o-Phenyl-enediammonium bis-(3-carb-oxy-4-hydroxy-benzene-sulfonate).

In the title salt, C(6)H(10)N(2) (2+)·2C(7)H(5)O(6)S(-), the negative charge of the anion resides on the sulfonate group. In the crystal, the cations and anions are -linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network. The complete dication is generated by crystallographic twofold symmetry.

Related literature

For related structures, see: Bakasova et al. (1991 ▶); Du et al. (2008 ▶); Meng et al. (2008 ▶); Raj et al. (2003 ▶); Smith (2005 ▶); Smith et al. (2004 ▶, 2005a ▶,b ▶,c ▶, 2006 ▶); Wang & Wei (2007 ▶).

Experimental

Crystal data

C6H10N2 2+·2C7H5O6S−

M = 544.50

Monoclinic,

a = 11.667 (2) Å

b = 16.081 (3) Å

c = 12.356 (3) Å

β = 105.90 (3)°

V = 2229.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 566 K

0.30 × 0.28 × 0.24 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.902, T max = 0.923

11440 measured reflections

2543 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.108

S = 1.00

2543 reflections

178 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049071/ng2658sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049071/ng2658Isup2.hkl

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

C6H10N22+·2C7H5O6S−	F(000) = 1128
Mr = 544.50	Dx = 1.622 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6744 reflections
a = 11.667 (2) Å	θ = 3.3–27.6°
b = 16.081 (3) Å	µ = 0.31 mm−1
c = 12.356 (3) Å	T = 566 K
β = 105.90 (3)°	Block, dark-blue
V = 2229.5 (9) Å3	0.30 × 0.28 × 0.24 mm
Z = 4

Rigaku SCXmini diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
dtfind.ref scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.902, Tmax = 0.923	l = −15→15
11440 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0426P)2 + 3.7751P] where P = (Fo2 + 2Fc2)/3
2543 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.34 e Å−3
5 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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
C1	0.1315 (2)	0.73023 (13)	0.37688 (17)	0.0286 (5)
C2	0.0224 (2)	0.71605 (15)	0.40005 (19)	0.0334 (5)
C3	−0.0144 (2)	0.63524 (16)	0.4130 (2)	0.0400 (6)
H3	−0.0870	0.6259	0.4285	0.048*
C4	0.0566 (2)	0.56927 (14)	0.40305 (19)	0.0338 (5)
H4	0.0314	0.5153	0.4108	0.041*
C5	0.16661 (19)	0.58267 (13)	0.38137 (17)	0.0255 (4)
C6	0.20342 (19)	0.66230 (13)	0.36823 (17)	0.0265 (4)
H6	0.2765	0.6711	0.3535	0.032*
C7	0.1671 (2)	0.81562 (14)	0.35783 (19)	0.0340 (5)
C8	0.5460 (2)	0.77864 (15)	0.2988 (2)	0.0463 (7)
H8	0.5770	0.8288	0.3315	0.056*
C9	0.5925 (2)	0.70459 (15)	0.3483 (2)	0.0379 (6)
H9	0.6545	0.7047	0.4142	0.046*
C10	0.54644 (18)	0.63079 (13)	0.29932 (17)	0.0258 (4)
S1	0.25193 (5)	0.49616 (3)	0.36307 (5)	0.03052 (16)
O1	0.37475 (17)	0.52318 (12)	0.3896 (2)	0.0617 (6)
O2	0.23442 (14)	0.43243 (10)	0.43955 (14)	0.0367 (4)
O3	−0.05305 (18)	0.77829 (12)	0.40738 (17)	0.0513 (5)
H3A	−0.014 (3)	0.8226 (13)	0.403 (3)	0.077*
O4	0.2075 (2)	0.47241 (12)	0.24585 (15)	0.0656 (7)
O5	0.27040 (17)	0.82146 (10)	0.33577 (16)	0.0444 (5)
H5A	0.276 (3)	0.8699 (10)	0.310 (2)	0.067*
O6	0.10406 (17)	0.87634 (10)	0.36053 (16)	0.0498 (5)
N1	0.59386 (18)	0.55255 (12)	0.35330 (17)	0.0326 (4)
H1A	0.6474 (19)	0.5606 (17)	0.4158 (14)	0.049*
H1B	0.620 (2)	0.5226 (15)	0.3080 (19)	0.049*
H1C	0.5367 (18)	0.5255 (15)	0.368 (2)	0.049*

