metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 18 December 2015; accepted 8 January 2016; online 16 January 2016)

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 asymmetric unit contains one sodium cation and one p-terphenyl-4,4′′-di­sulfonate anion on a centre of inversion.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compund is shown in Fig. 1[link]. The layers built up by the NaO7 polyhedra and the connection between these layers through the organic ligand are shown in Fig. 2[link].

[Figure 1]
Figure 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]
[Figure 2]
Figure 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.

Synthesis and crystallization

Disodium para-terphenyl-4,4′′di­sulfonate was synthesized according to the procedure given by Muesmann et al. (2011[Muesmann, T. W. T. (2011). Synthesis, 17, 2775-2780.]). 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 refinement details are summarized in Table 1[link].

Table 1
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)
V3) 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 diffractometer
Absorption correction Numerical (X-SHAPE and X-RED; Stoe, 2008[Stoe (2008). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.902, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections 1958, 1958, 1076
(sin θ/λ)max−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[Stoe (2008). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]), SHELXS2014/7 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]), DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Experimental top

Synthesis and crystallization top

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 top

The C—H H atoms were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(C,N) using a riding model with C—H = 0.95 Å.

Related literature top

For related literature, see: Muesmann (2011).

Experimental top

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 top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Structure description top

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.

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: 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).

