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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o135.
Published online 2007 December 6. doi:  10.1107/S1600536807061648
PMCID: PMC2915204

N,N′-Di-p-tolyl­ethyl­enediamine

Abstract

The asymmetric unit of the title compound, C16H20N2, contains two independent mol­ecules. The rings in each mol­ecule are oriented at dihedral angles of 78.94 (3) and 77.76 (3)°.

Related literature

For general background, see: Yang et al. (2004 [triangle]); Garcia-Marco et al. (2006 [triangle]). For related literature, see: Türkmen & Çetinkaya (2006 [triangle]); Grasa et al. (2001 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-0o135-scheme1.jpg

Experimental

Crystal data

  • C16H20N2
  • M r = 240.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o135-efi1.jpg
  • a = 8.9070 (18) Å
  • b = 25.252 (5) Å
  • c = 12.287 (3) Å
  • β = 90.30 (3)°
  • V = 2763.5 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 (2) K
  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.963, T max = 0.987
  • 5764 measured reflections
  • 5408 independent reflections
  • 2777 reflections with I > 2σ(I)
  • R int = 0.073
  • 3 standard reflections every 120 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.090
  • wR(F 2) = 0.205
  • S = 1.00
  • 5408 reflections
  • 325 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2000 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global, x1. DOI: 10.1107/S1600536807061648/hk2391sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061648/hk2391Isup2.hkl

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

Acknowledgments

The authors thank the Analysis Centre, Nanjing University, for carrying out the X-ray crystallographic analysis.

supplementary crystallographic information

Comment

N,N-Disubstituted ethylenediamine compounds are important subunits present in a number of naturally occurring compounds and have found numerous applications as active catalysts (Yang et al., 2004) and intermediates (Garcia-Marco et al., 2006). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of (I) (Fig. 1) contains two independent molecules, in which the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C2—C7), B (C10—C15), C (C18—C23) and D(C26—C31) are, of course, planar and the dihedral angles between them are A/B = 78.94 (3)° and C/D = 77.76 (3)°.

As can be seen from the packing diagram (Fig. 2), the molecules of (I) are elongated along the b axis and stacked along the a axis.

Experimental

N,N'-di-p-tolyl-ethylenediimine, (II), was firstly synthesized, according to a literature method (Türkmen & Çetinkaya, 2006). For the preparation of the title compound, (I), compound (II) (2.4 g, 10 mmol) was dissolved in methanol/furanidine (40/60 ml) and mixed with NaBH4 (3.8 g, 100 mmol) (Grasa et al., 2001). The mixture was kept at 298 K and stirred for 30 min, and then deionized water (200 ml) was used to quench the reaction. The mixture was extracted 3 times with ether (50 ml). Ether extracts were dried over MgSO4 and evaporated under reduced pressure to afford (I). The product was purified by repeated crystallization. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of ethanol (yield; 2.0 g, m.p. 366 K).

Refinement

H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram of (I).

