Poly[[{μ2-3-[(1H-benzimidazol-1-yl)meth­yl]benzoato}cadmium(II)] 0.1-hydrate]

Duan, L.; Wu, X.-W.; Ma, J.-P.

doi:10.1107/S1600536810013292

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m530

https://doi.org/10.1107/S1600536810013292

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Poly[[{μ₂-3-[(1H-benzimidazol-1-yl)methyl]benzoato}cadmium(II)] 0.1-hydrate]

Li Duan,^a Xiang-Wen Wu ^b ^* and Jian-Ping Ma ^a

^aCollege of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, People's Republic of China, and ^bState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: xwwu@sdnu.edu.cn

(Received 25 March 2010; accepted 10 April 2010; online 17 April 2010)

In the title polymeric compound, {[Cd(C₁₅H₁₁N₂O₂)₂]·0.1H₂O}_n, the Cd^II atom is coordinated by four carboxylate O atoms and two benzimidazole N atoms from four benzimidazolylmethylbenzoate anions in a distorted octahedral geometry. Each anion bridges two Cd atoms through the terminal carboxylate group and an imidazole N atom, forming polymeric complex chains running along the b axis. The uncoordinated water molecule is equally disordered over two sites; occupancies were fixed as 0.5 for each disordered component. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the use of benzimidazoles and benzimidazole derivatives in the construction of metal-organic frameworks, see: Li et al. (2010 ); Vijayan et al. (2006 ).

Experimental

Crystal data

[Cd(C₁₅H₁₁N₂O₂)₂]·0.1H₂O
M_r = 616.72
Monoclinic, P 2₁ /c
a = 12.7770 (18) Å
b = 10.8304 (15) Å
c = 18.522 (3) Å
β = 95.007 (2)°
V = 2553.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 298 K
0.51 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.656, T_max = 0.813
13062 measured reflections
4754 independent reflections
4031 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.03
4754 reflections
370 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.3559 (17)
Cd1—O2	2.3669 (17)
Cd1—O3	2.4209 (19)
Cd1—O4	2.3063 (19)
Cd1—N1ⁱ	2.2801 (19)
Cd1—N4ⁱⁱ	2.283 (2)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱⁱⁱ	0.93	2.59	3.357 (3)	140
C14—H14⋯O4^iv	0.93	2.41	3.261 (3)	152
C23—H23B⋯O2^v	0.97	2.58	3.277 (3)	129
C29—H29⋯O3^v	0.93	2.57	3.424 (3)	154
Symmetry codes: (iii) x, y-1, z; (iv) -x+2, -y+1, -z; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013292/xu2743sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013292/xu2743Isup2.hkl

checkCIF report

Comment top

The rational design and synthesis of supramolecular complexes are of great interest not only because of their potential applications but also owing to their intriguing structures. Benzimidazole and benzimidazole-containing derivatives acted as one of the useful classes of organic building blocks to construct metal-organic frameworks (MOFs) (Li et al., 2010; Vijayan et al., 2006). Supramolecular complexes based on bent unsymmetric ligands containing benzimidazole and carboxylic acid groups have been less extensively studied, so these bent unsymmetric ligands offer great potential for creating novel frameworks. In the present work, the new bent organic ligand 3-[(1H-benzimidazole-1-yl)methyl]benzoic acid (HL) was employed in a self-assembly reaction with cadmium (II) iodide under hydrothermal conditions to create the novel supramolecular complex [Cd(C₁₅H₁₁N₂O₂)₂0.10(H₂O)]_n (I).

The compound structure of (I) is shown in Fig. 1. The asymmetric unit contains two L ligands, one Cd(II) and 0.10 water molecule. Compound (I) crystallizes with one unique six-coordinated Cd(II) center in a distorted octahedral {Cd N₂O₄} environment involving four O atoms from the carboxylate groups of two L ligands and two N atoms from benzimidazole of two other L ligands.

Neighboring Cd(II) ions are bound together by the carboxylate groups and terminal benzimidazole N donors of two L ligands to form a {Cd₂L₂} bimetallic ring in which the diagonal Cd···Cd separation is 9.907 (6) Å. The dihedral angle between benzimidazole ring and benzene ring is 87.618 (113)°. Small amounts of disordered water molecules are located in the bimetallic ring. Each Cd (II) center of the bimetallic ring is further bonded with two other bridging ligands resulting in a novel infinite one-dimensional extended chains structure in the crystallographic c axis. The Cd···Cd distance between adjacent bimetallic rings is 10.830 (2) Å, and the dihedral angle of benzimidazole ring and benzene ring of the ligand is 62.467 (82)°, it is worthy noted that the Cd···Cd distance is longer than that of in the bimetallic ring, which may be caused by the different features of the ligand. (Fig. 2).

