Bis(2,2′-bipyridine-κ2N,N′)bis­(1H-indole-2-carboxyl­ato-κ2O,O′)cadmium–2,2′-bipyridine–water (1/0.5/2)

Li, Y.-X.; Zhang, B.-S.; Zheng, M.

doi:10.1107/S1600536811021064

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages m879-m880

doi:10.1107/S1600536811021064

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Bis(2,2′-bipyridine-κ²N,N′)bis(1H-indole-2-carboxylato-κ²O,O′)cadmium–2,2′-bipyridine–water (1/0.5/2)

Yun-Xia Li,^a Bi-Song Zhang ^a ^* and Miao Zheng ^a

^aCollege of Pharmaceutics and Material Engineering, Jinhua College of Profession and Technology, Jinhua, Zhejiang 321007, People's Republic of China
^*Correspondence e-mail: zbs_jy@163.com

(Received 13 April 2011; accepted 1 June 2011; online 11 June 2011)

The asymmetric unit of title compound, [Cd(C₉H₆NO₂)₂(C₁₀H₈N₂)₂]·0.5C₁₀H₈N₂·2H₂O, consists of one complex molecule, one half of an uncoordinated 2,2′-bipyridine molecule and two solvent water molecules. The uncoordinated 2,2′-bipyridine molecule is located on a center of symmetry. Within the complex molecule, the Cd^II atom is coordinated by four N atoms from two 2,2′-bipyridine ligands and three O atoms from two 1H-indole-2-carboxylate anion ligands, completing a distorted CdN₄O₃ pentagonal bipyramid. The molecules are assembled into one-dimensional chains along the [100] direction through classical hydrogen bonds (O—H⋯N, N—H⋯O and O—H⋯O). The resulting chains are further connected into two-dimensional supramolecular layers parallel to the (110) direction by intermolecular classical hydrogen bonds (N—H⋯O and O—H⋯O) from adjacent chains. A three-dimensional supramolecular network is formed via interlayer and O—H⋯O hydrogen bonds.

Related literature

For general background, see: Dillon et al. (2003 ). For related cadmium(II) complexes with bipyridine and 1,10-phenanthroline ligands, see: Zhang et al. (2005 ); Lou & Zhang (2007 ).

Experimental

Crystal data

[Cd(C₉H₆NO₂)₂(C₁₀H₈N₂)₂]·0.5C₁₀H₈N₂·2H₂O
M_r = 859.19
Triclinic, $[P \overline 1]$
a = 11.513 (2) Å
b = 12.945 (3) Å
c = 14.302 (3) Å
α = 114.95 (3)°
β = 94.27 (3)°
γ = 93.84 (3)°
V = 1915.8 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 290 K
0.26 × 0.19 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.865, T_max = 0.963
15180 measured reflections
6724 independent reflections
4444 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 1.17
6724 reflections
515 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −1.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5C⋯O5ⁱ	0.86	2.09	2.892 (9)	155
N6—H6C⋯O2ⁱⁱ	0.86	2.00	2.801 (8)	156
O5—H5A⋯O6	0.82	1.96	2.748 (8)	161
O5—H5B⋯N7ⁱⁱⁱ	0.82	2.09	2.879 (8)	161
O6—H6A⋯O5^iv	0.82	2.01	2.781 (7)	156
O6—H6B⋯O3^v	0.82	1.95	2.778 (6)	174
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) x+1, y, z; (iv) -x+1, -y+2, -z+1; (v) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg & Putz, 2004 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021064/rk2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021064/rk2274Isup2.hkl

