catena-Poly[[aqua­[1,4-bis­(1H-imidazol-4-yl)benzene]cadmium]-μ3-5-methyl­isophthalato]

Yang, S.-L.; Wang, D.-H.; Chen, S.-S.

doi:10.1107/S1600536811030509

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1174-m1175

doi:10.1107/S1600536811030509

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catena-Poly[[aqua[1,4-bis(1H-imidazol-4-yl)benzene]cadmium]-μ₃-5-methylisophthalato]

Sen-Lin Yang,^a De-Hai Wang ^a and Shui-Sheng Chen ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China
^*Correspondence e-mail: sscfync@163.com

(Received 20 July 2011; accepted 28 July 2011; online 2 August 2011)

In the title coordination polymer, [Cd(C₉H₆O₄)(C₁₂H₁₀N₄)(H₂O)]_n, the Cd^II atom has a NO₆ donor set and is coordinated by five carboxylate O atoms from three different 5-methyl-1,3-phenylenediacetate (pda²⁻) anions, one O atom from a water molecule and one N atom from a 1,4-bis(1H-imidazol-4-yl)benzene (L) ligand, displaying a highly distorted pentagonal–bipyramidal geometry. Each pda²⁻ anion acts as a μ₃-bridge, linking Cd^II atoms to form one-dimensional slabs extending parallel to [010]. In the crystal, adjacent molecules are linked through N—H⋯N and N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background to metal-organic hybrid materials, see: Bradshaw et al. (2005 ); Ockwig et al. (2005 ). For structures containing mixed ligands, see: Liu et al. (2007 ); Chen et al. (2006 ); Choi & Jeon (2003 ). For related structures, see: Chen et al. (2010 ; 2011 ).

Experimental

Crystal data

[Cd(C₉H₆O₄)(C₁₂H₁₀N₄)(H₂O)]
M_r = 518.80
Triclinic, $[P \overline 1]$
a = 6.9407 (9) Å
b = 9.8231 (13) Å
c = 15.506 (2) Å
α = 74.091 (2)°
β = 85.963 (2)°
γ = 70.707 (2)°
V = 959.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.815, T_max = 0.871
15863 measured reflections
4376 independent reflections
4161 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.128
S = 1.09
4376 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.222 (3)
Cd1—O1ⁱ	2.315 (3)
Cd1—O3ⁱⁱ	2.380 (3)
Cd1—O4ⁱⁱ	2.404 (2)
Cd1—O2ⁱ	2.473 (3)
Cd1—O5	2.520 (3)
Cd1—O3	2.539 (3)
Symmetry codes: (i) -x+1, -y-1, -z+2; (ii) -x+1, -y, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N4ⁱⁱⁱ	0.86	2.17	2.975 (4)	157
N3—H3⋯O4^iv	0.86	2.03	2.815 (4)	151
Symmetry codes: (iii) -x+2, -y, -z+1; (iv) -x+1, -y+1, -z+1.

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); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811030509/wm2517sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030509/wm2517Isup2.hkl

checkCIF report

Comment top

The rational design and synthesis of metal-organic frameworks (MOFs) has attracted considerable attention, which is stimulated by their intriguing aesthetic structures and topological features as well as their potential applications as materials (Bradshaw et al., 2005; Ockwig et al., 2005). The choice of suitable ligands is a key factor that greatly affects the structure and stabilization of the coordination architecture (Choi & Jeon 2003). For a more tunable ligand design mixed polycarboxylate and N-containing compounds (Liu et al., 2007; Chen et al., 2006) are favourable. Therefore we have focused on constructing complexes based on the organic ligand 1,4-di(1H-imidazol-4-yl)benzene (L) and polycarboxylate anions (Chen et al., 2010; 2011). As an extension of our work, we report the synthesis and structure of a new Cd^II complex (I), which was obtained by solvothermal reaction of CdI₂ with L and 5-methylisophthalic acid (H₂pda).

