Hydrazine-1,2-diium bis­(3-carb­oxy-4-hy­droxy­benzene­sulfonate) tetra­hydrate

Selvaraju, D.; Venkatesh, R.; Sundararajan, V.

doi:10.1107/S1600536811014231

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1236-o1237

doi:10.1107/S1600536811014231

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Hydrazine-1,2-diium bis(3-carboxy-4-hydroxybenzenesulfonate) tetrahydrate

Devipriya Selvaraju,^a Ranjithkumar Venkatesh ^a and Vairam Sundararajan ^a ^*

^aDepartment of Chemistry, Government College of Technology, Coimbatore 641 013, India
^*Correspondence e-mail: vamshen@yahoo.com

(Received 22 March 2011; accepted 15 April 2011; online 29 April 2011)

Reaction of 5-sulfosalicylic acid with hydrazine hydrate at pH = 1 results in the formation of the title hydrated salt, 0.5N₂H₆²⁺·C₇H₅O₆S⁻·2H₂O. The hydrazinium dications lie on centres of inversion. They are located between 3-carboxy-4-hydroxybenzenesulfonate anions, forming intermolecular N—H⋯O hydrogen bonds with sulfonate ions and water molecules of crystallisation. Further intra- and intermolecular O—H⋯O hydrogen bonds are observed in the crystal structure.

Related literature

For general background on hydrogen bonding in proton-transfer compounds of 3-carboxy-4-hydroxybenzenesulfonate anions with Lewis bases, see: Smith et al. (2004 , 2005 ). For recent related structures containing the 3-carboxy-4-hydroxybenzenesulfonate anion, see: Wang, Yang et al. (2008 ); Wang, Yao et al. (2008 ); Smith & Wermuth (2009 ); Hemamalini & Fun (2010 ); Yin et al. (2010 ). For related structures containing the N₂H₆²⁺ hydrazinium dication, see: Starosta & Leciejewicz (2008 ); Klapotke et al. (1996 ).

Experimental

Crystal data

0.5N₂H₆²⁺·C₇H₅O₆S⁻·2H₂O
M_r = 270.25
Triclinic, $[P \overline 1]$
a = 7.0620 (5) Å
b = 7.2069 (4) Å
c = 11.5995 (8) Å
α = 78.460 (3)°
β = 75.806 (3)°
γ = 77.379 (3)°
V = 551.77 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.823, T_max = 0.882
9320 measured reflections
2711 independent reflections
2582 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.12
2711 reflections
187 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O5	0.82	1.88	2.6074 (18)	146
O7—H7A⋯O2ⁱ	0.83 (2)	1.98 (2)	2.8036 (15)	177 (2)
O7—H7B⋯O8	0.85 (2)	1.84 (2)	2.6754 (17)	171 (2)
O4—H4⋯O7ⁱⁱ	0.79 (3)	1.89 (3)	2.6758 (16)	174 (3)
O8—H8B⋯O2ⁱⁱⁱ	0.86 (2)	2.00 (2)	2.8384 (16)	165 (2)
O8—H8A⋯O3^iv	0.87 (2)	1.95 (2)	2.8213 (17)	177 (3)
N1—H1A⋯O3^v	0.82 (2)	1.93 (2)	2.7493 (17)	175.2 (19)
N1—H1B⋯O7	0.94 (2)	1.84 (2)	2.7798 (16)	174.5 (19)
N1—H1C⋯O1^vi	0.91 (2)	1.84 (2)	2.6813 (16)	154 (2)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) x, y-1, z+1; (v) -x, -y+1, -z+1; (vi) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Bruno et al., 2002 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014231/zq2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014231/zq2096Isup2.hkl

checkCIF report

Comment top

5-Sulfosalicylic acid, a strong organic acid with pK_a = 2.85, donates its sulfonic protons to N-containing Lewis bases (Smith et al., 2004, 2005) forming organic salts (Wang, Yang et al., 2008; Wang, Yao et al., 2008; Smith & Wermuth, 2009; Hemamalini & Fun, 2010; Yin et al., 2010). Hydrazine as a diacidic base captures the H atoms of sulfonic groups from two acid molecules to form a dicationic hydrazinium salt. The molecular structure of the salt, C₇H₅O₆S.0.5(H₆N₂).2(H₂O), formed by the reaction of 5-sulfosalicylic acid with hydrazine hydrate at pH = 1 is shown in Fig.1 and the various types of hydrogen bonds involved in the crystal structure are reported in Table 1.

