3,3-Dibromo-1-ethyl-1H-2,1-benzo-thiazin-4(3H)-one 2,2-dioxide.

In the mol-ecule of the title compound, C(10)H(9)Br(2)NO(3)S, the S atom is four-coordinated in distorted tetra-hedral configuration. The heterocyclic thia-zine ring adopts a twist conformation. An intra-molecular C-H⋯O hydrogen bond results in the formation of a non-planar five-membered ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into infinite chains along the c axis.

Related literature

For related literature, see: Franzén (2000 ▶); Misu & Togo (2003 ▶); Shafiq et al. (2008 ▶); Tahir et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H9Br2NO3S

M = 383.06

Monoclinic,

a = 7.7979 (5) Å

b = 11.9645 (7) Å

c = 13.1231 (8) Å

β = 95.374 (3)°

V = 1218.98 (13) Å3

Z = 4

Mo Kα radiation

μ = 6.82 mm−1

T = 296 (2) K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.400, T max = 0.508

14754 measured reflections

3281 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.221

S = 1.02

3281 reflections

154 parameters

H-atom parameters constrained

Δρmax = 1.27 e Å−3

Δρmin = −1.61 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017510/hk2472sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017510/hk2472Isup2.hkl

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

C10H9Br2NO3S	F000 = 744
Mr = 383.06	Dx = 2.087 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 708 reflections
a = 7.7979 (5) Å	θ = 2.3–29.2º
b = 11.9645 (7) Å	µ = 6.82 mm−1
c = 13.1231 (8) Å	T = 296 (2) K
β = 95.374 (3)º	Prismatic, red
V = 1218.98 (13) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker KappaAPEXII CCD diffractometer	3281 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.059
Detector resolution: 7.40 pixels mm-1	θmax = 29.2º
T = 296(2) K	θmin = 2.3º
ω scans	h = −8→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −16→15
Tmin = 0.400, Tmax = 0.508	l = −17→18
14754 measured reflections

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.221	w = 1/[σ2(Fo2) + (0.1081P)2 + 4.0099P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3281 reflections	Δρmax = 1.27 e Å−3
154 parameters	Δρmin = −1.61 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.97364 (12)	0.08723 (8)	0.18987 (7)	0.0520 (3)
Br2	0.71557 (15)	−0.05878 (9)	0.04712 (7)	0.0616 (4)
S1	0.5854 (3)	0.09863 (16)	0.20346 (14)	0.0353 (5)
O1	0.5802 (9)	0.1912 (5)	0.1362 (5)	0.0554 (17)
O2	0.4378 (7)	0.0280 (5)	0.2029 (4)	0.0427 (14)
O3	0.7951 (9)	−0.1813 (5)	0.2399 (5)	0.0521 (16)
N1	0.6503 (9)	0.1398 (5)	0.3180 (5)	0.0346 (15)
C1	0.6964 (10)	0.0579 (6)	0.3926 (6)	0.0296 (16)
C2	0.6905 (11)	0.0854 (7)	0.4974 (6)	0.0405 (19)
H2	0.6569	0.1565	0.5163	0.049*
C3	0.7351 (12)	0.0054 (9)	0.5708 (7)	0.051 (2)
H3	0.7337	0.0242	0.6395	0.062*
C4	0.7809 (13)	−0.0996 (8)	0.5460 (7)	0.054 (2)
H4	0.8088	−0.1523	0.5970	0.064*
C5	0.7859 (11)	−0.1275 (7)	0.4450 (6)	0.044 (2)
H5	0.8149	−0.2001	0.4278	0.053*
C6	0.7480 (10)	−0.0488 (6)	0.3675 (6)	0.0319 (16)
C7	0.7694 (10)	−0.0849 (6)	0.2634 (6)	0.0347 (17)
C8	0.7569 (10)	0.0054 (7)	0.1794 (6)	0.0348 (17)
C9	0.6490 (12)	0.2600 (6)	0.3460 (7)	0.047 (2)
H9A	0.5998	0.3023	0.2873	0.056*
H9B	0.5745	0.2700	0.4005	0.056*
C10	0.8162 (14)	0.3057 (8)	0.3789 (9)	0.065 (3)
H10A	0.8047	0.3832	0.3958	0.098*
H10B	0.8902	0.2984	0.3248	0.098*
H10C	0.8651	0.2657	0.4381	0.098*