The asymmetric unit of (I) consists of one Cd^II atom, one L ligaqnd, one pda^2- anion and one coordinated water molecule. Each Cd^II atom has a NO₆ donor set and is coordinated by five carboxylate oxygen atoms from three different pda^2- anions, one water oxygen atom and one nitrogen atom from L, displaying a highly distorted pentagonal-bipyramidal geometry (Fig. 1). The pda^2- ligand acts as a µ₃– bridge with two monodentate carboxylate groups to form one-dimensional slabs parellel to [010] (Fig. 2). In the crystal, adjacent molecules are linked through N—H···N and N—H···O hydrogen bonding interactions into a three-dimensional network (Fig. 3).

Related literature top

For background to metal-organic hybrid materials, see: Bradshaw et al. (2005); Ockwig et al. (2005). For structures containing mixed ligands, see: Liu et al. (2007); Chen et al. (2006); Choi & Jeon (2003). For related structures, see: Chen et al. (2010; 2011).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. A mixture containing CdI₂ (36.6 mg, 0.1 mmol), L (21.0 mg, 0.1 mmol), H₂pda (18.0 mg, 0.1 mmol), DMF (N:N'- dimethylformamide, 1 ml), 10 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated at 453 K for 72 h. After cooling to room temperature within 12 h, colorless crystals of (I) suitable for X-ray diffraction analysis were obtained in 48% Yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination of the metal atom in compound (I). Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1 - x, -y, 2 - z (ii) x, 1 + y, z (iii) 1 - x, -1 - y, 2 - z.]
	Fig. 2. The slab formed from Cd^II atoms and pda^2- anions. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 3. The three-dimensional network formed by hydrogen bonding interactions in the structure of compound (I).

catena-Poly[[aqua[1,4-bis(1H-imidazol-4-yl)benzene]cadmium]- µ₃-5-methylisophthalato] top

Crystal data top

[Cd(C₉H₆O₄)(C₁₂H₁₀N₄)(H₂O)]	Z = 2
M_r = 518.80	F(000) = 516
Triclinic, P1	D_x = 1.789 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9407 (9) Å	Cell parameters from 9986 reflections
b = 9.8231 (13) Å	θ = 2.7–27.6°
c = 15.506 (2) Å	µ = 1.18 mm⁻¹
α = 74.091 (2)°	T = 296 K
β = 85.963 (2)°	Block, colorless
γ = 70.707 (2)°	0.18 × 0.16 × 0.12 mm
V = 959.4 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	4376 independent reflections
Radiation source: fine-focus sealed tube	4161 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→9
T_min = 0.815, T_max = 0.871	k = −12→12
15863 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.098P)² + 0.8397P] where P = (F_o² + 2F_c²)/3
4376 reflections	(Δ/σ)_max = 0.002
281 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[Cd(C₉H₆O₄)(C₁₂H₁₀N₄)(H₂O)]	γ = 70.707 (2)°
M_r = 518.80	V = 959.4 (2) Å³
Triclinic, P1	Z = 2
a = 6.9407 (9) Å	Mo Kα radiation
b = 9.8231 (13) Å	µ = 1.18 mm⁻¹
c = 15.506 (2) Å	T = 296 K
α = 74.091 (2)°	0.18 × 0.16 × 0.12 mm
β = 85.963 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4376 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4161 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.871	R_int = 0.022
15863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.09	Δρ_max = 0.86 e Å⁻³
4376 reflections	Δρ_min = −0.80 e Å⁻³
281 parameters

