Benzene-1,3,5-triyl tris-(methane-sulfonate).

In the mol-ecule of the title compound, C(9)H(12)O(9)S(3), the two methanesulfonate groups re located one above and one below the ring plane. The C-O-S angle range is 119.3 (2)-121.1 (2)°. This conformation is different from that of the benzene analog 1,2,5-tris-(p-toluene-sulfonate), which is a three-legged 'table' with all fragments of the p-toluene-sulfonate on top of the benzene ring. In the crystal, the supra-molecular aggregation is completed by the presence of C-H⋯O hydrogen bonds.

Related literature

For infrared spectroscopic studies related compounds, see: Grice et al. (2000 ▶); Yan & Yan (2001 ▶). For mass spectroscopy of related compounds, see: Chavez et al. (2003 ▶); Olivas et al. (2008 ▶); Madrigal et al. (2006 ▶). For examples of O⋯O inter­actions, see: Raghavaiah et al. (2006 ▶), and for a comprehensive theoretical treatment, see: Ni et al. (2004 ▶). For a related structure, see:, see: Vembu et al. (2003 ▶). For the IR spectrum, see: Skoog et al. (1997 ▶).

Experimental

Crystal data

C9H12O9S3

M = 360.37

Monoclinic,

a = 8.7810 (5) Å

b = 17.0053 (9) Å

c = 9.7746 (7) Å

β = 100.595 (5)°

V = 1434.69 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 298 K

0.40 × 0.24 × 0.10 mm

Data collection

Bruker P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.258, T max = 0.310

4418 measured reflections

4176 independent reflections

2333 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 97 reflections intensity decay: 4.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.177

S = 0.92

4176 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006641/bg2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006641/bg2322Isup2.hkl

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

C9H12O9S3	F(000) = 744
Mr = 360.37	Dx = 1.668 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 51 reflections
a = 8.7810 (5) Å	θ = 4.9–12.4°
b = 17.0053 (9) Å	µ = 0.56 mm−1
c = 9.7746 (7) Å	T = 298 K
β = 100.595 (5)°	Needle, colourless
V = 1434.69 (15) Å3	0.40 × 0.24 × 0.10 mm
Z = 4

Bruker P4 diffractometer	2333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 30.0°, θmin = 2.4°
2θ/ω scans	h = 0→12
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = 0→23
Tmin = 0.258, Tmax = 0.310	l = −13→13
4418 measured reflections	3 standard reflections every 97 reflections
4176 independent reflections	intensity decay: 4.3%

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) = 0.177	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
4176 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.88376 (11)	0.16428 (6)	0.42609 (9)	0.0390 (2)
S2	0.78601 (11)	0.00358 (6)	−0.20344 (8)	0.0376 (2)
S3	0.60481 (12)	−0.19992 (6)	0.32307 (10)	0.0441 (3)
O3	0.6500 (3)	0.00837 (15)	−0.1152 (2)	0.0362 (5)
O2	0.7498 (3)	−0.14794 (15)	0.3008 (3)	0.0414 (6)
O1	0.7281 (3)	0.13465 (16)	0.3276 (2)	0.0431 (6)
C2	0.7397 (4)	−0.0073 (2)	0.3185 (3)	0.0342 (7)
H2A	0.7576	−0.0108	0.4151	0.041*
C6	0.6987 (4)	0.0718 (2)	0.1073 (3)	0.0322 (7)
H6A	0.6893	0.1207	0.0640	0.039*
C4	0.7008 (4)	−0.0705 (2)	0.0917 (3)	0.0322 (7)
H4A	0.6932	−0.1159	0.0380	0.039*
C5	0.6872 (4)	0.0031 (2)	0.0319 (3)	0.0307 (7)
C3	0.7265 (4)	−0.0735 (2)	0.2358 (3)	0.0330 (7)
C1	0.7251 (4)	0.0646 (2)	0.2512 (3)	0.0323 (7)
O5	0.7038 (4)	−0.00487 (19)	−0.3418 (3)	0.0606 (9)
O4	0.8956 (4)	−0.05374 (18)	−0.1437 (3)	0.0564 (8)
C7	0.8698 (5)	0.0967 (2)	−0.1803 (4)	0.0463 (9)
H7A	0.9541	0.1000	−0.2302	0.069*
H7B	0.9079	0.1056	−0.0830	0.069*
H7C	0.7936	0.1359	−0.2148	0.069*
O9	0.9613 (4)	0.09894 (18)	0.4963 (3)	0.0619 (9)
O8	0.8301 (4)	0.22633 (19)	0.5033 (3)	0.0602 (8)
O7	0.4863 (4)	−0.19317 (19)	0.2031 (3)	0.0626 (8)
O6	0.6727 (4)	−0.27378 (18)	0.3633 (4)	0.0759 (10)
C9	0.9942 (5)	0.2029 (3)	0.3109 (5)	0.0559 (11)
H9B	1.0906	0.2223	0.3622	0.084*
H9C	0.9385	0.2452	0.2590	0.084*
H9D	1.0143	0.1625	0.2479	0.084*
C8	0.5441 (6)	−0.1548 (3)	0.4643 (5)	0.0608 (12)
H8B	0.4558	−0.1823	0.4855	0.091*
H8C	0.5165	−0.1012	0.4413	0.091*
H8D	0.6267	−0.1562	0.5436	0.091*