In the solid state, when viewed down the crystallographic b axis, these one-dimensional chains are arranged in an ···AA··· fashion stack through interchain π-π interaction between two benzimidazole ring, the centroid-to-centroid distance of ca. 3.7 Å (Fig. 3).

Related literature top

For the use of benzimidazoles and benzimidazole derivatives in the construction of metal-organic frameworks, see: Li et al. (2010); Vijayan et al. (2006).

Experimental top

A mixture of 3-[(1H-benzimidazole-1-yl)methyl)methyl]benzoic acid (25.2 mg, 0.10 mmol), CdI₂ (12.7 mg, 0.10 mmol) and deionized water (2 ml) was sealed in a 5 ml Teflon-lined stainless steel reactor and heated at 453 K for 40 h, and then cooled slowly to room temperature over a period of 50 h. Colorless single crystals were obtained from the reaction mixture.

Structure description top

For the use of benzimidazoles and benzimidazole derivatives in the construction of metal-organic frameworks, see: Li et al. (2010); Vijayan et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment around the Cd atom, displacement ellipsoids drawn at 30% probability level [symmetry codes: (i) x, 1+y, z; (ii) 1-x, 2-y, -z].
	Fig. 2. One-dimensional chain structure of (I), disordered water molecules located in the bimetallic ring.

Poly[[{µ₂-3-[(1H-benzimidazol-1-yl)methyl]benzoato}cadmium(II)] 0.10-hydrate] top

Crystal data top

[Cd(C₁₅H₁₁N₂O₂)₂]·0.1H₂O	F(000) = 1244
M_r = 616.72	D_x = 1.604 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7057 reflections
a = 12.7770 (18) Å	θ = 2.2–28.2°
b = 10.8304 (15) Å	µ = 0.90 mm⁻¹
c = 18.522 (3) Å	T = 298 K
β = 95.007 (2)°	Block, colourless
V = 2553.4 (6) Å³	0.51 × 0.30 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4754 independent reflections
Radiation source: fine-focus sealed tube	4031 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→12
T_min = 0.656, T_max = 0.813	k = −13→13
13062 measured reflections	l = −22→18