Special details top

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
Cd1	0.70159 (3)	−0.20380 (2)	1.035182 (12)	0.02480 (12)
C1	0.9950 (5)	0.1669 (4)	0.5262 (2)	0.0261 (6)
H1	1.0841	0.1400	0.4815	0.031*
C2	0.9908 (5)	0.0593 (4)	0.6057 (2)	0.0267 (6)
H2	1.0746	−0.0391	0.6127	0.032*
C3	0.8630 (5)	0.0969 (3)	0.6747 (2)	0.0241 (6)
C4	0.7404 (5)	0.2448 (4)	0.6627 (2)	0.0311 (7)
H4	0.6565	0.2726	0.7087	0.037*
C5	0.7415 (6)	0.3520 (4)	0.5827 (2)	0.0328 (7)
H5	0.6569	0.4503	0.5756	0.039*
C6	0.8676 (5)	0.3143 (3)	0.5130 (2)	0.0243 (6)
C7	0.8556 (4)	−0.0187 (3)	0.7570 (2)	0.0226 (5)
C8	0.7980 (5)	−0.0084 (3)	0.8415 (2)	0.0262 (6)
H8	0.7546	0.0796	0.8597	0.031*
C9	0.8833 (5)	−0.2419 (3)	0.8451 (2)	0.0254 (6)
H9	0.9102	−0.3448	0.8648	0.031*
C10	0.8657 (5)	0.4250 (3)	0.4273 (2)	0.0246 (6)
C11	0.7830 (6)	0.5769 (4)	0.4057 (2)	0.0338 (7)
H11	0.7115	0.6347	0.4433	0.041*
C12	0.9308 (6)	0.5092 (4)	0.2888 (2)	0.0350 (7)
H12	0.9784	0.5146	0.2308	0.042*
C13	0.3642 (4)	−0.1324 (3)	0.83307 (19)	0.0197 (5)
C14	0.3608 (4)	−0.2719 (3)	0.88386 (19)	0.0213 (5)
H14	0.3291	−0.2864	0.9443	0.026*
C15	0.4045 (4)	−0.3895 (3)	0.8449 (2)	0.0212 (5)
C16	0.4601 (5)	−0.3674 (3)	0.7544 (2)	0.0248 (6)
H16	0.4972	−0.4477	0.7290	0.030*
C17	0.4607 (5)	−0.2279 (3)	0.7021 (2)	0.0236 (6)
C18	0.4118 (4)	−0.1095 (3)	0.7421 (2)	0.0216 (5)
H18	0.4110	−0.0152	0.7081	0.026*
C19	0.3244 (4)	−0.0102 (3)	0.8788 (2)	0.0219 (5)
C20	0.3822 (5)	−0.5364 (3)	0.8978 (2)	0.0263 (6)
C21	0.5132 (6)	−0.2039 (4)	0.6041 (2)	0.0337 (7)
H21A	0.5255	−0.1060	0.5810	0.050*
H21B	0.4073	−0.2125	0.5714	0.050*
H21C	0.6403	−0.2780	0.5977	0.050*
N1	0.8142 (4)	−0.1499 (3)	0.89632 (18)	0.0255 (5)
N2	0.9098 (4)	−0.1684 (3)	0.76096 (17)	0.0245 (5)
H2A	0.9531	−0.2078	0.7172	0.029*
N3	0.8263 (5)	0.6276 (3)	0.3174 (2)	0.0344 (6)
H3	0.7919	0.7195	0.2862	0.041*
N4	0.9599 (5)	0.3820 (3)	0.35234 (18)	0.0317 (6)
O1	0.4754 (5)	−0.6519 (3)	0.87238 (19)	0.0408 (6)
O2	0.2711 (4)	−0.5384 (3)	0.9641 (2)	0.0344 (6)
O3	0.3531 (4)	−0.0476 (3)	0.96292 (17)	0.0282 (5)
O4	0.2703 (4)	0.1241 (3)	0.83420 (17)	0.0345 (5)
O5	1.0670 (4)	−0.3593 (3)	1.07976 (18)	0.0375 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04272 (18)	0.01512 (16)	0.01673 (15)	−0.01121 (11)	0.00698 (10)	−0.00380 (10)
C1	0.0299 (14)	0.0252 (15)	0.0192 (13)	−0.0072 (12)	0.0048 (11)	−0.0026 (11)
