Poly[[[μ-trans-1,2-bis­(pyridin-4-yl)ethene-κ2N:N′]-μ-iodido-copper(I)]–trans-1,2-bis­(pyridin-4-yl)ethene (1/0.25)]

Hoffman, J.L.; Akhigbe, J.E.; Reinheimer, E.W.; Smucker, B.W.

doi:10.1107/S2414314620009980

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 7| July 2020| x200998

https://doi.org/10.1107/S2414314620009980

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Poly[[[μ-trans-1,2-bis(pyridin-4-yl)ethene-κ²N:N′]-μ-iodido-copper(I)]–trans-1,2-bis(pyridin-4-yl)ethene (1/0.25)]

Jessica L. Hoffman,^a Jessie E. Akhigbe,^a Eric W. Reinheimer ^b and Bradley W. Smucker ^a ^*

^aAustin College, 900 N Grand, Sherman, TX 75090, USA, and ^bRigaku Oxford Diffraction, 9009 New Trails Dr., The Woodlands, TX 77381, USA
^*Correspondence e-mail: bsmucker@austincollege.edu

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 3 June 2020; accepted 20 July 2020; online 24 July 2020)

The title compound, {[CuI(bpe)]·0.25(bpe)}_n, was synthesized similarly to (CuI)₂(bpe) [Neal et al. (2019 ). IUCrData, 4, x190122] with red crystals grown from acetonitrile solutions of CuI and the bpe ligand [bpe = 1,2-bis(pyridin-4-yl)ethene, C₁₂H₁₀N₂]. The structure of the title compound is a type 1 complex in the Graham nomenclature [Graham et al. (2000 ). Inorg. Chem. 39, 5121–5132], having rhombic dimers of Cu₂I₂ that are bridged by two bpe ligands, to form oligomeric ribbons arranged as stairsteps. The step height is 2.8072 (11) Å, which is the Cu—Iⁱ distance of the dimer [symmetry code (i): 1 − x, 2 − y, 1 − z]. The resulting polymer displays a two-dimensional honeycomb framework along the (01 $[\overline1]$ ) plane, and disordered free bpe molecules fill the voids in the crystal.

Keywords: crystal structure; coordination polymer; CuI dimer; copper.

CCDC reference: 2017730

Structure description

The structure of the title compound contains discrete rhombic dimers of Cu₂I₂, where the Cu—I distance is 2.6891 (9) Å, the distance across the dimer (Cu—Iⁱ distance) is 2.8072 (11) Å, and the Cu⋯Cuⁱ separation is 3.544 (1) Å [symmetry code (i): 1 − x, 2 − y, 1 − z]. The approximately tetrahedral geometry around the Cu^I atoms has an N—Cu—N angle of 127.33 (17)° and I—Cu—Iⁱ angle of 99.74 (3)°. Each bpe ligand connects two copper(I) atoms to form oligomeric zigzag ribbons of CuI(bpe), which can be classified as a type 1 complex (Graham et al., 2000), where bpe is 1,2-bis(pyridin-4-yl)ethene. These ribbons are arranged as stairsteps with each stair resulting from the Cu₂I₂ dimer, hence the step height is 2.8072 (11) Å (the Cu—Iⁱ distance, Fig. 1). This packing is quite different from the analogous CuI(4,4′-bipyridyl) complex, where tetrameric units, composed of two Cu₂I₂ dimers bridged by two 4,4′-bipyridyl ligands, are linked by additional 4,4′-bipyridyl ligands to form interpenetrating hexagonal honeycomb sheets (Blake et al., 1999 ).

Figure 1
Displacement ellipsoid plot (50% probability level) of all non-H atoms for the oligomeric ribbons of Cu₂I₂ dimers bridged by bpe and arranged as stairsteps with 2.8072 (11) Å height (the Cu—Iⁱ distance). Cu—I and Cu—Iⁱ distances are shown. Guest bpe molecule are omitted for clarity.

The title compound is quite similar to structures of [CuI(bpe)] containing guest aniline or p-toluidine molecules (Yang et al., 2011 ), except that it contains a bpe molecule, which is disordered over two inversion centers, with occupancy of 0.25. In attempts at identifying this guest molecule, we considered bpe and acetonitrile (crystallization solvent). Refinements on either molecule required substantial restraints and yielded unsatisfactory results. The final model for both, however, gave normal displacement parameters. A lack of C≡N vibrations in the IR spectra of crystals ultimately led towards assigning the guest as a disordered bpe molecule. The use of SQUEEZE (Spek, 2015 ) also seemed less ideal as the position of the guest was evident in difference maps.

Synthesis and crystallization

The title compound was synthesized using the same procedure as reported in the synthesis of polymeric [(CuI)₂(bpe)] (Neal et al., 2019; Parmeggiani & Sacchetti, 2012 ). Red crystals were grown by layering an acetonitrile solution containing freshly prepared CuI, ascorbic acid and KI with another acetonitrile solution containing bpe in a thin tube. The concentration of bpe in this tube is inferred to be greater than the concentration of CuI to afford the red type 1 complexes of [CuI(bpe)] rather than the aforementioned complexes of [(CuI)₂(bpe)], which are type 2 (Graham et al., 2000). Similar structures of [(CuI)(bpe)] were reported with guest aniline or p-toluidine molecules but were made from solvothermal reactions (Yang et al., 2011).

Refinement

Details of the crystal data, data collection, and structure refinement are summarized in Table 1. One-half of the guest bpe molecule is placed close to an inversion center, and its occupancy was fixed to 0.5. As a result, the amount of guest bpe for each CuI(bpe) monomer is 0.25. The geometry of the disordered guest molecule was fully restrained using 1,2 and 1,3 distances from a known target. This molecule was also restrained to be flat, with standard deviation of 0.1 Å³, while displacement parameters were restrained, with effective standard deviation of 0.1 Å² to approximate an isotropic behaviour. Finally, rigid bond restraints were applied to the guest bpe molecule (Sheldrick, 2015b ).

Table 1
Experimental details

Crystal data
Chemical formula	[CuI(C₁₂H₁₀N₂)·0.25C₁₂H₁₀N₂
M_r	418.21
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	7.9004 (2), 10.4260 (3), 10.5078 (3)
α, β, γ (°)	99.903 (2), 104.930 (2), 110.061 (3)
V (Å³)	752.55 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	3.49
Crystal size (mm)	0.14 × 0.10 × 0.06

Data collection
Diffractometer	Rigaku XtaLAB Mini II
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, England.]$ )
T_min, T_max	0.838, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16024, 2683, 2021
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.03
No. of reflections	2683
No. of parameters	200
No. of restraints	87
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −1.01
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2017730

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314620009980/bh4052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620009980/bh4052Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620009980/bh4052Isup3.mol

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[[µ-trans-1,2-bis(pyridin-4-yl)ethene-κ²N:N']-µ-iodido-copper(I)]–trans-1,2-bis(pyridin-4-yl)ethene (1/0.25)] top

Crystal data top

[CuI(C₁₂H₁₀N₂)·0.25C₁₂H₁₀N₂	Z = 2
M_r = 418.21	F(000) = 404
Triclinic, P1	D_x = 1.846 Mg m⁻³
a = 7.9004 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4260 (3) Å	Cell parameters from 6736 reflections
c = 10.5078 (3) Å	θ = 2.1–24.7°
α = 99.903 (2)°	µ = 3.49 mm⁻¹
β = 104.930 (2)°	T = 293 K
γ = 110.061 (3)°	Block, red
V = 752.55 (4) Å³	0.14 × 0.10 × 0.06 mm

