Bis(μ-6-hydroxy­naphthalene-1-carboxyl­ato)bis­[(6-hydroxy­naphthalene-1-car­box­yl­ato)(1,10-phenanthroline)cadmium(II)] tetra­hydrate

Liu, C.-S.; Hu, M.; Guo, L.-Q.

doi:10.1107/S1600536809043475

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1432-m1433

https://doi.org/10.1107/S1600536809043475

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Bis(μ-6-hydroxynaphthalene-1-carboxylato)bis[(6-hydroxynaphthalene-1-carboxylato)(1,10-phenanthroline)cadmium(II)] tetrahydrate

Chun-Sen Liu,^a ^* Min Hu ^a and Liang-Qi Guo ^a

^aZhengzhou University of Light Industry, Henan Provincial Key Laboratory of Surface & Interface Science, Henan, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: chunsenliu@zzuli.edu.cn

(Received 20 October 2009; accepted 21 October 2009; online 28 October 2009)

The title complex, [Cd₂(C₁₁H₇O₃)₄(C₁₂H₈N₂)₂]·4H₂O, has a centrosymmetric binuclear structure in which two Cd^II atoms are both six-coordinated and bridged by 6-hydroxynaphthalene-1-carboxylate ligands, with a Cd⋯Cd separation of 3.671 (1) Å. The remaining coordination sites are occupied by two N atoms of a 1,10-phenanthroline ligand and two O atoms of a 6-hydroxynaphthalene-1-carboxylate ligand. The crystal packing is stabilized by O—H⋯O hydrogen-bonding interactions.

Related literature

For the preparation of functional coordination architectures, see: Barnett & Champness (2003 ); Comba & Schiek (2003 ); Telfer & Kuroda (2003 ); Robin & Fromm (2006 ); Tranchemontagne et al. (2009 ). For complexes with carboxylic acid ligands, see: Bania et al. (2007 ); Liu et al. (2006 ); Marsh (2004 ); Paz & Klinowski (2004 ); Qin et al. (2008 ); Shi et al. (2005 ); Wu et al. (2006 ); Xu et al. (2005 ); Ye et al. (2005 ).

Experimental

Crystal data

[Cd₂(C₁₁H₇O₃)₄(C₁₂H₈N₂)₂]·4H₂O
M_r = 1405.96
Monoclinic, P 2₁ /c
a = 11.7382 (11) Å
b = 15.1433 (14) Å
c = 18.2059 (13) Å
β = 116.430 (4)°
V = 2897.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 296 K
0.28 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.804, T_max = 0.868
20423 measured reflections
5096 independent reflections
4064 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.063
S = 1.03
5096 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O5ⁱ	0.85	2.15	2.934 (3)	154
O1W—H2⋯O1ⁱⁱ	0.85	2.03	2.872 (3)	170
O2W—H3⋯O1W	0.85	1.96	2.801 (4)	170
O2W—H4⋯O2	0.85	2.08	2.883 (3)	156
O5—H5B⋯O4ⁱⁱⁱ	0.82	1.84	2.664 (3)	176
O6—H6B⋯O2W^iv	0.82	1.91	2.728 (4)	180
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809043475/bt5107sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043475/bt5107Isup2.hkl

checkCIF report

Comment top

Metallosupramolecular species built from transition metal ions and organic bridging ligands have been rapidly developed in recent years because of their fascinating structural diversities and potential applications as functional materials (Barnett & Champness, 2003; Comba & Schiek, 2003; Telfer & Kuroda, 2003; Robin & Fromm, 2006; Tranchemontagne et al., 2009). The effective and facile approach for the synthesis of such complexes is still the appropriate choice of well designed organic ligands as bridges or terminal groups with metal ions as nodes. Among various ligands, the versatile carboxylic acid ligands, especially for the benzene- and naphthalene-based di- and multi-carboxylic acids, have been most widely employed in the preparation of various Cd^II–carboxylate complexes (Marsh, 2004; Paz & Klinowski, 2004; Qin et al., 2008; Shi et al., 2005; Wu et al., 2006; Xu et al., 2005). In contrast, the skillful use of monocarboxylic acid ligands with the naphthalene skeleton to construct functional Cd^II–carboxylate compounds has been less investigated to date (Bania et al., 2007; Liu et al., 2006). In addition, the introduction of 2,2'-bipyridyl-like bidentate chelating molecules, such as 1,10-phenanthroline or 2,2'-bipyridine, as an auxiliary co-ligand into the reaction systems involving carboxylic acids usually leads to new products and commonly reduces dimensionality of the networks formed (Ye et al., 2005). We report here the crystal structure of a Cd^II complex with mixed 2-naphthol-5-carboxylic acid and 1,10-phenanthroline as ligands.

The structure of the title complex consists of a centrosymmetric dinuclear unit and four lattice water molecules. The Cd^II center is six-coordinated in an distorted octahedral geometry, by two nitrogen donors atoms from one phenanthroline ligand and four O-atoms from three 2-naphthol-5-carboxylate ligands. For 2-naphthol-5-carboxylate, there exist two different kinds of coordination modes with the Cd^IIcenter, namely µ₁-η¹:η¹-chelating and µ₂-η²:η⁰-bridging modes. In this manner two Cd^IIcenter are connected to form a four-membered ring [Cd(1)–O(3)–Cd(1 A)–O(3 A)] with the Cd(1)···Cd(1 A) separation of 3.671 (1) Å (symmetry operation (A) = 1 - x, 1 - y, 1 - z).

