metal-organic compounds
Poly[(μ5-cis-cyclohex-4-ene-1,2-dicarboxylato)(μ3-cis-cyclohex-4-ene-1,2-dicarboxylato)dicadmium(II)]
aDepartment of Chemistry, Grand Valley State University, Allendale, MI 49401, USA, and bE-35A Holmes Hall, Michigan State University, 919 E. Shaw Lane, East Lansing, MI 48825, USA
*Correspondence e-mail: laduca@msu.edu
The title compound, [Cd2(C8H8O4)2]n, crystallizes in the centrosymmetric monoclinic P21/n Via cis-cyclohex-4-ene-1,2-dicarboxylate ligands in two different binding modes, square pyramidally and pentagonal bipyramidally coordinated Cd atoms are connected into coordination polymer layer motifs oriented parallel to the ab plane. These layered motifs are aggregated into the three-dimensional supramolecular of the title compound by means of crystal packing forces.
Keywords: cadmium; coordination polymer; layer; crystal structure.
CCDC reference: 1851771
Structure description
The dipodal tethering ligand propane-1,3-diylbis(piperidine-4,1-diyl)bis(pyridin-4-ylmethanone (4-pbpp) has recently proven useful in preparing metal 1,3-thiophenedicarboxylate coordination polymers with intriguing and diverse interpenetrated topologies (Sample & LaDuca, 2016). The title compound was prepared during synthetic attempts to prepare cadmium coordination polymers containing both cis-cyclohex-4-ene-1,2-dicarboxylate (chedc) and 4-pbpp ligands. There have only been two reports of cadmium chedc coordination polymers with dipyridyl-type coligands to the best of our knowledge. One possessed 1,10-phenanthroline capping coligands (Xu et al., 2010), and the other 4,4′-bipyridine tethering coligands (Cui et al., 2013).
The ). The crystallographic distinction within the chedc ligands arises from different binding modes. The Cd1 atom displays a distorted square-pyramidal coordination environment while the Cd2 atom displays a pentagonal–bipyramidal coordination geometry. Bond lengths and angles within the coordination environments are listed in Table 1.
of the title compound contains two crystallographically distinct Cd atoms (Cd1, Cd2) and two crystallographically distinct chedc ligands (chedc-A, chedc-B) (Fig. 1The Cd atoms and chedc ligands construct [Cd2(chedc-A)(chedc-B)]n ribbon motifs (Fig. 2) that are oriented parallel to the b-axis direction. Within the cores of the ribbon motifs are embedded [Cd(μ-O)]n chains with a Cd2⋯Cd2 internuclear distance of 3.606 (2) Å. The bridging oxygen atoms are the O3 atoms within the chedc-A ligands. The Cd1 atoms at the periphery of the ribbon motifs are anchored to the Cd1 atoms at the cores of the ribbon motifs by both chedc-A and chedc-B ligands.
The ribbon motifs are connected into [Cd2(chedc-A)(chedc-B)]n coordination polymer layers (Fig. 3) that are arranged parallel to the ab plane. The inter-ribbon connection is provided by O6 atoms belonging to the chedc-B ligands. Adjacent [Cd2(chedc-A)(chedc-B)]n coordination polymer layer motifs stack in an ABAB pattern along the c-axis direction, related by crystallographic glide planes (Fig. 4). Crystal packing forces provide the impetus for the layer aggregation.