	U11	U22	U33	U12	U13	U23
C1	0.0364 (12)	0.0250 (11)	0.0238 (10)	0.0015 (9)	0.0075 (9)	0.0000 (8)
C2	0.0353 (12)	0.0369 (13)	0.0288 (11)	0.0079 (10)	0.0101 (10)	0.0001 (10)
C3	0.0319 (13)	0.0456 (15)	0.0469 (14)	0.0002 (11)	0.0184 (11)	0.0031 (12)
C4	0.0349 (12)	0.0316 (12)	0.0364 (13)	−0.0060 (10)	0.0121 (10)	0.0003 (10)
C5	0.0297 (11)	0.0241 (10)	0.0233 (10)	0.0008 (8)	0.0080 (9)	−0.0009 (8)
C6	0.0278 (11)	0.0261 (11)	0.0258 (11)	−0.0005 (9)	0.0079 (9)	−0.0008 (8)
C7	0.0448 (14)	0.0277 (12)	0.0280 (12)	0.0027 (10)	0.0073 (10)	−0.0003 (9)
C8	0.0600 (18)	0.0249 (12)	0.0618 (17)	−0.0104 (11)	0.0298 (13)	−0.0116 (11)
C9	0.0422 (14)	0.0343 (13)	0.0382 (13)	−0.0092 (11)	0.0126 (11)	−0.0088 (10)
C10	0.0263 (11)	0.0235 (10)	0.0288 (11)	−0.0002 (8)	0.0094 (9)	0.0011 (8)
S1	0.0387 (3)	0.0218 (3)	0.0332 (3)	0.0037 (2)	0.0134 (2)	0.0026 (2)
O1	0.0403 (11)	0.0380 (11)	0.1180 (19)	0.0047 (8)	0.0410 (12)	0.0108 (11)
O2	0.0404 (9)	0.0279 (8)	0.0394 (9)	−0.0004 (7)	0.0070 (7)	0.0091 (7)
O3	0.0508 (12)	0.0455 (11)	0.0653 (12)	0.0171 (9)	0.0291 (10)	0.0021 (10)
O4	0.1183 (19)	0.0432 (11)	0.0312 (10)	0.0353 (12)	0.0134 (11)	−0.0044 (8)
O5	0.0530 (11)	0.0263 (9)	0.0593 (12)	−0.0020 (8)	0.0246 (9)	0.0068 (8)
O6	0.0623 (12)	0.0272 (9)	0.0616 (12)	0.0110 (8)	0.0200 (10)	0.0001 (8)
N1	0.0339 (11)	0.0304 (11)	0.0322 (11)	0.0019 (9)	0.0070 (8)	0.0050 (9)

