Poly[diaqua­bis(μ3-1H-benzimidazole-5,6-dicarboxyl­ato-κ4N3:O5,O5′:O6)bis­(μ2-1H,3H-benzimidazolium-5,6-dicarboxyl­ato-κ3O5,O5′:O6)digadolinium(III)]

Huang, J.-X.; Wu, Y.-Y.; Huang, C.-D.; Lian, Q.-Y.; Zeng, R.-H.

doi:10.1107/S1600536809046819

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1566-m1567

doi:10.1107/S1600536809046819

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Poly[diaquabis(μ₃-1H-benzimidazole-5,6-dicarboxylato-κ⁴N³:O⁵,O^5′:O⁶)bis(μ₂-1H,3H-benzimidazolium-5,6-dicarboxylato-κ³O⁵,O^5′:O⁶)digadolinium(III)]

Jie-Xuan Huang,^a Yi-Yi Wu,^a Chun-De Huang,^a Qing-Yang Lian ^a and Rong-Hua Zeng ^a,^b ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bKey Laboratory of Technology of Electrochemical Energy Storage and Power Generation in Guangdong Universities, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zrh321@yahoo.com.cn

(Received 19 October 2009; accepted 5 November 2009; online 14 November 2009)

In the title complex, [Gd₂(C₉H₄N₂O₄)₂(C₉H₅N₂O₄)₂(H₂O)₂]_n, two of the benzimidazole-5,6-dicarboxylate ligands are protonated at the imidazole groups. Each Gd^III ion is coordinated by six O atoms and one N atom from five ligands and one water molecule, displaying a distorted bicapped trigonal-prismatic geometry. The Gd^III ions are linked by the carboxylate groups and imidazole N atoms, forming a layer parallel to (001). These layers are further connected by O—H⋯O and N—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Related literature

For related structures, see: Gao et al. (2008 ); Lo et al. (2007 ); Wei et al. (2008 ); Yao et al. (2008 ).

Experimental

Crystal data

[Gd₂(C₉H₄N₂O₄)₂(C₉H₅N₂O₄)₂(H₂O)₂]
M_r = 1169.12
Monoclinic, P 2₁ /c
a = 18.7856 (11) Å
b = 12.7745 (7) Å
c = 15.4776 (9) Å
β = 108.010 (1)°
V = 3532.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.82 mm⁻¹
T = 296 K
0.25 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.448, T_max = 0.501
24827 measured reflections
6338 independent reflections
5929 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.049
S = 1.08
6338 reflections
595 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Gd1—O1	2.338 (2)
Gd1—O2	2.526 (2)
Gd1—O3ⁱ	2.350 (2)
Gd1—O5ⁱⁱ	2.461 (2)
Gd1—O6ⁱⁱ	2.499 (2)
Gd1—O8	2.314 (2)
Gd1—N6	2.617 (3)
Gd1—O1W	2.374 (2)
Gd2—O9	2.312 (2)
Gd2—O11ⁱⁱⁱ	2.539 (2)
Gd2—O12ⁱⁱⁱ	2.342 (2)
Gd2—O13^iv	2.267 (2)
Gd2—O15	2.449 (2)
Gd2—O16	2.520 (2)
Gd2—N1ⁱⁱⁱ	2.612 (3)
Gd2—O2W	2.384 (2)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7^v	0.84	1.80	2.629 (3)	167
O1W—H2W⋯O4ⁱ	0.82	1.92	2.670 (3)	153
O2W—H3W⋯O10^vi	0.86	1.74	2.590 (3)	172
O2W—H4WA⋯O15	0.82	2.14	2.716 (5)	127
O2W—H4WB⋯O2W^vi	0.82	1.91	2.723 (4)	170
N2—H2A⋯O14^vii	0.82 (4)	1.94 (4)	2.742 (3)	169 (3)
N3—H3A⋯O10^vii	0.81 (4)	1.94 (4)	2.731 (4)	166 (4)
N4—H4A⋯O16	0.84 (4)	1.97 (4)	2.801 (4)	170 (4)
N5—H5A⋯O4^v	0.83 (4)	1.96 (4)	2.772 (3)	165 (4)
N7—H7A⋯O5	0.77 (4)	2.08 (4)	2.845 (3)	171 (4)
N8—H8A⋯O7^viii	0.80 (4)	1.95 (4)	2.747 (3)	172 (4)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) -x+1, -y, -z; (vii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (viii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046819/hy2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046819/hy2247Isup2.hkl

checkCIF report

Comment top

In recent years, research on coordination polymers has made considerable progress in the fields of supramolecular chemistry and crystal engineering, because of their intriguing structural motifs and functional properties, such as molecular adsorption, magnetism and luminescence. In general, the structural motifs of these hybrid compounds are closely related to the geometries of metal centers and the number of coordination sites provided by multidentate ligands. On the other hand, the supramolecular interactions such as hydrogen-bonding, π–π stacking and metallophilic interactions also play the key roles in the recognition process forming final three-dimensional architectures. As a building block, benzimidazole-5,6-dicarboxylic acid is a good ligand with multifunctional coordination sites providing intriguing architectures and topologies (Gao et al., 2008; Lo et al., 2007; Wei et al., 2008; Yao et al., 2008). Recently, we obtained the title coordination polymer, which was synthesized under hydrothermal conditions.

