Poly[di­aqua­[μ4-2-(carboxyl­atometh­oxy)benzoato][μ2-2-(carboxyl­atometh­oxy)benzoato]dicad­mium(II)]

Gaskin, G.J.; LaDuca, R.L.

doi:10.1107/S2414314619009532

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 7| July 2019| x190953

https://doi.org/10.1107/S2414314619009532

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Poly[diaqua[μ₄-2-(carboxylatomethoxy)benzoato][μ₂-2-(carboxylatomethoxy)benzoato]dicadmium(II)]

Gabrielle J. Gaskin ^a and Robert L. LaDuca ^a ^*

^aE-35 Holmes Hall, Michigan State University, Lyman Briggs College, 919 E. Shaw Lane, East Lansing, MI 48825
^*Correspondence e-mail: laduca@msu.edu

Edited by A. J. Lough, University of Toronto, Canada (Received 25 June 2019; accepted 2 July 2019; online 9 July 2019)

In the title compound, [Cd₂(C₉H₆O₅)₂(H₂O)₂]_n, the crystallographically distinct Cd^II cations are coordinated in pentagonal–bipyramidal and octahedral fashions. The 2-(carboxymethoxy)benzoate (cmb) ligands connect the Cd atoms into [Cd₂(cmb)₂(H₂O)₂)]_n coordination polymer ribbons that are oriented along the a-axis direction. Supramolecular layers are formed parallel to (01 $[\overline{1}]$ ) by O—H⋯O hydrogen bonding between the ribbons. The supramolecular three-dimensional crystal structure of the title compound is then constructed by π–π stacking interactions with a centroid–centroid distance of 3.622 (2) Å between cmb ligands in adjacent layer motifs.

Keywords: crystal structure; cadmium; 2-(carboxymethoxy)benzoate; coordination polymer; hydrogen bonding; π–π interactions.

CCDC reference: 1937965

Structure description

The title compound was isolated during an exploratory synthetic effort aiming to produce a cadmium coordination polymer containing both 2-(carboxymethoxy)benzoate (cmb) and 4-pyridylisonicotinamide (4-pina) ligands. Cadmium succinate coordination polymers containing the 4-pina ligands and their geometric isomers have shown intriguing self-penetrated or interpenetrated topologies (Uebler et al., 2013 ).

The asymmetric unit of the title compound contains two crystallographically distinct Cd atoms (Cd1, Cd2), two crystallographically distinct cmb ligands (cmb-A, cmb-B) and two bound water molecules. There are no co-crystallized species in the title compound. The Cd1 atoms display a {CdO₇} distorted pentagonal–bipyramidal geometry with one bound water molecule in an axial position and another bound water molecule in the equatorial plane. A cmb-A ligand provides three O atom donors, two in equatorial positions and one in the other axial position. A chelating carboxylate group from a cmb-B ligand occupies the final two coordination positions at Cd1. The Cd2 atoms display a {CdO₆} distorted coordination octahedron. The nominal axial positions are taken up by single carboxylate O atom donors from two different cmb-B ligands. The nominal equatorial plane at Cd2 contains a chelating carboxylate group from a third cmb-B ligand, a single carboxylate O atom donor from a fourth cmb-B ligand, and a single carboxylate O atom donor from a cmb-A ligand. A displacement ellipsoid plot of the ligand set and coordination environments is shown in Fig. 1.

Figure 1
The coordination environments of the title compound, showing the pentagonal bipyramidal coordination at the Cd1 atom and the octahedral coordination at the Cd2 atom. Complete cmb-A and cmb-B ligands are shown. Displacement ellipsoids are drawn at the 50% probability level. Most H atoms have been omitted for clarity. Color code: Cd1, light violet; Cd2, deep purple, N, blue; O, red; C, black. H-atom positions are shown as sticks.

The cmb-A ligands have an exobidentate μ₂-κ⁴-O:O′,O′′,O′′′ bridging mode, binding to one Cd1 atom with three donor O atoms, and binding to one Cd2 atom with only one O donor atom (Fig. 2). The cmb-A ether O atoms bind to Cd1. The cmb-B ligands have an exotetradentate μ₄-κ⁵-O,O′:O′:O′′,O′′′:O′′′ bringing mode, binding to one Cd1 atom with a chelating carboxylate group, binding to two Cd2 atoms with single carboxylate O atom donors, and binding to a third Cd2 through a chelating carboxylate group (Fig. 3). The ether O atoms of the cmb-B ligands do not bind to either Cd1 or Cd2.

Figure 2
Exobidentate bridging mode of the cmb-A ligand.

Figure 3
Exobidentate bridging mode of the cmb-B ligand.

The Cd2 atoms and cmb-B ligands form a [Cd(cmb-B)]_n coordination polymer chain motif, in which spiro-fused {Cd₂O₂) rhomboid units construct the center of the chain (Fig. 4). The through-space Cd⋯Cd distance across the rhomboid units measures 3.632 (2) Å. The chain submotifs are oriented parallel to the a axis. These are decorated on their periphery by [Cd(cmb-A)(H₂O)₂] coordination fragments, resulting in one-dimensional [Cd₂(cmb)₂(H₂O)₂)]_n coordination polymer ribbons (Fig. 5).

Figure 4
Inner [Cd(cmb)]_n coordination polymer chain in the title compound, oriented parallel to the a axis. Spiro-fused {Cd₂O₂} rhomboid units make up the center of the chain, bracketed by cmb-B ligands

Figure 5
[Cd₂(cmb)₂(H₂O)₂)]_n coordination polymer ribbon in the title compound, oriented parallel to the a axis. The inner chain sub-motif is shown in purple.

Supramolecular interactions

Adjacent [Cd₂(cmb)₂(H₂O)₂)]_n coordination polymer ribbons interact by means of O–H⋯O hydrogen-bonding interactions (Table 1) between the bound water molecules and unligated cmb-A carboxylate O atoms, thereby constructing supramolecular layer motifs coincident with (01 $[\overline{1}]$ ) (Fig. 6). The O⋯O distance measures 2.788 (1) Å. In turn, the two-dimensional supramolecular layer motifs form the three-dimensional crystal structure of the title compound (Fig. 7) by means of π–π stacking mechanisms involving the aromatic rings of the cmb-A ligands on the ribbon periphery [centroid–centroid distance = 3.622 (2) Å]. The stacking occurs along the c-axis direction, in an AAA pattern.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11A⋯O9ⁱ	0.88	2.03	2.873 (3)	162
O11—H11B⋯O1ⁱ	0.88	1.91	2.782 (3)	178
O12—H12A⋯O2ⁱⁱ	0.90	1.94	2.788 (3)	158
O12—H12B⋯O2ⁱ	0.90	1.86	2.756 (3)	174
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z.

Figure 6
Supramolecular layer in the title compound, oriented parallel to (01 $[\overline{1}]$ ). O—H⋯O hydrogen-bonding interactions (Table 1

) between neighboring ribbons are shown as dashed lines.

Figure 7
AAA pattern stacking of supramolecular layer motifs along the c-axis direction in the title compound, mediated by interlayer π–π stacking interactions, which are shown as dashed lines. Ring centroids of the cmb ligands are shown as teal spheres.

Synthesis and crystallization

Cd(NO₃)₂^.4H₂O (115 mg, 0.37 mmol), 2-(carboxymethoxy)benzoic acid (73 mg, 0.37 mmol), 4-pyridylisonicotinamide (79 mg, 0.37 mmol) and 0.75 ml of a 1.0 M NaOH solution were placed into 10 ml distilled H₂O in a Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 393 K for 2 d, and then cooled slowly to 273 K. Colorless crystals of the title complex (75 mg, 62% yield based on Cd) 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(C₉H₆O₅)₂(H₂O)₂]
M_r	649.11
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	6.3966 (9), 11.7504 (16), 13.3579 (19)
α, β, γ (°)	104.407 (1), 96.978 (1), 93.267 (1)
V (Å³)	961.3 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.28
Crystal size (mm)	0.19 × 0.18 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014/5)
T_min, T_max	0.663, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	10335, 3536, 3172
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.057, 1.06
No. of reflections	3536
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.46
Computer programs: COSMO (Bruker, 2009 ), SAINT (Bruker, 2013 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1937965

