N,N′-Bis[3,5-bis­(2,6-diisopropyl­phen­yl)phen­yl]butane-2,3-diimine

Lohr, T.L.; Piers, W.E.; Parvez, M.

doi:10.1107/S1600536811031254

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2281

doi:10.1107/S1600536811031254

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N,N′-Bis[3,5-bis(2,6-diisopropylphenyl)phenyl]butane-2,3-diimine

Tracy L. Lohr,^a Warren E. Piers ^a and Masood Parvez ^a ^*

^aDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: parvez@ucalgary.ca

(Received 26 July 2011; accepted 2 August 2011; online 11 August 2011)

The title molecule, C₆₄H₈₀N₂, lies on an inversion center wherein the central butanediimine fragment [N=C(Me)—C(Me)=N] is essentially planar [maximum deviation = 0.002 (2) Å] and its mean plane forms a dihedral of 70.88 (10)° with the attached benzene ring. In the symmetry-unique part of the molecule, the dihedral angles between the benzene ring bonded to the N atom and the other two benzene rings are 89.61 (6) and 82.77 (6)°.

Related literature

For background to water splitting, see: Yang & Hall (2010 ); Kee et al. (2011 ); Blakemore et al. (2010 ). For related structures, see: Ionkin & Marshall (2004 ); Zou et al. (2008 ); Lohr et al. (2011 ).

Experimental

Crystal data

C₆₄H₈₀N₂
M_r = 877.30
Triclinic, $[P \overline 1]$
a = 8.512 (3) Å
b = 11.513 (3) Å
c = 16.501 (6) Å
α = 101.456 (18)°
β = 97.471 (13)°
γ = 99.505 (17)°
V = 1540.8 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.05 mm⁻¹
T = 173 K
0.16 × 0.14 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII CCD detector
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.992, T_max = 0.997
10648 measured reflections
5610 independent reflections
4274 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.197
S = 1.06
5610 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031254/lh5297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031254/lh5297Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031254/lh5297Isup3.cml

checkCIF report

Comment top

To meet the ever-growing demand for green and carbon neutral energy, water splitting for the generation of hydrogen fuel represents an appealing strategy. To do their part, chemists have been looking at the steps towards organometallic mono-nuclear water splitting. (Yang & Hall, 2010; Kee et al., 2011; Blakemore et al., 2010). Our group is currently exploring the usage of platinum to mediate this reaction in an effort to understand the fundamental steps of O—H and O—O bond activation. This research is directed at synthesizing and studying plausible intermediates (Pt—OH and Pt—H species) in order to determine what role they play in the water activation process. The title compound was synthesized as a ligand to stabilize and isolate these highly reactive monomeric species for further mechanistic study.

In the title compound (Fig. 1), the central butanediimine fragment (N═ C(Me)–C(Me)═N) is essentially planar (maximum deviation of C1 being 0.002 (2) Å). The benzene ring (C3–C8) lies at 70.88 (10)° with respect to the mean-plane of the butanediimine fragment. The dihedral angles between the benzene ring bonded to N1 and benzene rings C9–C14 and C21–C26 are 89.61 (6) and 82.77 (6)°, respectively. The molecular dimesions in the title compound agree very well with the corresponding molecular dimensions reported in a few closely related compounds (Ionkin & Marshall, 2004; Zou et al., 2008; Lohr et al., 2011).

Related literature top

For background to water splitting, see: Yang & Hall (2010); Kee et al. (2011); Blakemore et al. (2010). For related structures, see: Ionkin & Marshall (2004); Zou et al. (2008); Lohr et al. (2011).

Experimental top

Synthesis of (ArN=C(Me)—C(Me)=NAr) (Ar = 3,5-bis(2,6-diisopropylphenyl)benzene): In air, 3,5-bis(2,6-diisopropylphenyl)aniline (0.190 g, 0.471 mmol) and 2,3-butadione (0.021 ml, 0.236 mmol) were dissolved in MeOH (35 ml). To this yellow solution were added 3 drops of formic acid and the mixture was stirred at room temperature and a bright yellow precipitate formed overnight. The mixture was stirred for 14 h, cooled, filtered, washed with cold MeOH (3 x 5 ml), and dried over an aspirator for 3 h. The title compound was isolated as a light yellow solid (0.183 g, 45%). X-ray quality crystals were obtained through slow cooling to 243 K in concentrated ethyl acetate.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The title molecule with displacement ellipsoids plotted at 30% probability level (Farrugia, 1997). Primed atoms are related by the symmetry code (-x, -y+1, -z).

N,N'-Bis[3,5-bis(2,6-diisopropylphenyl)phenyl]butane-2,3-diimine top

Crystal data top

C₆₄H₈₀N₂	Z = 1
M_r = 877.30	F(000) = 478
Triclinic, P1	D_x = 0.945 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.512 (3) Å	Cell parameters from 6423 reflections
b = 11.513 (3) Å	θ = 1.0–25.4°
c = 16.501 (6) Å	µ = 0.05 mm⁻¹
α = 101.456 (18)°	T = 173 K
β = 97.471 (13)°	Prism, pale yellow
γ = 99.505 (17)°	0.16 × 0.14 × 0.06 mm
V = 1540.8 (9) Å³

Data collection top

Nonius KappaCCD diffractometer with Bruker APEXII CCD detector	5610 independent reflections
Radiation source: fine-focus sealed tube	4274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 25.4°, θ_min = 1.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
T_min = 0.992, T_max = 0.997	k = −12→13
10648 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0937P)² + 0.8313P] where P = (F_o² + 2F_c²)/3
5610 reflections	(Δ/σ)_max = 0.003
307 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₆₄H₈₀N₂	γ = 99.505 (17)°
M_r = 877.30	V = 1540.8 (9) Å³
Triclinic, P1	Z = 1
a = 8.512 (3) Å	Mo Kα radiation
b = 11.513 (3) Å	µ = 0.05 mm⁻¹
c = 16.501 (6) Å	T = 173 K
α = 101.456 (18)°	0.16 × 0.14 × 0.06 mm
β = 97.471 (13)°

Data collection top

Nonius KappaCCD diffractometer with Bruker APEXII CCD detector	5610 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	4274 reflections with I > 2σ(I)
T_min = 0.992, T_max = 0.997	R_int = 0.028
10648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
5610 reflections	Δρ_min = −0.26 e Å⁻³
307 parameters

Special details top

Experimental. ¹H NMR (400 MHz, CDCl₃): δ = 1.08 (d, 24H, CH(CH₃)₂), 1.15 (d, 24H, CH(CH₃)₂), 2.23 (s, 6H, N═C–CH₃), 2.84 (m, 8H, CH(CH₃)₂), 6.62 (d, 4H, Ar–H), 6.79 (t, 2H, Ar–H), 7.21 (d, 8H, Ar-H), 7.34 (t, 4H, Ar–H). ¹³C NMR (100 MHz, CDCl₃): δ = 15.64 (N═C–CH₃), 24.31 (CH(CH₃)₂), 24.44 (CH(CH₃)₂), 30.65 (CH(CH₃)₂), 118.09 (Ar–CH), 122.71 (Ar–CH), 126.91 (Ar–CH), 128.09 (Ar–CH), 139.08 (Ar–C), 141.66 (Ar–C), 146.84 (Ar–C), 150.89 (Ar–C), 169.06 (N═C–CH₃).