Figures top
[Figure 1] 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]
[Figure 2] 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.
Disodium p-terphenyl-4,4''-disulfonate top
Crystal data top
2Na+·C18H12O6S22F(000) = 444
Mr = 434.38Dx = 1.651 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.662 (4) ÅCell parameters from 8528 reflections
b = 8.2854 (17) Åθ = 2.3–27.5°
c = 5.9719 (12) ŵ = 0.39 mm1
β = 91.38 (3)°T = 293 K
V = 873.7 (3) Å3Needle, light brown
Z = 20.16 × 0.11 × 0.05 mm
Data collection top
Stoe IPDS-2
diffractometer
1958 independent reflections
Radiation source: fine-focus sealed tube1076 reflections with I > 2σ(I)
Phi scanθmax = 27.4°, θmin = 2.3°
Absorption correction: numerical
(X-SHAPE and X-RED; Stoe, 2008)
h = 57
Tmin = 0.902, Tmax = 0.975k = 1010
1958 measured reflectionsl = 2220
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.27 e Å3
127 parametersΔρmin = 0.40 e Å3
Crystal data top
2Na+·C18H12O6S22V = 873.7 (3) Å3
Mr = 434.38Z = 2
Monoclinic, P21/cMo Kα radiation
a = 17.662 (4) ŵ = 0.39 mm1
b = 8.2854 (17) ÅT = 293 K
c = 5.9719 (12) Å0.16 × 0.11 × 0.05 mm
β = 91.38 (3)°
Data collection top
Stoe IPDS-2
diffractometer
1958 measured reflections
Absorption correction: numerical
(X-SHAPE and X-RED; Stoe, 2008)
1958 independent reflections
Tmin = 0.902, Tmax = 0.9751076 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.05Δρmax = 0.27 e Å3
1958 reflectionsΔρmin = 0.40 e Å3
127 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.10160 (5)1.00677 (12)0.39209 (13)0.0449 (2)
O50.08018 (12)1.1730 (3)0.4403 (4)0.0498 (6)
O60.05617 (12)0.9457 (3)0.2019 (4)0.0474 (6)
C10.34588 (18)1.0039 (5)0.1584 (5)0.0493 (7)
C20.42455 (18)1.0013 (5)0.0773 (5)0.0505 (8)
C90.3260 (2)0.9301 (6)0.3564 (6)0.0654 (11)
H9A0.36330.87900.44280.079*
C30.4476 (2)1.1005 (7)0.0914 (8)0.0807 (14)
H3A0.41271.17100.15740.097*
C40.4789 (2)0.9009 (6)0.1670 (8)0.0817 (14)
H4A0.46600.83140.28220.098*
C100.2884 (2)1.0803 (6)0.0367 (7)0.0645 (11)
H10A0.30001.13190.09650.077*
C60.2524 (2)0.9299 (6)0.4299 (6)0.0634 (11)
H6A0.24070.87820.56280.076*
C70.2145 (2)1.0822 (5)0.1072 (7)0.0649 (11)
H7A0.17701.13390.02200.078*
C80.19665 (17)1.0068 (5)0.3051 (5)0.0463 (7)
O70.09890 (13)0.8979 (3)0.5831 (4)0.0505 (6)
Na10.02020 (7)0.81590 (17)0.8734 (2)0.0487 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0426 (4)0.0493 (5)0.0430 (4)0.0006 (5)0.0020 (3)0.0003 (5)
O50.0458 (13)0.0521 (15)0.0517 (13)0.0020 (11)0.0052 (10)0.0035 (12)
O60.0448 (12)0.0556 (16)0.0413 (11)0.0021 (10)0.0059 (9)0.0040 (10)
C10.0439 (16)0.056 (2)0.0484 (16)0.000 (2)0.0054 (13)0.001 (2)
C20.0453 (16)0.053 (2)0.0529 (18)0.002 (2)0.0064 (14)0.002 (2)
C90.0453 (19)0.093 (3)0.058 (2)0.007 (2)0.0037 (17)0.018 (2)
C30.049 (2)0.109 (4)0.085 (3)0.016 (2)0.013 (2)0.040 (3)
C40.053 (2)0.114 (4)0.079 (3)0.019 (3)0.021 (2)0.042 (3)
C100.0454 (19)0.085 (3)0.064 (2)0.006 (2)0.0119 (17)0.024 (2)
C60.0454 (19)0.089 (3)0.056 (2)0.004 (2)0.0047 (17)0.016 (2)
C70.047 (2)0.083 (3)0.065 (2)0.006 (2)0.0078 (17)0.026 (2)
C80.0422 (16)0.054 (2)0.0432 (15)0.0004 (18)0.0050 (13)0.0035 (18)
O70.0488 (13)0.0572 (15)0.0455 (12)0.0003 (12)0.0026 (10)0.0134 (12)
Na10.0523 (8)0.0521 (8)0.0416 (6)0.0023 (7)0.0004 (6)0.0007 (6)
Geometric parameters (Å, º) top
S1—O71.456 (2)C4—H4A0.9300
S1—O51.459 (3)C10—C71.381 (5)
S1—O61.465 (2)C10—H10A0.9300
S1—C81.769 (3)C6—C81.377 (5)
S1—Na1i3.0225 (17)C6—H6A0.9300
S1—Na1ii3.0363 (18)C7—C81.380 (5)
O5—Na1iii2.424 (3)C7—H7A0.9300
O5—Na1i2.550 (3)O7—Na12.348 (3)
O6—Na1iv2.313 (3)O7—Na1ii2.560 (3)
O6—Na1i2.428 (3)Na1—O6vi2.313 (3)
O6—Na1ii2.487 (3)Na1—O5vii2.424 (3)
C1—C91.384 (5)Na1—O6i2.428 (3)
C1—C101.388 (5)Na1—O6viii2.487 (3)
C1—C21.483 (5)Na1—O5i2.550 (3)
C2—C31.369 (5)Na1—O7viii2.560 (3)
C2—C41.369 (5)Na1—S1i3.0225 (17)
C9—C61.381 (5)Na1—S1viii3.0363 (18)
