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Acta Cryst. (2009). E65, m351    [ doi:10.1107/S160053680900676X ]

trans-Bis[1,3-bis(2-methoxyphenyl)triazenido]dimethanolcadmium(II)

M. K. Rofouei, M. R. Melardi, H. R. Khalili Ghaydari and M. Barkhi

Abstract top

In the title compound, [Cd(C14H14N3O2)2(CH3OH)2], each cadmium(II) center is six-coordinated by an N atom and an O atom of two 1,3-bis(2-methoxyphenyl)triazene ligands and by the O atoms of two methanol molecules. The distorted octahedral coordination geometry of the Cd atom has two N and two O atoms in the equatorial plane, and two O atoms in axial positions. The complex is stabilized by intramolecular O-H...O and O-H...N hydrogen bonds. In the crystal structure the complexes are linked into chains via intermolecular C-H...[pi] stacking interactions. One of the methanol C atoms is disordered with ouccupancies of 0.7:0.3.

Comment top

Recently, we have reported on the crystal structures of silver(I), copper(I), and mercry(II) complexes of the ligand [1,3-di(2-methoxy)benzene]triazene (Payehghadr et al., 2006; Rofouei & Hashempur 2008; Rofouei, Melardi et al., 2008). Here we report on the crystal structure of the cadmium(II) complex of the same ligand.

The molecular structure of the title complex is illustrated in Fig. 1. A view along the a axis of the crystal packing is given in Fig. 2. The title complex crystallizes in the non-centrosymmetric space group P212121; the Flack X factor is 0.04 (3). Each cadmium(II) center is six-coordinated by an N-atom and an O-atom of two [1,3-di(2-methoxy)benzene]triazene ligands, and by the O-atom of two molecules of methanol. The octahedral coordination geometry of the cadmium atom has two N- and two O-atoms in the equatorial plane, and two O-atoms in axial positions. The Cd—N and Cd—O bond lengths are in the expected range for such coordination bonds.

The complex is stabilized by intramolecular O—H···O and O—H···N hydrogen bonds (Table 1). Another noticeable feature of the title compound is the presence of C—H···π stacking interactions (Fig. 3 and Table 1).

Related literature top

For complexes of the title ligand, see: Payehghadr et al. (2006); Rofouei, Shamsipur et al. (2006); Rofouei, Melardi et al. (2008); Rofouei & Hashempur (2008).

Experimental top

The synthesis of the ligand 1,3-bis(2-methoxybenzene)triazene has been reported previously (Rofouei, Shamsipur et al., 2006). For the preparation of the cadmium(II) complex a solution of cadmium acetate monohydrate (248 mg, 1 mmol) in methanol (10 ml) was carefully added to a solution of 1,3-bis(2-methoxybenzene)triazene, (514 mg, 2 mmol) in dichloromethane (20 ml) with stirring at 40 °C. The solution was then cooled to rt and after several days needle-like red crystals of the title compound were isolated (yield; 550 mg, 80%).

