trans-Bis(4-amino­pyridine-κN)bis­(quin­ox­aline-2,3-di­thiol­ato-κ2S,S′)platinum(IV) dimethyl sulfoxide monosolvate

Hu, J.; Nesterov, V.V.; Smucker, B.W.

doi:10.1107/S2414314622001018

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 2| February 2022| x220101

https://doi.org/10.1107/S2414314622001018

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trans-Bis(4-aminopyridine-κN)bis(quinoxaline-2,3-dithiolato-κ²S,S′)platinum(IV) dimethyl sulfoxide monosolvate

Jiandu Hu,^a Volodymyr V. Nesterov ^b and Bradley W. Smucker ^a ^*

^aAustin College, 900 N Grand, Sherman, TX 75090, USA, and ^bDepartment of Chemistry, University of North Texas, 1508 W. Mulberry, Denton, TX, 76201, USA
^*Correspondence e-mail: bsmucker@austincollege.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 18 January 2022; accepted 28 January 2022; online 3 February 2022)

In the structure of the title solvated complex, [Pt(C₈H₄N₂S₂)₂(C₅H₆N₂)₂]·C₂H₆OS or trans-[Pt(4-ap)₂(qdt)₂]·dmso (4-ap = 4-aminopyridyl, C₅H₆N₂; qdt = quinoxaline-2,3-dithiolate, C₈H₄N₂S₂; dmso = dimethyl sulfoxide, C₂H₆OS) the centrosymmetric complex exhibits Pt—S distances in agreement with other Pt^IV—S bond lengths found in platinum(IV) dithiolene complexes. The qdt ligands have intermolecular interactions with an amine hydrogen atom on a 4-ap ligand (hydrogen bonding) and have sandwich π–π interactions with a neighboring qdt ligand.

Keywords: crystal structure; platinum(IV); dithiolene.

CCDC reference: 2145270

Structure description

The title trans-[Pt(4-ap)₂(qdt)₂] ((4-ap = 4-aminopyridyl; qdt = quinoxaline-2,3-dithiolate) complex is located about an inversion center and has the central Pt^IV atom in a pseudo-octahedral N₂S₄ coordination environment (Fig. 1). In contrast to the shorter Pt^II—S distances in salts of [Pt(mnt)₂]^2– (mnt = maleonitriledithiolate), such as 2.295 (2) and 2.2958 (19) Å with the tetraphenylphosphine cation (Begum et al., 2014 ) or 2.290 (2) and 2.282 (2) Å with the tetrabutylammonium cation (Güntner et al., 1989 ), the Pt^IV—S distances of the title coordination compound are 2.3514 (11) Å (Pt1—S1) and 2.3495 (11) Å (Pt1—S2). These distances are similar to those in other platinum(IV) complexes containing bis(dithiolene) ligands and either trans-bis(NH₃) co-ligands, with Pt—S distances of 2.3434 (8) and 2.3461 (7) Å (Siddiqui et al., 2020 ), or trans-bis(PMe₃) co-ligands, with a Pt—S distance of 2.3619 (8) Å (Chandrasekaran et al., 2014 ). The Pt1—N1 distance in the title complex is 2.063 (4) Å, which is similar to the Pt—N distance of 2.055 (2) Å in the aforementioned trans-[Pt(NH₃)₂(mnt)₂] complex (Siddiqui et al., 2020).

Figure 1
The molecular structure of the title complex drawn with displacement ellipsoids at the 50% probability level. Non-labeled atoms are generated by symmetry operation −x + 1, −y + 1, −z. The disordered dmso solvate molecule is shown with only one orientation.

The chelating qdt ligands of this platinum(IV) complex are slightly canted relative to the platinum-sulfur atoms, with a 15.59 (11)° angle between the plane of all the non-H atoms of the qdt ligand versus the plane containing Pt, S1, S2, S1 (1 − x, 1 − y, −z) and S2 (1 − x, 1 − y, −z). This tilt enables sandwich packing between intermolecular qdt ligands with a distance between centroids of the two qdt rings of 3.610 Å (Fig. 2), within the range of π–π interactions (Sinnokrot et al., 2002 ). The basicity of the nitrogen atom on the coordinating qdt ligand (Cummings & Eisenberg, 1995b ) makes it suitable for hydrogen bonding. This is observed between the amine hydrogen H4A and the N3 (x, y + 1, z) atom on a neighboring qdt ligand, with a distance of 2.23 Å (Table 1, Fig. 2). N—H⋯O hydrogen bonding is observed between the complex and the O atom of the dmso solvent molecule.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N3ⁱ	0.87	2.30	3.085 (7)	151
N4—H4B⋯O1ⁱⁱ	0.87	2.28	3.045 (11)	148
Symmetry codes: (i) x, y+1, z; (ii) .

