metal-organic compounds
Polymeric structure of disodium p-terphenyl-4,4′′-disulfonate [Na2(O3S-C6H4-C6H4-C6H4-SO3]
aMax-Eyth-Strasse 2, 24118 Kiel, Germany
*Correspondence e-mail: Stock@ac.uni-kiel.de
In the title compound, 2Na+·C18H12O6S22−, the sodium ion is sevenfold coordinated by O atoms of five sulfonate groups (two in a chelating and three in a monodentate binding mode). They form (100) layers of edge-, corner- and face-sharing [NaO7] polyherdra which are interconnected by the terphenyl moieties. The contains one sodium cation and one p-terphenyl-4,4′′-disulfonate anion on a centre of inversion.
CCDC reference: 1446149
Structure description
The title compund is shown in Fig. 1. The layers built up by the NaO7 polyhedra and the connection between these layers through the organic ligand are shown in Fig. 2.
Synthesis and crystallization
Disodium para-terphenyl-4,4′′disulfonate was synthesized according to the procedure given by Muesmann et al. (2011). The compound was heated at 130°C solvothermally for 4 h in dilute nitric acid. After cooling to room temperature for 4 d crystals were obtained.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1446149
10.1107/S2414314616000390/bt4001sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616000390/bt4001Isup2.hkl
Disodium para-terphenyl-4,4''disulfonate was synthesized according to the procedure given by Muesmann et al. (2011). The compound was heated at 130 °C solvothermally for 4 h in dilute nitric acid. After cooling to room temperature for 4 d crystals were obtained.
Disodium para-terphenyl-4,4''disulfonate was synthesized according to the procedure given by Muesmann et al. (2011). The compound was heated at 130°C solvothermally for 4 h in dilute nitric acid. After cooling to room temperature for 4 d crystals were obtained.
The title compund is shown in Fig. 1. The layers built up by the NaO7 polyhedra and the connection between these layers through the organic ligand are shown in Fig. 2.
Data collection: X-AREA (Stoe, 2008); cell
X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. : Part of the crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. [Symmetry code: (i) 1 − x, 2 − y, −z] | |
Fig. 2. : Part of the crystal structure of the title compound. The layers built up by the NaO7 polyhedra and the connection between these layers through the organic ligand are shown. |
2Na+·C18H12O6S22− | F(000) = 444 |
Mr = 434.38 | Dx = 1.651 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.662 (4) Å | Cell parameters from 8528 reflections |
b = 8.2854 (17) Å | θ = 2.3–27.5° |
c = 5.9719 (12) Å | µ = 0.39 mm−1 |
β = 91.38 (3)° | T = 293 K |
V = 873.7 (3) Å3 | Needle, light brown |
Z = 2 | 0.16 × 0.11 × 0.05 mm |
Stoe IPDS-2 diffractometer | 1958 independent reflections |
Radiation source: fine-focus sealed tube | 1076 reflections with I > 2σ(I) |
Phi scan | θmax = 27.4°, θmin = 2.3° |
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008) | h = −5→7 |
Tmin = 0.902, Tmax = 0.975 | k = −10→10 |
1958 measured reflections | l = −22→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1958 reflections | Δρmax = 0.27 e Å−3 |
127 parameters | Δρmin = −0.40 e Å−3 |
2Na+·C18H12O6S22− | V = 873.7 (3) Å3 |
Mr = 434.38 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.662 (4) Å | µ = 0.39 mm−1 |
b = 8.2854 (17) Å | T = 293 K |
c = 5.9719 (12) Å | 0.16 × 0.11 × 0.05 mm |
β = 91.38 (3)° |
Stoe IPDS-2 diffractometer | 1958 measured reflections |
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008) | 1958 independent reflections |
Tmin = 0.902, Tmax = 0.975 | 1076 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.27 e Å−3 |
1958 reflections | Δρmin = −0.40 e Å−3 |
127 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.10160 (5) | 1.00677 (12) | 0.39209 (13) | 0.0449 (2) | |
O5 | 0.08018 (12) | 1.1730 (3) | 0.4403 (4) | 0.0498 (6) | |
O6 | 0.05617 (12) | 0.9457 (3) | 0.2019 (4) | 0.0474 (6) | |
C1 | 0.34588 (18) | 1.0039 (5) | 0.1584 (5) | 0.0493 (7) | |
C2 | 0.42455 (18) | 1.0013 (5) | 0.0773 (5) | 0.0505 (8) | |
C9 | 0.3260 (2) | 0.9301 (6) | 0.3564 (6) | 0.0654 (11) | |
H9A | 0.3633 | 0.8790 | 0.4428 | 0.079* | |
C3 | 0.4476 (2) | 1.1005 (7) | −0.0914 (8) | 0.0807 (14) | |
H3A | 0.4127 | 1.1710 | −0.1574 | 0.097* | |
C4 | 0.4789 (2) | 0.9009 (6) | 0.1670 (8) | 0.0817 (14) | |
H4A | 0.4660 | 0.8314 | 0.2822 | 0.098* | |
C10 | 0.2884 (2) | 1.0803 (6) | 0.0367 (7) | 0.0645 (11) | |
H10A | 0.3000 | 1.1319 | −0.0965 | 0.077* | |
C6 | 0.2524 (2) | 0.9299 (6) | 0.4299 (6) | 0.0634 (11) | |
H6A | 0.2407 | 0.8782 | 0.5628 | 0.076* | |
C7 | 0.2145 (2) | 1.0822 (5) | 0.1072 (7) | 0.0649 (11) | |
H7A | 0.1770 | 1.1339 | 0.0220 | 0.078* | |
C8 | 0.19665 (17) | 1.0068 (5) | 0.3051 (5) | 0.0463 (7) | |
O7 | 0.09890 (13) | 0.8979 (3) | 0.5831 (4) | 0.0505 (6) | |
Na1 | 0.02020 (7) | 0.81590 (17) | 0.8734 (2) | 0.0487 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0426 (4) | 0.0493 (5) | 0.0430 (4) | −0.0006 (5) | 0.0020 (3) | −0.0003 (5) |
O5 | 0.0458 (13) | 0.0521 (15) | 0.0517 (13) | 0.0020 (11) | 0.0052 (10) | −0.0035 (12) |
O6 | 0.0448 (12) | 0.0556 (16) | 0.0413 (11) | −0.0021 (10) | −0.0059 (9) | −0.0040 (10) |
C1 | 0.0439 (16) | 0.056 (2) | 0.0484 (16) | 0.000 (2) | 0.0054 (13) | −0.001 (2) |
C2 | 0.0453 (16) | 0.053 (2) | 0.0529 (18) | 0.002 (2) | 0.0064 (14) | 0.002 (2) |
C9 | 0.0453 (19) | 0.093 (3) | 0.058 (2) | 0.007 (2) | 0.0037 (17) | 0.018 (2) |
C3 | 0.049 (2) | 0.109 (4) | 0.085 (3) | 0.016 (2) | 0.013 (2) | 0.040 (3) |
C4 | 0.053 (2) | 0.114 (4) | 0.079 (3) | 0.019 (3) | 0.021 (2) | 0.042 (3) |
C10 | 0.0454 (19) | 0.085 (3) | 0.064 (2) | 0.006 (2) | 0.0119 (17) | 0.024 (2) |
C6 | 0.0454 (19) | 0.089 (3) | 0.056 (2) | 0.004 (2) | 0.0047 (17) | 0.016 (2) |
