Di-μ-chlorido-bis­[(2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)copper(II)] bis­(tri­fluoro­methane­sulfonate)

Adrian, R.A.; Duarte, J.J.; Arman, H.D.

doi:10.1107/S2414314621010968

metal-organic compounds

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ISSN: 2414-3146

Volume 6| Part 10| October 2021| x211096

https://doi.org/10.1107/S2414314621010968

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Di-μ-chlorido-bis[(2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)copper(II)] bis(trifluoromethanesulfonate)

Rafael A. Adrian,^a ^* Jose J. Duarte ^a and Hadi D. Arman ^b

^aDepartment of Chemistry and Biochemistry, University of the Incarnate Word, San Antonio TX 78209, USA, and ^bDepartment of Chemistry, The University of Texas at San Antonio, San Antonio TX 78249, USA
^*Correspondence e-mail: adrian@uiwtx.edu

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 18 October 2021; accepted 20 October 2021; online 21 October 2021)

In the centrosymmetric title complex, [Cu₂Cl₂(C₁₅H₁₁N₃)₂](CF₃O₃S)₂, the Cu^II metal center is fivefold coordinated by two chloride ions and three nitrogen atoms of the terpyridine ligand in a distorted square-pyramidal geometry; two trifluoromethanesulfonate ions complete the outer coordination sphere. π–π stacking interactions between the pyridyl rings in adjacent molecules contribute to the alignment of the complexes in columns along the a-axis. This structure represents the first example of a binuclear dication of formula [Cu(terpy)₂Cl₂]²⁺ with trifluoromethanesulfonate as counter-ions.

Keywords: crystal structure; terpyridine; copper; trifluoromethanesulfonate salt; bridging chloride; π–π stacking.

CCDC reference: 2116881

Structure description

Terpyridines are some of the most studied nitrogen-based tridentate ligands in coordination chemistry, and their metal complexes have found application in catalysis (Wei et al., 2019 ; Choroba et al., 2019 ), supramolecular chemistry (Wei et al., 2019), and medicinal chemistry (Glišić et al., 2018 ; Malarz et al., 2021 ; Li et al., 2020 ). Recently, copper(II) terpyridine complexes have received much attention due to their remarkable cytotoxicity and ability to interact with DNA (Karges et al., 2021 ); herein, we report the synthesis and structure of the title copper(II) terpyridine complex.

The asymmetric unit of the title compound, depicted in Fig. 1, consists of half of a centrosymmetric dication [Cu(terpy)₂Cl₂]²⁺ and one trifluoromethanesulfonate ion completing the outer coordination sphere. The Cu—N, and Cu—Cl distances, as well as, the Cl—Cu—Cl, N—Cu—Cl and N—Cu—N angles are in good agreement with the reported values in similar copper(II) terpyridine complexes currently available in the CSD (version 5.42 with update September 2021; Rojo et al., 1987 ; refcode FECJEC; Valdés-Martínez et al., 2002; refcode HULZAP; Gasser et al., 2004 ; refcode HULZAP01). All relevant bond lengths and angles involving the Cu atom are presented in Table 1.

Table 1
Selected geometric parameters (Å, °)

Cu1—Cl1	2.2265 (5)	Cu1—N2	1.9420 (17)
Cu1—Cl1ⁱ	2.7660 (6)	Cu1—N1	2.0397 (18)
Cu1—N3	2.0278 (19)

Cl1—Cu1—Cl1ⁱ	89.944 (18)	N2—Cu1—N3	80.39 (7)
N3—Cu1—Cl1ⁱ	90.30 (5)	N2—Cu1—N1	80.11 (7)
N3—Cu1—Cl1	99.82 (5)	N1—Cu1—Cl1	99.60 (5)
N3—Cu1—N1	159.58 (7)	N1—Cu1—Cl1ⁱ	95.97 (5)
N2—Cu1—Cl1ⁱ	90.83 (5)	Cu1—Cl1—Cu1ⁱ	90.056 (18)
N2—Cu1—Cl1	179.20 (5)
Symmetry code: (i) .

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level; H atoms are omitted for clarity. Symmetry operator for generating equivalent atoms: (i) 1 − x, 1 − y, 1 − z.

