Butyl 3-oxo-2,3-dihydro-benzo[d][1,2]thia-zole-2-carboxyl-ate.

The title compound, C(12)H(13)NO(3)S, was synthesised by the reaction of benzo[d]isothia-zol-3(2H)-one with butyl alcohol in toluene. The benzoisothia-zolone ring system is almost planar with a mean deviation of 0.041 (1) Å. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the sythesis of benzoisothia­zolone deriv­atives, see: Davis (1972 ▶); Elgazwy & Abdel-Sattar (2003 ▶). For the biological activity of 1,2-benzoisothia­zolone derivatives, see: Taubert et al. (2002 ▶). For structural studies of related alkyl 3-oxo-2,3-dihydro-1,2-benzothia­zole-2-carboxyl­ate derivatives, see: Wang et al. (2011a ▶,b ▶); Xu & Yin (2006 ▶); Cavalca et al. (1969 ▶).

Experimental

Crystal data

C12H13NO3S

M = 251.29

Monoclinic,

a = 11.730 (3) Å

b = 11.925 (3) Å

c = 8.443 (2) Å

β = 95.791 (4)°

V = 1175.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 153 K

0.62 × 0.36 × 0.10 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.851, T max = 0.973

9917 measured reflections

3092 independent reflections

2647 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 1.00

3092 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104791X/kp2366sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104791X/kp2366Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104791X/kp2366Isup3.cml

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

C12H13NO3S	F(000) = 528
Mr = 251.29	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.730 (3) Å	Cell parameters from 3724 reflections
b = 11.925 (3) Å	θ = 2.8–29.1°
c = 8.443 (2) Å	µ = 0.27 mm−1
β = 95.791 (4)°	T = 153 K
V = 1175.0 (6) Å3	Prism, colourless
Z = 4	0.62 × 0.36 × 0.10 mm

Rigaku AFC10/Saturn724+ diffractometer	3092 independent reflections
Radiation source: fine-focus sealed tube	2647 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.0°
phi and ω scans	h = −16→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→16
Tmin = 0.851, Tmax = 0.973	l = −10→11
9917 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.360P] where P = (Fo2 + 2Fc2)/3
3092 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
S1	0.46675 (3)	0.51858 (3)	0.70649 (4)	0.01717 (10)
O1	0.40826 (8)	0.82060 (8)	0.83392 (12)	0.0214 (2)
O2	0.25897 (8)	0.56323 (8)	0.54771 (12)	0.0200 (2)
O3	0.24088 (9)	0.74791 (8)	0.59858 (13)	0.0257 (2)
N1	0.39346 (9)	0.64470 (9)	0.71407 (13)	0.0174 (2)
C1	0.56998 (11)	0.56720 (11)	0.85277 (15)	0.0159 (3)
C2	0.66483 (12)	0.50761 (11)	0.92167 (17)	0.0195 (3)
H2	0.6789	0.4326	0.8912	0.023*
C3	0.73755 (12)	0.56198 (12)	1.03597 (17)	0.0235 (3)
H3	0.8024	0.5230	1.0848	0.028*
C4	0.71858 (13)	0.67273 (13)	1.08206 (18)	0.0249 (3)
H4	0.7702	0.7075	1.1611	0.030*
C5	0.62513 (12)	0.73131 (12)	1.01296 (16)	0.0212 (3)
H5	0.6122	0.8068	1.0423	0.025*
C6	0.54993 (11)	0.67727 (11)	0.89886 (15)	0.0163 (3)
C7	0.44594 (11)	0.72650 (11)	0.81747 (15)	0.0165 (3)
C8	0.29136 (11)	0.66070 (11)	0.61571 (16)	0.0180 (3)
C9	0.16309 (12)	0.57154 (11)	0.42454 (17)	0.0203 (3)
H9A	0.1843	0.6183	0.3352	0.024*
H9B	0.0962	0.6062	0.4681	0.024*
C10	0.13447 (12)	0.45390 (11)	0.36782 (17)	0.0206 (3)
H10A	0.1160	0.4074	0.4590	0.025*
H10B	0.2019	0.4204	0.3242	0.025*
C11	0.03285 (13)	0.45355 (13)	0.23998 (18)	0.0257 (3)
H11A	−0.0345	0.4867	0.2844	0.031*
H11B	0.0513	0.5011	0.1498	0.031*
C12	0.00234 (15)	0.33608 (15)	0.1787 (2)	0.0366 (4)
H12A	0.0677	0.3039	0.1310	0.044*
H12B	−0.0639	0.3401	0.0983	0.044*
H12C	−0.0164	0.2887	0.2674	0.044*

