catena-Poly[[[(benzene-1,3,5-tricarboxylic acid)(1,10-phenanthroline)cadmium(II)]-[mu]-oxalato] 1H-benzotriazole solvate monohydrate]

In the title compound, [Cd(C₂O₄)(C₁₂H₈N₂)(C₉H₆O₆)]·C₆H₅N₃·H₂O, the Cd^II atom has a distorted penta­gonal-bipyramidal geometry, defined by two N atoms and five O atoms from bidentate 1,10-phenanthroline ligands, oxalate ligands and benzene-1,3,5-tricarboxylic acid ligands. The oxalate ligands in the asymmetric unit possess inversion symmetry. The triazole molecule is not coordinated to the Cd atom. The structure of the title compound features a one-dimensional chain running along the crystallographic a axis, and a three-dimensional supra­molecular network is formed via aromatic [pi]-[pi] inter­actions and hydrogen-bonding inter­actions.

S1. Comment

Rational design and synthesis of metal-organic polymers is of current interest in the field of supramolecular chemistry and crystal engineering. Benzene-1,3,5-tricarboxylic acid (H₃BTC), as a popular organic ligand, has been investigated in the construction of metal-organic frameworks. As a multi-carboxylate ligand, benzene-1,3,5-tricarboxylic acid exhibits versatile binding modes in the construction of polymeric complexes. It can act as H₂BTC^- (Ying & Mao, 2004), HBTC^2-(Shi et al., 2004) and BTC^3- (Almeida Paz & Kilnowski, 2004) anions and serve as µ₂ (Cheng et al., 2004), µ₃ (Zheng et al., 2004), µ₄ (Shi et al., 2003), µ₅ (Wang et al., 2003) and µ₆ (Serre et al., 2004) linkers. So far, some structures of metal-organic polymers containing benzene-1,3,5-tricarboxylic acid and 1,10-phenanthroline have been reported, such as catena-[bis(µ₃-benzenecarboxylic acid -3,5-dicarboxylato)bis(1,10-phenanthroline)dicadmium(II) (µ₂-benzenenecarboxylic acid -3,5-dicarboxylato)bis(1,10-phenanthroline)cadmium(II)] (Shi et al., 2004), catena-[(µ₃-1,3,5-benzenetricarboxylato) -(1,10-phenanthroline)indium] (Gomez-Lor et al., 2005), catena-[(µ₂-1,3-dicarboxybenzene-5-carboxylato)diaqua (1,10-phenanthroline)manganese(II)1,3-dicarboxybenzene-5-carboxylate monohydrate] (Majumder et al., 2005), catena-[(µ₂-benaene-1,3-dicarboxylato-5-carboxylic acid)-aqua- (1,10-phenanthroline)-cobalt(II)] (Plater et al., 2001) and bis[diaqua-bis(1,10-phenathroline)manganese(II)]hexaaquacopper(II) bis(1,3,5-benzenetricarboxylate)docosahydrate clathrate (Qiu et al., 2005). We report here the structure of [Cd(C₉H₆O₆)(C₁₂H₈N₂)(C₂O₄)]·(C₆H₅N₃)·H₂O, (I), which contains four different organic ligands.

