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

Khan, I.U.; Shafiq, M.; Arshad, M.N.

doi:10.1107/S160053681004078X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2839

https://doi.org/10.1107/S160053681004078X

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

Islam Ullah Khan,^a ^* Muhammad Shafiq ^a and Muhammad Nadeem Arshad ^a

^aMaterials Chemistry laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 30 September 2010; accepted 11 October 2010; online 20 October 2010)

In the title compound, C₁₁H₁₃NO₃S, a benzothiazine derivative, the heterocycle adopts a sofa conformation. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Volovenko et al. (2007 ). For a related structure, see: Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₁H₁₃NO₃S
M_r = 239.28
Triclinic, $[P \overline 1]$
a = 7.9448 (2) Å
b = 8.0701 (3) Å
c = 9.6267 (2) Å
α = 87.468 (2)°
β = 84.097 (2)°
γ = 64.453 (1)°
V = 553.92 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.28 × 0.21 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.925, T_max = 0.967
12058 measured reflections
2765 independent reflections
2229 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.07
2765 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.96	2.57	3.346 (2)	138
C8—H8A⋯O3ⁱⁱ	0.97	2.55	3.453 (2)	155
C2—H2⋯O1ⁱⁱⁱ	0.93	2.55	3.4665 (19)	170
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004078X/bt5369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004078X/bt5369Isup2.hkl

checkCIF report

Comment top

Here we report the crystal structure of title compound in countinuation to the previously published 3,3-dichloro-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide derivative (Shafiq et al., 2009). The difference between the two compounds is a propyl which differ just only in substitution at N and at the methylene C atom in the benzothiazine ring. The heterocycle adopts a sofa conformation. Weak C—H···O type hydrogen bonds connect the molecules to a three dimensional network.

Related literature top

For the synthesis of the title compound, see: Volovenko et al. (2007). For a related structure, see: Shafiq et al. (2009).

Experimental top

The title compound was prepared following the available literature procedure (Volovenko et al., 2007).

Structure description top

For the synthesis of the title compound, see: Volovenko et al. (2007). For a related structure, see: Shafiq et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Unit cell packing diagram showing the hydrogen bonding with dashed lines.

