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

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ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages m1510-m1511

Bis(μ-4-methyl­benzoato)-κ3O,O′:O;κ3O:O,O′-bis­­[aqua­(4-methyl­benzoato-κ2O,O′)(nicotinamide-κN1)cadmium]

aDepartment of Physics, Karabük University, 78050 Karabük, Turkey, bDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 12 November 2012; accepted 15 November 2012; online 24 November 2012)

In the dinuclear centrosymmetric title compound, [Cd2(C8H7O2)4(C6H6N2O)2(H2O)2], the CdII ion is chelated by two carboxyl­ate groups from 4-methyl­benzoate anions, and is further coordinated by one nicotinamide and one water mol­ecule; a carboxyl­ate O atom from an adjacent 4-methyl­benzoate anion bridges to the CdII ion, completing the irregular coordination sphere of the seven ligand atoms. In the crystal, inter­molecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The methyl­benzene moiety of one bridging 4-methyl­benzoate anion is disordered over two orientations of equal occupancy.

Related literature

For niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Greenaway et al. (1984[Greenaway, F. T., Pezeshk, A., Cordes, A. W., Noble, M. C. & Sorenson, J. R. J. (1984). Inorg. Chim. Acta, 93, 67-71.]); Hökelek & Necefoğlu (1996[Hökelek, T. & Necefoğlu, H. (1996). Acta Cryst. C52, 1128-1131.]); Hökelek et al. (2009a[Hökelek, T., Yılmaz, F., Tercan, B., Gürgen, F. & Necefoğlu, H. (2009a). Acta Cryst. E65, m1416-m1417.],b[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009b). Acta Cryst. E65, m627-m628.],c[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009c). Acta Cryst. E65, m1037-m1038.],d[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009d). Acta Cryst. E65, m1365-m1366.], 2010a[Hökelek, T., Süzen, Y., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2010a). Acta Cryst. E66, m782-m783.],b[Hökelek, T., Sağlam, E. G., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2010b). Acta Cryst. E66, m1559-m1560.]); Zaman et al. (2012[Zaman, I. G., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m198-m199.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd2(C8H7O2)4(C6H6N2O)2(H2O)2]

  • Mr = 1045.65

  • Triclinic, [P \overline 1]

  • a = 9.5935 (2) Å

  • b = 10.3084 (2) Å

  • c = 12.6606 (3) Å

  • α = 68.326 (3)°

  • β = 74.999 (3)°

  • γ = 66.916 (2)°

  • V = 1060.81 (5) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.07 mm−1

  • T = 100 K

  • 0.36 × 0.31 × 0.28 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.687, Tmax = 0.741

  • 16908 measured reflections

  • 4169 independent reflections

  • 4085 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.019

  • wR(F2) = 0.048

  • S = 1.05

  • 4169 reflections

  • 256 parameters

  • H-atom parameters constrained

  • Δρmax = 1.08 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Selected bond lengths (Å)

Cd1—O1 2.6353 (13)
Cd1—O2 2.2722 (13)
Cd1—O2i 2.5273 (12)
Cd1—O3 2.3739 (13)
Cd1—O4 2.3403 (13)
Cd1—O5 2.2987 (13)
Cd1—N1 2.3243 (15)
Symmetry code: (i) -x+2, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O1ii 0.86 2.10 2.931 (2) 162
N2—H2B⋯O4i 0.86 2.14 2.963 (2) 161
O5—H5A⋯O3iii 0.87 1.89 2.761 (2) 177
O5—H5B⋯O6iv 0.84 1.87 2.689 (2) 165
C3A—H3A⋯O3i 0.93 2.39 3.303 (3) 169
C11—H11⋯O5iii 0.93 2.60 3.481 (2) 159
C17—H17⋯O4i 0.93 2.45 3.286 (2) 150
C21—H21⋯O3iii 0.93 2.51 3.352 (3) 150
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound, (I), consists of dimeric units located around a crystallographic symmetry centre and made up of two Cd cations, four 4-methylbenzoate (PMB) anions, two nicotinamide (NA) ligands and two water molecules (Fig. 1). Each Cd(II) unit is chelated by the carboxylate O atoms of the two PMB anions, and the two monomeric units are bridged through the two oxygen atoms of the two carboxylate groups about an inversion center. The coordination number of each CdII atom is seven. The Cd1···Cd1i distance is 3.7796 (2) Å and O1-Cd1-O1i angle is 76.19 (4)° (symmetry code: (i) -x, -y, 1 - z).

