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

In the title compound, C(10)H(9)Cl(2)NO(3)S, the S atom, which is a component atom of a heterocyclic ring, shows tetra-hedral coordination. The heterocyclic ring is not planar.

Related literature

For related compounds, see: Arshad et al. (2008 ▶); Shafiq, Khan et al. (2008 ▶); Shafiq, Tahir et al. (2008 ▶); Tahir et al. (2008 ▶).

Experimental

Crystal data

C10H9Cl2NO3S

M = 294.14

Monoclinic,

a = 7.7416 (2) Å

b = 11.9185 (3) Å

c = 12.9614 (3) Å

β = 95.995 (2)°

V = 1189.39 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.72 mm−1

T = 296 (2) K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.838, T max = 0.881

12499 measured reflections

3082 independent reflections

1872 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.01

3082 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.28 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/S1600536809003079/ng2539sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003079/ng2539Isup2.hkl

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

C10H9Cl2NO3S	F(000) = 600
Mr = 294.14	Dx = 1.643 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3082 reflections
a = 7.7416 (2) Å	θ = 2.3–28.7°
b = 11.9185 (3) Å	µ = 0.72 mm−1
c = 12.9614 (3) Å	T = 296 K
β = 95.995 (2)°	Prismatic, colorless
V = 1189.39 (5) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.838, Tmax = 0.881	l = −17→15
12499 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.046P)2 + 0.3265P] where P = (Fo2 + 2Fc2)/3
3082 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.28 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
Cl1	0.45866 (9)	0.41954 (6)	0.18953 (6)	0.0592 (3)
Cl2	0.21735 (10)	0.55261 (7)	0.05418 (5)	0.0649 (3)
S1	0.08395 (8)	0.40174 (5)	0.20115 (5)	0.0421 (2)
O1	0.2953 (3)	0.68290 (16)	0.23915 (16)	0.0637 (8)
O2	−0.0624 (2)	0.47361 (15)	0.19971 (13)	0.0498 (6)
O3	0.0781 (3)	0.30825 (16)	0.13333 (15)	0.0635 (7)
N1	0.1508 (3)	0.36020 (16)	0.31795 (15)	0.0420 (7)
C1	0.1973 (3)	0.4423 (2)	0.39506 (17)	0.0359 (7)
C2	0.1918 (3)	0.4159 (2)	0.49864 (19)	0.0472 (9)
C3	0.2348 (4)	0.4945 (3)	0.5745 (2)	0.0579 (10)
C4	0.2803 (4)	0.6011 (3)	0.5502 (2)	0.0592 (10)
C5	0.2877 (3)	0.6290 (2)	0.4482 (2)	0.0510 (9)
C6	0.2506 (3)	0.5507 (2)	0.36908 (18)	0.0369 (7)
C7	0.2704 (3)	0.5872 (2)	0.26343 (19)	0.0418 (8)
C8	0.2613 (3)	0.4951 (2)	0.17788 (17)	0.0419 (8)
C9	0.1481 (4)	0.2393 (2)	0.3441 (2)	0.0549 (10)
C10	0.3251 (4)	0.1952 (3)	0.3774 (3)	0.0811 (14)
H2	0.15879	0.34423	0.51707	0.0567*
H3	0.23274	0.47473	0.64379	0.0693*
H4	0.30605	0.65411	0.60215	0.0711*
H5	0.31804	0.70172	0.43143	0.0612*
H9A	0.09821	0.19756	0.28397	0.0658*
H9B	0.07472	0.22786	0.39944	0.0658*
H10A	0.31778	0.11692	0.39385	0.1217*
H10B	0.37431	0.23552	0.43749	0.1217*
H10C	0.39743	0.20468	0.32215	0.1217*