As shown in Fig. 1, the asymmetric unit contains one Cd atom, one H₃BTC ligand, one 1,10-phenanthroline ligand, two half oxalate ligands, one uncoordinated benzotriazole molecule and one solvent water molecule. The Cd^II ion is coordinated by five O atoms of one H₃BTC ligand and two oxalate ligands, and two N atoms from the 1,10-phenanthroline ligand, showing a distorted pentagonal–bipyramidal geometry. The two half oxalate ligands in the asymmetric unit possess inversion symmetry. The Cd—O bond distances range from 2.287 (3) to 2.525 (4) Å, and the Cd—N bond distances are 2.334 (4) and 2.351 (4) Å (Fig. 1). Adjacent Cd atoms are linked by oxalate ligands, forming one-dimensional chains running along the crystallographic a axis (Fig. 2). The dihedral angles between the oxalate and 1,10-phenanthroline ligands are 72.348 (s.u. value?) and 82.871 (s.u.?)°. The chains of (I) are linked by O—H···O hydrogen bonds involving the hydroxy groups of H₃BTC ligands and carboxyl groups of oxalate ligands (O2—H1···O8^iv, O6—H3···O9ⁱⁱⁱ; all symmetry codes as in Table 1), resulting in two-dimensional layers (Fig. 3). Although the benzotriazole ligands are not coordinated to the Cd atom, they take part in the construction of the three-dimensional hydrogen-bond network. These sheets are further linked into a three-dimensional supramolecular network via O —H···N, N—H···O, and O—H···O hydrogen bonds (O4—H2···N3, N5—H5A···O1Wⁱⁱ, O1W—H4···O1ⁱ, O1W—H5···O10) (Fig. 3), and details are given in Table 1. Meanwhile, the three-dimensional network of the title compound is stabilized by strong π–π stacking interactions between the 1,10-phenanthroline ligands and H₃BTC ligands. As shown in Fig. 3, the face-to-face distance between adjacent 1,10-phenanthroline ligands is 3.324 (3) Å, and that between the H₃BTC ligands and the benzotriazole system is 3.414 (3) Å. These strong π–π stacking and hydrogen-bonding interactions play important roles in forming the resulting three-dimensional supramolecular network.

Related literature

For related literature, see: Almeida Paz & Kilnowski (2004); Cheng et al. (2004); Gomez-Lor, Gutierrez-Puebla, Iglesias, Monge, Ruiz-Valero & Snejko (2005); Majumder et al. (2005); Plater et al. (2001); Qiu et al. (2005); Serre et al. (2004); Shi et al. (2003, 2004); Wang et al. (2003); Ying & Mao (2004); Zheng et al. (2004).

S2. Experimental

The title compound was prepared by hydrothermal methods. A mixture of Cd(NO₃)₂·6H₂O (0.17 g 0.5 mmol), H₃BTC (0.13 g 0.6 mmol), 1,10-phenanthroline (0.1 g 0.6 mmol), oxalic acid (0.027 g 0.3 mmol), benzotriazole (0.06 g 0.5 mmol) and water (10 ml) was stirred for 20 min in air. The mixture was then transferred to a 23 ml Teflon reactor and kept at 433 K for 72 h under autogenous pressure. Crystals suitable for X-ray analysis were obtained after the mixture was cooled to room temperature.

S3. Refinement

All H atoms were initially located in a difference Fourier map. H atoms of hydroxy groups and water molecules were then constrained to an ideal geometry with O—H distances of 0.85 Å and U_iso(H) values of 1.5U_eq(O). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93 Å, an N—H distance of 0.86 Å and U_iso(H) values of 1.2U_eq(C,N).

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. [symmetry code: i = -x + 1,-y,-z + 1; ii = -x,-y,-z + 1]
	Fig. 2. View of the one-dimensional zigzag chain running along a axis.
	Fig. 3. Perspective views of the two and three-dimensional supramolecular networks along the b axis.

catena-Poly[[[(1,10-phenanthroline-κ²N,N')(benzene-1,3,5-tricarboxylic acid-O)cadmium(II)]-µ-oxalato] 1H-benzotriazole solvate monohydrate]

Crystal data

[Cd(C2O4)(C9H6O6)(C12H8N2)]·C6H5N3·H2O	Z = 2
Mr = 727.91	F(000) = 732
Triclinic, P1	Dx = 1.750 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4531 (19) Å	Cell parameters from 13575 reflections
b = 10.869 (2) Å	θ = 3.0–27.5°
c = 14.100 (3) Å	µ = 0.87 mm^−1
α = 87.86 (3)°	T = 298 K
β = 73.28 (3)°	Block, colorless
γ = 84.63 (3)°	0.26 × 0.25 × 0.16 mm
V = 1381.3 (5) Å^3