Related literature top

For the preparation of functional coordination architectures, see: Barnett & Champness (2003); Comba & Schiek (2003); Telfer & Kuroda (2003); Robin & Fromm (2006); Tranchemontagne et al.(2009). For complexes with carboxylic acid ligands, see: Bania et al. (2007); Liu et al. (2006); Marsh (2004); Paz & Klinowski (2004); Qin et al. (2008); Shi et al. (2005); Wu et al. (2006); Xu et al. (2005); Ye et al. (2005).

Experimental top

A mixed solution of 2-naphthol-5-carboxylic acid (0.05 mmol) and 1,10-phenanthroline (0.05 mmol) in CH₃OH (10 ml) in the presence of excess 2,6-dimethylpyridine (ca 0.05 ml for adjusting the pH value to basic condition) was carefully layered on top of a H₂O solution (15 ml) of Cd(ClO₄)₂ (0.1 mmol) in a test tube. Yellow single crystals suitable for X-ray analysis of the title complex (I) appeared at the tube wall after ca three weeks at room temperature. Yield: ~30% based on 2-naphthol-5-carboxylic acid. Elemental analysis calculated for C₆₈H₅₂Cd₂N₄O₁₆: C 58.09, H 3.73, N 3.98%; found: C 59.16, H 3.65, N 3.85%. IR (KBr pellet, cm^-1): 3403 s (br), 2977m, 2931m, 2770w, 2559w, 1597m, 1554m, 1521 s, 1468w, 1422m, 1377 s, 1302m, 1243m, 1148m, 1100w, 1049w, 953m, 847m, 791m, 767m, 725m, 663m, 604w.

Structure description top

For the preparation of functional coordination architectures, see: Barnett & Champness (2003); Comba & Schiek (2003); Telfer & Kuroda (2003); Robin & Fromm (2006); Tranchemontagne et al.(2009). For complexes with carboxylic acid ligands, see: Bania et al. (2007); Liu et al. (2006); Marsh (2004); Paz & Klinowski (2004); Qin et al. (2008); Shi et al. (2005); Wu et al. (2006); Xu et al. (2005); Ye et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix A are generated by the symmetry operation (1 – x, 1 – y, 1 – z). Four free water molecules are omitted for clarity.

Bis(µ-6-hydroxynaphthalene-1-carboxylato)bis[(6-hydroxynaphthalene- 1-carboxylato)(1,10-phenanthroline)cadmium(II)] tetrahydrate top

Crystal data top

[Cd₂(C₁₁H₇O₃)₄(C₁₂H₈N₂)₂]·4H₂O	F(000) = 1424
M_r = 1405.96	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7382 (11) Å	Cell parameters from 5160 reflections
b = 15.1433 (14) Å	θ = 2.4–23.9°
c = 18.2059 (13) Å	µ = 0.81 mm⁻¹
β = 116.430 (4)°	T = 296 K
V = 2897.9 (4) Å³	Block, yellow
Z = 2	0.28 × 0.21 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5096 independent reflections
Radiation source: fine-focus sealed tube	4064 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.804, T_max = 0.868	k = −18→18
20423 measured reflections	l = −21→21

