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

In the title compound, C(10)H(10)BrNO(3)S, the S atom is four-coordinated in a distorted tetra-hedral configuration with nearly equal S=O bond distances; the S-C and S-N bond lengths are 1.755 (3) and 1.649 (3) Å, respectively. The heterocyclic thia-zine ring adopts a twist conformation. Adjacent mol-ecules are attached to each other through inter-molecular C-H⋯O hydrogen bonds, forming R(2) (2)(8) and R(2) (2)(14) ring motifs. The mol-ecules are stabilized by intra- and inter-molecular hydrogen bonds, forming a three-dimensional polymeric network.

Related literature

For previous work on benzothia­zines, see: Arshad et al. (2008 ▶); Shafiq, Khan et al. (2008 ▶); Shafiq, Tahir et al. (2008 ▶); Tahir et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For synthesis, see: Lombardino (1972 ▶).

Experimental

Crystal data

C10H10BrNO3S

M = 304.16

Triclinic,

a = 7.7164 (2) Å

b = 7.9729 (3) Å

c = 10.4579 (3) Å

α = 86.767 (2)°

β = 75.773 (1)°

γ = 66.912 (2)°

V = 573.13 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.76 mm−1

T = 296 (2) K

0.28 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.486, T max = 0.639

12369 measured reflections

2846 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.095

S = 1.02

2846 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.91 e Å−3

Δρmin = −0.58 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/S1600536809002621/at2711sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002621/at2711Isup2.hkl

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

C10H10BrNO3S	Z = 2
Mr = 304.16	F(000) = 304
Triclinic, P1	Dx = 1.762 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7164 (2) Å	Cell parameters from 2847 reflections
b = 7.9729 (3) Å	θ = 2.0–28.3°
c = 10.4579 (3) Å	µ = 3.76 mm−1
α = 86.767 (2)°	T = 296 K
β = 75.773 (1)°	Needle, colourless
γ = 66.912 (2)°	0.28 × 0.16 × 0.12 mm
V = 573.13 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	1840 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.0°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.486, Tmax = 0.639	l = −13→13
12369 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.3304P] where P = (Fo2 + 2Fc2)/3
2846 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.91 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.36240 (6)	0.15247 (6)	−0.35948 (3)	0.0686 (2)
S1	−0.00069 (12)	0.19519 (10)	0.32296 (7)	0.0435 (3)
O1	0.2170 (4)	−0.2056 (3)	0.0770 (3)	0.0705 (10)
O2	−0.1737 (3)	0.2464 (3)	0.2787 (2)	0.0578 (8)
O3	−0.0156 (4)	0.2267 (3)	0.4583 (2)	0.0668 (10)
N1	0.1437 (4)	0.2891 (3)	0.2351 (2)	0.0450 (9)
C1	0.1999 (4)	0.2535 (4)	0.0977 (3)	0.0358 (9)
C2	0.2376 (5)	0.3826 (4)	0.0126 (3)	0.0444 (10)
C3	0.2876 (5)	0.3511 (4)	−0.1214 (3)	0.0471 (11)
C4	0.3017 (4)	0.1895 (4)	−0.1739 (3)	0.0423 (10)
C5	0.2710 (4)	0.0580 (4)	−0.0934 (3)	0.0416 (10)
C6	0.2210 (4)	0.0869 (4)	0.0432 (3)	0.0361 (9)
C7	0.1935 (4)	−0.0623 (4)	0.1248 (3)	0.0427 (10)
C8	0.1398 (6)	−0.0343 (4)	0.2718 (3)	0.0493 (11)
C9	0.1564 (5)	0.4465 (4)	0.2950 (3)	0.0465 (11)
C10	0.3622 (5)	0.4137 (5)	0.2925 (4)	0.0635 (14)
H2	0.22872	0.49140	0.04727	0.0533*
H3	0.31214	0.43846	−0.17724	0.0564*
H5	0.28342	−0.05116	−0.12983	0.0499*
H8A	0.065 (5)	−0.092 (5)	0.313 (4)	0.0591*
H8B	0.247 (5)	−0.063 (5)	0.306 (3)	0.0591*
H9A	0.092 (5)	0.550 (5)	0.245 (3)	0.0558*
H9B	0.085 (5)	0.457 (4)	0.382 (3)	0.0558*
H10A	0.43344	0.41151	0.20285	0.0948*
H10B	0.36403	0.50981	0.34278	0.0948*
H10C	0.42109	0.29879	0.33010	0.0948*