Data collection top

Rigaku XtaLAB Mini II diffractometer	2683 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source	2021 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.033
ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (CrysAlis Pro; Rigaku OD, 2019)	h = −9→9
T_min = 0.838, T_max = 1.000	k = −12→12
16024 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0389P)² + 1.4132P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2683 reflections	Δρ_max = 0.60 e Å⁻³
200 parameters	Δρ_min = −1.01 e Å⁻³
87 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0018 (8)
Primary atom site location: dual

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.26536 (6)	0.84672 (5)	0.33204 (4)	0.06679 (19)
Cu1	0.47272 (12)	0.86742 (10)	0.58757 (8)	0.0777 (3)
N1	0.6174 (6)	0.7452 (5)	0.5719 (5)	0.0605 (12)
N2	0.3214 (6)	0.8771 (5)	0.7122 (4)	0.0515 (10)
C1	0.6526 (9)	0.6715 (7)	0.6588 (6)	0.0683 (16)
H1	0.603438	0.674885	0.730152	0.082*
C2	0.7563 (8)	0.5909 (6)	0.6505 (6)	0.0657 (16)
H2	0.773735	0.540343	0.713949	0.079*
C3	0.8346 (8)	0.5847 (6)	0.5482 (6)	0.0572 (14)
C4	0.7964 (9)	0.6579 (7)	0.4552 (7)	0.0743 (18)
H4	0.843618	0.655522	0.382777	0.089*
C5	0.6875 (9)	0.7351 (7)	0.4697 (7)	0.0752 (18)
H5	0.661750	0.782544	0.404776	0.090*
C6	0.9505 (8)	0.5005 (6)	0.5415 (6)	0.0614 (15)
H6	0.953705	0.443793	0.600578	0.074*
C7	0.0594 (8)	0.9694 (6)	1.0045 (5)	0.0578 (14)
H7	0.093427	0.942977	1.084213	0.069*
C8	0.3474 (10)	0.8408 (8)	0.8268 (6)	0.090 (2)
H8	0.427047	0.792999	0.844460	0.108*
C9	0.2652 (10)	0.8686 (8)	0.9223 (6)	0.089 (2)
H9	0.290839	0.840143	1.001801	0.107*
C10	0.1457 (7)	0.9378 (5)	0.9018 (5)	0.0470 (12)
C11	0.1145 (8)	0.9735 (6)	0.7811 (6)	0.0625 (15)
H11	0.034006	1.020025	0.760252	0.075*
C12	0.2020 (8)	0.9406 (6)	0.6906 (6)	0.0643 (16)
H12	0.175498	0.964583	0.608684	0.077*
C13	0.9182 (15)	0.4586 (15)	1.002 (3)	0.207 (11)	0.5
H13	0.901139	0.363730	1.005612	0.248*	0.5
C14	0.7563 (17)	0.4951 (16)	0.9907 (15)	0.157 (8)	0.5
C15	0.7591 (17)	0.6220 (15)	1.0534 (17)	0.173 (9)	0.5
H15	0.873366	0.708859	1.090084	0.207*	0.5
C16	0.5871 (15)	0.6190 (9)	1.0550 (15)	0.265 (11)
H16	0.587357	0.707340	1.100402	0.318*	0.5
H	0.298137	0.295930	0.924152	0.318*	0.5
N17	0.4132 (18)	0.5088 (14)	1.002 (3)	0.268 (16)	0.5
C18	0.5760 (17)	0.3832 (16)	0.926 (2)	0.161 (8)	0.5
H18	0.568167	0.300260	0.863881	0.193*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0821 (3)	0.0961 (3)	0.0635 (3)	0.0621 (3)	0.0395 (2)	0.0464 (2)
Cu1	0.0954 (6)	0.1227 (7)	0.0726 (5)	0.0872 (6)	0.0535 (4)	0.0401 (5)
N1	0.068 (3)	0.084 (3)	0.065 (3)	0.056 (3)	0.039 (2)	0.030 (2)
N2	0.061 (3)	0.068 (3)	0.053 (2)	0.045 (2)	0.033 (2)	0.025 (2)
C1	0.081 (4)	0.100 (5)	0.067 (4)	0.067 (4)	0.043 (3)	0.039 (3)
C2	0.075 (4)	0.084 (4)	0.076 (4)	0.057 (4)	0.041 (3)	0.039 (3)
C3	0.055 (3)	0.064 (3)	0.077 (4)	0.043 (3)	0.032 (3)	0.028 (3)
C4	0.091 (4)	0.104 (5)	0.085 (4)	0.076 (4)	0.059 (4)	0.046 (4)
C5	0.098 (5)	0.106 (5)	0.082 (4)	0.081 (4)	0.058 (4)	0.052 (4)
C6	0.064 (4)	0.064 (3)	0.086 (4)	0.044 (3)	0.041 (3)	0.034 (3)
C7	0.073 (4)	0.088 (4)	0.047 (3)	0.055 (3)	0.036 (3)	0.034 (3)
C8	0.123 (6)	0.162 (7)	0.073 (4)	0.123 (6)	0.062 (4)	0.064 (4)
C9	0.129 (6)	0.160 (7)	0.065 (4)	0.122 (6)	0.061 (4)	0.070 (4)
C10	0.050 (3)	0.063 (3)	0.046 (3)	0.035 (3)	0.026 (2)	0.021 (2)
C11	0.082 (4)	0.093 (4)	0.067 (3)	0.071 (4)	0.050 (3)	0.046 (3)
C12	0.094 (4)	0.094 (4)	0.064 (3)	0.073 (4)	0.054 (3)	0.050 (3)
C13	0.23 (2)	0.15 (2)	0.20 (2)	0.062 (19)	0.00 (2)	0.10 (2)
C14	0.27 (2)	0.124 (12)	0.066 (11)	0.082 (13)	0.017 (13)	0.050 (10)
C15	0.162 (16)	0.099 (11)	0.17 (2)	0.014 (12)	−0.024 (16)	0.035 (12)
C16	0.229 (17)	0.209 (17)	0.233 (19)	0.099 (14)	−0.031 (15)	−0.085 (14)
N17	0.192 (18)	0.28 (3)	0.23 (3)	0.106 (17)	0.02 (2)	−0.12 (2)
C18	0.24 (2)	0.124 (14)	0.120 (17)	0.089 (14)	0.042 (17)	0.043 (12)

