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

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ISSN: 2056-9890

Bis[μ-2,2′-di­methyl-1,1′-(oxydi­ethyl­ene)bis­­(1H-benzimidazole)-κ2N3:N3′]bis­­[bis­­(4-meth­oxy­benzoato-κ2O,O′)cadmium(II)]

aWeifang Vocational College, Weifang 261041, People's Republic of China
*Correspondence e-mail: dianying_zhao@yahoo.com.cn

(Received 12 February 2010; accepted 12 March 2010; online 20 March 2010)

The title complex, [Cd2(C8H7O3)4(C20H22N4O)2], forms a dimer of the paddle-wheel type, located on a crystallographic inversion centre. The CdII ion is hexa­coordinated by four carboxylate O atoms [Cd⋯O = 2.280 (2)–2.404 (2) Å] from two chelating 4-methoxy­benzoate anions, and two N atoms [Cd⋯N = 2.313 (2) and 2.332 (2) Å] from one chelating 2,2′-dimethyl-3,3′-(oxydiethyl­ene)bis­(1H-benzimidazole) ligand. In the crystal, mol­ecules are linked by a weak inter­molecular C—H⋯O hydrogen bond and an inter­molecular C—H⋯π inter­action.

Related literature

For a related structure, see: Zhao et al. (2002[Zhao, Q.-H., Ma, Y.-P., Wang, Q.-H. & Fang, R.-B. (2002). Chin. J. Struct. Chem. 21, 513-516.]). For bis­(imid­azole) ligands with –CH2– spacers as N-donor bridging ligands, see: Hoskins et al. (1997[Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc. 119, 2952-2953.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd2(C8H7O3)4(C20H22N4O)2]

  • Mr = 1498.18

  • Triclinic, [P \overline 1]

  • a = 9.0379 (5) Å

  • b = 13.8130 (8) Å

  • c = 13.9361 (6) Å

  • α = 88.143 (4)°

  • β = 86.539 (4)°

  • γ = 74.863 (4)°

  • V = 1676.11 (15) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.71 mm−1

  • T = 293 K

  • 0.28 × 0.24 × 0.21 mm

Data collection
  • Oxford Diffraction Gemini R Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.831, Tmax = 0.902

  • 12519 measured reflections

  • 7555 independent reflections

  • 4356 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.051

  • S = 0.85

  • 7555 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C21—H21⋯O7i 0.93 2.50 3.333 (3) 149
C6—H6⋯Cgii 0.93 2.76 3.684 (5) 170
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Bis(imidazole) ligands with –CH2- spacers are a good candidate for N-donor bridging ligand (Hoskins et al., 1997). Up to now, 2,2'-bis(2-methyl-1H-benzimidazole)ether ligand, as a flexible ligand, is rarely investigated in constructing coordination polymers.

In the title compound (Fig. 1), the CdII ion is hexacoordinated by four O atoms from two chelating 4-methoxybenzoate anions, and two N atoms from one chelating 2,2'-bis(2-methyl-1H-benzimidazole)ether ligand. The Cd–O distances are found in the range from 2.280 (2) to 2.404 (2) Å, which is similar to previous report (Zhao et al., 2002). The Cd–N distances are 2.313 (2) and 2.332 (2) Å, respectively. The crystal structure (Fig. 2) is stabilized by a weak intermolecular C–H···O hydrogen bond between the benzene H atom of 2-methyl-1H-benzimidazole ring and the O atom of diethyl ether group, with a C21–H21···O7 (Table 1 & Fig. 2). The crystal structure is further stabilized by an inetrmolecular C–H···π interaction between the aryl H atom of 4-methoxybenzoate group and the benzene ring of neighboring 4-methoxybenzoate group, with a C6-H6···Cg (Table 1 & Fig. 3; Cg is the centroid of the C10-C15 benzene ring).

Related literature top

For a related structure, see: Zhao et al. (2002). For bis(imidazole) ligands with –CH2- spacers as N-donor bridging ligands, see: Hoskins et al. (1997).

Experimental top

An aqueous solution (10 ml) of 4-methoxybenzoic acid (0.072 g, 0.4 mmol ), 2,2'-bis(2-methylbenzimidazole)ether (0.065 g, 0.2 mmol) and Cd(Ac)2 (0.046 g, 0.2 mmol) was added in and sealed in 18 ml Teflon-lined stainless steel container. The container was heated to 140 °C and held at that temperature for 72 h, then cooled to room temperature at a rate of 10 °C/h. And then the title compound was isolated.