Crystal data

C16H20N2F000 = 1040
Mr = 240.34Dx = 1.155 Mg m3
Monoclinic, P21/nMelting point: 366 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 8.9070 (18) ÅCell parameters from 25 reflections
b = 25.252 (5) Åθ = 10–13º
c = 12.287 (3) ŵ = 0.07 mm1
β = 90.30 (3)ºT = 298 (2) K
V = 2763.5 (10) Å3Block, yellow
Z = 80.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.073
Radiation source: fine-focus sealed tubeθmax = 26.1º
Monochromator: graphiteθmin = 1.6º
T = 298(2) Kh = −10→10
ω/2θ scansk = 0→31
Absorption correction: ψ scan(North et al., 1968)l = 0→15
Tmin = 0.963, Tmax = 0.9873 standard reflections
5764 measured reflections every 120 reflections
5408 independent reflections intensity decay: none
2777 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.090H-atom parameters constrained
wR(F2) = 0.205  w = 1/[σ2(Fo2) + (0.030P)2 + 5.P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5408 reflectionsΔρmax = 0.24 e Å3
325 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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*/Ueq
N10.6890 (4)0.29404 (14)0.1934 (3)0.0578 (10)
H1A0.74050.27590.23960.069*
N20.7171 (4)0.18725 (14)0.1110 (3)0.0583 (9)
H2A0.73860.17880.17700.070*
N30.1908 (4)0.29364 (15)0.0572 (3)0.0604 (10)
H3B0.24020.27550.01020.072*
N40.2184 (4)0.18680 (14)0.1392 (3)0.0589 (10)
H4B0.23980.17860.07320.071*
C10.2841 (5)0.4526 (2)0.3496 (4)0.0787 (15)
H1B0.26370.47810.29360.118*
H1C0.32710.47010.41170.118*
H1D0.19220.43550.37030.118*
C20.3925 (4)0.41180 (17)0.3077 (3)0.0505 (10)
C30.4474 (5)0.41291 (17)0.2034 (3)0.0546 (11)
H3A0.41760.44030.15760.065*
C40.5447 (5)0.37524 (17)0.1638 (3)0.0519 (10)
H4A0.58000.37780.09290.062*
C50.5898 (4)0.33369 (16)0.2295 (3)0.0438 (9)
C60.5381 (5)0.33210 (17)0.3359 (3)0.0524 (10)
H6A0.56950.30520.38240.063*
C70.4398 (5)0.37049 (18)0.3731 (3)0.0547 (11)
H7A0.40470.36840.44420.066*
C80.7036 (5)0.28406 (17)0.0793 (3)0.0539 (11)
H8A0.75530.31340.04490.065*
H8B0.60490.28080.04620.065*
C90.7923 (5)0.23291 (18)0.0624 (4)0.0621 (12)
H9A0.80480.2268−0.01490.075*
H9B0.89130.23670.09470.075*
C100.6120 (4)0.15681 (16)0.0544 (3)0.0472 (10)
C110.5711 (4)0.10780 (17)0.0971 (3)0.0505 (10)
H11A0.61380.09640.16230.061*
C120.4682 (5)0.07583 (18)0.0440 (3)0.0552 (11)
H12A0.44200.04360.07510.066*
C130.4026 (4)0.09042 (17)−0.0545 (3)0.0491 (10)
C140.4421 (5)0.13987 (17)−0.0947 (3)0.0541 (11)
H14A0.39870.1516−0.15930.065*
C150.5450 (5)0.17251 (17)−0.0407 (3)0.0534 (11)
H15A0.56840.2054−0.07000.064*
C160.3006 (5)0.05418 (19)−0.1158 (4)0.0711 (13)
H16A0.28690.0221−0.07510.107*
H16B0.34400.0460−0.18520.107*
H16C0.20520.0711−0.12670.107*
C17−0.2095 (6)0.4545 (2)−0.0923 (4)0.0838 (16)
H17A−0.23770.4474−0.16640.126*
H17B−0.16200.4886−0.08810.126*
H17C−0.29740.4543−0.04750.126*
C18−0.1028 (5)0.41301 (19)−0.0536 (4)0.0593 (12)
C19−0.0466 (5)0.41364 (19)0.0526 (4)0.0604 (12)
H19A−0.07370.44100.09910.073*
C200.0485 (5)0.37439 (18)0.0901 (3)0.0581 (11)
H20A0.08290.37560.16170.070*
C210.0935 (4)0.33335 (18)0.0231 (3)0.0496 (10)
C220.0385 (5)0.33360 (18)−0.0840 (3)0.0530 (11)
H22A0.06760.3070−0.13180.064*