checkCIF report

Comment top

The indole-2-carboxylic acid moiety is present in a great number of molecules with a broad spectrum of pharmacological activity, anticonvulsant, antihypertensive and antifungal properties. It has been found that the biological activities of the therapeutic agents are considerably increased when they are bonded into metal complex molecules (Dillon et al., 2003). Cadmium(II) ion with 1.10-phenanthroline and pyridine ligands can respectively form CdN₄O₄ dodecahedron and CdN₄O₃ polyhedron complex molecules (Lou & Zhang, 2007, Zhang et al., 2005). In this paper, we report synthesis and structure of a new cadium coordination complex with indole-2-formic acid and 2,2'-bipyridine ligands. The crystal structure of the title compound consists of one complex Cd(C₁₀H₈N₂)₂(C₉H₇NO₂)₂ molecule, one half uncoordinated 2,2'-bipyridine molecule and two lattice water molecules (Fig. 1). The uncoordinated 2,2'-bipyridine molecule placed in the center of symmetry (0, 1, 1/2 ). In the complex molecule, the Cd^II atom is coordinated by four N atoms from two 2,2'-bipyridine ligands, three O atoms from two 2-indolyl-formic acid anions ligands, completing a distorted CdN₄O₃ pentagonal bipyramid. The equatorial positions of the Cd^II ion are occupied by two carboxylate O atoms (O3, O4) and three N atoms (N2, N1, N3) from different 2,2'-bipyridine molecules, and the axial ones by the other one N atom (N4) and one carboxylate O atom (O1). The Cd1—N bond length is 2.364 (4) Å to 2.450 (5) Å, and Cd1—O bond lengths are 2.239 (4) Å and 2.653 (4) Å. In the crystal structure, classical O5—H5B···N6, N6—H6C···O2ⁱⁱ and O6—H6A···O5^iv hydrogen bonding interactions (Table 1) form one-dimensional chains. The chains are connected with each other via intermolecular hydrogen bonds (N5—H5C···O5ⁱ, O6—H6A···O5^iv) from adjacent chains to form a two-dimensional layer (Fig. 2). Furthermore, a three-dimensional network is formed via intermolecular forces between layers and hydrogen bonds (O6—H6A···O5^iv). Symmetry codes: (i) x, y - 1, z; (ii) -x + 1, -y, -z; (iv) -x + 1, -y + 2, -z + 1.

Related literature top

For general background, see: Dillon et al. (2003). For related cadmium(II) complexes with bipyridine and 1,10-phenanthroline ligands, see: Zhang et al. (2005); Lou & Zhang (2007).

Experimental top

CdCl₂.6H₂O (0.11 g, 0.54 mmol) was dissolved in appropriate amount of water, and then 1M Na₂CO₃ solution was added. CdCO₃ was obtained by filtration, which was then washed with distilled water for 5 times. The freshly prepared CdCO₃, 2-indolyl-formic acid (0.0725 g, 0.5 mmol), 2,2'-bipyridine (0.0781 g, 0.5 mmol), CH₃OH/H₂O (v/v = 1:2, 15 ml) were mixed and stirred for 2.0 h. Subsequently, the resulting cream suspension was heated in a 23 ml Teflon-lined stainless steel autoclave at 433 K for 5800 min. After that, autoclave was cooled to room temperature according to the procedure at 2600 min. The solid was filtered off. The resulting filtrate was allowed to stand at room temperature, and slow evaporation for 4 months afforded colourless block single crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Symmetry code: (i) -x, -y + 2, -z + 1.
	Fig. 2. A packing diagram of the title compound. H atoms are omitted for clarity.

Bis(2,2'-bipyridine-κ²N,N')bis(1H-indole-2- carboxylato-κ²O,O')cadmium–2,2'-bipyridine–water (1/0.5/2) top

Crystal data top

[Cd(C₉H₆NO₂)₂(C₁₀H₈N₂)₂]·0.5C₁₀H₈N₂·2H₂O	Z = 2
M_r = 859.19	F(000) = 878
Triclinic, P1	D_x = 1.489 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.513 (2) Å	Cell parameters from 10384 reflections
b = 12.945 (3) Å	θ = 3.2–25°
c = 14.302 (3) Å	µ = 0.63 mm⁻¹
α = 114.95 (3)°	T = 290 K
β = 94.27 (3)°	Block, colourless
γ = 93.84 (3)°	0.26 × 0.19 × 0.06 mm
V = 1915.8 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	6724 independent reflections
Radiation source: fine-focus sealed tube	4444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→12
T_min = 0.865, T_max = 0.963	k = −15→15
15180 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.P)² + 4.4876P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
6724 reflections	Δρ_max = 1.26 e Å⁻³
515 parameters	Δρ_min = −1.55 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