Refinement top

C-bound H-atoms were geometrically positioned (C–H 0.93 Å) and refined using a riding model, with Uiso = 1.2Ueq (C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x+1, -y+1, -z+1.]
[Figure 2] Fig. 2. C–H···O interactions (dotted lines) in the title compound. [Symmetry code: (i) x+1, y, z; (iii) x-1, y, z.]
[Figure 3] Fig. 3. C–H···π interactions (dotted lines) in the title compound. [Symmetry code: (ii) -x+2, -y, -z; (iv) -x+1, -y+1, -z+1.]
Bis[µ-2,2'-dimethyl-1,1'-(oxydiethylene)bis(1H-benzimidazole)- κ2N3:N3']bis[bis(4-methoxybenzoato- κ2O,O')cadmium(II)] top
Crystal data top
[Cd2(C8H7O3)4(C20H22N4O)2]Z = 1
Mr = 1498.18F(000) = 768
Triclinic, P1Dx = 1.484 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0379 (5) ÅCell parameters from 4356 reflections
b = 13.8130 (8) Åθ = 2.8–29.2°
c = 13.9361 (6) ŵ = 0.71 mm1
α = 88.143 (4)°T = 293 K
β = 86.539 (4)°Block, colorless
γ = 74.863 (4)°0.28 × 0.24 × 0.21 mm
V = 1676.11 (15) Å3
Data collection top
Oxford Diffraction Gemini R Ultra
diffractometer
7555 independent reflections
Radiation source: fine-focus sealed tube4356 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.0 pixels mm-1θmax = 29.2°, θmin = 2.8°
ω scanh = 127
Absorption correction: multi-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
k = 1816
Tmin = 0.831, Tmax = 0.902l = 1817
12519 measured reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0113P)2]
where P = (Fo2 + 2Fc2)/3
7555 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Cd2(C8H7O3)4(C20H22N4O)2]γ = 74.863 (4)°
Mr = 1498.18V = 1676.11 (15) Å3
Triclinic, P1Z = 1
a = 9.0379 (5) ÅMo Kα radiation
b = 13.8130 (8) ŵ = 0.71 mm1
c = 13.9361 (6) ÅT = 293 K
α = 88.143 (4)°0.28 × 0.24 × 0.21 mm
β = 86.539 (4)°
Data collection top
Oxford Diffraction Gemini R Ultra
diffractometer
7555 independent reflections
Absorption correction: multi-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
4356 reflections with I > 2σ(I)
Tmin = 0.831, Tmax = 0.902Rint = 0.027
12519 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.051H-atom parameters constrained
S = 0.85Δρmax = 0.38 e Å3
7555 reflectionsΔρmin = 0.34 e Å3
433 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
xyzUiso*/Ueq
Cd10.94281 (2)0.230266 (15)0.254883 (14)0.04683 (7)
C11.2095 (3)0.1039 (2)0.19577 (17)0.0473 (7)
C21.3622 (3)0.03887 (18)0.16114 (16)0.0422 (7)
C31.4938 (3)0.06938 (19)0.16937 (16)0.0490 (7)
H31.48700.13110.19660.059*
C41.6363 (3)0.0106 (2)0.13810 (17)0.0583 (8)
H41.72410.03260.14400.070*
C51.6461 (3)0.0806 (2)0.09832 (18)0.0557 (8)
C61.5159 (3)0.11242 (19)0.08944 (17)0.0561 (8)
H61.52310.17420.06240.067*
C71.3742 (3)0.05289 (18)0.12062 (16)0.0505 (7)
H71.28640.07480.11420.061*
C81.9160 (4)0.1138 (3)0.0596 (2)0.1036 (13)
H8A2.00000.16680.03520.155*
H8B1.93670.09650.12260.155*
H8C1.90390.05620.01750.155*
C90.7323 (4)0.29694 (19)0.1234 (2)0.0550 (8)
C100.6093 (3)0.33063 (18)0.05549 (19)0.0491 (7)