C23−0.0559 (5)0.37197 (19)−0.1190 (3)0.0582 (11)
H23A−0.09090.3706−0.19040.070*
C240.2085 (5)0.28304 (18)0.1726 (3)0.0576 (11)
H24A0.11060.28070.20650.069*
H24B0.26360.31170.20680.069*
C250.2919 (5)0.23195 (18)0.1878 (4)0.0612 (12)
H25A0.39110.23550.15650.073*
H25B0.30440.22550.26520.073*
C260.1144 (4)0.15593 (17)0.1944 (3)0.0494 (10)
C270.0724 (5)0.10681 (17)0.1522 (3)0.0554 (11)
H27A0.11300.09570.08640.067*
C28−0.0276 (4)0.07439 (19)0.2054 (3)0.0563 (11)
H28A−0.05220.04170.17540.068*
C29−0.0921 (4)0.08947 (18)0.3025 (4)0.0528 (11)
C30−0.0557 (4)0.13840 (18)0.3422 (3)0.0543 (11)
H30A−0.10020.15000.40620.065*
C310.0463 (5)0.17143 (17)0.2895 (3)0.0532 (11)
H31A0.06860.20440.31900.064*
C32−0.1948 (5)0.0527 (2)0.3631 (4)0.0749 (14)
H32A−0.20450.02010.32360.112*
H32B−0.29180.06890.37040.112*
H32C−0.15360.04560.43400.112*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.061 (2)0.063 (2)0.049 (2)0.0077 (19)−0.0055 (17)−0.0029 (18)
N20.060 (2)0.058 (2)0.057 (2)−0.0088 (19)−0.0006 (17)−0.0001 (18)
N30.062 (2)0.067 (3)0.053 (2)0.006 (2)0.0096 (18)−0.0017 (18)
N40.056 (2)0.063 (2)0.058 (2)−0.0058 (19)0.0077 (17)−0.0012 (19)
C10.068 (3)0.073 (4)0.096 (4)−0.001 (3)0.024 (3)−0.004 (3)
C20.044 (2)0.050 (3)0.057 (3)−0.008 (2)0.0098 (19)0.000 (2)
C30.055 (3)0.050 (3)0.058 (3)0.007 (2)0.002 (2)0.011 (2)
C40.055 (3)0.055 (3)0.045 (2)−0.002 (2)0.0029 (19)0.006 (2)
C50.037 (2)0.047 (2)0.047 (2)−0.0055 (18)−0.0002 (16)−0.0055 (19)
C60.056 (3)0.055 (3)0.047 (2)−0.005 (2)−0.0011 (19)0.006 (2)
C70.057 (3)0.061 (3)0.046 (2)−0.013 (2)0.014 (2)0.001 (2)
C80.054 (3)0.054 (3)0.054 (3)−0.003 (2)0.013 (2)0.001 (2)
C90.047 (3)0.070 (3)0.069 (3)−0.004 (2)0.012 (2)−0.008 (2)
C100.043 (2)0.050 (3)0.048 (2)0.0009 (19)0.0076 (18)−0.0017 (19)
C110.051 (3)0.053 (3)0.047 (2)0.005 (2)0.0049 (19)0.007 (2)
C120.051 (3)0.053 (3)0.061 (3)0.002 (2)0.004 (2)0.007 (2)
C130.039 (2)0.048 (3)0.061 (3)0.0031 (19)0.0045 (19)−0.005 (2)
C140.057 (3)0.057 (3)0.048 (2)0.009 (2)−0.003 (2)0.000 (2)
C150.060 (3)0.046 (3)0.055 (3)−0.003 (2)0.008 (2)0.007 (2)
C160.065 (3)0.066 (3)0.083 (3)0.002 (3)−0.008 (3)−0.006 (3)
C170.082 (4)0.068 (3)0.101 (4)0.012 (3)−0.029 (3)−0.003 (3)
C180.062 (3)0.058 (3)0.058 (3)−0.007 (2)−0.003 (2)0.001 (2)
C190.059 (3)0.058 (3)0.064 (3)0.003 (2)−0.002 (2)−0.013 (2)
C200.067 (3)0.064 (3)0.043 (2)−0.002 (2)−0.005 (2)−0.006 (2)
C210.041 (2)0.057 (3)0.051 (2)−0.002 (2)0.0087 (18)0.002 (2)
C220.053 (3)0.059 (3)0.047 (2)−0.008 (2)0.0018 (19)−0.007 (2)
C230.058 (3)0.068 (3)0.048 (2)−0.011 (2)−0.003 (2)0.001 (2)
C240.052 (3)0.064 (3)0.057 (3)−0.010 (2)−0.006 (2)−0.003 (2)
C250.037 (2)0.071 (3)0.075 (3)0.001 (2)−0.001 (2)0.005 (3)
C260.037 (2)0.060 (3)0.052 (2)0.004 (2)0.0011 (18)−0.003 (2)
C270.053 (3)0.059 (3)0.054 (3)0.006 (2)0.007 (2)−0.010 (2)
C280.044 (2)0.064 (3)0.061 (3)−0.002 (2)0.001 (2)−0.006 (2)
C290.037 (2)0.057 (3)0.064 (3)0.006 (2)0.0062 (19)0.005 (2)
C300.044 (2)0.069 (3)0.050 (2)0.008 (2)0.0035 (19)−0.005 (2)
C310.054 (3)0.051 (3)0.054 (2)0.003 (2)0.001 (2)−0.008 (2)
C320.055 (3)0.078 (4)0.092 (4)−0.004 (3)0.011 (3)0.012 (3)

Geometric parameters (Å, °)

N1—C51.409 (5)N3—C211.389 (5)
N1—C81.430 (5)N3—C241.451 (5)
N1—H1A0.8600N3—H3B0.8600
N2—C101.394 (5)N4—C261.389 (5)
N2—C91.462 (5)N4—C251.443 (5)
N2—H2A0.8600N4—H4B0.8600
C1—C21.504 (6)C17—C181.491 (6)
C1—H1B0.9600C17—H17A0.9600
C1—H1C0.9600C17—H17B0.9600
C1—H1D0.9600C17—H17C0.9600
C2—C31.374 (5)C18—C231.377 (6)
C2—C71.381 (6)C18—C191.396 (6)
C3—C41.378 (6)C19—C201.381 (6)
C3—H3A0.9300C19—H19A0.9300
C4—C51.383 (5)C20—C211.384 (6)
C4—H4A0.9300C20—H20A0.9300
C5—C61.389 (5)C21—C221.402 (5)
C6—C71.385 (6)C22—C231.352 (6)
C6—H6A0.9300C22—H22A0.9300
C7—H7A0.9300C23—H23A0.9300
C8—C91.529 (6)C24—C251.500 (6)
C8—H8A0.9700C24—H24A0.9700
C8—H8B0.9700C24—H24B0.9700
C9—H9A0.9700C25—H25A0.9700
C9—H9B0.9700C25—H25B0.9700
C10—C151.368 (5)C26—C311.376 (5)
C10—C111.393 (5)C26—C271.395 (6)
C11—C121.383 (6)C27—C281.378 (6)
C11—H11A0.9300C27—H27A0.9300
C12—C131.391 (6)C28—C291.380 (6)
C12—H12A0.9300C28—H28A0.9300
C13—C141.389 (6)C29—C301.367 (6)
C13—C161.491 (6)C29—C321.504 (6)
C14—C151.398 (6)C30—C311.396 (6)
C14—H14A0.9300C30—H30A0.9300
C15—H15A0.9300C31—H31A0.9300
C16—H16A0.9600C32—H32A0.9600
C16—H16B0.9600C32—H32B0.9600
C16—H16C0.9600C32—H32C0.9600
C5—N1—C8119.7 (3)C21—N3—C24119.5 (4)
C5—N1—H1A120.2C21—N3—H3B120.3
C8—N1—H1A120.2C24—N3—H3B120.3
C10—N2—C9122.6 (4)C26—N4—C25122.9 (4)
C10—N2—H2A118.7C26—N4—H4B118.5
C9—N2—H2A118.7C25—N4—H4B118.5
C2—C1—H1B109.5C18—C17—H17A109.5
C2—C1—H1C109.5C18—C17—H17B109.5
H1B—C1—H1C109.5H17A—C17—H17B109.5
C2—C1—H1D109.5C18—C17—H17C109.5
H1B—C1—H1D109.5H17A—C17—H17C109.5
H1C—C1—H1D109.5H17B—C17—H17C109.5
C3—C2—C7116.7 (4)C23—C18—C19116.4 (4)
C3—C2—C1122.5 (4)C23—C18—C17122.6 (4)
C7—C2—C1120.8 (4)C19—C18—C17121.0 (4)
C2—C3—C4122.9 (4)C20—C19—C18121.4 (4)
C2—C3—H3A118.5C20—C19—H19A119.3
C4—C3—H3A118.5C18—C19—H19A119.3
C3—C4—C5119.9 (4)C19—C20—C21121.2 (4)
C3—C4—H4A120.1C19—C20—H20A119.4
C5—C4—H4A120.1C21—C20—H20A119.4
C4—C5—C6118.4 (4)C20—C21—N3122.9 (4)
C4—C5—N1122.4 (4)C20—C21—C22117.0 (4)
C6—C5—N1119.2 (4)N3—C21—C22120.0 (4)
C7—C6—C5120.2 (4)C23—C22—C21121.0 (4)
C7—C6—H6A119.9C23—C22—H22A119.5
C5—C6—H6A119.9C21—C22—H22A119.5
C2—C7—C6121.8 (4)C22—C23—C18123.0 (4)
C2—C7—H7A119.1C22—C23—H23A118.5
C6—C7—H7A119.1C18—C23—H23A118.5
N1—C8—C9109.4 (4)N3—C24—C25109.4 (4)
N1—C8—H8A109.8N3—C24—H24A109.8
C9—C8—H8A109.8C25—C24—H24A109.8
N1—C8—H8B109.8N3—C24—H24B109.8
C9—C8—H8B109.8C25—C24—H24B109.8
H8A—C8—H8B108.2H24A—C24—H24B108.2
