metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

catena-Poly[[bis­­{2-[3-(carb­­oxy­meth­yl)adamantan-1-yl]acetato-κ2O,O′}cadmium(II)]-μ-N,N′-bis­­(pyridine-4-carbox­amido)­piperazine-κ2N:N′]

CROSSMARK_Color_square_no_text.svg

aHope College, Department of Chemistry, Holland, MI 49423, USA, and bE-35 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 2 September 2016; accepted 4 November 2016; online 10 November 2016)

In the title compound, [Cd(C14H19O4)2(C16H16N4O2)]n, the CdII cation is coordinated in a distorted octa­hedral fashion by trans pyridyl N-atom donors from two N,N′-bis­(pyridine-4-carboxamido)­piperazine (bpcp) ligands, and chelating carboxyl­ate groups from two 2-[3-(carb­oxy­meth­yl)adamantan-1-yl]acetate ligands. [Cd(adaH)(bpcp)]n coordination polymer chains are oriented along [-111] and aggregate into supra­molecular layers parallel to (122) by O—H⋯O hydrogen-bonding inter­actions. The supra­molecular three-dimensional crystal structure is then constructed by inter­layer C—H⋯O non-classical inter­actions. The O atoms of one of the carboxyl­ate groups were refined as disordered over two sets of sites, with occupancies 0.553 (7) and 0.447 (7).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound was isolated during an exploratory synthetic effort aiming to produce divalent metal coordination polymers containing both adamantanedi­acetate (ada) and N,N′-bis­(4-pyridyl­carboxamide)­piperazine (bpcp) ligands. Coordination polymers containing both phthalate (pht) and bpcp ligands show significant topological differences depending on coordination-environment preferences at the divalent metal ion. {[Cd2(pht)2(bpcp)(H2O)2]n displayed a 3-D structure built from the bpcp pillaring of [Cd(pht)(H2O)]n layer motifs into a 4,5-connected binodal net with rare (4462)(4466) tcs topology; this material fluoresced with a blue–violet hue upon UV excitation. {[Co(pht)(bpcp)(H2O)2]·H2O}n possesses an acentric (4,4) grid-layer topology. {[Cu2(pht)2(bpcp)(H2O)2]n exhibits binding of bpcp C=O amide O atoms and a previously unreported 4,4-connected binodal layer structure with (4.648)2(4264) topology (Wang et al., 2011[Wang, C. Y., Wilseck, Z. M., Supkowski, R. M. & LaDuca, R. L. (2011). CrystEngComm, 13, 1391-1399.]). It was hoped that the ada ligand would afford different coordination polymer topologies than previous pht analogs, due to its rigid non-aromatic adamantyl core along with its flexible pendant acetate arms.

The asymmetric unit of the title compound contains a CdII cation, two anionic adaH ligands protonated at their unligated carboxyl­ate termini, and halves of two crystallographically distinct bpcp ligands whose central piperazinyl rings are sited over crystallographic inversion centers (Fig. 1[link]). The CdII ion is bound by trans pyridyl N atoms from two bpcp ligands, and chelating carboxyl­ate groups from two adaH ligands. Each adaH ligand has a pendant, protonated carboxyl­ate group that is unligated. Bond lengths and angles (Table 1[link]) are consistent with an octa­hedral coordination environment for the CdII atom with two chelating groups. The dipodal bpcp ligands connect [Cd(adaH)2] fragments into [Cd(adaH)2(bpcp)]n coordination polymer chains that are oriented along the [[\overline{1}]11] direction (Fig. 2[link]). The Cd⋯Cd distances through the crystallographically distinct anti-conformation bpcp ligands measure 16.53 (2) and 16.68 (2) Å.

Table 1
Selected geometric parameters (Å, °)

Cd1—O5 2.419 (2) Cd1—O8 2.258 (9)
Cd1—O6 2.285 (2) Cd1—N1 2.301 (3)
Cd1—O7 2.351 (6) Cd1—N3 2.296 (3)
       
O6—Cd1—O5 54.87 (9) O8—Cd1—N1 126.6 (2)
O6—Cd1—O7 115.9 (2) O8—Cd1—N3 104.4 (3)
O6—Cd1—N1 100.50 (10) N1—Cd1—O5 92.25 (11)
O6—Cd1—N3 131.49 (9) N1—Cd1—O7 84.08 (19)
O7—Cd1—O5 169.4 (2) N3—Cd1—O5 81.78 (9)
O8—Cd1—O5 136.7 (2) N3—Cd1—O7 108.7 (2)
O8—Cd1—O6 95.4 (3) N3—Cd1—N1 102.00 (10)
[Figure 1]
Figure 1
The coordination environment of the title compound, showing octa­hedral coordination at the CdII cation. Complete bpcp ligands are shown. Displacement ellipsoids are drawn at the 50% probability level. Most H atoms have been omitted for clarity. Color code: Cd, violet; N, blue; O, red; C, black; H, pink.
[Figure 2]
Figure 2
Coordination polymer chain in the title compound, oriented parallel to [[\overline{1}]11].

Supra­molecular O—H⋯O inter­actions (Table 2[link]) anchor adjacent [Cd(adaH)2(bpcp)]n coordination polymer chains into supra­molecular layers parallel to the (122) plane (Fig. 3[link]). These supra­molecular layers stack and inter­digitate in order to construct the three-dimensional crystal structure of the title compound, by means of C—H⋯O inter­actions between bpcp piperazinyl carbon atoms and C=O moieties belonging to pendant adaH carboxyl­ate groups (Fig. 4[link]).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4⋯O5i 0.84 1.75 2.588 (3) 175
O10—H10⋯O7ii 0.84 1.89 2.725 (8) 171
O10—H10⋯O7Aii 0.84 1.70 2.520 (6) 165
C39—H39A⋯O4 0.99 2.52 3.135 (4) 120
C47—H47B⋯O6 0.99 2.55 3.163 (4) 120
C55—H55B⋯O7A 0.99 2.46 3.009 (7) 115
C62—H62B⋯O10 0.99 2.53 3.115 (4) 117
C63—H63B⋯O8A 0.99 2.47 3.107 (8) 121
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y+2, -z+1.
[Figure 3]
Figure 3
Supra­molecular layer in the title compound, oriented parallel to the (122) plane. O—H⋯O hydrogen-bonding inter­actions are shown as dashed lines.
[Figure 4]
Figure 4
Stacking of supra­molecular layer motifs in the title compound, mediated by inter­layer C—H⋯O non-classical inter­actions.

Synthesis and crystallization

Cd(NO3)2·4H2O (114 mg, 0.37 mmol), 1,3-adamantanedi­acetic acid (93 mg, 0.37 mmol), bpcp (110 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. Colourless crystals of the title complex (107 mg, 32% yield based on 1,3-adamantanedi­acetic acid) 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 3[link]. The O atoms of one of the carboxyl­ate groups were refined as disordered over two sets of sites, with occupancies 0.553 (7) and 0.447 (7).

