research communications
of tris[4-(naphthalen-1-yl)phenyl]amine
aKansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan, bOsaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan, cOkayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan, and dOsaka Kyoiku University, 4-698-1 Asahigaoka, Kashiwara, Osaka 582-8582, Japan
*Correspondence e-mail: myano@kansai-u.ac.jp
In the title molecule, C48H33N, the central N atom shows no pyramidalization, so that the N atom and the three C atoms bound to the N atom lie almost in the same plane. The three para-phenylene rings bonded to the N atom are in a propeller form. All of the naphthalene ring systems are slightly bent. In the crystal, molecules form an inversion dimer, through two pairs of C—H⋯π interactions, which further interacts with the adjacent dimer via another two pairs of C—H⋯π interactions, forming a column structure along the a axis. There are no significant interactions between these column structures.
Keywords: crystal structure; triarylamine; hole transporter; organic electronics; electroluminescence.
CCDC reference: 2031765
1. Chemical context
Triarylamines (TAAs) having various substituents at their para-positions are widely known to give the corresponding stable cation radicals upon chemical or electrochemical one electron oxidation (Seo et al., 1966). π-Extended TAAs with extra aromatic rings at the periphery have received considerable attention as key components in the fields of organic devices. Among them, the title compound was first synthesized by Kwon et al. (2010) as a hole-transporting material in organic light-emitting diodes. Recently, phosphorescent organic light-emitting diodes were also reported by using the title compound as the hole-transporting material (Krucaite et al., 2019). Until now, no of this compound has been reported. We report herein the of the title compound.
2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The three naphthalene ring systems are slightly bent, with r.m.s. deviations of 0.038 (2), 0.055 (2) and 0.044 (2) Å, respectively, for the C8–C17, C24–C33 and C40–C49 ring systems. The C atoms at the 1-, 3- and 7-positions show the largest deviations from the mean planes [1-positions: −0.0464 (16) Å for C8, 0.0766 (18) Å for C24, and 0.0518 (17) Å for C40; 3-positions: 0.0468 (19) Å for C10, −0.068 (2) Å for C26, and −0.056 (2) Å for C42; 7-positions: 0.041 (2) Å for C15, −0.067 (2) Å for C31, and −0.051 (2) Å for C47]. In all cases, the C atoms at the 3- and 7-positions deviate from the mean plane to the same side, while the C atoms at 1-positions deviate to the opposite side. The central N1 atom shows no pyramidalization, with a deviation from the plane of the bonded C atoms (C2, C18 and C34) of 0.0402 (14) Å. The three para-phenylene rings are bonded to the N atom in propeller-wise, which is a common arrangement for Ph3N fragments. The torsion angles C3—C2—N1—C34, C19—C18—N1—C2 and C35—C34—N1—C18 are −35.0 (2), −60.6 (2) and −30.3 (2)°, respectively. The para-phenylene ring and the mean plane of the neighboring naphthalene ring system are inclined to each other by 54.66 (7)° for (C2–C7)/(C8–C17), 48.80 (7)° for (C18–C23)/(C24–C33) and 56.21 (7)° for (C34–C39)/(C40–C49).
3. Supramolecular features
In the crystal, each molecule interacts with two others via four intermolecular C—H⋯π interactions (Table 1). The molecules are linked by complementary C—H⋯π interactions [C9—H9⋯Cg1i and C20—H20⋯Cg2i; Cg1 and Cg2 are the centroids of the C24–C28/C33 and C2–C7 rings, respectively; symmetry code: (i) −x + 1, −y, −z + 2], forming an inversion dimer (Fig. 2). The other inversion dimer is formed by complementary C—H⋯π interactions [C23—H23⋯Cg2ii and C47—H47⋯Cg3ii; Cg3 is the centroid of the C12–C17 ring; symmetry code: (ii) −x, −y, −z + 2] (Fig. 3). As a result, the molecules form a column structure by intermolecular C—H⋯π interactions along [100], and there is no significant interaction between the column structures (Fig. 4).
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.41, update August 2020; Groom et al., 2016) for compounds containing triphenylamines yielded 4384 hits (including 3640 hits for non-polymeric compounds). Limiting the search to non-polymeric triphenylamines with the same aromatic ring at the three para-positions, there were 19 hits (16 compounds), which included eleven hits (nine compounds) with heteroaromatic rings and eight hits (seven compounds) with phenyl rings. The seven compounds with phenyl rings at the three para-position of the triphenylamine skeleton include tris(biphenyl-4-yl)amine [WEHLIE (Inada et al., 1994); WEHLIE01 (Nieger et al., 2017)] and its perchlorate salt (BPHAMP10; Brown et al., 1977), tris[4-(2,3,4,5,6-pentaphenylphenyl)phenyl]amine (PULSAR; Gagnon et al., 2010), tri[4-(4-formylphenyl)phenyl]amine (DEHYUN; Fang et al., 2017), tri[4-(3-formylphenyl)phenyl]amine (MADJAF; Mondal et al., 2016), tris[4′-(4,6-diaminotriazin-2-yl)biphenyl-4-yl]amine (MUNNER; Feng et al., 2020) and tri[4-(4-methoxycarbonylphenyl)phenyl]amine (XAXKIT; Zhang et al., 2017). It is notable that there is only one reported example where the three polycyclic aromatic groups on the periphery of the tripenylamine skeleton are the same, viz. tris[4-(quinolin-2-yl)phenyl]amine (BEFCEX; Hariharan et al., 2016).