Figure 2
The packing of the complexes showing the hydrogen bonding between the H4A amine hydrogen atom and the N3 (x, y + 1, z) atom on a neighboring qdt ligand as well as the sandwich orientation between adjacent qdt ligands and the distance (Å) between centroids of two qdt rings. Displacement ellipsoids are drawn at the 50% probability level; the dmso solvate is omitted for clarity.

Synthesis and crystallization

An orange solution of the anionic qdt ligand was prepared by combining 9.3 mg of 2,3-quinoxalinedithiol (Cummings & Eisenberg, 1995a ) and 7.7 mg of NaHCO₃ with 25 ml of water and heating at 333 K for 5 h. Upon cooling to room temperature, the orange solution was added, via cannula, to a Schlenk flask containing 34.3 mg of [Pt(4-ap)₄](BF₄)₂, prepared in a similar manner to [Pt(pyz)₄](BF₄)₂ (Derry et al., 2008 ), and 7.9 mg of NaHCO₃. The solution was stirred for 7 d with the exclusion of light. The resulting orange–brown solid was collected via vacuum filtration in air and washed with 3 × 10 ml of water and 15 ml of diethyl ether to give 7.4 mg (28% for [Pt(4-ap)₂(qdt)]). Oxidation of platinum(II) to platinum(IV) likely occurred upon prolonged air exposure of the compound in solution (Geiger et al., 2001 ; Siddiqui et al., 2020).

Light-yellow crystals of the title compound were grown by slow diffusion of water into a dmso solution of the platinum complex.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The dmso solvent molecule is disordered about an inversion center and shows half occupancy.

Table 2
Experimental details

Crystal data
Chemical formula	[Pt(C₈H₄N₂S₂)₂(C₅H₆N₂)₂]·C₂H₆OS
M_r	845.96
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	200
a, b, c (Å)	7.74108 (18), 9.8690 (2), 10.47021 (18)
α, β, γ (°)	99.6963 (16), 102.9798 (17), 100.9394 (19)
V (Å³)	746.43 (3)
Z	1
Radiation type	Cu Kα
μ (mm⁻¹)	12.39
Crystal size (mm)	0.03 × 0.02 × 0.01

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Yarnton, England.]$ )
T_min, T_max	0.671, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15557, 3130, 3097
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.083, 1.11
No. of reflections	3130
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.33, −1.21
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Rigaku Corporation, Yarnton, England.]$ ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) Mercury (Macrae et al., 2020 ), and OLEX2 (Dolomanov et al., 2009).

Structural data

CCDC reference: 2145270

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622001018/wm4160sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622001018/wm4160Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622001018/wm4160Isup3.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 refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

trans-Bis(4-aminopyridine-κN)bis(quinoxaline-2,3-dithiolato-κ²S,S')platinum(IV) dimethyl sulfoxide monosolvate top

Crystal data top

[Pt(C₈H₄N₂S₂)₂(C₅H₆N₂)₂]·C₂H₆OS	Z = 1
M_r = 845.96	F(000) = 416
Triclinic, P1	D_x = 1.882 Mg m⁻³
a = 7.74108 (18) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.8690 (2) Å	Cell parameters from 10134 reflections
c = 10.47021 (18) Å	θ = 4.7–77.2°
α = 99.6963 (16)°	µ = 12.39 mm⁻¹
β = 102.9798 (17)°	T = 200 K
γ = 100.9394 (19)°	Plate, clear light yellow
V = 746.43 (3) Å³	0.03 × 0.02 × 0.01 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3130 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3097 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.7°, θ_min = 4.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	k = −12→12
T_min = 0.671, T_max = 1.000	l = −11→13
15557 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0335P)² + 2.9739P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 1.33 e Å⁻³
3130 reflections	Δρ_min = −1.21 e Å⁻³
218 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00059 (15)