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

Crystal data top

C₁₁H₁₃NO₃S	Z = 2
M_r = 239.28	F(000) = 252
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9448 (2) Å	Cell parameters from 5097 reflections
b = 8.0701 (3) Å	θ = 2.2–21.8°
c = 9.6267 (2) Å	µ = 0.28 mm⁻¹
α = 87.468 (2)°	T = 296 K
β = 84.097 (2)°	Needle, light brown
γ = 64.453 (1)°	0.28 × 0.21 × 0.12 mm
V = 553.92 (2) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2765 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.925, T_max = 0.967	k = −10→10
12058 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0604P)² + 0.0882P] where P = (F_o² + 2F_c²)/3
2765 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃S	γ = 64.453 (1)°
M_r = 239.28	V = 553.92 (2) Å³
Triclinic, P1	Z = 2
a = 7.9448 (2) Å	Mo Kα radiation
b = 8.0701 (3) Å	µ = 0.28 mm⁻¹
c = 9.6267 (2) Å	T = 296 K
α = 87.468 (2)°	0.28 × 0.21 × 0.12 mm
β = 84.097 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2765 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2229 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.967	R_int = 0.027
12058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
2765 reflections	Δρ_min = −0.38 e Å⁻³
146 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.44648 (6)	0.31465 (5)	0.66978 (4)	0.04181 (14)
O1	0.2757 (2)	0.71661 (17)	0.91660 (14)	0.0633 (4)
O2	0.62535 (17)	0.25460 (17)	0.71992 (15)	0.0584 (3)
O3	0.4391 (2)	0.2879 (2)	0.52525 (12)	0.0680 (4)
N1	0.31827 (18)	0.22605 (17)	0.76115 (12)	0.0380 (3)
C1	0.28023 (19)	0.26527 (18)	0.90617 (14)	0.0313 (3)
C2	0.2496 (2)	0.1412 (2)	0.99954 (16)	0.0408 (3)
H2	0.2519	0.0338	0.9661	0.049*
C3	0.2161 (2)	0.1770 (2)	1.14058 (16)	0.0473 (4)
H3	0.1951	0.0935	1.2012	0.057*
C4	0.2129 (2)	0.3344 (2)	1.19393 (17)	0.0494 (4)
H4	0.1947	0.3549	1.2898	0.059*
C5	0.2372 (2)	0.4602 (2)	1.10331 (16)	0.0421 (3)
H5	0.2322	0.5679	1.1384	0.051*
C6	0.26911 (19)	0.42939 (18)	0.95988 (14)	0.0323 (3)
C7	0.2874 (2)	0.57493 (19)	0.87064 (16)	0.0376 (3)
C8	0.3163 (3)	0.5469 (2)	0.71447 (16)	0.0447 (4)
H8A	0.3812	0.6171	0.6723	0.054*
H8B	0.1953	0.5924	0.6773	0.054*
C9	0.3171 (2)	0.0585 (2)	0.70536 (16)	0.0398 (3)
H9A	0.3717	−0.0425	0.7696	0.048*
H9B	0.3936	0.0264	0.6168	0.048*
C10	0.1214 (2)	0.0854 (2)	0.68464 (17)	0.0461 (4)
H10A	0.0411	0.1345	0.7699	0.055*
H10B	0.1236	−0.0331	0.6673	0.055*
C11	0.0384 (3)	0.2133 (3)	0.5651 (2)	0.0662 (5)
H11A	0.0339	0.3315	0.5821	0.099*
H11B	−0.0860	0.2258	0.5575	0.099*
H11C	0.1149	0.1637	0.4797	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0535 (3)	0.0410 (2)	0.0377 (2)	−0.02944 (19)	0.01063 (16)	−0.00505 (15)
O1	0.0991 (11)	0.0410 (7)	0.0630 (8)	−0.0439 (7)	0.0020 (7)	−0.0069 (6)
O2	0.0442 (7)	0.0516 (7)	0.0801 (9)	−0.0240 (6)	0.0097 (6)	−0.0051 (6)
O3	0.1086 (11)	0.0773 (9)	0.0367 (7)	−0.0615 (9)	0.0177 (7)	−0.0119 (6)
N1	0.0526 (7)	0.0369 (6)	0.0339 (6)	−0.0295 (6)	0.0055 (5)	−0.0063 (5)
C1	0.0338 (7)	0.0295 (7)	0.0321 (7)	−0.0157 (5)	−0.0007 (5)	−0.0004 (5)
C2	0.0499 (9)	0.0319 (7)	0.0438 (8)	−0.0219 (7)	0.0001 (6)	0.0035 (6)
C3	0.0532 (10)	0.0467 (9)	0.0407 (9)	−0.0222 (8)	−0.0008 (7)	0.0127 (7)
C4	0.0580 (10)	0.0567 (10)	0.0307 (7)	−0.0227 (8)	−0.0012 (7)	0.0008 (7)
C5	0.0479 (9)	0.0413 (8)	0.0382 (8)	−0.0201 (7)	−0.0012 (6)	−0.0070 (6)
C6	0.0338 (7)	0.0294 (7)	0.0353 (7)	−0.0151 (5)	−0.0021 (5)	−0.0008 (5)
C7	0.0419 (8)	0.0297 (7)	0.0438 (8)	−0.0184 (6)	−0.0010 (6)	−0.0004 (6)
C8	0.0595 (10)	0.0351 (8)	0.0426 (8)	−0.0249 (7)	0.0003 (7)	0.0064 (6)
C9	0.0488 (9)	0.0321 (7)	0.0419 (8)	−0.0211 (6)	0.0016 (6)	−0.0089 (6)
C10	0.0573 (10)	0.0497 (9)	0.0436 (8)	−0.0347 (8)	−0.0039 (7)	−0.0002 (7)
C11	0.0646 (12)	0.0862 (15)	0.0562 (11)	−0.0401 (11)	−0.0128 (9)	0.0161 (10)

Geometric parameters (Å, º) top

S1—O2	1.4191 (14)	C5—C6	1.3915 (19)
S1—O3	1.4282 (13)	C5—H5	0.9300
S1—N1	1.6464 (12)	C6—C7	1.473 (2)
S1—C8	1.7535 (16)	C7—C8	1.509 (2)
O1—C7	1.2069 (18)	C8—H8A	0.9700
N1—C1	1.4178 (17)	C8—H8B	0.9700
N1—C9	1.4808 (17)	C9—C10	1.508 (2)
C1—C2	1.3982 (19)	C9—H9A	0.9700
C1—C6	1.4070 (18)	C9—H9B	0.9700
C2—C3	1.375 (2)	C10—C11	1.513 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.380 (2)	C10—H10B	0.9700
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.373 (2)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600