In the crystal packing of the title compound, π–π stacking interactions between the N1 and N3 pyridyl ring of adjacent molecules are observed, with a centroid-to-centroid (Cg⋯Cg) distance of 3.658 (1) Å and an offset distance of 1.723 Å. No other supramolecuar interaction is present in the crystal packing of the title compound.

Synthesis and crystallization

The title compound was obtained as product of the reaction of 2,2′:6′,2′′-terpyridine (0.100 g, 0.429 mmol) with copper(II) chloride dihydrate (0.073 g, 0.429 mmol) in acetonitrile after the addition of silver trifluoromethanesulfonate (0.110 g, 0.429 mmol) and filtration using a 0.45 µm PTFE syringe filter. Crystals suitable for X-ray diffraction of the title compound were obtained by vapor diffusion of diethyl ether over the resulting acetonitrile solution at 278 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were located in a difference map and refined in idealized positions using a riding model with atomic displacement parameters of U_iso(H) = 1.2U_eq(C) and with a C—H distance of 0.95 Å.

Table 2
Experimental details

Crystal data
Chemical formula	[Cu₂Cl₂(C₁₅H₁₁N₃)₂](CF₃O₃S)₂
M_r	962.65
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	98
a, b, c (Å)	7.2767 (2), 9.8394 (2), 13.1746 (3)
α, β, γ (°)	106.667 (2), 91.226 (2), 105.453 (2)
V (Å³)	866.08 (4)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.59
Crystal size (mm)	0.47 × 0.17 × 0.1

Data collection
Diffractometer	XtaLAB AFC12 (RCD3): Kappa single
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	0.741, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	33748, 3982, 3889
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.094, 1.08
No. of reflections	3982
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.41
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2116881

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621010968/bt4119sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621010968/bt4119Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621010968/bt4119Isup3.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: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Di-µ-chlorido-bis[(2,2':6',2''-terpyridine-κ³N,N',N'')copper(II)] bis(trifluoromethanesulfonate) top

Crystal data top

[Cu₂Cl₂(C₁₅H₁₁N₃)₂](CF₃O₃S)₂	Z = 1
M_r = 962.65	F(000) = 482
Triclinic, P1	D_x = 1.846 Mg m⁻³
a = 7.2767 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8394 (2) Å	Cell parameters from 14071 reflections
c = 13.1746 (3) Å	θ = 3.1–29.5°
α = 106.667 (2)°	µ = 1.59 mm⁻¹
β = 91.226 (2)°	T = 98 K
γ = 105.453 (2)°	Block, clear bluish green
V = 866.08 (4) Å³	0.47 × 0.17 × 0.1 mm

Data collection top

XtaLAB AFC12 (RCD3): Kappa single diffractometer	3889 reflections with I > 2σ(I)
Radiation source: Rotating-anode X-ray tube, Rigaku (Mo) X-ray Source	R_int = 0.047
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −9→9
T_min = 0.741, T_max = 1.000	k = −12→12
33748 measured reflections	l = −16→17
3982 independent 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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0529P)² + 0.6752P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
3982 reflections	Δρ_max = 0.55 e Å⁻³
253 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints

Special details top

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. H atoms were located in a difference map and refined in idealized positions using a riding model with atomic displacement parameters of U_iso(H) = 1.2U_eq(C) and with a C—H distance of 0.95 Å.