The unit cell of the crystal structure of the title compound contains eight (N₂H₆)²⁺ units located at the unit cell corners (centres of inversion) which contribute to 1/8 of the charge of each cell, two compensating 3-carboxy-4-hydroxybenzenesulfonate anions, and four isolated water molecules. The anions are held by intermolecular N—H···O hydrogen bonds in all directions with the hydrazinium ions. These N···O interactions fall in the range of 2.6813 (16)–2.7798 (16) Å. In addition, the intramolecular O6—H6···O5 hydrogen bond [D···A = 2.6074 (18) Å] and intermolecular O—H···O hydrogen bonds, O7—H7······O2 [D···A = 2.8036 (15) Å] between sulfonyl O atoms and water molecules, O4—H4···O7 [D···A = 2.6758 (16) Å] between carboxyl H atoms and isolated water molecules, and O7—H7B···O8 [D···A = 2.6754 (17) Å] between lattice water molecules, stabilize the molecular conformation and the crystal structure.

The N1—N1ⁱ distance of 1.433 (2) Å (symmetry code: (i) -x, -y, -z + 2) is in a good agreement with the values reported by Starosta & Leciejewicz (2008) and Klapotke et al. (1996). The hydrazinium ion has a staggered conformation due to the symmetry imposed by the centre of inversion located in the middle of the N—N bond.

Related literature top

For general background on hydrogen bonding in proton-transfer compounds of 3-carboxy-4-hydroxybenzenesulfonate anion with Lewis bases, see: Smith et al. (2004, 2005). For recent related structures containing the 3-carboxy-4-hydroxybenzenesulfonate anion, see: Wang, Yang et al. (2008); Wang, Yao et al. (2008); Smith & Wermuth (2009); Hemamalini & Fun (2010); Yin et al. (2010). For related structures containing the N₂H₆²⁺ hydrazinium dication, see: Starosta & Leciejewicz (2008); Klapotke et al. (1996).

Experimental top

The title compound was synthesized by dissolving 5-sulfosalicylicacid dihydrate (2 mmol, 0.508 g) and hydrazine hydrate (99.98% pure; 1 mmol, 0.05 ml) in 30 ml of distilled water at pH = 1. The mixture was stirred for 4 h at ambient temperature and then filtered. The resulting clear solution was kept for three weeks in a wooden enclosure. Colourless prismatic crystals suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound (I), showing displacement ellipsoids at the 50% probability level. Symmetry code: 1 - x, 1 - y, 1 - z.
	Fig. 2. The packing diagram of title compound (I).

Hydrazine-1,2-diium bis(3-carboxy-4-hydroxybenzenesulfonate) tetrahydrate top

Crystal data top

0.5N₂H₆²⁺·C₇H₅O₆S⁻·2H₂O	Z = 2
M_r = 270.25	F(000) = 282
Triclinic, P1	D_x = 1.627 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0620 (5) Å	Cell parameters from 6221 reflections
b = 7.2069 (4) Å	θ = 2.5–26.2°
c = 11.5995 (8) Å	µ = 0.33 mm⁻¹
α = 78.460 (3)°	T = 296 K
β = 75.806 (3)°	Block, colourless
γ = 77.379 (3)°	0.50 × 0.40 × 0.30 mm
V = 551.77 (6) Å³

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2711 independent reflections
Radiation source: fine-focus sealed tube	2582 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω and ϕ scans	θ_max = 28.2°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→9
T_min = 0.823, T_max = 0.882	k = −9→9
9320 measured reflections	l = −13→15

Refinement top

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0527P)² + 0.1344P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2711 reflections	Δρ_max = 0.41 e Å⁻³
187 parameters	Δρ_min = −0.52 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.12 (4)

