4-Hydrazinyl-idene-1-methyl-3H-2λ,1-benzothia-zine-2,2-dione.

In the title compound, C(9)H(11)N(3)O(2)S, the thia-zine ring adopts a half-chair conformation. In the crystal structure N-H⋯N hydrogen bonds connect two mol-ecules into a centrosymmetric dimer, forming an R(2) (2)(6) ring motif. These dimers are further connected into chains by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Shafiq et al. (2011b ▶). For information on 1,2 and 2,1-benzothia­zine, see: Shafiq et al. (2011a ▶); Arshad et al. (2011 ▶). For related structures, see: Tahir et al. (2008 ▶); Khan et al. (2010 ▶); Shafiq et al. (2009 ▶); Arshad et al. (2009 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11N3O2S

M = 225.27

Monoclinic,

a = 6.6643 (2) Å

b = 9.6834 (3) Å

c = 15.5890 (5) Å

β = 97.699 (1)°

V = 996.94 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.41 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.884, T max = 0.947

8966 measured reflections

2426 independent reflections

2114 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.111

S = 0.93

2426 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.29 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 for Windows (Farrugia, 1997 ▶) and 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/S1600536811027577/bt5565sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027577/bt5565Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027577/bt5565Isup3.cml

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

C9H11N3O2S	F(000) = 472
Mr = 225.27	Dx = 1.501 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5698 reflections
a = 6.6643 (2) Å	θ = 3.7–28.3°
b = 9.6834 (3) Å	µ = 0.31 mm−1
c = 15.5890 (5) Å	T = 296 K
β = 97.699 (1)°	Needle, yellow
V = 996.94 (5) Å3	0.41 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2426 independent reflections
Radiation source: fine-focus sealed tube	2114 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 28.3°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→8
Tmin = 0.884, Tmax = 0.947	k = −11→12
8966 measured reflections	l = −19→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0763P)2 + 0.3098P] where P = (Fo2 + 2Fc2)/3
2426 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.8692 (2)	0.28978 (14)	0.04960 (9)	0.0354 (3)
C2	0.7617 (2)	0.38627 (17)	−0.00433 (10)	0.0460 (4)
H2	0.6510	0.4306	0.0138	0.055*
C3	0.8167 (3)	0.41727 (17)	−0.08437 (11)	0.0491 (4)
H3	0.7420	0.4811	−0.1200	0.059*
C4	0.9815 (3)	0.35393 (17)	−0.11144 (10)	0.0468 (4)
H4	1.0209	0.3765	−0.1647	0.056*
C5	1.0884 (2)	0.25656 (16)	−0.05909 (10)	0.0409 (3)
H5	1.1990	0.2134	−0.0781	0.049*
C6	1.0349 (2)	0.22102 (13)	0.02180 (9)	0.0328 (3)
C7	1.1508 (2)	0.11464 (13)	0.07523 (8)	0.0341 (3)
C8	1.0878 (3)	0.07413 (16)	0.16103 (10)	0.0454 (4)
H8A	1.2040	0.0386	0.1987	0.054*
H8B	0.9866	0.0017	0.1524	0.054*
C9	0.6206 (3)	0.3164 (2)	0.15568 (14)	0.0609 (5)
H9A	0.6343	0.4141	0.1652	0.091*
H9B	0.5906	0.2723	0.2076	0.091*
H9C	0.5128	0.2991	0.1096	0.091*
N1	0.80990 (19)	0.26108 (15)	0.13215 (9)	0.0446 (3)
N2	1.30403 (19)	0.06040 (13)	0.04671 (8)	0.0427 (3)
N3	1.4169 (2)	−0.03646 (17)	0.09606 (11)	0.0565 (4)
O1	1.14407 (18)	0.31926 (13)	0.22310 (7)	0.0515 (3)
O2	0.8941 (2)	0.17659 (15)	0.28274 (8)	0.0587 (3)
S1	0.98824 (5)	0.21730 (4)	0.20972 (2)	0.03865 (15)
H1N	1.357 (3)	−0.087 (2)	0.1305 (13)	0.046*
H2N	1.494 (3)	−0.070 (2)	0.0678 (12)	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0314 (6)	0.0370 (7)	0.0375 (7)	0.0038 (5)	0.0035 (5)	−0.0031 (5)
C2	0.0376 (7)	0.0488 (8)	0.0501 (8)	0.0144 (6)	0.0008 (6)	−0.0016 (7)
C3	0.0513 (8)	0.0484 (8)	0.0442 (8)	0.0120 (7)	−0.0065 (6)	0.0047 (6)
C4	0.0572 (9)	0.0476 (8)	0.0345 (7)	0.0076 (7)	0.0028 (6)	0.0034 (6)
C5	0.0457 (8)	0.0419 (7)	0.0356 (7)	0.0095 (6)	0.0075 (6)	−0.0007 (6)
C6	0.0338 (6)	0.0312 (6)	0.0334 (6)	0.0043 (5)	0.0040 (5)	−0.0026 (5)
C7	0.0363 (6)	0.0317 (6)	0.0350 (6)	0.0052 (5)	0.0076 (5)	−0.0005 (5)
C8	0.0563 (9)	0.0386 (7)	0.0445 (8)	0.0131 (6)	0.0188 (7)	0.0076 (6)
C9	0.0404 (8)	0.0763 (12)	0.0702 (12)	0.0155 (8)	0.0231 (8)	0.0002 (10)
N1	0.0331 (6)	0.0560 (7)	0.0470 (7)	0.0112 (5)	0.0137 (5)	0.0033 (6)
N2	0.0440 (6)	0.0422 (6)	0.0437 (6)	0.0151 (5)	0.0122 (5)	0.0063 (5)
N3	0.0554 (8)	0.0581 (9)	0.0595 (9)	0.0307 (7)	0.0210 (7)	0.0176 (7)
O1	0.0558 (7)	0.0577 (7)	0.0402 (6)	−0.0082 (5)	0.0041 (5)	−0.0058 (5)
O2	0.0627 (7)	0.0715 (8)	0.0479 (7)	0.0109 (6)	0.0288 (6)	0.0109 (6)
S1	0.0408 (2)	0.0428 (2)	0.0345 (2)	0.00504 (13)	0.01310 (14)	0.00140 (12)