Synthesis and crystallization
Cd(NO3)2.4H2O (115 mg, 0.37 mmol), cis-cyclohex-4-ene-1,2-dicarboxylic acid (63 mg, 0.37 mol), propane-1,3-diylbis(piperidine-4,1-diyl)bis(pyridin-4-ylmethanone (153 mg, 0.37 mol) and 0.75 ml of a 1.0 M NaOH solution were placed into 10 ml of distilled H2O in a Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 393 K for 48 h, and then cooled slowly to 278 K. Colorless block-shaped crystals of the title compound were isolated after washing with distilled water and acetone, and drying in air.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1851771
https://doi.org/10.1107/S2414314618009240/lh4036sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009240/lh4036Isup2.hkl
Data collection: COSMO (Bruker, 2015); cell
APEX2 (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[Cd2(C8H8CdO4)2] | F(000) = 1088 |
Mr = 561.09 | Dx = 2.243 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8377 (11) Å | Cell parameters from 5975 reflections |
b = 7.0700 (8) Å | θ = 2.4–25.3° |
c = 24.268 (3) Å | µ = 2.60 mm−1 |
β = 100.120 (1)° | T = 173 K |
V = 1661.6 (3) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.16 × 0.15 mm |
Bruker APEXII CCD diffractometer | 3038 independent reflections |
Radiation source: sealed tube | 2500 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.4 pixels mm-1 | θmax = 25.3°, θmin = 1.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −8→8 |
Tmin = 0.613, Tmax = 0.745 | l = −29→29 |
12875 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0444P)2 + 3.7886P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3038 reflections | Δρmax = 1.47 e Å−3 |
235 parameters | Δρmin = −0.83 e Å−3 |
0 restraints |
Experimental. Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using omega and phi scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in OLEX2. |
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. Hydrogen atoms bound to C were placed in calculated positions with a riding model with Uiso = 1.2Ueq. |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.39348 (4) | 0.94716 (6) | 0.74436 (2) | 0.02049 (14) | |
Cd2 | 0.76663 (4) | 0.61706 (5) | 0.76431 (2) | 0.01681 (13) | |
O1 | 0.3949 (4) | 0.8233 (6) | 0.65823 (15) | 0.0237 (9) | |
O2 | 0.5952 (4) | 0.8119 (5) | 0.71409 (14) | 0.0194 (8) | |
O3 | 0.7149 (4) | 0.4133 (5) | 0.69043 (16) | 0.0224 (9) | |
O4 | 0.5747 (4) | 0.1907 (5) | 0.65224 (16) | 0.0300 (10) | |
O5 | 0.4160 (4) | 0.8240 (6) | 0.82752 (17) | 0.0317 (10) | |
O6 | 0.2972 (4) | 0.6105 (5) | 0.77425 (16) | 0.0244 (9) | |