Crystal data top

[Cd(C₉H₆NO₂)₂(C₁₀H₈N₂)₂]·0.5C₁₀H₈N₂·2H₂O	γ = 93.84 (3)°
M_r = 859.19	V = 1915.8 (9) Å³
Triclinic, P1	Z = 2
a = 11.513 (2) Å	Mo Kα radiation
b = 12.945 (3) Å	µ = 0.63 mm⁻¹
c = 14.302 (3) Å	T = 290 K
α = 114.95 (3)°	0.26 × 0.19 × 0.06 mm
β = 94.27 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6724 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4444 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.963	R_int = 0.058
15180 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.17	Δρ_max = 1.26 e Å⁻³
6724 reflections	Δρ_min = −1.55 e Å⁻³
515 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.36632 (4)	0.14575 (4)	0.19144 (3)	0.03937 (15)
N1	0.3953 (4)	0.3521 (4)	0.2404 (4)	0.0463 (12)
N2	0.3905 (4)	0.1847 (4)	0.0463 (3)	0.0414 (11)
N3	0.2855 (4)	0.2010 (4)	0.3542 (3)	0.0421 (11)
N4	0.1600 (4)	0.1689 (4)	0.1760 (4)	0.0512 (13)
N5	0.7181 (4)	0.2314 (4)	0.4379 (3)	0.0427 (11)
H5C	0.6805	0.1670	0.4272	0.051*
N6	0.2909 (4)	−0.2837 (4)	−0.0315 (3)	0.0460 (12)
H6C	0.3187	−0.2581	−0.0727	0.055*
N7	−0.1248 (4)	0.9667 (5)	0.4058 (4)	0.0660 (15)
O1	0.5438 (3)	0.1593 (3)	0.2739 (3)	0.0506 (10)
O2	0.6372 (3)	0.2675 (4)	0.2080 (3)	0.0620 (12)
O3	0.3234 (4)	−0.0430 (3)	0.2186 (3)	0.0583 (11)
O4	0.3252 (3)	−0.0426 (3)	0.0641 (3)	0.0558 (11)
O5	0.6427 (3)	1.0228 (3)	0.4546 (3)	0.0622 (12)
H5A	0.5887	0.9811	0.4117	0.093*
H5B	0.7061	0.9968	0.4473	0.093*
O6	0.4400 (4)	0.8833 (4)	0.3526 (3)	0.0711 (13)
H6A	0.3978	0.9092	0.3991	0.107*
H6B	0.4082	0.9014	0.3094	0.107*
C1	0.3993 (5)	0.4320 (5)	0.3376 (5)	0.0562 (17)
H1	0.3943	0.4085	0.3905	0.067*
C2	0.4103 (5)	0.5467 (6)	0.3634 (5)	0.0623 (18)
H2	0.4143	0.6000	0.4323	0.075*
C3	0.4153 (6)	0.5814 (5)	0.2856 (6)	0.0674 (19)
H3	0.4206	0.6588	0.3004	0.081*
C4	0.4124 (5)	0.4995 (6)	0.1847 (5)	0.0623 (18)
H4	0.4159	0.5215	0.1309	0.075*
C5	0.4043 (5)	0.3852 (5)	0.1639 (5)	0.0429 (14)
C6	0.4060 (4)	0.2936 (5)	0.0575 (4)	0.0413 (14)
C7	0.4251 (5)	0.3177 (6)	−0.0262 (5)	0.0568 (17)
H7	0.4340	0.3933	−0.0172	0.068*
C8	0.4309 (5)	0.2301 (6)	−0.1221 (5)	0.0570 (17)
H8	0.4443	0.2457	−0.1784	0.068*
C9	0.4166 (5)	0.1195 (6)	−0.1335 (5)	0.0501 (15)
H9	0.4205	0.0587	−0.1976	0.060*
C10	0.3961 (4)	0.0996 (5)	−0.0480 (5)	0.0464 (15)
H10	0.3857	0.0243	−0.0562	0.056*
C11	0.3500 (5)	0.2125 (5)	0.4401 (5)	0.0542 (16)
H11	0.4272	0.1958	0.4352	0.065*
C12	0.3092 (6)	0.2475 (6)	0.5350 (5)	0.0668 (19)
H12	0.3571	0.2540	0.5930	0.080*
C13	0.1967 (7)	0.2724 (6)	0.5417 (5)	0.070 (2)
H13	0.1667	0.2984	0.6054	0.084*
C14	0.1268 (6)	0.2589 (6)	0.4539 (5)	0.0622 (18)
H14	0.0492	0.2747	0.4579	0.075*
C15	0.1731 (5)	0.2216 (4)	0.3596 (4)	0.0415 (14)
C16	0.1037 (5)	0.2016 (5)	0.2606 (4)	0.0435 (14)
C17	−0.0148 (5)	0.2143 (6)	0.2558 (6)	0.0626 (18)
H17	−0.0530	0.2360	0.3151	0.075*