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619009532/lh4046sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619009532/lh4046Isup3.hkl

checkCIF report

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[diaqua[µ₄-2-(carboxylatomethoxy)benzoato][µ₂-2-(carboxylatomethoxy)benzoato]dicadmium(II)] top

Crystal data top

[Cd₂(C₉H₆O₅)₂(H₂O)₂]	Z = 2
M_r = 649.11	F(000) = 632
Triclinic, P1	D_x = 2.243 Mg m⁻³
a = 6.3966 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7504 (16) Å	Cell parameters from 7284 reflections
c = 13.3579 (19) Å	θ = 3.2–25.4°
α = 104.407 (1)°	µ = 2.28 mm⁻¹
β = 96.978 (1)°	T = 173 K
γ = 93.267 (1)°	Block, colourless
V = 961.3 (2) Å³	0.19 × 0.18 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	3536 independent reflections
Radiation source: sealed tube	3172 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.36 pixels mm^-1	θ_max = 25.4°, θ_min = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2014/5)	k = −14→13
T_min = 0.663, T_max = 0.745	l = −16→16
10335 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0194P)² + 1.6836P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3536 reflections	Δρ_max = 0.96 e Å⁻³
291 parameters	Δρ_min = −0.46 e Å⁻³

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 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 structure was solved by the direct method using the SHELXT program and refined by least squares method on F2, SHELXL, 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. The structure was refined by Least Squares using version 2018/3 of XL (Sheldrick, 2015) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.

