catena-Poly[[[diaqua­cadmium(II)]-μ-2,2′-bipyridine-6,6′-dicarboxyl­ato] dihydrate]

Knight, J.; Amoroso, A.; Edwards, P.; Ooi, L.-L.

doi:10.1107/S1600536806046423

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 12| December 2006| Pages m3306-m3308

https://doi.org/10.1107/S1600536806046423

catena-Poly[[[diaquacadmium(II)]-μ-2,2′-bipyridine-6,6′-dicarboxylato] dihydrate]

James C. Knight,^a ^* Angelo J. Amoroso,^a Peter G. Edwards ^a and Li-Ling Ooi ^a

^aMain Building, School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: knightjc@cardiff.ac.uk

(Received 11 October 2006; accepted 3 November 2006; online 15 November 2006)

The title hydrated 2,2′-bipyridine-6,6′-dicarboxylate–cadmium(II) complex, {[Cd(C₁₂H₂N₂O₄)(H₂O)₂]·2H₂O}_n, crystallizes with eight oxygen-bridged monomer units in the unit cell. The divalent cadmium ion is seven-coordinate, and the coordination polyhedron can best be described as slightly distorted pentagonal–bipyramidal.

Comment

The title compound, (I), has been synthesized as part of a study investigating complex stability. Specifically, the research is part of initial investigations towards generating Gd^III-based contrast agents for applications in magnetic resonance imaging (MRI), where overall complex stability is crucial in preventing dissociation in vivo, due to the well documented interference of Gd³⁺ in biological processes (Cacheris, 1990 ).

The research aims to elucidate structural features that contribute significantly to overall stability. A comprehensive series of transition metals has been considered, providing an insight into competition reactions which may compromise the effectiveness of the ability of the ligands to coordinate to the Gd³⁺ ion and neutralize its potential toxicity (Caravan, 1999 ).

In this complex, the Cd atom is located at the centre of a distorted pentagonal bipyramid of seven coordinating atoms (five O atoms and two N atoms; Fig. 1). One of these donor atoms (O4ⁱ) originates from another symmetry-related complex (x − $[{1\over 2}]$ , $[{1\over 2}]$ − y, z). The bond lengths are comparable to those of similar polymeric cadmium-based complexes (Deloume & Loiseleur, 1974 ). The bridging behaviour results in the formation of a polymer, which extends in a zigzag fashion (see Fig. 2).

The donor atoms O4ⁱ and O5 are located in the axial positions, with N1, N2, O1, O3 and O6 in the equatorial plane. The deviation of the equatorial angles N1—Cd1—N2, N2—Cd1—O3, O3—Cd1—O6, O6—Cd1—O1, O1—Cd1—N1 (Table 1) from the theoretical average angle of 72° can be explained by the narrow bite angle resulting from the coordination of the rigid tetradentate ligand. While the bridging carboxylate group lies almost perpendicular to the tetradentate ligand at 88.75 (13)°, the axial water molecule appears to lean away from the more sterically demanding ligand, tending towards the equatorial water donor at a more acute angle of 82.08 (12)°.

The oxygen-bridged polymer is formed via coordination of one of the carbonyl O atoms (O4ⁱ) to the cadmium in an axial orientation at an average angle of 90.10° to the pentagonal plane. The molecular packing is layered, with intermolecular π-stacking between bipyridine rings (N1/C1–C5 and N2/C6–C10) at a centroid–centroid distance of 3.267 Å. The equatorially coordinating water molecule (O6) is hydrogen bonded to a solvent water molecule (O8), which in turn is bonded to a second solvent water molecule (O7) which is hydrogen bonded to the axially coordinating water (O5) (see Fig. 3). All significant hydrogen bonds are listed in Table 2.

Figure 1
Perspective view of the asymmetric unit, expanded to complete the Cd coordination, showing the atom numbering. Displacement ellipsoids are shown at the 50% probability level. H atoms are represented by circles of arbitrary size. [Symmetry code: (i) x − $[{1\over 2}]$ , $[{1\over 2}]$ − y, z.]

Figure 2
Fragment of the title structure, showing an oxygen-bridged chain extended in a zigzag fashion along the c axis. The dashed line indicates a hydrogen bond.

Figure 3
The molecular packing projected on the bc plane showing hydrogen bonds (dashed lines) holding the layered chains together in the crystal structure.

Experimental

To an aqueous solution (5 ml water) of 2,2-bipyridine-6,6-dicarboxylate disodium salt (0.05 mol) was added an aqueous solution (5 ml water) of cadmium(II) perchlorate (0.05 mol) and the solution was stirred continuously at room temperature for 5 h. A white precipitate was collected via filtration and redissolved in the minimum amount of hot deionized water. Slow evaporation of the solution yielded well defined crystals suitable for X-ray diffraction. ¹H NMR (D₂O): 8.48 (d, 2H, J = 9.63 Hz, py-H1), 8.16 (t, 2H, J = 9.75 Hz, py-H2), 8.08 (d, 2H, J = 7.60 Hz, py-H3).

Crystal data

[Cd(C₁₂H₂N₂O₄)(H₂O)₂]·2H₂O
M_r = 422.63
Orthorhombic, P c a b
a = 8.665 (5) Å
b = 17.392 (5) Å
c = 18.812 (5) Å
V = 2835 (2) Å³
Z = 8
D_x = 1.999 Mg m⁻³
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 150 (2) K
Block, colourless
0.52 × 0.4 × 0.22 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.492, T_max = 0.722
13837 measured reflections
3234 independent reflections
2349 reflections with I > 2σ(I)
R_int = 0.092
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.131
S = 1.04
3234 reflections
208 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0704P)² + 1.3489P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Cd1	2.388 (4)
N2—Cd1	2.418 (4)
O1—Cd1	2.413 (3)
O3—Cd1	2.423 (4)
O4—Cd1	2.332 (4)
O5—Cd1	2.287 (3)
O6—Cd1	2.336 (4)

O5—Cd1—O4	164.37 (12)
O5—Cd1—O6	82.08 (12)
O4—Cd1—O6	85.52 (13)
O5—Cd1—N1	91.00 (13)
O4—Cd1—N1	94.87 (13)
O6—Cd1—N1	149.28 (13)
O5—Cd1—O1	80.18 (12)
O4—Cd1—O1	88.70 (13)
O6—Cd1—O1	81.88 (12)
N1—Cd1—O1	67.44 (13)
O5—Cd1—N2	102.44 (13)
O4—Cd1—N2	93.18 (13)
O6—Cd1—N2	144.24 (13)
N1—Cd1—N2	66.47 (14)
O1—Cd1—N2	133.86 (12)
O5—Cd1—O3	98.34 (13)
O4—Cd1—O3	88.24 (13)
O6—Cd1—O3	77.80 (12)
N1—Cd1—O3	132.91 (13)
O1—Cd1—O3	159.62 (12)
N2—Cd1—O3	66.44 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱ	0.85	2.26	3.055 (5)	156
O7—H7B⋯O5ⁱⁱ	0.87	1.88	2.729 (5)	167
O8—H8A⋯O6ⁱⁱⁱ	0.88	2.02	2.814 (5)	150
O8—H8B⋯O7^iv	0.86	2.00	2.816 (6)	158
Symmetry codes: (i) -x+2, -y, -z; (ii) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) -x+1, -y, -z.

The carbon bound H atoms were placed in calculated positions using a riding model with U_iso(H) = 1.2U_eq(C) and C—H = 0.95. The solvent water H atoms were located and refined with U_iso(H) = 1.2U_eq(O)]; however, the H atoms on the coordinating water molecules could not be found at geometrically sensible positions and were not included in the refinement.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806046423/fi2017sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806046423/fi2017Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

catena-Poly[[[diaquacadmium(II)]-µ-2,2'-bipyridine-6,6'-dicarboxylato] dihydrate] top