	U11	U22	U33	U12	U13	U23
Cl1	0.0513 (4)	0.0709 (5)	0.0564 (4)	0.0130 (3)	0.0109 (3)	0.0003 (4)
Cl2	0.0770 (5)	0.0835 (6)	0.0339 (3)	0.0038 (4)	0.0045 (3)	0.0121 (3)
S1	0.0482 (3)	0.0423 (4)	0.0347 (3)	−0.0006 (3)	−0.0011 (3)	−0.0072 (3)
O1	0.0897 (15)	0.0416 (12)	0.0612 (13)	−0.0127 (10)	0.0142 (11)	0.0090 (10)
O2	0.0442 (10)	0.0585 (12)	0.0450 (10)	0.0060 (8)	−0.0028 (8)	−0.0015 (9)
O3	0.0797 (14)	0.0552 (12)	0.0542 (12)	−0.0042 (10)	−0.0001 (10)	−0.0249 (10)
N1	0.0558 (13)	0.0286 (11)	0.0403 (12)	−0.0035 (9)	−0.0005 (9)	0.0020 (9)
C1	0.0369 (12)	0.0374 (13)	0.0327 (12)	0.0025 (10)	0.0006 (9)	−0.0007 (10)
C2	0.0503 (14)	0.0531 (17)	0.0383 (14)	0.0035 (12)	0.0047 (11)	0.0094 (12)
C3	0.0592 (18)	0.082 (2)	0.0317 (14)	0.0094 (16)	0.0013 (12)	−0.0010 (14)
C4	0.0635 (18)	0.073 (2)	0.0393 (16)	0.0020 (16)	−0.0035 (13)	−0.0213 (15)
C5	0.0576 (17)	0.0452 (16)	0.0488 (16)	−0.0049 (12)	−0.0008 (12)	−0.0114 (13)
C6	0.0403 (13)	0.0362 (13)	0.0336 (12)	0.0004 (10)	0.0004 (10)	−0.0020 (10)
C7	0.0415 (13)	0.0429 (15)	0.0408 (14)	−0.0032 (11)	0.0032 (10)	0.0014 (12)
C8	0.0464 (14)	0.0494 (15)	0.0299 (13)	0.0041 (11)	0.0034 (10)	0.0034 (11)
C9	0.0631 (18)	0.0348 (15)	0.0662 (19)	−0.0044 (13)	0.0045 (14)	0.0063 (13)
C10	0.075 (2)	0.0483 (19)	0.121 (3)	0.0103 (16)	0.015 (2)	0.0158 (19)