C2	0.0300 (14)	0.0203 (14)	0.0218 (14)	−0.0019 (11)	0.0034 (11)	−0.0013 (11)
C3	0.0292 (14)	0.0218 (14)	0.0177 (13)	−0.0080 (11)	0.0024 (11)	−0.0004 (11)
C4	0.0399 (17)	0.0245 (15)	0.0242 (15)	−0.0078 (13)	0.0128 (13)	−0.0051 (12)
C5	0.0430 (17)	0.0196 (14)	0.0275 (16)	−0.0039 (13)	0.0088 (13)	−0.0028 (12)
C6	0.0289 (14)	0.0229 (14)	0.0190 (13)	−0.0095 (11)	−0.0005 (11)	−0.0007 (11)
C7	0.0247 (13)	0.0199 (13)	0.0205 (13)	−0.0078 (10)	0.0034 (10)	−0.0013 (11)
C8	0.0343 (15)	0.0197 (14)	0.0225 (14)	−0.0081 (11)	0.0046 (11)	−0.0042 (11)
C9	0.0303 (14)	0.0192 (13)	0.0212 (14)	−0.0040 (11)	0.0037 (11)	−0.0022 (11)
C10	0.0309 (14)	0.0219 (14)	0.0207 (14)	−0.0108 (11)	0.0008 (11)	−0.0023 (11)
C11	0.0473 (19)	0.0228 (15)	0.0242 (15)	−0.0069 (13)	0.0038 (13)	−0.0013 (12)
C12	0.053 (2)	0.0300 (17)	0.0193 (15)	−0.0135 (15)	0.0011 (14)	−0.0014 (13)
C13	0.0239 (12)	0.0148 (12)	0.0210 (13)	−0.0068 (10)	−0.0010 (10)	−0.0047 (10)
C14	0.0256 (13)	0.0186 (13)	0.0170 (12)	−0.0055 (10)	0.0010 (10)	−0.0027 (10)
C15	0.0270 (13)	0.0142 (12)	0.0230 (14)	−0.0098 (10)	−0.0012 (10)	−0.0017 (10)
C16	0.0302 (14)	0.0202 (14)	0.0239 (14)	−0.0060 (11)	0.0038 (11)	−0.0088 (11)
C17	0.0280 (13)	0.0233 (14)	0.0192 (13)	−0.0074 (11)	0.0011 (10)	−0.0063 (11)
C18	0.0271 (13)	0.0170 (12)	0.0205 (13)	−0.0090 (10)	0.0001 (10)	−0.0021 (10)
C19	0.0268 (13)	0.0170 (13)	0.0237 (14)	−0.0083 (10)	0.0015 (10)	−0.0071 (11)
C20	0.0380 (16)	0.0144 (13)	0.0265 (15)	−0.0121 (11)	−0.0059 (12)	0.0006 (11)
C21	0.0416 (17)	0.0353 (18)	0.0250 (16)	−0.0131 (14)	0.0069 (13)	−0.0104 (13)
N1	0.0338 (13)	0.0205 (12)	0.0194 (12)	−0.0088 (10)	0.0043 (10)	−0.0019 (10)
N2	0.0289 (12)	0.0222 (12)	0.0177 (11)	−0.0036 (10)	0.0036 (9)	−0.0043 (9)
N3	0.0479 (16)	0.0234 (13)	0.0248 (14)	−0.0109 (12)	−0.0001 (12)	0.0040 (11)
N4	0.0429 (15)	0.0265 (14)	0.0190 (12)	−0.0070 (11)	0.0041 (11)	−0.0014 (11)
O1	0.0698 (18)	0.0153 (11)	0.0350 (13)	−0.0136 (11)	0.0124 (13)	−0.0058 (10)
O2	0.0423 (13)	0.0209 (12)	0.0370 (14)	−0.0133 (10)	0.0063 (11)	−0.0004 (10)
O3	0.0406 (13)	0.0226 (11)	0.0226 (12)	−0.0102 (9)	0.0013 (9)	−0.0081 (9)
O4	0.0589 (15)	0.0151 (10)	0.0270 (12)	−0.0103 (10)	0.0033 (11)	−0.0042 (9)
O5	0.0406 (13)	0.0366 (14)	0.0313 (13)	−0.0107 (11)	0.0052 (10)	−0.0063 (11)