Table 3
Experimental details

Crystal data
Chemical formula [Cd(C14H19O4)2(C16H16N4O2)]
Mr 911.31
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 6.3660 (11), 15.282 (3), 21.575 (4)
α, β, γ (°) 88.968 (2), 87.985 (2), 79.217 (2)
V3) 2060.4 (6)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.59
Crystal size (mm) 0.46 × 0.21 × 0.05
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS, Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.663, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 34440, 7598, 6439
Rint 0.054
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.06
No. of reflections 7598
No. of parameters 535
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.66, −0.40
Computer programs: COSMO (Bruker, 2009[Bruker (2009). COSMO. Bruker AXS Inc., Madison, Wisconsin, USA.]), APEX2 (Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), CrystalMaker (Palmer, 2013[Palmer, D. (2013). CrystalMaker. CrystalMaker Software, Bicester, England.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: CrystalMaker (Palmer, 2013); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[[bis{2-[3-(carboxymethyl)adamantan-1-yl]acetato-κ2O,O'}cadmium(II)]-µ-N,N'-bis(pyridine-4-carboxamido)piperazine-κ2N:N'] top
Crystal data top
[Cd(C14H19O4)2(C16H16N4O2)]Z = 2
Mr = 911.31F(000) = 948
Triclinic, P1Dx = 1.469 Mg m3
a = 6.3660 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.282 (3) ÅCell parameters from 9913 reflections
c = 21.575 (4) Åθ = 2.3–22.8°
α = 88.968 (2)°µ = 0.59 mm1
β = 87.985 (2)°T = 173 K
γ = 79.217 (2)°Rectangular, colourless
V = 2060.4 (6) Å30.46 × 0.21 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
7598 independent reflections
Radiation source: sealed tube6439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 836.6 pixels mm-1θmax = 25.4°, θmin = 1.4°
ω scansh = 77
Absorption correction: multi-scan
(SADABS, Bruker, 2014)
k = 1818
Tmin = 0.663, Tmax = 0.745l = 2526
34440 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0658P)2 + 0.9489P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
7598 reflectionsΔρmax = 1.66 e Å3
535 parametersΔρmin = 0.40 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cd11.01461 (4)0.77868 (2)0.76254 (2)0.02423 (10)
O10.3830 (5)0.4755 (2)0.64910 (13)0.0519 (8)
O20.0779 (4)1.09521 (17)0.85291 (12)0.0419 (7)
O31.2617 (5)0.18816 (18)1.02438 (13)0.0523 (8)
O41.2537 (4)0.32992 (16)1.04814 (12)0.0389 (6)
H41.17350.31781.07750.058*
O50.9966 (5)0.69784 (19)0.85940 (12)0.0485 (8)
O61.2922 (4)0.68106 (16)0.80394 (11)0.0351 (6)
O71.0787 (14)0.8339 (5)0.6626 (3)0.0366 (8)0.447 (7)
O7A0.9608 (11)0.8550 (4)0.6640 (2)0.0366 (8)0.553 (7)
O81.220 (2)0.8710 (6)0.7198 (4)0.0366 (8)0.447 (7)
O8A1.2179 (16)0.8909 (5)0.7366 (3)0.0366 (8)0.553 (7)
O90.8949 (6)1.3052 (3)0.44493 (15)0.0786 (12)
O101.1218 (7)1.17740 (19)0.44569 (13)0.0768 (12)
H101.07371.17300.41040.115*
N10.8480 (5)0.68192 (18)0.71065 (12)0.0273 (6)
N20.5755 (5)0.47731 (19)0.55966 (13)0.0314 (7)
N30.7295 (4)0.87221 (17)0.80842 (12)0.0247 (6)
N40.1051 (4)1.02679 (19)0.94668 (13)0.0281 (6)
C200.6470 (6)0.7088 (2)0.69111 (16)0.0307 (8)
H200.57610.76800.69950.037*
C210.5399 (6)0.6536 (2)0.65924 (16)0.0303 (8)
H210.39860.67460.64590.036*
C220.9459 (6)0.5989 (2)0.69811 (16)0.0288 (7)
H221.08770.57950.71160.035*
C230.8506 (6)0.5399 (2)0.66644 (16)0.0314 (8)
H230.92650.48140.65800.038*
C240.6436 (5)0.5668 (2)0.64722 (15)0.0261 (7)
C250.5219 (6)0.5032 (2)0.61819 (16)0.0289 (8)
C260.4487 (6)0.4211 (2)0.52913 (16)0.0331 (8)
H26A0.36490.39320.56070.040*
H26B0.54520.37300.50640.040*
C270.7015 (5)0.5238 (2)0.51571 (16)0.0310 (8)
H27A0.80840.47990.49270.037*
