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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1566–m1567.
Published online 2009 November 14. doi:  10.1107/S1600536809046819
PMCID: PMC2971816

Poly[diaqua­bis(μ3-1H-benzimidazole-5,6-dicarboxyl­ato-κ4 N 3:O 5,O 5′:O 6)bis­(μ2-1H,3H-benzimidazolium-5,6-dicarboxyl­ato-κ3 O 5,O 5′:O 6)digadolinium(III)]

Abstract

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 GdIII 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 GdIII 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 [triangle]); Lo et al. (2007 [triangle]); Wei et al. (2008 [triangle]); Yao et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1566-scheme1.jpg

Experimental

Crystal data

  • [Gd2(C9H4N2O4)2(C9H5N2O4)2(H2O)2]
  • M r = 1169.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1566-efi5.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.020
  • wR(F 2) = 0.049
  • S = 1.08
  • 6338 reflections
  • 595 parameters
  • 13 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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 GdIII 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 GdIII 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.

Experimental

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.

Refinement

Water H atoms were tentatively located in difference Fourier maps and fixed in refinements, with Uiso(H) = 1.5Ueq(O). One of the H atoms of O2W is disordered over two sites (O4WA and O4WB), each with an occupancy factor of 0.5. H atoms on N atoms were tentatively located in difference Fourier maps and refined with distance restraints of N—H = 0.82 (1) Å and with Uiso(H) = 1.2Ueq(N). H atoms attached to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Figures

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, ...
Fig. 2.
A view of the three-dimensional supramolecular network. Hydrogen bonds are shown as dashed lines.

Crystal data

[Gd2(C9H4N2O4)2(C9H5N2O4)2(H2O)2]F(000) = 2264
Mr = 1169.12Dx = 2.198 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7234 reflections
a = 18.7856 (11) Åθ = 2.6–28.2°
b = 12.7745 (7) ŵ = 3.82 mm1
c = 15.4776 (9) ÅT = 296 K
β = 108.010 (1)°Block, colorless
V = 3532.3 (3) Å30.25 × 0.24 × 0.21 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer6338 independent reflections
Radiation source: fine-focus sealed tube5929 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −21→22
Tmin = 0.448, Tmax = 0.501k = −15→15
24827 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.021P)2 + 3.3986P] where P = (Fo2 + 2Fc2)/3
6338 reflections(Δ/σ)max = 0.002
595 parametersΔρmax = 0.63 e Å3
13 restraintsΔρmin = −0.55 e Å3

