A rare `mesh of trees' (mot) net: poly[aquahemi[μ₄-1,6-bis­(1,2,4-triazol-1-yl)hexa­ne]­(μ₂-5-nitro­isophthalato)cadmium(II)]

In the title coordination compound, [Cd(C₈H₃NO₆)(C₅H₈N₃)_0.5(H₂O)]_n, each Cd^II atom is six-coordinated in a distorted octa­hedral environment surrounded by three carboxyl­ate O atoms from two different 5-nitro­isophthalate (5-NIP²⁻) ligands, two N atoms from two distinct 1,6-bis­(1,2,4-triazol-1-yl)hexane (bth) ligands and one water mol­ecule. The Cd^II centres are bridged by the bth ligands, which lie across centres of inversion, to give a honeycomb-like two-dimensional layer structure; the layers are further connected by the bridging 5-NIP²⁻ ligands with a κ²;κ¹-μ₂ coordination mode to generate the final three-dimensional structure. Topologically, taking the the Cd^II atoms and the bth ligands as different four-connected nodes and the 5-NIP²⁻ ligands as linkers, the three-dimensional structure can be simplified to a rare `mesh of trees' (mot) net with the Schäfli symbol (6⁶)(6⁴.8²)₂.

S1. Comment

The rational design and synthesis of metal–organic frameworks (MOFs) constructed from organic ligands and metal ions through a self-assembly route has undergone rapid development in recent years owing to their fascinating structural topologies and potential applications as functional materials (Abrahams et al., 1999; Eddaoudi et al., 2001; Farha et al., 2010). The topologies of MOFs can often be controlled and modified by properly selecting the coordination geometry preferred by the metal ion and the chemical structure of the organic ligand chosen. Organic carboxylate ligands have been extensively used to construct MOFs with various properties and topologies (Li et al., 2005; Eddaoudi, Kim, Rosi et al., 2002). 5-Nitroisophthalate (5-NIP^2-), as one type of bridging aromatic dicarboxylate ligand, has been widely studied (Liu et al., 2010; Huang et al., 2011; Sarma et al., 2011). The nitro group (–NO₂) which can act as a hydrogen-bond acceptor or coordinate to the metal centers influences the final coordination structure (Du et al., 2008; Ye et al., 2008).

The selection of the second ligand is also significant. By comparison with pyridine-containing ligands, imidazole- or triazole-containing ligands have seldom been used (Ma et al., 2003; Tian et al., 2008). Structures with 1,6-bis(1,2,4-triazol-1-yl)hexane (bth) and Cd^II are really rare with only a few reported (Liu et al., 2007; Liang et al., 2009). Mot net (mot = mesh of trees) is a well known topology, first introduced to crystal design by Batten et al. (2009). Reported crystal structures with a mot net are rare (Wen et al., 2009). Here we report the synthesis and structure of Cd(C₈H₃NO₆)(C₅H₈N₃)_0.5(H₂O), (I), which crystallizes in this topology.

Selected bond lengths and angles for (I) are given in Table 1. As shown in Fig. 1, the asymmetric unit of (I) contains one Cd^II atom, one 5-NIP^2-, one half bth ligand and one coordinated water molecule. A centre of symmetry falls on the mid-point of the C13—C13ⁱⁱⁱ bond of the bth [symmetry code: (iii) -x + 1,-y,-z + 2]. Each Cd^II atom is six-coordinated in a distorted octahedral environment surrounded by three carboxylate oxygen atoms from two different 5-NIP^2- anions, two nitrogen atoms from two distinct bth ligands and one water molecule, with average Cd—O_carboxylate and Cd—N distances of 2.330 (9) and 2.387 (7) Å, respectively. The N2—Cd1—N3 angle, which is close to 180° (Table 1), and the N—Cd—O angle range of 84.31 (7) to 100.12 (8)° are consistent with a distorted octahedral coordination environment about the Cd. The Cd^II atoms are bridged by the bth ligands to form a honeycomb-like two-dimensional layer structure (Fig. 2) in which the bth ligands act as µ₄-bridging ligands with two nitrogen atoms in each triazoyl coordinated to the different Cd^II atoms. This µ₄-bridging mode has not been reported before and may be rationalized through the weaker coordination ability of the 2-position nitrogen atom because of the stereo-hindrance from the adjacent hexane carbon chain. The two-dimensional layers are further connected by the bridging 5-NIP^2- ligands with the (κ²)-(κ¹)-µ₃ coordination mode to generate the final three-dimensional structure (Fig. 3).

It is noteworthy that (I) possesses a three-dimensional net while the Cd^II structure [{Cd₄(D-ca)₄(bth)₄}₃.2H₂O]_n (D-H₂ca = D-camphor acid) reported by Liang et al. (2009) exists only as a two- dimensional sheet although the bond lengths and angles of the coordination bonds in the two structures have no significant difference. This indicates that the 5-NIP^2-, which is spatially different from the D-ca^2-, influences the final structure of (I).

Using the simplification principle (Natarajan et al., 2009; Tranchemontagne et al., 2009), the Cd^II centre and the bth ligands are defined as different four-connected nodes, while the 5-NIP^2- serve as linkers. On the basis of this concept of chemical topology, the overall structure is a three-dimensional mot net with the Schäfli symbol of (6⁶)(6⁴.8²)₂ (Fig. 4) (Wen et al., 2009). However, as a four-connected net, this mot net, which is named after MOF-112 (Batten et al., 2009; Eddaoudi, Kim, Vodak et al., 2002), is related to the NbO and CdSO₄ nets (Bai et al., 2010; Friedrichs et al., 2003) although it contains two different square-planar nodes. For one node all its connected neighbours are mutually perpendicular, whereas for the other node half are perpendicular and half are coplanar. Thus we have constructed an unusual mot net based on both 5-NIP^2- and bth ligands.

Related literature

For related literature, see: Abrahams et al. (1999); Bai et al. (2010); Batten et al. (2009); Du et al. (2008); Eddaoudi et al. (2001); Eddaoudi, Kim, Rosi, Vodak, Wachter, O'Keeffe & Yaghi (2002); Eddaoudi, Kim, Vodak, Sudik, Wachter, O'Keeffe & Yaghi (2002); Farha & Hupp (2010); Friedrichs et al. (2003); Li et al. (2005); Liang et al. (2009); Liu et al. (2007); Ma et al. (2003); Tian et al. (2008); Wen et al. (2009); Ye et al. (2008).

S2. Experimental

A mixture of CdCl₂.2.5H₂O (0.1 mmol), 5-nitroisophthalic acid (0.1 mmol), 1,6-bis(1,2,4-triazol-1-yl)hexane (0.1 mmol) and NaOH (0.2 mmol) was dissolved in distilled water (12 ml). The resulting solution was stirred for about 0.5 h at room temperature, sealed in a 25 ml Teflon-lined stainless steel autoclave and heated at 443 K for 3 d under autogenous pressure. Afterwards, the reaction system was cooled slowly to room temperature. Colourless block-shaped crystals of (I) suitable for single-crystal X-ray diffraction analysis were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature (yield 72%, based on Cd^II).

S3. Refinement

All C-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (triazole and arene) or 0.97 Å (methylene) and U_iso(H) = 1.2U_eq(C). The water H atom was located in a difference Fourier map and initially included in the subsequent refinement using the restraints O—H = 0.85 Å, H···H = 1.39 Å and U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The atom numbering and local coordination of Cd^II cations in the title compound, (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii. [Symmetry codes: (i) x + 1, y, z; (ii) x, -y + 1/2, z - 1/2.]
	Fig. 2. The honeycomb-like two-dimensional layer structure of (I) in the bc plane, constructed from Cd^II atoms and bth ligands. H atoms have been omitted for clarity.
	Fig. 3. A view of the three-dimensional structure of (I). The two-dimensional layers based on Cd^II atoms and bth ligands are connected by the bridging 5-NIP^2- ligands to generate the three-dimensional structure. H atoms have been omitted for clarity.
	Fig. 4. A schematic representation of the formation of the final three-dimensional mot net. The Cd^II centre and the bth ligands act as nodes, while bridging 5-NIP^2- ligands act as linkers.