Geometric parameters (Å, º) top

I1—Cu1	2.6891 (9)	C9—C10	1.370 (7)
I1—Cu1ⁱ	2.8072 (11)	C9—H9	0.9300
Cu1—N1	1.996 (4)	C10—C11	1.368 (7)
Cu1—N2	2.000 (4)	C11—C12	1.374 (6)
N1—C1	1.326 (7)	C11—H11	0.9300
N1—C5	1.333 (6)	C12—H12	0.9300
N2—C8	1.311 (7)	C13—C13^iv	1.300 (10)
N2—C12	1.322 (6)	C13—C14	1.437 (9)
C1—C2	1.367 (7)	C13—H13	0.9609
C1—H1	0.9300	C14—N17^v	1.348 (15)
C2—C3	1.375 (7)	C14—C15	1.363 (9)
C2—H2	0.9300	C14—C18	1.394 (9)
C3—C4	1.376 (8)	C15—C16	1.353 (9)
C3—C6	1.475 (7)	C15—N17^v	1.45 (2)
C4—C5	1.383 (7)	C15—H15	0.9607
C4—H4	0.9300	C15—H^v	1.11 (2)
C5—H5	0.9300	C16—C18^v	1.348 (9)
C6—C6ⁱⁱ	1.314 (10)	C16—N17	1.350 (9)
C6—H6	0.9300	C16—N17^v	1.362 (9)
C7—C7ⁱⁱⁱ	1.297 (9)	C16—H16	0.9608
C7—C10	1.466 (6)	C16—H^v	0.967 (18)
C7—H7	0.9300	N17—C18^v	1.21 (2)
C8—C9	1.370 (7)	N17—N17^v	1.45 (2)
C8—H8	0.9300	C18—H18	0.9607