Geometric parameters (Å, º) top

Cd1—N1	2.222 (3)	C11—H11	0.9300
Cd1—O1ⁱ	2.315 (3)	C12—N3	1.325 (5)
Cd1—O3ⁱⁱ	2.380 (3)	C12—N4	1.326 (4)
Cd1—O4ⁱⁱ	2.404 (2)	C12—H12	0.9300
Cd1—O2ⁱ	2.473 (3)	C13—C14	1.388 (4)
Cd1—O5	2.520 (3)	C13—C18	1.399 (4)
Cd1—O3	2.539 (3)	C13—C19	1.497 (4)
Cd1—C20ⁱ	2.716 (3)	C14—C15	1.384 (4)
Cd1—C19ⁱⁱ	2.735 (3)	C14—H14	0.9300
C1—C6	1.392 (4)	C15—C16	1.407 (4)
C1—C2	1.392 (4)	C15—C20	1.503 (4)
C1—H1	0.9300	C16—C17	1.389 (4)
C2—C3	1.391 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.399 (4)
C3—C4	1.388 (4)	C17—C21	1.510 (4)
C3—C7	1.469 (4)	C18—H18	0.9300
C4—C5	1.391 (5)	C19—O4	1.252 (4)
C4—H4	0.9300	C19—O3	1.266 (4)
C5—C6	1.394 (5)	C19—Cd1ⁱⁱ	2.735 (3)
C5—H5	0.9300	C20—O2	1.241 (5)
C6—C10	1.465 (4)	C20—O1	1.260 (4)
C7—C8	1.364 (4)	C20—Cd1ⁱ	2.716 (3)
C7—N2	1.377 (4)	C21—H21A	0.9600
C8—N1	1.389 (4)	C21—H21B	0.9600
C8—H8	0.9300	C21—H21C	0.9600
C9—N1	1.315 (4)	N2—H2A	0.8600
C9—N2	1.340 (4)	N3—H3	0.8600
C9—H9	0.9300	O1—Cd1ⁱ	2.315 (3)
C10—C11	1.362 (5)	O2—Cd1ⁱ	2.473 (3)
C10—N4	1.392 (4)	O3—Cd1ⁱⁱ	2.380 (3)
C11—N3	1.371 (5)	O4—Cd1ⁱⁱ	2.404 (2)