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) top

	x	y	z	U_iso*/U_eq
N1	0.0422 (2)	0.46436 (15)	0.09717 (11)	0.0335 (4)
C1	0.0718 (2)	0.49926 (18)	0.03123 (12)	0.0303 (5)
C2	0.2367 (3)	0.5377 (3)	0.01107 (16)	0.0541 (7)
H2A	0.2353	0.5091	−0.0491	0.065*
H2B	0.3152	0.5032	0.0429	0.065*
H2C	0.2674	0.6261	0.0262	0.065*
C3	0.1702 (2)	0.46292 (18)	0.16106 (12)	0.0295 (4)
C4	0.2616 (2)	0.56921 (18)	0.21263 (13)	0.0307 (5)
H4	0.2407	0.6449	0.2042	0.037*
C5	0.3836 (2)	0.56590 (17)	0.27654 (12)	0.0286 (4)
C6	0.4108 (2)	0.45436 (17)	0.28880 (12)	0.0278 (4)
H6	0.4941	0.4515	0.3323	0.033*
C7	0.3184 (2)	0.34646 (17)	0.23857 (12)	0.0272 (4)
C8	0.1969 (2)	0.35137 (18)	0.17475 (12)	0.0291 (4)
H8	0.1322	0.2787	0.1405	0.035*
C9	0.4870 (2)	0.68017 (17)	0.33082 (13)	0.0317 (5)
C10	0.6300 (3)	0.73029 (18)	0.30592 (14)	0.0374 (5)
C11	0.7271 (3)	0.8346 (2)	0.35794 (17)	0.0466 (6)
H11	0.8251	0.8689	0.3425	0.056*
C12	0.6828 (3)	0.8886 (2)	0.43142 (17)	0.0519 (7)
H12	0.7500	0.9602	0.4658	0.062*
C13	0.5419 (3)	0.8399 (2)	0.45557 (15)	0.0468 (6)
H13	0.5125	0.8787	0.5062	0.056*
C14	0.4423 (3)	0.73418 (19)	0.40628 (13)	0.0370 (5)
C15	0.6785 (3)	0.6753 (2)	0.22388 (16)	0.0466 (6)
H15	0.6063	0.5943	0.2010	0.056*
C16	0.6502 (5)	0.7543 (3)	0.1599 (2)	0.0793 (10)
H16A	0.6741	0.7153	0.1058	0.095*
H16B	0.7214	0.8339	0.1802	0.095*
H16C	0.5373	0.7639	0.1532	0.095*
C17	0.8506 (4)	0.6567 (4)	0.2347 (3)	0.0946 (12)
H17A	0.8753	0.6198	0.1802	0.114*
H17B	0.8642	0.6033	0.2734	0.114*
H17C	0.9240	0.7348	0.2574	0.114*
C18	0.2893 (3)	0.6814 (2)	0.43511 (14)	0.0420 (5)
H18	0.2390	0.6038	0.3939	0.050*
C19	0.3249 (4)	0.6521 (3)	0.52078 (18)	0.0652 (8)
H19A	0.2246	0.6125	0.5352	0.078*
H19B	0.3705	0.7269	0.5631	0.078*
H19C	0.4025	0.5979	0.5193	0.078*
C20	0.1674 (4)	0.7648 (3)	0.4347 (2)	0.0641 (8)
H20A	0.0657	0.7246	0.4474	0.077*
H20B	0.1480	0.7835	0.3793	0.077*
H20C	0.2103	0.8398	0.4773	0.077*
C21	0.3505 (2)	0.22790 (17)	0.25381 (13)	0.0299 (5)
C22	0.2565 (3)	0.16664 (18)	0.30220 (14)	0.0350 (5)
C23	0.2938 (3)	0.0592 (2)	0.31816 (15)	0.0437 (6)
H23	0.2319	0.0170	0.3511	0.052*
C24	0.4189 (3)	0.0126 (2)	0.28706 (16)	0.0487 (6)
H24	0.4431	−0.0604	0.2991	0.058*
C25	0.5085 (3)	0.0721 (2)	0.23850 (16)	0.0458 (6)
H25	0.5936	0.0389	0.2168	0.055*
C26	0.4766 (3)	0.18020 (18)	0.22058 (14)	0.0361 (5)
C27	0.1190 (3)	0.2182 (2)	0.33720 (16)	0.0427 (6)
H27	0.0728	0.2616	0.2958	0.051*
C28	0.1793 (3)	0.3116 (2)	0.42019 (17)	0.0512 (6)
H28A	0.0904	0.3498	0.4371	0.061*
H28B	0.2673	0.3734	0.4130	0.061*
H28C	0.2189	0.2714	0.4636	0.061*
C29	−0.0188 (3)	0.1216 (3)	0.3474 (2)	0.0591 (7)
H29A	−0.1114	0.1585	0.3595	0.071*
H29B	0.0173	0.0855	0.3938	0.071*
H29C	−0.0507	0.0587	0.2954	0.071*
C30	0.5731 (3)	0.2413 (2)	0.16369 (16)	0.0451 (6)
H30	0.5383	0.3200	0.1632	0.054*
C31	0.7519 (4)	0.2698 (4)	0.1956 (3)	0.1020 (15)
H31A	0.8079	0.3124	0.1585	0.122*
H31B	0.7908	0.1945	0.1968	0.122*
H31C	0.7738	0.3211	0.2524	0.122*
C32	0.5319 (6)	0.1666 (4)	0.0742 (2)	0.1061 (15)
H32A	0.5925	0.2083	0.0382	0.127*
H32B	0.4158	0.1560	0.0541	0.127*
H32C	0.5608	0.0873	0.0725	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0301 (9)	0.0400 (10)	0.0312 (10)	0.0074 (7)	−0.0019 (7)	0.0138 (8)
C1	0.0313 (11)	0.0313 (10)	0.0286 (11)	0.0088 (8)	0.0014 (9)	0.0074 (8)
C2	0.0316 (12)	0.093 (2)	0.0397 (14)	0.0075 (12)	0.0007 (10)	0.0285 (14)
C3	0.0246 (10)	0.0375 (11)	0.0286 (11)	0.0064 (8)	0.0043 (8)	0.0128 (9)
C4	0.0326 (11)	0.0319 (10)	0.0302 (11)	0.0097 (8)	0.0035 (8)	0.0117 (8)
C5	0.0314 (10)	0.0290 (10)	0.0267 (10)	0.0076 (8)	0.0049 (8)	0.0078 (8)
C6	0.0261 (10)	0.0321 (10)	0.0251 (10)	0.0058 (8)	−0.0006 (8)	0.0092 (8)
C7	0.0254 (10)	0.0307 (10)	0.0265 (10)	0.0045 (8)	0.0035 (8)	0.0098 (8)
C8	0.0271 (10)	0.0296 (10)	0.0294 (11)	0.0023 (8)	0.0023 (8)	0.0077 (8)
C9	0.0364 (11)	0.0275 (10)	0.0310 (11)	0.0097 (8)	−0.0019 (9)	0.0083 (8)
C10	0.0391 (12)	0.0291 (10)	0.0425 (13)	0.0062 (9)	0.0003 (10)	0.0094 (9)
C11	0.0443 (13)	0.0325 (11)	0.0568 (16)	−0.0004 (10)	0.0009 (11)	0.0073 (11)
C12	0.0585 (16)	0.0284 (11)	0.0561 (16)	−0.0006 (11)	−0.0109 (13)	0.0008 (11)
C13	0.0632 (16)	0.0343 (12)	0.0376 (13)	0.0111 (11)	−0.0010 (11)	0.0009 (10)
C14	0.0451 (13)	0.0336 (11)	0.0321 (12)	0.0119 (9)	−0.0011 (9)	0.0079 (9)
C15	0.0421 (13)	0.0396 (12)	0.0538 (15)	0.0015 (10)	0.0132 (11)	0.0024 (11)
C16	0.107 (3)	0.072 (2)	0.064 (2)	0.0133 (19)	0.0287 (19)	0.0196 (16)
C17	0.063 (2)	0.120 (3)	0.092 (3)	0.037 (2)	0.0111 (19)	−0.012 (2)
C18	0.0510 (14)	0.0400 (12)	0.0347 (12)	0.0113 (10)	0.0077 (10)	0.0051 (10)
C19	0.0736 (19)	0.079 (2)	0.0486 (17)	0.0145 (16)	0.0124 (14)	0.0271 (15)
C20	0.0597 (17)	0.0632 (17)	0.076 (2)	0.0236 (14)	0.0172 (15)	0.0188 (15)
C21	0.0306 (10)	0.0269 (10)	0.0302 (11)	0.0051 (8)	−0.0021 (8)	0.0070 (8)
C22	0.0348 (11)	0.0327 (11)	0.0368 (12)	0.0023 (9)	0.0004 (9)	0.0133 (9)
C23	0.0505 (14)	0.0346 (11)	0.0473 (14)	0.0039 (10)	0.0033 (11)	0.0188 (10)
C24	0.0617 (16)	0.0318 (12)	0.0558 (15)	0.0148 (11)	0.0010 (12)	0.0181 (11)
C25	0.0482 (14)	0.0384 (12)	0.0532 (15)	0.0188 (10)	0.0048 (11)	0.0097 (11)
C26	0.0360 (12)	0.0315 (11)	0.0393 (12)	0.0073 (9)	0.0006 (9)	0.0073 (9)
C27	0.0364 (12)	0.0452 (13)	0.0540 (15)	0.0071 (10)	0.0116 (10)	0.0267 (11)
C28	0.0538 (15)	0.0447 (13)	0.0623 (17)	0.0130 (11)	0.0265 (13)	0.0154 (12)
C29	0.0464 (15)	0.0633 (17)	0.0720 (19)	0.0000 (13)	0.0172 (13)	0.0301 (15)
C30	0.0430 (13)	0.0446 (13)	0.0543 (15)	0.0151 (10)	0.0167 (11)	0.0153 (11)
C31	0.0421 (17)	0.141 (4)	0.144 (4)	0.0071 (19)	0.017 (2)	0.090 (3)
C32	0.157 (4)	0.088 (3)	0.063 (2)	−0.014 (3)	0.046 (2)	0.0058 (19)