H27B0.77840.56300.53860.037*
C280.7140 (6)0.9614 (2)0.81094 (16)0.0297 (8)
H280.82800.98710.79370.036*
C290.5407 (6)1.0161 (2)0.83741 (16)0.0313 (8)
H290.53371.07880.83730.038*
C300.3922 (5)0.8874 (2)0.86200 (15)0.0274 (7)
H300.28210.85960.87960.033*
C310.5701 (5)0.8369 (2)0.83379 (16)0.0273 (7)
H310.57980.77420.83230.033*
C320.3744 (5)0.9794 (2)0.86457 (15)0.0249 (7)
C330.1756 (5)1.0396 (2)0.88815 (16)0.0282 (8)
C340.0928 (5)1.0825 (2)0.96999 (16)0.0297 (8)
H34A0.17231.11390.93500.036*
H34B0.05911.12770.99840.036*
C350.2294 (5)0.9761 (2)0.99571 (16)0.0286 (7)
H35A0.27451.01751.02510.034*
H35B0.35950.93850.97740.034*
C361.4832 (5)0.2699 (2)0.96492 (16)0.0292 (8)
H36A1.54140.21060.94720.035*
H36B1.60280.29090.98450.035*
C371.3202 (6)0.2583 (2)1.01475 (16)0.0300 (8)
C381.4063 (5)0.3342 (2)0.91128 (15)0.0234 (7)
C391.3826 (5)0.4327 (2)0.93002 (14)0.0214 (7)
H39A1.27450.44560.96440.026*
H39B1.52070.44340.94510.026*
C401.3142 (5)0.4960 (2)0.87499 (14)0.0219 (7)
C411.1010 (5)0.4776 (2)0.85260 (15)0.0246 (7)
H41A1.05260.51800.81750.030*
H41B0.99110.48910.88660.030*
C421.1275 (5)0.3800 (2)0.83188 (15)0.0262 (7)
H420.98820.36920.81660.031*
C431.2974 (6)0.3612 (2)0.77995 (16)0.0308 (8)
H43A1.25350.40020.74370.037*
H43B1.31380.29850.76680.037*
C441.5108 (5)0.3787 (2)0.80314 (16)0.0291 (8)
H441.62300.36630.76920.035*
C451.5764 (5)0.3171 (2)0.85828 (16)0.0289 (8)
H45A1.71510.32720.87320.035*
H45B1.59500.25440.84510.035*
C461.1921 (5)0.3186 (2)0.88754 (16)0.0271 (7)
H46A1.20560.25570.87520.032*
H46B1.08050.33080.92100.032*
C471.4843 (5)0.4763 (2)0.82269 (15)0.0250 (7)
H47A1.62240.48810.83700.030*
H47B1.44140.51590.78670.030*
C481.2923 (6)0.5928 (2)0.89746 (15)0.0267 (7)
H48A1.20590.59960.93670.032*
H48B1.43620.60440.90630.032*
C491.1894 (6)0.6612 (2)0.85122 (15)0.0265 (7)
C501.1503 (7)0.8897 (2)0.67748 (19)0.0422 (10)
C511.2182 (8)0.9543 (2)0.62969 (19)0.0495 (12)
H51A1.20080.93270.58760.059*
H51B1.37160.95610.63430.059*
C541.0852 (6)1.0500 (2)0.63679 (15)0.0284 (8)
C550.8450 (6)1.0508 (2)0.63406 (17)0.0353 (9)
H55A0.81361.02490.59450.042*
H55B0.79981.01410.66850.042*
C560.7213 (6)1.1458 (3)0.6391 (2)0.0425 (10)
H560.56471.14540.63760.051*
C570.7669 (7)1.1850 (3)0.69993 (19)0.0457 (10)
H57A0.72171.14910.73490.055*
H57B0.68471.24650.70350.055*
C581.0049 (7)1.1856 (2)0.70306 (16)0.0374 (9)
H581.03511.21160.74330.045*
C591.0709 (7)1.2423 (2)0.64891 (16)0.0360 (9)
H59A1.22541.24380.65080.043*
H59B0.99041.30410.65250.043*
C600.7866 (6)1.2033 (3)0.58516 (19)0.0403 (9)
H60A0.75271.17900.54530.048*
H60B0.70501.26490.58880.048*
C611.0261 (5)1.2038 (2)0.58651 (15)0.0254 (7)
C621.1482 (6)1.1075 (2)0.58227 (15)0.0277 (7)
H62A1.30391.10710.58260.033*
H62B1.11701.08160.54270.033*
C631.1315 (6)1.0908 (2)0.69754 (16)0.0316 (8)
H63A1.28641.09140.69920.038*
H63B1.09181.05410.73280.038*
C641.0972 (6)1.2643 (2)0.53469 (16)0.0320 (8)
H64A1.04491.32710.54640.038*
H64B1.25551.25430.53300.038*
C651.0233 (7)1.2516 (2)0.47122 (17)0.0377 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03120 (16)0.01866 (14)0.02213 (15)0.00346 (10)0.00096 (10)0.00224 (9)
O10.065 (2)0.066 (2)0.0358 (16)0.0418 (17)0.0161 (14)0.0080 (14)
O20.0466 (16)0.0373 (15)0.0335 (15)0.0112 (12)0.0066 (12)0.0099 (12)
O30.080 (2)0.0363 (16)0.0477 (17)0.0291 (15)0.0000 (15)0.0065 (13)
O40.0488 (17)0.0282 (14)0.0371 (15)0.0036 (12)0.0140 (12)0.0059 (11)
O50.0503 (18)0.0446 (16)0.0373 (15)0.0199 (14)0.0143 (13)0.0214 (13)
O60.0327 (14)0.0330 (14)0.0382 (15)0.0044 (11)0.0001 (11)0.0164 (11)
O70.0536 (16)0.038 (2)0.0242 (15)0.024 (2)0.015 (2)0.0141 (15)
O7A0.0536 (16)0.038 (2)0.0242 (15)0.024 (2)0.015 (2)0.0141 (15)
O80.0536 (16)0.038 (2)0.0242 (15)0.024 (2)0.015 (2)0.0141 (15)