N1—Cd1—O1ⁱ	142.24 (10)	N2—C9—H9	124.3
N1—Cd1—O3ⁱⁱ	88.65 (10)	C11—C10—N4	109.0 (3)
O1ⁱ—Cd1—O3ⁱⁱ	121.73 (9)	C11—C10—C6	129.7 (3)
N1—Cd1—O4ⁱⁱ	133.01 (10)	N4—C10—C6	121.3 (3)
O1ⁱ—Cd1—O4ⁱⁱ	84.74 (9)	C10—C11—N3	106.4 (3)
O3ⁱⁱ—Cd1—O4ⁱⁱ	54.72 (8)	C10—C11—H11	126.8
N1—Cd1—O2ⁱ	93.84 (10)	N3—C11—H11	126.8
O1ⁱ—Cd1—O2ⁱ	54.45 (9)	N3—C12—N4	112.3 (3)
O3ⁱⁱ—Cd1—O2ⁱ	175.37 (8)	N3—C12—H12	123.8
O4ⁱⁱ—Cd1—O2ⁱ	125.04 (9)	N4—C12—H12	123.8
N1—Cd1—O5	86.01 (9)	C14—C13—C18	120.3 (3)
O1ⁱ—Cd1—O5	101.86 (10)	C14—C13—C19	118.4 (3)
O3ⁱⁱ—Cd1—O5	109.61 (10)	C18—C13—C19	121.2 (3)
O4ⁱⁱ—Cd1—O5	81.20 (9)	C15—C14—C13	120.2 (3)
O2ⁱ—Cd1—O5	74.49 (10)	C15—C14—H14	119.9
N1—Cd1—O3	84.46 (9)	C13—C14—H14	119.9
O1ⁱ—Cd1—O3	84.22 (10)	C14—C15—C16	119.2 (3)
O3ⁱⁱ—Cd1—O3	72.80 (10)	C14—C15—C20	120.1 (3)
O4ⁱⁱ—Cd1—O3	107.31 (9)	C16—C15—C20	120.6 (3)
O2ⁱ—Cd1—O3	103.55 (9)	C17—C16—C15	121.3 (3)
O5—Cd1—O3	170.12 (9)	C17—C16—H16	119.4
N1—Cd1—C20ⁱ	119.82 (10)	C15—C16—H16	119.4
O1ⁱ—Cd1—C20ⁱ	27.56 (10)	C16—C17—C18	118.7 (3)
O3ⁱⁱ—Cd1—C20ⁱ	149.23 (10)	C16—C17—C21	120.9 (3)
O4ⁱⁱ—Cd1—C20ⁱ	104.05 (9)	C18—C17—C21	120.5 (3)
O2ⁱ—Cd1—C20ⁱ	27.15 (10)	C13—C18—C17	120.2 (3)
O5—Cd1—C20ⁱ	85.50 (10)	C13—C18—H18	119.9
O3—Cd1—C20ⁱ	96.99 (9)	C17—C18—H18	119.9
N1—Cd1—C19ⁱⁱ	112.60 (10)	O4—C19—O3	121.7 (3)
O1ⁱ—Cd1—C19ⁱⁱ	103.13 (9)	O4—C19—C13	120.5 (3)
O3ⁱⁱ—Cd1—C19ⁱⁱ	27.54 (9)	O3—C19—C13	117.8 (3)
O4ⁱⁱ—Cd1—C19ⁱⁱ	27.23 (9)	O4—C19—Cd1ⁱⁱ	61.48 (16)
O2ⁱ—Cd1—C19ⁱⁱ	151.79 (10)	O3—C19—Cd1ⁱⁱ	60.39 (17)
O5—Cd1—C19ⁱⁱ	96.88 (9)	C13—C19—Cd1ⁱⁱ	173.5 (2)
O3—Cd1—C19ⁱⁱ	89.19 (8)	O2—C20—O1	122.8 (3)
C20ⁱ—Cd1—C19ⁱⁱ	127.55 (10)	O2—C20—C15	118.6 (3)
C6—C1—C2	120.8 (3)	O1—C20—C15	118.6 (3)
C6—C1—H1	119.6	O2—C20—Cd1ⁱ	65.48 (18)
C2—C1—H1	119.6	O1—C20—Cd1ⁱ	58.25 (17)
C3—C2—C1	120.9 (3)	C15—C20—Cd1ⁱ	168.7 (2)
C3—C2—H2	119.5	C17—C21—H21A	109.5
C1—C2—H2	119.5	C17—C21—H21B	109.5
C4—C3—C2	118.4 (3)	H21A—C21—H21B	109.5
C4—C3—C7	121.3 (3)	C17—C21—H21C	109.5
C2—C3—C7	120.3 (3)	H21A—C21—H21C	109.5
C3—C4—C5	120.7 (3)	H21B—C21—H21C	109.5
C3—C4—H4	119.6	C9—N1—C8	105.8 (3)
C5—C4—H4	119.6	C9—N1—Cd1	127.0 (2)
C4—C5—C6	121.0 (3)	C8—N1—Cd1	126.6 (2)
C4—C5—H5	119.5	C9—N2—C7	107.9 (3)
C6—C5—H5	119.5	C9—N2—H2A	126.1
C1—C6—C5	118.1 (3)	C7—N2—H2A	126.1
C1—C6—C10	120.3 (3)	C12—N3—C11	107.5 (3)
C5—C6—C10	121.6 (3)	C12—N3—H3	126.3
C8—C7—N2	105.6 (3)	C11—N3—H3	126.3
C8—C7—C3	131.0 (3)	C12—N4—C10	104.8 (3)
N2—C7—C3	123.3 (3)	C20—O1—Cd1ⁱ	94.2 (2)
C7—C8—N1	109.3 (3)	C20—O2—Cd1ⁱ	87.4 (2)
C7—C8—H8	125.4	C19—O3—Cd1ⁱⁱ	92.07 (19)
N1—C8—H8	125.4	C19—O3—Cd1	121.7 (2)
N1—C9—N2	111.4 (3)	Cd1ⁱⁱ—O3—Cd1	107.20 (10)
N1—C9—H9	124.3	C19—O4—Cd1ⁱⁱ	91.29 (19)