poly[aquahemi[µ₄-1,6-bis(1,2,4- triazol-1-yl)hexane](µ₂-5-nitroisophthalato)cadmium(II)]

Crystal data

[Cd(C8H3NO6)(C5H8N3)0.5(H2O)]	F(000) = 892
Mr = 449.67	Dx = 1.934 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5181 reflections
a = 10.292 (2) Å	θ = 2.4–27.4°
b = 11.250 (3) Å	µ = 1.46 mm^−1
c = 13.339 (3) Å	T = 296 K
β = 90.644 (3)°	Block, colourless
V = 1544.4 (6) Å^3	0.26 × 0.21 × 0.19 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	3547 independent reflections
Radiation source: fine-focus sealed tube	2898 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
ω scan	θmax = 27.5°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.699, Tmax = 0.757	k = −14→14
13260 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0291P)^2] where P = (Fo^2 + 2Fc^2)/3
3547 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −0.94 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6988 (3)	0.3327 (2)	0.79722 (18)	0.0233 (6)
C2	0.5665 (3)	0.3816 (2)	0.82080 (18)	0.0220 (6)
C3	0.4547 (3)	0.3118 (3)	0.81118 (18)	0.0237 (6)
H3	0.4614	0.2339	0.7885	0.028*
C4	0.3332 (3)	0.3581 (2)	0.83545 (18)	0.0232 (6)
C5	0.3245 (3)	0.4724 (2)	0.87323 (19)	0.0254 (6)
H5	0.2446	0.5036	0.8916	0.031*
C6	0.4364 (3)	0.5394 (2)	0.88330 (18)	0.0238 (6)
C7	0.5570 (3)	0.4974 (2)	0.85558 (19)	0.0246 (6)
H7	0.6301	0.5458	0.8601	0.030*
C8	0.2117 (3)	0.2854 (3)	0.8158 (2)	0.0280 (6)
C9	0.9551 (3)	0.2301 (3)	1.01494 (19)	0.0284 (6)
H9	0.9976	0.3025	1.0077	0.034*
C10	0.8673 (3)	0.0817 (3)	1.08156 (19)	0.0269 (6)
H10	0.8351	0.0275	1.1277	0.032*
C11	0.7925 (3)	−0.0242 (3)	0.9249 (2)	0.0309 (7)
H11A	0.8052	−0.0998	0.9586	0.037*
H11B	0.8315	−0.0299	0.8592	0.037*
C12	0.6489 (3)	−0.0015 (3)	0.9123 (2)	0.0306 (6)
H12A	0.6132	−0.0602	0.8664	0.037*
H12B	0.6368	0.0761	0.8820	0.037*
C13	0.5726 (3)	−0.0060 (3)	1.00951 (19)	0.0272 (6)
H13A	0.5899	−0.0809	1.0433	0.033*
H13B	0.6016	0.0577	1.0533	0.033*
Cd1	0.934937 (19)	0.232936 (17)	0.766421 (13)	0.02273 (8)
N1	0.8593 (2)	0.0692 (2)	0.98266 (15)	0.0241 (5)
N2	0.9162 (2)	0.1647 (2)	0.93785 (15)	0.0267 (5)
N3	0.9276 (2)	0.1822 (2)	1.10526 (15)	0.0265 (5)
N4	0.4279 (3)	0.6597 (2)	0.92699 (16)	0.0305 (6)
O1	0.79671 (18)	0.39733 (18)	0.81099 (14)	0.0309 (5)
O2	0.7075 (2)	0.22703 (17)	0.76492 (15)	0.0283 (4)