C18	−0.0748 (6)	0.1945 (7)	0.1626 (6)	0.083 (2)
H18	−0.1545	0.2021	0.1582	0.099*
C19	−0.0180 (6)	0.1636 (8)	0.0765 (6)	0.099 (3)
H19	−0.0570	0.1515	0.0129	0.119*
C20	0.1004 (5)	0.1506 (7)	0.0866 (5)	0.085 (3)
H20	0.1396	0.1280	0.0278	0.101*
C21	0.6248 (5)	0.2348 (5)	0.2767 (4)	0.0424 (14)
C22	0.7075 (4)	0.2856 (5)	0.3740 (4)	0.0406 (14)
C23	0.7796 (4)	0.3861 (5)	0.4152 (4)	0.0446 (14)
H23	0.7892	0.4380	0.3864	0.054*
C24	0.8374 (4)	0.3962 (5)	0.5108 (4)	0.0410 (14)
C25	0.9183 (5)	0.4786 (5)	0.5900 (5)	0.0546 (16)
H25	0.9451	0.5456	0.5856	0.066*
C26	0.9571 (5)	0.4596 (6)	0.6732 (5)	0.0598 (18)
H26	1.0104	0.5143	0.7256	0.072*
C27	0.9183 (5)	0.3594 (6)	0.6811 (5)	0.0600 (18)
H27	0.9473	0.3480	0.7381	0.072*
C28	0.8382 (5)	0.2776 (5)	0.6066 (5)	0.0538 (16)
H28	0.8114	0.2115	0.6126	0.065*
C29	0.7985 (4)	0.2967 (5)	0.5217 (4)	0.0400 (13)
C31	0.3117 (5)	−0.0931 (5)	0.1209 (5)	0.0449 (14)
C32	0.2787 (4)	−0.2191 (5)	0.0709 (4)	0.0392 (13)
C33	0.2308 (5)	−0.2888 (5)	0.1117 (5)	0.0524 (16)
H33	0.2147	−0.2664	0.1799	0.063*
C34	0.2103 (5)	−0.4011 (5)	0.0308 (4)	0.0480 (15)
C35	0.1611 (5)	−0.5075 (5)	0.0239 (5)	0.0614 (18)
H35	0.1328	−0.5130	0.0810	0.074*
C36	0.1561 (6)	−0.6015 (6)	−0.0683 (6)	0.074 (2)
H36	0.1226	−0.6717	−0.0742	0.088*
C37	0.1997 (6)	−0.5951 (6)	−0.1537 (6)	0.070 (2)
H37	0.1962	−0.6615	−0.2151	0.084*
C38	0.2484 (6)	−0.4927 (6)	−0.1504 (5)	0.0606 (17)
H38	0.2776	−0.4890	−0.2079	0.073*
C39	0.2515 (5)	−0.3961 (5)	−0.0576 (4)	0.0441 (14)
C41	−0.1487 (6)	0.9382 (7)	0.3045 (6)	0.083 (2)
H41	−0.2270	0.9264	0.2776	0.100*
C42	−0.0659 (7)	0.9251 (6)	0.2373 (6)	0.077 (2)
H42	−0.0875	0.9037	0.1671	0.092*
C43	0.0489 (6)	0.9446 (5)	0.2767 (5)	0.0643 (18)
H43	0.1077	0.9376	0.2339	0.077*
C44	0.0766 (5)	0.9749 (5)	0.3810 (5)	0.0550 (16)
H44	0.1547	0.9888	0.4090	0.066*
C45	−0.0117 (5)	0.9847 (5)	0.4443 (4)	0.0465 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0375 (2)	0.0444 (3)	0.0352 (2)	0.00611 (17)	0.00440 (16)	0.01586 (19)
N1	0.049 (3)	0.040 (3)	0.050 (3)	0.009 (2)	0.009 (2)	0.019 (3)
N2	0.042 (3)	0.044 (3)	0.036 (3)	0.009 (2)	0.005 (2)	0.015 (2)
N3	0.051 (3)	0.045 (3)	0.027 (3)	0.007 (2)	0.008 (2)	0.011 (2)
N4	0.035 (3)	0.075 (4)	0.043 (3)	0.014 (2)	0.006 (2)	0.023 (3)
N5	0.048 (3)	0.042 (3)	0.037 (3)	0.000 (2)	−0.002 (2)	0.018 (2)
N6	0.053 (3)	0.051 (3)	0.034 (3)	0.006 (2)	0.005 (2)	0.019 (3)
N7	0.047 (3)	0.085 (4)	0.063 (4)	0.000 (3)	−0.002 (3)	0.031 (3)
O1	0.042 (2)	0.050 (3)	0.056 (3)	0.0005 (19)	−0.0068 (19)	0.022 (2)
O2	0.048 (2)	0.101 (4)	0.048 (3)	0.000 (2)	0.006 (2)	0.044 (3)
O3	0.071 (3)	0.044 (3)	0.050 (3)	0.001 (2)	0.010 (2)	0.011 (2)
O4	0.063 (3)	0.047 (3)	0.070 (3)	0.007 (2)	0.010 (2)	0.036 (2)
O5	0.051 (2)	0.071 (3)	0.068 (3)	0.002 (2)	0.001 (2)	0.035 (3)
O6	0.083 (3)	0.072 (3)	0.054 (3)	−0.004 (3)	0.005 (2)	0.026 (3)