In the title compound (Fig. 1), two of the benzimidazole-5,6-dicarboxylate ligands are protonated at the imidazole groups. Each Gd^III ion is eight-coordinated by six O atoms one N atom from five ligands and one water molecule. The coordination geometry can be described as distorted bicapped trigonal prismatic, with Gd—O distances and O—Gd—O angles ranging from 2.267 (2) to 2.539 (2) Å (Table 1) and 52.14 (7) to 156.82 (8)°, respectively. The benzimidazole-5,6-dicarboxylate ligands acting as bridging ligands link the Gd^III centers into a layer parallel to the (0 0 1) plane. O—H···O and N—H···O hydrogen bonds (Table 2) connect the layers into a three-dimensional supramolecular motif (Fig. 2). Within the layer, the π–π stacking interactions between neighboring imidazole and benzene rings [centroid–centroid distances = 3.629 (3), 3.755 (4), 3.656 (3) and 3.606 (3) Å] enhance the stability of the crystal structure.

Related literature top

For related structures, see: Gao et al. (2008); Lo et al. (2007); Wei et al. (2008); Yao et al. (2008).

Experimental top

A mixture of Gd₂O₃ (0.363 g, 1 mmol), benzimidazole-5,6-dicarboxylic acid (0.206 g, 1 mmol), water (10 ml) in the presence of HClO₄ (0.039 g, 0.385 mmol) was stirred vigorously for 30 min and then sealed in a Teflon-lined stainless-steel autoclave (20 ml capacity). The autoclave was heated and maintained at 433 K for 3 d, and then cooled to room temperature at 5 K h^-1. The colorless block crystals were obtained.

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: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are shown at the 50% probability level. H atoms have been omitted for clarity. [Symmetry codes: (i) -x, -1/2+y, 1/2-z; (ii) -x, 1/2+y, 1/2-z; (iii) 1-x, -1/2+y, 1/2-z; (iv) 1-x, 1/2+y, 1/2-z.]
	Fig. 2. A view of the three-dimensional supramolecular network. Hydrogen bonds are shown as dashed lines.

Poly[diaquabis(µ₃-1H-benzimidazole-5,6-dicarboxylato- κ⁴N³:O⁵,O^5':O⁶)bis(µ₂- 1H,3H-benzimidazolium-5,6-dicarboxylato- κ³O⁵,O^5':O⁶)digadolinium(III)] top

Crystal data top

[Gd₂(C₉H₄N₂O₄)₂(C₉H₅N₂O₄)₂(H₂O)₂]	F(000) = 2264
M_r = 1169.12	D_x = 2.198 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7234 reflections
a = 18.7856 (11) Å	θ = 2.6–28.2°
b = 12.7745 (7) Å	µ = 3.82 mm⁻¹
c = 15.4776 (9) Å	T = 296 K
β = 108.010 (1)°	Block, colorless
V = 3532.3 (3) Å³	0.25 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	6338 independent reflections
Radiation source: fine-focus sealed tube	5929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→22
T_min = 0.448, T_max = 0.501	k = −15→15
24827 measured reflections	l = −18→18