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1	0.500000	0.500000	0.000000	0.02644 (11)
S1	0.81596 (15)	0.56972 (12)	0.10110 (12)	0.0312 (2)
S2	0.46861 (16)	0.38023 (12)	0.17238 (12)	0.0317 (2)
N1	0.4661 (5)	0.6809 (4)	0.1128 (4)	0.0302 (8)
N2	1.0148 (6)	0.4701 (4)	0.2823 (4)	0.0340 (9)
N3	0.7159 (6)	0.2878 (4)	0.3258 (4)	0.0326 (9)
N4	0.4058 (8)	1.0482 (5)	0.3409 (5)	0.0487 (12)
H4A	0.459240	1.121162	0.316472	0.058*
H4B	0.291608	1.048543	0.329940	0.058*
C1	0.8464 (6)	0.4641 (5)	0.2183 (5)	0.0286 (9)
C2	1.0401 (7)	0.3838 (5)	0.3712 (5)	0.0344 (10)
C3	1.2200 (8)	0.3870 (6)	0.4442 (6)	0.0429 (12)
H3	1.319219	0.449873	0.434033	0.051*
C4	1.2469 (9)	0.2974 (7)	0.5296 (6)	0.0485 (14)
H4	1.364634	0.300343	0.577882	0.058*
C5	1.0979 (9)	0.2013 (6)	0.5445 (6)	0.0475 (14)
H5	1.117997	0.140023	0.601820	0.057*
C6	0.9238 (9)	0.1967 (6)	0.4759 (5)	0.0441 (13)
H6	0.826180	0.132057	0.486098	0.053*
C7	0.8918 (7)	0.2901 (5)	0.3894 (5)	0.0344 (10)
C8	0.6925 (7)	0.3742 (5)	0.2431 (5)	0.0297 (9)
C9	0.5791 (8)	0.8073 (5)	0.1265 (6)	0.0392 (12)
H9	0.672540	0.811304	0.083782	0.047*
C10	0.5625 (8)	0.9305 (6)	0.2007 (6)	0.0419 (12)
H10	0.643536	1.015621	0.207214	0.050*
C11	0.4242 (8)	0.9282 (5)	0.2661 (5)	0.0377 (11)
C12	0.3087 (8)	0.7949 (6)	0.2519 (6)	0.0408 (12)
H12	0.214927	0.787183	0.294259	0.049*
C13	0.3334 (7)	0.6769 (5)	0.1764 (5)	0.0344 (10)
H13	0.255025	0.590151	0.168660	0.041*
S3	1.0758 (5)	1.0293 (4)	0.0794 (4)	0.0557 (8)	0.5
O1	1.0037 (13)	0.9818 (10)	0.1907 (10)	0.058 (2)	0.5
C1A	1.000 (3)	0.8879 (17)	−0.058 (2)	0.072 (5)	0.5
H1AA	1.061993	0.814997	−0.040118	0.108*	0.5
H1AB	1.023516	0.918671	−0.135433	0.108*	0.5
H1AC	0.870658	0.851496	−0.073236	0.108*	0.5
C1B	0.950 (3)	1.150 (2)	0.030 (2)	0.072 (5)	0.5
H1BA	0.821992	1.107133	0.008588	0.108*	0.5
H1BB	0.979222	1.177789	−0.047899	0.108*	0.5
H1BC	0.979797	1.232401	0.101768	0.108*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02549 (16)	0.02164 (15)	0.02864 (16)	0.00156 (10)	0.00498 (10)	0.00351 (10)
S1	0.0253 (5)	0.0292 (5)	0.0350 (6)	−0.0001 (4)	0.0036 (4)	0.0095 (4)
S2	0.0294 (6)	0.0311 (6)	0.0341 (6)	0.0030 (4)	0.0081 (5)	0.0111 (5)
N1	0.032 (2)	0.0230 (18)	0.035 (2)	0.0056 (15)	0.0114 (17)	0.0015 (15)
N2	0.033 (2)	0.033 (2)	0.033 (2)	0.0061 (17)	0.0046 (17)	0.0048 (17)
N3	0.040 (2)	0.0248 (19)	0.030 (2)	0.0051 (16)	0.0079 (17)	0.0045 (16)
N4	0.055 (3)	0.031 (2)	0.060 (3)	0.008 (2)	0.025 (3)	0.000 (2)
C1	0.029 (2)	0.025 (2)	0.029 (2)	0.0064 (17)	0.0039 (18)	0.0018 (17)
C2	0.041 (3)	0.033 (2)	0.029 (2)	0.012 (2)	0.006 (2)	0.0035 (19)
C3	0.040 (3)	0.047 (3)	0.036 (3)	0.014 (2)	0.003 (2)	0.002 (2)
C4	0.055 (4)	0.054 (3)	0.030 (3)	0.025 (3)	−0.004 (2)	0.001 (2)
C5	0.066 (4)	0.041 (3)	0.033 (3)	0.022 (3)	−0.001 (3)	0.009 (2)
C6	0.062 (4)	0.033 (3)	0.034 (3)	0.012 (2)	0.007 (3)	0.006 (2)
C7	0.044 (3)	0.029 (2)	0.026 (2)	0.010 (2)	0.003 (2)	0.0031 (18)
C8	0.034 (2)	0.025 (2)	0.028 (2)	0.0053 (18)	0.0069 (19)	0.0029 (18)
C9	0.040 (3)	0.025 (2)	0.052 (3)	0.001 (2)	0.022 (2)	0.003 (2)
C10	0.045 (3)	0.028 (2)	0.051 (3)	0.001 (2)	0.020 (3)	0.001 (2)
C11	0.040 (3)	0.031 (2)	0.040 (3)	0.008 (2)	0.010 (2)	0.004 (2)
C12	0.038 (3)	0.035 (3)	0.049 (3)	0.003 (2)	0.018 (2)	0.005 (2)
C13	0.032 (2)	0.028 (2)	0.041 (3)	0.0019 (19)	0.011 (2)	0.004 (2)
S3	0.0454 (16)	0.0553 (18)	0.0601 (19)	−0.0016 (14)	0.0131 (14)	0.0125 (15)
O1	0.053 (5)	0.062 (6)	0.065 (6)	0.013 (4)	0.023 (4)	0.020 (5)
C1A	0.078 (13)	0.045 (9)	0.108 (16)	0.036 (8)	0.035 (11)	0.020 (9)
C1B	0.087 (13)	0.063 (11)	0.087 (12)	0.055 (10)	0.026 (10)	0.026 (9)