	U11	U22	U33	U12	U13	U23
S1	0.0487 (5)	0.0386 (5)	0.0283 (4)	−0.0024 (4)	0.0034 (4)	−0.0045 (4)
S2	0.0461 (5)	0.0422 (5)	0.0263 (4)	0.0004 (4)	0.0117 (3)	−0.0044 (4)
S3	0.0552 (6)	0.0307 (5)	0.0477 (5)	−0.0008 (4)	0.0132 (4)	0.0047 (4)
O3	0.0369 (12)	0.0483 (15)	0.0229 (10)	−0.0022 (11)	0.0046 (9)	−0.0009 (10)
O2	0.0424 (14)	0.0375 (14)	0.0441 (14)	0.0047 (11)	0.0076 (11)	0.0099 (11)
O1	0.0468 (15)	0.0410 (14)	0.0376 (13)	0.0089 (12)	−0.0021 (11)	−0.0150 (11)
C2	0.0375 (17)	0.0410 (19)	0.0238 (14)	0.0003 (15)	0.0043 (12)	0.0003 (14)
C6	0.0343 (17)	0.0335 (17)	0.0283 (15)	0.0000 (14)	0.0042 (13)	−0.0020 (13)
C4	0.0338 (17)	0.0338 (17)	0.0296 (16)	−0.0035 (14)	0.0072 (13)	−0.0048 (13)
C5	0.0297 (15)	0.0382 (17)	0.0244 (14)	−0.0032 (14)	0.0056 (12)	−0.0015 (14)
C3	0.0316 (17)	0.0335 (17)	0.0341 (16)	0.0002 (14)	0.0062 (14)	0.0028 (14)
C1	0.0325 (17)	0.0363 (18)	0.0287 (15)	0.0047 (14)	0.0066 (13)	−0.0075 (14)
O5	0.076 (2)	0.081 (2)	0.0242 (12)	−0.0115 (18)	0.0093 (13)	−0.0115 (13)
O4	0.0625 (19)	0.0546 (18)	0.0561 (17)	0.0207 (15)	0.0218 (14)	−0.0017 (14)
C7	0.046 (2)	0.048 (2)	0.046 (2)	−0.0071 (18)	0.0088 (18)	0.0034 (18)
O9	0.069 (2)	0.0528 (18)	0.0534 (17)	−0.0063 (15)	−0.0173 (15)	0.0123 (14)
O8	0.069 (2)	0.066 (2)	0.0465 (16)	−0.0050 (16)	0.0130 (14)	−0.0271 (15)
O7	0.065 (2)	0.0585 (19)	0.0591 (18)	−0.0198 (16)	−0.0012 (16)	−0.0021 (15)
O6	0.095 (3)	0.0401 (17)	0.099 (3)	0.0165 (17)	0.036 (2)	0.0248 (17)
C9	0.071 (3)	0.044 (2)	0.059 (2)	−0.005 (2)	0.028 (2)	−0.002 (2)
C8	0.073 (3)	0.062 (3)	0.053 (2)	0.001 (2)	0.028 (2)	0.001 (2)

