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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 2| Part 8| August 2017| x171221
https://doi.org/10.1107/S2414314617012214

2-(Pyridin-2-yl)-1,8-naphthyridine

CROSSMARK_Color_square_no_text.svg
Ryosuke Abe,a Tsugiko Takaseb and Dai Oyamac*

aGraduate School of Science and Engineering, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, bInstitute of Environmental Radioactivity, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, and cDepartment of Industrial Systems Engineering, Cluster of Science and Engineering, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan
*Correspondence e-mail: daio@sss.fukushima-u.ac.jp

Edited by I. Brito, University of Antofagasta, Chile (Received 19 August 2017; accepted 23 August 2017; online 30 August 2017)

The title compound, C13H9N3, has three symmetry-independent mol­ecules in the asymmetric unit. The dihedral angles between the naphthyridine ring system and the pyridine group are in the range 3.927 (4)–7.362 (4)°. In the crystal, C—H⋯N inter­actions and aromatic π–π stacking [centroid–centroid distances = 3.5755 (7) and 3.6544 (7) Å] generate a three-dimensional network.

CCDC reference: 1570310

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

Structure description

1,8-Naphthyridines are key components of several anti­bacterial agents (Stanforth, 1996[Stanforth, S. P. (1996). In Comprehensive Heterocyclic Chemistry II, edited by C. A. Ramsden, Vol. 7, ch. 7.15. Tarrytown: Pergamon Press.]). In addition to medicinal applications, 1,8-naphthyridine and its derivatives have been employed in coordination chemistry. For example, the title compound is utilized not only as a bidendate ligand (Oyama & Hamada, 2008[Oyama, D. & Hamada, T. (2008). Acta Cryst. E64, m442-m443.]), but also as a bridging ligand for binuclear complexes (Campos-Fernández et al., 2002[Campos-Fernández, C. S., Thomson, L. M., Galán-Mascarós, J. R., Ouyang, X. & Dunbar, K. R. (2002). Inorg. Chem. 41, 1523-1533.]). Although numerous crystal structures of metal complexes containing the title compound have been described (Oyama & Hamada, 2008[Oyama, D. & Hamada, T. (2008). Acta Cryst. E64, m442-m443.]; Oyama et al., 2011[Oyama, D., Yuzuriya, K. & Takase, T. (2011). Acta Cryst. E67, m737-m738.], 2017[Oyama, D., Abe, R. & Takase, T. (2017). Chem. Lett. 46, 1412-1414.]), no structural characterization of the title compound has been reported so far.

The title compound crystallizes with three mol­ecules in the asymmetric unit (Fig. 1[link]), which exhibit comparable bond lengths and angles. As expected, the naphthyridine ring system is almost planar. Additionally, the two aromatic groups tend to be coplanar in the related compounds with 1,8-naphthyridyl and aromatic ring systems (Sinha et al., 2009[Sinha, A., Rahaman, S. M. W., Sarkar, M., Saha, B., Daw, P. & Bera, J. K. (2009). Inorg. Chem. 48, 11114-11122.]). The pyridine rings make dihedral angles of 3.927 (4)–7.362 (4)° with the naphthyridine ring systems in the title compound. All H atoms attached to C atoms are clearly visible in the difference map and the assignment of N atoms in aromatic rings is unambiguous. Although the title compound exists in a cis conformation on coordinating to metals (Oyama & Hamada, 2008[Oyama, D. & Hamada, T. (2008). Acta Cryst. E64, m442-m443.]; Oyama et al., 2011[Oyama, D., Yuzuriya, K. & Takase, T. (2011). Acta Cryst. E67, m737-m738.], 2017[Oyama, D., Abe, R. & Takase, T. (2017). Chem. Lett. 46, 1412-1414.]), the pyridine N atom exists in a trans conformation with respect to the naphthyridine N atoms in the present case. The bond lengths and angles are within normal ranges [C—N = 1.3188 (16)–1.3665 (15) Å, C—C = 1.3591 (17)–1.4224 (18) Å and C—N—C = 116.74 (12)–118.15 (11)°]. These values are similar to those of a related aryl-substituted 1,8-naphthyridine (Xiong et al., 2016[Xiong, B., Zhang, S., Jiang, H. & Zhang, M. (2016). Org. Lett. 18, 724-727.]).

[Figure 1]
Figure 1
The three independent mol­ecules of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius.

In the crystal packing, supra­molecular layers in the ab plane are stabilized by C—H⋯N and π–π inter­actions [Cg⋯Cg = 3.5755 (7) and 3.6544 (7) Å] (Table 1[link] and Fig. 2[link]). These effects lead to small dihedral angles between the naphthyridine ring system and the pyridine group. Meanwhile, the inter­planar distance between rings Cg1 and Cg7iv [symmetry code: (iv) −x + 1, y + [1 \over 2], −z + 1; Cg1 and Cg7 are the centroids of the N2/C6–C10 and N6/C22–C26 rings, respectively] is longer [3.8082 (7) Å], suggesting that one unit consists of three mol­ecules.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯N4i 1.008 (15) 2.529 (17) 3.4161 (16) 146.6 (14)
C7—H7⋯N1 0.962 (16) 2.462 (17) 2.8037 (16) 100.6 (12)
C12—H12⋯N1ii 0.967 (15) 2.616 (17) 3.4845 (16) 149.6 (14)
C15—H15⋯N8iii 0.949 (15) 2.507 (17) 3.3470 (16) 147.6 (14)
C17—H17⋯N5 0.940 (16) 2.453 (16) 2.7856 (15) 100.7 (12)
C20—H20⋯N4 0.985 (16) 2.460 (17) 2.8036 (15) 100.0 (12)
C33—H33⋯N7 0.948 (16) 2.456 (16) 2.7944 (16) 100.9 (13)
C38—H38⋯N2i 0.991 (16) 2.511 (17) 3.4016 (16) 149.5 (14)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+1]; (ii) [-x+2, y+{\script{1\over 2}}, -z+1]; (iii) [-x+2, y+{\script{1\over 2}}, -z].
[Figure 2]
Figure 2
A view along the a axis, showing weak C—H⋯N hydrogen bonds (blue) and π–π contacts (green). Ring centroids are shown as coloured spheres.

Synthesis and crystallization

The precursor (2-amino­nicotinaldehyde) and the title compound were synthesized according to the method of Campos-Fernández et al. (2002[Campos-Fernández, C. S., Thomson, L. M., Galán-Mascarós, J. R., Ouyang, X. & Dunbar, K. R. (2002). Inorg. Chem. 41, 1523-1533.]). A direct condensation reaction using 2-amino­nicotinaldehyde (696 mg, 5.70 mmol), 2-acetyl­pyridine (1.0 ml, 8.92 mmol) and potassium hydroxide (25 mg, 0.45 mmol) in methanol (5 ml) afforded a light-brown solid in 80% yield. The crude product was recrystallized from an acetone–diethyl ether mixture (1:30 v/v) at room temperature to give good-quality crystals suitable for X-ray diffraction.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The crystal studied was an inversion twin, with twin fractions of 0.7 (11) and 0.3 (11).

Table 2
Experimental details

Crystal data
Chemical formula C13H9N3
Mr 207.23
Crystal system, space group Monoclinic, P21
Temperature (K) 93
a, b, c (Å) 6.1708 (2), 16.9596 (7), 14.2882 (6)
β (°) 99.9699 (19)
V (Å3) 1472.74 (10)
Z 6
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.45 × 0.20 × 0.10
 
Data collection
Diffractometer Rigaku Saturn724
Absorption correction Multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.928, 0.991
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 14789, 6626, 6058
Rint 0.014
(sin θ/λ)max (Å−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.093, 1.04
No. of reflections 6626
No. of parameters 515
No. of restraints 1
H-atom treatment Only H-atom coordinates refined
Δρmax, Δρmin (e Å−3) 0.35, −0.19
Computer programs: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]), SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1570310

Crystal structure: contains datablocks General, I. DOI: https://doi.org/10.1107/S2414314617012214/bx4007sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012214/bx4007Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012214/bx4007Isup3.mol

checkCIF report


Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-(Pyridin-2-yl)-1,8-naphthyridine top
Crystal data top
C13H9N3F(000) = 648.00
Mr = 207.23Dx = 1.402 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ybCell parameters from 4248 reflections
a = 6.1708 (2) Åθ = 3.1–27.5°
b = 16.9596 (7) ŵ = 0.09 mm−1
c = 14.2882 (6) ÅT = 93 K
β = 99.9699 (19)°Prism, yellow
V = 1472.74 (10) Å30.45 × 0.20 × 0.10 mm
Z = 6
Data collection top
Rigaku Saturn724
diffractometer		6058 reflections with F2 > 2.0σ(F2)
Detector resolution: 28.944 pixels mm-1Rint = 0.014
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)		h = −8→8
Tmin = 0.928, Tmax = 0.991k = −22→22
14789 measured reflectionsl = −18→18
6626 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093Only H-atom coordinates refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0695P)2]
where P = (Fo2 + 2Fc2)/3
6626 reflections(Δ/σ)max = 0.001
515 parametersΔρmax = 0.35 e Å−3
1 restraintΔρmin = −0.19 e Å−3
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). All H atoms were identified in a difference Fourier map and their positions refined freely with Uiso(H) = 1.2Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.87594 (17)0.28801 (6)0.69204 (7)0.0204 (3)
N20.66559 (16)0.46716 (6)0.57649 (7)0.0172 (2)
N30.57101 (16)0.58104 (6)0.49070 (7)0.0195 (2)
N40.70483 (16)0.59955 (6)0.12837 (7)0.0207 (3)
N50.92194 (17)0.42608 (6)0.25484 (7)0.0177 (2)
N61.01665 (17)0.31352 (6)0.34193 (7)0.0209 (3)
N70.53827 (17)0.42723 (6)−0.01887 (7)0.0233 (3)
N80.75468 (17)0.25164 (6)0.10279 (7)0.0179 (2)
N90.85512 (17)0.14117 (6)0.19418 (7)0.0209 (3)
C10.8171 (3)0.23280 (7)0.74938 (9)0.0218 (3)
C20.6213 (2)0.23424 (7)0.78485 (9)0.0221 (3)
C30.4808 (2)0.29730 (8)0.76089 (9)0.0221 (3)
C40.5402 (2)0.35602 (7)0.70257 (9)0.0195 (3)
C50.73813 (19)0.34860 (6)0.66848 (8)0.0168 (3)
C60.80663 (19)0.40977 (7)0.60424 (8)0.0162 (3)
C71.01571 (19)0.40401 (7)0.57595 (8)0.0192 (3)
C81.07842 (18)0.46107 (7)0.51931 (8)0.0189 (3)
C90.93315 (19)0.52367 (7)0.48811 (8)0.0170 (3)
C100.72520 (19)0.52397 (7)0.51823 (8)0.0163 (3)
C110.9799 (2)0.58520 (7)0.42822 (8)0.0196 (3)
C120.8255 (2)0.64204 (7)0.40108 (8)0.0212 (3)
C130.6239 (2)0.63686 (7)0.43447 (8)0.0203 (3)
C140.7579 (3)0.64916 (7)0.06284 (9)0.0230 (3)
C150.9466 (2)0.64282 (7)0.02335 (9)0.0224 (3)
C161.0919 (2)0.58223 (8)0.05402 (9)0.0222 (3)
C171.03995 (19)0.52957 (7)0.12084 (8)0.0189 (3)
C180.84483 (19)0.54007 (7)0.15603 (8)0.0168 (3)
C190.77970 (19)0.48275 (7)0.22518 (8)0.0162 (3)
C200.5714 (2)0.48967 (7)0.25356 (8)0.0182 (3)
C210.50999 (19)0.43385 (7)0.31242 (8)0.0191 (3)
C220.65624 (18)0.37180 (7)0.34473 (8)0.0171 (3)
C230.86361 (19)0.37057 (7)0.31452 (8)0.0169 (3)
C240.6076 (2)0.31011 (7)0.40441 (8)0.0208 (3)
C250.7604 (2)0.25285 (7)0.43064 (8)0.0218 (3)
C260.9624 (3)0.25739 (7)0.39766 (9)0.0221 (3)
C270.5951 (3)0.48079 (8)−0.07890 (9)0.0257 (3)
C280.7876 (3)0.47778 (8)−0.11602 (9)0.0245 (3)
C290.9295 (3)0.41530 (8)−0.09078 (9)0.0238 (3)
C300.8740 (2)0.35895 (7)−0.02897 (9)0.0206 (3)
C310.6778 (2)0.36714 (7)0.00599 (8)0.0179 (3)
C320.61384 (19)0.30907 (7)0.07453 (8)0.0173 (3)
C330.4090 (2)0.31726 (7)0.10632 (8)0.0200 (3)
C340.3500 (2)0.26294 (7)0.16728 (9)0.0214 (3)
C350.49601 (19)0.20031 (7)0.19869 (8)0.0185 (3)