Crystal data top

0.5N₂H₆²⁺·C₇H₅O₆S⁻·2H₂O	γ = 77.379 (3)°
M_r = 270.25	V = 551.77 (6) Å³
Triclinic, P1	Z = 2
a = 7.0620 (5) Å	Mo Kα radiation
b = 7.2069 (4) Å	µ = 0.33 mm⁻¹
c = 11.5995 (8) Å	T = 296 K
α = 78.460 (3)°	0.50 × 0.40 × 0.30 mm
β = 75.806 (3)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2711 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2582 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.882	R_int = 0.057
9320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	6 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.41 e Å⁻³
2711 reflections	Δρ_min = −0.52 e Å⁻³
187 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.28715 (19)	1.12543 (18)	0.37831 (12)	0.0277 (3)
H7	0.2576	1.2577	0.3783	0.033*
C2	0.36576 (19)	1.05458 (18)	0.27144 (12)	0.0268 (3)
C3	0.4096 (2)	0.8553 (2)	0.27042 (15)	0.0373 (3)
H1	0.4618	0.8079	0.1981	0.045*
C4	0.3755 (3)	0.7304 (2)	0.37640 (16)	0.0434 (4)
H3	0.4049	0.5983	0.3756	0.052*
C5	0.2966 (2)	0.8008 (2)	0.48587 (14)	0.0364 (3)
C6	0.2515 (2)	1.00021 (19)	0.48664 (13)	0.0290 (3)
C7	0.1686 (2)	1.0757 (2)	0.60113 (13)	0.0323 (3)
N1	0.01665 (18)	−0.00608 (18)	0.93729 (10)	0.0272 (3)
O1	0.59710 (15)	1.13796 (16)	0.06468 (10)	0.0369 (3)
O7	−0.03247 (17)	0.36335 (14)	0.80737 (10)	0.0340 (3)
O2	0.40796 (15)	1.40062 (14)	0.17028 (9)	0.0333 (3)
O8	0.19337 (19)	0.5388 (2)	0.88950 (13)	0.0505 (3)
O3	0.24335 (15)	1.22941 (15)	0.07799 (10)	0.0356 (3)
O4	0.1284 (2)	1.26416 (17)	0.58929 (11)	0.0445 (3)
O5	0.1392 (2)	0.97087 (18)	0.69881 (10)	0.0454 (3)
O6	0.2667 (2)	0.67267 (18)	0.58729 (12)	0.0568 (4)
H6	0.2187	0.7301	0.6450	0.085*
S1	0.40819 (4)	1.21604 (4)	0.13623 (3)	0.02543 (16)
H7A	−0.144 (2)	0.430 (3)	0.8122 (19)	0.046 (5)*
H7B	0.043 (3)	0.425 (3)	0.825 (2)	0.062 (7)*
H4	0.086 (4)	1.300 (4)	0.653 (2)	0.058 (7)*
H8B	0.312 (3)	0.559 (4)	0.858 (2)	0.069 (7)*
H8A	0.208 (4)	0.446 (3)	0.949 (2)	0.091 (10)*
H1A	−0.060 (3)	−0.070 (3)	0.9285 (17)	0.035 (5)*
H1B	−0.008 (3)	0.118 (3)	0.8930 (19)	0.045 (5)*
H1C	0.144 (3)	−0.067 (3)	0.9181 (19)	0.047 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0271 (6)	0.0250 (6)	0.0312 (6)	−0.0017 (5)	−0.0065 (5)	−0.0078 (5)
C2	0.0240 (6)	0.0262 (6)	0.0300 (6)	−0.0008 (4)	−0.0065 (5)	−0.0067 (5)
C3	0.0428 (8)	0.0286 (7)	0.0387 (8)	0.0024 (6)	−0.0068 (6)	−0.0130 (6)
C4	0.0567 (10)	0.0237 (6)	0.0467 (9)	0.0024 (6)	−0.0108 (8)	−0.0092 (6)
C5	0.0438 (8)	0.0273 (7)	0.0374 (7)	−0.0021 (6)	−0.0134 (6)	−0.0018 (6)
C6	0.0289 (6)	0.0291 (6)	0.0303 (6)	−0.0027 (5)	−0.0090 (5)	−0.0069 (5)
C7	0.0331 (7)	0.0350 (7)	0.0300 (7)	−0.0061 (5)	−0.0079 (5)	−0.0063 (5)
N1	0.0263 (6)	0.0313 (6)	0.0243 (6)	−0.0042 (4)	−0.0055 (4)	−0.0061 (4)
O1	0.0251 (5)	0.0461 (6)	0.0361 (5)	−0.0001 (4)	0.0002 (4)	−0.0140 (5)
O7	0.0362 (6)	0.0295 (5)	0.0361 (5)	−0.0013 (4)	−0.0069 (4)	−0.0105 (4)
O2	0.0336 (5)	0.0292 (5)	0.0376 (5)	−0.0074 (4)	−0.0033 (4)	−0.0094 (4)
O8	0.0391 (7)	0.0573 (8)	0.0577 (8)	−0.0184 (6)	−0.0190 (6)	0.0066 (6)
O3	0.0306 (5)	0.0376 (5)	0.0417 (6)	−0.0068 (4)	−0.0152 (4)	−0.0031 (4)
O4	0.0646 (8)	0.0348 (6)	0.0307 (6)	−0.0039 (5)	−0.0029 (5)	−0.0115 (4)
O5	0.0622 (8)	0.0433 (6)	0.0285 (5)	−0.0086 (5)	−0.0079 (5)	−0.0034 (5)
O6	0.0906 (11)	0.0314 (6)	0.0418 (7)	−0.0058 (6)	−0.0132 (7)	0.0033 (5)
S1	0.0201 (2)	0.0276 (2)	0.0285 (2)	−0.00186 (12)	−0.00404 (13)	−0.00819 (13)

