6-Bromo-1-methyl-4-[2-(4-methyl-benzyl-idene)hydrazinyl-idene]-3H-2λ,1-benzothia-zine-2,2-dione.

In the title compound, C(17)H(16)BrN(3)O(2)S, the two fused rings are twisted by a dihedral angle of 6.61 (15)°. The thia-zine ring adopts a sofa conformation. The toluene ring is oriented at dihedral angles of 15.5 (2) and 20.6 (2)° with respect to the bromo-benzene and thia-zine rings, respectively. The benzyl-idene system is approximately planar [r.m.s. deviation = 0.0388 Å]. In the cyrstal, weak inter-molecular C-H⋯O hydrogen bonds connects the mol-ecules into a chain along the b axis.

Related literature

For the synthesis of the title compound, see: Shafiq et al. (2011 ▶). For related structures, see: Khan et al. (2010 ▶); Shafiq et al. (2009 ▶); Arshad et al. (2009 ▶).

Experimental

Crystal data

C17H16BrN3O2S

M = 406.30

Monoclinic,

a = 9.1077 (6) Å

b = 6.8328 (4) Å

c = 14.1765 (9) Å

β = 96.807 (3)°

V = 876.00 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.48 mm−1

T = 296 K

0.32 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.504, T max = 0.790

10166 measured reflections

4119 independent reflections

2881 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.078

S = 0.97

4119 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 1771 Friedel pairs

Flack parameter: 0.004 (8)

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/S1600536811028406/pv2429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028406/pv2429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028406/pv2429Isup3.cml

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

C17H16BrN3O2S	F(000) = 412
Mr = 406.30	Dx = 1.540 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3801 reflections
a = 9.1077 (6) Å	θ = 2.3–23.7°
b = 6.8328 (4) Å	µ = 2.48 mm−1
c = 14.1765 (9) Å	T = 296 K
β = 96.807 (3)°	Needle, yellow
V = 876.00 (10) Å3	0.32 × 0.12 × 0.10 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	4119 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.504, Tmax = 0.790	k = −8→9
10166 measured reflections	l = −18→18

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0256P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.018
4119 reflections	Δρmax = 0.29 e Å−3
220 parameters	Δρmin = −0.36 e Å−3
1 restraint	Absolute structure: Flack (1983), 1771 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.004 (8)