O8A0.0536 (16)0.038 (2)0.0242 (15)0.024 (2)0.015 (2)0.0141 (15)
O90.082 (3)0.099 (3)0.0389 (19)0.027 (2)0.0125 (17)0.0103 (18)
O100.170 (4)0.0308 (17)0.0270 (16)0.008 (2)0.020 (2)0.0007 (13)
N10.0369 (17)0.0242 (15)0.0224 (14)0.0103 (13)0.0001 (12)0.0005 (11)
N20.0412 (18)0.0311 (16)0.0267 (16)0.0193 (14)0.0009 (13)0.0005 (12)
N30.0270 (15)0.0230 (14)0.0232 (14)0.0031 (12)0.0020 (11)0.0001 (11)
N40.0227 (15)0.0291 (15)0.0282 (16)0.0050 (12)0.0026 (12)0.0042 (12)
C200.0310 (19)0.0261 (18)0.034 (2)0.0018 (15)0.0024 (15)0.0030 (15)
C210.0297 (19)0.0267 (18)0.034 (2)0.0037 (15)0.0035 (15)0.0018 (15)
C220.0283 (18)0.0264 (18)0.0308 (19)0.0024 (14)0.0014 (14)0.0007 (14)
C230.036 (2)0.0235 (18)0.034 (2)0.0024 (15)0.0035 (16)0.0019 (14)
C240.0308 (19)0.0282 (18)0.0206 (17)0.0094 (15)0.0005 (14)0.0025 (13)
C250.035 (2)0.0247 (18)0.0281 (19)0.0086 (15)0.0025 (15)0.0040 (14)
C260.042 (2)0.0326 (19)0.0291 (19)0.0186 (17)0.0002 (16)0.0013 (15)
C270.0293 (18)0.034 (2)0.033 (2)0.0160 (16)0.0038 (15)0.0008 (15)
C280.035 (2)0.0223 (17)0.0317 (19)0.0061 (15)0.0072 (15)0.0027 (14)
C290.041 (2)0.0198 (17)0.033 (2)0.0071 (15)0.0060 (16)0.0012 (14)
C300.0265 (18)0.0274 (18)0.0287 (18)0.0064 (14)0.0007 (14)0.0050 (14)
C310.0316 (19)0.0174 (16)0.0321 (19)0.0029 (14)0.0001 (15)0.0040 (14)
C320.0295 (18)0.0236 (17)0.0201 (17)0.0021 (14)0.0010 (13)0.0011 (13)
C330.0315 (19)0.0213 (17)0.0307 (19)0.0030 (14)0.0045 (15)0.0002 (14)
C340.0263 (18)0.0291 (18)0.0297 (19)0.0033 (14)0.0036 (14)0.0049 (14)
C350.0232 (17)0.0308 (19)0.0293 (18)0.0009 (14)0.0019 (14)0.0035 (14)
C360.0313 (19)0.0191 (17)0.0337 (19)0.0039 (14)0.0008 (15)0.0042 (14)
C370.036 (2)0.0261 (18)0.0281 (18)0.0047 (15)0.0086 (15)0.0079 (14)
C380.0261 (17)0.0184 (16)0.0248 (17)0.0024 (13)0.0011 (13)0.0018 (13)
C390.0231 (16)0.0204 (16)0.0206 (16)0.0040 (13)0.0005 (13)0.0009 (13)
C400.0242 (17)0.0188 (16)0.0229 (17)0.0049 (13)0.0024 (13)0.0041 (13)
C410.0236 (17)0.0244 (17)0.0252 (17)0.0030 (13)0.0029 (13)0.0075 (13)
C420.0235 (17)0.0294 (18)0.0283 (18)0.0116 (14)0.0032 (14)0.0025 (14)
C430.040 (2)0.0284 (19)0.0264 (18)0.0118 (16)0.0002 (15)0.0013 (14)
C440.0302 (19)0.0289 (18)0.0286 (18)0.0072 (15)0.0075 (14)0.0046 (14)
C450.0258 (18)0.0226 (17)0.036 (2)0.0006 (14)0.0006 (15)0.0022 (14)
C460.0308 (19)0.0193 (16)0.0317 (19)0.0067 (14)0.0002 (15)0.0019 (14)
C470.0272 (18)0.0243 (17)0.0243 (17)0.0070 (14)0.0018 (13)0.0026 (13)
C480.0366 (19)0.0208 (17)0.0225 (17)0.0039 (14)0.0050 (14)0.0020 (13)
C490.041 (2)0.0167 (16)0.0233 (17)0.0082 (15)0.0025 (15)0.0007 (13)
C500.066 (3)0.0191 (18)0.035 (2)0.0014 (18)0.025 (2)0.0020 (16)
C510.074 (3)0.024 (2)0.043 (2)0.0037 (19)0.030 (2)0.0120 (17)
C540.041 (2)0.0177 (16)0.0254 (18)0.0040 (14)0.0086 (15)0.0039 (13)
C550.046 (2)0.035 (2)0.031 (2)0.0236 (18)0.0005 (16)0.0025 (16)
C560.0224 (19)0.050 (2)0.055 (3)0.0083 (17)0.0019 (17)0.015 (2)
C570.053 (3)0.031 (2)0.047 (2)0.0049 (18)0.022 (2)0.0045 (18)
C580.065 (3)0.0276 (19)0.0221 (18)0.0155 (18)0.0006 (17)0.0005 (14)
C590.060 (3)0.0227 (18)0.0292 (19)0.0158 (17)0.0044 (17)0.0005 (15)
C600.037 (2)0.040 (2)0.044 (2)0.0055 (17)0.0073 (17)0.0111 (18)
C610.0344 (19)0.0189 (16)0.0242 (17)0.0077 (14)0.0045 (14)0.0040 (13)
C620.0349 (19)0.0219 (17)0.0258 (18)0.0056 (14)0.0052 (14)0.0040 (13)
C630.0318 (19)0.037 (2)0.0271 (19)0.0091 (16)0.0022 (15)0.0107 (15)
C640.049 (2)0.0180 (17)0.0308 (19)0.0099 (15)0.0045 (16)0.0040 (14)
C650.058 (3)0.030 (2)0.029 (2)0.0184 (18)0.0004 (18)0.0094 (16)
Geometric parameters (Å, º) top
Cd1—O52.419 (2)C36—C381.538 (4)
Cd1—O62.285 (2)C38—C391.545 (4)
Cd1—O72.351 (6)C38—C451.538 (5)
Cd1—O7A2.411 (5)C38—C461.534 (5)