C360.70007 (19)0.19762 (7)0.16541 (8)0.0175 (3)
C370.4553 (2)0.14189 (7)0.26402 (9)0.0219 (3)
C380.6114 (2)0.08649 (7)0.29344 (9)0.0231 (3)
C390.8090 (3)0.08885 (7)0.25631 (9)0.0226 (3)
H10.918 (3)0.1879 (9)0.7651 (10)0.0261*
H20.588 (3)0.1882 (9)0.8247 (10)0.0265*
H30.338 (3)0.3016 (9)0.7824 (10)0.0266*
H40.450 (3)0.4017 (9)0.6859 (10)0.0233*
H71.110 (3)0.3603 (9)0.5981 (10)0.0230*
H81.222 (3)0.4602 (9)0.5002 (10)0.0227*
H111.126 (3)0.5869 (9)0.4105 (10)0.0235*
H120.852 (3)0.6858 (9)0.3612 (10)0.0254*
H130.515 (3)0.6776 (9)0.4162 (10)0.0244*
H140.650 (3)0.6926 (9)0.0445 (10)0.0276*
H150.972 (3)0.6769 (9)−0.0263 (10)0.0268*
H161.231 (3)0.5731 (9)0.0279 (10)0.0267*
H171.131 (3)0.4865 (9)0.1423 (10)0.0226*
H200.477 (3)0.5351 (9)0.2313 (10)0.0218*
H210.366 (3)0.4350 (9)0.3317 (10)0.0229*
H240.458 (3)0.3102 (9)0.4236 (10)0.0250*
H250.737 (3)0.2052 (10)0.4710 (10)0.0261*
H261.076 (3)0.2168 (9)0.4170 (10)0.0265*
H270.489 (3)0.5225 (10)−0.0949 (11)0.0309*
H280.826 (3)0.5167 (10)−0.1569 (11)0.0293*
H291.073 (3)0.4118 (9)−0.1160 (10)0.0286*
H300.970 (3)0.3149 (9)−0.0107 (10)0.0247*
H330.317 (3)0.3607 (9)0.0848 (10)0.0240*
H340.210 (3)0.2664 (9)0.1898 (10)0.0257*
H370.314 (3)0.1435 (9)0.2909 (10)0.0263*
H380.589 (3)0.0444 (9)0.3389 (11)0.0278*
H390.926 (3)0.0485 (9)0.2772 (10)0.0271*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0203 (6)0.0204 (5)0.0210 (5)0.0033 (5)0.0048 (4)0.0011 (4)
N20.0162 (5)0.0183 (5)0.0176 (5)−0.0002 (4)0.0040 (4)−0.0010 (4)
N30.0200 (5)0.0199 (5)0.0191 (5)0.0020 (4)0.0047 (4)0.0008 (4)
N40.0219 (5)0.0185 (5)0.0221 (5)0.0016 (4)0.0049 (4)0.0023 (4)
N50.0195 (5)0.0167 (5)0.0171 (5)0.0017 (4)0.0033 (4)0.0006 (4)
N60.0230 (6)0.0206 (5)0.0194 (5)0.0053 (4)0.0046 (4)0.0024 (4)
N70.0246 (6)0.0228 (6)0.0219 (5)0.0041 (5)0.0022 (4)0.0012 (5)
N80.0189 (5)0.0176 (5)0.0174 (5)−0.0010 (4)0.0037 (4)−0.0010 (4)
N90.0208 (5)0.0201 (5)0.0227 (5)0.0013 (4)0.0062 (4)0.0014 (4)
C10.0236 (7)0.0211 (6)0.0205 (6)0.0051 (5)0.0035 (5)0.0005 (5)
C20.0243 (7)0.0210 (6)0.0206 (6)−0.0032 (5)0.0029 (5)0.0012 (5)
C30.0182 (6)0.0241 (6)0.0244 (6)−0.0025 (5)0.0043 (5)0.0002 (5)
C40.0158 (6)0.0192 (6)0.0230 (6)0.0016 (5)0.0023 (5)0.0000 (5)
C50.0157 (6)0.0178 (6)0.0161 (5)−0.0014 (5)0.0005 (5)−0.0033 (5)
C60.0157 (6)0.0164 (6)0.0155 (5)−0.0006 (5)0.0001 (5)−0.0026 (5)
C70.0158 (6)0.0199 (6)0.0212 (6)0.0022 (5)0.0009 (5)−0.0021 (5)
C80.0127 (6)0.0232 (6)0.0212 (6)−0.0019 (5)0.0039 (5)−0.0040 (5)
C90.0153 (6)0.0191 (6)0.0166 (6)−0.0039 (5)0.0028 (5)−0.0051 (5)
C100.0151 (6)0.0183 (6)0.0152 (5)−0.0000 (5)0.0022 (5)−0.0020 (5)
C110.0175 (6)0.0223 (6)0.0199 (6)−0.0043 (5)0.0060 (5)−0.0026 (5)
C120.0252 (7)0.0199 (6)0.0191 (6)−0.0052 (5)0.0056 (5)−0.0005 (5)
C130.0222 (6)0.0194 (6)0.0194 (6)0.0028 (5)0.0036 (5)0.0006 (5)
C140.0274 (7)0.0185 (6)0.0235 (6)0.0013 (5)0.0052 (5)0.0035 (5)
C150.0293 (7)0.0178 (6)0.0207 (6)−0.0053 (5)0.0062 (5)−0.0002 (5)
C160.0218 (7)0.0246 (7)0.0210 (6)−0.0039 (5)0.0061 (5)−0.0032 (5)
C170.0176 (6)0.0183 (6)0.0200 (6)−0.0005 (5)0.0011 (5)−0.0022 (5)
C180.0194 (6)0.0148 (6)0.0157 (5)−0.0015 (5)0.0013 (5)−0.0012 (5)
C190.0164 (6)0.0163 (6)0.0155 (6)−0.0022 (5)0.0018 (5)−0.0026 (5)
C200.0166 (6)0.0170 (6)0.0202 (6)0.0009 (5)0.0010 (5)−0.0018 (5)
C210.0139 (6)0.0219 (6)0.0212 (6)−0.0017 (5)0.0027 (5)−0.0029 (5)
C220.0165 (6)0.0186 (6)0.0156 (5)−0.0032 (5)0.0012 (5)−0.0023 (5)
C230.0161 (6)0.0184 (6)0.0160 (6)−0.0007 (5)0.0017 (5)−0.0028 (5)
C240.0192 (6)0.0236 (7)0.0196 (6)−0.0043 (5)0.0035 (5)−0.0014 (5)
C250.0281 (7)0.0194 (6)0.0171 (6)−0.0037 (5)0.0018 (5)0.0026 (5)
C260.0255 (7)0.0193 (6)0.0207 (6)0.0033 (5)0.0020 (5)0.0011 (5)
C270.0298 (7)0.0246 (7)0.0218 (6)0.0063 (6)0.0015 (6)0.0037 (5)
C280.0303 (7)0.0211 (6)0.0209 (6)−0.0019 (6)0.0016 (5)0.0037 (5)
C290.0222 (7)0.0257 (7)0.0232 (6)−0.0037 (5)0.0030 (5)0.0008 (5)
C300.0200 (6)0.0181 (6)0.0227 (6)0.0016 (5)0.0011 (5)−0.0009 (5)
C310.0205 (6)0.0167 (6)0.0153 (5)−0.0017 (5)−0.0001 (5)−0.0031 (5)
C320.0164 (6)0.0181 (6)0.0167 (6)−0.0022 (5)0.0015 (5)−0.0039 (5)
C330.0179 (6)0.0219 (6)0.0196 (6)0.0030 (5)0.0017 (5)−0.0047 (5)
C340.0163 (6)0.0267 (7)0.0221 (6)−0.0008 (5)0.0053 (5)−0.0067 (5)
C350.0181 (6)0.0206 (6)0.0173 (6)−0.0034 (5)0.0043 (5)−0.0058 (5)
C360.0169 (6)0.0191 (6)0.0173 (6)−0.0022 (5)0.0045 (5)−0.0030 (5)
C370.0225 (7)0.0234 (6)0.0214 (6)−0.0073 (5)0.0079 (5)−0.0052 (5)