O7 | 0.6164 (4) | 0.4686 (5) | 0.80826 (16) | 0.0233 (9) | |
O8 | 0.5445 (4) | 0.1854 (5) | 0.77511 (16) | 0.0230 (8) | |
C1 | 0.5190 (6) | 0.7816 (8) | 0.6655 (2) | 0.0199 (12) | |
C2 | 0.5848 (5) | 0.7039 (8) | 0.6184 (2) | 0.0180 (11) | |
H2 | 0.6872 | 0.7182 | 0.6291 | 0.022* | |
C3 | 0.5376 (6) | 0.8158 (8) | 0.5642 (2) | 0.0213 (12) | |
H3A | 0.5285 | 0.9507 | 0.5738 | 0.026* | |
H3B | 0.6100 | 0.8068 | 0.5407 | 0.026* | |
C4 | 0.4048 (6) | 0.7508 (8) | 0.5308 (2) | 0.0270 (13) | |
H4 | 0.3630 | 0.8274 | 0.5004 | 0.032* | |
C5 | 0.3402 (6) | 0.5921 (8) | 0.5409 (2) | 0.0280 (14) | |
H5 | 0.2540 | 0.5634 | 0.5180 | 0.034* | |
C6 | 0.3978 (6) | 0.4568 (8) | 0.5867 (3) | 0.0275 (14) | |
H6A | 0.3835 | 0.3253 | 0.5728 | 0.033* | |
H6B | 0.3483 | 0.4724 | 0.6185 | 0.033* | |
C7 | 0.5525 (6) | 0.4926 (7) | 0.6064 (2) | 0.0204 (12) | |
H7 | 0.5974 | 0.4602 | 0.5737 | 0.025* | |
C8 | 0.6151 (6) | 0.3584 (7) | 0.6527 (2) | 0.0203 (12) | |
C9 | 0.3695 (6) | 0.6591 (8) | 0.8208 (2) | 0.0219 (12) | |
C10 | 0.4064 (6) | 0.5202 (7) | 0.8687 (2) | 0.0191 (12) | |
H10 | 0.3235 | 0.5082 | 0.8871 | 0.023* | |
C11 | 0.5243 (6) | 0.5972 (8) | 0.9129 (2) | 0.0240 (13) | |
H11A | 0.5956 | 0.6531 | 0.8938 | 0.029* | |
H11B | 0.4879 | 0.6994 | 0.9341 | 0.029* | |
C12 | 0.5896 (6) | 0.4506 (9) | 0.9528 (2) | 0.0270 (13) | |
H12 | 0.6480 | 0.4913 | 0.9861 | 0.032* | |
C13 | 0.5711 (6) | 0.2671 (9) | 0.9448 (2) | 0.0302 (14) | |
H13 | 0.6184 | 0.1837 | 0.9724 | 0.036* | |
C14 | 0.4806 (6) | 0.1819 (8) | 0.8949 (2) | 0.0265 (13) | |
H14A | 0.3970 | 0.1294 | 0.9068 | 0.032* | |
H14B | 0.5305 | 0.0757 | 0.8809 | 0.032* | |
C15 | 0.4357 (5) | 0.3224 (7) | 0.8468 (2) | 0.0178 (11) | |
H15 | 0.3470 | 0.2743 | 0.8247 | 0.021* | |
C16 | 0.5398 (5) | 0.3300 (8) | 0.8071 (2) | 0.0180 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0174 (2) | 0.0198 (2) | 0.0242 (2) | 0.00097 (16) | 0.00357 (17) | −0.00307 (16) |
Cd2 | 0.0151 (2) | 0.0146 (2) | 0.0210 (2) | −0.00088 (14) | 0.00367 (16) | 0.00038 (15) |
O1 | 0.018 (2) | 0.030 (2) | 0.022 (2) | 0.0032 (17) | 0.0035 (16) | −0.0028 (17) |
O2 | 0.0166 (19) | 0.021 (2) | 0.0191 (19) | 0.0036 (16) | −0.0009 (15) | −0.0020 (16) |
O3 | 0.023 (2) | 0.022 (2) | 0.022 (2) | 0.0041 (16) | 0.0017 (17) | −0.0045 (16) |
O4 | 0.043 (3) | 0.012 (2) | 0.031 (2) | −0.0039 (18) | −0.0055 (19) | −0.0007 (18) |
O5 | 0.046 (3) | 0.019 (2) | 0.029 (2) | −0.0047 (19) | 0.003 (2) | −0.0005 (18) |
O6 | 0.022 (2) | 0.029 (2) | 0.021 (2) | −0.0074 (17) | 0.0020 (17) | 0.0037 (17) |
O7 | 0.024 (2) | 0.021 (2) | 0.027 (2) | −0.0083 (17) | 0.0091 (17) | −0.0044 (17) |