Geometric parameters (Å, º) top

N1—C1	1.273 (3)	C18—C19	1.522 (3)
N1—C3	1.419 (2)	C18—C20	1.525 (4)
C1—C1ⁱ	1.498 (4)	C18—H18	1.0000
C1—C2	1.500 (3)	C19—H19A	0.9800
C2—H2A	0.9800	C19—H19B	0.9800
C2—H2B	0.9800	C19—H19C	0.9800
C2—H2C	0.9800	C20—H20A	0.9800
C3—C4	1.388 (3)	C20—H20B	0.9800
C3—C8	1.397 (3)	C20—H20C	0.9800
C4—C5	1.391 (3)	C21—C22	1.407 (3)
C4—H4	0.9500	C21—C26	1.408 (3)
C5—C6	1.390 (3)	C22—C23	1.392 (3)
C5—C9	1.501 (3)	C22—C27	1.525 (3)
C6—C7	1.396 (3)	C23—C24	1.380 (4)
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.393 (3)	C24—C25	1.378 (4)
C7—C21	1.498 (3)	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.395 (3)
C9—C14	1.406 (3)	C25—H25	0.9500
C9—C10	1.405 (3)	C26—C30	1.524 (3)
C10—C11	1.393 (3)	C27—C29	1.529 (3)
C10—C15	1.515 (3)	C27—C28	1.531 (4)
C11—C12	1.377 (4)	C27—H27	1.0000
C11—H11	0.9500	C28—H28A	0.9800
C12—C13	1.379 (4)	C28—H28B	0.9800
C12—H12	0.9500	C28—H28C	0.9800
C13—C14	1.396 (3)	C29—H29A	0.9800
C13—H13	0.9500	C29—H29B	0.9800
C14—C18	1.518 (3)	C29—H29C	0.9800
C15—C17	1.508 (4)	C30—C31	1.504 (4)
C15—C16	1.545 (4)	C30—C32	1.518 (4)
C15—H15	1.0000	C30—H30	1.0000
C16—H16A	0.9800	C31—H31A	0.9800
C16—H16B	0.9800	C31—H31B	0.9800
C16—H16C	0.9800	C31—H31C	0.9800
C17—H17A	0.9800	C32—H32A	0.9800
C17—H17B	0.9800	C32—H32B	0.9800
C17—H17C	0.9800	C32—H32C	0.9800

