Ethyl­enediammonium bis­(3,4-dihy­droxy­benzoate) monohydrate

Zhu, L.-C.

doi:10.1107/S1600536810042182

organic compounds

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Volume 66| Part 11| November 2010| Page o2893

https://doi.org/10.1107/S1600536810042182

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Ethylenediammonium bis(3,4-dihydroxybenzoate) monohydrate

Li-Cai Zhu ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China
^*Correspondence e-mail: licaizhu1977@yahoo.com.cn

(Received 12 October 2010; accepted 18 October 2010; online 23 October 2010)

In the title compound, C₂H₁₀N₂²⁺·2C₇H₅O₄⁻·H₂O, the cation lies on a centre of symmetry. The crystal structure is stabilized by various intermolecular O—H⋯O and N—H⋯O hydrogen bonds, and by weak π–π stacking interactions with centroid–centroid distances between symmetry-related benzene rings ranging from 3.5249 (13) to 3.7566 (14) Å.

Related literature

For protocatechuic acid (3,4-dihydroxybenzoic acid) and its pharmacological activity, see: An et al. (2006 ); Guan et al. (2006 ); Lin et al. (2009 ); Tseng et al. (1998 ); Yip et al. (2006 ). For related structures, see: Mazurek et al. (2007 ); Xu et al. (2008 ).

Experimental

Crystal data

C₂H₁₀N₂²⁺·2C₇H₅O₄⁻·H₂O
M_r = 386.36
Triclinic, $[P \overline 1]$
a = 6.8489 (8) Å
b = 10.7999 (12) Å
c = 12.0137 (13) Å
α = 75.866 (1)°
β = 81.387 (2)°
γ = 83.599 (1)°
V = 849.40 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.25 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.969
4432 measured reflections
3011 independent reflections
2215 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 1.02
3011 reflections
256 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2ⁱ	0.89	2.04	2.904 (3)	163
N1—H1C⋯O4ⁱⁱ	0.89	1.94	2.803 (3)	163
N1—H1D⋯O4	0.89	1.98	2.741 (3)	143
N2—H2B⋯O3ⁱⁱⁱ	0.89	2.09	2.931 (3)	158
N2—H2B⋯O6ⁱⁱⁱ	0.89	2.54	3.079 (3)	120
N2—H2C⋯O8	0.89	1.90	2.742 (2)	157
N2—H2D⋯O7^iv	0.89	1.94	2.799 (3)	163
O1—H1A⋯O1W^v	0.82	1.94	2.753 (3)	169
O2—H2A⋯O7^vi	0.82	1.95	2.755 (2)	168
O5—H5A⋯O3	0.82	2.07	2.834 (2)	156
O5—H5A⋯O4	0.82	2.35	3.014 (3)	139
O6—H6⋯O1W^vii	0.82	1.90	2.686 (2)	160
O1W—H1W⋯O3	0.85 (2)	1.86 (2)	2.676 (2)	159 (3)
O1W—H2W⋯O8^vi	0.88 (2)	1.85 (2)	2.725 (2)	173 (3)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) x-1, y, z; (v) -x, -y+2, -z+1; (vi) x-1, y+1, z; (vii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042182/su2221sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042182/su2221Isup2.hkl

checkCIF report

Comment top

Protocatechuic acid (3,4-dihydroxybenzoic acid) is one of the main secondary metabolites in the plant kingdom (Guan et al., 2006). Significantly, it has been found that protocatechuic acid and its derivatives possess diverse pharmacological activities such as, antioxidant, antiapoptosis, anticarcinogen, anticoagulatory and antiinflammatory (An et al., 2006; Lin et al., 2009; Tseng et al., 1998; Yip et al., 2006). Herein, we report on the molecular and crystal structure of the title compound.

In the asymmetric unit of the title compound, illustrated in Fig. 1, there are two half protonated ethylenediammonium cations located about inversion centers, two singly deprotonated 3,4-dihydroxybenzoate anions, and one water molecule of crystallization. The bond distances and angles in the title compound are normal (Mazurek et al., 2007; Xu et al., 2008).

In the crystal the cations and anions are self-assembled by various intermolecular O—H···O and N—H···O hydrogen bonds (Table 1 and Fig. 2) to form a supramolecular network. The crystal structure is further stabilized by weak π-π stacking interactions (Fig. 2) occurring between adjacent benzene rings, with centroid-to-centroid distances of 3.5249 (13) Å [Cg1···Cg1ⁱ; Cg1 = centroid of ring (C1-C6); symmetry code (i) = 1-x, 2-y, 1-z], 3.7165 (13) Å [Cg1···Cg1ⁱⁱ; Cg1 = centroid of ring (C1-C6); symmetry code (ii) = -x, 2-y, 1-z] and 3.7566 (14) [Cg2···Cg2ⁱⁱⁱ; Cg2 = centroid of ring (C8-C13); symmetry code (iii) = 2-x, 1-y, -z] .

