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ISSN: 2414-3146

Ethidium tetra­phenyl­borate aceto­nitrile disolvate

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aDepartment of Applied Chemistry, Faculty of Science Division I, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan
*Correspondence e-mail: sadakiyo@rs.tus.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 September 2022; accepted 26 September 2022; online 11 October 2022)

In the title solvated salt, (C21H20N3){B(C6H5)4}·2CH3CN (systematic name 3,8-di­amino-5-ethyl-6-phenyl­phenanthridin-5-ium tetra­phenyl­borate aceto­nitrile disolvate), the dihedral angle between the tricyclic fused ring system (r.m.s. deviation = 0.021 Å) and the pendant phenyl group of the ethidium cation is 84.91 (7)°. The {B(C6H5)4} anion has a typical tetra­hedral structure. The aceto­nitrile solvent mol­ecules do not accept hydrogen bonds from the –NH2 groups of the ethidium ions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The bromide salt of the C21H20N3+ ethidium cation is an important chemical in various research fields such as biochemistry (Chen et al., 2000[Chen, W., Turro, N. J. & Tomalia, D. A. (2000). Langmuir, 16, 15-19.]) and materials chemistry (Ma et al., 2016[Ma, H., Liu, B., Li, B., Zhang, L., Li, Y.-G., Tan, H.-Q., Zang, H.-Y. & Zhu, G. (2016). J. Am. Chem. Soc. 138, 5897-5903.]). In this work, the crystal structure of a new solvated ethidium salt, (C21H20N3){B(C6H5)4}·2CH3CN, including a bulky anion, tetra­phenyl­borate, was determined.

One ethidium cation, one tetra­phenyl­borate anion and two aceto­nitrile mol­ecules exist in a unit cell as the crystallographically independent components (Fig. 1[link]). The ethidium cation shows an almost planer structure in the π-conjugated part (r.m.s. deviation for C1–C13/N1 = 0.021 Å), while that part was observed as a puckered structure in ethidium hepta­fluoro­butrate (Shimazaki et al., 2022[Shimazaki, R. & Sadakiyo, M. (2022). IUCrData, 7, x220884.]). The dihedral angle between the tricyclic fused ring system and the pendant C16–C21 phenyl group is 84.91 (7)°. The tetra­phenyl­borate anion has a typical tetra­hedral structure around the B atom and aceto­nitrile solvent mol­ecules are incorporated in the voids of the structure.

[Figure 1]
Figure 1
The mol­ecular structure of (C21H20N3){B(C6H5)4}·2CH3CN with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

In the extended structure of the title compound, the ethidium cations do not show a ππ-dimerized structure [i.e., the closest CgCg separation between the ethidium cations is 4.4611 (5) Å], which is a clear difference between the title structure and that of ethidium hepta­fluoro­butrate (Shimazaki et al., 2022[Shimazaki, R. & Sadakiyo, M. (2022). IUCrData, 7, x220884.]). There are no hydrogen bonds between the hydrogen-bonding donor (i.e., –NH2 on the ethidium cation) and acceptor (i.e., –CN on the aceto­nitrile unit) sites in the title salt but two N—H⋯π inter­actions occur (Fig. 2[link], Table 1[link]). There are also a number of short C—H⋯π inter­actions (Tsuzuki et al., 2000[Tsuzuki, S., Honda, K., Uchimaru, T., Mikami, M. & Tanabe, K. (2000). J. Am. Chem. Soc. 122, 3746-3753.]) involving aromatic rings of both anion and cation as acceptors (Fig. 3[link]), which are presumably one of the main cohesive inter­actions in this crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1–Cg5 and Cg8 are the centroids of the C22–C27, C28–C33, C34–C39, C40–C45, N1/C1/C2/C7/C8/C13 and C16–C21 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯Cg1i 0.88 2.45 3.303 (2) 165
N2—H2ACg4i 0.88 2.62 3.3297 (18) 139
C21—H21⋯Cg3ii 0.95 2.75 3.685 (2) 167
C25—H25⋯Cg8i 0.95 2.79 3.632 (2) 148
C36—H36⋯Cg5iii 0.95 2.81 3.3593 (18) 118
C48—H48⋯Cg2 0.98 2.78 3.609 (2) 143
C48—H48ACg3 0.99 2.61 3.488 (2) 149
Symmetry codes: (i) [-x, -y, -z+1]; (ii) x, y, z+1; (iii) [x, y, z-1].
[Figure 2]
Figure 2
Packing of the title compound viewed along the b-axis direction.
[Figure 3]
Figure 3
A short contact between the components with a C—H⋯π inter­action, exemplified by ethidium and tetra­phenyl­borate.

Synthesis and crystallization

Firstly, silver tetra­phenyl­borate was synthesized according to a previous report (Borodin et al., 2021[Borodin, O., Shchukin, Y., Robertson, C. C., Richter, S. & von Delius, M. (2021). J. Am. Chem. Soc. 143, 16448-16457.]). An aqueous solution (2.7 ml) of sodium tetra­phenyl­borate (182 mg, 0.53 mmol) was mixed with an aqueous solution (1.1 ml) of silver(I) nitrate (181 mg, 1.06 mmol). The mixture was then stirred for 1 h at room temperature. The resulting precipitate, silver(I) tetra­phenyl­borate, was collected by filtration. Next, the obtained powder of silver(I) tetra­phenyl­borate was dissolved in DMSO (50 ml), and then a DMSO solution (10 ml) of ethidium bromide (184 mg, 0.47 mmol) was added to this solution. After stirring for 18 h at room temperature, the resulting precipitate was removed by centrifugation. After adding water to the remaining solution, the resulting powder was collected by centrifugation. The sample powder was again dissolved in acetone, and the insoluble precipitate was removed. The crude powder of the target compound was obtained by vacuum concentration of the remaining solution (185 mg, 0.29 mmol, yield 62%). The title crystal was prepared by recrystallization through slow evaporation (3 days at room temperature) of a solution of the crude powder (30 mg) dissolved in a mixed solvent (4 ml, CH3CN: H2O = 9: 1).

Refinement

Details of crystal data, data collections, and structure refinements are shown in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C21H20N3+·C24H20B·2CH3N
Mr 715.72
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 90
a, b, c (Å) 13.5215 (13), 13.5537 (14), 13.6079 (14)
α, β, γ (°) 92.202 (4), 113.379 (3), 117.604 (4)
V3) 1951.3 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.30 × 0.30 × 0.15
 
Data collection
Diffractometer Bruker PHOTON II CPAD
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.678, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 24904, 9444, 7510
Rint 0.069
(sin θ/λ)max−1) 0.724
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.149, 1.03
No. of reflections 9444
No. of parameters 498
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.32, −0.41
Computer programs: APEX4 and SAINT (Bruker, 2021[Bruker (2021). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SIR2019 (Burla et al., 2015[Burla, M. C., Caliandro, R., Carrozzini, B., Cascarano, G. L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A. & Polidori, G. (2015). J. Appl. Cryst. 48, 306-309.]), SHELXL2018/3 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg, 2014[Brandenburg, K. (2014). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Yadokari-XG (Kabuto 2009[Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Japan, 51, 218-224.]).

Structural data


Computing details top

Data collection: APEX4 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SIR2019 (Burla 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018); molecular graphics: DIAMOND (Brandenburg 1999); software used to prepare material for publication: Yadokari-XG (Kabuto 2009).

3,8-Diamino-5-ethyl-6-phenylphenanthridin-5-ium tetraphenylborate acetonitrile disolvate top
Crystal data top
C21H20N3+·C24H20B·2CH3NZ = 2
Mr = 715.72F(000) = 760
Triclinic, P1Dx = 1.218 Mg m3
a = 13.5215 (13) ÅMo Kα radiation, λ = 0.71069 Å
b = 13.5537 (14) ÅCell parameters from 5009 reflections
c = 13.6079 (14) Åθ = 2.8–30.7°
α = 92.202 (4)°µ = 0.07 mm1
β = 113.379 (3)°T = 90 K
γ = 117.604 (4)°Platelet, red
V = 1951.3 (3) Å30.30 × 0.30 × 0.15 mm
Data collection top
Bruker PHOTON II CPAD
diffractometer
7510 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
φ and ω scansθmax = 31.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1919
Tmin = 0.678, Tmax = 0.746k = 1718
24904 measured reflectionsl = 1819
9444 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6357P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
9444 reflectionsΔρmax = 0.32 e Å3
498 parametersΔρmin = 0.41 e Å3
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

All hydrogen atoms are geometrically fixed using a riding-model approximation with C–H = 0.95 (for phenyl), 0.98 (for methyl), 0.99 (for methylene), and N–H = 0.88 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.10283 (13)0.18417 (12)0.65451 (11)0.0151 (3)
C20.02177 (13)0.12168 (12)0.64193 (12)0.0158 (3)
C30.05470 (14)0.03582 (13)0.69845 (12)0.0178 (3)
H30.0077230.0218890.7473510.021*
C40.17723 (14)0.02804 (13)0.68301 (12)0.0180 (3)
C50.26821 (14)0.00588 (14)0.60872 (13)0.0208 (3)
H50.3529260.0503530.5962730.025*
C60.23797 (14)0.07748 (14)0.55434 (13)0.0196 (3)
H60.3015490.0901900.5055730.024*
C70.11306 (13)0.14519 (13)0.56974 (12)0.0160 (3)
C80.07585 (14)0.23343 (13)0.51487 (12)0.0166 (3)
C90.16161 (15)0.26139 (13)0.44044 (13)0.0203 (3)
H90.2468310.2210040.4271400.024*
C100.12532 (16)0.34412 (14)0.38777 (13)0.0221 (3)
H100.1855470.3595700.3374380.026*
C110.00140 (16)0.40759 (14)0.40713 (12)0.0206 (3)
C120.08861 (15)0.38404 (13)0.48036 (12)0.0202 (3)
H120.1742440.4271170.4950540.024*
C130.05015 (14)0.29626 (13)0.53290 (12)0.0162 (3)
C140.26588 (14)0.32666 (13)0.61385 (13)0.0190 (3)
H140.3236860.3207480.6828340.023*
H14A0.2965700.4097240.6196500.023*
C150.26718 (16)0.27342 (16)0.51465 (14)0.0250 (4)
H150.3533040.3140130.5237890.037*
H15A0.2380710.1914900.5095680.037*
H15B0.2109870.2803590.4464600.037*
C160.19764 (13)0.15390 (13)0.72163 (12)0.0159 (3)
C170.19897 (14)0.06352 (14)0.67151 (13)0.0216 (3)
H170.1394500.0217090.5959160.026*
C180.28669 (15)0.03388 (15)0.73113 (14)0.0237 (3)
H180.2877810.0274850.6963750.028*
C190.37266 (14)0.09448 (14)0.84176 (13)0.0207 (3)
H190.4332500.0749120.8827140.025*
C200.37059 (14)0.18335 (13)0.89275 (13)0.0198 (3)
H200.4295250.2242260.9686500.024*
C210.28259 (14)0.21321 (13)0.83343 (12)0.0182 (3)
H210.2804680.2734620.8688480.022*
C220.12205 (13)0.29457 (13)0.13371 (12)0.0165 (3)
C230.05756 (14)0.18979 (13)0.05175 (12)0.0186 (3)
H230.0875100.1861050.0000940.022*
C240.04892 (14)0.09093 (13)0.04352 (13)0.0211 (3)
H240.0904560.0219820.0134820.025*
C250.09401 (14)0.09344 (14)0.11858 (13)0.0218 (3)
H250.1673240.0269410.1124360.026*
C260.03077 (14)0.19422 (14)0.20276 (13)0.0203 (3)
H260.0595780.1964480.2556580.024*
C270.07526 (14)0.29226 (13)0.20949 (12)0.0182 (3)
H270.1174570.3602570.2678570.022*
C280.27575 (14)0.53038 (13)0.20596 (12)0.0165 (3)
C290.39743 (14)0.62668 (13)0.27226 (13)0.0214 (3)
H290.4676120.6180680.2881910.026*
C300.42072 (17)0.73433 (14)0.31598 (14)0.0277 (4)
H300.5050850.7969660.3601630.033*
C310.32062 (18)0.74988 (15)0.29491 (15)0.0285 (4)
H310.3353200.8223680.3258000.034*
C320.19867 (17)0.65776 (15)0.22795 (15)0.0277 (4)
H320.1291700.6675200.2118160.033*
C330.17714 (14)0.55105 (14)0.18411 (14)0.0212 (3)
H330.0925980.4897710.1376430.025*
C340.24620 (13)0.42353 (12)0.02563 (12)0.0156 (3)
C350.13375 (14)0.37692 (13)0.07495 (12)0.0182 (3)
H350.0556750.3278500.0752500.022*
C360.13246 (15)0.39999 (13)0.17433 (13)0.0201 (3)
H360.0544000.3658360.2406880.024*
C370.24450 (15)0.47252 (13)0.17690 (13)0.0203 (3)
H370.2438510.4890550.2442950.024*
C380.35770 (15)0.52053 (13)0.07894 (13)0.0201 (3)
H380.4354000.5700050.0791030.024*
C390.35716 (14)0.49611 (13)0.01924 (12)0.0179 (3)
H390.4356720.5302040.0851290.021*
C400.36523 (13)0.38498 (12)0.22126 (12)0.0154 (3)
C410.40842 (14)0.33088 (13)0.17341 (12)0.0182 (3)
H410.3742760.3108120.0947290.022*
C420.49936 (15)0.30514 (14)0.23617 (13)0.0210 (3)
H420.5269830.2697540.2001850.025*
C430.54946 (14)0.33132 (14)0.35131 (13)0.0216 (3)
H430.6116570.3144780.3947300.026*
C440.50703 (14)0.38249 (13)0.40172 (13)0.0200 (3)
H440.5390460.3994320.4801920.024*
C450.41752 (14)0.40920 (13)0.33769 (12)0.0176 (3)
H450.3908850.4452020.3743050.021*
C460.35854 (19)0.00009 (19)0.12689 (16)0.0409 (5)
H460.2885110.0795450.1073700.061*
H46A0.3979720.0044800.0790280.061*
H46B0.3264310.0524230.1162670.061*
C470.45173 (15)0.03317 (15)0.24280 (15)0.0261 (4)
C480.23117 (19)0.69337 (16)0.02061 (17)0.0344 (4)
H480.2841780.7158010.0601170.052*
H48A0.1989980.6118520.0514680.052*
H48B0.1600800.7042400.0366500.052*
C490.30580 (16)0.76501 (15)0.07085 (14)0.0267 (4)
N10.13589 (11)0.26686 (11)0.60274 (10)0.0160 (3)
N20.21233 (13)0.10941 (12)0.73872 (12)0.0244 (3)
H20.1561120.1226430.7863590.029*
H2A0.2910770.1483920.7268360.029*
N30.03525 (15)0.49152 (13)0.35363 (12)0.0277 (3)
H3A0.1138660.5319370.3653860.033*
H3B0.0216400.5049840.3075390.033*
B10.25161 (15)0.40776 (14)0.14659 (13)0.0148 (3)
N40.52247 (15)0.05982 (14)0.33369 (14)0.0347 (4)
N50.36569 (16)0.82227 (15)0.10868 (14)0.0370 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0162 (7)0.0135 (7)0.0130 (6)0.0067 (6)0.0060 (6)0.0022 (5)
C20.0156 (6)0.0140 (7)0.0153 (7)0.0070 (6)0.0060 (6)0.0023 (5)
C30.0158 (7)0.0159 (7)0.0185 (7)0.0073 (6)0.0065 (6)0.0051 (6)
C40.0179 (7)0.0149 (7)0.0182 (7)0.0061 (6)0.0088 (6)0.0036 (6)
C50.0167 (7)0.0217 (8)0.0227 (8)0.0086 (6)0.0098 (6)0.0049 (6)
C60.0168 (7)0.0230 (8)0.0189 (7)0.0111 (6)0.0074 (6)0.0053 (6)
C70.0174 (7)0.0152 (7)0.0149 (7)0.0087 (6)0.0071 (6)0.0022 (5)
C80.0186 (7)0.0152 (7)0.0151 (7)0.0095 (6)0.0066 (6)0.0024 (6)
C90.0198 (7)0.0190 (7)0.0193 (7)0.0112 (6)0.0055 (6)0.0029 (6)
C100.0279 (8)0.0210 (8)0.0178 (7)0.0160 (7)0.0072 (7)0.0058 (6)
C110.0302 (8)0.0180 (7)0.0161 (7)0.0139 (7)0.0115 (7)0.0055 (6)
C120.0225 (7)0.0188 (7)0.0196 (7)0.0095 (6)0.0115 (6)0.0064 (6)
C130.0196 (7)0.0151 (7)0.0130 (6)0.0096 (6)0.0063 (6)0.0027 (5)
C140.0151 (7)0.0201 (7)0.0197 (7)0.0068 (6)0.0090 (6)0.0077 (6)
C150.0249 (8)0.0330 (9)0.0246 (8)0.0170 (7)0.0157 (7)0.0107 (7)
C160.0139 (6)0.0157 (7)0.0181 (7)0.0067 (5)0.0085 (6)0.0063 (6)
C170.0185 (7)0.0212 (8)0.0189 (7)0.0092 (6)0.0052 (6)0.0004 (6)
C180.0234 (8)0.0239 (8)0.0259 (8)0.0154 (7)0.0101 (7)0.0035 (7)
C190.0170 (7)0.0224 (8)0.0239 (8)0.0118 (6)0.0086 (6)0.0087 (6)
C200.0164 (7)0.0192 (7)0.0188 (7)0.0076 (6)0.0057 (6)0.0058 (6)
C210.0181 (7)0.0153 (7)0.0183 (7)0.0079 (6)0.0072 (6)0.0036 (6)
C220.0141 (6)0.0164 (7)0.0180 (7)0.0081 (6)0.0064 (6)0.0065 (6)
C230.0186 (7)0.0184 (7)0.0178 (7)0.0087 (6)0.0086 (6)0.0053 (6)
C240.0177 (7)0.0156 (7)0.0221 (7)0.0060 (6)0.0060 (6)0.0035 (6)
C250.0150 (7)0.0192 (8)0.0266 (8)0.0062 (6)0.0088 (6)0.0099 (6)
C260.0189 (7)0.0225 (8)0.0234 (8)0.0114 (6)0.0123 (7)0.0104 (6)
C270.0183 (7)0.0174 (7)0.0178 (7)0.0086 (6)0.0084 (6)0.0053 (6)
C280.0188 (7)0.0168 (7)0.0166 (7)0.0088 (6)0.0110 (6)0.0077 (6)
C290.0190 (7)0.0188 (8)0.0231 (8)0.0093 (6)0.0078 (6)0.0037 (6)
C300.0289 (8)0.0180 (8)0.0281 (8)0.0088 (7)0.0110 (7)0.0028 (7)
C310.0402 (10)0.0198 (8)0.0346 (9)0.0172 (8)0.0234 (8)0.0097 (7)
C320.0340 (9)0.0286 (9)0.0421 (10)0.0224 (8)0.0284 (9)0.0199 (8)
C330.0186 (7)0.0196 (8)0.0291 (8)0.0093 (6)0.0146 (7)0.0113 (6)
C340.0172 (7)0.0133 (7)0.0181 (7)0.0085 (6)0.0090 (6)0.0054 (5)
C350.0180 (7)0.0162 (7)0.0208 (7)0.0088 (6)0.0094 (6)0.0069 (6)
C360.0226 (7)0.0188 (7)0.0171 (7)0.0122 (6)0.0063 (6)0.0048 (6)
C370.0316 (8)0.0189 (7)0.0189 (7)0.0164 (7)0.0151 (7)0.0093 (6)
C380.0219 (7)0.0175 (7)0.0243 (8)0.0091 (6)0.0149 (7)0.0085 (6)
C390.0169 (7)0.0165 (7)0.0180 (7)0.0074 (6)0.0079 (6)0.0044 (6)
C400.0147 (6)0.0116 (6)0.0192 (7)0.0050 (5)0.0092 (6)0.0056 (5)
C410.0211 (7)0.0187 (7)0.0171 (7)0.0100 (6)0.0112 (6)0.0068 (6)
C420.0245 (8)0.0207 (8)0.0265 (8)0.0142 (6)0.0164 (7)0.0102 (6)
C430.0184 (7)0.0213 (8)0.0256 (8)0.0112 (6)0.0092 (7)0.0103 (6)
C440.0183 (7)0.0193 (7)0.0176 (7)0.0080 (6)0.0061 (6)0.0063 (6)
C450.0187 (7)0.0156 (7)0.0186 (7)0.0080 (6)0.0100 (6)0.0038 (6)
C460.0347 (10)0.0394 (11)0.0310 (10)0.0191 (9)0.0014 (9)0.0018 (9)
C470.0193 (7)0.0234 (8)0.0353 (10)0.0121 (7)0.0113 (8)0.0083 (7)
C480.0413 (10)0.0282 (9)0.0399 (10)0.0185 (8)0.0236 (9)0.0132 (8)
C490.0274 (8)0.0283 (9)0.0222 (8)0.0168 (7)0.0072 (7)0.0040 (7)
N10.0146 (6)0.0159 (6)0.0151 (6)0.0068 (5)0.0063 (5)0.0036 (5)
N20.0199 (6)0.0234 (7)0.0297 (7)0.0095 (6)0.0131 (6)0.0137 (6)
N30.0381 (8)0.0284 (8)0.0284 (7)0.0221 (7)0.0193 (7)0.0173 (6)
B10.0133 (7)0.0148 (7)0.0153 (7)0.0062 (6)0.0072 (6)0.0042 (6)
N40.0264 (8)0.0353 (9)0.0360 (9)0.0156 (7)0.0093 (7)0.0132 (7)
N50.0351 (9)0.0424 (10)0.0347 (8)0.0198 (8)0.0176 (8)0.0133 (8)
Geometric parameters (Å, º) top
C1—N11.3411 (19)C26—H260.9500
C1—C21.422 (2)C27—H270.9500
C1—C161.494 (2)C28—C291.402 (2)
C2—C31.416 (2)C28—C331.408 (2)
C2—C71.420 (2)C28—B11.645 (2)
C3—C41.385 (2)C29—C301.393 (2)
C3—H30.9500C29—H290.9500
C4—N21.372 (2)C30—C311.385 (3)
C4—C51.416 (2)C30—H300.9500
C5—C61.367 (2)C31—C321.386 (3)
C5—H50.9500C31—H310.9500
C6—C71.417 (2)C32—C331.392 (2)
C6—H60.9500C32—H320.9500
C7—C81.432 (2)C33—H330.9500
C8—C131.413 (2)C34—C391.403 (2)
C8—C91.421 (2)C34—C351.406 (2)
C9—C101.357 (2)C34—B11.645 (2)
C9—H90.9500C35—C361.395 (2)
C10—C111.416 (2)C35—H350.9500
C10—H100.9500C36—C371.388 (2)
C11—N31.371 (2)C36—H360.9500
C11—C121.388 (2)C37—C381.391 (2)
C12—C131.409 (2)C37—H370.9500
C12—H120.9500C38—C391.391 (2)
C13—N11.4103 (19)C38—H380.9500
C14—N11.4929 (19)C39—H390.9500
C14—C151.516 (2)C40—C411.402 (2)
C14—H140.9900C40—C451.405 (2)
C14—H14A0.9900C40—B11.647 (2)
C15—H150.9800C41—C421.397 (2)
C15—H15A0.9800C41—H410.9500
C15—H15B0.9800C42—C431.390 (2)
C16—C171.390 (2)C42—H420.9500
C16—C211.394 (2)C43—C441.388 (2)
C17—C181.389 (2)C43—H430.9500
C17—H170.9500C44—C451.396 (2)
C18—C191.387 (2)C44—H440.9500
C18—H180.9500C45—H450.9500
C19—C201.384 (2)C46—C471.456 (3)
C19—H190.9500C46—H460.9800
C20—C211.393 (2)C46—H46A0.9800
C20—H200.9500C46—H46B0.9800
C21—H210.9500C47—N41.132 (2)
C22—C271.402 (2)C48—C491.456 (3)
C22—C231.407 (2)C48—H480.9800
C22—B11.643 (2)C48—H48A0.9800
C23—C241.398 (2)C48—H48B0.9800
C23—H230.9500C49—N51.141 (2)
C24—C251.388 (2)N2—H20.8800
C24—H240.9500N2—H2A0.8800
C25—C261.389 (2)N3—H3A0.8800
C25—H250.9500N3—H3B0.8800
C26—C271.397 (2)
N1—C1—C2121.19 (13)C26—C27—H27118.6
N1—C1—C16118.78 (12)C22—C27—H27118.6
C2—C1—C16119.96 (13)C29—C28—C33114.76 (14)
C3—C2—C7120.71 (13)C29—C28—B1122.18 (13)
C3—C2—C1120.51 (13)C33—C28—B1122.68 (13)
C7—C2—C1118.76 (14)C30—C29—C28123.39 (15)
C4—C3—C2120.53 (14)C30—C29—H29118.3
C4—C3—H3119.7C28—C29—H29118.3
C2—C3—H3119.7C31—C30—C29119.88 (16)
N2—C4—C3122.46 (14)C31—C30—H30120.1
N2—C4—C5119.23 (13)C29—C30—H30120.1
C3—C4—C5118.29 (14)C30—C31—C32118.79 (16)
C6—C5—C4122.05 (14)C30—C31—H31120.6
C6—C5—H5119.0C32—C31—H31120.6
C4—C5—H5119.0C31—C32—C33120.57 (15)
C5—C6—C7120.87 (14)C31—C32—H32119.7
C5—C6—H6119.6C33—C32—H32119.7
C7—C6—H6119.6C32—C33—C28122.58 (15)
C6—C7—C2117.53 (14)C32—C33—H33118.7
C6—C7—C8123.39 (14)C28—C33—H33118.7
C2—C7—C8119.07 (13)C39—C34—C35115.19 (14)
C13—C8—C9117.15 (14)C39—C34—B1120.42 (12)
C13—C8—C7120.24 (13)C35—C34—B1124.11 (13)
C9—C8—C7122.61 (14)C36—C35—C34122.49 (14)
C10—C9—C8121.91 (15)C36—C35—H35118.8
C10—C9—H9119.0C34—C35—H35118.8
C8—C9—H9119.0C37—C36—C35120.44 (14)
C9—C10—C11120.63 (15)C37—C36—H36119.8
C9—C10—H10119.7C35—C36—H36119.8
C11—C10—H10119.7C36—C37—C38118.73 (14)
N3—C11—C12121.56 (15)C36—C37—H37120.6
N3—C11—C10119.15 (15)C38—C37—H37120.6
C12—C11—C10119.29 (15)C39—C38—C37120.01 (14)
C11—C12—C13120.01 (14)C39—C38—H38120.0
C11—C12—H12120.0C37—C38—H38120.0
C13—C12—H12120.0C38—C39—C34123.13 (14)
C12—C13—N1120.74 (13)C38—C39—H39118.4
C12—C13—C8120.97 (14)C34—C39—H39118.4
N1—C13—C8118.27 (13)C41—C40—C45115.24 (13)
N1—C14—C15110.96 (12)C41—C40—B1122.78 (13)
N1—C14—H14109.4C45—C40—B1121.73 (13)
C15—C14—H14109.4C42—C41—C40122.97 (14)
N1—C14—H14A109.4C42—C41—H41118.5
C15—C14—H14A109.4C40—C41—H41118.5
H14—C14—H14A108.0C43—C42—C41119.98 (14)
C14—C15—H15109.5C43—C42—H42120.0
C14—C15—H15A109.5C41—C42—H42120.0
H15—C15—H15A109.5C44—C43—C42118.84 (14)
C14—C15—H15B109.5C44—C43—H43120.6
H15—C15—H15B109.5C42—C43—H43120.6
H15A—C15—H15B109.5C43—C44—C45120.31 (14)
C17—C16—C21119.83 (14)C43—C44—H44119.8
C17—C16—C1118.98 (13)C45—C44—H44119.8
C21—C16—C1121.18 (13)C44—C45—C40122.63 (14)
C18—C17—C16120.48 (14)C44—C45—H45118.7
C18—C17—H17119.8C40—C45—H45118.7
C16—C17—H17119.8C47—C46—H46109.5
C19—C18—C17119.55 (15)C47—C46—H46A109.5
C19—C18—H18120.2H46—C46—H46A109.5
C17—C18—H18120.2C47—C46—H46B109.5
C20—C19—C18120.29 (14)H46—C46—H46B109.5
C20—C19—H19119.9H46A—C46—H46B109.5
C18—C19—H19119.9N4—C47—C46178.3 (2)
C19—C20—C21120.39 (14)C49—C48—H48109.5
C19—C20—H20119.8C49—C48—H48A109.5
C21—C20—H20119.8H48—C48—H48A109.5
C20—C21—C16119.43 (14)C49—C48—H48B109.5
C20—C21—H21120.3H48—C48—H48B109.5
C16—C21—H21120.3H48A—C48—H48B109.5
C27—C22—C23115.56 (14)N5—C49—C48179.0 (2)
C27—C22—B1122.38 (13)C1—N1—C13122.40 (12)
C23—C22—B1121.80 (13)C1—N1—C14119.54 (12)
C24—C23—C22122.44 (14)C13—N1—C14117.99 (12)
C24—C23—H23118.8C4—N2—H2120.0
C22—C23—H23118.8C4—N2—H2A120.0
C25—C24—C23120.04 (14)H2—N2—H2A120.0
C25—C24—H24120.0C11—N3—H3A120.0
C23—C24—H24120.0C11—N3—H3B120.0
C24—C25—C26119.28 (14)H3A—N3—H3B120.0
C24—C25—H25120.4C22—B1—C28112.62 (12)
C26—C25—H25120.4C22—B1—C34112.51 (12)
C25—C26—C27119.86 (15)C28—B1—C34103.66 (12)
C25—C26—H26120.1C22—B1—C40104.63 (12)
C27—C26—H26120.1C28—B1—C40111.81 (12)
C26—C27—C22122.77 (14)C34—B1—C40111.84 (12)
N1—C1—C2—C3179.05 (13)C28—C29—C30—C310.3 (3)
C16—C1—C2—C34.1 (2)C29—C30—C31—C321.6 (3)
N1—C1—C2—C72.4 (2)C30—C31—C32—C331.0 (3)
C16—C1—C2—C7174.45 (13)C31—C32—C33—C280.9 (3)
C7—C2—C3—C41.0 (2)C29—C28—C33—C322.0 (2)
C1—C2—C3—C4177.60 (13)B1—C28—C33—C32175.08 (15)
C2—C3—C4—N2177.87 (14)C39—C34—C35—C360.7 (2)
C2—C3—C4—C50.6 (2)B1—C34—C35—C36174.57 (14)
N2—C4—C5—C6177.17 (14)C34—C35—C36—C370.9 (2)
C3—C4—C5—C61.4 (2)C35—C36—C37—C380.7 (2)
C4—C5—C6—C70.5 (2)C36—C37—C38—C390.4 (2)
C5—C6—C7—C21.1 (2)C37—C38—C39—C340.3 (2)
C5—C6—C7—C8179.81 (14)C35—C34—C39—C380.4 (2)
C3—C2—C7—C61.8 (2)B1—C34—C39—C38174.51 (14)
C1—C2—C7—C6176.79 (13)C45—C40—C41—C421.6 (2)
C3—C2—C7—C8179.41 (13)B1—C40—C41—C42176.04 (14)
C1—C2—C7—C82.0 (2)C40—C41—C42—C431.2 (2)
C6—C7—C8—C13178.95 (13)C41—C42—C43—C440.3 (2)
C2—C7—C8—C130.2 (2)C42—C43—C44—C451.3 (2)
C6—C7—C8—C90.5 (2)C43—C44—C45—C400.9 (2)
C2—C7—C8—C9179.27 (13)C41—C40—C45—C440.6 (2)
C13—C8—C9—C100.5 (2)B1—C40—C45—C44175.05 (13)
C7—C8—C9—C10179.00 (14)C2—C1—N1—C130.4 (2)
C8—C9—C10—C111.2 (2)C16—C1—N1—C13176.45 (12)
C9—C10—C11—N3179.20 (14)C2—C1—N1—C14177.17 (12)
C9—C10—C11—C120.3 (2)C16—C1—N1—C140.33 (19)
N3—C11—C12—C13179.28 (14)C12—C13—N1—C1179.70 (13)
C10—C11—C12—C131.2 (2)C8—C13—N1—C11.9 (2)
C11—C12—C13—N1176.47 (13)C12—C13—N1—C143.5 (2)
C11—C12—C13—C81.9 (2)C8—C13—N1—C14174.94 (12)
C9—C8—C13—C121.0 (2)C15—C14—N1—C197.48 (16)
C7—C8—C13—C12179.44 (13)C15—C14—N1—C1379.45 (16)
C9—C8—C13—N1177.37 (13)C27—C22—B1—C2830.72 (19)
C7—C8—C13—N12.2 (2)C23—C22—B1—C28155.40 (13)
N1—C1—C16—C1793.33 (17)C27—C22—B1—C34147.44 (14)
C2—C1—C16—C1783.56 (18)C23—C22—B1—C3438.68 (19)
N1—C1—C16—C2187.83 (18)C27—C22—B1—C4090.93 (16)
C2—C1—C16—C2195.29 (17)C23—C22—B1—C4082.95 (16)
C21—C16—C17—C181.8 (2)C29—C28—B1—C22148.75 (14)
C1—C16—C17—C18179.33 (14)C33—C28—B1—C2238.68 (19)
C16—C17—C18—C190.6 (3)C29—C28—B1—C3489.37 (16)
C17—C18—C19—C200.5 (2)C33—C28—B1—C3483.20 (16)
C18—C19—C20—C210.3 (2)C29—C28—B1—C4031.28 (19)
C19—C20—C21—C160.9 (2)C33—C28—B1—C40156.15 (14)
C17—C16—C21—C202.0 (2)C39—C34—B1—C22164.01 (13)
C1—C16—C21—C20179.19 (14)C35—C34—B1—C2222.4 (2)
C27—C22—C23—C242.3 (2)C39—C34—B1—C2874.04 (16)
B1—C22—C23—C24176.53 (14)C35—C34—B1—C2899.51 (16)
C22—C23—C24—C250.7 (2)C39—C34—B1—C4046.58 (18)
C23—C24—C25—C261.3 (2)C35—C34—B1—C40139.86 (14)
C24—C25—C26—C271.4 (2)C41—C40—B1—C2293.19 (16)
C25—C26—C27—C220.3 (2)C45—C40—B1—C2280.86 (16)
C23—C22—C27—C262.1 (2)C41—C40—B1—C28144.63 (14)
B1—C22—C27—C26176.30 (14)C45—C40—B1—C2841.32 (18)
C33—C28—C29—C301.4 (2)C41—C40—B1—C3428.87 (19)
B1—C28—C29—C30174.54 (15)C45—C40—B1—C34157.08 (13)
Hydrogen-bond geometry (Å, º) top
Cg1–Cg5 and Cg8 are the centroids of the C22–C27, C28–C33, C34–C39, C40–C45, N1/C1/C2/C7/C8/C13 and C16–C21 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···Cg1i0.882.453.303 (2)165
N2—H2A···Cg4i0.882.623.3297 (18)139
C21—H21···Cg3ii0.952.753.685 (2)167
C25—H25···Cg8i0.952.793.632 (2)148
C36—H36···Cg5iii0.952.813.3593 (18)118
C48—H48···Cg20.982.783.609 (2)143
C48—H48A···Cg30.992.613.488 (2)149
Symmetry codes: (i) x, y, z+1; (ii) x, y, z+1; (iii) x, y, z1.
 

Funding information

Funding for this research was provided by: Japan Society for the Promotion of Science (grant No. 21K05089).

References

First citationBorodin, O., Shchukin, Y., Robertson, C. C., Richter, S. & von Delius, M. (2021). J. Am. Chem. Soc. 143, 16448–16457.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationBrandenburg, K. (2014). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2021). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBurla, M. C., Caliandro, R., Carrozzini, B., Cascarano, G. L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A. & Polidori, G. (2015). J. Appl. Cryst. 48, 306–309.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationChen, W., Turro, N. J. & Tomalia, D. A. (2000). Langmuir, 16, 15–19.  Web of Science CrossRef Google Scholar
First citationKabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Japan, 51, 218–224.  CrossRef Google Scholar
First citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
First citationMa, H., Liu, B., Li, B., Zhang, L., Li, Y.-G., Tan, H.-Q., Zang, H.-Y. & Zhu, G. (2016). J. Am. Chem. Soc. 138, 5897–5903.  Web of Science CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationShimazaki, R. & Sadakiyo, M. (2022). IUCrData, 7, x220884.  Google Scholar
First citationTsuzuki, S., Honda, K., Uchimaru, T., Mikami, M. & Tanabe, K. (2000). J. Am. Chem. Soc. 122, 3746–3753.  Web of Science CrossRef CAS Google Scholar

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