Polymeric structure of disodium p-terphenyl-4,4′′-di­sulfonate [Na2(O3S-C6H4-C6H4-C6H4-SO3]

Albat, M.; Stock, N.

doi:10.1107/S2414314616000390

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160039

doi:10.1107/S2414314616000390

Open

access

Polymeric structure of disodium p-terphenyl-4,4′′-disulfonate [Na₂(O₃S-C₆H₄-C₆H₄-C₆H₄-SO₃]

Martin Albat ^a and Norbert Stock ^a ^*

^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.

Keywords: crystal structure; p-terphenyl-4,4′′-disulfonate; coordination polymer.

CCDC reference: 1446149

3D view (loading...)

Chemical scheme

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.

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
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 ). 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.

Table 1
Experimental details

Crystal data
Chemical formula	2Na⁺·C₁₈H₁₂O₆S₂²⁻
M_r	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 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED; Stoe, 2008 )
T_min, T_max	0.902, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	1958, 1958, 1076
(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
Δρ_max, Δρ_min (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 ).

Structural data

CCDC reference: 1446149

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616000390/bt4001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000390/bt4001Isup2.hkl

checkCIF report

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 U_eq(H) = 1.2 U_eq(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.

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

	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.

Disodium p-terphenyl-4,4''-disulfonate top

Crystal data top

2Na⁺·C₁₈H₁₂O₆S₂²⁻	F(000) = 444
M_r = 434.38	D_x = 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

Data collection top

Stoe IPDS-2 diffractometer	1958 independent reflections
Radiation source: fine-focus sealed tube	1076 reflections with I > 2σ(I)
Phi scan	θ_max = 27.4°, θ_min = 2.3°
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008)	h = −5→7
T_min = 0.902, T_max = 0.975	k = −10→10
1958 measured reflections	l = −22→20

Refinement top

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(F_o²) + (0.035P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1958 reflections	Δρ_max = 0.27 e Å⁻³
127 parameters	Δρ_min = −0.40 e Å⁻³

Crystal data top

2Na⁺·C₁₈H₁₂O₆S₂²⁻	V = 873.7 (3) Å³
M_r = 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)°

Data collection top

Stoe IPDS-2 diffractometer	1958 measured reflections
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008)	1958 independent reflections
T_min = 0.902, T_max = 0.975	1076 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
1958 reflections	Δρ_min = −0.40 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—Na1^iv	2.313 (3)	O7—Na1ⁱⁱ	2.560 (3)
O6—Na1ⁱ	2.428 (3)	Na1—O6^vi	2.313 (3)
O6—Na1ⁱⁱ	2.487 (3)	Na1—O5^vii	2.424 (3)
C1—C9	1.384 (5)	Na1—O6ⁱ	2.428 (3)
C1—C10	1.388 (5)	Na1—O6^viii	2.487 (3)
C1—C2	1.483 (5)	Na1—O5ⁱ	2.550 (3)
C2—C3	1.369 (5)	Na1—O7^viii	2.560 (3)
C2—C4	1.369 (5)	Na1—S1ⁱ	3.0225 (17)
C9—C6	1.381 (5)	Na1—S1^viii	3.0363 (18)
C9—H9A	0.9300	Na1—Na1ⁱⁱ	3.1794 (11)
C3—C4^v	1.385 (5)	Na1—Na1^viii	3.1794 (11)
C3—H3A	0.9300	Na1—Na1^ix	3.486 (3)
C4—C3^v	1.385 (5)

O7—S1—O5	114.63 (15)	O6^vi—Na1—O6^viii	133.41 (10)
O7—S1—O6	111.47 (15)	O7—Na1—O6^viii	77.66 (9)
O5—S1—O6	109.83 (14)	O5^vii—Na1—O6^viii	87.72 (9)
O7—S1—C8	106.21 (15)	O6ⁱ—Na1—O6^viii	141.19 (6)
O5—S1—C8	108.07 (17)	O6^vi—Na1—O5ⁱ	141.12 (10)
O6—S1—C8	106.16 (14)	O7—Na1—O5ⁱ	81.99 (9)
O7—S1—Na1ⁱ	132.52 (10)	O5^vii—Na1—O5ⁱ	81.46 (8)
O5—S1—Na1ⁱ	57.32 (10)	O6ⁱ—Na1—O5ⁱ	57.40 (8)
O6—S1—Na1ⁱ	52.52 (10)	O6^viii—Na1—O5ⁱ	84.76 (8)
C8—S1—Na1ⁱ	120.96 (12)	O6^vi—Na1—O7^viii	76.82 (9)
O7—S1—Na1ⁱⁱ	57.24 (11)	O7—Na1—O7^viii	103.72 (10)
O5—S1—Na1ⁱⁱ	135.55 (10)	O5^vii—Na1—O7^viii	80.34 (9)
O6—S1—Na1ⁱⁱ	54.37 (10)	O6ⁱ—Na1—O7^viii	161.12 (9)
C8—S1—Na1ⁱⁱ	116.17 (14)	O6^viii—Na1—O7^viii	57.13 (8)
Na1ⁱ—S1—Na1ⁱⁱ	94.50 (3)	O5ⁱ—Na1—O7^viii	138.08 (10)
S1—O5—Na1ⁱⁱⁱ	138.38 (14)	O6^vi—Na1—S1ⁱ	113.35 (8)
S1—O5—Na1ⁱ	93.89 (12)	O7—Na1—S1ⁱ	84.18 (7)
Na1ⁱⁱⁱ—O5—Na1ⁱ	79.42 (8)	O5^vii—Na1—S1ⁱ	87.65 (7)
S1—O6—Na1^iv	162.26 (15)	O6ⁱ—Na1—S1ⁱ	28.61 (5)
S1—O6—Na1ⁱ	98.87 (12)	O6^viii—Na1—S1ⁱ	113.16 (7)
Na1^iv—O6—Na1ⁱ	94.66 (9)	O5ⁱ—Na1—S1ⁱ	28.79 (6)
S1—O6—Na1ⁱⁱ	97.02 (12)	O7^viii—Na1—S1ⁱ	164.60 (8)
Na1^iv—O6—Na1ⁱⁱ	82.89 (8)	O6^vi—Na1—S1^viii	104.97 (7)
Na1ⁱ—O6—Na1ⁱⁱ	129.73 (10)	O7—Na1—S1^viii	89.64 (8)
C9—C1—C10	116.8 (3)	O5^vii—Na1—S1^viii	84.49 (7)
C9—C1—C2	122.2 (3)	O6ⁱ—Na1—S1^viii	169.62 (7)
C10—C1—C2	121.0 (3)	O6^viii—Na1—S1^viii	28.61 (5)
C3—C2—C4	115.8 (3)	O5ⁱ—Na1—S1^viii	112.26 (7)
C3—C2—C1	122.0 (3)	O7^viii—Na1—S1^viii	28.58 (5)
C4—C2—C1	122.3 (3)	S1ⁱ—Na1—S1^viii	141.04 (5)
C6—C9—C1	122.2 (3)	O6^vi—Na1—Na1ⁱⁱ	161.83 (7)
C6—C9—H9A	118.9	O7—Na1—Na1ⁱⁱ	52.60 (7)
C1—C9—H9A	118.9	O5^vii—Na1—Na1ⁱⁱ	106.25 (8)
C2—C3—C4^v	122.2 (4)	O6ⁱ—Na1—Na1ⁱⁱ	96.78 (7)
C2—C3—H3A	118.9	O6^viii—Na1—Na1ⁱⁱ	46.20 (7)
C4^v—C3—H3A	118.9	O5ⁱ—Na1—Na1ⁱⁱ	48.55 (6)
C2—C4—C3^v	122.1 (4)	O7^viii—Na1—Na1ⁱⁱ	102.09 (8)
C2—C4—H4A	119.0	S1ⁱ—Na1—Na1ⁱⁱ	71.96 (4)
C3^v—C4—H4A	119.0	S1^viii—Na1—Na1ⁱⁱ	73.82 (5)
C7—C10—C1	122.0 (3)	O6^vi—Na1—Na1^viii	50.90 (6)
C7—C10—H10A	119.0	O7—Na1—Na1^viii	143.71 (6)
C1—C10—H10A	119.0	O5^vii—Na1—Na1^viii	52.03 (7)
C8—C6—C9	119.6 (3)	O6ⁱ—Na1—Na1^viii	116.16 (7)
C8—C6—H6A	120.2	O6^viii—Na1—Na1^viii	95.35 (8)
C9—C6—H6A	120.2	O5ⁱ—Na1—Na1^viii	133.37 (7)
C8—C7—C10	119.6 (3)	O7^viii—Na1—Na1^viii	46.78 (6)
C8—C7—H7A	120.2	S1ⁱ—Na1—Na1^viii	130.06 (4)
C10—C7—H7A	120.2	S1^viii—Na1—Na1^viii	70.96 (5)
C7—C8—C6	119.9 (3)	Na1ⁱⁱ—Na1—Na1^viii	139.82 (9)
C7—C8—S1	119.3 (3)	O6^vi—Na1—Na1^ix	43.95 (6)
C6—C8—S1	120.8 (3)	O7—Na1—Na1^ix	101.42 (9)
S1—O7—Na1	142.06 (15)	O5^vii—Na1—Na1^ix	93.94 (8)
S1—O7—Na1ⁱⁱ	94.19 (12)	O6ⁱ—Na1—Na1^ix	41.39 (6)
Na1—O7—Na1ⁱⁱ	80.62 (8)	O6^viii—Na1—Na1^ix	176.86 (9)
O6^vi—Na1—O7	109.65 (10)	O5ⁱ—Na1—Na1^ix	98.12 (8)
O6^vi—Na1—O5^vii	91.54 (9)	O7^viii—Na1—Na1^ix	120.51 (8)
O7—Na1—O5^vii	158.81 (10)	S1ⁱ—Na1—Na1^ix	69.61 (5)
O6^vi—Na1—O6ⁱ	85.34 (9)	S1^viii—Na1—Na1^ix	148.90 (6)
O7—Na1—O6ⁱ	87.94 (9)	Na1ⁱⁱ—Na1—Na1^ix	135.44 (7)
O5^vii—Na1—O6ⁱ	94.19 (9)	Na1^viii—Na1—Na1^ix	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⁻
M_r	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)
T_min, T_max	0.902, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	1958, 1958, 1076
R_int	?
(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
Δρ_max, Δρ_min (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.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160039

doi:10.1107/S2414314616000390

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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