The average Cd-O bond length (Table 1) is 2.4080 (13) Å, and the Cd atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C9/O4) by -0.5904 (1) and 0.3109 (1) Å, respectively. In (I), the O1-Cd1-O2 and O3-Cd1-O4 angles are 52.85 (4) and 55.62 (4) °, respectively. The corresponding O-M-O (where M is a metal) angles are 53.71 (4)° and 54.59 (4)° in [Cd2(HB)4(INA)2].4H2O (Zaman et al., 2012), 55.71 (5)° and 117.52 (4)° in [Cd2(MAB)4(NA)2(H2O)2] (Hökelek et al., 2010b), 55.96 (4)° and 53.78 (4)° in [Cd2(DMAB)4(NA)2(H2O)2] (Hökelek et al., 2010a), 52.91 (4)° and 53.96 (4)° in [Cd(FB)2(INA)2(H2O)].H2O (Hökelek et al., 2009a), 60.70 (4)° in [Co(DMAB)2(INA)(H2O)2] (Hökelek et al., 2009b), 58.45 (9)° in [Mn(DMAB)2(INA)(H2O)2] (Hökelek et al., 2009c), 60.03 (6)° in [Zn(MAB)2(INA)2].H2O (Hökelek et al., 2009d), 58.3 (3)° in [Zn2(DENA)2(HB)4].2H2O (Hökelek & Necefoğlu, 1996) [where NA, INA, DENA, HB, FB, MAB and DMAB are nicotinamide, isonicotinamide, N,N-diethylnicotinamide, 3- or 4-hydroxybenzoate, 4-formylbenzoate, 4-methylaminobenzoate and 4-dimethylaminobenzoate, respectively] and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

The dihedral angle between the planar carboxylate group (O3/C9/O4) and the adjacent benzene ring B (C10-C15) is 7.21 (19) °, while those between rings B, C (N1/C17-C21), D (Cd1/O1/O2/C1) and E (Cd1/O3/O4/C9) are B/C = 59.55 (7) and D/E = 63.01 (5)°.

In the crystal structure, intermolecular O-H···O, N-H···O and C-H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure.

Related literature top

For niacin, see: Krishnamachari (1974). For N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Greenaway et al. (1984); Hökelek & Necefoğlu (1996); Hökelek et al. (2009a,b,c,d, 2010a,b); Zaman et al. (2012).

Experimental top

The title compound was prepared by the reaction of 3CdSO4.8H2O (1.285 g, 5 mmol) in H2O (50 ml) and NA (1.220 g, 10 mmol) in H2O (20 ml) with sodium 4-methylbenzoate (1.580 g, 10 mmol) in H2O (400 ml). The mixture was filtered and set aside to crystallize at ambient temperature for three weeks, giving colorless single crystals.

Refinement top

Atoms H51 and H52 (for H2O) were located in a difference Fourier map and their positions were kept fixed during the refinement process. The remaining H atoms were positioned geometrically with N—H = 0.86 Å (for NH2), C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N,O), where x = 1.5 for methyl and water H atoms and x = 1.2 for NH2 and aromatic H atoms. In the benzene ring A (C2-C7), the C2, C3, C4, C5 C6, C7 and the attached H3, H4, H6, H7 atoms, respectively, together with the C8, H81, H82 and H83 atoms of the methyl group attached at C5 are disordered over two orientations. During the refinement process the disordered C2A, C3A, H3A, C4A, H4A, C5A, C6A, H6A, C7A, H7A, C8A, H8A1, H8A2, H8A3 and C2B, C3B, H3B, C4B, H4B, C5B, C6B, H6B, C7B, H7B, C8B, H8B1, H8B2, H8B3 atoms were refined with occupancies ratios of 0.50:0.50.