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

	x	y	z	U_iso*/U_eq
Cu1	0.49265 (4)	0.41355 (3)	0.60172 (2)	0.01772 (10)
Cl1	0.62384 (8)	0.36614 (6)	0.44902 (4)	0.02026 (13)
S1	0.50126 (8)	0.15121 (6)	0.79698 (4)	0.02142 (13)
F2	0.7785 (2)	0.02432 (18)	0.78751 (14)	0.0396 (4)
F1	0.6642 (2)	0.06787 (19)	0.93864 (12)	0.0395 (4)
F3	0.5041 (2)	−0.11260 (17)	0.80642 (16)	0.0478 (4)
O1	0.6469 (2)	0.29199 (17)	0.83604 (12)	0.0239 (3)
O3	0.3333 (2)	0.1385 (2)	0.85354 (15)	0.0336 (4)
O2	0.4661 (3)	0.0941 (2)	0.68265 (13)	0.0360 (4)
N3	0.2255 (3)	0.27262 (19)	0.55326 (14)	0.0188 (4)
N2	0.3802 (3)	0.45334 (19)	0.73563 (14)	0.0168 (3)
N1	0.7290 (3)	0.55151 (19)	0.70135 (14)	0.0184 (4)
C11	0.1030 (3)	0.2851 (2)	0.62992 (16)	0.0192 (4)
C5	0.6901 (3)	0.6111 (2)	0.80261 (16)	0.0189 (4)
C10	0.1958 (3)	0.3840 (2)	0.73629 (16)	0.0186 (4)
C6	0.4902 (3)	0.5499 (2)	0.82254 (16)	0.0179 (4)
C9	0.1110 (3)	0.4087 (2)	0.83124 (17)	0.0220 (4)
H9	−0.019262	0.358669	0.833457	0.026*
C15	0.1555 (3)	0.1851 (2)	0.45439 (17)	0.0220 (4)
H15	0.240897	0.174252	0.401071	0.026*
C14	−0.0386 (3)	0.1094 (2)	0.42706 (18)	0.0238 (5)
H14	−0.084305	0.047636	0.356325	0.029*
C12	−0.0910 (3)	0.2144 (2)	0.60811 (17)	0.0212 (4)
H12	−0.173957	0.225959	0.662670	0.025*
C13	−0.1631 (3)	0.1253 (2)	0.50390 (18)	0.0231 (4)
H13	−0.296333	0.076425	0.486484	0.028*
C7	0.4138 (3)	0.5820 (2)	0.91921 (16)	0.0208 (4)
H7	0.489630	0.651756	0.981351	0.025*
C4	0.8284 (3)	0.7197 (3)	0.87846 (17)	0.0225 (4)
H4	0.798549	0.759683	0.948670	0.027*
C8	0.2229 (3)	0.5089 (3)	0.92254 (17)	0.0237 (5)
H8	0.168203	0.527811	0.988179	0.028*
C2	1.0514 (3)	0.7057 (3)	0.74756 (18)	0.0241 (5)
H2	1.176548	0.735707	0.727006	0.029*
C16	0.6177 (3)	0.0264 (3)	0.83346 (19)	0.0266 (5)
C1	0.9066 (3)	0.5979 (2)	0.67581 (17)	0.0216 (4)
H1	0.934595	0.555208	0.605681	0.026*
C3	1.0114 (3)	0.7691 (3)	0.84983 (18)	0.0254 (5)
H3	1.107711	0.845362	0.899683	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02295 (16)	0.01815 (15)	0.01013 (14)	0.00641 (11)	0.00275 (10)	0.00076 (10)
Cl1	0.0282 (3)	0.0213 (2)	0.0128 (2)	0.0121 (2)	0.00591 (19)	0.00269 (19)
S1	0.0221 (3)	0.0223 (3)	0.0156 (3)	0.0060 (2)	−0.00080 (19)	−0.0002 (2)
F2	0.0382 (9)	0.0427 (9)	0.0461 (9)	0.0246 (7)	0.0131 (7)	0.0132 (7)
F1	0.0508 (10)	0.0437 (9)	0.0241 (7)	0.0128 (8)	−0.0061 (7)	0.0120 (7)
F3	0.0458 (10)	0.0206 (7)	0.0667 (12)	0.0001 (7)	−0.0117 (8)	0.0074 (7)
O1	0.0284 (8)	0.0199 (7)	0.0201 (8)	0.0056 (6)	0.0030 (6)	0.0021 (6)
O3	0.0230 (8)	0.0371 (10)	0.0371 (10)	0.0075 (7)	0.0075 (7)	0.0066 (8)
O2	0.0400 (10)	0.0429 (11)	0.0171 (8)	0.0111 (9)	−0.0078 (7)	−0.0016 (7)
N3	0.0262 (9)	0.0162 (8)	0.0132 (8)	0.0065 (7)	0.0020 (7)	0.0028 (7)
N2	0.0215 (9)	0.0152 (8)	0.0130 (8)	0.0063 (7)	0.0008 (6)	0.0021 (6)
N1	0.0239 (9)	0.0182 (8)	0.0133 (8)	0.0075 (7)	0.0024 (7)	0.0038 (7)
C11	0.0269 (11)	0.0159 (9)	0.0149 (9)	0.0073 (8)	0.0010 (8)	0.0037 (8)
C5	0.0248 (11)	0.0190 (10)	0.0141 (9)	0.0087 (8)	0.0032 (8)	0.0043 (8)
C10	0.0237 (10)	0.0167 (9)	0.0157 (10)	0.0073 (8)	0.0014 (8)	0.0039 (8)
C6	0.0234 (10)	0.0152 (9)	0.0144 (9)	0.0058 (8)	0.0014 (8)	0.0030 (8)
C9	0.0227 (11)	0.0225 (10)	0.0186 (10)	0.0053 (9)	0.0042 (8)	0.0039 (8)
C15	0.0332 (12)	0.0176 (10)	0.0144 (10)	0.0080 (9)	0.0016 (8)	0.0031 (8)
C14	0.0362 (12)	0.0149 (9)	0.0167 (10)	0.0056 (9)	−0.0045 (9)	0.0011 (8)
C12	0.0247 (11)	0.0182 (10)	0.0205 (10)	0.0065 (8)	0.0017 (8)	0.0054 (8)
C13	0.0259 (11)	0.0158 (10)	0.0246 (11)	0.0040 (8)	−0.0045 (9)	0.0039 (8)
C7	0.0256 (11)	0.0210 (10)	0.0122 (9)	0.0061 (9)	0.0010 (8)	0.0000 (8)
C4	0.0261 (11)	0.0241 (11)	0.0157 (10)	0.0088 (9)	0.0031 (8)	0.0020 (8)
C8	0.0282 (12)	0.0277 (11)	0.0134 (10)	0.0087 (9)	0.0055 (8)	0.0025 (8)
C2	0.0215 (11)	0.0285 (11)	0.0233 (11)	0.0074 (9)	0.0034 (8)	0.0093 (9)
C16	0.0308 (12)	0.0197 (10)	0.0240 (11)	0.0049 (9)	−0.0022 (9)	0.0010 (9)
C1	0.0266 (11)	0.0250 (11)	0.0166 (10)	0.0114 (9)	0.0055 (8)	0.0075 (8)
C3	0.0256 (11)	0.0275 (11)	0.0198 (11)	0.0063 (9)	−0.0014 (9)	0.0036 (9)