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

xyzUiso*/UeqOcc. (<1)
Gd10.028568 (8)0.296570 (11)0.225244 (9)0.01343 (5)
Gd20.524307 (8)−0.054993 (10)0.209686 (9)0.01317 (5)
N60.10953 (14)0.1586 (2)0.17264 (18)0.0208 (6)
N50.12241 (15)0.0250 (2)0.08627 (19)0.0251 (6)
H5A0.111 (2)−0.029 (3)0.056 (2)0.030*
C230.07832 (18)0.0751 (2)0.1265 (2)0.0218 (7)
H230.03020.05290.12220.026*
C250.24026 (17)0.2316 (2)0.1949 (2)0.0220 (7)
H250.23670.28630.23310.026*
C210.25303 (17)0.0637 (2)0.0817 (2)0.0215 (7)
H210.25690.00770.04490.026*
C240.18074 (16)0.1631 (2)0.1607 (2)0.0181 (6)
C220.18850 (17)0.0794 (2)0.1059 (2)0.0197 (6)
C200.31133 (16)0.1340 (2)0.11398 (19)0.0166 (6)
C260.30518 (17)0.2172 (2)0.1711 (2)0.0178 (6)
N30.36219 (16)0.1575 (2)0.4264 (2)0.0312 (7)
H3A0.375 (2)0.212 (3)0.453 (3)0.037*
C130.28840 (17)0.0294 (2)0.3540 (2)0.0199 (7)
N40.35934 (15)0.0200 (2)0.3445 (2)0.0256 (6)
H4A0.372 (2)−0.029 (3)0.316 (2)0.031*
C150.29033 (17)0.1190 (2)0.4058 (2)0.0195 (6)
C140.40105 (19)0.0970 (3)0.3890 (2)0.0334 (8)
H140.45110.10730.39340.040*
C270.36712 (17)0.2947 (2)0.2069 (2)0.0207 (7)
C190.38033 (17)0.1168 (2)0.0861 (2)0.0181 (6)
O110.41746 (14)0.30726 (19)0.17120 (17)0.0342 (6)
O100.37957 (14)0.15189 (19)0.01034 (16)0.0338 (6)
C170.16278 (17)0.0978 (2)0.39339 (19)0.0163 (6)
C120.22389 (17)−0.0299 (2)0.3229 (2)0.0206 (7)
H120.2230−0.09120.29020.025*
C160.22774 (17)0.1551 (2)0.4263 (2)0.0199 (7)
H160.22950.21530.46070.024*
C110.16054 (17)0.0050 (2)0.3421 (2)0.0177 (6)
C100.08996 (17)−0.0570 (2)0.3073 (2)0.0185 (7)
C180.09517 (16)0.1407 (2)0.41501 (19)0.0161 (6)
O80.05302 (12)0.20217 (15)0.35883 (14)0.0207 (5)
O70.08767 (13)0.11675 (18)0.48980 (14)0.0269 (5)
O50.08938 (12)−0.13723 (16)0.25772 (16)0.0266 (5)
O60.03295 (12)−0.03134 (16)0.32721 (15)0.0246 (5)
O120.36722 (13)0.3474 (2)0.27665 (18)0.0391 (7)
C360.40339 (17)−0.1991 (2)0.1826 (2)0.0185 (6)
C330.20968 (17)−0.2999 (2)0.1476 (2)0.0192 (6)
C350.33593 (17)−0.2677 (2)0.1548 (2)0.0175 (6)
C340.27150 (17)−0.2345 (2)0.1727 (2)0.0200 (7)
H340.2699−0.17050.20060.024*
O160.40712 (12)−0.12307 (16)0.23682 (15)0.0246 (5)
O150.45572 (13)−0.21597 (18)0.15068 (17)0.0320 (6)
O90.43302 (13)0.06471 (18)0.13734 (16)0.0294 (5)
N70.14022 (15)−0.2953 (2)0.16138 (19)0.0242 (6)
H7A0.127 (2)−0.248 (3)0.184 (2)0.029*
C280.40817 (17)−0.4085 (2)0.09601 (19)0.0163 (6)
C290.33774 (16)−0.3652 (2)0.11096 (19)0.0159 (6)
C320.10256 (17)−0.3811 (3)0.1275 (2)0.0233 (7)
H320.0547−0.39680.12920.028*
O140.41716 (12)−0.40122 (17)0.02045 (14)0.0237 (5)
N80.14248 (15)−0.4412 (2)0.09098 (19)0.0219 (6)
H8A0.126 (2)−0.495 (3)0.066 (2)0.026*
C310.21123 (16)−0.3943 (2)0.1031 (2)0.0168 (6)
C300.27505 (17)−0.4281 (2)0.0840 (2)0.0192 (6)
H300.2755−0.49110.05390.023*
C10.13784 (17)0.4457 (2)0.3037 (2)0.0188 (7)
C20.19826 (17)0.5268 (2)0.3348 (2)0.0176 (6)