C1	0.069 (4)	0.047 (4)	0.044 (4)	0.008 (3)	0.019 (3)	0.009 (3)
C2	0.062 (4)	0.048 (4)	0.061 (5)	0.009 (3)	0.017 (3)	0.007 (4)
C3	0.074 (5)	0.033 (4)	0.088 (6)	0.008 (3)	0.013 (4)	0.018 (4)
C4	0.068 (4)	0.053 (4)	0.065 (5)	0.010 (3)	0.011 (3)	0.024 (4)
C5	0.039 (3)	0.037 (4)	0.055 (4)	0.010 (3)	0.003 (3)	0.022 (3)
C6	0.035 (3)	0.049 (4)	0.046 (4)	0.007 (3)	0.005 (3)	0.026 (3)
C7	0.064 (4)	0.056 (4)	0.061 (4)	0.007 (3)	0.009 (3)	0.035 (4)
C8	0.071 (4)	0.069 (5)	0.039 (4)	0.014 (4)	0.012 (3)	0.029 (4)
C9	0.045 (3)	0.063 (4)	0.042 (4)	0.018 (3)	0.008 (3)	0.021 (3)
C10	0.042 (3)	0.054 (4)	0.049 (4)	0.008 (3)	0.005 (3)	0.027 (3)
C11	0.059 (4)	0.062 (4)	0.040 (4)	0.007 (3)	0.009 (3)	0.020 (3)
C12	0.084 (5)	0.074 (5)	0.043 (4)	0.004 (4)	0.006 (4)	0.027 (4)
C13	0.098 (6)	0.070 (5)	0.046 (4)	0.023 (4)	0.029 (4)	0.023 (4)
C14	0.061 (4)	0.071 (5)	0.056 (4)	0.023 (4)	0.026 (3)	0.023 (4)
C15	0.044 (3)	0.034 (3)	0.046 (4)	0.007 (3)	0.017 (3)	0.014 (3)
C16	0.040 (3)	0.038 (3)	0.049 (4)	0.007 (3)	0.010 (3)	0.014 (3)
C17	0.039 (3)	0.076 (5)	0.076 (5)	0.016 (3)	0.018 (3)	0.031 (4)
C18	0.045 (4)	0.120 (7)	0.092 (6)	0.020 (4)	0.006 (4)	0.054 (6)
C19	0.052 (5)	0.179 (9)	0.074 (6)	0.018 (5)	−0.008 (4)	0.064 (6)
C20	0.046 (4)	0.156 (8)	0.053 (5)	0.018 (4)	0.001 (3)	0.045 (5)
C21	0.036 (3)	0.048 (4)	0.046 (4)	0.019 (3)	0.007 (3)	0.020 (3)
C22	0.033 (3)	0.055 (4)	0.035 (3)	0.009 (3)	0.007 (2)	0.019 (3)
C23	0.039 (3)	0.049 (4)	0.049 (4)	0.000 (3)	0.007 (3)	0.025 (3)
C24	0.035 (3)	0.044 (4)	0.043 (4)	0.003 (3)	0.006 (3)	0.018 (3)
C25	0.056 (4)	0.050 (4)	0.053 (4)	−0.007 (3)	0.001 (3)	0.020 (3)
C26	0.057 (4)	0.063 (5)	0.046 (4)	−0.012 (3)	−0.004 (3)	0.015 (4)
C27	0.050 (4)	0.076 (5)	0.053 (4)	−0.001 (3)	−0.007 (3)	0.030 (4)
C28	0.055 (4)	0.059 (4)	0.053 (4)	−0.002 (3)	−0.002 (3)	0.032 (4)
C29	0.037 (3)	0.047 (4)	0.037 (3)	0.002 (3)	0.004 (2)	0.020 (3)
C31	0.034 (3)	0.043 (4)	0.054 (4)	0.011 (3)	0.008 (3)	0.015 (3)
C32	0.042 (3)	0.037 (3)	0.037 (3)	0.008 (3)	0.008 (2)	0.013 (3)
C33	0.063 (4)	0.053 (4)	0.043 (4)	0.002 (3)	0.013 (3)	0.021 (3)
C34	0.048 (3)	0.046 (4)	0.044 (4)	0.004 (3)	0.003 (3)	0.015 (3)
C35	0.071 (4)	0.048 (4)	0.066 (5)	−0.004 (3)	0.009 (3)	0.027 (4)
C36	0.086 (5)	0.047 (5)	0.080 (6)	−0.005 (4)	−0.010 (4)	0.023 (4)
C37	0.094 (5)	0.043 (4)	0.057 (5)	0.008 (4)	−0.013 (4)	0.008 (4)
C38	0.075 (5)	0.062 (5)	0.039 (4)	0.013 (4)	−0.003 (3)	0.016 (4)
C39	0.046 (3)	0.045 (4)	0.036 (3)	0.003 (3)	−0.002 (3)	0.013 (3)
C41	0.058 (5)	0.114 (7)	0.067 (5)	−0.005 (4)	−0.007 (4)	0.033 (5)
C42	0.088 (6)	0.080 (6)	0.053 (5)	0.002 (4)	−0.001 (4)	0.022 (4)
C43	0.079 (5)	0.055 (4)	0.061 (5)	0.014 (4)	0.017 (4)	0.024 (4)
C44	0.048 (4)	0.052 (4)	0.070 (5)	0.007 (3)	0.007 (3)	0.030 (4)
C45	0.045 (3)	0.041 (4)	0.054 (4)	0.001 (3)	0.002 (3)	0.022 (3)