Data collection

Rigaku R-AXIS RAPID IP diffractometer	6247 independent reflections
Radiation source: fine-focus sealed tube	4186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 0.01 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.806, Tmax = 0.874	l = −17→18
13575 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 1.7244P] where P = (Fo^2 + 2Fc^2)/3
6247 reflections	(Δ/σ)max < 0.001
415 parameters	Δρmax = 0.77 e Å^−3
1 restraint	Δρmin = −1.12 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
Cd1	0.25785 (4)	0.16874 (3)	0.45375 (3)	0.02870 (12)
O1	0.3962 (5)	0.0266 (3)	−0.1666 (3)	0.0486 (10)
O2	0.5701 (5)	0.1450 (3)	−0.2533 (3)	0.0459 (10)
H1	0.5782	0.0942	−0.2993	0.069*
O4	0.7595 (4)	0.4547 (3)	−0.0909 (3)	0.0463 (10)
H2	0.7843	0.5214	−0.0731	0.070*
O3	0.6867 (5)	0.4668 (4)	0.0728 (3)	0.0612 (13)
O5	0.3123 (5)	0.2107 (4)	0.2699 (3)	0.0500 (11)
O6	0.2047 (4)	0.0848 (3)	0.1978 (3)	0.0480 (10)
H3	0.1543	0.0740	0.2575	0.072*
O7	0.4061 (4)	0.1331 (3)	0.5625 (2)	0.0330 (8)
O8	0.5869 (4)	0.0063 (3)	0.5938 (2)	0.0329 (8)
O9	−0.0845 (4)	−0.0802 (3)	0.6070 (2)	0.0354 (8)
O10	0.1028 (4)	0.0381 (3)	0.5778 (3)	0.0390 (9)
C1	0.3917 (5)	0.1986 (4)	0.0953 (3)	0.0271 (10)
C2	0.3884 (6)	0.1408 (4)	0.0104 (4)	0.0327 (12)
H2A	0.3247	0.0793	0.0142	0.039*
C3	0.4805 (6)	0.1749 (4)	−0.0807 (3)	0.0297 (11)
C4	0.5771 (6)	0.2653 (4)	−0.0873 (4)	0.0335 (12)
H4A	0.6406	0.2860	−0.1483	0.040*
C5	0.5786 (6)	0.3252 (4)	−0.0012 (4)	0.0303 (11)
C6	0.4871 (6)	0.2906 (4)	0.0885 (4)	0.0317 (11)
H6A	0.4890	0.3293	0.1458	0.038*
C7	0.3011 (6)	0.1660 (5)	0.1951 (4)	0.0334 (12)
C8	0.4779 (6)	0.1075 (4)	−0.1706 (4)	0.0324 (12)
C9	0.6803 (6)	0.4218 (5)	−0.0023 (4)	0.0348 (12)
C10	0.5094 (7)	0.3610 (5)	0.3434 (4)	0.0416 (14)
H10A	0.5596	0.2904	0.3100	0.050*
C11	0.5716 (7)	0.4726 (6)	0.3180 (4)	0.0495 (16)
H11A	0.6596	0.4766	0.2675	0.059*
C12	0.5023 (7)	0.5759 (6)	0.3679 (5)	0.0502 (16)
H12A	0.5433	0.6512	0.3523	0.060*
C13	0.3690 (7)	0.5687 (5)	0.4428 (4)	0.0402 (14)
C14	0.2895 (8)	0.6719 (5)	0.4999 (5)	0.0506 (17)
H14A	0.3271	0.7488	0.4871	0.061*
C15	0.1615 (8)	0.6614 (5)	0.5718 (5)	0.0510 (16)
H15A	0.1133	0.7300	0.6087	0.061*
C16	0.0998 (6)	0.5446 (5)	0.5912 (4)	0.0369 (13)