Geometric parameters (Å, º) top

Pt1—S1	2.3514 (11)	C4—C5	1.404 (10)
Pt1—S1ⁱ	2.3514 (11)	C5—H5	0.9300
Pt1—S2	2.3495 (11)	C5—C6	1.366 (9)
Pt1—S2ⁱ	2.3495 (11)	C6—H6	0.9300
Pt1—N1	2.063 (4)	C6—C7	1.413 (7)
Pt1—N1ⁱ	2.063 (4)	C9—H9	0.9300
S1—C1	1.743 (5)	C9—C10	1.373 (7)
S2—C8	1.741 (5)	C10—H10	0.9300
N1—C9	1.346 (6)	C10—C11	1.393 (8)
N1—C13	1.342 (6)	C11—C12	1.407 (7)
N2—C1	1.310 (6)	C12—H12	0.9300
N2—C2	1.371 (7)	C12—C13	1.363 (7)
N3—C7	1.369 (7)	C13—H13	0.9300
N3—C8	1.323 (6)	S3—O1	1.505 (10)
N4—H4A	0.8662	S3—C1A	1.728 (19)
N4—H4B	0.8665	S3—C1B	1.752 (16)
N4—C11	1.355 (7)	C1A—H1AA	0.9600
C1—C8	1.446 (7)	C1A—H1AB	0.9600
C2—C3	1.421 (8)	C1A—H1AC	0.9600
C2—C7	1.402 (8)	C1B—H1BA	0.9600
C3—H3	0.9300	C1B—H1BB	0.9600
C3—C4	1.370 (8)	C1B—H1BC	0.9600
C4—H4	0.9300