Geometric parameters (Å, º) top

Cd1—O1	2.239 (4)	C12—H12	0.9300
Cd1—O4	2.336 (4)	C13—C14	1.378 (9)
Cd1—N2	2.364 (4)	C13—H13	0.9300
Cd1—N3	2.408 (4)	C14—C15	1.389 (7)
Cd1—N4	2.419 (4)	C14—H14	0.9300
Cd1—N1	2.450 (5)	C15—C16	1.484 (8)
Cd1—O3	2.653 (4)	C16—C17	1.385 (7)
N1—C1	1.333 (7)	C17—C18	1.368 (9)
N1—C5	1.340 (7)	C17—H17	0.9300
N2—C10	1.344 (7)	C18—C19	1.357 (9)
N2—C6	1.347 (7)	C18—H18	0.9300
N3—C11	1.333 (7)	C19—C20	1.388 (9)
N3—C15	1.341 (6)	C19—H19	0.9300
N4—C20	1.325 (7)	C20—H20	0.9300
N4—C16	1.335 (7)	C21—C22	1.491 (7)
N5—C22	1.371 (6)	C22—C23	1.365 (7)
N5—C29	1.372 (6)	C23—C24	1.425 (7)
N5—H5C	0.8600	C23—H23	0.9300
N6—C32	1.370 (6)	C24—C25	1.407 (7)
N6—C39	1.375 (7)	C24—C29	1.410 (7)
N6—H6C	0.8600	C25—C26	1.364 (8)
N7—C41	1.336 (8)	C25—H25	0.9300
N7—C45	1.341 (7)	C26—C27	1.395 (8)
O1—C21	1.290 (6)	C26—H26	0.9300
O2—C21	1.236 (6)	C27—C28	1.371 (8)
O3—C31	1.261 (7)	C27—H27	0.9300
O4—C31	1.250 (7)	C28—C29	1.389 (7)
O5—H5A	0.8200	C28—H28	0.9300
O5—H5B	0.8200	C31—C32	1.486 (7)
O6—H6A	0.8200	C32—C33	1.372 (7)
O6—H6B	0.8200	C33—C34	1.415 (8)
C1—C2	1.364 (8)	C33—H33	0.9300
C1—H1	0.9300	C34—C39	1.408 (7)
C2—C3	1.368 (9)	C34—C35	1.413 (8)
C2—H2	0.9300	C35—C36	1.359 (9)
C3—C4	1.380 (8)	C35—H35	0.9300
C3—H3	0.9300	C36—C37	1.387 (9)
C4—C5	1.376 (8)	C36—H36	0.9300
C4—H4	0.9300	C37—C38	1.384 (9)
C5—C6	1.486 (8)	C37—H37	0.9300
C6—C7	1.387 (7)	C38—C39	1.383 (8)
C7—C8	1.373 (8)	C38—H38	0.9300
C7—H7	0.9300	C41—C42	1.371 (9)
C8—C9	1.368 (8)	C41—H41	0.9300
C8—H8	0.9300	C42—C43	1.361 (9)
C9—C10	1.384 (7)	C42—H42	0.9300
C9—H9	0.9300	C43—C44	1.377 (8)
C10—H10	0.9300	C43—H43	0.9300
C11—C12	1.369 (8)	C44—C45	1.389 (8)
C11—H11	0.9300	C44—H44	0.9300
C12—C13	1.356 (9)	C45—C45ⁱ	1.468 (11)