	U11	U22	U33	U12	U13	U23
Br1	0.0447 (6)	0.0622 (6)	0.0509 (6)	−0.0139 (4)	0.0134 (4)	−0.0031 (4)
Br2	0.0757 (8)	0.0722 (7)	0.0374 (5)	−0.0052 (5)	0.0077 (5)	−0.0101 (4)
S1	0.0405 (12)	0.0358 (10)	0.0293 (10)	0.0021 (9)	0.0010 (8)	0.0063 (8)
O1	0.069 (4)	0.048 (3)	0.049 (4)	0.003 (3)	−0.001 (3)	0.021 (3)
O2	0.032 (3)	0.053 (4)	0.043 (3)	−0.010 (3)	0.005 (3)	−0.007 (3)
O3	0.074 (5)	0.035 (3)	0.047 (4)	0.009 (3)	0.010 (3)	−0.009 (3)
N1	0.049 (4)	0.026 (3)	0.028 (3)	0.002 (3)	0.000 (3)	−0.001 (2)
C1	0.027 (4)	0.031 (4)	0.030 (4)	−0.006 (3)	0.000 (3)	−0.002 (3)
C2	0.041 (5)	0.050 (5)	0.031 (4)	−0.003 (4)	0.001 (4)	−0.012 (4)
C3	0.057 (6)	0.066 (6)	0.032 (4)	−0.012 (5)	0.005 (4)	−0.005 (4)
C4	0.056 (6)	0.060 (6)	0.043 (5)	−0.004 (5)	−0.003 (4)	0.020 (4)
C5	0.046 (5)	0.044 (5)	0.044 (5)	0.000 (4)	0.009 (4)	0.014 (4)
C6	0.030 (4)	0.034 (4)	0.033 (4)	−0.001 (3)	0.006 (3)	−0.004 (3)
C7	0.031 (4)	0.035 (4)	0.038 (4)	0.001 (3)	0.000 (3)	0.000 (3)
C8	0.037 (5)	0.040 (4)	0.027 (4)	−0.008 (4)	0.004 (3)	−0.004 (3)
C9	0.058 (6)	0.026 (4)	0.056 (5)	0.013 (4)	0.005 (4)	0.000 (4)
C10	0.069 (7)	0.036 (5)	0.091 (8)	−0.011 (5)	0.008 (6)	−0.011 (5)