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) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.022P)² + 1.6679P] where P = (F_o² + 2F_c²)/3
5096 reflections	(Δ/σ)_max = 0.002
406 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Cd₂(C₁₁H₇O₃)₄(C₁₂H₈N₂)₂]·4H₂O	V = 2897.9 (4) Å³
M_r = 1405.96	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7382 (11) Å	µ = 0.81 mm⁻¹
b = 15.1433 (14) Å	T = 296 K
c = 18.2059 (13) Å	0.28 × 0.21 × 0.18 mm
β = 116.430 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5096 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4064 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.868	R_int = 0.037
20423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
5096 reflections	Δρ_min = −0.41 e Å⁻³
406 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	0.648118 (18)	0.537570 (13)	0.499232 (12)	0.03367 (7)
O1	0.64852 (18)	0.68046 (12)	0.45742 (12)	0.0398 (5)
O2	0.65340 (19)	0.67592 (12)	0.57928 (12)	0.0462 (5)
O3	0.56800 (17)	0.45469 (13)	0.57326 (11)	0.0410 (5)
O4	0.51162 (19)	0.46283 (14)	0.67285 (12)	0.0490 (5)
O5	0.5108 (2)	1.04569 (13)	0.70518 (13)	0.0550 (6)
H5B	0.5048	1.0182	0.7421	0.082*
O6	1.0184 (2)	0.17488 (14)	0.63847 (15)	0.0648 (7)
H6B	1.0940	0.1780	0.6711	0.097*
N1	0.7308 (2)	0.42210 (15)	0.45474 (14)	0.0359 (5)
N2	0.8635 (2)	0.52345 (14)	0.59125 (13)	0.0332 (5)
C1	0.6666 (3)	0.3693 (2)	0.39153 (19)	0.0494 (8)
H1A	0.5793	0.3778	0.3619	0.059*
C2	0.7228 (3)	0.3020 (2)	0.3672 (2)	0.0591 (9)
H2A	0.6736	0.2655	0.3234	0.071*
C3	0.8509 (3)	0.2903 (2)	0.4086 (2)	0.0570 (9)
H3A	0.8906	0.2469	0.3920	0.068*
C4	0.9226 (3)	0.34400 (19)	0.47602 (18)	0.0410 (7)
C5	1.0570 (3)	0.3349 (2)	0.5234 (2)	0.0498 (8)
H5A	1.1002	0.2935	0.5075	0.060*
C6	1.1222 (3)	0.3842 (2)	0.5897 (2)	0.0486 (8)
H6A	1.2097	0.3767	0.6191	0.058*
C7	1.0592 (2)	0.44858 (19)	0.61633 (17)	0.0380 (7)
C8	1.1219 (3)	0.4995 (2)	0.6869 (2)	0.0549 (9)
H8A	1.2089	0.4925	0.7190	0.066*
C9	1.0569 (3)	0.5592 (2)	0.7088 (2)	0.0566 (9)
H9A	1.0981	0.5926	0.7563	0.068*
C10	0.9269 (3)	0.5697 (2)	0.65892 (18)	0.0433 (7)
H10A	0.8828	0.6113	0.6740	0.052*
C11	0.9278 (2)	0.46242 (17)	0.56963 (16)	0.0307 (6)
C12	0.8583 (3)	0.40913 (17)	0.49782 (16)	0.0323 (6)
C13	0.6536 (2)	0.71904 (18)	0.52027 (18)	0.0363 (7)
C14	0.6668 (2)	0.81874 (18)	0.52391 (16)	0.0347 (6)
C15	0.7268 (3)	0.85596 (19)	0.48148 (17)	0.0386 (7)
H15A	0.7517	0.8200	0.4498	0.046*
C16	0.7511 (3)	0.94664 (19)	0.48501 (18)	0.0427 (7)
H16A	0.7918	0.9704	0.4559	0.051*
C17	0.7152 (3)	1.0001 (2)	0.53121 (17)	0.0423 (7)
H17A	0.7340	1.0601	0.5347	0.051*
C18	0.6500 (2)	0.96592 (18)	0.57379 (16)	0.0340 (6)
C19	0.6096 (3)	1.02198 (19)	0.61936 (17)	0.0404 (7)
H19A	0.6262	1.0822	0.6213	0.048*
C20	0.5467 (3)	0.98935 (19)	0.66048 (17)	0.0398 (7)
C21	0.5185 (3)	0.89926 (19)	0.65634 (18)	0.0442 (7)
H21A	0.4743	0.8774	0.6840	0.053*
C22	0.5550 (3)	0.84284 (19)	0.61223 (18)	0.0410 (7)
H22A	0.5339	0.7833	0.6095	0.049*
C23	0.6245 (2)	0.87360 (17)	0.57055 (16)	0.0335 (6)
C24	0.5938 (3)	0.44834 (18)	0.64928 (17)	0.0367 (7)
C25	0.7267 (3)	0.42322 (18)	0.70921 (16)	0.0347 (6)
C26	0.7973 (3)	0.35801 (17)	0.69061 (16)	0.0338 (6)
C27	0.7474 (3)	0.30337 (18)	0.61980 (18)	0.0424 (7)
H27A	0.6619	0.3082	0.5827	0.051*
C28	0.8219 (3)	0.24406 (19)	0.60497 (19)	0.0480 (8)
H28A	0.7865	0.2093	0.5580	0.058*
C29	0.9512 (3)	0.23452 (19)	0.6594 (2)	0.0472 (8)
C30	1.0025 (3)	0.28396 (19)	0.72909 (18)	0.0435 (7)
H30A	1.0880	0.2771	0.7655	0.052*
C31	0.9281 (3)	0.34535 (18)	0.74713 (17)	0.0365 (7)
C32	0.9808 (3)	0.3957 (2)	0.81986 (17)	0.0436 (7)
H32A	1.0659	0.3879	0.8567	0.052*
C33	0.9095 (3)	0.4554 (2)	0.83720 (17)	0.0464 (8)
H33A	0.9455	0.4872	0.8859	0.056*
C34	0.7818 (3)	0.4687 (2)	0.78147 (17)	0.0426 (7)
H34A	0.7335	0.5093	0.7939	0.051*
O1W	0.5418 (2)	0.73556 (15)	0.79947 (13)	0.0609 (6)
H1	0.5421	0.6825	0.8149	0.073*
H2	0.5660	0.7580	0.8469	0.073*
O2W	0.7302 (2)	0.68503 (16)	0.75316 (14)	0.0703 (7)
H3	0.6802	0.7035	0.7721	0.084*
H4	0.7056	0.6987	0.7031	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02669 (11)	0.03283 (12)	0.04132 (13)	0.00375 (9)	0.01496 (9)	0.00190 (10)
O1	0.0447 (12)	0.0340 (11)	0.0414 (12)	0.0026 (9)	0.0198 (10)	−0.0031 (9)
O2	0.0598 (14)	0.0343 (11)	0.0479 (13)	0.0056 (10)	0.0270 (11)	0.0014 (10)
O3	0.0316 (10)	0.0542 (13)	0.0301 (11)	−0.0029 (9)	0.0075 (9)	0.0117 (9)
O4	0.0383 (12)	0.0630 (14)	0.0435 (12)	0.0081 (11)	0.0163 (10)	−0.0038 (11)
O5	0.0792 (16)	0.0432 (13)	0.0489 (13)	0.0118 (12)	0.0342 (12)	−0.0012 (10)
O6	0.0744 (16)	0.0466 (14)	0.0730 (17)	0.0131 (12)	0.0324 (14)	−0.0038 (12)
N1	0.0318 (13)	0.0312 (13)	0.0397 (14)	0.0015 (10)	0.0115 (11)	0.0006 (11)
N2	0.0292 (12)	0.0337 (13)	0.0361 (13)	0.0014 (10)	0.0139 (10)	−0.0006 (10)
C1	0.0446 (18)	0.0463 (19)	0.0471 (19)	−0.0024 (15)	0.0114 (16)	−0.0044 (16)
C2	0.067 (2)	0.046 (2)	0.056 (2)	−0.0020 (18)	0.0203 (19)	−0.0174 (17)
C3	0.069 (2)	0.0444 (19)	0.061 (2)	0.0089 (18)	0.033 (2)	−0.0127 (17)
C4	0.0452 (18)	0.0364 (16)	0.0466 (18)	0.0077 (14)	0.0252 (15)	0.0014 (14)
C5	0.050 (2)	0.0442 (19)	0.066 (2)	0.0179 (16)	0.0366 (18)	0.0073 (17)
C6	0.0339 (17)	0.057 (2)	0.058 (2)	0.0144 (15)	0.0232 (16)	0.0130 (17)
C7	0.0286 (15)	0.0434 (17)	0.0413 (17)	0.0048 (13)	0.0150 (13)	0.0091 (14)
C8	0.0307 (16)	0.073 (2)	0.048 (2)	0.0028 (16)	0.0065 (15)	−0.0003 (18)
C9	0.0446 (19)	0.070 (2)	0.0421 (19)	−0.0030 (17)	0.0071 (16)	−0.0167 (17)
C10	0.0415 (18)	0.0455 (17)	0.0406 (18)	0.0021 (14)	0.0163 (15)	−0.0077 (14)
C11	0.0273 (14)	0.0303 (14)	0.0359 (15)	0.0041 (12)	0.0153 (12)	0.0036 (13)
C12	0.0336 (15)	0.0288 (14)	0.0366 (15)	0.0026 (12)	0.0175 (13)	0.0048 (13)
C13	0.0286 (15)	0.0334 (16)	0.0427 (18)	0.0056 (12)	0.0121 (14)	0.0006 (14)
C14	0.0280 (14)	0.0348 (15)	0.0349 (16)	0.0049 (12)	0.0083 (13)	0.0021 (12)
C15	0.0352 (16)	0.0419 (17)	0.0360 (16)	0.0018 (13)	0.0134 (13)	0.0005 (13)
C16	0.0426 (17)	0.0462 (19)	0.0410 (17)	−0.0068 (14)	0.0202 (15)	0.0031 (14)
C17	0.0462 (18)	0.0326 (15)	0.0426 (18)	−0.0050 (14)	0.0148 (15)	0.0028 (14)
C18	0.0309 (14)	0.0323 (15)	0.0297 (14)	0.0017 (13)	0.0053 (12)	0.0023 (13)
C19	0.0437 (17)	0.0351 (17)	0.0333 (16)	0.0014 (14)	0.0091 (14)	0.0011 (13)
C20	0.0432 (17)	0.0392 (17)	0.0327 (16)	0.0085 (14)	0.0130 (14)	0.0006 (13)
C21	0.0475 (18)	0.0427 (18)	0.0476 (18)	0.0024 (15)	0.0259 (15)	0.0053 (15)
C22	0.0408 (17)	0.0339 (16)	0.0490 (18)	0.0008 (13)	0.0206 (15)	0.0017 (14)
C23	0.0309 (15)	0.0321 (15)	0.0309 (15)	0.0026 (12)	0.0078 (12)	0.0038 (12)
C24	0.0340 (16)	0.0339 (16)	0.0351 (16)	−0.0029 (13)	0.0091 (13)	0.0011 (13)
C25	0.0339 (15)	0.0378 (15)	0.0297 (15)	0.0010 (13)	0.0118 (13)	0.0065 (13)
C26	0.0359 (15)	0.0317 (15)	0.0300 (15)	−0.0030 (12)	0.0111 (13)	0.0048 (12)
C27	0.0440 (17)	0.0339 (16)	0.0391 (17)	−0.0035 (14)	0.0095 (14)	0.0031 (14)
C28	0.062 (2)	0.0311 (16)	0.0436 (18)	−0.0045 (15)	0.0170 (17)	−0.0027 (14)
C29	0.062 (2)	0.0304 (16)	0.055 (2)	0.0074 (15)	0.0315 (18)	0.0066 (15)
C30	0.0400 (17)	0.0386 (17)	0.0448 (19)	0.0066 (14)	0.0124 (15)	0.0089 (15)
C31	0.0370 (16)	0.0338 (16)	0.0342 (16)	0.0014 (13)	0.0119 (13)	0.0077 (13)
C32	0.0370 (16)	0.0505 (19)	0.0340 (16)	0.0031 (15)	0.0076 (14)	0.0050 (14)
C33	0.0462 (18)	0.055 (2)	0.0288 (15)	−0.0015 (16)	0.0087 (14)	−0.0054 (15)
C34	0.0422 (17)	0.0482 (18)	0.0359 (16)	0.0041 (15)	0.0161 (14)	0.0001 (15)
O1W	0.0763 (16)	0.0583 (15)	0.0430 (13)	−0.0083 (13)	0.0220 (12)	−0.0003 (11)
O2W	0.0676 (16)	0.0829 (18)	0.0647 (16)	0.0084 (14)	0.0332 (13)	0.0077 (14)