C17	−0.0364 (7)	0.5321 (6)	0.6623 (4)	0.0488 (16)
H17A	−0.0880	0.5996	0.6993	0.059*
C18	−0.0919 (7)	0.4204 (6)	0.6763 (4)	0.0484 (15)
H18A	−0.1821	0.4102	0.7233	0.058*
C19	−0.0128 (6)	0.3208 (5)	0.6196 (4)	0.0408 (13)
H19A	−0.0522	0.2445	0.6299	0.049*
C20	0.1721 (6)	0.4420 (4)	0.5371 (4)	0.0327 (12)
C21	0.3114 (6)	0.4526 (4)	0.4619 (4)	0.0309 (11)
C22	0.0072 (5)	−0.0119 (4)	0.5524 (4)	0.0256 (10)
C23	0.4963 (6)	0.0410 (4)	0.5446 (3)	0.0267 (11)
C24	0.9473 (6)	0.6964 (5)	0.0006 (4)	0.0391 (13)
C25	0.8760 (7)	0.6869 (6)	0.1018 (5)	0.0538 (16)
H25A	0.8084	0.6285	0.1267	0.065*
C26	0.9099 (9)	0.7671 (6)	0.1628 (5)	0.065 (2)
H26A	0.8634	0.7639	0.2305	0.078*
C27	1.0133 (9)	0.8541 (6)	0.1253 (6)	0.069 (2)
H27A	1.0339	0.9063	0.1695	0.083*
C28	1.0843 (8)	0.8656 (6)	0.0280 (6)	0.0599 (19)
H28A	1.1532	0.9231	0.0039	0.072*
C29	1.0467 (7)	0.7848 (5)	−0.0342 (5)	0.0445 (14)
N1	0.3820 (5)	0.3495 (4)	0.4128 (3)	0.0297 (9)
N2	0.1159 (5)	0.3299 (4)	0.5516 (3)	0.0329 (10)
N3	0.9349 (6)	0.6333 (4)	−0.0780 (4)	0.0489 (13)
N4	1.0211 (6)	0.6779 (5)	−0.1586 (4)	0.0562 (14)
N5	1.0893 (6)	0.7689 (4)	−0.1338 (4)	0.0525 (13)
H5A	1.1518	0.8116	−0.1754	0.063*
O1W	0.2543 (5)	−0.0888 (4)	0.7141 (3)	0.0547 (11)
H4	0.3013	−0.0447	0.7410	0.082*
H5	0.2266	−0.0444	0.6707	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.0316 (2)	0.02563 (18)	0.0303 (2)	−0.00916 (14)	−0.00884 (16)	−0.00132 (14)
O1	0.062 (3)	0.047 (2)	0.043 (2)	−0.025 (2)	−0.018 (2)	−0.0085 (19)
O2	0.066 (3)	0.049 (2)	0.0216 (19)	−0.019 (2)	−0.0054 (19)	−0.0065 (17)
O4	0.060 (3)	0.049 (2)	0.029 (2)	−0.033 (2)	−0.002 (2)	−0.0009 (17)
O3	0.081 (3)	0.072 (3)	0.035 (2)	−0.051 (3)	−0.009 (2)	−0.008 (2)
O5	0.065 (3)	0.060 (3)	0.027 (2)	−0.038 (2)	−0.007 (2)	−0.0065 (19)
O6	0.058 (3)	0.058 (2)	0.030 (2)	−0.037 (2)	−0.006 (2)	−0.0001 (18)
O7	0.039 (2)	0.0296 (18)	0.0340 (19)	0.0001 (16)	−0.0165 (18)	−0.0099 (15)
O8	0.040 (2)	0.0326 (18)	0.0311 (19)	−0.0011 (16)	−0.0169 (18)	−0.0079 (15)
O9	0.035 (2)	0.045 (2)	0.0267 (18)	−0.0186 (17)	−0.0071 (17)	0.0048 (16)
O10	0.042 (2)	0.045 (2)	0.036 (2)	−0.0224 (18)	−0.0155 (18)	0.0042 (17)
C1	0.029 (3)	0.030 (2)	0.021 (2)	−0.006 (2)	−0.003 (2)	−0.004 (2)
C2	0.039 (3)	0.027 (2)	0.034 (3)	−0.011 (2)	−0.012 (3)	−0.004 (2)
