Poly[hemi(ethyl­enediammonium) [di-μ-oxalato-indium(III)] dihydrate]

Sun, Q.; Liu, Y.; Li, H.; Luo, Z.

doi:10.1107/S1600536809008381

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages m394-m395

doi:10.1107/S1600536809008381

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Poly[hemi(ethylenediammonium) [di-μ-oxalato-indium(III)] dihydrate]

Qiaozhen Sun,^a ^* Yang Liu,^a Hongwu Li ^a and Zhi Luo ^a

^aDepartment of Materials Chemistry, School of Materials Science and Engineering, Key Laboratory of Non-ferrous Metals of the Ministry of Education, Central South University, Changsha 410083, People's Republic of China
^*Correspondence e-mail: rosesunqz@yahoo.com.cn

(Received 22 February 2009; accepted 7 March 2009; online 14 March 2009)

In title compound, {(C₂H₁₀N₂)_0.5[In(C₂O₄)₂]·2H₂O}_n, the unique In^III ion is coordinated by eight O atoms from four oxalate ligands in a distorted square-antiprismatic environment. The doubly bis-chelating oxalate ligands act as bridging ligands connecting symmetry-related In^III ions and forming a three-dimensional open framework structure. Ethylenediammonium cations and water molecules occupy the voids within the structure. The unique ethylenediammonium cation and one water molecule both lie on a twofold rotation axis. One of the other two water molecules residing on general crystallographic sites was refined as disordered with half occupancy. In the crystal structure, cations and water molecules are linked to the anionic framework via intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For background information on open-framework materials, see: Fang et al. (2004 ); Li et al. (2008 ); Serre et al. (2006 ); Sun et al. (2006 ). For related materials containing the oxalate ligand, see: Audebrand et al. (2001 , 2004 ); Kokunov et al. (2004 ); Stock et al. (2000 ); Chakrabarti & Natarajan (2002 ); Evans & Lin (2001 ); Vaidhyanathan et al. (2001 ); Gavilan et al. (2007 ); Bataille et al. (2000 ); Trombe et al. (2001 ); Yuan et al. (2004 ). For indium oxaltes, see: Audebrand et al. (2003 ); Bulc et al. (1983 ); Bulc & Golič (1983 ); Chen et al. (2003 ); Huang & Lii (1998 ); Jeanneau et al. (2003 ); Yang et al. (2005 ); For the bond-valence method, see: Brown (1996 ). For bond distances and angles for bridging bidentate oxalate groups, see: Hann (1957 ).

Experimental

Crystal data

(C₂H₁₀N₂)_0.5[In(C₂O₄)₂]·2H₂O
M_r = 357.95
Orthorhombic, F d d 2
a = 15.8498 (4) Å
b = 31.1643 (8) Å
c = 8.6618 (2) Å
V = 4278.48 (18) Å³
Z = 16
Mo Kα radiation
μ = 2.26 mm⁻¹
T = 293 K
0.40 × 0.38 × 0.38 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.426, T_max = 0.467 (expected range = 0.387–0.424)
7189 measured reflections
1679 independent reflections
1673 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.046
S = 1.06
1679 reflections
160 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.71 e Å⁻³
Absolute structure: Flack (1983 ), 668 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯OW1ⁱ	0.89	2.35	2.880 (8)	118
N1—H1B⋯O7ⁱⁱ	0.89	2.47	2.956 (5)	115
N1—H1B⋯OW3	0.89	2.21	2.825 (8)	126
N1—H1C⋯O4ⁱ	0.89	2.44	3.140 (6)	136
N1—H1C⋯O5ⁱⁱⁱ	0.89	2.38	3.166 (5)	147
OW1—HW1A⋯O2^iv	0.85	2.04	2.889 (5)	180
OW2—HW2B⋯O1ⁱⁱⁱ	0.85	2.46	3.241 (15)	153
OW2—HW2A⋯O3	0.85	2.39	3.12 (3)	145
OW3—HW3B⋯O8^v	0.85	2.19	2.870 (6)	137
OW3—HW3A⋯O7	0.85	2.26	2.971 (7)	141
OW3—HW3A⋯O3ⁱⁱ	0.85	2.40	2.962 (6)	124
Symmetry codes: (i) x, y, z-1; (ii) $[x+{\script{1\over 4}}, -y+{\script{3\over 4}}, z-{\script{1\over 4}}]$ ; (iii) $[-x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (v) $[x-{\script{1\over 4}}, -y+{\script{3\over 4}}, z-{\script{3\over 4}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008381/lh2779sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008381/lh2779Isup2.hkl

