Tris(1,10-phenanthroline)cadmium 3,3′-dicarb­oxy-4,4′-diazenedi­yl­dibenzoate–4,4′-diazenediyldiphthalic acid–methanol (1/0.5/1)

Wang, J.; Lu, L.; Wei-Ping, W.; He, X.-Y.; Tao, W.

doi:10.1107/S160053681102068X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages m867-m868

doi:10.1107/S160053681102068X

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Tris(1,10-phenanthroline)cadmium 3,3′-dicarboxy-4,4′-diazenediyldibenzoate–4,4′-diazenediyldiphthalic acid–methanol (1/0.5/1)

Jun Wang,^a,^b ^* Lu Lu,^a,^b Wu Wei-Ping,^a,^b Xi-Yang He ^b and Wang Tao ^b

^aInstitute of Functionalized Materials, Sichuan University of Science and Engineering, Zigong 643000, People's Republic of China, and ^bCollege of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, People's Republic of China
^*Correspondence e-mail: scwangjun2011@126.com

(Received 9 May 2011; accepted 30 May 2011; online 11 June 2011)

In the title compoud, [Cd(C₁₂H₈N₂)₃](C₁₆H₈N₂O₈)·0.5C₁₆H₁₀N₂O₈·CH₃OH, the Cd^II atom has a distorted octahedral coordination formed by six N atoms from three separate phenanthroline ligands. One of the 4,4′-diazenediyldiphthalic acid molecules is arranged around an inversion center and possesses two –COOH groups, while the other is partially deprotonated and is a dianion for charge balance. It can be noted that, in the undeprotonated acid, the –COOH groups are disordered over two positions by rotation around the C—C bond linking the –COOH group to the phenyl ring. Surprisingly, the H atom is not involved in the disorder. In the dianion, the remaining H atom is located between the two COO groups. These deprotonated and undeprotonated molecules are linked by O—H⋯O hydrogen bonds, forming a chain developing parallel to the [111] direction. The methanol solvent molecule is highly disordered; it was not considered in the final model by elimination of its contribution from the intensity data.

Related literature

For background to crystal engineering, see: Yaghi et al. (2003 ); Kitagawa et al. (2004 ). For rigid carboxylic acids, see: Banerjee et al. (2008 ); Liu, Huang et al. (2011 ). For related chelating N-donor ligands, see: Liu, Jia & Wang (2011 ); Liu (2011 ); Breneman & Parker (1993 ).

Experimental

Crystal data

[Cd(C₁₂H₈N₂)₃](C₁₆H₈N₂O₈)·0.5C₁₆H₁₀N₂O₈·CH₄O
M_r = 1220.43
Triclinic, $[p \overline 1]$
a = 13.6902 (9) Å
b = 13.7659 (9) Å
c = 16.9518 (11) Å
α = 79.022 (1)°
β = 73.492 (1)°
γ = 64.439 (1)°
V = 2754.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 298 K
0.23 × 0.16 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.900, T_max = 0.968
21086 measured reflections
10030 independent reflections
8170 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.103
S = 1.07
9876 reflections
775 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O7	1.15	1.24	2.386 (4)	174
O10—H10A⋯O11	1.10	1.41	2.367 (4)	141

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 , 2010 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102068X/dn2688sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102068X/dn2688Isup2.hkl

checkCIF report

Comment top

In the past decade, much progress has been achieved in the synthesis and structural characterization of metal-organic frameworks(MOFs) due to their potential applications (Yaghi et al., 2003; Kitagawa et al., 2004). Generally, the multidentate organic ligands containing coordination sites of O donors are widely used as building blocks in the construction of MOFs (Banerjee et al., 2008; Liu, Huang et al., 2011). On the other hand, 1, 10-Phenanthroline, one of those ligands, has usually been used to construct a great variety of structurally interesting entities, such as monomers(Breneman & Parker, 1993; Liu, Jia & Wang, 2011; Liu, 2011). Herein, we are interested in self-assemblies of Cd(II) ion with H₄L and phenanthroline, which led to the preparation of the title compound.

In the asymmetric unit of title compound, there are one Cd(II) ion, three phen ligands, one deprotonated H₂L, a half undeprotonated H₄L ligand and one methanol molecule. As shown in Fig. 1. The Cd(II) atom is six-coordinated in a slightly distorted octahedral geometry defined by six N atoms from three different phen ligands. Interestingly, one of the (4,4'-diazenediyldiphthalic acid) is arranged around inversion center and possess two COOH groups, while the other is partially deprotonated and it is a dianion for balancing the charge. The Cd-N bond distances range from 2.329 (3) to 2.366 (3)Å. The N4-Cd1-N5 and N1-Cd1-N5 bond angles are 90.58 (9) and 93.19 (9)°, respectively. From the above values, it appears that the three phen ligands are nearly perpendicular to each other.

In H₂L, the acidic H atom is nearly engaged in a bridging O···H···O interactions (Table 1). Furthermore, The molecules of H₄L are linked by O-H···O hydrogen bonds to two H₂L on both sides, forming a one-dimensional chain with void parallel to the [1 1 1] direction (Fig. 2, Table 1). The disordered methanol molecule is located in the void. The Cd(II) complexes are antiparallel to the above chains. The above hydrogen bonds could participate to the stabilization of the title complex.

Related literature top

For background to crystal engineering, see: Yaghi et al. (2003); Kitagawa et al. (2004). For rigid carboxylic acids, see: Banerjee et al. (2008); Liu, Huang et al. (2011). For related chelating N-donor ligands, see: Liu, Jia & Wang (2011); Liu (2011); Breneman & Parker (1993).