Cl1—C8	1.766 (2)	C5—C6	1.394 (3)
Cl2—C8	1.744 (2)	C6—C7	1.460 (3)
S1—O2	1.4189 (18)	C7—C8	1.557 (3)
S1—O3	1.417 (2)	C9—C10	1.489 (4)
S1—N1	1.625 (2)	C2—H2	0.9300
S1—C8	1.817 (2)	C3—H3	0.9300
O1—C7	1.204 (3)	C4—H4	0.9300
N1—C1	1.418 (3)	C5—H5	0.9300
N1—C9	1.481 (3)	C9—H9A	0.9700
C1—C2	1.384 (3)	C9—H9B	0.9700
C1—C6	1.408 (3)	C10—H10A	0.9600
C2—C3	1.374 (4)	C10—H10B	0.9600
C3—C4	1.364 (5)	C10—H10C	0.9600
C4—C5	1.370 (4)
Cl1···O1	3.469 (2)	C2···C3iv	3.506 (4)
Cl1···O3	3.244 (2)	C2···C2iv	3.586 (3)
Cl1···N1	3.127 (2)	C3···C2iv	3.506 (4)
Cl1···C1	3.520 (2)	C3···O2iv	3.363 (3)
Cl2···O3	3.306 (2)	C3···C1iv	3.491 (4)
Cl2···O1	2.867 (2)	C6···O2	3.229 (3)
Cl2···O2	3.1604 (18)	C9···O2viii	3.273 (3)
Cl2···O2i	3.3972 (18)	C10···C2	3.285 (4)
Cl1···H10C	3.1500	C10···O2viii	3.418 (4)
Cl2···H10Aii	3.0600	C1···H10B	2.8500
O1···Cl1	3.469 (2)	C2···H10B	2.7400
O1···Cl2	2.867 (2)	C2···H9B	2.6900
O2···Cl2	3.1604 (18)	C9···H2	2.5600
O2···C6	3.229 (3)	C10···H2	2.9300
O2···Cl2i	3.3972 (18)	H2···C9	2.5600
O2···C10iii	3.418 (4)	H2···C10	2.9300
O2···C3iv	3.363 (3)	H2···H9B	2.1100
O2···C9iii	3.273 (3)	H2···H10B	2.4300
O3···C2ii	3.359 (3)	H2···O3vii	2.4800
O3···Cl2	3.306 (2)	H3···O2iv	2.6100
O3···Cl1	3.244 (2)	H4···O1ix	2.6400
O1···H5	2.4900	H5···O1	2.4900
O1···H10Cv	2.6000	H9A···O3	2.3500
O1···H4vi	2.6400	H9A···O2viii	2.6900
O2···H3iv	2.6100	H9B···C2	2.6900
O2···H9Aiii	2.6900	H9B···H2	2.1100
O2···H10Aiii	2.7900	H10A···O2viii	2.7900
O3···H9A	2.3500	H10A···Cl2vii	3.0600
O3···H2ii	2.4800	H10B···C1	2.8500
N1···Cl1	3.127 (2)	H10B···C2	2.7400
C1···Cl1	3.520 (2)	H10B···H2	2.4300
C1···C3iv	3.491 (4)	H10C···Cl1	3.1500
C2···O3vii	3.359 (3)	H10C···O1x	2.6000
C2···C10	3.285 (4)
O2—S1—O3	119.52 (12)	Cl1—C8—C7	108.92 (16)
O2—S1—N1	111.86 (11)	Cl2—C8—S1	108.36 (12)
O2—S1—C8	104.14 (11)	Cl2—C8—C7	111.57 (17)
O3—S1—N1	108.95 (11)	S1—C8—C7	107.00 (15)
O3—S1—C8	110.75 (12)	N1—C9—C10	112.0 (2)
N1—S1—C8	99.71 (11)	C1—C2—H2	120.00
S1—N1—C1	118.62 (16)	C3—C2—H2	120.00
S1—N1—C9	119.93 (16)	C2—C3—H3	119.00
C1—N1—C9	121.25 (19)	C4—C3—H3	119.00
N1—C1—C2	119.7 (2)	C3—C4—H4	120.00
N1—C1—C6	121.6 (2)	C5—C4—H4	120.00
C2—C1—C6	118.7 (2)	C4—C5—H5	119.00
C1—C2—C3	120.6 (2)	C6—C5—H5	119.00
C2—C3—C4	121.3 (2)	N1—C9—H9A	109.00
C3—C4—C5	119.1 (3)	N1—C9—H9B	109.00
C4—C5—C6	121.4 (2)	C10—C9—H9A	109.00
C1—C6—C5	118.8 (2)	C10—C9—H9B	109.00
C1—C6—C7	124.1 (2)	H9A—C9—H9B	108.00
C5—C6—C7	117.2 (2)	C9—C10—H10A	109.00
O1—C7—C6	124.2 (2)	C9—C10—H10B	110.00
O1—C7—C8	118.6 (2)	C9—C10—H10C	109.00
C6—C7—C8	117.2 (2)	H10A—C10—H10B	110.00
Cl1—C8—Cl2	111.28 (13)	H10A—C10—H10C	109.00
Cl1—C8—S1	109.60 (13)	H10B—C10—H10C	109.00
O2—S1—N1—C1	−57.1 (2)	N1—C1—C2—C3	−179.4 (2)
O2—S1—N1—C9	117.7 (2)	C6—C1—C2—C3	1.0 (4)
O3—S1—N1—C1	168.51 (19)	N1—C1—C6—C5	177.4 (2)
O3—S1—N1—C9	−16.6 (2)	N1—C1—C6—C7	−2.8 (4)
C8—S1—N1—C1	52.5 (2)	C2—C1—C6—C5	−3.1 (3)
C8—S1—N1—C9	−132.7 (2)	C2—C1—C6—C7	176.8 (2)
O2—S1—C8—Cl1	174.51 (11)	C1—C2—C3—C4	1.5 (4)
O2—S1—C8—Cl2	−63.88 (14)	C2—C3—C4—C5	−1.8 (5)
O2—S1—C8—C7	56.55 (17)	C3—C4—C5—C6	−0.3 (4)
O3—S1—C8—Cl1	−55.78 (15)	C4—C5—C6—C1	2.8 (4)
O3—S1—C8—Cl2	65.83 (16)	C4—C5—C6—C7	−177.1 (2)
O3—S1—C8—C7	−173.73 (16)	C1—C6—C7—O1	170.6 (3)
N1—S1—C8—Cl1	58.88 (14)	C1—C6—C7—C8	−10.4 (3)
N1—S1—C8—Cl2	−179.52 (12)	C5—C6—C7—O1	−9.6 (4)
N1—S1—C8—C7	−59.08 (17)	C5—C6—C7—C8	169.4 (2)
S1—N1—C1—C2	156.00 (19)	O1—C7—C8—Cl1	103.2 (2)
S1—N1—C1—C6	−24.5 (3)	O1—C7—C8—Cl2	−20.0 (3)
C9—N1—C1—C2	−18.8 (4)	O1—C7—C8—S1	−138.4 (2)
C9—N1—C1—C6	160.7 (2)	C6—C7—C8—Cl1	−75.9 (2)
S1—N1—C9—C10	118.6 (2)	C6—C7—C8—Cl2	160.91 (17)
C1—N1—C9—C10	−66.7 (3)	C6—C7—C8—S1	42.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3vii	0.9300	2.4800	3.359 (3)	157.00
C10—H10C···O1x	0.9600	2.6000	3.445 (4)	147.00