C110.6409 (4)0.3618 (2)0.0378 (2)0.0682 (9)
H110.74080.36200.05790.082*
C120.5249 (5)0.3923 (2)0.1003 (2)0.0759 (10)
H120.54750.41270.16250.091*
C130.3752 (4)0.3931 (2)0.0725 (2)0.0659 (9)
C140.3418 (3)0.3637 (2)0.0201 (2)0.0629 (9)
H140.24150.36490.04060.075*
C150.4595 (3)0.33262 (18)0.08161 (18)0.0543 (8)
H150.43640.31200.14370.065*
C160.1153 (5)0.4292 (3)0.1140 (3)0.1410 (19)
H16A0.05360.45090.16830.212*
H16B0.08150.47650.06320.212*
H16C0.10530.36450.09200.212*
C170.6274 (3)0.14017 (18)0.39082 (17)0.0476 (7)
H17A0.55310.12110.43440.071*
H17B0.65380.09400.33860.071*
H17C0.58490.20670.36600.071*
C180.7663 (3)0.13819 (16)0.44216 (18)0.0371 (6)
C190.9933 (3)0.14764 (15)0.47397 (17)0.0336 (6)
C201.1423 (3)0.15861 (16)0.47225 (19)0.0418 (7)
H201.18870.17810.41620.050*
C211.2181 (3)0.13993 (18)0.5554 (2)0.0504 (7)
H211.31790.14650.55550.060*
C221.1499 (3)0.11128 (18)0.6402 (2)0.0529 (7)
H221.20420.10040.69580.064*
C231.0033 (3)0.09874 (17)0.64291 (19)0.0449 (7)
H230.95830.07800.69890.054*
C240.9266 (3)0.11808 (15)0.55947 (17)0.0340 (6)
C250.6691 (2)0.08745 (16)0.60518 (16)0.0413 (6)
H25A0.72090.03700.65050.050*
H25B0.60050.05910.57090.050*
C260.5759 (3)0.17790 (17)0.65981 (16)0.0439 (7)
H26A0.50330.15820.70550.053*
H26B0.64300.20660.69500.053*
C270.3805 (3)0.32728 (17)0.63788 (17)0.0456 (7)
H27A0.42650.36860.67540.055*
H27B0.31310.29900.68040.055*
C280.2916 (3)0.38904 (16)0.55925 (16)0.0417 (7)
H28A0.36130.41380.51530.050*
H28B0.24430.34720.52330.050*
C290.3390 (3)0.59244 (19)0.6021 (2)0.0642 (9)
H29A0.41300.53820.57090.096*
H29B0.37770.60720.66100.096*
H29C0.32050.65070.56060.096*
C300.1930 (3)0.56328 (18)0.62326 (17)0.0418 (7)
C310.0241 (3)0.47285 (17)0.62709 (16)0.0356 (6)
C320.0560 (3)0.40092 (18)0.62173 (18)0.0490 (7)
H320.01180.33900.59410.059*
C330.2046 (3)0.4258 (2)0.6594 (2)0.0625 (8)
H330.26280.37960.65720.075*
C340.2700 (3)0.5184 (2)0.7009 (2)0.0595 (8)
H340.37090.53220.72590.071*
C350.1908 (3)0.58992 (19)0.70604 (17)0.0482 (7)
H350.23570.65170.73380.058*
C360.0400 (3)0.56591 (16)0.66778 (15)0.0349 (6)
N10.8906 (2)0.16039 (13)0.40196 (13)0.0367 (5)
N20.7832 (2)0.11225 (13)0.53661 (14)0.0344 (5)
N30.1729 (2)0.47365 (13)0.59854 (13)0.0386 (5)
N40.0680 (2)0.62167 (13)0.66601 (13)0.0386 (5)
O11.0920 (2)0.07181 (13)0.19366 (12)0.0593 (5)
O21.20357 (19)0.18917 (13)0.22786 (12)0.0616 (5)
O31.7801 (2)0.14625 (15)0.06458 (14)0.0859 (7)
O40.8677 (2)0.30016 (15)0.10123 (13)0.0741 (6)
O50.6979 (2)0.26483 (14)0.20601 (13)0.0668 (6)
O60.2704 (3)0.42284 (17)0.14127 (14)0.0963 (8)
O70.49629 (16)0.24959 (11)0.59312 (10)0.0405 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04789 (13)0.04216 (11)0.04792 (12)0.00858 (9)0.00742 (9)0.00793 (9)
C10.056 (2)0.0430 (17)0.0361 (15)0.0029 (15)0.0046 (14)0.0003 (13)
C20.0511 (18)0.0391 (15)0.0299 (14)0.0010 (13)0.0037 (13)0.0019 (12)
C30.060 (2)0.0428 (16)0.0369 (15)0.0009 (15)0.0005 (14)0.0064 (13)