Experimental top

The Cd(AC)₂.H₂O(19mg, 0.1mmol) was added dropwise slowly to ligand H₄L(16mg, 0.06mmol) and phen (20mg, 0.01mmol) methanol solution(15mL). The pH of the mixture solution was adjusted to about 3.5 with 2N HAC solution. Then, the reaction mixture was stirred for 15 days at room temperature. Crystals of (I) were obtained at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: APEX2 (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (van der Sluis & Spek, 1990; Spek, 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-labelling scheme. Thermal displacement are drawn at the 30% probability level. Only the major components of the disordered carboxylate groups are represented. H atoms have been omitted for clarity. [symmetric codes: -x+1, -y, -z+1].
	Fig. 2. View of the 1D chain formed by the O-H···O hydrogen bonds linking the H4L and H2L molecules. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

Tris(1,10-phenanthroline)cadmium 3,3'-dicarboxy-4,4'–diazenediyldibenzoate– 4,4'-diazenediyldiphthalic acid–methanol (1/0.5/1) top

Crystal data top

[Cd(C₁₂H₈N₂)₃](C₁₆H₈N₂O₈)·0.5C₁₆H₁₀N₂O₈·CH₄O	Z = 2
M_r = 1220.43	F(000) = 1244
Triclinic, p1	D_x = 1.471 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 13.6902 (9) Å	Cell parameters from 10030 reflections
b = 13.7659 (9) Å	θ = 2.4–25.2°
c = 16.9518 (11) Å	µ = 0.47 mm⁻¹
α = 79.022 (1)°	T = 298 K
β = 73.492 (1)°	Block, red
γ = 64.439 (1)°	0.23 × 0.16 × 0.07 mm
V = 2754.7 (3) Å³