5. Synthesis and crystallization
The title compound was prepared by a modification of the previously reported Suzuki–Miyaura coupling reaction (Kwon et al., 2010). Tris(4-bromophenyl)amine (2.00 g, 4.15 mmol), 1-naphthylboronic acid (3.57 g, 20.7 mmol), tetrakis(triphenylphosphine)palladium(0) (240 mg, 0.21 mmol), K2CO3 (2.87 g, 20.7 mmol), toluene (42 mL) and water (10.4 mL) were placed in a 100 mL round-bottom flask. After the solution was purged with nitrogen for 10 minutes, it was heated at 373 K under nitrogen for 24 h. The reaction mixture was extracted with ethyl acetate. After drying over anhydrous Na2SO4, the organic layer was evaporated. The residue was redissolved in a small amount of ethyl acetate. The addition of a large amount of methanol gave the pure product as a white precipitate (845 mg, 1.35 mmol, 33%). Colorless single crystals suitable for X-ray diffraction were obtained by means of the vapor diffusion method from chloroform as a rich solvent and n-hexane as a poor solvent after standing for one week.
6. Refinement
Crystal data, data collection and structure . C-bound H atoms were placed in geometrically calculated positions (C—H = 0.95 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). One outlier (011) was omitted from the refinement.
details are summarized in Table 2
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Supporting information
CCDC reference: 2031765
https://doi.org/10.1107/S2056989020012529/is5556sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020012529/is5556Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020012529/is5556Isup3.cml
Data collection: RAPID-AUTO (Rigaku, 2006); cell
RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SIR92 (Altomare, et al., 1994); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020), publCIF (Westrip, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2016).C48H33N | Z = 2 |
Mr = 623.80 | F(000) = 656.00 |
Triclinic, P1 | Dx = 1.259 Mg m−3 |
a = 10.0952 (4) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 13.0135 (6) Å | Cell parameters from 12529 reflections |
c = 13.5643 (5) Å | θ = 2.1–27.5° |
α = 74.429 (5)° | µ = 0.07 mm−1 |
β = 75.671 (5)° | T = 173 K |
γ = 78.309 (6)° | Block, colorless |
V = 1645.39 (13) Å3 | 0.50 × 0.40 × 0.25 mm |
Rigaku R-AXIS RAPID diffractometer | 5597 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.030 |
ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.689, Tmax = 0.982 | k = −16→16 |
16018 measured reflections | l = −17→17 |
7480 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0463P)2 + 0.6997P] where P = (Fo2 + 2Fc2)/3 |
7480 reflections | (Δ/σ)max < 0.001 |
442 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Primary atom site location: structure-invariant direct methods |
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.14801 (14) | 0.09044 (10) | 1.02472 (10) | 0.0266 (3) | |
C2 | 0.16313 (15) | −0.00593 (12) | 1.10268 (12) | 0.0232 (3) | |
C3 | 0.13832 (16) | −0.00538 (12) | 1.20859 (12) | 0.0259 (3) | |
H3 | 0.1124 | 0.0612 | 1.2295 | 0.031* | |
C4 | 0.15124 (16) | −0.10144 (12) | 1.28352 (12) | 0.0260 (3) | |
H4 | 0.1334 | −0.0992 | 1.3551 | 0.031* | |
C5 | 0.18977 (15) | −0.20126 (12) | 1.25653 (12) | 0.0240 (3) | |
C6 | 0.21653 (16) | −0.20035 (12) | 1.15008 (12) | 0.0248 (3) | |
H6 | 0.2436 | −0.2668 | 1.1291 | 0.030* | |
C7 | 0.20467 (15) | −0.10512 (12) | 1.07433 (12) | 0.0248 (3) | |
H7 | 0.2249 | −0.1073 | 1.0026 | 0.030* | |
C8 | 0.21175 (16) | −0.30334 (12) | 1.33678 (12) | 0.0259 (3) | |
C9 | 0.29701 (17) | −0.30985 (13) | 1.40386 (13) | 0.0311 (4) | |
H9 | 0.3343 | −0.2476 | 1.4016 | 0.037* | |
C10 | 0.33033 (19) | −0.40671 (14) | 1.47592 (14) | 0.0357 (4) | |
H10 | 0.3897 | −0.4092 | 1.5212 | 0.043* | |
C11 | 0.27776 (19) | −0.49663 (14) | 1.48081 (14) | 0.0358 (4) | |
H11 | 0.3029 | −0.5620 | 1.5283 | 0.043* | |
C12 | 0.18616 (18) | −0.49406 (13) | 1.41617 (13) | 0.0305 (4) | |
C13 | 0.12495 (19) | −0.58567 (14) | 1.42374 (15) | 0.0371 (4) | |
H13 | 0.1493 | −0.6515 | 1.4709 | 0.045* | |
C14 | 0.0320 (2) | −0.58075 (15) | 1.36455 (15) | 0.0413 (4) | |
H14 | −0.0071 | −0.6431 | 1.3700 | 0.050* | |
C15 | −0.00617 (19) | −0.48328 (15) | 1.29518 (15) | 0.0386 (4) | |
H15 | −0.0724 | −0.4799 | 1.2550 | 0.046* | |
C16 | 0.05106 (17) | −0.39365 (14) | 1.28512 (13) | 0.0316 (4) | |
H16 | 0.0241 | −0.3287 | 1.2378 | 0.038* | |
C17 | 0.15007 (16) | −0.39574 (13) | 1.34394 (12) | 0.0269 (3) | |
C18 | 0.23208 (16) | 0.09424 (11) | 0.92230 (12) | 0.0242 (3) | |
C19 | 0.37499 (17) | 0.07939 (12) | 0.90874 (13) | 0.0281 (3) | |
H19 | 0.4165 | 0.0695 | 0.9669 | 0.034* | |
C20 | 0.45771 (17) | 0.07890 (13) | 0.81001 (13) | 0.0291 (4) | |
H20 | 0.5554 | 0.0670 | 0.8019 | 0.035* | |
C21 | 0.39922 (17) | 0.09568 (12) | 0.72244 (13) | 0.0275 (3) | |
C22 | 0.25551 (17) | 0.11267 (13) | 0.73763 (13) | 0.0296 (4) | |
H22 | 0.2133 | 0.1256 | 0.6793 | 0.036* | |
C23 | 0.17291 (16) | 0.11113 (13) | 0.83621 (13) | 0.0278 (3) | |
H23 | 0.0752 | 0.1217 | 0.8448 | 0.033* | |
C24 | 0.48684 (17) | 0.10367 (13) | 0.61483 (13) | 0.0291 (4) | |
C25 | 0.45260 (18) | 0.18906 (13) | 0.53581 (13) | 0.0321 (4) | |
H25 | 0.3686 | 0.2363 | 0.5493 | 0.039* | |
C26 | 0.5382 (2) | 0.20880 (16) | 0.43537 (14) | 0.0430 (5) | |
H26 | 0.5112 | 0.2679 | 0.3821 | 0.052* | |
C27 | 0.6607 (2) | 0.14220 (16) | 0.41495 (14) | 0.0415 (4) | |
H27 | 0.7210 | 0.1574 | 0.3485 | 0.050* | |
C28 | 0.69744 (18) | 0.05122 (14) | 0.49235 (13) | 0.0330 (4) | |
C29 | 0.8225 (2) | −0.02024 (16) | 0.47202 (15) | 0.0416 (4) | |
H29 | 0.8847 | −0.0036 | 0.4067 | 0.050* | |
C30 | 0.8555 (2) | −0.11158 (16) | 0.54362 (16) | 0.0423 (5) | |
H30 | 0.9398 | −0.1580 | 0.5286 | 0.051* | |
C31 | 0.76354 (19) | −0.13658 (15) | 0.64002 (15) | 0.0381 (4) | |
H31 | 0.7841 | −0.2022 | 0.6887 | 0.046* | |
C32 | 0.64506 (18) | −0.06841 (13) | 0.66525 (13) | 0.0307 (4) | |
H32 | 0.5862 | −0.0861 | 0.7320 | 0.037* | |
C33 | 0.60871 (17) | 0.02880 (13) | 0.59287 (13) | 0.0297 (4) | |
C34 | 0.04483 (15) | 0.17917 (12) | 1.04198 (12) | 0.0236 (3) | |
C35 | 0.06416 (16) | 0.28295 (12) | 0.98293 (12) | 0.0265 (3) | |
H35 | 0.1471 | 0.2937 | 0.9324 | 0.032* | |
C36 | −0.03641 (17) | 0.37021 (12) | 0.99736 (13) | 0.0275 (3) | |
H36 | −0.0224 | 0.4398 | 0.9551 | 0.033* | |
C37 | −0.15856 (16) | 0.35813 (12) | 1.07296 (12) | 0.0257 (3) | |
C38 | −0.17683 (16) | 0.25404 (12) | 1.13011 (12) | 0.0264 (3) | |
H38 | −0.2595 | 0.2433 | 1.1809 | 0.032* | |
C39 | −0.07832 (16) | 0.16580 (12) | 1.11521 (12) | 0.0256 (3) | |
H39 | −0.0946 | 0.0957 | 1.1550 | 0.031* | |
C40 | −0.26129 (16) | 0.45250 (12) | 1.09758 (13) | 0.0270 (3) | |
C41 | −0.29800 (18) | 0.46387 (14) | 1.19948 (14) | 0.0330 (4) | |
H41 | −0.2614 | 0.4097 | 1.2524 | 0.040* | |
C42 | −0.38881 (19) | 0.55428 (15) | 1.22681 (15) | 0.0376 (4) | |
H42 | −0.4133 | 0.5601 | 1.2976 | 0.045* | |
C43 | −0.44133 (18) | 0.63313 (14) | 1.15188 (15) | 0.0358 (4) | |
H43 | −0.4994 | 0.6951 | 1.1705 | 0.043* | |
C44 | −0.41071 (16) | 0.62406 (12) | 1.04683 (14) | 0.0298 (4) | |
C45 | −0.46871 (18) | 0.70263 (14) | 0.96833 (15) | 0.0372 (4) | |
H45 | −0.5255 | 0.7657 | 0.9854 | 0.045* | |
C46 | −0.44480 (19) | 0.68960 (14) | 0.86875 (15) | 0.0398 (4) | |
H46 | −0.4853 | 0.7432 | 0.8174 | 0.048* | |
C47 | −0.36022 (19) | 0.59692 (15) | 0.84179 (14) | 0.0376 (4) | |
H47 | −0.3453 | 0.5874 | 0.7727 | 0.045* | |
C48 | −0.29959 (17) | 0.52080 (13) | 0.91465 (13) | 0.0314 (4) | |
H48 | −0.2416 | 0.4592 | 0.8951 | 0.038* | |
C49 | −0.32131 (16) | 0.53158 (12) | 1.01890 (13) | 0.0264 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0254 (7) | 0.0233 (6) | 0.0238 (7) | 0.0055 (5) | −0.0008 (5) | −0.0039 (5) |
C2 | 0.0173 (7) | 0.0223 (7) | 0.0265 (8) | 0.0025 (6) | −0.0038 (6) | −0.0045 (6) |
C3 | 0.0246 (8) | 0.0248 (7) | 0.0278 (8) | 0.0040 (6) | −0.0067 (6) | −0.0094 (7) |
C4 | 0.0226 (8) | 0.0300 (8) | 0.0245 (8) | 0.0012 (6) | −0.0045 (6) | −0.0089 (7) |
C5 | 0.0189 (7) | 0.0241 (7) | 0.0267 (8) | −0.0006 (6) | −0.0044 (6) | −0.0044 (6) |
C6 | 0.0221 (8) | 0.0218 (7) | 0.0295 (8) | 0.0011 (6) | −0.0037 (6) | −0.0088 (6) |
C7 | 0.0207 (8) | 0.0273 (8) | 0.0249 (8) | 0.0016 (6) | −0.0034 (6) | −0.0086 (6) |
C8 | 0.0230 (8) | 0.0259 (8) | 0.0251 (8) | 0.0009 (6) | −0.0020 (6) | −0.0059 (6) |
C9 | 0.0313 (9) | 0.0282 (8) | 0.0326 (9) | −0.0022 (7) | −0.0089 (7) | −0.0044 (7) |
C10 | 0.0348 (10) | 0.0369 (9) | 0.0336 (9) | 0.0018 (7) | −0.0142 (8) | −0.0040 (8) |
C11 | 0.0374 (10) | 0.0282 (8) | 0.0344 (9) | 0.0032 (7) | −0.0084 (8) | 0.0004 (7) |
C12 | 0.0311 (9) | 0.0267 (8) | 0.0284 (8) | 0.0009 (6) | −0.0001 (7) | −0.0066 (7) |
C13 | 0.0388 (10) | 0.0272 (8) | 0.0387 (10) | −0.0022 (7) | −0.0010 (8) | −0.0049 (8) |
C14 | 0.0409 (11) | 0.0342 (9) | 0.0480 (11) | −0.0125 (8) | 0.0020 (9) | −0.0132 (9) |
C15 | 0.0339 (10) | 0.0446 (10) | 0.0394 (10) | −0.0102 (8) | −0.0057 (8) | −0.0116 (9) |
C16 | 0.0278 (9) | 0.0338 (9) | 0.0305 (9) | −0.0041 (7) | −0.0028 (7) | −0.0060 (7) |
C17 | 0.0240 (8) | 0.0276 (8) | 0.0252 (8) | −0.0001 (6) | 0.0002 (6) | −0.0070 (7) |
C18 | 0.0234 (8) | 0.0184 (7) | 0.0266 (8) | 0.0018 (6) | −0.0006 (6) | −0.0057 (6) |
C19 | 0.0260 (8) | 0.0273 (8) | 0.0283 (8) | 0.0021 (6) | −0.0069 (7) | −0.0050 (7) |
C20 | 0.0208 (8) | 0.0284 (8) | 0.0348 (9) | 0.0005 (6) | −0.0019 (6) | −0.0081 (7) |
C21 | 0.0283 (8) | 0.0236 (7) | 0.0288 (8) | −0.0029 (6) | −0.0013 (7) | −0.0078 (7) |
C22 | 0.0283 (9) | 0.0318 (8) | 0.0294 (8) | −0.0035 (7) | −0.0065 (7) | −0.0084 (7) |
C23 | 0.0205 (8) | 0.0295 (8) | 0.0320 (9) | −0.0011 (6) | −0.0028 (6) | −0.0088 (7) |
C24 | 0.0309 (9) | 0.0284 (8) | 0.0291 (8) | −0.0077 (7) | −0.0050 (7) | −0.0068 (7) |
C25 | 0.0335 (9) | 0.0310 (8) | 0.0309 (9) | −0.0045 (7) | −0.0072 (7) | −0.0048 (7) |
C26 | 0.0542 (12) | 0.0436 (10) | 0.0297 (9) | −0.0134 (9) | −0.0123 (9) | 0.0021 (8) |
C27 | 0.0475 (12) | 0.0501 (11) | 0.0246 (9) | −0.0151 (9) | −0.0010 (8) | −0.0046 (8) |
C28 | 0.0348 (10) | 0.0396 (9) | 0.0274 (8) | −0.0123 (7) | −0.0004 (7) | −0.0128 (8) |
C29 | 0.0372 (11) | 0.0522 (11) | 0.0377 (10) | −0.0112 (9) | 0.0036 (8) | −0.0210 (9) |
C30 | 0.0321 (10) | 0.0448 (11) | 0.0517 (12) | −0.0020 (8) | 0.0002 (8) | −0.0250 (10) |
C31 | 0.0381 (10) | 0.0336 (9) | 0.0439 (10) | −0.0026 (7) | −0.0057 (8) | −0.0155 (8) |
C32 | 0.0321 (9) | 0.0269 (8) | 0.0318 (9) | −0.0053 (7) | −0.0017 (7) | −0.0081 (7) |
C33 | 0.0304 (9) | 0.0315 (8) | 0.0287 (8) | −0.0088 (7) | −0.0016 (7) | −0.0104 (7) |
C34 | 0.0210 (8) | 0.0227 (7) | 0.0255 (8) | 0.0038 (6) | −0.0050 (6) | −0.0076 (6) |
C35 | 0.0223 (8) | 0.0261 (8) | 0.0285 (8) | −0.0016 (6) | 0.0000 (6) | −0.0081 (7) |
C36 | 0.0280 (8) | 0.0208 (7) | 0.0314 (8) | −0.0021 (6) | −0.0031 (7) | −0.0058 (7) |
C37 | 0.0243 (8) | 0.0247 (7) | 0.0271 (8) | 0.0040 (6) | −0.0060 (6) | −0.0092 (6) |
C38 | 0.0208 (8) | 0.0286 (8) | 0.0252 (8) | 0.0020 (6) | −0.0017 (6) | −0.0055 (7) |
C39 | 0.0251 (8) | 0.0219 (7) | 0.0262 (8) | 0.0013 (6) | −0.0054 (6) | −0.0028 (6) |
C40 | 0.0226 (8) | 0.0243 (7) | 0.0323 (9) | 0.0020 (6) | −0.0034 (6) | −0.0096 (7) |
C41 | 0.0295 (9) | 0.0340 (9) | 0.0332 (9) | 0.0047 (7) | −0.0065 (7) | −0.0109 (7) |
C42 | 0.0333 (10) | 0.0438 (10) | 0.0365 (10) | 0.0040 (8) | −0.0034 (8) | −0.0212 (8) |
C43 | 0.0266 (9) | 0.0318 (9) | 0.0481 (11) | 0.0052 (7) | −0.0023 (8) | −0.0199 (8) |
C44 | 0.0206 (8) | 0.0247 (8) | 0.0412 (10) | 0.0000 (6) | −0.0018 (7) | −0.0094 (7) |
C45 | 0.0274 (9) | 0.0256 (8) | 0.0499 (11) | 0.0035 (7) | −0.0020 (8) | −0.0046 (8) |
C46 | 0.0298 (9) | 0.0335 (9) | 0.0434 (11) | 0.0003 (7) | −0.0063 (8) | 0.0077 (8) |
C47 | 0.0336 (10) | 0.0413 (10) | 0.0320 (9) | −0.0039 (8) | −0.0035 (7) | −0.0024 (8) |
C48 | 0.0285 (9) | 0.0288 (8) | 0.0331 (9) | 0.0007 (7) | −0.0027 (7) | −0.0075 (7) |
C49 | 0.0207 (8) | 0.0233 (7) | 0.0324 (9) | −0.0009 (6) | −0.0017 (6) | −0.0070 (7) |
N1—C2 | 1.4159 (19) | C25—C26 | 1.410 (2) |
N1—C34 | 1.4179 (18) | C25—H25 | 0.9500 |
N1—C18 | 1.4315 (19) | C26—C27 | 1.372 (3) |
C2—C3 | 1.398 (2) | C26—H26 | 0.9500 |
C2—C7 | 1.399 (2) | C27—C28 | 1.410 (3) |
C3—C4 | 1.389 (2) | C27—H27 | 0.9500 |
C3—H3 | 0.9500 | C28—C29 | 1.423 (3) |
C4—C5 | 1.397 (2) | C28—C33 | 1.426 (2) |
C4—H4 | 0.9500 | C29—C30 | 1.359 (3) |
C5—C6 | 1.399 (2) | C29—H29 | 0.9500 |
C5—C8 | 1.491 (2) | C30—C31 | 1.404 (3) |
C6—C7 | 1.387 (2) | C30—H30 | 0.9500 |
C6—H6 | 0.9500 | C31—C32 | 1.366 (2) |
C7—H7 | 0.9500 | C31—H31 | 0.9500 |
C8—C9 | 1.376 (2) | C32—C33 | 1.422 (2) |
C8—C17 | 1.433 (2) | C32—H32 | 0.9500 |
C9—C10 | 1.410 (2) | C34—C39 | 1.395 (2) |
C9—H9 | 0.9500 | C34—C35 | 1.397 (2) |
C10—C11 | 1.359 (3) | C35—C36 | 1.383 (2) |
C10—H10 | 0.9500 | C35—H35 | 0.9500 |
C11—C12 | 1.414 (3) | C36—C37 | 1.401 (2) |
C11—H11 | 0.9500 | C36—H36 | 0.9500 |
C12—C13 | 1.419 (2) | C37—C38 | 1.392 (2) |
C12—C17 | 1.430 (2) | C37—C40 | 1.493 (2) |
C13—C14 | 1.360 (3) | C38—C39 | 1.382 (2) |
C13—H13 | 0.9500 | C38—H38 | 0.9500 |
C14—C15 | 1.408 (3) | C39—H39 | 0.9500 |
C14—H14 | 0.9500 | C40—C41 | 1.380 (2) |
C15—C16 | 1.364 (3) | C40—C49 | 1.429 (2) |
C15—H15 | 0.9500 | C41—C42 | 1.411 (2) |
C16—C17 | 1.417 (2) | C41—H41 | 0.9500 |
C16—H16 | 0.9500 | C42—C43 | 1.361 (3) |
C18—C23 | 1.387 (2) | C42—H42 | 0.9500 |
C18—C19 | 1.388 (2) | C43—C44 | 1.413 (3) |
C19—C20 | 1.393 (2) | C43—H43 | 0.9500 |
C19—H19 | 0.9500 | C44—C45 | 1.415 (2) |
C20—C21 | 1.401 (2) | C44—C49 | 1.429 (2) |
C20—H20 | 0.9500 | C45—C46 | 1.363 (3) |
C21—C22 | 1.394 (2) | C45—H45 | 0.9500 |
C21—C24 | 1.497 (2) | C46—C47 | 1.408 (3) |
C22—C23 | 1.387 (2) | C46—H46 | 0.9500 |
C22—H22 | 0.9500 | C47—C48 | 1.364 (2) |
C23—H23 | 0.9500 | C47—H47 | 0.9500 |
C24—C25 | 1.375 (2) | C48—C49 | 1.417 (2) |
C24—C33 | 1.428 (2) | C48—H48 | 0.9500 |
C2—N1—C34 | 122.34 (13) | C26—C25—H25 | 118.9 |
C2—N1—C18 | 118.41 (12) | C27—C26—C25 | 119.68 (17) |
C34—N1—C18 | 119.01 (12) | C27—C26—H26 | 120.2 |
C3—C2—C7 | 118.28 (14) | C25—C26—H26 | 120.2 |
C3—C2—N1 | 121.81 (14) | C26—C27—C28 | 120.15 (17) |
C7—C2—N1 | 119.91 (14) | C26—C27—H27 | 119.9 |
C4—C3—C2 | 120.50 (14) | C28—C27—H27 | 119.9 |
C4—C3—H3 | 119.8 | C27—C28—C29 | 121.05 (16) |
C2—C3—H3 | 119.8 | C27—C28—C33 | 120.29 (16) |
C3—C4—C5 | 121.84 (15) | C29—C28—C33 | 118.65 (16) |
C3—C4—H4 | 119.1 | C30—C29—C28 | 121.74 (17) |
C5—C4—H4 | 119.1 | C30—C29—H29 | 119.1 |
C4—C5—C6 | 116.98 (14) | C28—C29—H29 | 119.1 |
C4—C5—C8 | 121.42 (14) | C29—C30—C31 | 119.25 (18) |
C6—C5—C8 | 121.44 (14) | C29—C30—H30 | 120.4 |
C7—C6—C5 | 121.86 (14) | C31—C30—H30 | 120.4 |
C7—C6—H6 | 119.1 | C32—C31—C30 | 121.33 (18) |
C5—C6—H6 | 119.1 | C32—C31—H31 | 119.3 |
C6—C7—C2 | 120.52 (14) | C30—C31—H31 | 119.3 |
C6—C7—H7 | 119.7 | C31—C32—C33 | 120.81 (16) |
C2—C7—H7 | 119.7 | C31—C32—H32 | 119.6 |
C9—C8—C17 | 119.14 (14) | C33—C32—H32 | 119.6 |
C9—C8—C5 | 118.90 (15) | C32—C33—C28 | 118.03 (15) |
C17—C8—C5 | 121.93 (14) | C32—C33—C24 | 123.46 (15) |
C8—C9—C10 | 121.53 (16) | C28—C33—C24 | 118.49 (15) |
C8—C9—H9 | 119.2 | C39—C34—C35 | 118.44 (13) |
C10—C9—H9 | 119.2 | C39—C34—N1 | 121.76 (14) |
C11—C10—C9 | 120.23 (17) | C35—C34—N1 | 119.78 (14) |
C11—C10—H10 | 119.9 | C36—C35—C34 | 120.59 (14) |
C9—C10—H10 | 119.9 | C36—C35—H35 | 119.7 |
C10—C11—C12 | 120.84 (16) | C34—C35—H35 | 119.7 |
C10—C11—H11 | 119.6 | C35—C36—C37 | 121.41 (14) |
C12—C11—H11 | 119.6 | C35—C36—H36 | 119.3 |
C11—C12—C13 | 121.65 (16) | C37—C36—H36 | 119.3 |
C11—C12—C17 | 119.32 (15) | C38—C37—C36 | 117.18 (14) |
C13—C12—C17 | 118.99 (16) | C38—C37—C40 | 120.52 (14) |
C14—C13—C12 | 121.10 (17) | C36—C37—C40 | 122.16 (14) |
C14—C13—H13 | 119.4 | C39—C38—C37 | 122.02 (14) |
C12—C13—H13 | 119.4 | C39—C38—H38 | 119.0 |
C13—C14—C15 | 120.00 (17) | C37—C38—H38 | 119.0 |
C13—C14—H14 | 120.0 | C38—C39—C34 | 120.31 (14) |
C15—C14—H14 | 120.0 | C38—C39—H39 | 119.8 |
C16—C15—C14 | 120.66 (18) | C34—C39—H39 | 119.8 |
C16—C15—H15 | 119.7 | C41—C40—C49 | 119.25 (14) |
C14—C15—H15 | 119.7 | C41—C40—C37 | 118.67 (14) |
C15—C16—C17 | 121.18 (16) | C49—C40—C37 | 122.08 (14) |
C15—C16—H16 | 119.4 | C40—C41—C42 | 121.39 (16) |
C17—C16—H16 | 119.4 | C40—C41—H41 | 119.3 |
C16—C17—C12 | 118.04 (15) | C42—C41—H41 | 119.3 |
C16—C17—C8 | 123.11 (15) | C43—C42—C41 | 120.07 (17) |
C12—C17—C8 | 118.82 (15) | C43—C42—H42 | 120.0 |
C23—C18—C19 | 119.28 (14) | C41—C42—H42 | 120.0 |
C23—C18—N1 | 120.95 (14) | C42—C43—C44 | 120.94 (15) |
C19—C18—N1 | 119.77 (14) | C42—C43—H43 | 119.5 |
C18—C19—C20 | 120.17 (15) | C44—C43—H43 | 119.5 |
C18—C19—H19 | 119.9 | C43—C44—C45 | 122.04 (15) |
C20—C19—H19 | 119.9 | C43—C44—C49 | 119.32 (15) |
C19—C20—C21 | 121.09 (15) | C45—C44—C49 | 118.62 (16) |
C19—C20—H20 | 119.5 | C46—C45—C44 | 121.35 (16) |
C21—C20—H20 | 119.5 | C46—C45—H45 | 119.3 |
C22—C21—C20 | 117.70 (15) | C44—C45—H45 | 119.3 |
C22—C21—C24 | 120.65 (15) | C45—C46—C47 | 120.13 (17) |
C20—C21—C24 | 121.49 (15) | C45—C46—H46 | 119.9 |
C23—C22—C21 | 121.31 (16) | C47—C46—H46 | 119.9 |
C23—C22—H22 | 119.3 | C48—C47—C46 | 120.19 (18) |
C21—C22—H22 | 119.3 | C48—C47—H47 | 119.9 |
C18—C23—C22 | 120.43 (15) | C46—C47—H47 | 119.9 |
C18—C23—H23 | 119.8 | C47—C48—C49 | 121.42 (16) |
C22—C23—H23 | 119.8 | C47—C48—H48 | 119.3 |
C25—C24—C33 | 119.01 (15) | C49—C48—H48 | 119.3 |
C25—C24—C21 | 118.78 (15) | C48—C49—C44 | 118.24 (15) |
C33—C24—C21 | 122.12 (14) | C48—C49—C40 | 122.85 (14) |
C24—C25—C26 | 122.10 (17) | C44—C49—C40 | 118.88 (15) |
C24—C25—H25 | 118.9 | ||
C34—N1—C2—C3 | −35.0 (2) | C24—C25—C26—C27 | −0.8 (3) |
C18—N1—C2—C3 | 150.63 (15) | C25—C26—C27—C28 | 3.3 (3) |
C34—N1—C2—C7 | 145.32 (15) | C26—C27—C28—C29 | 178.57 (18) |
C18—N1—C2—C7 | −29.0 (2) | C26—C27—C28—C33 | −1.1 (3) |
C7—C2—C3—C4 | −1.7 (2) | C27—C28—C29—C30 | −176.10 (19) |
N1—C2—C3—C4 | 178.66 (14) | C33—C28—C29—C30 | 3.5 (3) |
C2—C3—C4—C5 | 0.4 (2) | C28—C29—C30—C31 | 0.3 (3) |
C3—C4—C5—C6 | 0.7 (2) | C29—C30—C31—C32 | −3.2 (3) |
C3—C4—C5—C8 | 176.20 (15) | C30—C31—C32—C33 | 2.1 (3) |
C4—C5—C6—C7 | −0.4 (2) | C31—C32—C33—C28 | 1.8 (3) |
C8—C5—C6—C7 | −175.91 (14) | C31—C32—C33—C24 | −179.57 (17) |
C5—C6—C7—C2 | −0.9 (2) | C27—C28—C33—C32 | 175.11 (17) |
C3—C2—C7—C6 | 2.0 (2) | C29—C28—C33—C32 | −4.5 (2) |
N1—C2—C7—C6 | −178.37 (14) | C27—C28—C33—C24 | −3.6 (2) |
C4—C5—C8—C9 | −51.0 (2) | C29—C28—C33—C24 | 176.78 (16) |
C6—C5—C8—C9 | 124.33 (17) | C25—C24—C33—C32 | −172.66 (16) |
C4—C5—C8—C17 | 130.98 (17) | C21—C24—C33—C32 | 10.7 (3) |
C6—C5—C8—C17 | −53.7 (2) | C25—C24—C33—C28 | 6.0 (2) |
C17—C8—C9—C10 | 3.1 (2) | C21—C24—C33—C28 | −170.65 (15) |
C5—C8—C9—C10 | −175.02 (15) | C2—N1—C34—C39 | −26.1 (2) |
C8—C9—C10—C11 | −0.2 (3) | C18—N1—C34—C39 | 148.20 (15) |
C9—C10—C11—C12 | −1.8 (3) | C2—N1—C34—C35 | 155.43 (15) |
C10—C11—C12—C13 | −176.88 (17) | C18—N1—C34—C35 | −30.3 (2) |
C10—C11—C12—C17 | 0.8 (3) | C39—C34—C35—C36 | 0.3 (2) |
C11—C12—C13—C14 | 176.91 (17) | N1—C34—C35—C36 | 178.83 (15) |
C17—C12—C13—C14 | −0.8 (3) | C34—C35—C36—C37 | 1.7 (3) |
C12—C13—C14—C15 | −0.7 (3) | C35—C36—C37—C38 | −2.5 (2) |
C13—C14—C15—C16 | 1.2 (3) | C35—C36—C37—C40 | 173.31 (15) |
C14—C15—C16—C17 | −0.1 (3) | C36—C37—C38—C39 | 1.3 (2) |
C15—C16—C17—C12 | −1.4 (2) | C40—C37—C38—C39 | −174.58 (16) |
C15—C16—C17—C8 | −179.29 (16) | C37—C38—C39—C34 | 0.7 (2) |
C11—C12—C17—C16 | −175.91 (15) | C35—C34—C39—C38 | −1.5 (2) |
C13—C12—C17—C16 | 1.8 (2) | N1—C34—C39—C38 | −179.98 (15) |
C11—C12—C17—C8 | 2.1 (2) | C38—C37—C40—C41 | 51.8 (2) |
C13—C12—C17—C8 | 179.79 (15) | C36—C37—C40—C41 | −123.81 (18) |
C9—C8—C17—C16 | 173.91 (15) | C38—C37—C40—C49 | −128.84 (17) |
C5—C8—C17—C16 | −8.0 (2) | C36—C37—C40—C49 | 55.5 (2) |
C9—C8—C17—C12 | −4.0 (2) | C49—C40—C41—C42 | −2.8 (3) |
C5—C8—C17—C12 | 174.10 (14) | C37—C40—C41—C42 | 176.55 (16) |
C2—N1—C18—C23 | 118.54 (16) | C40—C41—C42—C43 | −0.6 (3) |
C34—N1—C18—C23 | −56.0 (2) | C41—C42—C43—C44 | 2.6 (3) |
C2—N1—C18—C19 | −60.6 (2) | C42—C43—C44—C45 | 177.23 (17) |
C34—N1—C18—C19 | 124.90 (16) | C42—C43—C44—C49 | −1.1 (3) |
C23—C18—C19—C20 | −1.6 (2) | C43—C44—C45—C46 | −176.00 (17) |
N1—C18—C19—C20 | 177.57 (14) | C49—C44—C45—C46 | 2.4 (3) |
C18—C19—C20—C21 | 1.5 (2) | C44—C45—C46—C47 | −0.4 (3) |
C19—C20—C21—C22 | −0.1 (2) | C45—C46—C47—C48 | −1.3 (3) |
C19—C20—C21—C24 | 175.28 (15) | C46—C47—C48—C49 | 1.0 (3) |
C20—C21—C22—C23 | −1.1 (2) | C47—C48—C49—C44 | 0.9 (2) |
C24—C21—C22—C23 | −176.59 (15) | C47—C48—C49—C40 | 178.92 (16) |
C19—C18—C23—C22 | 0.3 (2) | C43—C44—C49—C48 | 175.83 (16) |
N1—C18—C23—C22 | −178.81 (14) | C45—C44—C49—C48 | −2.6 (2) |
C21—C22—C23—C18 | 1.1 (2) | C43—C44—C49—C40 | −2.2 (2) |
C22—C21—C24—C25 | 45.1 (2) | C45—C44—C49—C40 | 179.36 (15) |
C20—C21—C24—C25 | −130.13 (17) | C41—C40—C49—C48 | −173.82 (16) |
C22—C21—C24—C33 | −138.26 (17) | C37—C40—C49—C48 | 6.8 (2) |
C20—C21—C24—C33 | 46.5 (2) | C41—C40—C49—C44 | 4.1 (2) |
C33—C24—C25—C26 | −3.9 (3) | C37—C40—C49—C44 | −175.20 (15) |
C21—C24—C25—C26 | 172.84 (16) |
Cg1, Cg2 and Cg3 are the centroids of the rings C24–C28/C33, C2–C7 and C12–C17, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cg1i | 0.95 | 2.65 | 3.5309 (19) | 154 |
C20—H20···Cg2i | 0.95 | 2.91 | 3.8029 (19) | 156 |
C23—H23···Cg2ii | 0.95 | 2.71 | 3.6165 (18) | 159 |
C47—H47···Cg3ii | 0.95 | 2.99 | 3.660 (2) | 129 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2. |
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