organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

Edited by P. Bombicz, Hungarian Academy of Sciences, Hungary (Received 21 February 2017; accepted 6 April 2017; online 11 April 2017)

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.

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

Structure description

Aryl-substituted 2,6-di­amino­pyridines are used as blue luminous materials (Chen et al., 2001[Chen, T. R., Chen, J. D., Keng, T. C. & Wang, J. C. (2001). Tetrahedron Lett. 42, 7915-7917.]) and as part of mol­ecular receptors (Yao et al., 2009[Yao, B., Wang, D. X., Gong, H. Y., Huang, Z. Y. & Wang, M. X. (2009). J. Org. Chem. 74, 5361-5368.]; Fa et al., 2014[Fa, S. X., Wang, L. X., Wang, D. X., Zhao, L. & Wang, M. X. (2014). J. Org. Chem. 79, 3559-3571.]). For related structures, see: Chen et al. (2001[Chen, T. R., Chen, J. D., Keng, T. C. & Wang, J. C. (2001). Tetrahedron Lett. 42, 7915-7917.]), Klinga et al. (1994[Klinga, M., Polamo, M. & Leskelä, M. (1994). Acta Cryst. C50, 2051-2054.]), Berry et al. (2003[Berry, J. F., Cotton, F. A., Lei, P., Lu, T. & Murillo, C. A. (2003). Inorg. Chem. 42, 3534-3539.]) and Wang et al. (2007[Wang, C. J., Ma, H. R., Wang, Y. Y., Liu, P., Zhou, L. J., Shi, Q. Z. & Peng, S. M. (2007). Cryst. Growth Des. 7, 1811-1817.]).

The title mol­ecule has an unsymmetrical structure (Fig. 1[link]), 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.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and H atoms are shown as small spheres.

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[link] and Fig. 2[link]). These inter­actions are thought to be one of the reasons for lowering mol­ecular symmetry.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centriods of the C12–C17 and C18–C23 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C29—H29⋯N1i 0.95 2.71 3.4649 (18) 137
C15—H15⋯Cg4ii 0.95 3.00 3.8133 (17) 145
C28—H28⋯Cg3i 0.95 2.80 3.5831 (17) 140
Symmetry codes: (i) x, y+1, z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].
[Figure 2]
Figure 2
A view of the inter­molecular inter­actions in the title compound. [Symmetry codes:(i) x, y + 1, z; (ii) x, y − 1, z.]

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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C29H23N3
Mr 413.52
Crystal system, space group Monoclinic, P21/c
Temperature (K) 93
a, b, c (Å) 19.949 (4), 5.6952 (10), 20.921 (4)
β (°) 113.152 (2)
V3) 2185.5 (7)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.12 × 0.10 × 0.06
 
Data collection
Diffractometer Rigaku Saturn724+
Absorption correction Numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.992, 0.996
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 16972, 4997, 4014
Rint 0.027
(sin θ/λ)max−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 1.08
No. of reflections 4997
No. of parameters 289
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.23, −0.21
Computer programs: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]), SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CrystalStructure (Rigaku, 2014[Rigaku (2014). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Structural data


Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: 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).

