Poly[(μ5-cis-cyclo­hex-4-ene-1,2-di­carboxyl­ato)(μ3-cis-cyclo­hex-4-ene-1,2-di­carboxyl­ato)dicadmium(II)]

LaDuca, A.R.; LaDuca, R.L.

doi:10.1107/S2414314618009240

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 7| July 2018| x180924

https://doi.org/10.1107/S2414314618009240

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Poly[(μ₅-cis-cyclohex-4-ene-1,2-dicarboxylato)(μ₃-cis-cyclohex-4-ene-1,2-dicarboxylato)dicadmium(II)]

Andrew R. LaDuca ^a ^* and Robert L. LaDuca ^b

^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

Edited by A. J. Lough, University of Toronto, Canada (Received 13 June 2018; accepted 26 June 2018; online 6 July 2018)

The title compound, [Cd₂(C₈H₈O₄)₂]_n, crystallizes in the centrosymmetric monoclinic P2₁/n space group. 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 crystal structure 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 asymmetric unit of the title compound contains two crystallographically distinct Cd atoms (Cd1, Cd2) and two crystallographically distinct chedc ligands (chedc-A, chedc-B) (Fig. 1). 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.

Table 1
Selected geometric parameters (Å, °)

Cd1—O1	2.269 (4)	Cd2—O2	2.346 (3)
Cd1—O2	2.430 (4)	Cd2—O3	2.286 (4)
Cd1—O5	2.173 (4)	Cd2—O3^iv	2.357 (4)
Cd1—O6ⁱ	2.181 (4)	Cd2—O4^iv	2.387 (4)
Cd1—O8ⁱⁱ	2.283 (4)	Cd2—O7	2.231 (4)
Cd2—O2ⁱⁱⁱ	2.555 (4)	Cd2—O8^iv	2.286 (4)

O1—Cd1—O2	55.39 (12)	O3—Cd2—O3^iv	155.99 (11)
O1—Cd1—O8ⁱⁱ	118.49 (14)	O3—Cd2—O4^iv	145.60 (13)
O5—Cd1—O1	133.22 (15)	O3^iv—Cd2—O4^iv	54.92 (13)
O5—Cd1—O2	99.66 (14)	O4^iv—Cd2—O2ⁱⁱⁱ	76.42 (12)
O5—Cd1—O6ⁱ	110.36 (16)	O7—Cd2—O2ⁱⁱⁱ	82.99 (13)
O5—Cd1—O8ⁱⁱ	92.17 (15)	O7—Cd2—O2	92.78 (14)
O6ⁱ—Cd1—O1	99.08 (14)	O7—Cd2—O3	90.21 (14)
O6ⁱ—Cd1—O2	149.76 (13)	O7—Cd2—O3^iv	101.45 (13)
O6ⁱ—Cd1—O8ⁱⁱ	99.42 (14)	O7—Cd2—O4^iv	94.95 (14)
O8ⁱⁱ—Cd1—O2	82.52 (13)	O7—Cd2—O8^iv	162.73 (14)
O2—Cd2—O2ⁱⁱⁱ	155.57 (11)	O8^iv—Cd2—O2ⁱⁱⁱ	79.75 (12)
O2—Cd2—O3^iv	73.13 (13)	O8^iv—Cd2—O2	102.80 (13)
O2—Cd2—O4^iv	128.00 (13)	O8^iv—Cd2—O3	83.70 (14)
O3^iv—Cd2—O2ⁱⁱⁱ	131.30 (12)	O8^iv—Cd2—O3^iv	90.31 (14)
O3—Cd2—O2ⁱⁱⁱ	70.49 (12)	O8^iv—Cd2—O4^iv	81.41 (14)
O3—Cd2—O2	85.52 (13)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The coordination environments within the title compound, showing the square-pyramidal coordination at atom Cd1 and the pentagonal–bipyramidal coordination at atom Cd2. Displacement ellipsoids are drawn at the 50% probability level. All non-H atoms are labeled. Color code: Cd1, violet; Cd2, blue; O, red; C, black; H, pink. The symmetry codes are as listed in Table 1

The 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.

Figure 2
[Cd₂(chedc-A)(chedc-B)]_n ribbon motif parallel to b-axis direction in the crystal structure of the title compound. Color code: Cd1, violet; Cd2, blue; chedc-A ligands, green, chedc-B ligands, purple.

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.

Figure 3
[Cd₂(chedc-A)(chedc-B)]_n coordination polymer layer motif in the title compound, oriented parallel to the ab plane. Color code: Cd1, violet; Cd2, blue.

