1-(2-Methyl­phen­yl)-4,4′-bipyridin-1-ium tetra­fluorido­borate

Welton, C.E.; Nesterov, V.N.; Smucker, B.W.

doi:10.1107/S2414314622002486

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 3| March 2022| x220248

https://doi.org/10.1107/S2414314622002486

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1-(2-Methylphenyl)-4,4′-bipyridin-1-ium tetrafluoridoborate

Claire E. Welton,^a Vladimir N. Nesterov ^b and Bradley W. Smucker ^a ^*

^aAustin College, 900 N Grand, Sherman, TX 75090, USA, and ^bUniversity of North Texas, 1155 Union Circle, Denton, TX 76203-5070, USA
^*Correspondence e-mail: bsmucker@austincollege.edu

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 12 January 2022; accepted 3 March 2022; online 10 March 2022)

Crystals of the title compound, C₁₇H₁₅N₂⁺·BF₄⁻, were unexpectedly grown from crystallization attempts of [Pt(4,4′-bpy)₄](BF₄)₂ [Smith et al. (2019 ). Comments Inorg. Chem. 39, 188–215] using toluene and acetonitrile. The tetrafluoroborate anion and the central pyridinium ring of the cation are disordered, with atomic site occupancies close to ½. The tolyl group of the cation has a 75.31 (11)° twist relative to the unsubstituted pyridyl group. This rotation allows for a centrosymmetric dimer of cations with weak hydrogen bonding between the pyridyl nitrogen atom and a methyl H atom on the neighbouring cation.

Keywords: crystal structure; bipyridinium; hydrogen bond.

CCDC reference: 2156182

Structure description

For each cation of the title structure, the ring of the tolyl group is twisted relative to the monosubstituted 4,4′-bipyridinium with a 75.31 (11)° rotation between planes (comprised of the tolyl ring (C11–C16) versus the unsubstituted pyridyl ring (N1/C1–C5) (Fig. 1) ; the central pyridinium ring (C6, C7, C9, C10) is disordered over two orientations with refined occupancies of 0.507 (6) and 0.493 (6). This twist is similar to the 78.12° between corresponding planes of a N-naphthyl monosubstituted 4,4′-bipyridinium cation (Lin & Zhao, 2015 ). The twisted conformation in the title compound allows for head-to-tail packing between two cations (Fig. 2). The molecules in this dimer are slightly offset, which enables intermolecular hydrogen bonding (H⋯N = 2.613 Å) between one cation's methyl hydrogen, H17A, and N1 (1 − x, 2 − y, 1 − z) on the pyridyl group of the other cation (Table 1). The offset bipyridinium rings results in an intermolecular C9⋯C1 (1 − x, 2 − y, 1 − z) distance of 3.363 (10) Å (Fig. 2). The twisted tolyl ring is face-to-face with a pyridyl group of another dimer (− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z) at a distance (centroids of each ring) of 3.712 Å. The position of this adjacent dimer results in an N1⋯H10 (− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z) distance of 2.369 Å between the pyridyl nitrogen atom and the hydrogen atom on the other pyridinium ring (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯N1ⁱ	0.96	2.61	3.450 (6)	146
Symmetry code: (i) .

Figure 1
Ellipsoid (50% probability level) representation of the cation with disordered atoms omitted for clarity.

Figure 2
Ellipsoid (50% probability level) representation of the packing of the cations with the distances (Å) between the ring centroids of pyridyl-tolyl groups, N1⋯H10(− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z), H17A⋯N1(1 − x, 2 − y, 1 − z), and C9⋯C1(1 − x, 2 − y, 1 − z). Disordered atoms are omitted.

The C—N distance between the pyridinium and tolyl group is 1.487 (4) Å. This is longer than the C—N bond lengths observed in N-aryl structures of monosubstituted 4,4′-bipyridinium in: N-phenyl [1.460 (2) Å; Coe et al., 1998 ], N-naphthyl [1.455 (2) Å; Lin & Zhao, 2015], or N-biphenyl [1.449 (5) Å; Schoder et al., 2019 ]. The adjacent methyl group of the tolyl group is a likely factor for this longer C—N bond length, which is corroborated by the longer C—N bond distances of 1.463 (9) and 1.482 (9) Å resulting from an ortho-methyl group in the structure of the disubstituted N,N′-bis(3-methyl-4-carboxylatophenyl)-4,4′-bipyridinium bridging ligand (Wang et al., 2020 ).

Synthesis and crystallization

Colourless plate-shaped crystals of the title compound grew as a product from crystallization attempts using liquid diffusion of toluene into an acetonitrile solution of [Pt(4,4′-bpy)₄](BF₄)₂ (Smith et al., 2019).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. In the crystal structure, both the BF₄⁻ anion and four atoms of the central pyridinium ring (C6, C7, C9, C10) in the cation are disordered over two sets of sites, with a ratio of occupancies at ca 51 and 49%. These two occupancies of the pyridinium ring form a dihedral angle of about 30°. All our attempts to improve the quality of the refinement, such as disordering of the entire cation or only some of its rings, gave us similar results.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₂⁺·BF₄⁻
M_r	334.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	11.4260 (5), 9.0735 (3), 15.5434 (5)
β (°)	102.118 (4)
V (Å³)	1575.54 (10)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.00
Crystal size (mm)	0.10 × 0.09 × 0.01

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.845, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16394, 2786, 2296
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.108, 0.378, 1.63
No. of reflections	2786
No. of parameters	240
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.24
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2156182

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002486/bh4067sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002486/bh4067Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622002486/bh4067Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2414314622002486/bh4067Isup4.cml

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: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-(2-Methylphenyl)-4,4'-bipyridin-1-ium tetrafluoridoborate top

Crystal data top

C₁₇H₁₅N₂⁺·BF₄⁻	F(000) = 688
M_r = 334.12	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.4260 (5) Å	Cell parameters from 4873 reflections
b = 9.0735 (3) Å	θ = 4.4–74.8°
c = 15.5434 (5) Å	µ = 1.00 mm⁻¹
β = 102.118 (4)°	T = 200 K
V = 1575.54 (10) Å³	Plate, colourless
Z = 4	0.10 × 0.09 × 0.01 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2786 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2296 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.0000 pixels mm^-1	θ_max = 66.6°, θ_min = 5.4°
ω scans	h = −13→13
Absorption correction: gaussian (CrysAlis Pro; Rigaku OD, 2019)	k = −8→10
T_min = 0.845, T_max = 1.000	l = −18→18
16394 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.108	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.378	H-atom parameters constrained
S = 1.63	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
2786 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.45 e Å⁻³
30 restraints	Δρ_min = −0.24 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1	0.3153 (14)	0.3155 (13)	0.6447 (8)	0.164 (4)	0.493 (6)
F2	0.4760 (14)	0.312 (2)	0.7610 (8)	0.169 (6)	0.493 (6)
F3	0.3583 (14)	0.524 (2)	0.7352 (10)	0.152 (5)	0.493 (6)
F4	0.4860 (11)	0.4406 (9)	0.6437 (8)	0.155 (4)	0.493 (6)
B1	0.415 (3)	0.402 (3)	0.6907 (18)	0.113 (3)	0.493 (6)
F1A	0.3290 (16)	0.530 (2)	0.7158 (11)	0.145 (5)	0.507 (6)
F2A	0.4771 (16)	0.372 (2)	0.7621 (12)	0.202 (8)	0.507 (6)
F3A	0.4091 (17)	0.418 (2)	0.6267 (7)	0.214 (9)	0.507 (6)
F4A	0.2994 (13)	0.3047 (13)	0.7003 (10)	0.193 (5)	0.507 (6)
B1A	0.380 (2)	0.409 (3)	0.7088 (17)	0.113 (3)	0.507 (6)
N1	0.2687 (4)	0.9335 (5)	0.3262 (2)	0.1134 (9)
N2	0.4946 (2)	0.8531 (3)	0.78218 (17)	0.0764 (8)
C1	0.2431 (4)	1.0258 (6)	0.3851 (3)	0.1134 (9)
H1	0.190962	1.102669	0.364388	0.136*
C2	0.2866 (4)	1.0187 (5)	0.4745 (3)	0.0982 (12)
H2	0.264380	1.088352	0.511920	0.118*
C3	0.3641 (3)	0.9056 (4)	0.5073 (2)	0.0768 (9)
C4	0.3920 (4)	0.8102 (5)	0.4469 (2)	0.0979 (12)
H4	0.443970	0.732164	0.465446	0.118*
C5	0.3441 (4)	0.8285 (6)	0.3586 (3)	0.1134 (9)
H5	0.366517	0.762100	0.319478	0.136*
C6	0.3935 (8)	0.9217 (10)	0.7527 (5)	0.0836 (12)	0.493 (6)
H6	0.349547	0.957945	0.792095	0.100*	0.493 (6)
C7	0.3526 (8)	0.9402 (9)	0.6654 (5)	0.0836 (12)	0.493 (6)
H7	0.281258	0.991286	0.646357	0.100*	0.493 (6)
C8	0.4113 (3)	0.8872 (3)	0.60354 (19)	0.0694 (8)
C9	0.5101 (8)	0.7906 (12)	0.6389 (7)	0.0836 (12)	0.493 (6)
H9	0.547025	0.737002	0.601039	0.100*	0.493 (6)
C10	0.5484 (9)	0.7783 (13)	0.7254 (8)	0.0836 (12)	0.493 (6)
H10	0.613277	0.717412	0.747470	0.100*	0.493 (6)
C11	0.5354 (3)	0.8302 (4)	0.8786 (2)	0.0833 (10)
C12	0.6227 (3)	0.9222 (4)	0.9257 (2)	0.0893 (11)
C13	0.6571 (4)	0.8949 (5)	1.0169 (2)	0.0947 (11)
H13	0.716373	0.952582	1.051149	0.114*
C14	0.6053 (4)	0.7857 (5)	1.0553 (2)	0.1002 (13)
H14	0.629212	0.770262	1.115608	0.120*
C15	0.5208 (5)	0.7005 (5)	1.0085 (3)	0.1115 (14)
H15	0.486885	0.625935	1.036254	0.134*
C16	0.4823 (4)	0.7217 (5)	0.9174 (2)	0.1013 (12)
H16	0.422234	0.663387	0.884552	0.122*
C17	0.6795 (5)	1.0384 (6)	0.8840 (3)	0.1146 (14)
H17A	0.699061	1.001150	0.830901	0.172*
H17B	0.751317	1.070252	0.923432	0.172*
H17C	0.625551	1.120184	0.870080	0.172*
C6A	0.5156 (8)	0.7563 (13)	0.7254 (8)	0.0836 (12)	0.507 (6)
H6A	0.560901	0.673187	0.745238	0.100*	0.507 (6)
C7A	0.4714 (8)	0.7748 (12)	0.6354 (7)	0.0836 (12)	0.507 (6)
H7A	0.486638	0.701903	0.597120	0.100*	0.507 (6)
C9A	0.3999 (7)	1.0067 (10)	0.6624 (5)	0.0836 (12)	0.507 (6)
H9A	0.367388	1.096731	0.640958	0.100*	0.507 (6)
C10A	0.4385 (7)	0.9833 (9)	0.7510 (5)	0.0836 (12)	0.507 (6)
H10A	0.426844	1.055966	0.790597	0.100*	0.507 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.204 (9)	0.136 (6)	0.124 (7)	−0.009 (5)	−0.031 (7)	0.010 (6)
F2	0.148 (7)	0.277 (17)	0.081 (5)	0.003 (8)	0.023 (4)	0.057 (7)
F3	0.141 (8)	0.197 (11)	0.134 (10)	−0.064 (7)	0.068 (8)	−0.078 (8)
F4	0.212 (9)	0.108 (4)	0.184 (9)	0.036 (5)	0.129 (8)	0.021 (4)
B1	0.133 (14)	0.138 (5)	0.064 (10)	−0.010 (7)	0.013 (5)	0.003 (5)
F1A	0.168 (10)	0.168 (9)	0.093 (5)	0.019 (8)	0.011 (5)	0.007 (6)
F2A	0.160 (9)	0.250 (16)	0.165 (11)	0.061 (10)	−0.038 (7)	−0.008 (9)
F3A	0.270 (15)	0.282 (17)	0.102 (5)	0.184 (15)	0.066 (8)	0.042 (7)
F4A	0.208 (9)	0.140 (6)	0.200 (12)	−0.022 (5)	−0.026 (11)	−0.006 (8)
B1A	0.133 (14)	0.138 (5)	0.064 (10)	−0.010 (7)	0.013 (5)	0.003 (5)
N1	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
N2	0.0827 (15)	0.0889 (17)	0.0585 (15)	0.0092 (12)	0.0171 (11)	−0.0079 (11)
C1	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
C2	0.114 (3)	0.110 (3)	0.067 (2)	−0.004 (2)	0.0120 (18)	0.0072 (18)
C3	0.0793 (17)	0.093 (2)	0.0607 (18)	−0.0261 (15)	0.0203 (13)	−0.0015 (14)
C4	0.112 (3)	0.119 (3)	0.065 (2)	−0.007 (2)	0.0234 (19)	−0.0141 (18)
C5	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
C6	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C7	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C8	0.0727 (15)	0.0772 (17)	0.0618 (18)	−0.0103 (12)	0.0219 (12)	−0.0022 (12)
C9	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C10	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C11	0.0872 (19)	0.095 (2)	0.068 (2)	0.0171 (16)	0.0167 (15)	−0.0106 (15)
C12	0.099 (2)	0.102 (2)	0.069 (2)	0.0096 (18)	0.0222 (17)	−0.0071 (16)
C13	0.106 (2)	0.116 (3)	0.061 (2)	0.027 (2)	0.0174 (17)	−0.0113 (18)
C14	0.126 (3)	0.113 (3)	0.063 (2)	0.032 (2)	0.023 (2)	−0.0025 (19)
C15	0.140 (3)	0.121 (3)	0.078 (2)	0.009 (3)	0.031 (2)	0.008 (2)
C16	0.129 (3)	0.115 (3)	0.063 (2)	0.000 (2)	0.029 (2)	0.0048 (18)
C17	0.128 (3)	0.137 (4)	0.074 (2)	−0.015 (3)	0.011 (2)	−0.004 (2)
C6A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C7A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C9A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C10A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)

Geometric parameters (Å, º) top

F1—B1	1.44 (3)	C7—C8	1.369 (8)
F2—B1	1.42 (3)	C8—C9	1.444 (11)
F3—B1	1.52 (3)	C8—C7A	1.271 (11)
F4—B1	1.248 (19)	C8—C9A	1.442 (8)
F1A—B1A	1.26 (3)	C9—H9	0.9300
F2A—B1A	1.28 (4)	C9—C10	1.329 (12)
F3A—B1A	1.39 (2)	C10—H10	0.9300
F4A—B1A	1.31 (3)	C11—C12	1.387 (5)
N1—C1	1.319 (6)	C11—C16	1.362 (5)
N1—C5	1.312 (7)	C12—C13	1.411 (5)
N2—C6	1.307 (8)	C12—C17	1.460 (6)
N2—C10	1.359 (11)	C13—H13	0.9300
N2—C11	1.487 (4)	C13—C14	1.356 (6)
N2—C6A	1.303 (11)	C14—H14	0.9300
N2—C10A	1.382 (8)	C14—C15	1.328 (6)
C1—H1	0.9300	C15—H15	0.9300
C1—C2	1.375 (6)	C15—C16	1.405 (5)
C2—H2	0.9300	C16—H16	0.9300
C2—C3	1.381 (5)	C17—H17A	0.9600
C3—C4	1.363 (5)	C17—H17B	0.9600
C3—C8	1.489 (4)	C17—H17C	0.9600
C4—H4	0.9300	C6A—C7A	1.393 (12)
C4—C5	1.376 (6)	C6A—H6A	0.9300
C5—H5	0.9300	C7A—H7A	0.9300
C6—H6	0.9300	C9A—C10A	1.372 (9)
C6—C7	1.350 (9)	C9A—H9A	0.9300
C7—H7	0.9300	C10A—H10A	0.9300

F2—B1—F1	106.1 (19)	C7A—C8—C9A	118.0 (6)
F2—B1—F3	104.7 (18)	C9A—C8—C3	119.5 (4)
F4—B1—F2	110 (2)	C8—C9—H9	119.9
F4—B1—F1	114 (2)	C10—C9—C8	120.1 (7)
F4—B1—F3	117 (2)	C10—C9—H9	119.9
F1—B1—F3	104.4 (19)	N2—C10—H10	119.4
F1A—B1A—F2A	122 (3)	C9—C10—N2	121.1 (8)
F1A—B1A—F3A	103 (2)	C9—C10—H10	119.4
F1A—B1A—F4A	108 (2)	C12—C11—N2	119.2 (3)
F2A—B1A—F3A	105.7 (17)	C16—C11—N2	118.2 (3)
F2A—B1A—F4A	112 (2)	C16—C11—C12	122.6 (3)
F4A—B1A—F3A	105 (2)	C11—C12—C13	116.3 (4)
C5—N1—C1	114.6 (4)	C11—C12—C17	122.5 (3)
C6—N2—C10	119.8 (6)	C13—C12—C17	121.2 (4)
C6—N2—C11	119.1 (4)	C12—C13—H13	119.5
C10—N2—C11	119.7 (6)	C14—C13—C12	121.1 (4)
C6A—N2—C11	121.7 (6)	C14—C13—H13	119.5
C6A—N2—C10A	118.5 (6)	C13—C14—H14	119.4
C10A—N2—C11	119.8 (4)	C15—C14—C13	121.2 (4)
N1—C1—H1	117.0	C15—C14—H14	119.4
N1—C1—C2	125.9 (5)	C14—C15—H15	119.6
C2—C1—H1	117.0	C14—C15—C16	120.7 (4)
C1—C2—H2	120.8	C16—C15—H15	119.6
C1—C2—C3	118.4 (4)	C11—C16—C15	118.1 (4)
C3—C2—H2	120.8	C11—C16—H16	120.9
C2—C3—C8	121.5 (3)	C15—C16—H16	120.9
C4—C3—C2	116.2 (3)	C12—C17—H17A	109.5
C4—C3—C8	122.2 (3)	C12—C17—H17B	109.5
C3—C4—H4	119.7	C12—C17—H17C	109.5
C3—C4—C5	120.5 (4)	H17A—C17—H17B	109.5
C5—C4—H4	119.7	H17A—C17—H17C	109.5
N1—C5—C4	124.3 (4)	H17B—C17—H17C	109.5
N1—C5—H5	117.9	C8—C7A—H7A	118.7
C4—C5—H5	117.9	C8—C7A—C6A	122.7 (8)
N2—C6—H6	119.8	N2—C6A—C7A	121.3 (9)
N2—C6—C7	120.4 (6)	N2—C6A—H6A	119.4
C7—C6—H6	119.8	N2—C10A—H10A	119.6
C6—C7—H7	118.5	C8—C9A—H9A	121.0
C6—C7—C8	123.0 (6)	C6A—C7A—H7A	118.7
C8—C7—H7	118.5	C7A—C6A—H6A	119.4
C7—C8—C3	122.6 (4)	C9A—C10A—N2	120.8 (6)
C7—C8—C9	113.9 (5)	C9A—C10A—H10A	119.6
C9—C8—C3	122.6 (5)	C10A—C9A—C8	117.9 (6)
C7A—C8—C3	122.2 (5)	C10A—C9A—H9A	121.0

N1—C1—C2—C3	−0.1 (6)	C7—C8—C9—C10	−10.3 (10)
N2—C6—C7—C8	1.4 (12)	C8—C3—C4—C5	178.2 (3)
N2—C11—C12—C13	179.8 (3)	C8—C9—C10—N2	1.4 (11)
N2—C11—C12—C17	−2.1 (5)	C8—C7A—C6A—N2	1.7 (11)
N2—C11—C16—C15	−179.9 (3)	C10—N2—C6—C7	−11.3 (11)
N2—C10A—C9A—C8	4.7 (11)	C10—N2—C11—C12	92.2 (6)
C1—N1—C5—C4	1.6 (7)	C10—N2—C11—C16	−89.8 (6)
C1—C2—C3—C4	0.7 (5)	C11—N2—C6—C7	−178.1 (6)
C1—C2—C3—C8	−177.6 (3)	C11—N2—C10—C9	176.6 (6)
C2—C3—C4—C5	−0.1 (5)	C11—N2—C6A—C7A	176.5 (5)
C2—C3—C8—C7	24.5 (6)	C11—N2—C10A—C9A	−179.9 (6)
C2—C3—C8—C9	−166.9 (6)	C11—C12—C13—C14	−1.1 (5)
C2—C3—C8—C7A	171.8 (6)	C12—C11—C16—C15	−1.9 (6)
C2—C3—C8—C9A	−14.9 (6)	C12—C13—C14—C15	0.4 (6)
C3—C4—C5—N1	−1.1 (7)	C13—C14—C15—C16	−0.4 (6)
C3—C8—C9—C10	−179.9 (5)	C14—C15—C16—C11	1.1 (6)
C3—C8—C7A—C6A	−179.7 (5)	C16—C11—C12—C13	1.9 (5)
C3—C8—C9A—C10A	176.6 (5)	C16—C11—C12—C17	180.0 (4)
C4—C3—C8—C7	−153.7 (6)	C17—C12—C13—C14	−179.2 (4)
C4—C3—C8—C9	14.9 (6)	C7A—C8—C9A—C10A	−9.8 (10)
C4—C3—C8—C7A	−6.4 (7)	C6A—N2—C11—C12	113.3 (6)
C4—C3—C8—C9A	166.9 (5)	C6A—N2—C11—C16	−68.7 (6)
C5—N1—C1—C2	−1.0 (7)	C6A—N2—C10A—C9A	3.6 (10)
C6—N2—C10—C9	9.9 (11)	C10A—N2—C11—C12	−63.2 (6)
C6—N2—C11—C12	−101.0 (6)	C10A—N2—C11—C16	114.9 (5)
C6—N2—C11—C16	77.0 (6)	C10A—N2—C6A—C7A	−7.0 (9)
C6—C7—C8—C3	178.7 (6)	C9A—C8—C7A—C6A	6.9 (10)
C6—C7—C8—C9	9.2 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···N1ⁱ	0.96	2.61	3.450 (6)	146

Symmetry code: (i) −x+1, −y+2, −z+1.

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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