Related literature top

For protocatechuic acid and its pharmacological activity, see: An et al. (2006); Guan et al. (2006); Lin et al. (2009); Tseng et al. (1998); Yip et al. (2006). For related structures, see: Mazurek et al. (2007); Xu et al. (2008).

Experimental top

A solution of ethylenediamine (1 mmol in 0.2 ml water) was added dropwise to a solution of protocatechuic acid (2 mmol) in acetonitrile (15 ml), and the mixture was stirred for 30 min at RT. After several days colourless block-like crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solution.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (A) 1 - x, -y, -z; (B) -x, 1 - y, 1 - z.
	Fig. 2. The crystal packing of the title compound showing the intermolecular hydrogen bonding interactions as broken lines (see Table 1 for details).

Ethylenediammonium bis(3,4-dihydroxybenzoate) monohydrate top

Crystal data top

C₂H₁₀N₂²⁺·2C₇H₅O₄⁻·H₂O	Z = 2
M_r = 386.36	F(000) = 408
Triclinic, P1	D_x = 1.511 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8489 (8) Å	Cell parameters from 1194 reflections
b = 10.7999 (12) Å	θ = 2.9–24.2°
c = 12.0137 (13) Å	µ = 0.13 mm⁻¹
α = 75.866 (1)°	T = 296 K
β = 81.387 (2)°	Block, colourless
γ = 83.599 (1)°	0.30 × 0.28 × 0.25 mm
V = 849.40 (16) Å³

Data collection top

Bruker APEXII area-detector diffractometer	3011 independent reflections
Radiation source: fine-focus sealed tube	2215 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
φ and ω scan	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.963, T_max = 0.969	k = −11→12
4432 measured reflections	l = −7→14