Cu1—I1—Cu1ⁱ	80.26 (3)	N17^v—C14—C15	64.6 (10)
N1—Cu1—N2	127.33 (17)	N17^v—C14—C18	52.3 (10)
N1—Cu1—I1	108.03 (13)	C15—C14—C18	116.2 (10)
N2—Cu1—I1	109.45 (12)	N17^v—C14—C13	160.3 (17)
N1—Cu1—I1ⁱ	107.96 (15)	C15—C14—C13	126.9 (13)
N2—Cu1—I1ⁱ	100.67 (13)	C18—C14—C13	116.2 (11)
I1—Cu1—I1ⁱ	99.74 (3)	C16—C15—C14	115.2 (10)
C1—N1—C5	115.8 (4)	C16—C15—N17^v	58.1 (6)
C1—N1—Cu1	124.3 (3)	C14—C15—N17^v	57.2 (8)
C5—N1—Cu1	119.9 (4)	C16—C15—H15	121.9
C8—N2—C12	115.1 (4)	C14—C15—H15	122.8
C8—N2—Cu1	124.8 (3)	N17^v—C15—H15	179.9
C12—N2—Cu1	119.5 (3)	C16—C15—H^v	44.9 (10)
N1—C1—C2	124.4 (5)	C14—C15—H^v	157.2 (16)
N1—C1—H1	117.8	N17^v—C15—H^v	102.3 (13)
C2—C1—H1	117.8	H15—C15—H^v	77.6
C1—C2—C3	119.9 (5)	C18^v—C16—N17	53.2 (10)
C1—C2—H2	120.1	C18^v—C16—C15	172.4 (16)
C3—C2—H2	120.1	N17—C16—C15	129.2 (11)
C2—C3—C4	116.6 (4)	C18^v—C16—N17^v	116.9 (11)
C2—C3—C6	119.8 (5)	N17—C16—N17^v	64.9 (11)
C4—C3—C6	123.5 (5)	C15—C16—N17^v	64.5 (9)
C3—C4—C5	119.8 (5)	C18^v—C16—H16	62.0
C3—C4—H4	120.1	N17—C16—H16	114.6
C5—C4—H4	120.1	C15—C16—H16	116.1
N1—C5—C4	123.5 (5)	N17^v—C16—H16	176.3
N1—C5—H5	118.3	C18^v—C16—H^v	125.1 (15)
C4—C5—H5	118.3	N17—C16—H^v	168 (3)
C6ⁱⁱ—C6—C3	125.1 (7)	C15—C16—H^v	54.4 (13)
C6ⁱⁱ—C6—H6	117.4	N17^v—C16—H^v	118.0 (18)
C3—C6—H6	117.4	H16—C16—H^v	63.3
C7ⁱⁱⁱ—C7—C10	126.7 (6)	C18^v—N17—C14^v	65.8 (8)
C7ⁱⁱⁱ—C7—H7	116.7	C18^v—N17—C16	63.3 (7)
C10—C7—H7	116.7	C14^v—N17—C16	128.9 (12)
N2—C8—C9	124.4 (5)	C18^v—N17—C16^v	168 (3)
N2—C8—H8	117.8	C14^v—N17—C16^v	115.6 (11)
C9—C8—H8	117.8	C16—N17—C16^v	115.1 (11)
C10—C9—C8	120.6 (5)	C18^v—N17—C15^v	123.2 (12)
C10—C9—H9	119.7	C14^v—N17—C15^v	58.2 (7)
C8—C9—H9	119.7	C16—N17—C15^v	172.1 (15)
C11—C10—C9	115.5 (4)	C16^v—N17—C15^v	57.5 (7)
C11—C10—C7	123.8 (4)	C18^v—N17—N17^v	120.1 (14)
C9—C10—C7	120.8 (4)	C14^v—N17—N17^v	171 (3)
C10—C11—C12	120.1 (5)	C16—N17—N17^v	58.0 (7)
C10—C11—H11	120.0	C16^v—N17—N17^v	57.1 (7)
C12—C11—H11	120.0	C15^v—N17—N17^v	114.5 (11)
N2—C12—C11	124.4 (5)	N17^v—C18—C16^v	63.5 (7)
N2—C12—H12	117.8	N17^v—C18—C14	61.9 (9)
C11—C12—H12	117.8	C16^v—C18—C14	125.2 (12)
C13^iv—C13—C14	124.7 (16)	N17^v—C18—H18	176.4
C13^iv—C13—H13	117.5	C16^v—C18—H18	117.6
C14—C13—H13	117.6	C14—C18—H18	117.2