C1—N1—C3	120.55 (18)	C19—C18—H18	107.5
N1—C1—C1ⁱ	116.3 (2)	C20—C18—H18	107.5
N1—C1—C2	125.69 (18)	C18—C19—H19A	109.5
C1ⁱ—C1—C2	118.0 (2)	C18—C19—H19B	109.5
C1—C2—H2A	109.5	H19A—C19—H19B	109.5
C1—C2—H2B	109.5	C18—C19—H19C	109.5
H2A—C2—H2B	109.5	H19A—C19—H19C	109.5
C1—C2—H2C	109.5	H19B—C19—H19C	109.5
H2A—C2—H2C	109.5	C18—C20—H20A	109.5
H2B—C2—H2C	109.5	C18—C20—H20B	109.5
C4—C3—C8	120.00 (17)	H20A—C20—H20B	109.5
C4—C3—N1	121.39 (17)	C18—C20—H20C	109.5
C8—C3—N1	118.50 (18)	H20A—C20—H20C	109.5
C3—C4—C5	120.56 (18)	H20B—C20—H20C	109.5
C3—C4—H4	119.7	C22—C21—C26	120.83 (18)
C5—C4—H4	119.7	C22—C21—C7	119.77 (18)
C6—C5—C4	118.94 (18)	C26—C21—C7	119.39 (17)
C6—C5—C9	119.98 (17)	C23—C22—C21	118.4 (2)
C4—C5—C9	121.07 (17)	C23—C22—C27	121.13 (19)
C5—C6—C7	121.37 (17)	C21—C22—C27	120.51 (18)
C5—C6—H6	119.3	C24—C23—C22	121.3 (2)
C7—C6—H6	119.3	C24—C23—H23	119.4
C8—C7—C6	118.96 (17)	C22—C23—H23	119.4
C8—C7—C21	121.08 (17)	C25—C24—C23	120.0 (2)
C6—C7—C21	119.95 (16)	C25—C24—H24	120.0
C7—C8—C3	120.13 (18)	C23—C24—H24	120.0
C7—C8—H8	119.9	C24—C25—C26	121.2 (2)
C3—C8—H8	119.9	C24—C25—H25	119.4
C14—C9—C10	120.88 (19)	C26—C25—H25	119.4
C14—C9—C5	120.06 (19)	C25—C26—C21	118.4 (2)
C10—C9—C5	119.04 (19)	C25—C26—C30	120.0 (2)
C11—C10—C9	118.5 (2)	C21—C26—C30	121.58 (18)
C11—C10—C15	119.7 (2)	C22—C27—C29	113.5 (2)
C9—C10—C15	121.77 (19)	C22—C27—C28	111.90 (19)
C12—C11—C10	120.8 (2)	C29—C27—C28	110.0 (2)
C12—C11—H11	119.6	C22—C27—H27	107.0
C10—C11—H11	119.6	C29—C27—H27	107.0
C11—C12—C13	120.7 (2)	C28—C27—H27	107.0
C11—C12—H12	119.7	C27—C28—H28A	109.5
C13—C12—H12	119.7	C27—C28—H28B	109.5
C12—C13—C14	120.6 (2)	H28A—C28—H28B	109.5
C12—C13—H13	119.7	C27—C28—H28C	109.5
C14—C13—H13	119.7	H28A—C28—H28C	109.5
C13—C14—C9	118.5 (2)	H28B—C28—H28C	109.5
C13—C14—C18	119.5 (2)	C27—C29—H29A	109.5
C9—C14—C18	122.01 (19)	C27—C29—H29B	109.5
C17—C15—C10	112.7 (2)	H29A—C29—H29B	109.5
C17—C15—C16	111.0 (3)	C27—C29—H29C	109.5
C10—C15—C16	109.8 (2)	H29A—C29—H29C	109.5
C17—C15—H15	107.7	H29B—C29—H29C	109.5
C10—C15—H15	107.7	C31—C30—C32	112.0 (3)
C16—C15—H15	107.7	C31—C30—C26	112.7 (2)
C15—C16—H16A	109.5	C32—C30—C26	110.6 (2)
C15—C16—H16B	109.5	C31—C30—H30	107.1
H16A—C16—H16B	109.5	C32—C30—H30	107.1
C15—C16—H16C	109.5	C26—C30—H30	107.1
H16A—C16—H16C	109.5	C30—C31—H31A	109.5
H16B—C16—H16C	109.5	C30—C31—H31B	109.5
C15—C17—H17A	109.5	H31A—C31—H31B	109.5
C15—C17—H17B	109.5	C30—C31—H31C	109.5
H17A—C17—H17B	109.5	H31A—C31—H31C	109.5
C15—C17—H17C	109.5	H31B—C31—H31C	109.5
H17A—C17—H17C	109.5	C30—C32—H32A	109.5
H17B—C17—H17C	109.5	C30—C32—H32B	109.5
C14—C18—C19	112.0 (2)	H32A—C32—H32B	109.5
C14—C18—C20	111.2 (2)	C30—C32—H32C	109.5
C19—C18—C20	111.0 (2)	H32A—C32—H32C	109.5
C14—C18—H18	107.5	H32B—C32—H32C	109.5