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0467P)² + 0.4204P] where P = (F_o² + 2F_c²)/3
3011 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.38 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂H₁₀N₂²⁺·2C₇H₅O₄⁻·H₂O	γ = 83.599 (1)°
M_r = 386.36	V = 849.40 (16) Å³
Triclinic, P1	Z = 2
a = 6.8489 (8) Å	Mo Kα radiation
b = 10.7999 (12) Å	µ = 0.13 mm⁻¹
c = 12.0137 (13) Å	T = 296 K
α = 75.866 (1)°	0.30 × 0.28 × 0.25 mm
β = 81.387 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	3011 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2215 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.969	R_int = 0.018
4432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.38 e Å⁻³
3011 reflections	Δρ_min = −0.22 e Å⁻³
256 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	0.2895 (3)	0.8335 (2)	0.5353 (2)	0.0292 (6)
H1	0.3031	0.7489	0.5769	0.035*
C2	0.2487 (3)	0.9308 (2)	0.5934 (2)	0.0301 (6)
H2	0.2322	0.9110	0.6738	0.036*
C3	0.2320 (3)	1.0577 (2)	0.5330 (2)	0.0262 (5)
C4	0.2557 (3)	1.0857 (2)	0.4127 (2)	0.0261 (5)
C5	0.2916 (3)	0.9881 (2)	0.3553 (2)	0.0268 (5)
H5	0.3037	1.0076	0.2748	0.032*
C6	0.3103 (3)	0.8606 (2)	0.4157 (2)	0.0258 (5)
C7	0.3510 (3)	0.7571 (2)	0.3514 (2)	0.0280 (5)
C8	0.7469 (3)	0.3983 (2)	0.1577 (2)	0.0295 (6)
H8	0.6571	0.3386	0.1610	0.035*
C9	0.6777 (3)	0.5199 (2)	0.1690 (2)	0.0297 (6)
C10	0.8130 (3)	0.6106 (2)	0.1619 (2)	0.0269 (5)
C11	1.0130 (3)	0.5753 (2)	0.1497 (2)	0.0291 (6)
H11	1.1030	0.6344	0.1481	0.035*
C12	1.0809 (3)	0.4523 (2)	0.1397 (2)	0.0286 (5)
H12	1.2163	0.4292	0.1318	0.034*
C13	0.9487 (3)	0.3636 (2)	0.1413 (2)	0.0258 (5)
C14	1.0255 (3)	0.2336 (2)	0.12291 (19)	0.0247 (5)
C15	0.5818 (4)	0.0203 (2)	0.0254 (2)	0.0299 (6)
H15A	0.5688	−0.0156	0.1082	0.036*
H15B	0.7091	−0.0117	−0.0085	0.036*
C16	0.0738 (4)	0.4632 (3)	0.5389 (2)	0.0377 (6)
H16A	0.1091	0.5173	0.5853	0.045*
H16B	0.0145	0.3896	0.5910	0.045*
N1	0.2550 (3)	0.41936 (18)	0.46971 (18)	0.0344 (5)
H1B	0.2249	0.3627	0.4335	0.052*
H1C	0.3452	0.3830	0.5164	0.052*
H1D	0.3036	0.4862	0.4178	0.052*
N2	0.5721 (3)	0.16219 (18)	0.00223 (18)	0.0323 (5)
H2B	0.5803	0.1949	−0.0737	0.048*
H2C	0.6723	0.1857	0.0298	0.048*
H2D	0.4579	0.1910	0.0367	0.048*
O1	0.1944 (3)	1.15782 (15)	0.58542 (14)	0.0342 (4)
H1A	0.1575	1.1311	0.6545	0.051*
O2	0.2417 (3)	1.21302 (14)	0.35551 (14)	0.0358 (4)
H2A	0.2385	1.2187	0.2865	0.054*
O3	0.3090 (2)	0.77974 (16)	0.24853 (15)	0.0343 (4)
O4	0.4239 (3)	0.64879 (15)	0.40190 (15)	0.0359 (4)
O5	0.4788 (3)	0.55228 (19)	0.1832 (2)	0.0518 (6)
H5A	0.4567	0.6128	0.2145	0.078*
O6	0.7346 (2)	0.73121 (15)	0.16717 (17)	0.0385 (5)
H6	0.8245	0.7775	0.1614	0.058*
O7	1.2060 (2)	0.19869 (15)	0.13369 (14)	0.0319 (4)
O8	0.9088 (2)	0.16349 (15)	0.09982 (15)	0.0344 (4)
O1W	−0.0308 (3)	0.90641 (16)	0.18631 (16)	0.0340 (4)
H1W	0.084 (4)	0.885 (3)	0.208 (2)	0.051*
H2W	−0.040 (4)	0.990 (2)	0.159 (2)	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0341 (14)	0.0220 (12)	0.0300 (14)	−0.0018 (10)	−0.0076 (11)	−0.0010 (10)
C2	0.0336 (14)	0.0305 (14)	0.0256 (13)	−0.0035 (10)	−0.0042 (11)	−0.0043 (11)
C3	0.0246 (12)	0.0263 (13)	0.0301 (14)	−0.0003 (10)	−0.0049 (10)	−0.0109 (11)
C4	0.0278 (13)	0.0202 (12)	0.0304 (14)	−0.0019 (9)	−0.0088 (10)	−0.0031 (10)
C5	0.0301 (13)	0.0284 (13)	0.0229 (13)	−0.0034 (10)	−0.0069 (10)	−0.0055 (10)
C6	0.0233 (12)	0.0222 (12)	0.0319 (14)	−0.0018 (9)	−0.0053 (10)	−0.0050 (10)
C7	0.0216 (12)	0.0260 (13)	0.0369 (15)	−0.0029 (10)	−0.0032 (11)	−0.0079 (11)
C8	0.0287 (13)	0.0263 (13)	0.0367 (15)	−0.0064 (10)	−0.0054 (11)	−0.0107 (11)
C9	0.0228 (12)	0.0336 (14)	0.0361 (15)	−0.0005 (10)	−0.0051 (11)	−0.0146 (11)
C10	0.0319 (13)	0.0220 (12)	0.0286 (13)	−0.0009 (10)	−0.0073 (10)	−0.0080 (10)
C11	0.0310 (13)	0.0260 (13)	0.0319 (14)	−0.0080 (10)	−0.0073 (11)	−0.0055 (11)
C12	0.0259 (13)	0.0261 (13)	0.0334 (14)	0.0002 (10)	−0.0084 (11)	−0.0041 (11)
C13	0.0271 (12)	0.0258 (12)	0.0250 (13)	−0.0001 (10)	−0.0062 (10)	−0.0057 (10)
C14	0.0304 (13)	0.0235 (12)	0.0191 (12)	−0.0016 (10)	−0.0052 (10)	−0.0016 (10)
C15	0.0289 (13)	0.0294 (13)	0.0317 (14)	0.0011 (10)	−0.0066 (10)	−0.0071 (11)
C16	0.0424 (15)	0.0335 (14)	0.0356 (15)	0.0022 (12)	−0.0085 (12)	−0.0051 (12)
N1	0.0377 (12)	0.0235 (11)	0.0413 (13)	−0.0021 (9)	−0.0100 (10)	−0.0031 (9)
N2	0.0302 (11)	0.0325 (12)	0.0365 (12)	−0.0019 (9)	−0.0078 (9)	−0.0105 (10)
O1	0.0466 (11)	0.0267 (9)	0.0298 (10)	−0.0037 (8)	−0.0008 (8)	−0.0098 (7)
O2	0.0575 (12)	0.0204 (9)	0.0296 (10)	−0.0020 (8)	−0.0139 (9)	−0.0018 (7)
O3	0.0369 (10)	0.0352 (10)	0.0339 (10)	0.0056 (8)	−0.0091 (8)	−0.0151 (8)
O4	0.0416 (10)	0.0203 (9)	0.0457 (11)	0.0010 (7)	−0.0107 (9)	−0.0057 (8)
O5	0.0277 (10)	0.0471 (13)	0.0925 (17)	−0.0009 (8)	−0.0053 (10)	−0.0408 (11)
O6	0.0314 (10)	0.0264 (9)	0.0618 (13)	−0.0010 (7)	−0.0062 (9)	−0.0183 (9)
O7	0.0299 (9)	0.0305 (9)	0.0351 (10)	0.0051 (7)	−0.0080 (8)	−0.0082 (8)
O8	0.0386 (10)	0.0249 (9)	0.0445 (11)	−0.0009 (7)	−0.0168 (8)	−0.0112 (8)
O1W	0.0348 (10)	0.0251 (9)	0.0438 (11)	−0.0016 (8)	−0.0115 (8)	−0.0074 (8)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C12—H12	0.9300
C1—C6	1.383 (3)	C13—C14	1.500 (3)
C1—H1	0.9300	C14—O8	1.262 (3)
C2—C3	1.386 (3)	C14—O7	1.268 (3)
C2—H2	0.9300	C15—N2	1.485 (3)
C3—O1	1.362 (3)	C15—C15ⁱ	1.506 (5)
C3—C4	1.391 (3)	C15—H15A	0.9700
C4—C5	1.376 (3)	C15—H15B	0.9700
C4—O2	1.379 (3)	C16—N1	1.486 (3)
C5—C6	1.393 (3)	C16—C16ⁱⁱ	1.507 (5)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.487 (3)	C16—H16B	0.9700
C7—O4	1.265 (3)	N1—H1B	0.8900
C7—O3	1.270 (3)	N1—H1C	0.8900
C8—C9	1.377 (3)	N1—H1D	0.8900
C8—C13	1.389 (3)	N2—H2B	0.8900
C8—H8	0.9300	N2—H2C	0.8900
C9—O5	1.364 (3)	N2—H2D	0.8900
C9—C10	1.401 (3)	O1—H1A	0.8200
C10—O6	1.365 (3)	O2—H2A	0.8200
C10—C11	1.376 (3)	O5—H5A	0.8200
C11—C12	1.385 (3)	O6—H6	0.8200
C11—H11	0.9300	O1W—H1W	0.85 (2)
C12—C13	1.384 (3)	O1W—H2W	0.88 (2)