N2—C9—C8111.9 (3)N4—C25—C24113.9 (3)
N2—C9—H9A109.2N4—C25—H25A108.8
C8—C9—H9A109.2C24—C25—H25A108.8
N2—C9—H9B109.2N4—C25—H25B108.8
C8—C9—H9B109.2C24—C25—H25B108.8
H9A—C9—H9B107.9H25A—C25—H25B107.7
C15—C10—C11117.8 (4)C31—C26—N4123.5 (4)
C15—C10—N2123.7 (4)C31—C26—C27116.8 (4)
C11—C10—N2118.5 (4)N4—C26—C27119.7 (4)
C12—C11—C10121.0 (4)C28—C27—C26121.6 (4)
C12—C11—H11A119.5C28—C27—H27A119.2
C10—C11—H11A119.5C26—C27—H27A119.2
C11—C12—C13122.0 (4)C27—C28—C29121.3 (4)
C11—C12—H12A119.0C27—C28—H28A119.3
C13—C12—H12A119.0C29—C28—H28A119.3
C14—C13—C12116.2 (4)C30—C29—C28117.3 (4)
C14—C13—C16121.8 (4)C30—C29—C32121.7 (4)
C12—C13—C16122.0 (4)C28—C29—C32121.0 (4)
C13—C14—C15121.9 (4)C29—C30—C31121.9 (4)
C13—C14—H14A119.1C29—C30—H30A119.0
C15—C14—H14A119.1C31—C30—H30A119.0
C10—C15—C14121.1 (4)C26—C31—C30121.0 (4)
C10—C15—H15A119.5C26—C31—H31A119.5
C14—C15—H15A119.5C30—C31—H31A119.5
C13—C16—H16A109.5C29—C32—H32A109.5
C13—C16—H16B109.5C29—C32—H32B109.5
H16A—C16—H16B109.5H32A—C32—H32B109.5
C13—C16—H16C109.5C29—C32—H32C109.5
H16A—C16—H16C109.5H32A—C32—H32C109.5
H16B—C16—H16C109.5H32B—C32—H32C109.5
C7—C2—C3—C40.1 (6)C23—C18—C19—C20−1.3 (7)
C1—C2—C3—C4−178.9 (4)C17—C18—C19—C20177.9 (5)
C2—C3—C4—C50.7 (6)C18—C19—C20—C211.0 (7)
C3—C4—C5—C6−1.8 (6)C19—C20—C21—N3178.9 (4)
C3—C4—C5—N1180.0 (4)C19—C20—C21—C220.2 (6)
C8—N1—C5—C4−22.9 (6)C24—N3—C21—C2021.4 (6)
C8—N1—C5—C6158.9 (4)C24—N3—C21—C22−159.9 (4)
C4—C5—C6—C72.1 (6)C20—C21—C22—C23−1.0 (6)
N1—C5—C6—C7−179.6 (4)N3—C21—C22—C23−179.8 (4)
C3—C2—C7—C60.2 (6)C21—C22—C23—C180.7 (7)
C1—C2—C7—C6179.2 (4)C19—C18—C23—C220.4 (7)
C5—C6—C7—C2−1.3 (6)C17—C18—C23—C22−178.7 (4)
C5—N1—C8—C9−168.9 (3)C21—N3—C24—C25168.1 (4)
C10—N2—C9—C889.0 (5)C26—N4—C25—C24−89.5 (5)
N1—C8—C9—N260.7 (5)N3—C24—C25—N4−59.3 (5)
C9—N2—C10—C15−14.7 (6)C25—N4—C26—C3115.1 (6)
C9—N2—C10—C11165.9 (4)C25—N4—C26—C27−166.1 (4)
C15—C10—C11—C121.0 (6)C31—C26—C27—C28−2.6 (6)
N2—C10—C11—C12−179.5 (4)N4—C26—C27—C28178.5 (4)
C10—C11—C12—C131.0 (6)C26—C27—C28—C290.7 (6)
C11—C12—C13—C14−2.3 (6)C27—C28—C29—C301.7 (6)
C11—C12—C13—C16175.2 (4)C27—C28—C29—C32−176.7 (4)
C12—C13—C14—C151.7 (6)C28—C29—C30—C31−2.2 (6)
C16—C13—C14—C15−175.9 (4)C32—C29—C30—C31176.2 (4)
C11—C10—C15—C14−1.6 (6)N4—C26—C31—C30−179.0 (4)
N2—C10—C15—C14179.0 (4)C27—C26—C31—C302.2 (6)
C13—C14—C15—C100.2 (6)C29—C30—C31—C260.2 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2391).

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