checkCIF report

Comment top

The synthesis of open-framework materials has emerged as an important area of research because of their potential applications in separation processes, ion exchange and catalysis. In the past few years, there has been considerable effort in designing open-framework structures formed by metal organic carboxylates because of its interesting structural features and the quality for apt design (Fang et al., 2004; Li et al., 2008; Serre et al., 2006; Sun et al., 2006) of which the oxalate ligand plays a major role in the assembly of metal-organic porous frameworks. Many metal oxalate structures are reported such as tin (Audebrand et al., 2001; Kokunov et al., 2004; Stock et al., 2000), zinc (Chakrabarti & Natarajan, 2002; Rvans & Lin, 2001; Vaidhyanathan et al., 2001), zirconium (Audebrand et al., 2004; Gavilan et al., 2007), rare earth (Bataille et al., 2000; Trombe et al., 2001; Yuan et al., 2004). The structures of these compounds vary from monomers, dimmers, chains, layered honeycomb networks to three dimensional frameworks. In this paper, we selected indium and synthesized the three-dimensional indium oxalate compound [(C₂N₂H₁₀)_0.5In(C₂O₄)₂.2H₂O]_n (Fig. 1). Although many indium oxalates have been reported (Audebrand et al., 2003; Bulc et al., 1983; Chen et al., 2003; Huang & Lii, 1998; Jeanneau et al., 2003; Yang et al., 2005), relatively a few of them are three dimensional open frameworks (Chen et al., 2003; Huang & Lii, 1998; Yang et al., 2005).

In the title structure, the In ion is coordinated by eight O atoms from four tetradentate oxalate groups, forming a distorted square antiprismatic arrangement (Fig. 2) in which atoms O1, O2, O5A and O6A (Symmetry code A: -x, 0.5 - y, 1/2 + z) are approximately in the same plane with a deviation of ca. 0.01 Å, while the other plane (formed by atoms O3, O4, O7B and O8B; Symmetry code B: x - 1/4, 0.75 - y, 1/4 + z) is significantly distorted, with a deviation of ca. 0.24 Å. The eight In—O bond distances vary between 2.168 (3) and 2.423 (3) Å (average 2.279 Å), which agrees well with the value 2.265 Å calculated for an eightfold coordinated indium atom with the bond valence method using the program VALENCE (Brown, 1996).

The indium ions are linked by the oxygen atoms of oxalate, giving rise to a three-dimensional interdependent porous framework (Fig. 3). The protonated ethylenediammonium and water molecules occupy the voids, interacting with oxalate anions through N—H···O and O—H···O hydrogen bonds. Without water molecules and cations, the framework exhibits voids possessing approximate dimensions of 6.9×14.5 Å along the crystallographic c axis and an analysis of the void shows that ca 44% of the space is empty. Thus, the ethylenediammonium and water molecules assigned to these cavities act as not only charge-compensating cations but also organic templates. The bond distances and angles for the bridging bidentate oxalate groups are in good agreement with the mean values reported by Hann (1957) for oxalate compounds, i.e., 1.24 and 1.52 Å, 118 and 123° for the C1—O1 and C1—C2 bond lengths and O1—C1—C2 and O1—C1—O5 angles, respectively.