C1—C2	1.398 (3)	C8—C9	1.380 (4)
C1—C6	1.399 (3)	C8—H8	0.9300
C1—C7	1.472 (3)	C9—C10	1.373 (3)
C2—O3	1.352 (3)	C9—H9	0.9300
C2—C3	1.391 (3)	C10—C10i	1.391 (4)
C3—C4	1.372 (3)	C10—N1	1.460 (3)
C3—H3	0.9300	S1—O2	1.4459 (16)
C4—C5	1.398 (3)	S1—O1	1.447 (2)
C4—H4	0.9300	S1—O4	1.4495 (19)
C5—C6	1.374 (3)	O3—H3A	0.86 (3)
C5—S1	1.761 (2)	O5—H5A	0.849 (10)
C6—H6	0.9300	N1—H1A	0.860 (10)
C7—O6	1.228 (3)	N1—H1B	0.856 (10)
C7—O5	1.310 (3)	N1—H1C	0.857 (10)
C8—C8i	1.378 (6)
C2—C1—C6	119.2 (2)	C8i—C8—H8	119.8
C2—C1—C7	119.8 (2)	C9—C8—H8	119.8
C6—C1—C7	121.0 (2)	C10—C9—C8	119.5 (2)
O3—C2—C3	117.2 (2)	C10—C9—H9	120.3
O3—C2—C1	122.6 (2)	C8—C9—H9	120.3
C3—C2—C1	120.2 (2)	C9—C10—C10i	120.17 (14)
C4—C3—C2	119.9 (2)	C9—C10—N1	119.4 (2)
C4—C3—H3	120.0	C10i—C10—N1	120.45 (11)
C2—C3—H3	120.0	O2—S1—O1	111.92 (12)
C3—C4—C5	120.4 (2)	O2—S1—O4	112.98 (12)
C3—C4—H4	119.8	O1—S1—O4	111.50 (15)
C5—C4—H4	119.8	O2—S1—C5	106.86 (10)
C6—C5—C4	120.0 (2)	O1—S1—C5	107.06 (11)
C6—C5—S1	121.00 (17)	O4—S1—C5	106.05 (11)
C4—C5—S1	118.93 (16)	C2—O3—H3A	104 (2)
C5—C6—C1	120.3 (2)	C7—O5—H5A	108 (2)
C5—C6—H6	119.8	C10—N1—H1A	111.8 (19)
C1—C6—H6	119.8	C10—N1—H1B	110.2 (19)
O6—C7—O5	122.7 (2)	H1A—N1—H1B	112 (3)
O6—C7—C1	122.7 (2)	C10—N1—H1C	108.4 (19)
O5—C7—C1	114.6 (2)	H1A—N1—H1C	107 (3)
C8i—C8—C9	120.33 (15)	H1B—N1—H1C	107 (3)
C6—C1—C2—O3	−178.6 (2)	C2—C1—C7—O6	−0.5 (3)
C7—C1—C2—O3	−0.9 (3)	C6—C1—C7—O6	177.2 (2)
C6—C1—C2—C3	−0.7 (3)	C2—C1—C7—O5	−179.4 (2)
C7—C1—C2—C3	177.0 (2)	C6—C1—C7—O5	−1.7 (3)
O3—C2—C3—C4	178.0 (2)	C8i—C8—C9—C10	0.1 (5)
C1—C2—C3—C4	0.0 (4)	C8—C9—C10—C10i	−0.1 (4)
C2—C3—C4—C5	0.9 (4)	C8—C9—C10—N1	−178.5 (2)
C3—C4—C5—C6	−1.0 (3)	C6—C5—S1—O2	147.63 (18)
C3—C4—C5—S1	−177.25 (19)	C4—C5—S1—O2	−36.1 (2)
C4—C5—C6—C1	0.2 (3)	C6—C5—S1—O1	27.6 (2)
S1—C5—C6—C1	176.44 (16)	C4—C5—S1—O1	−156.21 (19)
C2—C1—C6—C5	0.6 (3)	C6—C5—S1—O4	−91.6 (2)
C7—C1—C6—C5	−177.1 (2)	C4—C5—S1—O4	84.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.86 (1)	2.46 (2)	3.157 (3)	139 (2)
N1—H1B···O4i	0.86 (1)	2.42 (2)	3.176 (3)	147 (2)
N1—H1A···O2ii	0.86 (1)	1.94 (1)	2.795 (3)	174 (3)
N1—H1B···O6iii	0.86 (1)	2.46 (3)	2.836 (3)	107 (2)
N1—H1C···O1	0.86 (1)	1.98 (2)	2.755 (3)	150 (3)
O3—H3A···O6	0.86 (3)	1.82 (2)	2.600 (3)	151 (3)
O5—H5A···O4iv	0.85 (1)	1.82 (1)	2.668 (2)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.856 (10)	2.46 (2)	3.157 (3)	139 (2)
N1—H1B⋯O4i	0.856 (10)	2.424 (18)	3.176 (3)	147 (2)
N1—H1A⋯O2ii	0.860 (10)	1.939 (11)	2.795 (3)	174 (3)
N1—H1B⋯O6iii	0.856 (10)	2.46 (3)	2.836 (3)	107 (2)
N1—H1C⋯O1	0.857 (10)	1.979 (17)	2.755 (3)	150 (3)
O3—H3A⋯O6	0.86 (3)	1.82 (2)	2.600 (3)	151 (3)
O5—H5A⋯O4iv	0.849 (10)	1.819 (10)	2.668 (2)	178 (3)

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