C3	0.036 (3)	0.031 (3)	0.023 (2)	−0.006 (2)	−0.010 (2)	−0.006 (2)
C4	0.040 (3)	0.033 (3)	0.026 (3)	−0.005 (2)	−0.006 (2)	−0.001 (2)
C5	0.033 (3)	0.032 (3)	0.027 (3)	−0.009 (2)	−0.007 (2)	−0.003 (2)
C6	0.036 (3)	0.034 (3)	0.025 (3)	−0.012 (2)	−0.006 (2)	−0.005 (2)
C7	0.033 (3)	0.037 (3)	0.030 (3)	−0.011 (2)	−0.006 (2)	−0.004 (2)
C8	0.040 (3)	0.032 (3)	0.028 (3)	−0.002 (2)	−0.013 (3)	−0.003 (2)
C9	0.040 (3)	0.036 (3)	0.031 (3)	−0.012 (2)	−0.012 (3)	−0.002 (2)
C10	0.043 (3)	0.052 (3)	0.032 (3)	−0.016 (3)	−0.011 (3)	0.002 (3)
C11	0.044 (4)	0.071 (4)	0.039 (3)	−0.028 (3)	−0.015 (3)	0.014 (3)
C12	0.059 (4)	0.047 (3)	0.055 (4)	−0.028 (3)	−0.028 (4)	0.018 (3)
C13	0.047 (4)	0.034 (3)	0.052 (4)	−0.018 (3)	−0.032 (3)	0.008 (3)
C14	0.070 (5)	0.022 (3)	0.077 (5)	−0.011 (3)	−0.047 (4)	0.000 (3)
C15	0.064 (5)	0.031 (3)	0.066 (4)	0.002 (3)	−0.033 (4)	−0.014 (3)
C16	0.043 (3)	0.035 (3)	0.037 (3)	−0.002 (2)	−0.017 (3)	−0.009 (2)
C17	0.054 (4)	0.050 (4)	0.045 (4)	0.015 (3)	−0.021 (3)	−0.018 (3)
C18	0.039 (4)	0.069 (4)	0.033 (3)	0.000 (3)	−0.005 (3)	−0.004 (3)
C19	0.044 (4)	0.047 (3)	0.032 (3)	−0.008 (3)	−0.009 (3)	−0.001 (3)
C20	0.041 (3)	0.030 (3)	0.035 (3)	−0.002 (2)	−0.024 (3)	−0.002 (2)
C21	0.038 (3)	0.031 (3)	0.030 (3)	−0.010 (2)	−0.017 (3)	0.001 (2)
C22	0.023 (3)	0.025 (2)	0.030 (3)	−0.008 (2)	−0.006 (2)	−0.001 (2)
C23	0.034 (3)	0.027 (2)	0.020 (2)	−0.013 (2)	−0.005 (2)	−0.001 (2)
C24	0.043 (3)	0.037 (3)	0.045 (3)	−0.012 (3)	−0.023 (3)	0.002 (3)
C25	0.058 (4)	0.056 (4)	0.053 (4)	−0.016 (3)	−0.020 (4)	0.001 (3)
C26	0.084 (6)	0.067 (5)	0.055 (4)	−0.004 (4)	−0.036 (4)	−0.005 (4)
C27	0.082 (6)	0.051 (4)	0.092 (6)	−0.003 (4)	−0.050 (5)	−0.025 (4)
C28	0.060 (5)	0.039 (3)	0.095 (6)	−0.011 (3)	−0.042 (5)	−0.001 (4)
C29	0.042 (3)	0.035 (3)	0.060 (4)	−0.008 (3)	−0.020 (3)	0.004 (3)
N1	0.032 (2)	0.032 (2)	0.028 (2)	−0.0083 (19)	−0.010 (2)	−0.0023 (18)
N2	0.038 (3)	0.032 (2)	0.032 (2)	−0.0082 (19)	−0.013 (2)	−0.0004 (19)
N3	0.054 (3)	0.053 (3)	0.044 (3)	−0.029 (3)	−0.015 (3)	0.004 (2)
N4	0.063 (4)	0.057 (3)	0.053 (3)	−0.028 (3)	−0.018 (3)	0.003 (3)
N5	0.054 (3)	0.051 (3)	0.053 (3)	−0.024 (3)	−0.013 (3)	0.013 (3)
O1W	0.073 (3)	0.050 (2)	0.050 (3)	−0.028 (2)	−0.025 (2)	0.007 (2)