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

	x	y	z	U_iso*/U_eq
Cd1	0.30111 (3)	0.18731 (2)	0.26320 (2)	0.01372 (8)
Cd2	0.26261 (3)	0.56335 (2)	0.45843 (2)	0.01311 (7)
O1	0.6054 (4)	0.1503 (2)	0.19000 (17)	0.0199 (5)
O2	0.7503 (4)	0.0924 (2)	0.04417 (18)	0.0223 (5)
O3	0.3239 (4)	0.2625 (2)	0.10350 (17)	0.0192 (5)
O4	0.2524 (3)	0.37691 (19)	0.29797 (17)	0.0174 (5)
O5	0.1116 (4)	0.54112 (19)	0.29333 (17)	0.0206 (5)
O6	0.4298 (3)	0.08315 (19)	0.37674 (17)	0.0178 (5)
O7	0.5650 (3)	0.26916 (19)	0.42704 (17)	0.0165 (5)
O8	0.8603 (3)	0.22913 (18)	0.56197 (17)	0.0171 (5)
O9	1.0690 (3)	0.38854 (19)	0.49607 (16)	0.0154 (5)
O10	1.3856 (3)	0.45670 (19)	0.57865 (17)	0.0171 (5)
O11	−0.0206 (4)	0.1786 (2)	0.32737 (18)	0.0202 (5)
H11A	−0.0207	0.2381	0.3820	0.030*
H11B	−0.1387	0.1714	0.2845	0.030*
O12	0.1160 (4)	0.0302 (2)	0.14044 (17)	0.0215 (5)
H12A	0.1920	0.0021	0.0887	0.032*
H12B	0.0020	0.0533	0.1071	0.032*
C1	0.6117 (5)	0.1404 (3)	0.0939 (2)	0.0169 (7)
C2	0.4371 (5)	0.1873 (3)	0.0318 (2)	0.0173 (7)
H2A	0.4989	0.2321	−0.0129	0.021*
H2B	0.3400	0.1209	−0.0137	0.021*
C3	0.1492 (5)	0.3093 (3)	0.0643 (2)	0.0146 (7)
C4	0.0711 (5)	0.2810 (3)	−0.0415 (3)	0.0197 (7)
H4	0.1405	0.2289	−0.0905	0.024*
C5	−0.1080 (5)	0.3293 (3)	−0.0751 (3)	0.0223 (8)
H5	−0.1606	0.3105	−0.1475	0.027*
C6	−0.2112 (6)	0.4042 (3)	−0.0051 (3)	0.0224 (8)
H6	−0.3374	0.4343	−0.0286	0.027*
C7	−0.1298 (5)	0.4356 (3)	0.1002 (3)	0.0210 (7)
H7	−0.1995	0.4886	0.1483	0.025*
C8	0.0528 (5)	0.3903 (3)	0.1362 (2)	0.0149 (7)
C9	0.1449 (5)	0.4362 (3)	0.2489 (2)	0.0152 (7)
C10	0.5591 (5)	0.1631 (3)	0.4348 (2)	0.0140 (7)
C11	0.7138 (5)	0.1291 (3)	0.5142 (2)	0.0153 (7)
H11C	0.6386	0.1052	0.5673	0.018*
H11D	0.7889	0.0619	0.4798	0.018*
C12	1.0460 (5)	0.2124 (3)	0.6169 (2)	0.0130 (6)
C13	1.0573 (5)	0.1223 (3)	0.6671 (2)	0.0154 (7)
H13	0.9365	0.0691	0.6617	0.018*
C14	1.2463 (5)	0.1105 (3)	0.7252 (2)	0.0172 (7)
H14	1.2563	0.0473	0.7577	0.021*
C15	1.4200 (5)	0.1906 (3)	0.7360 (3)	0.0189 (7)
H15	1.5481	0.1835	0.7772	0.023*
C16	1.4071 (5)	0.2806 (3)	0.6867 (2)	0.0172 (7)
H16	1.5262	0.3362	0.6960	0.021*
C17	1.2230 (5)	0.2919 (3)	0.6235 (2)	0.0140 (7)
C18	1.2237 (5)	0.3837 (3)	0.5635 (2)	0.0132 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01275 (13)	0.01489 (13)	0.01405 (12)	0.00280 (9)	0.00192 (9)	0.00434 (9)