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.021P)² + 3.3986P] where P = (F_o² + 2F_c²)/3
6338 reflections	(Δ/σ)_max = 0.002
595 parameters	Δρ_max = 0.63 e Å⁻³
13 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Gd₂(C₉H₄N₂O₄)₂(C₉H₅N₂O₄)₂(H₂O)₂]	V = 3532.3 (3) Å³
M_r = 1169.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.7856 (11) Å	µ = 3.82 mm⁻¹
b = 12.7745 (7) Å	T = 296 K
c = 15.4776 (9) Å	0.25 × 0.24 × 0.21 mm
β = 108.010 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6338 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5929 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.501	R_int = 0.027
24827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	13 restraints
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.63 e Å⁻³
6338 reflections	Δρ_min = −0.55 e Å⁻³
595 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Gd1	0.028568 (8)	0.296570 (11)	0.225244 (9)	0.01343 (5)
Gd2	0.524307 (8)	−0.054993 (10)	0.209686 (9)	0.01317 (5)
N6	0.10953 (14)	0.1586 (2)	0.17264 (18)	0.0208 (6)
N5	0.12241 (15)	0.0250 (2)	0.08627 (19)	0.0251 (6)
H5A	0.111 (2)	−0.029 (3)	0.056 (2)	0.030*
C23	0.07832 (18)	0.0751 (2)	0.1265 (2)	0.0218 (7)
H23	0.0302	0.0529	0.1222	0.026*
C25	0.24026 (17)	0.2316 (2)	0.1949 (2)	0.0220 (7)
H25	0.2367	0.2863	0.2331	0.026*
C21	0.25303 (17)	0.0637 (2)	0.0817 (2)	0.0215 (7)
H21	0.2569	0.0077	0.0449	0.026*
C24	0.18074 (16)	0.1631 (2)	0.1607 (2)	0.0181 (6)
C22	0.18850 (17)	0.0794 (2)	0.1059 (2)	0.0197 (6)
C20	0.31133 (16)	0.1340 (2)	0.11398 (19)	0.0166 (6)
C26	0.30518 (17)	0.2172 (2)	0.1711 (2)	0.0178 (6)
N3	0.36219 (16)	0.1575 (2)	0.4264 (2)	0.0312 (7)
H3A	0.375 (2)	0.212 (3)	0.453 (3)	0.037*
C13	0.28840 (17)	0.0294 (2)	0.3540 (2)	0.0199 (7)
N4	0.35934 (15)	0.0200 (2)	0.3445 (2)	0.0256 (6)
H4A	0.372 (2)	−0.029 (3)	0.316 (2)	0.031*
C15	0.29033 (17)	0.1190 (2)	0.4058 (2)	0.0195 (6)
C14	0.40105 (19)	0.0970 (3)	0.3890 (2)	0.0334 (8)
H14	0.4511	0.1073	0.3934	0.040*
C27	0.36712 (17)	0.2947 (2)	0.2069 (2)	0.0207 (7)
C19	0.38033 (17)	0.1168 (2)	0.0861 (2)	0.0181 (6)
O11	0.41746 (14)	0.30726 (19)	0.17120 (17)	0.0342 (6)
O10	0.37957 (14)	0.15189 (19)	0.01034 (16)	0.0338 (6)
C17	0.16278 (17)	0.0978 (2)	0.39339 (19)	0.0163 (6)
C12	0.22389 (17)	−0.0299 (2)	0.3229 (2)	0.0206 (7)
H12	0.2230	−0.0912	0.2902	0.025*
C16	0.22774 (17)	0.1551 (2)	0.4263 (2)	0.0199 (7)
H16	0.2295	0.2153	0.4607	0.024*
C11	0.16054 (17)	0.0050 (2)	0.3421 (2)	0.0177 (6)
C10	0.08996 (17)	−0.0570 (2)	0.3073 (2)	0.0185 (7)
C18	0.09517 (16)	0.1407 (2)	0.41501 (19)	0.0161 (6)
O8	0.05302 (12)	0.20217 (15)	0.35883 (14)	0.0207 (5)
O7	0.08767 (13)	0.11675 (18)	0.48980 (14)	0.0269 (5)
O5	0.08938 (12)	−0.13723 (16)	0.25772 (16)	0.0266 (5)
O6	0.03295 (12)	−0.03134 (16)	0.32721 (15)	0.0246 (5)
O12	0.36722 (13)	0.3474 (2)	0.27665 (18)	0.0391 (7)
C36	0.40339 (17)	−0.1991 (2)	0.1826 (2)	0.0185 (6)
C33	0.20968 (17)	−0.2999 (2)	0.1476 (2)	0.0192 (6)
C35	0.33593 (17)	−0.2677 (2)	0.1548 (2)	0.0175 (6)
C34	0.27150 (17)	−0.2345 (2)	0.1727 (2)	0.0200 (7)
H34	0.2699	−0.1705	0.2006	0.024*
O16	0.40712 (12)	−0.12307 (16)	0.23682 (15)	0.0246 (5)
O15	0.45572 (13)	−0.21597 (18)	0.15068 (17)	0.0320 (6)
O9	0.43302 (13)	0.06471 (18)	0.13734 (16)	0.0294 (5)
N7	0.14022 (15)	−0.2953 (2)	0.16138 (19)	0.0242 (6)
H7A	0.127 (2)	−0.248 (3)	0.184 (2)	0.029*
C28	0.40817 (17)	−0.4085 (2)	0.09601 (19)	0.0163 (6)
C29	0.33774 (16)	−0.3652 (2)	0.11096 (19)	0.0159 (6)
C32	0.10256 (17)	−0.3811 (3)	0.1275 (2)	0.0233 (7)
H32	0.0547	−0.3968	0.1292	0.028*
O14	0.41716 (12)	−0.40122 (17)	0.02045 (14)	0.0237 (5)
N8	0.14248 (15)	−0.4412 (2)	0.09098 (19)	0.0219 (6)
H8A	0.126 (2)	−0.495 (3)	0.066 (2)	0.026*
C31	0.21123 (16)	−0.3943 (2)	0.1031 (2)	0.0168 (6)
C30	0.27505 (17)	−0.4281 (2)	0.0840 (2)	0.0192 (6)
H30	0.2755	−0.4911	0.0539	0.023*
C1	0.13784 (17)	0.4457 (2)	0.3037 (2)	0.0188 (7)
C2	0.19826 (17)	0.5268 (2)	0.3348 (2)	0.0176 (6)
O2	0.09162 (12)	0.42965 (17)	0.34523 (15)	0.0249 (5)
O1	0.13579 (12)	0.39355 (17)	0.23230 (16)	0.0287 (5)
C8	0.18820 (16)	0.6163 (2)	0.38430 (19)	0.0158 (6)
C7	0.24484 (17)	0.6887 (2)	0.4144 (2)	0.0185 (6)
H7	0.2389	0.7474	0.4471	0.022*
C4	0.32222 (16)	0.5828 (2)	0.3467 (2)	0.0175 (6)
C6	0.31138 (16)	0.6714 (2)	0.39437 (19)	0.0172 (6)
C3	0.26477 (16)	0.5098 (2)	0.3167 (2)	0.0193 (7)
H3	0.2711	0.4506	0.2849	0.023*
N1	0.39340 (14)	0.5868 (2)	0.33531 (17)	0.0190 (5)
N2	0.37599 (15)	0.7294 (2)	0.41004 (18)	0.0217 (6)
H2A	0.385 (2)	0.785 (3)	0.437 (2)	0.026*
C5	0.42138 (17)	0.6759 (2)	0.3735 (2)	0.0208 (7)
H5	0.4685	0.6999	0.3752	0.025*
C9	0.11320 (17)	0.6424 (2)	0.3956 (2)	0.0165 (6)
O4	0.10804 (12)	0.64817 (17)	0.47426 (14)	0.0242 (5)
O13	0.45307 (12)	−0.45613 (17)	0.16304 (14)	0.0247 (5)
O3	0.06077 (11)	0.66278 (16)	0.32358 (14)	0.0203 (5)
O1W	−0.00880 (13)	0.30447 (17)	0.06416 (14)	0.0264 (5)
H1W	0.0184	0.3242	0.0331	0.040*
H2W	−0.0314	0.2519	0.0407	0.040*
O2W	0.51762 (14)	−0.0852 (2)	0.05540 (15)	0.0346 (6)
H3W	0.5544	−0.1080	0.0390	0.052*
H4WA	0.4879	−0.1341	0.0480	0.052*	0.50