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
Br1	1.13358 (4)	1.44957 (7)	0.45270 (2)	0.08174 (14)
S1	0.72100 (10)	1.11072 (10)	0.03233 (5)	0.0611 (2)
O1	0.8404 (3)	0.9855 (3)	0.02125 (18)	0.0855 (8)
O2	0.6089 (3)	1.1379 (5)	−0.04538 (16)	0.0999 (9)
N1	0.7821 (3)	1.3277 (3)	0.06656 (16)	0.0589 (6)
N2	0.7702 (3)	0.9100 (3)	0.28328 (17)	0.0519 (6)
N3	0.6650 (3)	0.7615 (3)	0.26789 (18)	0.0556 (6)
C1	0.8667 (3)	1.3470 (4)	0.1553 (2)	0.0464 (6)
C2	0.9579 (4)	1.5101 (4)	0.1724 (2)	0.0590 (8)
H2	0.9654	1.5998	0.1238	0.071*
C3	1.0369 (4)	1.5402 (4)	0.2599 (2)	0.0625 (8)
H3	1.0959	1.6509	0.2707	0.075*
C4	1.0285 (3)	1.4062 (4)	0.3312 (2)	0.0539 (7)
C5	0.9427 (3)	1.2426 (4)	0.31626 (19)	0.0472 (7)
H5	0.9405	1.1516	0.3648	0.057*
C6	0.8585 (3)	1.2109 (4)	0.22905 (18)	0.0422 (6)
C7	0.7585 (3)	1.0412 (4)	0.21833 (19)	0.0430 (6)
C8	0.6452 (3)	1.0352 (4)	0.13283 (19)	0.0529 (7)
H8A	0.5630	1.1198	0.1430	0.063*
H8B	0.6077	0.9029	0.1235	0.063*
C9	0.6761 (3)	0.6340 (4)	0.3337 (2)	0.0497 (7)
H9	0.7494	0.6483	0.3847	0.060*
C10	0.5776 (3)	0.4669 (4)	0.33129 (17)	0.0448 (6)
C11	0.4620 (3)	0.4417 (5)	0.25878 (18)	0.0513 (6)
H11	0.4457	0.5356	0.2112	0.062*
C12	0.3723 (4)	0.2815 (4)	0.2565 (2)	0.0572 (8)
H12	0.2944	0.2689	0.2082	0.069*
C13	0.3960 (4)	0.1366 (4)	0.3257 (2)	0.0607 (8)
C14	0.5088 (4)	0.1620 (4)	0.3977 (2)	0.0614 (8)
H14	0.5244	0.0681	0.4454	0.074*
C15	0.5999 (3)	0.3245 (4)	0.4010 (2)	0.0562 (7)
H15	0.6763	0.3382	0.4503	0.067*
C16	0.2981 (4)	−0.0437 (6)	0.3201 (3)	0.0892 (11)
H16A	0.3586	−0.1589	0.3278	0.134*
H16B	0.2389	−0.0476	0.2594	0.134*
H16C	0.2347	−0.0387	0.3695	0.134*
C17	0.7742 (4)	1.4824 (6)	−0.0046 (3)	0.0913 (12)
H17A	0.7455	1.6028	0.0230	0.137*
H17B	0.7025	1.4480	−0.0572	0.137*
H17C	0.8693	1.4984	−0.0264	0.137*

	U11	U22	U33	U12	U13	U23