Computing details top

Data collection: APEX2 (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: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Primed atoms are generated by the symmetry operators: (') 2 - x, 2 - y, 1 - z.
Bis(µ-4-methylbenzoato)-κ3O,O':O; κ3O:O,O'-bis[aqua(4-methylbenzoato- κ2O,O')(nicotinamide-κN1)cadmium] top
Crystal data top
[Cd2(C8H7O2)4(C6H6N2O)2(H2O)2]Z = 1
Mr = 1045.65F(000) = 528
Triclinic, P1Dx = 1.637 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5935 (2) ÅCell parameters from 9926 reflections
b = 10.3084 (2) Åθ = 2.3–28.5°
c = 12.6606 (3) ŵ = 1.07 mm1
α = 68.326 (3)°T = 100 K
β = 74.999 (3)°Block, colorless
γ = 66.916 (2)°0.36 × 0.31 × 0.28 mm
V = 1060.81 (5) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
4169 independent reflections
Radiation source: fine-focus sealed tube4085 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.687, Tmax = 0.741k = 1212
16908 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0193P)2 + 1.1679P]
where P = (Fo2 + 2Fc2)/3
4169 reflections(Δ/σ)max = 0.002
256 parametersΔρmax = 1.08 e Å3
0 restraintsΔρmin = 0.72 e Å3
Crystal data top
[Cd2(C8H7O2)4(C6H6N2O)2(H2O)2]γ = 66.916 (2)°
Mr = 1045.65V = 1060.81 (5) Å3
Triclinic, P1Z = 1
a = 9.5935 (2) ÅMo Kα radiation
b = 10.3084 (2) ŵ = 1.07 mm1
c = 12.6606 (3) ÅT = 100 K
α = 68.326 (3)°0.36 × 0.31 × 0.28 mm
β = 74.999 (3)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
4169 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4085 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.741Rint = 0.021
16908 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.048H-atom parameters constrained
S = 1.05Δρmax = 1.08 e Å3
4169 reflectionsΔρmin = 0.72 e Å3
256 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cd10.817156 (14)0.963852 (13)0.512013 (10)0.01282 (5)
O10.96132 (15)0.68775 (14)0.62253 (11)0.0203 (3)
O21.01690 (14)0.88132 (13)0.61152 (10)0.0160 (3)
O30.66922 (14)1.01399 (14)0.36876 (11)0.0172 (3)
O40.90596 (15)0.86161 (14)0.36017 (11)0.0181 (3)
O50.64150 (14)0.86318 (13)0.64128 (11)0.0169 (3)
H5A0.54400.89870.63760.025*
H5B0.65770.77560.64440.025*
O60.63943 (16)1.59642 (15)0.65749 (14)0.0291 (3)
N10.67632 (17)1.17891 (16)0.56260 (13)0.0151 (3)
N20.87749 (18)1.44037 (18)0.62850 (15)0.0220 (3)
H2A0.91871.49750.63450.026*
H2B0.93421.35780.61570.026*
C11.02645 (19)0.74445 (19)0.65768 (15)0.0140 (3)
C2A1.1134 (3)0.6536 (3)0.7611 (2)0.0220 (5)0.50
C3A1.2108 (4)0.7037 (3)0.7882 (3)0.0220 (5)0.50
H3A1.23300.78780.73840.026*0.50
C4A1.2749 (3)0.6283 (4)0.8898 (3)0.0220 (5)0.50
H4A1.34000.66180.90790.026*0.50