Cd2	0.01108 (13)	0.01325 (12)	0.01568 (12)	0.00162 (9)	0.00207 (9)	0.00483 (9)
O1	0.0175 (12)	0.0270 (13)	0.0167 (12)	0.0076 (10)	0.0049 (9)	0.0059 (10)
O2	0.0186 (12)	0.0241 (13)	0.0225 (12)	0.0048 (10)	0.0077 (10)	−0.0004 (10)
O3	0.0222 (13)	0.0228 (12)	0.0136 (11)	0.0109 (10)	0.0050 (9)	0.0036 (9)
O4	0.0178 (12)	0.0172 (11)	0.0167 (11)	0.0041 (9)	−0.0005 (9)	0.0041 (9)
O5	0.0260 (13)	0.0169 (12)	0.0182 (12)	0.0067 (10)	0.0034 (10)	0.0018 (9)
O6	0.0166 (12)	0.0152 (11)	0.0203 (12)	−0.0024 (9)	−0.0036 (9)	0.0058 (9)
O7	0.0176 (12)	0.0155 (11)	0.0172 (11)	0.0037 (9)	0.0002 (9)	0.0060 (9)
O8	0.0125 (11)	0.0141 (11)	0.0242 (12)	−0.0011 (9)	−0.0044 (9)	0.0079 (9)
O9	0.0139 (11)	0.0163 (11)	0.0170 (11)	0.0024 (9)	0.0021 (9)	0.0061 (9)
O10	0.0150 (12)	0.0136 (11)	0.0242 (12)	0.0002 (9)	0.0069 (9)	0.0059 (9)
O11	0.0151 (12)	0.0232 (12)	0.0201 (12)	0.0011 (10)	0.0050 (9)	0.0002 (10)
O12	0.0172 (12)	0.0246 (13)	0.0185 (12)	0.0015 (10)	0.0036 (10)	−0.0025 (10)
C1	0.0169 (17)	0.0137 (15)	0.0183 (16)	−0.0014 (13)	0.0027 (13)	0.0016 (12)
C2	0.0165 (17)	0.0186 (16)	0.0176 (16)	0.0035 (13)	0.0076 (13)	0.0030 (13)
C3	0.0171 (17)	0.0115 (15)	0.0170 (16)	0.0006 (12)	0.0034 (13)	0.0069 (12)
C4	0.0237 (19)	0.0148 (16)	0.0192 (17)	0.0005 (14)	0.0040 (14)	0.0019 (13)
C5	0.0231 (19)	0.0214 (18)	0.0213 (17)	−0.0045 (14)	−0.0070 (14)	0.0098 (14)
C6	0.0183 (18)	0.0228 (18)	0.0267 (18)	0.0002 (14)	−0.0034 (14)	0.0110 (15)
C7	0.0176 (18)	0.0199 (17)	0.0273 (18)	0.0023 (14)	0.0026 (14)	0.0098 (14)
C8	0.0143 (16)	0.0128 (15)	0.0184 (16)	−0.0013 (12)	0.0015 (13)	0.0068 (12)
C9	0.0123 (16)	0.0181 (16)	0.0158 (15)	−0.0009 (13)	0.0031 (13)	0.0057 (13)
C10	0.0142 (16)	0.0139 (16)	0.0157 (15)	0.0036 (13)	0.0076 (13)	0.0039 (12)
C11	0.0136 (16)	0.0125 (15)	0.0193 (16)	−0.0012 (13)	0.0001 (13)	0.0049 (12)
C12	0.0102 (15)	0.0135 (15)	0.0143 (15)	0.0024 (12)	0.0010 (12)	0.0018 (12)
C13	0.0136 (16)	0.0155 (16)	0.0175 (16)	−0.0006 (13)	0.0019 (13)	0.0055 (12)
C14	0.0255 (18)	0.0144 (16)	0.0142 (15)	0.0062 (13)	0.0022 (13)	0.0078 (12)
C15	0.0172 (17)	0.0220 (17)	0.0189 (16)	0.0046 (14)	−0.0019 (13)	0.0090 (13)
C16	0.0115 (16)	0.0203 (17)	0.0185 (16)	−0.0013 (13)	0.0012 (13)	0.0036 (13)
C17	0.0164 (17)	0.0118 (15)	0.0143 (15)	0.0025 (12)	0.0022 (13)	0.0037 (12)
C18	0.0134 (16)	0.0113 (15)	0.0147 (15)	0.0041 (12)	0.0065 (13)	0.0001 (12)

