The title dicadmium compound, [Cd2(C10H8N2)5(H2O)6](C7H6NO2)2(ClO4)2·2H2O, is located around an inversion centre. Each CdII centre is coordinated by three N atoms from three different 4,4′-bipyridine ligands and three O atoms from three coordinating water molecules in a distorted octahedral coordination environment. In the dicadmium cation unit, one 4,4′-bipyridine (4,4′-bipy) molecule acts as a bidentate bridging ligand between two Cd metal ions, while the other four 4,4′-bipy molecules act only as monodentate terminal ligands, resulting in a rare `H-type' [Cd2(C10H8N2)5(H2O)6] host unit. These host units are connected to each other via π–π stacking interactions, giving rise to a three-dimensional supramolecular grid network with large cavities. The 3-aminobenzoate anions, perchlorate anions and water molecules are encapsulated in the cavities by numerous hydrogen-bonding interactions. To the best of our knowledge, this is the first example of a coordination compound based on both 4,4′-bipyridine ligands together with discrete 3-aminobenzoate anions.
Supporting information
CCDC reference: 833397
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
µ-4,4'-Bipyridine-
κ2N:
N'-bis[triaqua(4,4'-bipyridine-
κN)cadmium(II)] bis(3-aminobenzoate) bis(perchlorate) dihydrate
top
Crystal data top
[Cd2(C10H8N2)5(H2O)6](C7H6NO2)2(ClO4)2·2H2O | F(000) = 1652 |
Mr = 1621.00 | Dx = 1.603 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5600 reflections |
a = 7.4436 (1) Å | θ = 1.3–28.0° |
b = 19.0015 (4) Å | µ = 0.80 mm−1 |
c = 23.7517 (5) Å | T = 123 K |
β = 91.686 (1)° | Block, colourless |
V = 3357.98 (11) Å3 | 0.25 × 0.19 × 0.16 mm |
Z = 2 | |
Data collection top
Bruker APEXII area-detector diffractometer | 6746 independent reflections |
Radiation source: fine-focus sealed tube | 5834 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −9→8 |
Tmin = 0.826, Tmax = 0.883 | k = −21→23 |
29403 measured reflections | l = −25→29 |
Refinement top
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0253P)2 + 2.5909P] where P = (Fo2 + 2Fc2)/3 |
6746 reflections | (Δ/σ)max = 0.002 |
526 parameters | Δρmax = 0.47 e Å−3 |
26 restraints | Δρmin = −0.64 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cd1 | 0.31031 (2) | 0.278662 (8) | 0.463427 (6) | 0.01969 (6) | |
O1W | 0.0201 (2) | 0.32526 (8) | 0.47221 (7) | 0.0316 (4) | |
H1W | −0.0297 | 0.3584 | 0.4554 | 0.047* | |
H2W | −0.0333 | 0.3121 | 0.5005 | 0.047* | |
O2W | 0.4397 (2) | 0.38428 (9) | 0.46096 (8) | 0.0415 (5) | |
H3W | 0.3813 | 0.4213 | 0.4639 | 0.062* | |
H4W | 0.5413 | 0.3939 | 0.4491 | 0.062* | |
O3W | 0.5985 (2) | 0.23019 (8) | 0.46636 (7) | 0.0265 (4) | |
H5W | 0.6717 | 0.2466 | 0.4902 | 0.040* | |
H6W | 0.6514 | 0.2277 | 0.4357 | 0.040* | |
N1 | 0.2722 (3) | 0.26620 (9) | 0.36533 (8) | 0.0232 (4) | |
N2 | 0.3223 (3) | 0.22475 (11) | 0.06897 (8) | 0.0299 (5) | |
N3 | 0.3213 (3) | 0.28227 (9) | 0.56321 (8) | 0.0251 (4) | |
N4 | 0.2315 (3) | 0.28213 (10) | 0.85999 (8) | 0.0299 (5) | |
N5 | 0.2011 (2) | 0.16426 (9) | 0.46961 (7) | 0.0209 (4) | |
C1 | 0.2457 (3) | 0.32100 (12) | 0.33039 (10) | 0.0256 (5) | |
H1 | 0.2248 | 0.3660 | 0.3463 | 0.031* | |
C2 | 0.2474 (3) | 0.31496 (12) | 0.27244 (9) | 0.0250 (5) | |
H2 | 0.2277 | 0.3552 | 0.2493 | 0.030* | |
C3 | 0.2784 (3) | 0.24931 (12) | 0.24798 (9) | 0.0214 (5) | |
C4 | 0.2991 (3) | 0.19205 (12) | 0.28448 (9) | 0.0251 (5) | |
H4 | 0.3150 | 0.1460 | 0.2699 | 0.030* | |
C5 | 0.2964 (3) | 0.20278 (12) | 0.34173 (10) | 0.0261 (5) | |
H5 | 0.3124 | 0.1633 | 0.3659 | 0.031* | |
C6 | 0.2925 (3) | 0.24084 (12) | 0.18611 (9) | 0.0219 (5) | |
C7 | 0.3565 (3) | 0.29507 (12) | 0.15256 (10) | 0.0259 (5) | |
H7 | 0.3913 | 0.3388 | 0.1690 | 0.031* | |
C8 | 0.3687 (3) | 0.28473 (13) | 0.09541 (10) | 0.0304 (5) | |
H8 | 0.4126 | 0.3224 | 0.0734 | 0.036* | |
C9 | 0.2608 (3) | 0.17261 (13) | 0.10138 (10) | 0.0299 (5) | |
H9 | 0.2267 | 0.1296 | 0.0838 | 0.036* | |
C10 | 0.2444 (3) | 0.17827 (12) | 0.15897 (10) | 0.0259 (5) | |
H10 | 0.2006 | 0.1397 | 0.1800 | 0.031* | |
C11 | 0.0260 (3) | 0.15288 (12) | 0.45943 (10) | 0.0244 (5) | |
H11 | −0.0444 | 0.1901 | 0.4437 | 0.029* | |
C12 | −0.0577 (3) | 0.09004 (11) | 0.47062 (10) | 0.0249 (5) | |
H12 | −0.1829 | 0.0846 | 0.4628 | 0.030* | |
C13 | 0.0423 (3) | 0.03443 (11) | 0.49352 (9) | 0.0201 (5) | |
C14 | 0.2247 (3) | 0.04597 (11) | 0.50309 (10) | 0.0251 (5) | |
H14 | 0.2987 | 0.0095 | 0.5183 | 0.030* | |
C15 | 0.2981 (3) | 0.11044 (11) | 0.49041 (9) | 0.0236 (5) | |
H15 | 0.4236 | 0.1170 | 0.4967 | 0.028* | |
C16 | 0.2541 (3) | 0.33801 (12) | 0.59040 (9) | 0.0255 (5) | |
H16 | 0.2170 | 0.3778 | 0.5688 | 0.031* | |
C17 | 0.2363 (3) | 0.34034 (11) | 0.64802 (9) | 0.0246 (5) | |
H17 | 0.1890 | 0.3811 | 0.6653 | 0.030* | |
C18 | 0.2883 (3) | 0.28237 (11) | 0.68076 (9) | 0.0213 (5) | |
C19 | 0.3591 (3) | 0.22472 (11) | 0.65253 (10) | 0.0244 (5) | |
H19 | 0.3969 | 0.1841 | 0.6730 | 0.029* | |
C20 | 0.3739 (3) | 0.22690 (12) | 0.59493 (10) | 0.0259 (5) | |
H20 | 0.4239 | 0.1873 | 0.5766 | 0.031* | |
C21 | 0.2699 (3) | 0.28205 (11) | 0.74269 (10) | 0.0227 (5) | |
C22 | 0.2840 (3) | 0.34391 (12) | 0.77394 (10) | 0.0293 (5) | |
H22 | 0.3073 | 0.3874 | 0.7558 | 0.035* | |
C23 | 0.2638 (3) | 0.34150 (13) | 0.83142 (10) | 0.0332 (6) | |
H23 | 0.2733 | 0.3843 | 0.8520 | 0.040* | |
C24 | 0.2198 (3) | 0.22254 (13) | 0.82968 (10) | 0.0300 (5) | |
H24 | 0.1981 | 0.1797 | 0.8490 | 0.036* | |
C25 | 0.2375 (3) | 0.22016 (12) | 0.77217 (10) | 0.0273 (5) | |
H25 | 0.2277 | 0.1766 | 0.7527 | 0.033* | |
O1 | 0.7790 (2) | 0.42654 (9) | 0.43078 (7) | 0.0355 (4) | |
O2 | 0.9922 (3) | 0.48125 (14) | 0.38445 (9) | 0.0673 (7) | |
C26 | 0.8366 (3) | 0.45907 (13) | 0.38849 (11) | 0.0316 (6) | 0.64 |
C27 | 0.7223 (9) | 0.4677 (6) | 0.3351 (3) | 0.0260 (16) | 0.64 |
C28 | 0.5403 (7) | 0.4820 (2) | 0.3370 (2) | 0.0265 (11) | 0.64 |
H28 | 0.4860 | 0.4866 | 0.3726 | 0.032* | 0.64 |
C29 | 0.4330 (12) | 0.4902 (6) | 0.2869 (3) | 0.0262 (19) | 0.64 |
