6-Bromo-1-methyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

In the crystal structure of the title compound, C(9)H(8)BrNO(3)S, the thia-zine ring is in the twisted form. In the crystal, pairs of inter-molecular C-H⋯O hydrogen bonds form inversion dimers with an R(2) (2)(8) ring motif. Weak inter-molecular C-H⋯Br and C-H⋯π inter-actions are also present.

Related literature

For the structures of benzothia­zine derivatives, see: Arshad et al. (2008 ▶); Shafiq et al. (2008a ▶,b ▶); Tahir et al. (2008 ▶). For the related structure, 6-bromo-1-methyl-1H-benzo[c][1,2]thia­zin-4(3H)-one 2,2-dioxide, see: Shafiq et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis, see: Lombardino (1972 ▶).

Experimental

Crystal data

C9H8BrNO3S

M = 290.13

Monoclinic,

a = 5.4577 (3) Å

b = 12.6400 (8) Å

c = 15.1258 (10) Å

β = 96.204 (2)°

V = 1037.35 (11) Å3

Z = 4

Mo Kα radiation

μ = 4.15 mm−1

T = 296 K

0.20 × 0.17 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.439, T max = 0.540

11077 measured reflections

2234 independent reflections

1709 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.04

2234 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.35 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 datablocks global, I. DOI: 10.1107/S1600536809015980/fb2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015980/fb2142Isup2.hkl

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

C9H8BrNO3S	F(000) = 576
Mr = 290.13	Dx = 1.858 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2234 reflections
a = 5.4577 (3) Å	θ = 2.1–27.0°
b = 12.6400 (8) Å	µ = 4.15 mm−1
c = 15.1258 (10) Å	T = 296 K
β = 96.204 (2)°	Prism, yellow
V = 1037.35 (11) Å3	0.20 × 0.17 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2234 independent reflections
Radiation source: fine-focus sealed tube	1709 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 7.40 pixels mm-1	θmax = 27.0°, θmin = 2.1°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.439, Tmax = 0.540	l = −18→19
11077 measured reflections

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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F2) = 0.072	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0309P)2 + 0.4349P] where P = (Fo2 + 2Fc2)/3
2234 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.35 e Å−3
31 constraints

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
Br1	0.06150 (6)	0.57510 (2)	0.36727 (2)	0.05871 (14)
S1	0.74473 (12)	0.10243 (5)	0.40740 (4)	0.03706 (17)
O1	0.3779 (4)	0.23972 (17)	0.56688 (14)	0.0606 (6)
O2	0.5116 (4)	0.05733 (15)	0.37692 (14)	0.0529 (5)
O3	0.9592 (4)	0.03989 (16)	0.40469 (14)	0.0555 (6)
N1	0.7895 (4)	0.21290 (17)	0.35343 (14)	0.0385 (5)
C1	0.6129 (4)	0.29366 (19)	0.35581 (16)	0.0326 (6)
C2	0.5631 (5)	0.3622 (2)	0.28382 (19)	0.0403 (6)
H2	0.6430	0.3525	0.2332	0.048*
C3	0.3980 (5)	0.4437 (2)	0.2866 (2)	0.0430 (7)
H3	0.3650	0.4882	0.2378	0.052*
C4	0.2814 (5)	0.4595 (2)	0.36193 (19)	0.0409 (6)
C5	0.3200 (5)	0.3919 (2)	0.43312 (19)	0.0416 (6)
H5	0.2368	0.4024	0.4829	0.050*
C6	0.4846 (4)	0.3073 (2)	0.43087 (17)	0.0362 (6)
C7	0.5129 (5)	0.2357 (2)	0.50864 (18)	0.0407 (6)
C8	0.7204 (5)	0.1553 (2)	0.51326 (17)	0.0419 (6)
H8A	0.6884	0.0989	0.5540	0.050*
H8B	0.8745	0.1891	0.5355	0.050*
C9	0.9601 (4)	0.2116 (2)	0.28524 (19)	0.0415 (6)
H9A	0.8798	0.1812	0.2316	0.062*
H9B	1.1024	0.1701	0.3057	0.062*
H9C	1.0102	0.2826	0.2737	0.062*

	U11	U22	U33	U12	U13	U23
Br1	0.0680 (2)	0.0468 (2)	0.0609 (2)	0.02306 (14)	0.00505 (16)	0.00177 (15)
S1	0.0439 (3)	0.0358 (4)	0.0327 (4)	0.0072 (3)	0.0098 (3)	0.0042 (3)
O1	0.0815 (14)	0.0670 (14)	0.0380 (12)	0.0261 (11)	0.0282 (11)	0.0127 (11)
O2	0.0603 (12)	0.0441 (12)	0.0541 (14)	−0.0125 (9)	0.0050 (10)	0.0006 (10)
O3	0.0652 (12)	0.0557 (13)	0.0489 (13)	0.0284 (10)	0.0214 (10)	0.0133 (10)
N1	0.0420 (11)	0.0415 (13)	0.0350 (13)	0.0070 (9)	0.0179 (10)	0.0092 (10)
C1	0.0345 (12)	0.0319 (14)	0.0317 (15)	−0.0013 (10)	0.0052 (10)	0.0010 (11)
C2	0.0446 (14)	0.0398 (15)	0.0382 (17)	0.0001 (11)	0.0127 (12)	0.0070 (12)
C3	0.0523 (15)	0.0346 (15)	0.0423 (17)	−0.0010 (12)	0.0061 (13)	0.0102 (12)
C4	0.0426 (13)	0.0343 (14)	0.0453 (18)	0.0060 (11)	0.0026 (12)	−0.0001 (13)
C5	0.0483 (15)	0.0431 (15)	0.0347 (16)	0.0084 (12)	0.0104 (12)	−0.0017 (13)
C6	0.0415 (13)	0.0386 (15)	0.0288 (15)	0.0030 (11)	0.0051 (11)	0.0017 (11)
C7	0.0502 (14)	0.0431 (16)	0.0296 (15)	0.0072 (12)	0.0080 (12)	0.0006 (12)
C8	0.0523 (15)	0.0464 (17)	0.0274 (15)	0.0104 (12)	0.0058 (12)	0.0057 (12)
C9	0.0403 (13)	0.0444 (16)	0.0425 (17)	−0.0026 (11)	0.0171 (12)	−0.0018 (13)

