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The design and synthesis of functional coordination polymers is motivated not only by their structural beauty but also by their potential applications. ZnII and CdII coordination polymers are promising candidates for producing photoactive materials because these d10 metal ions not only possess a variety of coordination numbers and geometries, but also exhibit luminescence properties when bound to functional ligands. It is difficult to predict the final structure of such polymers because the assembly process is influenced by many subtle factors. Bis(imidazol-1-yl)-substituted alkane/benzene molecules are good bridging ligands because their flexibility allows them to bend and rotate when they coordinate to metal centres. Two new ZnII and CdII coordination polymers based on mixed ligands, namely, poly[[μ2-1,4-bis(imidazol-1-ylmethyl)benzene-κ2N3:N3′]bis(μ3-2,2-dimethylbutanoato-κ3O1:O4:O4′)dizinc(II)], [Zn2(C6H8O4)2(C14H14N4)]n, and poly[[μ2-1,4-bis(imidazol-1-ylmethyl)benzene-κ2N3:N3′]bis(μ3-2,2-dimethylbutanoato-κ5O1,O1′:O4,O4′:O4)dicadmium(II)], [Cd2(C6H8O4)2(C14H14N4)]n, have been synthesized under hydrothermal conditions and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and thermogravimetric analysis. Both complexes crystallize in the monoclinic space group C2/c with similar unit-cell parameters and feature two-dimensional structures formed by the interconnection of S-shaped Zn(Cd)–2,2-dimethylsuccinate chains with 1,4-bis(imidazol-1-ylmethyl)benzene bridges. However, the CdII and ZnII centres have different coordination numbers and the 2,2-dimethylsuccinate ligands display different coordination modes. Both complexes exhibit a blue photoluminescence in the solid state at room temperature.
Supporting information
CCDC references: 1488874; 1488873
For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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) and PLATON (Spek, 2009).
(dj3530) Poly[[µ
2-1,4-bis(imidazol-1-ylmethyl)benzene-
κ2N3:
N3']bis(µ
3-2,2-dimethylbutanoato-
κ3O1:
O4:
O4')dizinc(II)]
top
Crystal data top
[Zn2(C6H8O4)2(C14H14N4)] | F(000) = 1352 |
Mr = 657.28 | Dx = 1.646 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.059 (6) Å | Cell parameters from 3260 reflections |
b = 20.839 (13) Å | θ = 2.3–28.0° |
c = 13.198 (8) Å | µ = 1.87 mm−1 |
β = 106.567 (9)° | T = 296 K |
V = 2652 (3) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.25 × 0.21 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3263 independent reflections |
Radiation source: fine-focus sealed tube | 2617 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
phi and ω scans | θmax = 28.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −13→12 |
Tmin = 0.643, Tmax = 0.695 | k = −20→27 |
8289 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3263 reflections | Δρmax = 0.88 e Å−3 |
182 parameters | Δρmin = −0.70 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0216 (8) |
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 > 2sigma(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 | |
C1 | 0.2417 (2) | 0.89105 (12) | 0.72458 (18) | 0.0265 (5) | |
C2 | 0.1554 (2) | 0.88417 (12) | 0.60894 (17) | 0.0257 (5) | |
C3 | 0.1814 (3) | 0.93929 (11) | 0.54097 (19) | 0.0271 (5) | |
H3A | 0.1194 | 0.9339 | 0.4703 | 0.033* | |
H3B | 0.1553 | 0.9789 | 0.5689 | 0.033* | |
C4 | 0.3263 (3) | 0.94752 (11) | 0.53172 (18) | 0.0256 (5) | |
C5 | 0.1838 (4) | 0.81974 (13) | 0.5637 (2) | 0.0466 (8) | |
H5A | 0.1290 | 0.8164 | 0.4913 | 0.070* | |
H5B | 0.1600 | 0.7855 | 0.6038 | 0.070* | |
H5C | 0.2804 | 0.8169 | 0.5675 | 0.070* | |
C6 | 0.0026 (3) | 0.88723 (18) | 0.6077 (2) | 0.0508 (8) | |
H6A | −0.0553 | 0.8831 | 0.5363 | 0.076* | |
H6B | −0.0154 | 0.9276 | 0.6362 | 0.076* | |
H6C | −0.0170 | 0.8529 | 0.6498 | 0.076* | |
C7 | 0.3469 (2) | 0.90206 (12) | 1.11939 (18) | 0.0260 (5) | |
H7 | 0.3438 | 0.9450 | 1.1375 | 0.031* | |
C8 | 0.3431 (3) | 0.79762 (12) | 1.1277 (2) | 0.0337 (6) | |
H8 | 0.3367 | 0.7559 | 1.1507 | 0.040* | |
C9 | 0.3647 (3) | 0.81574 (12) | 1.0352 (2) | 0.0333 (6) | |
H9 | 0.3767 | 0.7880 | 0.9833 | 0.040* | |
C10 | 0.2962 (2) | 0.85880 (13) | 1.28073 (19) | 0.0307 (5) | |
H10A | 0.3337 | 0.8987 | 1.3150 | 0.037* | |
H10B | 0.3387 | 0.8238 | 1.3272 | 0.037* | |
C11 | 0.1424 (2) | 0.85765 (12) | 1.26456 (17) | 0.0255 (5) | |
C12 | 0.0702 (2) | 0.80013 (12) | 1.25671 (19) | 0.0302 (5) | |
H12 | 0.1173 | 0.7614 | 1.2606 | 0.036* | |
C13 | 0.0704 (3) | 0.91564 (12) | 1.25725 (19) | 0.0285 (5) | |
H13 | 0.1180 | 0.9543 | 1.2622 | 0.034* | |
Zn1 | 0.38320 (3) | 0.933764 (12) | 0.906393 (19) | 0.02351 (13) | |
O1 | 0.2788 (2) | 0.84343 (9) | 0.78101 (15) | 0.0447 (5) | |
O2 | 0.26604 (19) | 0.94784 (9) | 0.76064 (14) | 0.0347 (4) | |
O3 | 0.42509 (19) | 0.92307 (9) | 0.60092 (15) | 0.0367 (5) | |
O4 | 0.3406 (2) | 0.97935 (9) | 0.45507 (14) | 0.0414 (5) | |
N1 | 0.36634 (19) | 0.88157 (9) | 1.03007 (15) | 0.0265 (4) | |
N2 | 0.33239 (19) | 0.85287 (9) | 1.18050 (15) | 0.0249 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0207 (12) | 0.0412 (14) | 0.0194 (11) | 0.0023 (10) | 0.0085 (9) | −0.0014 (10) |
C2 | 0.0218 (12) | 0.0342 (13) | 0.0194 (11) | −0.0070 (9) | 0.0033 (9) | 0.0001 (9) |
C3 | 0.0225 (12) | 0.0360 (13) | 0.0207 (11) | 0.0015 (10) | 0.0028 (9) | 0.0052 (9) |
C4 | 0.0279 (13) | 0.0283 (12) | 0.0220 (11) | −0.0078 (9) | 0.0093 (9) | −0.0030 (9) |
C5 | 0.070 (2) | 0.0335 (14) | 0.0351 (15) | −0.0112 (14) | 0.0129 (14) | −0.0075 (11) |
C6 | 0.0230 (14) | 0.089 (2) | 0.0386 (16) | −0.0137 (14) | 0.0051 (12) | 0.0072 (15) |
C7 | 0.0226 (12) | 0.0299 (12) | 0.0262 (12) | 0.0015 (9) | 0.0081 (9) | 0.0020 (9) |
C8 | 0.0351 (14) | 0.0292 (13) | 0.0363 (14) | −0.0030 (11) | 0.0093 (11) | 0.0004 (10) |