C1—C2	1.390 (2)	C8—S1	1.7532 (15)
C1—C6	1.4068 (19)	C8—H8A	0.9700
C1—N1	1.4234 (19)	C8—H8B	0.9700
C2—C3	1.380 (2)	C9—N1	1.4616 (19)
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.373 (2)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.381 (2)	N1—S1	1.6338 (14)
C4—H4	0.9300	N2—N3	1.3721 (18)
C5—C6	1.398 (2)	N3—H1N	0.86 (2)
C5—H5	0.9300	N3—H2N	0.790 (19)
C6—C7	1.4761 (18)	O1—S1	1.4278 (12)
C7—N2	1.2801 (17)	O2—S1	1.4270 (12)
C7—C8	1.5063 (19)
C2—C1—C6	119.61 (14)	S1—C8—H8A	109.6
C2—C1—N1	119.68 (13)	C7—C8—H8B	109.6
C6—C1—N1	120.71 (13)	S1—C8—H8B	109.6
C3—C2—C1	121.03 (14)	H8A—C8—H8B	108.1
C3—C2—H2	119.5	N1—C9—H9A	109.5
C1—C2—H2	119.5	N1—C9—H9B	109.5
C4—C3—C2	120.07 (14)	H9A—C9—H9B	109.5
C4—C3—H3	120.0	N1—C9—H9C	109.5
C2—C3—H3	120.0	H9A—C9—H9C	109.5
C3—C4—C5	119.60 (15)	H9B—C9—H9C	109.5
C3—C4—H4	120.2	C1—N1—C9	120.59 (14)
C5—C4—H4	120.2	C1—N1—S1	117.21 (10)
C4—C5—C6	121.84 (14)	C9—N1—S1	118.42 (13)
C4—C5—H5	119.1	C7—N2—N3	119.27 (13)
C6—C5—H5	119.1	N2—N3—H1N	118.0 (13)
C5—C6—C1	117.81 (13)	N2—N3—H2N	108.4 (14)
C5—C6—C7	120.23 (12)	H1N—N3—H2N	121 (2)
C1—C6—C7	121.95 (13)	O2—S1—O1	117.61 (8)
N2—C7—C6	118.14 (12)	O2—S1—N1	107.94 (8)
N2—C7—C8	122.12 (12)	O1—S1—N1	111.81 (8)
C6—C7—C8	119.74 (11)	O2—S1—C8	111.06 (8)
C7—C8—S1	110.19 (10)	O1—S1—C8	107.46 (8)
C7—C8—H8A	109.6	N1—S1—C8	99.48 (8)
C6—C1—C2—C3	−0.9 (2)	C6—C7—C8—S1	−33.65 (17)
N1—C1—C2—C3	179.38 (15)	C2—C1—N1—C9	9.0 (2)
C1—C2—C3—C4	−0.9 (3)	C6—C1—N1—C9	−170.69 (15)
C2—C3—C4—C5	1.7 (3)	C2—C1—N1—S1	−148.76 (13)
C3—C4—C5—C6	−0.7 (3)	C6—C1—N1—S1	31.55 (18)
C4—C5—C6—C1	−1.1 (2)	C6—C7—N2—N3	178.54 (14)
C4—C5—C6—C7	178.92 (14)	C8—C7—N2—N3	−0.9 (2)
C2—C1—C6—C5	1.9 (2)	C1—N1—S1—O2	−172.78 (11)
N1—C1—C6—C5	−178.42 (13)	C9—N1—S1—O2	28.97 (17)
C2—C1—C6—C7	−178.15 (13)	C1—N1—S1—O1	56.36 (14)
N1—C1—C6—C7	1.5 (2)	C9—N1—S1—O1	−101.89 (15)
C5—C6—C7—N2	2.4 (2)	C1—N1—S1—C8	−56.87 (13)
C1—C6—C7—N2	−177.54 (13)	C9—N1—S1—C8	144.88 (15)
C5—C6—C7—C8	−178.13 (13)	C7—C8—S1—O2	169.33 (11)
C1—C6—C7—C8	1.9 (2)	C7—C8—S1—O1	−60.75 (13)
N2—C7—C8—S1	145.78 (13)	C7—C8—S1—N1	55.82 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···O1i	0.86 (2)	2.46 (2)	3.221 (2)	147.7 (17)
N3—H2N···N2ii	0.790 (19)	2.376 (19)	3.094 (2)	151.8 (19)
C8—H8A···O1i	0.97	2.59	3.4178 (19)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯O1i	0.86 (2)	2.46 (2)	3.221 (2)	147.7 (17)
N3—H2N⋯N2ii	0.790 (19)	2.376 (19)	3.094 (2)	151.8 (19)
C8—H8A⋯O1i	0.97	2.59	3.4178 (19)	144

Symmetry codes: (i) ; (ii) .