O3	0.2195 (2)	0.1788 (2)	0.7966 (2)	0.0532 (7)
O4	0.10397 (19)	0.34196 (18)	0.81974 (15)	0.0335 (5)
O5	0.3245 (2)	0.6908 (2)	0.96308 (16)	0.0414 (5)
O6	0.5260 (3)	0.7215 (2)	0.9266 (2)	0.0494 (6)
O1W	0.9971 (2)	0.06259 (18)	0.69136 (16)	0.0402 (5)
H1W	1.0768	0.0443	0.6986	0.060*
H2W	0.9523	−0.0003	0.6863	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0241 (16)	0.0285 (15)	0.0172 (12)	0.0007 (12)	0.0008 (10)	0.0037 (10)
C2	0.0193 (15)	0.0284 (14)	0.0182 (12)	0.0009 (11)	−0.0007 (10)	0.0029 (10)
C3	0.0251 (15)	0.0247 (13)	0.0211 (13)	−0.0003 (11)	−0.0018 (10)	0.0000 (11)
C4	0.0197 (15)	0.0293 (15)	0.0205 (12)	−0.0014 (11)	−0.0014 (10)	0.0027 (11)
C5	0.0197 (15)	0.0342 (16)	0.0224 (13)	0.0030 (12)	0.0006 (10)	0.0033 (11)
C6	0.0268 (16)	0.0247 (14)	0.0200 (13)	0.0026 (11)	−0.0021 (11)	0.0014 (10)
C7	0.0229 (15)	0.0279 (14)	0.0230 (13)	−0.0030 (11)	−0.0021 (11)	0.0022 (11)
C8	0.0227 (16)	0.0343 (18)	0.0269 (14)	−0.0044 (12)	−0.0004 (11)	0.0029 (12)
C9	0.0271 (17)	0.0333 (16)	0.0247 (14)	−0.0037 (12)	0.0011 (11)	0.0005 (12)
C10	0.0249 (16)	0.0345 (16)	0.0214 (13)	0.0023 (12)	0.0016 (11)	0.0031 (11)
C11	0.0291 (17)	0.0329 (16)	0.0307 (14)	−0.0035 (13)	0.0057 (12)	−0.0095 (12)
C12	0.0285 (17)	0.0394 (17)	0.0238 (14)	−0.0075 (13)	0.0001 (12)	−0.0038 (12)
C13	0.0278 (16)	0.0298 (15)	0.0240 (13)	−0.0034 (12)	0.0009 (11)	−0.0031 (11)
Cd1	0.02165 (12)	0.02590 (12)	0.02064 (11)	0.00008 (8)	0.00062 (7)	−0.00017 (8)
N1	0.0211 (13)	0.0293 (13)	0.0220 (11)	−0.0007 (10)	0.0025 (9)	−0.0008 (9)
N2	0.0248 (14)	0.0340 (14)	0.0214 (11)	−0.0034 (10)	0.0013 (9)	0.0021 (9)
N3	0.0250 (14)	0.0346 (13)	0.0200 (11)	0.0004 (11)	0.0001 (9)	−0.0007 (10)
N4	0.0357 (16)	0.0304 (14)	0.0254 (12)	0.0048 (11)	−0.0032 (10)	−0.0024 (10)
O1	0.0202 (11)	0.0325 (11)	0.0401 (11)	−0.0035 (9)	0.0020 (8)	−0.0029 (9)
O2	0.0251 (12)	0.0293 (11)	0.0305 (10)	0.0014 (8)	0.0004 (8)	−0.0032 (8)
O3	0.0312 (14)	0.0384 (14)	0.0899 (19)	−0.0079 (11)	−0.0043 (12)	−0.0158 (13)
O4	0.0190 (11)	0.0357 (12)	0.0458 (12)	−0.0025 (9)	−0.0028 (9)	0.0055 (9)
O5	0.0409 (15)	0.0409 (13)	0.0424 (13)	0.0126 (11)	0.0044 (10)	−0.0104 (10)
O6	0.0442 (17)	0.0346 (13)	0.0694 (17)	−0.0098 (11)	0.0026 (13)	−0.0152 (11)
O1W	0.0280 (13)	0.0329 (12)	0.0594 (14)	0.0058 (9)	−0.0064 (10)	−0.0101 (10)