Br1—C4	1.898 (3)	C3—C4	1.379 (4)
S1—O3	1.4169 (19)	C3—H3	0.9300
S1—O2	1.424 (2)	C4—C5	1.372 (4)
S1—N1	1.649 (2)	C5—C6	1.400 (3)
S1—C8	1.753 (3)	C5—H5	0.9300
O1—C7	1.209 (3)	C6—C7	1.479 (4)
N1—C1	1.407 (3)	C7—C8	1.518 (3)
N1—C9	1.463 (3)	C8—H8A	0.9700
C1—C2	1.395 (3)	C8—H8B	0.9700
C1—C6	1.407 (3)	C9—H9A	0.9600
C2—C3	1.373 (4)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
O3—S1—O2	118.63 (13)	C4—C5—C6	120.1 (2)
O3—S1—N1	106.93 (11)	C4—C5—H5	120.0
O2—S1—N1	110.70 (12)	C6—C5—H5	120.0
O3—S1—C8	112.54 (13)	C5—C6—C1	119.3 (2)
O2—S1—C8	107.17 (13)	C5—C6—C7	117.4 (2)
N1—S1—C8	99.15 (12)	C1—C6—C7	123.2 (2)
C1—N1—C9	121.1 (2)	O1—C7—C6	122.3 (2)
C1—N1—S1	117.60 (16)	O1—C7—C8	120.3 (2)
C9—N1—S1	118.62 (17)	C6—C7—C8	117.4 (2)
C2—C1—N1	120.5 (2)	C7—C8—S1	110.06 (18)
C2—C1—C6	118.8 (2)	C7—C8—H8A	109.6
N1—C1—C6	120.8 (2)	S1—C8—H8A	109.6
C3—C2—C1	121.1 (2)	C7—C8—H8B	109.6
C3—C2—H2	119.5	S1—C8—H8B	109.6
C1—C2—H2	119.5	H8A—C8—H8B	108.2
C2—C3—C4	119.8 (3)	N1—C9—H9A	109.5
C2—C3—H3	120.1	N1—C9—H9B	109.5
C4—C3—H3	120.1	H9A—C9—H9B	109.5
C5—C4—C3	120.9 (2)	N1—C9—H9C	109.5
C5—C4—Br1	119.3 (2)	H9A—C9—H9C	109.5
C3—C4—Br1	119.8 (2)	H9B—C9—H9C	109.5
O3—S1—N1—C1	−172.74 (19)	Br1—C4—C5—C6	−179.0 (2)
O2—S1—N1—C1	56.7 (2)	C4—C5—C6—C1	1.2 (4)
C8—S1—N1—C1	−55.7 (2)	C4—C5—C6—C7	−178.3 (2)
O3—S1—N1—C9	25.6 (2)	C2—C1—C6—C5	−3.1 (4)
O2—S1—N1—C9	−105.0 (2)	N1—C1—C6—C5	176.5 (2)
C8—S1—N1—C9	142.7 (2)	C2—C1—C6—C7	176.5 (2)
C9—N1—C1—C2	12.8 (4)	N1—C1—C6—C7	−3.9 (4)
S1—N1—C1—C2	−148.4 (2)	C5—C6—C7—O1	9.9 (4)
C9—N1—C1—C6	−166.8 (2)	C1—C6—C7—O1	−169.7 (3)
S1—N1—C1—C6	32.0 (3)	C5—C6—C7—C8	−170.1 (2)
N1—C1—C2—C3	−177.5 (2)	C1—C6—C7—C8	10.3 (4)
C6—C1—C2—C3	2.0 (4)	O1—C7—C8—S1	139.9 (2)
C1—C2—C3—C4	0.9 (4)	C6—C7—C8—S1	−40.0 (3)
C2—C3—C4—C5	−2.8 (4)	O3—S1—C8—C7	170.50 (19)
C2—C3—C4—Br1	177.9 (2)	O2—S1—C8—C7	−57.3 (2)
C3—C4—C5—C6	1.7 (4)	N1—S1—C8—C7	57.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.54	3.308 (4)	140
C8—H8A···O2ii	0.97	2.54	3.470 (3)	162
C9—H9B···O3	0.96	2.41	2.824 (3)	106
C5—H5···Br1iii	0.93	2.94	3.871 (3)	175
C9—H9A···Br1iv	0.96	3.01	3.871 (2)	150
C9—H9C···Cg1v	0.96	2.83	3.449 (3)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.54	3.308 (4)	140
C8—H8A⋯O2ii	0.97	2.54	3.470 (3)	162
C9—H9B⋯O3	0.96	2.41	2.824 (3)	106
C5—H5⋯Br1iii	0.93	2.94	3.871 (3)	175
C9—H9A⋯Br1iv	0.96	3.01	3.871 (2)	150
C9—H9C⋯Cg1v	0.96	2.83	3.449 (3)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the C1–C6 ring.