metal-organic compounds
Di-μ-azido-bis(μ-1,4,7,10,13,16-hexaoxacyclooctadecane)bis(5,10,15,20-tetraphenylporphyrinato)dicadmiumdisodium
aLaboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, 5019 Monastir, Tunisia, and bLaboratoire de Chimie de Coordination CNRS UPR 8241, 205 Route de Norbone, 31077 Toulouse Cedex 04, France
*Correspondence e-mail: hnasri1@gmail.com
The 2Na2(N3)2(C44H28N4)2(C12H24O6)2], consists of one half of the dimeric complex; the tetranuclear molecule lies about an inversion centre. The CdII atom is coordinated by the four pyrrole N atoms of the 5,10,15,20-tetraphenylporphyrinate ligand and one N atom of the axial azide ligand in a square-pyramidal geometry. The azide group is also linked to the NaI atom, which is surrounded by one 18-crown-6 molecule and additionally bonded to a second 18-crown-6 molecule trans to the azide group. The porphyrin core exhibits a major doming distortion (∼40%) and the is stabilized by weak C—H⋯π interactions. The molecular structure features weak intramolecular hydrogen bonds: two O—H⋯O interactions within the 18-crown-6 molecule and one C—H(18-crown-6)⋯N(azido) contact.
of the title compound, [CdRelated literature
For the synthesis of [Cd(TPP)] (TPP = 5,10,15,20-tetraphenylporphyrinato), see: Rodesiler et al. (1985). For related structures, see: Byrn et al. (1991); Mansour et al. (2010); Liu et al. (2009). For further details of geometric distortions in related compounds, see: Jentzen et al. (1997).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812048052/ng5303sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048052/ng5303Isup2.hkl
The [Cd(TPP)] complex (Rodesiler et al. 1985) (20 mg, 0.027 mmol) with an excess of sodium azide NaN3 (100 mg, 1.5 mmol) and 18-crown-6 (52 mg, 0.19 mmol) in chlorobenzene (10 ml) were stirred overnight at room temperature under air to yield a dark-purple solution. Crystals of the title complex were obtained by diffusion of hexanes through the chlorobenzene solution.
All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (methylene) and 0.95 Å (aromatic) with Uiso(H) = 1.2Ueq(Caromatic, methylene).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. A view of the molecular structure of the title molecule with the atom-numbering. Displacement ellipsoids are drawn at 50% and H atoms have been omitted. | |
Fig. 2. The crystal structure of the title compound plotted in projection along [100]. H atoms have been omitted. |
[Cd2Na2(N3)2(C44H28N4)2(C12H24O6)2] | F(000) = 2176.0 |
Mr = 2108.90 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 23347 reflections |
a = 11.4175 (3) Å | θ = 3.0–32.2° |
b = 19.5363 (4) Å | µ = 0.51 mm−1 |
c = 22.6086 (6) Å | T = 180 K |
β = 102.683 (2)° | Prism, dark purple |
V = 4919.9 (2) Å3 | 0.48 × 0.42 × 0.28 mm |
Z = 2 |
Oxford Diffraction Xcalibur (Sapphire1) diffractometer | 12338 independent reflections |
Radiation source: fine-focus sealed tube | 9493 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 8.2632 pixels mm-1 | θmax = 28.4°, θmin = 3.1° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −26→26 |
Tmin = 0.791, Tmax = 0.870 | l = −30→26 |
44385 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.041P)2] where P = (Fo2 + 2Fc2)/3 |
12338 reflections | (Δ/σ)max = 0.002 |
640 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Cd2Na2(N3)2(C44H28N4)2(C12H24O6)2] | V = 4919.9 (2) Å3 |
Mr = 2108.90 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.4175 (3) Å | µ = 0.51 mm−1 |
b = 19.5363 (4) Å | T = 180 K |
c = 22.6086 (6) Å | 0.48 × 0.42 × 0.28 mm |
β = 102.683 (2)° |
Oxford Diffraction Xcalibur (Sapphire1) diffractometer | 12338 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 9493 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 0.870 | Rint = 0.030 |
44385 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.54 e Å−3 |
12338 reflections | Δρmin = −0.39 e Å−3 |
640 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cd | 0.955191 (10) | 0.298901 (6) | 0.222285 (5) | 0.01846 (4) | |
C11 | 0.79257 (14) | 0.16615 (8) | 0.18211 (7) | 0.0200 (3) | |
C12 | 0.75768 (15) | 0.12022 (8) | 0.13139 (7) | 0.0228 (3) | |
H12 | 0.6898 | 0.0908 | 0.1236 | 0.027* | |
C13 | 0.84030 (15) | 0.12703 (9) | 0.09686 (8) | 0.0250 (4) | |
H13 | 0.8409 | 0.1034 | 0.0602 | 0.030* | |
C14 | 0.92715 (14) | 0.17697 (8) | 0.12627 (7) | 0.0210 (3) | |
C15 | 0.73057 (14) | 0.17493 (8) | 0.22913 (7) | 0.0196 (3) | |
C21 | 0.76402 (14) | 0.21780 (8) | 0.27977 (7) | 0.0198 (3) | |
C22 | 0.70306 (15) | 0.22250 (9) | 0.32908 (7) | 0.0235 (3) | |
H22 | 0.6331 | 0.1981 | 0.3327 | 0.028* | |
C23 | 0.76396 (14) | 0.26804 (9) | 0.36900 (7) | 0.0233 (3) | |
H23 | 0.7448 | 0.2816 | 0.4061 | 0.028* | |
C24 | 0.86392 (14) | 0.29252 (8) | 0.34505 (7) | 0.0192 (3) | |
C25 | 0.95047 (14) | 0.33965 (8) | 0.37323 (7) | 0.0193 (3) | |
C31 | 1.05490 (14) | 0.36012 (8) | 0.35404 (7) | 0.0187 (3) | |
C32 | 1.15390 (14) | 0.39757 (8) | 0.39028 (7) | 0.0221 (3) | |
H32 | 1.1575 | 0.4163 | 0.4294 | 0.026* | |
C33 | 1.24091 (14) | 0.40109 (8) | 0.35806 (7) | 0.0213 (3) | |
H33 | 1.3172 | 0.4223 | 0.3706 | 0.026* | |
C34 | 1.19591 (13) | 0.36672 (8) | 0.30123 (7) | 0.0185 (3) | |
C35 | 1.25978 (14) | 0.35663 (8) | 0.25478 (7) | 0.0191 (3) | |
C41 | 1.22266 (14) | 0.31638 (8) | 0.20222 (7) | 0.0199 (3) | |
C42 | 1.28971 (14) | 0.30580 (8) | 0.15556 (7) | 0.0221 (3) | |
H42 | 1.3652 | 0.3255 | 0.1543 | 0.027* | |
C43 | 1.22553 (15) | 0.26289 (9) | 0.11422 (7) | 0.0239 (3) | |
H43 | 1.2472 | 0.2469 | 0.0784 | 0.029* | |
C44 | 1.11770 (14) | 0.24567 (8) | 0.13440 (7) | 0.0210 (3) | |
C45 | 1.02922 (14) | 0.19925 (8) | 0.10574 (7) | 0.0220 (3) | |
C61 | 0.57959 (19) | 0.32908 (10) | 0.09250 (9) | 0.0379 (5) | |
H61A | 0.4970 | 0.3132 | 0.0748 | 0.046* | |
H61B | 0.5976 | 0.3189 | 0.1365 | 0.046* | |
C62 | 0.6662 (2) | 0.29300 (10) | 0.06335 (10) | 0.0400 (5) | |
H62A | 0.7492 | 0.3068 | 0.0826 | 0.048* | |
H62B | 0.6591 | 0.2429 | 0.0681 | 0.048* | |
C63 | 0.51419 (17) | 0.43920 (10) | 0.11408 (8) | 0.0329 (4) | |
H63A | 0.5162 | 0.4191 | 0.1545 | 0.039* | |
H63B | 0.4301 | 0.4388 | 0.0906 | 0.039* | |
C64 | 0.56024 (19) | 0.51090 (10) | 0.12088 (8) | 0.0372 (5) | |
H64A | 0.5172 | 0.5373 | 0.1469 | 0.045* | |
H64B | 0.6468 | 0.5109 | 0.1403 | 0.045* | |
C65 | 0.60174 (17) | 0.60662 (10) | 0.06432 (10) | 0.0363 (4) | |
H65A | 0.5969 | 0.6306 | 0.1023 | 0.044* | |
H65B | 0.5594 | 0.6350 | 0.0299 | 0.044* | |
C66 | 0.73074 (18) | 0.60012 (11) | 0.06112 (9) | 0.0392 (5) | |
H66A | 0.7690 | 0.6459 | 0.0649 | 0.047* | |
H66B | 0.7738 | 0.5712 | 0.0949 | 0.047* | |
C67 | 0.85595 (17) | 0.57584 (10) | −0.00566 (11) | 0.0420 (5) | |
H67A | 0.9129 | 0.5490 | 0.0250 | 0.050* | |
H67B | 0.8820 | 0.6243 | −0.0025 | 0.050* | |
C68 | 0.85524 (19) | 0.54956 (10) | −0.06700 (11) | 0.0439 (5) | |
H68A | 0.7950 | 0.5746 | −0.0975 | 0.053* | |
H68B | 0.9351 | 0.5562 | −0.0765 | 0.053* | |
C69 | 0.8252 (2) | 0.44956 (13) | −0.12541 (11) | 0.0554 (6) | |
H69A | 0.9025 | 0.4584 | −0.1370 | 0.066* | |
H69B | 0.7600 | 0.4700 | −0.1566 | 0.066* | |
C70 | 0.8059 (3) | 0.37510 (13) | −0.12149 (12) | 0.0630 (7) | |
H70A | 0.8078 | 0.3530 | −0.1607 | 0.076* | |
H70B | 0.8702 | 0.3548 | −0.0898 | 0.076* | |
C71 | 0.6697 (2) | 0.29346 (12) | −0.09761 (12) | 0.0543 (7) | |
H71A | 0.7117 | 0.2649 | −0.1226 | 0.065* | |
H71B | 0.5825 | 0.2846 | −0.1110 | 0.065* | |
C72 | 0.7101 (2) | 0.27356 (12) | −0.03293 (11) | 0.0491 (6) | |
H72A | 0.6993 | 0.2237 | −0.0282 | 0.059* | |
H72B | 0.7962 | 0.2846 | −0.0182 | 0.059* | |
C151 | 0.61833 (14) | 0.13391 (8) | 0.22497 (7) | 0.0205 (3) | |
C152 | 0.50758 (15) | 0.16382 (9) | 0.20413 (8) | 0.0283 (4) | |
H152 | 0.5028 | 0.2107 | 0.1928 | 0.034* | |
C153 | 0.40297 (18) | 0.12598 (12) | 0.19951 (10) | 0.0415 (5) | |
H153 | 0.3270 | 0.1472 | 0.1858 | 0.050* | |
C154 | 0.4095 (2) | 0.05846 (12) | 0.21466 (10) | 0.0476 (6) | |
H154 | 0.3379 | 0.0323 | 0.2101 | 0.057* | |
C156 | 0.62280 (18) | 0.06554 (9) | 0.24185 (9) | 0.0346 (4) | |
H156 | 0.6982 | 0.0444 | 0.2573 | 0.042* | |
C155 | 0.5182 (2) | 0.02790 (10) | 0.23634 (11) | 0.0475 (6) | |
H155 | 0.5219 | −0.0190 | 0.2476 | 0.057* | |
C251 | 0.93115 (14) | 0.37047 (9) | 0.43087 (7) | 0.0217 (3) | |
C252 | 0.89204 (19) | 0.43716 (10) | 0.43156 (9) | 0.0361 (4) | |
H252 | 0.8792 | 0.4637 | 0.3955 | 0.043* | |
C253 | 0.8714 (2) | 0.46554 (12) | 0.48412 (10) | 0.0491 (6) | |
H253 | 0.8448 | 0.5116 | 0.4840 | 0.059* | |
C254 | 0.8890 (2) | 0.42795 (11) | 0.53662 (9) | 0.0426 (5) | |
H254 | 0.8740 | 0.4477 | 0.5726 | 0.051* | |
C255 | 0.92830 (18) | 0.36194 (11) | 0.53656 (8) | 0.0357 (4) | |
H255 | 0.9417 | 0.3358 | 0.5729 | 0.043* | |
C256 | 0.94880 (17) | 0.33272 (10) | 0.48362 (8) | 0.0315 (4) | |
H256 | 0.9751 | 0.2866 | 0.4838 | 0.038* | |
C351 | 1.37943 (14) | 0.39124 (9) | 0.26353 (7) | 0.0213 (3) | |
C352 | 1.48392 (15) | 0.35385 (10) | 0.26812 (8) | 0.0266 (4) | |
H352 | 1.4800 | 0.3053 | 0.2655 | 0.032* | |
C353 | 1.59456 (16) | 0.38634 (11) | 0.27650 (8) | 0.0368 (5) | |
H353 | 1.6654 | 0.3601 | 0.2785 | 0.044* | |
C354 | 1.60158 (18) | 0.45626 (12) | 0.28195 (9) | 0.0429 (5) | |
H354 | 1.6776 | 0.4783 | 0.2887 | 0.051* | |
C355 | 1.4996 (2) | 0.49444 (11) | 0.27768 (9) | 0.0397 (5) | |
H355 | 1.5045 | 0.5428 | 0.2814 | 0.048* | |
C356 | 1.38891 (16) | 0.46187 (9) | 0.26790 (8) | 0.0302 (4) | |
H356 | 1.3181 | 0.4886 | 0.2641 | 0.036* | |
C451 | 1.04429 (15) | 0.16895 (10) | 0.04724 (8) | 0.0280 (4) | |
C452 | 1.0733 (2) | 0.10085 (11) | 0.04350 (10) | 0.0447 (5) | |
H452 | 1.0872 | 0.0728 | 0.0787 | 0.054* | |
C453 | 1.0821 (2) | 0.07327 (14) | −0.01290 (14) | 0.0646 (8) | |
H453 | 1.1020 | 0.0264 | −0.0158 | 0.078* | |
C454 | 1.0622 (2) | 0.11344 (18) | −0.06310 (12) | 0.0666 (9) | |
H454 | 1.0686 | 0.0945 | −0.1010 | 0.080* | |
C455 | 1.0333 (2) | 0.18053 (17) | −0.05956 (10) | 0.0575 (7) | |
H455 | 1.0188 | 0.2081 | −0.0950 | 0.069* | |
C456 | 1.02489 (17) | 0.20883 (12) | −0.00495 (9) | 0.0390 (5) | |
H456 | 1.0057 | 0.2560 | −0.0029 | 0.047* | |
N1 | 0.89440 (12) | 0.19971 (7) | 0.17725 (6) | 0.0217 (3) | |
N2 | 0.86096 (12) | 0.26054 (7) | 0.29118 (6) | 0.0203 (3) | |
N3 | 1.08356 (11) | 0.34256 (7) | 0.30064 (6) | 0.0187 (3) | |
N4 | 1.11881 (12) | 0.27945 (7) | 0.18739 (6) | 0.0217 (3) | |
N5 | 0.85120 (16) | 0.38938 (9) | 0.17817 (8) | 0.0395 (4) | |
N6 | 0.85280 (14) | 0.41290 (8) | 0.13048 (8) | 0.0376 (4) | |
N7 | 0.85002 (16) | 0.43766 (11) | 0.08343 (10) | 0.0583 (6) | |
Na | 0.67309 (6) | 0.44498 (4) | −0.00329 (3) | 0.03434 (17) | |
O1 | 0.58802 (11) | 0.40026 (6) | 0.08330 (6) | 0.0298 (3) | |
O2 | 0.54207 (11) | 0.54180 (6) | 0.06255 (6) | 0.0310 (3) | |
O6 | 0.63991 (12) | 0.31060 (6) | 0.00076 (6) | 0.0360 (3) | |
O3 | 0.73794 (11) | 0.57028 (6) | 0.00506 (6) | 0.0334 (3) | |
O4 | 0.82635 (13) | 0.47896 (7) | −0.06839 (6) | 0.0410 (3) | |
O5 | 0.69298 (14) | 0.36427 (8) | −0.10704 (7) | 0.0518 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd | 0.01716 (6) | 0.02225 (6) | 0.01685 (6) | −0.00263 (5) | 0.00563 (4) | −0.00278 (5) |
C11 | 0.0196 (8) | 0.0186 (8) | 0.0216 (8) | −0.0015 (6) | 0.0044 (6) | −0.0016 (6) |
C12 | 0.0237 (8) | 0.0204 (8) | 0.0245 (8) | −0.0039 (6) | 0.0053 (7) | −0.0040 (7) |
C13 | 0.0267 (9) | 0.0252 (9) | 0.0235 (9) | −0.0032 (7) | 0.0068 (7) | −0.0083 (7) |
C14 | 0.0210 (8) | 0.0226 (8) | 0.0205 (8) | −0.0024 (6) | 0.0068 (7) | −0.0049 (6) |
C15 | 0.0188 (8) | 0.0193 (7) | 0.0214 (8) | −0.0026 (6) | 0.0061 (6) | 0.0000 (6) |
C21 | 0.0182 (8) | 0.0215 (8) | 0.0208 (8) | −0.0029 (6) | 0.0065 (6) | 0.0004 (6) |
C22 | 0.0207 (8) | 0.0281 (9) | 0.0236 (8) | −0.0038 (6) | 0.0093 (7) | −0.0003 (7) |
C23 | 0.0206 (8) | 0.0309 (9) | 0.0202 (8) | −0.0019 (7) | 0.0086 (7) | −0.0013 (7) |
C24 | 0.0175 (7) | 0.0240 (8) | 0.0171 (7) | 0.0012 (6) | 0.0063 (6) | −0.0020 (6) |
C25 | 0.0199 (8) | 0.0209 (8) | 0.0181 (8) | 0.0018 (6) | 0.0060 (6) | −0.0022 (6) |
C31 | 0.0189 (8) | 0.0199 (8) | 0.0177 (7) | 0.0008 (6) | 0.0049 (6) | −0.0025 (6) |
C32 | 0.0245 (8) | 0.0230 (8) | 0.0190 (8) | −0.0022 (7) | 0.0056 (6) | −0.0051 (7) |
C33 | 0.0186 (8) | 0.0235 (8) | 0.0216 (8) | −0.0040 (6) | 0.0036 (6) | −0.0040 (7) |
C34 | 0.0169 (7) | 0.0192 (8) | 0.0196 (8) | −0.0004 (6) | 0.0043 (6) | 0.0009 (6) |
C35 | 0.0162 (7) | 0.0208 (8) | 0.0210 (8) | −0.0006 (6) | 0.0057 (6) | 0.0013 (6) |
C41 | 0.0165 (8) | 0.0235 (8) | 0.0207 (8) | −0.0013 (6) | 0.0065 (6) | 0.0002 (6) |
C42 | 0.0202 (8) | 0.0261 (9) | 0.0222 (8) | −0.0016 (6) | 0.0093 (6) | 0.0005 (7) |
C43 | 0.0230 (8) | 0.0303 (9) | 0.0209 (8) | 0.0003 (7) | 0.0103 (7) | −0.0016 (7) |
C44 | 0.0208 (8) | 0.0244 (8) | 0.0197 (8) | 0.0007 (6) | 0.0085 (6) | −0.0034 (6) |
C45 | 0.0216 (8) | 0.0264 (8) | 0.0196 (8) | −0.0008 (7) | 0.0081 (6) | −0.0046 (7) |
C61 | 0.0470 (12) | 0.0309 (10) | 0.0344 (11) | −0.0095 (9) | 0.0059 (9) | 0.0088 (9) |
C62 | 0.0441 (12) | 0.0273 (10) | 0.0433 (12) | 0.0012 (8) | −0.0017 (9) | 0.0067 (9) |
C63 | 0.0348 (10) | 0.0419 (11) | 0.0237 (9) | −0.0026 (8) | 0.0100 (8) | 0.0030 (8) |
C64 | 0.0427 (12) | 0.0448 (12) | 0.0235 (9) | 0.0007 (9) | 0.0055 (8) | −0.0022 (8) |
C65 | 0.0359 (11) | 0.0258 (10) | 0.0456 (12) | −0.0008 (8) | 0.0058 (9) | −0.0055 (9) |
C66 | 0.0362 (11) | 0.0347 (11) | 0.0441 (12) | −0.0065 (8) | 0.0030 (9) | −0.0082 (9) |
C67 | 0.0265 (10) | 0.0329 (11) | 0.0671 (15) | −0.0077 (8) | 0.0113 (10) | 0.0014 (10) |
C68 | 0.0361 (11) | 0.0372 (11) | 0.0645 (15) | −0.0014 (9) | 0.0241 (11) | 0.0149 (11) |
C69 | 0.0664 (17) | 0.0668 (17) | 0.0399 (13) | −0.0115 (13) | 0.0267 (12) | 0.0002 (12) |
C70 | 0.0738 (18) | 0.0661 (17) | 0.0622 (17) | −0.0110 (14) | 0.0436 (15) | −0.0202 (13) |
C71 | 0.0617 (16) | 0.0451 (14) | 0.0637 (16) | −0.0151 (11) | 0.0307 (13) | −0.0267 (12) |
C72 | 0.0434 (13) | 0.0357 (11) | 0.0723 (17) | 0.0059 (9) | 0.0213 (12) | −0.0117 (11) |
C151 | 0.0223 (8) | 0.0207 (8) | 0.0202 (8) | −0.0047 (6) | 0.0081 (6) | −0.0027 (6) |
C152 | 0.0246 (9) | 0.0295 (10) | 0.0299 (9) | −0.0050 (7) | 0.0043 (7) | 0.0027 (7) |
C153 | 0.0232 (10) | 0.0557 (14) | 0.0441 (12) | −0.0090 (9) | 0.0042 (9) | 0.0019 (10) |
C154 | 0.0401 (12) | 0.0531 (14) | 0.0526 (14) | −0.0289 (11) | 0.0170 (10) | −0.0047 (11) |
C156 | 0.0374 (11) | 0.0237 (9) | 0.0446 (12) | 0.0001 (8) | 0.0131 (9) | 0.0022 (8) |
C155 | 0.0630 (16) | 0.0250 (10) | 0.0608 (15) | −0.0171 (10) | 0.0273 (12) | −0.0012 (10) |
C251 | 0.0180 (8) | 0.0285 (9) | 0.0198 (8) | −0.0035 (6) | 0.0068 (6) | −0.0064 (7) |
C252 | 0.0494 (12) | 0.0324 (10) | 0.0289 (10) | 0.0084 (9) | 0.0140 (9) | −0.0026 (8) |
C253 | 0.0714 (16) | 0.0392 (12) | 0.0405 (12) | 0.0149 (11) | 0.0205 (11) | −0.0108 (10) |
C254 | 0.0523 (13) | 0.0511 (13) | 0.0305 (11) | −0.0047 (10) | 0.0220 (10) | −0.0164 (10) |
C255 | 0.0409 (11) | 0.0474 (12) | 0.0213 (9) | −0.0065 (9) | 0.0120 (8) | −0.0019 (8) |
C256 | 0.0366 (10) | 0.0334 (10) | 0.0259 (9) | −0.0001 (8) | 0.0101 (8) | −0.0015 (8) |
C351 | 0.0186 (8) | 0.0284 (9) | 0.0176 (8) | −0.0038 (6) | 0.0055 (6) | −0.0003 (7) |
C352 | 0.0209 (9) | 0.0368 (10) | 0.0220 (8) | −0.0010 (7) | 0.0042 (7) | 0.0051 (7) |
C353 | 0.0185 (9) | 0.0617 (14) | 0.0291 (10) | −0.0010 (9) | 0.0030 (7) | 0.0131 (9) |
C354 | 0.0273 (11) | 0.0715 (16) | 0.0281 (10) | −0.0240 (10) | 0.0023 (8) | 0.0087 (10) |
C355 | 0.0465 (12) | 0.0388 (11) | 0.0359 (11) | −0.0222 (10) | 0.0132 (9) | −0.0037 (9) |
C356 | 0.0300 (10) | 0.0295 (10) | 0.0332 (10) | −0.0056 (7) | 0.0115 (8) | −0.0027 (8) |
C451 | 0.0220 (9) | 0.0395 (10) | 0.0254 (9) | −0.0098 (7) | 0.0115 (7) | −0.0130 (8) |
C452 | 0.0498 (13) | 0.0425 (12) | 0.0495 (13) | −0.0070 (10) | 0.0272 (11) | −0.0187 (10) |
C453 | 0.0583 (16) | 0.0649 (17) | 0.082 (2) | −0.0199 (13) | 0.0394 (15) | −0.0508 (16) |
C454 | 0.0459 (14) | 0.121 (3) | 0.0415 (14) | −0.0345 (15) | 0.0288 (11) | −0.0446 (16) |
C455 | 0.0363 (13) | 0.113 (2) | 0.0262 (11) | −0.0203 (13) | 0.0136 (9) | −0.0123 (13) |
C456 | 0.0271 (10) | 0.0663 (15) | 0.0259 (10) | −0.0075 (9) | 0.0105 (8) | −0.0044 (9) |
N1 | 0.0209 (7) | 0.0252 (7) | 0.0210 (7) | −0.0036 (6) | 0.0088 (5) | −0.0059 (6) |
N2 | 0.0191 (7) | 0.0246 (7) | 0.0188 (7) | −0.0038 (5) | 0.0074 (5) | −0.0039 (6) |
N3 | 0.0168 (6) | 0.0221 (7) | 0.0179 (7) | −0.0004 (5) | 0.0057 (5) | −0.0008 (5) |
N4 | 0.0203 (7) | 0.0258 (7) | 0.0207 (7) | −0.0036 (5) | 0.0080 (6) | −0.0055 (6) |
N5 | 0.0441 (10) | 0.0371 (10) | 0.0324 (9) | 0.0111 (8) | −0.0021 (7) | 0.0051 (8) |
N6 | 0.0250 (8) | 0.0361 (9) | 0.0477 (11) | −0.0010 (7) | −0.0008 (7) | 0.0112 (8) |
N7 | 0.0320 (10) | 0.0777 (15) | 0.0622 (13) | −0.0044 (9) | 0.0041 (9) | 0.0414 (12) |
Na | 0.0301 (4) | 0.0364 (4) | 0.0349 (4) | −0.0041 (3) | 0.0035 (3) | 0.0096 (3) |
O1 | 0.0304 (7) | 0.0290 (7) | 0.0316 (7) | −0.0025 (5) | 0.0100 (5) | 0.0066 (5) |
O2 | 0.0317 (7) | 0.0307 (7) | 0.0285 (7) | −0.0027 (5) | 0.0018 (5) | −0.0008 (5) |
O6 | 0.0353 (8) | 0.0314 (7) | 0.0405 (8) | 0.0058 (5) | 0.0068 (6) | −0.0025 (6) |
O3 | 0.0248 (7) | 0.0324 (7) | 0.0421 (8) | −0.0053 (5) | 0.0057 (6) | −0.0019 (6) |
O4 | 0.0522 (9) | 0.0348 (8) | 0.0409 (8) | −0.0053 (6) | 0.0209 (7) | 0.0043 (6) |
O5 | 0.0538 (10) | 0.0521 (10) | 0.0553 (10) | −0.0120 (8) | 0.0244 (8) | −0.0128 (8) |
Cd—N3 | 2.2076 (13) | C68—H68A | 0.9900 |
Cd—N2 | 2.2093 (13) | C68—H68B | 0.9900 |
Cd—N4 | 2.2145 (13) | C69—O4 | 1.409 (3) |
Cd—N1 | 2.2278 (13) | C69—C70 | 1.477 (3) |
Cd—N5 | 2.2380 (16) | C69—H69A | 0.9900 |
C11—N1 | 1.360 (2) | C69—H69B | 0.9900 |
C11—C15 | 1.411 (2) | C70—O5 | 1.413 (3) |
C11—C12 | 1.442 (2) | C70—H70A | 0.9900 |
C12—C13 | 1.356 (2) | C70—H70B | 0.9900 |
C12—H12 | 0.9500 | C71—O5 | 1.433 (3) |
C13—C14 | 1.445 (2) | C71—C72 | 1.485 (3) |
C13—H13 | 0.9500 | C71—H71A | 0.9900 |
C14—N1 | 1.362 (2) | C71—H71B | 0.9900 |
C14—C45 | 1.414 (2) | C72—O6 | 1.419 (2) |
C15—C21 | 1.402 (2) | C72—H72A | 0.9900 |
C15—C151 | 1.497 (2) | C72—H72B | 0.9900 |
C21—N2 | 1.365 (2) | C151—C152 | 1.379 (2) |
C21—C22 | 1.441 (2) | C151—C156 | 1.387 (2) |
C22—C23 | 1.347 (2) | C152—C153 | 1.389 (2) |
C22—H22 | 0.9500 | C152—H152 | 0.9500 |
C23—C24 | 1.448 (2) | C153—C154 | 1.361 (3) |
C23—H23 | 0.9500 | C153—H153 | 0.9500 |
C24—N2 | 1.3626 (19) | C154—C155 | 1.367 (3) |
C24—C25 | 1.398 (2) | C154—H154 | 0.9500 |
C25—C31 | 1.413 (2) | C156—C155 | 1.385 (3) |
C25—C251 | 1.495 (2) | C156—H156 | 0.9500 |
C31—N3 | 1.3623 (19) | C155—H155 | 0.9500 |
C31—C32 | 1.441 (2) | C251—C252 | 1.379 (2) |
C32—C33 | 1.356 (2) | C251—C256 | 1.379 (2) |
C32—H32 | 0.9500 | C252—C253 | 1.378 (3) |
C33—C34 | 1.441 (2) | C252—H252 | 0.9500 |
C33—H33 | 0.9500 | C253—C254 | 1.372 (3) |
C34—N3 | 1.3641 (19) | C253—H253 | 0.9500 |
C34—C35 | 1.418 (2) | C254—C255 | 1.365 (3) |
C35—C41 | 1.410 (2) | C254—H254 | 0.9500 |
C35—C351 | 1.498 (2) | C255—C256 | 1.392 (2) |
C41—N4 | 1.365 (2) | C255—H255 | 0.9500 |
C41—C42 | 1.448 (2) | C256—H256 | 0.9500 |
C42—C43 | 1.346 (2) | C351—C352 | 1.383 (2) |
C42—H42 | 0.9500 | C351—C356 | 1.386 (2) |
C43—C44 | 1.444 (2) | C352—C353 | 1.389 (2) |
C43—H43 | 0.9500 | C352—H352 | 0.9500 |
C44—N4 | 1.365 (2) | C353—C354 | 1.372 (3) |
C44—C45 | 1.405 (2) | C353—H353 | 0.9500 |
C45—C451 | 1.493 (2) | C354—C355 | 1.368 (3) |
C61—O1 | 1.412 (2) | C354—H354 | 0.9500 |
C61—C62 | 1.482 (3) | C355—C356 | 1.389 (3) |
C61—H61A | 0.9900 | C355—H355 | 0.9500 |
C61—H61B | 0.9900 | C356—H356 | 0.9500 |
C62—O6 | 1.423 (2) | C451—C452 | 1.378 (3) |
C62—H62A | 0.9900 | C451—C456 | 1.390 (3) |
C62—H62B | 0.9900 | C452—C453 | 1.408 (3) |
C63—O1 | 1.425 (2) | C452—H452 | 0.9500 |
C63—C64 | 1.492 (3) | C453—C454 | 1.357 (4) |
C63—H63A | 0.9900 | C453—H453 | 0.9500 |
C63—H63B | 0.9900 | C454—C455 | 1.358 (4) |
C64—O2 | 1.424 (2) | C454—H454 | 0.9500 |
C64—H64A | 0.9900 | C455—C456 | 1.375 (3) |
C64—H64B | 0.9900 | C455—H455 | 0.9500 |
C65—O2 | 1.434 (2) | C456—H456 | 0.9500 |
C65—C66 | 1.496 (3) | N5—N6 | 1.176 (2) |
C65—H65A | 0.9900 | N6—N7 | 1.163 (2) |
C65—H65B | 0.9900 | N7—Na | 2.491 (2) |
C66—O3 | 1.414 (2) | Na—O1 | 2.5248 (14) |
C66—H66A | 0.9900 | Na—O2i | 2.5400 (14) |
C66—H66B | 0.9900 | Na—O3 | 2.5523 (14) |
C67—O3 | 1.425 (2) | Na—O4 | 2.6076 (15) |
C67—C68 | 1.477 (3) | Na—O6 | 2.6570 (15) |
C67—H67A | 0.9900 | Na—O5 | 2.8765 (17) |
C67—H67B | 0.9900 | Na—O2 | 3.0015 (15) |
C68—O4 | 1.417 (2) | O2—Nai | 2.5400 (14) |
N3—Cd—N2 | 84.58 (5) | O6—C72—H72B | 110.2 |
N3—Cd—N4 | 83.62 (5) | C71—C72—H72B | 110.2 |
N2—Cd—N4 | 140.58 (5) | H72A—C72—H72B | 108.5 |
N3—Cd—N1 | 142.01 (5) | C152—C151—C156 | 118.53 (16) |
N2—Cd—N1 | 82.88 (5) | C152—C151—C15 | 120.20 (15) |
N4—Cd—N1 | 83.71 (5) | C156—C151—C15 | 121.27 (15) |
N3—Cd—N5 | 104.25 (6) | C151—C152—C153 | 120.61 (18) |
N2—Cd—N5 | 106.81 (6) | C151—C152—H152 | 119.7 |
N4—Cd—N5 | 112.54 (6) | C153—C152—H152 | 119.7 |
N1—Cd—N5 | 113.69 (6) | C154—C153—C152 | 119.9 (2) |
N1—C11—C15 | 125.56 (14) | C154—C153—H153 | 120.0 |
N1—C11—C12 | 109.12 (14) | C152—C153—H153 | 120.0 |
C15—C11—C12 | 125.33 (14) | C153—C154—C155 | 120.55 (19) |
C13—C12—C11 | 106.93 (14) | C153—C154—H154 | 119.7 |
C13—C12—H12 | 126.5 | C155—C154—H154 | 119.7 |
C11—C12—H12 | 126.5 | C155—C156—C151 | 120.50 (19) |
C12—C13—C14 | 107.16 (14) | C155—C156—H156 | 119.7 |
C12—C13—H13 | 126.4 | C151—C156—H156 | 119.7 |
C14—C13—H13 | 126.4 | C154—C155—C156 | 119.85 (19) |
N1—C14—C45 | 125.20 (15) | C154—C155—H155 | 120.1 |
N1—C14—C13 | 108.75 (14) | C156—C155—H155 | 120.1 |
C45—C14—C13 | 126.05 (15) | C252—C251—C256 | 118.81 (16) |
C21—C15—C11 | 126.58 (14) | C252—C251—C25 | 120.04 (15) |
C21—C15—C151 | 116.55 (13) | C256—C251—C25 | 121.13 (15) |
C11—C15—C151 | 116.86 (14) | C253—C252—C251 | 120.48 (19) |
N2—C21—C15 | 125.71 (14) | C253—C252—H252 | 119.8 |
N2—C21—C22 | 108.92 (14) | C251—C252—H252 | 119.8 |
C15—C21—C22 | 125.35 (14) | C254—C253—C252 | 120.7 (2) |
C23—C22—C21 | 107.13 (14) | C254—C253—H253 | 119.7 |
C23—C22—H22 | 126.4 | C252—C253—H253 | 119.7 |
C21—C22—H22 | 126.4 | C255—C254—C253 | 119.36 (18) |
C22—C23—C24 | 107.51 (14) | C255—C254—H254 | 120.3 |
C22—C23—H23 | 126.2 | C253—C254—H254 | 120.3 |
C24—C23—H23 | 126.2 | C254—C255—C256 | 120.36 (18) |
N2—C24—C25 | 125.85 (14) | C254—C255—H255 | 119.8 |
N2—C24—C23 | 108.43 (14) | C256—C255—H255 | 119.8 |
C25—C24—C23 | 125.70 (14) | C251—C256—C255 | 120.29 (18) |
C24—C25—C31 | 127.32 (14) | C251—C256—H256 | 119.9 |
C24—C25—C251 | 115.96 (13) | C255—C256—H256 | 119.9 |
C31—C25—C251 | 116.71 (14) | C352—C351—C356 | 117.90 (15) |
N3—C31—C25 | 125.72 (14) | C352—C351—C35 | 121.20 (15) |
N3—C31—C32 | 108.70 (13) | C356—C351—C35 | 120.90 (15) |
C25—C31—C32 | 125.33 (14) | C351—C352—C353 | 120.83 (18) |
C33—C32—C31 | 107.21 (14) | C351—C352—H352 | 119.6 |
C33—C32—H32 | 126.4 | C353—C352—H352 | 119.6 |
C31—C32—H32 | 126.4 | C354—C353—C352 | 120.04 (19) |
C32—C33—C34 | 107.18 (14) | C354—C353—H353 | 120.0 |
C32—C33—H33 | 126.4 | C352—C353—H353 | 120.0 |
C34—C33—H33 | 126.4 | C355—C354—C353 | 120.28 (18) |
N3—C34—C35 | 125.46 (14) | C355—C354—H354 | 119.9 |
N3—C34—C33 | 108.69 (13) | C353—C354—H354 | 119.9 |
C35—C34—C33 | 125.78 (14) | C354—C355—C356 | 119.5 (2) |
C41—C35—C34 | 126.39 (14) | C354—C355—H355 | 120.3 |
C41—C35—C351 | 117.37 (13) | C356—C355—H355 | 120.3 |
C34—C35—C351 | 116.22 (14) | C351—C356—C355 | 121.45 (18) |
N4—C41—C35 | 125.85 (14) | C351—C356—H356 | 119.3 |
N4—C41—C42 | 108.38 (14) | C355—C356—H356 | 119.3 |
C35—C41—C42 | 125.75 (14) | C452—C451—C456 | 118.98 (18) |
C43—C42—C41 | 107.49 (14) | C452—C451—C45 | 120.86 (18) |
C43—C42—H42 | 126.3 | C456—C451—C45 | 120.12 (18) |
C41—C42—H42 | 126.3 | C451—C452—C453 | 119.4 (2) |
C42—C43—C44 | 107.31 (14) | C451—C452—H452 | 120.3 |
C42—C43—H43 | 126.3 | C453—C452—H452 | 120.3 |
C44—C43—H43 | 126.3 | C454—C453—C452 | 120.3 (2) |
N4—C44—C45 | 125.71 (14) | C454—C453—H453 | 119.9 |
N4—C44—C43 | 108.69 (14) | C452—C453—H453 | 119.9 |
C45—C44—C43 | 125.54 (14) | C453—C454—C455 | 120.5 (2) |
C44—C45—C14 | 127.44 (15) | C453—C454—H454 | 119.8 |
C44—C45—C451 | 116.95 (14) | C455—C454—H454 | 119.8 |
C14—C45—C451 | 115.61 (14) | C454—C455—C456 | 120.4 (2) |
O1—C61—C62 | 109.22 (16) | C454—C455—H455 | 119.8 |
O1—C61—H61A | 109.8 | C456—C455—H455 | 119.8 |
C62—C61—H61A | 109.8 | C455—C456—C451 | 120.5 (2) |
O1—C61—H61B | 109.8 | C455—C456—H456 | 119.8 |
C62—C61—H61B | 109.8 | C451—C456—H456 | 119.8 |
H61A—C61—H61B | 108.3 | C11—N1—C14 | 108.04 (13) |
O6—C62—C61 | 108.16 (16) | C11—N1—Cd | 124.64 (10) |
O6—C62—H62A | 110.1 | C14—N1—Cd | 123.68 (11) |
C61—C62—H62A | 110.1 | C24—N2—C21 | 108.01 (13) |
O6—C62—H62B | 110.1 | C24—N2—Cd | 123.66 (10) |
C61—C62—H62B | 110.1 | C21—N2—Cd | 125.06 (10) |
H62A—C62—H62B | 108.4 | C31—N3—C34 | 108.21 (13) |
O1—C63—C64 | 108.58 (15) | C31—N3—Cd | 124.20 (10) |
O1—C63—H63A | 110.0 | C34—N3—Cd | 126.78 (10) |
C64—C63—H63A | 110.0 | C41—N4—C44 | 108.13 (13) |
O1—C63—H63B | 110.0 | C41—N4—Cd | 125.23 (11) |
C64—C63—H63B | 110.0 | C44—N4—Cd | 123.33 (11) |
H63A—C63—H63B | 108.4 | N6—N5—Cd | 127.13 (14) |
O2—C64—C63 | 109.03 (15) | N7—N6—N5 | 177.1 (2) |
O2—C64—H64A | 109.9 | N6—N7—Na | 126.76 (14) |
C63—C64—H64A | 109.9 | N7—Na—O1 | 75.73 (6) |
O2—C64—H64B | 109.9 | N7—Na—O2i | 160.77 (7) |
C63—C64—H64B | 109.9 | O1—Na—O2i | 87.25 (5) |
H64A—C64—H64B | 108.3 | N7—Na—O3 | 79.92 (6) |
O2—C65—C66 | 112.97 (16) | O1—Na—O3 | 115.42 (5) |
O2—C65—H65A | 109.0 | O2i—Na—O3 | 99.95 (5) |
C66—C65—H65A | 109.0 | N7—Na—O4 | 85.99 (6) |
O2—C65—H65B | 109.0 | O1—Na—O4 | 161.06 (5) |
C66—C65—H65B | 109.0 | O2i—Na—O4 | 111.57 (5) |
H65A—C65—H65B | 107.8 | O3—Na—O4 | 65.03 (5) |
O3—C66—C65 | 109.27 (16) | N7—Na—O6 | 90.76 (6) |
O3—C66—H66A | 109.8 | O1—Na—O6 | 63.21 (4) |
C65—C66—H66A | 109.8 | O2i—Na—O6 | 89.42 (5) |
O3—C66—H66B | 109.8 | O3—Na—O6 | 170.52 (5) |
C65—C66—H66B | 109.8 | O4—Na—O6 | 112.92 (5) |
H66A—C66—H66B | 108.3 | N7—Na—O5 | 114.50 (7) |
O3—C67—C68 | 108.84 (17) | O1—Na—O5 | 123.73 (5) |
O3—C67—H67A | 109.9 | O2i—Na—O5 | 82.30 (5) |
C68—C67—H67A | 109.9 | O3—Na—O5 | 120.83 (5) |
O3—C67—H67B | 109.9 | O4—Na—O5 | 59.76 (5) |
C68—C67—H67B | 109.9 | O6—Na—O5 | 61.56 (5) |
H67A—C67—H67B | 108.3 | N7—Na—O2 | 92.99 (6) |
O4—C68—C67 | 108.21 (16) | O1—Na—O2 | 60.99 (4) |
O4—C68—H68A | 110.1 | O2i—Na—O2 | 70.60 (5) |
C67—C68—H68A | 110.1 | O3—Na—O2 | 61.77 (4) |
O4—C68—H68B | 110.1 | O4—Na—O2 | 126.07 (5) |
C67—C68—H68B | 110.1 | O6—Na—O2 | 121.01 (4) |
H68A—C68—H68B | 108.4 | O5—Na—O2 | 152.50 (5) |
O4—C69—C70 | 108.55 (18) | C61—O1—C63 | 112.76 (14) |
O4—C69—H69A | 110.0 | C61—O1—Na | 120.34 (11) |
C70—C69—H69A | 110.0 | C63—O1—Na | 124.29 (10) |
O4—C69—H69B | 110.0 | C64—O2—C65 | 112.14 (14) |
C70—C69—H69B | 110.0 | C64—O2—Nai | 117.33 (11) |
H69A—C69—H69B | 108.4 | C65—O2—Nai | 108.86 (11) |
O5—C70—C69 | 108.5 (2) | C64—O2—Na | 101.84 (10) |
O5—C70—H70A | 110.0 | C65—O2—Na | 106.55 (10) |
C69—C70—H70A | 110.0 | Nai—O2—Na | 109.40 (5) |
O5—C70—H70B | 110.0 | C72—O6—C62 | 112.94 (16) |
C69—C70—H70B | 110.0 | C72—O6—Na | 112.55 (13) |
H70A—C70—H70B | 108.4 | C62—O6—Na | 105.81 (10) |
O5—C71—C72 | 111.80 (19) | C66—O3—C67 | 111.37 (15) |
O5—C71—H71A | 109.3 | C66—O3—Na | 112.88 (11) |
C72—C71—H71A | 109.3 | C67—O3—Na | 109.29 (11) |
O5—C71—H71B | 109.3 | C69—O4—C68 | 111.87 (16) |
C72—C71—H71B | 109.3 | C69—O4—Na | 122.69 (13) |
H71A—C71—H71B | 107.9 | C68—O4—Na | 114.65 (11) |
O6—C72—C71 | 107.75 (18) | C70—O5—C71 | 112.78 (18) |
O6—C72—H72A | 110.2 | C70—O5—Na | 110.22 (13) |
C71—C72—H72A | 110.2 | C71—O5—Na | 110.93 (12) |
Symmetry code: (i) −x+1, −y+1, −z. |
Cg1, Cg2, Cg3 and Cg11 are the centroids of the N1/C11–C14, N2/C21–C24, N3/C31–C34 and C351–C356 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C62—H62A···N6 | 0.99 | 2.51 | 3.303 (3) | 137 |
C63—H63B···O3i | 0.99 | 2.56 | 3.489 (2) | 156 |
C65—H65B···O6i | 0.99 | 2.47 | 3.257 (2) | 136 |
C62—H62B···Cg1 | 0.99 | 2.90 | 3.555 (2) | 124 |
C63—H63A···Cg11ii | 0.99 | 2.75 | 3.662 (2) | 154 |
C71—H71A···Cg3iii | 0.99 | 2.88 | 3.535 (2) | 124 |
C353—H353···Cg2iv | 0.95 | 2.62 | 3.459 (2) | 147 |
C454—H454···Cg11iii | 0.95 | 2.82 | 3.697 (3) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x−3/2, −y−1/2, z−3/2; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Cd2Na2(N3)2(C44H28N4)2(C12H24O6)2] |
Mr | 2108.90 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 180 |
a, b, c (Å) | 11.4175 (3), 19.5363 (4), 22.6086 (6) |
β (°) | 102.683 (2) |
V (Å3) | 4919.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.48 × 0.42 × 0.28 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire1) diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.791, 0.870 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 44385, 12338, 9493 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.071, 1.02 |
No. of reflections | 12338 |
No. of parameters | 640 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.39 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012).
Cg1, Cg2, Cg3 and Cg11 are the centroids of the N1/C11–C14, N2/C21–C24, N3/C31–C34 and C351–C356 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C62—H62A···N6 | 0.99 | 2.51 | 3.303 (3) | 137.0 |
C63—H63B···O3i | 0.99 | 2.56 | 3.489 (2) | 156.0 |
C65—H65B···O6i | 0.99 | 2.47 | 3.257 (2) | 136.0 |
C62—H62B···Cg1 | 0.99 | 2.90 | 3.555 (2) | 124.0 |
C63—H63A···Cg11ii | 0.99 | 2.75 | 3.662 (2) | 154.0 |
C71—H71A···Cg3iii | 0.99 | 2.88 | 3.535 (2) | 124.0 |
C353—H353···Cg2iv | 0.95 | 2.62 | 3.459 (2) | 147.0 |
C454—H454···Cg11iii | 0.95 | 2.82 | 3.697 (3) | 153.0 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x−3/2, −y−1/2, z−3/2; (iv) x+1, y, z. |
Acknowledgements
The authors gratefully acknowledge financial support from the Ministry of Higher Education and Scientific Research of Tunisia.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of a systematic investigation of metalloporphyrins used as biomimetic models for hemoproteines and in several other domains (e.g. catalysis, medicine, electronic) several metalloporphyrin complexes has been characterized by our group (Mansour et al., 2010).
We report herein on the molecular structure of the title compound. The Cd atom is five-coordinated bound to the four porphyrin N atoms and to the nitrogen N5 atom of the azido ligand (Fig. 1). The Cd__N(azido) bond length [2.238 (2) Å] is in the range [2.250 (4) - 2.417 (6) Å] found for bridging µ2 (Cd-azido-M) moiety in non-porphyrin complexes where M is a metal atom (i.e., Liu et al. 2009).
The most interesting features of the structure of (I) are: (i) each [Cd(TPP)(N3)]- complex ion is strongly linked to the sodium atom of the counterion [Na(18-crown-6)]+ through the nitrogen N7 of the azido ligand where the Na__N(azido) distance is 2.492 (2) Å, (ii) the sodium atoms of two symmetry related [Na(18—C-6)]+ counterions are linked by two strong Na—O distances where the Na+ belongs to one 18-crown-6 molecule and the oxygen atom belong to the symmetry related adjacent ether crown molecule. The value of this distance [2.540 (1) Å] is shorter than the average Na—O(18-crown-6) which is 2.703 (2) Å.
The average equatorial cadmium-pyrrole N bond length (Cd—Np) [2.2148 (13) Å] is in the range [2.126 (9), 2.3167 (3) Å] for Cd porphyrin complexes (i.e., Byrn et al., 1991). The porphyrin core is not very distorted but present a major doming deformation as confirmed by the Normal Structural Decomposition (NSD) calculations (Jentzen, et al.,1997) with a value of 42%.
The molecular structure of (I) shows the presence of weak intramoleculair hydrogen bonds: two O—H···O bonds within the 18-crown-6 molecule and one C—H(18-crown-6)···N6(azido) bond. The crystal packing of the title compound is stabilized by C—H······π intermolecular interactions involving Cg pyrrole and phenyl centroids rings (Table 1 and Fig. 2).