Crystal data top

[Cd(C₁₂H₂N₂O₄)(H₂O)₂]·2H₂O	F(000) = 1664.0
M_r = 422.63	D_x = 1.999 Mg m⁻³
Orthorhombic, Pcab	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2bc 2ac	Cell parameters from 24536 reflections
a = 8.665 (5) Å	θ = 2.9–27.5°
b = 17.392 (5) Å	µ = 1.59 mm⁻¹
c = 18.812 (5) Å	T = 150 K
V = 2835 (2) Å³	Block, colourless
Z = 8	0.52 × 0.4 × 0.22 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	2349 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.092
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	θ_max = 27.5°, θ_min = 3.2°
T_min = 0.492, T_max = 0.722	h = −11→11
13837 measured reflections	k = −15→22
3234 independent reflections	l = −24→24

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.0704P)² + 1.3489P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.131	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.49 e Å⁻³
3234 reflections	Δρ_min = −0.53 e Å⁻³
208 parameters

Special details top

Experimental. 1H NMR (D2O): 8.48 (d, 2H, J = 9.63?Hz, py-H1), 8.16 (t, 2H, J = 9.75?Hz, py-H2), 8.08 (d, 2H, J = 7.60?Hz, py-H3). IR (KBr) cm-1: 1617.02 (–C=O), 1591.95, 1574.59, 1421.28, 1384.64, 1267.97, 1144.55, 1111.76, 1087.66, 1018.23, 909.272, 770.423.

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	0.8416 (5)	−0.0338 (3)	0.0556 (3)	0.0178 (11)
C2	0.8675 (6)	−0.0807 (3)	−0.0025 (3)	0.0199 (11)
H2	0.9326	−0.1244	0.0017	0.024*
C3	0.7986 (6)	−0.0636 (3)	−0.0662 (3)	0.0224 (12)
H3	0.8159	−0.0951	−0.1067	0.027*
C4	0.7035 (5)	0.0003 (3)	−0.0706 (3)	0.0200 (11)
H4	0.6551	0.0135	−0.1143	0.024*
C5	0.6802 (5)	0.0447 (3)	−0.0106 (3)	0.0179 (11)
C6	0.5794 (5)	0.1142 (3)	−0.0097 (3)	0.0168 (11)
C7	0.5030 (6)	0.1419 (3)	−0.0701 (3)	0.0221 (11)
H5	0.5132	0.1164	−0.1145	0.027*
C8	0.4132 (6)	0.2067 (3)	−0.0641 (3)	0.0251 (12)
H8	0.3603	0.2264	−0.1043	0.030*
C9	0.4004 (6)	0.2431 (3)	0.0014 (3)	0.0201 (11)
H7	0.3364	0.2870	0.0068	0.024*
C10	0.4827 (5)	0.2142 (3)	0.0590 (3)	0.0174 (11)
C11	0.9164 (5)	−0.0482 (3)	0.1272 (3)	0.0181 (11)
C12	0.4806 (6)	0.2505 (3)	0.1310 (3)	0.0174 (11)
N1	0.7503 (5)	0.0284 (2)	0.0518 (2)	0.0166 (9)
N2	0.5693 (5)	0.1500 (2)	0.0531 (2)	0.0177 (9)
O1	0.8860 (4)	−0.0007 (2)	0.17608 (17)	0.0217 (8)
O2	1.0017 (4)	−0.10573 (19)	0.1324 (2)	0.0240 (8)
O3	0.5496 (4)	0.2156 (2)	0.18009 (18)	0.0259 (8)
O4	0.9154 (4)	0.1849 (2)	0.13790 (19)	0.0245 (8)
O5	0.5412 (4)	0.01180 (19)	0.19987 (17)	0.0212 (8)
O6	0.7508 (4)	0.1238 (2)	0.27733 (19)	0.0225 (8)
O7	0.8528 (5)	−0.1242 (2)	−0.2466 (2)	0.0403 (11)
H7A	0.9337	−0.1427	−0.2277	0.048*
H7B	0.8762	−0.0776	−0.2593	0.048*
O8	0.3706 (4)	0.2275 (2)	0.29834 (19)	0.0292 (9)
H8A	0.3340	0.2731	0.3089	0.035*
H8B	0.2974	0.2057	0.2748	0.035*
Cd1	0.70612 (4)	0.103047 (19)	0.156370 (18)	0.01591 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.013 (2)	0.013 (3)	0.028 (3)	0.003 (2)	0.002 (2)	0.003 (2)
C2	0.021 (3)	0.008 (2)	0.031 (3)	0.000 (2)	0.003 (2)	−0.003 (2)
C3	0.032 (3)	0.014 (3)	0.022 (3)	0.000 (2)	0.001 (2)	−0.004 (2)
C4	0.022 (3)	0.018 (3)	0.020 (3)	−0.005 (2)	−0.002 (2)	−0.001 (2)
C5	0.017 (2)	0.012 (3)	0.025 (3)	−0.004 (2)	0.000 (2)	0.000 (2)
C6	0.016 (2)	0.014 (3)	0.021 (3)	−0.0046 (19)	0.002 (2)	0.004 (2)
C7	0.030 (3)	0.017 (3)	0.020 (3)	0.001 (2)	−0.002 (2)	−0.001 (2)
C8	0.025 (3)	0.027 (3)	0.024 (3)	0.006 (2)	−0.005 (2)	0.008 (2)
C9	0.019 (2)	0.016 (3)	0.025 (3)	0.001 (2)	−0.001 (2)	0.005 (2)
C10	0.017 (2)	0.008 (2)	0.026 (3)	−0.002 (2)	0.002 (2)	0.000 (2)
C11	0.013 (2)	0.014 (3)	0.028 (3)	−0.004 (2)	0.000 (2)	0.003 (2)
C12	0.019 (2)	0.009 (2)	0.024 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)
N1	0.017 (2)	0.013 (2)	0.020 (2)	−0.0026 (18)	−0.0001 (16)	−0.0021 (18)
N2	0.021 (2)	0.009 (2)	0.023 (2)	−0.0003 (18)	0.0023 (17)	0.0006 (17)
O1	0.0254 (19)	0.0185 (19)	0.0211 (17)	0.0056 (17)	−0.0025 (15)	0.0029 (15)
O2	0.026 (2)	0.016 (2)	0.030 (2)	0.0057 (16)	−0.0009 (16)	−0.0006 (16)
O3	0.035 (2)	0.019 (2)	0.0242 (19)	0.0089 (17)	−0.0019 (16)	−0.0007 (16)
O4	0.0254 (19)	0.0131 (19)	0.035 (2)	−0.0065 (16)	0.0008 (16)	−0.0008 (16)
O5	0.0236 (18)	0.0172 (18)	0.0228 (18)	−0.0057 (15)	−0.0001 (15)	0.0017 (15)
O6	0.0289 (19)	0.0156 (18)	0.023 (2)	0.0027 (16)	−0.0033 (15)	−0.0012 (16)
O7	0.040 (2)	0.019 (2)	0.061 (3)	−0.002 (2)	−0.016 (2)	0.017 (2)
O8	0.035 (2)	0.018 (2)	0.035 (2)	0.0018 (18)	0.0004 (18)	−0.0021 (17)
Cd1	0.0193 (2)	0.0107 (2)	0.0177 (2)	−0.00014 (14)	−0.00005 (14)	−0.00005 (14)