H4WB	0.5025	−0.0331	0.0237	0.052*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.01015 (8)	0.01374 (8)	0.01696 (8)	−0.00059 (5)	0.00501 (6)	0.00056 (5)
Gd2	0.01062 (8)	0.01412 (8)	0.01541 (8)	−0.00007 (5)	0.00497 (6)	−0.00022 (5)
N6	0.0124 (13)	0.0236 (14)	0.0276 (14)	−0.0025 (11)	0.0079 (11)	−0.0044 (11)
N5	0.0183 (15)	0.0242 (14)	0.0323 (16)	−0.0062 (12)	0.0071 (12)	−0.0130 (12)
C23	0.0146 (16)	0.0244 (16)	0.0278 (17)	−0.0023 (13)	0.0084 (14)	−0.0022 (13)
C25	0.0183 (17)	0.0186 (15)	0.0294 (17)	−0.0016 (13)	0.0077 (14)	−0.0101 (13)
C21	0.0188 (17)	0.0214 (16)	0.0252 (17)	−0.0004 (13)	0.0080 (14)	−0.0090 (13)
C24	0.0115 (15)	0.0204 (15)	0.0233 (16)	0.0007 (12)	0.0067 (12)	−0.0028 (12)
C22	0.0152 (16)	0.0202 (15)	0.0232 (16)	−0.0026 (12)	0.0052 (13)	−0.0044 (13)
C20	0.0123 (15)	0.0210 (15)	0.0155 (14)	0.0035 (12)	0.0029 (12)	0.0036 (12)
C26	0.0141 (16)	0.0166 (15)	0.0235 (16)	−0.0007 (12)	0.0067 (13)	−0.0023 (12)
N3	0.0182 (16)	0.0345 (17)	0.0425 (18)	−0.0092 (13)	0.0116 (13)	−0.0153 (14)
C13	0.0139 (16)	0.0242 (16)	0.0230 (16)	0.0032 (13)	0.0077 (13)	−0.0003 (13)
N4	0.0163 (15)	0.0311 (16)	0.0328 (16)	0.0008 (12)	0.0126 (12)	−0.0051 (13)
C15	0.0126 (16)	0.0225 (16)	0.0221 (16)	−0.0037 (12)	0.0036 (13)	−0.0016 (13)
C14	0.0156 (18)	0.043 (2)	0.044 (2)	−0.0055 (15)	0.0122 (16)	−0.0085 (17)
C27	0.0136 (16)	0.0185 (15)	0.0300 (18)	0.0017 (12)	0.0068 (14)	−0.0032 (13)
C19	0.0158 (16)	0.0151 (14)	0.0239 (16)	0.0016 (12)	0.0066 (13)	−0.0024 (12)
O11	0.0307 (14)	0.0418 (15)	0.0373 (14)	−0.0177 (11)	0.0211 (12)	−0.0165 (11)
O10	0.0385 (15)	0.0404 (14)	0.0280 (13)	0.0139 (12)	0.0184 (11)	0.0108 (11)
C17	0.0162 (16)	0.0181 (15)	0.0153 (14)	0.0015 (12)	0.0059 (12)	0.0001 (12)
C12	0.0199 (17)	0.0171 (15)	0.0272 (17)	−0.0006 (13)	0.0108 (14)	−0.0045 (13)
C16	0.0193 (17)	0.0188 (15)	0.0232 (16)	−0.0021 (12)	0.0090 (13)	−0.0043 (13)
C11	0.0144 (16)	0.0189 (15)	0.0205 (15)	−0.0001 (12)	0.0065 (13)	0.0003 (12)
C10	0.0178 (17)	0.0150 (15)	0.0227 (16)	−0.0015 (12)	0.0062 (13)	0.0010 (12)
C18	0.0144 (16)	0.0163 (14)	0.0185 (15)	−0.0019 (12)	0.0062 (12)	−0.0018 (12)
O8	0.0202 (12)	0.0202 (11)	0.0221 (11)	0.0063 (9)	0.0070 (9)	0.0064 (9)
O7	0.0288 (13)	0.0343 (13)	0.0225 (12)	0.0150 (10)	0.0151 (10)	0.0088 (10)
O5	0.0197 (12)	0.0208 (11)	0.0433 (14)	−0.0069 (9)	0.0155 (11)	−0.0133 (10)
O6	0.0162 (12)	0.0223 (11)	0.0380 (13)	−0.0038 (9)	0.0124 (10)	−0.0065 (10)
O12	0.0252 (14)	0.0405 (15)	0.0588 (17)	−0.0157 (11)	0.0233 (13)	−0.0302 (13)
C36	0.0173 (17)	0.0195 (15)	0.0186 (15)	−0.0020 (12)	0.0054 (13)	0.0015 (12)
C33	0.0130 (16)	0.0244 (16)	0.0213 (16)	0.0017 (12)	0.0066 (13)	−0.0002 (13)
C35	0.0150 (16)	0.0185 (15)	0.0189 (15)	−0.0016 (12)	0.0053 (13)	−0.0006 (12)
C34	0.0199 (17)	0.0160 (15)	0.0249 (16)	−0.0002 (12)	0.0083 (14)	−0.0042 (12)
O16	0.0219 (12)	0.0203 (11)	0.0351 (13)	−0.0064 (9)	0.0136 (10)	−0.0118 (10)
O15	0.0281 (14)	0.0341 (13)	0.0422 (15)	−0.0139 (11)	0.0232 (12)	−0.0182 (11)
O9	0.0184 (13)	0.0341 (13)	0.0370 (14)	0.0092 (10)	0.0106 (11)	0.0128 (11)
N7	0.0180 (15)	0.0282 (16)	0.0287 (16)	0.0006 (12)	0.0104 (12)	−0.0061 (12)
C28	0.0180 (16)	0.0127 (14)	0.0181 (15)	−0.0019 (12)	0.0052 (13)	−0.0002 (12)
C29	0.0155 (16)	0.0190 (15)	0.0146 (14)	−0.0001 (12)	0.0069 (12)	0.0003 (12)
C32	0.0122 (16)	0.0313 (18)	0.0259 (17)	−0.0018 (13)	0.0053 (13)	0.0008 (14)
O14	0.0258 (13)	0.0289 (12)	0.0184 (11)	0.0076 (10)	0.0097 (10)	0.0039 (9)
N8	0.0121 (14)	0.0244 (15)	0.0276 (15)	−0.0051 (11)	0.0039 (12)	−0.0046 (12)
C31	0.0120 (15)	0.0181 (15)	0.0187 (15)	−0.0029 (12)	0.0024 (12)	0.0000 (12)
C30	0.0177 (17)	0.0180 (15)	0.0216 (16)	−0.0004 (12)	0.0055 (13)	−0.0032 (12)
C1	0.0121 (16)	0.0158 (15)	0.0268 (17)	0.0017 (12)	0.0033 (13)	−0.0022 (12)
C2	0.0141 (16)	0.0158 (15)	0.0229 (16)	0.0003 (12)	0.0057 (13)	0.0001 (12)
O2	0.0235 (13)	0.0260 (12)	0.0282 (12)	−0.0070 (9)	0.0122 (10)	−0.0035 (10)
O1	0.0207 (13)	0.0270 (12)	0.0441 (14)	−0.0100 (10)	0.0186 (11)	−0.0172 (11)
C8	0.0141 (16)	0.0158 (14)	0.0165 (14)	0.0027 (12)	0.0033 (12)	0.0010 (11)
C7	0.0179 (16)	0.0194 (15)	0.0186 (15)	0.0029 (12)	0.0064 (13)	−0.0032 (12)
C4	0.0117 (16)	0.0212 (15)	0.0188 (15)	0.0003 (12)	0.0035 (12)	−0.0029 (12)
C6	0.0144 (16)	0.0192 (15)	0.0166 (15)	−0.0001 (12)	0.0029 (12)	−0.0004 (12)
C3	0.0138 (16)	0.0159 (15)	0.0276 (17)	0.0003 (12)	0.0057 (13)	−0.0060 (12)
N1	0.0104 (13)	0.0228 (13)	0.0229 (13)	−0.0027 (10)	0.0038 (11)	−0.0038 (11)
N2	0.0166 (14)	0.0196 (14)	0.0282 (15)	−0.0033 (11)	0.0060 (12)	−0.0092 (12)
C5	0.0154 (16)	0.0241 (16)	0.0240 (16)	−0.0015 (13)	0.0075 (13)	−0.0015 (13)
C9	0.0161 (16)	0.0110 (14)	0.0235 (16)	0.0036 (11)	0.0077 (13)	0.0013 (12)
O4	0.0261 (13)	0.0288 (12)	0.0214 (11)	0.0088 (10)	0.0128 (10)	0.0055 (9)
O13	0.0208 (12)	0.0322 (13)	0.0224 (12)	0.0071 (10)	0.0084 (10)	0.0112 (10)
O3	0.0131 (11)	0.0248 (11)	0.0218 (11)	0.0054 (9)	0.0038 (9)	0.0013 (9)
O1W	0.0313 (14)	0.0279 (12)	0.0216 (12)	−0.0129 (10)	0.0108 (10)	0.0001 (9)
O2W	0.0307 (14)	0.0532 (16)	0.0215 (12)	−0.0001 (12)	0.0108 (11)	−0.0028 (11)