N2,N2,N6,N6-Tetraphenylpyridine-2,6-diamine top
Crystal data top
C29H23N3F(000) = 872.00
Mr = 413.52Dx = 1.257 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 19.949 (4) ÅCell parameters from 6510 reflections
b = 5.6952 (10) Åθ = 2.0–31.1°
c = 20.921 (4) ŵ = 0.07 mm1
β = 113.152 (2)°T = 93 K
V = 2185.5 (7) Å3Block, colorless
Z = 40.12 × 0.10 × 0.06 mm
Data collection top
Rigaku Saturn724+
diffractometer
4014 reflections with F2 > 2.0σ(F2)
Detector resolution: 7.111 pixels mm-1Rint = 0.027
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
h = 2522
Tmin = 0.992, Tmax = 0.996k = 67
16972 measured reflectionsl = 2626
4997 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.21 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.22089 (5)0.05699 (18)0.02057 (5)0.0183 (2)
N20.13310 (5)0.10586 (18)0.07967 (5)0.0192 (2)
N30.31284 (6)0.2296 (2)0.11341 (5)0.0237 (2)
C10.15290 (6)0.0247 (2)0.01159 (6)0.0179 (2)
C20.10344 (6)0.0310 (2)0.02107 (6)0.0210 (3)
C30.12642 (7)0.0567 (2)0.08790 (7)0.0240 (3)
C40.19604 (7)0.1464 (2)0.12166 (7)0.0245 (3)
C50.24170 (6)0.1413 (2)0.08529 (6)0.0204 (3)
C60.06996 (6)0.2532 (2)0.10914 (6)0.0196 (2)
C70.01295 (7)0.1862 (2)0.17059 (6)0.0218 (3)
C80.04818 (7)0.3288 (3)0.19904 (7)0.0262 (3)
C90.05299 (7)0.5353 (3)0.16599 (7)0.0294 (3)
C100.00375 (7)0.6018 (2)0.10515 (7)0.0292 (3)
C110.06585 (7)0.4628 (2)0.07697 (7)0.0238 (3)
C120.17718 (6)0.0741 (2)0.11891 (6)0.0183 (2)
C130.21613 (7)0.1330 (2)0.11500 (6)0.0209 (3)
C140.25942 (7)0.1554 (2)0.15304 (6)0.0235 (3)
C150.26401 (7)0.0251 (2)0.19596 (7)0.0248 (3)
C160.22393 (7)0.2281 (2)0.20109 (7)0.0244 (3)
C170.18107 (7)0.2534 (2)0.16269 (6)0.0210 (3)
C180.35806 (6)0.2183 (2)0.18519 (6)0.0200 (3)
C190.35523 (7)0.0266 (2)0.22566 (7)0.0238 (3)
C200.40196 (7)0.0158 (3)0.29523 (7)0.0272 (3)
C210.45213 (7)0.1935 (3)0.32528 (7)0.0273 (3)
C220.45537 (7)0.3831 (2)0.28495 (7)0.0251 (3)
C230.40846 (7)0.3967 (2)0.21551 (6)0.0228 (3)
C240.34234 (6)0.3263 (2)0.06662 (6)0.0195 (2)
C250.39688 (7)0.2069 (2)0.05433 (7)0.0235 (3)
C260.42474 (7)0.3004 (3)0.00875 (7)0.0309 (3)
C270.39866 (8)0.5121 (3)0.02417 (7)0.0329 (3)
C280.34452 (8)0.6312 (3)0.01182 (7)0.0305 (3)
C290.31614 (7)0.5382 (2)0.03378 (7)0.0248 (3)
H20.055780.093480.0020.0252*
H30.093910.055350.111060.0288*
H40.212020.208490.16740.0294*
H70.015870.043610.192930.0262*
H80.086810.284750.241280.0314*
H90.095240.631030.185130.0353*
H100.000310.743090.08250.0350*
H110.105310.511160.035870.0286*
H130.213060.258480.086370.0251*
H140.286220.296040.149670.0282*
H150.294160.009490.221340.0298*
H160.225710.351060.231070.0292*
H170.154210.394040.166350.0252*