Geometric parameters (Å, º) top

C1—N1	1.342 (6)	C10—N2	1.350 (6)
C1—C2	1.381 (7)	C10—C12	1.494 (7)
C1—C11	1.515 (7)	C11—O2	1.247 (6)
C2—C3	1.371 (7)	C11—O1	1.264 (6)
C2—H2	0.9500	C12—O3	1.256 (6)
C3—C4	1.386 (7)	C12—O4ⁱ	1.265 (6)
C3—H3	0.9500	N1—Cd1	2.388 (4)
C4—C5	1.383 (7)	N2—Cd1	2.418 (4)
C4—H4	0.9500	O1—Cd1	2.413 (3)
C5—N1	1.351 (6)	O3—Cd1	2.423 (4)
C5—C6	1.492 (7)	O4—C12ⁱⁱ	1.265 (6)
C6—N2	1.340 (6)	O4—Cd1	2.332 (4)
C6—C7	1.400 (7)	O5—Cd1	2.287 (3)
C7—C8	1.373 (7)	O6—Cd1	2.336 (4)
C7—H5	0.9500	O7—H7A	0.8490
C8—C9	1.389 (7)	O7—H7B	0.8691
C8—H8	0.9500	O8—H8A	0.8762
C9—C10	1.390 (7)	O8—H8B	0.8617
C9—H7	0.9500