Cd1—O82.258 (9)C39—H39A0.9900
Cd1—O8A2.382 (7)C39—H39B0.9900
Cd1—N12.301 (3)C39—C401.540 (4)
Cd1—N32.296 (3)C40—C411.532 (4)
O1—C251.222 (4)C40—C471.530 (4)
O2—C331.224 (4)C40—C481.545 (4)
O3—C371.211 (4)C41—H41A0.9900
O4—H40.8400C41—H41B0.9900
O4—C371.315 (4)C41—C421.542 (5)
O5—C491.258 (4)C42—H421.0000
O6—C491.256 (4)C42—C431.522 (5)
O7—C501.097 (8)C42—C461.530 (5)
O7A—C501.445 (8)C43—H43A0.9900
O8—C501.040 (9)C43—H43B0.9900
O8A—C501.361 (8)C43—C441.535 (5)
O9—C651.194 (5)C44—H441.0000
O10—H100.8400C44—C451.524 (5)
O10—C651.309 (5)C44—C471.535 (5)
N1—C201.348 (4)C45—H45A0.9900
N1—C221.333 (4)C45—H45B0.9900
N2—C251.343 (4)C46—H46A0.9900
N2—C261.463 (4)C46—H46B0.9900
N2—C271.478 (4)C47—H47A0.9900
N3—C281.350 (4)C47—H47B0.9900
N3—C311.333 (4)C48—H48A0.9900
N4—C331.348 (4)C48—H48B0.9900
N4—C341.461 (4)C48—C491.507 (4)
N4—C351.465 (4)C50—C511.523 (5)
C20—H200.9500C51—H51A0.9900
C20—C211.386 (5)C51—H51B0.9900
C21—H210.9500C51—C541.553 (5)
C21—C241.392 (5)C54—C551.530 (5)
C22—H220.9500C54—C621.542 (4)
C22—C231.380 (5)C54—C631.523 (5)
C23—H230.9500C55—H55A0.9900
C23—C241.381 (5)C55—H55B0.9900
C24—C251.508 (5)C55—C561.520 (5)
C26—H26A0.9900C56—H561.0000
C26—H26B0.9900C56—C571.511 (6)
C26—C27i1.514 (5)C56—C601.538 (5)
C27—C26i1.514 (5)C57—H57A0.9900
C27—H27A0.9900C57—H57B0.9900
C27—H27B0.9900C57—C581.521 (6)
C28—H280.9500C58—H581.0000
C28—C291.368 (5)C58—C591.535 (5)
C29—H290.9500C58—C631.526 (5)
C29—C321.395 (5)C59—H59A0.9900
C30—H300.9500C59—H59B0.9900
C30—C311.375 (5)C59—C611.536 (5)
C30—C321.391 (5)C60—H60A0.9900
C31—H310.9500C60—H60B0.9900
C32—C331.497 (5)C60—C611.527 (5)
C34—H34A0.9900C61—C621.533 (4)
C34—H34B0.9900C61—C641.547 (4)
C34—C35ii1.526 (5)C62—H62A0.9900
C35—C34ii1.526 (5)C62—H62B0.9900
C35—H35A0.9900C63—H63A0.9900
C35—H35B0.9900C63—H63B0.9900
C36—H36A0.9900C64—H64A0.9900
C36—H36B0.9900C64—H64B0.9900
C36—C371.499 (5)C64—C651.491 (5)
O6—Cd1—O554.87 (9)C42—C41—H41B109.7
O6—Cd1—O7115.9 (2)C41—C42—H42109.2
O6—Cd1—O7A134.05 (19)C43—C42—C41110.2 (3)
O6—Cd1—O8A95.5 (2)C43—C42—H42109.2
O6—Cd1—N1100.50 (10)C43—C42—C46110.1 (3)
O6—Cd1—N3131.49 (9)C46—C42—C41108.9 (3)
O7—Cd1—O5169.4 (2)C46—C42—H42109.2
O7—Cd1—O8A53.4 (2)C42—C43—H43A109.8
O7A—Cd1—O5168.65 (17)C42—C43—H43B109.8
O8—Cd1—O5136.7 (2)C42—C43—C44109.3 (3)
O8—Cd1—O695.4 (3)H43A—C43—H43B108.3
O8—Cd1—O7A54.1 (3)C44—C43—H43A109.8
O8—Cd1—N1126.6 (2)C44—C43—H43B109.8
O8—Cd1—N3104.4 (3)C43—C44—H44109.5
O8A—Cd1—O5128.67 (17)C43—C44—C47109.4 (3)
N1—Cd1—O592.25 (11)C45—C44—C43108.9 (3)
N1—Cd1—O784.08 (19)C45—C44—H44109.5
N1—Cd1—O7A79.53 (15)C45—C44—C47110.0 (3)
N1—Cd1—O8A137.31 (16)C47—C44—H44109.5
N3—Cd1—O581.78 (9)C38—C45—H45A109.5
N3—Cd1—O7108.7 (2)C38—C45—H45B109.5
N3—Cd1—O7A92.20 (19)C44—C45—C38110.8 (3)
N3—Cd1—O8A96.2 (2)C44—C45—H45A109.5
N3—Cd1—N1102.00 (10)C44—C45—H45B109.5
C37—O4—H4109.5H45A—C45—H45B108.1
C49—O5—Cd189.69 (19)C38—C46—H46A109.7
C49—O6—Cd196.0 (2)C38—C46—H46B109.7
C50—O7—Cd196.5 (5)C42—C46—C38109.7 (3)
C50—O7A—Cd185.2 (3)C42—C46—H46A109.7
C50—O8—Cd1103.9 (7)C42—C46—H46B109.7
C50—O8A—Cd188.1 (4)H46A—C46—H46B108.2
C65—O10—H10109.5C40—C47—C44110.0 (3)
C20—N1—Cd1120.2 (2)C40—C47—H47A109.7
C22—N1—Cd1121.8 (2)C40—C47—H47B109.7
C22—N1—C20118.0 (3)C44—C47—H47A109.7
C25—N2—C26119.0 (3)C44—C47—H47B109.7
C25—N2—C27124.3 (3)H47A—C47—H47B108.2
C26—N2—C27113.3 (3)C40—C48—H48A108.9
C28—N3—Cd1123.5 (2)C40—C48—H48B108.9
C31—N3—Cd1118.5 (2)H48A—C48—H48B107.7
C31—N3—C28118.0 (3)C49—C48—C40113.3 (3)
C33—N4—C34119.2 (3)C49—C48—H48A108.9
C33—N4—C35126.2 (3)C49—C48—H48B108.9
C34—N4—C35113.1 (3)O5—C49—Cd162.76 (17)
N1—C20—H20118.7O5—C49—C48119.6 (3)
N1—C20—C21122.6 (3)O6—C49—Cd156.67 (17)
C21—C20—H20118.7O6—C49—O5119.4 (3)