Geometric parameters (Å, º)

Cd1—O8^i	2.287 (3)	C12—C13	1.399 (8)
Cd1—N2	2.334 (4)	C12—H12A	0.9300
Cd1—O9^ii	2.347 (3)	C13—C21	1.407 (7)
Cd1—N1	2.351 (4)	C13—C14	1.425 (8)
Cd1—O7	2.357 (3)	C14—C15	1.348 (9)
Cd1—O10	2.440 (4)	C14—H14A	0.9300
Cd1—O5	2.525 (4)	C15—C16	1.431 (8)
O1—C8	1.213 (6)	C15—H15A	0.9300
O2—C8	1.316 (6)	C16—C20	1.383 (7)
O2—H1	0.8500	C16—C17	1.401 (8)
O4—C9	1.315 (6)	C17—C18	1.352 (8)
O4—H2	0.8500	C17—H17A	0.9300
O3—C9	1.201 (6)	C18—C19	1.393 (8)
O5—C7	1.214 (6)	C18—H18A	0.9300
O6—C7	1.319 (6)	C19—N2	1.324 (7)
O6—H3	0.8499	C19—H19A	0.9300
O7—C23	1.236 (6)	C20—N2	1.360 (6)
O8—C23	1.273 (5)	C20—C21	1.445 (7)
O8—Cd1^i	2.287 (3)	C21—N1	1.354 (6)
O9—C22	1.260 (6)	C22—C22^ii	1.534 (9)
O9—Cd1^ii	2.347 (3)	C23—C23^i	1.549 (9)
O10—C22	1.238 (5)	C24—N3	1.364 (7)
C1—C2	1.383 (6)	C24—C29	1.384 (7)
C1—C6	1.391 (6)	C24—C25	1.397 (8)
C1—C7	1.472 (7)	C25—C26	1.366 (8)
C2—C3	1.388 (7)	C25—H25A	0.9300
C2—H2A	0.9300	C26—C27	1.403 (10)
C3—C4	1.386 (7)	C26—H26A	0.9300
C3—C8	1.495 (6)	C27—C28	1.350 (10)
C4—C5	1.403 (7)	C27—H27A	0.9300
C4—H4A	0.9300	C28—C29	1.400 (8)
C5—C6	1.373 (7)	C28—H28A	0.9300
C5—C9	1.485 (7)	C29—N5	1.359 (8)
C6—H6A	0.9300	N3—N4	1.300 (7)
C10—N1	1.329 (7)	N4—N5	1.338 (6)
C10—C11	1.388 (8)	N5—H5A	0.8600
C10—H10A	0.9300	O1W—H4	0.8500
C11—C12	1.356 (9)	O1W—H5	0.8500
C11—H11A	0.9300
O8^i—Cd1—N2	161.05 (12)	C13—C12—H12A	120.2
O8^i—Cd1—O9^ii	87.86 (12)	C12—C13—C21	117.5 (5)
N2—Cd1—O9^ii	103.10 (14)	C12—C13—C14	123.6 (5)
O8^i—Cd1—N1	112.36 (14)	C21—C13—C14	118.9 (6)
N2—Cd1—N1	71.21 (15)	C15—C14—C13	122.0 (5)
O9^ii—Cd1—N1	133.31 (12)	C15—C14—H14A	119.0
O8^i—Cd1—O7	71.17 (11)	C13—C14—H14A	119.0
N2—Cd1—O7	91.26 (13)	C14—C15—C16	120.0 (5)
O9^ii—Cd1—O7	142.92 (12)	C14—C15—H15A	120.0
N1—Cd1—O7	83.60 (12)	C16—C15—H15A	120.0
O8^i—Cd1—O10	86.14 (13)	C20—C16—C17	118.6 (5)
N2—Cd1—O10	83.79 (14)	C20—C16—C15	120.2 (6)
O9^ii—Cd1—O10	68.08 (11)	C17—C16—C15	121.2 (5)
N1—Cd1—O10	149.68 (13)	C18—C17—C16	119.1 (5)
O7—Cd1—O10	79.99 (12)	C18—C17—H17A	120.5
O8^i—Cd1—O5	84.27 (13)	C16—C17—H17A	120.5
N2—Cd1—O5	113.84 (14)	C17—C18—C19	119.3 (6)
O9^ii—Cd1—O5	70.34 (12)	C17—C18—H18A	120.3
