Diammonium biphenyl-4,4'-disulfonate.

In the title salt, 2NH(4) (+)·C(12)H(8)O(6)S(2) (2-), the dianion has crystallographic inversion symmetry. A three-dimensional framework is formed from primary hydrogen-bonded sheet structures comprising ammonium N-H⋯O(sulfonate) inter-actions and is linked peripherally through the biphenyl residues of the anions. This open framework has 43 Å(3) solvent-accessible voids.

Related literature

Biphenyl-4,4′-disulfonate clathrate structures may be found in: Russell et al. (1997 ▶); Swift, Pivovar et al. (1998 ▶); Swift, Reynolds & Ward (1998 ▶); Swift & Ward (2000 ▶); Pivovar et al. (2001 ▶).

Experimental

Crystal data

2NH4 +·C12H8O6S2 2−

M = 348.39

Monoclinic,

a = 14.778 (2) Å

b = 7.4138 (12) Å

c = 7.6647 (13) Å

β = 96.667 (13)°

V = 834.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 297 (2) K

0.40 × 0.30 × 0.11 mm

Data collection

Rigaku AFC 7R four-circle diffractometer

Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999 ▶) T min = 0.874, T max = 0.963

2129 measured reflections

1909 independent reflections

1030 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections frequency: 150 min intensity decay: 1.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.172

S = 0.86

1909 reflections

116 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.39 e Å−3

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999 ▶); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061995/ng2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061995/ng2396Isup2.hkl

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

2N1H4+·C12H8O6S22–	F000 = 364
Mr = 348.39	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Melting point > 573 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 14.778 (2) Å	Cell parameters from 25 reflections
b = 7.4138 (12) Å	θ = 13.7–17.1º
c = 7.6647 (13) Å	µ = 0.35 mm−1
β = 96.667 (13)º	T = 297 (2) K
V = 834.1 (2) Å3	Plate, colourless
Z = 2	0.40 × 0.30 × 0.11 mm

Rigaku AFC 7R four-circle diffractometer	Rint = 0.037
Radiation source: Rigaku rotating anode	θmax = 27.5º
Monochromator: graphite	θmin = 2.8º
T = 297(2) K	h = −8→19
ω–2θ scans	k = 0→9
Absorption correction: ψ scan(TEXSAN for Windows; Molecular Structure Corporation,1999)	l = −9→9
Tmin = 0.874, Tmax = 0.963	3 standard reflections
2129 measured reflections	every 150 min
1909 independent reflections	intensity decay: 1.6%
1030 reflections with I > 2σ(I)

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.1P)2 + 0.8639P] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max < 0.001
1909 reflections	Δρmax = 0.30 e Å−3
116 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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
S1	0.15898 (5)	0.00272 (12)	0.19165 (11)	0.0282 (2)
O11	0.15361 (18)	−0.1393 (4)	0.0601 (3)	0.0415 (8)
O12	0.14295 (19)	0.1783 (4)	0.1126 (4)	0.0458 (9)
O13	0.10228 (17)	−0.0332 (4)	0.3285 (3)	0.0442 (9)
C1	0.2732 (2)	0.0001 (5)	0.2931 (4)	0.0313 (9)
C2	0.3348 (3)	−0.1181 (8)	0.2409 (8)	0.079 (2)
C3	0.4233 (3)	−0.1161 (8)	0.3218 (8)	0.086 (2)
C4	0.4528 (2)	0.0004 (6)	0.4560 (5)	0.0383 (11)
C5	0.3888 (3)	0.1184 (8)	0.5045 (6)	0.0660 (18)
C6	0.3001 (3)	0.1182 (8)	0.4249 (7)	0.0664 (18)
N1	−0.0887 (3)	0.0292 (5)	0.2899 (5)	0.0376 (11)
H2	0.31710	−0.20180	0.14940	0.0940*
H3	0.46580	−0.19870	0.28270	0.1020*
H5	0.40600	0.20300	0.59550	0.0790*
H6	0.25740	0.20130	0.46240	0.0800*
H11	−0.107 (3)	0.055 (5)	0.175 (6)	0.039 (11)*
H12	−0.110 (3)	0.096 (7)	0.357 (6)	0.055 (15)*
H13	−0.027 (4)	0.035 (6)	0.299 (5)	0.055 (14)*
H14	−0.109 (3)	−0.076 (7)	0.323 (6)	0.053 (14)*

	U11	U22	U33	U12	U13	U23
S1	0.0262 (4)	0.0305 (4)	0.0273 (4)	−0.0015 (4)	0.0011 (3)	0.0018 (4)
O11	0.0439 (16)	0.0432 (15)	0.0345 (13)	0.0003 (13)	−0.0073 (11)	−0.0066 (12)
O12	0.0426 (16)	0.0346 (15)	0.0595 (17)	0.0035 (12)	0.0030 (13)	0.0109 (13)
O13	0.0284 (13)	0.073 (2)	0.0313 (13)	−0.0046 (13)	0.0043 (10)	0.0096 (13)
C1	0.0245 (15)	0.0370 (17)	0.0324 (16)	−0.0007 (17)	0.0030 (12)	−0.0043 (18)
C2	0.042 (3)	0.089 (4)	0.097 (4)	0.024 (3)	−0.026 (3)	−0.067 (3)
C3	0.041 (3)	0.098 (4)	0.110 (4)	0.028 (3)	−0.023 (3)	−0.073 (4)
C4	0.0226 (17)	0.051 (2)	0.0404 (19)	−0.0011 (19)	0.0003 (14)	−0.010 (2)
C5	0.034 (2)	0.090 (4)	0.071 (3)	0.010 (2)	−0.006 (2)	−0.053 (3)
C6	0.031 (2)	0.090 (4)	0.075 (3)	0.016 (2)	−0.007 (2)	−0.054 (3)
N1	0.039 (2)	0.046 (2)	0.0285 (17)	0.0049 (16)	0.0073 (14)	0.0010 (16)

S1—O11	1.454 (3)	C2—C3	1.381 (7)
S1—O12	1.444 (3)	C3—C4	1.375 (7)
S1—O13	1.441 (3)	C4—C5	1.371 (6)
S1—C1	1.775 (3)	C4—C4i	1.477 (4)
N1—H14	0.88 (5)	C5—C6	1.380 (6)
N1—H11	0.91 (5)	C2—H2	0.9500
N1—H12	0.80 (5)	C3—H3	0.9500
N1—H13	0.91 (6)	C5—H5	0.9500
C1—C6	1.361 (6)	C6—H6	0.9500
C1—C2	1.357 (6)
O11—S1—O12	111.65 (17)	C1—C2—C3	119.6 (5)
O11—S1—O13	112.42 (16)	C2—C3—C4	123.0 (5)
O11—S1—C1	105.58 (16)	C3—C4—C5	115.8 (4)
O12—S1—O13	113.02 (17)	C4i—C4—C5	121.6 (4)
O12—S1—C1	107.17 (17)	C3—C4—C4i	122.7 (4)
O13—S1—C1	106.43 (15)	C4—C5—C6	122.0 (5)
H12—N1—H14	101 (5)	C1—C6—C5	120.6 (5)
H13—N1—H14	113 (4)	C1—C2—H2	120.00
H11—N1—H14	113 (4)	C3—C2—H2	120.00
H11—N1—H12	113 (4)	C4—C3—H3	118.00
H11—N1—H13	104 (4)	C2—C3—H3	119.00
H12—N1—H13	113 (4)	C4—C5—H5	119.00
C2—C1—C6	119.1 (4)	C6—C5—H5	119.00
S1—C1—C2	121.0 (3)	C5—C6—H6	120.00
S1—C1—C6	120.0 (3)	C1—C6—H6	120.00
O11—S1—C1—C2	0.7 (4)	C1—C2—C3—C4	0.6 (9)
O11—S1—C1—C6	−179.5 (3)	C2—C3—C4—C5	−0.9 (8)
O12—S1—C1—C2	−118.4 (4)	C2—C3—C4—C4i	178.9 (5)
O12—S1—C1—C6	61.4 (4)	C3—C4—C5—C6	0.8 (7)
O13—S1—C1—C2	120.4 (4)	C4i—C4—C5—C6	−179.0 (5)
O13—S1—C1—C6	−59.8 (4)	C3—C4—C4i—C3i	−180.0 (5)
S1—C1—C2—C3	179.6 (4)	C3—C4—C4i—C5i	0.2 (7)
C6—C1—C2—C3	−0.2 (8)	C5—C4—C4i—C3i	−0.2 (7)
S1—C1—C6—C5	−179.7 (4)	C5—C4—C4i—C5i	180.0 (5)
C2—C1—C6—C5	0.1 (7)	C4—C5—C6—C1	−0.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O11ii	0.91 (5)	1.96 (4)	2.861 (5)	172 (4)
N1—H12···O11iii	0.80 (5)	2.18 (5)	2.922 (5)	153 (5)
N1—H12···O13iv	0.80 (5)	2.45 (5)	2.955 (4)	122 (4)
N1—H13···O13	0.91 (6)	1.96 (6)	2.841 (5)	162 (4)
N1—H14···O12v	0.88 (5)	1.97 (5)	2.848 (5)	174 (4)
C2—H2···O11	0.95	2.48	2.873 (6)	105
C6—H6···O12vi	0.95	2.33	3.243 (6)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O11i	0.91 (5)	1.96 (4)	2.861 (5)	172 (4)
N1—H12⋯O11ii	0.80 (5)	2.18 (5)	2.922 (5)	153 (5)
N1—H12⋯O13iii	0.80 (5)	2.45 (5)	2.955 (4)	122 (4)
N1—H13⋯O13	0.91 (6)	1.96 (6)	2.841 (5)	162 (4)
N1—H14⋯O12iv	0.88 (5)	1.97 (5)	2.848 (5)	174 (4)
C2—H2⋯O11	0.95	2.48	2.873 (6)	105
C6—H6⋯O12v	0.95	2.33	3.243 (6)	161

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