Geometric parameters (Å, º) top

Cd1—O1	2.298 (2)	O11—H11A	0.8766
Cd1—O3	2.520 (2)	O11—H11B	0.8772
Cd1—O4	2.208 (2)	O12—H12A	0.8993
Cd1—O6	2.283 (2)	O12—H12B	0.8991
Cd1—O7	2.537 (2)	C1—C2	1.520 (5)
Cd1—O11	2.330 (2)	C2—H2A	0.9900
Cd1—O12	2.296 (2)	C2—H2B	0.9900
Cd1—C10	2.742 (3)	C3—C4	1.391 (4)
Cd2—O4	2.648 (2)	C3—C8	1.401 (4)
Cd2—O5	2.243 (2)	C4—H4	0.9500
Cd2—O7ⁱ	2.297 (2)	C4—C5	1.383 (5)
Cd2—O9ⁱⁱ	2.526 (2)	C5—H5	0.9500
Cd2—O9ⁱ	2.338 (2)	C5—C6	1.375 (5)
Cd2—O10ⁱⁱ	2.361 (2)	C6—H6	0.9500
Cd2—O10ⁱⁱⁱ	2.374 (2)	C6—C7	1.388 (5)
O1—C1	1.266 (4)	C7—H7	0.9500
O2—C1	1.248 (4)	C7—C8	1.393 (5)
O3—C2	1.429 (4)	C8—C9	1.500 (4)
O3—C3	1.377 (4)	C10—C11	1.505 (4)
O4—C9	1.249 (4)	C11—H11C	0.9900
O5—C9	1.270 (4)	C11—H11D	0.9900
O6—C10	1.249 (4)	C12—C13	1.387 (4)
O7—Cd2ⁱ	2.297 (2)	C12—C17	1.405 (4)
O7—C10	1.275 (4)	C13—H13	0.9500
O8—C11	1.422 (3)	C13—C14	1.388 (5)
O8—C12	1.370 (4)	C14—H14	0.9500
O9—Cd2^iv	2.526 (2)	C14—C15	1.385 (5)
O9—Cd2ⁱ	2.338 (2)	C15—H15	0.9500
O9—C18	1.268 (4)	C15—C16	1.378 (5)
O10—Cd2ⁱⁱⁱ	2.374 (2)	C16—H16	0.9500
O10—Cd2^iv	2.361 (2)	C16—C17	1.397 (4)
O10—C18	1.269 (4)	C17—C18	1.496 (4)