C9 | 0.0347 (14) | 0.0346 (14) | 0.0308 (13) | −0.0031 (11) | 0.0095 (11) | −0.0063 (10) |
C10 | 0.0219 (12) | 0.0472 (15) | 0.0222 (12) | −0.0009 (11) | 0.0052 (9) | 0.0033 (10) |
C11 | 0.0224 (12) | 0.0377 (13) | 0.0172 (10) | −0.0001 (10) | 0.0066 (9) | 0.0019 (9) |
C12 | 0.0274 (13) | 0.0308 (13) | 0.0341 (13) | 0.0049 (10) | 0.0113 (10) | 0.0023 (10) |
C13 | 0.0306 (13) | 0.0295 (12) | 0.0244 (12) | −0.0049 (10) | 0.0060 (10) | −0.0001 (9) |
Zn1 | 0.01921 (18) | 0.0334 (2) | 0.01853 (17) | 0.00077 (10) | 0.00643 (11) | −0.00087 (10) |
O1 | 0.0543 (13) | 0.0521 (12) | 0.0265 (10) | 0.0087 (10) | 0.0095 (9) | 0.0137 (8) |
O2 | 0.0324 (10) | 0.0427 (10) | 0.0240 (9) | 0.0072 (8) | 0.0002 (7) | −0.0090 (7) |
O3 | 0.0198 (9) | 0.0593 (12) | 0.0326 (10) | 0.0003 (8) | 0.0098 (8) | 0.0108 (8) |
O4 | 0.0548 (12) | 0.0417 (11) | 0.0305 (10) | −0.0182 (9) | 0.0163 (9) | 0.0060 (8) |
N1 | 0.0199 (10) | 0.0356 (11) | 0.0239 (10) | −0.0011 (8) | 0.0061 (8) | 0.0004 (8) |
N2 | 0.0183 (10) | 0.0339 (11) | 0.0233 (10) | −0.0017 (8) | 0.0071 (8) | 0.0034 (8) |
Geometric parameters (Å, º) top
C1—O1 | 1.233 (3) | C8—C9 | 1.353 (4) |
C1—O2 | 1.273 (3) | C8—N2 | 1.366 (3) |
C1—C2 | 1.532 (3) | C8—H8 | 0.9300 |
C1—Zn1 | 2.575 (3) | C9—N1 | 1.374 (3) |
C2—C3 | 1.525 (3) | C9—H9 | 0.9300 |
C2—C5 | 1.529 (4) | C10—N2 | 1.474 (3) |
C2—C6 | 1.533 (4) | C10—C11 | 1.501 (3) |
C3—C4 | 1.506 (4) | C10—H10A | 0.9700 |
C3—H3A | 0.9700 | C10—H10B | 0.9700 |
C3—H3B | 0.9700 | C11—C12 | 1.390 (4) |
C4—O3 | 1.251 (3) | C11—C13 | 1.398 (4) |
C4—O4 | 1.252 (3) | C12—C12i | 1.372 (5) |
C5—H5A | 0.9600 | C12—H12 | 0.9300 |
C5—H5B | 0.9600 | C13—C13i | 1.374 (5) |
C5—H5C | 0.9600 | C13—H13 | 0.9300 |
C6—H6A | 0.9600 | Zn1—O2 | 1.970 (2) |
C6—H6B | 0.9600 | Zn1—O3ii | 1.971 (2) |
C6—H6C | 0.9600 | Zn1—O4iii | 2.008 (2) |
C7—N1 | 1.320 (3) | Zn1—N1 | 2.008 (2) |
C7—N2 | 1.338 (3) | O3—Zn1ii | 1.971 (2) |
C7—H7 | 0.9300 | O4—Zn1iv | 2.008 (2) |
| | | |
O1—C1—O2 | 122.0 (2) | N2—C8—H8 | 126.8 |
O1—C1—C2 | 121.0 (2) | C8—C9—N1 | 109.3 (2) |
O2—C1—C2 | 117.0 (2) | C8—C9—H9 | 125.3 |
O1—C1—Zn1 | 73.95 (15) | N1—C9—H9 | 125.3 |
O2—C1—Zn1 | 48.22 (11) | N2—C10—C11 | 112.30 (19) |
C2—C1—Zn1 | 165.08 (17) | N2—C10—H10A | 109.1 |
C3—C2—C5 | 110.4 (2) | C11—C10—H10A | 109.1 |
C3—C2—C1 | 111.84 (19) | N2—C10—H10B | 109.1 |
C5—C2—C1 | 110.8 (2) | C11—C10—H10B | 109.1 |
C3—C2—C6 | 107.6 (2) | H10A—C10—H10B | 107.9 |
C5—C2—C6 | 109.3 (2) | C12—C11—C13 | 119.4 (2) |
C1—C2—C6 | 106.7 (2) | C12—C11—C10 | 121.3 (2) |
C4—C3—C2 | 117.75 (19) | C13—C11—C10 | 119.3 (2) |
C4—C3—H3A | 107.9 | C12i—C12—C11 | 120.42 (14) |
C2—C3—H3A | 107.9 | C12i—C12—H12 | 119.8 |
C4—C3—H3B | 107.9 | C11—C12—H12 | 119.8 |
C2—C3—H3B | 107.9 | C13i—C13—C11 | 120.18 (14) |
H3A—C3—H3B | 107.2 | C13i—C13—H13 | 119.9 |
O3—C4—O4 | 123.7 (2) | C11—C13—H13 | 119.9 |
O3—C4—C3 | 118.7 (2) | O2—Zn1—O3ii | 106.87 (9) |
