (17)	N1—C16—C17	112.46 (18)
C5—C4—H4	120.4	N1—C16—H16A	109.1
C3—C4—H4	120.4	C17—C16—H16A	109.1
C4—C5—C6	121.62 (17)	N1—C16—H16B	109.1
C4—C5—H5	119.2	C17—C16—H16B	109.1
C6—C5—H5	119.2	H16A—C16—H16B	107.8
C5—C6—C1	118.50 (15)	C16—C17—H17A	109.5
C5—C6—C7	118.95 (15)	C16—C17—H17B	109.5
C1—C6—C7	122.54 (15)	H17A—C17—H17B	109.5
N2—C7—C6	119.48 (16)	C16—C17—H17C	109.5
N2—C7—C8	120.71 (16)	H17A—C17—H17C	109.5
C6—C7—C8	119.76 (15)	H17B—C17—H17C	109.5
C7—C8—S1	111.91 (12)	C9—C18—H18A	109.5
C7—C8—H8A	109.2	C9—C18—H18B	109.5
S1—C8—H8A	109.2	H18A—C18—H18B	109.5
C7—C8—H8B	109.2	C9—C18—H18C	109.5
S1—C8—H8B	109.2	H18A—C18—H18C	109.5
H8A—C8—H8B	107.9	H18B—C18—H18C	109.5
N3—C9—C10	115.90 (18)
O2—S1—N1—C1	−59.42 (16)	C1—C6—C7—N2	−176.73 (18)
O1—S1—N1—C1	169.72 (14)	C5—C6—C7—C8	179.76 (17)
C8—S1—N1—C1	54.52 (16)	C1—C6—C7—C8	0.7 (3)
O2—S1—N1—C16	111.72 (17)	N2—C7—C8—S1	−153.81 (16)
O1—S1—N1—C16	−19.14 (19)	C6—C7—C8—S1	28.8 (2)
C8—S1—N1—C16	−134.34 (16)	O2—S1—C8—C7	64.98 (16)
C7—N2—N3—C9	−125.1 (2)	O1—S1—C8—C7	−165.27 (14)
C16—N1—C1—C2	−21.2 (3)	N1—S1—C8—C7	−51.62 (16)
S1—N1—C1—C2	149.88 (15)	N2—N3—C9—C10	−178.94 (16)
C16—N1—C1—C6	157.43 (18)	N2—N3—C9—C18	2.2 (3)
S1—N1—C1—C6	−31.5 (2)	N3—C9—C10—C11	−159.4 (2)
C6—C1—C2—C3	0.7 (3)	C18—C9—C10—C11	19.5 (3)
N1—C1—C2—C3	179.27 (18)	N3—C9—C10—C15	18.7 (3)
C1—C2—C3—C4	0.8 (3)	C18—C9—C10—C15	−162.4 (2)
C2—C3—C4—C5	−1.1 (3)	C15—C10—C11—C12	−0.5 (3)
C3—C4—C5—C6	−0.1 (3)	C9—C10—C11—C12	177.6 (2)
C4—C5—C6—C1	1.5 (3)	C10—C11—C12—C13	1.2 (4)
C4—C5—C6—C7	−177.54 (17)	C11—C12—C13—C14	−1.0 (4)
C2—C1—C6—C5	−1.8 (3)	C12—C13—C14—C15	0.2 (3)
N1—C1—C6—C5	179.60 (17)	C13—C14—C15—C10	0.4 (3)
C2—C1—C6—C7	177.25 (16)	C11—C10—C15—C14	−0.3 (3)
N1—C1—C6—C7	−1.4 (3)	C9—C10—C15—C14	−178.37 (18)
N3—N2—C7—C6	−177.29 (16)	C1—N1—C16—C17	−69.1 (3)
N3—N2—C7—C8	5.3 (3)	S1—N1—C16—C17	120.06 (19)
C5—C6—C7—N2	2.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.43	3.390 (2)	170
C16—H16B···O2ii	0.97	2.52	3.481 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.43	3.390 (2)	170
C16—H16B⋯O2ii	0.97	2.52	3.481 (2)	171

Symmetry codes: (i) ; (ii) .