	U11	U22	U33	U12	U13	U23
Br1	0.0779 (3)	0.0861 (3)	0.0329 (2)	−0.0249 (2)	−0.0092 (2)	0.0002 (2)
S1	0.0540 (5)	0.0443 (4)	0.0344 (4)	−0.0260 (4)	−0.0036 (3)	0.0030 (3)
O1	0.113 (2)	0.0401 (13)	0.0672 (17)	−0.0416 (15)	−0.0168 (15)	−0.0010 (12)
O2	0.0464 (14)	0.0583 (14)	0.0673 (16)	−0.0232 (12)	−0.0074 (12)	0.0063 (12)
O3	0.098 (2)	0.0734 (16)	0.0341 (13)	−0.0463 (15)	−0.0033 (12)	0.0009 (11)
N1	0.0626 (17)	0.0467 (14)	0.0332 (14)	−0.0347 (14)	−0.0012 (12)	−0.0045 (11)
C1	0.0391 (16)	0.0356 (15)	0.0340 (16)	−0.0178 (13)	−0.0056 (12)	−0.0001 (12)
C2	0.0552 (19)	0.0351 (15)	0.0453 (19)	−0.0238 (15)	−0.0057 (15)	0.0010 (13)
C3	0.051 (2)	0.0462 (18)	0.0429 (19)	−0.0212 (16)	−0.0075 (15)	0.0110 (15)
C4	0.0425 (18)	0.0510 (18)	0.0307 (16)	−0.0164 (15)	−0.0074 (13)	0.0015 (14)
C5	0.0439 (18)	0.0377 (16)	0.0418 (18)	−0.0139 (14)	−0.0098 (14)	−0.0056 (14)
C6	0.0419 (17)	0.0324 (15)	0.0369 (16)	−0.0182 (13)	−0.0082 (13)	0.0005 (12)
C7	0.0487 (19)	0.0354 (16)	0.0491 (19)	−0.0198 (14)	−0.0158 (15)	0.0050 (14)
C8	0.061 (2)	0.0436 (18)	0.047 (2)	−0.0254 (18)	−0.0137 (17)	0.0121 (15)
C9	0.056 (2)	0.0423 (17)	0.0440 (19)	−0.0255 (17)	−0.0033 (16)	−0.0115 (15)
C10	0.065 (2)	0.066 (2)	0.071 (3)	−0.033 (2)	−0.023 (2)	−0.004 (2)