C7 | 0.047 (2) | 0.083 (3) | 0.065 (2) | 0.006 (2) | 0.0078 (17) | 0.026 (2) |
C8 | 0.0422 (16) | 0.054 (2) | 0.0432 (15) | 0.0004 (18) | 0.0050 (13) | −0.0035 (18) |
O7 | 0.0488 (13) | 0.0572 (15) | 0.0455 (12) | 0.0003 (12) | 0.0026 (10) | 0.0134 (12) |
Na1 | 0.0523 (8) | 0.0521 (8) | 0.0416 (6) | 0.0023 (7) | 0.0004 (6) | −0.0007 (6) |
S1—O7 | 1.456 (2) | C4—H4A | 0.9300 |
S1—O5 | 1.459 (3) | C10—C7 | 1.381 (5) |
S1—O6 | 1.465 (2) | C10—H10A | 0.9300 |
S1—C8 | 1.769 (3) | C6—C8 | 1.377 (5) |
S1—Na1i | 3.0225 (17) | C6—H6A | 0.9300 |
S1—Na1ii | 3.0363 (18) | C7—C8 | 1.380 (5) |
O5—Na1iii | 2.424 (3) | C7—H7A | 0.9300 |
O5—Na1i | 2.550 (3) | O7—Na1 | 2.348 (3) |
O6—Na1iv | 2.313 (3) | O7—Na1ii | 2.560 (3) |
O6—Na1i | 2.428 (3) | Na1—O6vi | 2.313 (3) |
O6—Na1ii | 2.487 (3) | Na1—O5vii | 2.424 (3) |
C1—C9 | 1.384 (5) | Na1—O6i | 2.428 (3) |
C1—C10 | 1.388 (5) | Na1—O6viii | 2.487 (3) |
C1—C2 | 1.483 (5) | Na1—O5i | 2.550 (3) |
C2—C3 | 1.369 (5) | Na1—O7viii | 2.560 (3) |
C2—C4 | 1.369 (5) | Na1—S1i | 3.0225 (17) |
C9—C6 | 1.381 (5) | Na1—S1viii | 3.0363 (18) |
C9—H9A | 0.9300 | Na1—Na1ii | 3.1794 (11) |
C3—C4v | 1.385 (5) | Na1—Na1viii | 3.1794 (11) |
C3—H3A | 0.9300 | Na1—Na1ix | 3.486 (3) |
C4—C3v | 1.385 (5) | ||
O7—S1—O5 | 114.63 (15) | O6vi—Na1—O6viii | 133.41 (10) |
O7—S1—O6 | 111.47 (15) | O7—Na1—O6viii | 77.66 (9) |
O5—S1—O6 | 109.83 (14) | O5vii—Na1—O6viii | 87.72 (9) |
O7—S1—C8 | 106.21 (15) | O6i—Na1—O6viii | 141.19 (6) |
O5—S1—C8 | 108.07 (17) | O6vi—Na1—O5i | 141.12 (10) |
O6—S1—C8 | 106.16 (14) | O7—Na1—O5i | 81.99 (9) |
O7—S1—Na1i | 132.52 (10) | O5vii—Na1—O5i | 81.46 (8) |
O5—S1—Na1i | 57.32 (10) | O6i—Na1—O5i | 57.40 (8) |
O6—S1—Na1i | 52.52 (10) | O6viii—Na1—O5i | 84.76 (8) |
C8—S1—Na1i | 120.96 (12) | O6vi—Na1—O7viii | 76.82 (9) |
O7—S1—Na1ii | 57.24 (11) | O7—Na1—O7viii | 103.72 (10) |
O5—S1—Na1ii | 135.55 (10) | O5vii—Na1—O7viii | 80.34 (9) |
O6—S1—Na1ii | 54.37 (10) | O6i—Na1—O7viii | 161.12 (9) |
C8—S1—Na1ii | 116.17 (14) | O6viii—Na1—O7viii | 57.13 (8) |
Na1i—S1—Na1ii | 94.50 (3) | O5i—Na1—O7viii | 138.08 (10) |
S1—O5—Na1iii | 138.38 (14) | O6vi—Na1—S1i | 113.35 (8) |
S1—O5—Na1i | 93.89 (12) | O7—Na1—S1i | 84.18 (7) |
Na1iii—O5—Na1i | 79.42 (8) | O5vii—Na1—S1i | 87.65 (7) |
S1—O6—Na1iv | 162.26 (15) | O6i—Na1—S1i | 28.61 (5) |
S1—O6—Na1i | 98.87 (12) | O6viii—Na1—S1i | 113.16 (7) |
Na1iv—O6—Na1i | 94.66 (9) | O5i—Na1—S1i | 28.79 (6) |
S1—O6—Na1ii | 97.02 (12) | O7viii—Na1—S1i | 164.60 (8) |
Na1iv—O6—Na1ii | 82.89 (8) | O6vi—Na1—S1viii | 104.97 (7) |
Na1i—O6—Na1ii | 129.73 (10) | O7—Na1—S1viii | 89.64 (8) |
C9—C1—C10 | 116.8 (3) | O5vii—Na1—S1viii | 84.49 (7) |
C9—C1—C2 | 122.2 (3) | O6i—Na1—S1viii | 169.62 (7) |
C10—C1—C2 | 121.0 (3) | O6viii—Na1—S1viii | 28.61 (5) |
C3—C2—C4 | 115.8 (3) | O5i—Na1—S1viii | 112.26 (7) |
C3—C2—C1 | 122.0 (3) | O7viii—Na1—S1viii | 28.58 (5) |
C4—C2—C1 | 122.3 (3) | S1i—Na1—S1viii | 141.04 (5) |
