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

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ISSN: 2414-3146

2,5-Bis[5-(3,5-dido­decyl­oxyphen­yl)-1,3,4-oxa­diazol-2-yl]-3,6-di­methyl­pyrazine

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aUniversity of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 10 January 2023; accepted 12 January 2023; online 17 January 2023)

The nearly planar mol­ecule of the title compound, C70H112N6O6, is centrosymmetric with two all-s-trans chains, the other two chains have an s-cis unit starting with the oxygen atoms. The chains are inter­digitated in the packing.

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

Structure description

Electron-deficient conjugated oligomers are inter­esting as electron-transporting mat­erials in organic electronics (Müllen & Wegner, 1998[Müllen, K. & Wegner, G. (1998). Electronic Materials: The Oligomer Approach. Weinheim: Wiley-VCH.]). The combination of rigid segments with flexible side chains may cause mesomorphism (Vorländer, 1923[Vorländer, D. (1923). Z. Phys. Chem. 105, 211-254.]). Alternating aryl­ene-1,3,4-oxa­diazo­lylene oligomers were first prepared by a Huisgen reaction (Sauer et al., 1960[Sauer, J., Huisgen, R. & Sturm, H. J. (1960). Tetrahedron, 11, 241-251.]). The title compound (Fig. 1[link]) was prepared via twofold acyl­ation of the di­alk­oxy­phenyl-tetra­zole with a pyrazinedi­carb­oxy­lic acid dichloride and thermal ring transformation. The centrosymmetric mol­ecule is located parallel to the (110) plane, the five aromatic rings are almost coplanar with torsion angles of −0.4 (4)° (N6—C5—C3—C2) and −2.0 (4)° (C11—C10—C8—N7). Two dodec­yloxy chains per mol­ecule are completely all-s-trans organized whereas the other pair shows an s-cis-conformation of the O16—C17—C18—C19 unit. Torsion angles at the all-trans chains are 179.3 (2) for C13—C14—O29—C30, 177.9 (5)° for C14—O29—C30—C31 and 178.1 (2)° for O29—C30—C31—C32 but for the other chain, 15.8 (3)° (C17—O16—C12—C13), 176.2 (2)° (C12—O16—C17—C18), and −55.3 (3)° for the O16—C17—C18—C19 unit. The packing is controlled by inter­action of the aliphatic chains (Fig. 2[link]), which are arranged in two planes subtending a dihedral angle of 7.63 (19)°. Deviation from planarity within the chains is only −0.481 (2) Å at C30 but −1.84 (2) Å at C18. Alternating all-trans chains and those with the s-cis unit are inter­digitated. The aromatic units of mol­ecules in different planes are displaced, C13 (phen­yl) is located above the pyrazine centroid.

[Figure 1]
Figure 1
View of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Atoms with suffix _a were generated by the symmetry operator −x + 1, −y + 1, −z + 1. H atoms were omitted for clarity.
[Figure 2]
Figure 2
Partial packing diagram. View along the b-axis.

Synthesis and crystallization

The title compound was prepared via a Huisgen reaction (Sauer et al., 1960[Sauer, J., Huisgen, R. & Sturm, H. J. (1960). Tetrahedron, 11, 241-251.]) of a central di­carb­oxy­lic acid chloride and tetra­zoles. 3,6-Di­methyl­pyrazine-2,5-di­carb­oxy­lic acid (0.1 g, 0.51 mmol) (Brunner et al., 1998[Brunner, H., Störiko, R. & Rominger, F. (1998). Eur. J. Inorg. Chem. pp. 771-781.]) was dissolved in thionyl chloride (5 ml) and after refluxing for 2 h, the reagent was evaporated, residues were removed by codistillation with toluene (10 ml). 5-(3,5-Dido­decyl­oxyphen­yl)tetra­zole (0.52 g, 1.02 mmol) (Rieth et al., 2015[Rieth, T., Glang, S., Borchmann, D. & Detert, H. (2015). Mol. Cryst. Liq. Cryst. 610, 89-99.]) and pyridine (3 ml) were added and the mixture refluxed for 24 h. Thereafter, water and diluted hydro­chloric acid were added and the product isolated via extraction with chloro­form, drying with MgSO4 and chromatography on silica using ethyl acetate as an eluent. Yield: 20 mg, 3% of a colorless material with m.p. = 399 K. IR (ATR): 2916, 2848, 1602, 1544, 1468, 1442, 1429, 1174; 1H NMR (CDCl3, 400 MHz; δ = 7.34 (d, J = 2.2 Hz, 4 H), 6.66 (t, J = 2.3 Hz, 2 H), 4.04 (t, J = 6.5 Hz, 8 H), 3.17 (s, 6 H), 1.82 (qui, J = 6.9 Hz, 8 H), 1.55-1.42 (qui,≃ 8 H), 1.42-1.20 (qui, ≃ 64 H), 0.93-0.83 (t, ≃ 12 H). Whereas the absorption spectrum of the title compound in cyclo­hexane peaks at 348 nm, three maxima appear in methanol (346, 361, and 379 nm), indicating aggregation. The emission of a solution in cyclo­hexane is centered at 403 nm, and in toluene at 409 nm. Crystallization was via slow evaporation of a solution in chloro­form/2-propanol.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C70H112N6O6
Mr 1133.65
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 120
a, b, c (Å) 8.1119 (3), 9.5566 (3), 22.2332 (8)
α, β, γ (°) 90.553 (3), 91.592 (3), 106.047 (3)
V3) 1655.50 (10)
Z 1
Radiation type Cu Kα
μ (mm−1) 0.56
Crystal size (mm) 0.14 × 0.08 × 0.03
 
Data collection
Diffractometer Stoe Stadivari
No. of measured, independent and observed [I > 2σ(I)] reflections 46250, 5582, 3360
Rint 0.090
(sin θ/λ)max−1) 0.601
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.143, 0.94
No. of reflections 5582
No. of parameters 373
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.57, −0.21
Computer programs: X-AREA WinXpose, Recipe andIntegrate (Stoe & Cie, 2019[Stoe & Cie (2019). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]).

Structural data


Computing details top

Data collection: X-AREA WinXpose (Stoe & Cie, 2019); cell refinement: X-AREA Recipe (Stoe & Cie, 2019); data reduction: X-AREA Integrate (Stoe & Cie, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020).

2,5-Bis[5-(3,5-didodecyloxyphenyl)-1,3,4-oxadiazol-2-yl]-3,6-dimethylpyrazine top
Crystal data top
C70H112N6O6F(000) = 622
Mr = 1133.65Dx = 1.137 Mg m3
Triclinic, P1Melting point: 399 K
a = 8.1119 (3) ÅCu Kα radiation, λ = 1.54178 Å
b = 9.5566 (3) ÅCell parameters from 12421 reflections
c = 22.2332 (8) Åθ = 2.0–71.5°
α = 90.553 (3)°µ = 0.56 mm1
β = 91.592 (3)°T = 120 K
γ = 106.047 (3)°Block, colorless
V = 1655.50 (10) Å30.14 × 0.08 × 0.03 mm
Z = 1
Data collection top
Stoe Stadivari
diffractometer
3360 reflections with I > 2σ(I)
Radiation source: microfocus tubeRint = 0.090
Detector resolution: 13.33 pixels mm-1θmax = 68.0°, θmin = 2.0°
rotation method, ω scansh = 99
46250 measured reflectionsk = 1111
5582 independent reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0817P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
5582 reflectionsΔρmax = 0.57 e Å3
373 parametersΔρmin = 0.21 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms were placed at calculated positions and were refined in the riding-model approximation with Caromatic–H = 0.95 Å, Cmethylene–H = 0.99 Å, and Cmethyl–H = 0.98 Å and with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The methyl groups were allowed to rotate but not to tip.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4330 (2)0.5972 (2)0.53110 (8)0.0250 (4)
C20.4840 (3)0.4951 (2)0.56115 (10)0.0248 (5)
C30.5511 (3)0.3976 (2)0.52863 (10)0.0240 (5)
C40.4685 (3)0.4954 (2)0.62820 (10)0.0289 (5)
H4A0.4178090.5728920.6403360.043*
H4B0.5825370.5124660.6475190.043*
H4C0.3949150.4011140.6405630.043*
C50.6013 (3)0.2776 (2)0.55730 (10)0.0244 (5)
N60.5959 (3)0.2403 (2)0.61295 (8)0.0300 (5)
N70.6494 (3)0.1122 (2)0.61502 (8)0.0304 (5)
C80.6824 (3)0.0848 (2)0.56041 (9)0.0245 (5)
O90.6569 (2)0.18470 (16)0.52090 (6)0.0244 (4)
C100.7459 (3)0.0346 (2)0.53796 (10)0.0236 (5)
C110.7808 (3)0.1302 (2)0.57946 (10)0.0247 (5)
H110.7579500.1208290.6207580.030*
C120.8500 (3)0.2404 (2)0.56000 (9)0.0241 (5)
C130.8827 (3)0.2539 (2)0.49996 (9)0.0240 (5)
H130.9313690.3282640.4869250.029*
C140.8443 (3)0.1580 (2)0.45843 (9)0.0228 (5)
C150.7753 (3)0.0471 (2)0.47684 (10)0.0240 (5)
H150.7490620.0182290.4486300.029*
O160.8803 (2)0.32816 (17)0.60445 (6)0.0287 (4)
C170.9903 (3)0.4195 (2)0.59294 (10)0.0277 (5)
H17A1.1037350.3601900.5800510.033*
H17B0.9389760.4920030.5607280.033*
C181.0092 (3)0.4953 (2)0.65108 (10)0.0291 (5)
H18A1.0899880.5549650.6452310.035*
H18B0.8965480.5621350.6607170.035*
C191.0742 (3)0.3907 (3)0.70426 (10)0.0304 (5)
H19A0.9869940.3393120.7133210.036*
H19B1.1802100.3168450.6930670.036*
C201.1118 (3)0.4684 (3)0.76074 (10)0.0307 (6)
H20A1.2141950.5030730.7541460.037*
H20B1.0136750.5548340.7669940.037*
C211.1432 (3)0.3723 (3)0.81777 (10)0.0333 (6)
H21A1.2400360.2849090.8113950.040*
H21B1.0399510.3391020.8249450.040*
C221.1837 (3)0.4506 (3)0.87345 (10)0.0323 (6)
H22A1.2891250.4808080.8667590.039*
H22B1.0885990.5397660.8789630.039*
C231.2092 (3)0.3569 (3)0.93082 (10)0.0334 (6)
H23A1.1040160.3261910.9373270.040*
H23B1.3047010.2679900.9253390.040*
C241.2490 (3)0.4354 (3)0.98696 (10)0.0319 (6)
H24A1.1538820.5246750.9923030.038*
H24B1.3546630.4654670.9805970.038*
C251.2732 (3)0.3418 (3)1.04433 (10)0.0335 (6)
H25A1.3671410.2518671.0387040.040*
H25B1.1668970.3127841.0509050.040*
C261.3151 (3)0.4182 (3)1.10030 (10)0.0338 (6)
H26A1.2213150.5081431.1060180.041*
H26B1.4216810.4468441.0939080.041*
C271.3385 (4)0.3235 (3)1.15719 (10)0.0374 (6)
H27A1.2318190.2949161.1635600.045*
H27B1.4321070.2334841.1514100.045*
C281.3808 (4)0.3996 (3)1.21353 (11)0.0446 (7)
H28A1.2876620.4880161.2200280.067*
H28B1.3935400.3338641.2485070.067*
H28C1.4881340.4256911.2081070.067*
O290.8808 (2)0.18117 (16)0.40032 (6)0.0284 (4)
C300.8427 (3)0.0874 (2)0.35478 (9)0.0287 (5)
H30A0.9103890.0146550.3627770.034*
H30B0.7192330.0920150.3543220.034*
C310.8895 (3)0.1410 (3)0.29551 (10)0.0326 (6)
H31A0.8252900.2447740.2894500.039*
H31B1.0134750.1345410.2967490.039*
C320.8501 (4)0.0542 (3)0.24239 (10)0.0329 (6)
H32A0.7341670.0408720.2464590.039*
H32B0.9337840.0433780.2431390.039*
C330.8580 (3)0.1298 (3)0.18232 (10)0.0320 (6)
H33A0.7762540.2282370.1823220.038*
H33B0.9746380.1417890.1783840.038*
C340.8164 (3)0.0486 (3)0.12775 (10)0.0319 (6)
H34A0.9080770.0436860.1239190.038*
H34B0.7073750.0238950.1341150.038*
C350.8002 (3)0.1378 (3)0.06942 (9)0.0317 (6)
H35A0.7096020.2305840.0736110.038*
H35B0.9097140.1616480.0630270.038*
C360.7566 (3)0.0591 (3)0.01426 (9)0.0321 (6)
H36A0.6488800.0326420.0210520.039*
H36B0.8490300.0321040.0091950.039*
C370.7354 (3)0.1514 (3)0.04338 (10)0.0332 (6)
H37A0.8433510.1776540.0501640.040*
H37B0.6434030.2428290.0381810.040*
C380.6913 (3)0.0740 (3)0.09865 (10)0.0324 (6)
H38A0.7842130.0166830.1042000.039*
H38B0.5843580.0464340.0916180.039*
C390.6675 (4)0.1669 (3)0.15610 (10)0.0349 (6)
H39A0.5769000.2588290.1501620.042*
H39B0.7756030.1921970.1637570.042*
C400.6186 (4)0.0908 (3)0.21120 (10)0.0377 (6)
H40A0.5137670.0609920.2028860.045*
H40B0.7120460.0017190.2186080.045*
C410.5864 (4)0.1877 (3)0.26715 (11)0.0446 (7)
H41A0.6916870.2132810.2768280.054*
H41B0.5518840.1356940.3008970.054*
H41C0.4948470.2766080.2599000.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0246 (11)0.0213 (10)0.0288 (11)0.0063 (10)0.0022 (8)0.0021 (7)
C20.0223 (13)0.0218 (12)0.0303 (12)0.0063 (12)0.0024 (9)0.0013 (9)
C30.0206 (12)0.0198 (12)0.0301 (12)0.0037 (11)0.0020 (9)0.0028 (9)
C40.0338 (14)0.0253 (12)0.0302 (13)0.0125 (12)0.0005 (10)0.0015 (9)
C50.0226 (12)0.0220 (12)0.0294 (12)0.0078 (11)0.0016 (9)0.0044 (9)
N60.0388 (13)0.0280 (11)0.0280 (11)0.0177 (11)0.0011 (9)0.0018 (8)
N70.0387 (13)0.0265 (11)0.0310 (11)0.0174 (11)0.0000 (9)0.0016 (8)
C80.0282 (13)0.0211 (12)0.0253 (12)0.0088 (12)0.0022 (9)0.0027 (8)
O90.0286 (9)0.0228 (8)0.0245 (8)0.0118 (8)0.0002 (6)0.0004 (6)
C100.0209 (12)0.0223 (12)0.0283 (12)0.0076 (11)0.0012 (9)0.0022 (9)
C110.0253 (13)0.0248 (12)0.0237 (11)0.0066 (12)0.0006 (9)0.0025 (8)
C120.0232 (13)0.0227 (12)0.0262 (12)0.0060 (12)0.0029 (9)0.0017 (9)
C130.0255 (13)0.0190 (11)0.0284 (12)0.0080 (11)0.0009 (9)0.0025 (8)
C140.0234 (12)0.0206 (12)0.0227 (11)0.0034 (11)0.0020 (8)0.0007 (8)
C150.0251 (13)0.0201 (11)0.0267 (11)0.0067 (11)0.0032 (9)0.0016 (8)
O160.0358 (10)0.0304 (9)0.0262 (8)0.0192 (9)0.0016 (7)0.0043 (6)
C170.0313 (14)0.0284 (13)0.0277 (12)0.0157 (12)0.0000 (9)0.0006 (9)
C180.0315 (14)0.0265 (12)0.0325 (13)0.0141 (12)0.0036 (10)0.0026 (9)
C190.0366 (15)0.0282 (13)0.0290 (12)0.0138 (13)0.0020 (10)0.0016 (9)
C200.0360 (15)0.0279 (13)0.0311 (13)0.0137 (13)0.0025 (10)0.0020 (9)
C210.0402 (16)0.0334 (14)0.0299 (13)0.0164 (14)0.0028 (10)0.0006 (10)
C220.0392 (15)0.0302 (13)0.0291 (13)0.0127 (13)0.0018 (10)0.0006 (9)
C230.0391 (16)0.0309 (14)0.0318 (13)0.0127 (14)0.0018 (11)0.0012 (10)
C240.0382 (15)0.0303 (14)0.0279 (13)0.0113 (13)0.0023 (10)0.0005 (10)
C250.0386 (16)0.0320 (14)0.0303 (13)0.0110 (14)0.0032 (10)0.0006 (10)
C260.0367 (15)0.0336 (14)0.0323 (13)0.0118 (13)0.0020 (11)0.0024 (10)
C270.0414 (16)0.0399 (15)0.0299 (13)0.0101 (15)0.0022 (11)0.0006 (10)
C280.0494 (18)0.0547 (18)0.0323 (14)0.0194 (16)0.0047 (12)0.0015 (12)
O290.0394 (10)0.0268 (9)0.0226 (8)0.0150 (9)0.0000 (7)0.0007 (6)
C300.0353 (14)0.0278 (13)0.0252 (12)0.0127 (13)0.0026 (10)0.0026 (9)
C310.0432 (16)0.0324 (14)0.0250 (12)0.0151 (14)0.0007 (10)0.0007 (9)
C320.0447 (16)0.0303 (13)0.0267 (12)0.0156 (13)0.0006 (10)0.0014 (9)
C330.0407 (16)0.0318 (13)0.0250 (12)0.0130 (13)0.0006 (10)0.0016 (9)
C340.0379 (15)0.0336 (14)0.0261 (12)0.0132 (13)0.0005 (10)0.0013 (9)
C350.0371 (15)0.0328 (14)0.0261 (13)0.0112 (13)0.0008 (10)0.0001 (10)
C360.0382 (15)0.0362 (14)0.0241 (12)0.0142 (14)0.0004 (10)0.0004 (10)
C370.0393 (15)0.0349 (14)0.0268 (12)0.0129 (14)0.0026 (10)0.0015 (10)
C380.0384 (15)0.0344 (14)0.0250 (12)0.0115 (13)0.0024 (10)0.0008 (9)
C390.0401 (16)0.0358 (14)0.0294 (13)0.0117 (14)0.0008 (11)0.0013 (10)
C400.0452 (17)0.0406 (15)0.0269 (13)0.0115 (15)0.0023 (11)0.0022 (10)
C410.0508 (19)0.0566 (18)0.0275 (14)0.0169 (17)0.0020 (12)0.0019 (12)
Geometric parameters (Å, º) top
N1—C21.338 (3)C25—C261.526 (3)
N1—C3i1.338 (3)C25—H25A0.9900
C2—C31.406 (3)C25—H25B0.9900
C2—C41.499 (3)C26—C271.524 (3)
C3—C51.465 (3)C26—H26A0.9900
C4—H4A0.9800C26—H26B0.9900
C4—H4B0.9800C27—C281.532 (3)
C4—H4C0.9800C27—H27A0.9900
C5—N61.290 (3)C27—H27B0.9900
C5—O91.369 (2)C28—H28A0.9800
N6—N71.408 (2)C28—H28B0.9800
N7—C81.290 (3)C28—H28C0.9800
C8—O91.357 (2)O29—C301.441 (2)
C8—C101.465 (3)C30—C311.505 (3)
C10—C111.382 (3)C30—H30A0.9900
C10—C151.396 (3)C30—H30B0.9900
C11—C121.394 (3)C31—C321.526 (3)
C11—H110.9500C31—H31A0.9900
C12—O161.362 (3)C31—H31B0.9900
C12—C131.380 (3)C32—C331.523 (3)
C13—C141.395 (3)C32—H32A0.9900
C13—H130.9500C32—H32B0.9900
C14—O291.363 (3)C33—C341.526 (3)
C14—C151.391 (3)C33—H33A0.9900
C15—H150.9500C33—H33B0.9900
O16—C171.437 (2)C34—C351.527 (3)
C17—C181.513 (3)C34—H34A0.9900
C17—H17A0.9900C34—H34B0.9900
C17—H17B0.9900C35—C361.528 (3)
C18—C191.525 (3)C35—H35A0.9900
C18—H18A0.9900C35—H35B0.9900
C18—H18B0.9900C36—C371.527 (3)
C19—C201.530 (3)C36—H36A0.9900
C19—H19A0.9900C36—H36B0.9900
C19—H19B0.9900C37—C381.525 (3)
C20—C211.532 (3)C37—H37A0.9900
C20—H20A0.9900C37—H37B0.9900
C20—H20B0.9900C38—C391.525 (3)
C21—C221.527 (3)C38—H38A0.9900
C21—H21A0.9900C38—H38B0.9900
C21—H21B0.9900C39—C401.529 (3)
C22—C231.527 (3)C39—H39A0.9900
C22—H22A0.9900C39—H39B0.9900
C22—H22B0.9900C40—C411.516 (3)
C23—C241.534 (3)C40—H40A0.9900
C23—H23A0.9900C40—H40B0.9900
C23—H23B0.9900C41—H41A0.9800
C24—C251.527 (3)C41—H41B0.9800
C24—H24A0.9900C41—H41C0.9800
C24—H24B0.9900
C2—N1—C3i118.49 (19)C24—C25—H25B108.8
N1—C2—C3118.7 (2)H25A—C25—H25B107.7
N1—C2—C4116.83 (18)C27—C26—C25113.1 (2)
C3—C2—C4124.49 (19)C27—C26—H26A109.0
N1i—C3—C2122.8 (2)C25—C26—H26A109.0
N1i—C3—C5114.69 (19)C27—C26—H26B109.0
C2—C3—C5122.4 (2)C25—C26—H26B109.0
C2—C4—H4A109.5H26A—C26—H26B107.8
C2—C4—H4B109.5C26—C27—C28113.3 (2)
H4A—C4—H4B109.5C26—C27—H27A108.9
C2—C4—H4C109.5C28—C27—H27A108.9
H4A—C4—H4C109.5C26—C27—H27B108.9
H4B—C4—H4C109.5C28—C27—H27B108.9
N6—C5—O9112.67 (18)H27A—C27—H27B107.7
N6—C5—C3129.76 (19)C27—C28—H28A109.5
O9—C5—C3117.52 (18)C27—C28—H28B109.5
C5—N6—N7106.03 (17)H28A—C28—H28B109.5
C8—N7—N6106.06 (17)C27—C28—H28C109.5
N7—C8—O9113.02 (18)H28A—C28—H28C109.5
N7—C8—C10128.27 (19)H28B—C28—H28C109.5
O9—C8—C10118.69 (18)C14—O29—C30118.34 (16)
C8—O9—C5102.21 (16)O29—C30—C31106.77 (17)
C11—C10—C15121.71 (19)O29—C30—H30A110.4
C11—C10—C8117.78 (19)C31—C30—H30A110.4
C15—C10—C8120.48 (19)O29—C30—H30B110.4
C10—C11—C12119.2 (2)C31—C30—H30B110.4
C10—C11—H11120.4H30A—C30—H30B108.6
C12—C11—H11120.4C30—C31—C32112.61 (19)
O16—C12—C13125.20 (19)C30—C31—H31A109.1
O16—C12—C11114.55 (19)C32—C31—H31A109.1
C13—C12—C11120.25 (19)C30—C31—H31B109.1
C12—C13—C14119.89 (19)C32—C31—H31B109.1
C12—C13—H13120.1H31A—C31—H31B107.8
C14—C13—H13120.1C33—C32—C31112.02 (19)
O29—C14—C15123.95 (19)C33—C32—H32A109.2
O29—C14—C13115.19 (18)C31—C32—H32A109.2
C15—C14—C13120.8 (2)C33—C32—H32B109.2
C14—C15—C10118.08 (19)C31—C32—H32B109.2
C14—C15—H15121.0H32A—C32—H32B107.9
C10—C15—H15121.0C32—C33—C34114.08 (19)
C12—O16—C17118.96 (17)C32—C33—H33A108.7
O16—C17—C18106.94 (17)C34—C33—H33A108.7
O16—C17—H17A110.3C32—C33—H33B108.7
C18—C17—H17A110.3C34—C33—H33B108.7
O16—C17—H17B110.3H33A—C33—H33B107.6
C18—C17—H17B110.3C33—C34—C35112.41 (19)
H17A—C17—H17B108.6C33—C34—H34A109.1
C17—C18—C19113.50 (19)C35—C34—H34A109.1
C17—C18—H18A108.9C33—C34—H34B109.1
C19—C18—H18A108.9C35—C34—H34B109.1
C17—C18—H18B108.9H34A—C34—H34B107.9
C19—C18—H18B108.9C34—C35—C36113.29 (19)
H18A—C18—H18B107.7C34—C35—H35A108.9
C18—C19—C20112.56 (19)C36—C35—H35A108.9
C18—C19—H19A109.1C34—C35—H35B108.9
C20—C19—H19A109.1C36—C35—H35B108.9
C18—C19—H19B109.1H35A—C35—H35B107.7
C20—C19—H19B109.1C37—C36—C35112.69 (19)
H19A—C19—H19B107.8C37—C36—H36A109.1
C19—C20—C21113.68 (19)C35—C36—H36A109.1
C19—C20—H20A108.8C37—C36—H36B109.1
C21—C20—H20A108.8C35—C36—H36B109.1
C19—C20—H20B108.8H36A—C36—H36B107.8
C21—C20—H20B108.8C38—C37—C36113.07 (19)
H20A—C20—H20B107.7C38—C37—H37A109.0
C22—C21—C20112.97 (19)C36—C37—H37A109.0
C22—C21—H21A109.0C38—C37—H37B109.0
C20—C21—H21A109.0C36—C37—H37B109.0
C22—C21—H21B109.0H37A—C37—H37B107.8
C20—C21—H21B109.0C37—C38—C39113.1 (2)
H21A—C21—H21B107.8C37—C38—H38A109.0
C21—C22—C23113.19 (19)C39—C38—H38A109.0
C21—C22—H22A108.9C37—C38—H38B109.0
C23—C22—H22A108.9C39—C38—H38B109.0
C21—C22—H22B108.9H38A—C38—H38B107.8
C23—C22—H22B108.9C38—C39—C40113.1 (2)
H22A—C22—H22B107.8C38—C39—H39A109.0
C22—C23—C24113.40 (19)C40—C39—H39A109.0
C22—C23—H23A108.9C38—C39—H39B109.0
C24—C23—H23A108.9C40—C39—H39B109.0
C22—C23—H23B108.9H39A—C39—H39B107.8
C24—C23—H23B108.9C41—C40—C39112.3 (2)
H23A—C23—H23B107.7C41—C40—H40A109.1
C25—C24—C23113.27 (19)C39—C40—H40A109.1
C25—C24—H24A108.9C41—C40—H40B109.1
C23—C24—H24A108.9C39—C40—H40B109.1
C25—C24—H24B108.9H40A—C40—H40B107.9
C23—C24—H24B108.9C40—C41—H41A109.5
H24A—C24—H24B107.7C40—C41—H41B109.5
C26—C25—C24113.68 (19)H41A—C41—H41B109.5
C26—C25—H25A108.8C40—C41—H41C109.5
C24—C25—H25A108.8H41A—C41—H41C109.5
C26—C25—H25B108.8H41B—C41—H41C109.5
C3i—N1—C2—C30.3 (4)O29—C14—C15—C10179.3 (2)
C3i—N1—C2—C4178.4 (2)C13—C14—C15—C100.0 (4)
N1—C2—C3—N1i0.4 (4)C11—C10—C15—C141.0 (3)
C4—C2—C3—N1i178.3 (2)C8—C10—C15—C14176.6 (2)
N1—C2—C3—C5176.6 (2)C13—C12—O16—C1715.8 (3)
C4—C2—C3—C54.8 (4)C11—C12—O16—C17164.1 (2)
N1i—C3—C5—N6177.5 (2)C12—O16—C17—C18176.2 (2)
C2—C3—C5—N60.4 (4)O16—C17—C18—C1955.3 (3)
N1i—C3—C5—O90.4 (3)C17—C18—C19—C20173.5 (2)
C2—C3—C5—O9176.7 (2)C18—C19—C20—C21168.7 (2)
O9—C5—N6—N70.7 (3)C19—C20—C21—C22179.0 (2)
C3—C5—N6—N7176.5 (2)C20—C21—C22—C23178.1 (2)
C5—N6—N7—C80.2 (3)C21—C22—C23—C24179.7 (2)
N6—N7—C8—O90.4 (3)C22—C23—C24—C25179.6 (2)
N6—N7—C8—C10178.7 (2)C23—C24—C25—C26179.2 (2)
N7—C8—O9—C50.8 (3)C24—C25—C26—C27179.9 (2)
C10—C8—O9—C5179.2 (2)C25—C26—C27—C28179.9 (2)
N6—C5—O9—C80.9 (3)C15—C14—O29—C301.4 (3)
C3—C5—O9—C8176.6 (2)C13—C14—O29—C30179.3 (2)
N7—C8—C10—C112.0 (4)C14—O29—C30—C31177.9 (2)
O9—C8—C10—C11176.2 (2)O29—C30—C31—C32178.1 (2)
N7—C8—C10—C15179.7 (2)C30—C31—C32—C33166.6 (2)
O9—C8—C10—C151.6 (4)C31—C32—C33—C34179.0 (2)
C15—C10—C11—C121.1 (4)C32—C33—C34—C35171.7 (2)
C8—C10—C11—C12176.6 (2)C33—C34—C35—C36179.4 (2)
C10—C11—C12—O16179.8 (2)C34—C35—C36—C37178.2 (2)
C10—C11—C12—C130.1 (4)C35—C36—C37—C38179.8 (2)
O16—C12—C13—C14179.2 (2)C36—C37—C38—C39179.2 (2)
C11—C12—C13—C140.9 (4)C37—C38—C39—C40178.4 (2)
C12—C13—C14—O29179.7 (2)C38—C39—C40—C41177.0 (2)
C12—C13—C14—C150.9 (4)
Symmetry code: (i) x+1, y+1, z+1.
 

Funding information

Funding for this research was provided by: Deutsche Forschungsgemeinschaft (DE 515/12-1).

References

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