C6—C1—C2—C3	−1.6 (5)	O3ⁱⁱ—Cd1—N1—C9	178.6 (3)
C1—C2—C3—C4	−0.4 (5)	O4ⁱⁱ—Cd1—N1—C9	142.9 (2)
C1—C2—C3—C7	178.2 (3)	O2ⁱ—Cd1—N1—C9	−5.3 (3)
C2—C3—C4—C5	1.6 (5)	O5—Cd1—N1—C9	68.9 (3)
C7—C3—C4—C5	−176.9 (3)	O3—Cd1—N1—C9	−108.5 (3)
C3—C4—C5—C6	−0.9 (6)	C20ⁱ—Cd1—N1—C9	−13.6 (3)
C2—C1—C6—C5	2.3 (5)	C19ⁱⁱ—Cd1—N1—C9	164.7 (3)
C2—C1—C6—C10	−176.8 (3)	O1ⁱ—Cd1—N1—C8	134.4 (3)
C4—C5—C6—C1	−1.1 (5)	O3ⁱⁱ—Cd1—N1—C8	−11.6 (3)
C4—C5—C6—C10	178.0 (3)	O4ⁱⁱ—Cd1—N1—C8	−47.3 (3)
C4—C3—C7—C8	−24.4 (5)	O2ⁱ—Cd1—N1—C8	164.5 (3)
C2—C3—C7—C8	157.1 (3)	O5—Cd1—N1—C8	−121.4 (3)
C4—C3—C7—N2	155.1 (3)	O3—Cd1—N1—C8	61.3 (3)
C2—C3—C7—N2	−23.4 (5)	C20ⁱ—Cd1—N1—C8	156.2 (3)
N2—C7—C8—N1	−0.8 (4)	C19ⁱⁱ—Cd1—N1—C8	−25.5 (3)
C3—C7—C8—N1	178.8 (3)	N1—C9—N2—C7	0.3 (4)
C1—C6—C10—C11	−167.0 (4)	C8—C7—N2—C9	0.3 (3)
C5—C6—C10—C11	13.8 (6)	C3—C7—N2—C9	−179.3 (3)
C1—C6—C10—N4	12.0 (5)	N4—C12—N3—C11	0.2 (5)
C5—C6—C10—N4	−167.2 (3)	C10—C11—N3—C12	−0.1 (4)
N4—C10—C11—N3	0.0 (4)	N3—C12—N4—C10	−0.2 (4)
C6—C10—C11—N3	179.1 (3)	C11—C10—N4—C12	0.1 (4)
C18—C13—C14—C15	0.0 (4)	C6—C10—N4—C12	−179.0 (3)
C19—C13—C14—C15	−177.5 (3)	O2—C20—O1—Cd1ⁱ	11.8 (4)
C13—C14—C15—C16	2.5 (4)	C15—C20—O1—Cd1ⁱ	−167.5 (2)
C13—C14—C15—C20	−174.4 (3)	O1—C20—O2—Cd1ⁱ	−11.0 (3)
C14—C15—C16—C17	−3.7 (5)	C15—C20—O2—Cd1ⁱ	168.3 (2)
C20—C15—C16—C17	173.2 (3)	O4—C19—O3—Cd1ⁱⁱ	−5.0 (3)
C15—C16—C17—C18	2.3 (5)	C13—C19—O3—Cd1ⁱⁱ	172.9 (2)
C15—C16—C17—C21	−177.8 (3)	O4—C19—O3—Cd1	−116.8 (3)
C14—C13—C18—C17	−1.4 (4)	C13—C19—O3—Cd1	61.2 (3)
C19—C13—C18—C17	176.1 (3)	Cd1ⁱⁱ—C19—O3—Cd1	−111.7 (2)
C16—C17—C18—C13	0.2 (4)	N1—Cd1—O3—C19	13.3 (2)
C21—C17—C18—C13	−179.7 (3)	O1ⁱ—Cd1—O3—C19	−130.6 (2)
C14—C13—C19—O4	−160.2 (3)	O3ⁱⁱ—Cd1—O3—C19	103.6 (3)
C18—C13—C19—O4	22.3 (4)	O4ⁱⁱ—Cd1—O3—C19	146.8 (2)
C14—C13—C19—O3	21.8 (4)	O2ⁱ—Cd1—O3—C19	−79.3 (3)
C18—C13—C19—O3	−155.7 (3)	C20ⁱ—Cd1—O3—C19	−106.1 (2)
