Ethane-1,2-diaminium 4,4'-sulfonyl-dibenzoate.

In the title salt, C(2)H(10)N(2) (2+)·C(14)H(8)O(6)S(2-), both the ethyl-ene-diaminium cations and the 4,4'-sulfonyl-dibenzoate dianions have crystallographic twofold rotational symmetry. They are inter-linked by aminium N-H⋯O(carboxyl-ate) hydrogen-bonding associations, giving sheets parallel to (101) and are further linked along [010], forming a three-dimensional structure.

Related literature

For the structure of 4,4′-sulfonyl­dibenzoic acid, see: Lian et al. (2007 ▶). For the structures of some metal complexes of the acid, see: Bannerjee et al. (2009 ▶); Jiao (2010 ▶); Pan et al. (2007 ▶); Wu et al. (2007 ▶); Zhuang & Jin (2007 ▶).

Experimental

Crystal data

C2H10N2 2+·C14H8O6S2−

M = 366.39

Monoclinic,

a = 15.2860 (8) Å

b = 4.8436 (2) Å

c = 11.9803 (6) Å

β = 111.812 (6)°

V = 823.51 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 200 K

0.35 × 0.25 × 0.08 mm

Data collection

Oxford Diffraction Gemini-S CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.98, T max = 0.99

5062 measured reflections

1607 independent reflections

1290 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.05

1607 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041274/lh5347sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041274/lh5347Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041274/lh5347Isup3.cml

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

C2H10N22+·C14H8O6S2−	F(000) = 384
Mr = 366.39	Dx = 1.478 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2936 reflections
a = 15.2860 (8) Å	θ = 3.5–28.6°
b = 4.8436 (2) Å	µ = 0.23 mm−1
c = 11.9803 (6) Å	T = 200 K
β = 111.812 (6)°	Plate, colourless
V = 823.51 (8) Å3	0.35 × 0.25 × 0.08 mm
Z = 2

Oxford Diffraction Gemini-S CCD detector diffractometer	1607 independent reflections
Radiation source: Enhance (Mo) X-ray source	1290 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −5→5
Tmin = 0.98, Tmax = 0.99	l = −14→14
5062 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3
1607 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	1.00000	0.61975 (12)	0.75000	0.0180 (2)
O1	1.03086 (9)	0.7681 (3)	0.66702 (11)	0.0249 (4)
O41	0.63470 (9)	−0.2635 (3)	0.51471 (11)	0.0301 (4)
O42	0.66855 (9)	−0.1734 (3)	0.35316 (10)	0.0243 (4)
C1	0.90679 (11)	0.3967 (3)	0.66620 (15)	0.0175 (5)
C2	0.90534 (12)	0.2888 (4)	0.55790 (16)	0.0225 (5)
C3	0.83192 (12)	0.1147 (4)	0.49238 (15)	0.0221 (5)
C4	0.76174 (11)	0.0437 (4)	0.53517 (14)	0.0176 (5)
C5	0.76491 (13)	0.1538 (4)	0.64426 (16)	0.0216 (5)
C6	0.83708 (12)	0.3320 (4)	0.71004 (16)	0.0221 (5)
C41	0.68270 (12)	−0.1474 (3)	0.46402 (15)	0.0192 (5)
N1A	0.61734 (10)	0.3312 (3)	0.23264 (13)	0.0242 (5)
C1A	0.51341 (13)	0.3110 (4)	0.19485 (16)	0.0273 (6)
H2	0.95280	0.33250	0.52980	0.0270*
H3	0.82960	0.04480	0.41900	0.0260*
H5	0.71830	0.10750	0.67330	0.0260*
H6	0.83850	0.40660	0.78220	0.0260*
H11A	0.63740	0.48570	0.27460	0.0290*
H12A	0.63270	0.33380	0.16790	0.0290*
H13A	0.64420	0.18630	0.27810	0.0290*
H14A	0.48380	0.46620	0.14350	0.0330*
H15A	0.49130	0.14250	0.14940	0.0330*

	U11	U22	U33	U12	U13	U23
S1	0.0190 (3)	0.0165 (3)	0.0174 (3)	0.0000	0.0055 (2)	0.0000
O1	0.0270 (7)	0.0217 (7)	0.0255 (7)	−0.0024 (5)	0.0091 (6)	0.0053 (6)
O41	0.0338 (8)	0.0381 (8)	0.0204 (7)	−0.0146 (6)	0.0123 (6)	−0.0022 (6)
O42	0.0310 (7)	0.0265 (7)	0.0153 (6)	−0.0061 (5)	0.0086 (5)	−0.0033 (5)
C1	0.0170 (8)	0.0169 (9)	0.0167 (8)	0.0018 (6)	0.0041 (7)	0.0021 (7)
C2	0.0214 (9)	0.0292 (10)	0.0195 (9)	−0.0025 (7)	0.0107 (7)	−0.0014 (8)
C3	0.0257 (9)	0.0265 (10)	0.0158 (9)	−0.0013 (8)	0.0098 (7)	−0.0031 (7)
C4	0.0177 (8)	0.0187 (9)	0.0148 (8)	0.0021 (7)	0.0041 (7)	0.0028 (7)
C5	0.0237 (9)	0.0244 (10)	0.0214 (9)	−0.0038 (7)	0.0140 (8)	−0.0008 (7)
C6	0.0268 (9)	0.0244 (10)	0.0169 (9)	−0.0014 (8)	0.0103 (8)	−0.0037 (7)
C41	0.0215 (9)	0.0185 (9)	0.0179 (9)	0.0027 (7)	0.0077 (7)	0.0027 (7)
N1A	0.0292 (9)	0.0254 (8)	0.0189 (8)	−0.0004 (7)	0.0099 (7)	−0.0003 (7)
C1A	0.0245 (10)	0.0361 (11)	0.0209 (10)	0.0020 (8)	0.0080 (8)	−0.0024 (8)