O20.09162 (12)0.42965 (17)0.34523 (15)0.0249 (5)
O10.13579 (12)0.39355 (17)0.23230 (16)0.0287 (5)
C80.18820 (16)0.6163 (2)0.38430 (19)0.0158 (6)
C70.24484 (17)0.6887 (2)0.4144 (2)0.0185 (6)
H70.23890.74740.44710.022*
C40.32222 (16)0.5828 (2)0.3467 (2)0.0175 (6)
C60.31138 (16)0.6714 (2)0.39437 (19)0.0172 (6)
C30.26477 (16)0.5098 (2)0.3167 (2)0.0193 (7)
H30.27110.45060.28490.023*
N10.39340 (14)0.5868 (2)0.33531 (17)0.0190 (5)
N20.37599 (15)0.7294 (2)0.41004 (18)0.0217 (6)
H2A0.385 (2)0.785 (3)0.437 (2)0.026*
C50.42138 (17)0.6759 (2)0.3735 (2)0.0208 (7)
H50.46850.69990.37520.025*
C90.11320 (17)0.6424 (2)0.3956 (2)0.0165 (6)
O40.10804 (12)0.64817 (17)0.47426 (14)0.0242 (5)
O130.45307 (12)−0.45613 (17)0.16304 (14)0.0247 (5)
O30.06077 (11)0.66278 (16)0.32358 (14)0.0203 (5)
O1W−0.00880 (13)0.30447 (17)0.06416 (14)0.0264 (5)
H1W0.01840.32420.03310.040*
H2W−0.03140.25190.04070.040*
O2W0.51762 (14)−0.0852 (2)0.05540 (15)0.0346 (6)
H3W0.5544−0.10800.03900.052*
H4WA0.4879−0.13410.04800.052*0.50
H4WB0.5025−0.03310.02370.052*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Gd10.01015 (8)0.01374 (8)0.01696 (8)−0.00059 (5)0.00501 (6)0.00056 (5)
Gd20.01062 (8)0.01412 (8)0.01541 (8)−0.00007 (5)0.00497 (6)−0.00022 (5)
N60.0124 (13)0.0236 (14)0.0276 (14)−0.0025 (11)0.0079 (11)−0.0044 (11)
N50.0183 (15)0.0242 (14)0.0323 (16)−0.0062 (12)0.0071 (12)−0.0130 (12)
C230.0146 (16)0.0244 (16)0.0278 (17)−0.0023 (13)0.0084 (14)−0.0022 (13)
C250.0183 (17)0.0186 (15)0.0294 (17)−0.0016 (13)0.0077 (14)−0.0101 (13)
C210.0188 (17)0.0214 (16)0.0252 (17)−0.0004 (13)0.0080 (14)−0.0090 (13)
C240.0115 (15)0.0204 (15)0.0233 (16)0.0007 (12)0.0067 (12)−0.0028 (12)
C220.0152 (16)0.0202 (15)0.0232 (16)−0.0026 (12)0.0052 (13)−0.0044 (13)
C200.0123 (15)0.0210 (15)0.0155 (14)0.0035 (12)0.0029 (12)0.0036 (12)
C260.0141 (16)0.0166 (15)0.0235 (16)−0.0007 (12)0.0067 (13)−0.0023 (12)
N30.0182 (16)0.0345 (17)0.0425 (18)−0.0092 (13)0.0116 (13)−0.0153 (14)
C130.0139 (16)0.0242 (16)0.0230 (16)0.0032 (13)0.0077 (13)−0.0003 (13)
N40.0163 (15)0.0311 (16)0.0328 (16)0.0008 (12)0.0126 (12)−0.0051 (13)
C150.0126 (16)0.0225 (16)0.0221 (16)−0.0037 (12)0.0036 (13)−0.0016 (13)
C140.0156 (18)0.043 (2)0.044 (2)−0.0055 (15)0.0122 (16)−0.0085 (17)
C270.0136 (16)0.0185 (15)0.0300 (18)0.0017 (12)0.0068 (14)−0.0032 (13)
C190.0158 (16)0.0151 (14)0.0239 (16)0.0016 (12)0.0066 (13)−0.0024 (12)
O110.0307 (14)0.0418 (15)0.0373 (14)−0.0177 (11)0.0211 (12)−0.0165 (11)
O100.0385 (15)0.0404 (14)0.0280 (13)0.0139 (12)0.0184 (11)0.0108 (11)
C170.0162 (16)0.0181 (15)0.0153 (14)0.0015 (12)0.0059 (12)0.0001 (12)
C120.0199 (17)0.0171 (15)0.0272 (17)−0.0006 (13)0.0108 (14)−0.0045 (13)
C160.0193 (17)0.0188 (15)0.0232 (16)−0.0021 (12)0.0090 (13)−0.0043 (13)
C110.0144 (16)0.0189 (15)0.0205 (15)−0.0001 (12)0.0065 (13)0.0003 (12)