C30 | 0.5172 (10) | 0.4824 (3) | 0.2360 (3) | 0.0307 (14) | 0.64 |
H30 | 0.4481 | 0.4867 | 0.2019 | 0.037* | 0.64 |
C31 | 0.6994 (8) | 0.4687 (2) | 0.23355 (19) | 0.0348 (10) | 0.64 |
H31 | 0.7533 | 0.4636 | 0.1980 | 0.042* | 0.64 |
C32 | 0.8033 (8) | 0.4623 (3) | 0.2825 (2) | 0.0317 (12) | 0.64 |
H32 | 0.9289 | 0.4542 | 0.2806 | 0.038* | 0.64 |
N6 | 0.2548 (5) | 0.50767 (18) | 0.28831 (15) | 0.0330 (8) | 0.64 |
H6A | 0.188 (5) | 0.501 (2) | 0.2576 (11) | 0.040* | 0.64 |
H6B | 0.197 (5) | 0.500 (2) | 0.3195 (10) | 0.040* | 0.64 |
C26' | 0.8366 (3) | 0.45907 (13) | 0.38849 (11) | 0.0316 (6) | 0.36 |
C27' | 0.6880 (19) | 0.4751 (13) | 0.3463 (5) | 0.0260 (16) | 0.36 |
C28' | 0.7224 (12) | 0.4660 (5) | 0.2906 (4) | 0.029 (2) | 0.36 |
H28' | 0.8407 | 0.4542 | 0.2799 | 0.035* | 0.36 |
C29' | 0.5846 (14) | 0.4737 (6) | 0.2483 (5) | 0.028 (2) | 0.36 |
C30' | 0.419 (2) | 0.4925 (13) | 0.2674 (6) | 0.038 (4) | 0.36 |
H30' | 0.3232 | 0.4990 | 0.2404 | 0.045* | 0.36 |
C31' | 0.3827 (10) | 0.5024 (3) | 0.3237 (4) | 0.0320 (17) | 0.36 |
H31' | 0.2656 | 0.5159 | 0.3345 | 0.038* | 0.36 |
C32' | 0.5174 (11) | 0.4928 (4) | 0.3644 (4) | 0.0256 (17) | 0.36 |
H32' | 0.4943 | 0.4980 | 0.4033 | 0.031* | 0.36 |
N6' | 0.6121 (10) | 0.4599 (4) | 0.1934 (3) | 0.0431 (16) | 0.36 |
H6'1 | 0.526 (8) | 0.480 (4) | 0.172 (3) | 0.052* | 0.36 |
H6'2 | 0.726 (4) | 0.464 (5) | 0.184 (4) | 0.052* | 0.36 |
Cl1 | 0.09831 (10) | 0.47981 (3) | 0.12530 (3) | 0.03987 (16) | |
O3 | 0.0727 (3) | 0.44133 (11) | 0.17691 (8) | 0.0561 (6) | |
O4 | −0.0576 (4) | 0.52103 (14) | 0.11161 (10) | 0.0752 (8) | |
O5 | 0.1284 (3) | 0.43147 (10) | 0.08081 (9) | 0.0538 (5) | |
O6 | 0.2501 (4) | 0.52602 (12) | 0.13228 (10) | 0.0765 (8) | |
O4W | 0.2417 (3) | 0.49913 (13) | 0.46777 (11) | 0.0576 (7) | |
H7W | 0.213 (6) | 0.519 (2) | 0.4954 (18) | 0.086* | |
H8W | 0.157 (5) | 0.491 (2) | 0.4480 (17) | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02180 (9) | 0.02047 (9) | 0.01688 (9) | −0.00327 (6) | 0.00201 (6) | 0.00091 (6) |
O1W | 0.0289 (9) | 0.0357 (9) | 0.0305 (9) | 0.0078 (7) | 0.0060 (7) | 0.0116 (7) |
O2W | 0.0347 (10) | 0.0247 (9) | 0.0660 (13) | −0.0087 (8) | 0.0164 (9) | −0.0025 (9) |
O3W | 0.0214 (8) | 0.0389 (9) | 0.0194 (8) | −0.0015 (7) | 0.0009 (6) | −0.0028 (7) |
N1 | 0.0269 (10) | 0.0233 (10) | 0.0194 (10) | −0.0018 (8) | 0.0012 (8) | 0.0012 (7) |
N2 | 0.0313 (11) | 0.0388 (12) | 0.0199 (11) | 0.0037 (9) | 0.0028 (9) | −0.0036 (9) |
N3 | 0.0269 (10) | 0.0263 (10) | 0.0221 (10) | −0.0028 (8) | 0.0021 (8) | −0.0020 (8) |
N4 | 0.0299 (11) | 0.0383 (12) | 0.0215 (11) | 0.0004 (9) | 0.0016 (9) | 0.0010 (9) |
N5 | 0.0234 (10) | 0.0209 (9) | 0.0185 (10) | −0.0039 (8) | −0.0001 (8) | 0.0015 (7) |
C1 | 0.0303 (12) | 0.0214 (11) | 0.0251 (13) | 0.0004 (9) | 0.0014 (10) | 0.0002 (9) |
C2 | 0.0316 (13) | 0.0218 (11) | 0.0214 (12) | 0.0023 (9) | −0.0009 (10) | 0.0025 (9) |
C3 | 0.0180 (11) | 0.0251 (11) | 0.0212 (12) | −0.0021 (9) | 0.0007 (9) | −0.0004 (9) |
C4 | 0.0331 (13) | 0.0196 (11) | 0.0228 (13) | 0.0005 (9) | 0.0020 (10) | −0.0017 (9) |
C5 | 0.0341 (13) | 0.0215 (11) | 0.0228 (13) | −0.0010 (10) | 0.0026 (10) | 0.0043 (9) |
C6 | 0.0181 (11) | 0.0276 (12) | 0.0202 (12) | 0.0034 (9) | 0.0005 (9) | −0.0001 (9) |
C7 | 0.0297 (12) | 0.0255 (12) | 0.0225 (13) | −0.0005 (9) | 0.0010 (10) | −0.0005 (9) |
C8 | 0.0324 (13) | 0.0353 (14) | 0.0236 (13) | 0.0008 (11) | 0.0039 (10) | 0.0046 (10) |
C9 | 0.0304 (13) | 0.0319 (13) | 0.0274 (13) | 0.0005 (10) | 0.0014 (10) | −0.0079 (10) |
C10 | 0.0276 (12) | 0.0257 (12) | 0.0246 (13) | −0.0008 (9) | 0.0015 (10) | −0.0006 (9) |
C11 | 0.0221 (11) | 0.0238 (11) | 0.0272 (13) | 0.0001 (9) | −0.0016 (9) | 0.0055 (9) |
C12 | 0.0200 (11) | 0.0247 (12) | 0.0297 (13) | −0.0022 (9) | −0.0013 (9) | 0.0047 (10) |
C13 | 0.0238 (11) | 0.0212 (11) | 0.0154 (11) | −0.0014 (9) | 0.0004 (9) | −0.0007 (8) |
C14 | 0.0240 (12) | 0.0200 (11) | 0.0309 (13) | −0.0002 (9) | −0.0043 (10) | 0.0026 (9) |
C15 | 0.0207 (11) | 0.0243 (11) | 0.0257 (13) | −0.0040 (9) | −0.0032 (9) | −0.0004 (9) |
C16 | 0.0303 (12) | 0.0239 (12) | 0.0222 (12) | −0.0016 (10) | 0.0005 (10) | 0.0020 (9) |
C17 | 0.0282 (12) | 0.0218 (11) | 0.0239 (12) | −0.0004 (9) | 0.0037 (10) | −0.0036 (9) |
C18 | 0.0200 (11) | 0.0236 (11) | 0.0202 (12) | −0.0045 (9) | 0.0011 (9) | −0.0013 (9) |
C19 | 0.0243 (12) | 0.0242 (11) | 0.0246 (13) | 0.0005 (9) | −0.0005 (9) | 0.0002 (9) |
C20 | 0.0273 (12) | 0.0246 (12) | 0.0258 (13) | 0.0015 (9) | 0.0010 (10) | −0.0041 (10) |
C21 | 0.0204 (11) | 0.0249 (12) | 0.0226 (12) | 0.0005 (9) | 0.0013 (9) | 0.0000 (9) |
C22 | 0.0376 (14) | 0.0249 (12) | 0.0253 (13) | −0.0064 (10) | 0.0024 (11) | −0.0017 (10) |
C23 | 0.0420 (15) | 0.0338 (14) | 0.0239 (13) | −0.0037 (11) | 0.0022 (11) | −0.0069 (10) |
C24 | 0.0344 (13) | 0.0299 (13) | 0.0258 (13) | 0.0027 (10) | 0.0022 (11) | 0.0074 (10) |
C25 | 0.0322 (13) | 0.0235 (12) | 0.0262 (13) | −0.0001 (10) | 0.0013 (10) | −0.0009 (10) |
O1 | 0.0363 (10) | 0.0351 (10) | 0.0353 (10) | −0.0036 (8) | 0.0022 (8) | 0.0067 (8) |
O2 | 0.0323 (11) | 0.123 (2) | 0.0467 (13) | −0.0245 (12) | −0.0048 (10) | 0.0212 (13) |
C26 | 0.0282 (13) | 0.0335 (13) | 0.0329 (14) | −0.0005 (10) | 0.0007 (11) | −0.0007 (11) |
C27 | 0.027 (3) | 0.019 (3) | 0.031 (3) | −0.002 (2) | 0.000 (3) | 0.000 (3) |
C28 | 0.031 (3) | 0.027 (2) | 0.023 (3) | −0.0065 (17) | 0.006 (2) | 0.000 (2) |
C29 | 0.034 (3) | 0.018 (3) | 0.027 (5) | −0.004 (2) | 0.009 (4) | −0.002 (4) |
C30 | 0.035 (4) | 0.024 (3) | 0.033 (4) | −0.003 (3) | 0.000 (3) | 0.005 (2) |
C31 | 0.048 (3) | 0.027 (2) | 0.029 (3) | 0.001 (2) | 0.008 (2) | 0.0005 (17) |
C32 | 0.033 (3) | 0.029 (2) | 0.033 (3) | 0.002 (3) | 0.005 (3) | 0.0024 (18) |
N6 | 0.031 (2) | 0.0359 (18) | 0.032 (2) | −0.0014 (15) | −0.0019 (16) | 0.0022 (15) |
C26' | 0.0282 (13) | 0.0335 (13) | 0.0329 (14) | −0.0005 (10) | 0.0007 (11) | −0.0007 (11) |
C27' | 0.027 (3) | 0.019 (3) | 0.031 (3) | −0.002 (2) | 0.000 (3) | 0.000 (3) |
C28' | 0.024 (5) | 0.019 (4) | 0.044 (7) | 0.000 (4) | 0.002 (5) | −0.004 (3) |
C29' | 0.025 (7) | 0.025 (5) | 0.032 (6) | 0.003 (5) | −0.003 (5) | −0.001 (4) |
C30' | 0.044 (7) | 0.031 (5) | 0.038 (11) | −0.010 (4) | −0.005 (8) | 0.008 (9) |
C31' | 0.027 (4) | 0.015 (3) | 0.053 (6) | −0.004 (3) | 0.000 (4) | 0.011 (3) |
C32' | 0.029 (4) | 0.019 (4) | 0.028 (5) | −0.002 (3) | 0.005 (4) | 0.009 (4) |
N6' | 0.045 (4) | 0.053 (4) | 0.031 (4) | 0.001 (3) | −0.007 (3) | −0.005 (3) |
Cl1 | 0.0533 (4) | 0.0340 (3) | 0.0315 (4) | −0.0004 (3) | −0.0120 (3) | 0.0001 (3) |
O3 | 0.0729 (15) | 0.0559 (13) | 0.0387 (12) | −0.0130 (11) | −0.0097 (11) | 0.0122 (10) |
O4 | 0.0855 (18) | 0.0884 (18) | 0.0511 (14) | 0.0487 (15) | −0.0075 (13) | −0.0035 (13) |
O5 | 0.0704 (15) | 0.0392 (11) | 0.0517 (13) | 0.0038 (10) | 0.0012 (11) | −0.0091 (9) |
O6 | 0.112 (2) | 0.0627 (15) | 0.0527 (14) | −0.0463 (14) | −0.0322 (14) | 0.0181 (12) |
O4W | 0.0419 (13) | 0.0631 (15) | 0.0668 (17) | 0.0129 (11) | −0.0162 (11) | −0.0307 (12) |
Geometric parameters (Å, º) top
Cd1—O2W | 2.2275 (16) | C17—C18 | 1.396 (3) |
Cd1—N5 | 2.3269 (17) | C17—H17 | 0.9500 |
Cd1—O3W | 2.3336 (15) | C18—C19 | 1.396 (3) |
Cd1—O1W | 2.3499 (16) | C18—C21 | 1.481 (3) |
Cd1—N1 | 2.3509 (18) | C19—C20 | 1.376 (3) |
Cd1—N3 | 2.3699 (19) | C19—H19 | 0.9500 |
O1W—H1W | 0.8274 | C20—H20 | 0.9500 |
O1W—H2W | 0.8294 | C21—C22 | 1.393 (3) |
O2W—H3W | 0.8315 | C21—C25 | 1.393 (3) |
O2W—H4W | 0.8349 | C22—C23 | 1.379 (3) |
O3W—H5W | 0.8340 | C22—H22 | 0.9500 |
O3W—H6W | 0.8393 | C23—H23 | 0.9500 |
N1—C1 | 1.342 (3) | C24—C25 | 1.377 (3) |
N1—C5 | 1.343 (3) | C24—H24 | 0.9500 |
N2—C8 | 1.342 (3) | C25—H25 | 0.9500 |
N2—C9 | 1.343 (3) | O1—C26 | 1.265 (3) |
N3—C16 | 1.345 (3) | O2—C26 | 1.239 (3) |
N3—C20 | 1.346 (3) | C26—C27 | 1.516 (6) |
N4—C23 | 1.342 (3) | C27—C28 | 1.384 (8) |
N4—C24 | 1.343 (3) | C27—C32 | 1.407 (8) |
N5—C11 | 1.337 (3) | C28—C29 | 1.423 (10) |
N5—C15 | 1.338 (3) | C28—H28 | 0.9500 |
C1—C2 | 1.382 (3) | C29—N6 | 1.369 (9) |
C1—H1 | 0.9500 | C29—C30 | 1.386 (9) |
C2—C3 | 1.398 (3) | C30—C31 | 1.384 (7) |
C2—H2 | 0.9500 | C30—H30 | 0.9500 |
C3—C4 | 1.397 (3) | C31—C32 | 1.382 (8) |
C3—C6 | 1.485 (3) | C31—H31 | 0.9500 |
C4—C5 | 1.376 (3) | C32—H32 | 0.9500 |
C4—H4 | 0.9500 | N6—H6A | 0.880 (10) |
C5—H5 | 0.9500 | N6—H6B | 0.881 (10) |
C6—C10 | 1.394 (3) | C27'—C28' | 1.366 (14) |
C6—C7 | 1.395 (3) | C27'—C32' | 1.394 (14) |
C7—C8 | 1.377 (3) | C28'—C29' | 1.422 (12) |
C7—H7 | 0.9500 | C28'—H28' | 0.9500 |
C8—H8 | 0.9500 | C29'—N6' | 1.351 (13) |
C9—C10 | 1.381 (3) | C29'—C30' | 1.376 (14) |
C9—H9 | 0.9500 | C30'—C31' | 1.386 (13) |
C10—H10 | 0.9500 | C30'—H30' | 0.9500 |
C11—C12 | 1.376 (3) | C31'—C32' | 1.383 (11) |
C11—H11 | 0.9500 | C31'—H31' | 0.9500 |
C12—C13 | 1.394 (3) | C32'—H32' | 0.9500 |
C12—H12 | 0.9500 | N6'—H6'1 | 0.882 (10) |
C13—C14 | 1.388 (3) | N6'—H6'2 | 0.882 (10) |
C13—C13i | 1.488 (4) | Cl1—O5 | 1.423 (2) |
C14—C15 | 1.378 (3) | Cl1—O4 | 1.430 (2) |
C14—H14 | 0.9500 | Cl1—O6 | 1.437 (2) |
C15—H15 | 0.9500 | Cl1—O3 | 1.445 (2) |
C16—C17 | 1.379 (3) | O4W—H7W | 0.79 (4) |
C16—H16 | 0.9500 | O4W—H8W | 0.79 (4) |
| | | |
O2W—Cd1—N5 | 174.51 (7) | C16—C17—C18 | 119.6 (2) |
O2W—Cd1—O3W | 87.63 (6) | C16—C17—H17 | 120.2 |
N5—Cd1—O3W | 87.24 (6) | C18—C17—H17 | 120.2 |
O2W—Cd1—O1W | 93.56 (6) | C19—C18—C17 | 117.0 (2) |
N5—Cd1—O1W | 91.30 (6) | C19—C18—C21 | 121.4 (2) |
O3W—Cd1—O1W | 173.12 (5) | C17—C18—C21 | 121.61 (19) |
O2W—Cd1—N1 | 95.99 (7) | C20—C19—C18 | 119.8 (2) |
N5—Cd1—N1 | 86.35 (6) | C20—C19—H19 | 120.1 |
O3W—Cd1—N1 | 94.23 (6) | C18—C19—H19 | 120.1 |
O1W—Cd1—N1 | 92.38 (6) | N3—C20—C19 | 123.3 (2) |
O2W—Cd1—N3 | 89.89 (7) | N3—C20—H20 | 118.3 |
N5—Cd1—N3 | 88.04 (6) | C19—C20—H20 | 118.3 |
O3W—Cd1—N3 | 88.68 (6) | C22—C21—C25 | 117.1 (2) |
O1W—Cd1—N3 | 84.55 (6) | C22—C21—C18 | 121.2 (2) |
N1—Cd1—N3 | 173.54 (6) | C25—C21—C18 | 121.7 (2) |
Cd1—O1W—H1W | 130.1 | C23—C22—C21 | 119.4 (2) |
Cd1—O1W—H2W | 115.0 | C23—C22—H22 | 120.3 |
H1W—O1W—H2W | 113.7 | C21—C22—H22 | 120.3 |
Cd1—O2W—H3W | 122.2 | N4—C23—C22 | 123.7 (2) |
Cd1—O2W—H4W | 127.1 | N4—C23—H23 | 118.1 |
H3W—O2W—H4W | 108.9 | C22—C23—H23 | 118.1 |
Cd1—O3W—H5W | 117.1 | N4—C24—C25 | 123.6 (2) |
Cd1—O3W—H6W | 116.8 | N4—C24—H24 | 118.2 |
H5W—O3W—H6W | 107.2 | C25—C24—H24 | 118.2 |
C1—N1—C5 | 117.20 (19) | C24—C25—C21 | 119.6 (2) |
C1—N1—Cd1 | 123.07 (15) | C24—C25—H25 | 120.2 |
C5—N1—Cd1 | 119.35 (14) | C21—C25—H25 | 120.2 |
C8—N2—C9 | 116.5 (2) | O2—C26—O1 | 124.5 (2) |
C16—N3—C20 | 116.9 (2) | O2—C26—C27 | 113.7 (4) |
C16—N3—Cd1 | 120.06 (15) | O1—C26—C27 | 121.5 (5) |
C20—N3—Cd1 | 122.56 (15) | C28—C27—C32 | 119.4 (5) |
C23—N4—C24 | 116.6 (2) | C28—C27—C26 | 121.3 (5) |
C11—N5—C15 | 117.13 (19) | C32—C27—C26 | 119.4 (5) |
C11—N5—Cd1 | 118.71 (14) | C27—C28—C29 | 121.3 (5) |
C15—N5—Cd1 | 123.48 (14) | C27—C28—H28 | 119.4 |
N1—C1—C2 | 123.1 (2) | C29—C28—H28 | 119.4 |
N1—C1—H1 | 118.5 | N6—C29—C30 | 120.7 (7) |
C2—C1—H1 | 118.5 | N6—C29—C28 | 121.8 (6) |
C1—C2—C3 | 119.6 (2) | C30—C29—C28 | 117.5 (6) |
C1—C2—H2 | 120.2 | C31—C30—C29 | 121.7 (7) |
C3—C2—H2 | 120.2 | C31—C30—H30 | 119.2 |
C4—C3—C2 | 117.0 (2) | C29—C30—H30 | 119.2 |
C4—C3—C6 | 121.3 (2) | C29—C30—H6'1 | 155 (2) |
C2—C3—C6 | 121.7 (2) | C32—C31—C30 | 120.4 (5) |
C5—C4—C3 | 119.6 (2) | C32—C31—H31 | 119.8 |
C5—C4—H4 | 120.2 | C30—C31—H31 | 119.8 |
C3—C4—H4 | 120.2 | C32—C31—H6'2 | 135 (2) |
N1—C5—C4 | 123.5 (2) | C30—C31—H6'2 | 104 (2) |
N1—C5—H5 | 118.3 | C31—C32—C27 | 119.7 (5) |
C4—C5—H5 | 118.3 | C31—C32—H32 | 120.1 |
C10—C6—C7 | 116.9 (2) | C27—C32—H32 | 120.1 |
C10—C6—C3 | 121.7 (2) | C29—N6—H6A | 118 (3) |
C7—C6—C3 | 121.4 (2) | C29—N6—H6B | 119 (3) |
C8—C7—C6 | 119.4 (2) | H6A—N6—H6B | 113 (4) |
C8—C7—H7 | 120.3 | C28'—C27'—C32' | 121.8 (9) |
C6—C7—H7 | 120.3 | C27'—C28'—C29' | 121.3 (9) |
N2—C8—C7 | 124.0 (2) | C27'—C28'—H28' | 119.4 |
N2—C8—H8 | 118.0 | C29'—C28'—H28' | 119.4 |
C7—C8—H8 | 118.0 | N6'—C29'—C30' | 122.1 (11) |
N2—C9—C10 | 123.5 (2) | N6'—C29'—C28' | 122.3 (10) |
N2—C9—H9 | 118.3 | C30'—C29'—C28' | 115.5 (11) |
C10—C9—H9 | 118.3 | C29'—C30'—C31' | 123.6 (14) |
C9—C10—C6 | 119.7 (2) | C29'—C30'—H30' | 118.2 |
C9—C10—H10 | 120.2 | C31'—C30'—H30' | 118.2 |
C6—C10—H10 | 120.2 | C32'—C31'—C30' | 120.0 (9) |
N5—C11—C12 | 123.4 (2) | C32'—C31'—H6B | 138.4 (12) |
N5—C11—H11 | 118.3 | C30'—C31'—H6B | 98.5 (14) |
C12—C11—H11 | 118.3 | C32'—C31'—H31' | 120.0 |
C11—C12—C13 | 119.6 (2) | C30'—C31'—H31' | 120.0 |
C11—C12—H12 | 120.2 | C31'—C32'—C27' | 117.8 (8) |
C13—C12—H12 | 120.2 | C31'—C32'—H32' | 121.1 |
C14—C13—C12 | 116.9 (2) | C27'—C32'—H32' | 121.1 |
C14—C13—C13i | 121.5 (2) | C29'—N6'—H6'1 | 110 (6) |
C12—C13—C13i | 121.5 (2) | C29'—N6'—H6'2 | 113 (6) |
C15—C14—C13 | 119.8 (2) | H6'1—N6'—H6'2 | 120 (8) |
C15—C14—H14 | 120.1 | O5—Cl1—O4 | 109.21 (14) |
C13—C14—H14 | 120.1 | O5—Cl1—O6 | 109.88 (16) |
N5—C15—C14 | 123.1 (2) | O4—Cl1—O6 | 108.77 (17) |
N5—C15—H15 | 118.4 | O5—Cl1—O3 | 109.33 (13) |
C14—C15—H15 | 118.4 | O4—Cl1—O3 | 110.12 (15) |
N3—C16—C17 | 123.3 (2) | O6—Cl1—O3 | 109.52 (13) |
N3—C16—H16 | 118.3 | H7W—O4W—H8W | 111 (4) |
C17—C16—H16 | 118.3 | | |
| | | |
O2W—Cd1—N1—C1 | −30.74 (18) | C11—C12—C13—C13i | 179.8 (2) |
N5—Cd1—N1—C1 | 154.24 (18) | C12—C13—C14—C15 | 0.5 (3) |
O3W—Cd1—N1—C1 | −118.80 (18) | C13i—C13—C14—C15 | 179.8 (2) |
O1W—Cd1—N1—C1 | 63.09 (18) | C11—N5—C15—C14 | −2.1 (3) |
O2W—Cd1—N1—C5 | 141.98 (17) | Cd1—N5—C15—C14 | 168.34 (17) |
N5—Cd1—N1—C5 | −33.04 (17) | C13—C14—C15—N5 | 1.0 (4) |
O3W—Cd1—N1—C5 | 53.92 (17) | C20—N3—C16—C17 | −0.5 (3) |
O1W—Cd1—N1—C5 | −124.19 (17) | Cd1—N3—C16—C17 | 172.10 (17) |
O2W—Cd1—N3—C16 | 52.33 (17) | N3—C16—C17—C18 | −0.5 (3) |
N5—Cd1—N3—C16 | −132.75 (17) | C16—C17—C18—C19 | 0.9 (3) |
O3W—Cd1—N3—C16 | 139.97 (17) | C16—C17—C18—C21 | −179.3 (2) |
O1W—Cd1—N3—C16 | −41.26 (16) | C17—C18—C19—C20 | −0.3 (3) |
O2W—Cd1—N3—C20 | −135.51 (18) | C21—C18—C19—C20 | 179.9 (2) |
N5—Cd1—N3—C20 | 39.41 (18) | C16—N3—C20—C19 | 1.2 (3) |
O3W—Cd1—N3—C20 | −47.87 (18) | Cd1—N3—C20—C19 | −171.23 (17) |
O1W—Cd1—N3—C20 | 130.90 (18) | C18—C19—C20—N3 | −0.8 (4) |
O3W—Cd1—N5—C11 | −167.58 (17) | C19—C18—C21—C22 | 148.9 (2) |
O1W—Cd1—N5—C11 | 19.15 (17) | C17—C18—C21—C22 | −30.9 (3) |
N1—Cd1—N5—C11 | −73.16 (17) | C19—C18—C21—C25 | −31.2 (3) |
N3—Cd1—N5—C11 | 103.65 (17) | C17—C18—C21—C25 | 149.0 (2) |
O3W—Cd1—N5—C15 | 22.14 (17) | C25—C21—C22—C23 | −0.7 (3) |
O1W—Cd1—N5—C15 | −151.13 (17) | C18—C21—C22—C23 | 179.2 (2) |
N1—Cd1—N5—C15 | 116.56 (18) | C24—N4—C23—C22 | 0.3 (4) |
N3—Cd1—N5—C15 | −66.63 (18) | C21—C22—C23—N4 | 0.3 (4) |
C5—N1—C1—C2 | −1.9 (3) | C23—N4—C24—C25 | −0.6 (4) |
Cd1—N1—C1—C2 | 171.01 (17) | N4—C24—C25—C21 | 0.2 (4) |
N1—C1—C2—C3 | −0.2 (4) | C22—C21—C25—C24 | 0.5 (3) |
C1—C2—C3—C4 | 2.5 (3) | C18—C21—C25—C24 | −179.4 (2) |
C1—C2—C3—C6 | −176.3 (2) | O2—C26—C27—C28 | −145.5 (8) |
C2—C3—C4—C5 | −2.9 (3) | O1—C26—C27—C28 | 40.2 (11) |
C6—C3—C4—C5 | 175.9 (2) | O2—C26—C27—C32 | 33.3 (11) |
C1—N1—C5—C4 | 1.5 (3) | O1—C26—C27—C32 | −141.0 (8) |
Cd1—N1—C5—C4 | −171.64 (18) | C32—C27—C28—C29 | 1.2 (15) |
C3—C4—C5—N1 | 0.9 (4) | C26—C27—C28—C29 | 180.0 (9) |
C4—C3—C6—C10 | 30.2 (3) | C27—C28—C29—N6 | −176.8 (9) |
C2—C3—C6—C10 | −151.1 (2) | C27—C28—C29—C30 | 0.6 (14) |
C4—C3—C6—C7 | −149.1 (2) | N6—C29—C30—C31 | 176.3 (8) |
C2—C3—C6—C7 | 29.6 (3) | C28—C29—C30—C31 | −1.2 (14) |
C10—C6—C7—C8 | 0.1 (3) | C29—C30—C31—C32 | −0.1 (10) |
C3—C6—C7—C8 | 179.5 (2) | C30—C31—C32—C27 | 1.9 (10) |
C9—N2—C8—C7 | 0.0 (4) | C28—C27—C32—C31 | −2.5 (14) |
C6—C7—C8—N2 | 0.0 (4) | C26—C27—C32—C31 | 178.7 (6) |
C8—N2—C9—C10 | −0.1 (3) | C32'—C27'—C28'—C29' | 0 (3) |
N2—C9—C10—C6 | 0.3 (4) | C27'—C28'—C29'—N6' | −174.9 (16) |
C7—C6—C10—C9 | −0.3 (3) | C27'—C28'—C29'—C30' | 2 (2) |
C3—C6—C10—C9 | −179.6 (2) | N6'—C29'—C30'—C31' | 175.4 (16) |
C15—N5—C11—C12 | 1.8 (3) | C28'—C29'—C30'—C31' | −1 (3) |
Cd1—N5—C11—C12 | −169.15 (18) | C29'—C30'—C31'—C32' | −1 (3) |
N5—C11—C12—C13 | −0.3 (4) | C30'—C31'—C32'—C27' | 2 (2) |
C11—C12—C13—C14 | −0.9 (3) | C28'—C27'—C32'—C31' | −1 (3) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C30—H30···O6 | 0.95 | 2.31 | 3.228 (6) | 163 |
C11—H11···N4ii | 0.95 | 2.61 | 3.406 (3) | 142 |
C14—H14···O4iii | 0.95 | 2.50 | 3.262 (3) | 137 |
C23—H23···O4iv | 0.95 | 2.58 | 3.336 (3) | 137 |
C31—H31···O3v | 0.95 | 2.48 | 3.166 (6) | 129 |
O1W—H1W···O1vi | 0.83 | 2.00 | 2.791 (2) | 160 |
O1W—H2W···N2vii | 0.83 | 2.10 | 2.924 (3) | 177 |
O2W—H3W···O4W | 0.83 | 1.81 | 2.641 (3) | 176 |
O2W—H4W···O1 | 0.83 | 1.94 | 2.765 (2) | 171 |
O3W—H6W···N4viii | 0.84 | 1.92 | 2.750 (3) | 170 |
N6—H6A···O3 | 0.88 (1) | 2.37 (2) | 3.196 (4) | 157 (4) |
N6—H6B···O2vi | 0.88 (1) | 2.23 (2) | 3.090 (4) | 166 (4) |
N6′—H6′1···O6 | 0.88 (1) | 2.41 (2) | 3.275 (7) | 167 (8) |
N6′—H6′2···O3v | 0.88 (1) | 2.63 (3) | 3.481 (8) | 162 (8) |
O4W—H7W···O1ix | 0.79 (4) | 2.04 (4) | 2.801 (3) | 163 (4) |
O4W—H8W···O2vi | 0.79 (4) | 1.93 (4) | 2.695 (3) | 165 (4) |
Symmetry codes: (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1; (v) x+1, y, z; (vi) x−1, y, z; (vii) x−1/2, −y+1/2, z+1/2; (viii) x+1/2, −y+1/2, z−1/2; (ix) −x+1, −y+1, −z+1. |
Table 3. π–π stacking interactions (Å, °) topCg1 is the centroid of the N1, C1–C5 ring.
Cg2 is the centroid of the N2, C6–C10 ring.
Cg3 is the centroid of the N3, C16–C20 ring.
Cg4 is the centroid of the N4, C21–C24 ring. |
CgI | CgJ | CgI···CgJa | CgI···P(J)b | CgJ···P(I)c | Slippage |
Cg1 | Cg4vii | 3.9576 (13) | 3.935 | 3.956 | 0.466 |
Cg1 | Cg4iii | 3.6423 (13) | 3.367 | 3.385 | 1.388 |
Cg2 | Cg3vii | 3.7461 (13) | 3.319 | 3.388 | 1.737 |
Cg3 | Cg2ii | 3.7245 (13) | 3.528 | 3.494 | 1.192 |
Symmetry codes: (ii) -1/2+x, 1/2-y,
1/2+z; (iii)1/2+x, 1/2-y,-1/2+z; (vii)
-1/2+x,
1/2-y, -1/2+z.
Notes:
(a) Distance between centroids.
(b) Perpendicular distance of CgI on ring plan J.
(c) Perpendicular distance of CgJ on ring plan I.
Slippage = vertical displacement between ring centroids. |