Geometric parameters (Å, º) top

Cu1—Cl1	2.2265 (5)	C10—C9	1.394 (3)
Cu1—Cl1ⁱ	2.7660 (6)	C6—C7	1.387 (3)
Cu1—N3	2.0278 (19)	C9—H9	0.9500
Cu1—N2	1.9420 (17)	C9—C8	1.390 (3)
Cu1—N1	2.0397 (18)	C15—H15	0.9500
S1—O1	1.4466 (17)	C15—C14	1.394 (3)
S1—O3	1.4409 (18)	C14—H14	0.9500
S1—O2	1.4392 (17)	C14—C13	1.376 (3)
S1—C16	1.826 (2)	C12—H12	0.9500
F2—C16	1.331 (3)	C12—C13	1.401 (3)
F1—C16	1.335 (3)	C13—H13	0.9500
F3—C16	1.337 (3)	C7—H7	0.9500
N3—C11	1.362 (3)	C7—C8	1.392 (3)
N3—C15	1.339 (3)	C4—H4	0.9500
N2—C10	1.335 (3)	C4—C3	1.391 (3)
N2—C6	1.336 (3)	C8—H8	0.9500
N1—C5	1.364 (3)	C2—H2	0.9500
N1—C1	1.336 (3)	C2—C1	1.384 (3)
C11—C10	1.481 (3)	C2—C3	1.386 (3)
C11—C12	1.380 (3)	C1—H1	0.9500
C5—C6	1.479 (3)	C3—H3	0.9500
C5—C4	1.388 (3)