Geometric parameters (Å, º) top

Cd1—O3ⁱ	2.2827 (18)	C11—C12	1.441 (4)
Cd1—O1	2.2945 (18)	C13—C14	1.516 (4)
Cd1—N1	2.314 (2)	C14—C15	1.377 (4)
Cd1—O3	2.3247 (18)	C14—C23	1.426 (4)
Cd1—N2	2.339 (2)	C15—C16	1.398 (4)
Cd1—O2	2.5370 (19)	C15—H15A	0.9300
Cd1—C13	2.771 (3)	C16—C17	1.363 (4)
Cd1—O4ⁱ	2.846 (2)	C16—H16A	0.9300
Cd1—Cd1ⁱ	3.6706 (5)	C17—C18	1.408 (4)
O1—C13	1.262 (3)	C17—H17A	0.9300
O2—C13	1.258 (3)	C18—C19	1.409 (4)
O3—C24	1.282 (3)	C18—C23	1.425 (4)
O3—Cd1ⁱ	2.2827 (18)	C19—C20	1.357 (4)
O4—C24	1.238 (3)	C19—H19A	0.9300
O4—Cd1ⁱ	2.846 (2)	C20—C21	1.398 (4)
O5—C20	1.369 (3)	C21—C22	1.366 (4)
O5—H5B	0.8200	C21—H21A	0.9300
O6—C29	1.360 (3)	C22—C23	1.418 (4)
O6—H6B	0.8200	C22—H22A	0.9300
N1—C1	1.326 (4)	C24—C25	1.501 (4)
N1—C12	1.360 (3)	C25—C34	1.366 (4)
N2—C10	1.322 (3)	C25—C26	1.424 (4)
N2—C11	1.358 (3)	C26—C27	1.420 (4)
C1—C2	1.389 (4)	C26—C31	1.431 (4)
C1—H1A	0.9300	C27—C28	1.362 (4)
C2—C3	1.361 (4)	C27—H27A	0.9300
C2—H2A	0.9300	C28—C29	1.403 (4)
C3—C4	1.399 (4)	C28—H28A	0.9300
C3—H3A	0.9300	C29—C30	1.362 (4)
C4—C12	1.402 (4)	C30—C31	1.411 (4)
C4—C5	1.428 (4)	C30—H30A	0.9300
C5—C6	1.334 (4)	C31—C32	1.410 (4)
C5—H5A	0.9300	C32—C33	1.360 (4)
C6—C7	1.432 (4)	C32—H32A	0.9300
C6—H6A	0.9300	C33—C34	1.402 (4)
C7—C8	1.394 (4)	C33—H33A	0.9300
C7—C11	1.406 (4)	C34—H34A	0.9300
C8—C9	1.353 (4)	O1W—H1	0.8500
C8—H8A	0.9300	O1W—H2	0.8500
C9—C10	1.395 (4)	O2W—H3	0.8499
C9—H9A	0.9300	O2W—H4	0.8502
C10—H10A	0.9300