Geometric parameters (Å, º)

C1—O1	1.254 (3)	C11—C12	1.508 (4)
C1—O2	1.268 (3)	C11—H11A	0.9700
C1—C2	1.505 (4)	C11—H11B	0.9700
C2—C7	1.387 (4)	C12—C13	1.524 (3)
C2—C3	1.397 (4)	C12—H12A	0.9700
C3—C4	1.396 (4)	C12—H12B	0.9700
C3—H3	0.9300	C13—C13^i	1.520 (5)
C4—C5	1.384 (4)	C13—H13A	0.9700
C4—C8	1.515 (4)	C13—H13B	0.9700
C5—C6	1.382 (4)	Cd1—O4^ii	2.238 (2)
C5—H5	0.9300	Cd1—O1W	2.258 (2)
C6—C7	1.382 (4)	Cd1—O2	2.342 (2)
C6—N4	1.477 (3)	Cd1—N3^iii	2.353 (2)
C7—H7	0.9300	Cd1—O1	2.412 (2)
C8—O3	1.229 (4)	Cd1—N2	2.422 (2)
C8—O4	1.280 (3)	N1—N2	1.365 (3)
C9—N2	1.322 (3)	N3—Cd1^iv	2.353 (2)
C9—N3	1.353 (3)	N4—O5	1.224 (3)
C9—H9	0.9300	N4—O6	1.226 (3)
C10—N3	1.326 (4)	O4—Cd1^v	2.238 (2)
C10—N1	1.328 (3)	O1W—H1W	0.8495
C10—H10	0.9300	O1W—H2W	0.8475
C11—N1	1.468 (3)
O1—C1—O2	122.2 (3)	H12A—C12—H12B	107.6
O1—C1—C2	119.0 (2)	C13^i—C13—C12	111.7 (3)
O2—C1—C2	118.7 (2)	C13^i—C13—H13A	109.3
C7—C2—C3	119.9 (2)	C12—C13—H13A	109.3
C7—C2—C1	118.7 (2)	C13^i—C13—H13B	109.3
C3—C2—C1	121.4 (2)	C12—C13—H13B	109.3
C4—C3—C2	120.5 (3)	H13A—C13—H13B	107.9
C4—C3—H3	119.7	O4^ii—Cd1—O1W	112.51 (8)
C2—C3—H3	119.7	O4^ii—Cd1—O2	142.34 (7)
C5—C4—C3	119.5 (3)	O1W—Cd1—O2	105.10 (7)
C5—C4—C8	120.5 (3)	O4^ii—Cd1—N3^iii	94.87 (8)
C3—C4—C8	119.9 (3)	O1W—Cd1—N3^iii	86.89 (8)
C6—C5—C4	119.0 (3)	O2—Cd1—N3^iii	88.96 (7)
C6—C5—H5	120.5	O4^ii—Cd1—O1	87.71 (7)
C4—C5—H5	120.5	O1W—Cd1—O1	158.59 (7)
C5—C6—C7	122.5 (3)	O2—Cd1—O1	55.35 (6)
C5—C6—N4	119.1 (2)	N3^iii—Cd1—O1	84.31 (7)
C7—C6—N4	118.4 (2)	O4^ii—Cd1—N2	86.75 (8)
C6—C7—C2	118.5 (3)	O1W—Cd1—N2	100.12 (8)
C6—C7—H7	120.7	O2—Cd1—N2	84.78 (7)
C2—C7—H7	120.7	N3^iii—Cd1—N2	171.61 (8)
O3—C8—O4	123.5 (3)	O1—Cd1—N2	87.53 (7)
O3—C8—C4	120.5 (3)	C10—N1—N2	109.3 (2)
O4—C8—C4	116.0 (3)	C10—N1—C11	128.3 (2)
N2—C9—N3	114.0 (3)	N2—N1—C11	122.3 (2)
N2—C9—H9	123.0	C9—N2—N1	103.0 (2)
N3—C9—H9	123.0	C9—N2—Cd1	122.11 (19)
N3—C10—N1	110.5 (2)	N1—N2—Cd1	134.58 (17)
N3—C10—H10	124.7	C10—N3—C9	103.3 (2)
N1—C10—H10	124.7	C10—N3—Cd1^iv	125.03 (17)