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0389P)² + 0.9163P] where P = (F_o² + 2F_c²)/3
4754 reflections	(Δ/σ)_max = 0.002
370 parameters	Δρ_max = 0.63 e Å⁻³
7 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cd(C₁₅H₁₁N₂O₂)₂]·0.1H₂O	V = 2553.4 (6) Å³
M_r = 616.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7770 (18) Å	µ = 0.90 mm⁻¹
b = 10.8304 (15) Å	T = 298 K
c = 18.522 (3) Å	0.51 × 0.30 × 0.24 mm
β = 95.007 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4754 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4031 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.813	R_int = 0.025
13062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	7 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
4754 reflections	Δρ_min = −0.37 e Å⁻³
370 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 > 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	Occ. (<1)
C1	0.83100 (17)	0.53070 (18)	−0.16646 (13)	0.0324 (5)
C2	0.86797 (18)	0.41005 (19)	−0.19581 (12)	0.0346 (5)
C3	0.8300 (2)	0.3700 (2)	−0.26403 (13)	0.0435 (6)
H3	0.7817	0.4180	−0.2921	0.052*
C4	0.8635 (3)	0.2588 (2)	−0.29070 (15)	0.0490 (7)
H4	0.8373	0.2319	−0.3364	0.059*
C5	0.9362 (2)	0.1874 (2)	−0.24938 (14)	0.0454 (6)
H5	0.9596	0.1136	−0.2679	0.055*
C6	0.9740 (2)	0.2256 (2)	−0.18067 (14)	0.0377 (5)
C7	0.93982 (18)	0.33745 (19)	−0.15452 (12)	0.0348 (5)
H7	0.9655	0.3641	−0.1086	0.042*
C8	1.0543 (2)	0.1491 (2)	−0.13545 (15)	0.0452 (6)
H8A	1.1135	0.1331	−0.1635	0.054*
H8B	1.0799	0.1964	−0.0930	0.054*
C9	0.91692 (18)	−0.0199 (2)	−0.12756 (13)	0.0389 (5)
H9	0.8618	0.0210	−0.1536	0.047*
C10	1.00732 (18)	−0.1589 (2)	−0.06694 (12)	0.0360 (5)
C11	1.0459 (2)	−0.2654 (2)	−0.03163 (14)	0.0426 (6)
H11	1.0041	−0.3352	−0.0285	0.051*
C12	1.1482 (2)	−0.2631 (2)	−0.00163 (15)	0.0484 (7)
H12	1.1758	−0.3327	0.0225	0.058*
C13	1.2117 (2)	−0.1596 (3)	−0.00641 (14)	0.0531 (7)
H13	1.2804	−0.1619	0.0147	0.064*
C14	1.1756 (2)	−0.0534 (2)	−0.04155 (13)	0.0457 (6)
H14	1.2179	0.0158	−0.0448	0.055*
C15	1.07229 (18)	−0.0563 (2)	−0.07173 (12)	0.0363 (5)
C16	0.6286 (2)	0.73215 (19)	−0.00888 (14)	0.0364 (5)
C17	0.5579 (2)	0.7302 (2)	0.05285 (15)	0.0410 (6)
C18	0.4722 (2)	0.6511 (2)	0.05053 (14)	0.0466 (6)
H18	0.4578	0.5994	0.0108	0.056*
C19	0.4086 (2)	0.6485 (3)	0.10666 (16)	0.0529 (7)
H19	0.3518	0.5945	0.1050	0.063*
C20	0.4286 (2)	0.7260 (3)	0.16554 (17)	0.0509 (7)
H20	0.3849	0.7244	0.2031	0.061*
C21	0.51359 (19)	0.8060 (2)	0.16893 (13)	0.0432 (6)
C22	0.57828 (19)	0.8061 (2)	0.11322 (13)	0.0424 (6)
H22	0.6366	0.8577	0.1159	0.051*
C23	0.5332 (2)	0.8948 (3)	0.23165 (14)	0.0527 (7)
H23A	0.5402	0.8491	0.2769	0.063*
H23B	0.5983	0.9392	0.2272	0.063*
C24	0.4122 (2)	1.0601 (2)	0.17843 (14)	0.0486 (6)
H24	0.4465	1.0692	0.1365	0.058*
C25	0.30136 (18)	1.0798 (2)	0.25785 (13)	0.0392 (5)
C26	0.2184 (2)	1.1123 (2)	0.29766 (14)	0.0484 (6)
H26	0.1676	1.1688	0.2800	0.058*
C27	0.2144 (2)	1.0575 (3)	0.36398 (15)	0.0555 (7)
H27	0.1595	1.0771	0.3918	0.067*
C28	0.2903 (2)	0.9734 (3)	0.39098 (15)	0.0547 (7)
H28	0.2853	0.9395	0.4367	0.066*
C29	0.3723 (2)	0.9388 (2)	0.35230 (14)	0.0471 (6)
H29	0.4227	0.8821	0.3702	0.056*
C30	0.37558 (18)	0.9936 (2)	0.28477 (12)	0.0379 (5)
Cd1	0.763197 (14)	0.744630 (14)	−0.112674 (10)	0.03670 (8)
N1	0.90940 (15)	−0.13374 (17)	−0.10222 (10)	0.0377 (4)
N2	1.01240 (15)	0.03038 (16)	−0.11170 (10)	0.0366 (4)
N3	0.44586 (16)	0.98322 (19)	0.23252 (11)	0.0432 (5)
N4	0.32673 (16)	1.12095 (18)	0.19014 (11)	0.0452 (5)
O1	0.84916 (15)	0.55239 (15)	−0.10022 (10)	0.0514 (4)
O2	0.78223 (15)	0.60416 (16)	−0.20854 (10)	0.0521 (4)
O3	0.60131 (16)	0.6789 (2)	−0.06556 (11)	0.0643 (5)
O4	0.71415 (17)	0.7877 (2)	0.00157 (11)	0.0640 (6)
O1W	0.593 (5)	0.141 (6)	0.104 (3)	0.116 (19)	0.05
H1O1	0.6060	0.1156	0.0620	0.174*	0.05
H2O1	0.6303	0.2043	0.1160	0.174*	0.05
O2W	0.540 (8)	0.031 (8)	0.020 (3)	0.19 (5)	0.05
H1O2	0.5317	0.0676	−0.0208	0.283*	0.05
H2O2	0.5297	−0.0465	0.0190	0.283*	0.05