Geometric parameters (Å, º) top

C1—C2	1.3775 (19)	N1—N1ⁱ	1.433 (2)
C1—C6	1.3954 (19)	N1—H1A	0.82 (2)
C1—H7	0.9300	N1—H1B	0.94 (2)
C2—C3	1.4030 (18)	N1—H1C	0.91 (2)
C2—S1	1.7594 (14)	O1—S1	1.4495 (10)
C3—C4	1.374 (2)	O7—H7A	0.826 (15)
C3—H1	0.9300	O7—H7B	0.847 (15)
C4—C5	1.403 (2)	O2—S1	1.4610 (10)
C4—H3	0.9300	O8—H8B	0.859 (16)
C5—O6	1.3453 (19)	O8—H8A	0.874 (17)
C5—C6	1.404 (2)	O3—S1	1.4599 (10)
C6—C7	1.473 (2)	O4—H4	0.79 (3)
C7—O5	1.2282 (18)	O6—H6	0.8200
C7—O4	1.3115 (19)

C2—C1—C6	120.48 (12)	O5—C7—C6	122.77 (14)
C2—C1—H7	119.8	O4—C7—C6	114.08 (13)
C6—C1—H7	119.8	N1ⁱ—N1—H1A	108.5 (13)
C1—C2—C3	120.22 (13)	N1ⁱ—N1—H1B	109.8 (13)
C1—C2—S1	119.44 (10)	H1A—N1—H1B	109.2 (19)
C3—C2—S1	120.34 (11)	N1ⁱ—N1—H1C	104.8 (14)
C4—C3—C2	119.94 (14)	H1A—N1—H1C	110.6 (18)
C4—C3—H1	120.0	H1B—N1—H1C	113.7 (18)
C2—C3—H1	120.0	H7A—O7—H7B	108.4 (18)
C3—C4—C5	120.36 (13)	H8B—O8—H8A	104 (2)
C3—C4—H3	119.8	C7—O4—H4	111.4 (18)
C5—C4—H3	119.8	C5—O6—H6	109.5
O6—C5—C4	118.15 (13)	O1—S1—O3	112.19 (7)
O6—C5—C6	122.23 (14)	O1—S1—O2	112.97 (6)
C4—C5—C6	119.63 (14)	O3—S1—O2	110.87 (6)
C1—C6—C5	119.37 (13)	O1—S1—C2	107.30 (6)
C1—C6—C7	120.56 (12)	O3—S1—C2	106.83 (6)
C5—C6—C7	120.07 (13)	O2—S1—C2	106.24 (6)
O5—C7—O4	123.15 (14)