Geometric parameters (Å, º) top

Gd1—O1	2.338 (2)	C16—H16	0.9300
Gd1—O2	2.526 (2)	C11—C10	1.495 (4)
Gd1—O3ⁱ	2.350 (2)	C10—O6	1.247 (4)
Gd1—O5ⁱⁱ	2.461 (2)	C10—O5	1.278 (4)
Gd1—O6ⁱⁱ	2.499 (2)	C18—O7	1.247 (4)
Gd1—O8	2.314 (2)	C18—O8	1.255 (3)
Gd1—N6	2.617 (3)	C36—O15	1.248 (4)
Gd1—O1W	2.374 (2)	C36—O16	1.271 (4)
Gd2—O9	2.312 (2)	C36—C35	1.491 (4)
Gd2—O11ⁱⁱⁱ	2.539 (2)	C33—C34	1.385 (4)
Gd2—O12ⁱⁱⁱ	2.342 (2)	C33—N7	1.387 (4)
Gd2—O13^iv	2.267 (2)	C33—C31	1.393 (4)
Gd2—O15	2.449 (2)	C35—C34	1.388 (4)
Gd2—O16	2.520 (2)	C35—C29	1.424 (4)
Gd2—N1ⁱⁱⁱ	2.612 (3)	C34—H34	0.9300
Gd2—O2W	2.384 (2)	N7—C32	1.323 (4)
N6—C23	1.316 (4)	N7—H7A	0.77 (4)
N6—C24	1.407 (4)	C28—O14	1.236 (4)
N5—C23	1.343 (4)	C28—O13	1.272 (4)
N5—C22	1.372 (4)	C28—C29	1.516 (4)
N5—H5A	0.83 (4)	C29—C30	1.380 (4)
C23—H23	0.9300	C32—N8	1.316 (4)
C25—C24	1.389 (4)	C32—H32	0.9300
C25—C26	1.391 (4)	N8—C31	1.382 (4)
C25—H25	0.9300	N8—H8A	0.80 (4)
C21—C20	1.385 (4)	C31—C30	1.390 (4)
C21—C22	1.390 (4)	C30—H30	0.9300
C21—H21	0.9300	C1—O2	1.247 (4)
C24—C22	1.400 (4)	C1—O1	1.281 (4)
C20—C26	1.411 (4)	C1—C2	1.502 (4)
C20—C19	1.504 (4)	C2—C3	1.380 (4)
C26—C27	1.498 (4)	C2—C8	1.420 (4)
N3—C14	1.314 (4)	C8—C7	1.378 (4)
N3—C15	1.378 (4)	C8—C9	1.510 (4)
N3—H3A	0.81 (4)	C7—C6	1.396 (4)
C13—C12	1.383 (4)	C7—H7	0.9300
C13—N4	1.391 (4)	C4—C3	1.392 (4)
C13—C15	1.392 (4)	C4—C6	1.400 (4)
N4—C14	1.313 (4)	C4—N1	1.403 (4)
N4—H4A	0.84 (4)	C6—N2	1.378 (4)
C15—C16	1.387 (4)	C3—H3	0.9300
C14—H14	0.9300	N1—C5	1.315 (4)
C27—O11	1.245 (4)	N2—C5	1.345 (4)
C27—O12	1.270 (4)	N2—H2A	0.82 (4)
C19—O10	1.251 (4)	C5—H5	0.9300
C19—O9	1.251 (4)	C9—O4	1.252 (4)
O11—Gd2^iv	2.539 (2)	C9—O3	1.266 (4)
C17—C16	1.378 (4)	O1W—H1W	0.84
C17—C11	1.420 (4)	O1W—H2W	0.82
C17—C18	1.513 (4)	O2W—H3W	0.86
C12—C11	1.386 (4)	O2W—H4WA	0.82
C12—H12	0.9300	O2W—H4WB	0.82