Br1—C8	1.947 (8)	C3—H3	0.9300
Br2—C8	1.898 (7)	C4—C5	1.371 (13)
S1—O1	1.415 (6)	C4—H4	0.9300
S1—O2	1.428 (6)	C5—C6	1.397 (11)
S1—N1	1.617 (6)	C5—H5	0.9300
S1—C8	1.792 (8)	C6—C7	1.457 (11)
O3—C7	1.215 (9)	C7—C8	1.540 (11)
N1—C1	1.408 (9)	C9—C10	1.442 (14)
N1—C9	1.486 (9)	C9—H9A	0.9700
C1—C6	1.388 (10)	C9—H9B	0.9700
C1—C2	1.418 (11)	C10—H10A	0.9600
C2—C3	1.380 (13)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.354 (14)
O1—S1—O2	119.0 (4)	C1—C6—C5	119.6 (7)
O1—S1—N1	109.3 (4)	C1—C6—C7	123.8 (7)
O2—S1—N1	111.5 (3)	C5—C6—C7	116.6 (7)
O1—S1—C8	110.8 (4)	O3—C7—C6	123.7 (7)
O2—S1—C8	104.2 (4)	O3—C7—C8	119.1 (7)
N1—S1—C8	100.3 (3)	C6—C7—C8	117.3 (6)
C1—N1—C9	120.6 (6)	C7—C8—S1	108.0 (5)
C1—N1—S1	118.2 (5)	C7—C8—Br2	111.4 (5)
C9—N1—S1	121.1 (5)	S1—C8—Br2	110.3 (4)
C6—C1—N1	122.4 (7)	C7—C8—Br1	107.8 (5)
C6—C1—C2	118.7 (7)	S1—C8—Br1	109.4 (4)
N1—C1—C2	118.9 (7)	Br2—C8—Br1	109.9 (4)
C3—C2—C1	119.1 (8)	C10—C9—N1	114.5 (7)
C3—C2—H2	120.4	C10—C9—H9A	108.6
C1—C2—H2	120.4	N1—C9—H9A	108.6
C4—C3—C2	122.1 (8)	C10—C9—H9B	108.6
C4—C3—H3	119.0	N1—C9—H9B	108.6
C2—C3—H3	119.0	H9A—C9—H9B	107.6
C3—C4—C5	119.4 (8)	C9—C10—H10A	109.5
C3—C4—H4	120.3	C9—C10—H10B	109.5
C5—C4—H4	120.3	H10A—C10—H10B	109.5
C4—C5—C6	121.1 (8)	C9—C10—H10C	109.5
C4—C5—H5	119.5	H10A—C10—H10C	109.5
C6—C5—H5	119.5	H10B—C10—H10C	109.5
O1—S1—N1—C1	−167.9 (6)	C1—C6—C7—O3	−171.2 (8)
O2—S1—N1—C1	58.5 (7)	C5—C6—C7—O3	10.1 (12)
C8—S1—N1—C1	−51.4 (6)	C1—C6—C7—C8	8.3 (11)
O1—S1—N1—C9	16.6 (8)	C5—C6—C7—C8	−170.4 (7)
O2—S1—N1—C9	−117.0 (7)	O3—C7—C8—S1	139.1 (7)
C8—S1—N1—C9	133.1 (7)	C6—C7—C8—S1	−40.4 (8)
C9—N1—C1—C6	−160.8 (7)	O3—C7—C8—Br2	17.8 (10)
S1—N1—C1—C6	23.7 (10)	C6—C7—C8—Br2	−161.7 (6)
C9—N1—C1—C2	19.1 (11)	O3—C7—C8—Br1	−102.8 (8)
S1—N1—C1—C2	−156.4 (6)	C6—C7—C8—Br1	77.7 (7)
C6—C1—C2—C3	−0.3 (12)	O1—S1—C8—C7	173.0 (5)
N1—C1—C2—C3	179.8 (8)	O2—S1—C8—C7	−57.8 (6)
C1—C2—C3—C4	−1.5 (14)	N1—S1—C8—C7	57.7 (6)
C2—C3—C4—C5	1.0 (15)	O1—S1—C8—Br2	−65.0 (5)
C3—C4—C5—C6	1.4 (14)	O2—S1—C8—Br2	64.1 (4)
N1—C1—C6—C5	−177.6 (7)	N1—S1—C8—Br2	179.6 (4)
C2—C1—C6—C5	2.6 (11)	O1—S1—C8—Br1	55.9 (5)
N1—C1—C6—C7	3.7 (12)	O2—S1—C8—Br1	−174.9 (4)
C2—C1—C6—C7	−176.1 (8)	N1—S1—C8—Br1	−59.4 (4)
C4—C5—C6—C1	−3.2 (13)	C1—N1—C9—C10	65.8 (11)
C4—C5—C6—C7	175.6 (8)	S1—N1—C9—C10	−118.8 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.52	3.390 (10)	157
C9—H9A···O1	0.97	2.38	2.876 (11)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.52	3.390 (10)	157
C9—H9A⋯O1	0.97	2.38	2.876 (11)	111

Symmetry code: (i) .