C380.0309 (7)0.0201 (6)0.0198 (6)−0.0068 (5)0.0082 (5)−0.0007 (5)
C390.0259 (7)0.0201 (6)0.0221 (6)−0.0008 (5)0.0050 (5)0.0007 (5)
Geometric parameters (Å, º) top
N1—C11.3353 (17)C25—C261.409 (2)
N1—C51.3391 (15)C27—C281.383 (2)
N2—C61.3200 (15)C28—C291.3823 (19)
N2—C101.3648 (16)C29—C301.3839 (19)
N3—C101.3665 (15)C30—C311.3944 (19)
N3—C131.3188 (16)C31—C321.4896 (18)
N4—C141.3408 (17)C32—C331.4219 (18)
N4—C181.3423 (16)C33—C341.3601 (18)
N5—C191.3210 (16)C34—C351.4148 (17)
N5—C231.3599 (16)C35—C361.4217 (18)
N6—C231.3614 (16)C35—C371.4133 (18)
N6—C261.3209 (17)C37—C381.3591 (17)
N7—C271.3371 (18)C38—C391.412 (2)
N7—C311.3418 (16)C1—H10.986 (15)
N8—C321.3212 (16)C2—H21.009 (15)
N8—C361.3630 (16)C3—H30.985 (16)
N9—C361.3656 (16)C4—H40.960 (15)
N9—C391.3205 (17)C7—H70.963 (15)
C1—C21.389 (2)C8—H80.972 (15)
C2—C31.3818 (18)C11—H110.978 (16)
C3—C41.3878 (19)C12—H120.968 (16)
C4—C51.3967 (19)C13—H130.967 (15)
C5—C61.4939 (17)C14—H140.998 (15)
C6—C71.4206 (18)C15—H150.949 (16)
C7—C81.3600 (17)C16—H161.004 (15)
C8—C91.4111 (16)C17—H170.941 (15)
C9—C101.4224 (18)C20—H200.984 (15)
C9—C111.4107 (17)C21—H210.973 (15)
C11—C121.3640 (17)C24—H241.008 (16)
C12—C131.4097 (19)C25—H251.017 (16)
C14—C151.383 (2)C26—H260.986 (15)
C15—C161.3840 (18)C27—H270.965 (16)
C16—C171.3848 (19)C28—H280.938 (17)
C17—C181.3942 (18)C29—H291.013 (16)
C18—C191.4901 (17)C30—H300.961 (15)
C19—C201.4178 (18)C33—H330.949 (15)
C20—C211.3630 (18)C34—H340.976 (16)
C21—C221.4109 (16)C37—H371.011 (16)
C22—C231.4197 (18)C38—H380.992 (16)
C22—C241.4144 (17)C39—H391.003 (15)
C24—C251.3602 (17)
N1···N23.5917 (14)C23···H34iv3.490 (16)
N1···C32.7870 (18)C24···H13vi3.588 (15)
N1···C72.8037 (16)C24···H373.589 (15)
N2···C42.8070 (17)C25···H73.453 (14)
N2···C82.8087 (16)C25···H13vi3.256 (15)
N2···C133.5052 (16)C26···H73.344 (14)
N3···C63.5166 (16)C26···H24iv3.146 (15)
N3···C112.8196 (17)C26···H34iv3.570 (16)
N4···N53.5885 (14)C26···H37iv3.453 (16)
N4···C162.7925 (18)C27···H4xi3.585 (14)
N4···C202.8035 (16)C27···H16ii3.320 (15)
N5···C172.7856 (16)C27···H29ii3.382 (15)
N5···C212.8072 (17)C28···H4xi3.460 (14)
N5···C263.4979 (16)C28···H163.518 (14)
N6···C193.5090 (16)C28···H39ix3.357 (16)
N6···C242.8199 (18)C29···H163.522 (14)
N7···N83.5874 (14)C29···H173.559 (14)
N7···C292.7901 (18)C29···H33iv3.284 (13)
N7···C332.7943 (17)C30···H15v3.286 (16)
N8···C302.8070 (17)C30···H173.441 (14)
N8···C342.8141 (18)C30···H33iv2.927 (13)
N8···C393.5059 (16)C31···H14xii3.587 (15)
N9···C323.5166 (16)C32···H14xii2.912 (15)
N9···C372.8172 (18)C32···H15v3.555 (16)
C1···C42.7088 (17)C33···H14xii2.995 (15)
C2···C52.7315 (17)C33···H15xii3.402 (15)
C6···C92.7464 (18)C33···H17ii3.427 (15)
C7···C102.7424 (17)C33···H30ii2.928 (14)
C9···C132.7216 (17)C34···H14xii3.252 (15)
C10···C122.7482 (17)C34···H15xii2.958 (14)
C14···C172.7075 (17)C34···H30ii3.268 (14)
C15···C182.7272 (18)C35···H14xii3.438 (14)
C19···C222.7367 (17)C35···H15xii3.479 (14)
C20···C232.7469 (17)C35···H27xii3.368 (16)
C22···C262.7222 (17)C36···H14xii3.380 (14)
C23···C252.7405 (18)C36···H15v3.092 (16)
C27···C302.7050 (18)C36···H16v3.560 (15)
C28···C312.7254 (19)C36···H27xii3.284 (16)
C32···C352.7431 (17)C36···H34iv3.315 (15)
C33···C362.7442 (17)C37···H253.338 (14)
C35···C392.7260 (17)C37···H27xii3.217 (16)
C36···C382.7468 (18)C37···H28xii2.991 (15)
N1···C12i3.4847 (17)C38···H4vi3.176 (16)
N2···C8ii3.5751 (15)C38···H253.226 (15)
N2···C38iii3.4016 (17)C38···H27xii3.000 (15)
N3···C213.5398 (16)C38···H28xii3.266 (15)
N3···C38iii3.4626 (18)C39···H263.373 (14)
N4···C2iii3.4160 (17)C39···H27xii2.915 (14)
N4···C273.5484 (17)C39···H28v3.114 (17)
N5···C21iv3.5817 (16)C39···H37iv3.208 (15)
N5···C323.5347 (15)H1···N4i2.957 (14)
N6···C83.5350 (16)H1···C11i3.414 (15)
N6···C363.5121 (15)H1···C12i3.169 (16)
N7···C183.4422 (15)H1···C14i2.961 (13)
N8···C15v3.3470 (18)H1···C15i3.089 (14)
N9···C15v3.5319 (18)H1···C16i3.155 (15)
N9···C263.4799 (16)H1···C17i3.129 (15)
C2···N4vi3.4160 (17)H1···C18i3.020 (15)
C2···C30vii3.5420 (17)H1···H3iv3.20 (2)
C4···C7ii3.5190 (16)H1···H11i3.01 (2)
C4···C28vii3.4559 (18)H1···H12i2.48 (3)
C6···C243.3620 (16)H1···H13vi3.390 (18)
C7···C4iv3.5190 (16)H1···H14i3.464 (19)
C7···C243.5704 (16)H1···H20vi3.57 (2)
C7···C253.4974 (16)H2···N4vi2.528 (16)
C7···C263.5342 (17)H2···C14vi2.959 (16)
C8···N2iv3.5751 (15)H2···C15i3.376 (14)
C8···N63.5350 (16)H2···C16i2.992 (14)
C8···C233.3663 (16)H2···C17i3.536 (15)
C9···C223.5410 (16)H2···H12vi3.455 (19)
C9···C233.5650 (17)H2···H13vi3.395 (19)
C10···C213.3756 (16)H2···H14vi2.57 (3)
C10···C223.5527 (17)H2···H16i2.95 (2)
C11···C193.4236 (16)H2···H20vi2.73 (2)
C12···N1viii3.4847 (17)H3···N1ii2.929 (14)
C12···C203.5261 (16)H3···N7vii3.593 (14)
C12···C26viii3.5365 (17)H3···C1ii3.376 (15)
C13···C203.5676 (17)H3···C14vi3.519 (16)
C14···C273.5440 (18)H3···H1ii3.20 (2)
C15···N8ix3.3470 (18)H3···H7ii2.935 (19)
C15···N9ix3.5319 (18)H3···H12vi2.93 (2)
C15···C283.4765 (18)H3···H14vi3.08 (2)
C16···C283.3146 (18)H3···H29xiii3.02 (3)
C16···C293.5470 (19)H4···C7ii2.862 (14)
C17···C20iv3.5577 (16)H4···C8ii3.169 (14)
C17···C283.5812 (17)H4···C27vii3.585 (14)
C17···C293.5566 (18)H4···C28vii3.460 (14)
C18···N73.4422 (15)H4···C38iii3.176 (16)
C18···C273.5864 (17)H4···H7ii2.355 (19)
C19···C113.4236 (16)H4···H8ii2.950 (19)
C20···C123.5261 (16)H4···H28vii3.52 (2)
C20···C133.5676 (17)H4···H38iii2.45 (3)
C20···C17ii3.5577 (16)H4···H39iii3.50 (3)
C21···N33.5398 (16)H7···C3iv3.152 (14)
C21···N5ii3.5817 (16)H7···C4iv2.809 (14)
C21···C103.3756 (16)H7···C253.453 (14)
C21···C333.5121 (17)H7···C263.344 (14)
C22···C93.5410 (16)H7···H3iv2.935 (19)
C22···C103.5527 (17)H7···H4iv2.355 (19)
C22···C343.4277 (16)H7···H12i3.02 (3)
C23···C83.3663 (16)H7···H263.53 (2)
C23···C93.5650 (17)H8···N2iv2.767 (14)
C24···C63.3620 (16)H8···N3iv2.993 (15)
C24···C73.5704 (16)H8···N63.452 (14)
C24···C343.5752 (17)H8···C10iv3.255 (15)
C24···C353.4469 (16)H8···C21iv3.493 (15)
C24···C373.5205 (17)H8···C233.495 (13)
C25···C73.4974 (16)H8···H4iv2.950 (19)
C25···C353.5450 (16)H8···H21iv2.74 (2)
C25···C373.3470 (17)H8···H24iv3.21 (2)
C25···C383.4677 (17)H8···H38viii2.78 (2)
C26···N93.4799 (16)H11···N3iv2.788 (14)
C26···C73.5342 (17)H11···C1viii3.426 (15)
C26···C12i3.5365 (17)H11···C13iv3.148 (15)
C26···C363.5776 (17)H11···C193.569 (14)
C26···C393.5331 (17)H11···H1viii3.01 (2)
C27···N43.5484 (17)H11···H13iv2.84 (2)
C27···C143.5440 (18)H11···H21iv3.27 (2)
C27···C183.5864 (17)H11···H25viii2.67 (2)
C27···C38x3.5890 (18)H12···N1viii2.614 (16)
C28···C4xi3.4559 (18)H12···C1viii2.899 (16)
C28···C153.4765 (18)H12···C2iii3.385 (14)
C28···C163.3146 (18)H12···C3iii3.099 (14)
C28···C173.5812 (17)H12···H1viii2.48 (3)
C29···C163.5470 (19)H12···H2iii3.455 (19)
C29···C173.5566 (18)H12···H3iii2.93 (2)
C30···C2xi3.5420 (17)H12···H7viii3.02 (3)
C30···C33iv3.5951 (17)H12···H25viii3.189 (19)
C32···N53.5347 (15)H12···H26viii3.17 (2)
C33···C213.5121 (17)H13···N1iii3.230 (14)
C33···C30ii3.5951 (17)H13···C1iii2.999 (13)
C34···C223.4277 (16)H13···C2iii3.007 (14)
C34···C243.5752 (17)H13···C3iii3.247 (15)
C35···C243.4469 (16)H13···C4iii3.457 (15)
C35···C253.5450 (16)H13···C5iii3.415 (15)
C36···N63.5121 (15)H13···C24iii3.588 (15)
C36···C263.5776 (17)H13···C25iii3.256 (15)
C37···C243.5205 (17)H13···H1iii3.390 (18)
C37···C253.3470 (17)H13···H2iii3.395 (19)
C38···N2vi3.4016 (17)H13···H11ii2.84 (2)
C38···N3vi3.4626 (18)H13···H203.56 (2)
C38···C253.4677 (17)H13···H24iii3.19 (2)
C38···C27xii3.5890 (18)H13···H25iii2.47 (3)
C39···C263.5331 (17)H13···H26viii3.228 (18)
N1···H23.284 (16)H14···N8x3.138 (14)
N1···H43.249 (15)H14···C2iii3.265 (16)
N1···H72.464 (16)H14···C3iii3.509 (16)
N2···H42.483 (16)H14···C31x3.587 (15)
N2···H73.259 (15)H14···C32x2.912 (15)
N3···H123.273 (16)H14···C33x2.995 (15)
N4···H153.254 (16)H14···C34x3.252 (15)
N4···H173.234 (15)H14···C35x3.438 (14)
N4···H202.458 (15)H14···C36x3.380 (14)
N5···H172.453 (15)H14···H1viii3.464 (19)
N5···H203.277 (14)H14···H2iii2.57 (3)
N6···H253.294 (16)H14···H3iii3.08 (2)
N7···H283.248 (17)H14···H16ii3.26 (2)
N7···H303.261 (15)H14···H273.55 (3)
N7···H332.457 (16)H14···H30ix3.23 (3)
N8···H302.508 (16)H14···H33x3.42 (3)
N8···H333.248 (15)H15···N8ix2.506 (16)
N9···H383.294 (16)H15···N9ix2.854 (16)
C1···H33.287 (15)H15···C30ix3.286 (16)
C2···H43.266 (15)H15···C32ix3.555 (16)
C3···H13.268 (15)H15···C33x3.402 (15)
C4···H23.325 (15)H15···C34x2.958 (14)
C5···H13.168 (15)H15···C35x3.479 (14)
C5···H33.282 (16)H15···C36ix3.092 (16)
C5···H72.670 (16)H15···H283.33 (3)
C6···H42.667 (16)H15···H30ix2.41 (3)
C6···H83.292 (15)H15···H34x2.85 (2)
C8···H112.687 (15)H16···N4iv3.060 (14)
C9···H73.279 (15)H16···N7iv3.257 (15)
C9···H123.285 (15)H16···N8ix3.566 (15)
C10···H83.304 (15)H16···N9ix3.331 (14)
C10···H113.309 (16)H16···C14iv3.454 (14)
C10···H133.153 (15)H16···C27iv3.320 (15)
C11···H82.694 (14)H16···C283.518 (14)
C11···H133.246 (15)H16···C293.522 (14)
C13···H113.287 (15)H16···C36ix3.560 (15)
C14···H163.307 (15)H16···H2viii2.95 (2)
C15···H173.248 (15)H16···H14iv3.26 (2)
C16···H143.291 (15)H16···H20iv3.106 (19)
C17···H153.246 (15)H16···H27iv2.70 (3)
C18···H143.165 (15)H16···H283.442 (19)
C18···H163.294 (16)H16···H293.46 (2)
C18···H202.674 (15)H17···C20iv2.901 (14)
C19···H172.645 (16)H17···C21iv3.194 (13)
C19···H213.290 (15)H17···C293.559 (14)
C21···H242.684 (15)H17···C303.441 (14)
C22···H203.301 (15)H17···C33iv3.427 (15)
C22···H253.343 (16)H17···H20iv2.433 (19)
C23···H213.306 (15)H17···H21iv2.972 (19)
C23···H243.331 (16)H17···H33iv2.62 (3)
C23···H263.161 (15)H20···C2iii3.432 (15)
C24···H212.692 (14)H20···C123.462 (13)
C24···H263.270 (15)H20···C133.364 (14)
C26···H243.321 (16)H20···C16ii3.260 (13)
C27···H293.299 (16)H20···C17ii2.883 (13)
C28···H303.252 (15)H20···H1iii3.57 (2)
C29···H273.264 (16)H20···H2iii2.73 (2)
C30···H283.224 (16)H20···H133.56 (2)
C31···H273.131 (16)H20···H16ii3.106 (19)
C31···H293.321 (16)H20···H17ii2.433 (19)
C31···H332.668 (16)H21···N33.450 (14)
C32···H302.692 (16)H21···N5ii2.776 (14)
C32···H343.298 (16)H21···N6ii3.005 (15)
C34···H372.722 (15)H21···C8ii3.491 (15)
C35···H333.263 (15)H21···C103.499 (13)
C35···H383.307 (15)H21···C23ii3.257 (15)
C36···H343.317 (15)H21···H8ii2.74 (2)
C36···H373.347 (16)H21···H11ii3.27 (2)
C36···H393.182 (15)H21···H17ii2.972 (19)
C37···H342.707 (14)H21···H343.54 (2)
C37···H393.286 (15)H24···N23.540 (15)
C39···H373.308 (15)H24···N6ii2.770 (14)
H1···H22.34 (3)H24···C63.496 (14)
H2···H32.47 (2)H24···C26ii3.146 (15)
H3···H42.36 (3)H24···H8ii3.21 (2)
H7···H82.37 (2)H24···H13vi3.19 (2)
H8···H112.52 (2)H24···H26ii2.83 (2)
H11···H122.40 (2)H24···H343.505 (19)
H12···H132.35 (3)H24···H373.43 (2)
H14···H152.40 (3)H25···N13.427 (14)
H15···H162.41 (2)H25···N3vi2.952 (16)
H16···H172.36 (2)H25···C11i2.897 (15)
H20···H212.40 (2)H25···C12i3.172 (14)
H21···H242.50 (2)H25···C13vi3.030 (16)
H24···H252.49 (2)H25···C373.338 (14)
H25···H262.36 (3)H25···C383.226 (15)
H27···H282.40 (3)H25···H11i2.67 (2)
H28···H292.35 (2)H25···H12i3.189 (19)
H29···H302.39 (3)H25···H13vi2.47 (3)
H33···H342.36 (3)H25···H373.493 (19)
H34···H372.56 (2)H25···H383.35 (2)
H37···H382.40 (2)H26···N3i3.286 (15)
H38···H392.40 (3)H26···N93.483 (14)
N1···H3iv2.929 (14)H26···C9i3.548 (15)
N1···H12i2.614 (16)H26···C10i3.559 (15)
N1···H13vi3.230 (14)H26···C11i3.202 (15)
N1···H253.427 (14)H26···C12i2.861 (14)
N1···H29vii3.500 (14)H26···C13i2.901 (14)
N2···H8ii2.767 (14)H26···C393.373 (14)
N2···H243.540 (15)H26···H73.53 (2)
N2···H37iii3.530 (15)H26···H12i3.17 (2)
N2···H38iii2.509 (16)H26···H13i3.228 (18)
N2···H39viii3.285 (14)H26···H24iv2.83 (2)
N3···H8ii2.993 (15)H26···H34iv3.59 (2)
N3···H11ii2.788 (14)H26···H37iv2.81 (3)
N3···H213.450 (14)H26···H393.51 (2)
N3···H25iii2.952 (16)H27···N43.490 (15)
N3···H26viii3.286 (15)H27···N9x3.086 (15)
N3···H37iii3.255 (14)H27···C143.339 (15)
N3···H38iii2.849 (16)H27···C35x3.368 (16)
N4···H1viii2.957 (14)H27···C36x3.284 (16)
N4···H2iii2.528 (16)H27···C37x3.217 (16)
N4···H16ii3.060 (14)H27···C38x3.000 (15)
N4···H273.490 (15)H27···C39x2.915 (14)
N5···H21iv2.776 (14)H27···H143.55 (3)
N5···H34iv3.453 (15)H27···H16ii2.70 (3)
N6···H83.452 (14)H27···H29ii3.15 (3)
N6···H21iv3.005 (15)H27···H38x3.46 (2)
N6···H24iv2.770 (14)H27···H39x3.351 (19)
N6···H34iv2.772 (16)H28···N9ix2.997 (17)
N6···H37iv3.562 (15)H28···C153.332 (16)
N7···H3xi3.593 (14)H28···C163.361 (15)
N7···H16ii3.257 (15)H28···C37x2.991 (15)
N7···H29ii2.977 (14)H28···C38x3.266 (15)
N8···H14xii3.138 (14)H28···C39ix3.114 (17)
N8···H15v2.506 (16)H28···H4xi3.52 (2)
N8···H16v3.566 (15)H28···H153.33 (3)
N8···H34iv2.878 (14)H28···H163.442 (19)
N9···H15v2.854 (16)H28···H37x2.91 (2)
N9···H16v3.331 (14)H28···H38x3.35 (2)
N9···H263.483 (14)H28···H39ix2.55 (3)
N9···H27xii3.086 (15)H29···N1xi3.500 (14)
N9···H28v2.997 (17)H29···N7iv2.977 (14)
N9···H34iv3.058 (15)H29···C5xi3.563 (14)
N9···H37iv2.930 (14)H29···C27iv3.382 (15)
C1···H3iv3.376 (15)H29···H3xiv3.02 (3)
C1···H11i3.426 (15)H29···H163.46 (2)
C1···H12i2.899 (16)H29···H27iv3.15 (3)
C1···H13vi2.999 (13)H29···H33iv3.123 (19)
C2···H12vi3.385 (14)H29···H39ix3.27 (2)
C2···H13vi3.007 (14)H30···C2xi3.585 (14)
C2···H14vi3.265 (16)H30···C14v3.422 (16)
C2···H20vi3.432 (15)H30···C15v2.974 (15)
C2···H30vii3.585 (14)H30···C33iv2.928 (14)
C3···H7ii3.152 (14)H30···C34iv3.268 (14)
C3···H12vi3.099 (14)H30···H14v3.23 (3)
C3···H13vi3.247 (15)H30···H15v2.41 (3)
C3···H14vi3.509 (16)H30···H33iv2.457 (19)
C4···H7ii2.809 (14)H30···H34iv3.099 (19)
C4···H13vi3.457 (15)H33···C17ii3.419 (16)
C4···H38iii3.321 (16)H33···C203.429 (14)
C5···H13vi3.415 (15)H33···C213.492 (14)
C5···H29vii3.563 (14)H33···C29ii3.284 (13)
C6···H243.496 (14)H33···C30ii2.927 (13)
C6···H38iii3.537 (16)H33···H14xii3.42 (3)
C6···H39viii3.186 (15)H33···H17ii2.62 (3)
C7···H4iv2.862 (14)H33···H29ii3.123 (19)
C7···H38viii3.475 (15)H33···H30ii2.457 (19)
C7···H39viii3.205 (15)H34···N5ii3.453 (15)
C8···H4iv3.169 (14)H34···N6ii2.772 (16)
C8···H21iv3.491 (15)H34···N8ii2.878 (14)
C8···H38viii2.979 (14)H34···N9ii3.058 (15)
C8···H39viii3.268 (15)H34···C23ii3.490 (16)
C9···H26viii3.548 (15)H34···C26ii3.570 (16)
C9···H38viii3.522 (13)H34···C36ii3.315 (15)
C9···H39viii3.341 (14)H34···H15xii2.85 (2)
C10···H8ii3.255 (15)H34···H213.54 (2)
C10···H213.499 (13)H34···H243.505 (19)
C10···H26viii3.559 (15)H34···H26ii3.59 (2)
C10···H37iii3.440 (15)H34···H30ii3.099 (19)
C10···H38iii3.067 (16)H37···N2vi3.530 (15)
C10···H39viii3.342 (14)H37···N3vi3.255 (14)
C11···H1viii3.414 (15)H37···N6ii3.562 (15)
C11···H25viii2.897 (15)H37···N9ii2.930 (14)
C11···H26viii3.202 (15)H37···C10vi3.440 (15)
C12···H1viii3.169 (16)H37···C243.589 (15)
C12···H203.462 (13)H37···C26ii3.453 (16)
C12···H25viii3.172 (14)H37···C39ii3.208 (15)
C12···H26viii2.861 (14)H37···H243.43 (2)
C13···H11ii3.148 (15)H37···H253.493 (19)
C13···H203.364 (14)H37···H26ii2.81 (3)
C13···H25iii3.030 (16)H37···H28xii2.91 (2)
C13···H26viii2.901 (14)H37···H39ii2.86 (2)
C14···H1viii2.961 (13)H38···N2vi2.509 (16)
C14···H2iii2.959 (16)H38···N3vi2.849 (16)
C14···H3iii3.519 (16)H38···C4vi3.321 (16)
C14···H16ii3.454 (14)H38···C6vi3.537 (16)
C14···H273.339 (15)H38···C7i3.475 (15)
C14···H30ix3.422 (16)H38···C8i2.979 (14)
C15···H1viii3.089 (14)H38···C9i3.522 (13)
C15···H2viii3.376 (14)H38···C10vi3.067 (16)
C15···H283.332 (16)H38···H4vi2.45 (3)
C15···H30ix2.974 (15)H38···H8i2.78 (2)
C16···H1viii3.155 (15)H38···H253.35 (2)
C16···H2viii2.992 (14)H38···H27xii3.46 (2)
C16···H20iv3.260 (13)H38···H28xii3.35 (2)
C16···H283.361 (15)H39···N2i3.285 (14)
C17···H1viii3.129 (15)H39···C6i3.186 (15)
C17···H2viii3.536 (15)H39···C7i3.205 (15)
C17···H20iv2.883 (13)H39···C8i3.268 (15)
C17···H33iv3.419 (16)H39···C9i3.341 (14)
C18···H1viii3.020 (15)H39···C10i3.342 (14)
C19···H113.569 (14)H39···C28v3.357 (16)
C20···H17ii2.901 (14)H39···H4vi3.50 (3)
C20···H333.429 (14)H39···H263.51 (2)
C21···H8ii3.493 (15)H39···H27xii3.351 (19)
C21···H17ii3.194 (13)H39···H28v2.55 (3)
C21···H333.492 (14)H39···H29v3.27 (2)
C23···H83.495 (13)H39···H37iv2.86 (2)
C23···H21iv3.257 (15)
C1—N1—C5117.64 (12)C34—C35—C36118.06 (11)
C6—N2—C10118.06 (11)C34—C35—C37124.02 (12)
C10—N3—C13116.77 (11)C36—C35—C37117.88 (11)
C14—N4—C18117.04 (11)N8—C36—N9115.40 (11)
C19—N5—C23118.14 (11)N8—C36—C35122.14 (11)
C23—N6—C26116.74 (12)N9—C36—C35122.47 (11)
C27—N7—C31117.27 (12)C35—C37—C38119.43 (13)
C32—N8—C36118.15 (11)C37—C38—C39118.43 (12)
C36—N9—C39116.88 (12)N9—C39—C38124.90 (12)
N1—C1—C2123.91 (12)N1—C1—H1116.9 (9)
C1—C2—C3118.10 (12)C2—C1—H1119.2 (9)
C2—C3—C4119.00 (13)C1—C2—H2118.0 (9)
C3—C4—C5118.84 (11)C3—C2—H2123.9 (9)
N1—C5—C4122.48 (11)C2—C3—H3122.5 (9)
N1—C5—C6116.90 (11)C4—C3—H3118.5 (9)
C4—C5—C6120.61 (10)C3—C4—H4121.8 (10)
N2—C6—C5117.04 (11)C5—C4—H4119.4 (10)
N2—C6—C7123.32 (11)C6—C7—H7119.3 (10)
C5—C6—C7119.64 (10)C8—C7—H7121.6 (10)
C6—C7—C8119.10 (11)C7—C8—H8121.5 (9)
C7—C8—C9119.52 (11)C9—C8—H8119.0 (9)
C8—C9—C10117.66 (11)C9—C11—H11118.3 (9)
C8—C9—C11124.24 (12)C12—C11—H11122.4 (9)
C10—C9—C11118.10 (11)C11—C12—H12121.8 (9)
N2—C10—N3115.33 (11)C13—C12—H12119.9 (9)
N2—C10—C9122.32 (11)N3—C13—H13116.4 (9)
N3—C10—C9122.35 (11)C12—C13—H13118.4 (9)
C9—C11—C12119.26 (12)N4—C14—H14114.5 (10)
C11—C12—C13118.29 (12)C15—C14—H14121.4 (9)
N3—C13—C12125.23 (11)C14—C15—H15121.1 (10)
N4—C14—C15124.10 (12)C16—C15—H15120.5 (10)
C14—C15—C16118.26 (12)C15—C16—H16123.0 (9)
C15—C16—C17118.86 (13)C17—C16—H16118.1 (9)
C16—C17—C18118.92 (11)C16—C17—H17122.0 (10)
N4—C18—C17122.80 (11)C18—C17—H17119.1 (10)
N4—C18—C19116.86 (11)C19—C20—H20119.0 (9)
C17—C18—C19120.31 (11)C21—C20—H20122.1 (9)
N5—C19—C18116.54 (11)C20—C21—H21121.7 (9)
N5—C19—C20123.59 (12)C22—C21—H21119.0 (9)
C18—C19—C20119.84 (11)C22—C24—H24117.6 (9)
C19—C20—C21118.80 (11)C25—C24—H24123.4 (9)
C20—C21—C22119.30 (12)C24—C25—H25124.4 (9)
C21—C22—C23118.07 (11)C26—C25—H25116.9 (9)
C21—C22—C24123.95 (12)N6—C26—H26115.5 (9)
C23—C22—C24117.97 (11)C25—C26—H26119.5 (9)
N5—C23—N6115.26 (11)N7—C27—H27114.0 (10)
N5—C23—C22122.06 (11)C28—C27—H27122.0 (10)
N6—C23—C22122.67 (11)C27—C28—H28122.6 (10)
C22—C24—C25119.01 (12)C29—C28—H28119.0 (10)
C24—C25—C26118.69 (12)C28—C29—H29120.3 (9)
N6—C26—C25124.92 (12)C30—C29—H29121.0 (9)
N7—C27—C28123.98 (13)C29—C30—H30120.1 (10)
C27—C28—C29118.41 (13)C31—C30—H30120.8 (10)
C28—C29—C30118.70 (13)C32—C33—H33119.3 (10)
C29—C30—C31119.07 (12)C34—C33—H33121.4 (10)
N7—C31—C30122.56 (12)C33—C34—H34121.4 (9)
N7—C31—C32116.43 (11)C35—C34—H34119.6 (9)
C30—C31—C32121.01 (11)C35—C37—H37119.7 (9)
N8—C32—C31116.94 (11)C38—C37—H37120.8 (9)
N8—C32—C33123.26 (12)C37—C38—H38121.9 (9)
C31—C32—C33119.80 (11)C39—C38—H38119.7 (9)
C32—C33—C34119.33 (11)N9—C39—H39115.5 (9)
C33—C34—C35119.02 (12)C38—C39—H39119.6 (9)
C1—N1—C5—C40.89 (16)C11—C9—C10—N2−179.70 (10)
C1—N1—C5—C6−179.97 (9)C11—C9—C10—N30.45 (16)
C5—N1—C1—C20.73 (17)C9—C11—C12—C130.09 (16)
C6—N2—C10—N3178.97 (9)C11—C12—C13—N30.13 (17)
C6—N2—C10—C9−0.89 (16)N4—C14—C15—C16−0.90 (18)
C10—N2—C6—C5179.62 (9)C14—C15—C16—C171.59 (17)
C10—N2—C6—C7−0.49 (16)C15—C16—C17—C18−0.98 (17)
C10—N3—C13—C12−0.06 (16)C16—C17—C18—N4−0.44 (17)
C13—N3—C10—N2179.90 (9)C16—C17—C18—C19177.64 (10)
C13—N3—C10—C9−0.24 (15)N4—C18—C19—N5−177.53 (9)
C14—N4—C18—C171.15 (16)N4—C18—C19—C204.20 (15)
C14—N4—C18—C19−176.99 (9)C17—C18—C19—N54.28 (15)
C18—N4—C14—C15−0.47 (17)C17—C18—C19—C20−173.98 (9)
C19—N5—C23—N6179.55 (9)N5—C19—C20—C21−2.03 (17)
C19—N5—C23—C220.40 (16)C18—C19—C20—C21176.11 (9)
C23—N5—C19—C18−176.97 (9)C19—C20—C21—C221.14 (16)
C23—N5—C19—C201.22 (16)C20—C21—C22—C230.34 (16)
C23—N6—C26—C25−0.39 (17)C20—C21—C22—C24−178.77 (10)
C26—N6—C23—N5−178.05 (9)C21—C22—C23—N5−1.17 (16)
C26—N6—C23—C221.10 (16)C21—C22—C23—N6179.73 (10)
C27—N7—C31—C30−0.64 (16)C21—C22—C24—C25179.46 (10)
C27—N7—C31—C32178.72 (9)C23—C22—C24—C250.34 (16)
C31—N7—C27—C28−0.21 (17)C24—C22—C23—N5177.99 (10)
C32—N8—C36—N9−178.06 (9)C24—C22—C23—N6−1.10 (16)
C32—N8—C36—C351.63 (16)C22—C24—C25—C260.32 (16)
C36—N8—C32—C31−179.91 (9)C24—C25—C26—N6−0.32 (18)
C36—N8—C32—C330.11 (16)N7—C27—C28—C290.81 (19)
C36—N9—C39—C381.07 (17)C27—C28—C29—C30−0.56 (18)
C39—N9—C36—N8178.70 (9)C28—C29—C30—C31−0.22 (17)
C39—N9—C36—C35−0.98 (16)C29—C30—C31—N70.86 (17)
N1—C1—C2—C3−1.29 (18)C29—C30—C31—C32−178.48 (10)
C1—C2—C3—C40.22 (17)N7—C31—C32—N8−177.05 (9)
C2—C3—C4—C51.26 (17)N7—C31—C32—C332.93 (15)
C3—C4—C5—N1−1.89 (17)C30—C31—C32—N82.33 (16)
C3—C4—C5—C6179.00 (10)C30—C31—C32—C33−177.69 (10)
N1—C5—C6—N2176.21 (9)N8—C32—C33—C34−1.46 (17)
N1—C5—C6—C7−3.69 (15)C31—C32—C33—C34178.56 (9)
C4—C5—C6—N2−4.63 (15)C32—C33—C34—C351.02 (16)
C4—C5—C6—C7175.47 (10)C33—C34—C35—C360.60 (16)
N2—C6—C7—C81.67 (17)C33—C34—C35—C37178.06 (10)
C5—C6—C7—C8−178.43 (9)C34—C35—C36—N8−2.00 (16)
C6—C7—C8—C9−1.43 (16)C34—C35—C36—N9177.67 (10)
C7—C8—C9—C100.15 (16)C34—C35—C37—C38−176.60 (10)
C7—C8—C9—C11−179.04 (10)C36—C35—C37—C380.86 (16)
C8—C9—C10—N21.06 (16)C37—C35—C36—N8−179.62 (10)
C8—C9—C10—N3−178.79 (9)C37—C35—C36—N90.05 (16)
C8—C9—C11—C12178.83 (10)C35—C37—C38—C39−0.81 (17)
C10—C9—C11—C12−0.36 (16)C37—C38—C39—N9−0.19 (18)
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) x+1, y, z; (v) −x+2, y−1/2, −z; (vi) −x+1, y−1/2, −z+1; (vii) x, y, z+1; (viii) −x+2, y+1/2, −z+1; (ix) −x+2, y+1/2, −z; (x) −x+1, y+1/2, −z; (xi) x, y, z−1; (xii) −x+1, y−1/2, −z; (xiii) x−1, y, z+1; (xiv) x+1, y, z−1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N4vi1.008 (15)2.529 (17)3.4161 (16)146.6 (14)
C7—H7···N10.962 (16)2.462 (17)2.8037 (16)100.6 (12)
C12—H12···N1viii0.967 (15)2.616 (17)3.4845 (16)149.6 (14)
C15—H15···N8ix0.949 (15)2.507 (17)3.3470 (16)147.6 (14)
C17—H17···N50.940 (16)2.453 (16)2.7856 (15)100.7 (12)
C20—H20···N40.985 (16)2.460 (17)2.8036 (15)100.0 (12)
C33—H33···N70.948 (16)2.456 (16)2.7944 (16)100.9 (13)
C38—H38···N2vi0.991 (16)2.511 (17)3.4016 (16)149.5 (14)
Symmetry codes: (vi) −x+1, y−1/2, −z+1; (viii) −x+2, y+1/2, −z+1; (ix) −x+2, y+1/2, −z.
 

Funding information

Funding for this research was provided by: Japan Society for the Promotion of Science (grant No. JP17K05799).

References

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ISSN: 2414-3146
Volume 2| Part 8| August 2017| x171221
https://doi.org/10.1107/S2414314617012214
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