C5A1.2417 (3)0.5027 (3)0.9642 (2)0.0220 (5)0.50
C6A1.1444 (4)0.4525 (3)0.9370 (2)0.0220 (5)0.50
H6A1.12220.36850.98680.026*0.50
C7A1.0803 (3)0.5280 (3)0.8355 (2)0.0220 (5)0.50
H7A1.01510.49450.81730.026*0.50
C8A1.305 (3)0.422 (4)1.079 (3)0.042 (3)0.50
H8A11.37200.46701.08440.064*0.50
H8A21.36080.31991.08300.064*0.50
H8A31.22210.42721.14030.064*0.50
C2B1.1134 (3)0.6556 (3)0.7575 (2)0.0196 (5)0.50
C3B1.1715 (4)0.7249 (2)0.8029 (3)0.0196 (5)0.50
H3B1.15940.82490.76910.024*0.50
C4B1.2478 (3)0.6447 (3)0.8986 (3)0.0196 (5)0.50
H4B1.28670.69110.92890.024*0.50
C5B1.2659 (3)0.4953 (3)0.9490 (2)0.0196 (5)0.50
C6B1.2078 (4)0.4260 (2)0.9036 (2)0.0196 (5)0.50
H6B1.21990.32600.93730.024*0.50
C7B1.1315 (3)0.5061 (3)0.8079 (2)0.0196 (5)0.50
H7B1.09270.45970.77760.024*0.50
C8B1.340 (3)0.414 (4)1.059 (3)0.042 (3)0.50
H8B11.28360.35221.11320.064*0.50
H8B21.34030.48421.09190.064*0.50
H8B31.44360.35321.04220.064*0.50
C90.7838 (2)0.93699 (19)0.31593 (15)0.0147 (3)
C100.7771 (2)0.9423 (2)0.19762 (15)0.0167 (4)
C110.6466 (2)1.0303 (2)0.14489 (17)0.0236 (4)
H110.55961.08090.18540.028*
C120.6455 (3)1.0431 (2)0.03214 (18)0.0266 (4)
H120.55741.10240.00220.032*
C130.7736 (3)0.9690 (2)0.03055 (16)0.0244 (4)
C140.9032 (3)0.8808 (2)0.02313 (18)0.0269 (4)
H140.98980.82980.01720.032*
C150.9059 (2)0.8675 (2)0.13545 (17)0.0222 (4)
H150.99410.80830.16960.027*
C160.7713 (3)0.9837 (3)0.15339 (18)0.0347 (5)
H16A0.77360.89180.15770.052*
H16B0.85891.00800.20060.052*
H16C0.67981.06050.17990.052*
C170.7412 (2)1.25977 (19)0.58365 (15)0.0149 (3)
H170.84711.23440.56970.018*
C180.6572 (2)1.37934 (19)0.62518 (16)0.0168 (4)
C190.4990 (2)1.4139 (2)0.64957 (19)0.0250 (4)
H190.43951.49150.67960.030*
C200.4319 (2)1.3308 (2)0.6283 (2)0.0277 (5)
H200.32651.35140.64430.033*
C210.5235 (2)1.2166 (2)0.58314 (17)0.0203 (4)
H210.47721.16370.56630.024*
C220.7261 (2)1.4797 (2)0.63911 (16)0.0186 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.01161 (7)0.01484 (7)0.01396 (7)0.00428 (5)0.00216 (5)0.00624 (5)
O10.0207 (7)0.0209 (7)0.0224 (7)0.0098 (5)0.0069 (5)0.0040 (5)
O20.0167 (6)0.0148 (6)0.0150 (6)0.0054 (5)0.0026 (5)0.0022 (5)
O30.0158 (6)0.0205 (6)0.0163 (6)0.0058 (5)0.0022 (5)0.0070 (5)
O40.0169 (6)0.0194 (6)0.0190 (6)0.0036 (5)0.0053 (5)0.0075 (5)
O50.0152 (6)0.0131 (6)0.0217 (7)0.0044 (5)0.0018 (5)0.0052 (5)
O60.0198 (7)0.0197 (7)0.0533 (10)0.0052 (6)0.0021 (7)0.0203 (7)
N10.0155 (7)0.0142 (7)0.0155 (7)0.0054 (6)0.0033 (6)0.0030 (6)
N20.0172 (8)0.0180 (8)0.0365 (10)0.0057 (6)0.0044 (7)0.0142 (7)
C10.0095 (8)0.0157 (8)0.0147 (8)0.0035 (7)0.0021 (6)0.0054 (7)