Br1	0.0823 (2)	0.0930 (2)	0.0655 (2)	−0.0207 (2)	−0.00971 (15)	−0.02718 (19)
S1	0.0823 (6)	0.0609 (4)	0.0395 (4)	−0.0132 (4)	0.0050 (4)	−0.0079 (3)
O1	0.1165 (19)	0.0679 (16)	0.0801 (16)	−0.0059 (15)	0.0453 (14)	−0.0163 (13)
O2	0.135 (2)	0.106 (2)	0.0500 (14)	−0.0347 (17)	−0.0242 (15)	0.0036 (13)
N1	0.0768 (18)	0.0526 (13)	0.0453 (13)	−0.0107 (13)	−0.0011 (12)	0.0057 (11)
N2	0.0566 (14)	0.0422 (13)	0.0553 (14)	−0.0149 (11)	−0.0005 (11)	0.0018 (11)
N3	0.0606 (16)	0.0462 (13)	0.0585 (15)	−0.0122 (11)	0.0003 (12)	0.0013 (11)
C1	0.0480 (17)	0.0447 (14)	0.0479 (16)	−0.0029 (12)	0.0112 (13)	−0.0047 (12)
C2	0.069 (2)	0.0496 (17)	0.0604 (19)	−0.0148 (15)	0.0168 (16)	0.0001 (13)
C3	0.063 (2)	0.0513 (16)	0.074 (2)	−0.0220 (14)	0.0096 (17)	−0.0113 (16)
C4	0.0504 (16)	0.0603 (19)	0.0498 (16)	−0.0115 (14)	0.0015 (12)	−0.0193 (14)
C5	0.0506 (17)	0.0493 (15)	0.0419 (15)	−0.0055 (12)	0.0064 (13)	−0.0036 (12)
C6	0.0419 (16)	0.0429 (13)	0.0422 (14)	−0.0058 (12)	0.0077 (12)	−0.0066 (11)
C7	0.0435 (16)	0.0438 (13)	0.0420 (14)	−0.0043 (12)	0.0063 (12)	−0.0083 (12)
C8	0.0521 (18)	0.0549 (15)	0.0515 (17)	−0.0131 (13)	0.0055 (14)	−0.0046 (13)
C9	0.0485 (16)	0.0483 (15)	0.0516 (16)	−0.0026 (13)	0.0036 (13)	−0.0007 (13)
C10	0.0486 (15)	0.0410 (13)	0.0463 (14)	0.0012 (14)	0.0120 (11)	0.0020 (13)
C11	0.0622 (17)	0.0427 (13)	0.0493 (14)	−0.0018 (17)	0.0083 (13)	0.0008 (15)
C12	0.060 (2)	0.0536 (16)	0.0583 (17)	−0.0074 (15)	0.0075 (15)	−0.0110 (15)
C13	0.064 (2)	0.0451 (15)	0.076 (2)	−0.0061 (15)	0.0235 (18)	−0.0048 (15)
C14	0.067 (2)	0.0470 (16)	0.073 (2)	−0.0025 (15)	0.0199 (18)	0.0145 (15)
C15	0.0551 (19)	0.0550 (16)	0.0592 (18)	0.0025 (15)	0.0101 (14)	0.0057 (15)
C16	0.088 (2)	0.0594 (18)	0.123 (3)	−0.027 (2)	0.025 (2)	−0.007 (3)
C17	0.094 (3)	0.085 (3)	0.089 (3)	−0.005 (2)	−0.015 (2)	0.034 (2)