C20—C21—H21120.7O6—C49—C48121.0 (3)
C20—C21—C24118.6 (3)C48—C49—Cd1176.8 (2)
C24—C21—H21120.7O7—C50—Cd159.7 (4)
N1—C22—H22118.5O7—C50—O8A119.6 (5)
N1—C22—C23123.0 (3)O7—C50—C51120.2 (5)
C23—C22—H22118.5O7A—C50—Cd162.6 (2)
C22—C23—H23120.4O7A—C50—C51116.1 (4)
C22—C23—C24119.2 (3)O8—C50—Cd154.1 (5)
C24—C23—H23120.4O8—C50—O7A116.8 (6)
C21—C24—C25119.2 (3)O8—C50—C51127.1 (7)
C23—C24—C21118.6 (3)O8A—C50—Cd161.7 (3)
C23—C24—C25122.0 (3)O8A—C50—C51118.9 (5)
O1—C25—N2122.7 (3)C51—C50—Cd1177.8 (3)
O1—C25—C24119.0 (3)C50—C51—H51A109.2
N2—C25—C24118.3 (3)C50—C51—H51B109.2
N2—C26—H26A109.6C50—C51—C54112.1 (3)
N2—C26—H26B109.6H51A—C51—H51B107.9
N2—C26—C27i110.3 (3)C54—C51—H51A109.2
H26A—C26—H26B108.1C54—C51—H51B109.2
C27i—C26—H26A109.6C55—C54—C51111.7 (3)
C27i—C26—H26B109.6C55—C54—C62107.8 (3)
N2—C27—C26i108.9 (3)C62—C54—C51108.1 (3)
N2—C27—H27A109.9C63—C54—C51110.9 (3)
N2—C27—H27B109.9C63—C54—C55109.3 (3)
C26i—C27—H27A109.9C63—C54—C62109.0 (3)
C26i—C27—H27B109.9C54—C55—H55A109.7
H27A—C27—H27B108.3C54—C55—H55B109.7
N3—C28—H28118.7H55A—C55—H55B108.2
N3—C28—C29122.6 (3)C56—C55—C54110.0 (3)
C29—C28—H28118.7C56—C55—H55A109.7
C28—C29—H29120.2C56—C55—H55B109.7
C28—C29—C32119.6 (3)C55—C56—H56109.2
C32—C29—H29120.2C55—C56—C60110.2 (3)
C31—C30—H30120.2C57—C56—C55109.7 (3)
C31—C30—C32119.6 (3)C57—C56—H56109.2
C32—C30—H30120.2C57—C56—C60109.4 (3)
N3—C31—C30122.8 (3)C60—C56—H56109.2
N3—C31—H31118.6C56—C57—H57A109.7
C30—C31—H31118.6C56—C57—H57B109.7
C29—C32—C33119.6 (3)C56—C57—C58109.8 (3)
C30—C32—C29117.4 (3)H57A—C57—H57B108.2
C30—C32—C33122.6 (3)C58—C57—H57A109.7
O2—C33—N4122.6 (3)C58—C57—H57B109.7
O2—C33—C32119.1 (3)C57—C58—H58109.7
N4—C33—C32118.2 (3)C57—C58—C59108.8 (3)
N4—C34—H34A109.8C57—C58—C63109.7 (3)
N4—C34—H34B109.8C59—C58—H58109.7
N4—C34—C35ii109.2 (3)C63—C58—H58109.7
H34A—C34—H34B108.3C63—C58—C59109.1 (3)
C35ii—C34—H34A109.8C58—C59—H59A109.5
C35ii—C34—H34B109.8C58—C59—H59B109.5
N4—C35—C34ii109.4 (3)C58—C59—C61110.7 (3)
N4—C35—H35A109.8H59A—C59—H59B108.1
N4—C35—H35B109.8C61—C59—H59A109.5
C34ii—C35—H35A109.8C61—C59—H59B109.5
C34ii—C35—H35B109.8C56—C60—H60A109.7
H35A—C35—H35B108.2C56—C60—H60B109.7
H36A—C36—H36B107.3H60A—C60—H60B108.2
C37—C36—H36A108.1C61—C60—C56109.8 (3)
C37—C36—H36B108.1C61—C60—H60A109.7
C37—C36—C38116.8 (3)C61—C60—H60B109.7
C38—C36—H36A108.1C59—C61—C64107.4 (3)
C38—C36—H36B108.1C60—C61—C59107.9 (3)
O3—C37—O4123.5 (3)C60—C61—C62108.6 (3)
O3—C37—C36122.5 (3)C60—C61—C64111.6 (3)
O4—C37—C36113.9 (3)C62—C61—C59108.8 (3)
C36—C38—C39112.2 (3)C62—C61—C64112.3 (3)
C36—C38—C45107.7 (3)C54—C62—H62A109.4
C45—C38—C39107.6 (3)C54—C62—H62B109.4
C46—C38—C36111.3 (3)C61—C62—C54111.3 (3)
C46—C38—C39109.0 (3)C61—C62—H62A109.4
C46—C38—C45109.0 (3)C61—C62—H62B109.4
C38—C39—H39A109.4H62A—C62—H62B108.0
C38—C39—H39B109.4C54—C63—C58110.4 (3)
H39A—C39—H39B108.0C54—C63—H63A109.6
C40—C39—C38111.4 (2)C54—C63—H63B109.6
C40—C39—H39A109.4C58—C63—H63A109.6
C40—C39—H39B109.4C58—C63—H63B109.6
C39—C40—C48108.2 (2)H63A—C63—H63B108.1
C41—C40—C39108.1 (2)C61—C64—H64A108.2
C41—C40—C48111.4 (3)C61—C64—H64B108.2
C47—C40—C39108.7 (3)H64A—C64—H64B107.4
C47—C40—C41109.4 (3)C65—C64—C61116.2 (3)
C47—C40—C48110.9 (3)C65—C64—H64A108.2
C40—C41—H41A109.7C65—C64—H64B108.2
C40—C41—H41B109.7O9—C65—O10123.1 (4)
C40—C41—C42110.0 (3)O9—C65—C64123.8 (4)
H41A—C41—H41B108.2O10—C65—C64113.1 (3)
C42—C41—H41A109.7
Cd1—O5—C49—O61.1 (3)C38—C39—C40—C4759.9 (3)
Cd1—O5—C49—C48177.5 (3)C38—C39—C40—C48179.6 (3)
Cd1—O6—C49—O51.2 (3)C39—C38—C45—C4459.0 (3)
Cd1—O6—C49—C48177.4 (3)C39—C38—C46—C4259.1 (3)
Cd1—O7—C50—O8A15.7 (8)C39—C40—C41—C4260.0 (3)
Cd1—O7—C50—C51177.5 (3)C39—C40—C47—C4458.5 (3)
Cd1—O7A—C50—O81.8 (8)C39—C40—C48—C49170.0 (3)
