5,5'-(Ethyne-1,2-di-yl)diisophthalic acid dimethyl sulfoxide tetra-solvate.

In the title compound, C18H10O8·4C2H6OS, the mid-point of the triple bond of the main mol-ecule is located on a special position, i.e. about an inversion center. The carboxyl groups are twisted slightly out of the planes of the aromatic rings to which they are attached, making dihedral angles of 24.89 (1) and 7.40 (2)°. The cystal packing features strong O-H⋯O hydrogen bonds, weaker C-H⋯O inter-actions and O⋯S contacts [3.0981 (11) Å] and displays channel-like voids extending along the a-axis direction which contain the dimethyl sulfoxide solvent mol-ecules.

Related literature

For the synthesis of the principal compound, see: Hausdorf et al. (2009 ▶); Zhou et al. (2007 ▶). For its use as linker mol­ecule in the formation of porous metal–organic framework structures, see: Hausdorf et al. (2009 ▶); Hu et al. (2009 ▶); Zheng et al. (2013 ▶). For metal–organic frameworks, see: Münch et al. (2011 ▶); Chen et al. (2005 ▶); Coles et al. (2002 ▶). For a similar hydrogen-bonded aggregate, see: Hauptvogel et al. (2011 ▶). For O—H⋯O hydrogen bonds, see: Bernstein et al. (1995 ▶); Katzsch et al. (2011 ▶). For C—H⋯O contacts, see: Desiraju & Steiner (1999 ▶); Katzsch & Weber (2012 ▶); Fischer et al. (2011 ▶). For O⋯S contacts, see: Lu et al. (2011 ▶). For π–π inter­actions, see: Hunter & Sanders (1990 ▶).

Experimental

Crystal data

C18H10O8·4C2H6OS

M = 666.81

Monoclinic,

a = 8.1406 (2) Å

b = 8.7328 (2) Å

c = 21.4351 (5) Å

β = 95.970 (1)°

V = 1515.56 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 100 K

0.60 × 0.42 × 0.36 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.807, T max = 0.877

20635 measured reflections

2666 independent reflections

2567 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.04

2666 reflections

197 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013068/rk2402sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013068/rk2402Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013068/rk2402Isup3.cml

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

C18H10O8·4C2H6OS	F(000) = 700
Mr = 666.81	Dx = 1.461 Mg m−3
Monoclinic, P21/n	Melting point > 623 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.1406 (2) Å	Cell parameters from 9934 reflections
b = 8.7328 (2) Å	θ = 2.5–49.6°
c = 21.4351 (5) Å	µ = 0.38 mm−1
β = 95.970 (1)°	T = 100 K
V = 1515.56 (6) Å3	Block, colourless
Z = 2	0.60 × 0.42 × 0.36 mm

Bruker APEXII CCD diffractometer	2666 independent reflections
Radiation source: fine-focus sealed tube	2567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω– and φ–scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.807, Tmax = 0.877	k = −10→10
20635 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0228P)2 + 1.1796P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2666 reflections	Δρmax = 0.32 e Å−3
197 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (7)

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
O1	−0.01957 (11)	0.64073 (11)	1.04506 (4)	0.0150 (2)
H1	−0.0882	0.5906	1.0635	0.023*
O2	−0.23612 (11)	0.67476 (11)	0.97291 (5)	0.0171 (2)
O3	−0.21203 (11)	1.12870 (12)	0.83853 (4)	0.0175 (2)
H3	−0.2524	1.1864	0.8095	0.026*
O4	0.02782 (12)	1.18846 (11)	0.80107 (5)	0.0188 (2)
C1	0.43140 (17)	0.98735 (16)	0.98804 (6)	0.0140 (3)
C2	0.26574 (16)	0.95657 (15)	0.96125 (6)	0.0126 (3)
C3	0.17287 (16)	0.84319 (15)	0.98761 (6)	0.0124 (3)
H3A	0.2215	0.7840	1.0219	0.015*
C4	0.01012 (16)	0.81681 (15)	0.96390 (6)	0.0120 (3)
C5	−0.06279 (16)	0.90560 (15)	0.91469 (6)	0.0122 (3)
H5	−0.1751	0.8894	0.8993	0.015*
C6	0.02860 (16)	1.01785 (15)	0.88804 (6)	0.0123 (3)
C7	0.19281 (16)	1.04245 (15)	0.91065 (6)	0.0128 (3)
H7	0.2556	1.1178	0.8917	0.015*
C8	−0.09463 (16)	0.70282 (15)	0.99368 (6)	0.0127 (3)
C9	−0.04995 (16)	1.12030 (15)	0.83737 (6)	0.0136 (3)
O1G	0.78072 (12)	0.50559 (12)	0.11049 (5)	0.0203 (2)
S1G	0.61418 (4)	0.44680 (4)	0.081415 (15)	0.01417 (10)
C1G	0.55281 (17)	0.31280 (16)	0.13740 (7)	0.0179 (3)
H1G1	0.6343	0.2300	0.1430	0.027*
H1G2	0.4446	0.2701	0.1224	0.027*
H1G3	0.5459	0.3647	0.1776	0.027*
C2G	0.47196 (17)	0.59699 (16)	0.09296 (7)	0.0187 (3)
H2G1	0.4814	0.6252	0.1374	0.028*
H2G2	0.3592	0.5620	0.0799	0.028*
H2G3	0.4971	0.6862	0.0679	0.028*
O1H	0.10288 (12)	0.21753 (11)	0.25639 (5)	0.0197 (2)
S1H	−0.00487 (4)	0.32301 (4)	0.212754 (15)	0.01365 (10)
C1H	−0.09563 (18)	0.45741 (18)	0.26201 (7)	0.0212 (3)
H1H1	−0.1821	0.4065	0.2829	0.032*
H1H2	−0.1439	0.5424	0.2365	0.032*
H1H3	−0.0105	0.4969	0.2936	0.032*
C2H	0.13616 (17)	0.45062 (17)	0.18084 (7)	0.0181 (3)
H2H1	0.2159	0.4890	0.2146	0.027*
H2H2	0.0750	0.5368	0.1604	0.027*
H2H3	0.1949	0.3960	0.1500	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0133 (5)	0.0160 (5)	0.0157 (5)	−0.0021 (4)	0.0013 (4)	0.0042 (4)
O2	0.0125 (5)	0.0181 (5)	0.0201 (5)	−0.0040 (4)	−0.0010 (4)	0.0017 (4)
O3	0.0128 (5)	0.0213 (5)	0.0175 (5)	0.0016 (4)	−0.0024 (4)	0.0052 (4)
O4	0.0194 (5)	0.0200 (5)	0.0172 (5)	0.0009 (4)	0.0030 (4)	0.0055 (4)
C1	0.0133 (6)	0.0144 (7)	0.0148 (6)	0.0008 (5)	0.0034 (5)	0.0024 (5)
C2	0.0102 (6)	0.0144 (6)	0.0136 (6)	0.0012 (5)	0.0028 (5)	−0.0030 (5)
C3	0.0125 (6)	0.0129 (6)	0.0119 (6)	0.0025 (5)	0.0014 (5)	−0.0007 (5)
C4	0.0125 (6)	0.0114 (6)	0.0124 (6)	0.0006 (5)	0.0026 (5)	−0.0036 (5)
C5	0.0107 (6)	0.0138 (6)	0.0119 (6)	0.0000 (5)	0.0004 (5)	−0.0039 (5)
C6	0.0134 (6)	0.0128 (6)	0.0110 (6)	0.0017 (5)	0.0019 (5)	−0.0032 (5)
C7	0.0129 (6)	0.0129 (6)	0.0132 (6)	−0.0004 (5)	0.0047 (5)	−0.0018 (5)
C8	0.0138 (7)	0.0109 (6)	0.0135 (6)	0.0015 (5)	0.0023 (5)	−0.0027 (5)
C9	0.0150 (7)	0.0128 (6)	0.0126 (6)	0.0000 (5)	−0.0005 (5)	−0.0033 (5)
O1G	0.0126 (5)	0.0287 (6)	0.0191 (5)	−0.0055 (4)	−0.0007 (4)	0.0071 (4)
S1G	0.01290 (18)	0.01668 (18)	0.01294 (17)	−0.00069 (13)	0.00131 (12)	0.00166 (12)
C1G	0.0165 (7)	0.0184 (7)	0.0188 (7)	−0.0021 (6)	0.0020 (5)	0.0053 (6)
C2G	0.0170 (7)	0.0164 (7)	0.0220 (7)	0.0015 (6)	−0.0001 (5)	0.0003 (6)
O1H	0.0208 (5)	0.0154 (5)	0.0210 (5)	−0.0003 (4)	−0.0066 (4)	0.0022 (4)
S1H	0.01273 (17)	0.01452 (18)	0.01321 (17)	−0.00085 (13)	−0.00095 (12)	−0.00052 (12)
C1H	0.0205 (7)	0.0250 (8)	0.0188 (7)	0.0030 (6)	0.0054 (6)	−0.0024 (6)
C2H	0.0152 (7)	0.0205 (7)	0.0187 (7)	−0.0021 (6)	0.0028 (5)	0.0009 (6)

O1—C8	1.3192 (16)	O1G—S1G	1.5213 (10)
O1—H1	0.8400	S1G—C2G	1.7837 (14)
O2—C8	1.2158 (16)	S1G—C1G	1.7843 (14)
O3—C9	1.3243 (16)	C1G—H1G1	0.9800
O3—H3	0.8400	C1G—H1G2	0.9800
O4—C9	1.2096 (17)	C1G—H1G3	0.9800
C1—C1i	1.200 (3)	C2G—H2G1	0.9800
C1—C2	1.4351 (19)	C2G—H2G2	0.9800
C2—C7	1.3990 (19)	C2G—H2G3	0.9800
C2—C3	1.3999 (19)	O1H—S1H	1.5239 (10)
C3—C4	1.3880 (18)	S1H—C2H	1.7864 (14)
C3—H3A	0.9500	S1H—C1H	1.7890 (14)
C4—C5	1.3913 (19)	C1H—H1H1	0.9800
C4—C8	1.4963 (18)	C1H—H1H2	0.9800
C5—C6	1.3890 (19)	C1H—H1H3	0.9800
C5—H5	0.9500	C2H—H2H1	0.9800
C6—C7	1.3904 (19)	C2H—H2H2	0.9800
C6—C9	1.4982 (18)	C2H—H2H3	0.9800
C7—H7	0.9500
C8—O1—H1	109.5	C2G—S1G—C1G	99.07 (7)
C9—O3—H3	109.5	S1G—C1G—H1G1	109.5
C1i—C1—C2	178.29 (18)	S1G—C1G—H1G2	109.5
C7—C2—C3	119.25 (12)	H1G1—C1G—H1G2	109.5
C7—C2—C1	121.00 (12)	S1G—C1G—H1G3	109.5
C3—C2—C1	119.70 (12)	H1G1—C1G—H1G3	109.5
C4—C3—C2	120.31 (12)	H1G2—C1G—H1G3	109.5
C4—C3—H3A	119.8	S1G—C2G—H2G1	109.5
C2—C3—H3A	119.8	S1G—C2G—H2G2	109.5
C3—C4—C5	120.05 (12)	H2G1—C2G—H2G2	109.5
C3—C4—C8	121.26 (12)	S1G—C2G—H2G3	109.5
C5—C4—C8	118.49 (12)	H2G1—C2G—H2G3	109.5
C6—C5—C4	120.04 (12)	H2G2—C2G—H2G3	109.5
C6—C5—H5	120.0	O1H—S1H—C2H	105.09 (6)
C4—C5—H5	120.0	O1H—S1H—C1H	106.32 (6)
C5—C6—C7	120.15 (12)	C2H—S1H—C1H	97.93 (7)
C5—C6—C9	120.87 (12)	S1H—C1H—H1H1	109.5
C7—C6—C9	118.87 (12)	S1H—C1H—H1H2	109.5
C6—C7—C2	120.16 (12)	H1H1—C1H—H1H2	109.5
C6—C7—H7	119.9	S1H—C1H—H1H3	109.5
C2—C7—H7	119.9	H1H1—C1H—H1H3	109.5
O2—C8—O1	124.18 (12)	H1H2—C1H—H1H3	109.5
O2—C8—C4	122.56 (12)	S1H—C2H—H2H1	109.5
O1—C8—C4	113.23 (11)	S1H—C2H—H2H2	109.5
O4—C9—O3	125.03 (12)	H2H1—C2H—H2H2	109.5
O4—C9—C6	123.21 (12)	S1H—C2H—H2H3	109.5
O3—C9—C6	111.74 (11)	H2H1—C2H—H2H3	109.5
O1G—S1G—C2G	104.99 (6)	H2H2—C2H—H2H3	109.5
O1G—S1G—C1G	104.22 (6)
C7—C2—C3—C4	−0.23 (19)	C3—C2—C7—C6	1.70 (19)
C1—C2—C3—C4	177.18 (12)	C1—C2—C7—C6	−175.67 (12)
C2—C3—C4—C5	−1.53 (19)	C3—C4—C8—O2	−178.09 (12)
C2—C3—C4—C8	−176.32 (12)	C5—C4—C8—O2	7.04 (19)
C3—C4—C5—C6	1.83 (19)	C3—C4—C8—O1	3.81 (17)
C8—C4—C5—C6	176.76 (11)	C5—C4—C8—O1	−171.06 (11)
C4—C5—C6—C7	−0.36 (19)	C5—C6—C9—O4	−158.78 (13)
C4—C5—C6—C9	−176.70 (12)	C7—C6—C9—O4	24.84 (19)
C5—C6—C7—C2	−1.41 (19)	C5—C6—C9—O3	22.60 (17)
C9—C6—C7—C2	175.00 (12)	C7—C6—C9—O3	−153.78 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Gii	0.84	1.71	2.5451 (13)	171
O3—H3···O1Hiii	0.84	1.76	2.5732 (13)	161
C1G—H1G2···O2iv	0.98	2.56	3.3138 (17)	134
C1G—H1G3···O4v	0.98	2.71	3.5351 (17)	143
C2G—H2G1···O1Hvi	0.98	2.57	3.5093 (18)	160
C2G—H2G2···O2iv	0.98	2.52	3.2783 (17)	135
C1H—H1H1···O4vii	0.98	2.57	3.5006 (18)	159
C1H—H1H2···O4viii	0.98	2.69	3.4427 (18)	134
C2H—H2H1···O1Hvi	0.98	2.52	3.3409 (17)	141
C2H—H2H2···O1ix	0.98	2.67	3.4738 (17)	139
C2H—H2H2···O1Gx	0.98	2.54	3.1574 (17)	121
C2H—H2H2···O4viii	0.98	2.70	3.4604 (18)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1G i	0.84	1.71	2.5451 (13)	171
O3—H3⋯O1H ii	0.84	1.76	2.5732 (13)	161
C1G—H1G2⋯O2iii	0.98	2.56	3.3138 (17)	134
C1G—H1G3⋯O4iv	0.98	2.71	3.5351 (17)	143
C2G—H2G1⋯O1H v	0.98	2.57	3.5093 (18)	160
C2G—H2G2⋯O2iii	0.98	2.52	3.2783 (17)	135
C1H—H1H1⋯O4vi	0.98	2.57	3.5006 (18)	159
C1H—H1H2⋯O4vii	0.98	2.69	3.4427 (18)	134
C2H—H2H1⋯O1H v	0.98	2.52	3.3409 (17)	141
C2H—H2H2⋯O1viii	0.98	2.67	3.4738 (17)	139
C2H—H2H2⋯O1G ix	0.98	2.54	3.1574 (17)	121
C2H—H2H2⋯O4vii	0.98	2.70	3.4604 (18)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .