(4Z)-1-Methyl-4-[(2E)-2-(4-methyl-benzyl-idene)hydrazin-1-yl-idene]-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(17)H(17)N(3)O(2)S, the dihedral angle between the aromatic rings is 6.3 (5)° and the C=N-N=C group is statistically planar [torsion angle = 179.8 (8)°]. The conformation of the thia-zine ring is an envelope, with the S atom displaced by 0.823 (9) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.012 Å). In the crystal, C-H⋯O inter-actions link the mol-ecules into C(5) chains propagating along [101]. The chains are consolidated by weak aromatic π-π stacking between the benzene and toluene rings [centroid-to-centroid separation = 3.826 (5) Å and inter-planar angle = 6.3 (4)°].

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011 ▶). For related structures, see: Shafiq, Khan et al. (2011 ▶); Shafiq et al. (2012 ▶). For C—H⋯O inter­actions, see: Steiner (2006 ▶). For graph-set nomenclature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H17N3O2S

M = 327.40

Monoclinic,

a = 7.899 (1) Å

b = 25.061 (3) Å

c = 8.1743 (11) Å

β = 101.114 (9)°

V = 1587.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.45 × 0.21 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

13483 measured reflections

2877 independent reflections

1897 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.120

wR(F 2) = 0.347

S = 1.15

2877 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.44 e Å−3

Δρmin = −0.46 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039529/zj2094sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039529/zj2094Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039529/zj2094Isup3.cml

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

C17H17N3O2S	F(000) = 688
Mr = 327.40	Dx = 1.370 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3678 reflections
a = 7.899 (1) Å	θ = 2.8–24.9°
b = 25.061 (3) Å	µ = 0.22 mm−1
c = 8.1743 (11) Å	T = 296 K
β = 101.114 (9)°	Blade, yellow
V = 1587.8 (3) Å3	0.45 × 0.21 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 25.3°, θmin = 2.7°
ω scans	h = −9→9
13483 measured reflections	k = −30→30
2877 independent reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.120	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.347	w = 1/[σ2(Fo2) + (0.0894P)2 + 15.6763P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2877 reflections	Δρmax = 1.44 e Å−3
215 parameters	Δρmin = −0.46 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (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	0.2464 (11)	0.6374 (3)	0.1249 (10)	0.0393 (19)
C2	0.0924 (11)	0.6173 (4)	0.0246 (12)	0.048 (2)
H2	−0.0062	0.6384	0.0023	0.058*
C3	0.0902 (12)	0.5668 (4)	−0.0386 (13)	0.052 (2)
H3	−0.0107	0.5539	−0.1047	0.063*
C4	0.2323 (12)	0.5349 (4)	−0.0072 (12)	0.050 (2)
H4	0.2283	0.5005	−0.0500	0.060*
C5	0.3802 (11)	0.5541 (3)	0.0875 (11)	0.042 (2)
H5	0.4779	0.5326	0.1070	0.050*
C6	0.3899 (10)	0.6050 (3)	0.1561 (10)	0.0329 (17)
C7	0.5555 (10)	0.6233 (3)	0.2611 (10)	0.0378 (19)
C8	0.5629 (11)	0.6777 (3)	0.3398 (11)	0.046 (2)
H8A	0.6805	0.6908	0.3583	0.055*
H8B	0.5283	0.6751	0.4471	0.055*
C9	0.9564 (11)	0.5776 (4)	0.4027 (12)	0.045 (2)
H9	0.928 (13)	0.538 (4)	0.348 (12)	0.07 (3)*
C10	1.1248 (10)	0.5891 (3)	0.5059 (10)	0.0362 (19)
C11	1.1580 (11)	0.6354 (4)	0.5998 (11)	0.045 (2)
H11	1.0710	0.6606	0.5980	0.054*
C12	1.3211 (11)	0.6445 (3)	0.6965 (11)	0.044 (2)
H12	1.3421	0.6755	0.7598	0.053*
C13	1.4514 (11)	0.6077 (4)	0.6988 (11)	0.043 (2)
C14	1.4177 (11)	0.5616 (4)	0.6071 (12)	0.051 (2)
H14	1.5050	0.5365	0.6101	0.062*
C15	1.2550 (10)	0.5515 (4)	0.5095 (10)	0.041 (2)
H15	1.2343	0.5202	0.4480	0.049*
C16	0.0902 (13)	0.7157 (4)	0.2205 (13)	0.059 (3)
H16A	0.0280	0.7308	0.1185	0.089*
H16B	0.1207	0.7435	0.3017	0.089*
H16C	0.0189	0.6899	0.2617	0.089*
C17	1.6295 (12)	0.6184 (5)	0.8015 (14)	0.064 (3)
H17A	1.7116	0.6205	0.7292	0.096*
H17B	1.6610	0.5900	0.8802	0.096*
H17C	1.6284	0.6516	0.8602	0.096*
S1	0.4268 (3)	0.72269 (9)	0.2121 (3)	0.0472 (7)
N1	0.2450 (9)	0.6901 (3)	0.1900 (11)	0.052 (2)
N2	0.6832 (9)	0.5911 (3)	0.2813 (9)	0.0448 (18)
N3	0.8324 (9)	0.6113 (3)	0.3859 (10)	0.0477 (19)
O1	0.4836 (11)	0.7265 (3)	0.0588 (9)	0.069 (2)
O2	0.4100 (10)	0.7710 (2)	0.3007 (9)	0.064 (2)