Refinement top

The OH H-atoms could be located in difference Fourier syntheses, and were refined as riding: O-H = 0.86 - 0.91 Å with Uiso(H) = 1.5Ueq(parent O-atom). The C-bound H-atoms were included in calculated positions and treated as riding: C-H = 0.95 - 0.98 Å with Uiso(H) = 1.2 or 1.5Ueq(parent C-atom).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with thermal ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the a axis of the crystal packing of the title compound.
[Figure 3] Fig. 3. C—H···π stacking interactions in the title compound (see Table 1 for details).
trans-Bis[1,3-bis(2-methoxyphenyl)triazenido]dimethanolcadmium(II) top
Crystal data top
[Cd(C14H14N3O2)2(CH4O)2]F(000) = 1416
Mr = 689.05Dx = 1.464 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6454 reflections
a = 11.0333 (10) Åθ = 2.4–28.4°
b = 13.1892 (12) ŵ = 0.75 mm−1
c = 21.4784 (17) ÅT = 100 K
V = 3125.5 (5) Å3Prism, red
Z = 40.50 × 0.40 × 0.30 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9074 independent reflections
Radiation source: fine-focus sealed tube8503 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.693, Tmax = 0.806k = −18→18
40482 measured reflectionsl = −30→30
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0582P)2 + 7.7532P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
9074 reflectionsΔρmax = 2.65 e Å−3
394 parametersΔρmin = −2.09 e Å−3
2 restraintsAbsolute structure: Flack (1983), 4009 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (3)
Crystal data top
[Cd(C14H14N3O2)2(CH4O)2]V = 3125.5 (5) Å3
Mr = 689.05Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.0333 (10) ŵ = 0.75 mm−1
b = 13.1892 (12) ÅT = 100 K
c = 21.4784 (17) Å0.50 × 0.40 × 0.30 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9074 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		8503 reflections with I > 2σ(I)
Tmin = 0.693, Tmax = 0.806Rint = 0.041
40482 measured reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.132Δρmax = 2.65 e Å−3
S = 1.07Δρmin = −2.09 e Å−3
9074 reflectionsAbsolute structure: Flack (1983), 4009 Friedel pairs
394 parametersFlack parameter: 0.04 (3)
2 restraints
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
xyzUiso*/UeqOcc. (<1)
Cd10.51781 (3)0.91405 (2)0.161135 (15)0.02659 (8)
O10.4292 (3)1.0353 (2)0.23583 (15)0.0268 (6)
O20.3751 (4)0.6433 (4)0.03403 (18)0.0480 (10)
O30.3595 (3)0.9780 (3)0.07339 (16)0.0324 (7)
O40.8882 (3)0.8905 (3)0.2077 (2)0.0440 (10)
O50.5567 (4)0.7740 (3)0.1042 (2)0.0455 (10)
H5O0.48320.74280.10540.068*
O60.6498 (3)0.8632 (4)0.2391 (2)0.0489 (11)
H6O0.71950.88960.23050.073*
N10.3595 (3)0.8468 (3)0.21076 (16)0.0205 (6)
N20.2922 (3)0.7694 (3)0.19269 (17)0.0232 (7)
N30.3298 (3)0.7260 (3)0.14246 (17)0.0257 (7)
N40.5715 (3)1.0479 (3)0.10768 (17)0.0229 (7)
N50.6843 (3)1.0783 (3)0.11376 (15)0.0234 (6)
N60.7468 (3)1.0152 (3)0.14575 (17)0.0234 (7)
C10.3554 (4)0.9904 (3)0.28023 (19)0.0222 (7)
C20.3200 (4)0.8898 (3)0.2670 (2)0.0231 (8)
C30.2489 (4)0.8391 (4)0.3104 (2)0.0270 (8)
H3A0.22790.77010.30360.032*
C40.2081 (5)0.8886 (4)0.3639 (2)0.0337 (10)
H4A0.15790.85370.39280.040*
C50.2404 (5)0.9878 (4)0.3750 (2)0.0361 (11)
H5A0.21071.02150.41090.043*
C60.3162 (4)1.0390 (4)0.3338 (2)0.0320 (9)
H6A0.34071.10670.34220.038*
C70.2556 (4)0.6430 (3)0.1242 (2)0.0277 (9)
C80.2825 (5)0.5977 (4)0.0674 (2)0.0376 (11)
C90.2153 (6)0.5154 (5)0.0456 (3)0.0469 (14)
H9A0.23440.48520.00660.056*
C100.1206 (6)0.4780 (5)0.0811 (3)0.0523 (16)
H10A0.07400.42260.06610.063*
C110.0932 (6)0.5205 (4)0.1384 (3)0.0455 (13)
H11A0.02860.49460.16290.055*
C120.1629 (4)0.6025 (3)0.1594 (3)0.0352 (10)
H12A0.14590.63090.19910.042*
C130.4891 (7)1.1271 (4)0.2534 (3)0.0533 (17)
H13A0.42851.17960.26190.080*
H13B0.54201.14940.21940.080*
H13C0.53771.11510.29080.080*
C140.4088 (7)0.5967 (7)−0.0236 (3)0.069 (2)
H14A0.46760.6398−0.04520.104*
H14B0.33670.5881−0.04970.104*
H14C0.44520.5303−0.01530.104*
C150.4934 (4)1.1159 (3)0.07856 (18)0.0234 (8)
C160.3771 (4)1.0781 (4)0.06114 (19)0.0276 (8)
C170.2928 (4)1.1424 (4)0.0334 (2)0.0309 (9)
H17A0.21561.11690.02180.037*
C180.3205 (4)1.2424 (4)0.0228 (2)0.0330 (10)
H18A0.26201.28540.00390.040*
C190.4324 (4)1.2816 (4)0.0393 (2)0.0328 (10)
H19A0.45111.35080.03160.039*
C200.5178 (4)1.2176 (3)0.06748 (19)0.0273 (8)
H20A0.59431.24450.07930.033*
C210.8696 (3)1.0449 (3)0.1529 (2)0.0230 (8)
C220.9429 (4)0.9784 (4)0.1876 (2)0.0287 (9)
C231.0637 (4)1.0021 (5)0.1995 (3)0.0418 (13)
H23A1.11200.95810.22420.050*
C241.1133 (4)1.0911 (5)0.1749 (2)0.0365 (10)
H24A1.19561.10780.18300.044*
C251.0437 (4)1.1540 (4)0.1393 (2)0.0328 (10)
H25A1.07831.21360.12200.039*
C260.9219 (4)1.1314 (3)0.1281 (2)0.0250 (8)
H26A0.87451.17570.10310.030*
C270.2458 (5)0.9342 (5)0.0562 (2)0.0404 (12)
H27A0.24820.86080.06350.061*
H27B0.23010.94730.01210.061*
H27C0.18100.96440.08140.061*
C280.9622 (5)0.8102 (5)0.2272 (4)0.0603 (19)
H28A0.91370.74820.23050.090*
H28B0.99720.82640.26800.090*
H28C1.02750.80000.19690.090*
C290.6093 (11)0.7716 (10)0.0456 (4)0.064 (3)*0.70
H29A0.60730.70210.02950.096*0.70
H29B0.69350.79460.04850.096*0.70
H29C0.56420.81630.01750.096*0.70
C29'0.566 (3)0.808 (3)0.0417 (7)0.077 (8)*0.30
H29D0.55720.75010.01340.116*0.30
H29E0.64510.83980.03520.116*0.30
H29F0.50170.85740.03330.116*0.30
C300.6405 (5)0.8652 (5)0.3049 (3)0.0467 (13)
H30A0.70280.82120.32300.070*
H30B0.56010.84110.31750.070*
H30C0.65220.93480.31980.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02329 (12)0.02162 (12)0.03485 (14)0.00110 (11)0.00678 (12)−0.00016 (12)
O10.0261 (15)0.0220 (14)0.0323 (16)−0.0034 (12)0.0021 (12)−0.0064 (12)
O20.048 (2)0.061 (3)0.0348 (19)−0.006 (2)0.0054 (17)−0.0208 (18)
O30.0271 (16)0.0336 (18)0.0366 (18)−0.0081 (13)−0.0058 (14)0.0037 (14)
O40.0236 (16)0.038 (2)0.070 (3)0.0085 (14)0.0058 (16)0.0222 (18)
O50.0288 (18)0.0344 (19)0.073 (3)−0.0035 (15)0.0166 (18)−0.0148 (19)
O60.0204 (17)0.061 (3)0.065 (3)−0.0055 (17)−0.0038 (17)0.032 (2)
N10.0189 (15)0.0203 (15)0.0224 (15)−0.0018 (12)−0.0004 (12)−0.0030 (12)
N20.0208 (16)0.0201 (16)0.0285 (17)0.0002 (13)−0.0048 (13)−0.0031 (13)
N30.0211 (16)0.0265 (18)0.0294 (17)0.0019 (13)−0.0018 (13)−0.0039 (14)
N40.0150 (15)0.0250 (16)0.0288 (17)−0.0040 (12)0.0019 (13)0.0020 (13)
N50.0177 (14)0.0298 (17)0.0227 (15)0.0007 (14)0.0019 (11)−0.0016 (15)
N60.0159 (14)0.0253 (17)0.0291 (18)0.0024 (12)0.0017 (12)−0.0001 (13)
C10.0201 (18)0.0230 (19)0.0234 (18)0.0004 (14)−0.0040 (14)−0.0028 (15)
C20.0174 (17)0.026 (2)0.0260 (19)0.0011 (14)−0.0030 (14)−0.0051 (15)
C30.0225 (19)0.030 (2)0.028 (2)0.0003 (16)−0.0046 (16)0.0017 (17)
C40.033 (2)0.045 (3)0.0239 (19)−0.0050 (19)0.0011 (17)−0.0019 (18)
C50.040 (3)0.039 (3)0.029 (2)0.000 (2)0.0004 (19)−0.012 (2)
C60.029 (2)0.033 (2)0.034 (2)−0.0015 (16)−0.0003 (19)−0.009 (2)
C70.027 (2)0.0216 (19)0.034 (2)0.0015 (15)−0.0083 (17)−0.0071 (16)
C80.039 (2)0.035 (3)0.039 (2)−0.001 (2)−0.0045 (19)−0.010 (2)
C90.058 (4)0.040 (3)0.042 (3)0.005 (3)−0.014 (3)−0.017 (2)
C100.058 (4)0.038 (3)0.060 (4)−0.008 (3)−0.014 (3)−0.019 (3)
C110.040 (3)0.037 (3)0.059 (3)−0.008 (2)−0.007 (2)−0.010 (2)
C120.035 (2)0.023 (2)0.048 (3)−0.0033 (15)−0.003 (2)−0.015 (2)
C130.067 (4)0.039 (3)0.054 (3)−0.027 (3)0.022 (3)−0.019 (2)
C140.071 (5)0.088 (6)0.049 (3)−0.009 (4)0.011 (3)−0.039 (4)
C150.0172 (19)0.0297 (18)0.0232 (16)0.0001 (14)0.0050 (14)0.0005 (13)
C160.0228 (18)0.034 (2)0.0262 (18)0.0000 (18)0.0023 (14)−0.0011 (19)
C170.023 (2)0.044 (3)0.025 (2)−0.0029 (18)−0.0042 (16)0.0062 (18)
C180.022 (2)0.043 (3)0.034 (2)0.0020 (19)−0.0067 (17)0.010 (2)
C190.028 (2)0.034 (2)0.036 (2)−0.0033 (18)−0.0043 (18)0.0115 (19)
C200.0176 (16)0.033 (2)0.0311 (19)0.0018 (17)0.0027 (16)0.0057 (16)
C210.0144 (15)0.0309 (19)0.0237 (19)0.0040 (14)0.0040 (14)−0.0017 (15)
C220.0186 (18)0.034 (2)0.034 (2)0.0083 (16)0.0056 (16)0.0106 (18)
C230.017 (2)0.062 (4)0.047 (3)0.008 (2)−0.0005 (19)0.019 (3)
C240.0221 (19)0.051 (3)0.037 (2)0.000 (2)−0.0034 (15)0.005 (2)
C250.019 (2)0.041 (3)0.038 (2)0.0002 (17)0.0052 (16)0.0045 (19)
C260.024 (2)0.027 (2)0.0243 (19)0.0000 (16)0.0000 (15)0.0013 (15)
C270.036 (2)0.053 (4)0.033 (2)−0.013 (2)−0.0098 (19)0.003 (2)
C280.029 (3)0.044 (3)0.107 (6)0.008 (2)0.004 (3)0.025 (3)
C300.031 (3)0.056 (4)0.052 (3)−0.004 (2)−0.008 (2)0.003 (3)
Geometric parameters (Å, °) top
Cd1—N42.188 (4)C11—C121.402 (7)
Cd1—N12.230 (3)C11—H11A0.9500
Cd1—O52.257 (4)C12—H12A0.9500
Cd1—O62.318 (4)C13—H13A0.9800
Cd1—O12.467 (3)C13—H13B0.9800
Cd1—O32.704 (3)C13—H13C0.9800
O1—C11.387 (5)C14—H14A0.9800
O1—C131.430 (6)C14—H14B0.9800
O2—C81.385 (7)C14—H14C0.9800
O2—C141.430 (7)C15—C201.389 (6)
O3—C161.360 (6)C15—C161.426 (6)
O3—C271.430 (6)C16—C171.393 (7)
O4—C221.377 (6)C17—C181.373 (7)
O4—C281.401 (6)C17—H17A0.9500
O5—C291.386 (8)C18—C191.385 (7)
O5—C29'1.419 (10)C18—H18A0.9500
O5—H5O0.91C19—C201.402 (6)
O6—C301.418 (8)C19—H19A0.9500
O6—H6O0.86C20—H20A0.9500
N1—N21.321 (5)C21—C261.385 (6)
N1—C21.404 (5)C21—C221.406 (6)
N2—N31.289 (5)C22—C231.392 (7)
N3—C71.423 (6)C23—C241.399 (8)
N4—N51.313 (5)C23—H23A0.9500
N4—C151.392 (5)C24—C251.365 (7)
N5—N61.281 (5)C24—H24A0.9500
N6—C211.419 (5)C25—C261.397 (6)
C1—C61.386 (6)C25—H25A0.9500
C1—C21.412 (6)C26—H26A0.9500
C2—C31.390 (6)C27—H27A0.9800
C3—C41.397 (7)C27—H27B0.9800
C3—H3A0.9500C27—H27C0.9800
C4—C51.376 (8)C28—H28A0.9800
C4—H4A0.9500C28—H28B0.9800
C5—C61.393 (7)C28—H28C0.9800
C5—H5A0.9500C29—H29A0.9800
C6—H6A0.9500C29—H29B0.9800
C7—C121.379 (7)C29—H29C0.9800
C7—C81.391 (7)C29'—H29D0.9800
C8—C91.396 (8)C29'—H29E0.9800
C9—C101.385 (10)C29'—H29F0.9800
C9—H9A0.9500C30—H30A0.9800
C10—C111.385 (9)C30—H30B0.9800
C10—H10A0.9500C30—H30C0.9800
N4—Cd1—N1141.63 (13)C11—C12—H12A119.0
N4—Cd1—O5108.95 (13)O1—C13—H13A109.5
N1—Cd1—O594.72 (13)O1—C13—H13B109.5
N4—Cd1—O6116.27 (14)H13A—C13—H13B109.5
N1—Cd1—O691.80 (13)O1—C13—H13C109.5
O5—Cd1—O692.01 (18)H13A—C13—H13C109.5
N4—Cd1—O185.74 (12)H13B—C13—H13C109.5
N1—Cd1—O168.68 (12)O2—C14—H14A109.5
O5—Cd1—O1163.40 (12)O2—C14—H14B109.5
O6—Cd1—O188.09 (15)H14A—C14—H14B109.5
N4—Cd1—O363.74 (12)O2—C14—H14C109.5
N1—Cd1—O387.22 (12)H14A—C14—H14C109.5
O5—Cd1—O390.02 (14)H14B—C14—H14C109.5
O6—Cd1—O3177.81 (15)C20—C15—N4125.4 (4)
O1—Cd1—O389.73 (11)C20—C15—C16117.8 (4)
C1—O1—C13116.8 (4)N4—C15—C16116.7 (4)
C1—O1—Cd1113.8 (2)O3—C16—C17125.4 (4)
C13—O1—Cd1122.5 (3)O3—C16—C15114.7 (4)
C8—O2—C14116.9 (5)C17—C16—C15120.0 (4)
C16—O3—C27117.9 (4)C18—C17—C16120.5 (4)
C16—O3—Cd1110.2 (2)C18—C17—H17A119.7
C27—O3—Cd1128.3 (3)C16—C17—H17A119.7
C22—O4—C28118.4 (4)C17—C18—C19121.0 (4)
C29—O5—Cd1126.2 (6)C17—C18—H18A119.5
C29'—O5—Cd1105.5 (15)C19—C18—H18A119.5
C29—O5—H5O112.8C18—C19—C20119.0 (4)
C29'—O5—H5O103.4C18—C19—H19A120.5
Cd1—O5—H5O100.7C20—C19—H19A120.5
C30—O6—Cd1132.0 (4)C15—C20—C19121.7 (4)
C30—O6—H6O105.7C15—C20—H20A119.2
Cd1—O6—H6O106.7C19—C20—H20A119.2
N2—N1—C2113.0 (3)C26—C21—C22118.5 (4)
N2—N1—Cd1127.4 (3)C26—C21—N6125.7 (4)
C2—N1—Cd1119.6 (3)C22—C21—N6115.7 (4)
N3—N2—N1114.1 (4)O4—C22—C23123.4 (4)
N2—N3—C7112.7 (4)O4—C22—C21116.1 (4)
N5—N4—C15115.7 (4)C23—C22—C21120.5 (5)
N5—N4—Cd1116.8 (3)C22—C23—C24119.6 (5)
C15—N4—Cd1126.0 (3)C22—C23—H23A120.2
N6—N5—N4111.4 (4)C24—C23—H23A120.2
N5—N6—C21113.1 (4)C25—C24—C23120.1 (4)
C6—C1—O1123.8 (4)C25—C24—H24A120.0
C6—C1—C2121.0 (4)C23—C24—H24A120.0
O1—C1—C2115.2 (4)C24—C25—C26120.5 (5)
C3—C2—N1123.9 (4)C24—C25—H25A119.7
C3—C2—C1118.3 (4)C26—C25—H25A119.7
N1—C2—C1117.8 (4)C21—C26—C25120.7 (4)
C2—C3—C4120.5 (4)C21—C26—H26A119.6
C2—C3—H3A119.7C25—C26—H26A119.6
C4—C3—H3A119.7O3—C27—H27A109.5
C5—C4—C3120.2 (5)O3—C27—H27B109.5
C5—C4—H4A119.9H27A—C27—H27B109.5
C3—C4—H4A119.9O3—C27—H27C109.5
C4—C5—C6120.5 (5)H27A—C27—H27C109.5
C4—C5—H5A119.8H27B—C27—H27C109.5
C6—C5—H5A119.8O4—C28—H28A109.5
C1—C6—C5119.3 (4)O4—C28—H28B109.5
C1—C6—H6A120.3H28A—C28—H28B109.5
C5—C6—H6A120.3O4—C28—H28C109.5
C12—C7—C8118.2 (4)H28A—C28—H28C109.5
C12—C7—N3125.0 (4)H28B—C28—H28C109.5
C8—C7—N3116.7 (4)O5—C29—H29A109.5
O2—C8—C7115.1 (5)O5—C29—H29B109.5
O2—C8—C9123.8 (5)O5—C29—H29C109.5
C7—C8—C9121.0 (5)O5—C29'—H29D109.5
C10—C9—C8119.5 (5)O5—C29'—H29E109.5
C10—C9—H9A120.2H29D—C29'—H29E109.5
C8—C9—H9A120.2O5—C29'—H29F109.5
C11—C10—C9120.7 (5)H29D—C29'—H29F109.5
C11—C10—H10A119.7H29E—C29'—H29F109.5
C9—C10—H10A119.7O6—C30—H30A109.5
C10—C11—C12118.6 (6)O6—C30—H30B109.5
C10—C11—H11A120.7H30A—C30—H30B109.5
C12—C11—H11A120.7O6—C30—H30C109.5
C7—C12—C11121.9 (5)H30A—C30—H30C109.5
C7—C12—H12A119.0H30B—C30—H30C109.5
N4—Cd1—O1—C1168.6 (3)Cd1—N1—C2—C3−160.1 (3)
N1—Cd1—O1—C117.8 (3)N2—N1—C2—C1−158.8 (4)
O5—Cd1—O1—C115.7 (7)Cd1—N1—C2—C119.5 (5)
O6—Cd1—O1—C1−74.9 (3)C6—C1—C2—C3−2.7 (6)
O3—Cd1—O1—C1104.9 (3)O1—C1—C2—C3178.1 (4)
N4—Cd1—O1—C13−41.5 (4)C6—C1—C2—N1177.6 (4)
N1—Cd1—O1—C13167.7 (4)O1—C1—C2—N1−1.5 (5)
O5—Cd1—O1—C13165.7 (6)N1—C2—C3—C4−176.8 (4)
O6—Cd1—O1—C1375.1 (4)C1—C2—C3—C43.6 (6)
O3—Cd1—O1—C13−105.1 (4)C2—C3—C4—C5−1.5 (7)
N4—Cd1—O3—C16−23.7 (3)C3—C4—C5—C6−1.5 (8)
N1—Cd1—O3—C16130.4 (3)O1—C1—C6—C5178.9 (4)
O5—Cd1—O3—C16−134.9 (3)C2—C1—C6—C5−0.2 (7)
O1—Cd1—O3—C1661.7 (3)C4—C5—C6—C12.3 (8)
N4—Cd1—O3—C27178.4 (4)N2—N3—C7—C12−8.4 (6)
N1—Cd1—O3—C27−27.5 (4)N2—N3—C7—C8174.1 (4)
O5—Cd1—O3—C2767.2 (4)C14—O2—C8—C7177.7 (6)
O1—Cd1—O3—C27−96.2 (4)C14—O2—C8—C9−5.4 (9)
N4—Cd1—O5—C291.8 (8)C12—C7—C8—O2179.0 (5)
N1—Cd1—O5—C29151.1 (7)N3—C7—C8—O2−3.3 (7)
O6—Cd1—O5—C29−116.9 (7)C12—C7—C8—C92.0 (8)
O1—Cd1—O5—C29153.0 (8)N3—C7—C8—C9179.6 (5)
O3—Cd1—O5—C2963.9 (7)O2—C8—C9—C10−177.0 (6)
N4—Cd1—O5—C29'−19.7 (16)C7—C8—C9—C10−0.2 (9)
N1—Cd1—O5—C29'129.6 (16)C8—C9—C10—C11−1.0 (10)
O6—Cd1—O5—C29'−138.4 (16)C9—C10—C11—C120.3 (10)
O1—Cd1—O5—C29'131.5 (16)C8—C7—C12—C11−2.6 (8)
O3—Cd1—O5—C29'42.4 (16)N3—C7—C12—C11180.0 (5)
N4—Cd1—O6—C30110.3 (5)C10—C11—C12—C71.5 (9)
N1—Cd1—O6—C30−42.6 (5)N5—N4—C15—C20−13.8 (6)
O5—Cd1—O6—C30−137.4 (5)Cd1—N4—C15—C20151.8 (3)
O1—Cd1—O6—C3026.0 (5)N5—N4—C15—C16168.8 (4)
N4—Cd1—N1—N2107.2 (4)Cd1—N4—C15—C16−25.5 (5)
O5—Cd1—N1—N2−21.8 (4)C27—O3—C16—C170.5 (7)
O6—Cd1—N1—N2−113.9 (4)Cd1—O3—C16—C17−160.0 (4)
O1—Cd1—N1—N2158.8 (4)C27—O3—C16—C15−179.0 (4)
O3—Cd1—N1—N268.0 (3)Cd1—O3—C16—C1520.6 (4)
N4—Cd1—N1—C2−70.8 (4)C20—C15—C16—O3−179.9 (4)
O5—Cd1—N1—C2160.2 (3)N4—C15—C16—O3−2.4 (5)
O6—Cd1—N1—C268.0 (3)C20—C15—C16—C170.6 (6)
O1—Cd1—N1—C2−19.2 (3)N4—C15—C16—C17178.1 (4)
O3—Cd1—N1—C2−110.0 (3)O3—C16—C17—C18−179.6 (4)
C2—N1—N2—N3−177.3 (3)C15—C16—C17—C18−0.2 (7)
Cd1—N1—N2—N34.6 (5)C16—C17—C18—C190.0 (8)
N1—N2—N3—C7−180.0 (4)C17—C18—C19—C20−0.3 (8)
N1—Cd1—N4—N5146.5 (3)N4—C15—C20—C19−178.2 (4)
O5—Cd1—N4—N5−88.5 (3)C16—C15—C20—C19−0.9 (6)
O6—Cd1—N4—N513.7 (4)C18—C19—C20—C150.8 (7)
O1—Cd1—N4—N599.4 (3)N5—N6—C21—C26−1.1 (6)
O3—Cd1—N4—N5−168.7 (3)N5—N6—C21—C22−179.9 (4)
N1—Cd1—N4—C15−19.0 (5)C28—O4—C22—C23−16.3 (9)
O5—Cd1—N4—C15106.0 (3)C28—O4—C22—C21163.1 (6)
O6—Cd1—N4—C15−151.9 (3)C26—C21—C22—O4−175.8 (4)
O1—Cd1—N4—C15−66.1 (3)N6—C21—C22—O43.1 (6)
O3—Cd1—N4—C1525.7 (3)C26—C21—C22—C233.5 (7)
C15—N4—N5—N6174.3 (3)N6—C21—C22—C23−177.6 (5)
Cd1—N4—N5—N67.2 (4)O4—C22—C23—C24177.1 (5)
N4—N5—N6—C21179.5 (3)C21—C22—C23—C24−2.2 (8)
C13—O1—C1—C614.6 (7)C22—C23—C24—C25−0.2 (9)
Cd1—O1—C1—C6166.3 (3)C23—C24—C25—C261.3 (8)
C13—O1—C1—C2−166.3 (5)C22—C21—C26—C25−2.5 (7)
Cd1—O1—C1—C2−14.5 (4)N6—C21—C26—C25178.7 (4)
N2—N1—C2—C321.6 (6)C24—C25—C26—C210.1 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···N30.911.882.710 (6)150
O6—H6O···O40.861.922.739 (5)157
C23—H23A···Cg1i0.952.823.655 (6)147
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···N30.911.882.710 (6)150
O6—H6O···O40.861.922.739 (5)157
C23—H23A···Cg1i0.952.823.655 (6)147
Symmetry codes: (i) x+1, y, z.
references
References top

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Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Payehghadr, M., Rofouei, M. K., Morsali, A. & Shamsipur, M. (2006). Inorg. Chim. Acta, 360, 1792–1798.

Rofouei, M. K. & Hashempur, T. (2008). Anal. Sci. 24, x229–x230.

Rofouei, M. K., Melardi, M. R., Barkhi, M. & Khalili Ghaydar, H. R. (2008). Anal. Sci. 24, x81–x82.

Rofouei, M. K., Shamsipur, M. & Payehghadr, M. (2006). Anal. Sci. 22, x79–x80.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.