O1—Cd1—O4	107.11 (14)	N3—C15—C14	120.3 (5)
O1—Cd1—N2	108.36 (14)	N3—C15—C16	116.3 (5)
O4—Cd1—N2	82.76 (15)	C14—C15—C16	123.4 (5)
O1—Cd1—N3	89.13 (15)	N4—C16—C17	121.4 (6)
O4—Cd1—N3	119.52 (14)	N4—C16—C15	117.2 (5)
N2—Cd1—N3	146.91 (16)	C17—C16—C15	121.4 (5)
O1—Cd1—N4	156.39 (15)	C18—C17—C16	119.2 (6)
O4—Cd1—N4	89.06 (16)	C18—C17—H17	120.4
N2—Cd1—N4	90.32 (16)	C16—C17—H17	120.4
N3—Cd1—N4	67.69 (16)	C19—C18—C17	119.9 (6)
O1—Cd1—N1	89.04 (15)	C19—C18—H18	120.0
O4—Cd1—N1	150.16 (15)	C17—C18—H18	120.0
N2—Cd1—N1	68.19 (16)	C18—C19—C20	117.8 (7)
N3—Cd1—N1	84.76 (16)	C18—C19—H19	121.1
N4—Cd1—N1	84.58 (16)	C20—C19—H19	121.1
O1—Cd1—O3	84.88 (14)	N4—C20—C19	123.2 (6)
O4—Cd1—O3	52.23 (13)	N4—C20—H20	118.4
N2—Cd1—O3	134.85 (15)	C19—C20—H20	118.4
N3—Cd1—O3	72.87 (14)	O2—C21—O1	125.9 (5)
N4—Cd1—O3	92.11 (15)	O2—C21—C22	119.4 (5)
N1—Cd1—O3	156.86 (15)	O1—C21—C22	114.6 (5)
C1—N1—C5	118.9 (5)	C23—C22—N5	109.8 (5)
C1—N1—Cd1	123.7 (4)	C23—C22—C21	129.4 (5)
C5—N1—Cd1	117.4 (4)	N5—C22—C21	120.8 (5)
C10—N2—C6	118.2 (5)	C22—C23—C24	106.9 (5)
C10—N2—Cd1	121.1 (4)	C22—C23—H23	126.5
C6—N2—Cd1	120.6 (4)	C24—C23—H23	126.5
C11—N3—C15	118.6 (5)	C25—C24—C29	118.0 (5)
C11—N3—Cd1	121.7 (4)	C25—C24—C23	135.2 (5)
C15—N3—Cd1	119.7 (4)	C29—C24—C23	106.8 (5)
C20—N4—C16	118.5 (5)	C26—C25—C24	119.6 (6)
C20—N4—Cd1	122.5 (4)	C26—C25—H25	120.2
C16—N4—Cd1	119.1 (4)	C24—C25—H25	120.2
C22—N5—C29	108.8 (4)	C25—C26—C27	121.1 (6)
C22—N5—H5C	125.6	C25—C26—H26	119.4
C29—N5—H5C	125.6	C27—C26—H26	119.4
C32—N6—C39	109.0 (5)	C28—C27—C26	121.3 (6)
C32—N6—H6C	125.5	C28—C27—H27	119.3
C39—N6—H6C	125.5	C26—C27—H27	119.3
C41—N7—C45	117.4 (6)	C27—C28—C29	117.7 (6)
C21—O1—Cd1	119.1 (3)	C27—C28—H28	121.1
C31—O3—Cd1	84.5 (3)	C29—C28—H28	121.1
C31—O4—Cd1	99.5 (4)	N5—C29—C28	130.1 (5)
H5A—O5—H5B	114.5	N5—C29—C24	107.7 (5)
H6A—O6—H6B	100.4	C28—C29—C24	122.3 (5)
N1—C1—C2	123.1 (6)	O4—C31—O3	123.7 (6)
N1—C1—H1	118.4	O4—C31—C32	118.5 (5)
C2—C1—H1	118.4	O3—C31—C32	117.7 (5)
C1—C2—C3	118.5 (6)	N6—C32—C33	109.2 (5)
C1—C2—H2	120.7	N6—C32—C31	121.3 (5)
C3—C2—H2	120.7	C33—C32—C31	129.6 (5)
C2—C3—C4	118.9 (6)	C32—C33—C34	107.4 (5)
C2—C3—H3	120.6	C32—C33—H33	126.3
C4—C3—H3	120.6	C34—C33—H33	126.3
C5—C4—C3	119.9 (6)	C39—C34—C35	119.1 (6)
C5—C4—H4	120.0	C39—C34—C33	106.9 (5)
C3—C4—H4	120.0	C35—C34—C33	134.1 (6)
N1—C5—C4	120.6 (6)	C36—C35—C34	118.5 (6)
N1—C5—C6	117.1 (5)	C36—C35—H35	120.8
C4—C5—C6	122.3 (6)	C34—C35—H35	120.8
N2—C6—C7	121.1 (5)	C35—C36—C37	121.5 (6)
N2—C6—C5	116.5 (5)	C35—C36—H36	119.3
C7—C6—C5	122.3 (5)	C37—C36—H36	119.3