C2—C1—C6	120.6 (2)	C12—C13—C8	119.0 (2)
C2—C1—H1	119.7	C12—C13—C14	119.6 (2)
C6—C1—H1	119.7	C8—C13—C14	121.4 (2)
C1—C2—C3	120.7 (2)	O8—C14—O7	123.1 (2)
C1—C2—H2	119.7	O8—C14—C13	119.3 (2)
C3—C2—H2	119.7	O7—C14—C13	117.6 (2)
O1—C3—C2	123.4 (2)	N2—C15—C15ⁱ	109.9 (2)
O1—C3—C4	117.6 (2)	N2—C15—H15A	109.7
C2—C3—C4	119.0 (2)	C15ⁱ—C15—H15A	109.7
C5—C4—O2	122.5 (2)	N2—C15—H15B	109.7
C5—C4—C3	120.1 (2)	C15ⁱ—C15—H15B	109.7
O2—C4—C3	117.4 (2)	H15A—C15—H15B	108.2
C4—C5—C6	121.0 (2)	N1—C16—C16ⁱⁱ	110.7 (3)
C4—C5—H5	119.5	N1—C16—H16A	109.5
C6—C5—H5	119.5	C16ⁱⁱ—C16—H16A	109.5
C1—C6—C5	118.6 (2)	N1—C16—H16B	109.5
C1—C6—C7	121.5 (2)	C16ⁱⁱ—C16—H16B	109.5
C5—C6—C7	119.9 (2)	H16A—C16—H16B	108.1
O4—C7—O3	122.3 (2)	C16—N1—H1B	109.5
O4—C7—C6	118.7 (2)	C16—N1—H1C	109.5
O3—C7—C6	119.1 (2)	H1B—N1—H1C	109.5
C9—C8—C13	121.0 (2)	C16—N1—H1D	109.5
C9—C8—H8	119.5	H1B—N1—H1D	109.5
C13—C8—H8	119.5	H1C—N1—H1D	109.5
O5—C9—C8	119.9 (2)	C15—N2—H2B	109.5
O5—C9—C10	120.6 (2)	C15—N2—H2C	109.5
C8—C9—C10	119.5 (2)	H2B—N2—H2C	109.5
O6—C10—C11	123.9 (2)	C15—N2—H2D	109.5
O6—C10—C9	116.5 (2)	H2B—N2—H2D	109.5
C11—C10—C9	119.6 (2)	H2C—N2—H2D	109.5
C10—C11—C12	120.3 (2)	C3—O1—H1A	109.5
C10—C11—H11	119.8	C4—O2—H2A	109.5
C12—C11—H11	119.8	C9—O5—H5A	109.5
C13—C12—C11	120.5 (2)	C10—O6—H6	109.5
C13—C12—H12	119.8	H1W—O1W—H2W	108 (2)
C11—C12—H12	119.8