C3—N1—C1—C1ⁱ	−178.3 (2)	C11—C10—C15—C17	51.1 (3)
C3—N1—C1—C2	2.1 (3)	C9—C10—C15—C17	−130.1 (3)
C1—N1—C3—C4	71.8 (3)	C11—C10—C15—C16	−73.1 (3)
C1—N1—C3—C8	−112.1 (2)	C9—C10—C15—C16	105.6 (3)
C8—C3—C4—C5	2.0 (3)	C13—C14—C18—C19	−58.5 (3)
N1—C3—C4—C5	178.11 (18)	C9—C14—C18—C19	121.9 (2)
C3—C4—C5—C6	−1.0 (3)	C13—C14—C18—C20	66.3 (3)
C3—C4—C5—C9	177.89 (19)	C9—C14—C18—C20	−113.3 (2)
C4—C5—C6—C7	−0.1 (3)	C8—C7—C21—C22	−83.0 (3)
C9—C5—C6—C7	−179.03 (18)	C6—C7—C21—C22	96.9 (2)
C5—C6—C7—C8	0.2 (3)	C8—C7—C21—C26	98.1 (2)
C5—C6—C7—C21	−179.70 (18)	C6—C7—C21—C26	−82.0 (2)
C6—C7—C8—C3	0.8 (3)	C26—C21—C22—C23	1.5 (3)
C21—C7—C8—C3	−179.31 (18)	C7—C21—C22—C23	−177.34 (19)
C4—C3—C8—C7	−1.9 (3)	C26—C21—C22—C27	−179.36 (19)
N1—C3—C8—C7	−178.08 (18)	C7—C21—C22—C27	1.8 (3)
C6—C5—C9—C14	−89.4 (2)	C21—C22—C23—C24	−0.5 (3)
C4—C5—C9—C14	91.7 (2)	C27—C22—C23—C24	−179.6 (2)
C6—C5—C9—C10	89.2 (2)	C22—C23—C24—C25	−0.7 (4)
C4—C5—C9—C10	−89.7 (2)	C23—C24—C25—C26	0.7 (4)
C14—C9—C10—C11	0.3 (3)	C24—C25—C26—C21	0.4 (3)
C5—C9—C10—C11	−178.33 (18)	C24—C25—C26—C30	−177.4 (2)
C14—C9—C10—C15	−178.52 (19)	C22—C21—C26—C25	−1.5 (3)
C5—C9—C10—C15	2.9 (3)	C7—C21—C26—C25	177.40 (19)
C9—C10—C11—C12	−1.1 (3)	C22—C21—C26—C30	176.3 (2)
C15—C10—C11—C12	177.8 (2)	C7—C21—C26—C30	−4.8 (3)
C10—C11—C12—C13	0.6 (4)	C23—C22—C27—C29	−30.5 (3)
C11—C12—C13—C14	0.6 (4)	C21—C22—C27—C29	150.4 (2)
C12—C13—C14—C9	−1.3 (3)	C23—C22—C27—C28	94.8 (2)
C12—C13—C14—C18	179.0 (2)	C21—C22—C27—C28	−84.3 (2)
C10—C9—C14—C13	0.9 (3)	C25—C26—C30—C31	−57.7 (4)
C5—C9—C14—C13	179.50 (18)	C21—C26—C30—C31	124.6 (3)
C10—C9—C14—C18	−179.45 (18)	C25—C26—C30—C32	68.6 (3)
C5—C9—C14—C18	−0.8 (3)	C21—C26—C30—C32	−109.2 (3)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₆₄H₈₀N₂
M_r	877.30
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.512 (3), 11.513 (3), 16.501 (6)
α, β, γ (°)	101.456 (18), 97.471 (13), 99.505 (17)
V (Å³)	1540.8 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.05
Crystal size (mm)	0.16 × 0.14 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer with Bruker APEXII CCD detector
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.992, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	10648, 5610, 4274
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.197, 1.06
No. of reflections	5610
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.26

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

Funding was provided by the NSERC of Canada in the form of a Doctoral Scholarship for TLL, and by an Alberta Innovates Studentship to TLL.

References

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