Trimesic acid dimethyl sulfoxide solvate: space group revision.

The structure of the title solvate, C(9)H(6)O(6)·C(2)H(6)OS, was determined 30 years ago [Herbstein, Kapon & Wasserman (1978 ▶). Acta Cryst. B34, 1613-1617], with data collected at room temperature, and refined in the space group P2(1). The present redetermination, based on high-resolution diffraction data, shows that the actual space group is more likely to be P2(1)/m. The crystal structure contains layers of trimesic acid molecules lying on mirror planes. A mirror plane also passes through the S and O atoms of the solvent molecule. The molecules in each layer are inter-connected through strong O-H⋯O hydrogen bonds, forming a two-dimensional supra-molecular network within each layer. The donor groups are the hydroxyls of the trimesic acid mol-ecules, while the acceptors are the carbonyl or the sulfoxide O atoms.

Related literature

For the first report on the title solvate structure, see: Herbstein et al. (1978 ▶). For the use of trimesic acid as a building block for supra­molecular networks, see: Almeida Paz & Klinowski (2004 ▶). For a description of hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C9H6O6·C2H6OS

M = 288.27

Monoclinic,

a = 8.7444 (7) Å

b = 6.8365 (7) Å

c = 10.7113 (8) Å

β = 96.195 (5)°

V = 636.59 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 298 (1) K

0.60 × 0.48 × 0.36 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.851, T max = 0.904

4582 measured reflections

2007 independent reflections

1772 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections every 97 reflections intensity decay: <1%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.112

S = 1.07

2007 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 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/S1600536808018655/fb2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018655/fb2098Isup2.hkl

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

C9H6O6·C2H6OS	F000 = 300
Mr = 288.27	Dx = 1.504 Mg m−3
Monoclinic, P21/m	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 45 reflections
a = 8.7444 (7) Å	θ = 4.7–13.8º
b = 6.8365 (7) Å	µ = 0.28 mm−1
c = 10.7113 (8) Å	T = 298 (1) K
β = 96.195 (5)º	Cell measurement pressure: 101(2) kPa
V = 636.59 (10) Å3	Prism, colourless
Z = 2	0.60 × 0.48 × 0.36 mm

Siemens P4 diffractometer	1772 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Monochromator: graphite	θmax = 30.0º
T = 298(1) K	θmin = 1.9º
P = 101(2) kPa	h = −12→12
2θ/ω scans	k = −9→1
Absorption correction: ψ scan(XSCANS; Siemens, 1996)	l = −15→15
Tmin = 0.851, Tmax = 0.904	3 standard reflections
4582 measured reflections	every 97 reflections
2007 independent reflections	intensity decay: <1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.1017P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2007 reflections	Δρmax = 0.38 e Å−3
123 parameters	Δρmin = −0.30 e Å−3
20 constraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (9)

	x	y	z	Uiso*/Ueq
C1	0.60335 (14)	0.2500	0.50040 (13)	0.0315 (3)
C2	0.65053 (16)	0.2500	0.38033 (13)	0.0356 (3)
H2A	0.5773	0.2500	0.3106	0.043*
C3	0.80576 (16)	0.2500	0.36384 (12)	0.0355 (3)
C4	0.91692 (16)	0.2500	0.46759 (13)	0.0361 (3)
H4A	1.0210	0.2500	0.4567	0.043*
C5	0.86956 (15)	0.2500	0.58847 (12)	0.0333 (3)
C6	0.71358 (15)	0.2500	0.60405 (13)	0.0325 (3)
H6A	0.6829	0.2500	0.6845	0.039*
C7	0.43539 (16)	0.2500	0.51484 (15)	0.0363 (3)
C8	0.84857 (18)	0.2500	0.23234 (14)	0.0428 (4)
C9	0.98606 (16)	0.2500	0.70011 (13)	0.0382 (4)
O1	0.40892 (13)	0.2500	0.63458 (12)	0.0512 (4)
H1	0.314 (4)	0.2500	0.640 (3)	0.079 (9)*
O2	0.33561 (13)	0.2500	0.42797 (12)	0.0527 (4)
O3	0.99843 (14)	0.2500	0.22789 (12)	0.0648 (5)
H3	1.018 (4)	0.2500	0.152 (4)	0.105 (12)*
O4	0.75495 (16)	0.2500	0.14056 (11)	0.0610 (4)
O5	0.92574 (13)	0.2500	0.80719 (10)	0.0548 (4)
H5	0.998 (3)	0.2500	0.868 (3)	0.063 (7)*
O6	1.12357 (13)	0.2500	0.69470 (12)	0.0600 (4)
S1	0.28919 (4)	0.2500	0.01135 (3)	0.04770 (18)
C10	0.35278 (17)	0.0539 (3)	0.11302 (15)	0.0600 (4)
H10A	0.4632	0.0522	0.1249	0.090*
H10B	0.3158	−0.0677	0.0764	0.090*
H10C	0.3137	0.0713	0.1927	0.090*
O7	0.11484 (13)	0.2500	0.00856 (11)	0.0620 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0208 (5)	0.0452 (7)	0.0285 (6)	0.000	0.0028 (4)	0.000
C2	0.0258 (6)	0.0547 (9)	0.0257 (6)	0.000	0.0002 (5)	0.000
C3	0.0276 (6)	0.0578 (9)	0.0212 (6)	0.000	0.0037 (4)	0.000
C4	0.0239 (6)	0.0595 (9)	0.0251 (6)	0.000	0.0043 (5)	0.000
C5	0.0229 (5)	0.0545 (8)	0.0226 (5)	0.000	0.0023 (4)	0.000
C6	0.0236 (6)	0.0498 (8)	0.0246 (6)	0.000	0.0045 (4)	0.000
C7	0.0227 (6)	0.0491 (8)	0.0371 (7)	0.000	0.0032 (5)	0.000
C8	0.0327 (7)	0.0727 (11)	0.0236 (6)	0.000	0.0052 (5)	0.000
C9	0.0233 (6)	0.0678 (10)	0.0234 (6)	0.000	0.0025 (4)	0.000
O1	0.0227 (5)	0.0914 (10)	0.0407 (6)	0.000	0.0092 (4)	0.000
O2	0.0261 (5)	0.0874 (10)	0.0433 (7)	0.000	−0.0024 (4)	0.000
O3	0.0320 (6)	0.1391 (16)	0.0244 (5)	0.000	0.0083 (4)	0.000
O4	0.0401 (6)	0.1171 (13)	0.0247 (5)	0.000	−0.0012 (4)	0.000
O5	0.0266 (5)	0.1159 (12)	0.0218 (5)	0.000	0.0026 (4)	0.000
O6	0.0216 (5)	0.1258 (13)	0.0330 (6)	0.000	0.0042 (4)	0.000
S1	0.0287 (2)	0.0895 (4)	0.0254 (2)	0.000	0.00491 (13)	0.000
C10	0.0550 (8)	0.0642 (9)	0.0587 (8)	−0.0010 (7)	−0.0031 (6)	−0.0050 (7)
O7	0.0275 (5)	0.1342 (15)	0.0238 (5)	0.000	0.0010 (4)	0.000