Cl1—Cu1—Cl1ⁱ	89.944 (18)	C8—C9—C10	117.9 (2)
N3—Cu1—Cl1ⁱ	90.30 (5)	C8—C9—H9	121.0
N3—Cu1—Cl1	99.82 (5)	N3—C15—H15	118.9
N3—Cu1—N1	159.58 (7)	N3—C15—C14	122.2 (2)
N2—Cu1—Cl1ⁱ	90.83 (5)	C14—C15—H15	118.9
N2—Cu1—Cl1	179.20 (5)	C15—C14—H14	120.4
N2—Cu1—N3	80.39 (7)	C13—C14—C15	119.1 (2)
N2—Cu1—N1	80.11 (7)	C13—C14—H14	120.4
N1—Cu1—Cl1	99.60 (5)	C11—C12—H12	120.7
N1—Cu1—Cl1ⁱ	95.97 (5)	C11—C12—C13	118.7 (2)
Cu1—Cl1—Cu1ⁱ	90.056 (18)	C13—C12—H12	120.7
O1—S1—C16	102.05 (10)	C14—C13—C12	119.2 (2)
O3—S1—O1	114.97 (10)	C14—C13—H13	120.4
O3—S1—C16	103.57 (11)	C12—C13—H13	120.4
O2—S1—O1	114.19 (11)	C6—C7—H7	121.0
O2—S1—O3	115.73 (12)	C6—C7—C8	118.1 (2)
O2—S1—C16	103.90 (11)	C8—C7—H7	121.0
C11—N3—Cu1	113.61 (14)	C5—C4—H4	120.6
C15—N3—Cu1	127.30 (15)	C5—C4—C3	118.8 (2)
C15—N3—C11	118.61 (19)	C3—C4—H4	120.6
C10—N2—Cu1	118.38 (14)	C9—C8—C7	121.0 (2)
C10—N2—C6	123.04 (18)	C9—C8—H8	119.5
C6—N2—Cu1	118.58 (14)	C7—C8—H8	119.5
C5—N1—Cu1	113.57 (14)	C1—C2—H2	120.5
C1—N1—Cu1	127.51 (15)	C1—C2—C3	119.1 (2)
C1—N1—C5	118.60 (19)	C3—C2—H2	120.5
N3—C11—C10	114.06 (19)	F2—C16—S1	111.78 (16)
N3—C11—C12	122.2 (2)	F2—C16—F1	107.3 (2)
C12—C11—C10	123.8 (2)	F2—C16—F3	107.8 (2)
N1—C5—C6	114.01 (18)	F1—C16—S1	110.99 (16)
N1—C5—C4	121.9 (2)	F1—C16—F3	106.5 (2)
C4—C5—C6	124.13 (19)	F3—C16—S1	112.25 (17)
N2—C10—C11	113.09 (18)	N1—C1—C2	122.5 (2)
N2—C10—C9	119.91 (19)	N1—C1—H1	118.7
C9—C10—C11	127.0 (2)	C2—C1—H1	118.7
N2—C6—C5	113.29 (18)	C4—C3—H3	120.5
N2—C6—C7	120.03 (19)	C2—C3—C4	119.1 (2)
C7—C6—C5	126.68 (19)	C2—C3—H3	120.5
C10—C9—H9	121.0