C100.0178 (17)0.0150 (15)0.0227 (16)−0.0015 (12)0.0062 (13)0.0010 (12)
C180.0144 (16)0.0163 (14)0.0185 (15)−0.0019 (12)0.0062 (12)−0.0018 (12)
O80.0202 (12)0.0202 (11)0.0221 (11)0.0063 (9)0.0070 (9)0.0064 (9)
O70.0288 (13)0.0343 (13)0.0225 (12)0.0150 (10)0.0151 (10)0.0088 (10)
O50.0197 (12)0.0208 (11)0.0433 (14)−0.0069 (9)0.0155 (11)−0.0133 (10)
O60.0162 (12)0.0223 (11)0.0380 (13)−0.0038 (9)0.0124 (10)−0.0065 (10)
O120.0252 (14)0.0405 (15)0.0588 (17)−0.0157 (11)0.0233 (13)−0.0302 (13)
C360.0173 (17)0.0195 (15)0.0186 (15)−0.0020 (12)0.0054 (13)0.0015 (12)
C330.0130 (16)0.0244 (16)0.0213 (16)0.0017 (12)0.0066 (13)−0.0002 (13)
C350.0150 (16)0.0185 (15)0.0189 (15)−0.0016 (12)0.0053 (13)−0.0006 (12)
C340.0199 (17)0.0160 (15)0.0249 (16)−0.0002 (12)0.0083 (14)−0.0042 (12)
O160.0219 (12)0.0203 (11)0.0351 (13)−0.0064 (9)0.0136 (10)−0.0118 (10)
O150.0281 (14)0.0341 (13)0.0422 (15)−0.0139 (11)0.0232 (12)−0.0182 (11)
O90.0184 (13)0.0341 (13)0.0370 (14)0.0092 (10)0.0106 (11)0.0128 (11)
N70.0180 (15)0.0282 (16)0.0287 (16)0.0006 (12)0.0104 (12)−0.0061 (12)
C280.0180 (16)0.0127 (14)0.0181 (15)−0.0019 (12)0.0052 (13)−0.0002 (12)
C290.0155 (16)0.0190 (15)0.0146 (14)−0.0001 (12)0.0069 (12)0.0003 (12)
C320.0122 (16)0.0313 (18)0.0259 (17)−0.0018 (13)0.0053 (13)0.0008 (14)
O140.0258 (13)0.0289 (12)0.0184 (11)0.0076 (10)0.0097 (10)0.0039 (9)
N80.0121 (14)0.0244 (15)0.0276 (15)−0.0051 (11)0.0039 (12)−0.0046 (12)
C310.0120 (15)0.0181 (15)0.0187 (15)−0.0029 (12)0.0024 (12)0.0000 (12)
C300.0177 (17)0.0180 (15)0.0216 (16)−0.0004 (12)0.0055 (13)−0.0032 (12)
C10.0121 (16)0.0158 (15)0.0268 (17)0.0017 (12)0.0033 (13)−0.0022 (12)
C20.0141 (16)0.0158 (15)0.0229 (16)0.0003 (12)0.0057 (13)0.0001 (12)
O20.0235 (13)0.0260 (12)0.0282 (12)−0.0070 (9)0.0122 (10)−0.0035 (10)
O10.0207 (13)0.0270 (12)0.0441 (14)−0.0100 (10)0.0186 (11)−0.0172 (11)
C80.0141 (16)0.0158 (14)0.0165 (14)0.0027 (12)0.0033 (12)0.0010 (11)
C70.0179 (16)0.0194 (15)0.0186 (15)0.0029 (12)0.0064 (13)−0.0032 (12)
C40.0117 (16)0.0212 (15)0.0188 (15)0.0003 (12)0.0035 (12)−0.0029 (12)
C60.0144 (16)0.0192 (15)0.0166 (15)−0.0001 (12)0.0029 (12)−0.0004 (12)
C30.0138 (16)0.0159 (15)0.0276 (17)0.0003 (12)0.0057 (13)−0.0060 (12)
N10.0104 (13)0.0228 (13)0.0229 (13)−0.0027 (10)0.0038 (11)−0.0038 (11)
N20.0166 (14)0.0196 (14)0.0282 (15)−0.0033 (11)0.0060 (12)−0.0092 (12)
C50.0154 (16)0.0241 (16)0.0240 (16)−0.0015 (13)0.0075 (13)−0.0015 (13)
C90.0161 (16)0.0110 (14)0.0235 (16)0.0036 (11)0.0077 (13)0.0013 (12)
O40.0261 (13)0.0288 (12)0.0214 (11)0.0088 (10)0.0128 (10)0.0055 (9)
O130.0208 (12)0.0322 (13)0.0224 (12)0.0071 (10)0.0084 (10)0.0112 (10)
O30.0131 (11)0.0248 (11)0.0218 (11)0.0054 (9)0.0038 (9)0.0013 (9)
O1W0.0313 (14)0.0279 (12)0.0216 (12)−0.0129 (10)0.0108 (10)0.0001 (9)
O2W0.0307 (14)0.0532 (16)0.0215 (12)−0.0001 (12)0.0108 (11)−0.0028 (11)