O2—S1—O3	117.98 (9)	O1—C7—C6	122.99 (14)
O2—S1—N1	111.54 (7)	O1—C7—C8	118.84 (13)
O3—S1—N1	107.86 (7)	C6—C7—C8	118.14 (12)
O2—S1—C8	107.87 (8)	C7—C8—S1	111.75 (10)
O3—S1—C8	110.27 (9)	C7—C8—H8A	109.3
N1—S1—C8	99.80 (7)	S1—C8—H8A	109.3
C1—N1—C9	120.81 (11)	C7—C8—H8B	109.3
C1—N1—S1	116.96 (9)	S1—C8—H8B	109.3
C9—N1—S1	117.37 (10)	H8A—C8—H8B	107.9
C2—C1—C6	118.28 (13)	N1—C9—C10	111.75 (13)
C2—C1—N1	120.18 (12)	N1—C9—H9A	109.3
C6—C1—N1	121.53 (12)	C10—C9—H9A	109.3
C3—C2—C1	120.42 (14)	N1—C9—H9B	109.3
C3—C2—H2	119.8	C10—C9—H9B	109.3
C1—C2—H2	119.8	H9A—C9—H9B	107.9
C2—C3—C4	121.32 (14)	C9—C10—C11	113.28 (15)
C2—C3—H3	119.3	C9—C10—H10A	108.9
C4—C3—H3	119.3	C11—C10—H10A	108.9
C5—C4—C3	118.96 (14)	C9—C10—H10B	108.9
C5—C4—H4	120.5	C11—C10—H10B	108.9
C3—C4—H4	120.5	H10A—C10—H10B	107.7
C4—C5—C6	121.20 (14)	C10—C11—H11A	109.5
C4—C5—H5	119.4	C10—C11—H11B	109.5
C6—C5—H5	119.4	H11A—C11—H11B	109.5
C5—C6—C1	119.74 (13)	C10—C11—H11C	109.5
C5—C6—C7	117.26 (12)	H11A—C11—H11C	109.5
C1—C6—C7	122.99 (12)	H11B—C11—H11C	109.5

O2—S1—N1—C1	59.41 (12)	C2—C1—C6—C5	3.0 (2)
O3—S1—N1—C1	−169.51 (11)	N1—C1—C6—C5	−178.04 (13)
C8—S1—N1—C1	−54.35 (12)	C2—C1—C6—C7	−176.18 (14)
O2—S1—N1—C9	−96.15 (12)	N1—C1—C6—C7	2.8 (2)
O3—S1—N1—C9	34.93 (14)	C5—C6—C7—O1	−0.1 (2)
C8—S1—N1—C9	150.09 (12)	C1—C6—C7—O1	179.13 (15)
C9—N1—C1—C2	3.0 (2)	C5—C6—C7—C8	−178.19 (13)
S1—N1—C1—C2	−151.64 (12)	C1—C6—C7—C8	1.0 (2)
C9—N1—C1—C6	−175.92 (13)	O1—C7—C8—S1	148.80 (14)
S1—N1—C1—C6	29.41 (17)	C6—C7—C8—S1	−32.99 (17)
C6—C1—C2—C3	−2.2 (2)	O2—S1—C8—C7	−61.58 (13)
N1—C1—C2—C3	178.80 (14)	O3—S1—C8—C7	168.29 (11)
C1—C2—C3—C4	−0.5 (2)	N1—S1—C8—C7	54.98 (12)
C2—C3—C4—C5	2.4 (3)	C1—N1—C9—C10	82.62 (17)
C3—C4—C5—C6	−1.6 (3)	S1—N1—C9—C10	−122.81 (12)
C4—C5—C6—C1	−1.1 (2)	N1—C9—C10—C11	70.53 (19)
C4—C5—C6—C7	178.08 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.96	2.57	3.346 (2)	138
C8—H8A···O3ⁱⁱ	0.97	2.55	3.453 (2)	155
C2—H2···O1ⁱⁱⁱ	0.93	2.55	3.4665 (19)	170

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃S
M_r	239.28
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9448 (2), 8.0701 (3), 9.6267 (2)
α, β, γ (°)	87.468 (2), 84.097 (2), 64.453 (1)
V (Å³)	553.92 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.28 × 0.21 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.925, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	12058, 2765, 2229
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.07
No. of reflections	2765
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.96	2.57	3.346 (2)	138.4
C8—H8A···O3ⁱⁱ	0.97	2.55	3.453 (2)	155.0
C2—H2···O1ⁱⁱⁱ	0.93	2.55	3.4665 (19)	169.9

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore.

References

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