C2A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C3A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C4A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C5A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C6A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C7A0.0206 (9)0.0223 (10)0.0217 (10)0.0072 (7)0.0045 (7)0.0038 (8)
C8A0.045 (9)0.042 (4)0.036 (8)0.020 (7)0.026 (6)0.012 (5)
C2B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C3B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C4B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C5B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C6B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C7B0.0151 (8)0.0173 (10)0.0238 (10)0.0035 (6)0.0062 (7)0.0027 (8)
C8B0.045 (9)0.042 (4)0.036 (8)0.020 (7)0.026 (6)0.012 (5)
C90.0188 (9)0.0142 (8)0.0145 (8)0.0106 (7)0.0021 (7)0.0023 (7)
C100.0223 (9)0.0166 (8)0.0148 (9)0.0112 (7)0.0028 (7)0.0033 (7)
C110.0226 (10)0.0288 (10)0.0200 (10)0.0069 (8)0.0040 (8)0.0090 (8)
C120.0306 (11)0.0297 (11)0.0206 (10)0.0097 (9)0.0094 (8)0.0051 (8)
C130.0385 (12)0.0239 (10)0.0152 (9)0.0165 (9)0.0040 (8)0.0039 (8)
C140.0320 (11)0.0288 (10)0.0208 (10)0.0107 (9)0.0012 (8)0.0109 (8)
C150.0243 (10)0.0229 (9)0.0201 (10)0.0084 (8)0.0034 (8)0.0063 (8)
C160.0517 (15)0.0386 (12)0.0174 (10)0.0179 (11)0.0054 (10)0.0086 (9)
C170.0149 (9)0.0154 (8)0.0143 (8)0.0061 (7)0.0021 (7)0.0029 (7)
C180.0159 (9)0.0137 (8)0.0208 (9)0.0059 (7)0.0024 (7)0.0042 (7)
C190.0169 (10)0.0172 (9)0.0415 (12)0.0037 (8)0.0008 (9)0.0137 (9)
C200.0129 (9)0.0203 (9)0.0503 (14)0.0045 (8)0.0028 (9)0.0131 (9)
C210.0172 (9)0.0156 (8)0.0298 (10)0.0073 (7)0.0056 (8)0.0050 (8)
C220.0199 (9)0.0153 (8)0.0214 (9)0.0063 (7)0.0028 (7)0.0060 (7)
Geometric parameters (Å, º) top
Cd1—O12.6353 (13)C2B—C7B1.3900
Cd1—O22.2722 (13)C3B—C4B1.3900
Cd1—O2i2.5273 (12)C3B—H3B0.9300
Cd1—O32.3739 (13)C4B—C5B1.3900
Cd1—O42.3403 (13)C4B—H4B0.9300
Cd1—O52.2987 (13)C5B—C6B1.3900
Cd1—N12.3243 (15)C5B—C8B1.53 (3)
Cd1—C92.7076 (17)C6B—C7B1.3900
N1—C171.345 (2)C6B—H6B0.9300
N1—C211.341 (2)C7B—H7B0.9300
N2—C221.330 (2)C8B—H8B10.9600
N2—H2A0.8600C8B—H8B20.9600
N2—H2B0.8600C8B—H8B30.9600
O1—C11.246 (2)C9—C101.496 (2)
O2—C11.288 (2)C10—C111.390 (3)
O2—Cd1i2.5273 (12)C10—C151.392 (3)
O3—C91.270 (2)C11—C121.387 (3)
O4—C91.263 (2)C11—H110.9300
O5—H5A0.8678C12—C131.389 (3)
O5—H5B0.8411C12—H120.9300
O6—C221.231 (2)C13—C141.389 (3)
C1—C2B1.491 (3)C13—C161.511 (3)
C1—C2A1.528 (3)C14—C151.383 (3)
C2A—C3A1.3900C14—H140.9300
C2A—C7A1.3900C15—H150.9300
C3A—C4A1.3900C16—H16A0.9600
C3A—H3A0.9300C16—H16B0.9600
C4A—C5A1.3900C16—H16C0.9600
C4A—H4A0.9300C17—C181.388 (2)