Geometric parameters (Å, °)

Gd1—O12.338 (2)C16—H160.9300
Gd1—O22.526 (2)C11—C101.495 (4)
Gd1—O3i2.350 (2)C10—O61.247 (4)
Gd1—O5ii2.461 (2)C10—O51.278 (4)
Gd1—O6ii2.499 (2)C18—O71.247 (4)
Gd1—O82.314 (2)C18—O81.255 (3)
Gd1—N62.617 (3)C36—O151.248 (4)
Gd1—O1W2.374 (2)C36—O161.271 (4)
Gd2—O92.312 (2)C36—C351.491 (4)
Gd2—O11iii2.539 (2)C33—C341.385 (4)
Gd2—O12iii2.342 (2)C33—N71.387 (4)
Gd2—O13iv2.267 (2)C33—C311.393 (4)
Gd2—O152.449 (2)C35—C341.388 (4)
Gd2—O162.520 (2)C35—C291.424 (4)
Gd2—N1iii2.612 (3)C34—H340.9300
Gd2—O2W2.384 (2)N7—C321.323 (4)
N6—C231.316 (4)N7—H7A0.77 (4)
N6—C241.407 (4)C28—O141.236 (4)
N5—C231.343 (4)C28—O131.272 (4)
N5—C221.372 (4)C28—C291.516 (4)
N5—H5A0.83 (4)C29—C301.380 (4)
C23—H230.9300C32—N81.316 (4)
C25—C241.389 (4)C32—H320.9300
C25—C261.391 (4)N8—C311.382 (4)
C25—H250.9300N8—H8A0.80 (4)
C21—C201.385 (4)C31—C301.390 (4)
C21—C221.390 (4)C30—H300.9300
C21—H210.9300C1—O21.247 (4)
C24—C221.400 (4)C1—O11.281 (4)
C20—C261.411 (4)C1—C21.502 (4)
C20—C191.504 (4)C2—C31.380 (4)
C26—C271.498 (4)C2—C81.420 (4)
N3—C141.314 (4)C8—C71.378 (4)
N3—C151.378 (4)C8—C91.510 (4)
N3—H3A0.81 (4)C7—C61.396 (4)
C13—C121.383 (4)C7—H70.9300
C13—N41.391 (4)C4—C31.392 (4)
C13—C151.392 (4)C4—C61.400 (4)
N4—C141.313 (4)C4—N11.403 (4)
N4—H4A0.84 (4)C6—N21.378 (4)
C15—C161.387 (4)C3—H30.9300
C14—H140.9300N1—C51.315 (4)
C27—O111.245 (4)N2—C51.345 (4)
C27—O121.270 (4)N2—H2A0.82 (4)
C19—O101.251 (4)C5—H50.9300
C19—O91.251 (4)C9—O41.252 (4)
O11—Gd2iv2.539 (2)C9—O31.266 (4)
C17—C161.378 (4)O1W—H1W0.84
C17—C111.420 (4)O1W—H2W0.82
C17—C181.513 (4)O2W—H3W0.86
C12—C111.386 (4)O2W—H4WA0.82
C12—H120.9300O2W—H4WB0.82
O8—Gd1—O1107.71 (8)N3—C14—H14124.8
O8—Gd1—O3i80.39 (7)O11—C27—O12120.5 (3)
O1—Gd1—O3i156.84 (7)O11—C27—C26122.0 (3)
O8—Gd1—O1W150.83 (7)O12—C27—C26117.5 (3)
O1—Gd1—O1W89.84 (8)O11—C27—Gd2iv64.70 (17)
O3i—Gd1—O1W75.13 (7)O12—C27—Gd2iv55.80 (16)
O8—Gd1—O5ii91.14 (7)C26—C27—Gd2iv173.3 (2)
O1—Gd1—O5ii127.16 (7)O10—C19—O9124.2 (3)
O3i—Gd1—O5ii72.98 (7)O10—C19—C20117.1 (3)
O1W—Gd1—O5ii96.56 (8)O9—C19—C20118.6 (3)
O8—Gd1—O6ii133.85 (7)C27—O11—Gd2iv88.98 (18)
O1—Gd1—O6ii81.62 (8)C16—C17—C11121.3 (3)
O3i—Gd1—O6ii108.82 (7)C16—C17—C18115.8 (3)
O1W—Gd1—O6ii70.40 (8)C11—C17—C18123.0 (3)
O5ii—Gd1—O6ii52.51 (7)C13—C12—C11117.9 (3)