Br1—C4	1.892 (3)	C8—H8A	0.9700
S1—O1	1.407 (3)	C8—H8B	0.9700
S1—O2	1.423 (3)	C9—C10	1.450 (4)
S1—N1	1.637 (3)	C9—H9	0.9300
S1—C8	1.734 (3)	C10—C15	1.384 (4)
N1—C1	1.402 (4)	C10—C11	1.392 (4)
N1—C17	1.457 (4)	C11—C12	1.364 (4)
N2—C7	1.281 (3)	C11—H11	0.9300
N2—N3	1.394 (3)	C12—C13	1.392 (4)
N3—C9	1.271 (3)	C12—H12	0.9300
C1—C2	1.394 (4)	C13—C14	1.371 (5)
C1—C6	1.408 (4)	C13—C16	1.518 (5)
C2—C3	1.374 (4)	C14—C15	1.384 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.373 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.366 (4)	C16—H16B	0.9600
C5—C6	1.392 (4)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.471 (4)	C17—H17B	0.9600
C7—C8	1.496 (4)	C17—H17C	0.9600
O1—S1—O2	119.10 (17)	S1—C8—H8B	109.5
O1—S1—N1	110.09 (15)	H8A—C8—H8B	108.1
O2—S1—N1	107.38 (15)	N3—C9—C10	121.9 (3)
O1—S1—C8	107.40 (14)	N3—C9—H9	119.1
O2—S1—C8	110.87 (15)	C10—C9—H9	119.1
N1—S1—C8	100.39 (13)	C15—C10—C11	118.3 (3)
C1—N1—C17	122.0 (3)	C15—C10—C9	119.9 (3)
C1—N1—S1	118.89 (18)	C11—C10—C9	121.7 (3)
C17—N1—S1	117.7 (2)	C12—C11—C10	121.0 (3)
C7—N2—N3	113.6 (2)	C12—C11—H11	119.5
C9—N3—N2	113.0 (2)	C10—C11—H11	119.5
C2—C1—N1	118.9 (3)	C11—C12—C13	120.7 (3)
C2—C1—C6	118.8 (3)	C11—C12—H12	119.6
N1—C1—C6	122.2 (2)	C13—C12—H12	119.6
C3—C2—C1	120.9 (3)	C14—C13—C12	118.4 (3)
C3—C2—H2	119.5	C14—C13—C16	121.7 (3)
C1—C2—H2	119.5	C12—C13—C16	119.9 (3)
C2—C3—C4	119.7 (3)	C13—C14—C15	121.3 (3)
C2—C3—H3	120.1	C13—C14—H14	119.3
C4—C3—H3	120.1	C15—C14—H14	119.3
C5—C4—C3	120.8 (3)	C14—C15—C10	120.2 (3)
C5—C4—Br1	119.2 (2)	C14—C15—H15	119.9
C3—C4—Br1	120.0 (2)	C10—C15—H15	119.9
C4—C5—C6	120.7 (3)	C13—C16—H16A	109.5
C4—C5—H5	119.7	C13—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C5—C6—C1	119.0 (2)	C13—C16—H16C	109.5
C5—C6—C7	118.9 (2)	H16A—C16—H16C	109.5
C1—C6—C7	122.0 (2)	H16B—C16—H16C	109.5
N2—C7—C6	118.7 (2)	N1—C17—H17A	109.5
N2—C7—C8	123.6 (2)	N1—C17—H17B	109.5
C6—C7—C8	117.7 (2)	H17A—C17—H17B	109.5
C7—C8—S1	110.75 (19)	N1—C17—H17C	109.5
C7—C8—H8A	109.5	H17A—C17—H17C	109.5
S1—C8—H8A	109.5	H17B—C17—H17C	109.5
C7—C8—H8B	109.5
O1—S1—N1—C1	−64.2 (3)	N3—N2—C7—C6	177.0 (2)
O2—S1—N1—C1	164.7 (2)	N3—N2—C7—C8	−1.1 (4)
C8—S1—N1—C1	48.8 (2)	C5—C6—C7—N2	−11.9 (4)
O1—S1—N1—C17	102.5 (3)	C1—C6—C7—N2	171.1 (3)
O2—S1—N1—C17	−28.6 (3)	C5—C6—C7—C8	166.3 (2)
C8—S1—N1—C17	−144.5 (3)	C1—C6—C7—C8	−10.6 (4)
C7—N2—N3—C9	−178.8 (2)	N2—C7—C8—S1	−139.9 (2)
C17—N1—C1—C2	−6.8 (4)	C6—C7—C8—S1	41.9 (3)
S1—N1—C1—C2	159.2 (2)	O1—S1—C8—C7	58.5 (2)
C17—N1—C1—C6	170.8 (3)	O2—S1—C8—C7	−169.9 (2)
S1—N1—C1—C6	−23.1 (4)	N1—S1—C8—C7	−56.6 (2)
N1—C1—C2—C3	176.7 (3)	N2—N3—C9—C10	−179.8 (2)
C6—C1—C2—C3	−1.1 (4)	N3—C9—C10—C15	175.6 (3)
C1—C2—C3—C4	1.3 (5)	N3—C9—C10—C11	−2.7 (4)
C2—C3—C4—C5	0.2 (5)	C15—C10—C11—C12	0.3 (4)
C2—C3—C4—Br1	−178.6 (2)	C9—C10—C11—C12	178.6 (3)
C3—C4—C5—C6	−1.8 (4)	C10—C11—C12—C13	−1.4 (4)
Br1—C4—C5—C6	177.0 (2)	C11—C12—C13—C14	2.1 (4)
C4—C5—C6—C1	2.0 (4)	C11—C12—C13—C16	−178.0 (3)
C4—C5—C6—C7	−175.1 (2)	C12—C13—C14—C15	−1.7 (4)
C2—C1—C6—C5	−0.5 (4)	C16—C13—C14—C15	178.4 (3)
N1—C1—C6—C5	−178.2 (2)	C13—C14—C15—C10	0.6 (4)
C2—C1—C6—C7	176.5 (2)	C11—C10—C15—C14	0.1 (4)
N1—C1—C6—C7	−1.2 (4)	C9—C10—C15—C14	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···O1i	0.96	2.64	3.546 (5)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯O1i	0.96	2.64	3.546 (5)	158

Symmetry code: (i) .