C5A—C6A1.3900C17—H170.9300
C5A—C8A1.53 (3)C18—C191.393 (3)
C6A—C7A1.3900C18—C221.506 (2)
C6A—H6A0.9300C19—C201.383 (3)
C7A—H7A0.9300C19—H190.9300
C8A—H8A10.9600C20—C211.382 (3)
C8A—H8A20.9600C20—H200.9300
C8A—H8A30.9600C21—H210.9300
C2B—C3B1.3900
O1—Cd1—C9101.80 (5)C4B—C3B—C2B120.0
O2—Cd1—O152.85 (4)C4B—C3B—H3B120.0
O2i—Cd1—O1116.34 (4)C2B—C3B—H3B120.0
O2—Cd1—O2i76.22 (5)C5B—C4B—C3B120.0
O2—Cd1—O3162.16 (4)C5B—C4B—H4B120.0
O2—Cd1—O4106.73 (4)C3B—C4B—H4B120.0
O2—Cd1—O5103.70 (4)C4B—C5B—C6B120.0
O2—Cd1—N199.20 (5)C4B—C5B—C8B118.4 (14)
O2—Cd1—C9134.23 (5)C6B—C5B—C8B121.5 (14)
O2i—Cd1—C986.97 (5)C7B—C6B—C5B120.0
O3—Cd1—O1119.67 (4)C7B—C6B—H6B120.0
O3—Cd1—O2i96.74 (4)C5B—C6B—H6B120.0
O3—Cd1—C927.97 (5)C6B—C7B—C2B120.0
O4—Cd1—O180.08 (4)C6B—C7B—H7B120.0
O4—Cd1—O2i81.30 (4)C2B—C7B—H7B120.0
O4—Cd1—O355.62 (4)C5B—C8B—H8B1109.5
O4—Cd1—C927.78 (5)C5B—C8B—H8B2109.5
O5—Cd1—O171.23 (4)H8B1—C8B—H8B2109.5
O5—Cd1—O2i167.88 (4)C5B—C8B—H8B3109.5
O5—Cd1—O386.63 (4)H8B1—C8B—H8B3109.5
O5—Cd1—O4109.99 (5)H8B2—C8B—H8B3109.5
O5—Cd1—N186.22 (5)O4—C9—O3120.53 (16)
O5—Cd1—C9101.04 (5)O4—C9—C10119.65 (16)
N1—Cd1—O1135.38 (5)O3—C9—C10119.74 (16)
N1—Cd1—O2i81.86 (5)O4—C9—Cd159.71 (9)
N1—Cd1—O395.92 (5)O3—C9—Cd161.25 (9)
N1—Cd1—O4144.53 (5)C10—C9—Cd1170.35 (12)
N1—Cd1—C9120.41 (5)C11—C10—C15118.92 (17)
C1—O1—Cd184.10 (10)C11—C10—C9120.69 (17)
Cd1—O2—Cd1i103.78 (5)C15—C10—C9120.21 (17)
C1—O2—Cd199.86 (11)C12—C11—C10120.23 (19)
C1—O2—Cd1i139.66 (11)C12—C11—H11119.9
C9—O3—Cd190.78 (10)C10—C11—H11119.9
C9—O4—Cd192.51 (10)C11—C12—C13121.2 (2)
Cd1—O5—H5A124.2C11—C12—H12119.4
Cd1—O5—H5B113.2C13—C12—H12119.4
H5A—O5—H5B99.0C14—C13—C12118.05 (18)
C17—N1—Cd1123.00 (12)C14—C13—C16121.1 (2)
C21—N1—Cd1118.75 (12)C12—C13—C16120.8 (2)
C21—N1—C17117.90 (16)C15—C14—C13121.3 (2)
C22—N2—H2A120.0C15—C14—H14119.4
C22—N2—H2B120.0C13—C14—H14119.4
H2A—N2—H2B120.0C14—C15—C10120.27 (19)
O1—C1—O2121.27 (16)C14—C15—H15119.9
O1—C1—C2B120.30 (18)C10—C15—H15119.9
O2—C1—C2B118.40 (18)C13—C16—H16A109.5
O1—C1—C2A120.12 (19)C13—C16—H16B109.5
O2—C1—C2A118.55 (18)H16A—C16—H16B109.5
C3A—C2A—C7A120.0C13—C16—H16C109.5
C3A—C2A—C1121.0 (2)H16A—C16—H16C109.5
C7A—C2A—C1118.6 (2)H16B—C16—H16C109.5
C4A—C3A—C2A120.0N1—C17—C18122.98 (17)
C4A—C3A—H3A120.0N1—C17—H17118.5
C2A—C3A—H3A120.0C18—C17—H17118.5
C3A—C4A—C5A120.0C17—C18—C19118.31 (17)
C3A—C4A—H4A120.0C17—C18—C22123.76 (16)
C5A—C4A—H4A120.0C19—C18—C22117.83 (16)
C6A—C5A—C4A120.0C20—C19—C18118.87 (18)
C6A—C5A—C8A118.9 (13)C20—C19—H19120.6
C4A—C5A—C8A121.0 (13)C18—C19—H19120.6
C7A—C6A—C5A120.0C21—C20—C19119.12 (18)
C7A—C6A—H6A120.0C21—C20—H20120.4
C5A—C6A—H6A120.0C19—C20—H20120.4
C6A—C7A—C2A120.0N1—C21—C20122.76 (17)
C6A—C7A—H7A120.0N1—C21—H21118.6
C2A—C7A—H7A120.0C20—C21—H21118.6
C3B—C2B—C7B120.0O6—C22—N2122.79 (17)
C3B—C2B—C1119.3 (2)O6—C22—C18118.32 (17)
C7B—C2B—C1120.6 (2)N2—C22—C18118.87 (16)
O2—Cd1—O1—C17.87 (10)Cd1—O2—C1—C2B162.66 (17)
O2i—Cd1—O1—C152.76 (11)Cd1i—O2—C1—C2B72.0 (2)
O3—Cd1—O1—C1168.40 (10)Cd1—O3—C9—O47.53 (16)
O4—Cd1—O1—C1127.81 (10)Cd1—O3—C9—C10168.99 (14)
O5—Cd1—O1—C1116.97 (11)Cd1—O4—C9—O37.64 (16)
N1—Cd1—O1—C153.31 (12)Cd1—O4—C9—C10168.88 (13)
C9—Cd1—O1—C1145.24 (10)Cd1—N1—C17—C18173.17 (13)
O1—Cd1—O2—Cd1i139.37 (7)C21—N1—C17—C180.1 (3)
O1—Cd1—O2—C17.69 (9)Cd1—N1—C21—C20171.10 (16)
O2i—Cd1—O2—Cd1i0.0C17—N1—C21—C202.3 (3)
O2i—Cd1—O2—C1147.05 (12)O1—C1—C2A—C3A167.42 (17)
O3—Cd1—O2—Cd1i68.42 (15)O1—C1—C2A—C7A19.9 (3)
O3—Cd1—O2—C178.64 (18)O2—C1—C2A—C3A15.5 (3)
O4—Cd1—O2—Cd1i76.33 (5)O2—C1—C2A—C7A157.16 (18)
O4—Cd1—O2—C170.73 (11)C2B—C1—C2A—C3A64 (16)
O5—Cd1—O2—Cd1i167.52 (4)C2B—C1—C2A—C7A124 (16)
O5—Cd1—O2—C145.42 (11)C1—C2A—C3A—C4A172.5 (3)
N1—Cd1—O2—Cd1i79.20 (5)C7A—C2A—C3A—C4A0.0
N1—Cd1—O2—C1133.75 (10)C1—C2A—C7A—C6A172.7 (3)
C9—Cd1—O2—Cd1i71.66 (7)C3A—C2A—C7A—C6A0.0
C9—Cd1—O2—C175.39 (12)C2A—C3A—C4A—C5A0.0
O1—Cd1—O3—C955.17 (11)C3A—C4A—C5A—C6A0.0
O2—Cd1—O3—C95.0 (2)C3A—C4A—C5A—C8A177.3 (11)
O2i—Cd1—O3—C970.38 (10)C4A—C5A—C6A—C7A0.0
O4—Cd1—O3—C94.23 (9)C8A—C5A—C6A—C7A177.4 (11)
O5—Cd1—O3—C9121.31 (10)C5A—C6A—C7A—C2A0.0
N1—Cd1—O3—C9152.85 (10)O1—C1—C2B—C3B173.29 (17)
O1—Cd1—O4—C9141.03 (10)O1—C1—C2B—C7B4.2 (3)
O2—Cd1—O4—C9172.81 (10)O2—C1—C2B—C3B4.7 (3)
O2i—Cd1—O4—C9100.13 (10)O2—C1—C2B—C7B177.77 (17)
O3—Cd1—O4—C94.26 (9)C2A—C1—C2B—C3B97 (16)
O5—Cd1—O4—C975.32 (10)C2A—C1—C2B—C7B81 (16)
N1—Cd1—O4—C937.61 (14)C1—C2B—C3B—C4B177.6 (2)
O1—Cd1—N1—C1777.16 (15)C7B—C2B—C3B—C4B0.0
O1—Cd1—N1—C2195.89 (14)C1—C2B—C7B—C6B177.5 (3)
O2—Cd1—N1—C1732.13 (14)C3B—C2B—C7B—C6B0.0
O2i—Cd1—N1—C1742.39 (13)C2B—C3B—C4B—C5B0.0
O2—Cd1—N1—C21140.92 (13)C3B—C4B—C5B—C6B0.0
O2i—Cd1—N1—C21144.57 (14)C3B—C4B—C5B—C8B175.6 (9)
O3—Cd1—N1—C17138.37 (13)C4B—C5B—C6B—C7B0.0
O3—Cd1—N1—C2148.58 (14)C8B—C5B—C6B—C7B175.5 (9)
O4—Cd1—N1—C17104.74 (14)C5B—C6B—C7B—C2B0.0
O4—Cd1—N1—C2182.21 (16)O3—C9—C10—C110.2 (3)
O5—Cd1—N1—C17135.41 (14)O3—C9—C10—C15174.98 (16)
O5—Cd1—N1—C2137.63 (14)O4—C9—C10—C11176.73 (17)
C9—Cd1—N1—C17124.00 (13)O4—C9—C10—C151.6 (3)
C9—Cd1—N1—C2162.95 (15)C9—C10—C11—C12175.15 (18)
O1—Cd1—C9—O3133.23 (9)C15—C10—C11—C120.1 (3)
O1—Cd1—C9—O439.26 (10)C9—C10—C15—C14175.38 (17)
O2—Cd1—C9—O3177.88 (8)C11—C10—C15—C140.1 (3)
O2i—Cd1—C9—O3110.49 (10)C10—C11—C12—C130.0 (3)
O2—Cd1—C9—O49.63 (13)C11—C12—C13—C140.2 (3)