O8—Gd1—O1	107.71 (8)	N3—C14—H14	124.8
O8—Gd1—O3ⁱ	80.39 (7)	O11—C27—O12	120.5 (3)
O1—Gd1—O3ⁱ	156.84 (7)	O11—C27—C26	122.0 (3)
O8—Gd1—O1W	150.83 (7)	O12—C27—C26	117.5 (3)
O1—Gd1—O1W	89.84 (8)	O11—C27—Gd2^iv	64.70 (17)
O3ⁱ—Gd1—O1W	75.13 (7)	O12—C27—Gd2^iv	55.80 (16)
O8—Gd1—O5ⁱⁱ	91.14 (7)	C26—C27—Gd2^iv	173.3 (2)
O1—Gd1—O5ⁱⁱ	127.16 (7)	O10—C19—O9	124.2 (3)
O3ⁱ—Gd1—O5ⁱⁱ	72.98 (7)	O10—C19—C20	117.1 (3)
O1W—Gd1—O5ⁱⁱ	96.56 (8)	O9—C19—C20	118.6 (3)
O8—Gd1—O6ⁱⁱ	133.85 (7)	C27—O11—Gd2^iv	88.98 (18)
O1—Gd1—O6ⁱⁱ	81.62 (8)	C16—C17—C11	121.3 (3)
O3ⁱ—Gd1—O6ⁱⁱ	108.82 (7)	C16—C17—C18	115.8 (3)
O1W—Gd1—O6ⁱⁱ	70.40 (8)	C11—C17—C18	123.0 (3)
O5ⁱⁱ—Gd1—O6ⁱⁱ	52.51 (7)	C13—C12—C11	117.9 (3)
O8—Gd1—O2	77.02 (7)	C13—C12—H12	121.1
O1—Gd1—O2	53.69 (7)	C11—C12—H12	121.1
O3ⁱ—Gd1—O2	148.38 (7)	C17—C16—C15	117.1 (3)
O1W—Gd1—O2	131.50 (7)	C17—C16—H16	121.4
O5ⁱⁱ—Gd1—O2	85.58 (8)	C15—C16—H16	121.4
O6ⁱⁱ—Gd1—O2	73.23 (7)	C12—C11—C17	120.6 (3)
O8—Gd1—N6	87.31 (8)	C12—C11—C10	118.5 (3)
O1—Gd1—N6	78.24 (8)	C17—C11—C10	120.9 (3)
O3ⁱ—Gd1—N6	80.57 (8)	O6—C10—O5	120.7 (3)
O1W—Gd1—N6	73.35 (8)	O6—C10—C11	120.3 (3)
O5ⁱⁱ—Gd1—N6	153.38 (8)	O5—C10—C11	118.9 (3)
O6ⁱⁱ—Gd1—N6	138.26 (8)	O6—C10—Gd1ⁱ	61.93 (15)
O2—Gd1—N6	119.76 (8)	O5—C10—Gd1ⁱ	60.23 (15)
O8—Gd1—C10ⁱⁱ	115.53 (8)	C11—C10—Gd1ⁱ	167.3 (2)
O1—Gd1—C10ⁱⁱ	106.09 (8)	O7—C18—O8	124.7 (3)
O3ⁱ—Gd1—C10ⁱⁱ	88.80 (8)	O7—C18—C17	117.4 (3)
O1W—Gd1—C10ⁱⁱ	79.89 (8)	O8—C18—C17	117.8 (3)
O5ⁱⁱ—Gd1—C10ⁱⁱ	26.78 (8)	C18—O8—Gd1	148.6 (2)
O6ⁱⁱ—Gd1—C10ⁱⁱ	26.11 (8)	C10—O5—Gd1ⁱ	92.99 (18)
O2—Gd1—C10ⁱⁱ	81.39 (8)	C10—O6—Gd1ⁱ	91.96 (17)
N6—Gd1—C10ⁱⁱ	152.92 (8)	C27—O12—Gd2^iv	97.54 (19)
O13^iv—Gd2—O9	87.94 (8)	O15—C36—O16	120.3 (3)
O13^iv—Gd2—O12ⁱⁱⁱ	107.11 (9)	O15—C36—C35	119.2 (3)
O9—Gd2—O12ⁱⁱⁱ	152.90 (8)	O16—C36—C35	120.5 (3)
O13^iv—Gd2—O2W	153.97 (8)	C34—C33—N7	132.7 (3)
O9—Gd2—O2W	79.66 (9)	C34—C33—C31	121.1 (3)
O12ⁱⁱⁱ—Gd2—O2W	77.24 (9)	N7—C33—C31	106.1 (3)
O13^iv—Gd2—O15	136.70 (8)	C34—C35—C29	120.9 (3)
O9—Gd2—O15	98.56 (8)	C34—C35—C36	118.6 (3)
O12ⁱⁱⁱ—Gd2—O15	85.94 (9)	C29—C35—C36	120.6 (3)
O2W—Gd2—O15	68.38 (8)	C33—C34—C35	117.8 (3)
O13^iv—Gd2—O16	89.20 (7)	C33—C34—H34	121.1
O9—Gd2—O16	75.74 (8)	C35—C34—H34	121.1
O12ⁱⁱⁱ—Gd2—O16	125.56 (8)	C36—O16—Gd2	91.50 (18)
O2W—Gd2—O16	109.44 (8)	C36—O15—Gd2	95.47 (18)
O15—Gd2—O16	52.14 (7)	C19—O9—Gd2	168.9 (2)
O13^iv—Gd2—O11ⁱⁱⁱ	80.34 (8)	C32—N7—C33	108.5 (3)
O9—Gd2—O11ⁱⁱⁱ	153.99 (8)	C32—N7—H7A	129 (3)
O12ⁱⁱⁱ—Gd2—O11ⁱⁱⁱ	52.97 (8)	C33—N7—H7A	123 (3)
O2W—Gd2—O11ⁱⁱⁱ	119.51 (8)	O14—C28—O13	123.9 (3)
O15—Gd2—O11ⁱⁱⁱ	75.38 (9)	O14—C28—C29	119.9 (3)
O16—Gd2—O11ⁱⁱⁱ	80.92 (8)	O13—C28—C29	116.1 (3)
O13^iv—Gd2—N1ⁱⁱⁱ	82.99 (8)	C30—C29—C35	120.7 (3)
O9—Gd2—N1ⁱⁱⁱ	79.84 (8)	C30—C29—C28	116.4 (3)
O12ⁱⁱⁱ—Gd2—N1ⁱⁱⁱ	79.83 (8)	C35—C29—C28	122.8 (3)
O2W—Gd2—N1ⁱⁱⁱ	72.39 (8)	N8—C32—N7	110.4 (3)
O15—Gd2—N1ⁱⁱⁱ	140.32 (8)	N8—C32—H32	124.8
O16—Gd2—N1ⁱⁱⁱ	154.59 (7)	N7—C32—H32	124.8
O11ⁱⁱⁱ—Gd2—N1ⁱⁱⁱ	121.11 (8)	C32—N8—C31	108.8 (3)
O13^iv—Gd2—C27ⁱⁱⁱ	93.85 (9)	C32—N8—H8A	122 (3)
O9—Gd2—C27ⁱⁱⁱ	178.09 (9)	C31—N8—H8A	130 (3)
O12ⁱⁱⁱ—Gd2—C27ⁱⁱⁱ	26.65 (9)	N8—C31—C30	131.9 (3)
O2W—Gd2—C27ⁱⁱⁱ	98.94 (9)	N8—C31—C33	106.3 (3)
O15—Gd2—C27ⁱⁱⁱ	79.68 (9)	C30—C31—C33	121.7 (3)
O16—Gd2—C27ⁱⁱⁱ	103.62 (8)	C29—C30—C31	117.8 (3)
O11ⁱⁱⁱ—Gd2—C27ⁱⁱⁱ	26.32 (8)	C29—C30—H30	121.1
N1ⁱⁱⁱ—Gd2—C27ⁱⁱⁱ	101.01 (8)	C31—C30—H30	121.1
C23—N6—C24	104.1 (3)	O2—C1—O1	121.3 (3)
C23—N6—Gd1	120.7 (2)	O2—C1—C2	121.7 (3)
C24—N6—Gd1	132.91 (19)	O1—C1—C2	117.0 (3)
C23—N5—C22	107.6 (3)	C3—C2—C8	121.1 (3)
C23—N5—H5A	126 (3)	C3—C2—C1	117.9 (3)
C22—N5—H5A	127 (3)	C8—C2—C1	121.0 (3)
N6—C23—N5	113.7 (3)	C1—O2—Gd1	88.55 (18)
N6—C23—H23	123.1	C1—O1—Gd1	96.42 (18)
N5—C23—H23	123.1	C7—C8—C2	120.3 (3)
C24—C25—C26	119.0 (3)	C7—C8—C9	117.6 (3)
C24—C25—H25	120.5	C2—C8—C9	121.6 (3)
C26—C25—H25	120.5	C8—C7—C6	118.0 (3)
C20—C21—C22	117.9 (3)	C8—C7—H7	121.0
C20—C21—H21	121.1	C6—C7—H7	121.0
C22—C21—H21	121.1	C3—C4—C6	119.5 (3)
C25—C24—C22	119.3 (3)	C3—C4—N1	130.8 (3)
C25—C24—N6	131.4 (3)	C6—C4—N1	109.6 (3)
C22—C24—N6	109.2 (3)	N2—C6—C7	132.6 (3)
N5—C22—C21	132.2 (3)	N2—C6—C4	105.3 (3)
N5—C22—C24	105.3 (3)	C7—C6—C4	122.1 (3)
C21—C22—C24	122.4 (3)	C2—C3—C4	118.9 (3)
C21—C20—C26	120.4 (3)	C2—C3—H3	120.5
C21—C20—C19	117.2 (3)	C4—C3—H3	120.5
C26—C20—C19	122.3 (3)	C5—N1—C4	103.9 (2)
C25—C26—C20	120.9 (3)	C5—N1—Gd2^iv	122.2 (2)
C25—C26—C27	117.3 (3)	C4—N1—Gd2^iv	132.34 (19)
C20—C26—C27	121.7 (3)	C5—N2—C6	106.9 (3)
C14—N3—C15	109.0 (3)	C5—N2—H2A	127 (3)
C14—N3—H3A	128 (3)	C6—N2—H2A	126 (3)
C15—N3—H3A	123 (3)	N1—C5—N2	114.3 (3)
C12—C13—N4	132.9 (3)	N1—C5—H5	122.9
C12—C13—C15	121.0 (3)	N2—C5—H5	122.9
N4—C13—C15	106.1 (3)	O4—C9—O3	124.8 (3)
C14—N4—C13	108.4 (3)	O4—C9—C8	118.8 (3)
C14—N4—H4A	127 (3)	O3—C9—C8	116.3 (3)
C13—N4—H4A	124 (3)	C28—O13—Gd2ⁱⁱⁱ	151.0 (2)
N3—C15—C16	131.9 (3)	C9—O3—Gd1ⁱⁱ	135.77 (18)
N3—C15—C13	106.0 (3)	H1W—O1W—H2W	108
C16—C15—C13	122.1 (3)	H3W—O2W—H4WA	106
N4—C14—N3	110.4 (3)	H3W—O2W—H4WB	105
N4—C14—H14	124.8