O3ⁱ—Cd1—O1	85.73 (7)	C9—C10—H10A	118.5
O3ⁱ—Cd1—N1	111.57 (8)	N2—C11—C7	121.9 (2)
O1—Cd1—N1	122.24 (7)	N2—C11—C12	118.7 (2)
O3ⁱ—Cd1—O3	74.38 (7)	C7—C11—C12	119.4 (2)
O1—Cd1—O3	139.69 (7)	N1—C12—C4	122.1 (3)
N1—Cd1—O3	97.80 (8)	N1—C12—C11	118.4 (2)
O3ⁱ—Cd1—N2	170.86 (7)	C4—C12—C11	119.5 (2)
O1—Cd1—N2	99.36 (7)	O2—C13—O1	121.1 (3)
N1—Cd1—N2	72.17 (8)	O2—C13—C14	121.2 (3)
O3—Cd1—N2	97.04 (7)	O1—C13—C14	117.6 (3)
O3ⁱ—Cd1—O2	91.52 (7)	O2—C13—Cd1	66.08 (15)
O1—Cd1—O2	53.75 (7)	O1—C13—Cd1	55.04 (14)
N1—Cd1—O2	156.67 (7)	C14—C13—Cd1	171.5 (2)
O3—Cd1—O2	91.47 (7)	C15—C14—C23	119.8 (3)
N2—Cd1—O2	85.51 (7)	C15—C14—C13	116.8 (3)
O3ⁱ—Cd1—C13	88.87 (7)	C23—C14—C13	123.4 (3)
O1—Cd1—C13	26.80 (7)	C14—C15—C16	121.4 (3)
N1—Cd1—C13	144.11 (8)	C14—C15—H15A	119.3
O3—Cd1—C13	116.46 (8)	C16—C15—H15A	119.3
N2—Cd1—C13	92.32 (8)	C17—C16—C15	119.9 (3)
O2—Cd1—C13	26.95 (7)	C17—C16—H16A	120.0
O3ⁱ—Cd1—O4ⁱ	49.13 (6)	C15—C16—H16A	120.0
O1—Cd1—O4ⁱ	74.60 (6)	C16—C17—C18	121.0 (3)
N1—Cd1—O4ⁱ	77.68 (7)	C16—C17—H17A	119.5
O3—Cd1—O4ⁱ	113.50 (6)	C18—C17—H17A	119.5
N2—Cd1—O4ⁱ	139.51 (7)	C17—C18—C19	120.7 (3)
O2—Cd1—O4ⁱ	118.02 (6)	C17—C18—C23	119.6 (3)
C13—Cd1—O4ⁱ	96.75 (7)	C19—C18—C23	119.7 (3)
O3ⁱ—Cd1—Cd1ⁱ	37.58 (5)	C20—C19—C18	120.9 (3)
O1—Cd1—Cd1ⁱ	115.89 (5)	C20—C19—H19A	119.5
N1—Cd1—Cd1ⁱ	108.34 (6)	C18—C19—H19A	119.5
O3—Cd1—Cd1ⁱ	36.79 (4)	C19—C20—O5	119.2 (3)
N2—Cd1—Cd1ⁱ	133.75 (5)	C19—C20—C21	120.0 (3)
O2—Cd1—Cd1ⁱ	91.87 (5)	O5—C20—C21	120.8 (3)
C13—Cd1—Cd1ⁱ	105.66 (6)	C22—C21—C20	120.9 (3)
O4ⁱ—Cd1—Cd1ⁱ	81.11 (4)	C22—C21—H21A	119.5
C13—O1—Cd1	98.15 (17)	C20—C21—H21A	119.5
C13—O2—Cd1	86.96 (16)	C21—C22—C23	121.0 (3)
C24—O3—Cd1ⁱ	107.21 (16)	C21—C22—H22A	119.5
C24—O3—Cd1	134.76 (17)	C23—C22—H22A	119.5
Cd1ⁱ—O3—Cd1	105.62 (7)	C22—C23—C18	117.4 (3)
C24—O4—Cd1ⁱ	81.45 (16)	C22—C23—C14	124.3 (3)
C20—O5—H5B	109.5	C18—C23—C14	118.3 (3)
C29—O6—H6B	109.5	O4—C24—O3	121.0 (3)
C1—N1—C12	117.9 (2)	O4—C24—C25	120.7 (3)
C1—N1—Cd1	126.5 (2)	O3—C24—C25	118.3 (2)
C12—N1—Cd1	115.64 (17)	C34—C25—C26	120.2 (3)
C10—N2—C11	118.4 (2)	C34—C25—C24	117.8 (3)
C10—N2—Cd1	126.87 (19)	C26—C25—C24	122.0 (2)
C11—N2—Cd1	114.69 (16)	C27—C26—C25	124.9 (3)
N1—C1—C2	123.5 (3)	C27—C26—C31	116.8 (3)
N1—C1—H1A	118.3	C25—C26—C31	118.3 (2)
C2—C1—H1A	118.3	C28—C27—C26	121.5 (3)
C3—C2—C1	119.0 (3)	C28—C27—H27A	119.2
C3—C2—H2A	120.5	C26—C27—H27A	119.2
C1—C2—H2A	120.5	C27—C28—C29	121.1 (3)
C2—C3—C4	119.6 (3)	C27—C28—H28A	119.4
C2—C3—H3A	120.2	C29—C28—H28A	119.4
C4—C3—H3A	120.2	O6—C29—C30	123.7 (3)
C3—C4—C12	117.9 (3)	O6—C29—C28	116.8 (3)
C3—C4—C5	123.0 (3)	C30—C29—C28	119.5 (3)
C12—C4—C5	119.1 (3)	C29—C30—C31	121.1 (3)
C6—C5—C4	121.9 (3)	C29—C30—H30A	119.4
C6—C5—H5A	119.1	C31—C30—H30A	119.4
C4—C5—H5A	119.1	C32—C31—C30	121.1 (3)
C5—C6—C7	120.8 (3)	C32—C31—C26	119.0 (3)
C5—C6—H6A	119.6	C30—C31—C26	119.9 (3)
C7—C6—H6A	119.6	C33—C32—C31	121.3 (3)
C8—C7—C11	117.5 (3)	C33—C32—H32A	119.4
C8—C7—C6	123.2 (3)	C31—C32—H32A	119.4
C11—C7—C6	119.3 (3)	C32—C33—C34	119.9 (3)
C9—C8—C7	120.4 (3)	C32—C33—H33A	120.1
C9—C8—H8A	119.8	C34—C33—H33A	120.1
C7—C8—H8A	119.8	C25—C34—C33	121.3 (3)
C8—C9—C10	118.8 (3)	C25—C34—H34A	119.3
C8—C9—H9A	120.6	C33—C34—H34A	119.3
C10—C9—H9A	120.6	H1—O1W—H2	95.3
N2—C10—C9	123.1 (3)	H3—O2W—H4	112.8
N2—C10—H10A	118.5