O8—Gd1—O277.02 (7)C13—C12—H12121.1
O1—Gd1—O253.69 (7)C11—C12—H12121.1
O3i—Gd1—O2148.38 (7)C17—C16—C15117.1 (3)
O1W—Gd1—O2131.50 (7)C17—C16—H16121.4
O5ii—Gd1—O285.58 (8)C15—C16—H16121.4
O6ii—Gd1—O273.23 (7)C12—C11—C17120.6 (3)
O8—Gd1—N687.31 (8)C12—C11—C10118.5 (3)
O1—Gd1—N678.24 (8)C17—C11—C10120.9 (3)
O3i—Gd1—N680.57 (8)O6—C10—O5120.7 (3)
O1W—Gd1—N673.35 (8)O6—C10—C11120.3 (3)
O5ii—Gd1—N6153.38 (8)O5—C10—C11118.9 (3)
O6ii—Gd1—N6138.26 (8)O6—C10—Gd1i61.93 (15)
O2—Gd1—N6119.76 (8)O5—C10—Gd1i60.23 (15)
O8—Gd1—C10ii115.53 (8)C11—C10—Gd1i167.3 (2)
O1—Gd1—C10ii106.09 (8)O7—C18—O8124.7 (3)
O3i—Gd1—C10ii88.80 (8)O7—C18—C17117.4 (3)
O1W—Gd1—C10ii79.89 (8)O8—C18—C17117.8 (3)
O5ii—Gd1—C10ii26.78 (8)C18—O8—Gd1148.6 (2)
O6ii—Gd1—C10ii26.11 (8)C10—O5—Gd1i92.99 (18)
O2—Gd1—C10ii81.39 (8)C10—O6—Gd1i91.96 (17)
N6—Gd1—C10ii152.92 (8)C27—O12—Gd2iv97.54 (19)
O13iv—Gd2—O987.94 (8)O15—C36—O16120.3 (3)
O13iv—Gd2—O12iii107.11 (9)O15—C36—C35119.2 (3)
O9—Gd2—O12iii152.90 (8)O16—C36—C35120.5 (3)
O13iv—Gd2—O2W153.97 (8)C34—C33—N7132.7 (3)
O9—Gd2—O2W79.66 (9)C34—C33—C31121.1 (3)
O12iii—Gd2—O2W77.24 (9)N7—C33—C31106.1 (3)
O13iv—Gd2—O15136.70 (8)C34—C35—C29120.9 (3)
O9—Gd2—O1598.56 (8)C34—C35—C36118.6 (3)
O12iii—Gd2—O1585.94 (9)C29—C35—C36120.6 (3)
O2W—Gd2—O1568.38 (8)C33—C34—C35117.8 (3)
O13iv—Gd2—O1689.20 (7)C33—C34—H34121.1
O9—Gd2—O1675.74 (8)C35—C34—H34121.1
O12iii—Gd2—O16125.56 (8)C36—O16—Gd291.50 (18)
O2W—Gd2—O16109.44 (8)C36—O15—Gd295.47 (18)
O15—Gd2—O1652.14 (7)C19—O9—Gd2168.9 (2)
O13iv—Gd2—O11iii80.34 (8)C32—N7—C33108.5 (3)
O9—Gd2—O11iii153.99 (8)C32—N7—H7A129 (3)
O12iii—Gd2—O11iii52.97 (8)C33—N7—H7A123 (3)
O2W—Gd2—O11iii119.51 (8)O14—C28—O13123.9 (3)
O15—Gd2—O11iii75.38 (9)O14—C28—C29119.9 (3)
O16—Gd2—O11iii80.92 (8)O13—C28—C29116.1 (3)
O13iv—Gd2—N1iii82.99 (8)C30—C29—C35120.7 (3)
O9—Gd2—N1iii79.84 (8)C30—C29—C28116.4 (3)
O12iii—Gd2—N1iii79.83 (8)C35—C29—C28122.8 (3)
O2W—Gd2—N1iii72.39 (8)N8—C32—N7110.4 (3)
O15—Gd2—N1iii140.32 (8)N8—C32—H32124.8
O16—Gd2—N1iii154.59 (7)N7—C32—H32124.8
O11iii—Gd2—N1iii121.11 (8)C32—N8—C31108.8 (3)
O13iv—Gd2—C27iii93.85 (9)C32—N8—H8A122 (3)
O9—Gd2—C27iii178.09 (9)C31—N8—H8A130 (3)
O12iii—Gd2—C27iii26.65 (9)N8—C31—C30131.9 (3)
O2W—Gd2—C27iii98.94 (9)N8—C31—C33106.3 (3)
O15—Gd2—C27iii79.68 (9)C30—C31—C33121.7 (3)