C8—C7—C6	120.1 (6)	C38—C37—C36	122.0 (6)
C8—C7—H7	119.9	C38—C37—H37	119.0
C6—C7—H7	119.9	C36—C37—H37	119.0
C9—C8—C7	118.9 (6)	C39—C38—C37	117.0 (6)
C9—C8—H8	120.6	C39—C38—H38	121.5
C7—C8—H8	120.6	C37—C38—H38	121.5
C8—C9—C10	119.0 (6)	N6—C39—C38	130.4 (6)
C8—C9—H9	120.5	N6—C39—C34	107.6 (5)
C10—C9—H9	120.5	C38—C39—C34	122.0 (6)
N2—C10—C9	122.7 (6)	N7—C41—C42	124.7 (7)
N2—C10—H10	118.7	N7—C41—H41	117.6
C9—C10—H10	118.7	C42—C41—H41	117.6
N3—C11—C12	123.9 (6)	C43—C42—C41	117.8 (7)
N3—C11—H11	118.1	C43—C42—H42	121.1
C12—C11—H11	118.1	C41—C42—H42	121.1
C13—C12—C11	117.8 (6)	C42—C43—C44	119.0 (6)
C13—C12—H12	121.1	C42—C43—H43	120.5
C11—C12—H12	121.1	C44—C43—H43	120.5
C12—C13—C14	119.9 (6)	C43—C44—C45	120.2 (6)
C12—C13—H13	120.1	C43—C44—H44	119.9
C14—C13—H13	120.1	C45—C44—H44	119.9
C13—C14—C15	119.5 (6)	N7—C45—C44	120.8 (6)
C13—C14—H14	120.2	N7—C45—C45ⁱ	116.2 (6)
C15—C14—H14	120.2	C44—C45—C45ⁱ	122.9 (7)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···O5ⁱⁱ	0.86	2.09	2.892 (9)	155
N6—H6C···O2ⁱⁱⁱ	0.86	2.00	2.801 (8)	156
O5—H5A···O6	0.82	1.96	2.748 (8)	161
O5—H5B···N7^iv	0.82	2.09	2.879 (8)	161
O6—H6A···O5^v	0.82	2.01	2.781 (7)	156
O6—H6B···O3^vi	0.82	1.95	2.778 (6)	174

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

Experimental details

Crystal data
Chemical formula	[Cd(C₉H₆NO₂)₂(C₁₀H₈N₂)₂]·0.5C₁₀H₈N₂·2H₂O
M_r	859.19
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	11.513 (2), 12.945 (3), 14.302 (3)
α, β, γ (°)	114.95 (3), 94.27 (3), 93.84 (3)
V (Å³)	1915.8 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.26 × 0.19 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.865, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	15180, 6724, 4444
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.17
No. of reflections	6724
No. of parameters	515
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.26, −1.55

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg & Putz, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···O5ⁱ	0.860	2.089	2.892 (9)	155
N6—H6C···O2ⁱⁱ	0.860	1.995	2.801 (8)	156
O5—H5A···O6	0.820	1.961	2.748 (8)	161
O5—H5B···N7ⁱⁱⁱ	0.820	2.090	2.879 (8)	161
O6—H6A···O5^iv	0.820	2.009	2.781 (7)	156
O6—H6B···O3^v	0.820	1.953	2.778 (6)	174

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

Acknowledgements

The authors gratefully acknowledge the financial support of the Education Office of Zhejiang province (grant No. 20051316) and the Scientific Research Fund of Ningbo University (grant No. XKL09078).

References

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