organic compounds
N2,N2,N6,N6-Tetraphenylpyridine-2,6-diamine
aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp
In the title compound, C29H23N3, the molecule has an unsymmetrical structure, although it can possess Cs symmetry. The NC3 units around the amino N atoms are approximately planar and make dihedral angles of 13.41 (5) and 31.05 (5)° with the pyridine ring. In the crystal, C—H⋯N interactions between the phenyl and pyridyl rings lead to a columnar stack along the b axis.
CCDC reference: 1542477
Structure description
Aryl-substituted 2,6-diaminopyridines are used as blue luminous materials (Chen et al., 2001) and as part of molecular receptors (Yao et al., 2009; Fa et al., 2014). For related structures, see: Chen et al. (2001), Klinga et al. (1994), Berry et al. (2003) and Wang et al. (2007).
The title molecule has an unsymmetrical structure (Fig. 1), although it can possess Cs symmetry. The N2/C1/C6/C12 (r.m.s. deviation = 0.023 Å) and N3/C5/C18/C24 (r.m.s. deviation = 0.008 Å) units around the amino N atoms are approximately planar and subtend dihedral angles of 13.41 (5) and 31.05 (5)°, respectively, to the N1/C1–C5 pyridyl ring, indicating some conjugation between them. As a result of steric repulsion, the four phenyl rings exhibit large dihedral angles to the pyridyl ring plane, viz. 67.17 (5)° for the C6–C11 ring, 42.64 (5)° for the C12–C17 ring, 59.26 (5)° for the C18–C23 ring and 85.25 (5)° for the C24–C29 ring. The C12–C17 and C24-C29 phenyl rings make a dihedral angle of 52.51 (5)° and are oriented syn to the diaminopyridine moiety.
In the crystal, C—H⋯N hydrogen bonds between the phenyl and pyridyl rings makes a columnar stack along the b axis and C—H⋯π interactions are also observed (Table 1 and Fig. 2). These interactions are thought to be one of the reasons for lowering molecular symmetry.
Synthesis and crystallization
The title compound was obtained as a minor product by the reaction of N,N′-(pyridine-2,6-diyl)diacetamide with bromobenzene in the presence of CuI.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1542477
https://doi.org/10.1107/S2414314617005211/zp4012sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005211/zp4012Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617005211/zp4012Isup3.cml
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).C29H23N3 | F(000) = 872.00 |
Mr = 413.52 | Dx = 1.257 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 19.949 (4) Å | Cell parameters from 6510 reflections |
b = 5.6952 (10) Å | θ = 2.0–31.1° |
c = 20.921 (4) Å | µ = 0.07 mm−1 |
β = 113.152 (2)° | T = 93 K |
V = 2185.5 (7) Å3 | Block, colorless |
Z = 4 | 0.12 × 0.10 × 0.06 mm |
Rigaku Saturn724+ diffractometer | 4014 reflections with F2 > 2.0σ(F2) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −25→22 |
Tmin = 0.992, Tmax = 0.996 | k = −6→7 |
16972 measured reflections | l = −26→26 |
4997 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0607P)2 + 0.3246P] where P = (Fo2 + 2Fc2)/3 |
4997 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Primary atom site location: structure-invariant direct methods |
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 | 0.22089 (5) | 0.05699 (18) | 0.02057 (5) | 0.0183 (2) | |
N2 | 0.13310 (5) | −0.10586 (18) | −0.07967 (5) | 0.0192 (2) | |