O1—Cd1—O3	65.56 (8)	Cd1—O11—H11B	119.2
O1—Cd1—O7	81.95 (8)	H11A—O11—H11B	110.1
O1—Cd1—O11	167.04 (8)	Cd1—O12—H12A	111.1
O1—Cd1—C10	80.86 (8)	Cd1—O12—H12B	110.7
O3—Cd1—O7	120.43 (7)	H12A—O12—H12B	103.0
O3—Cd1—C10	139.43 (9)	O1—C1—C2	118.9 (3)
O4—Cd1—O1	111.25 (8)	O2—C1—O1	124.9 (3)
O4—Cd1—O3	69.81 (8)	O2—C1—C2	116.3 (3)
O4—Cd1—O6	127.85 (8)	O3—C2—C1	108.5 (3)
O4—Cd1—O7	78.68 (7)	O3—C2—H2A	110.0
O4—Cd1—O11	81.56 (8)	O3—C2—H2B	110.0
O4—Cd1—O12	130.05 (8)	C1—C2—H2A	110.0
O4—Cd1—C10	104.76 (8)	C1—C2—H2B	110.0
O6—Cd1—O1	85.47 (8)	H2A—C2—H2B	108.4
O6—Cd1—O3	150.85 (8)	O3—C3—C4	122.7 (3)
O6—Cd1—O7	54.31 (7)	O3—C3—C8	117.0 (3)
O6—Cd1—O11	88.00 (8)	C4—C3—C8	120.3 (3)
O6—Cd1—O12	96.77 (8)	C3—C4—H4	120.2
O6—Cd1—C10	26.85 (8)	C5—C4—C3	119.6 (3)
O7—Cd1—C10	27.60 (8)	C5—C4—H4	120.2
O11—Cd1—O3	119.67 (8)	C4—C5—H5	119.6
O11—Cd1—O7	103.23 (8)	C6—C5—C4	120.8 (3)
O11—Cd1—C10	98.15 (9)	C6—C5—H5	119.6
O12—Cd1—O1	91.10 (8)	C5—C6—H6	120.2
O12—Cd1—O3	81.33 (8)	C5—C6—C7	119.6 (3)
O12—Cd1—O7	150.54 (8)	C7—C6—H6	120.2
O12—Cd1—O11	78.55 (8)	C6—C7—H7	119.6
O12—Cd1—C10	123.09 (9)	C6—C7—C8	120.8 (3)
O5—Cd2—O4	52.32 (7)	C8—C7—H7	119.6
O5—Cd2—O7ⁱ	128.03 (8)	C3—C8—C9	122.9 (3)
O5—Cd2—O9ⁱ	85.48 (8)	C7—C8—C3	118.6 (3)
O5—Cd2—O9ⁱⁱ	98.88 (8)	C7—C8—C9	118.4 (3)
O5—Cd2—O10ⁱⁱⁱ	96.64 (8)	O4—C9—O5	120.5 (3)
O5—Cd2—O10ⁱⁱ	142.74 (8)	O4—C9—C8	122.9 (3)
O7ⁱ—Cd2—O4	151.33 (8)	O5—C9—C8	116.6 (3)
O7ⁱ—Cd2—O9ⁱ	93.14 (8)	O6—C10—Cd1	55.65 (16)
O7ⁱ—Cd2—O9ⁱⁱ	129.27 (7)	O6—C10—O7	122.3 (3)
O7ⁱ—Cd2—O10ⁱⁱ	88.12 (8)	O6—C10—C11	117.2 (3)
O7ⁱ—Cd2—O10ⁱⁱⁱ	79.41 (8)	O7—C10—Cd1	67.22 (17)
O9ⁱⁱ—Cd2—O4	70.79 (7)	O7—C10—C11	120.4 (3)
O9ⁱ—Cd2—O4	114.63 (7)	C11—C10—Cd1	168.7 (2)
O9ⁱ—Cd2—O9ⁱⁱ	69.96 (8)	O8—C11—C10	107.5 (2)
O9ⁱ—Cd2—O10ⁱⁱⁱ	171.93 (7)	O8—C11—H11C	110.2
O9ⁱ—Cd2—O10ⁱⁱ	103.18 (8)	O8—C11—H11D	110.2
O10ⁱⁱ—Cd2—O4	92.11 (7)	C10—C11—H11C	110.2
O10ⁱⁱⁱ—Cd2—O4	72.43 (7)	C10—C11—H11D	110.2
O10ⁱⁱ—Cd2—O9ⁱⁱ	53.09 (7)	H11C—C11—H11D	108.5
O10ⁱⁱⁱ—Cd2—O9ⁱⁱ	117.19 (7)	O8—C12—C13	121.1 (3)
O10ⁱⁱ—Cd2—O10ⁱⁱⁱ	79.83 (8)	O8—C12—C17	117.7 (3)
C1—O1—Cd1	121.9 (2)	C13—C12—C17	121.2 (3)
C2—O3—Cd1	110.90 (18)	C12—C13—H13	120.2
C3—O3—Cd1	117.78 (18)	C12—C13—C14	119.6 (3)
C3—O3—C2	118.6 (2)	C14—C13—H13	120.2
Cd1—O4—Cd2	140.68 (10)	C13—C14—H14	119.9
C9—O4—Cd1	132.37 (19)	C15—C14—C13	120.1 (3)
C9—O4—Cd2	84.27 (17)	C15—C14—H14	119.9
C9—O5—Cd2	102.8 (2)	C14—C15—H15	120.0
C10—O6—Cd1	97.50 (19)	C16—C15—C14	120.0 (3)
Cd2ⁱ—O7—Cd1	145.62 (10)	C16—C15—H15	120.0
C10—O7—Cd1	85.18 (17)	C15—C16—H16	119.2
C10—O7—Cd2ⁱ	128.9 (2)	C15—C16—C17	121.5 (3)
C12—O8—C11	118.3 (2)	C17—C16—H16	119.2
Cd2ⁱ—O9—Cd2^iv	110.04 (8)	C12—C17—C18	123.0 (3)
C18—O9—Cd2^iv	89.97 (18)	C16—C17—C12	117.5 (3)
C18—O9—Cd2ⁱ	122.20 (19)	C16—C17—C18	119.4 (3)
Cd2^iv—O10—Cd2ⁱⁱⁱ	100.17 (8)	O9—C18—O10	119.3 (3)
C18—O10—Cd2ⁱⁱⁱ	133.07 (19)	O9—C18—C17	121.7 (3)
C18—O10—Cd2^iv	97.67 (19)	O10—C18—C17	119.0 (3)
Cd1—O11—H11A	109.7