Data collection top

Bruker APEXII area-detector diffractometer	10030 independent reflections
Radiation source: fine-focus sealed tube	8170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −16→16
T_min = 0.900, T_max = 0.968	k = −16→16
21086 measured reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0643P)²] where P = (F_o² + 2F_c²)/3
9876 reflections	(Δ/σ)_max = 0.002
775 parameters	Δρ_max = 0.66 e Å⁻³
10 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cd(C₁₂H₈N₂)₃](C₁₆H₈N₂O₈)·0.5C₁₆H₁₀N₂O₈·CH₄O	γ = 64.439 (1)°
M_r = 1220.43	V = 2754.7 (3) Å³
Triclinic, p1	Z = 2
a = 13.6902 (9) Å	Mo Kα radiation
b = 13.7659 (9) Å	µ = 0.47 mm⁻¹
c = 16.9518 (11) Å	T = 298 K
α = 79.022 (1)°	0.23 × 0.16 × 0.07 mm
β = 73.492 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	10030 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	8170 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.968	R_int = 0.021
21086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	10 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	Δρ_max = 0.66 e Å⁻³
9876 reflections	Δρ_min = −0.29 e Å⁻³
775 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cd1	0.194625 (14)	0.318919 (15)	0.770925 (10)	0.05192 (9)
N1	0.2000 (2)	0.34134 (18)	0.90344 (14)	0.0644 (6)
N2	0.01626 (18)	0.36033 (18)	0.85645 (13)	0.0572 (5)
N3	0.15295 (17)	0.48840 (18)	0.69513 (12)	0.0523 (5)
N4	0.36188 (17)	0.33952 (19)	0.70773 (13)	0.0564 (5)
N5	0.29240 (19)	0.12915 (19)	0.78538 (14)	0.0620 (6)
N6	0.16334 (18)	0.2430 (2)	0.67404 (13)	0.0606 (6)
C1	0.2886 (3)	0.3350 (3)	0.9249 (2)	0.0823 (10)
H1	0.3524	0.3293	0.8841	0.099*
C2	0.2888 (4)	0.3367 (3)	1.0074 (3)	0.1024 (14)
H2	0.3520	0.3315	1.0212	0.123*
C3	0.1961 (5)	0.3460 (3)	1.0661 (2)	0.1059 (16)
H3	0.1958	0.3469	1.1209	0.127*
C4	0.0990 (4)	0.3544 (2)	1.04590 (18)	0.0860 (12)
C5	−0.0037 (5)	0.3647 (3)	1.1045 (2)	0.1116 (18)
H5	−0.0082	0.3654	1.1602	0.134*
C6	−0.0918 (5)	0.3733 (3)	1.0815 (3)	0.1185 (18)
H6	−0.1566	0.3798	1.1214	0.142*
C7	−0.0899 (3)	0.3729 (2)	0.9969 (2)	0.0820 (10)
C8	−0.1819 (3)	0.3822 (3)	0.9691 (3)	0.1015 (14)
H8	−0.2486	0.3894	1.0067	0.122*
C9	−0.1726 (3)	0.3806 (3)	0.8892 (3)	0.0946 (12)
H9	−0.2326	0.3864	0.8704	0.114*
C10	−0.0726 (2)	0.3703 (2)	0.8339 (2)	0.0712 (8)
H10	−0.0679	0.3703	0.7781	0.085*
C11	0.0094 (3)	0.3614 (2)	0.93751 (16)	0.0601 (7)
C12	0.1051 (3)	0.3525 (2)	0.96180 (15)	0.0626 (8)
C13	0.0526 (2)	0.5588 (2)	0.68553 (16)	0.0583 (7)
H13	−0.0080	0.5412	0.7110	0.070*
C14	0.0339 (3)	0.6570 (3)	0.63954 (18)	0.0697 (8)
H14	−0.0374	0.7036	0.6338	0.084*
C15	0.1219 (3)	0.6841 (3)	0.60295 (18)	0.0750 (9)
H15	0.1111	0.7495	0.5713	0.090*
C16	0.2285 (3)	0.6139 (2)	0.61277 (17)	0.0660 (7)
C17	0.3245 (3)	0.6384 (3)	0.5782 (2)	0.0926 (11)
H17	0.3167	0.7045	0.5485	0.111*
C18	0.4240 (3)	0.5685 (4)	0.5879 (3)	0.0999 (12)
H18	0.4841	0.5879	0.5663	0.120*
C19	0.4426 (3)	0.4638 (3)	0.63071 (19)	0.0755 (9)
C20	0.5488 (3)	0.3843 (4)	0.6386 (2)	0.0932 (12)
H20	0.6116	0.3996	0.6170	0.112*
C21	0.5585 (3)	0.2864 (4)	0.6775 (2)	0.0920 (11)
H21	0.6279	0.2326	0.6811	0.110*
C22	0.4630 (2)	0.2680 (3)	0.71172 (19)	0.0726 (8)
H22	0.4705	0.2009	0.7394	0.087*
C23	0.3510 (2)	0.4370 (2)	0.66705 (15)	0.0566 (6)
C24	0.2412 (2)	0.5148 (2)	0.65882 (14)	0.0535 (6)
C25	0.3575 (3)	0.0734 (3)	0.8377 (2)	0.0772 (9)
H25	0.3637	0.1106	0.8752	0.093*
C26	0.4165 (3)	−0.0373 (3)	0.8390 (3)	0.0953 (12)
H26	0.4623	−0.0732	0.8758	0.114*
C27	0.4066 (3)	−0.0921 (3)	0.7864 (3)	0.1054 (15)
H27	0.4456	−0.1666	0.7869	0.126*
C28	0.3383 (3)	−0.0383 (3)	0.7308 (2)	0.0828 (10)
C29	0.3250 (4)	−0.0914 (4)	0.6713 (4)	0.1158 (17)
H29	0.3618	−0.1660	0.6700	0.139*
C30	0.2617 (4)	−0.0357 (4)	0.6188 (3)	0.1181 (18)
H30	0.2533	−0.0728	0.5824	0.142*
C31	0.2052 (3)	0.0796 (3)	0.6155 (2)	0.0846 (11)
C32	0.1410 (3)	0.1409 (4)	0.5584 (2)	0.0984 (13)
H32	0.1332	0.1070	0.5194	0.118*
C33	0.0908 (3)	0.2482 (4)	0.5601 (2)	0.0996 (14)
H33	0.0481	0.2894	0.5221	0.119*
C34	0.1026 (3)	0.2983 (3)	0.61885 (17)	0.0736 (9)
H34	0.0668	0.3730	0.6195	0.088*
C35	0.2147 (2)	0.1351 (3)	0.67309 (17)	0.0629 (7)
C36	0.2826 (2)	0.0746 (2)	0.73160 (18)	0.0635 (7)
N7	0.48610 (19)	0.04145 (17)	0.51715 (13)	0.0576 (5)
C37	0.4210 (2)	0.1386 (2)	0.47573 (14)	0.0520 (6)
C38	0.3927 (2)	0.2337 (2)	0.50901 (16)	0.0608 (7)
H38	0.4161	0.2321	0.5558	0.073*
C39	0.3303 (2)	0.3303 (2)	0.47330 (16)	0.0599 (7)
H39	0.3127	0.3939	0.4959	0.072*