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0276 (11)	0.0245 (11)	0.0458 (13)	−0.0005 (9)	0.0073 (9)	0.0016 (10)
C2	0.0350 (12)	0.0288 (11)	0.0412 (12)	−0.0022 (9)	0.0100 (10)	0.0029 (9)
C3	0.0504 (15)	0.0370 (12)	0.0432 (14)	0.0018 (11)	0.0044 (11)	0.0055 (10)
C4	0.067 (2)	0.0428 (15)	0.0380 (14)	−0.0062 (12)	0.0084 (13)	−0.0037 (10)
C5	0.0568 (16)	0.0309 (12)	0.0505 (15)	0.0000 (11)	0.0158 (12)	−0.0062 (11)
C6	0.0386 (13)	0.0256 (11)	0.0503 (15)	−0.0008 (10)	0.0129 (11)	0.0036 (10)
C7	0.0372 (12)	0.0294 (11)	0.0385 (12)	−0.0044 (9)	0.0083 (10)	0.0007 (9)
C8	0.0419 (14)	0.0282 (11)	0.0662 (17)	−0.0012 (10)	0.0090 (12)	0.0062 (11)
C9	0.0350 (12)	0.0326 (12)	0.0493 (14)	0.0032 (10)	0.0046 (10)	0.0035 (10)
C10	0.0404 (13)	0.0336 (11)	0.0351 (12)	0.0027 (10)	0.0094 (10)	−0.0003 (9)
C11	0.0510 (16)	0.0365 (13)	0.0414 (14)	0.0029 (11)	0.0095 (12)	0.0054 (10)
C12	0.0550 (17)	0.0471 (15)	0.0434 (15)	0.0145 (12)	0.0051 (12)	0.0107 (11)
C13	0.0462 (15)	0.0593 (17)	0.0524 (16)	0.0098 (13)	−0.0042 (12)	0.0031 (13)
C14	0.0447 (14)	0.0426 (13)	0.0497 (14)	−0.0023 (11)	0.0042 (11)	−0.0030 (11)
C15	0.0412 (13)	0.0304 (11)	0.0378 (12)	0.0042 (10)	0.0061 (10)	−0.0023 (9)
C16	0.0384 (13)	0.0269 (11)	0.0452 (14)	−0.0031 (9)	0.0112 (11)	−0.0023 (10)
C17	0.0385 (14)	0.0345 (12)	0.0509 (15)	0.0034 (10)	0.0084 (11)	0.0027 (10)
C18	0.0459 (15)	0.0400 (13)	0.0541 (15)	−0.0020 (11)	0.0059 (12)	−0.0005 (11)
C19	0.0378 (14)	0.0499 (15)	0.0721 (19)	−0.0043 (12)	0.0115 (13)	0.0071 (14)
C20	0.0416 (15)	0.0574 (16)	0.0559 (17)	0.0085 (13)	0.0164 (13)	0.0101 (13)
C21	0.0366 (13)	0.0459 (14)	0.0474 (14)	0.0140 (11)	0.0049 (11)	0.0039 (12)
C22	0.0368 (13)	0.0391 (13)	0.0517 (15)	0.0029 (11)	0.0059 (11)	−0.0013 (11)
C23	0.0418 (15)	0.0668 (18)	0.0492 (15)	0.0196 (13)	0.0020 (11)	−0.0045 (13)
C24	0.0482 (15)	0.0547 (15)	0.0440 (14)	0.0086 (13)	0.0100 (11)	0.0013 (12)
C25	0.0355 (12)	0.0361 (12)	0.0461 (13)	0.0013 (10)	0.0033 (10)	−0.0067 (10)
C26	0.0395 (14)	0.0475 (14)	0.0584 (16)	0.0066 (12)	0.0058 (12)	−0.0059 (12)
C27	0.0398 (14)	0.0694 (18)	0.0588 (17)	0.0026 (14)	0.0134 (12)	−0.0082 (14)
C28	0.0491 (16)	0.0676 (19)	0.0482 (15)	−0.0075 (14)	0.0084 (12)	0.0032 (13)
C29	0.0426 (14)	0.0488 (14)	0.0492 (15)	0.0010 (12)	0.0001 (11)	0.0005 (12)
C30	0.0337 (12)	0.0384 (12)	0.0413 (13)	0.0008 (10)	0.0016 (10)	−0.0059 (10)
Cd1	0.03766 (12)	0.02956 (11)	0.04360 (12)	0.00121 (7)	0.00763 (8)	−0.00008 (7)
N1	0.0387 (11)	0.0303 (10)	0.0445 (11)	−0.0010 (8)	0.0060 (8)	0.0040 (8)
N2	0.0372 (11)	0.0261 (9)	0.0472 (11)	0.0011 (8)	0.0074 (8)	0.0017 (8)
N3	0.0388 (11)	0.0478 (12)	0.0430 (11)	0.0139 (9)	0.0037 (9)	−0.0014 (9)
N4	0.0440 (12)	0.0424 (11)	0.0493 (12)	0.0095 (10)	0.0047 (9)	0.0013 (9)
O1	0.0683 (13)	0.0342 (9)	0.0515 (11)	0.0076 (9)	0.0046 (9)	−0.0052 (8)
O2	0.0575 (11)	0.0395 (9)	0.0585 (11)	0.0113 (9)	0.0012 (9)	−0.0032 (8)
O3	0.0602 (13)	0.0797 (14)	0.0554 (12)	−0.0188 (11)	0.0183 (10)	−0.0185 (11)
O4	0.0643 (14)	0.0727 (12)	0.0587 (13)	−0.0255 (11)	0.0259 (10)	−0.0174 (11)
O1W	0.11 (2)	0.11 (2)	0.12 (2)	−0.003 (10)	0.007 (10)	0.002 (10)
O2W	0.30 (13)	0.18 (8)	0.08 (6)	0.15 (9)	−0.04 (5)	0.03 (5)

