3,3-Dichloro-1-ethyl-1H-2,1-benzothia­zin-4(3H)-one 2,2-dioxide

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Ahmad, S.; Arshad, M.N.

doi:10.1107/S1600536809003079

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o430

doi:10.1107/S1600536809003079

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3,3-Dichloro-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Saeed Ahmad ^c and Muhammad Nadeem Arshad ^a

^aGovernment College University, Department of Chemistry, Lahore, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Science and Technology Bannu, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 January 2009; accepted 24 January 2009; online 31 January 2009)

In the title compound, C₁₀H₉Cl₂NO₃S, the S atom, which is a component atom of a heterocyclic ring, shows tetrahedral 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_r = 294.14
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.110
S = 1.01
3082 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003079/ng2539sup1.cif

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

checkCIF report

Comment top

In continuation to the formation of different 2,1-Benzothiazine (Shafiq, Khan et al., 2008), (Tahir et al., 2008), (Arshad et al., 2008), the title compound (I), (Fig 1), has been prepared.

We compare the bond distances and bond angles realised in (I) with the corresponding values observed in 3,3-Dibromo-1-ethyl-1H-2,1-benzothiazin- 4(3H)-one 2,2-dioxide (II) (Shafiq, Tahir et al., 2008), which is structural isomer of (I). The bond distances S1—C8 [1.817 (2) Å] and S1—N1 [1.625 (2) Å] are larger as compared to 1.792 (8) and 1.617 (6) Å, respectively. This change in the thiazine ring is observed due to the reduction of C–Cl [1.744 (2), 1.766 (2) Å] bonds as compared with C—Br [1.898 (7), 1.947 (8) Å] bonds. The dihedral angle of benzene ring with N-ethyl moiety and the SO₂ group is 78.08 (25)° and 77.99 (11)°, respectively. There exist intermolecular H-bonds (Table 1), due to which the molecules are connected in helical way along the c axis.

Related literature top

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

Experimental top

The title copound was prepared following the same method as in Shafiq, Tahir et al. (2008). A mixture of 1-Ethyl-1H-2,1 benzothiazin-4(3H)-one 2,2 dioxide (Shafiq, Khan et al., 2008)(34 mg, 0.151 mmol), N-Chloro Succinamide (40.2 mg, 0.302 mmol) and Benzoylperoxide (2.11 mg, 0.009 mmol) in Carbon Tetra Chloride (10 ml), was heated under reflux for two hours. CCl₄ was evaporated under reduced pressure and the residue was recrystallized in ethanol for X-ray diffraction studies.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); 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 (Spek, 2003).

Figures top

	Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines show the intramolecular H-bonds.
	Fig. 2. The partial packing figure (PLATON: Spek, 2003) which shows that molecules are connected through intermolecular H-bonds along the c axis in helical way.

3,3-Dichloro-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide top

Crystal data top

C₁₀H₉Cl₂NO₃S	F(000) = 600
M_r = 294.14	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.7°, θ_min = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
T_min = 0.838, T_max = 0.881	l = −17→15
12499 measured reflections

Refinement top

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(F_o²) + (0.046P)² + 0.3265P] where P = (F_o² + 2F_c²)/3
3082 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₀H₉Cl₂NO₃S	V = 1189.39 (5) Å³
M_r = 294.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7416 (2) Å	µ = 0.72 mm⁻¹
b = 11.9185 (3) Å	T = 296 K
c = 12.9614 (3) Å	0.24 × 0.20 × 0.18 mm
β = 95.995 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3082 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1872 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.881	R_int = 0.041
12499 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
3082 reflections	Δρ_min = −0.28 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···C3^iv	3.506 (4)
Cl1···O3	3.244 (2)	C2···C2^iv	3.586 (3)
Cl1···N1	3.127 (2)	C3···C2^iv	3.506 (4)
Cl1···C1	3.520 (2)	C3···O2^iv	3.363 (3)
Cl2···O3	3.306 (2)	C3···C1^iv	3.491 (4)
Cl2···O1	2.867 (2)	C6···O2	3.229 (3)
Cl2···O2	3.1604 (18)	C9···O2^viii	3.273 (3)
Cl2···O2ⁱ	3.3972 (18)	C10···C2	3.285 (4)
Cl1···H10C	3.1500	C10···O2^viii	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···C3^iv	3.363 (3)	H2···H9B	2.1100
O2···C9ⁱⁱⁱ	3.273 (3)	H2···H10B	2.4300
O3···C2ⁱⁱ	3.359 (3)	H2···O3^vii	2.4800
O3···Cl2	3.306 (2)	H3···O2^iv	2.6100
O3···Cl1	3.244 (2)	H4···O1^ix	2.6400
O1···H5	2.4900	H5···O1	2.4900
O1···H10C^v	2.6000	H9A···O3	2.3500
O1···H4^vi	2.6400	H9A···O2^viii	2.6900
O2···H3^iv	2.6100	H9B···C2	2.6900
O2···H9Aⁱⁱⁱ	2.6900	H9B···H2	2.1100
O2···H10Aⁱⁱⁱ	2.7900	H10A···O2^viii	2.7900
O3···H9A	2.3500	H10A···Cl2^vii	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···C3^iv	3.491 (4)	H10C···Cl1	3.1500
C2···O3^vii	3.359 (3)	H10C···O1^x	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)

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2; (vi) x, −y+3/2, z−1/2; (vii) x, −y+1/2, z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) x, −y+3/2, z+1/2; (x) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^vii	0.9300	2.4800	3.359 (3)	157.00
C10—H10C···O1^x	0.9600	2.6000	3.445 (4)	147.00

Symmetry codes: (vii) x, −y+1/2, z+1/2; (x) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉Cl₂NO₃S
M_r	294.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7416 (2), 11.9185 (3), 12.9614 (3)
β (°)	95.995 (2)
V (Å³)	1189.39 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.838, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	12499, 3082, 1872
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.110, 1.01
No. of reflections	3082
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Acknowledgements

MS greatfully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042-120567-PS2-276).

References

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