O4—C4—C3 | 117.6 (2) | O2—Zn1—O4iii | 93.18 (8) |
C2—C5—H5A | 109.5 | O3ii—Zn1—O4iii | 114.74 (8) |
C2—C5—H5B | 109.5 | O2—Zn1—N1 | 135.11 (9) |
H5A—C5—H5B | 109.5 | O3ii—Zn1—N1 | 106.80 (8) |
C2—C5—H5C | 109.5 | O4iii—Zn1—N1 | 98.81 (9) |
H5A—C5—H5C | 109.5 | O2—Zn1—C1 | 28.81 (8) |
H5B—C5—H5C | 109.5 | O3ii—Zn1—C1 | 101.78 (8) |
C2—C6—H6A | 109.5 | O4iii—Zn1—C1 | 119.89 (8) |
C2—C6—H6B | 109.5 | N1—Zn1—C1 | 114.70 (9) |
H6A—C6—H6B | 109.5 | C1—O2—Zn1 | 102.97 (15) |
C2—C6—H6C | 109.5 | C4—O3—Zn1ii | 120.23 (16) |
H6A—C6—H6C | 109.5 | C4—O4—Zn1iv | 145.14 (17) |
H6B—C6—H6C | 109.5 | C7—N1—C9 | 105.8 (2) |
N1—C7—N2 | 111.1 (2) | C7—N1—Zn1 | 128.25 (17) |
N1—C7—H7 | 124.4 | C9—N1—Zn1 | 125.87 (17) |
N2—C7—H7 | 124.4 | C7—N2—C8 | 107.5 (2) |
C9—C8—N2 | 106.3 (2) | C7—N2—C10 | 125.0 (2) |
C9—C8—H8 | 126.8 | C8—N2—C10 | 127.2 (2) |
| | | |
O1—C1—C2—C3 | −151.1 (2) | O2—C1—Zn1—N1 | 141.44 (16) |
O2—C1—C2—C3 | 32.7 (3) | C2—C1—Zn1—N1 | 148.8 (6) |
Zn1—C1—C2—C3 | 26.6 (7) | O1—C1—O2—Zn1 | 6.0 (3) |
O1—C1—C2—C5 | −27.4 (3) | C2—C1—O2—Zn1 | −177.87 (17) |
O2—C1—C2—C5 | 156.4 (2) | O3ii—Zn1—O2—C1 | 83.74 (16) |
Zn1—C1—C2—C5 | 150.2 (6) | O4iii—Zn1—O2—C1 | −159.21 (16) |
O1—C1—C2—C6 | 91.5 (3) | N1—Zn1—O2—C1 | −53.4 (2) |
O2—C1—C2—C6 | −84.6 (3) | O4—C4—O3—Zn1ii | 0.2 (3) |
Zn1—C1—C2—C6 | −90.8 (6) | C3—C4—O3—Zn1ii | −178.96 (16) |
C5—C2—C3—C4 | −62.2 (3) | O3—C4—O4—Zn1iv | −83.7 (4) |
C1—C2—C3—C4 | 61.7 (3) | C3—C4—O4—Zn1iv | 95.4 (3) |
C6—C2—C3—C4 | 178.6 (2) | N2—C7—N1—C9 | −0.3 (3) |
C2—C3—C4—O3 | −20.7 (3) | N2—C7—N1—Zn1 | 176.15 (15) |
C2—C3—C4—O4 | 160.0 (2) | C8—C9—N1—C7 | 0.5 (3) |
N2—C8—C9—N1 | −0.5 (3) | C8—C9—N1—Zn1 | −176.07 (17) |
N2—C10—C11—C12 | 84.2 (3) | O2—Zn1—N1—C7 | −109.6 (2) |
N2—C10—C11—C13 | −95.7 (3) | O3ii—Zn1—N1—C7 | 113.3 (2) |
C13—C11—C12—C12i | −0.8 (4) | O4iii—Zn1—N1—C7 | −6.0 (2) |
C10—C11—C12—C12i | 179.2 (3) | C1—Zn1—N1—C7 | −134.76 (19) |
C12—C11—C13—C13i | 0.2 (4) | O2—Zn1—N1—C9 | 66.3 (2) |
C10—C11—C13—C13i | −179.8 (3) | O3ii—Zn1—N1—C9 | −70.9 (2) |
O1—C1—Zn1—O2 | −174.7 (2) | O4iii—Zn1—N1—C9 | 169.9 (2) |
C2—C1—Zn1—O2 | 7.4 (6) | C1—Zn1—N1—C9 | 41.1 (2) |
O1—C1—Zn1—O3ii | 81.61 (16) | N1—C7—N2—C8 | 0.0 (3) |
O2—C1—Zn1—O3ii | −103.66 (16) | N1—C7—N2—C10 | −173.93 (19) |
C2—C1—Zn1—O3ii | −96.3 (6) | C9—C8—N2—C7 | 0.3 (3) |
O1—C1—Zn1—O4iii | −150.59 (14) | C9—C8—N2—C10 | 174.1 (2) |
O2—C1—Zn1—O4iii | 24.13 (18) | C11—C10—N2—C7 | 89.6 (3) |
C2—C1—Zn1—O4iii | 31.5 (7) | C11—C10—N2—C8 | −83.2 (3) |
O1—C1—Zn1—N1 | −33.28 (17) | | |
Symmetry codes: (i) −x, y, −z+5/2; (ii) −x+1, y, −z+3/2; (iii) x, −y+2, z+1/2; (iv) x, −y+2, z−1/2. |
(dj3531) Poly[[µ
2-1,4-bis(imidazol-1-ylmethyl)benzene-
κ2N3:
N3']bis(µ
3-2,2-dimethylbutanoato-
κ3O1:
O4:
O4')dicadmium(II)]
top
Crystal data top
[Cd2(C6H8O4)2(C14H14N4)] | F(000) = 1496 |
Mr = 751.34 | Dx = 1.835 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.575 (3) Å | Cell parameters from 4764 reflections |