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2ⁱⁱⁱ	0.89	2.04	2.904 (3)	163
N1—H1C···O4^iv	0.89	1.94	2.803 (3)	163
N1—H1D···O4	0.89	1.98	2.741 (3)	143
N2—H2B···O3^v	0.89	2.09	2.931 (3)	158
N2—H2B···O6^v	0.89	2.54	3.079 (3)	120
N2—H2C···O8	0.89	1.90	2.742 (2)	157
N2—H2D···O7^vi	0.89	1.94	2.799 (3)	163
O1—H1A···O1W^vii	0.82	1.94	2.753 (3)	169
O2—H2A···O7^viii	0.82	1.95	2.755 (2)	168
O5—H5A···O3	0.82	2.07	2.834 (2)	156
O5—H5A···O4	0.82	2.35	3.014 (3)	139
O6—H6···O1W^ix	0.82	1.90	2.686 (2)	160
O1W—H1W···O3	0.85 (2)	1.86 (2)	2.676 (2)	159 (3)
O1W—H2W···O8^viii	0.88 (2)	1.85 (2)	2.725 (2)	173 (3)

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

Experimental details

Crystal data
Chemical formula	C₂H₁₀N₂²⁺·2C₇H₅O₄⁻·H₂O
M_r	386.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8489 (8), 10.7999 (12), 12.0137 (13)
α, β, γ (°)	75.866 (1), 81.387 (2), 83.599 (1)
V (Å³)	849.40 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.28 × 0.25

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	4432, 3011, 2215
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 1.02
No. of reflections	3011
No. of parameters	256
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2ⁱ	0.89	2.04	2.904 (3)	162.8
N1—H1C···O4ⁱⁱ	0.89	1.94	2.803 (3)	163.1
N1—H1D···O4	0.89	1.98	2.741 (3)	142.9
N2—H2B···O3ⁱⁱⁱ	0.89	2.09	2.931 (3)	158.2
N2—H2B···O6ⁱⁱⁱ	0.89	2.54	3.079 (3)	119.6
N2—H2C···O8	0.89	1.90	2.742 (2)	156.9
N2—H2D···O7^iv	0.89	1.94	2.799 (3)	162.5
O1—H1A···O1W^v	0.82	1.94	2.753 (3)	169.2
O2—H2A···O7^vi	0.82	1.95	2.755 (2)	168.2
O5—H5A···O3	0.82	2.07	2.834 (2)	155.8
O5—H5A···O4	0.82	2.35	3.014 (3)	138.5
O6—H6···O1W^vii	0.82	1.90	2.686 (2)	160.3
O1W—H1W···O3	0.85 (2)	1.86 (2)	2.676 (2)	159 (3)
O1W—H2W···O8^vi	0.88 (2)	1.85 (2)	2.725 (2)	173 (3)

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

Acknowledgements

The author acknowledges South China Normal University for supporting this work.

References

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