N1—C1—C2	122.0 (4)	O3—C12—C10	117.2 (4)
N1—C1—C11	115.6 (4)	O4ⁱ—C12—C10	118.3 (5)
C2—C1—C11	122.4 (4)	C1—N1—C5	118.7 (4)
C3—C2—C1	119.5 (5)	C1—N1—Cd1	119.3 (3)
C3—C2—H2	120.3	C5—N1—Cd1	122.0 (3)
C1—C2—H2	120.3	C6—N2—C10	119.6 (4)
C2—C3—C4	119.0 (5)	C6—N2—Cd1	121.3 (3)
C2—C3—H3	120.5	C10—N2—Cd1	119.1 (3)
C4—C3—H3	120.5	C11—O1—Cd1	120.8 (3)
C3—C4—C5	119.0 (5)	C12—O3—Cd1	121.4 (3)
C3—C4—H4	120.5	C12ⁱⁱ—O4—Cd1	154.9 (3)
C5—C4—H4	120.5	H7A—O7—H7B	106.1
N1—C5—C4	121.8 (5)	H8A—O8—H8B	104.4
N1—C5—C6	115.1 (4)	O5—Cd1—O4	164.37 (12)
C4—C5—C6	123.1 (5)	O5—Cd1—O6	82.08 (12)
N2—C6—C7	121.7 (4)	O4—Cd1—O6	85.52 (13)
N2—C6—C5	115.1 (4)	O5—Cd1—N1	91.00 (13)
C7—C6—C5	123.2 (5)	O4—Cd1—N1	94.87 (13)
C8—C7—C6	118.9 (5)	O6—Cd1—N1	149.28 (13)
C8—C7—H5	120.5	O5—Cd1—O1	80.18 (12)
C6—C7—H5	120.5	O4—Cd1—O1	88.70 (13)
C7—C8—C9	119.5 (5)	O6—Cd1—O1	81.88 (12)
C7—C8—H8	120.3	N1—Cd1—O1	67.44 (13)
C9—C8—H8	120.3	O5—Cd1—N2	102.44 (13)
C8—C9—C10	119.0 (5)	O4—Cd1—N2	93.18 (13)
C8—C9—H7	120.5	O6—Cd1—N2	144.24 (13)
C10—C9—H7	120.5	N1—Cd1—N2	66.47 (14)
N2—C10—C9	121.3 (4)	O1—Cd1—N2	133.86 (12)
N2—C10—C12	115.5 (4)	O5—Cd1—O3	98.34 (13)
C9—C10—C12	123.2 (5)	O4—Cd1—O3	88.24 (13)
O2—C11—O1	126.1 (5)	O6—Cd1—O3	77.80 (12)
O2—C11—C1	117.2 (4)	N1—Cd1—O3	132.91 (13)
O1—C11—C1	116.7 (4)	O1—Cd1—O3	159.62 (12)
O3—C12—O4ⁱ	124.5 (5)	N2—Cd1—O3	66.44 (12)

