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. 2022 Mar 10;7(Pt 3):x220248. doi: 10.1107/S2414314622002486

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

Claire E Welton a, Vladimir N Nesterov b, Bradley W Smucker a,*
Editor: S Bernèsc
PMCID: PMC9462016  PMID: 36339800

In the crystal structure of the title compound, the cations pack as dimers connected by weak hydrogen bonds between the pyridyl nitro­gen and a methyl hydrogen atom on the neighbouring cation.

Keywords: crystal structure, bipyridinium, hydrogen bond

Abstract

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. graphic file with name x-07-x220248-scheme1-3D1.jpg

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 (− Inline graphic  + x, Inline graphic  − y, − Inline graphic  + z) at a distance (centroids of each ring) of 3.712 Å. The position of this adjacent dimer results in an N1⋯H10 (− Inline graphic  + x, Inline graphic  − y, − Inline graphic  + z) distance of 2.369 Å between the pyridyl nitro­gen atom and the hydrogen atom on the other pyridinium ring (Fig. 2 ▸).

Figure 1.

Figure 1

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

Figure 2.

Figure 2

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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(− Inline graphic  + x, Inline graphic  − y, − Inline graphic  + z), H17A⋯N1(1 − x, 2 − y, 1 − z), and C9⋯C1(1 − x, 2 − y, 1 − z). Disordered atoms are omitted.

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
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Symmetry code: (i) Inline graphic .

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 ▸)
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[F 2 > 2σ(F 2)], wR(F 2), 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
Δρmax, Δρmin (e Å−3) 0.45, −0.24
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Computer programs: CrysAlis PRO (Rigaku OD, 2019 ▸), SHELXT2018/2 (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸), OLEX2 (Dolomanov et al., 2009 ▸), and Mercury (Macrae et al., 2020 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314622002486/bh4067sup1.cif

x-07-x220248-sup1.cif (553.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622002486/bh4067Isup2.hkl

x-07-x220248-Isup2.hkl (222.9KB, hkl)
Click here for additional data file. (2.6KB, mol)

Supporting information file. DOI: 10.1107/S2414314622002486/bh4067Isup3.mol

Click here for additional data file. (7.1KB, cml)

Supporting information file. DOI: 10.1107/S2414314622002486/bh4067Isup4.cml

CCDC reference: 2156182

Additional supporting information: crystallographic information; 3D view; checkCIF report

full crystallographic data

Crystal data

C17H15N2+·BF4− F(000) = 688
Mr = 334.12 Dx = 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
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Data collection

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 Rint = 0.023
Detector resolution: 10.0000 pixels mm-1 θmax = 66.6°, θmin = 5.4°
ω scans h = −13→13
Absorption correction: gaussian (CrysAlis Pro; Rigaku OD, 2019) k = −8→10
Tmin = 0.845, Tmax = 1.000 l = −18→18
16394 measured reflections
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Refinement

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(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2786 reflections (Δ/σ)max < 0.001
240 parameters Δρmax = 0.45 e Å−3
30 restraints Δρmin = −0.24 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq 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)
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C17—H17A···N1i 0.96 2.61 3.450 (6) 146
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Symmetry code: (i) −x+1, −y+2, −z+1.

Funding Statement

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

References

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  2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
  3. Lin, F. & Zhao, X. (2015). Tetrahedron, 71, 1124–1131.
  4. Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. [DOI] [PMC free article] [PubMed]
  5. Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.
  6. Schoder, S., Schröder, H. V., Cera, L., Puttreddy, R., Güttler, A., Resch-Genger, U., Rissanen, K. & Schalley, C. A. (2019). Chem. Eur. J. 25, 3257–3261. [DOI] [PubMed]
  7. Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
  8. Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
  9. Smith, J. B., Otten, B. M., Derry, P. J., Browning, C., Bodenstedt, K. W., Sandridge, J. H., Satumtira, N. T., Zilaie, M., Payne, J., Nuti, R., Omary, M. A. & Smucker, B. W. (2019). Comments Inorg. Chem. 39, 188–215.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314622002486/bh4067sup1.cif

x-07-x220248-sup1.cif (553.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622002486/bh4067Isup2.hkl

x-07-x220248-Isup2.hkl (222.9KB, hkl)
Click here for additional data file. (2.6KB, mol)

Supporting information file. DOI: 10.1107/S2414314622002486/bh4067Isup3.mol

Click here for additional data file. (7.1KB, cml)

Supporting information file. DOI: 10.1107/S2414314622002486/bh4067Isup4.cml

CCDC reference: 2156182

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from IUCrData are provided here courtesy of International Union of Crystallography

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