O3ⁱ—Cd1—O1—C13	95.96 (16)	C3—C4—C12—N1	−1.3 (4)
N1—Cd1—O1—C13	−151.16 (15)	C5—C4—C12—N1	179.1 (3)
O3—Cd1—O1—C13	36.3 (2)	C3—C4—C12—C11	176.6 (3)
N2—Cd1—O1—C13	−76.40 (17)	C5—C4—C12—C11	−3.0 (4)
O2—Cd1—O1—C13	0.94 (15)	N2—C11—C12—N1	−0.2 (4)
O4ⁱ—Cd1—O1—C13	144.66 (17)	C7—C11—C12—N1	178.4 (2)
Cd1ⁱ—Cd1—O1—C13	72.82 (16)	N2—C11—C12—C4	−178.1 (2)
O3ⁱ—Cd1—O2—C13	−84.52 (16)	C7—C11—C12—C4	0.4 (4)
O1—Cd1—O2—C13	−0.94 (15)	Cd1—O2—C13—O1	1.6 (3)
N1—Cd1—O2—C13	87.3 (2)	Cd1—O2—C13—C14	−175.2 (2)
O3—Cd1—O2—C13	−158.93 (16)	Cd1—O1—C13—O2	−1.8 (3)
N2—Cd1—O2—C13	104.13 (16)	Cd1—O1—C13—C14	175.09 (19)
O4ⁱ—Cd1—O2—C13	−41.20 (17)	O3ⁱ—Cd1—C13—O2	95.57 (16)
Cd1ⁱ—Cd1—O2—C13	−122.12 (15)	O1—Cd1—C13—O2	178.3 (3)
O3ⁱ—Cd1—O3—C24	−135.2 (3)	N1—Cd1—C13—O2	−137.55 (16)
O1—Cd1—O3—C24	−71.9 (3)	O3—Cd1—C13—O2	23.67 (17)
N1—Cd1—O3—C24	114.5 (3)	N2—Cd1—C13—O2	−75.37 (16)
N2—Cd1—O3—C24	41.6 (3)	O4ⁱ—Cd1—C13—O2	144.16 (15)
O2—Cd1—O3—C24	−44.1 (3)	Cd1ⁱ—Cd1—C13—O2	61.53 (16)
C13—Cd1—O3—C24	−54.6 (3)	O3ⁱ—Cd1—C13—O1	−82.76 (16)
O4ⁱ—Cd1—O3—C24	−165.6 (2)	N1—Cd1—C13—O1	44.1 (2)
Cd1ⁱ—Cd1—O3—C24	−135.2 (3)	O3—Cd1—C13—O1	−154.66 (15)
O3ⁱ—Cd1—O3—Cd1ⁱ	0.0	N2—Cd1—C13—O1	106.30 (16)
O1—Cd1—O3—Cd1ⁱ	63.32 (13)	O2—Cd1—C13—O1	−178.3 (3)
N1—Cd1—O3—Cd1ⁱ	−110.30 (9)	O4ⁱ—Cd1—C13—O1	−34.17 (16)
N2—Cd1—O3—Cd1ⁱ	176.82 (8)	Cd1ⁱ—Cd1—C13—O1	−116.79 (15)
O2—Cd1—O3—Cd1ⁱ	91.16 (8)	O2—C13—C14—C15	148.9 (3)
C13—Cd1—O3—Cd1ⁱ	80.68 (9)	O1—C13—C14—C15	−28.0 (4)
O4ⁱ—Cd1—O3—Cd1ⁱ	−30.40 (10)	O2—C13—C14—C23	−28.9 (4)
O3ⁱ—Cd1—N1—C1	4.9 (3)	O1—C13—C14—C23	154.2 (3)
O1—Cd1—N1—C1	−94.0 (2)	C23—C14—C15—C16	2.0 (4)
O3—Cd1—N1—C1	81.1 (2)	C13—C14—C15—C16	−175.9 (3)
N2—Cd1—N1—C1	176.0 (3)	C14—C15—C16—C17	0.0 (4)
O2—Cd1—N1—C1	−166.4 (2)	C15—C16—C17—C18	−2.0 (4)
C13—Cd1—N1—C1	−115.8 (2)	C16—C17—C18—C19	−178.0 (3)
O4ⁱ—Cd1—N1—C1	−31.4 (2)	C16—C17—C18—C23	1.9 (4)
Cd1ⁱ—Cd1—N1—C1	44.8 (2)	C17—C18—C19—C20	180.0 (3)
O3ⁱ—Cd1—N1—C12	−176.18 (17)	C23—C18—C19—C20	0.1 (4)
O1—Cd1—N1—C12	84.91 (19)	C18—C19—C20—O5	178.9 (2)
O3—Cd1—N1—C12	−99.96 (18)	C18—C19—C20—C21	−1.6 (4)
N2—Cd1—N1—C12	−5.04 (18)	C19—C20—C21—C22	0.9 (4)
O2—Cd1—N1—C12	12.6 (3)	O5—C20—C21—C22	−179.6 (3)
C13—Cd1—N1—C12	63.1 (2)	C20—C21—C22—C23	1.2 (4)
O4ⁱ—Cd1—N1—C12	147.59 (19)	C21—C22—C23—C18	−2.5 (4)
Cd1ⁱ—Cd1—N1—C12	−136.24 (17)	C21—C22—C23—C14	179.5 (3)
O1—Cd1—N2—C10	61.9 (2)	C17—C18—C23—C22	−178.0 (3)
N1—Cd1—N2—C10	−177.1 (2)	C19—C18—C23—C22	1.9 (4)
O2—Cd1—N2—C10	9.8 (2)	C17—C18—C23—C14	0.2 (4)
C13—Cd1—N2—C10	35.9 (2)	C19—C18—C23—C14	−180.0 (2)
O4ⁱ—Cd1—N2—C10	139.1 (2)	C15—C14—C23—C22	176.0 (3)
Cd1ⁱ—Cd1—N2—C10	−78.5 (2)	C13—C14—C23—C22	−6.3 (4)
O1—Cd1—N2—C11	−116.08 (18)	C15—C14—C23—C18	−2.1 (4)
N1—Cd1—N2—C11	4.91 (17)	C13—C14—C23—C18	175.7 (2)
O2—Cd1—N2—C11	−168.20 (18)	Cd1ⁱ—O4—C24—O3	9.9 (2)
C13—Cd1—N2—C11	−142.10 (18)	Cd1ⁱ—O4—C24—C25	−170.3 (3)
O4ⁱ—Cd1—N2—C11	−38.9 (2)	Cd1ⁱ—O3—C24—O4	−12.9 (3)
Cd1ⁱ—Cd1—N2—C11	103.51 (17)	Cd1—O3—C24—O4	121.9 (3)
C12—N1—C1—C2	−0.1 (4)	Cd1ⁱ—O3—C24—C25	167.38 (19)
Cd1—N1—C1—C2	178.8 (2)	Cd1—O3—C24—C25	−57.8 (4)
N1—C1—C2—C3	−1.8 (5)	O4—C24—C25—C34	−43.3 (4)
C1—C2—C3—C4	2.1 (5)	O3—C24—C25—C34	136.4 (3)
C2—C3—C4—C12	−0.7 (5)	O4—C24—C25—C26	140.3 (3)
C2—C3—C4—C5	178.9 (3)	O3—C24—C25—C26	−40.0 (4)
C3—C4—C5—C6	−176.8 (3)	C34—C25—C26—C27	176.1 (3)
C12—C4—C5—C6	2.8 (5)	C24—C25—C26—C27	−7.6 (4)
C4—C5—C6—C7	0.2 (5)	C34—C25—C26—C31	−3.4 (4)
C5—C6—C7—C8	177.5 (3)	C24—C25—C26—C31	172.8 (2)
C5—C6—C7—C11	−2.8 (4)	C25—C26—C27—C28	178.1 (3)
C11—C7—C8—C9	0.5 (5)	C31—C26—C27—C28	−2.4 (4)
C6—C7—C8—C9	−179.9 (3)	C26—C27—C28—C29	0.1 (4)
C7—C8—C9—C10	−1.1 (5)	C27—C28—C29—O6	−178.7 (3)
C11—N2—C10—C9	0.4 (4)	C27—C28—C29—C30	1.5 (5)
Cd1—N2—C10—C9	−177.5 (2)	O6—C29—C30—C31	179.5 (3)
C8—C9—C10—N2	0.7 (5)	C28—C29—C30—C31	−0.7 (4)
C10—N2—C11—C7	−1.0 (4)	C29—C30—C31—C32	179.1 (3)
Cd1—N2—C11—C7	177.1 (2)	C29—C30—C31—C26	−1.6 (4)
C10—N2—C11—C12	177.4 (2)	C27—C26—C31—C32	−177.7 (2)
Cd1—N2—C11—C12	−4.4 (3)	C25—C26—C31—C32	1.9 (4)
C8—C7—C11—N2	0.6 (4)	C27—C26—C31—C30	3.1 (4)
C6—C7—C11—N2	−179.0 (3)	C25—C26—C31—C30	−177.3 (2)
C8—C7—C11—C12	−177.9 (3)	C30—C31—C32—C33	179.6 (3)
C6—C7—C11—C12	2.5 (4)	C26—C31—C32—C33	0.3 (4)
C1—N1—C12—C4	1.7 (4)	C31—C32—C33—C34	−1.1 (5)
Cd1—N1—C12—C4	−177.4 (2)	C26—C25—C34—C33	2.7 (4)
C1—N1—C12—C11	−176.2 (2)	C24—C25—C34—C33	−173.7 (3)
Cd1—N1—C12—C11	4.7 (3)	C32—C33—C34—C25	−0.4 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O5ⁱⁱ	0.85	2.15	2.934 (3)	154
O1W—H2···O1ⁱⁱⁱ	0.85	2.03	2.872 (3)	170
O2W—H3···O1W	0.85	1.96	2.801 (4)	170
O2W—H4···O2	0.85	2.08	2.883 (3)	156
O5—H5B···O4^iv	0.82	1.84	2.664 (3)	176
O6—H6B···O2W^v	0.82	1.91	2.728 (4)	180