Geometric parameters (Å, º) top

Cd1—O1	2.3559 (17)	C15—N2	1.384 (3)
Cd1—O2	2.3669 (17)	C16—O3	1.221 (3)
Cd1—O3	2.4209 (19)	C16—O4	1.248 (3)
Cd1—O4	2.3063 (19)	C16—C17	1.518 (3)
Cd1—N1ⁱ	2.2801 (19)	C17—C18	1.388 (3)
Cd1—N4ⁱⁱ	2.283 (2)	C17—C22	1.394 (4)
C1—O2	1.243 (3)	C18—C19	1.375 (4)
C1—O1	1.251 (3)	C18—H18	0.9300
C1—C2	1.507 (3)	C19—C20	1.382 (4)
C2—C3	1.383 (3)	C19—H19	0.9300
C2—C7	1.387 (3)	C20—C21	1.386 (4)
C3—C4	1.384 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.377 (3)
C4—C5	1.386 (4)	C21—C23	1.512 (4)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.385 (4)	C23—N3	1.472 (3)
C5—H5	0.9300	C23—H23A	0.9700
C6—C7	1.390 (3)	C23—H23B	0.9700
C6—C8	1.513 (4)	C24—N4	1.310 (3)
C7—H7	0.9300	C24—N3	1.344 (3)
C8—N2	1.475 (3)	C24—H24	0.9300
C8—H8A	0.9700	C25—C26	1.389 (3)
C8—H8B	0.9700	C25—C30	1.392 (3)
C9—N1	1.326 (3)	C25—N4	1.395 (3)
C9—N2	1.345 (3)	C26—C27	1.369 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—N1	1.387 (3)	C27—C28	1.392 (4)
C10—C15	1.395 (3)	C27—H27	0.9300
C10—C11	1.395 (3)	C28—C29	1.372 (4)
C11—C12	1.376 (4)	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.389 (3)
C12—C13	1.391 (4)	C29—H29	0.9300
C12—H12	0.9300	C30—N3	1.381 (3)
C13—C14	1.380 (4)	O1W—H1O1	0.8500
C13—H13	0.9300	O1W—H2O1	0.8501
C14—C15	1.388 (3)	O2W—H1O2	0.8499
C14—H14	0.9300	O2W—H2O2	0.8500