b = 20.477 (5) Å | θ = 2.4–28.6° |
c = 13.938 (3) Å | µ = 1.62 mm−1 |
β = 115.703 (14)° | T = 296 K |
V = 2719.6 (12) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.21 × 0.17 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3381 independent reflections |
Radiation source: fine-focus sealed tube | 2963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
phi and ω scans | θmax = 28.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −13→14 |
Tmin = 0.678, Tmax = 0.770 | k = −27→26 |
8603 measured reflections | l = −18→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.0557P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.012 |
3381 reflections | Δρmax = 1.05 e Å−3 |
184 parameters | Δρmin = −1.36 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0034 (2) |
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 > 2sigma(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 | |
Cd1 | 0.773049 (19) | 0.177121 (9) | 0.923802 (13) | 0.02770 (11) | |
O1 | 0.7807 (2) | 0.10343 (10) | 0.79074 (15) | 0.0394 (5) | |
O2 | 0.7278 (2) | 0.20682 (9) | 0.75732 (15) | 0.0372 (5) | |
O3 | 0.5599 (2) | 0.13698 (13) | 0.9058 (2) | 0.0559 (6) | |
O4 | 0.6247 (2) | 0.22514 (11) | 0.9983 (2) | 0.0575 (7) | |
N1 | 0.9369 (2) | 0.12452 (11) | 1.05943 (17) | 0.0299 (5) | |
N2 | 1.1256 (2) | 0.09868 (10) | 1.20142 (16) | 0.0269 (4) | |
C1 | 0.7430 (3) | 0.14979 (13) | 0.72774 (19) | 0.0261 (5) | |
C2 | 0.7199 (3) | 0.14116 (13) | 0.6126 (2) | 0.0288 (5) | |
C3 | 0.6051 (3) | 0.18709 (13) | 0.5407 (2) | 0.0305 (6) | |
H3A | 0.6391 | 0.2315 | 0.5579 | 0.037* | |
H3B | 0.5886 | 0.1789 | 0.4677 | 0.037* | |
C4 | 0.5334 (3) | 0.18223 (13) | 0.9529 (2) | 0.0317 (6) | |
C5 | 0.6856 (4) | 0.07069 (15) | 0.5756 (2) | 0.0462 (8) | |
H5A | 0.7557 | 0.0423 | 0.6253 | 0.069* | |
H5B | 0.6843 | 0.0659 | 0.5066 | 0.069* | |
H5C | 0.5953 | 0.0594 | 0.5715 | 0.069* | |
C6 | 0.8570 (4) | 0.1594 (2) | 0.6071 (3) | 0.0487 (8) | |
H6A | 0.8828 | 0.2033 | 0.6326 | 0.073* | |
H6B | 0.8442 | 0.1566 | 0.5347 | 0.073* | |
H6C | 0.9299 | 0.1299 | 0.6506 | 0.073* | |
C7 | 1.0450 (3) | 0.14716 (13) | 1.1438 (2) | 0.0292 (5) | |
H7 | 1.0624 | 0.1912 | 1.1608 | 0.035* | |
C8 | 1.0673 (3) | 0.04124 (13) | 1.1521 (2) | 0.0353 (6) | |
H8 | 1.1007 | −0.0007 | 1.1742 | 0.042* | |
C9 | 0.9504 (3) | 0.05839 (14) | 1.0643 (2) | 0.0362 (6) | |
H9 | 0.8888 | 0.0293 | 1.0148 | 0.043* | |
C10 | 1.2580 (3) | 0.10580 (16) | 1.2965 (2) | 0.0342 (6) | |
H10A | 1.2668 | 0.0707 | 1.3456 | 0.041* | |
H10B | 1.2572 | 0.1467 | 1.3313 | 0.041* | |
C11 | 1.3831 (3) | 0.10469 (13) | 1.27156 (19) | 0.0286 (5) | |
C12 | 1.4418 (3) | 0.04608 (13) | 1.2605 (2) | 0.0354 (6) | |
H12 | 1.4020 | 0.0067 | 1.2668 | 0.042* | |
C13 | 1.4413 (3) | 0.16262 (14) | 1.2602 (2) | 0.0320 (6) | |
H13 | 1.4027 | 0.2021 | 1.2676 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02447 (15) | 0.03472 (15) | 0.01904 (14) | −0.00038 (6) | 0.00488 (10) | 0.00079 (6) |