C40	0.2928 (2)	0.3353 (2)	0.40435 (15)	0.0526 (6)
C43	0.2217 (3)	0.4439 (2)	0.3717 (2)	0.0631 (7)
O1	0.1197 (5)	0.4801 (7)	0.3911 (5)	0.095 (2)	0.65
O2	0.2763 (8)	0.4987 (8)	0.3310 (6)	0.089 (3)	0.65
H2A	0.2330	0.5659	0.3341	0.107*
O1B	0.1409 (11)	0.4604 (12)	0.3517 (11)	0.141 (8)	0.35
O2B	0.2661 (17)	0.5111 (14)	0.3622 (12)	0.099 (6)	0.35
C41	0.3216 (2)	0.2387 (2)	0.37008 (14)	0.0494 (6)
C44	0.2883 (2)	0.2380 (2)	0.29324 (17)	0.0586 (7)
O3	0.2267 (4)	0.3186 (3)	0.2611 (3)	0.0802 (12)	0.65
O4	0.3291 (4)	0.1439 (5)	0.2683 (4)	0.098 (2)	0.65
H4A	0.2887	0.1363	0.2425	0.117*
O3B	0.3059 (11)	0.2912 (9)	0.2303 (5)	0.116 (4)	0.35
O4B	0.2695 (8)	0.1541 (8)	0.2944 (6)	0.083 (3)	0.35
C42	0.3845 (2)	0.1411 (2)	0.40667 (15)	0.0517 (6)
H42	0.4023	0.0769	0.3848	0.062*
N12	0.06170 (18)	1.02786 (18)	0.86767 (13)	0.0547 (5)
N13	0.11991 (18)	0.94232 (17)	0.90151 (13)	0.0538 (5)
O5	−0.0929 (4)	0.9112 (3)	0.5944 (2)	0.1661 (18)
O6	−0.1637 (2)	1.0836 (2)	0.56001 (16)	0.1144 (10)
H6A	−0.1735	1.1648	0.5767	0.172*
O7	−0.18108 (17)	1.24773 (18)	0.60126 (13)	0.0793 (6)
O8	−0.1673 (2)	1.30459 (18)	0.70774 (17)	0.0948 (8)
O9	0.4026 (3)	0.6922 (2)	1.0424 (2)	0.1316 (12)
O10	0.4367 (2)	0.7670 (2)	1.1261 (2)	0.1290 (12)
H10A	0.4264	0.8509	1.1267	0.194*
O11	0.3728 (3)	0.9370 (2)	1.1782 (2)	0.1315 (12)
O12	0.2653 (3)	1.1037 (2)	1.15481 (17)	0.1148 (10)
C45	0.0172 (2)	1.0163 (2)	0.80526 (15)	0.0519 (6)
C46	0.0319 (3)	0.9203 (2)	0.78078 (19)	0.0736 (8)
H46	0.0727	0.8546	0.8060	0.088*
C47	−0.0152 (3)	0.9238 (3)	0.7178 (2)	0.0824 (10)
H47	−0.0078	0.8591	0.7026	0.099*
C48	−0.0734 (2)	1.0197 (2)	0.67622 (17)	0.0662 (8)
C49	−0.0908 (2)	1.1174 (2)	0.70260 (15)	0.0514 (6)
C50	−0.0443 (2)	1.1117 (2)	0.76747 (15)	0.0518 (6)
H50	−0.0556	1.1760	0.7860	0.062*
C51	−0.1117 (3)	1.0008 (3)	0.6058 (2)	0.0994 (12)
C52	−0.1511 (2)	1.2309 (2)	0.66752 (18)	0.0610 (7)
C53	0.1621 (2)	0.9608 (2)	0.96310 (15)	0.0488 (6)
C54	0.1289 (2)	1.0597 (2)	0.99084 (17)	0.0595 (7)
H54	0.0742	1.1203	0.9712	0.071*
C55	0.1778 (3)	1.0679 (2)	1.04835 (18)	0.0651 (7)
H55	0.1543	1.1352	1.0675	0.078*
C56	0.2602 (2)	0.9811 (2)	1.07910 (16)	0.0571 (6)
C57	0.2943 (2)	0.8789 (2)	1.05090 (16)	0.0546 (6)
C58	0.2426 (2)	0.8717 (2)	0.99353 (15)	0.0532 (6)
H58	0.2631	0.8046	0.9752	0.064*
C59	0.3030 (3)	1.0095 (3)	1.1414 (2)	0.0810 (9)
C60	0.3838 (3)	0.7717 (3)	1.0739 (2)	0.0827 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.05361 (13)	0.06166 (14)	0.04453 (12)	−0.02190 (9)	−0.01962 (8)	−0.00342 (8)
N1	0.0808 (16)	0.0558 (14)	0.0554 (13)	−0.0139 (12)	−0.0365 (12)	−0.0029 (10)
N2	0.0637 (14)	0.0519 (13)	0.0554 (12)	−0.0245 (11)	−0.0103 (10)	−0.0048 (10)
N3	0.0538 (12)	0.0627 (14)	0.0449 (11)	−0.0227 (11)	−0.0190 (9)	−0.0039 (10)
N4	0.0521 (12)	0.0708 (15)	0.0526 (12)	−0.0257 (11)	−0.0233 (10)	0.0007 (11)
N5	0.0610 (13)	0.0639 (15)	0.0584 (13)	−0.0244 (12)	−0.0127 (11)	−0.0012 (11)
N6	0.0547 (12)	0.0854 (18)	0.0498 (12)	−0.0323 (13)	−0.0129 (10)	−0.0117 (11)
C1	0.087 (2)	0.081 (2)	0.081 (2)	−0.0110 (18)	−0.0500 (18)	−0.0171 (17)
C2	0.135 (3)	0.078 (2)	0.100 (3)	−0.009 (2)	−0.084 (3)	−0.016 (2)
C3	0.192 (5)	0.053 (2)	0.065 (2)	−0.017 (2)	−0.069 (3)	−0.0049 (16)
C4	0.158 (3)	0.0394 (16)	0.0476 (16)	−0.0200 (19)	−0.038 (2)	−0.0007 (12)
C5	0.204 (5)	0.062 (2)	0.0389 (17)	−0.041 (3)	−0.003 (3)	−0.0063 (15)
C6	0.179 (5)	0.075 (3)	0.070 (3)	−0.053 (3)	0.027 (3)	−0.014 (2)
C7	0.111 (3)	0.0466 (17)	0.0665 (19)	−0.0316 (18)	0.0153 (18)	−0.0100 (14)
C8	0.088 (3)	0.076 (2)	0.126 (4)	−0.047 (2)	0.031 (2)	−0.027 (2)
C9	0.071 (2)	0.090 (3)	0.122 (3)	−0.042 (2)	0.007 (2)	−0.028 (2)
C10	0.0635 (18)	0.068 (2)	0.089 (2)	−0.0317 (15)	−0.0121 (16)	−0.0143 (16)
C11	0.0825 (19)	0.0346 (13)	0.0551 (15)	−0.0213 (13)	−0.0101 (14)	0.0010 (11)
C12	0.100 (2)	0.0324 (13)	0.0431 (14)	−0.0154 (14)	−0.0183 (14)	0.0010 (10)
C13	0.0577 (16)	0.0640 (18)	0.0541 (14)	−0.0205 (14)	−0.0224 (12)	−0.0019 (13)
C14	0.0742 (19)	0.068 (2)	0.0602 (17)	−0.0160 (16)	−0.0284 (15)	−0.0015 (14)
C15	0.097 (2)	0.0594 (19)	0.0598 (17)	−0.0251 (18)	−0.0210 (16)	0.0052 (14)
C16	0.078 (2)	0.0650 (19)	0.0563 (16)	−0.0317 (16)	−0.0158 (14)	0.0008 (13)
C17	0.100 (3)	0.084 (3)	0.094 (3)	−0.050 (2)	−0.015 (2)	0.014 (2)
C18	0.089 (3)	0.116 (3)	0.109 (3)	−0.066 (3)	−0.014 (2)	0.005 (2)
C19	0.0676 (19)	0.096 (2)	0.0718 (19)	−0.0449 (18)	−0.0179 (15)	0.0045 (17)
C20	0.061 (2)	0.136 (4)	0.095 (3)	−0.053 (2)	−0.0219 (18)	0.005 (2)
C21	0.0534 (18)	0.126 (3)	0.091 (2)	−0.033 (2)	−0.0298 (17)	0.018 (2)
C22	0.0569 (17)	0.090 (2)	0.0690 (18)	−0.0251 (16)	−0.0276 (14)	0.0075 (16)
C23	0.0578 (15)	0.0749 (19)	0.0478 (13)	−0.0322 (14)	−0.0185 (11)	−0.0052 (13)
C24	0.0620 (15)	0.0641 (17)	0.0421 (12)	−0.0283 (13)	−0.0173 (11)	−0.0054 (12)
C25	0.073 (2)	0.078 (2)	0.0716 (19)	−0.0264 (18)	−0.0208 (16)	0.0133 (16)
C26	0.074 (2)	0.078 (3)	0.105 (3)	−0.018 (2)	−0.014 (2)	0.018 (2)
C27	0.086 (3)	0.059 (2)	0.133 (4)	−0.023 (2)	0.015 (3)	0.004 (2)
C28	0.069 (2)	0.062 (2)	0.104 (3)	−0.0292 (17)	0.0109 (19)	−0.0153 (19)
C29	0.096 (3)	0.087 (3)	0.161 (5)	−0.045 (3)	0.018 (3)	−0.055 (3)
C30	0.105 (3)	0.128 (4)	0.144 (4)	−0.075 (3)	0.029 (3)	−0.080 (3)
C31	0.073 (2)	0.120 (3)	0.081 (2)	−0.060 (2)	0.0130 (17)	−0.048 (2)
C32	0.087 (2)	0.166 (4)	0.073 (2)	−0.072 (3)	−0.0019 (19)	−0.052 (3)
C33	0.079 (2)	0.180 (5)	0.0632 (19)	−0.063 (3)	−0.0178 (17)	−0.033 (2)
C34	0.0666 (18)	0.111 (3)	0.0562 (16)	−0.0403 (18)	−0.0193 (14)	−0.0155 (16)
C35	0.0541 (15)	0.084 (2)	0.0579 (16)	−0.0384 (15)	0.0067 (12)	−0.0243 (15)
C36	0.0571 (16)	0.0684 (19)	0.0662 (17)	−0.0337 (15)	0.0049 (13)	−0.0154 (14)
N7	0.0637 (13)	0.0574 (14)	0.0516 (12)	−0.0198 (12)	−0.0285 (10)	0.0084 (10)
C37	0.0526 (14)	0.0575 (16)	0.0452 (13)	−0.0186 (12)	−0.0207 (11)	0.0040 (11)
C38	0.0716 (17)	0.0683 (18)	0.0506 (14)	−0.0268 (15)	−0.0311 (13)	0.0003 (13)
C39	0.0719 (17)	0.0559 (17)	0.0599 (15)	−0.0240 (14)	−0.0277 (13)	−0.0074 (13)
C40	0.0526 (14)	0.0529 (15)	0.0550 (14)	−0.0199 (12)	−0.0217 (11)	0.0012 (12)
C43	0.0640 (19)	0.0543 (17)	0.0762 (19)	−0.0180 (15)	−0.0359 (16)	−0.0002 (14)
O1	0.060 (3)	0.084 (4)	0.140 (5)	−0.017 (2)	−0.045 (3)	−0.001 (3)
O2	0.070 (3)	0.063 (4)	0.114 (6)	−0.012 (2)	−0.031 (3)	0.019 (3)
O1B	0.150 (12)	0.061 (7)	0.27 (2)	−0.038 (8)	−0.175 (14)	0.028 (10)
O2B	0.113 (12)	0.055 (6)	0.163 (17)	−0.046 (8)	−0.094 (12)	0.039 (8)
C41	0.0494 (13)	0.0536 (15)	0.0466 (13)	−0.0177 (11)	−0.0212 (10)	0.0014 (11)
C44	0.0609 (16)	0.0626 (18)	0.0563 (16)	−0.0191 (15)	−0.0303 (13)	−0.0017 (14)
O3	0.109 (3)	0.065 (2)	0.069 (3)	−0.017 (2)	−0.059 (2)	0.0042 (19)
O4	0.103 (4)	0.081 (3)	0.108 (5)	0.004 (3)	−0.073 (3)	−0.033 (3)
O3B	0.216 (12)	0.129 (9)	0.073 (6)	−0.120 (9)	−0.090 (7)	0.048 (6)
O4B	0.138 (9)	0.080 (6)	0.077 (6)	−0.067 (7)	−0.066 (6)	0.014 (4)
C42	0.0540 (14)	0.0502 (15)	0.0501 (13)	−0.0155 (12)	−0.0215 (11)	−0.0008 (11)
N12	0.0634 (13)	0.0537 (13)	0.0542 (12)	−0.0239 (11)	−0.0294 (10)	0.0053 (10)
N13	0.0614 (13)	0.0530 (13)	0.0548 (12)	−0.0228 (11)	−0.0295 (10)	0.0027 (10)
O5	0.259 (4)	0.091 (2)	0.181 (3)	−0.015 (2)	−0.168 (3)	−0.038 (2)
O6	0.145 (2)	0.108 (2)	0.0991 (18)	−0.0198 (17)	−0.0903 (18)	−0.0079 (15)
O7	0.0750 (13)	0.0851 (15)	0.0726 (13)	−0.0197 (12)	−0.0455 (11)	0.0188 (11)
O8	0.123 (2)	0.0525 (13)	0.122 (2)	−0.0230 (13)	−0.0799 (17)	0.0138 (13)
O9	0.139 (3)	0.0675 (17)	0.177 (3)	0.0176 (16)	−0.102 (2)	−0.0270 (18)
O10	0.127 (2)	0.095 (2)	0.159 (3)	0.0114 (17)	−0.112 (2)	−0.0156 (18)
O11	0.159 (3)	0.101 (2)	0.163 (3)	−0.0201 (19)	−0.130 (2)	−0.0109 (19)
O12	0.187 (3)	0.0809 (18)	0.116 (2)	−0.0481 (19)	−0.107 (2)	−0.0005 (15)
C45	0.0580 (15)	0.0523 (15)	0.0498 (13)	−0.0201 (12)	−0.0269 (11)	0.0032 (11)
C46	0.097 (2)	0.0518 (17)	0.0747 (19)	−0.0153 (16)	−0.0518 (17)	0.0024 (14)
C47	0.113 (3)	0.0549 (18)	0.089 (2)	−0.0175 (18)	−0.059 (2)	−0.0120 (16)
C48	0.0746 (18)	0.0665 (19)	0.0618 (16)	−0.0175 (15)	−0.0382 (14)	−0.0072 (14)
C49	0.0473 (13)	0.0580 (16)	0.0498 (13)	−0.0184 (12)	−0.0221 (11)	0.0036 (11)
C50	0.0552 (14)	0.0515 (15)	0.0548 (14)	−0.0225 (12)	−0.0235 (11)	0.0014 (11)
C51	0.120 (3)	0.090 (3)	0.097 (3)	−0.016 (2)	−0.072 (2)	−0.018 (2)
C52	0.0511 (15)	0.0621 (18)	0.0705 (17)	−0.0218 (13)	−0.0271 (13)	0.0111 (14)
C53	0.0534 (14)	0.0505 (15)	0.0501 (13)	−0.0245 (12)	−0.0233 (11)	0.0052 (11)
C54	0.0721 (17)	0.0458 (15)	0.0662 (16)	−0.0172 (13)	−0.0413 (14)	0.0062 (12)
C55	0.089 (2)	0.0464 (15)	0.0704 (17)	−0.0236 (15)	−0.0430 (16)	0.0002 (13)
C56	0.0682 (17)	0.0582 (17)	0.0555 (15)	−0.0278 (14)	−0.0328 (13)	0.0067 (12)
C57	0.0543 (14)	0.0538 (16)	0.0586 (15)	−0.0196 (12)	−0.0272 (12)	0.0062 (12)
C58	0.0599 (15)	0.0466 (14)	0.0560 (14)	−0.0190 (12)	−0.0233 (12)	−0.0010 (11)
C59	0.111 (3)	0.074 (2)	0.081 (2)	−0.039 (2)	−0.061 (2)	0.0057 (17)
C60	0.076 (2)	0.068 (2)	0.095 (2)	−0.0058 (17)	−0.0465 (18)	−0.0026 (18)

Geometric parameters (Å, º) top

Cd1—N6	2.327 (2)	C31—C32	1.398 (6)
Cd1—N2	2.343 (2)	C31—C35	1.412 (4)
Cd1—N4	2.350 (2)	C32—C33	1.336 (6)
Cd1—N1	2.350 (2)	C32—H32	0.9300
Cd1—N3	2.355 (2)	C33—C34	1.395 (5)
Cd1—N5	2.367 (2)	C33—H33	0.9300
N1—C1	1.327 (4)	C34—H34	0.9300
N1—C12	1.358 (4)	C35—C36	1.443 (4)
N2—C10	1.321 (4)	N7—N7ⁱ	1.240 (4)
N2—C11	1.353 (3)	N7—C37	1.430 (3)
N3—C13	1.330 (3)	C37—C38	1.379 (4)
N3—C24	1.357 (3)	C37—C42	1.387 (3)
N4—C22	1.320 (4)	C38—C39	1.368 (4)
N4—C23	1.354 (3)	C38—H38	0.9300
N5—C25	1.331 (4)	C39—C40	1.383 (3)
N5—C36	1.353 (4)	C39—H39	0.9300
N6—C34	1.331 (4)	C40—C41	1.405 (4)
N6—C35	1.342 (4)	C40—C43	1.492 (4)
C1—C2	1.404 (5)	C43—O1B	1.164 (10)
C1—H1	0.9300	C43—O1	1.227 (6)
C2—C3	1.344 (6)	C43—O2	1.266 (7)
C2—H2	0.9300	C43—O2B	1.274 (12)
C3—C4	1.417 (6)	O2—H2A	0.8587
C3—H3	0.9300	O2B—H2A	0.8314
C4—C12	1.409 (4)	C41—C42	1.385 (3)
C4—C5	1.439 (6)	C41—C44	1.500 (3)
C5—C6	1.321 (6)	C44—O3B	1.201 (7)
C5—H5	0.9300	C44—O3	1.209 (5)
C6—C7	1.428 (6)	C44—O4	1.273 (6)
C6—H6	0.9300	C44—O4B	1.283 (9)
C7—C11	1.409 (4)	O4—H4A	0.8427
C7—C8	1.414 (6)	O4B—H4A	0.8941
C8—C9	1.328 (6)	C42—H42	0.9300
C8—H8	0.9300	N12—N13	1.242 (3)
C9—C10	1.388 (4)	N12—C45	1.425 (3)
C9—H9	0.9300	N13—C53	1.435 (3)
C10—H10	0.9300	O5—C51	1.189 (5)
C11—C12	1.432 (4)	O6—C51	1.298 (4)
C13—C14	1.383 (4)	O6—H6A	1.1480
C13—H13	0.9300	O7—C52	1.251 (3)
C14—C15	1.360 (4)	O7—H6A	1.2413
C14—H14	0.9300	O8—C52	1.236 (4)
C15—C16	1.397 (4)	O9—C60	1.203 (4)
C15—H15	0.9300	O10—C60	1.271 (4)
C16—C24	1.402 (4)	O10—H10A	1.1042
C16—C17	1.434 (5)	O11—C59	1.256 (4)
C17—C18	1.320 (5)	O11—H10A	1.4085
C17—H17	0.9300	O12—C59	1.212 (4)
C18—C19	1.435 (5)	C45—C50	1.369 (3)
C18—H18	0.9300	C45—C46	1.375 (4)
C19—C23	1.400 (4)	C46—C47	1.379 (4)
C19—C20	1.417 (5)	C46—H46	0.9300
C20—C21	1.351 (5)	C47—C48	1.390 (4)
C20—H20	0.9300	C47—H47	0.9300
C21—C22	1.381 (4)	C48—C49	1.400 (4)
C21—H21	0.9300	C48—C51	1.536 (4)
C22—H22	0.9300	C49—C50	1.394 (3)
C23—C24	1.449 (4)	C49—C52	1.513 (4)
C25—C26	1.382 (5)	C50—H50	0.9300
C25—H25	0.9300	C53—C54	1.366 (4)
C26—C27	1.340 (6)	C53—C58	1.379 (3)
C26—H26	0.9300	C54—C55	1.375 (4)
C27—C28	1.396 (6)	C54—H54	0.9300
C27—H27	0.9300	C55—C56	1.380 (4)
C28—C36	1.406 (4)	C55—H55	0.9300
C28—C29	1.444 (6)	C56—C57	1.410 (4)
C29—C30	1.318 (7)	C56—C59	1.522 (4)
C29—H29	0.9300	C57—C58	1.395 (3)
C30—C31	1.433 (6)	C57—C60	1.524 (4)
C30—H30	0.9300	C58—H58	0.9300