C6—C1—C2—C3	0.4 (2)	C4—C5—C6—C7	180.00 (15)
C6—C1—C2—S1	179.78 (10)	C1—C6—C7—O5	−178.27 (14)
C1—C2—C3—C4	−0.5 (2)	C5—C6—C7—O5	1.3 (2)
S1—C2—C3—C4	−179.82 (13)	C1—C6—C7—O4	2.0 (2)
C2—C3—C4—C5	0.1 (3)	C5—C6—C7—O4	−178.35 (14)
C3—C4—C5—O6	−179.70 (16)	C1—C2—S1—O1	139.04 (11)
C3—C4—C5—C6	0.3 (3)	C3—C2—S1—O1	−41.61 (14)
C2—C1—C6—C5	0.0 (2)	C1—C2—S1—O3	−100.46 (12)
C2—C1—C6—C7	179.62 (12)	C3—C2—S1—O3	78.89 (13)
O6—C5—C6—C1	179.65 (14)	C1—C2—S1—O2	17.95 (13)
C4—C5—C6—C1	−0.4 (2)	C3—C2—S1—O2	−162.70 (12)
O6—C5—C6—C7	0.0 (2)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O5	0.82	1.88	2.6074 (18)	146
O7—H7A···O2ⁱⁱ	0.83 (2)	1.98 (2)	2.8036 (15)	177 (2)
O7—H7B···O8	0.85 (2)	1.84 (2)	2.6754 (17)	171 (2)
O4—H4···O7ⁱⁱⁱ	0.79 (3)	1.89 (3)	2.6758 (16)	174 (3)
O8—H8B···O2^iv	0.86 (2)	2.00 (2)	2.8384 (16)	165 (2)
O8—H8A···O3^v	0.87 (2)	1.95 (2)	2.8213 (17)	177 (3)
N1—H1A···O3^vi	0.82 (2)	1.93 (2)	2.7493 (17)	175.2 (19)
N1—H1B···O7	0.94 (2)	1.84 (2)	2.7798 (16)	174.5 (19)
N1—H1C···O1^vii	0.91 (2)	1.84 (2)	2.6813 (16)	154 (2)

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+2, −z+1; (v) x, y−1, z+1; (vi) −x, −y+1, −z+1; (vii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	0.5N₂H₆²⁺·C₇H₅O₆S⁻·2H₂O
M_r	270.25
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0620 (5), 7.2069 (4), 11.5995 (8)
α, β, γ (°)	78.460 (3), 75.806 (3), 77.379 (3)
V (Å³)	551.77 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.823, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	9320, 2711, 2582
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.12
No. of reflections	2711
No. of parameters	187
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.52

Computer programs: , APEX2 (Bruker, 2004) and SAINT (Bruker, 2004), SAINT (Bruker, 2004) and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O5	0.82	1.88	2.6074 (18)	146.4
O7—H7A···O2ⁱ	0.826 (15)	1.978 (15)	2.8036 (15)	177 (2)
O7—H7B···O8	0.847 (15)	1.836 (16)	2.6754 (17)	171 (2)
O4—H4···O7ⁱⁱ	0.79 (3)	1.89 (3)	2.6758 (16)	174 (3)
O8—H8B···O2ⁱⁱⁱ	0.859 (16)	2.001 (18)	2.8384 (16)	165 (2)
O8—H8A···O3^iv	0.874 (17)	1.948 (17)	2.8213 (17)	177 (3)
N1—H1A···O3^v	0.82 (2)	1.93 (2)	2.7493 (17)	175.2 (19)
N1—H1B···O7	0.94 (2)	1.84 (2)	2.7798 (16)	174.5 (19)
N1—H1C···O1^vi	0.91 (2)	1.84 (2)	2.6813 (16)	154 (2)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) x, y−1, z+1; (v) −x, −y+1, −z+1; (vi) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the services of Sophisticated Test and Instrumentation Centre, Cochin University, Kochi, for providing the single-crystal X-ray diffraction data. We thank the All India Council for Technical Education, New Delhi (grant-in-aid No. 8023/BOR/RID/RPS-012/2009-10), for financial support of this work.

References

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Volume 67| Part 5| May 2011| Pages o1236-o1237

doi:10.1107/S1600536811014231

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

Hydrazine-1,2-diium bis­­(3-carb­­oxy-4-hy­dr­oxy­benzene­sulfonate) tetra­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Hydrazine-1,2-diium bis(3-carboxy-4-hydroxybenzenesulfonate) tetrahydrate