S1—Pt1—S1ⁱ	180.0	C5—C6—H6	120.0
S2—Pt1—S1	88.43 (4)	C5—C6—C7	120.0 (6)
S2ⁱ—Pt1—S1ⁱ	88.43 (4)	C7—C6—H6	120.0
S2—Pt1—S1ⁱ	91.57 (4)	N3—C7—C2	121.3 (4)
S2ⁱ—Pt1—S1	91.57 (4)	N3—C7—C6	119.1 (5)
S2ⁱ—Pt1—S2	180.0	C2—C7—C6	119.6 (5)
N1ⁱ—Pt1—S1ⁱ	89.99 (12)	N3—C8—S2	116.7 (4)
N1ⁱ—Pt1—S1	90.01 (12)	N3—C8—C1	121.3 (4)
N1—Pt1—S1	89.99 (12)	C1—C8—S2	121.9 (4)
N1—Pt1—S1ⁱ	90.01 (12)	N1—C9—H9	118.6
N1—Pt1—S2	90.33 (12)	N1—C9—C10	122.9 (5)
N1ⁱ—Pt1—S2ⁱ	90.33 (12)	C10—C9—H9	118.6
N1—Pt1—S2ⁱ	89.67 (12)	C9—C10—H10	120.0
N1ⁱ—Pt1—S2	89.67 (12)	C9—C10—C11	120.0 (5)
N1ⁱ—Pt1—N1	180.0	C11—C10—H10	120.0
C1—S1—Pt1	103.03 (16)	N4—C11—C10	121.2 (5)
C8—S2—Pt1	102.34 (17)	N4—C11—C12	122.6 (5)
C9—N1—Pt1	120.7 (3)	C10—C11—C12	116.2 (5)
C13—N1—Pt1	121.6 (3)	C11—C12—H12	119.8
C13—N1—C9	117.7 (4)	C13—C12—C11	120.5 (5)
C1—N2—C2	117.3 (4)	C13—C12—H12	119.8
C8—N3—C7	117.1 (4)	N1—C13—C12	122.7 (5)
H4A—N4—H4B	108.6	N1—C13—H13	118.7
C11—N4—H4A	109.7	C12—C13—H13	118.7
C11—N4—H4B	110.6	O1—S3—C1A	106.8 (8)
N2—C1—S1	116.9 (4)	O1—S3—C1B	104.6 (9)
N2—C1—C8	121.8 (4)	C1A—S3—C1B	103.1 (11)
C8—C1—S1	121.3 (4)	S3—C1A—H1AA	109.5
N2—C2—C3	119.6 (5)	S3—C1A—H1AB	109.5
N2—C2—C7	121.1 (5)	S3—C1A—H1AC	109.5
C7—C2—C3	119.3 (5)	H1AA—C1A—H1AB	109.5
C2—C3—H3	120.0	H1AA—C1A—H1AC	109.5
C4—C3—C2	120.0 (6)	H1AB—C1A—H1AC	109.5
C4—C3—H3	120.0	S3—C1B—H1BA	109.5
C3—C4—H4	119.8	S3—C1B—H1BB	109.5
C3—C4—C5	120.4 (6)	S3—C1B—H1BC	109.5
C5—C4—H4	119.8	H1BA—C1B—H1BB	109.5
C4—C5—H5	119.6	H1BA—C1B—H1BC	109.5
C6—C5—C4	120.7 (5)	H1BB—C1B—H1BC	109.5
C6—C5—H5	119.6

Pt1—S1—C1—N2	173.6 (3)	C2—C3—C4—C5	0.6 (8)
Pt1—S1—C1—C8	−6.3 (4)	C3—C2—C7—N3	177.0 (5)
Pt1—S2—C8—N3	−166.6 (3)	C3—C2—C7—C6	−2.5 (7)
Pt1—S2—C8—C1	16.4 (4)	C3—C4—C5—C6	−0.9 (9)
Pt1—N1—C9—C10	−179.9 (5)	C4—C5—C6—C7	−0.5 (9)
Pt1—N1—C13—C12	179.8 (4)	C5—C6—C7—N3	−177.3 (5)
S1—C1—C8—S2	−7.3 (6)	C5—C6—C7—C2	2.2 (8)
S1—C1—C8—N3	175.8 (4)	C7—N3—C8—S2	−175.4 (3)
N1—C9—C10—C11	0.1 (10)	C7—N3—C8—C1	1.7 (7)
N2—C1—C8—S2	172.8 (4)	C7—C2—C3—C4	1.1 (8)
N2—C1—C8—N3	−4.1 (7)	C8—N3—C7—C2	2.3 (7)
N2—C2—C3—C4	−177.7 (5)	C8—N3—C7—C6	−178.2 (5)
N2—C2—C7—N3	−4.2 (7)	C9—N1—C13—C12	0.7 (8)
N2—C2—C7—C6	176.3 (5)	C9—C10—C11—N4	179.4 (6)
N4—C11—C12—C13	−179.5 (6)	C9—C10—C11—C12	0.6 (9)
C1—N2—C2—C3	−179.4 (4)	C10—C11—C12—C13	−0.7 (9)
C1—N2—C2—C7	1.8 (7)	C11—C12—C13—N1	0.0 (9)
C2—N2—C1—S1	−177.8 (3)	C13—N1—C9—C10	−0.7 (8)
C2—N2—C1—C8	2.2 (7)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3ⁱⁱ	0.87	2.30	3.085 (7)	151
N4—H4B···O1ⁱⁱⁱ	0.87	2.28	3.045 (11)	148

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

Funding information

Funding for this research was provided by: National Science Foundation (grant No. 1726652 to UNT); Welch Foundation (grant No. AD-0007 to Austin College).

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