O8 | 0.026 (2) | 0.018 (2) | 0.028 (2) | 0.0025 (17) | 0.0099 (17) | −0.0079 (17) |
C1 | 0.023 (3) | 0.015 (3) | 0.021 (3) | −0.003 (2) | 0.004 (2) | 0.003 (2) |
C2 | 0.015 (3) | 0.021 (3) | 0.018 (3) | 0.002 (2) | 0.002 (2) | 0.000 (2) |
C3 | 0.027 (3) | 0.015 (3) | 0.023 (3) | 0.004 (2) | 0.008 (2) | 0.004 (2) |
C4 | 0.033 (3) | 0.024 (3) | 0.021 (3) | 0.008 (3) | −0.004 (3) | 0.001 (2) |
C5 | 0.023 (3) | 0.032 (4) | 0.027 (3) | 0.003 (3) | −0.001 (3) | −0.007 (3) |
C6 | 0.028 (3) | 0.020 (3) | 0.029 (3) | −0.003 (2) | −0.010 (3) | −0.001 (3) |
C7 | 0.025 (3) | 0.015 (3) | 0.020 (3) | −0.001 (2) | 0.002 (2) | −0.003 (2) |
C8 | 0.023 (3) | 0.018 (3) | 0.021 (3) | 0.008 (2) | 0.006 (2) | −0.003 (2) |
C9 | 0.020 (3) | 0.022 (3) | 0.028 (3) | 0.001 (2) | 0.015 (2) | −0.001 (2) |
C10 | 0.019 (3) | 0.017 (3) | 0.023 (3) | −0.002 (2) | 0.008 (2) | −0.003 (2) |
C11 | 0.022 (3) | 0.026 (3) | 0.022 (3) | −0.003 (2) | 0.001 (2) | −0.006 (2) |
C12 | 0.022 (3) | 0.038 (4) | 0.020 (3) | 0.001 (3) | 0.001 (2) | −0.006 (3) |
C13 | 0.031 (3) | 0.032 (4) | 0.027 (3) | 0.008 (3) | 0.000 (3) | 0.005 (3) |
C14 | 0.032 (3) | 0.022 (3) | 0.028 (3) | −0.002 (3) | 0.011 (3) | 0.001 (3) |
C15 | 0.016 (3) | 0.015 (3) | 0.024 (3) | 0.000 (2) | 0.006 (2) | −0.004 (2) |
C16 | 0.012 (3) | 0.020 (3) | 0.020 (3) | 0.000 (2) | −0.001 (2) | 0.001 (2) |
Cd1—O1 | 2.269 (4) | C3—H3A | 0.9900 |
Cd1—O2 | 2.430 (4) | C3—H3B | 0.9900 |
Cd1—O5 | 2.173 (4) | C3—C4 | 1.483 (8) |
Cd1—O6i | 2.181 (4) | C4—H4 | 0.9500 |
Cd1—O8ii | 2.283 (4) | C4—C5 | 1.332 (8) |
Cd2—O2iii | 2.555 (4) | C5—H5 | 0.9500 |
Cd2—O2 | 2.346 (3) | C5—C6 | 1.500 (8) |
Cd2—O3 | 2.286 (4) | C6—H6A | 0.9900 |
Cd2—O3iv | 2.357 (4) | C6—H6B | 0.9900 |
Cd2—O4iv | 2.387 (4) | C6—C7 | 1.534 (8) |
Cd2—O7 | 2.231 (4) | C7—H7 | 1.0000 |
Cd2—O8iv | 2.286 (4) | C7—C8 | 1.515 (7) |
O1—C1 | 1.239 (6) | C8—Cd2iii | 2.739 (5) |
O2—Cd2iv | 2.554 (4) | C9—C10 | 1.517 (8) |
O2—C1 | 1.300 (6) | C10—H10 | 1.0000 |
O3—Cd2iii | 2.357 (4) | C10—C11 | 1.534 (7) |
O3—C8 | 1.280 (7) | C10—C15 | 1.542 (7) |
O4—Cd2iii | 2.387 (4) | C11—H11A | 0.9900 |
O4—C8 | 1.250 (7) | C11—H11B | 0.9900 |
O5—C9 | 1.253 (7) | C11—C12 | 1.486 (8) |
O6—Cd1v | 2.181 (4) | C12—H12 | 0.9500 |
O6—C9 | 1.271 (7) | C12—C13 | 1.320 (8) |
O7—C16 | 1.233 (6) | C13—H13 | 0.9500 |
O8—Cd1vi | 2.283 (4) | C13—C14 | 1.497 (8) |
O8—Cd2iii | 2.286 (4) | C14—H14A | 0.9900 |
O8—C16 | 1.290 (6) | C14—H14B | 0.9900 |
C1—C2 | 1.512 (7) | C14—C15 | 1.538 (8) |
C2—H2 | 1.0000 | C15—H15 | 1.0000 |
C2—C3 | 1.535 (7) | C15—C16 | 1.524 (7) |
C2—C7 | 1.545 (7) | ||