Cd1—O1—C1—O2	−161.2 (2)	O8—C12—C13—C14	−177.7 (3)
Cd1—O1—C1—C2	17.5 (4)	O8—C12—C17—C16	174.8 (3)
Cd1—O3—C2—C1	−35.1 (3)	O8—C12—C17—C18	−7.4 (4)
Cd1—O3—C3—C4	−134.4 (3)	C2—O3—C3—C4	3.9 (4)
Cd1—O3—C3—C8	47.0 (3)	C2—O3—C3—C8	−174.8 (3)
Cd1—O4—C9—O5	167.2 (2)	C3—O3—C2—C1	−176.0 (3)
Cd1—O4—C9—C8	−14.0 (5)	C3—C4—C5—C6	−0.5 (5)
Cd1—O6—C10—O7	8.9 (3)	C3—C8—C9—O4	−31.0 (5)
Cd1—O6—C10—C11	−169.8 (2)	C3—C8—C9—O5	147.8 (3)
Cd1—O7—C10—O6	−8.0 (3)	C4—C3—C8—C7	4.2 (5)
Cd1—O7—C10—C11	170.7 (3)	C4—C3—C8—C9	−172.0 (3)
Cd1—C10—C11—O8	124.5 (10)	C4—C5—C6—C7	2.6 (5)
Cd2—O4—C9—O5	3.3 (3)	C5—C6—C7—C8	−1.3 (5)
Cd2—O4—C9—C8	−177.9 (3)	C6—C7—C8—C3	−2.1 (5)
Cd2—O5—C9—O4	−4.0 (3)	C6—C7—C8—C9	174.2 (3)
Cd2—O5—C9—C8	177.1 (2)	C7—C8—C9—O4	152.9 (3)
Cd2ⁱ—O7—C10—Cd1	174.7 (2)	C7—C8—C9—O5	−28.3 (4)
Cd2ⁱ—O7—C10—O6	166.7 (2)	C8—C3—C4—C5	−2.9 (5)
Cd2ⁱ—O7—C10—C11	−14.6 (4)	C11—O8—C12—C13	−30.0 (4)
Cd2ⁱ—O9—C18—O10	−115.1 (3)	C11—O8—C12—C17	152.0 (3)
Cd2^iv—O9—C18—O10	−1.2 (3)	C12—O8—C11—C10	−163.6 (3)
Cd2^iv—O9—C18—C17	−179.4 (2)	C12—C13—C14—C15	2.2 (5)
Cd2ⁱ—O9—C18—C17	66.8 (3)	C12—C17—C18—O9	−6.1 (5)
Cd2^iv—O10—C18—O9	1.3 (3)	C12—C17—C18—O10	175.8 (3)
Cd2ⁱⁱⁱ—O10—C18—O9	−110.4 (3)	C13—C12—C17—C16	−3.2 (4)
Cd2ⁱⁱⁱ—O10—C18—C17	67.8 (4)	C13—C12—C17—C18	174.6 (3)
Cd2^iv—O10—C18—C17	179.5 (2)	C13—C14—C15—C16	−1.6 (5)
O1—C1—C2—O3	14.8 (4)	C14—C15—C16—C17	−1.5 (5)
O2—C1—C2—O3	−166.4 (3)	C15—C16—C17—C12	3.9 (5)
O3—C3—C4—C5	178.5 (3)	C15—C16—C17—C18	−174.0 (3)
O3—C3—C8—C7	−177.2 (3)	C16—C17—C18—O9	171.7 (3)
O3—C3—C8—C9	6.7 (4)	C16—C17—C18—O10	−6.4 (4)
O6—C10—C11—O8	173.0 (3)	C17—C12—C13—C14	0.2 (5)
O7—C10—C11—O8	−5.7 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11A···O9ⁱⁱ	0.88	2.03	2.873 (3)	162
O11—H11B···O1ⁱⁱ	0.88	1.91	2.782 (3)	178
O12—H12A···O2^v	0.90	1.94	2.788 (3)	158
O12—H12B···O2ⁱⁱ	0.90	1.86	2.756 (3)	174

Symmetry codes: (ii) x−1, y, z; (v) −x+1, −y, −z.

Acknowledgements

GJG thanks her mother for serving as a constant, unconditional positive influence in her life.

Funding information

Funding for this work was provided by the Honors College of Michigan State University.

References

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