	U11	U22	U33	U12	U13	U23
S1	0.01792 (16)	0.01312 (15)	0.01945 (18)	0.00089 (11)	−0.00322 (12)	−0.00196 (12)
O1	0.0219 (5)	0.0150 (4)	0.0263 (5)	0.0014 (4)	−0.0018 (4)	−0.0037 (4)
O2	0.0185 (5)	0.0153 (5)	0.0242 (5)	−0.0012 (4)	−0.0070 (4)	−0.0002 (4)
O3	0.0224 (5)	0.0175 (5)	0.0349 (6)	0.0041 (4)	−0.0082 (4)	−0.0033 (4)
N1	0.0166 (5)	0.0134 (5)	0.0212 (6)	0.0012 (4)	−0.0036 (4)	−0.0016 (4)
C1	0.0160 (6)	0.0163 (6)	0.0151 (6)	−0.0025 (5)	0.0002 (5)	−0.0003 (5)
C2	0.0192 (7)	0.0177 (6)	0.0211 (7)	0.0019 (5)	0.0001 (5)	0.0002 (5)
C3	0.0193 (7)	0.0257 (7)	0.0240 (7)	0.0017 (5)	−0.0050 (5)	0.0014 (6)
C4	0.0226 (7)	0.0256 (7)	0.0247 (7)	−0.0031 (6)	−0.0065 (6)	−0.0022 (6)
C5	0.0221 (7)	0.0185 (6)	0.0222 (7)	−0.0019 (5)	−0.0012 (5)	−0.0032 (5)
C6	0.0168 (6)	0.0155 (6)	0.0163 (6)	−0.0010 (5)	0.0005 (5)	0.0002 (5)
C7	0.0171 (6)	0.0154 (6)	0.0166 (6)	−0.0021 (5)	0.0005 (5)	−0.0009 (5)
C8	0.0167 (6)	0.0166 (6)	0.0201 (7)	−0.0017 (5)	−0.0012 (5)	0.0003 (5)
C9	0.0169 (6)	0.0191 (7)	0.0232 (7)	−0.0015 (5)	−0.0072 (5)	0.0007 (5)
C10	0.0183 (6)	0.0184 (6)	0.0238 (7)	−0.0032 (5)	−0.0046 (5)	0.0001 (5)
C11	0.0225 (7)	0.0278 (8)	0.0250 (7)	−0.0027 (6)	−0.0068 (6)	−0.0017 (6)
C12	0.0340 (9)	0.0348 (9)	0.0383 (9)	−0.0091 (7)	−0.0096 (7)	−0.0082 (7)