	U11	U22	U33	U12	U13	U23
C1	0.038 (5)	0.036 (4)	0.042 (5)	−0.003 (4)	0.004 (4)	0.001 (4)
C2	0.033 (5)	0.049 (5)	0.061 (6)	0.006 (4)	0.004 (4)	0.006 (4)
C3	0.038 (5)	0.050 (6)	0.062 (6)	−0.016 (4)	−0.009 (4)	0.003 (5)
C4	0.057 (6)	0.033 (5)	0.061 (6)	−0.008 (4)	0.016 (5)	−0.011 (4)
C5	0.032 (4)	0.039 (5)	0.054 (5)	0.004 (4)	0.006 (4)	−0.004 (4)
C6	0.031 (4)	0.032 (4)	0.037 (4)	0.000 (3)	0.009 (3)	0.000 (3)
C7	0.036 (4)	0.042 (5)	0.036 (5)	−0.001 (4)	0.007 (4)	−0.001 (4)
C8	0.042 (5)	0.051 (5)	0.043 (5)	−0.001 (4)	0.006 (4)	−0.006 (4)
C9	0.039 (5)	0.047 (5)	0.048 (5)	0.001 (4)	0.010 (4)	−0.004 (4)
C10	0.034 (4)	0.040 (4)	0.035 (4)	0.004 (3)	0.008 (4)	0.006 (3)
C11	0.042 (5)	0.045 (5)	0.051 (5)	0.007 (4)	0.015 (4)	0.000 (4)
C12	0.043 (5)	0.041 (5)	0.046 (5)	−0.003 (4)	0.004 (4)	−0.004 (4)
C13	0.038 (5)	0.050 (5)	0.040 (5)	−0.003 (4)	0.005 (4)	0.011 (4)
C14	0.036 (5)	0.055 (6)	0.062 (6)	0.013 (4)	0.006 (4)	0.000 (5)
C15	0.038 (5)	0.045 (5)	0.040 (5)	0.006 (4)	0.006 (4)	−0.004 (4)
C16	0.067 (7)	0.051 (6)	0.066 (7)	0.013 (5)	0.028 (5)	0.005 (5)
C17	0.034 (5)	0.086 (8)	0.065 (7)	−0.001 (5)	−0.004 (5)	0.013 (6)
S1	0.0551 (15)	0.0354 (12)	0.0503 (14)	−0.0034 (10)	0.0081 (11)	−0.0015 (10)
N1	0.038 (4)	0.040 (4)	0.078 (6)	0.005 (3)	0.010 (4)	−0.012 (4)
N2	0.030 (4)	0.048 (4)	0.053 (5)	−0.001 (3)	0.001 (3)	−0.004 (3)
N3	0.035 (4)	0.054 (5)	0.052 (5)	−0.006 (3)	0.002 (3)	−0.007 (4)
O1	0.099 (6)	0.059 (4)	0.057 (4)	−0.025 (4)	0.033 (4)	0.004 (3)
O2	0.081 (5)	0.037 (3)	0.073 (5)	0.004 (3)	0.010 (4)	−0.013 (3)