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7^v	0.84	1.80	2.629 (3)	167
O1W—H2W···O4ⁱ	0.82	1.92	2.670 (3)	153
O2W—H3W···O10^vi	0.86	1.74	2.590 (3)	172
O2W—H4WA···O15	0.82	2.14	2.716 (5)	127
O2W—H4WB···O2W^vi	0.82	1.91	2.723 (4)	170
N2—H2A···O14^vii	0.82 (4)	1.94 (4)	2.742 (3)	169 (3)
N3—H3A···O10^vii	0.81 (4)	1.94 (4)	2.731 (4)	166 (4)
N4—H4A···O16	0.84 (4)	1.97 (4)	2.801 (4)	170 (4)
N5—H5A···O4^v	0.83 (4)	1.96 (4)	2.772 (3)	165 (4)
N7—H7A···O5	0.77 (4)	2.08 (4)	2.845 (3)	171 (4)
N8—H8A···O7^viii	0.80 (4)	1.95 (4)	2.747 (3)	172 (4)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, −y, −z; (vii) x, −y+1/2, z+1/2; (viii) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Gd₂(C₉H₄N₂O₄)₂(C₉H₅N₂O₄)₂(H₂O)₂]
M_r	1169.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.7856 (11), 12.7745 (7), 15.4776 (9)
β (°)	108.010 (1)
V (Å³)	3532.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.82
Crystal size (mm)	0.25 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.448, 0.501
No. of measured, independent and observed [I > 2σ(I)] reflections	24827, 6338, 5929
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.049, 1.08
No. of reflections	6338
No. of parameters	595
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.55