C6—C9—C1 | 122.2 (3) | O6vi—Na1—Na1ii | 161.83 (7) |
C6—C9—H9A | 118.9 | O7—Na1—Na1ii | 52.60 (7) |
C1—C9—H9A | 118.9 | O5vii—Na1—Na1ii | 106.25 (8) |
C2—C3—C4v | 122.2 (4) | O6i—Na1—Na1ii | 96.78 (7) |
C2—C3—H3A | 118.9 | O6viii—Na1—Na1ii | 46.20 (7) |
C4v—C3—H3A | 118.9 | O5i—Na1—Na1ii | 48.55 (6) |
C2—C4—C3v | 122.1 (4) | O7viii—Na1—Na1ii | 102.09 (8) |
C2—C4—H4A | 119.0 | S1i—Na1—Na1ii | 71.96 (4) |
C3v—C4—H4A | 119.0 | S1viii—Na1—Na1ii | 73.82 (5) |
C7—C10—C1 | 122.0 (3) | O6vi—Na1—Na1viii | 50.90 (6) |
C7—C10—H10A | 119.0 | O7—Na1—Na1viii | 143.71 (6) |
C1—C10—H10A | 119.0 | O5vii—Na1—Na1viii | 52.03 (7) |
C8—C6—C9 | 119.6 (3) | O6i—Na1—Na1viii | 116.16 (7) |
C8—C6—H6A | 120.2 | O6viii—Na1—Na1viii | 95.35 (8) |
C9—C6—H6A | 120.2 | O5i—Na1—Na1viii | 133.37 (7) |
C8—C7—C10 | 119.6 (3) | O7viii—Na1—Na1viii | 46.78 (6) |
C8—C7—H7A | 120.2 | S1i—Na1—Na1viii | 130.06 (4) |
C10—C7—H7A | 120.2 | S1viii—Na1—Na1viii | 70.96 (5) |
C7—C8—C6 | 119.9 (3) | Na1ii—Na1—Na1viii | 139.82 (9) |
C7—C8—S1 | 119.3 (3) | O6vi—Na1—Na1ix | 43.95 (6) |
C6—C8—S1 | 120.8 (3) | O7—Na1—Na1ix | 101.42 (9) |
S1—O7—Na1 | 142.06 (15) | O5vii—Na1—Na1ix | 93.94 (8) |
S1—O7—Na1ii | 94.19 (12) | O6i—Na1—Na1ix | 41.39 (6) |
Na1—O7—Na1ii | 80.62 (8) | O6viii—Na1—Na1ix | 176.86 (9) |
O6vi—Na1—O7 | 109.65 (10) | O5i—Na1—Na1ix | 98.12 (8) |
O6vi—Na1—O5vii | 91.54 (9) | O7viii—Na1—Na1ix | 120.51 (8) |
O7—Na1—O5vii | 158.81 (10) | S1i—Na1—Na1ix | 69.61 (5) |
O6vi—Na1—O6i | 85.34 (9) | S1viii—Na1—Na1ix | 148.90 (6) |
O7—Na1—O6i | 87.94 (9) | Na1ii—Na1—Na1ix | 135.44 (7) |
O5vii—Na1—O6i | 94.19 (9) | Na1viii—Na1—Na1ix | 83.61 (5) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+3/2; (iv) x, y, z−1; (v) −x+1, −y+2, −z; (vi) x, y, z+1; (vii) −x, y−1/2, −z+3/2; (viii) x, −y+3/2, z+1/2; (ix) −x, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | 2Na+·C18H12O6S22− |
Mr | 434.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.662 (4), 8.2854 (17), 5.9719 (12) |
β (°) | 91.38 (3) |
V (Å3) | 873.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.16 × 0.11 × 0.05 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Numerical (X-SHAPE and X-RED; Stoe, 2008) |
Tmin, Tmax | 0.902, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1958, 1958, 1076 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.103, 1.05 |
No. of reflections | 1958 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.40 |
Computer programs: X-AREA (Stoe, 2008), SHELXS2014/7 (Sheldrick, 2008), SHELXL2014/7 (Sheldrick, 2015), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2010).
Acknowledgements
The authors like to thank Inke Jess for collecting the single-crystal data.
References
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Muesmann, T. W. T. (2011). Synthesis, 17, 2775–2780. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Stoe (2008). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.