Cd1—O7A—C50—C51178.1 (3)C40—C41—C42—C4358.9 (3)
Cd1—O8—C50—O7A1.9 (9)C40—C41—C42—C4662.0 (3)
Cd1—O8—C50—C51177.8 (3)C40—C48—C49—O5102.6 (4)
Cd1—O8A—C50—O715.4 (8)C40—C48—C49—O676.1 (4)
Cd1—O8A—C50—C51177.6 (3)C41—C40—C47—C4459.3 (3)
Cd1—N1—C20—C21179.5 (3)C41—C40—C48—C4951.3 (4)
Cd1—N1—C22—C23179.2 (3)C41—C42—C43—C4459.5 (4)
Cd1—N3—C28—C29178.7 (3)C41—C42—C46—C3861.0 (3)
Cd1—N3—C31—C30179.6 (3)C42—C43—C44—C4560.2 (4)
O7—C50—C51—C54115.1 (7)C42—C43—C44—C4760.1 (4)
O7A—C50—C51—C5480.1 (5)C43—C42—C46—C3859.8 (3)
O8—C50—C51—C5495.7 (10)C43—C44—C45—C3860.0 (4)
O8A—C50—C51—C5478.0 (7)C43—C44—C47—C4060.4 (3)
N1—C20—C21—C240.3 (5)C45—C38—C39—C4059.4 (3)
N1—C22—C23—C240.8 (5)C45—C38—C46—C4258.0 (3)
N3—C28—C29—C321.8 (5)C45—C44—C47—C4059.2 (3)
C20—N1—C22—C230.2 (5)C46—C38—C39—C4058.6 (3)
C20—C21—C24—C231.3 (5)C46—C38—C45—C4459.0 (3)
C20—C21—C24—C25174.1 (3)C46—C42—C43—C4460.6 (3)
C21—C24—C25—O171.0 (4)C47—C40—C41—C4258.2 (3)
C21—C24—C25—N2110.8 (4)C47—C40—C48—C4970.8 (4)
C22—N1—C20—C210.5 (5)C47—C44—C45—C3859.9 (4)
C22—C23—C24—C211.5 (5)C48—C40—C41—C42178.8 (3)
C22—C23—C24—C25173.7 (3)C48—C40—C47—C44177.4 (3)
C23—C24—C25—O1104.2 (4)C50—C51—C54—C5555.4 (5)
C23—C24—C25—N273.9 (4)C50—C51—C54—C62173.8 (4)
C25—N2—C26—C27i102.6 (4)C50—C51—C54—C6366.7 (5)
C25—N2—C27—C26i102.1 (4)C51—C54—C55—C56178.2 (3)
C26—N2—C25—O16.5 (5)C51—C54—C62—C61179.1 (3)
C26—N2—C25—C24175.4 (3)C51—C54—C63—C58178.3 (3)
C26—N2—C27—C26i56.8 (4)C54—C55—C56—C5760.0 (4)
C27—N2—C25—O1164.4 (4)C54—C55—C56—C6060.5 (4)
C27—N2—C25—C2417.5 (5)C55—C54—C62—C6160.1 (4)
C27—N2—C26—C27i57.6 (4)C55—C54—C63—C5858.2 (4)
C28—N3—C31—C300.2 (5)C55—C56—C57—C5860.2 (4)
C28—C29—C32—C301.4 (5)C55—C56—C60—C6159.5 (4)
C28—C29—C32—C33174.2 (3)C56—C57—C58—C5959.9 (4)
C29—C32—C33—O255.0 (5)C56—C57—C58—C6359.4 (4)
C29—C32—C33—N4128.7 (4)C56—C60—C61—C5959.7 (4)
C30—C32—C33—O2117.5 (4)C56—C60—C61—C6258.2 (4)
C30—C32—C33—N458.9 (5)C56—C60—C61—C64177.5 (3)
C31—N3—C28—C291.1 (5)C57—C56—C60—C6161.2 (4)
C31—C30—C32—C290.5 (5)C57—C58—C59—C6159.9 (4)
C31—C30—C32—C33173.1 (3)C57—C58—C63—C5458.7 (4)
C32—C30—C31—N30.1 (5)C58—C59—C61—C6059.7 (4)
C33—N4—C34—C35ii135.2 (3)C58—C59—C61—C6258.1 (4)
C33—N4—C35—C34ii136.2 (3)C58—C59—C61—C64179.9 (3)
C34—N4—C33—O21.5 (5)C59—C58—C63—C5460.4 (4)
C34—N4—C33—C32177.8 (3)C59—C61—C62—C5457.5 (4)
C34—N4—C35—C34ii58.0 (4)C59—C61—C64—C65166.6 (3)
C35—N4—C33—O2166.5 (3)C60—C56—C57—C5860.8 (4)
C35—N4—C33—C3217.2 (5)C60—C61—C62—C5459.7 (4)
C35—N4—C34—C35ii57.9 (4)C60—C61—C64—C6548.5 (4)
C36—C38—C39—C40177.7 (3)C61—C64—C65—O9110.9 (4)
C36—C38—C45—C44179.9 (3)C61—C64—C65—O1072.3 (5)
C36—C38—C46—C42176.7 (3)C62—C54—C55—C5659.6 (4)
C37—C36—C38—C3976.8 (4)C62—C54—C63—C5859.4 (4)
C37—C36—C38—C45165.0 (3)C62—C61—C64—C6573.8 (4)
C37—C36—C38—C4645.6 (4)C63—C54—C55—C5658.8 (4)
C38—C36—C37—O3115.1 (4)C63—C54—C62—C6158.4 (4)
C38—C36—C37—O467.4 (4)C63—C58—C59—C6159.7 (4)
C38—C39—C40—C4158.8 (3)C64—C61—C62—C54176.3 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O5iii0.841.752.588 (3)175
O10—H10···O7iv0.841.892.725 (8)171
O10—H10···O7Aiv0.841.702.520 (6)165
C39—H39A···O40.992.523.135 (4)120
C47—H47B···O60.992.553.163 (4)120
C55—H55B···O7A0.992.463.009 (7)115
C62—H62B···O100.992.533.115 (4)117
C63—H63B···O8A0.992.473.107 (8)121
Symmetry codes: (iii) x+2, y+1, z+2; (iv) x+2, y+2, z+1.
 

Acknowledgements

Funding for this work was provided by the Honors College of Michigan State University. JZT thanks the Michigan State University Chemistry Department Research Experiences for Undergraduates Program for her participation in this research project (NSF grant No. CHE-1358842).

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