Cu1—N3—C11—C10	−7.7 (2)	N1—C5—C4—C3	0.2 (3)
Cu1—N3—C11—C12	170.55 (16)	C11—N3—C15—C14	1.5 (3)
Cu1—N3—C15—C14	−170.07 (15)	C11—C10—C9—C8	−178.6 (2)
Cu1—N2—C10—C11	−0.7 (2)	C11—C12—C13—C14	0.8 (3)
Cu1—N2—C10—C9	179.33 (15)	C5—N1—C1—C2	−1.1 (3)
Cu1—N2—C6—C5	−1.4 (2)	C5—C6—C7—C8	−177.9 (2)
Cu1—N2—C6—C7	179.33 (15)	C5—C4—C3—C2	−1.7 (3)
Cu1—N1—C5—C6	7.0 (2)	C10—N2—C6—C5	179.27 (18)
Cu1—N1—C5—C4	−172.78 (16)	C10—N2—C6—C7	0.0 (3)
Cu1—N1—C1—C2	171.97 (16)	C10—C11—C12—C13	178.98 (19)
O1—S1—C16—F2	−60.24 (18)	C10—C9—C8—C7	−0.1 (3)
O1—S1—C16—F1	59.49 (19)	C6—N2—C10—C11	178.63 (18)
O1—S1—C16—F3	178.50 (17)	C6—N2—C10—C9	−1.4 (3)
O3—S1—C16—F2	−179.95 (16)	C6—C5—C4—C3	−179.6 (2)
O3—S1—C16—F1	−60.22 (19)	C6—C7—C8—C9	−1.1 (3)
O3—S1—C16—F3	58.8 (2)	C15—N3—C11—C10	179.69 (18)
O2—S1—C16—F2	58.73 (19)	C15—N3—C11—C12	−2.1 (3)
O2—S1—C16—F1	178.47 (17)	C15—C14—C13—C12	−1.5 (3)
O2—S1—C16—F3	−62.5 (2)	C12—C11—C10—N2	−172.60 (19)
N3—C11—C10—N2	5.6 (3)	C12—C11—C10—C9	7.4 (3)
N3—C11—C10—C9	−174.4 (2)	C4—C5—C6—N2	175.9 (2)
N3—C11—C12—C13	1.0 (3)	C4—C5—C6—C7	−4.9 (3)
N3—C15—C14—C13	0.3 (3)	C1—N1—C5—C6	−178.99 (18)
N2—C10—C9—C8	1.4 (3)	C1—N1—C5—C4	1.3 (3)
N2—C6—C7—C8	1.2 (3)	C1—C2—C3—C4	1.9 (3)
N1—C5—C6—N2	−3.8 (3)	C3—C2—C1—N1	−0.4 (3)
N1—C5—C6—C7	175.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We are thankful for the support of the Department of Chemistry and Biochemistry at the University of the Incarnate Word and the X-ray Diffraction Laboratory at The University of Texas at San Antonio.

Funding information

Funding for this research was provided by: Welch Foundation (award No. BN0032).

References

Choroba, K., Machura, B., Kula, S., Raposo, L. R., Fernandes, A. R., Kruszynski, R., Erfurt, K., Shul'pina, L. S., Kozlov, Y. N. & Shul'pin, G. B. (2019). Dalton Trans. 48, 12656–12673. Web of Science CSD CrossRef CAS PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gasser, G., Labat, G. & Stoeckli-Evans, H. (2004). Acta Cryst. E60, m244–m246. CSD CrossRef IUCr Journals Google Scholar
Glišić, B. Đ., Nikodinovic-Runic, J., Ilic-Tomic, T., Wadepohl, H., Veselinović, A., Opsenica, I. M. & Djuran, M. I. (2018). Polyhedron, 139, 313–322. Google Scholar
Karges, J., Xiong, K., Blacque, O., Chao, H. & Gasser, G. (2021). Inorg. Chim. Acta, 516, 120137. CSD CrossRef Google Scholar
Li, C., Xu, F., Zhao, Y., Zheng, W., Zeng, W., Luo, Q., Wang, Z., Wu, K., Du, J. & Wang, F. (2020). Front. Chem. 8, 210. CrossRef PubMed Google Scholar
Malarz, K., Zych, D., Gawecki, R., Kuczak, M., Musioł, R. & Mrozek-Wilczkiewicz, A. (2021). Eur. J. Med. Chem. 212, 113032. CrossRef PubMed Google Scholar
Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, England. Google Scholar
Rojo, T., Arriortua, M. I., Ruiz, J., Darriet, J., Villeneuve, G. & Beltran-Porter, D. (1987). J. Chem. Soc. Dalton Trans. pp. 285–291. CSD CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Valdés-Martínez, J., Salazar-Mendoza, D. & Toscano, R. A. (2002). Acta Cryst. E58, m712–m714. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, C., He, Y., Shi, X. & Song, Z. (2019). Coord. Chem. Rev. 385, 1–19. CrossRef CAS PubMed Google Scholar

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