Related literature top

For background information on open-framework materials, see: Fang et al. (2004); Li et al. (2008); Serre et al. (2006); Sun et al. (2006). For related materials containing the oxalate ligand, see: Audebrand et al. (2001, 2004); Kokunov et al. (2004); Stock et al. (2000); Chakrabarti & Natarajan (2002); Rvans & Lin (2001); Vaidhyanathan et al. (2001); Gavilan et al. (2007); Bataille et al. (2000); Trombe et al. (2001); Yuan et al. (2004). For indium oxaltes, see: Audebrand et al. (2003); Bulc et al. (1983); Bulc & Golič (1983); Chen et al. (2003); Huang & Lii (1998); Jeanneau et al. (2003); Yang et al. (2005); For the bond-valence method, see: Brown (1996). For bond distances and angles for bridging bidentate oxalate groups, see: Hann (1957).

Experimental top

A mixture of Ti(SO₄)₂ (0.2 g, 0.84 mmol), H₂C₂O₄.2H₂O (1.0 g, 7.93 mmol), InCl₃.4H₂O (2 ml, 0.5 mol/L) and H₂N(CH₂)₂NH₂ (0.2 ml, CR) in H₂O (5.0 ml) was sealed in a 20 ml stainless-steal reactor with Teflon liner and heated at 393 K for 2 days under autogenously pressure. Colorless crystals were isolated after the reaction solution was cooled gradually and washed with water.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The distorted square antiprismatic environment of Indium. Symmetry codes A: -x, 0.5 - y, 1/2 + z; B: x - 1/4, 0.75 - y, 1/4 + z.
	Fig. 3. Part of the crystal structure viewed crystal along the c axis, the ethylenediammonium and water molecules reside in the voids.

Poly[hemi(ethylenediammonium) [di-µ-oxalato-indium(III)] dihydrate] top

Crystal data top

(C₂H₁₀N₂)_0.5[In(C₂O₄)₂]·2H₂O	F(000) = 2800
M_r = 357.95	D_x = 2.223 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 7228 reflections
a = 15.8498 (4) Å	θ = 2.6–27.9°
b = 31.1643 (8) Å	µ = 2.26 mm⁻¹
c = 8.6618 (2) Å	T = 293 K
V = 4278.48 (18) Å³	Block, colourless
Z = 16	0.4 × 0.38 × 0.38 mm

Data collection top

Bruker SMART CCD diffractometer	1679 independent reflections
Radiation source: fine-focus sealed tube	1673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
T_min = 0.426, T_max = 0.467	k = −36→36
7189 measured reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.018	w = 1/[σ²(F_o²) + (0.0322P)² + 7.4478P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.046	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.45 e Å⁻³
1679 reflections	Δρ_min = −0.71 e Å⁻³
160 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.00087 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 668 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (3)

Crystal data top

(C₂H₁₀N₂)_0.5[In(C₂O₄)₂]·2H₂O	V = 4278.48 (18) Å³
M_r = 357.95	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 15.8498 (4) Å	µ = 2.26 mm⁻¹
b = 31.1643 (8) Å	T = 293 K
c = 8.6618 (2) Å	0.4 × 0.38 × 0.38 mm

Data collection top

Bruker SMART CCD diffractometer	1679 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1673 reflections with I > 2σ(I)
T_min = 0.426, T_max = 0.467	R_int = 0.025
7189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	H-atom parameters constrained
wR(F²) = 0.046	Δρ_max = 0.45 e Å⁻³
S = 1.06	Δρ_min = −0.71 e Å⁻³
1679 reflections	Absolute structure: Flack (1983), 668 Friedel pairs
160 parameters	Absolute structure parameter: 0.00 (3)
13 restraints