N3 | 0.31284 (6) | 0.2296 (2) | 0.11341 (5) | 0.0237 (2) | |
C1 | 0.15290 (6) | −0.0247 (2) | −0.01159 (6) | 0.0179 (2) | |
C2 | 0.10344 (6) | −0.0310 (2) | 0.02107 (6) | 0.0210 (3) | |
C3 | 0.12642 (7) | 0.0567 (2) | 0.08790 (7) | 0.0240 (3) | |
C4 | 0.19604 (7) | 0.1464 (2) | 0.12166 (7) | 0.0245 (3) | |
C5 | 0.24170 (6) | 0.1413 (2) | 0.08529 (6) | 0.0204 (3) | |
C6 | 0.06996 (6) | −0.2532 (2) | −0.10914 (6) | 0.0196 (2) | |
C7 | 0.01295 (7) | −0.1862 (2) | −0.17059 (6) | 0.0218 (3) | |
C8 | −0.04818 (7) | −0.3288 (3) | −0.19904 (7) | 0.0262 (3) | |
C9 | −0.05299 (7) | −0.5353 (3) | −0.16599 (7) | 0.0294 (3) | |
C10 | 0.00375 (7) | −0.6018 (2) | −0.10515 (7) | 0.0292 (3) | |
C11 | 0.06585 (7) | −0.4628 (2) | −0.07697 (7) | 0.0238 (3) | |
C12 | 0.17718 (6) | −0.0741 (2) | −0.11891 (6) | 0.0183 (2) | |
C13 | 0.21613 (7) | 0.1330 (2) | −0.11500 (6) | 0.0209 (3) | |
C14 | 0.25942 (7) | 0.1554 (2) | −0.15304 (6) | 0.0235 (3) | |
C15 | 0.26401 (7) | −0.0251 (2) | −0.19596 (7) | 0.0248 (3) | |
C16 | 0.22393 (7) | −0.2281 (2) | −0.20109 (7) | 0.0244 (3) | |
C17 | 0.18107 (7) | −0.2534 (2) | −0.16269 (6) | 0.0210 (3) | |
C18 | 0.35806 (6) | 0.2183 (2) | 0.18519 (6) | 0.0200 (3) | |
C19 | 0.35523 (7) | 0.0266 (2) | 0.22566 (7) | 0.0238 (3) | |
C20 | 0.40196 (7) | 0.0158 (3) | 0.29523 (7) | 0.0272 (3) | |
C21 | 0.45213 (7) | 0.1935 (3) | 0.32528 (7) | 0.0273 (3) | |
C22 | 0.45537 (7) | 0.3831 (2) | 0.28495 (7) | 0.0251 (3) | |
C23 | 0.40846 (7) | 0.3967 (2) | 0.21551 (6) | 0.0228 (3) | |
C24 | 0.34234 (6) | 0.3263 (2) | 0.06662 (6) | 0.0195 (2) | |
C25 | 0.39688 (7) | 0.2069 (2) | 0.05433 (7) | 0.0235 (3) | |
C26 | 0.42474 (7) | 0.3004 (3) | 0.00875 (7) | 0.0309 (3) | |
C27 | 0.39866 (8) | 0.5121 (3) | −0.02417 (7) | 0.0329 (3) | |
C28 | 0.34452 (8) | 0.6312 (3) | −0.01182 (7) | 0.0305 (3) | |
C29 | 0.31614 (7) | 0.5382 (2) | 0.03378 (7) | 0.0248 (3) | |
H2 | 0.05578 | −0.09348 | −0.002 | 0.0252* | |
H3 | 0.09391 | 0.05535 | 0.11106 | 0.0288* | |
H4 | 0.21202 | 0.20849 | 0.1674 | 0.0294* | |
H7 | 0.01587 | −0.04361 | −0.19293 | 0.0262* | |
H8 | −0.08681 | −0.28475 | −0.24128 | 0.0314* | |
H9 | −0.09524 | −0.63103 | −0.18513 | 0.0353* | |
H10 | 0.00031 | −0.74309 | −0.0825 | 0.0350* | |
H11 | 0.10531 | −0.51116 | −0.03587 | 0.0286* | |
H13 | 0.21306 | 0.25848 | −0.08637 | 0.0251* | |
H14 | 0.28622 | 0.29604 | −0.14967 | 0.0282* | |
H15 | 0.29416 | −0.00949 | −0.22134 | 0.0298* | |
H16 | 0.22571 | −0.35106 | −0.23107 | 0.0292* | |
H17 | 0.15421 | −0.39404 | −0.16635 | 0.0252* | |
H19 | 0.3213 | −0.09649 | 0.20555 | 0.0286* | |
H20 | 0.39959 | −0.11459 | 0.32259 | 0.0327* | |
H21 | 0.48393 | 0.18543 | 0.37298 | 0.0327* | |
H22 | 0.48998 | 0.50438 | 0.30504 | 0.0301* | |
H23 | 0.41067 | 0.52825 | 0.18848 | 0.0274* | |
H25 | 0.41495 | 0.06202 | 0.07707 | 0.0281* | |
H26 | 0.46187 | 0.21904 | 0.00005 | 0.0371* | |
H27 | 0.418 | 0.5757 | −0.05533 | 0.0395* | |
H28 | 0.32672 | 0.77647 | −0.03445 | 0.0366* | |
H29 | 0.27894 | 0.61958 | 0.04235 | 0.0298* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0165 (5) | 0.0207 (5) | 0.0176 (5) | −0.0013 (4) | 0.0066 (4) | −0.0004 (4) |
N2 | 0.0183 (5) | 0.0224 (5) | 0.0177 (5) | −0.0051 (4) | 0.0078 (4) | −0.0031 (4) |
N3 | 0.0184 (5) | 0.0362 (6) | 0.0155 (5) | −0.0090 (5) | 0.0056 (4) | 0.0007 (4) |
C1 | 0.0178 (6) | 0.0182 (6) | 0.0176 (6) | −0.0009 (5) | 0.0070 (5) | −0.0009 (4) |
C2 | 0.0160 (6) | 0.0258 (6) | 0.0213 (6) | −0.0042 (5) | 0.0074 (5) | −0.0035 (5) |
C3 | 0.0226 (6) | 0.0295 (7) | 0.0247 (6) | −0.0051 (5) | 0.0145 (5) | −0.0039 (5) |
C4 | 0.0248 (6) | 0.0313 (7) | 0.0200 (6) | −0.0072 (5) | 0.0116 (5) | −0.0074 (5) |
C5 | 0.0186 (6) | 0.0231 (6) | 0.0193 (6) | −0.0041 (5) | 0.0071 (5) | −0.0009 (5) |
C6 | 0.0167 (6) | 0.0240 (6) | 0.0193 (6) | −0.0033 (5) | 0.0083 (5) | −0.0046 (5) |
C7 | 0.0219 (6) | 0.0268 (7) | 0.0179 (6) | 0.0008 (5) | 0.0090 (5) | −0.0024 (5) |
C8 | 0.0199 (6) | 0.0363 (8) | 0.0197 (6) | 0.0010 (5) | 0.0051 (5) | −0.0070 (5) |
C9 | 0.0224 (6) | 0.0335 (8) | 0.0316 (7) | −0.0086 (6) | 0.0098 (6) | −0.0127 (6) |
C10 | 0.0297 (7) | 0.0241 (7) | 0.0343 (7) | −0.0073 (6) | 0.0131 (6) | −0.0031 (6) |
C11 | 0.0231 (6) | 0.0236 (6) | 0.0225 (6) | −0.0015 (5) | 0.0066 (5) | −0.0015 (5) |
C12 | 0.0164 (5) | 0.0224 (6) | 0.0156 (5) | 0.0012 (5) | 0.0056 (4) | 0.0018 (5) |
C13 | 0.0224 (6) | 0.0216 (6) | 0.0180 (6) | −0.0009 (5) | 0.0073 (5) | 0.0002 (5) |
C14 | 0.0212 (6) | 0.0284 (7) | 0.0203 (6) | −0.0035 (5) | 0.0075 (5) | 0.0040 (5) |
C15 | 0.0209 (6) | 0.0355 (7) | 0.0202 (6) | 0.0032 (5) | 0.0103 (5) | 0.0056 (5) |
C16 | 0.0231 (6) | 0.0302 (7) | 0.0199 (6) | 0.0044 (5) | 0.0086 (5) | −0.0015 (5) |
C17 | 0.0198 (6) | 0.0230 (6) | 0.0198 (6) | 0.0003 (5) | 0.0073 (5) | −0.0002 (5) |
C18 | 0.0176 (6) | 0.0262 (6) | 0.0167 (6) | −0.0012 (5) | 0.0073 (5) | −0.0016 (5) |
C19 | 0.0257 (6) | 0.0248 (6) | 0.0225 (6) | −0.0049 (5) | 0.0113 (5) | −0.0029 (5) |
C20 | 0.0307 (7) | 0.0312 (7) | 0.0227 (6) | 0.0012 (6) | 0.0135 (6) | 0.0040 (5) |
C21 | 0.0236 (6) | 0.0393 (8) | 0.0174 (6) | 0.0021 (6) | 0.0063 (5) | −0.0011 (5) |
C22 | 0.0206 (6) | 0.0317 (7) | 0.0219 (6) | −0.0045 (5) | 0.0073 (5) | −0.0060 (5) |
C23 | 0.0211 (6) | 0.0255 (7) | 0.0224 (6) | −0.0025 (5) | 0.0091 (5) | −0.0004 (5) |
C24 | 0.0166 (5) | 0.0258 (6) | 0.0148 (5) | −0.0057 (5) | 0.0045 (5) | −0.0019 (5) |
C25 | 0.0183 (6) | 0.0276 (7) | 0.0220 (6) | −0.0011 (5) | 0.0053 (5) | −0.0002 (5) |
C26 | 0.0223 (7) | 0.0461 (9) | 0.0268 (7) | −0.0060 (6) | 0.0123 (6) | −0.0078 (6) |
C27 | 0.0282 (7) | 0.0505 (9) | 0.0189 (6) | −0.0193 (7) | 0.0081 (6) | −0.0002 (6) |
C28 | 0.0290 (7) | 0.0293 (7) | 0.0241 (7) | −0.0105 (6) | 0.0007 (6) | 0.0061 (6) |
C29 | 0.0196 (6) | 0.0252 (7) | 0.0255 (6) | −0.0022 (5) | 0.0043 (5) | −0.0011 (5) |
N1—C1 | 1.3384 (14) | C24—C25 | 1.390 (2) |
N1—C5 | 1.3394 (16) | C24—C29 | 1.3850 (18) |
N2—C1 | 1.3985 (16) | C25—C26 | 1.385 (2) |
N2—C6 | 1.4354 (15) | C26—C27 | 1.384 (2) |
N2—C12 | 1.4309 (19) | C27—C28 | 1.383 (2) |
N3—C5 | 1.3988 (16) | C28—C29 | 1.392 (2) |
N3—C18 | 1.4170 (14) | C2—H2 | 0.950 |
N3—C24 | 1.4357 (19) | C3—H3 | 0.950 |
C1—C2 | 1.404 (2) | C4—H4 | 0.950 |
C2—C3 | 1.3822 (18) | C7—H7 | 0.950 |
C3—C4 | 1.3847 (18) | C8—H8 | 0.950 |
C4—C5 | 1.398 (2) | C9—H9 | 0.950 |
C6—C7 | 1.3937 (15) | C10—H10 | 0.950 |
C6—C11 | 1.3886 (19) | C11—H11 | 0.950 |
C7—C8 | 1.3895 (18) | C13—H13 | 0.950 |
C8—C9 | 1.386 (2) | C14—H14 | 0.950 |
C9—C10 | 1.3827 (16) | C15—H15 | 0.950 |
C10—C11 | 1.3908 (18) | C16—H16 | 0.950 |
C12—C13 | 1.3971 (18) | C17—H17 | 0.950 |