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

Experimental details

Crystal data
Chemical formula	[Cd₂(C₁₁H₇O₃)₄(C₁₂H₈N₂)₂]·4H₂O
M_r	1405.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.7382 (11), 15.1433 (14), 18.2059 (13)
β (°)	116.430 (4)
V (Å³)	2897.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.28 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.804, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	20423, 5096, 4064
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.063, 1.03
No. of reflections	5096
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.41

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O5ⁱ	0.8500	2.1500	2.934 (3)	154.00
O1W—H2···O1ⁱⁱ	0.8500	2.0300	2.872 (3)	170.00
O2W—H3···O1W	0.8500	1.9600	2.801 (4)	170.00
O2W—H4···O2	0.8500	2.0800	2.883 (3)	156.00
O5—H5B···O4ⁱⁱⁱ	0.8200	1.8400	2.664 (3)	176.00
O6—H6B···O2W^iv	0.8200	1.9100	2.728 (4)	180.00

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

Acknowledgements

This work was supported by the start-up fund for PhDs in Natural Scientific Research of Zhengzhou University of Light Industry (Nos. 2007BSJJ001 and 20801049).

References

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Volume 65| Part 11| November 2009| Pages m1432-m1433

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

Bis(μ-6-hy­droxy­naphthalene-1-carboxyl­ato)bis­­[(6-hy­droxy­naphthalene-1-car­box­yl­ato)(1,10-phenanthroline)cadmium(II)] tetra­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-6-hydroxynaphthalene-1-carboxylato)bis[(6-hydroxynaphthalene-1-carboxylato)(1,10-phenanthroline)cadmium(II)] tetrahydrate