O2—C1—O1	122.3 (2)	C21—C22—H22	119.4
O2—C1—C2	119.0 (2)	C17—C22—H22	119.4
O1—C1—C2	118.7 (2)	N3—C23—C21	110.3 (2)
C3—C2—C7	119.2 (2)	N3—C23—H23A	109.6
C3—C2—C1	120.4 (2)	C21—C23—H23A	109.6
C7—C2—C1	120.4 (2)	N3—C23—H23B	109.6
C2—C3—C4	120.3 (2)	C21—C23—H23B	109.6
C2—C3—H3	119.9	H23A—C23—H23B	108.1
C4—C3—H3	119.9	N4—C24—N3	113.9 (2)
C3—C4—C5	120.1 (3)	N4—C24—H24	123.0
C3—C4—H4	119.9	N3—C24—H24	123.0
C5—C4—H4	119.9	C26—C25—C30	120.5 (2)
C6—C5—C4	120.3 (2)	C26—C25—N4	130.1 (2)
C6—C5—H5	119.8	C30—C25—N4	109.4 (2)
C4—C5—H5	119.8	C27—C26—C25	117.2 (2)
C5—C6—C7	119.0 (2)	C27—C26—H26	121.4
C5—C6—C8	120.8 (2)	C25—C26—H26	121.4
C7—C6—C8	120.2 (2)	C26—C27—C28	121.8 (2)
C2—C7—C6	121.0 (2)	C26—C27—H27	119.1
C2—C7—H7	119.5	C28—C27—H27	119.1
C6—C7—H7	119.5	C29—C28—C27	122.1 (3)
N2—C8—C6	113.3 (2)	C29—C28—H28	119.0
N2—C8—H8A	108.9	C27—C28—H28	119.0
C6—C8—H8A	108.9	C28—C29—C30	116.0 (2)
N2—C8—H8B	108.9	C28—C29—H29	122.0
C6—C8—H8B	108.9	C30—C29—H29	122.0
H8A—C8—H8B	107.7	N3—C30—C29	132.0 (2)
N1—C9—N2	113.1 (2)	N3—C30—C25	105.6 (2)
N1—C9—H9	123.5	C29—C30—C25	122.4 (2)
N2—C9—H9	123.5	N1ⁱ—Cd1—N4ⁱⁱ	92.79 (7)
N1—C10—C15	109.32 (19)	N1ⁱ—Cd1—O4	95.25 (7)
N1—C10—C11	130.6 (2)	N4ⁱⁱ—Cd1—O4	106.60 (8)
C15—C10—C11	120.1 (2)	N1ⁱ—Cd1—O1	97.51 (7)
C12—C11—C10	117.3 (2)	N4ⁱⁱ—Cd1—O1	146.09 (7)
C12—C11—H11	121.3	O4—Cd1—O1	104.51 (8)
C10—C11—H11	121.3	N1ⁱ—Cd1—O2	107.34 (7)
C11—C12—C13	121.9 (2)	N4ⁱⁱ—Cd1—O2	90.99 (7)
C11—C12—H12	119.1	O4—Cd1—O2	150.71 (7)
C13—C12—H12	119.1	O1—Cd1—O2	55.10 (6)
C14—C13—C12	121.9 (3)	N1ⁱ—Cd1—O3	149.16 (7)
C14—C13—H13	119.0	N4ⁱⁱ—Cd1—O3	90.86 (8)
C12—C13—H13	119.0	O4—Cd1—O3	54.52 (7)
C13—C14—C15	116.0 (2)	O1—Cd1—O3	96.36 (7)
C13—C14—H14	122.0	O2—Cd1—O3	103.21 (6)
C15—C14—H14	122.0	C9—N1—C10	105.02 (19)
N2—C15—C14	131.5 (2)	C9—N1—Cd1ⁱⁱⁱ	126.26 (16)
N2—C15—C10	105.7 (2)	C10—N1—Cd1ⁱⁱⁱ	128.69 (14)
C14—C15—C10	122.9 (2)	C9—N2—C15	106.92 (18)
O3—C16—O4	122.7 (2)	C9—N2—C8	129.3 (2)
O3—C16—C17	119.8 (2)	C15—N2—C8	123.54 (19)
O4—C16—C17	117.4 (2)	C24—N3—C30	106.6 (2)
C18—C17—C22	118.8 (2)	C24—N3—C23	126.0 (2)
C18—C17—C16	120.3 (2)	C30—N3—C23	126.9 (2)
C22—C17—C16	120.9 (2)	C24—N4—C25	104.5 (2)
C19—C18—C17	120.4 (3)	C24—N4—Cd1ⁱⁱ	126.74 (17)
C19—C18—H18	119.8	C25—N4—Cd1ⁱⁱ	128.66 (15)
C17—C18—H18	119.8	C1—O1—Cd1	91.43 (13)
C18—C19—C20	120.2 (3)	C1—O2—Cd1	91.13 (14)
C18—C19—H19	119.9	C16—O3—Cd1	89.01 (15)
C20—C19—H19	119.9	C16—O4—Cd1	93.73 (15)
C19—C20—C21	120.4 (2)	H1O1—O1W—H2O1	111.1
C19—C20—H20	119.8	O2W^iv—O2W—H1O1	167.2
C21—C20—H20	119.8	O2W^iv—O2W—H1O2	73.8
C22—C21—C20	119.1 (2)	H1O1—O2W—H1O2	102.1
C22—C21—C23	120.3 (2)	O2W^iv—O2W—H2O2	53.3
C20—C21—C23	120.6 (2)	H1O1—O2W—H2O2	136.9
C21—C22—C17	121.2 (2)	H1O2—O2W—H2O2	115.8