C12—C17 | 1.3937 (19) | C19—H19 | 0.950 |
C13—C14 | 1.391 (2) | C20—H20 | 0.950 |
C14—C15 | 1.392 (2) | C21—H21 | 0.950 |
C15—C16 | 1.385 (2) | C22—H22 | 0.950 |
C16—C17 | 1.392 (2) | C23—H23 | 0.950 |
C18—C19 | 1.3963 (19) | C25—H25 | 0.950 |
C18—C23 | 1.3945 (17) | C26—H26 | 0.950 |
C19—C20 | 1.3872 (17) | C27—H27 | 0.950 |
C20—C21 | 1.3881 (19) | C28—H28 | 0.950 |
C21—C22 | 1.387 (2) | C29—H29 | 0.950 |
C22—C23 | 1.3868 (16) | ||
N1···C3 | 2.761 (2) | C20···H27xi | 3.0597 |
N1···C12 | 2.7986 (17) | C21···H14xi | 3.5492 |
N1···C13 | 2.8335 (18) | C21···H15xi | 3.4211 |
N1···C18 | 3.5752 (14) | C21···H22xii | 3.5219 |
N1···C24 | 2.7047 (15) | C21···H23xii | 3.0133 |
N1···C25 | 3.4065 (19) | C21···H25xiii | 3.3689 |
N1···C29 | 3.2838 (18) | C21···H27xi | 3.2235 |
N2···C5 | 3.5645 (15) | C22···H15xi | 3.2474 |
N3···C1 | 3.5433 (15) | C22···H20ii | 3.2761 |
C1···C4 | 2.7522 (19) | C22···H22xii | 3.3164 |
C1···C7 | 3.5218 (15) | C22···H23xii | 3.2196 |
C1···C11 | 3.0406 (17) | C22···H25xiii | 3.1925 |
C1···C13 | 3.037 (2) | C23···H15xi | 3.1187 |
C2···C5 | 2.7316 (16) | C23···H19ii | 3.3335 |
C2···C6 | 2.8351 (18) | C23···H22xii | 3.1572 |
C2···C11 | 3.0997 (18) | C25···H21xiii | 3.5425 |
C4···C18 | 3.0005 (18) | C25···H22xii | 3.1400 |
C4···C19 | 3.1387 (17) | C25···H28i | 3.0618 |
C5···C19 | 2.9917 (16) | C26···H21xiii | 3.2718 |
C5···C25 | 3.423 (2) | C26···H21ix | 3.4794 |
C5···C29 | 3.120 (2) | C26···H27iii | 2.9808 |
C6···C9 | 2.7781 (18) | C26···H28i | 3.4865 |
C6···C17 | 2.850 (2) | C27···H20ix | 3.2659 |
C7···C10 | 2.776 (2) | C27···H21xiii | 3.2619 |
C7···C12 | 3.0862 (19) | C27···H21ix | 3.4158 |
C7···C17 | 3.315 (2) | C27···H26iii | 3.0392 |
C8···C11 | 2.7769 (17) | C27···H27iii | 3.4074 |
C11···C12 | 3.484 (2) | C28···H21xiii | 3.5253 |
C12···C15 | 2.806 (2) | C28···H25ii | 3.0656 |
C13···C16 | 2.778 (2) | C29···H25ii | 3.4934 |
C14···C17 | 2.7668 (19) | H2···C2iv | 3.1232 |
C18···C21 | 2.7940 (17) | H2···C3iv | 3.3688 |
C18···C25 | 3.125 (2) | H2···C10ii | 3.4371 |
C18···C29 | 3.4597 (19) | H2···C10v | 3.3971 |
C19···C22 | 2.7754 (18) | H2···H2iv | 2.4980 |
C20···C23 | 2.770 (2) | H2···H3iv | 2.9686 |
C23···C24 | 2.8935 (17) | H2···H10ii | 2.5647 |
C23···C25 | 3.461 (2) | H2···H10v | 2.6075 |
C24···C27 | 2.769 (2) | H3···C6iv | 3.4432 |
C25···C28 | 2.7764 (19) | H3···C7iv | 2.9561 |
C26···C29 | 2.774 (2) | H3···C8iv | 2.8226 |
N1···C29i | 3.4649 (18) | H3···C9v | 3.3906 |
C2···C10ii | 3.5741 (17) | H3···C9iv | 3.1933 |
C10···C2i | 3.5741 (17) | H3···C10v | 3.2083 |
C17···C28i | 3.5964 (17) | H3···H2iv | 2.9686 |
C25···C28i | 3.553 (2) | H3···H7iv | 3.2687 |
C26···C27iii | 3.572 (2) | H3···H8iv | 3.0745 |
C27···C26iii | 3.572 (2) | H3···H9v | 2.8652 |
C28···C17ii | 3.5964 (17) | H3···H10v | 2.4838 |
C28···C25ii | 3.553 (2) | H3···H16vi | 3.5138 |
C29···N1ii | 3.4649 (18) | H4···C14xi | 3.5796 |
N1···H2 | 3.2532 | H4···C15xi | 3.1888 |
N1···H4 | 3.2618 | H4···H8iv | 3.4428 |
N1···H13 | 2.4641 | H4···H9iv | 3.4692 |
N1···H25 | 3.5759 | H4···H14xi | 3.5191 |
N1···H29 | 3.3764 | H4···H15xi | 2.8359 |
N2···H2 | 2.6449 | H4···H16vi | 2.8765 |
N2···H7 | 2.6176 | H7···C7viii | 3.3669 |
N2···H11 | 2.6219 | H7···C8viii | 2.8575 |
N2···H13 | 2.6543 | H7···C9ii | 3.3457 |
N2···H17 | 2.6000 | H7···C9viii | 3.3138 |
N3···H4 | 2.6687 | H7···C10ii | 3.1798 |
N3···H19 | 2.6338 | H7···H3iv | 3.2687 |
N3···H23 | 2.5998 | H7···H8viii | 2.7573 |
N3···H25 | 2.6183 | H7···H9ii | 3.2780 |
N3···H29 | 2.6098 | H7···H9viii | 3.5270 |
C1···H3 | 3.2483 | H7···H10ii | 2.9878 |
C1···H11 | 2.9078 | H8···C7vii | 3.5964 |
C1···H13 | 2.8223 | H8···C12vii | 3.2211 |
C2···H4 | 3.2727 | H8···C13vii | 3.1331 |
C2···H11 | 2.9887 | H8···C14vii | 3.2977 |
C4···H2 | 3.2705 | H8···C15vii | 3.5277 |
C4···H19 | 2.7909 | H8···C16vii | 3.5663 |
C5···H3 | 3.2361 | H8···C17vii | 3.4240 |
C5···H13 | 3.4722 | H8···H3iv | 3.0745 |
C5···H19 | 2.7466 | H8···H4iv | 3.4428 |
C5···H25 | 3.5561 | H8···H7vii | 2.7573 |
C5···H29 | 3.0503 | H8···H13vii | 3.5020 |
C6···H2 | 2.5359 | H8···H16viii | 3.5851 |
C6···H8 | 3.2645 | H8···H17viii | 2.9070 |
C6···H10 | 3.2609 | H9···C3v | 3.3757 |
C6···H17 | 2.5461 | H9···C15vii | 3.3618 |
C7···H2 | 3.3286 | H9···C16vii | 2.7852 |
C7···H9 | 3.2639 | H9···C17vii | 3.0441 |
C7···H11 | 3.2681 | H9···H3v | 2.8652 |
C7···H17 | 3.0255 | H9···H4iv | 3.4692 |
C8···H10 | 3.2544 | H9···H7i | 3.2780 |
C9···H7 | 3.2643 | H9···H7vii | 3.5270 |
C9···H11 | 3.2622 | H9···H16vii | 2.7982 |
C10···H2 | 3.5149 | H9···H17vii | 3.2261 |
C10···H8 | 3.2542 | H10···N2i | 3.3416 |
C11···H2 | 2.6783 | H10···C1i | 3.2386 |
C11···H7 | 3.2678 | H10···C2i | 2.8481 |
C11···H9 | 3.2630 | H10···C2v | 3.1116 |
C11···H17 | 3.0577 | H10···C3v | 3.0609 |
C12···H7 | 2.9775 | H10···C6i | 3.3602 |
C12···H14 | 3.2698 | H10···C7i | 3.1928 |
C12···H16 | 3.2737 | H10···H2i | 2.5647 |
C13···H15 | 3.2793 | H10···H2v | 2.6075 |
C13···H17 | 3.2626 | H10···H3v | 2.4838 |
C14···H16 | 3.2518 | H10···H7i | 2.9878 |
C15···H13 | 3.2759 | H11···N1i | 3.2586 |
C15···H17 | 3.2654 | H11···C1i | 3.0552 |
C16···H14 | 3.2498 | H11···C2i | 3.1971 |
C17···H7 | 3.3240 | H11···C3i | 3.4761 |
C17···H13 | 3.2638 | H11···C5i | 3.5105 |
C17···H15 | 3.2713 | H11···H13i | 3.0404 |
C18···H4 | 2.7887 | H11···H29i | 3.2822 |
C18···H20 | 3.2666 | H13···C11ii | 3.4112 |
C18···H22 | 3.2679 | H13···C17ii | 3.1441 |
C18···H25 | 3.0357 | H13···H8viii | 3.5020 |
C18···H29 | 3.5967 | H13···H11ii | 3.0404 |
C19···H4 | 2.8254 | H13···H17ii | 2.5592 |
C19···H21 | 3.2691 | H13···H28i | 3.4526 |
C19···H23 | 3.2662 | H14···C16ii | 2.9992 |
C20···H22 | 3.2535 | H14···C17ii | 3.2575 |
C21···H19 | 3.2670 | H14···C19ix | 3.5415 |
C21···H23 | 3.2631 | H14···C20ix | 3.1467 |
C22···H20 | 3.2527 | H14···C21ix | 3.5492 |
C23···H19 | 3.2668 | H14···H4ix | 3.5191 |
C23···H21 | 3.2662 | H14···H16ii | 2.6039 |
C23···H25 | 3.5120 | H14···H17ii | 3.0741 |
C24···H13 | 3.2487 | H14···H20ix | 3.1266 |
C24···H23 | 2.6358 | H15···C18ix | 3.1875 |
C24···H26 | 3.2574 | H15···C19x | 3.5282 |
C24···H28 | 3.2592 | H15···C19ix | 3.3675 |
C25···H23 | 3.2702 | H15···C20x | 3.5317 |
C25···H27 | 3.2576 | H15···C20ix | 3.4734 |
C25···H29 | 3.2647 | H15···C21ix | 3.4211 |
C26···H14 | 3.3793 | H15···C22ix | 3.2474 |
C26···H28 | 3.2559 | H15···C23ix | 3.1187 |
C27···H14 | 2.9679 | H15···H4ix | 2.8359 |
C27···H25 | 3.2590 | H15···H19x | 2.8844 |
C27···H29 | 3.2603 | H15···H20x | 2.8865 |
C28···H13 | 3.2558 | H15···H23ix | 3.5244 |
C28···H14 | 3.2674 | H16···C4x | 3.3523 |
C28···H26 | 3.2550 | H16···C14i | 3.1865 |
C29···H13 | 3.0032 | H16···C19x | 3.2147 |
C29···H23 | 3.0389 | H16···C20x | 3.4676 |
C29···H25 | 3.2642 | H16···H3x | 3.5138 |
C29···H27 | 3.2603 | H16···H4x | 2.8765 |
H2···H3 | 2.3403 | H16···H8vii | 3.5851 |
H2···H11 | 2.7726 | H16···H9viii | 2.7982 |
H3···H4 | 2.3490 | H16···H14i | 2.6039 |
H4···H19 | 2.6530 | H16···H19x | 2.7335 |
H7···H8 | 2.3401 | H16···H20x | 3.2045 |
H7···H17 | 3.2714 | H17···C13i | 2.9821 |
H8···H9 | 2.3351 | H17···C14i | 3.2569 |
H9···H10 | 2.3308 | H17···H8vii | 2.9070 |
H10···H11 | 2.3403 | H17···H9viii | 3.2261 |
H11···H17 | 3.3079 | H17···H13i | 2.5592 |
H13···H14 | 2.3344 | H17···H14i | 3.0741 |
H13···H29 | 3.2289 | H17···H28i | 3.5963 |
H14···H15 | 2.3426 | H19···C15vi | 3.4709 |
H14···H27 | 3.0436 | H19···C16vi | 3.4014 |
H14···H28 | 3.5240 | H19···C23i | 3.3335 |
H15···H16 | 2.3392 | H19···H15vi | 2.8844 |
H16···H17 | 2.3338 | H19···H16vi | 2.7335 |
H19···H20 | 2.3320 | H19···H23i | 2.8939 |
H20···H21 | 2.3382 | H19···H29i | 3.5662 |
H21···H22 | 2.3387 | H20···C15vi | 3.2940 |
H22···H23 | 2.3312 | H20···C16vi | 3.4588 |
H23···H25 | 3.5563 | H20···C22i | 3.2761 |
H23···H29 | 3.1946 | H20···C27xi | 3.2659 |
H25···H26 | 2.3363 | H20···H14xi | 3.1266 |
H26···H27 | 2.3317 | H20···H15vi | 2.8865 |
H27···H28 | 2.3323 | H20···H16vi | 3.2045 |
H28···H29 | 2.3437 | H20···H22i | 2.9353 |
N1···H11ii | 3.2586 | H20···H23i | 3.5421 |
N1···H28i | 3.2009 | H20···H27xi | 2.4433 |
N1···H29i | 2.7092 | H21···C25xii | 3.5425 |
N2···H10ii | 3.3416 | H21···C26xii | 3.2718 |
N2···H29i | 3.4038 | H21···C26xi | 3.4794 |
C1···H10ii | 3.2386 | H21···C27xii | 3.2619 |
C1···H11ii | 3.0552 | H21···C27xi | 3.4158 |
C1···H29i | 3.0771 | H21···C28xii | 3.5253 |
C2···H2iv | 3.1232 | H21···H23xii | 3.0003 |
C2···H10ii | 2.8481 | H21···H25xiii | 2.8467 |
C2···H10v | 3.1116 | H21···H26xi | 2.9115 |
C2···H11ii | 3.1971 | H21···H27xii | 3.5921 |
C3···H2iv | 3.3688 | H21···H27xi | 2.7825 |
C3···H9v | 3.3757 | H22···C18xiii | 3.1982 |
C3···H10v | 3.0609 | H22···C19xiii | 3.3946 |
C3···H11ii | 3.4761 | H22···C20ii | 3.3652 |
C4···H16vi | 3.3523 | H22···C20xiii | 3.5508 |
C5···H11ii | 3.5105 | H22···C21xiii | 3.5219 |
C5···H29i | 3.2728 | H22···C22xiii | 3.3164 |
C6···H3iv | 3.4432 | H22···C23xiii | 3.1572 |
C6···H10ii | 3.3602 | H22···C25xiii | 3.1400 |
C7···H3iv | 2.9561 | H22···H20ii | 2.9353 |
C7···H7vii | 3.3669 | H22···H23xii | 3.3299 |
C7···H8viii | 3.5964 | H22···H23xiii | 3.5548 |
C7···H10ii | 3.1928 | H22···H25xiii | 2.4717 |
C8···H3iv | 2.8226 | H23···C19ii | 3.2495 |
C8···H7vii | 2.8575 | H23···C21xiii | 3.0133 |
C9···H3v | 3.3906 | H23···C22xiii | 3.2196 |
C9···H3iv | 3.1933 | H23···H15xi | 3.5244 |
C9···H7i | 3.3457 | H23···H19ii | 2.8939 |
C9···H7vii | 3.3138 | H23···H20ii | 3.5421 |
C10···H2i | 3.4371 | H23···H21xiii | 3.0003 |
C10···H2v | 3.3971 | H23···H22xii | 3.5548 |
C10···H3v | 3.2083 | H23···H22xiii | 3.3299 |
C10···H7i | 3.1798 | H25···C21xii | 3.3689 |
C11···H13i | 3.4112 | H25···C22xii | 3.1925 |
C12···H8viii | 3.2211 | H25···C28i | 3.0656 |
C12···H28i | 2.9327 | H25···C29i | 3.4934 |
C13···H8viii | 3.1331 | H25···H21xii | 2.8467 |
C13···H17ii | 2.9821 | H25···H22xii | 2.4717 |
C13···H28i | 2.9842 | H25···H28i | 2.8208 |
C14···H4ix | 3.5796 | H25···H29i | 3.5622 |
C14···H8viii | 3.2977 | H26···C27iii | 3.0392 |
C14···H16ii | 3.1865 | H26···H21ix | 2.9115 |
C14···H17ii | 3.2569 | H26···H26xiv | 2.9226 |
C14···H28i | 3.1617 | H26···H26iii | 3.5438 |
C15···H4ix | 3.1888 | H26···H27iii | 2.5036 |
C15···H8viii | 3.5277 | H26···H28i | 3.5515 |
C15···H9viii | 3.3618 | H27···C20ix | 3.0597 |
C15···H19x | 3.4709 | H27···C21ix | 3.2235 |
C15···H20x | 3.2940 | H27···C26iii | 2.9808 |
C15···H28i | 3.3068 | H27···C27iii | 3.4074 |
C16···H8viii | 3.5663 | H27···H20ix | 2.4433 |
C16···H9viii | 2.7852 | H27···H21xiii | 3.5921 |
C16···H14i | 2.9992 | H27···H21ix | 2.7825 |
C16···H19x | 3.4014 | H27···H26iii | 2.5036 |
C16···H20x | 3.4588 | H27···H27iii | 3.2941 |
C16···H28i | 3.2769 | H28···N1ii | 3.2009 |
C17···H8viii | 3.4240 | H28···C12ii | 2.9327 |
C17···H9viii | 3.0441 | H28···C13ii | 2.9842 |
C17···H13i | 3.1441 | H28···C14ii | 3.1617 |
C17···H14i | 3.2575 | H28···C15ii | 3.3068 |
C17···H28i | 3.0886 | H28···C16ii | 3.2769 |
C18···H15xi | 3.1875 | H28···C17ii | 3.0886 |
C18···H22xii | 3.1982 | H28···C25ii | 3.0618 |
C19···H14xi | 3.5415 | H28···C26ii | 3.4865 |
C19···H15vi | 3.5282 | H28···H13ii | 3.4526 |
C19···H15xi | 3.3675 | H28···H17ii | 3.5963 |
C19···H16vi | 3.2147 | H28···H25ii | 2.8208 |
C19···H22xii | 3.3946 | H28···H26ii | 3.5515 |
C19···H23i | 3.2495 | H29···N1ii | 2.7092 |
C20···H14xi | 3.1467 | H29···N2ii | 3.4038 |
C20···H15vi | 3.5317 | H29···C1ii | 3.0771 |
C20···H15xi | 3.4734 | H29···C5ii | 3.2728 |
C20···H16vi | 3.4676 | H29···H11ii | 3.2822 |
C20···H22i | 3.3652 | H29···H19ii | 3.5662 |
C20···H22xii | 3.5508 | H29···H25ii | 3.5622 |
C1—N1—C5 | 118.87 (12) | C24—C29—C28 | 119.73 (14) |
C1—N2—C6 | 118.65 (11) | C1—C2—H2 | 121.112 |
C1—N2—C12 | 123.46 (9) | C3—C2—H2 | 121.119 |
C6—N2—C12 | 117.44 (10) | C2—C3—H3 | 119.450 |
C5—N3—C18 | 123.18 (12) | C4—C3—H3 | 119.452 |
C5—N3—C24 | 118.12 (9) | C3—C4—H4 | 121.547 |
C18—N3—C24 | 118.63 (10) | C5—C4—H4 | 121.569 |
N1—C1—N2 | 116.84 (12) | C6—C7—H7 | 120.153 |
N1—C1—C2 | 122.10 (11) | C8—C7—H7 | 120.150 |
N2—C1—C2 | 121.06 (10) | C7—C8—H8 | 119.883 |
C1—C2—C3 | 117.77 (11) | C9—C8—H8 | 119.887 |
C2—C3—C4 | 121.10 (15) | C8—C9—H9 | 120.023 |
C3—C4—C5 | 116.88 (13) | C10—C9—H9 | 120.027 |
N1—C5—N3 | 114.45 (12) | C9—C10—H10 | 119.846 |
N1—C5—C4 | 123.25 (10) | C11—C10—H10 | 119.840 |
N3—C5—C4 | 122.28 (11) | C6—C11—H11 | 120.123 |
N2—C6—C7 | 119.74 (11) | C10—C11—H11 | 120.125 |
N2—C6—C11 | 120.24 (9) | C12—C13—H13 | 120.001 |
C7—C6—C11 | 120.02 (11) | C14—C13—H13 | 119.990 |
C6—C7—C8 | 119.70 (12) | C13—C14—H14 | 119.524 |
C7—C8—C9 | 120.23 (11) | C15—C14—H14 | 119.533 |
C8—C9—C10 | 119.95 (12) | C14—C15—H15 | 120.523 |
C9—C10—C11 | 120.31 (13) | C16—C15—H15 | 120.524 |
C6—C11—C10 | 119.75 (11) | C15—C16—H16 | 119.727 |
N2—C12—C13 | 121.74 (12) | C17—C16—H16 | 119.723 |
N2—C12—C17 | 119.35 (11) | C12—C17—H17 | 119.679 |
C13—C12—C17 | 118.90 (13) | C16—C17—H17 | 119.708 |
C12—C13—C14 | 120.01 (12) | C18—C19—H19 | 119.997 |
C13—C14—C15 | 120.94 (13) | C20—C19—H19 | 119.992 |
C14—C15—C16 | 118.95 (15) | C19—C20—H20 | 119.651 |
C15—C16—C17 | 120.55 (14) | C21—C20—H20 | 119.664 |
C12—C17—C16 | 120.61 (12) | C20—C21—H21 | 120.340 |
N3—C18—C19 | 121.16 (11) | C22—C21—H21 | 120.337 |
N3—C18—C23 | 119.59 (12) | C21—C22—H22 | 119.764 |
C19—C18—C23 | 119.20 (10) | C23—C22—H22 | 119.757 |
C18—C19—C20 | 120.01 (12) | C18—C23—H23 | 119.855 |
C19—C20—C21 | 120.69 (13) | C22—C23—H23 | 119.850 |
C20—C21—C22 | 119.32 (11) | C24—C25—H25 | 120.185 |
C21—C22—C23 | 120.48 (12) | C26—C25—H25 | 120.183 |
C18—C23—C22 | 120.30 (12) | C25—C26—H26 | 119.895 |
N3—C24—C25 | 119.92 (11) | C27—C26—H26 | 119.891 |
N3—C24—C29 | 119.78 (13) | C26—C27—H27 | 119.916 |
C25—C24—C29 | 120.30 (14) | C28—C27—H27 | 119.919 |
C24—C25—C26 | 119.63 (12) | C27—C28—H28 | 120.024 |
C25—C26—C27 | 120.21 (15) | C29—C28—H28 | 120.017 |
C26—C27—C28 | 120.17 (16) | C24—C29—H29 | 120.133 |
C27—C28—C29 | 119.96 (13) | C28—C29—H29 | 120.135 |
C1—N1—C5—N3 | −177.95 (9) | C3—C4—C5—N3 | 179.10 (10) |
C1—N1—C5—C4 | 0.67 (17) | N2—C6—C7—C8 | −179.94 (11) |
C5—N1—C1—N2 | 178.55 (9) | N2—C6—C11—C10 | 178.61 (11) |
C5—N1—C1—C2 | −1.86 (16) | C7—C6—C11—C10 | −2.0 (2) |
C1—N2—C6—C7 | 122.77 (12) | C11—C6—C7—C8 | 0.6 (2) |
C1—N2—C6—C11 | −57.80 (15) | C6—C7—C8—C9 | 0.9 (2) |
C6—N2—C1—N1 | 162.66 (9) | C7—C8—C9—C10 | −1.1 (2) |
C6—N2—C1—C2 | −16.93 (15) | C8—C9—C10—C11 | −0.2 (2) |
C1—N2—C12—C13 | −38.32 (14) | C9—C10—C11—C6 | 1.7 (2) |
C1—N2—C12—C17 | 142.21 (9) | N2—C12—C13—C14 | 178.86 (8) |
C12—N2—C1—N1 | −9.43 (15) | N2—C12—C17—C16 | −179.52 (8) |
C12—N2—C1—C2 | 170.98 (9) | C13—C12—C17—C16 | 0.99 (15) |
C6—N2—C12—C13 | 149.50 (9) | C17—C12—C13—C14 | −1.67 (15) |
C6—N2—C12—C17 | −29.97 (13) | C12—C13—C14—C15 | 0.78 (15) |
C12—N2—C6—C7 | −64.67 (14) | C13—C14—C15—C16 | 0.80 (16) |
C12—N2—C6—C11 | 114.77 (12) | C14—C15—C16—C17 | −1.49 (16) |
C5—N3—C18—C19 | 35.16 (18) | C15—C16—C17—C12 | 0.60 (16) |
C5—N3—C18—C23 | −147.51 (11) | N3—C18—C19—C20 | 177.64 (12) |
C18—N3—C5—N1 | −147.66 (11) | N3—C18—C23—C22 | −177.09 (11) |
C18—N3—C5—C4 | 33.71 (18) | C19—C18—C23—C22 | 0.3 (2) |
C5—N3—C24—C25 | −109.07 (11) | C23—C18—C19—C20 | 0.3 (2) |
C5—N3—C24—C29 | 70.77 (14) | C18—C19—C20—C21 | −0.4 (2) |
C24—N3—C5—N1 | 29.38 (15) | C19—C20—C21—C22 | −0.2 (2) |
C24—N3—C5—C4 | −149.25 (11) | C20—C21—C22—C23 | 0.8 (2) |
C18—N3—C24—C25 | 68.10 (14) | C21—C22—C23—C18 | −0.8 (2) |
C18—N3—C24—C29 | −112.06 (11) | N3—C24—C25—C26 | 179.54 (9) |
C24—N3—C18—C19 | −141.86 (11) | N3—C24—C29—C28 | −179.69 (8) |
C24—N3—C18—C23 | 35.46 (17) | C25—C24—C29—C28 | 0.15 (16) |
N1—C1—C2—C3 | 1.73 (16) | C29—C24—C25—C26 | −0.29 (16) |
N2—C1—C2—C3 | −178.70 (9) | C24—C25—C26—C27 | 0.28 (17) |
C1—C2—C3—C4 | −0.40 (17) | C25—C26—C27—C28 | −0.12 (18) |
C2—C3—C4—C5 | −0.69 (18) | C26—C27—C28—C29 | −0.02 (18) |
C3—C4—C5—N1 | 0.59 (18) | C27—C28—C29—C24 | 0.01 (17) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x, −y, −z; (v) −x, −y−1, −z; (vi) x, −y−1/2, z+1/2; (vii) −x, y−1/2, −z−1/2; (viii) −x, y+1/2, −z−1/2; (ix) x, −y+1/2, z−1/2; (x) x, −y−1/2, z−1/2; (xi) x, −y+1/2, z+1/2; (xii) −x+1, y−1/2, −z+1/2; (xiii) −x+1, y+1/2, −z+1/2; (xiv) −x+1, −y, −z. |
Cg3 and Cg4 are the centriods of the C12–C17 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C29—H29···N1ii | 0.95 | 2.71 | 3.4649 (18) | 137 |
C15—H15···Cg4ix | 0.95 | 3.00 | 3.8133 (17) | 145 |
C28—H28···Cg3ii | 0.95 | 2.80 | 3.5831 (17) | 140 |
Symmetry codes: (ii) x, y+1, z; (ix) x, −y+1/2, z−1/2. |
Acknowledgements
This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST).
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