N1—Cd1—O5	70.51 (13)	C19—C18—H18A	120.3
O7—Cd1—O5	134.10 (13)	N2—C19—C18	122.9 (5)
O10—Cd1—O5	137.58 (12)	N2—C19—H19A	118.5
C8—O2—H1	110.0	C18—C19—H19A	118.5
C9—O4—H2	96.1	N2—C20—C16	122.1 (5)
C7—O5—Cd1	141.0 (3)	N2—C20—C21	118.1 (4)
C7—O6—H3	109.0	C16—C20—C21	119.8 (5)
C23—O7—Cd1	115.5 (3)	N1—C21—C13	122.5 (5)
C23—O8—Cd1^i	118.6 (3)	N1—C21—C20	118.3 (4)
C22—O9—Cd1^ii	120.8 (3)	C13—C21—C20	119.2 (5)
C22—O10—Cd1	116.4 (3)	O10—C22—O9	125.3 (4)
C2—C1—C6	119.7 (4)	O10—C22—C22^ii	119.1 (5)
C2—C1—C7	123.3 (4)	O9—C22—C22^ii	115.6 (5)
C6—C1—C7	117.0 (4)	O7—C23—O8	125.2 (4)
C1—C2—C3	119.7 (4)	O7—C23—C23^i	119.2 (5)
C1—C2—H2A	120.2	O8—C23—C23^i	115.6 (5)
C3—C2—H2A	120.2	N3—C24—C29	108.8 (5)
C4—C3—C2	120.7 (4)	N3—C24—C25	131.1 (5)
C4—C3—C8	121.0 (5)	C29—C24—C25	120.1 (5)
C2—C3—C8	118.3 (4)	C26—C25—C24	117.1 (6)
C3—C4—C5	119.5 (5)	C26—C25—H25A	121.4
C3—C4—H4A	120.2	C24—C25—H25A	121.4
C5—C4—H4A	120.2	C25—C26—C27	121.4 (7)
C6—C5—C4	119.3 (5)	C25—C26—H26A	119.3
C6—C5—C9	118.1 (4)	C27—C26—H26A	119.3
C4—C5—C9	122.6 (5)	C28—C27—C26	122.9 (6)
C5—C6—C1	121.2 (4)	C28—C27—H27A	118.5
C5—C6—H6A	119.4	C26—C27—H27A	118.5
C1—C6—H6A	119.4	C27—C28—C29	115.3 (6)
O5—C7—O6	121.9 (5)	C27—C28—H28A	122.3
O5—C7—C1	123.0 (5)	C29—C28—H28A	122.3
O6—C7—C1	115.1 (4)	N5—C29—C24	103.5 (5)
O1—C8—O2	123.7 (5)	N5—C29—C28	133.4 (6)
O1—C8—C3	122.3 (5)	C24—C29—C28	123.1 (6)
O2—C8—C3	114.0 (4)	C10—N1—C21	117.6 (4)
O3—C9—O4	123.4 (5)	C10—N1—Cd1	126.4 (4)
O3—C9—C5	121.7 (5)	C21—N1—Cd1	115.9 (3)
O4—C9—C5	114.9 (4)	C19—N2—C20	118.0 (5)
N1—C10—C11	123.5 (6)	C19—N2—Cd1	125.6 (4)
N1—C10—H10A	118.3	C20—N2—Cd1	116.4 (4)
C11—C10—H10A	118.3	N4—N3—C24	108.4 (5)
C12—C11—C10	119.2 (6)	N3—N4—N5	108.4 (5)
C12—C11—H11A	120.4	N4—N5—C29	110.9 (5)
C10—C11—H11A	120.4	N4—N5—H5A	124.5
C11—C12—C13	119.7 (5)	C29—N5—H5A	124.5
C11—C12—H12A	120.2	H4—O1W—H5	107.7

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H4···O1^iii	0.85	1.99	2.824 (5)	165
N5—H5A···O1W^iv	0.86	1.93	2.775 (6)	166
O6—H3···O9^ii	0.85	1.83	2.659 (5)	163
O2—H1···O8^v	0.85	1.79	2.636 (5)	172
O4—H2···N3	0.85	1.94	2.711 (6)	150
O1W—H5···O10	0.85	2.12	2.942 (5)	164

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