O1—Cd1—O2 | 55.39 (12) | C4—C3—C2 | 114.4 (5) |
O1—Cd1—O8ii | 118.49 (14) | C4—C3—H3A | 108.7 |
O5—Cd1—O1 | 133.22 (15) | C4—C3—H3B | 108.7 |
O5—Cd1—O2 | 99.66 (14) | C3—C4—H4 | 117.8 |
O5—Cd1—O6i | 110.36 (16) | C5—C4—C3 | 124.3 (5) |
O5—Cd1—O8ii | 92.17 (15) | C5—C4—H4 | 117.8 |
O6i—Cd1—O1 | 99.08 (14) | C4—C5—H5 | 118.6 |
O6i—Cd1—O2 | 149.76 (13) | C4—C5—C6 | 122.8 (5) |
O6i—Cd1—O8ii | 99.42 (14) | C6—C5—H5 | 118.6 |
O8ii—Cd1—O2 | 82.52 (13) | C5—C6—H6A | 109.5 |
O2—Cd2—O2iii | 155.57 (11) | C5—C6—H6B | 109.5 |
O2—Cd2—O3iv | 73.13 (13) | C5—C6—C7 | 110.6 (5) |
O2—Cd2—O4iv | 128.00 (13) | H6A—C6—H6B | 108.1 |
O3iv—Cd2—O2iii | 131.30 (12) | C7—C6—H6A | 109.5 |
O3—Cd2—O2iii | 70.49 (12) | C7—C6—H6B | 109.5 |
O3—Cd2—O2 | 85.52 (13) | C2—C7—H7 | 105.4 |
O3—Cd2—O3iv | 155.99 (11) | C6—C7—C2 | 112.2 (4) |
O3—Cd2—O4iv | 145.60 (13) | C6—C7—H7 | 105.4 |
O3iv—Cd2—O4iv | 54.92 (13) | C8—C7—C2 | 115.0 (4) |
O4iv—Cd2—O2iii | 76.42 (12) | C8—C7—C6 | 112.3 (5) |
O7—Cd2—O2iii | 82.99 (13) | C8—C7—H7 | 105.4 |
O7—Cd2—O2 | 92.78 (14) | O3—C8—Cd2iii | 59.3 (3) |
O7—Cd2—O3 | 90.21 (14) | O3—C8—C7 | 120.1 (5) |
O7—Cd2—O3iv | 101.45 (13) | O4—C8—Cd2iii | 60.6 (3) |
O7—Cd2—O4iv | 94.95 (14) | O4—C8—O3 | 119.8 (5) |
O7—Cd2—O8iv | 162.73 (14) | O4—C8—C7 | 120.0 (5) |
O8iv—Cd2—O2iii | 79.75 (12) | C7—C8—Cd2iii | 178.8 (4) |
O8iv—Cd2—O2 | 102.80 (13) | O5—C9—O6 | 120.1 (5) |
O8iv—Cd2—O3 | 83.70 (14) | O5—C9—C10 | 118.0 (5) |
O8iv—Cd2—O3iv | 90.31 (14) | O6—C9—C10 | 121.9 (5) |
O8iv—Cd2—O4iv | 81.41 (14) | C9—C10—H10 | 107.1 |
C1—O1—Cd1 | 97.3 (3) | C9—C10—C11 | 110.9 (5) |
Cd1—O2—Cd2iv | 92.24 (12) | C9—C10—C15 | 110.9 (4) |
Cd2—O2—Cd1 | 128.66 (15) | C11—C10—H10 | 107.1 |
Cd2—O2—Cd2iv | 94.67 (12) | C11—C10—C15 | 113.5 (4) |
C1—O2—Cd1 | 88.2 (3) | C15—C10—H10 | 107.1 |
C1—O2—Cd2iv | 121.8 (3) | C10—C11—H11A | 108.9 |
C1—O2—Cd2 | 128.5 (3) | C10—C11—H11B | 108.9 |
Cd2—O3—Cd2iii | 101.89 (14) | H11A—C11—H11B | 107.7 |
C8—O3—Cd2iii | 92.9 (3) | C12—C11—C10 | 113.3 (5) |
C8—O3—Cd2 | 142.2 (3) | C12—C11—H11A | 108.9 |
C8—O4—Cd2iii | 92.3 (3) | C12—C11—H11B | 108.9 |
C9—O5—Cd1 | 106.0 (4) | C11—C12—H12 | 118.1 |
C9—O6—Cd1v | 130.8 (3) | C13—C12—C11 | 123.8 (5) |
C16—O7—Cd2 | 144.7 (4) | C13—C12—H12 | 118.1 |
Cd1vi—O8—Cd2iii | 103.74 (14) | C12—C13—H13 | 117.9 |
C16—O8—Cd1vi | 133.8 (3) | C12—C13—C14 | 124.2 (5) |
C16—O8—Cd2iii | 122.5 (3) | C14—C13—H13 | 117.9 |
O1—C1—Cd1 | 55.8 (3) | C13—C14—H14A | 108.8 |
O1—C1—O2 | 119.1 (5) | C13—C14—H14B | 108.8 |
O1—C1—C2 | 121.5 (5) | C13—C14—C15 | 113.9 (5) |
O2—C1—Cd1 | 63.3 (3) | H14A—C14—H14B | 107.7 |