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	Occ. (<1)
In1	0.013694 (15)	0.314689 (7)	0.33266 (6)	0.01510 (11)
O1	−0.06449 (17)	0.27864 (9)	0.1683 (4)	0.0277 (6)
O2	0.10165 (19)	0.26861 (9)	0.1750 (4)	0.0290 (7)
O3	0.04152 (19)	0.35822 (9)	0.1416 (3)	0.0241 (6)
O4	0.14920 (17)	0.34173 (8)	0.3713 (3)	0.0220 (6)
C1	−0.0334 (2)	0.25113 (11)	0.0817 (7)	0.0194 (7)
C2	0.0620 (2)	0.24552 (11)	0.0823 (7)	0.0204 (7)
C3	0.1128 (2)	0.37559 (10)	0.1357 (4)	0.0165 (7)
C4	0.1740 (2)	0.36645 (11)	0.2696 (5)	0.0180 (8)
O5	−0.07692 (18)	0.22769 (9)	−0.0061 (3)	0.0259 (7)
O6	0.09025 (18)	0.21856 (9)	−0.0112 (4)	0.0302 (7)
O7	0.13838 (16)	0.39927 (8)	0.0302 (3)	0.0223 (6)
O8	0.24530 (18)	0.38498 (9)	0.2625 (4)	0.0231 (6)
C5	0.2294 (3)	0.2715 (2)	−0.2277 (8)	0.0535 (16)
H5C	0.1687	0.2676	−0.2275	0.064*
H5A	0.2444	0.2864	−0.1332	0.064*
N1	0.2527 (3)	0.29883 (17)	−0.3608 (6)	0.0502 (12)
H1A	0.3035	0.2913	−0.3949	0.075*
H1B	0.2534	0.3262	−0.3316	0.075*
H1C	0.2150	0.2954	−0.4360	0.075*
OW1	0.2500	0.2500	0.3570 (7)	0.0504 (16)
HW1A	0.2938	0.2445	0.3040	0.050*
OW2	0.0119 (6)	0.3117 (3)	−0.173 (3)	0.069 (2)	0.50
HW2B	0.0188	0.2848	−0.1847	0.083*	0.50
HW2A	0.0010	0.3173	−0.0793	0.083*	0.50
OW3	0.1418 (3)	0.36723 (19)	−0.2928 (7)	0.1000 (17)
HW3B	0.1123	0.3788	−0.3632	0.120*
HW3A	0.1542	0.3857	−0.2244	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.01446 (16)	0.01545 (14)	0.01540 (15)	−0.00012 (8)	−0.00093 (14)	0.00069 (11)
O1	0.0185 (13)	0.0268 (13)	0.0378 (17)	−0.0013 (11)	0.0018 (14)	−0.0157 (13)
O2	0.0224 (15)	0.0289 (15)	0.0358 (17)	0.0008 (12)	−0.0078 (14)	−0.0104 (13)
O3	0.0187 (14)	0.0299 (14)	0.0237 (15)	−0.0058 (12)	−0.0031 (12)	0.0086 (11)
O4	0.0264 (15)	0.0220 (12)	0.0176 (15)	−0.0037 (10)	−0.0021 (11)	0.0065 (10)
C1	0.0209 (18)	0.0154 (15)	0.0218 (17)	−0.0017 (14)	0.001 (2)	0.0002 (16)
C2	0.0220 (19)	0.0194 (16)	0.0199 (17)	0.0002 (14)	0.000 (2)	−0.0018 (17)
C3	0.0177 (19)	0.0139 (15)	0.0179 (17)	0.0038 (13)	0.0005 (15)	0.0001 (14)
C4	0.019 (2)	0.0132 (15)	0.0214 (17)	0.0010 (14)	−0.0015 (16)	−0.0011 (14)
O5	0.0193 (15)	0.0251 (13)	0.0333 (17)	−0.0004 (11)	−0.0037 (13)	−0.0135 (13)
O6	0.0213 (15)	0.0324 (15)	0.0369 (19)	0.0024 (12)	0.0032 (14)	−0.0131 (14)
O7	0.0224 (13)	0.0229 (12)	0.0217 (14)	−0.0042 (10)	−0.0032 (11)	0.0066 (10)
O8	0.0180 (13)	0.0273 (15)	0.0239 (15)	−0.0057 (11)	−0.0039 (13)	0.0084 (12)
C5	0.031 (3)	0.080 (4)	0.049 (4)	−0.020 (2)	0.006 (3)	−0.016 (3)
N1	0.028 (2)	0.074 (3)	0.049 (3)	−0.006 (2)	−0.011 (2)	−0.001 (2)
OW1	0.026 (2)	0.086 (4)	0.039 (4)	0.024 (2)	0.000	0.000
OW2	0.084 (4)	0.067 (4)	0.055 (4)	0.013 (4)	−0.002 (5)	−0.006 (4)
OW3	0.083 (3)	0.146 (4)	0.072 (3)	0.016 (3)	−0.030 (3)	−0.045 (3)