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Gd1—O1	2.338 (2)	Gd2—O9	2.312 (2)
Gd1—O2	2.526 (2)	Gd2—O11ⁱⁱⁱ	2.539 (2)
Gd1—O3ⁱ	2.350 (2)	Gd2—O12ⁱⁱⁱ	2.342 (2)
Gd1—O5ⁱⁱ	2.461 (2)	Gd2—O13^iv	2.267 (2)
Gd1—O6ⁱⁱ	2.499 (2)	Gd2—O15	2.449 (2)
Gd1—O8	2.314 (2)	Gd2—O16	2.520 (2)
Gd1—N6	2.617 (3)	Gd2—N1ⁱⁱⁱ	2.612 (3)
Gd1—O1W	2.374 (2)	Gd2—O2W	2.384 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7^v	0.84	1.80	2.629 (3)	167
O1W—H2W···O4ⁱ	0.82	1.92	2.670 (3)	153
O2W—H3W···O10^vi	0.86	1.74	2.590 (3)	172
O2W—H4WA···O15	0.82	2.14	2.716 (5)	127
O2W—H4WB···O2W^vi	0.82	1.91	2.723 (4)	170
N2—H2A···O14^vii	0.82 (4)	1.94 (4)	2.742 (3)	169 (3)
N3—H3A···O10^vii	0.81 (4)	1.94 (4)	2.731 (4)	166 (4)
N4—H4A···O16	0.84 (4)	1.97 (4)	2.801 (4)	170 (4)
N5—H5A···O4^v	0.83 (4)	1.96 (4)	2.772 (3)	165 (4)
N7—H7A···O5	0.77 (4)	2.08 (4)	2.845 (3)	171 (4)
N8—H8A···O7^viii	0.80 (4)	1.95 (4)	2.747 (3)	172 (4)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, −y, −z; (vii) x, −y+1/2, z+1/2; (viii) x, −y−1/2, z−1/2.

Acknowledgements

The authors acknowledge the Students' Extracurricular Scientific Research Projects of South China Normal University and the Key Laboratory of Electrochemical Technology of Energy Storage and Power Generation in Guangdong Universities for supporting this work.

References

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