S1—N1	1.7368 (12)	C5—C6	1.3964 (18)
S1—C1	1.7395 (14)	C5—H5	0.9500
O1—C7	1.2192 (16)	C6—C7	1.4614 (18)
O2—C8	1.3346 (16)	C9—C10	1.5092 (19)
O2—C9	1.4561 (16)	C9—H9A	0.9900
O3—C8	1.1983 (16)	C9—H9B	0.9900
N1—C8	1.3998 (17)	C10—C11	1.5252 (19)
N1—C7	1.4086 (16)	C10—H10A	0.9900
C1—C6	1.3958 (18)	C10—H10B	0.9900
C1—C2	1.3967 (19)	C11—C12	1.523 (2)
C2—C3	1.383 (2)	C11—H11A	0.9900
C2—H2	0.9500	C11—H11B	0.9900
C3—C4	1.401 (2)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.379 (2)	C12—H12C	0.9800
C4—H4	0.9500
N1—S1—C1	89.82 (6)	O3—C8—N1	124.93 (12)
C8—O2—C9	114.44 (10)	O2—C8—N1	109.02 (11)
C8—N1—C7	124.58 (11)	O2—C9—C10	107.12 (10)
C8—N1—S1	119.55 (9)	O2—C9—H9A	110.3
C7—N1—S1	115.82 (9)	C10—C9—H9A	110.3
C6—C1—C2	120.79 (12)	O2—C9—H9B	110.3
C6—C1—S1	112.75 (10)	C10—C9—H9B	110.3
C2—C1—S1	126.47 (11)	H9A—C9—H9B	108.5
C3—C2—C1	117.48 (13)	C9—C10—C11	111.11 (12)
C3—C2—H2	121.3	C9—C10—H10A	109.4
C1—C2—H2	121.3	C11—C10—H10A	109.4
C2—C3—C4	122.12 (13)	C9—C10—H10B	109.4
C2—C3—H3	118.9	C11—C10—H10B	109.4
C4—C3—H3	118.9	H10A—C10—H10B	108.0
C5—C4—C3	120.13 (13)	C12—C11—C10	112.52 (13)
C5—C4—H4	119.9	C12—C11—H11A	109.1
C3—C4—H4	119.9	C10—C11—H11A	109.1
C4—C5—C6	118.55 (13)	C12—C11—H11B	109.1
C4—C5—H5	120.7	C10—C11—H11B	109.1
C6—C5—H5	120.7	H11A—C11—H11B	107.8
C1—C6—C5	120.93 (12)	C11—C12—H12A	109.5
C1—C6—C7	113.75 (12)	C11—C12—H12B	109.5
C5—C6—C7	125.32 (12)	H12A—C12—H12B	109.5
O1—C7—N1	124.56 (12)	C11—C12—H12C	109.5
O1—C7—C6	127.68 (12)	H12A—C12—H12C	109.5
N1—C7—C6	107.76 (11)	H12B—C12—H12C	109.5
O3—C8—O2	126.03 (12)
C1—S1—N1—C8	−179.43 (11)	S1—N1—C7—O1	177.71 (11)
C1—S1—N1—C7	3.08 (10)	C8—N1—C7—C6	179.85 (12)
N1—S1—C1—C6	−2.42 (10)	S1—N1—C7—C6	−2.81 (14)
N1—S1—C1—C2	177.76 (13)	C1—C6—C7—O1	−179.65 (13)
C6—C1—C2—C3	−0.2 (2)	C5—C6—C7—O1	0.4 (2)
S1—C1—C2—C3	179.58 (11)	C1—C6—C7—N1	0.89 (16)
C1—C2—C3—C4	−0.3 (2)	C5—C6—C7—N1	−179.04 (13)
C2—C3—C4—C5	−0.1 (2)	C9—O2—C8—O3	9.8 (2)
C3—C4—C5—C6	0.9 (2)	C9—O2—C8—N1	−171.42 (11)
C2—C1—C6—C5	1.1 (2)	C7—N1—C8—O3	5.8 (2)
S1—C1—C6—C5	−178.74 (11)	S1—N1—C8—O3	−171.40 (12)
C2—C1—C6—C7	−178.84 (12)	C7—N1—C8—O2	−172.92 (12)
S1—C1—C6—C7	1.32 (15)	S1—N1—C8—O2	9.83 (15)
C4—C5—C6—C1	−1.4 (2)	C8—O2—C9—C10	−177.04 (12)
C4—C5—C6—C7	178.51 (13)	O2—C9—C10—C11	178.90 (12)
C8—N1—C7—O1	0.4 (2)	C9—C10—C11—C12	179.42 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.46	3.1610 (19)	131
C2—H2···O3i	0.95	2.39	3.2987 (18)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.46	3.1610 (19)	131
C2—H2⋯O3i	0.95	2.39	3.2987 (18)	159

Symmetry code: (i) .