N1—C1—C2—C3	0.1 (8)	C10—C12—O3—Cd1	7.5 (6)
C11—C1—C2—C3	−178.7 (4)	C12ⁱⁱ—O4—Cd1—O5	−122.0 (8)
C1—C2—C3—C4	−0.4 (7)	C12ⁱⁱ—O4—Cd1—O6	−84.5 (8)
C2—C3—C4—C5	−0.4 (7)	C12ⁱⁱ—O4—Cd1—N1	126.3 (8)
C3—C4—C5—N1	1.5 (7)	C12ⁱⁱ—O4—Cd1—O1	−166.4 (8)
C3—C4—C5—C6	−179.6 (4)	C12ⁱⁱ—O4—Cd1—N2	59.7 (8)
N1—C5—C6—N2	−1.4 (6)	C12ⁱⁱ—O4—Cd1—O3	−6.6 (8)
C4—C5—C6—N2	179.6 (4)	C1—N1—Cd1—O5	−75.5 (4)
N1—C5—C6—C7	177.1 (4)	C5—N1—Cd1—O5	101.3 (4)
C4—C5—C6—C7	−1.9 (7)	C1—N1—Cd1—O4	90.0 (4)
N2—C6—C7—C8	−1.3 (7)	C5—N1—Cd1—O4	−93.2 (4)
C5—C6—C7—C8	−179.7 (5)	C1—N1—Cd1—O6	0.6 (5)
C6—C7—C8—C9	0.1 (8)	C5—N1—Cd1—O6	177.4 (3)
C7—C8—C9—C10	1.9 (8)	C1—N1—Cd1—O1	3.4 (3)
C8—C9—C10—N2	−2.8 (7)	C5—N1—Cd1—O1	−179.7 (4)
C8—C9—C10—C12	178.1 (5)	C1—N1—Cd1—N2	−178.7 (4)
N1—C1—C11—O2	179.8 (4)	C5—N1—Cd1—N2	−1.8 (3)
C2—C1—C11—O2	−1.3 (7)	C1—N1—Cd1—O3	−177.9 (3)
N1—C1—C11—O1	0.0 (6)	C5—N1—Cd1—O3	−1.0 (4)
C2—C1—C11—O1	178.9 (4)	C11—O1—Cd1—O5	91.6 (3)
N2—C10—C12—O3	−4.8 (6)	C11—O1—Cd1—O4	−99.4 (4)
C9—C10—C12—O3	174.4 (5)	C11—O1—Cd1—O6	174.9 (4)
N2—C10—C12—O4ⁱ	172.5 (4)	C11—O1—Cd1—N1	−3.6 (3)
C9—C10—C12—O4ⁱ	−8.3 (7)	C11—O1—Cd1—N2	−6.2 (4)
C2—C1—N1—C5	0.9 (7)	C11—O1—Cd1—O3	179.2 (4)
C11—C1—N1—C5	179.9 (4)	C6—N2—Cd1—O5	−84.6 (4)
C2—C1—N1—Cd1	177.9 (4)	C10—N2—Cd1—O5	96.3 (3)
C11—C1—N1—Cd1	−3.2 (5)	C6—N2—Cd1—O4	94.9 (4)
C4—C5—N1—C1	−1.7 (7)	C10—N2—Cd1—O4	−84.2 (3)
C6—C5—N1—C1	179.3 (4)	C6—N2—Cd1—O6	−178.3 (3)
C4—C5—N1—Cd1	−178.6 (3)	C10—N2—Cd1—O6	2.5 (5)
C6—C5—N1—Cd1	2.4 (5)	C6—N2—Cd1—N1	1.0 (3)
C7—C6—N2—C10	0.4 (7)	C10—N2—Cd1—N1	−178.1 (4)
C5—C6—N2—C10	178.9 (4)	C6—N2—Cd1—O1	3.6 (4)
C7—C6—N2—Cd1	−178.7 (4)	C10—N2—Cd1—O1	−175.5 (3)
C5—C6—N2—Cd1	−0.2 (5)	C6—N2—Cd1—O3	−178.4 (4)
C9—C10—N2—C6	1.6 (7)	C10—N2—Cd1—O3	2.5 (3)
C12—C10—N2—C6	−179.2 (4)	C12—O3—Cd1—O5	−105.5 (4)
C9—C10—N2—Cd1	−179.2 (4)	C12—O3—Cd1—O4	88.8 (4)
C12—C10—N2—Cd1	−0.1 (5)	C12—O3—Cd1—O6	174.6 (4)
O2—C11—O1—Cd1	−176.6 (4)	C12—O3—Cd1—N1	−6.3 (4)
C1—C11—O1—Cd1	3.3 (5)	C12—O3—Cd1—O1	170.3 (4)
O4ⁱ—C12—O3—Cd1	−169.6 (4)	C12—O3—Cd1—N2	−5.5 (3)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) 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
O7—H7A···O4ⁱⁱⁱ	0.85	2.26	3.055 (5)	156
O7—H7B···O5^iv	0.87	1.88	2.729 (5)	167
O8—H8A···O6ⁱ	0.88	2.02	2.814 (5)	150
O8—H8B···O7^v	0.86	2.00	2.816 (6)	158

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

Acknowledgements

This project was supported by the MRC (research grant No. G0300261).

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