C1—C6	1.378 (11)	C10—C15	1.391 (11)
C1—C2	1.421 (12)	C11—C12	1.394 (12)
C1—N1	1.424 (11)	C11—H11	0.9300
C2—C3	1.366 (13)	C12—C13	1.378 (12)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.362 (13)	C13—C14	1.377 (13)
C3—H3	0.9300	C13—C17	1.517 (12)
C4—C5	1.359 (12)	C14—C15	1.398 (12)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.388 (11)	C15—H15	0.9300
C5—H5	0.9300	C16—N1	1.445 (11)
C6—C7	1.493 (11)	C16—H16A	0.9600
C7—N2	1.278 (10)	C16—H16B	0.9600
C7—C8	1.502 (12)	C16—H16C	0.9600
C8—S1	1.757 (9)	C17—H17A	0.9600
C8—H8A	0.9700	C17—H17B	0.9600
C8—H8B	0.9700	C17—H17C	0.9600
C9—N3	1.280 (11)	S1—O1	1.414 (7)
C9—C10	1.459 (12)	S1—O2	1.430 (6)
C9—H9	1.10 (10)	S1—N1	1.632 (8)
C10—C11	1.390 (12)	N2—N3	1.410 (9)
C6—C1—C2	118.7 (7)	C13—C12—C11	120.3 (8)
C6—C1—N1	122.8 (7)	C13—C12—H12	119.8
C2—C1—N1	118.4 (7)	C11—C12—H12	119.8
C3—C2—C1	119.5 (8)	C14—C13—C12	119.3 (8)
C3—C2—H2	120.2	C14—C13—C17	120.8 (9)
C1—C2—H2	120.2	C12—C13—C17	120.0 (9)
C4—C3—C2	121.5 (8)	C13—C14—C15	121.5 (8)
C4—C3—H3	119.2	C13—C14—H14	119.3
C2—C3—H3	119.2	C15—C14—H14	119.3
C5—C4—C3	119.1 (8)	C10—C15—C14	119.0 (8)
C5—C4—H4	120.4	C10—C15—H15	120.5
C3—C4—H4	120.4	C14—C15—H15	120.5
C4—C5—C6	122.0 (8)	N1—C16—H16A	109.5
C4—C5—H5	119.0	N1—C16—H16B	109.5
C6—C5—H5	119.0	H16A—C16—H16B	109.5
C1—C6—C5	119.2 (7)	N1—C16—H16C	109.5
C1—C6—C7	121.6 (7)	H16A—C16—H16C	109.5
C5—C6—C7	119.3 (7)	H16B—C16—H16C	109.5
N2—C7—C6	117.5 (7)	C13—C17—H17A	109.5
N2—C7—C8	123.6 (8)	C13—C17—H17B	109.5
C6—C7—C8	118.9 (7)	H17A—C17—H17B	109.5
C7—C8—S1	111.0 (6)	C13—C17—H17C	109.5
C7—C8—H8A	109.4	H17A—C17—H17C	109.5
S1—C8—H8A	109.4	H17B—C17—H17C	109.5
C7—C8—H8B	109.4	O1—S1—O2	117.9 (4)
S1—C8—H8B	109.4	O1—S1—N1	111.0 (5)
H8A—C8—H8B	108.0	O2—S1—N1	108.3 (4)
N3—C9—C10	121.7 (8)	O1—S1—C8	107.9 (5)
N3—C9—H9	118 (5)	O2—S1—C8	110.4 (4)
C10—C9—H9	120 (5)	N1—S1—C8	99.7 (4)
C11—C10—C15	119.6 (8)	C1—N1—C16	123.0 (8)
C11—C10—C9	122.5 (8)	C1—N1—S1	115.8 (6)
C15—C10—C9	117.9 (8)	C16—N1—S1	120.9 (6)
C10—C11—C12	120.3 (8)	C7—N2—N3	113.4 (7)
C10—C11—H11	119.8	C9—N3—N2	111.1 (7)
C12—C11—H11	119.8
C6—C1—C2—C3	−0.3 (13)	C11—C12—C13—C17	178.7 (8)
N1—C1—C2—C3	−179.7 (9)	C12—C13—C14—C15	1.1 (14)
C1—C2—C3—C4	0.4 (15)	C17—C13—C14—C15	−178.9 (9)
C2—C3—C4—C5	−0.9 (15)	C11—C10—C15—C14	−0.5 (12)
C3—C4—C5—C6	1.3 (14)	C9—C10—C15—C14	179.8 (8)
C2—C1—C6—C5	0.7 (12)	C13—C14—C15—C10	−0.2 (14)
N1—C1—C6—C5	−179.9 (8)	C7—C8—S1—O1	−60.6 (7)
C2—C1—C6—C7	−179.6 (8)	C7—C8—S1—O2	169.2 (6)
N1—C1—C6—C7	−0.3 (12)	C7—C8—S1—N1	55.4 (7)
C4—C5—C6—C1	−1.2 (13)	C6—C1—N1—C16	−153.1 (9)
C4—C5—C6—C7	179.1 (8)	C2—C1—N1—C16	26.3 (13)
C1—C6—C7—N2	−178.7 (8)	C6—C1—N1—S1	32.7 (11)
C5—C6—C7—N2	0.9 (11)	C2—C1—N1—S1	−147.9 (7)
C1—C6—C7—C8	2.5 (11)	O1—S1—N1—C1	57.5 (8)
C5—C6—C7—C8	−177.9 (8)	O2—S1—N1—C1	−171.6 (6)
N2—C7—C8—S1	148.3 (7)	C8—S1—N1—C1	−56.1 (7)
C6—C7—C8—S1	−33.0 (9)	O1—S1—N1—C16	−116.9 (8)
N3—C9—C10—C11	4.0 (13)	O2—S1—N1—C16	14.1 (9)
N3—C9—C10—C15	−176.4 (8)	C8—S1—N1—C16	129.5 (8)
C15—C10—C11—C12	0.3 (13)	C6—C7—N2—N3	−178.3 (7)
C9—C10—C11—C12	179.9 (8)	C8—C7—N2—N3	0.4 (12)
C10—C11—C12—C13	0.6 (13)	C10—C9—N3—N2	−179.7 (7)
C11—C12—C13—C14	−1.3 (13)	C7—N2—N3—C9	179.8 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2i	0.96	2.59	3.468 (13)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2i	0.96	2.59	3.468 (13)	153

Symmetry code: (i) .