C14—C15—C20—O2	20.9 (4)	C19ⁱⁱ—Cd1—O3—C19	126.1 (2)
C16—C15—C20—O2	−156.0 (3)	N1—Cd1—O3—Cd1ⁱⁱ	−90.31 (11)
C14—C15—C20—O1	−159.8 (3)	O1ⁱ—Cd1—O3—Cd1ⁱⁱ	125.78 (11)
C16—C15—C20—O1	23.3 (4)	O3ⁱⁱ—Cd1—O3—Cd1ⁱⁱ	0.0
C14—C15—C20—Cd1ⁱ	129.5 (11)	O4ⁱⁱ—Cd1—O3—Cd1ⁱⁱ	43.14 (12)
C16—C15—C20—Cd1ⁱ	−47.4 (13)	O2ⁱ—Cd1—O3—Cd1ⁱⁱ	177.06 (8)
N2—C9—N1—C8	−0.8 (4)	C20ⁱ—Cd1—O3—Cd1ⁱⁱ	150.26 (11)
N2—C9—N1—Cd1	170.7 (2)	C19ⁱⁱ—Cd1—O3—Cd1ⁱⁱ	22.49 (11)
C7—C8—N1—C9	1.0 (4)	O3—C19—O4—Cd1ⁱⁱ	5.0 (3)
C7—C8—N1—Cd1	−170.6 (2)	C13—C19—O4—Cd1ⁱⁱ	−172.9 (2)
O1ⁱ—Cd1—N1—C9	−35.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱⁱⁱ	0.86	2.17	2.975 (4)	157
N3—H3···O4^iv	0.86	2.03	2.815 (4)	151

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

Experimental details

Crystal data
Chemical formula	[Cd(C₉H₆O₄)(C₁₂H₁₀N₄)(H₂O)]
M_r	518.80
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9407 (9), 9.8231 (13), 15.506 (2)
α, β, γ (°)	74.091 (2), 85.963 (2), 70.707 (2)
V (Å³)	959.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.815, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	15863, 4376, 4161
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.128, 1.09
No. of reflections	4376
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.80

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N1	2.222 (3)	Cd1—O2ⁱ	2.473 (3)
Cd1—O1ⁱ	2.315 (3)	Cd1—O5	2.520 (3)
Cd1—O3ⁱⁱ	2.380 (3)	Cd1—O3	2.539 (3)
Cd1—O4ⁱⁱ	2.404 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4ⁱⁱⁱ	0.86	2.17	2.975 (4)	156.6
N3—H3···O4^iv	0.86	2.03	2.815 (4)	150.5

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

Acknowledgements

This work was supported by the Natural Science Foundation of Anhui Provincial Education Commission (No. KJ2011B128).

References

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