O2—C1—C2—C3	−13.5 (3)	N2—C9—N1—Cd1ⁱⁱⁱ	178.46 (14)
O1—C1—C2—C3	165.4 (2)	C15—C10—N1—C9	0.5 (2)
O2—C1—C2—C7	167.1 (2)	C11—C10—N1—C9	−178.3 (2)
O1—C1—C2—C7	−14.1 (3)	C15—C10—N1—Cd1ⁱⁱⁱ	−177.58 (14)
C7—C2—C3—C4	−0.1 (3)	C11—C10—N1—Cd1ⁱⁱⁱ	3.7 (3)
C1—C2—C3—C4	−179.6 (2)	N1—C9—N2—C15	−1.0 (3)
C2—C3—C4—C5	−0.6 (4)	N1—C9—N2—C8	174.0 (2)
C3—C4—C5—C6	1.3 (4)	C14—C15—N2—C9	179.9 (2)
C4—C5—C6—C7	−1.4 (4)	C10—C15—N2—C9	1.2 (2)
C4—C5—C6—C8	−179.3 (2)	C14—C15—N2—C8	4.6 (4)
C3—C2—C7—C6	0.0 (3)	C10—C15—N2—C8	−174.1 (2)
C1—C2—C7—C6	179.53 (19)	C6—C8—N2—C9	3.7 (3)
C5—C6—C7—C2	0.7 (3)	C6—C8—N2—C15	177.9 (2)
C8—C6—C7—C2	178.6 (2)	N4—C24—N3—C30	0.4 (3)
C5—C6—C8—N2	−68.0 (3)	N4—C24—N3—C23	173.8 (2)
C7—C6—C8—N2	114.1 (2)	C29—C30—N3—C24	−178.3 (3)
N1—C10—C11—C12	179.6 (2)	C25—C30—N3—C24	−0.2 (3)
C15—C10—C11—C12	0.9 (3)	C29—C30—N3—C23	8.4 (4)
C10—C11—C12—C13	−0.4 (4)	C25—C30—N3—C23	−173.5 (2)
C11—C12—C13—C14	−0.1 (4)	C21—C23—N3—C24	−57.8 (3)
C12—C13—C14—C15	0.0 (4)	C21—C23—N3—C30	114.2 (3)
C13—C14—C15—N2	−178.0 (2)	N3—C24—N4—C25	−0.5 (3)
C13—C14—C15—C10	0.5 (3)	N3—C24—N4—Cd1ⁱⁱ	−177.37 (16)
N1—C10—C15—N2	−1.1 (2)	C26—C25—N4—C24	−179.8 (3)
C11—C10—C15—N2	177.8 (2)	C30—C25—N4—C24	0.3 (3)
N1—C10—C15—C14	−179.9 (2)	C26—C25—N4—Cd1ⁱⁱ	−2.9 (4)
C11—C10—C15—C14	−1.0 (3)	C30—C25—N4—Cd1ⁱⁱ	177.13 (16)
O3—C16—C17—C18	11.5 (4)	O2—C1—O1—Cd1	−0.3 (2)
O4—C16—C17—C18	−167.4 (2)	C2—C1—O1—Cd1	−179.18 (17)
O3—C16—C17—C22	−169.4 (2)	N1ⁱ—Cd1—O1—C1	−105.75 (14)
O4—C16—C17—C22	11.7 (4)	N4ⁱⁱ—Cd1—O1—C1	0.8 (2)
C22—C17—C18—C19	0.4 (4)	O4—Cd1—O1—C1	156.81 (13)
C16—C17—C18—C19	179.5 (2)	O2—Cd1—O1—C1	0.18 (12)
C17—C18—C19—C20	0.8 (4)	O3—Cd1—O1—C1	101.87 (14)
C18—C19—C20—C21	−0.6 (4)	O1—C1—O2—Cd1	0.3 (2)
C19—C20—C21—C22	−0.7 (4)	C2—C1—O2—Cd1	179.18 (17)
C19—C20—C21—C23	177.3 (2)	N1ⁱ—Cd1—O2—C1	86.91 (14)
C20—C21—C22—C17	2.0 (4)	N4ⁱⁱ—Cd1—O2—C1	−179.86 (14)
C23—C21—C22—C17	−176.1 (2)	O4—Cd1—O2—C1	−51.9 (2)
C18—C17—C22—C21	−1.8 (4)	O1—Cd1—O2—C1	−0.19 (12)
C16—C17—C22—C21	179.1 (2)	O3—Cd1—O2—C1	−88.75 (14)
C22—C21—C23—N3	114.7 (3)	O4—C16—O3—Cd1	−1.1 (3)
C20—C21—C23—N3	−63.4 (3)	C17—C16—O3—Cd1	−180.0 (2)
C30—C25—C26—C27	1.0 (4)	N1ⁱ—Cd1—O3—C16	−12.4 (2)
N4—C25—C26—C27	−178.9 (2)	N4ⁱⁱ—Cd1—O3—C16	−109.26 (16)
C25—C26—C27—C28	0.4 (4)	O4—Cd1—O3—C16	0.63 (15)
C26—C27—C28—C29	−1.2 (5)	O1—Cd1—O3—C16	103.93 (16)
C27—C28—C29—C30	0.5 (4)	O2—Cd1—O3—C16	159.52 (15)
C28—C29—C30—N3	178.7 (3)	O3—C16—O4—Cd1	1.2 (3)
C28—C29—C30—C25	0.8 (4)	C17—C16—O4—Cd1	−179.96 (18)
C26—C25—C30—N3	−180.0 (2)	N1ⁱ—Cd1—O4—C16	172.73 (17)
N4—C25—C30—N3	0.0 (3)	N4ⁱⁱ—Cd1—O4—C16	78.24 (18)
C26—C25—C30—C29	−1.6 (4)	O1—Cd1—O4—C16	−88.09 (18)
N4—C25—C30—C29	178.3 (2)	O2—Cd1—O4—C16	−46.4 (3)
N2—C9—N1—C10	0.3 (3)	O3—Cd1—O4—C16	−0.61 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱⁱⁱ	0.93	2.59	3.357 (3)	140
C14—H14···O4^v	0.93	2.41	3.261 (3)	152
C23—H23B···O2^vi	0.97	2.58	3.277 (3)	129
C29—H29···O3^vi	0.93	2.57	3.424 (3)	154