C40.0528 (19)0.068 (2)0.0498 (17)0.0067 (16)0.0032 (14)0.0045 (16)
C50.054 (2)0.059 (2)0.0409 (16)0.0074 (17)0.0022 (15)0.0010 (15)
C60.075 (2)0.0405 (16)0.0442 (17)0.0004 (16)0.0034 (16)0.0085 (14)
C70.0609 (19)0.0439 (16)0.0419 (15)0.0066 (14)0.0048 (14)0.0046 (13)
C80.055 (2)0.148 (3)0.091 (3)0.003 (2)0.010 (2)0.020 (2)
C90.068 (2)0.0412 (17)0.053 (2)0.0072 (15)0.0030 (18)0.0066 (15)
C100.068 (2)0.0361 (15)0.0391 (16)0.0071 (14)0.0003 (16)0.0015 (13)
C110.085 (3)0.072 (2)0.051 (2)0.0273 (19)0.0034 (18)0.0011 (17)
C120.114 (3)0.072 (2)0.0429 (19)0.028 (2)0.000 (2)0.0098 (17)
C130.091 (3)0.0497 (19)0.0435 (19)0.0071 (18)0.0110 (19)0.0019 (15)
C140.066 (2)0.066 (2)0.0431 (18)0.0052 (16)0.0005 (16)0.0039 (16)
C150.066 (2)0.0508 (18)0.0351 (15)0.0040 (15)0.0013 (16)0.0025 (14)
C160.099 (4)0.198 (5)0.084 (3)0.038 (3)0.027 (2)0.016 (3)
C170.0413 (17)0.0509 (16)0.0511 (16)0.0130 (13)0.0025 (13)0.0019 (14)
C180.0364 (16)0.0291 (14)0.0437 (16)0.0040 (11)0.0011 (13)0.0089 (12)
C190.0294 (15)0.0241 (13)0.0464 (16)0.0047 (11)0.0006 (13)0.0077 (12)
C200.0369 (16)0.0325 (14)0.0556 (17)0.0090 (12)0.0040 (14)0.0066 (13)
C210.0314 (16)0.0420 (16)0.078 (2)0.0070 (13)0.0111 (16)0.0064 (16)
C220.0484 (19)0.0469 (17)0.0625 (19)0.0069 (14)0.0207 (15)0.0007 (15)
C230.0390 (17)0.0416 (16)0.0514 (17)0.0058 (13)0.0041 (14)0.0026 (13)
C240.0308 (15)0.0232 (13)0.0455 (16)0.0013 (11)0.0040 (13)0.0037 (12)
C250.0354 (15)0.0378 (14)0.0472 (15)0.0054 (12)0.0020 (12)0.0068 (13)
C260.0364 (15)0.0487 (16)0.0426 (15)0.0049 (13)0.0024 (12)0.0002 (14)
C270.0359 (15)0.0441 (16)0.0506 (16)0.0005 (12)0.0033 (13)0.0089 (14)
C280.0370 (15)0.0353 (14)0.0485 (15)0.0026 (12)0.0063 (13)0.0086 (13)
C290.0430 (17)0.0524 (17)0.098 (2)0.0163 (14)0.0126 (16)0.0176 (17)
C300.0304 (15)0.0378 (15)0.0560 (16)0.0082 (12)0.0053 (13)0.0032 (13)
C310.0322 (14)0.0345 (14)0.0391 (14)0.0075 (12)0.0001 (11)0.0008 (12)
C320.0457 (17)0.0370 (15)0.0637 (18)0.0106 (13)0.0043 (14)0.0079 (14)
C330.0524 (19)0.0510 (18)0.091 (2)0.0266 (15)0.0065 (17)0.0072 (17)
C340.0380 (17)0.0600 (19)0.080 (2)0.0164 (15)0.0138 (15)0.0012 (17)
C350.0434 (17)0.0414 (15)0.0552 (17)0.0063 (13)0.0122 (14)0.0034 (13)
C360.0353 (15)0.0328 (14)0.0341 (14)0.0054 (12)0.0015 (12)0.0015 (11)
N10.0355 (13)0.0345 (11)0.0408 (12)0.0106 (10)0.0035 (11)0.0064 (10)
N20.0261 (12)0.0313 (11)0.0435 (13)0.0039 (9)0.0001 (10)0.0002 (10)
N30.0336 (12)0.0297 (11)0.0479 (12)0.0015 (9)0.0050 (10)0.0039 (10)
N40.0316 (12)0.0336 (11)0.0490 (12)0.0075 (10)0.0091 (10)0.0069 (10)
O10.0546 (13)0.0521 (12)0.0682 (13)0.0111 (10)0.0139 (11)0.0117 (10)
O20.0597 (13)0.0456 (11)0.0735 (13)0.0047 (9)0.0152 (10)0.0232 (10)
O30.0643 (15)0.0859 (15)0.0865 (15)0.0171 (13)0.0079 (13)0.0158 (13)
O40.0643 (15)0.0898 (16)0.0635 (13)0.0134 (12)0.0025 (11)0.0008 (12)
O50.0669 (14)0.0808 (15)0.0548 (12)0.0223 (11)0.0142 (10)0.0164 (11)
O60.119 (2)0.1003 (18)0.0488 (13)0.0132 (16)0.0250 (15)0.0070 (13)