N6—Cd1—N2	94.62 (8)	C28—C29—H29	119.5
N6—Cd1—N4	105.02 (7)	C29—C30—C31	122.7 (4)
N2—Cd1—N4	157.03 (8)	C29—C30—H30	118.7
N6—Cd1—N1	155.72 (9)	C31—C30—H30	118.7
N2—Cd1—N1	71.50 (8)	C32—C31—C35	117.8 (4)
N4—Cd1—N1	93.53 (8)	C32—C31—C30	123.8 (4)
N6—Cd1—N3	93.24 (8)	C35—C31—C30	118.4 (4)
N2—Cd1—N3	96.00 (7)	C33—C32—C31	119.7 (3)
N4—Cd1—N3	71.47 (8)	C33—C32—H32	120.1
N1—Cd1—N3	107.65 (7)	C31—C32—H32	120.1
N6—Cd1—N5	71.49 (9)	C32—C33—C34	119.8 (4)
N2—Cd1—N5	107.14 (7)	C32—C33—H33	120.1
N4—Cd1—N5	90.59 (8)	C34—C33—H33	120.1
N1—Cd1—N5	93.15 (8)	N6—C34—C33	122.3 (4)
N3—Cd1—N5	152.94 (8)	N6—C34—H34	118.8
C1—N1—C12	119.9 (3)	C33—C34—H34	118.8
C1—N1—Cd1	125.3 (2)	N6—C35—C31	121.7 (3)
C12—N1—Cd1	114.47 (18)	N6—C35—C36	119.1 (2)
C10—N2—C11	118.5 (3)	C31—C35—C36	119.2 (3)
C10—N2—Cd1	125.79 (19)	N5—C36—C28	121.5 (3)
C11—N2—Cd1	115.24 (19)	N5—C36—C35	118.5 (3)
C13—N3—C24	118.3 (2)	C28—C36—C35	119.9 (3)
C13—N3—Cd1	126.23 (18)	N7ⁱ—N7—C37	114.0 (3)
C24—N3—Cd1	115.46 (16)	C38—C37—C42	119.8 (2)
C22—N4—C23	117.9 (2)	C38—C37—N7	116.4 (2)
C22—N4—Cd1	126.4 (2)	C42—C37—N7	123.9 (2)
C23—N4—Cd1	115.55 (16)	C39—C38—C37	120.1 (2)
C25—N5—C36	118.4 (3)	C39—C38—H38	119.9
C25—N5—Cd1	126.9 (2)	C37—C38—H38	119.9
C36—N5—Cd1	114.70 (19)	C38—C39—C40	121.4 (2)
C34—N6—C35	118.7 (3)	C38—C39—H39	119.3
C34—N6—Cd1	125.1 (2)	C40—C39—H39	119.3
C35—N6—Cd1	116.16 (18)	C39—C40—C41	118.7 (2)
N1—C1—C2	121.8 (4)	C39—C40—C43	117.5 (2)
N1—C1—H1	119.1	C41—C40—C43	123.7 (2)
C2—C1—H1	119.1	O1B—C43—O1	34.1 (9)
C3—C2—C1	119.0 (4)	O1B—C43—O2	115.9 (11)
C3—C2—H2	120.5	O1—C43—O2	123.8 (7)
C1—C2—H2	120.5	O1B—C43—O2B	125.6 (12)
C2—C3—C4	121.1 (3)	O1—C43—O2B	116.8 (11)
C2—C3—H3	119.4	O2—C43—O2B	24.9 (12)
C4—C3—H3	119.4	O1B—C43—C40	122.9 (9)
C12—C4—C3	116.6 (4)	O1—C43—C40	122.5 (5)
C12—C4—C5	118.4 (4)	O2—C43—C40	113.2 (6)
C3—C4—C5	125.0 (4)	O2B—C43—C40	111.2 (9)
C6—C5—C4	122.0 (4)	C43—O2—H2A	108.0
C6—C5—H5	119.0	C43—O2B—H2A	109.2
C4—C5—H5	119.0	C42—C41—C40	119.6 (2)
C5—C6—C7	121.5 (4)	C42—C41—C44	118.6 (2)
C5—C6—H6	119.2	C40—C41—C44	121.8 (2)
C7—C6—H6	119.2	O3B—C44—O3	48.8 (6)
C11—C7—C8	117.8 (3)	O3B—C44—O4	101.9 (7)
C11—C7—C6	118.5 (4)	O3—C44—O4	124.8 (4)
C8—C7—C6	123.7 (4)	O3B—C44—O4B	121.9 (7)
C9—C8—C7	119.7 (3)	O3—C44—O4B	113.5 (6)
C9—C8—H8	120.1	O4—C44—O4B	35.3 (5)
C7—C8—H8	120.1	O3B—C44—C41	123.7 (5)
C8—C9—C10	119.4 (4)	O3—C44—C41	122.6 (3)
C8—C9—H9	120.3	O4—C44—C41	112.5 (4)
C10—C9—H9	120.3	O4B—C44—C41	111.6 (5)
N2—C10—C9	123.4 (3)	C44—O4—H4A	112.4
N2—C10—H10	118.3	C44—O4B—H4A	107.8
C9—C10—H10	118.3	C41—C42—C37	120.3 (2)
N2—C11—C7	121.1 (3)	C41—C42—H42	119.8
N2—C11—C12	118.5 (2)	C37—C42—H42	119.8
C7—C11—C12	120.4 (3)	N13—N12—C45	115.8 (2)
N1—C12—C4	121.5 (3)	N12—N13—C53	112.3 (2)
N1—C12—C11	119.3 (2)	C51—O6—H6A	114.1
C4—C12—C11	119.2 (3)	C52—O7—H6A	113.3
N3—C13—C14	123.3 (3)	C60—O10—H10A	104.8
N3—C13—H13	118.3	C59—O11—H10A	104.9
C14—C13—H13	118.3	C50—C45—C46	119.4 (2)
C15—C14—C13	118.7 (3)	C50—C45—N12	114.6 (2)
C15—C14—H14	120.6	C46—C45—N12	125.9 (2)
C13—C14—H14	120.6	C45—C46—C47	118.4 (3)
C14—C15—C16	120.1 (3)	C45—C46—H46	120.8
C14—C15—H15	120.0	C47—C46—H46	120.8
C16—C15—H15	120.0	C46—C47—C48	123.0 (3)
C15—C16—C24	117.9 (3)	C46—C47—H47	118.5
C15—C16—C17	123.2 (3)	C48—C47—H47	118.5
C24—C16—C17	118.9 (3)	C47—C48—C49	118.5 (2)
C18—C17—C16	121.0 (3)	C47—C48—C51	112.5 (3)
C18—C17—H17	119.5	C49—C48—C51	128.9 (3)
C16—C17—H17	119.5	C50—C49—C48	117.3 (2)
C17—C18—C19	122.4 (3)	C50—C49—C52	114.5 (2)
C17—C18—H18	118.8	C48—C49—C52	128.1 (2)
C19—C18—H18	118.8	C45—C50—C49	123.3 (2)
C23—C19—C20	117.2 (3)	C45—C50—H50	118.4
C23—C19—C18	118.6 (3)	C49—C50—H50	118.4
C20—C19—C18	124.1 (3)	O5—C51—O6	121.7 (3)
C21—C20—C19	119.8 (3)	O5—C51—C48	119.4 (3)
C21—C20—H20	120.1	O6—C51—C48	118.8 (3)
C19—C20—H20	120.1	O8—C52—O7	122.8 (3)
C20—C21—C22	118.6 (3)	O8—C52—C49	115.9 (2)
C20—C21—H21	120.7	O7—C52—C49	121.3 (3)
C22—C21—H21	120.7	C54—C53—C58	119.8 (2)
N4—C22—C21	124.2 (3)	C54—C53—N13	124.1 (2)
N4—C22—H22	117.9	C58—C53—N13	116.1 (2)
C21—C22—H22	117.9	C53—C54—C55	118.8 (2)
N4—C23—C19	122.2 (3)	C53—C54—H54	120.6
N4—C23—C24	118.7 (2)	C55—C54—H54	120.6
C19—C23—C24	119.1 (3)	C54—C55—C56	123.2 (3)
N3—C24—C16	121.7 (2)	C54—C55—H55	118.4
N3—C24—C23	118.5 (2)	C56—C55—H55	118.4
C16—C24—C23	119.8 (2)	C55—C56—C57	118.1 (2)
N5—C25—C26	123.1 (4)	C55—C56—C59	114.0 (3)
N5—C25—H25	118.5	C57—C56—C59	127.8 (2)
C26—C25—H25	118.5	C58—C57—C56	117.9 (2)
C27—C26—C25	119.0 (4)	C58—C57—C60	113.7 (2)
C27—C26—H26	120.5	C56—C57—C60	128.5 (2)
C25—C26—H26	120.5	C53—C58—C57	122.2 (2)
C26—C27—C28	120.6 (4)	C53—C58—H58	118.9
C26—C27—H27	119.7	C57—C58—H58	118.9
C28—C27—H27	119.7	O12—C59—O11	122.1 (3)
C27—C28—C36	117.4 (4)	O12—C59—C56	117.3 (3)
C27—C28—C29	123.8 (4)	O11—C59—C56	120.6 (3)
C36—C28—C29	118.7 (4)	O9—C60—O10	120.9 (3)
C30—C29—C28	120.9 (4)	O9—C60—C57	119.1 (3)
C30—C29—H29	119.5	O10—C60—C57	119.9 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	1.15	1.24	2.386 (4)	174
O10—H10A···O11	1.10	1.41	2.367 (4)	141