Br1—C4	1.893 (3)	C6—C7	1.477 (4)
S1—O2	1.421 (3)	C7—C8	1.496 (4)
S1—O3	1.420 (2)	C9—C10	1.499 (6)
S1—N1	1.649 (3)	C2—H2	0.9300
S1—C8	1.755 (3)	C3—H3	0.9300
O1—C7	1.202 (4)	C5—H5	0.9300
N1—C1	1.406 (4)	C8—H8A	0.89 (4)
N1—C9	1.481 (4)	C8—H8B	0.92 (4)
C1—C2	1.393 (4)	C9—H9A	0.98 (4)
C1—C6	1.409 (4)	C9—H9B	0.93 (3)
C2—C3	1.369 (4)	C10—H10A	0.9600
C3—C4	1.383 (4)	C10—H10B	0.9600
C4—C5	1.364 (4)	C10—H10C	0.9600
C5—C6	1.393 (4)
Br1···Br1i	3.5704 (5)	C2···H9A	2.61 (3)
Br1···H8Bii	3.00 (4)	C2···H10A	2.8500
O1···C2iii	3.324 (4)	C9···H2	2.5500
O2···C6	3.254 (4)	C10···H2	2.9400
O2···C10iv	3.263 (5)	H2···O1ix	2.4200
O2···C3v	3.418 (4)	H2···C9	2.5500
O3···C8vi	3.252 (4)	H2···C10	2.9400
O1···H9Aiii	2.84 (4)	H2···H9A	2.0600
O1···H2iii	2.4200	H2···H10A	2.4300
O1···H5	2.4700	H3···O2v	2.5900
O2···H10Civ	2.9000	H5···O1	2.4700
O2···H5vii	2.7400	H5···O2vii	2.7400
O2···H3v	2.5900	H8A···O3vi	2.57 (4)
O3···H9B	2.29 (3)	H8B···Br1ii	3.00 (4)
O3···H8Avi	2.57 (4)	H9A···O1ix	2.84 (4)
O3···H9Bviii	2.90 (3)	H9A···C2	2.61 (3)
C2···O1ix	3.324 (4)	H9A···H2	2.0600
C2···C10	3.348 (5)	H9B···O3	2.29 (3)
C2···C2v	3.472 (5)	H9B···O3viii	2.90 (3)
C3···O2v	3.418 (4)	H9B···H9Bviii	2.49 (4)
C6···O2	3.254 (4)	H10A···C1	2.9900
C8···O3vi	3.252 (4)	H10A···C2	2.8500
C10···C2	3.348 (5)	H10A···H2	2.4300
C10···O2x	3.263 (5)	H10C···O2x	2.9000
C1···H10A	2.9900
O2—S1—O3	118.87 (16)	S1—C8—C7	112.1 (2)
O2—S1—N1	110.91 (14)	N1—C9—C10	111.6 (3)
O2—S1—C8	106.97 (18)	C1—C2—H2	120.00
O3—S1—N1	107.50 (16)	C3—C2—H2	120.00
O3—S1—C8	111.51 (15)	C2—C3—H3	120.00
N1—S1—C8	99.36 (16)	C4—C3—H3	120.00
S1—N1—C1	117.1 (2)	C4—C5—H5	120.00
S1—N1—C9	118.39 (19)	C6—C5—H5	120.00
C1—N1—C9	121.6 (2)	S1—C8—H8A	104 (2)
N1—C1—C2	120.3 (3)	S1—C8—H8B	104 (2)
N1—C1—C6	121.0 (3)	C7—C8—H8A	113 (3)
C2—C1—C6	118.7 (3)	C7—C8—H8B	112 (2)
C1—C2—C3	120.7 (3)	H8A—C8—H8B	111 (3)
C2—C3—C4	120.1 (3)	N1—C9—H9A	104 (2)
Br1—C4—C3	119.3 (2)	N1—C9—H9B	105 (2)
Br1—C4—C5	120.0 (2)	C10—C9—H9A	115 (2)
C3—C4—C5	120.7 (3)	C10—C9—H9B	110 (3)
C4—C5—C6	120.1 (3)	H9A—C9—H9B	111 (3)
C1—C6—C5	119.6 (3)	C9—C10—H10A	109.00
C1—C6—C7	122.9 (3)	C9—C10—H10B	110.00
C5—C6—C7	117.4 (3)	C9—C10—H10C	109.00
O1—C7—C6	122.2 (3)	H10A—C10—H10B	109.00
O1—C7—C8	119.4 (3)	H10A—C10—H10C	109.00
C6—C7—C8	118.4 (3)	H10B—C10—H10C	109.00
O2—S1—N1—C1	−56.8 (3)	N1—C1—C6—C5	178.0 (3)
O2—S1—N1—C9	104.3 (2)	N1—C1—C6—C7	−2.4 (5)
O3—S1—N1—C1	171.7 (2)	C2—C1—C6—C5	−2.6 (5)
O3—S1—N1—C9	−27.2 (3)	C2—C1—C6—C7	177.1 (3)
C8—S1—N1—C1	55.5 (3)	C1—C2—C3—C4	−0.2 (6)
C8—S1—N1—C9	−143.4 (3)	C2—C3—C4—Br1	177.9 (3)
O2—S1—C8—C7	61.0 (3)	C2—C3—C4—C5	−1.7 (6)
O3—S1—C8—C7	−167.5 (3)	Br1—C4—C5—C6	−178.2 (3)
N1—S1—C8—C7	−54.3 (3)	C3—C4—C5—C6	1.3 (5)
S1—N1—C1—C2	149.4 (3)	C4—C5—C6—C1	0.8 (5)
S1—N1—C1—C6	−31.2 (4)	C4—C5—C6—C7	−178.8 (3)
C9—N1—C1—C2	−11.1 (5)	C1—C6—C7—O1	−178.0 (3)
C9—N1—C1—C6	168.3 (3)	C1—C6—C7—C8	0.4 (5)
S1—N1—C9—C10	125.2 (3)	C5—C6—C7—O1	1.7 (5)
C1—N1—C9—C10	−74.6 (4)	C5—C6—C7—C8	180.0 (3)
N1—C1—C2—C3	−178.3 (3)	O1—C7—C8—S1	−150.2 (3)
C6—C1—C2—C3	2.2 (5)	C6—C7—C8—S1	31.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ix	0.9300	2.4200	3.324 (4)	165.00
C3—H3···O2v	0.9300	2.5900	3.418 (4)	148.00
C8—H8A···O3vi	0.89 (4)	2.57 (4)	3.252 (4)	134 (3)
C9—H9B···O3	0.93 (3)	2.29 (3)	2.850 (4)	118 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.9300	2.4200	3.324 (4)	165.00
C3—H3⋯O2ii	0.9300	2.5900	3.418 (4)	148.00
C8—H8A⋯O3iii	0.89 (4)	2.57 (4)	3.252 (4)	134 (3)
C9—H9B⋯O3	0.93 (3)	2.29 (3)	2.850 (4)	118 (2)

Symmetry codes: (i) ; (ii) ; (iii) .