O70.0341 (10)0.0372 (9)0.0416 (9)0.0048 (8)0.0035 (8)0.0005 (8)
Geometric parameters (Å, º) top
Cd1—O52.280 (2)C18—N11.328 (3)
Cd1—O22.286 (2)C18—N21.360 (3)
Cd1—N12.313 (2)C19—N11.384 (3)
Cd1—N4i2.332 (2)C19—C201.392 (3)
Cd1—O42.383 (2)C19—C241.400 (3)
Cd1—O12.404 (2)C20—C211.365 (3)
Cd1—C12.682 (2)C20—H200.9300
Cd1—C92.687 (3)C21—C221.394 (3)
C1—O11.255 (3)C21—H210.9300
C1—O21.261 (3)C22—C231.378 (3)
C1—C21.498 (3)C22—H220.9300
C2—C31.373 (3)C23—C241.373 (3)
C2—C71.380 (3)C23—H230.9300
C3—C41.385 (3)C24—N21.376 (3)
C3—H30.9300C25—N21.462 (2)
C4—C51.373 (3)C25—C261.512 (3)
C4—H40.9300C25—H25A0.9700
C5—C61.372 (4)C25—H25B0.9700
C5—O31.377 (3)C26—O71.418 (3)
C6—C71.383 (3)C26—H26A0.9700
C6—H60.9300C26—H26B0.9700
C7—H70.9300C27—O71.419 (2)
C8—O31.410 (4)C27—C281.504 (3)
C8—H8A0.9600C27—H27A0.9700
C8—H8B0.9600C27—H27B0.9700
C8—H8C0.9600C28—N31.460 (2)
C9—O41.255 (3)C28—H28A0.9700
C9—O51.271 (3)C28—H28B0.9700
C9—C101.476 (4)C29—C301.488 (3)
C10—C151.374 (3)C29—H29A0.9600
C10—C111.394 (3)C29—H29B0.9600
C11—C121.375 (4)C29—H29C0.9600
C11—H110.9300C30—N41.325 (2)
C12—C131.382 (4)C30—N31.355 (3)
C12—H120.9300C31—C321.380 (3)
C13—O61.366 (4)C31—N31.382 (3)
C13—C141.379 (4)C31—C361.389 (3)
C14—C151.378 (4)C32—C331.372 (3)
C14—H140.9300C32—H320.9300
C15—H150.9300C33—C341.389 (3)
C16—O61.411 (4)C33—H330.9300
C16—H16A0.9600C34—C351.369 (3)
C16—H16B0.9600C34—H340.9300
C16—H16C0.9600C35—C361.392 (3)
C17—C181.476 (3)C35—H350.9300
C17—H17A0.9600C36—N41.391 (3)
C17—H17B0.9600N4—Cd1i2.3316 (18)
C17—H17C0.9600
O5—Cd1—O2153.09 (6)H17B—C17—H17C109.5
O5—Cd1—N195.61 (7)N1—C18—N2111.6 (2)
O2—Cd1—N1107.43 (7)N1—C18—C17124.4 (2)
O5—Cd1—N4i100.00 (6)N2—C18—C17124.0 (2)
O2—Cd1—N4i94.51 (6)N1—C19—C20130.8 (2)
N1—Cd1—N4i88.28 (6)N1—C19—C24109.5 (2)
O5—Cd1—O455.99 (6)C20—C19—C24119.7 (2)
O2—Cd1—O499.60 (7)C21—C20—C19118.0 (2)
N1—Cd1—O4151.45 (7)C21—C20—H20121.0
N4i—Cd1—O498.77 (7)C19—C20—H20121.0
O5—Cd1—O1110.51 (7)C20—C21—C22121.7 (2)
O2—Cd1—O155.85 (6)C20—C21—H21119.1
N1—Cd1—O192.78 (6)C22—C21—H21119.1
N4i—Cd1—O1149.19 (7)C23—C22—C21121.1 (3)
O4—Cd1—O194.88 (6)C23—C22—H22119.4
O5—Cd1—C1134.16 (8)C21—C22—H22119.4
O2—Cd1—C127.98 (7)C24—C23—C22117.2 (2)
N1—Cd1—C1102.11 (7)C24—C23—H23121.4
N4i—Cd1—C1122.23 (8)C22—C23—H23121.4
O4—Cd1—C197.40 (7)C23—C24—N2132.5 (2)
O1—Cd1—C127.89 (7)C23—C24—C19122.3 (2)
O5—Cd1—C928.14 (7)N2—C24—C19105.2 (2)
O2—Cd1—C9126.59 (8)N2—C25—C26112.38 (18)
N1—Cd1—C9123.67 (8)N2—C25—H25A109.1
N4i—Cd1—C9100.99 (7)C26—C25—H25A109.1
O4—Cd1—C927.85 (7)N2—C25—H25B109.1
O1—Cd1—C9103.90 (7)C26—C25—H25B109.1
C1—Cd1—C9117.52 (8)H25A—C25—H25B107.9
O1—C1—O2121.8 (2)O7—C26—C25108.62 (18)
O1—C1—C2119.6 (2)O7—C26—H26A110.0
O2—C1—C2118.5 (3)C25—C26—H26A110.0
O1—C1—Cd163.63 (12)O7—C26—H26B110.0
O2—C1—Cd158.28 (12)C25—C26—H26B110.0
C2—C1—Cd1176.4 (2)H26A—C26—H26B108.3
C3—C2—C7118.5 (2)O7—C27—C28107.24 (18)
C3—C2—C1120.6 (2)O7—C27—H27A110.3
C7—C2—C1120.9 (3)C28—C27—H27A110.3
C2—C3—C4121.7 (2)O7—C27—H27B110.3
C2—C3—H3119.2C28—C27—H27B110.3
C4—C3—H3119.2H27A—C27—H27B108.5
C5—C4—C3119.0 (3)N3—C28—C27111.16 (18)
C5—C4—H4120.5N3—C28—H28A109.4
C3—C4—H4120.5C27—C28—H28A109.4
C6—C5—C4120.2 (2)N3—C28—H28B109.4
C6—C5—O3114.9 (3)C27—C28—H28B109.4
C4—C5—O3124.9 (3)H28A—C28—H28B108.0
C5—C6—C7120.3 (3)C30—C29—H29A109.5
C5—C6—H6119.9C30—C29—H29B109.5
C7—C6—H6119.9H29A—C29—H29B109.5
C2—C7—C6120.4 (3)C30—C29—H29C109.5
C2—C7—H7119.8H29A—C29—H29C109.5
C6—C7—H7119.8H29B—C29—H29C109.5
O3—C8—H8A109.5N4—C30—N3112.5 (2)
O3—C8—H8B109.5N4—C30—C29124.4 (2)
H8A—C8—H8B109.5N3—C30—C29123.00 (18)
O3—C8—H8C109.5C32—C31—N3132.2 (2)
H8A—C8—H8C109.5C32—C31—C36122.7 (2)
H8B—C8—H8C109.5N3—C31—C36105.0 (2)
O4—C9—O5120.3 (3)C33—C32—C31116.3 (2)
O4—C9—C10121.5 (3)C33—C32—H32121.8
O5—C9—C10118.3 (3)C31—C32—H32121.8
O4—C9—Cd162.46 (17)C32—C33—C34121.6 (2)
O5—C9—Cd157.83 (15)C32—C33—H33119.2
C10—C9—Cd1176.0 (2)C34—C33—H33119.2
C15—C10—C11117.4 (3)C35—C34—C33122.2 (2)
C15—C10—C9121.5 (3)C35—C34—H34118.9
C11—C10—C9121.1 (3)C33—C34—H34118.9
C12—C11—C10120.2 (3)C34—C35—C36117.0 (2)
C12—C11—H11119.9C34—C35—H35121.5
C10—C11—H11119.9C36—C35—H35121.5
C11—C12—C13121.2 (3)C31—C36—N4110.24 (18)
C11—C12—H12119.4C31—C36—C35120.2 (2)
C13—C12—H12119.4N4—C36—C35129.5 (2)
O6—C13—C14124.9 (3)C18—N1—C19105.8 (2)
O6—C13—C12115.9 (3)C18—N1—Cd1133.21 (19)
C14—C13—C12119.2 (3)C19—N1—Cd1120.40 (15)
C15—C14—C13118.9 (3)C18—N2—C24107.93 (19)
C15—C14—H14120.5C18—N2—C25127.4 (2)
C13—C14—H14120.5C24—N2—C25124.6 (2)
C10—C15—C14123.0 (3)C30—N3—C31107.50 (17)
C10—C15—H15118.5C30—N3—C28126.2 (2)
C14—C15—H15118.5C31—N3—C28126.0 (2)
O6—C16—H16A109.5C30—N4—C36104.68 (18)
O6—C16—H16B109.5C30—N4—Cd1i125.24 (16)
H16A—C16—H16B109.5C36—N4—Cd1i129.08 (12)
O6—C16—H16C109.5C1—O1—Cd188.48 (14)
H16A—C16—H16C109.5C1—O2—Cd193.74 (16)
H16B—C16—H16C109.5C5—O3—C8118.3 (3)
C18—C17—H17A109.5C9—O4—Cd189.69 (18)
C18—C17—H17B109.5C9—O5—Cd194.03 (17)
H17A—C17—H17B109.5C13—O6—C16117.5 (3)
C18—C17—H17C109.5C26—O7—C27112.89 (16)
H17A—C17—H17C109.5
O5—Cd1—C1—O137.75 (19)C24—C19—N1—Cd1171.44 (12)
O2—Cd1—C1—O1177.0 (2)O5—Cd1—N1—C185.74 (19)
N1—Cd1—C1—O172.59 (16)O2—Cd1—N1—C18160.18 (18)
N4i—Cd1—C1—O1168.27 (14)N4i—Cd1—N1—C18105.63 (19)
O4—Cd1—C1—O186.45 (16)O4—Cd1—N1—C180.3 (3)
C9—Cd1—C1—O166.10 (17)O1—Cd1—N1—C18105.19 (19)
O5—Cd1—C1—O2145.23 (14)C1—Cd1—N1—C18131.74 (19)
N1—Cd1—C1—O2104.42 (15)C9—Cd1—N1—C183.6 (2)
N4i—Cd1—C1—O28.75 (17)O5—Cd1—N1—C19163.82 (15)
O4—Cd1—C1—O296.54 (15)O2—Cd1—N1—C1930.26 (16)
O1—Cd1—C1—O2177.0 (2)N4i—Cd1—N1—C1963.93 (15)
C9—Cd1—C1—O2116.88 (15)O4—Cd1—N1—C19169.23 (14)
O2—C1—C2—C33.7 (4)O1—Cd1—N1—C1985.25 (15)
O1—C1—C2—C74.6 (4)C1—Cd1—N1—C1958.70 (16)
O2—C1—C2—C7176.5 (2)C9—Cd1—N1—C19166.00 (14)
C7—C2—C3—C40.1 (4)N1—C18—N2—C240.2 (2)
C1—C2—C3—C4179.9 (2)C17—C18—N2—C24179.51 (19)
C2—C3—C4—C50.3 (4)N1—C18—N2—C25177.09 (17)
C3—C4—C5—C60.3 (4)C17—C18—N2—C253.6 (3)
C3—C4—C5—O3179.9 (2)C23—C24—N2—C18178.7 (2)
C4—C5—C6—C70.1 (4)C19—C24—N2—C180.6 (2)
O3—C5—C6—C7179.9 (2)C23—C24—N2—C254.2 (3)
C3—C2—C7—C60.2 (3)C19—C24—N2—C25177.59 (17)
C1—C2—C7—C6179.6 (2)C26—C25—N2—C1892.4 (3)
C5—C6—C7—C20.2 (4)C26—C25—N2—C2484.0 (3)
O5—Cd1—C9—O4178.7 (2)N4—C30—N3—C310.0 (3)
O2—Cd1—C9—O416.14 (18)C29—C30—N3—C31178.7 (2)
N1—Cd1—C9—O4176.70 (13)N4—C30—N3—C28173.5 (2)
N4i—Cd1—C9—O487.99 (15)C29—C30—N3—C287.8 (4)
O1—Cd1—C9—O473.70 (15)C32—C31—N3—C30178.5 (3)
C1—Cd1—C9—O447.55 (18)C36—C31—N3—C300.8 (3)
O2—Cd1—C9—O5165.18 (12)C32—C31—N3—C285.0 (4)
N1—Cd1—C9—O54.62 (17)C36—C31—N3—C28174.3 (2)
N4i—Cd1—C9—O590.69 (14)C27—C28—N3—C3083.1 (3)
O4—Cd1—C9—O5178.7 (2)C27—C28—N3—C3189.2 (3)
O1—Cd1—C9—O5107.62 (14)N3—C30—N4—C360.7 (3)
C1—Cd1—C9—O5133.77 (14)C29—C30—N4—C36177.9 (3)
O4—C9—C10—C15176.2 (2)N3—C30—N4—Cd1i168.72 (15)
O5—C9—C10—C153.4 (4)C29—C30—N4—Cd1i12.6 (4)
O4—C9—C10—C113.8 (4)C31—C36—N4—C301.2 (3)
O5—C9—C10—C11176.7 (2)C35—C36—N4—C30178.6 (3)
C15—C10—C11—C120.5 (4)C31—C36—N4—Cd1i167.67 (15)
C9—C10—C11—C12179.5 (3)C35—C36—N4—Cd1i9.8 (4)
C10—C11—C12—C130.2 (5)O2—C1—O1—Cd13.0 (3)
C11—C12—C13—O6178.7 (3)C2—C1—O1—Cd1178.2 (2)
C11—C12—C13—C140.6 (4)O5—Cd1—O1—C1152.03 (15)
O6—C13—C14—C15178.1 (3)O2—Cd1—O1—C11.69 (14)
C12—C13—C14—C151.2 (4)N1—Cd1—O1—C1110.92 (16)
C11—C10—C15—C140.0 (4)N4i—Cd1—O1—C119.6 (2)
C9—C10—C15—C14179.9 (2)O4—Cd1—O1—C196.60 (16)
C13—C14—C15—C100.9 (4)C9—Cd1—O1—C1123.35 (16)
N1—C19—C20—C21179.4 (2)O1—C1—O2—Cd13.1 (3)
C24—C19—C20—C210.1 (3)C2—C1—O2—Cd1178.02 (19)
C19—C20—C21—C220.4 (3)O5—Cd1—O2—C164.7 (2)
C20—C21—C22—C231.3 (4)N1—Cd1—O2—C182.98 (15)
C21—C22—C23—C241.6 (3)N4i—Cd1—O2—C1172.59 (14)
C22—C23—C24—N2179.1 (2)O4—Cd1—O2—C187.72 (15)
C22—C23—C24—C191.1 (3)O1—Cd1—O2—C11.69 (14)
N1—C19—C24—C23179.2 (2)C9—Cd1—O2—C180.15 (16)
C20—C19—C24—C230.3 (3)C6—C5—O3—C8171.9 (3)
N1—C19—C24—N20.8 (2)C4—C5—O3—C87.8 (4)
C20—C19—C24—N2178.71 (18)O5—C9—O4—Cd11.3 (2)
N2—C25—C26—O760.9 (3)C10—C9—O4—Cd1179.2 (2)
O7—C27—C28—N3177.81 (19)O5—Cd1—O4—C90.75 (14)
N3—C31—C32—C33179.0 (2)O2—Cd1—O4—C9166.92 (14)
C36—C31—C32—C330.2 (4)N1—Cd1—O4—C95.8 (2)
C31—C32—C33—C340.2 (4)N4i—Cd1—O4—C996.95 (15)
C32—C33—C34—C350.3 (5)O1—Cd1—O4—C9110.76 (15)
C33—C34—C35—C360.1 (4)C1—Cd1—O4—C9138.70 (16)
C32—C31—C36—N4178.2 (2)O4—C9—O5—Cd11.4 (2)
N3—C31—C36—N41.2 (3)C10—C9—O5—Cd1179.12 (19)
C32—C31—C36—C350.5 (4)O2—Cd1—O5—C927.0 (2)
N3—C31—C36—C35178.9 (2)N1—Cd1—O5—C9176.14 (14)
C34—C35—C36—C310.3 (4)N4i—Cd1—O5—C994.63 (14)
C34—C35—C36—N4177.5 (2)O4—Cd1—O5—C90.74 (13)
N2—C18—N1—C190.3 (2)O1—Cd1—O5—C981.04 (15)
C17—C18—N1—C19179.0 (2)C1—Cd1—O5—C963.23 (18)
N2—C18—N1—Cd1170.34 (13)C14—C13—O6—C163.7 (4)
C17—C18—N1—Cd110.3 (3)C12—C13—O6—C16177.0 (3)
C20—C19—N1—C18178.7 (2)C25—C26—O7—C27167.09 (19)
C24—C19—N1—C180.7 (2)C28—C27—O7—C26172.20 (19)
C20—C19—N1—Cd19.2 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
C21—H21···O7ii0.932.503.333 (3)149
C6—H6···Cgiii0.932.763.684 (5)170
Symmetry codes: (ii) x+1, y, z; (iii) x+2, y, z.

Experimental details

Crystal data
Chemical formula[Cd2(C8H7O3)4(C20H22N4O)2]
Mr1498.18
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.0379 (5), 13.8130 (8), 13.9361 (6)
α, β, γ (°)88.143 (4), 86.539 (4), 74.863 (4)
V3)1676.11 (15)
Z1
Radiation typeMo Kα
µ (mm1)0.71
Crystal size (mm)0.28 × 0.24 × 0.21
Data collection
DiffractometerOxford Diffraction Gemini R Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis CCD; Oxford Diffraction, 2006)
Tmin, Tmax0.831, 0.902
No. of measured, independent and
observed [I > 2σ(I)] reflections
12519, 7555, 4356
Rint0.027
(sin θ/λ)max1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.051, 0.85
No. of reflections7555
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
C21—H21···O7i0.932.503.333 (3)148.7
C6—H6···Cgii0.932.7643.684 (5)169.77
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z.
 

Acknowledgements

The author thanks Weifang Vocational College for support.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc. 119, 2952–2953.  CSD CrossRef CAS Web of Science Google Scholar
First citationOxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, Q.-H., Ma, Y.-P., Wang, Q.-H. & Fang, R.-B. (2002). Chin. J. Struct. Chem. 21, 513–516.  CAS Google Scholar

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