H190.32130.096490.205550.0286*
H200.399590.114590.322590.0327*
H210.483930.185430.372980.0327*
H220.489980.504380.305040.0301*
H230.410670.528250.188480.0274*
H250.414950.062020.077070.0281*
H260.461870.219040.000050.0371*
H270.4180.57570.055330.0395*
H280.326720.776470.034450.0366*
H290.278940.619580.042350.0298*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0165 (5)0.0207 (5)0.0176 (5)0.0013 (4)0.0066 (4)0.0004 (4)
N20.0183 (5)0.0224 (5)0.0177 (5)0.0051 (4)0.0078 (4)0.0031 (4)
N30.0184 (5)0.0362 (6)0.0155 (5)0.0090 (5)0.0056 (4)0.0007 (4)
C10.0178 (6)0.0182 (6)0.0176 (6)0.0009 (5)0.0070 (5)0.0009 (4)
C20.0160 (6)0.0258 (6)0.0213 (6)0.0042 (5)0.0074 (5)0.0035 (5)
C30.0226 (6)0.0295 (7)0.0247 (6)0.0051 (5)0.0145 (5)0.0039 (5)
C40.0248 (6)0.0313 (7)0.0200 (6)0.0072 (5)0.0116 (5)0.0074 (5)
C50.0186 (6)0.0231 (6)0.0193 (6)0.0041 (5)0.0071 (5)0.0009 (5)
C60.0167 (6)0.0240 (6)0.0193 (6)0.0033 (5)0.0083 (5)0.0046 (5)
C70.0219 (6)0.0268 (7)0.0179 (6)0.0008 (5)0.0090 (5)0.0024 (5)
C80.0199 (6)0.0363 (8)0.0197 (6)0.0010 (5)0.0051 (5)0.0070 (5)
C90.0224 (6)0.0335 (8)0.0316 (7)0.0086 (6)0.0098 (6)0.0127 (6)
C100.0297 (7)0.0241 (7)0.0343 (7)0.0073 (6)0.0131 (6)0.0031 (6)
C110.0231 (6)0.0236 (6)0.0225 (6)0.0015 (5)0.0066 (5)0.0015 (5)
C120.0164 (5)0.0224 (6)0.0156 (5)0.0012 (5)0.0056 (4)0.0018 (5)
C130.0224 (6)0.0216 (6)0.0180 (6)0.0009 (5)0.0073 (5)0.0002 (5)
C140.0212 (6)0.0284 (7)0.0203 (6)0.0035 (5)0.0075 (5)0.0040 (5)
C150.0209 (6)0.0355 (7)0.0202 (6)0.0032 (5)0.0103 (5)0.0056 (5)
C160.0231 (6)0.0302 (7)0.0199 (6)0.0044 (5)0.0086 (5)0.0015 (5)
C170.0198 (6)0.0230 (6)0.0198 (6)0.0003 (5)0.0073 (5)0.0002 (5)
C180.0176 (6)0.0262 (6)0.0167 (6)0.0012 (5)0.0073 (5)0.0016 (5)
C190.0257 (6)0.0248 (6)0.0225 (6)0.0049 (5)0.0113 (5)0.0029 (5)
C200.0307 (7)0.0312 (7)0.0227 (6)0.0012 (6)0.0135 (6)0.0040 (5)
C210.0236 (6)0.0393 (8)0.0174 (6)0.0021 (6)0.0063 (5)0.0011 (5)
C220.0206 (6)0.0317 (7)0.0219 (6)0.0045 (5)0.0073 (5)0.0060 (5)
C230.0211 (6)0.0255 (7)0.0224 (6)0.0025 (5)0.0091 (5)0.0004 (5)
C240.0166 (5)0.0258 (6)0.0148 (5)0.0057 (5)0.0045 (5)0.0019 (5)
C250.0183 (6)0.0276 (7)0.0220 (6)0.0011 (5)0.0053 (5)0.0002 (5)
C260.0223 (7)0.0461 (9)0.0268 (7)0.0060 (6)0.0123 (6)0.0078 (6)
C270.0282 (7)0.0505 (9)0.0189 (6)0.0193 (7)0.0081 (6)0.0002 (6)
C280.0290 (7)0.0293 (7)0.0241 (7)0.0105 (6)0.0007 (6)0.0061 (6)
C290.0196 (6)0.0252 (7)0.0255 (6)0.0022 (5)0.0043 (5)0.0011 (5)
Geometric parameters (Å, º) top
N1—C11.3384 (14)C24—C251.390 (2)
N1—C51.3394 (16)C24—C291.3850 (18)
N2—C11.3985 (16)C25—C261.385 (2)
N2—C61.4354 (15)C26—C271.384 (2)
N2—C121.4309 (19)C27—C281.383 (2)
N3—C51.3988 (16)C28—C291.392 (2)
N3—C181.4170 (14)C2—H20.950
N3—C241.4357 (19)C3—H30.950
C1—C21.404 (2)C4—H40.950
C2—C31.3822 (18)C7—H70.950
C3—C41.3847 (18)C8—H80.950
C4—C51.398 (2)C9—H90.950
C6—C71.3937 (15)C10—H100.950
C6—C111.3886 (19)C11—H110.950
C7—C81.3895 (18)C13—H130.950
C8—C91.386 (2)C14—H140.950
C9—C101.3827 (16)C15—H150.950
C10—C111.3908 (18)C16—H160.950
C12—C131.3971 (18)C17—H170.950
C12—C171.3937 (19)C19—H190.950
C13—C141.391 (2)C20—H200.950
C14—C151.392 (2)C21—H210.950
C15—C161.385 (2)C22—H220.950
C16—C171.392 (2)C23—H230.950
C18—C191.3963 (19)C25—H250.950
C18—C231.3945 (17)C26—H260.950
C19—C201.3872 (17)C27—H270.950
C20—C211.3881 (19)C28—H280.950
C21—C221.387 (2)C29—H290.950
C22—C231.3868 (16)
N1···C32.761 (2)C20···H27xi3.0597
N1···C122.7986 (17)C21···H14xi3.5492
N1···C132.8335 (18)C21···H15xi3.4211
N1···C183.5752 (14)C21···H22xii3.5219
N1···C242.7047 (15)C21···H23xii3.0133
N1···C253.4065 (19)C21···H25xiii3.3689
N1···C293.2838 (18)C21···H27xi3.2235
N2···C53.5645 (15)C22···H15xi3.2474
N3···C13.5433 (15)C22···H20ii3.2761
C1···C42.7522 (19)C22···H22xii3.3164
C1···C73.5218 (15)C22···H23xii3.2196
C1···C113.0406 (17)C22···H25xiii3.1925
C1···C133.037 (2)C23···H15xi3.1187
C2···C52.7316 (16)C23···H19ii3.3335
C2···C62.8351 (18)C23···H22xii3.1572
C2···C113.0997 (18)C25···H21xiii3.5425
C4···C183.0005 (18)C25···H22xii3.1400
C4···C193.1387 (17)C25···H28i3.0618
C5···C192.9917 (16)C26···H21xiii3.2718
C5···C253.423 (2)C26···H21ix3.4794
C5···C293.120 (2)C26···H27iii2.9808
C6···C92.7781 (18)C26···H28i3.4865
C6···C172.850 (2)C27···H20ix3.2659
C7···C102.776 (2)C27···H21xiii3.2619
C7···C123.0862 (19)C27···H21ix3.4158
C7···C173.315 (2)C27···H26iii3.0392
C8···C112.7769 (17)C27···H27iii3.4074
C11···C123.484 (2)C28···H21xiii3.5253
C12···C152.806 (2)C28···H25ii3.0656
C13···C162.778 (2)C29···H25ii3.4934
C14···C172.7668 (19)H2···C2iv3.1232
C18···C212.7940 (17)H2···C3iv3.3688
C18···C253.125 (2)H2···C10ii3.4371
C18···C293.4597 (19)H2···C10v3.3971
C19···C222.7754 (18)H2···H2iv2.4980
C20···C232.770 (2)H2···H3iv2.9686
C23···C242.8935 (17)H2···H10ii2.5647
C23···C253.461 (2)H2···H10v2.6075
C24···C272.769 (2)H3···C6iv3.4432
C25···C282.7764 (19)H3···C7iv2.9561
C26···C292.774 (2)H3···C8iv2.8226
N1···C29i3.4649 (18)H3···C9v3.3906
C2···C10ii3.5741 (17)H3···C9iv3.1933
C10···C2i3.5741 (17)H3···C10v3.2083
C17···C28i3.5964 (17)H3···H2iv2.9686
C25···C28i3.553 (2)H3···H7iv3.2687
C26···C27iii3.572 (2)H3···H8iv3.0745
C27···C26iii3.572 (2)H3···H9v2.8652
C28···C17ii3.5964 (17)H3···H10v2.4838
C28···C25ii3.553 (2)H3···H16vi3.5138
C29···N1ii3.4649 (18)H4···C14xi3.5796
N1···H23.2532H4···C15xi3.1888
N1···H43.2618H4···H8iv3.4428
N1···H132.4641H4···H9iv3.4692
N1···H253.5759H4···H14xi3.5191
N1···H293.3764H4···H15xi2.8359
N2···H22.6449H4···H16vi2.8765
N2···H72.6176H7···C7viii3.3669
N2···H112.6219H7···C8viii2.8575
N2···H132.6543H7···C9ii3.3457
N2···H172.6000H7···C9viii3.3138
N3···H42.6687H7···C10ii3.1798
N3···H192.6338H7···H3iv3.2687
N3···H232.5998H7···H8viii2.7573
N3···H252.6183H7···H9ii3.2780
N3···H292.6098H7···H9viii3.5270
C1···H33.2483H7···H10ii2.9878
C1···H112.9078H8···C7vii3.5964
C1···H132.8223H8···C12vii3.2211
C2···H43.2727H8···C13vii3.1331
C2···H112.9887H8···C14vii3.2977
C4···H23.2705H8···C15vii3.5277
C4···H192.7909H8···C16vii3.5663
C5···H33.2361H8···C17vii3.4240
C5···H133.4722H8···H3iv3.0745
C5···H192.7466H8···H4iv3.4428
C5···H253.5561H8···H7vii2.7573
C5···H293.0503H8···H13vii3.5020
C6···H22.5359H8···H16viii3.5851
C6···H83.2645H8···H17viii2.9070
C6···H103.2609H9···C3v3.3757
C6···H172.5461H9···C15vii3.3618
C7···H23.3286H9···C16vii2.7852
C7···H93.2639H9···C17vii3.0441
C7···H113.2681H9···H3v2.8652
C7···H173.0255H9···H4iv3.4692
C8···H103.2544H9···H7i3.2780
C9···H73.2643H9···H7vii3.5270
C9···H113.2622H9···H16vii2.7982
C10···H23.5149H9···H17vii3.2261
C10···H83.2542H10···N2i3.3416
C11···H22.6783H10···C1i3.2386
C11···H73.2678H10···C2i2.8481
C11···H93.2630H10···C2v3.1116
C11···H173.0577H10···C3v3.0609
C12···H72.9775H10···C6i3.3602
C12···H143.2698H10···C7i3.1928
C12···H163.2737H10···H2i2.5647
C13···H153.2793H10···H2v2.6075
C13···H173.2626H10···H3v2.4838
C14···H163.2518H10···H7i2.9878
C15···H133.2759H11···N1i3.2586
C15···H173.2654H11···C1i3.0552
C16···H143.2498H11···C2i3.1971
C17···H73.3240H11···C3i3.4761
C17···H133.2638H11···C5i3.5105
C17···H153.2713H11···H13i3.0404
C18···H42.7887H11···H29i3.2822
C18···H203.2666H13···C11ii3.4112
C18···H223.2679H13···C17ii3.1441
C18···H253.0357H13···H8viii3.5020
C18···H293.5967H13···H11ii3.0404
C19···H42.8254H13···H17ii2.5592
C19···H213.2691H13···H28i3.4526
C19···H233.2662H14···C16ii2.9992
C20···H223.2535H14···C17ii3.2575
C21···H193.2670H14···C19ix3.5415
C21···H233.2631H14···C20ix3.1467
C22···H203.2527H14···C21ix3.5492
C23···H193.2668H14···H4ix3.5191
C23···H213.2662H14···H16ii2.6039
C23···H253.5120H14···H17ii3.0741
C24···H133.2487H14···H20ix3.1266
C24···H232.6358H15···C18ix3.1875
C24···H263.2574H15···C19x3.5282
C24···H283.2592H15···C19ix3.3675
C25···H233.2702H15···C20x3.5317
C25···H273.2576H15···C20ix3.4734
C25···H293.2647H15···C21ix3.4211
C26···H143.3793H15···C22ix3.2474
C26···H283.2559H15···C23ix3.1187
C27···H142.9679H15···H4ix2.8359
C27···H253.2590H15···H19x2.8844
C27···H293.2603H15···H20x2.8865
C28···H133.2558H15···H23ix3.5244
C28···H143.2674H16···C4x3.3523
C28···H263.2550H16···C14i3.1865
C29···H133.0032H16···C19x3.2147
C29···H233.0389H16···C20x3.4676
C29···H253.2642H16···H3x3.5138
C29···H273.2603H16···H4x2.8765
H2···H32.3403H16···H8vii3.5851
H2···H112.7726H16···H9viii2.7982
H3···H42.3490H16···H14i2.6039
H4···H192.6530H16···H19x2.7335
H7···H82.3401H16···H20x3.2045
H7···H173.2714H17···C13i2.9821
H8···H92.3351H17···C14i3.2569
H9···H102.3308H17···H8vii2.9070
H10···H112.3403H17···H9viii3.2261
H11···H173.3079H17···H13i2.5592
H13···H142.3344H17···H14i3.0741
H13···H293.2289H17···H28i3.5963
H14···H152.3426H19···C15vi3.4709
H14···H273.0436H19···C16vi3.4014
H14···H283.5240H19···C23i3.3335
H15···H162.3392H19···H15vi2.8844
H16···H172.3338H19···H16vi2.7335
H19···H202.3320H19···H23i2.8939
H20···H212.3382H19···H29i3.5662
H21···H222.3387H20···C15vi3.2940
H22···H232.3312H20···C16vi3.4588
H23···H253.5563H20···C22i3.2761
H23···H293.1946H20···C27xi3.2659
H25···H262.3363H20···H14xi3.1266
H26···H272.3317H20···H15vi2.8865
H27···H282.3323H20···H16vi3.2045
H28···H292.3437H20···H22i2.9353
N1···H11ii3.2586H20···H23i3.5421
N1···H28i3.2009H20···H27xi2.4433
N1···H29i2.7092H21···C25xii3.5425
N2···H10ii3.3416H21···C26xii3.2718
N2···H29i3.4038H21···C26xi3.4794
C1···H10ii3.2386H21···C27xii3.2619
C1···H11ii3.0552H21···C27xi3.4158
C1···H29i3.0771H21···C28xii3.5253
C2···H2iv3.1232H21···H23xii3.0003
C2···H10ii2.8481H21···H25xiii2.8467
C2···H10v3.1116H21···H26xi2.9115
C2···H11ii3.1971H21···H27xii3.5921
C3···H2iv3.3688H21···H27xi2.7825
C3···H9v3.3757H22···C18xiii3.1982
C3···H10v3.0609H22···C19xiii3.3946
C3···H11ii3.4761H22···C20ii3.3652
C4···H16vi3.3523H22···C20xiii3.5508
C5···H11ii3.5105H22···C21xiii3.5219
C5···H29i3.2728H22···C22xiii3.3164
C6···H3iv3.4432H22···C23xiii3.1572
C6···H10ii3.3602H22···C25xiii3.1400
C7···H3iv2.9561H22···H20ii2.9353
C7···H7vii3.3669H22···H23xii3.3299
C7···H8viii3.5964H22···H23xiii3.5548
C7···H10ii3.1928H22···H25xiii2.4717
C8···H3iv2.8226H23···C19ii3.2495
C8···H7vii2.8575H23···C21xiii3.0133
C9···H3v3.3906H23···C22xiii3.2196
C9···H3iv3.1933H23···H15xi3.5244
C9···H7i3.3457H23···H19ii2.8939
C9···H7vii3.3138H23···H20ii3.5421
C10···H2i3.4371H23···H21xiii3.0003
C10···H2v3.3971H23···H22xii3.5548
C10···H3v3.2083H23···H22xiii3.3299
C10···H7i3.1798H25···C21xii3.3689
C11···H13i3.4112H25···C22xii3.1925
C12···H8viii3.2211H25···C28i3.0656
C12···H28i2.9327H25···C29i3.4934
C13···H8viii3.1331H25···H21xii2.8467
C13···H17ii2.9821H25···H22xii2.4717
C13···H28i2.9842H25···H28i2.8208
C14···H4ix3.5796H25···H29i3.5622
C14···H8viii3.2977H26···C27iii3.0392
C14···H16ii3.1865H26···H21ix2.9115
C14···H17ii3.2569H26···H26xiv2.9226
C14···H28i3.1617H26···H26iii3.5438
C15···H4ix3.1888H26···H27iii2.5036
C15···H8viii3.5277H26···H28i3.5515
C15···H9viii3.3618H27···C20ix3.0597
C15···H19x3.4709H27···C21ix3.2235
C15···H20x3.2940H27···C26iii2.9808
C15···H28i3.3068H27···C27iii3.4074
C16···H8viii3.5663H27···H20ix2.4433
C16···H9viii2.7852H27···H21xiii3.5921
C16···H14i2.9992H27···H21ix2.7825
C16···H19x3.4014H27···H26iii2.5036
C16···H20x3.4588H27···H27iii3.2941
C16···H28i3.2769H28···N1ii3.2009
C17···H8viii3.4240H28···C12ii2.9327
C17···H9viii3.0441H28···C13ii2.9842
C17···H13i3.1441H28···C14ii3.1617
C17···H14i3.2575H28···C15ii3.3068
C17···H28i3.0886H28···C16ii3.2769
C18···H15xi3.1875H28···C17ii3.0886
C18···H22xii3.1982H28···C25ii3.0618
C19···H14xi3.5415H28···C26ii3.4865
C19···H15vi3.5282H28···H13ii3.4526
C19···H15xi3.3675H28···H17ii3.5963
C19···H16vi3.2147H28···H25ii2.8208
C19···H22xii3.3946H28···H26ii3.5515
C19···H23i3.2495H29···N1ii2.7092
C20···H14xi3.1467H29···N2ii3.4038
C20···H15vi3.5317H29···C1ii3.0771
C20···H15xi3.4734H29···C5ii3.2728
C20···H16vi3.4676H29···H11ii3.2822
C20···H22i3.3652H29···H19ii3.5662
C20···H22xii3.5508H29···H25ii3.5622
C1—N1—C5118.87 (12)C24—C29—C28119.73 (14)
C1—N2—C6118.65 (11)C1—C2—H2121.112
C1—N2—C12123.46 (9)C3—C2—H2121.119
C6—N2—C12117.44 (10)C2—C3—H3119.450
C5—N3—C18123.18 (12)C4—C3—H3119.452
C5—N3—C24118.12 (9)C3—C4—H4121.547
C18—N3—C24118.63 (10)C5—C4—H4121.569
N1—C1—N2116.84 (12)C6—C7—H7120.153
N1—C1—C2122.10 (11)C8—C7—H7120.150
N2—C1—C2121.06 (10)C7—C8—H8119.883
C1—C2—C3117.77 (11)C9—C8—H8119.887
C2—C3—C4121.10 (15)C8—C9—H9120.023
C3—C4—C5116.88 (13)C10—C9—H9120.027
N1—C5—N3114.45 (12)C9—C10—H10119.846
N1—C5—C4123.25 (10)C11—C10—H10119.840
N3—C5—C4122.28 (11)C6—C11—H11120.123
N2—C6—C7119.74 (11)C10—C11—H11120.125
N2—C6—C11120.24 (9)C12—C13—H13120.001
C7—C6—C11120.02 (11)C14—C13—H13119.990
C6—C7—C8119.70 (12)C13—C14—H14119.524
C7—C8—C9120.23 (11)C15—C14—H14119.533
C8—C9—C10119.95 (12)C14—C15—H15120.523
C9—C10—C11120.31 (13)C16—C15—H15120.524
C6—C11—C10119.75 (11)C15—C16—H16119.727
N2—C12—C13121.74 (12)C17—C16—H16119.723
N2—C12—C17119.35 (11)C12—C17—H17119.679
C13—C12—C17118.90 (13)C16—C17—H17119.708
C12—C13—C14120.01 (12)C18—C19—H19119.997
C13—C14—C15120.94 (13)C20—C19—H19119.992
C14—C15—C16118.95 (15)C19—C20—H20119.651
C15—C16—C17120.55 (14)C21—C20—H20119.664
C12—C17—C16120.61 (12)C20—C21—H21120.340
N3—C18—C19121.16 (11)C22—C21—H21120.337
N3—C18—C23119.59 (12)C21—C22—H22119.764
C19—C18—C23119.20 (10)C23—C22—H22119.757
C18—C19—C20120.01 (12)C18—C23—H23119.855
C19—C20—C21120.69 (13)C22—C23—H23119.850
C20—C21—C22119.32 (11)C24—C25—H25120.185
C21—C22—C23120.48 (12)C26—C25—H25120.183
C18—C23—C22120.30 (12)C25—C26—H26119.895
N3—C24—C25119.92 (11)C27—C26—H26119.891
N3—C24—C29119.78 (13)C26—C27—H27119.916
C25—C24—C29120.30 (14)C28—C27—H27119.919
C24—C25—C26119.63 (12)C27—C28—H28120.024
C25—C26—C27120.21 (15)C29—C28—H28120.017
C26—C27—C28120.17 (16)C24—C29—H29120.133
C27—C28—C29119.96 (13)C28—C29—H29120.135
C1—N1—C5—N3177.95 (9)C3—C4—C5—N3179.10 (10)
C1—N1—C5—C40.67 (17)N2—C6—C7—C8179.94 (11)
C5—N1—C1—N2178.55 (9)N2—C6—C11—C10178.61 (11)
C5—N1—C1—C21.86 (16)C7—C6—C11—C102.0 (2)
C1—N2—C6—C7122.77 (12)C11—C6—C7—C80.6 (2)
C1—N2—C6—C1157.80 (15)C6—C7—C8—C90.9 (2)
C6—N2—C1—N1162.66 (9)C7—C8—C9—C101.1 (2)
C6—N2—C1—C216.93 (15)C8—C9—C10—C110.2 (2)
C1—N2—C12—C1338.32 (14)C9—C10—C11—C61.7 (2)
C1—N2—C12—C17142.21 (9)N2—C12—C13—C14178.86 (8)
C12—N2—C1—N19.43 (15)N2—C12—C17—C16179.52 (8)
C12—N2—C1—C2170.98 (9)C13—C12—C17—C160.99 (15)
C6—N2—C12—C13149.50 (9)C17—C12—C13—C141.67 (15)
C6—N2—C12—C1729.97 (13)C12—C13—C14—C150.78 (15)
C12—N2—C6—C764.67 (14)C13—C14—C15—C160.80 (16)
C12—N2—C6—C11114.77 (12)C14—C15—C16—C171.49 (16)
C5—N3—C18—C1935.16 (18)C15—C16—C17—C120.60 (16)
C5—N3—C18—C23147.51 (11)N3—C18—C19—C20177.64 (12)
C18—N3—C5—N1147.66 (11)N3—C18—C23—C22177.09 (11)
C18—N3—C5—C433.71 (18)C19—C18—C23—C220.3 (2)
C5—N3—C24—C25109.07 (11)C23—C18—C19—C200.3 (2)
C5—N3—C24—C2970.77 (14)C18—C19—C20—C210.4 (2)
C24—N3—C5—N129.38 (15)C19—C20—C21—C220.2 (2)
C24—N3—C5—C4149.25 (11)C20—C21—C22—C230.8 (2)
C18—N3—C24—C2568.10 (14)C21—C22—C23—C180.8 (2)
C18—N3—C24—C29112.06 (11)N3—C24—C25—C26179.54 (9)
C24—N3—C18—C19141.86 (11)N3—C24—C29—C28179.69 (8)
C24—N3—C18—C2335.46 (17)C25—C24—C29—C280.15 (16)
N1—C1—C2—C31.73 (16)C29—C24—C25—C260.29 (16)
N2—C1—C2—C3178.70 (9)C24—C25—C26—C270.28 (17)
C1—C2—C3—C40.40 (17)C25—C26—C27—C280.12 (18)
C2—C3—C4—C50.69 (18)C26—C27—C28—C290.02 (18)
C3—C4—C5—N10.59 (18)C27—C28—C29—C240.01 (17)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x, y, z; (v) x, y1, z; (vi) x, y1/2, z+1/2; (vii) x, y1/2, z1/2; (viii) x, y+1/2, z1/2; (ix) x, y+1/2, z1/2; (x) x, y1/2, z1/2; (xi) x, y+1/2, z+1/2; (xii) x+1, y1/2, z+1/2; (xiii) x+1, y+1/2, z+1/2; (xiv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg4 are the centriods of the C12–C17 and C18–C23 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C29—H29···N1ii0.952.713.4649 (18)137
C15—H15···Cg4ix0.953.003.8133 (17)145
C28—H28···Cg3ii0.952.803.5831 (17)140
Symmetry codes: (ii) x, y+1, z; (ix) x, y+1/2, z1/2.
 

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST).

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