S1—O1	1.4407 (14)	C2—C3	1.390 (3)
S1—C1	1.7726 (17)	C3—C4	1.393 (3)
S1—O1i	1.4407 (14)	C4—C41	1.509 (2)
S1—C1i	1.7726 (17)	C4—C5	1.396 (2)
O41—C41	1.247 (2)	C5—C6	1.392 (3)
O42—C41	1.270 (2)	C2—H2	0.9300
N1A—C1A	1.485 (3)	C3—H3	0.9300
N1A—H13A	0.8900	C5—H5	0.9300
N1A—H11A	0.8900	C6—H6	0.9300
N1A—H12A	0.8900	C1A—C1Aii	1.522 (3)
C1—C2	1.391 (2)	C1A—H14A	0.9700
C1—C6	1.388 (3)	C1A—H15A	0.9700
O1—S1—C1	108.27 (8)	C4—C5—C6	120.77 (18)
O1—S1—O1i	120.17 (9)	C1—C6—C5	118.97 (17)
O1—S1—C1i	107.12 (8)	O42—C41—C4	116.17 (16)
O1i—S1—C1	107.12 (8)	O41—C41—O42	124.21 (16)
C1—S1—C1i	104.90 (8)	O41—C41—C4	119.61 (15)
O1i—S1—C1i	108.27 (8)	C3—C2—H2	121.00
C1A—N1A—H11A	109.00	C1—C2—H2	120.00
C1A—N1A—H12A	110.00	C2—C3—H3	120.00
C1A—N1A—H13A	109.00	C4—C3—H3	120.00
H11A—N1A—H12A	109.00	C4—C5—H5	120.00
H11A—N1A—H13A	109.00	C6—C5—H5	120.00
H12A—N1A—H13A	109.00	C5—C6—H6	120.00
C2—C1—C6	121.32 (16)	C1—C6—H6	121.00
S1—C1—C2	119.21 (14)	N1A—C1A—C1Aii	109.76 (15)
S1—C1—C6	119.47 (13)	N1A—C1A—H14A	110.00
C1—C2—C3	118.96 (17)	N1A—C1A—H15A	110.00
C2—C3—C4	120.83 (16)	H14A—C1A—H15A	108.00
C3—C4—C41	120.53 (15)	C1Aii—C1A—H14A	110.00
C3—C4—C5	119.13 (17)	C1Aii—C1A—H15A	110.00
C5—C4—C41	120.35 (16)
O1—S1—C1—C2	30.61 (16)	C2—C3—C4—C5	1.2 (3)
O1—S1—C1—C6	−149.72 (14)	C2—C3—C4—C41	−179.47 (17)
O1i—S1—C1—C2	161.56 (14)	C3—C4—C5—C6	−0.1 (3)
O1i—S1—C1—C6	−18.77 (16)	C41—C4—C5—C6	−179.47 (17)
C1i—S1—C1—C2	−83.51 (15)	C3—C4—C41—O41	162.10 (17)
C1i—S1—C1—C6	96.15 (15)	C3—C4—C41—O42	−19.4 (2)
S1—C1—C2—C3	−179.80 (14)	C5—C4—C41—O41	−18.5 (3)
C6—C1—C2—C3	0.5 (3)	C5—C4—C41—O42	159.93 (17)
S1—C1—C6—C5	−179.17 (14)	C4—C5—C6—C1	−0.7 (3)
C2—C1—C6—C5	0.5 (3)	N1A—C1A—C1Aii—N1Aii	171.97 (14)
C1—C2—C3—C4	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O42iii	0.89	1.87	2.760 (2)	174
N1A—H12A···O41iv	0.89	1.88	2.740 (2)	163
N1A—H13A···O42	0.89	1.93	2.798 (2)	164
C2—H2···O1v	0.93	2.51	3.200 (2)	131
C5—H5···O42vi	0.93	2.56	3.344 (2)	143
C6—H6···O1i	0.93	2.55	2.915 (2)	104
C1A—H14A···O41vii	0.97	2.46	3.384 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O42i	0.89	1.87	2.760 (2)	174
N1A—H12A⋯O41ii	0.89	1.88	2.740 (2)	163
N1A—H13A⋯O42	0.89	1.93	2.798 (2)	164

Symmetry codes: (i) ; (ii) .