O16—Gd2—C27iii103.62 (8)C29—C30—C31117.8 (3)
O11iii—Gd2—C27iii26.32 (8)C29—C30—H30121.1
N1iii—Gd2—C27iii101.01 (8)C31—C30—H30121.1
C23—N6—C24104.1 (3)O2—C1—O1121.3 (3)
C23—N6—Gd1120.7 (2)O2—C1—C2121.7 (3)
C24—N6—Gd1132.91 (19)O1—C1—C2117.0 (3)
C23—N5—C22107.6 (3)C3—C2—C8121.1 (3)
C23—N5—H5A126 (3)C3—C2—C1117.9 (3)
C22—N5—H5A127 (3)C8—C2—C1121.0 (3)
N6—C23—N5113.7 (3)C1—O2—Gd188.55 (18)
N6—C23—H23123.1C1—O1—Gd196.42 (18)
N5—C23—H23123.1C7—C8—C2120.3 (3)
C24—C25—C26119.0 (3)C7—C8—C9117.6 (3)
C24—C25—H25120.5C2—C8—C9121.6 (3)
C26—C25—H25120.5C8—C7—C6118.0 (3)
C20—C21—C22117.9 (3)C8—C7—H7121.0
C20—C21—H21121.1C6—C7—H7121.0
C22—C21—H21121.1C3—C4—C6119.5 (3)
C25—C24—C22119.3 (3)C3—C4—N1130.8 (3)
C25—C24—N6131.4 (3)C6—C4—N1109.6 (3)
C22—C24—N6109.2 (3)N2—C6—C7132.6 (3)
N5—C22—C21132.2 (3)N2—C6—C4105.3 (3)
N5—C22—C24105.3 (3)C7—C6—C4122.1 (3)
C21—C22—C24122.4 (3)C2—C3—C4118.9 (3)
C21—C20—C26120.4 (3)C2—C3—H3120.5
C21—C20—C19117.2 (3)C4—C3—H3120.5
C26—C20—C19122.3 (3)C5—N1—C4103.9 (2)
C25—C26—C20120.9 (3)C5—N1—Gd2iv122.2 (2)
C25—C26—C27117.3 (3)C4—N1—Gd2iv132.34 (19)
C20—C26—C27121.7 (3)C5—N2—C6106.9 (3)
C14—N3—C15109.0 (3)C5—N2—H2A127 (3)
C14—N3—H3A128 (3)C6—N2—H2A126 (3)
C15—N3—H3A123 (3)N1—C5—N2114.3 (3)
C12—C13—N4132.9 (3)N1—C5—H5122.9
C12—C13—C15121.0 (3)N2—C5—H5122.9
N4—C13—C15106.1 (3)O4—C9—O3124.8 (3)
C14—N4—C13108.4 (3)O4—C9—C8118.8 (3)
C14—N4—H4A127 (3)O3—C9—C8116.3 (3)
C13—N4—H4A124 (3)C28—O13—Gd2iii151.0 (2)
N3—C15—C16131.9 (3)C9—O3—Gd1ii135.77 (18)
N3—C15—C13106.0 (3)H1W—O1W—H2W108
C16—C15—C13122.1 (3)H3W—O2W—H4WA106
N4—C14—N3110.4 (3)H3W—O2W—H4WB105
N4—C14—H14124.8

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, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W···O7v0.841.802.629 (3)167
O1W—H2W···O4i0.821.922.670 (3)153
O2W—H3W···O10vi0.861.742.590 (3)172
O2W—H4WA···O150.822.142.716 (5)127
O2W—H4WB···O2Wvi0.821.912.723 (4)170
N2—H2A···O14vii0.82 (4)1.94 (4)2.742 (3)169 (3)
N3—H3A···O10vii0.81 (4)1.94 (4)2.731 (4)166 (4)
N4—H4A···O160.84 (4)1.97 (4)2.801 (4)170 (4)
N5—H5A···O4v0.83 (4)1.96 (4)2.772 (3)165 (4)
N7—H7A···O50.77 (4)2.08 (4)2.845 (3)171 (4)
N8—H8A···O7viii0.80 (4)1.95 (4)2.747 (3)172 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2247).

References

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