Experimental details

Crystal data
Chemical formula	[Cd(C₁₂H₈N₂)₃](C₁₆H₈N₂O₈)·0.5C₁₆H₁₀N₂O₈·CH₄O
M_r	1220.43
Crystal system, space group	Triclinic, p1
Temperature (K)	298
a, b, c (Å)	13.6902 (9), 13.7659 (9), 16.9518 (11)
α, β, γ (°)	79.022 (1), 73.492 (1), 64.439 (1)
V (Å³)	2754.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.23 × 0.16 × 0.07

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.900, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	21086, 10030, 8170
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.103, 1.07
No. of reflections	9876
No. of parameters	775
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.29

Computer programs: APEX2 (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (van der Sluis & Spek, 1990; Spek, 2003), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006, 2010), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	1.15	1.24	2.386 (4)	174.3
O10—H10A···O11	1.10	1.41	2.367 (4)	140.5

Acknowledgements

We express our thanks for the great contribution of Professor Matthias Zeller to the refinement. The authors acknowledge financial assistance from Sichuan University of Science and Engineering, the Institute of Functionalized Materials (grant Nos. 2009xjkpL003 and 2010XJKYL005), the Education Committee of Sichuan Province (grant No. 09ZA057), and the Committee of Science and Technology of Sichuan Province (grant No. 2010GZ0130).

References

Banerjee, R., Phan, A., Wang, B., Knobler, C., Furukawa, F., O'Keffe, M. & Yaghi, O. M. (2008). Science, 319, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 67| Part 7| July 2011| Pages m867-m868

doi:10.1107/S160053681102068X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tris(1,10-phenanthroline)cadmium 3,3′-dicarb­­oxy-4,4′-diazenedi­yl­dibenzoate–4,4′-diazenediyldiphthalic acid–methanol (1/0.5/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Tris(1,10-phenanthroline)cadmium 3,3′-dicarboxy-4,4′-diazenediyldibenzoate–4,4′-diazenediyldiphthalic acid–methanol (1/0.5/1)