C1—C6	1.3895 (18)	C8—O4	1.2095 (19)
C1—C2	1.3925 (19)	C8—O3	1.3165 (19)
C1—C7	1.4933 (18)	C9—O6	1.2101 (17)
C2—C3	1.3876 (19)	C9—O5	1.3131 (17)
C2—H2A	0.9300	O1—H1	0.84 (3)
C3—C4	1.3952 (19)	O3—H3	0.85 (4)
C3—C8	1.496 (2)	O5—H5	0.86 (3)
C4—C5	1.4014 (18)	S1—O7	1.5217 (12)
C4—H4A	0.9300	S1—C10i	1.7781 (17)
C5—C6	1.3918 (18)	S1—C10	1.7781 (17)
C5—C9	1.4849 (19)	C10—H10A	0.9600
C6—H6A	0.9300	C10—H10B	0.9600
C7—O2	1.2049 (19)	C10—H10C	0.9600
C7—O1	1.3277 (19)
C6—C1—C2	119.26 (12)	O1—C7—C1	112.08 (12)
C6—C1—C7	121.50 (12)	O4—C8—O3	124.03 (14)
C2—C1—C7	119.24 (12)	O4—C8—C3	123.31 (15)
C3—C2—C1	120.60 (12)	O3—C8—C3	112.66 (13)
C3—C2—H2A	119.7	O6—C9—O5	122.46 (13)
C1—C2—H2A	119.7	O6—C9—C5	124.08 (13)
C2—C3—C4	120.37 (12)	O5—C9—C5	113.46 (12)
C2—C3—C8	117.87 (12)	C7—O1—H1	110 (2)
C4—C3—C8	121.76 (13)	C8—O3—H3	110 (2)
C3—C4—C5	119.08 (12)	C9—O5—H5	109.3 (19)
C3—C4—H4A	120.5	O7—S1—C10i	104.98 (6)
C5—C4—H4A	120.5	O7—S1—C10	104.98 (6)
C6—C5—C4	120.13 (12)	C10i—S1—C10	97.87 (11)
C6—C5—C9	119.97 (12)	S1—C10—H10A	109.5
C4—C5—C9	119.91 (12)	S1—C10—H10B	109.5
C1—C6—C5	120.56 (12)	H10A—C10—H10B	109.5
C1—C6—H6A	119.7	S1—C10—H10C	109.5
C5—C6—H6A	119.7	H10A—C10—H10C	109.5
O2—C7—O1	123.97 (14)	H10B—C10—H10C	109.5
O2—C7—C1	123.94 (14)
C6—C1—C2—C3	0.0	C6—C1—C7—O2	180.0
C7—C1—C2—C3	180.0	C2—C1—C7—O2	0.0
C1—C2—C3—C4	0.0	C6—C1—C7—O1	0.0
C1—C2—C3—C8	180.0	C2—C1—C7—O1	180.0
C2—C3—C4—C5	0.0	C2—C3—C8—O4	0.0
C8—C3—C4—C5	180.0	C4—C3—C8—O4	180.0
C3—C4—C5—C6	0.0	C2—C3—C8—O3	180.0
C3—C4—C5—C9	180.0	C4—C3—C8—O3	0.0
C2—C1—C6—C5	0.0	C6—C5—C9—O6	180.0
C7—C1—C6—C5	180.0	C4—C5—C9—O6	0.0
C4—C5—C6—C1	0.0	C6—C5—C9—O5	0.0
C9—C5—C6—C1	180.0	C4—C5—C9—O5	180.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6ii	0.84 (3)	1.82 (3)	2.6435 (16)	165 (3)
O3—H3···O7iii	0.85 (4)	1.83 (4)	2.6593 (17)	164 (4)
O5—H5···O7iv	0.86 (3)	1.73 (3)	2.5723 (16)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6i	0.84 (3)	1.82 (3)	2.6435 (16)	165 (3)
O3—H3⋯O7ii	0.85 (4)	1.83 (4)	2.6593 (17)	164 (4)
O5—H5⋯O7iii	0.86 (3)	1.73 (3)	2.5723 (16)	169 (3)

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