Figure 4
ABAB stacking pattern of the [Cd₂(chedc-A)(chedc-B)]_n coordination polymer layer motifs to construct the three-dimensional crystal structure of the title compound.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Cd₂(C₈H₈CdO₄)₂]
M_r	561.09
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.8377 (11), 7.0700 (8), 24.268 (3)
β (°)	100.120 (1)
V (Å³)	1661.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.60
Crystal size (mm)	0.25 × 0.16 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.613, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	12875, 3038, 2500
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.07
No. of reflections	3038
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.47, −0.84
Computer programs: COSMO, APEX2 and SAINT (Bruker, 2015), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 )and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1851771

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009240/lh4036sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009240/lh4036Isup2.hkl

checkCIF report

Computing details top

Data collection: COSMO (Bruker, 2015); cell refinement: 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).

Poly[(µ₅-cis-cyclohex-4-ene-1,2-dicarboxylato)(µ₃-cis-cyclohex-4-ene-1,2-dicarboxylato)dicadmium(II)] top

Crystal data top

[Cd₂(C₈H₈CdO₄)₂]	F(000) = 1088
M_r = 561.09	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	3038 independent reflections
Radiation source: sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.4 pixels mm^-1	θ_max = 25.3°, θ_min = 1.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −8→8
T_min = 0.613, T_max = 0.745	l = −29→29
12875 measured reflections

Refinement top

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(F_o²) + (0.0444P)² + 3.7886P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3038 reflections	Δρ_max = 1.47 e Å⁻³
235 parameters	Δρ_min = −0.83 e Å⁻³
0 restraints

Special details top

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 U_iso = 1.2U_eq.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O3^iv	2.357 (4)	C6—H6B	0.9900
Cd2—O4^iv	2.387 (4)	C6—C7	1.534 (8)
Cd2—O7	2.231 (4)	C7—H7	1.0000
Cd2—O8^iv	2.286 (4)	C7—C8	1.515 (7)
O1—C1	1.239 (6)	C8—Cd2ⁱⁱⁱ	2.739 (5)
O2—Cd2^iv	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—Cd1^v	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—Cd1^vi	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—O3^iv	73.13 (13)	C5—C6—C7	110.6 (5)
O2—Cd2—O4^iv	128.00 (13)	H6A—C6—H6B	108.1
O3^iv—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—O3^iv	155.99 (11)	C6—C7—C2	112.2 (4)
O3—Cd2—O4^iv	145.60 (13)	C6—C7—H7	105.4
O3^iv—Cd2—O4^iv	54.92 (13)	C8—C7—C2	115.0 (4)
O4^iv—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—O3^iv	101.45 (13)	O4—C8—Cd2ⁱⁱⁱ	60.6 (3)
O7—Cd2—O4^iv	94.95 (14)	O4—C8—O3	119.8 (5)
O7—Cd2—O8^iv	162.73 (14)	O4—C8—C7	120.0 (5)
O8^iv—Cd2—O2ⁱⁱⁱ	79.75 (12)	C7—C8—Cd2ⁱⁱⁱ	178.8 (4)
O8^iv—Cd2—O2	102.80 (13)	O5—C9—O6	120.1 (5)
O8^iv—Cd2—O3	83.70 (14)	O5—C9—C10	118.0 (5)
O8^iv—Cd2—O3^iv	90.31 (14)	O6—C9—C10	121.9 (5)
O8^iv—Cd2—O4^iv	81.41 (14)	C9—C10—H10	107.1
C1—O1—Cd1	97.3 (3)	C9—C10—C11	110.9 (5)
Cd1—O2—Cd2^iv	92.24 (12)	C9—C10—C15	110.9 (4)
Cd2—O2—Cd1	128.66 (15)	C11—C10—H10	107.1
Cd2—O2—Cd2^iv	94.67 (12)	C11—C10—C15	113.5 (4)
C1—O2—Cd1	88.2 (3)	C15—C10—H10	107.1
C1—O2—Cd2^iv	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—Cd1^v	130.8 (3)	C13—C12—C11	123.8 (5)
C16—O7—Cd2	144.7 (4)	C13—C12—H12	118.1
Cd1^vi—O8—Cd2ⁱⁱⁱ	103.74 (14)	C12—C13—H13	117.9
C16—O8—Cd1^vi	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)
Cd1^v—O6—C9—O5	−136.2 (4)	C2—C7—C8—O3	−17.8 (7)
Cd1^v—O6—C9—C10	45.9 (7)	C2—C7—C8—O4	166.3 (5)
Cd1^vi—O8—C16—O7	−161.3 (4)	C3—C2—C7—C6	−60.2 (6)
Cd1^vi—O8—C16—C15	20.7 (7)	C3—C2—C7—C8	169.8 (5)
Cd2^iv—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)
Cd2^iv—O2—C1—O1	−93.7 (5)	C5—C6—C7—C8	−179.9 (5)
Cd2^iv—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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