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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m430.
Published online 2010 March 20. doi:  10.1107/S1600536810009505
PMCID: PMC2983921

Bis[μ-2,2′-dimethyl-1,1′-(oxydiethyl­ene)bis­(1H-benzimidazole)-κ2 N 3:N 3′]bis­[bis­(4-methoxy­benzoato-κ2 O,O′)cadmium(II)]

Abstract

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 [triangle]). For bis­(imid­azole) ligands with –CH2– spacers as N-donor bridging ligands, see: Hoskins et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m430-scheme1.jpg

Experimental

Crystal data

  • [Cd2(C8H7O3)4(C20H22N4O)2]
  • M r = 1498.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m430-efi1.jpg
  • 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 [triangle]) T min = 0.831, T max = 0.902
  • 12519 measured reflections
  • 7555 independent reflections
  • 4356 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009505/lx2137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009505/lx2137Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author thanks Weifang Vocational College for support.

supplementary crystallographic information

Comment

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).

Experimental

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

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

Figures

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.]
Fig. 2.
C–H···O interactions (dotted lines) in the title compound. [Symmetry code: (i) x+1, y, z; (iii) x-1, y, z.]
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.]

Crystal data

[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

Oxford Diffraction Gemini R Ultra diffractometer7555 independent reflections
Radiation source: fine-focus sealed tube4356 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 10.0 pixels mm-1θmax = 29.2°, θmin = 2.8°
ω scanh = −12→7
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006)k = −18→16
Tmin = 0.831, Tmax = 0.902l = −18→17
12519 measured reflections

Refinement

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 = 0.85w = 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 = −0.33 e Å3

Special details

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)

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)
H61.5231−0.17420.06240.067*
C71.3742 (3)−0.05289 (18)0.12062 (16)0.0505 (7)
H71.2864−0.07480.11420.061*
C81.9160 (4)−0.1138 (3)0.0596 (2)0.1036 (13)
H8A2.0000−0.16680.03520.155*
H8B1.9367−0.09650.12260.155*
H8C1.9039−0.05620.01750.155*
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)
H110.74080.3620−0.05790.082*
C120.5249 (5)0.3923 (2)−0.1003 (2)0.0759 (10)
H120.54750.4127−0.16250.091*
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)
H16A0.05360.4509−0.16830.212*
H16B0.08150.4765−0.06320.212*
H16C0.10530.3645−0.09200.212*
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)
C32−0.0560 (3)0.40092 (18)0.62173 (18)0.0490 (7)
H32−0.01180.33900.59410.059*
C33−0.2046 (3)0.4258 (2)0.6594 (2)0.0625 (8)
H33−0.26280.37960.65720.075*
C34−0.2700 (3)0.5184 (2)0.7009 (2)0.0595 (8)
H34−0.37090.53220.72590.071*
C35−0.1908 (3)0.58992 (19)0.70604 (17)0.0482 (7)
H35−0.23570.65170.73380.058*
C36−0.0400 (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)

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, °)

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—O1−37.75 (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—C18−160.18 (18)
N4i—Cd1—C1—O1168.27 (14)N4i—Cd1—N1—C18105.63 (19)
O4—Cd1—C1—O1−86.45 (16)O4—Cd1—N1—C180.3 (3)
C9—Cd1—C1—O1−66.10 (17)O1—Cd1—N1—C18−105.19 (19)
O5—Cd1—C1—O2145.23 (14)C1—Cd1—N1—C18−131.74 (19)
N1—Cd1—C1—O2−104.42 (15)C9—Cd1—N1—C183.6 (2)
N4i—Cd1—C1—O2−8.75 (17)O5—Cd1—N1—C19−163.82 (15)
O4—Cd1—C1—O296.54 (15)O2—Cd1—N1—C1930.26 (16)
O1—Cd1—C1—O2−177.0 (2)N4i—Cd1—N1—C19−63.93 (15)
C9—Cd1—C1—O2116.88 (15)O4—Cd1—N1—C19−169.23 (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—C7−176.5 (2)C9—Cd1—N1—C19−166.00 (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—C5−0.3 (4)N1—C18—N2—C25177.09 (17)
C3—C4—C5—C60.3 (4)C17—C18—N2—C25−3.6 (3)
C3—C4—C5—O3−179.9 (2)C23—C24—N2—C18−178.7 (2)
C4—C5—C6—C7−0.1 (4)C19—C24—N2—C18−0.6 (2)
O3—C5—C6—C7−179.9 (2)C23—C24—N2—C254.2 (3)
C3—C2—C7—C60.2 (3)C19—C24—N2—C25−177.59 (17)
C1—C2—C7—C6−179.6 (2)C26—C25—N2—C18−92.4 (3)
C5—C6—C7—C2−0.2 (4)C26—C25—N2—C2484.0 (3)
O5—Cd1—C9—O4178.7 (2)N4—C30—N3—C310.0 (3)
O2—Cd1—C9—O4−16.14 (18)C29—C30—N3—C31−178.7 (2)
N1—Cd1—C9—O4−176.70 (13)N4—C30—N3—C28−173.5 (2)
N4i—Cd1—C9—O487.99 (15)C29—C30—N3—C287.8 (4)
O1—Cd1—C9—O4−73.70 (15)C32—C31—N3—C30−178.5 (3)
C1—Cd1—C9—O4−47.55 (18)C36—C31—N3—C300.8 (3)
O2—Cd1—C9—O5165.18 (12)C32—C31—N3—C28−5.0 (4)
N1—Cd1—C9—O54.62 (17)C36—C31—N3—C28174.3 (2)
N4i—Cd1—C9—O5−90.69 (14)C27—C28—N3—C3083.1 (3)
O4—Cd1—C9—O5−178.7 (2)C27—C28—N3—C31−89.2 (3)
O1—Cd1—C9—O5107.62 (14)N3—C30—N4—C36−0.7 (3)
C1—Cd1—C9—O5133.77 (14)C29—C30—N4—C36177.9 (3)
O4—C9—C10—C15−176.2 (2)N3—C30—N4—Cd1i168.72 (15)
O5—C9—C10—C153.4 (4)C29—C30—N4—Cd1i−12.6 (4)
O4—C9—C10—C113.8 (4)C31—C36—N4—C301.2 (3)
O5—C9—C10—C11−176.7 (2)C35—C36—N4—C30178.6 (3)
C15—C10—C11—C12−0.5 (4)C31—C36—N4—Cd1i−167.67 (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—O6−178.7 (3)C2—C1—O1—Cd1−178.2 (2)
C11—C12—C13—C140.6 (4)O5—Cd1—O1—C1152.03 (15)
O6—C13—C14—C15178.1 (3)O2—Cd1—O1—C1−1.69 (14)
C12—C13—C14—C15−1.2 (4)N1—Cd1—O1—C1−110.92 (16)
C11—C10—C15—C140.0 (4)N4i—Cd1—O1—C1−19.6 (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—C21−179.4 (2)O1—C1—O2—Cd1−3.1 (3)
C24—C19—C20—C21−0.1 (3)C2—C1—O2—Cd1178.02 (19)
C19—C20—C21—C22−0.4 (3)O5—Cd1—O2—C1−64.7 (2)
C20—C21—C22—C231.3 (4)N1—Cd1—O2—C182.98 (15)
C21—C22—C23—C24−1.6 (3)N4i—Cd1—O2—C1172.59 (14)
C22—C23—C24—N2179.1 (2)O4—Cd1—O2—C1−87.72 (15)
C22—C23—C24—C191.1 (3)O1—Cd1—O2—C11.69 (14)
N1—C19—C24—C23179.2 (2)C9—Cd1—O2—C1−80.15 (16)
C20—C19—C24—C23−0.3 (3)C6—C5—O3—C8171.9 (3)
N1—C19—C24—N20.8 (2)C4—C5—O3—C8−7.8 (4)
C20—C19—C24—N2−178.71 (18)O5—C9—O4—Cd11.3 (2)
N2—C25—C26—O760.9 (3)C10—C9—O4—Cd1−179.2 (2)
O7—C27—C28—N3−177.81 (19)O5—Cd1—O4—C9−0.75 (14)
N3—C31—C32—C33179.0 (2)O2—Cd1—O4—C9166.92 (14)
C36—C31—C32—C33−0.2 (4)N1—Cd1—O4—C95.8 (2)
C31—C32—C33—C34−0.2 (4)N4i—Cd1—O4—C9−96.95 (15)
C32—C33—C34—C350.3 (5)O1—Cd1—O4—C9110.76 (15)
C33—C34—C35—C36−0.1 (4)C1—Cd1—O4—C9138.70 (16)
C32—C31—C36—N4178.2 (2)O4—C9—O5—Cd1−1.4 (2)
N3—C31—C36—N4−1.2 (3)C10—C9—O5—Cd1179.12 (19)
C32—C31—C36—C350.5 (4)O2—Cd1—O5—C9−27.0 (2)
N3—C31—C36—C35−178.9 (2)N1—Cd1—O5—C9−176.14 (14)
C34—C35—C36—C31−0.3 (4)N4i—Cd1—O5—C994.63 (14)
C34—C35—C36—N4−177.5 (2)O4—Cd1—O5—C90.74 (13)
N2—C18—N1—C190.3 (2)O1—Cd1—O5—C9−81.04 (15)
C17—C18—N1—C19−179.0 (2)C1—Cd1—O5—C9−63.23 (18)
N2—C18—N1—Cd1−170.34 (13)C14—C13—O6—C163.7 (4)
C17—C18—N1—Cd110.3 (3)C12—C13—O6—C16−177.0 (3)
C20—C19—N1—C18178.7 (2)C25—C26—O7—C27167.09 (19)
C24—C19—N1—C18−0.7 (2)C28—C27—O7—C26−172.20 (19)
C20—C19—N1—Cd1−9.2 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2137).

References

  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc 119, 2952–2953.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhao, Q.-H., Ma, Y.-P., Wang, Q.-H. & Fang, R.-B. (2002). Chin. J. Struct. Chem 21, 513–516.

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