C9—H9A0.9300Na1—Na1ii3.1794 (11)
C3—C4v1.385 (5)Na1—Na1viii3.1794 (11)
C3—H3A0.9300Na1—Na1ix3.486 (3)
C4—C3v1.385 (5)
O7—S1—O5114.63 (15)O6vi—Na1—O6viii133.41 (10)
O7—S1—O6111.47 (15)O7—Na1—O6viii77.66 (9)
O5—S1—O6109.83 (14)O5vii—Na1—O6viii87.72 (9)
O7—S1—C8106.21 (15)O6i—Na1—O6viii141.19 (6)
O5—S1—C8108.07 (17)O6vi—Na1—O5i141.12 (10)
O6—S1—C8106.16 (14)O7—Na1—O5i81.99 (9)
O7—S1—Na1i132.52 (10)O5vii—Na1—O5i81.46 (8)
O5—S1—Na1i57.32 (10)O6i—Na1—O5i57.40 (8)
O6—S1—Na1i52.52 (10)O6viii—Na1—O5i84.76 (8)
C8—S1—Na1i120.96 (12)O6vi—Na1—O7viii76.82 (9)
O7—S1—Na1ii57.24 (11)O7—Na1—O7viii103.72 (10)
O5—S1—Na1ii135.55 (10)O5vii—Na1—O7viii80.34 (9)
O6—S1—Na1ii54.37 (10)O6i—Na1—O7viii161.12 (9)
C8—S1—Na1ii116.17 (14)O6viii—Na1—O7viii57.13 (8)
Na1i—S1—Na1ii94.50 (3)O5i—Na1—O7viii138.08 (10)
S1—O5—Na1iii138.38 (14)O6vi—Na1—S1i113.35 (8)
S1—O5—Na1i93.89 (12)O7—Na1—S1i84.18 (7)
Na1iii—O5—Na1i79.42 (8)O5vii—Na1—S1i87.65 (7)
S1—O6—Na1iv162.26 (15)O6i—Na1—S1i28.61 (5)
S1—O6—Na1i98.87 (12)O6viii—Na1—S1i113.16 (7)
Na1iv—O6—Na1i94.66 (9)O5i—Na1—S1i28.79 (6)
S1—O6—Na1ii97.02 (12)O7viii—Na1—S1i164.60 (8)
Na1iv—O6—Na1ii82.89 (8)O6vi—Na1—S1viii104.97 (7)
Na1i—O6—Na1ii129.73 (10)O7—Na1—S1viii89.64 (8)
C9—C1—C10116.8 (3)O5vii—Na1—S1viii84.49 (7)
C9—C1—C2122.2 (3)O6i—Na1—S1viii169.62 (7)
C10—C1—C2121.0 (3)O6viii—Na1—S1viii28.61 (5)
C3—C2—C4115.8 (3)O5i—Na1—S1viii112.26 (7)
C3—C2—C1122.0 (3)O7viii—Na1—S1viii28.58 (5)
C4—C2—C1122.3 (3)S1i—Na1—S1viii141.04 (5)
C6—C9—C1122.2 (3)O6vi—Na1—Na1ii161.83 (7)
C6—C9—H9A118.9O7—Na1—Na1ii52.60 (7)
C1—C9—H9A118.9O5vii—Na1—Na1ii106.25 (8)
C2—C3—C4v122.2 (4)O6i—Na1—Na1ii96.78 (7)
C2—C3—H3A118.9O6viii—Na1—Na1ii46.20 (7)
C4v—C3—H3A118.9O5i—Na1—Na1ii48.55 (6)
C2—C4—C3v122.1 (4)O7viii—Na1—Na1ii102.09 (8)
C2—C4—H4A119.0S1i—Na1—Na1ii71.96 (4)
C3v—C4—H4A119.0S1viii—Na1—Na1ii73.82 (5)
C7—C10—C1122.0 (3)O6vi—Na1—Na1viii50.90 (6)
C7—C10—H10A119.0O7—Na1—Na1viii143.71 (6)
C1—C10—H10A119.0O5vii—Na1—Na1viii52.03 (7)
C8—C6—C9119.6 (3)O6i—Na1—Na1viii116.16 (7)
C8—C6—H6A120.2O6viii—Na1—Na1viii95.35 (8)
C9—C6—H6A120.2O5i—Na1—Na1viii133.37 (7)
C8—C7—C10119.6 (3)O7viii—Na1—Na1viii46.78 (6)
C8—C7—H7A120.2S1i—Na1—Na1viii130.06 (4)
C10—C7—H7A120.2S1viii—Na1—Na1viii70.96 (5)
C7—C8—C6119.9 (3)Na1ii—Na1—Na1viii139.82 (9)
C7—C8—S1119.3 (3)O6vi—Na1—Na1ix43.95 (6)
C6—C8—S1120.8 (3)O7—Na1—Na1ix101.42 (9)
S1—O7—Na1142.06 (15)O5vii—Na1—Na1ix93.94 (8)
S1—O7—Na1ii94.19 (12)O6i—Na1—Na1ix41.39 (6)
Na1—O7—Na1ii80.62 (8)O6viii—Na1—Na1ix176.86 (9)
O6vi—Na1—O7109.65 (10)O5i—Na1—Na1ix98.12 (8)
O6vi—Na1—O5vii91.54 (9)O7viii—Na1—Na1ix120.51 (8)
O7—Na1—O5vii158.81 (10)S1i—Na1—Na1ix69.61 (5)
O6vi—Na1—O6i85.34 (9)S1viii—Na1—Na1ix148.90 (6)
O7—Na1—O6i87.94 (9)Na1ii—Na1—Na1ix135.44 (7)
O5vii—Na1—O6i94.19 (9)Na1viii—Na1—Na1ix83.61 (5)
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+3/2, z1/2; (iii) x, y+1/2, z+3/2; (iv) x, y, z1; (v) x+1, y+2, z; (vi) x, y, z+1; (vii) x, y1/2, z+3/2; (viii) x, y+3/2, z+1/2; (ix) x, y+2, z+2.

Experimental details

Crystal data
Chemical formula2Na+·C18H12O6S22
Mr434.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)17.662 (4), 8.2854 (17), 5.9719 (12)
β (°) 91.38 (3)
V3)873.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.16 × 0.11 × 0.05
Data collection
DiffractometerStoe IPDS2
Absorption correctionNumerical
(X-SHAPE and X-RED; Stoe, 2008)
Tmin, Tmax0.902, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
1958, 1958, 1076
Rint?
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.103, 1.05
No. of reflections1958
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationMuesmann, T. W. T. (2011). Synthesis, 17, 2775–2780.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationStoe (2008). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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