O2—C1—C2 | 119.4 (5) | C15—C14—H14A | 108.8 |
C2—C1—Cd1 | 175.1 (4) | C15—C14—H14B | 108.8 |
C1—C2—H2 | 108.1 | C10—C15—H15 | 107.1 |
C1—C2—C3 | 110.8 (4) | C14—C15—C10 | 111.7 (4) |
C1—C2—C7 | 113.1 (4) | C14—C15—H15 | 107.1 |
C3—C2—H2 | 108.1 | C16—C15—C10 | 111.9 (4) |
C3—C2—C7 | 108.4 (4) | C16—C15—C14 | 111.6 (4) |
C7—C2—H2 | 108.1 | C16—C15—H15 | 107.1 |
C2—C3—H3A | 108.7 | O7—C16—O8 | 123.8 (5) |
C2—C3—H3B | 108.7 | O7—C16—C15 | 119.3 (5) |
H3A—C3—H3B | 107.6 | O8—C16—C15 | 116.8 (5) |
Cd1—O1—C1—O2 | 2.4 (5) | O6—C9—C10—C11 | 164.5 (5) |
Cd1—O1—C1—C2 | −175.1 (4) | O6—C9—C10—C15 | 37.4 (7) |
Cd1—O2—C1—O1 | −2.2 (5) | C1—C2—C3—C4 | −85.0 (6) |
Cd1—O2—C1—C2 | 175.3 (4) | C1—C2—C7—C6 | 63.1 (6) |
Cd1—O5—C9—O6 | −14.5 (6) | C1—C2—C7—C8 | −67.0 (6) |
Cd1—O5—C9—C10 | 163.5 (4) | C2—C3—C4—C5 | −10.2 (8) |
Cd1v—O6—C9—O5 | −136.2 (4) | C2—C7—C8—O3 | −17.8 (7) |
Cd1v—O6—C9—C10 | 45.9 (7) | C2—C7—C8—O4 | 166.3 (5) |
Cd1vi—O8—C16—O7 | −161.3 (4) | C3—C2—C7—C6 | −60.2 (6) |
Cd1vi—O8—C16—C15 | 20.7 (7) | C3—C2—C7—C8 | 169.8 (5) |
Cd2iv—O2—C1—Cd1 | −91.5 (3) | C3—C4—C5—C6 | −1.9 (9) |
Cd2—O2—C1—Cd1 | 140.6 (4) | C4—C5—C6—C7 | −17.5 (8) |
Cd2—O2—C1—O1 | 138.4 (4) | C5—C6—C7—C2 | 48.7 (6) |
Cd2iv—O2—C1—O1 | −93.7 (5) | C5—C6—C7—C8 | −179.9 (5) |
Cd2iv—O2—C1—C2 | 83.8 (5) | C6—C7—C8—O3 | −147.8 (5) |
Cd2—O2—C1—C2 | −44.1 (6) | C6—C7—C8—O4 | 36.3 (7) |
Cd2—O3—C8—Cd2iii | −113.7 (5) | C7—C2—C3—C4 | 39.7 (6) |
Cd2iii—O3—C8—O4 | −2.9 (5) | C9—C10—C11—C12 | −164.9 (5) |
Cd2—O3—C8—O4 | −116.6 (6) | C9—C10—C15—C14 | 177.1 (4) |
Cd2—O3—C8—C7 | 67.4 (8) | C9—C10—C15—C16 | 51.2 (6) |
Cd2iii—O3—C8—C7 | −178.9 (4) | C10—C11—C12—C13 | 14.2 (8) |
Cd2iii—O4—C8—O3 | 2.9 (5) | C10—C15—C16—O7 | 19.9 (7) |
Cd2iii—O4—C8—C7 | 178.9 (4) | C10—C15—C16—O8 | −162.0 (4) |
Cd2—O7—C16—O8 | 13.4 (10) | C11—C10—C15—C14 | 51.5 (6) |
Cd2—O7—C16—C15 | −168.7 (4) | C11—C10—C15—C16 | −74.4 (6) |
Cd2iii—O8—C16—O7 | 19.6 (7) | C11—C12—C13—C14 | −1.0 (10) |
Cd2iii—O8—C16—C15 | −158.4 (3) | C12—C13—C14—C15 | 13.3 (8) |
O1—C1—C2—C3 | 44.2 (7) | C13—C14—C15—C10 | −37.7 (7) |
O1—C1—C2—C7 | −77.8 (6) | C13—C14—C15—C16 | 88.4 (6) |
O2—C1—C2—C3 | −133.3 (5) | C14—C15—C16—O7 | −106.0 (6) |
O2—C1—C2—C7 | 104.8 (6) | C14—C15—C16—O8 | 72.1 (6) |
O5—C9—C10—C11 | −13.4 (7) | C15—C10—C11—C12 | −39.4 (7) |
O5—C9—C10—C15 | −140.4 (5) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+3/2, y+1/2, −z+3/2; (v) −x+1/2, y−1/2, −z+3/2; (vi) x, y−1, z. |
Funding information
We thank the Honors College of Michigan State University for funding this work.
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