Geometric parameters (Å, º) top

In1—O5ⁱ	2.168 (3)	C4—O8	1.270 (5)
In1—O3	2.185 (3)	O5—In1ⁱⁱⁱ	2.168 (3)
In1—O1	2.196 (3)	O6—In1ⁱⁱⁱ	2.370 (3)
In1—O8ⁱⁱ	2.230 (3)	O7—In1^iv	2.327 (3)
In1—O7ⁱⁱ	2.327 (3)	O8—In1^iv	2.230 (3)
In1—O4	2.331 (3)	C5—N1	1.480 (8)
In1—O6ⁱ	2.370 (3)	C5—C5^v	1.492 (12)
In1—O2	2.423 (3)	C5—H5C	0.9700
O1—C1	1.242 (5)	C5—H5A	0.9700
O2—C2	1.248 (6)	N1—H1A	0.8900
O3—C3	1.253 (5)	N1—H1B	0.8900
O4—C4	1.235 (5)	N1—H1C	0.8900
C1—O5	1.260 (6)	OW1—HW1A	0.8500
C1—C2	1.522 (6)	OW2—HW2B	0.8502
C2—O6	1.250 (6)	OW2—HW2A	0.8500
C3—O7	1.243 (4)	OW3—HW3B	0.8498
C3—C4	1.539 (5)	OW3—HW3A	0.8500

O5ⁱ—In1—O3	140.63 (11)	C4—O4—In1	114.7 (2)
O5ⁱ—In1—O1	111.52 (10)	O1—C1—O5	123.2 (4)
O3—In1—O1	86.60 (12)	O1—C1—C2	118.2 (4)
O5ⁱ—In1—O8ⁱⁱ	92.22 (11)	O5—C1—C2	118.7 (4)
O3—In1—O8ⁱⁱ	96.82 (11)	O2—C2—O6	128.6 (4)
O1—In1—O8ⁱⁱ	137.63 (10)	O2—C2—C1	115.8 (4)
O5ⁱ—In1—O7ⁱⁱ	144.54 (11)	O6—C2—C1	115.5 (4)
O3—In1—O7ⁱⁱ	74.02 (11)	O7—C3—O3	125.5 (4)
O1—In1—O7ⁱⁱ	68.82 (10)	O7—C3—C4	117.2 (3)
O8ⁱⁱ—In1—O7ⁱⁱ	71.65 (10)	O3—C3—C4	117.3 (3)
O5ⁱ—In1—O4	72.66 (9)	O4—C4—O8	127.0 (4)
O3—In1—O4	72.43 (9)	O4—C4—C3	116.8 (3)
O1—In1—O4	142.91 (10)	O8—C4—C3	116.1 (3)
O8ⁱⁱ—In1—O4	76.46 (10)	C1—O5—In1ⁱⁱⁱ	119.2 (3)
O7ⁱⁱ—In1—O4	129.79 (9)	C2—O6—In1ⁱⁱⁱ	114.5 (3)
O5ⁱ—In1—O6ⁱ	71.78 (10)	C3—O7—In1^iv	115.0 (2)
O3—In1—O6ⁱ	147.56 (11)	C4—O8—In1^iv	118.0 (3)
O1—In1—O6ⁱ	75.75 (11)	N1—C5—C5^v	114.0 (4)
O8ⁱⁱ—In1—O6ⁱ	79.52 (11)	N1—C5—H5C	108.7
O7ⁱⁱ—In1—O6ⁱ	74.28 (10)	C5^v—C5—H5C	108.7
O4—In1—O6ⁱ	135.78 (10)	N1—C5—H5A	108.7
O5ⁱ—In1—O2	74.70 (10)	C5^v—C5—H5A	108.7
O3—In1—O2	79.93 (11)	H5C—C5—H5A	107.6
O1—In1—O2	69.90 (11)	C5—N1—H1A	109.5
O8ⁱⁱ—In1—O2	152.36 (10)	C5—N1—H1B	109.5
O7ⁱⁱ—In1—O2	131.86 (10)	H1A—N1—H1B	109.5
O4—In1—O2	76.41 (9)	C5—N1—H1C	109.5
O6ⁱ—In1—O2	117.54 (10)	H1A—N1—H1C	109.5
C1—O1—In1	121.4 (3)	H1B—N1—H1C	109.5
C2—O2—In1	114.5 (3)	HW2B—OW2—HW2A	109.8
C3—O3—In1	118.7 (2)	HW3B—OW3—HW3A	109.8