Symmetry codes: (iii) x, y−1, z; (v) −x+2, −y+1, −z; (vi) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₅H₁₁N₂O₂)₂]·0.1H₂O
M_r	616.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.7770 (18), 10.8304 (15), 18.522 (3)
β (°)	95.007 (2)
V (Å³)	2553.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.51 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.656, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	13062, 4754, 4031
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.03
No. of reflections	4754
No. of parameters	370
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.37

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—O1	2.3559 (17)	Cd1—O4	2.3063 (19)
Cd1—O2	2.3669 (17)	Cd1—N1ⁱ	2.2801 (19)
Cd1—O3	2.4209 (19)	Cd1—N4ⁱⁱ	2.283 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱⁱⁱ	0.93	2.59	3.357 (3)	140
C14—H14···O4^iv	0.93	2.41	3.261 (3)	152
C23—H23B···O2^v	0.97	2.58	3.277 (3)	129
C29—H29···O3^v	0.93	2.57	3.424 (3)	154

Symmetry codes: (iii) x, y−1, z; (iv) −x+2, −y+1, −z; (v) x, −y+3/2, z+1/2.

Acknowledgements

We are grateful to the Young Scientists Fund of Shandong Province of China (grant No. 2007BS04002) and the Open Foundation of the State Key Laboratory of Crystal Materials of Shandong University, China (KF0801) for support.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H., Wei, Z., Gong, Q. & Han, Q. (2010). Acta Cryst. E66, m267. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vijayan, N., Bhagavannarayana, G., Balamurugan, N., Babu, R. R., Maurya, K. K., Gopalakrishnan, R. & Ramasamy, P. (2006). J. Cryst. Growth, 293, 318–323. Web of Science CrossRef CAS Google Scholar