O2i—Cd1—C9—O477.02 (10)C11—C12—C13—C16180.00 (19)
O3—Cd1—C9—O4172.49 (16)C12—C13—C14—C150.4 (3)
O4—Cd1—C9—O3172.49 (16)C16—C13—C14—C15179.8 (2)
O5—Cd1—C9—O360.34 (10)C13—C14—C15—C100.4 (3)
O5—Cd1—C9—O4112.15 (10)N1—C17—C18—C192.1 (3)
N1—Cd1—C9—O331.76 (11)N1—C17—C18—C22174.19 (16)
N1—Cd1—C9—O4155.75 (9)C17—C18—C19—C201.9 (3)
Cd1—O1—C1—O213.02 (15)C22—C18—C19—C20174.68 (19)
Cd1—O1—C1—C2A164.00 (18)C17—C18—C22—O6167.60 (18)
Cd1—O1—C1—C2B164.90 (18)C17—C18—C22—N210.9 (3)
Cd1—O2—C1—O115.30 (18)C19—C18—C22—O68.8 (3)
Cd1i—O2—C1—O1110.02 (19)C19—C18—C22—N2172.76 (19)
Cd1—O2—C1—C2A161.77 (16)C18—C19—C20—C210.3 (3)
Cd1i—O2—C1—C2A72.9 (2)C19—C20—C21—N12.5 (3)
Symmetry code: (i) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.862.102.931 (2)162
N2—H2B···O4i0.862.142.963 (2)161
O5—H5A···O3iii0.871.892.761 (2)177
O5—H5B···O6iv0.841.872.689 (2)165
C3A—H3A···O3i0.932.393.303 (3)169
C11—H11···O5iii0.932.603.481 (2)159
C17—H17···O4i0.932.453.286 (2)150
C21—H21···O3iii0.932.513.352 (3)150
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+1, z; (iii) x+1, y+2, z+1; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formula[Cd2(C8H7O2)4(C6H6N2O)2(H2O)2]
Mr1045.65
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.5935 (2), 10.3084 (2), 12.6606 (3)
α, β, γ (°)68.326 (3), 74.999 (3), 66.916 (2)
V3)1060.81 (5)
Z1
Radiation typeMo Kα
µ (mm1)1.07
Crystal size (mm)0.36 × 0.31 × 0.28
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.687, 0.741
No. of measured, independent and
observed [I > 2σ(I)] reflections
16908, 4169, 4085
Rint0.021
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.048, 1.05
No. of reflections4169
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.08, 0.72

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Selected bond lengths (Å) top
Cd1—O12.6353 (13)Cd1—O42.3403 (13)
Cd1—O22.2722 (13)Cd1—O52.2987 (13)
Cd1—O2i2.5273 (12)Cd1—N12.3243 (15)
Cd1—O32.3739 (13)
Symmetry code: (i) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.862.102.931 (2)162
N2—H2B···O4i0.862.142.963 (2)161
O5—H5A···O3iii0.871.892.761 (2)177
O5—H5B···O6iv0.841.872.689 (2)165
C3A—H3A···O3i0.932.393.303 (3)169
C11—H11···O5iii0.932.603.481 (2)159
C17—H17···O4i0.932.453.286 (2)150
C21—H21···O3iii0.932.513.352 (3)150
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+1, z; (iii) x+1, y+2, z+1; (iv) x, y1, z.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

References

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COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages m1510-m1511
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