Symmetry codes: (i) −x, −y+1/2, z+1/2; (ii) x−1/4, −y+3/4, z+1/4; (iii) −x, −y+1/2, z−1/2; (iv) x+1/4, −y+3/4, z−1/4; (v) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···OW1^vi	0.89	2.35	2.880 (8)	118
N1—H1B···O7^iv	0.89	2.47	2.956 (5)	115
N1—H1B···OW3	0.89	2.21	2.825 (8)	126
N1—H1C···O4^vi	0.89	2.44	3.140 (6)	136
N1—H1C···O5ⁱⁱⁱ	0.89	2.38	3.166 (5)	147
OW1—HW1A···O2^v	0.85	2.04	2.889 (5)	180
OW2—HW2B···O1ⁱⁱⁱ	0.85	2.46	3.241 (15)	153
OW2—HW2A···O3	0.85	2.39	3.12 (3)	145
OW3—HW3B···O8^vii	0.85	2.19	2.870 (6)	137
OW3—HW3A···O7	0.85	2.26	2.971 (7)	141
OW3—HW3A···O3^iv	0.85	2.40	2.962 (6)	124

Symmetry codes: (iii) −x, −y+1/2, z−1/2; (iv) x+1/4, −y+3/4, z−1/4; (v) −x+1/2, −y+1/2, z; (vi) x, y, z−1; (vii) x−1/4, −y+3/4, z−3/4.

Experimental details

Crystal data
Chemical formula	(C₂H₁₀N₂)_0.5[In(C₂O₄)₂]·2H₂O
M_r	357.95
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	15.8498 (4), 31.1643 (8), 8.6618 (2)
V (Å³)	4278.48 (18)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	2.26
Crystal size (mm)	0.4 × 0.38 × 0.38

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.426, 0.467
No. of measured, independent and observed [I > 2σ(I)] reflections	7189, 1679, 1673
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.046, 1.06
No. of reflections	1679
No. of parameters	160
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.71
Absolute structure	Flack (1983), 668 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···OW1ⁱ	0.89	2.35	2.880 (8)	118.2
N1—H1B···O7ⁱⁱ	0.89	2.47	2.956 (5)	114.9
N1—H1B···OW3	0.89	2.21	2.825 (8)	125.9
N1—H1C···O4ⁱ	0.89	2.44	3.140 (6)	135.7
N1—H1C···O5ⁱⁱⁱ	0.89	2.38	3.166 (5)	147.1
OW1—HW1A···O2^iv	0.85	2.04	2.889 (5)	179.5
OW2—HW2B···O1ⁱⁱⁱ	0.85	2.46	3.241 (15)	152.8
OW2—HW2A···O3	0.85	2.39	3.12 (3)	145.2
OW3—HW3B···O8^v	0.85	2.19	2.870 (6)	137.4
OW3—HW3A···O7	0.85	2.26	2.971 (7)	141.3
OW3—HW3A···O3ⁱⁱ	0.85	2.40	2.962 (6)	123.7

Symmetry codes: (i) x, y, z−1; (ii) x+1/4, −y+3/4, z−1/4; (iii) −x, −y+1/2, z−1/2; (iv) −x+1/2, −y+1/2, z; (v) x−1/4, −y+3/4, z−3/4.

Acknowledgements

The authors acknowledge financial support from the Innovation Program for College Students of Central South University (grant No. 081053308).

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