O1 | 0.0466 (12) | 0.0422 (11) | 0.0241 (9) | 0.0139 (9) | 0.0105 (9) | 0.0099 (8) |
O2 | 0.0530 (13) | 0.0323 (10) | 0.0244 (9) | −0.0021 (9) | 0.0149 (9) | −0.0015 (8) |
O3 | 0.0362 (12) | 0.0746 (16) | 0.0618 (15) | −0.0112 (11) | 0.0259 (11) | −0.0277 (13) |
O4 | 0.0390 (13) | 0.0442 (12) | 0.0766 (17) | −0.0176 (10) | 0.0133 (12) | −0.0101 (12) |
N1 | 0.0260 (11) | 0.0362 (11) | 0.0240 (10) | 0.0039 (9) | 0.0076 (9) | 0.0001 (9) |
N2 | 0.0222 (10) | 0.0359 (11) | 0.0202 (10) | 0.0022 (9) | 0.0070 (8) | 0.0014 (8) |
C1 | 0.0195 (12) | 0.0343 (13) | 0.0206 (11) | 0.0011 (10) | 0.0049 (9) | 0.0023 (10) |
C2 | 0.0300 (14) | 0.0364 (13) | 0.0208 (12) | 0.0042 (10) | 0.0117 (10) | 0.0036 (10) |
C3 | 0.0326 (15) | 0.0365 (13) | 0.0202 (13) | 0.0047 (11) | 0.0096 (11) | 0.0065 (10) |
C4 | 0.0270 (14) | 0.0385 (15) | 0.0214 (13) | −0.0050 (10) | 0.0028 (11) | 0.0060 (10) |
C5 | 0.064 (2) | 0.0387 (16) | 0.0335 (16) | 0.0079 (15) | 0.0191 (14) | −0.0023 (12) |
C6 | 0.0310 (16) | 0.080 (2) | 0.0383 (18) | 0.0061 (17) | 0.0183 (14) | 0.0065 (17) |
C7 | 0.0275 (13) | 0.0337 (13) | 0.0237 (12) | 0.0012 (10) | 0.0085 (10) | 0.0019 (10) |
C8 | 0.0363 (15) | 0.0306 (13) | 0.0330 (14) | 0.0019 (11) | 0.0094 (12) | −0.0005 (11) |
C9 | 0.0360 (15) | 0.0360 (13) | 0.0314 (14) | 0.0000 (12) | 0.0099 (12) | −0.0037 (11) |
C10 | 0.0262 (13) | 0.0524 (16) | 0.0205 (12) | 0.0020 (12) | 0.0069 (10) | 0.0009 (11) |
C11 | 0.0237 (12) | 0.0402 (14) | 0.0166 (11) | 0.0022 (10) | 0.0039 (9) | 0.0022 (10) |
C12 | 0.0343 (15) | 0.0328 (13) | 0.0399 (15) | −0.0034 (11) | 0.0169 (12) | 0.0003 (11) |
C13 | 0.0362 (16) | 0.0332 (12) | 0.0241 (13) | 0.0021 (11) | 0.0108 (11) | −0.0021 (10) |
Geometric parameters (Å, º) top
Cd1—N1 | 2.212 (2) | C3—H3A | 0.9700 |
Cd1—O2 | 2.2406 (19) | C3—H3B | 0.9700 |
Cd1—O3 | 2.309 (2) | C4—C3ii | 1.508 (4) |
Cd1—O4i | 2.310 (2) | C5—H5A | 0.9600 |
Cd1—O1 | 2.419 (2) | C5—H5B | 0.9600 |
Cd1—O4 | 2.433 (3) | C5—H5C | 0.9600 |
Cd1—C1 | 2.670 (3) | C6—H6A | 0.9600 |
Cd1—C4 | 2.737 (3) | C6—H6B | 0.9600 |
O1—C1 | 1.236 (3) | C6—H6C | 0.9600 |
O2—C1 | 1.272 (3) | C7—H7 | 0.9300 |
O3—C4 | 1.236 (4) | C8—C9 | 1.355 (4) |
O4—C4 | 1.255 (3) | C8—H8 | 0.9300 |
O4—Cd1i | 2.310 (2) | C9—H9 | 0.9300 |
N1—C7 | 1.319 (3) | C10—C11 | 1.506 (4) |
N1—C9 | 1.360 (4) | C10—H10A | 0.9700 |
N2—C7 | 1.328 (3) | C10—H10B | 0.9700 |
N2—C8 | 1.367 (3) | C11—C13 | 1.377 (4) |
N2—C10 | 1.459 (3) | C11—C12 | 1.390 (4) |
C1—C2 | 1.525 (3) | C12—C12iii | 1.384 (6) |
C2—C5 | 1.522 (4) | C12—H12 | 0.9304 |
C2—C3 | 1.519 (4) | C13—C13iii | 1.388 (6) |
C2—C6 | 1.531 (4) | C13—H13 | 0.9306 |
C3—C4ii | 1.508 (4) | | |
| | | |
N1—Cd1—O2 | 138.88 (8) | C1—C2—C6 | 107.5 (2) |
N1—Cd1—O3 | 106.58 (9) | C3—C2—C6 | 108.6 (2) |
O2—Cd1—O3 | 102.97 (9) | C4ii—C3—C2 | 116.1 (2) |
N1—Cd1—O4i | 89.25 (9) | C4ii—C3—H3A | 108.3 |