C5—N1—C1—C2	1.2 (10)	C13^iv—C13—C14—C15	−43 (5)
Cu1—N1—C1—C2	−178.1 (5)	C13^iv—C13—C14—C18	147 (3)
N1—C1—C2—C3	1.1 (11)	N17^v—C14—C15—C16	−2.9 (18)
C1—C2—C3—C4	−2.4 (9)	C18—C14—C15—C16	5.8 (16)
C1—C2—C3—C6	178.5 (6)	C13—C14—C15—C16	−164.1 (18)
C2—C3—C4—C5	1.4 (10)	C18—C14—C15—N17^v	8.7 (18)
C6—C3—C4—C5	−179.5 (6)	C13—C14—C15—N17^v	−161 (2)
C1—N1—C5—C4	−2.3 (10)	C14—C15—C16—N17	−1 (2)
Cu1—N1—C5—C4	177.0 (5)	N17^v—C15—C16—N17	−4 (3)
C3—C4—C5—N1	1.0 (11)	C14—C15—C16—N17^v	2.9 (18)
C2—C3—C6—C6ⁱⁱ	−172.0 (8)	C15—C16—N17—C18^v	171 (2)
C4—C3—C6—C6ⁱⁱ	8.9 (12)	N17^v—C16—N17—C18^v	167 (3)
C12—N2—C8—C9	−2.1 (11)	C18^v—C16—N17—C14^v	6 (2)
Cu1—N2—C8—C9	169.2 (6)	C15—C16—N17—C14^v	177 (2)
N2—C8—C9—C10	0.4 (13)	N17^v—C16—N17—C14^v	173 (5)
C8—C9—C10—C11	0.9 (11)	C18^v—C16—N17—C16^v	−167 (3)
C8—C9—C10—C7	−179.2 (7)	C15—C16—N17—C16^v	4 (3)
C7ⁱⁱⁱ—C7—C10—C11	1.9 (12)	N17^v—C16—N17—C16^v	0.001 (1)
C7ⁱⁱⁱ—C7—C10—C9	−178.0 (8)	C18^v—C16—N17—N17^v	−167 (3)
C9—C10—C11—C12	−0.5 (9)	C15—C16—N17—N17^v	4 (3)
C7—C10—C11—C12	179.6 (6)	C15—C14—C18—N17^v	−10 (2)
C8—N2—C12—C11	2.6 (10)	C13—C14—C18—N17^v	161 (2)
Cu1—N2—C12—C11	−169.2 (5)	N17^v—C14—C18—C16^v	−5 (2)
C10—C11—C12—N2	−1.3 (10)	C15—C14—C18—C16^v	−15 (3)
C13^iv—C13—C14—N17^v	−163 (4)	C13—C14—C18—C16^v	156 (2)

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

Funding information

Funding for this research was provided by: Welch Foundation (grant No. AD-0007 to the Chemistry Department at Austin College); Jerry Taylor and Nancy Bryant Foundation (gift to Austin College Science Division).

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