N1—C11—C12	113.0 (2)	C9—N3—Cd1^iv	130.33 (19)
N1—C11—H11A	109.0	O5—N4—O6	124.0 (3)
C12—C11—H11A	109.0	O5—N4—C6	118.2 (3)
N1—C11—H11B	109.0	O6—N4—C6	117.8 (2)
C12—C11—H11B	109.0	C1—O1—Cd1	89.70 (17)
H11A—C11—H11B	107.8	C1—O2—Cd1	92.56 (16)
C11—C12—C13	114.4 (2)	C8—O4—Cd1^v	112.63 (18)
C11—C12—H12A	108.7	Cd1—O1W—H1W	115.6
C13—C12—H12A	108.7	Cd1—O1W—H2W	126.0
C11—C12—H12B	108.7	H1W—O1W—H2W	109.4
C13—C12—H12B	108.7
O1—C1—C2—C7	1.0 (4)	O4^ii—Cd1—N2—C9	27.7 (2)
O2—C1—C2—C7	−179.6 (2)	O1W—Cd1—N2—C9	140.0 (2)
O1—C1—C2—C3	−177.1 (2)	O2—Cd1—N2—C9	−115.6 (2)
O2—C1—C2—C3	2.3 (4)	O1—Cd1—N2—C9	−60.2 (2)
C7—C2—C3—C4	0.6 (4)	O4^ii—Cd1—N2—N1	−160.0 (2)
C1—C2—C3—C4	178.7 (2)	O1W—Cd1—N2—N1	−47.7 (2)
C2—C3—C4—C5	−2.7 (4)	O2—Cd1—N2—N1	56.7 (2)
C2—C3—C4—C8	174.4 (2)	O1—Cd1—N2—N1	112.2 (2)
C3—C4—C5—C6	1.9 (4)	N1—C10—N3—C9	0.2 (3)
C8—C4—C5—C6	−175.2 (2)	N1—C10—N3—Cd1^iv	168.00 (17)
C4—C5—C6—C7	1.0 (4)	N2—C9—N3—C10	−0.4 (3)
C4—C5—C6—N4	−177.8 (2)	N2—C9—N3—Cd1^iv	−167.28 (19)
C5—C6—C7—C2	−3.1 (4)	C5—C6—N4—O5	8.0 (4)
N4—C6—C7—C2	175.7 (2)	C7—C6—N4—O5	−170.9 (2)
C3—C2—C7—C6	2.2 (4)	C5—C6—N4—O6	−173.4 (3)
C1—C2—C7—C6	−175.9 (2)	C7—C6—N4—O6	7.7 (4)
C5—C4—C8—O3	−169.2 (3)	O2—C1—O1—Cd1	−3.8 (2)
C3—C4—C8—O3	13.7 (4)	C2—C1—O1—Cd1	175.5 (2)
C5—C4—C8—O4	11.4 (4)	O4^ii—Cd1—O1—C1	−170.08 (15)
C3—C4—C8—O4	−165.7 (2)	O1W—Cd1—O1—C1	28.6 (3)
N1—C11—C12—C13	−66.0 (3)	O2—Cd1—O1—C1	2.13 (14)
C11—C12—C13—C13^i	−174.7 (3)	N3^iii—Cd1—O1—C1	94.80 (15)
N3—C10—N1—N2	0.0 (3)	N2—Cd1—O1—C1	−83.23 (15)
N3—C10—N1—C11	−175.3 (3)	O1—C1—O2—Cd1	3.9 (3)
C12—C11—N1—C10	82.1 (4)	C2—C1—O2—Cd1	−175.38 (19)
C12—C11—N1—N2	−92.6 (3)	O4^ii—Cd1—O2—C1	10.7 (2)
N3—C9—N2—N1	0.4 (3)	O1W—Cd1—O2—C1	−172.41 (15)
N3—C9—N2—Cd1	174.86 (18)	N3^iii—Cd1—O2—C1	−85.92 (15)
C10—N1—N2—C9	−0.3 (3)	O1—Cd1—O2—C1	−2.11 (14)
C11—N1—N2—C9	175.4 (2)	N2—Cd1—O2—C1	88.49 (15)
C10—N1—N2—Cd1	−173.63 (19)	O3—C8—O4—Cd1^v	−8.3 (4)
C11—N1—N2—Cd1	2.0 (4)	C4—C8—O4—Cd1^v	171.09 (17)

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