O2—Cd1—O4i | 95.60 (9) | C2—C3—H3A | 108.3 |
O3—Cd1—O4i | 126.55 (9) | C4ii—C3—H3B | 108.3 |
N1—Cd1—O1 | 94.43 (7) | C2—C3—H3B | 108.3 |
O2—Cd1—O1 | 55.84 (7) | H3A—C3—H3B | 107.4 |
O3—Cd1—O1 | 92.89 (8) | O3—C4—O4 | 119.4 (3) |
O4i—Cd1—O1 | 137.42 (9) | O3—C4—C3ii | 122.0 (2) |
N1—Cd1—O4 | 104.06 (9) | O4—C4—C3ii | 118.6 (3) |
O2—Cd1—O4 | 116.41 (8) | O3—C4—Cd1 | 56.96 (16) |
O3—Cd1—O4 | 53.87 (8) | O4—C4—Cd1 | 62.74 (18) |
O4i—Cd1—O4 | 72.91 (9) | C3ii—C4—Cd1 | 175.12 (19) |
O1—Cd1—O4 | 145.23 (8) | C2—C5—H5A | 109.5 |
N1—Cd1—C1 | 118.30 (8) | C2—C5—H5B | 109.5 |
O2—Cd1—C1 | 28.33 (8) | H5A—C5—H5B | 109.5 |
O3—Cd1—C1 | 97.88 (8) | C2—C5—H5C | 109.5 |
O4i—Cd1—C1 | 119.10 (9) | H5A—C5—H5C | 109.5 |
O1—Cd1—C1 | 27.55 (7) | H5B—C5—H5C | 109.5 |
O4—Cd1—C1 | 135.16 (8) | C2—C6—H6A | 109.5 |
N1—Cd1—C4 | 108.93 (8) | C2—C6—H6B | 109.5 |
O2—Cd1—C4 | 110.33 (8) | H6A—C6—H6B | 109.5 |
O3—Cd1—C4 | 26.66 (8) | C2—C6—H6C | 109.5 |
O4i—Cd1—C4 | 99.91 (9) | H6A—C6—H6C | 109.5 |
O1—Cd1—C4 | 118.58 (8) | H6B—C6—H6C | 109.5 |
O4—Cd1—C4 | 27.30 (8) | N1—C7—N2 | 110.9 (2) |
C1—Cd1—C4 | 116.91 (8) | N1—C7—H7 | 124.5 |
C1—O1—Cd1 | 87.57 (16) | N2—C7—H7 | 124.5 |
C1—O2—Cd1 | 94.95 (15) | C9—C8—N2 | 105.5 (2) |
C4—O3—Cd1 | 96.38 (18) | C9—C8—H8 | 127.3 |
C4—O4—Cd1i | 160.8 (2) | N2—C8—H8 | 127.3 |
C4—O4—Cd1 | 90.0 (2) | C8—C9—N1 | 109.8 (2) |
Cd1i—O4—Cd1 | 107.09 (9) | C8—C9—H9 | 125.1 |
C7—N1—C9 | 105.9 (2) | N1—C9—H9 | 125.1 |
C7—N1—Cd1 | 130.22 (18) | N2—C10—C11 | 112.5 (2) |
C9—N1—Cd1 | 123.63 (18) | N2—C10—H10A | 109.1 |
C7—N2—C8 | 108.0 (2) | C11—C10—H10A | 109.1 |
C7—N2—C10 | 125.9 (2) | N2—C10—H10B | 109.1 |
C8—N2—C10 | 126.0 (2) | C11—C10—H10B | 109.1 |
O1—C1—O2 | 121.5 (2) | H10A—C10—H10B | 107.8 |
O1—C1—C2 | 120.9 (2) | C13—C11—C12 | 119.2 (3) |
O2—C1—C2 | 117.6 (2) | C13—C11—C10 | 119.6 (2) |
O1—C1—Cd1 | 64.88 (14) | C12—C11—C10 | 121.1 (2) |
O2—C1—Cd1 | 56.73 (12) | C12iii—C12—C11 | 120.28 (16) |
C2—C1—Cd1 | 174.20 (18) | C12iii—C12—H12 | 120.0 |
C5—C2—C1 | 111.9 (2) | C11—C12—H12 | 119.7 |
C5—C2—C3 | 111.0 (2) | C11—C13—C13iii | 120.50 (16) |
C1—C2—C3 | 109.8 (2) | C11—C13—H13 | 119.7 |
C5—C2—C6 | 107.8 (3) | C13iii—C13—H13 | 119.8 |
| | | |
N1—Cd1—O1—C1 | −151.59 (16) | O2—Cd1—C1—C2 | −9.7 (17) |
O2—Cd1—O1—C1 | −2.20 (15) | O3—Cd1—C1—C2 | 93.1 (18) |
O3—Cd1—O1—C1 | 101.53 (17) | O4i—Cd1—C1—C2 | −46.8 (18) |
O4i—Cd1—O1—C1 | −57.9 (2) | O1—Cd1—C1—C2 | 174.1 (19) |
O4—Cd1—O1—C1 | 85.8 (2) | O4—Cd1—C1—C2 | 47.9 (18) |
C4—Cd1—O1—C1 | 94.03 (17) | C4—Cd1—C1—C2 | 73.4 (18) |
N1—Cd1—O2—C1 | 52.7 (2) | O1—C1—C2—C5 | 24.9 (4) |
O3—Cd1—O2—C1 | −82.47 (16) | O2—C1—C2—C5 | −158.1 (3) |
O4i—Cd1—O2—C1 | 147.99 (15) | Cd1—C1—C2—C5 | −148.9 (17) |
O1—Cd1—O2—C1 | 2.15 (14) | O1—C1—C2—C3 | 148.6 (3) |
O4—Cd1—O2—C1 | −138.33 (15) | O2—C1—C2—C3 | −34.3 (3) |
C4—Cd1—O2—C1 | −109.26 (15) | Cd1—C1—C2—C3 | −25.2 (19) |
N1—Cd1—O3—C4 | 99.30 (19) | O1—C1—C2—C6 | −93.3 (3) |
O2—Cd1—O3—C4 | −109.63 (19) | O2—C1—C2—C6 | 83.7 (3) |
O4i—Cd1—O3—C4 | −2.4 (2) | Cd1—C1—C2—C6 | 92.8 (18) |
O1—Cd1—O3—C4 | −165.21 (19) | C5—C2—C3—C4ii | 69.4 (3) |
O4—Cd1—O3—C4 | 3.77 (17) | C1—C2—C3—C4ii | −54.8 (3) |
C1—Cd1—O3—C4 | −137.98 (19) | C6—C2—C3—C4ii | −172.2 (3) |
N1—Cd1—O4—C4 | −104.13 (18) | Cd1—O3—C4—O4 | −6.8 (3) |
O2—Cd1—O4—C4 | 83.32 (19) | Cd1—O3—C4—C3ii | 174.3 (2) |
O3—Cd1—O4—C4 | −3.68 (16) | Cd1i—O4—C4—O3 | 159.6 (6) |
O4i—Cd1—O4—C4 | 171.1 (2) | Cd1—O4—C4—O3 | 6.4 (3) |
O1—Cd1—O4—C4 | 15.9 (3) | Cd1i—O4—C4—C3ii | −21.5 (9) |
C1—Cd1—O4—C4 | 56.7 (2) | Cd1—O4—C4—C3ii | −174.7 (2) |
N1—Cd1—O4—Cd1i | 84.77 (11) | Cd1i—O4—C4—Cd1 | 153.2 (8) |
O2—Cd1—O4—Cd1i | −87.78 (11) | N1—Cd1—C4—O3 | −89.4 (2) |
O3—Cd1—O4—Cd1i | −174.78 (17) | O2—Cd1—C4—O3 | 78.2 (2) |
O4i—Cd1—O4—Cd1i | 0.0 | O4i—Cd1—C4—O3 | 178.0 (2) |
O1—Cd1—O4—Cd1i | −155.21 (8) | O1—Cd1—C4—O3 | 16.9 (2) |
C1—Cd1—O4—Cd1i | −114.35 (11) | O4—Cd1—C4—O3 | −173.4 (3) |
C4—Cd1—O4—Cd1i | −171.1 (2) | C1—Cd1—C4—O3 | 48.0 (2) |
O2—Cd1—N1—C7 | 96.3 (3) | N1—Cd1—C4—O4 | 83.99 (19) |
O3—Cd1—N1—C7 | −129.5 (2) | O2—Cd1—C4—O4 | −108.44 (18) |
O4i—Cd1—N1—C7 | −1.3 (2) | O3—Cd1—C4—O4 | 173.4 (3) |
O1—Cd1—N1—C7 | 136.2 (2) | O4i—Cd1—C4—O4 | −8.6 (2) |
O4—Cd1—N1—C7 | −73.5 (2) | O1—Cd1—C4—O4 | −169.76 (17) |
C1—Cd1—N1—C7 | 121.7 (2) | C1—Cd1—C4—O4 | −138.60 (18) |
C4—Cd1—N1—C7 | −101.6 (2) | N1—Cd1—C4—C3ii | −169 (2) |
O2—Cd1—N1—C9 | −76.8 (3) | O2—Cd1—C4—C3ii | −1 (2) |
O3—Cd1—N1—C9 | 57.4 (2) | O3—Cd1—C4—C3ii | −80 (2) |
O4i—Cd1—N1—C9 | −174.5 (2) | O4i—Cd1—C4—C3ii | 98 (2) |
O1—Cd1—N1—C9 | −37.0 (2) | O1—Cd1—C4—C3ii | −63 (2) |
O4—Cd1—N1—C9 | 113.3 (2) | O4—Cd1—C4—C3ii | 107 (2) |
C1—Cd1—N1—C9 | −51.5 (3) | C1—Cd1—C4—C3ii | −32 (2) |
C4—Cd1—N1—C9 | 85.3 (2) | C9—N1—C7—N2 | 0.0 (3) |
Cd1—O1—C1—O2 | 3.8 (2) | Cd1—N1—C7—N2 | −174.09 (17) |
Cd1—O1—C1—C2 | −179.3 (2) | C8—N2—C7—N1 | 0.0 (3) |
Cd1—O2—C1—O1 | −4.1 (3) | C10—N2—C7—N1 | 176.2 (2) |
Cd1—O2—C1—C2 | 178.9 (2) | C7—N2—C8—C9 | 0.0 (3) |
N1—Cd1—C1—O1 | 32.60 (19) | C10—N2—C8—C9 | −176.2 (2) |
O2—Cd1—C1—O1 | 176.2 (3) | N2—C8—C9—N1 | 0.0 (4) |
O3—Cd1—C1—O1 | −81.08 (17) | C7—N1—C9—C8 | 0.0 (3) |
O4i—Cd1—C1—O1 | 139.02 (16) | Cd1—N1—C9—C8 | 174.58 (19) |
O4—Cd1—C1—O1 | −126.24 (16) | C7—N2—C10—C11 | −93.5 (3) |
C4—Cd1—C1—O1 | −100.76 (17) | C8—N2—C10—C11 | 82.0 (3) |
N1—Cd1—C1—O2 | −143.55 (15) | N2—C10—C11—C13 | 96.7 (3) |
O3—Cd1—C1—O2 | 102.77 (16) | N2—C10—C11—C12 | −83.8 (3) |
O4i—Cd1—C1—O2 | −37.14 (17) | C13—C11—C12—C12iii | 0.7 (5) |
O1—Cd1—C1—O2 | −176.2 (3) | C10—C11—C12—C12iii | −178.9 (3) |
O4—Cd1—C1—O2 | 57.60 (19) | C12—C11—C13—C13iii | −1.2 (5) |
C4—Cd1—C1—O2 | 83.08 (17) | C10—C11—C13—C13iii | 178.4 (3) |
N1—Cd1—C1—C2 | −153.3 (18) | | |
Symmetry codes: (i) −x+3/2, −y+1/2, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+3, y, −z+5/2. |
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