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

In the title compound, C(11)H(13)NO(3)S, a benzothia-zine derivative, the heterocycle adopts a sofa conformation. In the crystal, weak C-H⋯O hydrogen bonds connect the mol-ecules 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 = 239.28

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.07

2765 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.38 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004078X/bt5369Isup2.hkl

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

C11H13NO3S	Z = 2
Mr = 239.28	F(000) = 252
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0604P)2 + 0.0882P] where P = (Fo2 + 2Fc2)/3
2765 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .