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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o434.
Published online 2008 January 11. doi:  10.1107/S1600536807067086
PMCID: PMC2960209

1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl­methyl]imidazolium hexa­fluoro­phos­phate

Abstract

In the title compound, C20H19N2 +·PF6 , the two benzocyclo­butene units are essentially planar and they form dihedral angles of 38.0 (2) and 72.7 (2)°, with the central imidazolium ring. In the crystal structure, weak C—H(...)π and π-–π stacking inter­actions [centroid–centroid distance = 3.742 (2) Å] contribute to the stability of the crystal structure. The PF6 ion is disordered over two positions with site occupancies of 0.869 (9) and 0.131 (9).

Related literature

For related literature, see: Farona (1996 [triangle]); Kirchhoff & Bruza (1993 [triangle]); Michellys et al. (2001 [triangle]); Nemeto & Fukumoto (1998 [triangle]); Zhang et al. (2006 [triangle]).

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Object name is e-64-0o434-scheme1.jpg

Experimental

Crystal data

  • C20H19N2 +·F6P
  • M r = 432.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o434-efi1.jpg
  • a = 9.311 (3) Å
  • b = 10.138 (3) Å
  • c = 10.562 (3) Å
  • α = 86.82 (2)°
  • β = 86.44 (2)°
  • γ = 73.61 (2)°
  • V = 953.9 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 296 (2) K
  • 0.28 × 0.25 × 0.18 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 3558 measured reflections
  • 3522 independent reflections
  • 2238 reflections with I > 2σ(I)
  • R int = 0.006
  • 3 standard reflections every 300 reflections intensity decay: 4.6%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 0.223
  • S = 1.15
  • 3522 reflections
  • 299 parameters
  • 81 restraints
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 [triangle]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067086/ci2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067086/ci2536Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (grant No. 20574046) for financial support.

supplementary crystallographic information

Comment

Benzocyclobutenes (BCBs) are important building blocks for new polymers and advanced materials (Nemeto & Fukumoto, 1998; Michellys et al., 2001). Most of the reported benzocyclobutene monomers in the literature are bis-BCB-functionalized compounds owing to their highly crosslinked structure and their excellent properties such as the insolubility, low solvent pickup and good thermal stability (Farona, 1996; Zhang et al., 2006; Kirchhoff & Bruza, 1993). We report here the crystal structure of the title compound, a novel bisbenzocyclobutene-terminated imidazolium which was obtained by an anion metathesis between 1-(4-benzocyclobutenyl)-3-(4-benzocyclobutenylmethyl) imidazolium choloride and hexafluorophosphate ammonium.

The two benzocyclobutene units are essentially planar. The plane of the C1—C8 and C13—C20 benzocyclobutene units form dihedral angles of 38.0 (2) and 72.7 (2)°, respectively, with the central imidazolium ring.

A combination of intermolecular π-π and C—H···π interactions provide packing forces in the crystal structure of the title compound. A π-π interaction between C13—C15/C18—C20 benzene ring and its symmetry- related counterpart at (-x, 1 - y, -z), with their centroids separated by 3.742 (2) Å, plays an important part in the connection of two adjacent molecules. In addition, a weak C—H···π interaction between C2—H2B group and C3—C8 benzene ring at (1 - x, -1 - y, 1 - z) contributes to the crystal packing (Table 1).

Experimental

4-(N-imidazolyl)benzocyclobutene (5 mmol, 850 mg) and 4-cholomethylbenzocyclobutene (5 mmol, 760 mg) were placed in a two-necked round-bottomed flask under a nitrogen atmosphere, and the mixture was heated at 353 K for 3 h. After the reaction was completed, the resulting 1-(4-benzocyclobutenyl)-3-(4-benzocyclobutenylmethyl)imidazolium chloride, [BBMI][Cl-], was obtained in 85% yield (1.381 g). [BBMI][Cl-] was dissolved in deioned water, and NH4PF6 was added to replace Cl- ions by PF6- ions, to obtain the title compound as a white solid (yield 1.331 g). Colourless crystals of the title compound were obtained by recrystallization of the solid from acetone and ethanol (1:1 v/v). 1 H NMR (400 MHz, CDCl3,): δ 8.84 (s, 1H), 7.41 (t, 1H), 7.31 (m, 2H), 7.27 (2 d, 1H), 7.22 (d, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.15 (s, 1H), 7.09 (d, J = 7.6 Hz, 1H), 5.37 (s, 2H), 3.21 (s, 4H), 3.17 (s, 4H); 13C NMR (100 MHz, CDCl3,): δ 148.58, 148.04, 7.65, 147.21, 133.71, 133.42, 130.78, 128.20, 124.45, 123.53, 122.77, 121.88, 121.46, 117.09, 54.52, 29.47, 29.32 p.p.m.

Refinement

H atoms were positioned geometrically and refined in the riding model approximation with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2Ueq(C). Four F atoms of the PF6- ion are disordered over two positions (F3,F4,F5,F6/F3A,F4A,F5A,F6A) with refined occupancies of 0.869 (9) and 0.131 (9). The disordered F atoms were restrained to be coplanar, with the F···F distances restrained to be equal. The displacement parameters of disordered F atoms were restrained to be approximately isotropic.

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C20H19N2+·F6PZ = 2
Mr = 432.34F000 = 444
Triclinic, P1Dx = 1.505 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.311 (3) ÅCell parameters from 20 reflections
b = 10.138 (3) Åθ = 4.9–9.1º
c = 10.562 (3) ŵ = 0.21 mm1
α = 86.82 (2)ºT = 296 (2) K
β = 86.44 (2)ºBlock, colourless
γ = 73.61 (2)º0.28 × 0.25 × 0.18 mm
V = 953.9 (5) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.006
Radiation source: fine-focus sealed tubeθmax = 25.5º
Monochromator: graphiteθmin = 1.9º
T = 296(2) Kh = −10→11
ω/2θ scansk = −2→12
Absorption correction: nonel = −12→12
3558 measured reflections3 standard reflections
3522 independent reflections every 300 reflections
2238 reflections with I > 2σ(I) intensity decay: 4.6%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.223  w = 1/[σ2(Fo2) + (0.1349P)2] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
3522 reflectionsΔρmax = 0.64 e Å3
299 parametersΔρmin = −0.41 e Å3
81 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
N10.3258 (3)−0.0608 (3)0.3056 (3)0.0388 (7)
N20.1779 (3)0.1062 (3)0.1997 (3)0.0412 (7)
C10.7078 (6)−0.4108 (5)0.5742 (4)0.0654 (13)
H1A0.6556−0.43100.65200.078*
H1B0.7911−0.37580.59170.078*
C20.7481 (5)−0.5286 (5)0.4784 (4)0.0658 (13)
H2A0.8522−0.55470.44760.079*
H2B0.7152−0.60860.50660.079*
C30.6426 (4)−0.4283 (4)0.3899 (4)0.0486 (10)
C40.5802 (5)−0.4138 (4)0.2742 (4)0.0534 (11)
H40.6062−0.48380.21660.064*
C50.4756 (4)−0.2881 (4)0.2472 (3)0.0477 (10)
H50.4297−0.27310.17000.057*
C60.4397 (4)−0.1854 (4)0.3348 (3)0.0385 (8)
C70.5044 (4)−0.2001 (4)0.4520 (3)0.0452 (9)
H70.4809−0.13040.50990.054*
C80.6057 (5)−0.3256 (4)0.4753 (3)0.0474 (9)
C90.2990 (4)0.0017 (3)0.1915 (3)0.0381 (8)
H90.3572−0.02470.11750.046*
C100.1233 (5)0.1122 (4)0.3233 (4)0.0583 (12)
H100.03780.17590.35520.070*
C110.2151 (5)0.0095 (4)0.3902 (4)0.0525 (10)
H110.2059−0.01040.47680.063*
C120.1133 (4)0.2028 (4)0.0937 (3)0.0457 (9)
H12A0.01010.20260.08540.055*
H12B0.16880.17150.01500.055*
C130.1181 (4)0.3462 (4)0.1145 (3)0.0394 (8)
C14−0.0027 (4)0.4358 (4)0.1797 (3)0.0414 (9)
H14−0.08820.41030.20720.050*
C150.0126 (4)0.5639 (4)0.2006 (3)0.0446 (9)
C16−0.0632 (5)0.7005 (4)0.2603 (5)0.0611 (12)
H16A−0.07690.69450.35200.073*
H16B−0.15500.75220.22150.073*
C170.0771 (5)0.7460 (4)0.2122 (4)0.0613 (12)
H17A0.05690.82180.14960.074*
H17B0.13600.76220.27930.074*
C180.1361 (4)0.6058 (4)0.1564 (3)0.0448 (9)
C190.2544 (4)0.5185 (4)0.0891 (4)0.0494 (10)
H190.33750.54640.05830.059*
C200.2429 (4)0.3886 (4)0.0702 (3)0.0465 (10)
H200.32090.32710.02640.056*
P10.67915 (11)0.11989 (10)0.17994 (9)0.0466 (4)
F10.5204 (3)0.1791 (4)0.2485 (3)0.0890 (10)
F20.8367 (3)0.0567 (3)0.1101 (3)0.0964 (11)
F30.6267 (4)0.0006 (4)0.1205 (3)0.0908 (17)0.869 (9)
F40.7321 (5)0.0220 (4)0.2990 (3)0.109 (2)0.869 (9)
F50.7340 (4)0.2334 (4)0.2388 (5)0.112 (2)0.869 (9)
F60.6275 (5)0.2124 (5)0.0586 (4)0.120 (2)0.869 (9)
F3A0.6793 (7)−0.018 (2)0.2185 (12)0.127 (14)0.131 (9)
F4A0.7527 (10)0.1314 (12)0.3022 (15)0.090 (10)0.131 (9)
F5A0.6805 (7)0.260 (2)0.1369 (12)0.103 (11)0.131 (9)
F6A0.6104 (10)0.1040 (12)0.0613 (16)0.093 (10)0.131 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0443 (17)0.0364 (15)0.0320 (15)−0.0048 (13)−0.0036 (12)−0.0025 (12)
N20.0480 (18)0.0395 (16)0.0332 (15)−0.0068 (14)−0.0038 (13)−0.0028 (12)
C10.075 (3)0.066 (3)0.047 (2)−0.005 (2)−0.023 (2)0.011 (2)
C20.064 (3)0.065 (3)0.056 (3)0.002 (2)−0.013 (2)0.012 (2)
C30.046 (2)0.051 (2)0.042 (2)−0.0017 (18)−0.0069 (16)0.0010 (17)
C40.050 (2)0.055 (2)0.046 (2)0.0046 (18)−0.0117 (17)−0.0145 (18)
C50.049 (2)0.055 (2)0.0348 (19)−0.0043 (18)−0.0110 (16)−0.0087 (17)
C60.0361 (18)0.0414 (19)0.0340 (17)−0.0041 (15)−0.0050 (14)0.0004 (14)
C70.057 (2)0.048 (2)0.0287 (17)−0.0099 (18)−0.0066 (16)−0.0024 (15)
C80.055 (2)0.050 (2)0.0331 (18)−0.0094 (18)−0.0107 (16)0.0070 (16)
C90.044 (2)0.0407 (19)0.0286 (16)−0.0088 (16)−0.0053 (14)−0.0017 (14)
C100.068 (3)0.049 (2)0.042 (2)0.008 (2)0.0080 (19)−0.0024 (18)
C110.061 (3)0.050 (2)0.0356 (19)0.0015 (19)0.0081 (18)−0.0034 (16)
C120.052 (2)0.046 (2)0.0351 (18)−0.0040 (17)−0.0135 (16)−0.0021 (16)
C130.0406 (19)0.0434 (19)0.0305 (17)−0.0041 (15)−0.0117 (14)0.0019 (14)
C140.0363 (19)0.043 (2)0.0417 (19)−0.0050 (15)−0.0094 (15)0.0040 (15)
C150.041 (2)0.043 (2)0.044 (2)−0.0004 (16)−0.0123 (16)0.0019 (16)
C160.058 (3)0.043 (2)0.075 (3)−0.0011 (19)−0.008 (2)−0.008 (2)
C170.063 (3)0.050 (2)0.071 (3)−0.015 (2)−0.014 (2)−0.002 (2)
C180.045 (2)0.047 (2)0.0414 (19)−0.0100 (17)−0.0131 (16)0.0077 (16)
C190.042 (2)0.064 (3)0.044 (2)−0.0179 (19)−0.0051 (17)0.0037 (18)
C200.040 (2)0.056 (2)0.0373 (19)−0.0024 (17)−0.0069 (16)−0.0042 (17)
P10.0469 (6)0.0481 (6)0.0409 (6)−0.0061 (5)−0.0024 (4)−0.0045 (4)
F10.0595 (17)0.125 (2)0.0650 (17)0.0038 (16)0.0102 (13)−0.0246 (17)
F20.0592 (18)0.098 (2)0.127 (3)−0.0126 (16)0.0273 (18)−0.042 (2)
F30.093 (3)0.122 (4)0.078 (3)−0.060 (3)0.027 (2)−0.048 (3)
F40.165 (4)0.074 (3)0.054 (2)0.023 (3)−0.021 (2)0.0058 (18)
F50.105 (3)0.082 (3)0.158 (5)−0.031 (2)0.003 (3)−0.061 (3)
F60.151 (4)0.106 (4)0.060 (2)0.024 (3)0.002 (2)0.034 (2)
F3A0.122 (19)0.094 (16)0.18 (2)−0.059 (14)−0.017 (16)0.033 (16)
F4A0.077 (13)0.105 (19)0.079 (13)−0.006 (12)−0.049 (11)0.013 (12)
F5A0.140 (19)0.086 (15)0.091 (17)−0.050 (13)0.001 (14)0.004 (13)
F6A0.145 (18)0.095 (17)0.052 (12)−0.048 (14)−0.024 (11)−0.012 (12)

Geometric parameters (Å, °)

N1—C91.334 (4)C12—H12B0.97
N1—C111.382 (4)C13—C201.395 (5)
N1—C61.435 (4)C13—C141.400 (5)
N2—C91.313 (4)C14—C151.378 (5)
N2—C101.370 (5)C14—H140.93
N2—C121.484 (4)C15—C181.381 (6)
C1—C81.517 (5)C15—C161.518 (5)
C1—C21.558 (6)C16—C171.552 (7)
C1—H1A0.97C16—H16A0.97
C1—H1B0.97C16—H16B0.97
C2—C31.522 (5)C17—C181.510 (5)
C2—H2A0.97C17—H17A0.97
C2—H2B0.97C17—H17B0.97
C3—C41.368 (5)C18—C191.387 (5)
C3—C81.371 (5)C19—C201.378 (5)
C4—C51.395 (5)C19—H190.93
C4—H40.93C20—H200.93
C5—C61.386 (5)P1—F3A1.43 (3)
C5—H50.93P1—F5A1.47 (2)
C6—C71.393 (5)P1—F6A1.48 (2)
C7—C81.373 (5)P1—F4A1.524 (18)
C7—H70.93P1—F51.556 (4)
C9—H90.93P1—F61.563 (4)
C10—C111.343 (5)P1—F41.572 (4)
C10—H100.93P1—F11.576 (3)
C11—H110.93P1—F21.579 (3)
C12—C131.497 (5)P1—F31.597 (4)
C12—H12A0.97
C9—N1—C11107.5 (3)C15—C14—H14122.0
C9—N1—C6126.8 (3)C13—C14—H14122.0
C11—N1—C6125.4 (3)C14—C15—C18123.0 (3)
C9—N2—C10108.2 (3)C14—C15—C16144.1 (4)
C9—N2—C12125.8 (3)C18—C15—C1693.0 (3)
C10—N2—C12125.9 (3)C15—C16—C1786.7 (3)
C8—C1—C286.7 (3)C15—C16—H16A114.2
C8—C1—H1A114.2C17—C16—H16A114.2
C2—C1—H1A114.2C15—C16—H16B114.2
C8—C1—H1B114.2C17—C16—H16B114.2
C2—C1—H1B114.2H16A—C16—H16B111.4
H1A—C1—H1B111.4C18—C17—C1686.8 (3)
C3—C2—C186.3 (3)C18—C17—H17A114.2
C3—C2—H2A114.3C16—C17—H17A114.2
C1—C2—H2A114.3C18—C17—H17B114.2
C3—C2—H2B114.3C16—C17—H17B114.2
C1—C2—H2B114.3H17A—C17—H17B111.3
H2A—C2—H2B111.4C15—C18—C19121.1 (4)
C4—C3—C8122.4 (3)C15—C18—C1793.5 (3)
C4—C3—C2144.0 (4)C19—C18—C17145.3 (4)
C8—C3—C293.5 (3)C20—C19—C18116.7 (4)
C3—C4—C5116.3 (3)C20—C19—H19121.6
C3—C4—H4121.8C18—C19—H19121.6
C5—C4—H4121.8C19—C20—C13122.2 (3)
C6—C5—C4120.5 (3)C19—C20—H20118.9
C6—C5—H5119.8C13—C20—H20118.9
C4—C5—H5119.8F3A—P1—F5A178.4 (5)
C5—C6—C7123.0 (3)F3A—P1—F6A88.8 (6)
C5—C6—N1118.5 (3)F5A—P1—F6A90.0 (6)
C7—C6—N1118.5 (3)F3A—P1—F4A89.6 (6)
C8—C7—C6114.7 (3)F5A—P1—F4A91.5 (6)
C8—C7—H7122.7F6A—P1—F4A178.2 (6)
C6—C7—H7122.7F5—P1—F692.2 (3)
C3—C8—C7123.1 (3)F5—P1—F489.7 (3)
C3—C8—C193.5 (3)F6—P1—F4177.9 (2)
C7—C8—C1143.4 (3)F3A—P1—F191.1 (2)
N2—C9—N1109.6 (3)F5A—P1—F190.1 (2)
N2—C9—H9125.2F6A—P1—F191.5 (2)
N1—C9—H9125.2F4A—P1—F189.5 (2)
C11—C10—N2107.8 (3)F5—P1—F189.43 (19)
C11—C10—H10126.1F6—P1—F190.82 (19)
N2—C10—H10126.1F4—P1—F190.17 (19)
C10—C11—N1106.8 (3)F3A—P1—F287.5 (2)
C10—C11—H11126.6F5A—P1—F291.3 (2)
N1—C11—H11126.6F6A—P1—F287.4 (2)
N2—C12—C13111.8 (3)F4A—P1—F291.5 (2)
N2—C12—H12A109.3F5—P1—F292.30 (19)
C13—C12—H12A109.3F6—P1—F289.4 (2)
N2—C12—H12B109.3F4—P1—F289.5 (2)
C13—C12—H12B109.3F1—P1—F2178.25 (18)
H12A—C12—H12B107.9F5—P1—F3178.5 (2)
C20—C13—C14120.9 (3)F6—P1—F388.8 (3)
C20—C13—C12119.8 (3)F4—P1—F389.3 (2)
C14—C13—C12119.3 (3)F1—P1—F391.61 (18)
C15—C14—C13116.0 (4)F2—P1—F386.66 (17)
C8—C1—C2—C30.8 (3)C12—N2—C10—C11−178.3 (4)
C1—C2—C3—C4−177.7 (7)N2—C10—C11—N1−0.8 (5)
C1—C2—C3—C8−0.9 (4)C9—N1—C11—C100.7 (5)
C8—C3—C4—C5−0.3 (7)C6—N1—C11—C10−174.1 (4)
C2—C3—C4—C5176.0 (6)C9—N2—C12—C13−115.5 (4)
C3—C4—C5—C60.3 (7)C10—N2—C12—C1363.2 (5)
C4—C5—C6—C70.4 (7)N2—C12—C13—C2089.8 (4)
C4—C5—C6—N1−176.8 (4)N2—C12—C13—C14−89.5 (4)
C9—N1—C6—C5−35.6 (6)C20—C13—C14—C15−2.4 (5)
C11—N1—C6—C5138.2 (4)C12—C13—C14—C15177.0 (3)
C9—N1—C6—C7147.2 (4)C13—C14—C15—C182.5 (5)
C11—N1—C6—C7−39.0 (5)C13—C14—C15—C16−178.8 (5)
C5—C6—C7—C8−0.9 (6)C14—C15—C16—C17−179.7 (5)
N1—C6—C7—C8176.2 (3)C18—C15—C16—C17−0.8 (3)
C4—C3—C8—C7−0.3 (7)C15—C16—C17—C180.8 (3)
C2—C3—C8—C7−178.1 (4)C14—C15—C18—C19−1.0 (6)
C4—C3—C8—C1178.7 (4)C16—C15—C18—C19179.7 (3)
C2—C3—C8—C10.9 (4)C14—C15—C18—C17−179.9 (3)
C6—C7—C8—C30.9 (6)C16—C15—C18—C170.9 (3)
C6—C7—C8—C1−177.5 (6)C16—C17—C18—C15−0.9 (3)
C2—C1—C8—C3−0.9 (4)C16—C17—C18—C19−179.2 (6)
C2—C1—C8—C7177.7 (6)C15—C18—C19—C20−0.7 (5)
C10—N2—C9—N1−0.2 (4)C17—C18—C19—C20177.3 (5)
C12—N2—C9—N1178.7 (3)C18—C19—C20—C130.8 (5)
C11—N1—C9—N2−0.3 (4)C14—C13—C20—C190.8 (5)
C6—N1—C9—N2174.4 (3)C12—C13—C20—C19−178.6 (3)
C9—N2—C10—C110.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2B···Cg1i0.973.003.813 (5)143

Symmetry codes: (i) −x+1, −y−1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2536).

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