S1—O9	1.413 (3)	C2—H2A	0.9300
S1—O8	1.427 (3)	C6—C5	1.375 (5)
S1—O1	1.601 (3)	C6—C1	1.389 (4)
S1—C9	1.744 (4)	C6—H6A	0.9300
S2—O4	1.418 (3)	C4—C5	1.377 (5)
S2—O5	1.418 (3)	C4—C3	1.385 (4)
S2—O3	1.598 (3)	C4—H4A	0.9300
S2—C7	1.744 (4)	C7—H7A	0.9600
S3—O6	1.415 (3)	C7—H7B	0.9600
S3—O7	1.422 (3)	C7—H7C	0.9600
S3—O2	1.598 (3)	C9—H9B	0.9600
S3—C8	1.745 (4)	C9—H9C	0.9600
O3—C5	1.417 (4)	C9—H9D	0.9600
O2—C3	1.414 (4)	C8—H8B	0.9600
O1—C1	1.404 (4)	C8—H8C	0.9600
C2—C3	1.379 (5)	C8—H8D	0.9600
C2—C1	1.383 (5)
O9—S1—O8	120.1 (2)	C3—C4—H4A	121.6
O9—S1—O1	109.04 (16)	C6—C5—C4	123.5 (3)
O8—S1—O1	102.84 (16)	C6—C5—O3	118.1 (3)
O9—S1—C9	109.5 (2)	C4—C5—O3	118.3 (3)
O8—S1—C9	109.9 (2)	C2—C3—C4	123.1 (3)
O1—S1—C9	104.17 (19)	C2—C3—O2	118.5 (3)
O4—S2—O5	120.70 (19)	C4—C3—O2	118.2 (3)
O4—S2—O3	109.32 (16)	C2—C1—C6	122.9 (3)
O5—S2—O3	102.73 (16)	C2—C1—O1	120.4 (3)
O4—S2—C7	109.43 (19)	C6—C1—O1	116.6 (3)
O5—S2—C7	110.14 (19)	S2—C7—H7A	109.5
O3—S2—C7	102.88 (17)	S2—C7—H7B	109.5
O6—S3—O7	120.5 (2)	H7A—C7—H7B	109.5
O6—S3—O2	102.92 (19)	S2—C7—H7C	109.5
O7—S3—O2	108.86 (16)	H7A—C7—H7C	109.5
O6—S3—C8	110.1 (2)	H7B—C7—H7C	109.5
O7—S3—C8	109.5 (2)	S1—C9—H9B	109.5
O2—S3—C8	103.4 (2)	S1—C9—H9C	109.5
C5—O3—S2	119.3 (2)	H9B—C9—H9C	109.5
C3—O2—S3	120.2 (2)	S1—C9—H9D	109.5
C1—O1—S1	121.1 (2)	H9B—C9—H9D	109.5
C3—C2—C1	116.9 (3)	H9C—C9—H9D	109.5
C3—C2—H2A	121.5	S3—C8—H8B	109.5
C1—C2—H2A	121.5	S3—C8—H8C	109.5
C5—C6—C1	116.8 (3)	H8B—C8—H8C	109.5
C5—C6—H6A	121.6	S3—C8—H8D	109.5
C1—C6—H6A	121.6	H8B—C8—H8D	109.5
C5—C4—C3	116.8 (3)	H8C—C8—H8D	109.5
C5—C4—H4A	121.6
O4—S2—O3—C5	39.6 (3)	S2—O3—C5—C4	−85.2 (3)
O5—S2—O3—C5	168.9 (3)	C1—C2—C3—C4	0.4 (5)
C7—S2—O3—C5	−76.7 (3)	C1—C2—C3—O2	176.3 (3)
O6—S3—O2—C3	168.7 (3)	C5—C4—C3—C2	−0.6 (5)
O7—S3—O2—C3	39.7 (3)	C5—C4—C3—O2	−176.4 (3)
C8—S3—O2—C3	−76.6 (3)	S3—O2—C3—C2	98.7 (3)
O9—S1—O1—C1	−40.3 (3)	S3—O2—C3—C4	−85.2 (3)
O8—S1—O1—C1	−168.7 (3)	C3—C2—C1—C6	−0.1 (5)
C9—S1—O1—C1	76.6 (3)	C3—C2—C1—O1	176.3 (3)
C1—C6—C5—C4	−0.2 (5)	C5—C6—C1—C2	0.0 (5)
C1—C6—C5—O3	175.9 (3)	C5—C6—C1—O1	−176.5 (3)
C3—C4—C5—C6	0.4 (5)	S1—O1—C1—C2	69.1 (4)
C3—C4—C5—O3	−175.6 (3)	S1—O1—C1—C6	−114.3 (3)
S2—O3—C5—C6	98.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O5i	0.93	2.51	3.392 (4)	159
C9—H9D···O4ii	0.96	2.32	3.259 (5)	166
C4—H4A···O6iii	0.93	2.52	3.444 (4)	172
C9—H9C···O8iv	0.96	2.55	3.312 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O5i	0.93	2.51	3.392 (4)	159
C9—H9D⋯O4ii	0.96	2.32	3.259 (5)	166
C4—H4A⋯O6iii	0.93	2.52	3.444 (4)	172
C9—H9C⋯O8iv	0.96	2.55	3.312 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .