2-(2-Oxothio-lan-3-yl)isoindoline-1,3-dione.

In the title compound, C(12)H(9)NO(3)S, the isoindoline-1,3-dione group is almost planar, with an r.m.s. deviation of 0.020 Å, whereas the heterocyclic ring approximates to an envelope with the methyl-ene group not adjacent to the S atom in the flap position. A short intra-molecular C-H⋯O contact generates an S(6) ring motif. In the crystal structure, weak aromatic π-π stacking inter-actions occur between the centroids of the benzene rings at a distance of 3.558 (2) Å.

Related literature

For background to isocoumarins, see: Hussain et al. (2001 ▶); Lee et al. (2001 ▶); Nozawa et al. (1981 ▶). For related crystal structures, see: Beck et al. (2007 ▶); Freer & Kraut (1965 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H9NO3S

M = 247.26

Monoclinic,

a = 8.0601 (13) Å

b = 6.9860 (11) Å

c = 19.709 (3) Å

β = 99.296 (9)°

V = 1095.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.24 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.978

14781 measured reflections

1934 independent reflections

1105 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.151

S = 1.02

1934 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043400/hb5705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043400/hb5705Isup2.hkl

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

C12H9NO3S	F(000) = 512
Mr = 247.26	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1105 reflections
a = 8.0601 (13) Å	θ = 2.1–25.0°
b = 6.9860 (11) Å	µ = 0.29 mm−1
c = 19.709 (3) Å	T = 296 K
β = 99.296 (9)°	Needle, colourless
V = 1095.2 (3) Å3	0.24 × 0.10 × 0.08 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1934 independent reflections
Radiation source: fine-focus sealed tube	1105 reflections with I > 2σ(I)
graphite	Rint = 0.093
Detector resolution: 8.2 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.968, Tmax = 0.978	l = −23→23
14781 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.3208P] where P = (Fo2 + 2Fc2)/3
1934 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.31 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
S1	1.27260 (14)	0.17317 (15)	0.21281 (6)	0.0666 (4)
O1	1.0043 (4)	0.2417 (4)	0.01824 (15)	0.0690 (11)
O2	0.6135 (4)	0.3134 (4)	0.15927 (16)	0.0694 (11)
O3	1.0050 (3)	−0.0304 (4)	0.16664 (14)	0.0619 (11)
N1	0.8391 (4)	0.2932 (4)	0.10189 (16)	0.0463 (11)
C1	0.8677 (5)	0.2558 (5)	0.0348 (2)	0.0496 (14)
C2	0.6994 (5)	0.2417 (5)	−0.0077 (2)	0.0445 (14)
C3	0.6538 (6)	0.2073 (5)	−0.0763 (2)	0.0600 (16)
C4	0.4821 (7)	0.1996 (6)	−0.1015 (2)	0.0724 (19)
C5	0.3638 (6)	0.2223 (6)	−0.0585 (3)	0.073 (2)
C6	0.4108 (5)	0.2546 (5)	0.0105 (3)	0.0580 (16)
C7	0.5801 (4)	0.2646 (5)	0.0350 (2)	0.0469 (14)
C8	0.6676 (5)	0.2926 (5)	0.1061 (2)	0.0486 (14)
C9	0.9686 (4)	0.3132 (5)	0.1613 (2)	0.0492 (12)
C10	1.0927 (5)	0.4715 (5)	0.1568 (2)	0.0537 (16)
C11	1.2487 (5)	0.4309 (5)	0.2093 (2)	0.0553 (16)
C12	1.0662 (5)	0.1259 (5)	0.17663 (18)	0.0444 (12)
H3	0.73362	0.18977	−0.10491	0.0718*
H4	0.44640	0.17879	−0.14821	0.0870*
H5	0.25006	0.21559	−0.07677	0.0880*
H6	0.33150	0.26915	0.03956	0.0696*
H9	0.91266	0.34070	0.20085	0.0591*
H10A	1.04437	0.59374	0.16649	0.0646*
H10B	1.12157	0.47652	0.11092	0.0646*
H11A	1.23521	0.48081	0.25402	0.0667*
H11B	1.34670	0.49028	0.19538	0.0667*

	U11	U22	U33	U12	U13	U23
S1	0.0529 (7)	0.0572 (7)	0.0828 (9)	0.0032 (5)	−0.0094 (6)	0.0022 (6)
O1	0.0456 (18)	0.086 (2)	0.078 (2)	−0.0061 (15)	0.0178 (16)	−0.0142 (16)
O2	0.0619 (19)	0.075 (2)	0.076 (2)	−0.0060 (16)	0.0255 (17)	−0.0102 (16)
O3	0.0674 (19)	0.0400 (16)	0.078 (2)	−0.0076 (14)	0.0106 (16)	−0.0004 (14)
N1	0.0420 (19)	0.0466 (18)	0.049 (2)	0.0011 (14)	0.0038 (16)	0.0021 (15)
C1	0.040 (2)	0.042 (2)	0.067 (3)	−0.0027 (18)	0.009 (2)	0.0031 (18)
C2	0.043 (2)	0.037 (2)	0.052 (3)	−0.0082 (16)	0.003 (2)	0.0049 (17)
C3	0.069 (3)	0.051 (2)	0.058 (3)	−0.013 (2)	0.004 (2)	0.009 (2)
C4	0.091 (4)	0.056 (3)	0.059 (3)	−0.017 (3)	−0.022 (3)	0.010 (2)
C5	0.054 (3)	0.044 (3)	0.111 (5)	−0.006 (2)	−0.019 (3)	0.018 (3)
C6	0.041 (2)	0.037 (2)	0.092 (4)	−0.0023 (18)	−0.001 (2)	0.004 (2)
C7	0.039 (2)	0.029 (2)	0.069 (3)	−0.0025 (16)	−0.002 (2)	0.0051 (17)
C8	0.042 (2)	0.038 (2)	0.068 (3)	−0.0018 (17)	0.016 (2)	0.0010 (19)
C9	0.046 (2)	0.048 (2)	0.053 (2)	−0.0043 (18)	0.006 (2)	−0.0034 (19)
C10	0.061 (3)	0.041 (2)	0.058 (3)	−0.005 (2)	0.006 (2)	−0.0018 (18)
C11	0.056 (3)	0.053 (2)	0.056 (3)	−0.007 (2)	0.006 (2)	−0.009 (2)
C12	0.048 (2)	0.042 (2)	0.044 (2)	−0.0006 (18)	0.0098 (19)	0.0016 (17)

S1—C11	1.811 (4)	C6—C7	1.374 (6)
S1—C12	1.733 (4)	C7—C8	1.477 (5)
O1—C1	1.202 (5)	C9—C10	1.503 (5)
O2—C8	1.207 (5)	C9—C12	1.532 (5)
O3—C12	1.201 (5)	C10—C11	1.521 (6)
N1—C1	1.403 (5)	C3—H3	0.9300
N1—C8	1.398 (5)	C4—H4	0.9300
N1—C9	1.444 (5)	C5—H5	0.9300
C1—C2	1.478 (6)	C6—H6	0.9300
C2—C3	1.364 (5)	C9—H9	0.9800
C2—C7	1.386 (5)	C10—H10A	0.9700
C3—C4	1.394 (7)	C10—H10B	0.9700
C4—C5	1.383 (7)	C11—H11A	0.9700
C5—C6	1.370 (8)	C11—H11B	0.9700
C11—S1—C12	94.86 (18)	S1—C12—O3	125.6 (3)
C1—N1—C8	111.7 (3)	S1—C12—C9	110.3 (2)
C1—N1—C9	125.1 (3)	O3—C12—C9	124.1 (3)
C8—N1—C9	123.0 (3)	C2—C3—H3	121.00
O1—C1—N1	124.6 (4)	C4—C3—H3	122.00
O1—C1—C2	129.6 (4)	C3—C4—H4	119.00
N1—C1—C2	105.7 (3)	C5—C4—H4	119.00
C1—C2—C3	130.5 (4)	C4—C5—H5	119.00
C1—C2—C7	108.2 (3)	C6—C5—H5	119.00
C3—C2—C7	121.3 (4)	C5—C6—H6	121.00
C2—C3—C4	116.9 (4)	C7—C6—H6	121.00
C3—C4—C5	121.4 (4)	N1—C9—H9	107.00
C4—C5—C6	121.3 (5)	C10—C9—H9	107.00
C5—C6—C7	117.2 (4)	C12—C9—H9	107.00
C2—C7—C6	121.9 (4)	C9—C10—H10A	110.00
C2—C7—C8	108.7 (3)	C9—C10—H10B	110.00
C6—C7—C8	129.5 (4)	C11—C10—H10A	110.00
O2—C8—N1	123.4 (4)	C11—C10—H10B	110.00
O2—C8—C7	131.0 (4)	H10A—C10—H10B	108.00
N1—C8—C7	105.6 (3)	S1—C11—H11A	110.00
N1—C9—C10	115.1 (3)	S1—C11—H11B	110.00
N1—C9—C12	111.0 (3)	C10—C11—H11A	110.00
C10—C9—C12	108.3 (3)	C10—C11—H11B	110.00
C9—C10—C11	107.9 (3)	H11A—C11—H11B	109.00
S1—C11—C10	106.4 (2)
C12—S1—C11—C10	−19.3 (3)	C1—C2—C7—C6	−178.6 (3)
C11—S1—C12—O3	−178.8 (4)	C1—C2—C7—C8	−0.4 (4)
C11—S1—C12—C9	−0.9 (3)	C3—C2—C7—C6	−0.3 (6)
C8—N1—C1—O1	−177.2 (3)	C3—C2—C7—C8	178.0 (3)
C8—N1—C1—C2	3.5 (4)	C2—C3—C4—C5	−1.2 (6)
C9—N1—C1—O1	−2.4 (6)	C3—C4—C5—C6	0.5 (6)
C9—N1—C1—C2	178.3 (3)	C4—C5—C6—C7	0.4 (6)
C1—N1—C8—O2	176.8 (3)	C5—C6—C7—C2	−0.5 (5)
C1—N1—C8—C7	−3.8 (4)	C5—C6—C7—C8	−178.3 (4)
C9—N1—C8—O2	1.9 (5)	C2—C7—C8—O2	−178.1 (4)
C9—N1—C8—C7	−178.7 (3)	C2—C7—C8—N1	2.5 (4)
C1—N1—C9—C10	59.6 (4)	C6—C7—C8—O2	−0.1 (7)
C1—N1—C9—C12	−63.9 (4)	C6—C7—C8—N1	−179.5 (4)
C8—N1—C9—C10	−126.2 (3)	N1—C9—C10—C11	−160.7 (3)
C8—N1—C9—C12	110.3 (4)	C12—C9—C10—C11	−35.8 (4)
O1—C1—C2—C3	0.8 (7)	N1—C9—C12—S1	148.7 (2)
O1—C1—C2—C7	178.9 (4)	N1—C9—C12—O3	−33.4 (5)
N1—C1—C2—C3	−180.0 (4)	C10—C9—C12—S1	21.4 (4)
N1—C1—C2—C7	−1.8 (4)	C10—C9—C12—O3	−160.7 (4)
C1—C2—C3—C4	179.0 (4)	C9—C10—C11—S1	34.4 (4)
C7—C2—C3—C4	1.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1	0.97	2.52	3.149 (5)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1	0.97	2.52	3.149 (5)	122